Neuroprotective activity of galloylated cyanogenic glucosides and hydrolysable tannins isolated from leaves of Phyllagathis rotundifolia.

PubMed

Tan, Hooi Poay; Wong, Daniel Zin Hua; Ling, Sui Kiong; Chuah, Cheng Hock; Kadir, Habsah Abdul

2012-01-01

The galloylated cyanogenic glucosides based on prunasin (1-7), gallotannins (8-14), ellagitannins (15-17), ellagic acid derivatives (18, 19) and gallic acid (20) isolated from the leaves of Phyllagathis rotundifolia (Melastomataceae) were investigated for their neuroprotective activity against hydrogen peroxide (H(2)O(2))-induced oxidative damage in NG108-15 hybridoma cell line. Among these compounds, the gallotannins and ellagitannins exhibited remarkable neuroprotective activities against oxidative damage in vitro as compared to galloylated cyanogenic glucosides and ellagic acid derivatives in a dose-dependent manner. They could be explored further as potential natural neuroprotectors in various remedies of neurodegenerative diseases. Copyright © 2011 Elsevier B.V. All rights reserved.

One new galloyl glycoside from fresh leaves of Psidium guajava L.

PubMed

Shu, Ji-cheng; Chou, Gui-xin; Wang, Zheng-tao

2010-03-01

To investigate the chemical constituents of Psidium Guajava L, the EtOH/H2O extract of the fresh leaves was subjected to various chromatography. Five constituents with galloyl moiety were isolated and elucidated as 1-O-(1, 2-propanediol)-6-O-galloyl-beta-D-glucopyranoside (1), gallic acid (2), ellagic acid (3), ellagic acid-4-O-beta-D-glucopyranoside (4) and quercetin-3-O-(6"-galloyl) beta-D-galactopyranoside (5) by spectroscopic methods, including 2D NMR and HR-ESI-MS spectrometry as well as by comparison with published data. Compounds 4 and 5 were obtained from P. guajava for the first time, and compound 1 is a new polyhydroxyl compound.

Behavior of ellagitannins, gallic acid, and ellagic acid under alkaline conditions

Treesearch

Richard W. Hemingway; W.E. Hillis

1971-01-01

Examination of the rates of hydrolysis of different ellagitannins under conditions comparable with cold soda and alkaline-groundwood pulping processes showed that some ellagitannins are notably resistant to hydrolysis. The rate of hydrolysis was dependent upon the pH and tempemture of the solution and particularly upon the structure of the compound. Decarboxylation of...

Ultra-high performance liquid chromatography coupled to mass spectrometry applied to the identification of valuable phenolic compounds from Eucalyptus wood.

PubMed

Santos, Sónia A O; Vilela, Carla; Freire, Carmen S R; Neto, Carlos Pascoal; Silvestre, Armando J D

2013-11-01

Ultra-high performance liquid chromatography (UHPLC) was applied for the first time in the analysis of wood extracts. The potential of this technique coupled to ion trap mass spectrometry in the rapid and effective detection and identification of bioactive components in complex vegetal samples was demonstrated. Several dozens of compounds were detected in less than 30min of analysis time, corresponding to more than 3-fold reduction in time, when compared to conventional HPLC analysis of similar extracts. The phenolic chemical composition of Eucalyptus grandis, Eucalyptus urograndis (E. grandis×E. urophylla) and Eucalyptus maidenii wood extracts was assessed for the first time, with the identification of 51 phenolic compounds in the three wood extracts. Twenty of these compounds are reported for the first time as Eucalyptus genus components. Ellagic acid and ellagic acid-pentoside are the major components in all extracts, followed by gallic and quinic acids in E. grandis and E. urograndis and ellagic acid-pentoside isomer, isorhamnetin-hexoside and gallic acid in E. maidenii. The antioxidant scavenging activity of the extracts was evaluated, with E. grandis wood extract showing the lowest IC50 value. Moreover, the antioxidant activity of these extracts was higher than that of the commercial antioxidant BHT and of those of the corresponding bark extracts. These results, together with the phenolic content values, open good perspectives for the exploitation of these renewable resources as a source of valuable phenolic compounds. Copyright © 2013 Elsevier B.V. All rights reserved.

Investigation of antioxidant ability of grape seeds extract to prevent oxidatively induced DNA damage by gas chromatography-tandem mass spectrometry.

PubMed

Aybastıer, Önder; Dawbaa, Sam; Demir, Cevdet

2018-01-01

Phenolic compounds have been studied elaborately for their efficacy to improve health and to protect against a wide variety of diseases. Herein this study, different analysis methods were implemented to evaluate the antioxidant properties of catechin and cyanidin using their standard substances and as they found in the grape seeds extracts. Total phenol contents were 107.39±8.94mg GAE/g dw of grape seeds for grape seed extract (GSE) and 218.32±10.66mg GAE/g dw of grape seeds for acid-hydrolyzed grape seed extract (AcGSE). The extracts were analyzed by HPLC-DAD system and the results showed the presence of catechin, gallic acid, chlorogenic acid and ellagic acid in the processed methanolic extract and cyanidin, gallic acid and ellagic acid in the processed acidified methanolic extract. The protective abilities of catechin and cyanidin were tested against the oxidation of DNA. The results showed that cyanidin has better protection of DNA against oxidation than catechin. GSE and AcGSE were revealed to inhibit the oxidatively induced DNA damage. GSE decreased about 57% of damage caused by the Fenton control sample. This study could show new aspects of the antioxidant profiles of cyanidin and catechin. Copyright © 2017 Elsevier B.V. All rights reserved.

In vitro digestibility, free and bound phenolic profiles and antioxidant activity of thermally treated Eragrostis tef L.

PubMed

Koubová, Eva; Mrázková, Martina; Sumczynski, Daniela; Orsavová, Jana

2018-06-01

Total phenolic content, phenolic profile and antioxidant activity were determined in free and bound phenolic fractions of thermally treated brown and white teff grains. Phenolic content in raw brown and white teff (1540 and 992 mg gallic acid equivalent kg -1 ) as well as antioxidant activity (6.3 and 5.5 mmol trolox equivalent kg -1 ) were higher in free phenolic fractions. The most significant decrease in total phenolics was observed after application of the sous-vide method (35% for brown teff and 11% for white teff). Main free phenolics of heat-treated teff were ferulic, protocatechuic, p-coumaric and ellagic acids, rutin and epigallocatechin. Main bound phenolics were ferulic, gallic, sinapic and ellagic acids, catechin and epigallocatechin. The detrimental effect on free and bound quercetin and bound cinnamic acid concentrations was also examined during heat treatment. Thermally treated brown teff showed a high level of in vitro organic matter digestibility if water cooking and rice cooker (both 99.5%) and sous-vide (96.5%) methods were applied. The sous-vide method may be recommended as the most suitable hydrothermal treatment for grains of teff when compared with water cooking and rice cooker methods. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

Understanding the native Californian diet: Identification of condensed and hydrolyzable tannins in tanoak acorns (Lithocarpus densiflorus).

PubMed

Meyers, Katherine J; Swiecki, Tedmund J; Mitchell, Alyson E

2006-10-04

The tanoak (Lithocarpus densiflorus) acorn was a staple food in the Native American diet and is still used in traditional dishes. Acorns from the genus Quercus have been shown to contain a large range of hydrolyzable tannins. However, neither hydrolyzable nor condensed tannins have been characterized in tanoak acorns. The aim of this study was to identify the full range of hydrolyzable and condensed tannins in extracts of tanoak acorns using liquid chromatography/electrospray ionization-mass spectrometry/mass spectrometry. Condensed tannins were identified as B type oligomers of (epi)-catechin (procyanidins) with a degree of polymerization up to six. Oligomers up to and including tetramers were identified by UV spectra and MS detection whereas pentamers and hexamers were detected only by MS. The total concentration of condensed tannins was 464 mg/100 g acorn pericarp. The concentration of propocyanidin monomers, dimers, trimers, and tetramers in acorn pericarp (mg/100 g acorn pericarp) were 95 +/- 10.9, 148 +/- 35.0, 90 +/- 17.9, and 131 +/- 1.9, respectively. No procyanidins were found in the acorn cotyledon tissue. A total of 22 hydrolyzable tannins were identified in methanolic extracts of acorn cotyledon tissue. Gallic acid derivatives predominated and included galloylated esters of glucose, hexahydrodiphenoyl esters of glucose, and methylated gallates. Galloylated esters of glucose were present as isomers of galloyl glucose, digalloyl glucose, and trigalloyl glucose. Mass spectral fragmentation patterns indicate the presence of one gallic acid-galloyl glucose isomer and two gallic acid-digalloyl-glucose isomers. No isomers of tetragalloyl glucose and pentagalloyl glucose were identified. Ellagic acid and ellagic acid pentoside were also identified.

Ellagic Acid: A Logical Lead for Drug Development?

PubMed

Shakeri, Abolfazl; Zirak, Mohammad Reza; Sahebkar, Amirhossein

2018-01-01

Naturally occurring polyphenols are the subject of increasing attention due to their potent antioxidant activity and their marked effects on the prevention of various oxidative stress-associated diseases such as cancer. Ellagic acid (EA) is an herbal polyphenol that is structurally a condensed dimer of gallic acid. This review aims to provide a comprehensive and updated overview on the biological activities of EA and potential therapeutic applications. EA is found in fruits and nuts, either in the combined form with hexahydroxydiphenic acid or in the bound form (ellagitannins). EA exhibits many biological properties such as antioxidant, anti-diabetic, anticancer and apoptosis-inducing activities. These biological and pharmacological properties are relevant to the treatment of several human diseases. Owing to its multiple mechanisms of action, EA represents a potential therapeutic agent against human diseases particularly cancer. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

Acid hydrolysis of crude tannins from infructescence of Platycarya strobilacea Sieb. et Zucc to produce ellagic acid.

PubMed

Zhang, Liangliang; Wang, Yongmei; Xu, Man

2014-01-01

The infructescence of Platycarya strobilacea Sieb. et Zucc is a well-known traditional medicine in China, Japan and Korea. The infructescence of P. strobilacea Sieb. et Zucc is a rich source of ellagitannins that are composed of ellagic acid (EA) and gallic acid, linked to a sugar moiety. The aim of this study was to prepare EA by acid hydrolysis of crude tannins from the infructescence of P. strobilacea Sieb. et Zucc, and establish a new technological processing method for EA. The natural antioxidant EA was prepared by using the water extraction of infructescence of P. strobilacea Sieb. et Zucc, evaporation, condensation, acid hydrolysis and prepared by the process of crystallisation. The yield percentage of EA from crude EA was more than 20% and the purity of the product was more than 98%, as identified by using HPLC. The structure was identified on the basis of spectroscopic analysis and comparison with authentic compound.

Isolation and characterization of ellagitannins as the major polyphenolic components of Longan (Dimocarpus longan Lour) seeds.

PubMed

Sudjaroen, Yuttana; Hull, William E; Erben, Gerhard; Würtele, Gerd; Changbumrung, Supranee; Ulrich, Cornelia M; Owen, Robert W

2012-05-01

Longan (Dimocarpus longan Lour, syn. Euphoria longan Lam.) represents an important fruit in Northern Thailand and has significant economic impact. The fruit is either consumed fresh or as commercially prepared dried and canned products. The canning industry in Thailand produces considerable quantities of waste products, in particular Longan seeds. Because these seeds may be an exploitable source of natural phenolic antioxidants, it was of interest to identify, purify and quantitate the major potential antioxidant phenolics contained therein. The polyphenolic fraction from ground Longan seeds was obtained by extraction with methanol after delipidation with hexane. The hexane extract contained predominantly long-chain fatty acids with major contributions from palmitic (35%) and oleic (28%) acids. The polyphenolic fraction (80.90 g/kg dry weight) was dominated by ellagic acid (25.84 g/kg) and the known ellagitannins corilagin (13.31 g/kg), chebulagic acid (13.06 g/kg), ellagic acid 4-O-α-l-arabinofuranoside (9.93 g/kg), isomallotinic acid (8.56 g/kg) and geraniin (5.79 g/kg). Structure elucidation was performed with mass spectrometry and complete assignment of (1)H and (13)C NMR signals. The methanol extracts exhibited strong antioxidant capacities with an IC(50) of 154 μg/ml for reactive oxygen species attack on salicylic acid and 78 μg/ml for inhibition of xanthine oxidase in the hypoxanthine/xanthine oxidase assay. The extracts were less effective in the 2-deoxyguanosine assay (IC(50)=2.46 mg/ml), indicating that gallates along with ellagic acid and its congeners exert their potential antioxidant effects predominantly by precipitation of proteins such as xanthine oxidase. This was confirmed for the pure compounds gallic acid, methyl gallate, ellagic acid and corilagin. Copyright © 2012 Elsevier Ltd. All rights reserved.

Profile of Polyphenol Compounds of Five Muscadine Grapes Cultivated in the United States and in Newly Adapted Locations in China

PubMed Central

Wei, Zheng; Luo, Jianming; Huang, Yu; Guo, Wenfeng; Zhang, Yali; Guan, Huan; Xu, Changmou; Lu, Jiang

2017-01-01

Polyphenol compositions and concentrations in skins and seeds of five muscadine grapes (cv. “Noble”, “Alachua”, “Carlos”, “Fry”, and “Granny Val”) cultivated in the United States (Tallahassee-Florida, TA-FL) and South China (Nanning-Guangxi, NN-GX and Pu’er-Yunnan, PE-YN) were investigated, using ultra performance liquid chromatography tandem triple quadrupole time-of-flight mass spectrometry (UPLC Triple TOF MS/MS). Fourteen ellagitannins were newly identified in these muscadine grapes. The grapes grown in NN-GX accumulated higher levels of ellagic acid, methyl brevifolin carboxylate, and ellagic acid glucoside in skins, and penta-O-galloyl-glucose in seeds. In PE-YN, more flavonols were detected in skins, and higher contents of flavan-3-ols, ellagic acid, and methyl gallate were identified in seeds. Abundant seed gallic acid and flavonols were found among the grapes grown in TA-FL. Based on principal component analysis (PCA) of 54 evaluation parameters, various cultivars grown in different locations could be grouped together and vice versa for the same cultivar cultivated in different regions. This is the result of the interaction between genotype and environmental conditions, which apparently influences the polyphenol synthesis and accumulation. PMID:28335440

Improved Quantification of Free and Ester-Bound Gallic Acid in Foods and Beverages by UHPLC-MS/MS.

PubMed

Newsome, Andrew G; Li, Yongchao; van Breemen, Richard B

2016-02-17

Hydrolyzable tannins are measured routinely during the characterization of food and beverage samples. Most methods for the determination of hydrolyzable tannins use hydrolysis or methanolysis to convert complex tannins to small molecules (gallic acid, methyl gallate, and ellagic acid) for quantification by HPLC-UV. Often unrecognized, analytical limitations and variability inherent in these approaches for the measurement of hydrolyzable tannins include the variable mass fraction (0-0.90) that is released as analyte, contributions of sources other than tannins to hydrolyzable gallate (can exceed >10 wt %/wt), the measurement of both free and total analyte, and lack of controls to account for degradation. An accurate, specific, sensitive, and higher-throughput approach for the determination of hydrolyzable gallate based on ultrahigh-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) that overcomes these limitations was developed.

Exploring the Degradation of Gallotannins Catalyzed by Tannase Produced by Aspergillus niger GH1 for Ellagic Acid Production in Submerged and Solid-State Fermentation.

PubMed

Chávez-González, Mónica L; Guyot, Sylvain; Rodríguez-Herrera, Raul; Prado-Barragán, Arely; Aguilar, Cristóbal N

2018-06-01

Due to great interest on producing bioactive compounds for functional foods and biopharmaceuticals, it is important to explore the microbial degradation of potential sources of target biomolecules. Gallotannins are polyphenols present in nature, an example of them is tannic acid which is susceptible to enzymatic hydrolysis. This hydrolysis is performed by tannase or tannin acyl hydrolase, releasing in this way, biomolecules with high-added value. In the present study, chemical profiles obtained after fungal degradation of tannic acid under two bioprocesses (submerged fermentation (SmF) and solid state fermentation (SSF)) were determined. In both fermentation systems (SmF and SSF), Aspergillus niger GH1 strain and tannic acid as a sole carbon source and inducer were used (the presence of tannic acid promotes production of enzyme tannase). In case of SSF, polyurethane foam (PUF) was used like as support of fermentation; culture medium only was used in case of submerged fermentation. Fermentation processes were monitored during 72 h; samples were taken kinetically every 8 h; and all extracts obtained were partially purified to obtain polyphenolic fraction and then were analyzed by liquid chromatography-mass spectrometry (LC-MS). Molecules like gallic acid and n-galloyl glucose were identified as intermediates in degradation of tannic acid; during SSF was identified ellagic acid production. The results obtained in this study will contribute to biotechnological production of ellagic acid.

Protective effect of gallic acid and Syzygium cumini extract against oxidative stress-induced cellular injury in human lymphocytes.

PubMed

De Bona, Karine Santos; Bonfanti, Gabriela; Bitencourt, Paula Eliete Rodrigues; da Silva, Thainan Paz; Borges, Raphaela Maleski; Boligon, Aline; Pigatto, Aline; Athayde, Margareth Lynde; Moretto, Maria Beatriz

2016-01-01

Syzygium cumini (Myrtaceae) presents antioxidant, anti-inflammatory, hypoglycemic and antibacterial effects; however, the cellular and molecular mechanisms of action in the immune system are not yet completely elucidated. This study evaluates the in vitro effect of gallic acid and aqueous S. cumini leaf extract (ASc) on adenosine deaminase (ADA) and dipeptidyl peptidase IV (DPP-IV) activities, cell viability and oxidative stress parameters in lymphocytes exposed to 2, 2'-azobis-2-amidinopropane dihydrochloride (AAPH). Lymphocytes were incubated with ASc (100 and 500 µg/ml) and gallic acid (50 and 200 µM) at 37 °C for 30 min followed by incubation with AAPH (1 mM) at 37 °C for 2 h. After the incubation time, the lymphocytes were used for determinations of ADA, DPP-IV and lactate dehydrogenase (LDH) activities, lipid peroxidation, protein thiol (P-SH) group levels and cellular viability by colorimetric methods. (i) HPLC fingerprinting of ASc revealed the presence of catechin, epicatechin, rutin, quercitrin, isoquercitrin, quercetin, kaempferol and chlorogenic, caffeic, gallic and ellagic acids; (ii) for the first time, ASc reduced the AAPH-induced increase in ADA activity, but no effect was observed on DPP-IV activity; (iii) ASc increased P-SH groups and cellular viability and decreased LDH activity, but was not able to reduce the AAPH-induced lipid peroxidation; (iv) gallic acid showed less protective effects than ASc. ASc affects the purinergic system and may modulate adenosine levels, indicating that the extract of this plant exhibits immunomodulatory properties. ASc also may potentially prevent the cellular injury induced by oxidative stress, highlighting its cytoprotective effects.

Evaluation of Toxicological Effects of an Aqueous Extract of Shells from the Pecan Nut Carya illinoinensis (Wangenh.) K. Koch and the Possible Association with Its Inorganic Constituents and Major Phenolic Compounds.

PubMed

Porto, Luiz Carlos S; da Silva, Juliana; Sousa, Karen; Ambrozio, Mariana L; de Almeida, Aline; Dos Santos, Carla Eliete I; Dias, Johnny F; Allgayer, Mariangela C; Dos Santos, Marcela S; Pereira, Patrícia; Ferraz, Alexandre B F; Picada, Jaqueline N

2016-01-01

Background. Industrial processing of the pecan nut Carya illinoinensis K. Koch generated a large amount of shells, which have been used to prepare nutritional supplements and medicinal products; however, the safe use of shells requires assessment. This study evaluated the toxic, genotoxic, and mutagenic effects of pecan shell aqueous extract (PSAE) and the possible contribution of phenolic compounds, ellagic and gallic acids, and inorganic elements present in PSAE to induce toxicity. Results. Levels of inorganic elements like K, P, Cl, and Rb quantified using the Particle-Induced X-Ray Emission method were higher in PSAE than in pecan shells, while Mg and Mn levels were higher in shells. Mice showed neurobehavioral toxicity when given high PSAE doses (200-2,000 mg kg(-1)). The LD50 was 1,166.3 mg kg(-1). However, PSAE (50-200 mg·kg(-1)) and the phenolic compounds (10-100 mg·kg(-1)) did not induce DNA damage or mutagenicity evaluated using the comet assay and micronucleus test. Treatment with ellagic acid (10-100 mg·kg(-1)) decreased triglyceride and glucose levels, while treatments with PSAE and gallic acid had no effect. Conclusion. Pecan shell toxicity might be associated with high concentrations of inorganic elements such as Mn, Al, Cu, and Fe acting on the central nervous system, besides phytochemical components, suggesting that the definition of the safe dose should take into account the consumption of micronutrients.

Evaluation of Toxicological Effects of an Aqueous Extract of Shells from the Pecan Nut Carya illinoinensis (Wangenh.) K. Koch and the Possible Association with Its Inorganic Constituents and Major Phenolic Compounds

PubMed Central

Porto, Luiz Carlos S.; Sousa, Karen; Ambrozio, Mariana L.; de Almeida, Aline; dos Santos, Carla Eliete I.; Dias, Johnny F.; Allgayer, Mariangela C.; dos Santos, Marcela S.; Pereira, Patrícia; Picada, Jaqueline N.

2016-01-01

Background. Industrial processing of the pecan nut Carya illinoinensis K. Koch generated a large amount of shells, which have been used to prepare nutritional supplements and medicinal products; however, the safe use of shells requires assessment. This study evaluated the toxic, genotoxic, and mutagenic effects of pecan shell aqueous extract (PSAE) and the possible contribution of phenolic compounds, ellagic and gallic acids, and inorganic elements present in PSAE to induce toxicity. Results. Levels of inorganic elements like K, P, Cl, and Rb quantified using the Particle-Induced X-Ray Emission method were higher in PSAE than in pecan shells, while Mg and Mn levels were higher in shells. Mice showed neurobehavioral toxicity when given high PSAE doses (200–2,000 mg kg−1). The LD50 was 1,166.3 mg kg−1. However, PSAE (50–200 mg·kg−1) and the phenolic compounds (10–100 mg·kg−1) did not induce DNA damage or mutagenicity evaluated using the comet assay and micronucleus test. Treatment with ellagic acid (10–100 mg·kg−1) decreased triglyceride and glucose levels, while treatments with PSAE and gallic acid had no effect. Conclusion. Pecan shell toxicity might be associated with high concentrations of inorganic elements such as Mn, Al, Cu, and Fe acting on the central nervous system, besides phytochemical components, suggesting that the definition of the safe dose should take into account the consumption of micronutrients. PMID:27525021

Antioxidants of Phyllanthus emblica L. Bark Extract Provide Hepatoprotection against Ethanol-Induced Hepatic Damage: A Comparison with Silymarin

PubMed Central

Chaphalkar, Renuka; Apte, Kishori G.; Talekar, Yogesh

2017-01-01

Phyllanthus emblica L. (amla) has been used in Ayurveda as a potent rasayan for treatment of hepatic disorders. Most of the pharmacological studies, however, are largely focused on PE fruit, while the rest of the parts of PE, particularly, bark, remain underinvestigated. Therefore, we aimed to investigate the protective effect of the hydroalcoholic extract of Phyllanthus emblica bark (PEE) in ethanol-induced hepatotoxicity model in rats. Total phenolic, flavonoid, and tannin content and in vitro antioxidant activities were determined by using H2O2 scavenging and ABTS decolorization assays. Our results showed that PEE was rich in total phenols (99.523 ± 1.91 mg GAE/g), total flavonoids (389.33 ± 1.25 mg quercetin hydrate/g), and total tannins (310 ± 0.21 mg catechin/g), which clearly support its strong antioxidant potential. HPTLC-based quantitative analysis revealed the presence of the potent antioxidants gallic acid (25.05 mg/g) and ellagic acid (13.31 mg/g). Moreover, one-month PEE treatment (500 and 1000 mg/kg, p.o.) followed by 30-day 70% ethanol (10 mL/kg) administration showed hepatoprotection as evidenced by significant restoration of ALT (p < 0.01), AST (p < 0.001), ALP (p < 0.05), and TP (p < 0.001) and further confirmed by liver histopathology. PEE-mediated hepatoprotection could be due to its free radical scavenging and antioxidant activity that may be ascribed to its antioxidant components, namely, ellagic acid and gallic acid. Thus, the results of the present study support the therapeutic claims made in Ayurveda about Phyllanthus emblica. PMID:28168009

Polyphenolic profile and bioactivity study of Oenothera speciosa Nutt. aerial parts.

PubMed

Marzouk, Mohamed S; Moharram, Fatma A; El Dib, Rabab A; El-Shenawy, Siham M; Tawfike, Ahmed F

2009-04-07

Two new flavonol glycosides, myricetin 4'-O-alpha-L-rhamnopyranoside (1) and quercetin 3'-O-alpha-L-rhamnopyranoside (2), together with a novel biflavonol compound, speciin (3), as well as eleven phenolic metabolites, namely myricitrin (4), europetin 3-O-alpha-L-(1)C(4)-rhamnopyranoside (5), quercitrin (6), hyperin (7), rhamnetin 3-O-beta-galacto-pyranoside (8), caffeic acid (9), caffeic acid methyl ester (10), chlorogenic acid (11), chlorogenic acid methyl ester (12), gallic acid (13) and gallic acid methyl ester (14), were identified from the 80 % methanol extract of the aerial parts (leaves and stems) of Oenothera speciosa Nutt. (Onagraceae). In addition myricetin (15), quercetin (16) and ellagic acid (17) were identified from the chloroform extract. The structures were established depending on their chemical and physical analyses (UV, HR-ESIMS, 1D and 2D NMR). It was found that 80 % aqueous methanol extract of O. speciosa is non-toxic to mice up to 5 g kg(-1)b wt. The investigated extract exhibited significant antihyperglycaemic and anti-inflammatory activities in a dose dependant manner. Also, the 80 % methanol extract, myricitrin(4) and hyperin(7) showed potent antioxidant activity in vitro using 1,1-diphenyl 2-picryl hydrazyl (DPPH) radical assay.

Metabolite profiling of polyphenols in the Tunisian plant Tamarix aphylla (L.) Karst.

PubMed

Mahfoudhi, Adel; Prencipe, Francesco Pio; Mighri, Zine; Pellati, Federica

2014-10-01

In this study, a detailed investigation on the composition of polyphenols of Tamarix aphylla (L.) Karst., consisting of phenolic acids and flavonoids, was carried out. In order to optimize the yield of secondary metabolites, three extraction techniques were compared, including dynamic maceration, ultrasound-assisted extraction and Soxhlet extraction. The latter technique provided the best results in terms of both recovery and selectivity, using ethyl acetate as extraction solvent for 2h. The analysis of T. aphylla polyphenols was performed by means of HPLC-UV/DAD, HPLC-ESI-MS and MS(2), using an ion trap mass analyzer. Phenolic acids and flavonoids were separated on an Ascentis C18 column (250mm×4.6mm I.D., 5μm), with a mobile phase composed of 0.1M formic acid in water and acetonitrile, under gradient elution. The proposed method was fully validated in agreement with ICH guidelines and then applied to the analysis of T. aphylla leaves and stems. A total of 14 phenolic compounds were characterized for the first time in this plant extracts by using UV, MS and MS(2) data. The amount of total phenolics was found to be 993.1±22.5μg/g in the leaves and 113.1±25.8μg/g in the stems, respectively. The most abundant constituents found in the leaves include ellagic acid (211.4±10.8μg/g), quercetin (125.7±4.7μg/g) and gallic acid (120.6±1.2μg/g), whereas those in the stems were ellagic acid (44.4±3.9μg/g), gallic acid (24.3±3.3μg/g) and kaempferol (16.3±1.6μg/g). The developed method can be considered a useful tool for the metabolite profiling of T. aphylla, which represents a potential source of bioactive compounds to be used in phytotherapy. Copyright © 2014 Elsevier B.V. All rights reserved.

Ellagic acid, phenolic acids, and flavonoids in Malaysian honey extracts demonstrate in vitro anti-inflammatory activity.

PubMed

Kassim, Mustafa; Achoui, Mouna; Mustafa, Mohd Rais; Mohd, Mustafa Ali; Yusoff, Kamaruddin Mohd

2010-09-01

Natural honey has been used in traditional medicine of different cultures throughout the world. This study looked into the extraction of Malaysian honey and the evaluation of the anti-inflammatory activity of these extracts. It was hypothesized that honey extracts contain varying amounts of phenolic compounds and that they possess different in vitro anti-inflammatory activities. Honey extracts were analyzed using liquid chromatography-mass spectrometry to identify and compare phenolic compounds, whereas high-performance liquid chromatography was used for their quantification. Subsequently, honey methanol extract (HME) and honey ethyl acetate extract (HEAE) were tested in vitro for their effect on nitric oxide production in stimulated macrophages. The extracts were also tested for their effects on tumor necrosis factor-α (TNF) cytotoxicity in L929 cells. The major phenolics in the extracts were ellagic, gallic, and ferulic acids; myricetin; chlorogenic acid; and caffeic acid. Other compounds found in lower concentrations were hesperetin, p-coumaric acid, chrysin, quercetin, luteolin, and kaempferol. Ellagic acid was the most abundant of the phenolic compounds recorded, with mean concentrations of 3295.83 and 626.74 μg/100 g of honey in HME and HEAE, respectively. The median maximal effective concentrations for in vitro nitric oxide inhibition by HEAE and HME were calculated to be 37.5 and 271.7 μg/mL, respectively. The median maximal effective concentrations for protection from TNF cytotoxicity by HEAE and HME were 168.1 and 235.4 μg/mL, respectively. In conclusion, HEAE exhibited greater activity in vitro, whereas HME contained a higher concentration of phenolic compounds per 100 g of honey. Copyright © 2010 Elsevier Inc. All rights reserved.

Analysis of hydrolyzable tannins and other phenolic compounds in emblic leafflower (Phyllanthus emblica L.) fruits by high performance liquid chromatography-electrospray ionization mass spectrometry.

PubMed

Yang, Baoru; Kortesniemi, Maaria; Liu, Pengzhan; Karonen, Maarit; Salminen, Juha-Pekka

2012-09-05

Phenolic compounds were extracted from dried emblic leafflower (Phyllanthus emblica L.) fruits with methanol and separated by Sephadex LH-20 column chromatography. The raw extracts and fractions were analyzed with HPLC coupled with diode array UV spectroscopy, electrospray ionization mass spectrometry, and tandem mass spectrometry. Mucic acid gallate, mucic acid lactone gallate, monogalloylglucose, gallic acid, digalloylglucose, putranjivain A, galloyl-HHDP-glucose, elaeocarpusin, and chebulagic acid were suggested to be the most abundant compounds in the crude methanol extracts of the fruits. In addition, 144 peaks were detected, of which 67 were tentatively identified mostly as ellagitannins, flavonoids, and simple gallic acid derivatives in the fractions. The results indicated the presence of neochebulagic acid, isomers of neochebuloyl galloylglucose, chebuloyl neochebuloyl galloylglucose, ellagic acid glycosides, quercetin glycosides, and eriodictyol coumaroyl glycosides in the fruits. The study provides a systematic report of the retention data and characteristics of UV, MS, and MS/MS spectra of the phenolic compounds in the fruits of emblic leafflower. The fruits of two varieties (Ping Dan No 1 and Fruity) from Guangxi Province differed from those of wild Tian Chuan emblic leafflower from Fujian Province in the content and profile of phenolic compounds.

Tannin analysis of chestnut bark samples (Castanea sativa Mill.) by HPLC-DAD-MS.

PubMed

Comandini, Patrizia; Lerma-García, María Jesús; Simó-Alfonso, Ernesto Francisco; Toschi, Tullia Gallina

2014-08-15

In the present investigation, an HPLC-DAD/ESI-MS method for the complete analysis of tannins and other phenolic compounds of different commercial chestnut bark samples was developed. A total of seven compounds (vescalin, castalin, gallic acid, vescalagin, 1-O-galloyl castalagin, castalagin and ellagic acid) were separated and quantified, being 1-O-galloyl castalagin tentatively identified and found for the first time in chestnut bark samples. Thus, this method provided information regarding the composition and quality of chestnut bark samples, which is required since these samples are commercialised due to their biochemical properties as ingredients of food supplements. Copyright © 2014 Elsevier Ltd. All rights reserved.

Comparison between cachaça and rum using pattern recognition methods.

PubMed

Cardoso, Daniel R; Andrade-Sobrinho, Luiz G; Leite-Neto, Alexandre F; Reche, Roni V; Isique, William D; Ferreira, Marcia M C; Lima-Neto, Benedito S; Franco, Douglas W

2004-06-02

The differentiation between cachaça and rum using analytical data referred to alcohols (methanol, propanol, isobutanol, and isopentanol), acetaldehyde, ethyl acetate, organic acids (octanoic acid, decanoic acid, and dodecanoic acid), metals (Al, Ca, Co, Cu, Cr, Fe, Mg, Mn, Ni, Na, and Zn), and polyphenols (protocatechuic acid, sinapaldehyde, syringaldehyde, ellagic acid, syringic acid, gallic acid, (-)-epicatechin, vanillic acid, vanillin, p-coumaric acid, coniferaldehyde, coniferyl alcohol, kaempferol, and quercetin) is described. The organic and metal analyte contents were determined in 18 cachaça and 21 rum samples using chromatographic methods (GC-MS, GC-FID, and HPLC-UV-vis) and inductively coupled plasma atomic emission spectrometry, respectively. The analytical data of the above compounds, when treated by principal component analysis, hierarchical cluster analysis, discriminant analysis, and K-nearest neighbor analysis, provide a very good discrimination between the two classes of beverages.

Survey of antioxidant capacity and phenolic composition of blueberry, blackberry, and strawberry in Nanjing*

PubMed Central

Huang, Wu-yang; Zhang, Hong-cheng; Liu, Wen-xu; Li, Chun-yang

2012-01-01

Berries are a good source of natural antioxidants. In the present study, the total antioxidant capacity and phenolic composition of three berry fruits (blueberry, blackberry, and strawberry) cultivated in Nanjing were investigated. Blueberry, with a Trolox equivalent antioxidant capacity (TEAC) value of 14.98 mmol Trolox/100 g dry weight (DW), exhibited the strongest total antioxidant capacity using both the 2,2-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) and the 2,2-diphenyl-1-picrylhydrazyl (DPPH) methods. Blueberry also had the highest total phenolic content (TPC, 9.44 mg gallic acid/g DW), total flavonoid content (TFC, 36.08 mg rutin/g DW), and total anthocyanidin content (TAC, 24.38 mg catechin/g DW). A preliminary analysis using high performance liquid chromatography (HPLC) showed that the blueberry, blackberry, and strawberry samples tested contained a range of phenolic acids (including gallic acid, protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid, p-coumaric acid, ferulic acid, ellagic acid, and cinnamic acid) and various types of flavonoids (flavone: luteolin; flavonols: rutin, myricetin, quercetrin, and quercetin; flavanols: gallocatechin, epigallocatechin, catechin, and catechin gallate; anthocyanidins: malvidin-3-galactoside, malvidin-3-glucoside, and cyanidin). In particular, the blueberries had high levels of proanthocyanidins and anthocyanidins, which might be responsible for their strong antioxidant activities. These results indicate a potential market role for berries (especially blueberries) as a functional food ingredient or nutraceutical. PMID:22302422

Validated Method for the Characterization and Quantification of Extractable and Nonextractable Ellagitannins after Acid Hydrolysis in Pomegranate Fruits, Juices, and Extracts.

PubMed

García-Villalba, Rocío; Espín, Juan Carlos; Aaby, Kjersti; Alasalvar, Cesarettin; Heinonen, Marina; Jacobs, Griet; Voorspoels, Stefan; Koivumäki, Tuuli; Kroon, Paul A; Pelvan, Ebru; Saha, Shikha; Tomás-Barberán, Francisco A

2015-07-29

Pomegranates are one of the main highly valuable sources of ellagitannins. Despite the potential health benefits of these compounds, reliable data on their content in pomegranates and derived extracts and food products is lacking, as it is usually underestimated due to their complexity, diversity, and lack of commercially available standards. This study describes a new method for the analysis of the extractable and nonextractable ellagitannins based on the quantification of the acid hydrolysis products that include ellagic acid, gallic acid, sanguisorbic acid dilactone, valoneic acid dilactone, and gallagic acid dilactone in pomegranate samples. The study also shows the occurrence of ellagitannin C-glycosides in pomegranates. The method was optimized using a pomegranate peel extract. To quantify nonextractable ellagitannins, freeze-dried pomegranate fruit samples were directly hydrolyzed with 4 M HCl in water at 90 °C for 24 h followed by extraction of the pellet with dimethyl sulfoxide/methanol (50:50, v/v). The method was validated and reproducibility was assessed by means of an interlaboratory trial, showing high reproducibility across six laboratories with relative standard deviations below 15%. Their applicability was demonstrated in several pomegranate extracts, different parts of pomegranate fruit (husk, peels, and mesocarp), and commercial juices. A large variability has been found in the ellagitannin content (150-750 mg of hydrolysis products/g) and type (gallagic acid/ellagic acid ratios between 4 and 0.15) of the 11 pomegranate extracts studied.

New Electrochemical Evaluation of the Antioxidant Capacity of Beverages with Polyoxometalates as Redox Probes.

PubMed

Ueda, Tadaharu; Okumura, Takashi; Tanaka, Yukino; Akase, Saki; Shimamura, Tomoko; Ukeda, Hiroyuki

2016-01-01

A new method was developed to evaluate antioxidant activity based on the redox properties of polyoxometalates, which are partially reduced by antioxidants to generate a limiting potential. The polyoxometalates [PMo12O40](3-), [PVW11O40](4-) and [SV2W10O40]4- formed in situ were used as electrochemical probes for the new evaluation method, and their formation conditions were optimized to evaluate the antioxidant activities of gallic acid, ellagic acid, catechin, quercetin, morin, trans-ferulic acid, sesamol, α-tocopherol, δ-tocopherol and L-ascorbic acid. The observed difference between initial potential and limiting potential (ΔE) were compared with spectrophotometrically evaluated antioxidant activities. In addition, the antioxidant capacities of five beverages (Japanese green tea, concentrated catechin-containing green tea, grapefruit juice, red wine and Japanese sake) were evaluated.

The hepatoprotective effect of Phyllanthus emblica L. fruit on high fat diet-induced non-alcoholic fatty liver disease (NAFLD) in SD rats.

PubMed

Huang, Cheng-Ze; Tung, Yu-Tang; Hsia, Shih-Min; Wu, Chi-Hao; Yen, Gow-Chin

2017-02-22

Non-alcoholic fatty liver disease (NAFLD), the most common chronic liver disease, is closely associated with metabolic syndrome and refers to the accumulation of hepatic steatosis not due to excess alcohol consumption. Phyllanthus emblica L. is a rich source of gallic acid and many known medicinally phytochemicals such as tannins, lignans, flavonoids, alkaloids, vitamin C, mucic acid, and ellagic acid. Our previous study has revealed that P. emblica exhibits inhibitory effects on hepatic steatosis and liver fibrosis in vitro, as well as gallic acid improves high fat diet (HFD)-induced dyslipidaemia, hepatosteatosis, and oxidative stress in vivo. Therefore, the aim of this study was to investigate the hepatoprotective effect of the water extract of P. emblica L. fruit (WEPE) on NAFLD in an animal model. The results showed that WEPE could significantly decrease body weight, peritoneal fat and epididymal fat, enhance the antioxidant enzyme activities, and improve steatosis through elevating adiponectin in adipocytes and PPAR-α in the liver as well as lowering SREBP-1c in the liver of rats fed with a high fat diet (HFD). This might be an explanation for the hepatic fat deposition-lowering effect of WEPE. These results demonstrate that WEPE could be beneficial for the amelioration of HFD-induced steatosis.

Effect of wine inhibitors on free pineapple stem bromelain activity in a model wine system.

PubMed

Esti, Marco; Benucci, Ilaria; Liburdi, Katia; Garzillo, Anna Maria Vittoria

2011-04-13

The influence of potential inhibitors, naturally present in wine, on the activity of stem bromelain was investigated in order to evaluate the applicability of this enzyme for protein stabilization in white wine. Bromelain proteolytic activity was tested against a synthetic substrate (Bz-Phe-Val-Arg-pNA) in a model wine system after adding ethanol, sulfur dioxide (SO(2)), skin, seed, and gallic and ellagic tannins at the average range of their concentration in wine. All the inhibitors of stem bromelain activity tested turned out to be reversible. Ethanol was a competitive inhibitor with a rather limited effect. Gallic and ellagic tannins have no inhibitory effect on stem bromelain activity, while both seed and skin tannins were uncompetitive inhibitors. The strongest inhibition effect was revealed for sulfur dioxide, which was a mixed-type inhibitor for the enzyme activity. This study provides useful information relative to a future biotechnological application of stem bromelain in winemaking.

Effect of ellagic acid on proliferation, cell adhesion and apoptosis in SH-SY5Y human neuroblastoma cells.

PubMed

Fjaeraa, Christina; Nånberg, Eewa

2009-05-01

Ellagic acid, a polyphenolic compound found in berries, fruits and nuts, has been shown to possess growth-inhibiting and apoptosis promoting activities in cancer cell lines in vitro. The objective of this study was to investigate the effect of ellagic acid in human neuroblastoma SH-SY5Y cells. In cultures of SH-SY5Y cells incubated with ellagic acid, time- and concentration-dependent inhibitory effects on cell number were demonstrated. Ellagic acid induced cell detachment, decreased cell viability and induced apoptosis as measured by DNA strand breaks. Ellagic acid-induced alterations in cell cycle were also observed. Simultaneous treatment with all-trans retinoic acid did not rescue the cells from ellagic acid effects. Furthermore, the results suggested that pre-treatment with all-trans retinoic acid to induce differentiation and cell cycle arrest did not rescue the cells from ellagic acid-induced cell death.

Effects of cultivar, fruit number and reflected photosynthetically active radiation on Fragaria x ananassa productivity and fruit ellagic acid and ascorbic acid concentrations.

PubMed

Atkinson, C J; Dodds, P A A; Ford, Y Y; Le Mière, J; Taylor, J M; Blake, P S; Paul, N

2006-03-01

A number of strawberry varieties were surveyed for their total ellagic acid concentration, and attempts were made to determine if ellagic acid and ascorbic acid concentrations of two strawberry cultivars could be increased by polythene reflective mulches. After adjusting crop yields and cultivation using polythene mulches with two different PAR reflective capacities, field- and polytunnel-grown strawberries were analysed for ellagic acid and ascorbic acid concentrations by HPLC. Comparative measurements of yield and fruit quality were determined along with plant developmental changes. Ellagic acid concentration varied widely with strawberry cultivar (60-341 microg g(-1) frozen weight), as did the ratio of conjugated ellagic acid : free ellagic acid. Also, there was significant year-to-year variation in total ellagic acid concentration with some cultivars. Mulches with different reflective capacities impacted on strawberry production; highly reflective mulches significantly increased growth and yield, the latter due to increases in fruit size and number. Highly reflective mulches significantly increased total concentrations of ellagic acid and ascorbic acid relative to control in fruit of different cultivars. The potential of agronomic practices to enhance the concentration and amounts of these important dietary bioactive compounds is discussed.

Characterization of ellagitannins, gallotannins, and bound proanthocyanidins from California almond (Prunus dulcis) varieties.

PubMed

Xie, Liyang; Roto, Anna V; Bolling, Bradley W

2012-12-12

Extractable and bound proanthocyanidins and hydrolyzable tannins were characterized in Nonpareil, Carmel, and Butte almond varieties from California, with n = 3 samples/variety. Bound proanthocyanidins were recovered from extracted defatted almond residue by hydrolysis with 4 N sodium hydroxide and represented 3-21% of the total proanthocyanidin content among varieties. The bound proanthocyanidins were recovered primarily as monomers and dimers. In contrast, acid hydrolysis of extracted almond residue did not yield bound proanthocyanidins. Hydrolyzable tannins were characterized in aqueous acetone extracts of defatted almond using two-dimensional TLC and further quantitated by HPLC following acid hydrolysis. Almond hydrolyzable tannin content was 54.7 ± 2.3 mg ellagic acid and 27.4 ± 7.3 mg gallic acid per 100 g almond among varieties. The tannin contents of Nonpareil, Carmel, and Butte almond varieties were not significantly different. Thus, bound proanthocyanidins and hydrolyzable tannins significantly contribute to almond polyphenol content.

Quantitative and fingerprint analyses of Chinese sweet tea plant (Rubus Suavissimus S. Lee)

PubMed Central

Chou, Guixin; Xu, Shun-Jun; Liu, Dong; Koh, Gar Yee; Zhang, Jian; Liu, Zhijun

2009-01-01

Quality of botanical food is increasingly assessed by the content of multiple bioactive compounds. In this study we report, for the first time, an HPLC fingerprinting method for the quality evaluation of Rubus suavissimus leaves possessing multiple bioactivities. Five constituents, gallic acid, rutin, ellagic acid, rubusoside, and steviol monoside were quantified and used in developing qualitative chromatographic fingerprints. The limits of detection and quantification ranged from 0.29 μg/mL to 37.86 μg/mL. The relative standard deviations (RSDs) of intra- and inter-day precisions were no more than 3.14% and 3.01%, respectively. The average recoveries were between 93.1% and 97.5%. The developed method was validated in analyzing fourteen leaf samples with satisfactory results. The contents of the five marker compounds accounted for an average of about 6% w/w with a variability of 16% among the fourteen samples collected from a single site and year. Gallic acid was the least whereas steviol monoside the most variable compounds among the fourteen leaf samples. The characteristic compound rubusoside that is responsible for the sweet taste accounted for 5% of leaf weight. The validated method can now be used to quantitatively and qualitatively assess the quality of Rubus suavissimus leaves as traditional beverage or potential medicines. PMID:19138116

Identification of Ellagic Acid from Plant Rhodiola rosea L. as an Anti-Ebola Virus Entry Inhibitor.

PubMed

Cui, Qinghua; Du, Ruikun; Anantpadma, Manu; Schafer, Adam; Hou, Lin; Tian, Jingzhen; Davey, Robert A; Cheng, Han; Rong, Lijun

2018-03-27

The recent 2014-2016 West African Ebola virus epidemic underscores the need for the development of novel anti-Ebola therapeutics, due to the high mortality rates of Ebola virus infections and the lack of FDA-approved vaccine or therapy that is available for the prevention and treatment. Traditional Chinese medicines (TCMs) represent a huge reservoir of bioactive chemicals and many TCMs have been shown to have antiviral activities. 373 extracts from 128 TCMs were evaluated using a high throughput assay to screen for inhibitors of Ebola virus cell entry. Extract of Rhodiola rosea displayed specific and potent inhibition against cell entry of both Ebola virus and Marburg virus. In addition, twenty commercial compounds that were isolated from Rhodiola rosea were evaluated using the pseudotyped Ebola virus entry assay, and it was found that ellagic acid and gallic acid, which are two structurally related compounds, are the most effective ones. The activity of the extract and the two pure compounds were validated using infectious Ebola virus. The time-of-addition experiments suggest that, mechanistically, the Rhodiola rosea extract and the effective compounds act at an early step in the infection cycle following initial cell attachment, but prior to viral/cell membrane fusion. Our findings provide evidence that Rhodiola rosea has potent anti-filovirus properties that may be developed as a novel anti-Ebola treatment.

Identification of Ellagic Acid from Plant Rhodiola rosea L. as an Anti-Ebola Virus Entry Inhibitor

PubMed Central

Cui, Qinghua; Du, Ruikun; Anantpadma, Manu; Schafer, Adam; Hou, Lin; Tian, Jingzhen; Cheng, Han; Rong, Lijun

2018-01-01

The recent 2014–2016 West African Ebola virus epidemic underscores the need for the development of novel anti-Ebola therapeutics, due to the high mortality rates of Ebola virus infections and the lack of FDA-approved vaccine or therapy that is available for the prevention and treatment. Traditional Chinese medicines (TCMs) represent a huge reservoir of bioactive chemicals and many TCMs have been shown to have antiviral activities. 373 extracts from 128 TCMs were evaluated using a high throughput assay to screen for inhibitors of Ebola virus cell entry. Extract of Rhodiola rosea displayed specific and potent inhibition against cell entry of both Ebola virus and Marburg virus. In addition, twenty commercial compounds that were isolated from Rhodiola rosea were evaluated using the pseudotyped Ebola virus entry assay, and it was found that ellagic acid and gallic acid, which are two structurally related compounds, are the most effective ones. The activity of the extract and the two pure compounds were validated using infectious Ebola virus. The time-of-addition experiments suggest that, mechanistically, the Rhodiola rosea extract and the effective compounds act at an early step in the infection cycle following initial cell attachment, but prior to viral/cell membrane fusion. Our findings provide evidence that Rhodiola rosea has potent anti-filovirus properties that may be developed as a novel anti-Ebola treatment. PMID:29584652

Effect of different polyphenol sources on the efficiency of ellagic acid release by Aspergillus niger.

PubMed

Sepúlveda, Leonardo; de la Cruz, Reynaldo; Buenrostro, José Juan; Ascacio-Valdés, Juan Alberto; Aguilera-Carbó, Antonio Francisco; Prado, Arely; Rodríguez-Herrera, Raúl; Aguilar, Cristóbal Noé

2016-01-01

Fungal hydrolysis of ellagitannins produces hexahydroxydiphenic acid, which is considered an intermediate molecule in ellagic acid release. Ellagic acid has important and desirable beneficial health properties. The aim of this work was to identify the effect of different sources of ellagitannins on the efficiency of ellagic acid release by Aspergillus niger. Three strains of A. niger (GH1, PSH and HT4) were assessed for ellagic acid release from different polyphenol sources: cranberry, creosote bush, and pomegranate used as substrate. Polyurethane foam was used as support for solid-state culture in column reactors. Ellagitannase activity was measured for each of the treatments. Ellagic acid was quantified by high performance liquid chromatography. When pomegranate polyphenols were used, a maximum value of ellagic acid (350.21 mg/g) was reached with A. niger HT4 in solid-state culture. The highest amount of ellagitannase (5176.81 U/l) was obtained at 8h of culture when cranberry polyphenols and strain A. niger PSH were used. Results demonstrated the effect of different polyphenol sources and A. niger strains on ellagic acid release. It was observed that the best source for releasing ellagic acid was pomegranate polyphenols and A. niger HT4 strain, which has the ability to degrade these compounds for obtaining a potent bioactive molecule such as ellagic acid. Copyright © 2015 Asociación Argentina de Microbiología. Publicado por Elsevier España, S.L.U. All rights reserved.

Comparison of bioactive components in pressurized and pasteurized longan juices fortified with encapsulated Lactobacillus casei 01

NASA Astrophysics Data System (ADS)

Chaikham, Pittaya; Apichartsrangkoon, Arunee

2012-06-01

In this study, longan juice was subjected to a high pressure of 500 MPa for 30 min and compared with a juice pasteurized at 90°C/2 min. Probiotic Lactobacillus casei 01 was fortified into both juices and the shelf life of these products was studied. Their bioactive components such as ascorbic acid, gallic acid and ellagic acid were analyzed by High Performance Liquid Chromatography (HPLC). Total phenolic compounds and 2,2-Diphenyl-1-picrythydrazyl radical-scavenging activity were determined by colorimetric and spectrophotometric methods. It was found that the pressurized longan juice retained higher amounts of bioactive compounds than the pasteurized juice. In terms of storage stability, bioactive compounds in both processed juices decreased according to the increase in storage time. The survivability of probiotic L. casei 01 in both processed juices declined from 9 to 6 log CFU/mL after 4 weeks of storage.

Evaluation of antioxidant capacity and flavor profile change of pomegranate wine during fermentation and aging process.

PubMed

Lan, Yongli; Wu, Jin; Wang, Xuejiao; Sun, Xuchun; Hackman, Robert M; Li, Zhixi; Feng, Xianchao

2017-10-01

Antioxidant properties and flavor characteristic profile of pomegranate wine during winemaking were investigated. The total phenol content and radical scavenging activity exhibited a slightly decrease in the end edge. Punicalagins and gallic acid were revealed to be the most abundant phenolic compounds, followed by ellagic acid and vanillic acid. These constituents were mainly responsible for the effective antioxidant capacity of pomegranate wine. The major changes of flavor qualities occurred in the initial stage, particularly 0-4day of fermentation. Fermentation significantly reduced the relative content of aldehydes, ketones, heterocyclic and aromatic compounds, but promoted the generation of esters and alcohols. This is the first time of using E-nose and E-tongue to monitor odour and taste changes in the brewing process of pomegranate wine. The study may provide a promising instruction for improving functional features and quality control of the pomegranate wine. Copyright © 2017 Elsevier Ltd. All rights reserved.

Effect of processing and storage on the antioxidant ellagic acid derivatives and flavonoids of red raspberry (Rubus idaeus) jams.

PubMed

Zafrilla, P; Ferreres, F; Tomás-Barberán, F A

2001-08-01

From red raspberries, ellagic acid, its 4-arabinoside, its 4' (4' '-acetyl) arabinoside, and its 4' (4' '-acetyl)xyloside, as well as quercetin and kaempferol 3-glucosides, were identified. In addition, two unidentified ellagic acid derivatives were detected. The free radical scavenging activity of the ellagic acid derivatives was evaluated by using the DPPH method and compared to that of Trolox. All of the isolated compounds showed antioxidant activity. The effect of processing to obtain jams on raspberry phenolics was evaluated. The flavonol content decreased slightly with processing and more markedly during storage of the jams. The ellagic acid derivatives, with the exception of ellagic acid itself, remained quite stable with processing and during 6 months of jam storage. The content of free ellagic acid increased 3-fold during the storage period. The initial content (10 mg/kg of fresh weight of raspberries) increased 2-fold with processing, and it continued increasing up to 35 mg/kg after 1 month of storage of the jam. Then a slight decrease was observed until 6 months of storage had elapsed. The increase observed in ellagic acid could be explained by a release of ellagic acid from ellagitannins with the thermal treatment.

Simultaneous determination and characterization of tannins and triterpene saponins from the fruits of various species of Terminalia and Phyllantus emblica using a UHPLC-UV-MS method: application to triphala.

PubMed

Avula, Bharathi; Wang, Yan-Hong; Wang, Mei; Shen, Yun-Heng; Khan, Ikhlas A

2013-01-01

Terminalia species are a rich source of tannins. Many preparations of these species are used in traditional medicine and have many different ethnobotanical applications. A simple UHPLC method was developed for the simultaneous analysis of such hydrolysable tannins and triterpene saponins from the fruit rinds of different species of Terminalia (T. chebula, T. arjuna, T. bellirica) and Phyllantus emblica. A separation by LC was achieved using a reversed-phase column and a water/acetonitrile mobile phase, both containing formic acid, using a gradient system and a temperature of 40°C. Eight hydrolysable tannins (gallic acid, gallic acid methyl ester, corilagin, chebulagic acid, 1,2,3,6-tetra-O-galloyl-β-D-glucose, ellagic acid, chebulinic acid, and 1,2,3,4,6-penta-O-galloyl-β-D-glucose) and six triterpene saponins (arjunglucoside-I, arjunglucoside-III, chebuloside II, bellericoside, arjunetin, and arjunglucoside-II) could be separated within 20 minutes. The wavelength used for detection with the diode array detector was 254 and 275 nm for tannins and 205 nm for triterpene saponins. The method was validated for linearity, repeatability, limits of detection, and limits of quantification. The developed method is economical, fast, and especially suitable for quality control analysis of tannins and triterpene saponins in various plant samples and commercial products of Terminalia. Georg Thieme Verlag KG Stuttgart · New York.

Effects of Phenolic Compounds on Growth of Colletotrichum spp. In Vitro.

PubMed

Roy, Sutapa; Nuckles, Etta; Archbold, Douglas D

2018-05-01

Colletotrichum acutatum is responsible for anthracnose fruit rot, one of the most devastating diseases in strawberry. Phenolic compounds have been described as contributors to anthracnose resistance in strawberry (Fragaria x ananassa, Duch.). Six isolates of Colletotrichum acutatum and four isolates of three other Colletotrichum species, C. gloeosporioides, C. fragariae, and C. graminicola, associated with disease symptoms were investigated in this study. The potential inhibitory effect of phenolic acids (gallic acid, caffeic acid, chlorogenic acid, ferulic acid, trans-cinnamic acid, p-coumaric acid, salicylic acid), flavonoids (catechin, quercetin, naringenin), and ellagic acid, which are naturally found in strawberry, were screened against two different spore suspension concentrations of the Colletotrichum isolates at 5, 10, 50 mM in vitro. Among the phenolic acids and flavonoids tested in this study, only trans-cinnamic acid, ferulic acid, and p-coumaric acid inhibited fungal growth. The inhibitory effects were concentration-dependent but also varied with the spore suspension concentration of the isolates. The results demonstrated that trans-cinnamic acid had the greatest inhibitory effect on all Colletotrichum spp. isolates tested.

Identification of nonvolatile compounds in clove (Syzygium aromaticum) from Manado

NASA Astrophysics Data System (ADS)

Fathoni, A.; Saepudin, E.; Cahyana, A. H.; Rahayu, D. U. C.; Haib, J.

2017-07-01

Syzygium aromaticum (clove) are native to Indonesia and have been widely used in food industry due to their flavor. Nonvolatile compounds contribute to flavor, mainly in their taste. Currently, there is very little information available about nonvolatile compounds in clove. Identification of nonvolatile compounds is important to improve clove's value. Compound extraction was conducted by maceration in ethanol. Fractionations of the extract were performed by using gravity column chromatography on silica gel and Sephadex LH-20 as stationary phase. Nonvolatile compounds were identified by Liquid Chromatography-Tandem Mass Spectrometry (LC-MS/MS). LC-MS/MS was operated in negative mode with 0.1 % formic acid in water and acetonitrile as mobile phase. Nonvolatile compounds were identified by fragment analysis and compared to references. Several compounds had been identified and characterized asquinic acid, monogalloylglucose, gallic acid, digalloylglucose, isobiflorin, biflorin, ellagic acid, hydroxygallic acid, luteolin, quercetin, naringenin, kaempferol, isorhamnetin, dimethoxyluteolin, and rhamnetin. These compounds had two main flavor perceptions, i.e. astringent, and bitter.

Chronic administration of ellagic acid improved the cognition in middle-aged overweight men.

PubMed

Liu, Ying; Yu, Shuyi; Wang, Fen; Yu, Haitao; Li, Xueli; Dong, Wanru; Lin, Ruichao; Liu, Qingshan

2018-03-01

This study aimed to investigate if ellagic acid has beneficial effects on cognitive deficits in middle-aged overweight individuals and to propose a possible mechanism. A total of 150 middle-aged male participants, including 76 normal-weight and 74 overweight men, aged between 45 to 55 years, were recruited for this study. Both normal-weight and overweight participants were administered either 50 mg ellagic acid or placebo cellulose daily for 12 weeks. Blood lipids, peripheral brain-derived neurotrophic factor (BDNF), and saliva cortisol were assessed on the last day of the procedure to investigate the effects induced by ellagic acid. The results revealed that ellagic acid treatment improved the levels of blood lipid metabolism with a 4.7% decline in total cholesterol, 7.3% decline in triglycerides, 26.5% increase in high-density lipoprotein, and 6.5% decline in low-density lipoprotein. Additionally, ellagic acid increased plasma BDNF by 21.2% in the overweight group and showed no effects on normal-weight participants. Moreover, the increased saliva cortisol level in overweight individuals was inhibited by 22.7% in a 12-week ellagic acid treatment. Also, compared with placebo, overweight individuals who consumed ellagic acid showed enhanced cognitive function as measured by the Wechsler Adult Intelligence Scale-Revised and the Montreal Cognitive Assessment. To the best of our knowledge, this is the first report showing that ellagic acid prevents cognitive deficits through normalization of lipid metabolism, increase in plasma BDNF level, and reduction of saliva cortisol concentration. These results indicate that ellagic acid has a potential to restore cognitive performance related to mild age-related declines.

Preparation of ellagic acid molecularly imprinted polymeric microspheres based on distillation-precipitation polymerization for the efficient purification of a crude extract.

PubMed

Zhang, Hua; Zhao, Shangge; Zhang, Lu; Han, Bo; Yao, Xincheng; Chen, Wen; Hu, Yanli

2016-08-01

Molecularly imprinted polymeric microspheres with a high recognition ability toward the template molecule, ellagic acid, were synthesized based on distillation-precipitation polymerization. The as-obtained polymers were characterized by scanning electron microscopy, infrared spectroscopy, and thermogravimetric analysis. Static, dynamic, and selective binding tests were adopted to study the binding properties and the molecular recognition ability of the prepared polymers for ellagic acid. The results indicated that the maximum static adsorption capacity of the prepared polymers toward ellagic acid was 37.07 mg/g and the adsorption equilibrium time was about 100 min when the concentration of ellagic acid was 40 mg/mL. Molecularly imprinted polymeric microspheres were also highly selective toward ellagic acid compared with its analogue quercetin. It was found that the content of ellagic acid in the pomegranate peel extract was enhanced from 23 to 86% after such molecularly imprinted solid-phase extraction process. This work provides an efficient way for effective separation and enrichment of ellagic acid from complex matrix, which is especially valuable in industrial production. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chromatographic and Spectrophotometric Analysis of Phenolic Compounds from Fruits of Libidibia ferrea Martius

PubMed Central

Ferreira, Magda R. A.; Fernandes, Mônica T. M.; da Silva, Wliana A. V.; Bezerra, Isabelle C. F.; de Souza, Tatiane P.; Pimentel, Maria F.; Soares, Luiz A. L.

2016-01-01

Background: Libidibia ferrea (Mart. ex Tul.) L.P. Queiroz (Fabaceae) is a tree which is native to Brazil, widely known as “Jucá,” where its herbal derivatives are used in folk medicine with several therapeutic properties. The constituents, which have already been described in the fruit, are mainly hydrolysable tannins (gallic acid [GA] and ellagic acid [EA]). Objective: The aim of this study was to investigate the phenolic variability in the fruit of L. ferrea by ultraviolet/visible (UV/VIS) and chromatographic methods (high-performance liquid chromatography [HPLC]/high-performance thin layer chromatography [HPTLC]). Materials and Methods: Several samples were collected from different regions of Brazil and the qualitative (fingerprints by HPTLC and HPLC) and quantitative analysis (UV/VIS and HPLC) of polyphenols were performed. Results: The HPTLC and HPLC profiles allowed separation and identification of both major analytical markers: EA and GA. The chemical profiles were similar in a number of spots or peaks for the samples, but some differences could be observed in the intensity or area of the analytical markers for HPTLC or HPLC, respectively. Regarding the quantitative analysis, the polyphenolic content by UV/VIS ranged from 13.99 to 37.86 g% expressed as GA or from 10.75 to 29.09 g% expressed as EA. The contents of EA and GA by liquid chromatography-reversed phase (LC-RP) method ranged from 0.57 to 2.68 g% and from 0.54 to 3.23 g%, respectively. Conclusion: The chemical profiles obtained by HPTLC or HPLC, as well as the quantitative analysis by spectrophotometry or LC-RP method, were suitable for discrimination of each herbal sample and can be used as tools for the comparative analysis of the fruits from L. ferrea. SUMMARY The polyphenols of fruits of Libidibia ferrea can be quantified by UV/VIS and HPLCThe HPLC method was able to detect the gallic and ellagic acids in several samples of fruits of Libidibia ferreaThe phenolic profiles of fruits from Libidibia ferrea by HPTLC and HPLC were reproductible. Abbreviations used: HPTLC: high performance thin layer chromatography, HPLC: high performance liquid chromatography, UV-Vis: spectrophotometry PMID:27279721

Pomegranate ellagitannins stimulate growth of gut bacteria in vitro: Implications for prebiotic and metabolic effects.

PubMed

Li, Zhaoping; Summanen, Paula H; Komoriya, Tomoe; Henning, Susanne M; Lee, Ru-Po; Carlson, Eliisa; Heber, David; Finegold, Sydney M

2015-08-01

The present study investigated the effect of pomegranate extract (POMx) and pomegranate juice (POM juice) on the growth of major groups of intestinal bacteria: Enterobacteriaceae, Bacteroides fragilis group, clostridia, bifidobacteria, and lactobacilli, and the utilization of pomegranate polyphenols by Bifidobacterium and Lactobacillus. The total phenolic content of the pomegranate extract and juice was determined using the Folin-Ciocalteau colorimetric method and reported as gallic acid equivalent (GAE). The polyphenol composition was determined by HPLC. Stool specimens were incubated with 400, 100, and 25 μg/ml GAE POMx and POM juice and subjected to selective culture. Bifidobacterium and Lactobacillus strains were incubated with 400 μg/ml GAE POMx and POM juice and metabolites were analyzed. POMx and POM juice increased the mean counts of Bifidobacterium and Lactobacillus and significantly inhibited the growth of B. fragilis group, clostridia, and Enterobacteriaceae in a dose-response manner. Bifidobacterium and Lactobacillus utilized ellagic acid and glycosyl ellagic acid but little or no punicalin was utilized. Neither POMx nor POM juice was converted to urolithins by the test bacteria or the in vitro stool cultures. The effect of pomegranate on the gut bacteria considered to be beneficial (Bifidobacterium and Lactobacillus) suggests that pomegranate may potentially work as a prebiotic. The concept that polyphenols such as those in pomegranate impact gut microbiota populations may establish a new role for polyphenols in human health. Published by Elsevier Ltd.

Online solid-phase extraction with high-performance liquid chromatography and mass spectrometry for the determination of five tannins in traditional Chinese medicine injections.

PubMed

Sun, Meng; Lin, Yuanyuan; Zhang, Jie; Zheng, Shaohua; Wang, Sicen

2016-03-01

A rapid analytical method based on online solid-phase extraction with high-performance liquid chromatography and mass spectrometry has been established and applied to the determination of tannin compounds that may cause adverse effects in traditional Chinese medicine injections. Different solid-phase extraction sorbents have been compared and the elution buffer was optimized. The performance of the method was verified by evaluation of recovery (≥40%), repeatability (RSD ≤ 6%), linearity (r(2) ≥ 0.993), and limit of quantification (≤0.35 μg/mL). Five tannin compounds, gallic acid, cianidanol, gallocatechin gallate, ellagic acid, and penta-O-galloylglucose, were identified with concentrations ranging from 3.1-37.4 μg/mL in the analyzed traditional Chinese medicine injections. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Changes in polyphenolics during maturation of Java plum (Syzygium cumini Lam.).

PubMed

Lestario, Lydia Ninan; Howard, Luke R; Brownmiller, Cindi; Stebbins, Nathan B; Liyanage, Rohana; Lay, Jackson O

2017-10-01

Java plum (Syzygium cumini Lam.) is a rich source of polyphenolics with many purported health benefits, but the effect of maturation on polyphenolic content is unknown. Freeze-dried samples of Java plum from seven different maturity stages were analyzed for anthocyanin, flavonol, flavanonol and hydrolysable tannin composition by HPLC. Anthocyanins were first detected at the green-pink stage of maturity and increased throughout maturation with the largest increase occurring from the dark purple to black stages of maturation. Levels of gallotannins, ellagitannins, flavonols, gallic acid and ellagic acid were highest at early stages of maturation and decreased as the fruit ripened. For production of antioxidant-rich nutraceutical ingredients, fruit should be harvested immature to obtain extracts rich in hydrolysable tannins and flavonols. The exceptional anthocyanin content of black fruit may prove useful as a source of a natural colorant. Copyright © 2017 Elsevier Ltd. All rights reserved.

Sea Buckthorn (Hippophae rhamnoides L.) Leaf Extracts Protect Neuronal PC-12 Cells from Oxidative Stress.

PubMed

Cho, Chi Heung; Jang, Holim; Lee, Migi; Kang, Hee; Heo, Ho Jjn; Kim, Dae-Ok

2017-07-28

The present study was carried out to investigate the antioxidative and neuroprotective effects of sea buckthorn ( Hippophae rhamnoides L.) leaves (SBL) harvested at different times. Reversed-phase high-performance liquid chromatography analysis revealed five major phenolic compounds: ellagic acid, gallic acid, isorhamnetin, kaempferol, and quercetin. SBL harvested in August had the highest total phenolic and flavonoid contents and antioxidant capacity. Treatment of neuronal PC-12 cells with the ethyl acetate fraction of SBL harvested in August increased their viability and membrane integrity and reduced intracellular oxidative stress in a dose-dependent manner. The relative populations of both early and late apoptotic PC-12 cells were decreased by treatment with the SBL ethyl acetate fraction, based on flow cytometry analysis using annexin V-FITC/PI staining. These findings suggest that SBL can serve as a good source of antioxidants and medicinal agents that attenuate oxidative stress.

Pomegranate juice and prostate cancer: importance of the characterisation of the active principle.

PubMed

Chrubasik-Hausmann, Sigrun; Vlachojannis, Christian; Zimmermann, Benno

2014-11-01

Two exploratory clinical studies investigating proprietary pomegranate products showed a trend of effectiveness in increasing prostate-specific antigen doubling time in patients with prostate cancer. A recent clinical study did not support these results. We therefore analysed a lot of the marketed pomegranate blend for co-active pomegranate compounds. The high-performance liquid chromatography method was used to detect punicalagin, ellagic acid and anthocyanins. Total polyphenoles were determined by the Folin-Ciocalteu method using gallic acid as reference. The results show that the co-active compounds in the daily dose of the pomegranate blend were far below those previously tested and that the photometric assessment is not reliable for the standardisation of study medications. Not pomegranate but the low amount of co-active compounds in the proprietary pomegranate blend was responsible for its clinical ineffectiveness. Copyright © 2014 John Wiley & Sons, Ltd.

Antimicrobial activity and phytochemical characterization of Carya illinoensis.

PubMed

Bottari, Nathieli Bianchin; Lopes, Leonardo Quintana Soares; Pizzuti, Kauana; Filippi Dos Santos Alves, Camilla; Corrêa, Marcos Saldanha; Bolzan, Leandro Perger; Zago, Adriana; de Almeida Vaucher, Rodrigo; Boligon, Aline Augusti; Giongo, Janice Luehring; Baldissera, Matheus Dellaméa; Santos, Roberto Christ Vianna

2017-03-01

Carya illinoensis is a widespread species, belonging to the Juglandaceae family, commonly known as Pecan. Popularly, the leaves have been used in the treatment of smoking as a hypoglycemic, cleansing, astringent, keratolytic, antioxidant, and antimicrobial agent. The following research aimed to identify for the first time the phytochemical compounds present in the leaves of C. illinoensis and carry out the determination of antimicrobial activity of aqueous and ethanolic extracts. The antimicrobial activity was tested against 20 microorganisms by determining the minimum inhibitory concentration (MIC). Phenolic acids (gallic acid and ellagic acid), flavonoids (rutin), and tannins (catechins and epicatechins) were identified by HPLC-DAD and may be partially responsible for the antimicrobial activity against Gram-positive, Gram-negative, and yeast. The results showed MIC values between 25 mg/mL and 0.78 mg/mL. The extracts were also able to inhibit the production of germ tubes by Candida albicans. Copyright © 2017 Elsevier Ltd. All rights reserved.

Optimization of pulsed ultrasound-assisted technique for extraction of phenolics from pomegranate peel of Malas variety: Punicalagin and hydroxybenzoic acids.

PubMed

Kazemi, Milad; Karim, Roselina; Mirhosseini, Hamed; Abdul Hamid, Azizah

2016-09-01

Pomegranate peel is a rich source of phenolic compounds (such as punicalagin and hydroxybenzoic acids). However, the content of such bioactive compounds in the peel extract can be affected by extraction type and condition. It was hypothesized that the optimization of a pulsed ultrasound-assisted extraction (PUAE) technique could result in the pomegranate peel extract with higher yield and antioxidant activity. The main goal was to optimize PUAE condition resulting in the highest yield and antioxidant activity as well as the highest contents of punicalagin and hydroxybenzoic acids. The operation at the intensity level of 105W/cm(2) and duty cycle of 50% for a short time (10min) had a high efficiency for extraction of phenolics from pomegranate peel. The application of such short extraction can save the energy and cost of the production. Punicalagin and ellagic acid were the most predominant phenolic compounds quantified in the pomegranate peel extract (PPE) from Malas variety. PPE contained a minor content of gallic acid. Copyright © 2016 Elsevier Ltd. All rights reserved.

Estimation of ellagic acid and/or repaglinide effects on insulin signaling, oxidative stress, and inflammatory mediators of liver, pancreas, adipose tissue, and brain in insulin resistant/type 2 diabetic rats.

PubMed

Amin, Mohamed M; Arbid, Mahmoud S

2017-02-01

Even though ellagic acid has previously been valued in many models of cancer, so far its full mechanistic effect as a natural antiapoptotic agent in the prevention of type 2 diabetes complications has not been completely elucidated, which was the goal of this study. We fed albino rats a high-fat fructose diet (HFFD) for 2 months to induce insulin resistance/type 2 diabetes and then treated the rats with ellagic acid (10 mg/kg body weight, orally) and/or repaglinide (0.5 mg/kg body weight, orally) for 2 weeks. At the serum level, ellagic acid challenged the consequences of HFFD, significantly improving the glucose/insulin balance, liver enzymes, lipid profile, inflammatory cytokines, redox level, adipokines, ammonia, and manganese. At the tissue level (liver, pancreas, adipose tissue, and brain), ellagic acid significantly enhanced insulin signaling, autophosphorylation, adiponectin receptors, glucose transporters, inflammatory mediators, and apoptotic markers. Remarkably, combined treatment with both ellagic acid and repaglinide had a more pronounced effect than treatment with either alone. These outcomes give new insight into the promising molecular mechanisms by which ellagic acid modulates numerous factors induced in the progression of diabetes.

Effect of high hydrostatic pressure on the polyphenols and antioxidant activity of plantain pulp (Musa paradisiaca AAB).

PubMed

Jiménez-Martínez, Miriam C; Montalvo-González, Efigenia; Sáyago-Ayerdi, Sonia G; Mercado-Mercado, Gilberto; Ramírez-de León, José A; Paz-Gamboa, Ernestina; Vivar-Vera, Maria A

2017-06-01

The impact of high-pressure processing (HPP) on the polyphenol (PP) content and antioxidant activity (AOX) of plantain pulp was evaluated. Pressures of 400, 500 and 600 MPa were applied to plantain pulp for 90 and 180 s at room temperature (25 °C). Polyphenoloxidase activity, extractable (EPP) and non-extractable PP (NEPP) contents, flavonoid content and AOX (FRAP, ABTS •+ ) were evaluated. In addition, PP identification was performed using high-performance liquid chromatography. Polyphenoloxidase activity was inhibited after HPP under all of the conditions studied. Increases of 110.80% and 137.40% in EPP content under conditions of 500 MPa/180 s and 600 MPa/90 s were observed with a simultaneous improvement in the AOX with increments of up to 128.71%. The treatment under conditions of 500 MPa/90 s had the highest total PP content, including the highest content of flavonoids (0.22 g ellagic acid equivalents kg -1  dry weight) and the proportion of NEPP that contained hydrolysable PPs (91.12 g gallic acid equivalents kg -1  dry weight with high AOX. The identified PPs included catechin, quercetin, gallic and hydroxybenzoic acids. HPP performed at a room temperature can be used for improving the total content of PP compounds in plantain pulp under specific pressure and time conditions. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

A Pharmacological Update of Ellagic Acid.

PubMed

Ríos, José-Luis; Giner, Rosa M; Marín, Marta; Recio, M Carmen

2018-05-30

Ellagic acid is a common metabolite present in many medicinal plants and vegetables. It is present either in free form or as part of more complex molecules (ellagitannins), which can be metabolized to liberate ellagic acid and several of its metabolites, including urolithins. While ellagic acid's antioxidant properties are doubtless responsible for many of its pharmacological activities, other mechanisms have also been implicated in its various effects, including its ability to reduce the lipidemic profile and lipid metabolism, alter pro-inflammatory mediators (tumor necrosis factor- α , interleukin-1 β , interleukin-6), and decrease the activity of nuclear factor- κ B while increasing nuclear factor erythroid 2-related factor 2 expression. These events play an important role in ellagic acid's anti-atherogenic, anti-inflammatory, and neuroprotective effects. Several of these activities, together with the effect of ellagic acid on insulin, glycogen, phosphatases, aldose reductase, sorbitol accumulation, advanced glycation end-product formation, and resistin secretion, may explain its effects on metabolic syndrome and diabetes. In addition, results from recent research have increased the interest in ellagic acid, both as a potential protective agent of the liver and skin and as a potential anticancer agent, due to the specific mechanisms affecting cell proliferation, apoptosis, DNA damage, and angiogenesis and its aforementioned anti-inflammatory properties. Taken together, these effects make ellagic acid a highly interesting compound that may contribute to different aspects of health; however, more studies are needed, especially on the compound's pharmacokinetic profile. In this review, we selected papers published from 2005 to the present. Georg Thieme Verlag KG Stuttgart · New York.

Involvement of the GABAergic system in the anxiolytic-like effect of the flavonoid ellagic acid in mice.

PubMed

Girish, Chandrashekaran; Raj, Vishnu; Arya, Jayasree; Balakrishnan, Sadasivam

2013-06-15

Anxiolytic-like effects of dietary flavonoids are relatively well known. Ellagic acid is a naturally occurring flavonoid compound which is abundant in many plants and fruits. The present study was designed to investigate the antianxiety-like effect of ellagic acid in mice using an elevated plus-maze test. The involvement of the GABAergic and serotonergic systems in the antianxiety-like activity of ellagic acid was also studied. Our results showed that ellagic acid treatment (25, 50 and 100 mg/kg, p.o.), produced a significant increase in the percentage of time spent and entry into the open arms, with a profile comparable to that of diazepam (1 mg/kg, p.o.). Unlike diazepam, the anxiolytic doses of ellagic acid did not prolong the duration of sodium thiopental-induced loss of righting reflex, indicating that this flavonoid is non-hypnotic. The anxiolytic effect observed with ellagic acid treatment (25 mg/kg, p.o.) was antagonized by pretreatment with picrotoxin (a non-competitive GABAA receptor antagonist, 1 mg/kg, i.p.) and flumazenil (a benzodiazepine site antagonist, 1 mg/kg, i.p.) but not with p-chlorophenylalanine (a serotonin synthesis inhibitor, 100 mg/kg, i.p.) and pindolol (a β-adrenoceptors blocker/5-HT1A/1B receptor antagonist, 10 mg/kg, i.p.). Taken together, the data demonstrated that acute and chronic administration of ellagic acid to mice has produced antianxiety-like effect when tested in the elevated plus-maze. The experiments with different receptor blockers suggest an involvement of GABAergic system in the anxiolytic action of this bioflavonoid. However, this action is not seems to be mediated through serotonergic system. Copyright © 2013 Elsevier B.V. All rights reserved.

Determination of hydrolyzable tannins in the fruit of Terminalia chebula Retz. by high-performance liquid chromatography and capillary electrophoresis.

PubMed

Juang, Lih-Jeng; Sheu, Shuenn-Jyi; Lin, Ta-Chen

2004-06-01

A RP-HPLC method for determining fourteen components (gallic acid, chebulic acid, 1,6-di-O-galloyl-D-glucose, punicalagin, 3,4,6-tri-O-galloyl-D-glucose, casuarinin, chebulanin, corilagin, neochebulinic acid, terchebulin, ellagic acid, chebulagic acid, chebulinic acid, and 1,2,3,4,6-penta-O-galloyl-D-glucose) in the fruit of Terminalia chebula Retz. is described. The separation was achieved within 80 min using a binary gradient with mobile phases consisting of a pH 2.7 phosphoric acid solution and an 80% CH3CN solution. Capillary electrophoretic analyses were also attempted, and it was found that CZE (25 mM Na2B4O7, 5 mM NaH2PO4, pH 7.0) was an efficient method for the separation of gallotannins, while an MEKC method (25 mM Na2B4O7, 5 mM NaH2PO4, 20 mM SDS, pH 7.0, and 10% acetonitrile) provided a better separation for most of the tannins examined. The HPLC and CE methods developed were both successfully applied to the assay of tannins in commercial samples of Chebulae Fructus.

Reevaluation of the effect of ellagic acid on N-methyl-N-nitrosourea DNA alkylation and mutagenicity

DOE Office of Scientific and Technical Information (OSTI.GOV)

Lord, H.L.; Josephy, P.D.; Snieckus, V.A.

N-Methyl-N-nitrosourea (MNU) is a reactive, mutagenic methylating agent. MNU methylates DNA at various sites, including guanine N{sup 7}, guanine O{sup 6}, and adenine N{sup 3}. Dixit and Gold ((1986) Proc. Natl, Acad. Sci. U.S.A. 83, 8039-8043) reported that ellagic acid, a phenolic natural product, inhibited the mutagenicity of MNU in Salmonella typhimurium strain TA 100, inhibited salmon sperm DNA alkylation by ({sup 3}H)MNU, and also greatly reduced the ratio of guanine O{sup 6} to guanine N{sup 7} alkylation. We have examined the MNU-induced alkylation of calf thymus DNA and evaluated the effect of ellagic acid on this binding. Ellagic acidmore » had only a slight effect on total alkylation and did not alter the ratio of methylation at guanine-O{sup 6} and -N{sup 7} positions. In further experiments, ellagic acid did not significantly inhibit MNU mutagenicity. These findings do not support the potential use of ellagic acid as an inhibitor of biological damage induced by nitrosoureas.« less

Enhancing fluorescence intensity of Ellagic acid in Borax-HCl-CTAB micelles

NASA Astrophysics Data System (ADS)

Wang, Feng; Huang, Wei; Zhang, Shuai; Liu, Guokui; Li, Kexiang; Tang, Bo

2011-03-01

Ellagic acid (C 14H 6O 8), a naturally occurring phytochemical, found mainly in berries and some nuts, has anticarcinogenic and antioxidant properties. It is found that fluorescence of Ellagic acid (EA) is greatly enhanced by micelle of cetyltrimethylammonium bromide (CTAB) surfactant. Based on this effect, a sensitive proposed fluorimetric method was applied for the determination of Ellagic acid in aqueous solution. In the Borax-HCl buffer, the fluorescence intensity of Ellagic acid in the presence of CTAB is proportional to the concentration of Ellagic acid in range from 8.0 × 10 -10 to 4.0 × 10 -5 mol L -1; and the detection limits are 3.2 × 10 -10 mol L -1 and 5.9 × 10 -10 mol L -1 excited at 266 nm and 388 nm, respectively. The actual samples of pomegranate rinds are simply manipulated and satisfactorily determined. The interaction mechanism studies argue that the negative EA-Borax complex is formed and solubilized in the cationic surfactant CTAB micelle in this system. The fluorescence intensity of EA enhances because the CTAB micelle provides a hydrophobic microenvironment for EA-Borax complex, which can prevent collision with water molecules and decrease the energy loss of EA-Borax complex.

Phenolic Compounds of Pomegranate Byproducts (Outer Skin, Mesocarp, Divider Membrane) and Their Antioxidant Activities.

PubMed

Ambigaipalan, Priyatharini; de Camargo, Adriano Costa; Shahidi, Fereidoon

2016-08-31

Pomegranate peel was separated into outer leathery skin (PS), mesocarp (PM), and divider membrane (PD), and its phenolic compounds were extracted as free (F), esterified (E), and insoluble-bound (B) forms for the first time. The total phenolic content followed the order PD > PM > PS. ABTS(•+), DPPH, and hydroxyl radical scavenging activities and metal chelation were evaluated. In addition, pomegranate peel extracts showed inhibitory effects against α-glucosidase activity, lipase activity, and cupric ion-induced LDL-cholesterol oxidation as well as peroxyl and hydroxyl radical-induced DNA scission. Seventy-nine phenolic compounds were identified using HPLC-DAD-ESI-MS(n) mainly in the form of insoluble-bound. Thirty compounds were identified for the first time. Gallic acid was the major phenolic compound in pomegranate peel, whereas kaempferol 3-O-glucoside was the major flavonoid. Moreover, ellagic acid and monogalloyl-hexoside were the major hydrolyzable tannins, whereas the dominant proanthocyanidin was procyanidin dimers. Proanthocyanidins were detected for the first time.

Self nanoemulsifying drug delivery system of stabilized ellagic acid-phospholipid complex with improved dissolution and permeability.

PubMed

Avachat, Amelia M; Patel, Vijay G

2015-07-01

Ellagic acid (EA), a plant polyphenol known for its wide-range of health benefits has limited use due to its low oral bioavailability. In this study, a new self-nanoemulsifying drug delivery system (SNEDDS), based on the phospholipid complex technique, was developed to improve the oral bioavailability of ellagic acid. Ellagic acid-phospholipid complex was prepared by an anti-solvent method and characterized. Enhanced lipophilicity after the formation of ellagic acid-phospholipid complex was verified through solubility studies. Preliminary screening was carried out to select oil, surfactant and co-surfactant. Ternary phase diagrams were constructed to identify the area of nanoemulsification. Formulations were optimized on the basis of globule size, cloud point and robustness to dilution. The optimized SNEDDS of ellagic acid-phospholipid complex showed mean globule size of 106 ± 0.198 nm and cloud point at 83-85 °C. The in vitro drug release from SNEDDS was found to be higher compared to EA suspension and complex, while ex vivo studies showed increased permeation from SNEDDS compared to EA suspension. Moreover, SNEDDS overcome the food effect which was shown by EA suspension. Thus, SNEDDS were found to be influential in improving the release performance of EA, indicating their potential to improve the oral bioavailability of EA.

Phytochemical Analysis and Antifungal Activity of Extracts from Leaves and Fruit Residues of Brazilian Savanna Plants Aiming Its Use as Safe Fungicides.

PubMed

Breda, Caroline Alves; Gasperini, Alessandra Marcon; Garcia, Vera Lucia; Monteiro, Karin Maia; Bataglion, Giovana Anceski; Eberlin, Marcos Nogueira; Duarte, Marta Cristina Teixeira

2016-08-01

The increasing demand for safe food without preservatives or pesticides residues has encouraged several studies on natural products with antifungal activity and low toxicity. In this study, ethanolic extracts from leaves and fruit residues (peel and seeds) of three Brazilian savanna species (Acrocomia aculeata, Campomanesia adamantium and Caryocar brasiliense) were evaluated against phytopathogenic fungi. Additionally, the most active extract was chemically characterized by ESI-MS and its oral acute toxicity was evaluated. Extracts from C. brasiliense (pequi) peel and leaves were active against Alternaria alternata, Alternaria solani and Venturia pirina with minimal inhibitory concentrations between 350 and 1000 µg/mL. When incorporated in solid media, these extracts extended the lag phase of A. alternata and A. solani and reduced the growth rate of A. solani. Pequi peel extract showed better antifungal activity and their ESI-MS analysis revealed the presence of substances widely reported as antifungal such as gallic acid, quinic acid, ellagic acid, glucogalin and corilagin. The oral acute toxicity was relatively low, being considered safe for use as a potential natural fungicide.

Contribution of individual phenolics to antioxidant activity and in vitro digestibility of wild rices (Zizania aquatica L.).

PubMed

Sumczynski, Daniela; Kotásková, Eva; Orsavová, Jana; Valášek, Pavel

2017-03-01

Zizania aquatica L. was analysed for total flavonoids, phenolics and HPLC profile in both free and bound phenolic fractions. The highest content of flavonoids (378-455mgRE/kg) was detected in bound fractions, while the highest polyphenols content (1061-2988mgGAE/kg) was determined in free fractions. Additionally, predominant phenolics were identified. To understand the contribution of individual phenolics to an antioxidant activity their mutual correlations were evaluated. Regarding free flavonoids, the main contributors to an antioxidant activity (r>0.7111) were epigallocatechin, epicatechin and rutin; while epicatechin, quercetin and rutin were the main contributors in bound fractions (r>0.6868). Concerning free phenolic acids, the main contributors to an antioxidant activity (r>0.7585) were ferulic, vanillic, ellagic, sinapic and syringic acids; while caffeic, sinapic, syringic, o-coumaric, p-hydroxy benzoic, vanillic, protocatechuic, gallic and cinnamic acids were the main contributors in bound fractions of wild rice (r>0.6538). Finally, in vitro organic matter and dry matter digestibility were assessed. Copyright © 2016 Elsevier Ltd. All rights reserved.

Study on the stability control strategy of Triphala solution based on the balance of physical stability and chemical stabilities.

PubMed

Huang, Hao-Zhou; Zhao, Sheng-Yu; Ke, Xiu-Mei; Lin, Jun-Zhi; Huang, Shu-Sen; Xu, Run-Chun; Ma, Hong-Yan; Zhang, Yi; Han, Li; Zhang, Ding-Kun

2018-06-04

Triphala is a well-known prescription in Indian Ayurveda and TCM medicine for its great effect on gingivitis and hyperlipidemia. However, its solution is unstable for the containing of excessive polyphenol, leading to the production of sediment in the short term and the decrease of efficacy. Based on the analysis of sediment formation, a novel control strategy is proposed. To conduct the analysis, the sediment formation was recorded for a consecutive five days. The changes in the composition of the supernatant and the sediment were studied by the HPLC profile analysis. The main components of the sediment were identified as corilagin, ellagic acid and gallic acid, and the amount of ellagic acid sediment increased with the storage time. Then, with a series of pH status adjustments of the Triphala solution, the physical and chemical stabilities were acquired by Turbiscan and HPLC respectively. The results showed that as the pH value increased, so did the physical stability, but the particle size and TSI of the association decreased. While the fingerprint of chemical profile similarity decreased, so did the chemical stability. Combining physical and chemical stability parameters, an equilibrium point was found out. When the pH value was adjusted to 5.0, both the physical and chemical stabilities were better: the verification test showed that the sedimentation inhibition rates on the 3rd, 5th,10th and15th days were 41%, 55%, 41%, and 23%, respectively. This manuscript provided a new control strategy that will pique pharmaceutical and food development engineers' interest and trigger research ideas controlling the quality of decoction. Copyright © 2018 Elsevier B.V. All rights reserved.

Effects of Fruit Ellagitannin Extracts, Ellagic Acid, and Their Colonic Metabolite, Urolithin A, on Wnt Signaling

PubMed Central

Sharma, Meenakshi; Li, Liya; Celver, Jeremy; Killian, Caroline; Kovoor, Abraham; Seeram, Navindra P.

2010-01-01

Recent data suggest that ellagitannins (ETs), a class of hydrolyzable tannins found in some fruits and nuts, may have beneficial effects against colon cancer. In the stomach and gut, ETs hydrolyze to release ellagic acid (EA) and are converted by gut microbiota to urolithin-A (UA; 3,8-dihydroxy-6H-dibenzopyran-6-one) type metabolites which may persist in the colon through enterohepatic circulation. However, little is known about the mechanisms of action of either the native compounds or their metabolites on colon carcinogenesis. Components of Wnt signaling pathways are known to play a pivotal role in human colon carcinogenesis and inappropriate activation of the signaling cascade is observed in 90% of colorectal cancers. Here we investigated the effects of UA, EA, and ET rich fruit extracts on Wnt signaling in a human 293T cell line using a luciferase reporter of canonical Wnt pathway-mediated transcriptional activation. The ET extracts were obtained from strawberry (Fragaria annassa), Jamun berry (Eugenia jambolana), and pomegranate (Punica granatum) fruit and were all standardized to phenolic content (as gallic acid equivalents, GAEs, by the Folin Ciocalteau method) and to EA content (by high performance liquid chromatography methods): strawberry=20.5% GAE, 5.0% EA; Jamun berry= 20.5% GAE, 4.2% EA; pomegranate= 55% GAE, 3.5% EA. The ET-extracts (IC50=28.0-30.0 μg/mL), EA (IC50=19.0 μg/mL; 63 μM) and UA (IC50=9.0 μg/mL; 39 μM) inhibited Wnt signaling suggesting that ET-rich foods have potential against colon carcinogenesis and that urolithins are relevant bioactive constituents in the colon. PMID:20014760

Ellagic acid attenuates high-carbohydrate, high-fat diet-induced metabolic syndrome in rats.

PubMed

Panchal, Sunil K; Ward, Leigh; Brown, Lindsay

2013-03-01

Fruits and nuts may prevent or reverse common human health conditions such as obesity, diabetes and hypertension; together, these conditions are referred to as metabolic syndrome, an increasing problem. This study has investigated the responses to ellagic acid, present in many fruits and nuts, in a diet-induced rat model of metabolic syndrome. Eight- to nine-week-old male Wistar rats were divided into four groups for 16-week feeding with cornstarch diet (C), cornstarch diet supplemented with ellagic acid (CE), high-carbohydrate, high-fat diet (H) and high-carbohydrate, high-fat diet supplemented with ellagic acid (HE). CE and HE rats were given 0.8 g/kg ellagic acid in food from week 8 to 16 only. At the end of 16 weeks, cardiovascular, hepatic and metabolic parameters along with protein levels of Nrf2, NF-κB and CPT1 in the heart and the liver were characterised. High-carbohydrate, high-fat diet-fed rats developed cardiovascular remodelling, impaired ventricular function, impaired glucose tolerance, non-alcoholic fatty liver disease with increased protein levels of NF-κB and decreased protein levels of Nrf2 and CPT1 in the heart and the liver. Ellagic acid attenuated these diet-induced symptoms of metabolic syndrome with normalisation of protein levels of Nrf2, NF-κB and CPT1. Ellagic acid derived from nuts and fruits such as raspberries and pomegranates may provide a useful dietary supplement to decrease the characteristic changes in metabolism and in cardiac and hepatic structure and function induced by a high-carbohydrate, high-fat diet by suppressing oxidative stress and inflammation.

Ellagic acid protects endothelial cells from oxidized low-density lipoprotein-induced apoptosis by modulating the PI3K/Akt/eNOS pathway

DOE Office of Scientific and Technical Information (OSTI.GOV)

Ou, Hsiu-Chung; Lee, Wen-Jane; Tunghai University, Taichung, Taiwan

Endothelial apoptosis is a driving force in atherosclerosis development. Oxidized low-density lipoprotein (oxLDL) promotes inflammatory and thrombotic processes and is highly atherogenic, as it stimulates macrophage cholesterol accumulation and foam cell formation. Previous studies have shown that the phosphatidylinositol 3-kinase/Akt/endothelial nitric oxide synthase/nitric oxide (PI3K/Akt/eNOS/NO) pathway is involved in oxLDL-induced endothelial apoptosis. Ellagic acid, a natural polyphenol found in berries and nuts, has in recent years been the subject of intense research within the fields of cancer and inflammation. However, its protective effects against oxLDL-induced injury in vascular endothelial cells have not been clarified. In the present study, we investigatedmore » the anti-apoptotic effect of ellagic acid in human umbilical vein endothelial cells (HUVECs) exposed to oxLDL and explored the possible mechanisms. Our results showed that pretreatment with ellagic acid (5-20 {mu}M) significantly attenuated oxLDL-induced cytotoxicity, apoptotic features, and generation of reactive oxygen species (ROS). In addition, the anti-apoptotic effect of ellagic acid was partially inhibited by a PI3K inhibitor (wortmannin) and a specific eNOS inhibitor (cavtratin) but not by an ERK inhibitor (PD98059). In exploring the underlying mechanisms of ellagic acid action, we found that oxLDL decreased Akt and eNOS phosphorylation, which in turn activated NF-{kappa}B and downstream pro-apoptotic signaling events including calcium accumulation, destabilization of mitochondrial permeability, and disruption of the balance between pro- and anti-apoptotic Bcl-2 proteins. Those alterations induced by oxLDL, however, were attenuated by pretreatment with ellagic acid. The inhibition of oxLDL-induced endothelial apoptosis by ellagic acid is due at least in part to its anti-oxidant activity and its ability to modulate the PI3K/Akt/eNOS signaling pathway.« less

HPLC determination of phenolic acids, flavonoids and juglone in walnut leaves.

PubMed

Nour, Violeta; Trandafir, Ion; Cosmulescu, Sina

2013-10-01

A high-performance liquid chromatographic method with gradient elution and diode-array detection was developed to quantify free phenolic acids (gallic, vanillic, chlorogenic, caffeic, syringic, p-coumaric, ferulic, sinapic, salycilic, elagic and trans-cinnamic), flavonoids (catechin, epicatechin, rutin, myricetin and quercetin) and juglone in walnut leaves. Chromatographic separation was performed on a Hypersil Gold C18 column (5 µm particle size, 250 × 4.6 mm) and detection was conducted at three different wavelengths (254, 278 and 300 nm) according to the absorption maxima of the analyzed compounds. Validation procedures were conducted and the method was proven to be precise, accurate and sensitive. The developed method has been applied to analyze walnut leaves samples from nine different cultivars, with the same agricultural, geographical and climatic conditions. The experimental results revealed high concentrations of myricetin, catechin hydrate and rutin, and low concentrations of quercetin and epicatechin aglycones. Ellagic acid was established as the dominating phenolic acid of walnut leaves, followed by trans-cinnamic, chlorogenic and caffeic acids. Juglone content varied between 44.55 and 205.12 mg/100 g fresh weight. Significant differences were detected among cultivars for the concentration levels of phenolics.

Altered sensitivity to ellagic acid in neuroblastoma cells undergoing differentiation with 12-O-tetradecanoylphorbol-13-acetate and all-trans retinoic acid.

PubMed

Alfredsson, Christina Fjæraa; Rendel, Filip; Liang, Qui-Li; Sundström, Birgitta E; Nånberg, Eewa

2015-12-01

Ellagic acid has previously been reported to induce reduced proliferation and activation of apoptosis in several tumor cell lines including our own previous data from non-differentiated human neuroblastoma SH-SY5Y cells. The aim of this study was now to investigate if in vitro differentiation with the phorbol ester 12-O- tetradecanoylphorbol-13-acetate or the vitamin A derivative all-trans retinoic acid altered the sensitivity to ellagic acid in SH-SY5Y cells. The methods used were cell counting and LDH-assay for evaluation of cell number and cell death, flow cytometric analysis of SubG1- and TUNEL-analysis for apoptosis and western blot for expression of apoptosis-associated proteins. In vitro differentiation was shown to reduce the sensitivity to ellagic acid with respect to cell detachment, loss of viability and activation of apoptosis. The protective effect was phenotype-specific and most prominent in all-trans retinoic acid-differentiated cultures. Differentiation-dependent up-regulation of Bcl-2 and integrin expression is introduced as possible protective mechanisms. The presented data also point to a positive correlation between proliferative activity and sensitivity to ellagic-acid-induced cell detachment. In conclusion, the presented data emphasize the need to consider degree of neuronal differentiation and phenotype of neuroblastoma cells when discussing a potential pharmaceutical application of ellagic acid in tumor treatment. Copyright © 2015 Elsevier Masson SAS. All rights reserved.

Anti-cancer Effects of Polyphenolic Compounds in Epidermal Growth Factor Receptor Tyrosine Kinase Inhibitor-resistant Non-small Cell Lung Cancer

PubMed Central

Jeong, Hyungmin; Phan, Ai N. H.; Choi, Jong-Whan

2017-01-01

Background: Polyphenolic phytochemicals are natural compounds, easily found in fruits and vegetables. Importantly, polyphenols have been intensively studied as excellent antioxidant activity which contributes to anticancer function of the natural compounds. Lung cancer has been reported to mainly account for cancer-related deaths in the world. Moreover, epidermal growth factor receptor tyrosine kinase inhibitor (TKI) resistance is one of the biggest issues in cancer treatment, especially in nonsmall cell lung cancer (NSCLC). Even though several studies both in preclinical and clinical trials have showed promising therapeutic effects of polyphenolic compounds in anticancer therapy, the function of the natural compounds in TKI-resistant (TKIR) lung cancer remains poorly studied. Objective: The aim of this study is to screen polyphenolic compounds as potential anticancer adjuvants which suppress TKIR lung cancer. Materials and Methods: Colony formation and thiazolyl blue tetrazolium blue assay were performed in the pair-matched TKI-sensitive (TKIS) versus TKIR tumor cell lines to investigate the therapeutic effect of polyphenolic compounds in TKIR NSCLC. Results: Our data show that equol, kaempferol, resveratrol, and ellagic acid exhibit strong anticancer effect in HCC827 panel. Moreover, the inhibitory effect of most of tested polyphenolic compounds was highly selective for TKIR lung cancer cell line H1993 while sparing the TKIS one H2073. Conclusion: This study provides an important screening of potential polyphenolic compounds for drug development to overcome TKI resistance in advanced lung cancer. SUMMARY The study provides an important screening of potential polyphenolic compounds for drug development to overcome tyrosine kinase inhibitor (TKI) resistance in advance lung cancerEquol, kaempferol, resveratrol, and ellagic acid show strong anticancer effect in HCC827 panel, including TKI-sensitive (TKIS) and TKI-resistant clonesThe inhibitory effect of polyphenolic compounds such as equol, kaempferol, resveratrol, ellagic acid, gallic acid, p-Coumaric, and hesperidin is highly selective for TKI-resistant lung cancer cell line H1993 while sparing the TKIS one H2073. Abbreviations used: EGFR: Epidermal growth factor receptor, EMT: Epithelial-to-mesenchymal transition, GTP: Green tea polyphenols, IGF1R: Insulin-like growth factor 1 receptor, MET: Met proto-oncogene, MTT: Thiazolyl blue tetrazolium blue, NSCLC: Non-small cell lung cancer, ROS: Reactive oxygen species, RTK: Receptor tyrosine kinase, STAT3: Signal transducer and activator of transcription 3, TKIR: TKI-resistant, TKIs: Tyrosine kinase inhibitors, TKIS: TKI-sensitive. PMID:29200719

"Two-dimensional" molecularly imprinted solid-phase extraction coupled with crystallization and high performance liquid chromatography for fast semi-preparative purification of tannins from pomegranate husk extract.

PubMed

Sun, Guangying; Liu, Yanfang; Ahat, Hasanjan; Shen, Aijin; Liang, Xinmiao; Xue, Xingya; Luo, Yuqin; Yang, Jian; Liu, Zhao-Sheng; Aisa, Haji Akber

2017-07-07

In this study, "two dimensional" molecularly imprinted solid-phase extraction (2D-MIP-SPE) of semi-preparative grade was constructed to fast purify ellagitannins in pomegranate husk extract with the help of crystallization and reverse-phase liquid chromatgoraphy (RPLC). Ellagic acid and punicalagin imprinted polymers were synthesized in batch mode and two semi-preparative MIP-SPE columns were individually packed. After investigaing "functional complementation", 2D-MIP-SPE was constructed using ellagic acid MIP and punicalagin MIP-SPE as the first and second dimension, respectively. Then, pomegranate husk extract was fast divided into four fractions individually enriching in ellagic acid, granatin A, punicalagin and ellagic acid glucoside by 2D-MIP-SPE. With the aid of crystallization and RPLC, ellagic acid (13.5mg) and punicalagin (53.4mg) were fast obtained in 30min. Ellagic acid glucoside was purified to the purity near 100% with a recovery of 86.1%. Granatin A (92%) was directly obtained by 2D-MIP-SPE with the recovery of 81.8%. All above indicated that 2D-MIP-SPE was highly efficient in natural product purification. The concept of "functional complementation" was expected to be a useful tool in the construction of 2D-MIP-SPE. Copyright © 2017 Elsevier B.V. All rights reserved.

Flavonols and ellagic acid derivatives in peels of different species of jabuticaba (Plinia spp.) identified by HPLC-DAD-ESI/MSn.

PubMed

Neves, Nathália de Andrade; Stringheta, Paulo César; Gómez-Alonso, Sergio; Hermosín-Gutiérrez, Isidro

2018-06-30

Extracts of jabuticaba peels show complex chromatographic profiles at 360 nm, with some peaks presenting UV-Vis spectra resembling those of flavonol glycosides and others resembling that of ellagic acid. The presence and tentative identification of these phenolic compounds were comprehensively studied in four species of Brazilian jabuticaba fruit - Plinia trunciflora, variety 'jabuticaba de cabinho'; P. caulifora, varieties 'jabuticaba paulista' and 'jabuticaba canaã-açu'; P. jaboticaba, variety 'jabuticaba sabará'; and P. phitrantha, variety 'jabuticaba branca-vinho' - using HPLC-DAD-ESI-MS n . Seventeen flavonols derived from quercetin and three from myricetin and eighteen derivatives of ellagic acid and eleven of methyl ellagic acid were detected. Most of them were newly described and mainly occurred in glycosylated and acylglycosylated forms. Some compounds were missing in one variety, such as the absence of methyl ellagic acid derivatives in 'jabuticaba branca-vinho', and others only appeared in one variety, thus suggesting potential capacity for varietal differentiation. Copyright © 2018 Elsevier Ltd. All rights reserved.

Preparation and CO 2 adsorption properties of soft-templated mesoporous carbons derived from chestnut tannin precursors

DOE PAGES

Nelson, Kimberly M.; Mahurin, Shannon Mark; Mayes, Richard T.; ...

2015-10-09

This paper presents a soft templating approach for mesoporous carbon using the polyphenolic heterogeneous biomass, chestnut tannin, as the carbon precursor. By varying synthesis parameters such as tannin:surfactant ratio, cross-linker, reaction time and acid catalyst, the pore structure could be controllably modulated from lamellar to a more ordered hexagonal array. Carbonization at 600 °C under nitrogen produced a bimodal micro-mesoporous carbonaceous material exhibiting enhanced hydrogen bonding with the soft template, similar to that shown by soft-templating of phenolic-formaldehyde resins, allowing for a tailorable pore size. By utilizing the acidic nature of chestnut tannin (i.e. gallic and ellagic acid), hexagonal-type mesostructuresmore » were formed without the use of an acid catalyst. The porous carbon materials were activated with ammonia to increase the available surface area and incorporate nitrogen-containing functionality which led to a maximum CO 2 adsorption capacity at 1 bar of 3.44 mmol/g and 2.27 mmol/g at 0 °C and 25 °C, respectively. The ammonia-activated carbon exhibited multiple peaks in the adsorption energy distribution which indicates heterogeneity of adsorption sites for CO 2 capture.« less

Buchanania obovata: Functionality and Phytochemical Profiling of the Australian Native Green Plum.

PubMed

Fyfe, Selina A; Netzel, Gabriele; Netzel, Michael E; Sultanbawa, Yasmina

2018-05-04

The green plum is the fruit of Buchanania obovata Engl. and is an Australian Indigenous bush food. Very little study has been done on the green plum, so this is an initial screening study of the functional properties and phytochemical profile found in the flesh and seed. The flesh was shown to have antimicrobial properties effective against gram negative ( Escherichia coli 9001—NCTC) and gram positive ( Staphylococcus aureus 6571—NCTC) bacteria. Scanning electron microscopy analysis shows that the antimicrobial activity causes cell wall disintegration and cytoplasmic leakage in both bacteria. Antioxidant 2,2-diphenyl-1-picrylhydrazyl (DPPH) testing shows the flesh has high radical scavenging activity (106.3 ± 28.6 μM Trolox equivalant/g Dry Weight in methanol). The flesh and seed contain a range of polyphenols including gallic acid, ellagic acid, p-coumaric acid, kaempferol, quercetin and trans-ferulic acid that may be responsible for this activity. The seed is eaten as a bush food and contains a delphinidin-based anthocyanin. The green plum has potential as a functional ingredient in food products for its antimicrobial and antioxidant activity, and further investigation into its bioactivity, chemical composition and potential applications in different food products is warranted.

Phenolic Compounds and Antioxidant Activity of Phalaenopsis Orchid Hybrids

PubMed Central

Minh, Truong Ngoc; Khang, Do Tan; Tuyen, Phung Thi; Minh, Luong The; Anh, La Hoang; Quan, Nguyen Van; Ha, Pham Thi Thu; Quan, Nguyen Thanh; Toan, Nguyen Phu; Elzaawely, Abdelnaser Abdelghany; Xuan, Tran Dang

2016-01-01

Phalaenopsis spp. is the most commercially and economically important orchid, but their plant parts are often left unused, which has caused environmental problems. To date, reports on phytochemical analyses were most available on endangered and medicinal orchids. The present study was conducted to determine the total phenolics, total flavonoids, and antioxidant activity of ethanol extracts prepared from leaves and roots of six commercial hybrid Phalaenopsis spp. Leaf extracts of “Chian Xen Queen” contained the highest total phenolics with a value of 11.52 ± 0.43 mg gallic acid equivalent per g dry weight and the highest total flavonoids (4.98 ± 0.27 mg rutin equivalent per g dry weight). The antioxidant activity of root extracts evaluated by DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical scavenging assay and β-carotene bleaching method was higher than those of the leaf extracts. Eleven phenolic compounds were identified, namely, protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid, syringic acid, vanillin, ferulic acid, sinapic acid, p-coumaric acid, benzoic acid, and ellagic acid. Ferulic, p-coumaric and sinapic acids were concentrated largely in the roots. The results suggested that the root extracts from hybrid Phalaenopsis spp. could be a potential source of natural antioxidants. This study also helps to reduce the amount of this orchid waste in industrial production, as its roots can be exploited for pharmaceutical purposes. PMID:27649250

Potential Application of Nanoemulsions for Skin Delivery of Pomegranate Peel Polyphenols.

PubMed

Baccarin, Thaisa; Lemos-Senna, Elenara

2017-11-01

Pomegranate peel and seeds have demonstrated to possess antioxidant compounds with potential application to protect the skin against the ultraviolet radiation damage. However, the photoprotection activity is dependent on the amount of these compounds that reach the viable skin layers. In this paper, we describe the in vitro skin permeation and retention of the major pomegranate peel polyphenols using Franz diffusion cells, after entrapping a ethyl acetate fraction (EAF) from Punica granatum peel extract into nanoemulsions (NEs) prepared with pomegranate seed oil (PSO) or medium chain triglyceride oil (MCT). The in vitro skin permeation of gallic acid (GA), ellagic acid (EA), and punicalagin (PC) was evaluated using a HPLC-DAD validated method. After 8 h of skin permeation, all polyphenol compounds were mostly retained in the skin and did not reach the receptor compartment. However, a 2.2-fold enhancement of the retained amount of gallic acid in the stratum corneum was verified after EAF-loaded NEs are applied, when compared with the free EAF. GA and EA were delivered to the viable epidermis and dermis only when nanoemulsions were applied onto the skin. The mean retained amounts of GA and EA in the EP and DE after applying the EAF-loaded PSO-NE were 1.78 and 1.36 μg cm -2 and 1.10 and 0.97 μg cm -2 , respectively. Similar values were obtained after applying the EAF-loaded MCT-NE. The skin permeation results were supported by the confocal microscopy images. These results evidenced the promising application of nanoemulsions to deliver the pomegranate polyphenols into the deeper skin layers.

Evolution of ellagitannin content and profile during fruit ripening in Fragaria spp.

PubMed

Gasperotti, Mattia; Masuero, Domenico; Guella, Graziano; Palmieri, Luisa; Martinatti, Paolo; Pojer, Elisa; Mattivi, Fulvio; Vrhovsek, Urska

2013-09-11

Ellagitannins and ellagic acid conjugates are polyphenols present in the human diet, in particular strawberries (Fragaria spp.). The first aim of this study was isolation and structural characterization of casuarictin and 3-O-methyl ellagic acid 3'-O-α-rhamnopyranoside, which were found to be abundant in Fragaria spp., along with agrimoniin. The second aim was accurate profiling and quantification of 26 ellagitannins and ellagic acid conjugates in six Fragaria x ananassa cultivars and two Fragaria vesca species. The third aim was to describe the ellagitannins behavior during fruit ripening from the green stage to over-ripeness. It was shown that there are major qualitative and quantitative differences in the amount and profile of ellagitannins and ellagic acid conjugates between Fragaria spp. Genotype is a major factor in defining ellagitannin concentration and patterns between strawberries, and variable behavior of the genotypes was observed, in the context of a significant drop in ellagitannins during ripening.

Recent Advances in Anticancer Activities and Drug Delivery Systems of Tannins.

PubMed

Cai, Yuee; Zhang, Jinming; Chen, Nelson G; Shi, Zhi; Qiu, Jiange; He, Chengwei; Chen, Meiwan

2017-07-01

Tannins, polyphenols in medicinal plants, have been divided into two groups of hydrolysable and condensed tannins, including gallotannins, ellagitannins, and (-)-epigallocatechin-3-gallate (EGCG). Potent anticancer activities have been observed in tannins (especially EGCG) with multiple mechanisms, such as apoptosis, cell cycle arrest, and inhibition of invasion and metastases. Furthermore, the combinational effects of tannins and anticancer drugs have been demonstrated in this review, including chemoprotective, chemosensitive, and antagonizing effects accompanying with anticancer effect. However, the applications of tannins have been hindered due to their poor liposolubility, low bioavailability, off-taste, and shorter half-life time in human body, such as EGCG, gallic acid, and ellagic acid. To tackle these obstacles, novel drug delivery systems have been employed to deliver tannins with the aim of improving their applications, such as gelatin nanoparticles, micelles, nanogold, liposomes, and so on. In this review, the chemical characteristics, anticancer properties, and drug delivery systems of tannins were discussed with an attempt to provide a systemic reference to promote the development of tannins as anticancer agents. © 2016 Wiley Periodicals, Inc.

A comparison of antioxidative and anti-inflammatory activities of sword beans and soybeans fermented with Bacillus subtilis.

PubMed

Han, Seon Su; Hur, Sun Jin; Lee, Si Kyung

2015-08-01

This study was conducted to determine the antioxidative and anti-inflammatory activities of non-fermented or Bacillus subtilis-fermented soybeans and sword beans (red and white). The total flavonoid content in both sword bean types was higher (1.9-2.5-fold) than that in soybeans. The total phenolic content in fermented red sword beans was 2.5-fold greater than that in non-fermented red sword beans. HPLC profiles revealed that gallic acid, methyl gallate, and ellagic acid were major phenolic components of non-fermented/fermented red sword beans. DPPH radical scavenging activity and ferric-reducing antioxidant power were higher in fermented red sword beans than in other beans. Non-fermented/fermented red sword beans had higher nitrite scavenging activity than butylated hydroxytoluene and non-fermented/fermented soybeans. The hyaluronidase inhibitory activity of non-fermented/fermented red sword beans was higher (1.5-2.6-fold) than that of non-fermented/fermented soybeans. These results suggest that B. subtilis-fermented sword beans are potential natural antioxidant sources and anti-inflammatory agents for the food industry.

Potential Use of Plant Waste from the Moth Orchid (Phalaenopsis Sogo Yukidian “V3”) as an Antioxidant Source

PubMed Central

Thi Tuyen, Phung; Van Quan, Nguyen; Thi Thu Ha, Pham; Thanh Quan, Nguyen; Fan, Xinyan; Mai Van, Truong; Dang Khanh, Tran

2017-01-01

This research was conducted to exploit the waste of used plant parts from the widely marketed moth orchid cultivar (Phalaenopsis Sogo Yukidian “V3”). Various extracts of roots, stems, and leaves were evaluated for total phenolics, total flavonoids, and antioxidant capacity. The bound extract from stems contained the highest total phenolics (5.092 ± 0.739 mg GAE (gallic acid equivalent)/g DW (dry weight)). The maximum total flavonoids (2.218 ± 0.021 mg RE (rutin equivalent)/g DW) were found in the hexane extract of leaves. Ethyl acetate extract from roots showed the greatest antioxidant activity compared to other extracts. Of these extracts, the IC50 values of these samples were 0.070 mg/mL, and 0.450 mg/mL in a free radical 1,-diphenyl-picryl-hydrazyl (DPPH) assay and reducing power method, respectively. The lipid peroxidation inhibition (LPI) was found to be 94.2% using the β-carotene bleaching method. Five phenolic compounds including caffeic acid, syringic acid, vanillin, ellagic acid, and cinnamic acid were quantified by high performance liquid chromatography (HPLC). It is suggested that the roots of the hybrid Phalaenopsis Sogo Yukidian “V3” cultivar may be exploited as an effective source of antioxidants. PMID:28953245

Antibacterial Effect of Gallic Acid against Aeromonas hydrophila and Aeromonas sobria Through Damaging Membrane Integrity.

PubMed

Lu, Jing; Wang, Zhenning; Ren, Mengrou; Huang, Guoren; Fang, Baochen; Bu, Xiujuan; Liu, Yanhui; Guan, Shuang

In the study, we investigated the antibacterial activity and mechanism of gallic acid against Aeromonas hydrophila and Aeromonas sobria. Gallic acid showed strong antimicrobial activity against the two bacteria. Furthermore, the antibacterial mechanism of gallic acid (0, 3, 6, 12 mM) was performed by membrane integrity assay and scanning electron microscopy (SEM) assay. The results showed that gallic acid notably increased the released material absorption value at 260, 280 nm and electric conductivity in a dose-dependent manner. Moreover, the SEM assay showed that gallic acid induced severe shrink of bacterial intima and irregular morphology in a dose-dependent manner. The SDS-PAGE profiles further confirmed that gallic acid could damage bacterial cells. These results indicated gallic acid exhibited antibacterial effect by destroying membrane integrity of A. hydrophila and A. sobria. Hence, gallic acid has great potential as a new natural food preservative in food fresh-keeping and storage.

Transglycosylation of gallic acid by using Leuconostoc glucansucrase and its characterization as a functional cosmetic agent.

PubMed

Nam, Seung-Hee; Park, Jeongjin; Jun, Woojin; Kim, Doman; Ko, Jin-A; Abd El-Aty, A M; Choi, Jin Young; Kim, Do-Ik; Yang, Kwang-Yeol

2017-12-22

Gallic acid glycoside was enzymatically synthesized by using dextransucrase and sucrose from gallic acid. After purification by butanol partitioning and preparative HPLC, gallic acid glucoside was detected at m/z 355 (C 13 , H 16 , O 10 , Na) + by matrix-assisted laser desorption ionization time-of-flight mass spectrometry. The yield of gallic acid glucoside was found to be 35.7% (114 mM) by response surface methodology using a reaction mixture of 319 mM gallic acid, 355 mM sucrose, and 930 mU/mL dextransucrase. The gallic acid glucoside obtained showed 31% higher anti-lipid peroxidation and stronger inhibition (Ki = 1.23 mM) against tyrosinase than that shown by gallic acid (Ki = 1.98 mM). In UVB-irradiated human fibroblast cells, gallic acid glucoside lowered matrix metalloproteinase-1 levels and increased the collagen content, which was indicative of a stronger anti-aging effect than that of gallic acid or arbutin. These results indicated that gallic acid glucoside is likely a superior cosmetic ingredient with skin-whitening and anti-aging functions.

Electron-beam irradiation effects on phytochemical constituents and antioxidant capacity of pecan kernels [ Carya illinoinensis (Wangenh.) K. Koch] during storage.

PubMed

Villarreal-Lozoya, Jose E; Lombardini, Leonardo; Cisneros-Zevallos, Luis

2009-11-25

Pecans kernels (Kanza and Desirable cultivars) were irradiated with 0, 1.5, and 3.0 kGy using electron-beam (E-beam) irradiation and stored under accelerated conditions [40 degrees C and 55-60% relative humidity (RH)] for 134 days. Antioxidant capacity (AC) using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and oxygen radical absorbance capacity (ORAC) assays, phenolic (TP) and condensed tannin (CT) content, high-performance liquid chromatography (HPLC) phenolic profile, tocopherol content, peroxide value (PV), and fatty acid profiles were determined during storage. Irradiation decreased TP and CT with no major detrimental effects in AC. Phenolic profiles after hydrolysis were similar among treatments (e.g., gallic and ellagic acid, catechin, and epicatechin). Tocopherol content decreased with irradiation (>21 days), and PV increased at later stages (>55 days), with no change in fatty acid composition among treatments. Color lightness decreased, and a reddish brown hue developed during storage. A proposed mechanism of kernel oxidation is presented, describing the events taking place. In general, E-beam irradiation had slight effects on phytochemical constituents and could be considered a potential tool for pecan kernel decontamination.

Gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancers by accelerating EGFR turnover.

PubMed

Nam, Boas; Rho, Jin Kyung; Shin, Dong-Myung; Son, Jaekyoung

2016-10-01

Gallic acid is a common botanic phenolic compound, which is present in plants and foods worldwide. Gallic acid is implicated in various biological processes such as cell growth and apoptosis. Indeed, gallic acid has been shown to induce apoptosis in many cancer types. However, the molecular mechanisms of gallic acid-induced apoptosis in cancer, particularly lung cancer, are still unclear. Here, we report that gallic acid induces apoptosis in EGFR-mutant non-small cell lung cancer (NSCLC) cells, but not in EGFR-WT NSCLC cells. Treatment with gallic acid resulted in a significant reduction in proliferation and induction of apoptosis, only in EGFR-mutant NSCLC cells. Interestingly, treatment with gallic acid led to a robust decrease in EGFR levels, which is critical for NSCLC survival. Treatment with gallic acid had no significant effect on transcription, but induced EGFR turnover. Indeed, treatment with a proteasome inhibitor dramatically reversed gallic acid-induced EGFR downregulation. Moreover, treatment with gallic acid induced EGFR turnover leading to apoptosis in EGFR-TKI (tyrosine kinase inhibitor)-resistant cell lines, which are dependent on EGFR signaling for survival. Thus, these studies suggest that gallic acid can induce apoptosis in EGFR-dependent lung cancers that are dependent on EGFR for growth and survival via acceleration of EGFR turnover. Copyright © 2016 Elsevier Ltd. All rights reserved.

Gallic acid reduces cell viability, proliferation, invasion and angiogenesis in human cervical cancer cells

PubMed Central

ZHAO, BING; HU, MENGCAI

2013-01-01

Gallic acid is a trihydroxybenzoic acid, also known as 3,4,5-trihydroxybenzoic acid, which is present in plants worldwide, including Chinese medicinal herbs. Gallic acid has been shown to have cytotoxic effects in certain cancer cells, without damaging normal cells. The objective of the present study was to determine whether gallic acid is able to inhibit human cervical cancer cell viability, proliferation and invasion and suppress cervical cancer cell-mediated angiogenesis. Treatment of HeLa and HTB-35 human cancer cells with gallic acid decreased cell viability in a dose-dependent manner. BrdU proliferation and tube formation assays indicated that gallic acid significantly decreased human cervical cancer cell proliferation and tube formation in human umbilical vein endothelial cells, respectively. Additionally, gallic acid decreased HeLa and HTB-35 cell invasion in vitro. Western blot analysis demonstrated that the expression of ADAM17, EGFR, p-Akt and p-Erk was suppressed by gallic acid in the HeLa and HTB-35 cell lines. These data indicate that the suppression of ADAM17 and the downregulation of the EGFR, Akt/p-Akt and Erk/p-Erk signaling pathways may contribute to the suppression of cancer progression by Gallic acid. Gallic acid may be a valuable candidate for the treatment of cervical cancer. PMID:24843386

Gallic Acid Induces Apoptosis in Human Gastric Adenocarcinoma Cells.

PubMed

Tsai, Chung-Lin; Chiu, Ying-Ming; Ho, Tin-Yun; Hsieh, Chin-Tung; Shieh, Dong-Chen; Lee, Yi-Ju; Tsay, Gregory J; Wu, Yi-Ying

2018-04-01

Gastric cancer is one of the most common malignant cancers with a poor prognosis and high mortality rate worldwide. Current treatment of gastric cancer includes surgery and chemotherapy as the main modalities, but the potentially severe side-effects of chemotherapy present a considerable challenge. Gallic acid is a trihydroxybenzoic acid found to exert an anticancer effect against a variety of cancer cells. The purpose of this study was to determine the anti-cancer activity of Galla chinensis and its main component gallic acid on human gastric adenocarcinoma cells. MTT assay and cell death ELISA were used to determine the apoptotic effect of Gallic Chinensis and gallic acid on human gastric adenocarcinoma cells. To determine the pathway and relevant components by which gallic acid-induced apoptosis is mediated through, cells were transfected with siRNA (Fas, FasL, DR5, p53) using Lipofectamine 2000. Reults: Gallic Chinensis and gallic acid induced apoptosis of human gastric adenocarcinoma cells. Gallic acid induced up-regulation of Fas, FasL, and DR5 expression in AGS cells. Transfection of cells with Fas, FasL, or DR5 siRNA reduced gallic acid-induced cell death. In addition, p53 was shown to be involved in gallic acid-mediated Fas, FasL, and DR5 expression as well as cell apoptosis in AGS cells. These results suggest that gallic acid has a potential role in the treatment of gastric cancer. Copyright© 2018, International Institute of Anticancer Research (Dr. George J. Delinasios), All rights reserved.

Gallic acid attenuates calcium calmodulin-dependent kinase II-induced apoptosis in spontaneously hypertensive rats.

PubMed

Jin, Li; Piao, Zhe Hao; Liu, Chun Ping; Sun, Simei; Liu, Bin; Kim, Gwi Ran; Choi, Sin Young; Ryu, Yuhee; Kee, Hae Jin; Jeong, Myung Ho

2018-03-01

Hypertension causes cardiac hypertrophy and leads to heart failure. Apoptotic cells are common in hypertensive hearts. Ca 2+ /calmodulin-dependent protein kinase II (CaMKII) is associated with apoptosis. We recently demonstrated that gallic acid reduces nitric oxide synthase inhibition-induced hypertension. Gallic acid is a trihydroxybenzoic acid and has been shown to have beneficial effects, such as anti-cancer, anti-calcification and anti-oxidant activity. The purpose of this study was to determine whether gallic acid regulates cardiac hypertrophy and apoptosis in essential hypertension. Gallic acid significantly lowered systolic and diastolic blood pressure in spontaneously hypertensive rats (SHRs). Wheat germ agglutinin (WGA) and H&E staining revealed that gallic acid reduced cardiac enlargement in SHRs. Gallic acid treatment decreased cardiac hypertrophy marker genes, including atrial natriuretic peptide (ANP) and brain natriuretic peptide (BNP), in SHRs. The four isoforms, α, β, δ and γ, of CaMKII were increased in SHRs and were significantly reduced by gallic acid administration. Gallic acid reduced cleaved caspase-3 protein as well as bax, p53 and p300 mRNA levels in SHRs. CaMKII δ overexpression induced bax and p53 expression, which was attenuated by gallic acid treatment in H9c2 cells. Gallic acid treatment reduced DNA fragmentation and the TUNEL positive cells induced by angiotensin II. Taken together, gallic acid could be a novel therapeutic for the treatment of hypertension through suppression of CaMKII δ-induced apoptosis. © 2017 The Authors. Journal of Cellular and Molecular Medicine published by John Wiley & Sons Ltd and Foundation for Cellular and Molecular Medicine.

Negative Effect of Ellagic Acid on Cytosolic pH Regulation and Glycolytic Flux in Human Endometrial Cancer Cells.

PubMed

Abdelazeem, Khalid N M; Singh, Yogesh; Lang, Florian; Salker, Madhuri S

2017-01-01

Key properties of tumor cells include enhanced glycolytic flux with excessive consumption of glucose and formation of lactate. As glycolysis is highly sensitive to cytosolic pH, maintenance of glycolysis requires export of H+ ions, which is in part accomplished by Na+/H+ exchangers, such as NHE1. The carrier is sensitive to oxidative stress. Growth of tumor cells could be suppressed by the polyphenol Ellagic acid, which is found in various fruits and vegetables. An effect of Ellagic acid on transport processes has, however, never been reported. The present study thus elucidated an effect of Ellagic acid on cytosolic pH (pHi), NHE1 transcript levels, NHE1 protein abundance, Na+/H+ exchanger activity, and lactate release. Experiments were performed in Ishikawa cells without or with prior Ellagic acid (20 µM) treatment. NHE1 transcript levels were determined by qRT-PCR, NHE1 protein abundance by Western blotting, pHi utilizing (2',7'-bis-(2-carboxyethyl)-5-(and-6)-carboxyfluorescein [BCECF] fluorescence, Na+/H+ exchanger activity from Na+ dependent realkalinization after an ammonium pulse, cell volume from forward scatter in flow cytometry, reactive oxygen species (ROS) from 2',7'-dichlorodihydrofluorescein fluorescence, glucose uptake utilizing 2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose, and lactate concentration in the supernatant utilizing a colorimetric (570 nm)/ fluorometric enzymatic assay. A 48 hour treatment with Ellagic acid (20 µM) significantly decreased NHE1 transcript levels by 75%, NHE1 protein abundance by 95%, pHi from 7.24 ± 0.01 to 7.02 ± 0.01, Na+/H+ exchanger activity by 77%, forward scatter by 10%, ROS by 82%, glucose uptake by 58%, and lactate release by 15%. Ellagic acid (20µM) markedly down-regulates ROS formation and NHE1 expression leading to decreased Na+/H+ exchanger activity, pHi, glucose uptake and lactate release in endometrial cancer cells. Those effects presumably contribute to reprogramming and growth inhibition of tumor cells. © 2017 The Author(s). Published by S. Karger AG, Basel.

Evaluation of antiproliferative, anti-type 2 diabetes, and antihypertension potentials of ellagitannins from strawberries (Fragaria × ananassa Duch.) using in vitro models.

PubMed

Pinto, Marcia da Silva; de Carvalho, Joao Ernesto; Lajolo, Franco Maria; Genovese, Maria Inés; Shetty, Kalidas

2010-10-01

Strawberries represent the main source of ellagic acid derivatives in the Brazilian diet, corresponding to more than 50% of all phenolic compounds found in the fruit. There is a particular interest in the determination of the ellagic acid content in fruits because of possible chemopreventive benefits. In the present study, the potential health benefits of purified ellagitannins from strawberries were evaluated in relation to the antiproliferative activity and in vitro inhibition of α-amylase, α-glucosidase, and angiotensin I-converting enzyme (ACE) relevant for potential management of hyperglycemia and hypertension. Therefore, a comparison among ellagic acid, purified ellagitannins, and a strawberry extract was done to evaluate the possible synergistic effects of phenolics. In relation to the antiproliferative activity, it was observed that ellagic acid had the highest percentage inhibition of cell proliferation. The strawberry extract had lower efficacy in inhibiting the cell proliferation, indicating that in the case of this fruit there is no synergism. Purified ellagitannins had high α-amylase and ACE inhibitory activities. However, these compounds had low α-glucosidase inhibitory activity. These results suggested that the ellagitannins and ellagic acid have good potential for the management of hyperglycemia and hypertension linked to type 2 diabetes. However, further studies with animal and human models are needed to advance the in vitro assay-based biochemical rationale from this study.

Polyphenolic profile as a useful tool to identify the wood used in wine aging.

PubMed

Sanz, Miriam; Fernández de Simón, Brígida; Cadahía, Estrella; Esteruelas, Enrique; Muñoz, Angel Ma; Hernández, Ma Teresa; Estrella, Isabel

2012-06-30

Although oak wood is the main material used in cooperage, other species are being considered as possible sources of wood for the production of wines and their derived products. In this work we have compared the phenolic composition of acacia (Robinia pseudoacacia), chestnut (Castanea sativa), cherry (Prunus avium) and ash (Fraxinus excelsior and F. americana) heartwoods, by using HPLC-DAD/ESI-MS/MS (some of these data have been showed in previous paper), as well as the changes that toasting intensity at cooperage produce in each polyphenolic profile. Before toasting, each wood shows a different and specific polyphenolic profile, with both qualitative and quantitative differences among them. Toasting notably changed these profiles, in general, proportionally to toasting intensity and led to a minor differentiation among species in toasted woods, although we also found phenolic markers in toasted woods. Thus, methyl syringate, benzoic acid, methyl vanillate, p-hydroxybenzoic acid, 3,4,5-trimethylphenol and p-coumaric acid, condensed tannins of the procyanidin type, and the flavonoids naringenin, aromadendrin, isosakuranetin and taxifolin will be a good tool to identify cherry wood. In acacia wood the chemical markers will be the aldehydes gallic and β-resorcylic and two not fully identified hydroxycinnamic compounds, condensed tannins of the prorobinetin type, and when using untoasted wood, dihydrorobinetin, and in toasted acacia wood, robinetin. In untoasted ash wood, the presence of secoiridoids, phenylethanoid glycosides, or di and oligolignols will be a good tool, especially oleuropein, ligstroside and olivil, together verbascoside and isoverbascoside in F. excelsior, and oleoside in F. americana. In toasted ash wood, tyrosol, syringaresinol, cyclolovil, verbascoside and olivil, could be used to identify the botanical origin. In addition, in ash wood, seasoned and toasted, neither hydrolysable nor condensed tannins were detected. Lastly, in chestnut wood, gallic and ellagic acids and hydrolysable tannins of both the gallotannin and ellagitannin type, can be used as chemical markers. Copyright © 2011 Elsevier B.V. All rights reserved.

Gallic acid targets acute myeloid leukemia via Akt/mTOR-dependent mitochondrial respiration inhibition.

PubMed

Gu, Ruixin; Zhang, Minqin; Meng, Hu; Xu, Dandan; Xie, Yonghua

2018-06-05

Gallic acid is one of the many phenolic acids that can be found in dietary substances and traditional medicine herbs. The anti-cancer activities of gallic acid have been shown in various cancers but its underlying molecular mechanisms are not well understood. In this study, we show Akt/mammalian target of rapamycin (mTOR)-dependent inhibition of mitochondrial respiration as a mechanism of gallic acid's action in acute myeloid leukemia (AML). Gallic acid significantly induces apoptosis of AML cell lines, primary mononuclear cells (MNC) and CD34 stem/progenitors isolated form AML patients via caspase-dependent pathway. It also significantly enhances two standard AML chemotherapeutic agents' efficacy in vitro cell culture system and in vivo xenograft model. Gallic acid inhibits dose- and time-dependent mitochondrial respiration, leading to decreased ATP production and oxidative stress. Overexpression of constitutively active Akt restores gallic acid-mediated inhibition of mTOR signaling, mitochondrial dysfunction, energy crisis and apoptosis. Our results demonstrate that mitochondrial respiration inhibition by gallic acid is a consequence of Akt/mTOR signaling suppression. Our findings suggest that combination therapy with gallic acid may enhance antileukemic efficacy of standard chemotherapeutic agents in AML. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

Probing Gallic Acid for Its Broad Spectrum Applications.

PubMed

Choubey, Sneha; Goyal, Soniya; Varughese, Lesley Rachel; Kumar, Vinod

2018-03-29

Gallic acid and its derivatives not only exhibit excellent antioxidant, anticarcinogenic, antimutagenic, antimicrobial properties but also provide protection to the cells against oxidative stress. Gallic acid (3, 4, 5-trihydroxybenzoic acid), a low molecular triphenolic compound has arised as an efficient apoptosis inducing agent. The antimicrobial and other biological properties of gallic acid and its derivatives seemed to be linked with the hydrolysis of ester linkage between gallic acid and polyols like tannins hydrolyzed after ripening of many edible fruits. Gallic acid serves a natural defense mechanism against microbial infections and modulation of immune-responses. The current review updates us with the diverse roles played by gallic acid, its antioxidant potential, action mechanism and more importantly the diverse array of applications in therapeutic and pharmaceutical area. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

The effect of gallic acid on cytotoxicity, Ca(2+) homeostasis and ROS production in DBTRG-05MG human glioblastoma cells and CTX TNA2 rat astrocytes.

PubMed

Hsu, Shu-Shong; Chou, Chiang-Ting; Liao, Wei-Chuan; Shieh, Pochuen; Kuo, Daih-Huang; Kuo, Chun-Chi; Jan, Chung-Ren; Liang, Wei-Zhe

2016-05-25

Gallic acid, a polyhydroxylphenolic compound, is widely distributed in various plants, fruits and foods. It has been shown that gallic acid passes into blood brain barrier and reaches the brain tissue of middle cerebral artery occlusion rats. However, the effect of gallic acid on Ca(2+) signaling in glia cells is unknown. This study explored whether gallic acid affected Ca(2+) homeostasis and induced Ca(2+)-associated cytotoxicity in DBTRG-05MG human glioblastoma cells and CTX TNA2 rat astrocytes. Gallic acid (20-40 μM) concentration-dependently induced cytotoxicity and intracellular Ca(2+) level ([Ca(2+)]i) increases in DBTRG-05MG cells but not in CTX TNA2 cells. In DBTRG-05MG cells, the Ca(2+) response was decreased by half by removal of extracellular Ca(2+). In Ca(2+)-containing medium, gallic acid-induced Ca(2+) entry was inhibited by store-operated Ca(2+) channel inhibitors (2-APB, econazole and SKF96365). In Ca(2+)-free medium, pretreatment with the endoplasmic reticulum Ca(2+) pump inhibitor thapsigargin abolished gallic acid-induced [Ca(2+)]i increases. Conversely, incubation with gallic acid also abolished thapsigargin-induced [Ca(2+)]i increases. Inhibition of phospholipase C with U73122 abolished gallic acid-induced [Ca(2+)]i increases. Gallic acid significantly caused cytotoxicity in DBTRG-05MG cells, which was partially prevented by prechelating cytosolic Ca(2+) with BAPTA-AM. Moreover, gallic acid activated mitochondrial apoptotic pathways that involved ROS production. Together, in DBTRG-05MG cells but not in CTX TNA2 cells, gallic acid induced [Ca(2+)]i increases by causing Ca(2+) entry via 2-APB, econazole and SKF96365-sensitive store-operated Ca(2+) entry, and phospholipase C-dependent release from the endoplasmic reticulum. This Ca(2+) signal subsequently evoked mitochondrial pathways of apoptosis that involved ROS production. Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

Gallic Acid Inhibited Matrix Invasion and AP-1/ETS-1-Mediated MMP-1 Transcription in Human Nasopharyngeal Carcinoma Cells

PubMed Central

S. Pang, Jong-Hwei; Yen, Jia-Hau; Wu, Hsiao-Ting; Huang, Sheng-Teng

2017-01-01

Gallic acid is a trihydroxybenzoic acid found in natural herbal plants. Gallic acid has been reported to inhibit the migration and invasive capability of various cancers. Little is known about the underlying mechanisms of invasion responsible for cancer metastasis via gallic acid. The present study was intended to investigate the anti-invasive effect of gallic acid on human nasopharyngeal carcinoma cells (NPC-BM1) and its related mechanism. Gallic acid inhibited the invasion of NPC-BM1 cells dose- and time-dependently without significant cytotoxic effect. Affymetrix oligonucleotide microarray analysis revealed matrix metalloproteinase-1 (MMP-1) as the most down-regulated gene in NPC-BM1 cells by gallic acid. The cytosolic and secreted MMP-1 levels were both found to be inhibited by gallic acid as demonstrated by western blot analysis and ELISA respectively. The mRNA expression and transcription of MMP-1 gene was also down-regulated as determined by RT/real-time PCR and promoter activity assay. The expression of two major transcription binding factors in the MMP-1 promoter, AP-1 and ETS-1, were demonstrated to be reduced by gallic acid in NPC-BM1 cells. The effect of gallic acid was associated with the inhibition of p38 MAPK signaling pathway. In addition, gallic acid enhanced the gene expression of tissue inhibitor of matrix metalloproteinase-1 (TIMP-1) which further suppressed the MMP-1 activity. These findings may be useful to develop a novel chemotherapeutic agent to inhibit the metastasis of nasopharyngeal cancer. PMID:28672814

Gallic Acid Inhibited Matrix Invasion and AP-1/ETS-1-Mediated MMP-1 Transcription in Human Nasopharyngeal Carcinoma Cells.

PubMed

Pang, Jong-Hwei S; Yen, Jia-Hau; Wu, Hsiao-Ting; Huang, Sheng-Teng

2017-06-24

Gallic acid is a trihydroxybenzoic acid found in natural herbal plants. Gallic acid has been reported to inhibit the migration and invasive capability of various cancers. Little is known about the underlying mechanisms of invasion responsible for cancer metastasis via gallic acid. The present study was intended to investigate the anti-invasive effect of gallic acid on human nasopharyngeal carcinoma cells (NPC-BM1) and its related mechanism. Gallic acid inhibited the invasion of NPC-BM1 cells dose- and time-dependently without significant cytotoxic effect. Affymetrix oligonucleotide microarray analysis revealed matrix metalloproteinase-1 (MMP-1) as the most down-regulated gene in NPC-BM1 cells by gallic acid. The cytosolic and secreted MMP-1 levels were both found to be inhibited by gallic acid as demonstrated by western blot analysis and ELISA respectively. The mRNA expression and transcription of MMP-1 gene was also down-regulated as determined by RT/real-time PCR and promoter activity assay. The expression of two major transcription binding factors in the MMP-1 promoter, AP-1 and ETS-1, were demonstrated to be reduced by gallic acid in NPC-BM1 cells. The effect of gallic acid was associated with the inhibition of p38 MAPK signaling pathway. In addition, gallic acid enhanced the gene expression of tissue inhibitor of matrix metalloproteinase-1 (TIMP-1) which further suppressed the MMP-1 activity. These findings may be useful to develop a novel chemotherapeutic agent to inhibit the metastasis of nasopharyngeal cancer.

An Efficient Protocol for Preparation of Gallic Acid from Terminalia bellirica (Gaertn.) Roxb by Combination of Macroporous Resin and Preparative High-Performance Liquid Chromatography.

PubMed

Zou, Denglang; Chen, Tao; Chen, Chen; Li, Hongmei; Liu, Yongling; Li, Yulin

2016-08-01

In this article, macroporous resin column chromatography and preparative high-performance liquid chromatography were applied for preparation of gallic acid from Terminalia bellirica (Gaertn.) Roxb. In the first step, six kinds of resins were investigated by adsorption and desorption tests and AB-8 macroporous resin was selected for the enrichment of gallic acid. As a result, 20 g of gallic acid at a purity of 71% could be separated from 100 g of crude extract in which the content of gallic acid was 16.7% and the recovery of gallic acid reached 85.0%. In the second step, preparative high-performance liquid chromatography was selected to purify gallic acid. As a result, 640 mg of gallic acid at a purity of 99.1% was obtained from 1 g of sample in 35 min. The results demonstrated that macroporous resin coupled with preparative high-performance liquid chromatography was suitable for preparation of gallic acid from T. bellirica (Gaertn.) Roxb. © The Author 2016. Published by Oxford University Press. All rights reserved. For Permissions, please email: journals.permissions@oup.com.

Gallic Acid Protects 6-OHDA Induced Neurotoxicity by Attenuating Oxidative Stress in Human Dopaminergic Cell Line.

PubMed

Chandrasekhar, Y; Phani Kumar, G; Ramya, E M; Anilakumar, K R

2018-06-01

Gallic acid is one of the most important polyphenolic compounds, which is considered an excellent free radical scavenger. 6-Hydroxydopamine (6-OHDA) is a neurotoxin, which has been implicated in mainly Parkinson's disease (PD). In this study, we investigated the molecular mechanism of the neuroprotective effects of gallic acid on 6-OHDA induced apoptosis in human dopaminergic cells, SH-SY5Y. Our results showed that 6-OHDA induced cytotoxicity in SH-SY5Y cells was suppressed by pre-treatment with gallic acid. The percentage of live cells (90%) was high in the pre-treatment of gallic acid when compared with 6-OHDA alone treated cell line. Moreover, gallic acid was very effective in attenuating the disruption of mitochondrial membrane potential, elevated levels of intracellular ROS and apoptotic cell death induced by 6-OHDA. Gallic acid also lowered the ratio of the pro-apoptotic Bax protein and the anti-apoptotic Bcl-2 protein in SH-SY5Y cells. 6-OHDA exposure was up-regulated caspase-3 and Keap-1 and, down-regulated Nrf2, BDNF and p-CREB, which were sufficiently reverted by gallic acid pre-treatment. These findings indicate that gallic acid is able to protect the neuronal cells against 6-OHDA induced injury and proved that gallic acid might potentially serve as an agent for prevention of several human neurodegenerative diseases caused by oxidative stress and apoptosis.

Nanoencapsulation of gallic acid and evaluation of its cytotoxicity and antioxidant activity.

PubMed

de Cristo Soares Alves, Aline; Mainardes, Rubiana Mara; Khalil, Najeh Maissar

2016-03-01

Gallic acid is an important polyphenol compound presenting various biological activities. The objective of this study was to prepare, characterize and evaluate poly(lactic-co-glycolic acid) (PLGA) nanoparticles coated or not with polysorbate 80 (PS80) containing gallic acid. Nanoparticles coated or not with PS80 were produced by emulsion solvent evaporation method and presented a mean size of around 225 nm, gallic acid encapsulation efficiency of around 26% and zeta potential of -22 mV. Nanoparticle formulations were stable during storage, except nanoparticles coated with PS80 stored at room temperature. In vitro release profile demonstrated a quite sustained gallic acid release from nanoparticles and PS80-coating decreased drug release. Cytotoxicity over red blood cells was assessed and gallic acid-loaded PLGA nanoparticles at all analyzed concentrations demonstrated lack of hemolysis, while PS80-nanoparticles containing gallic acid were cytotoxic only in higher concentrations. Antioxidant potential of nanoparticles containing gallic acid was assessed and PLGA uncoated nanoparticles presented greater efficacy than PS80-coated PLGA nanoparticles. Copyright © 2015 Elsevier B.V. All rights reserved.

Optimization of ultrasound-assisted hydroalcoholic extraction of phenolic compounds from walnut leaves using response surface methodology.

PubMed

Nour, Violeta; Trandafir, Ion; Cosmulescu, Sina

2016-10-01

Context Walnut leaves are highly appreciated for their pharmacological effects and therapeutic properties which are mainly attributed to their high content of phenolic compounds. Objective This study optimizes ultrasound assisted hydroalcoholic extraction (UAE) of phenolic compounds from dried walnut leaves by the maximization of total phenolics content (TPC) and total flavanoids content (TFC) of the extracts. Materials and methods Optimal conditions with regard to ethanol concentration (X1: 12.17-95.83% v/v), extraction time (X2: 8.17-91.83 min) and liquid-to-solid ratio (X3: 4.96-25.04 v/w) were identified using central composite design combined with response surface methodology. A high-performance liquid chromatography method with diode-array detection was used to quantify phenolic acids (gallic, vanillic, chlorogenic, caffeic, syringic, p-coumaric, ferulic, sinapic, salicylic, ellagic and trans-cinnamic), flavonoids (catechin, epicatechin, rutin, myricetin and quercetin) and juglone in the extracts. Results Liquid-to-solid ratio and ethanol concentration proved to be the primary factors affecting the extraction efficiency. The maximum predicted TPC, under the optimized conditions (61% ethanol concentration, 51.28 min extraction time and 4.96 v/w liquid-to-solid ratio) was 10125.4 mg gallic acid equivalents per liter while maximum TFC (2925 mg quercetin equivalents per liter) occurred at 67.83% ethanol concentration, 4.96 v/w liquid-to-solid ratio and 49.37 min extraction time. High significant correlations were found between antioxidant activity and both TPC (R(2 )=( )0.81) and TFC (R(2 )=( )0.78). Discussion and conclusion Extracts very rich in polyphenols could be obtained from walnut leaves by using UAE, aimed at preparing dietary supplements, nutraceuticals or functional food ingredients.

Evaluation of antimutagenic and protective effects of Parkinsonia aculeata L. leaves against H2O2 induced damage in pBR322 DNA.

PubMed

Sharma, Sonia; Sharma, Sushant; Vig, Adarsh Pal

2016-01-01

The in vitro antimutagenic and DNA protecting potential of organic (methanol, hexane, n-butanol) and aqueous extract/fractions of Parkinsonia aculeata L. (Fabaceae) was investigated by employing Ames assay and DNA nicking assay. DNA damage by hydroxyl radicals was effectively inhibited by all the extract/fractions. A marked antimutagenic effect was observed against 4-Nitro-o-phenylenediamine and sodium azide (direct acting mutagens) and 2-Aminofluorene (indirect acting mutagen) in TA98 and TA100 strains of Salmonella typhimurium. In Ames assay, two different modes of experiments i.e. pre-incubation and co-incubation were performed and it was observed that all the extract/fractions showed better results in the pre-incubation as compared to co- incubation mode. Out of all the extract/fractions tested, n-butanol fraction was found to be the most effective in preventing DNA damage and inhibiting mutagenesis. UHPLC analysis of extract/fractions revealed presence of polyphenols such as gallic acid, catechin, chlorogenic acid, caffeic acid, umbelliferone, coumaric acid, rutin, and ellagic acid etc. DNA protecting and antimutagenic activity of this plant could be attributed to presence of these polyphenols. The results of this study indicate the presence of potent antioxidant factors in Parkinsonia aculeata L, which are being explored further for their mechanism of action.

Antinociceptive and Anti-Inflammatory Activities of Bridelia retusa Methanolic Fruit Extract in Experimental Animals

PubMed Central

Kumar, Tekeshwar; Jain, Vishal

2014-01-01

Antinociceptive and anti-inflammatory potentials of methanolic extract of Bridelia retusa fruit (BRME) were evaluated against different animal models in rodents. Antinociceptive effects of BRME were assessed in mice using the acetic acid-induced writhing and formalin test. Anti-inflammatory effects of BRME in three different doses, namely, 100, 200, and 400 mg/kg, were evaluated by utilizing different animal models representing various changes associated with inflammation, namely, carrageenan-induced paw oedema, histamine and serotonin-induced paw oedema, arachidonic acid-induced paw oedema, formalin-induced paw oedema, TPA-induced ear oedema, acetic acid-induced vascular permeability, total WBC count in paw fluid, and myeloperoxidase assay. Also BRME was phytochemically evaluated using chromatographic method. The BRME did not exhibit any signs of toxicity up to a dose of 2000 mg/kg. The extract showed statistical significant inhibition of induced nociception and inflammation in dose dependent manner. The higher dose of extract significantly inhibited pain and inflammation against control (P < 0.001). HPLC results revealed the presence of gallic acid and ellagic acid as phytoconstituents in BRME and it was proven as anti-inflammatory agents. The present study scientifically demonstrated the antinociceptive and anti-inflammatory potential of fruit of B. retusa methanolic extract. These effects may be attributed to the presence of polyphenolic phytoconstituents in the extract. PMID:25506619

Effect of gallic and protocatechuic acids on the metabolism of ethyl carbamate in Chinese yellow rice wine brewing.

PubMed

Zhou, Wanyi; Fang, Ruosi; Chen, Qihe

2017-10-15

It was studied that gallic and protocatechuic acids played important roles in ethyl carbamate (EC) forming. Gallic and protocatechuic acids can reduce the arginine consumption through inhibiting the arginine deiminase enzyme. Therefore, they are generally added to regulate EC catabolism in the course of yellow rice wine leavening at the third day. In this work, gallic and protocatechuic acids made little influence on the growth of Saccharomyces cerevisiae. Besides, the addition of 200mg/L gallic or protocatechuic acid could prevent the transformation from urea/citrulline to EC. Gallic acid showed better inhibiting effect that the content of EC could be reduced by 91.9% at most. Furthermore, the production of amino acids and volatile flavor compounds are not markedly affected by phenolic compounds. The discoveries reveal that EC can be reduced by supplying gallic acid or protocatechuic acid while yellow rice wine leavening. Copyright © 2017 Elsevier Ltd. All rights reserved.

Combined Efficacy of Gallic Acid and MiADMSA with Limited Beneficial Effects Over MiADMSA Against Arsenic-induced Oxidative Stress in Mouse

PubMed Central

Pachauri, Vidhu; Flora, SJS

2015-01-01

Gallic acid is an organic acid known for its antioxidant and anticancer properties. The present study is focused on evaluating the role of gallic acid in providing better therapeutic outcomes against arsenic-induced toxicity. Animals pre-exposed to arsenic were treated with monoisoamyl meso-2,3-dimercaptosuccinic acid (MiADMSA), a new chelating drug, alone and in combination with gallic acid, consecutively for 10 days. The study suggests that (1) gallic acid in presence of MiADMSA is only moderately beneficial against arsenic, (2) monotherapy with gallic acid is more effective than in combination with MiADMSA after arsenic exposure in reducing oxidative injury, and (3) MiADMSA monotherapy as reported previously provides significant therapeutic efficacy against arsenic. Thus, based on the present results, we conclude that gallic acid is effective against arsenic-induced oxidative stress but provides limited additional beneficial effects when administered in combination with MiADMSA. We still recommend that lower doses of gallic acid be evaluated both individually and in combination with MiADMSA, as it might not exhibit the shortcomings we observed with higher doses in this study. PMID:26339189

Combined Efficacy of Gallic Acid and MiADMSA with Limited Beneficial Effects Over MiADMSA Against Arsenic-induced Oxidative Stress in Mouse.

PubMed

Pachauri, Vidhu; Flora, Sjs

2015-01-01

Gallic acid is an organic acid known for its antioxidant and anticancer properties. The present study is focused on evaluating the role of gallic acid in providing better therapeutic outcomes against arsenic-induced toxicity. Animals pre-exposed to arsenic were treated with monoisoamyl meso-2,3-dimercaptosuccinic acid (MiADMSA), a new chelating drug, alone and in combination with gallic acid, consecutively for 10 days. The study suggests that (1) gallic acid in presence of MiADMSA is only moderately beneficial against arsenic, (2) monotherapy with gallic acid is more effective than in combination with MiADMSA after arsenic exposure in reducing oxidative injury, and (3) MiADMSA monotherapy as reported previously provides significant therapeutic efficacy against arsenic. Thus, based on the present results, we conclude that gallic acid is effective against arsenic-induced oxidative stress but provides limited additional beneficial effects when administered in combination with MiADMSA. We still recommend that lower doses of gallic acid be evaluated both individually and in combination with MiADMSA, as it might not exhibit the shortcomings we observed with higher doses in this study.

Bioactive compounds and sensory quality of black and white mulberries grown in Spain.

PubMed

Calín-Sánchez, Angel; Martínez-Nicolás, Juan José; Munera-Picazo, Sandra; Carbonell-Barrachina, Angel A; Legua, Pilar; Hernández, Francisca

2013-12-01

The objective of this study was to evaluate and compare, for the first time, white and black mulberry species in terms of main phytochemical, volatile composition and sensory profile characteristics in eight Spanish clones. The results showed that black and white mulberry species displayed significant different characteristics. PLS analysis has allowed grouping of the clones into four groups (i) MA1, MA2 and MN2, (ii) MN3 and MN4, (iii) MA3 and MA4, and (iv) MN1. Experimental results proved that Spanish mulberries have potential for fresh consumption due to their high antioxidant capacity (10.7-86.1 mg Trolox 100 g(-1)), polyphenol (76.7-180 mg gallic acid 100 g(-1)) and ellagic acid content (8.7-15.5 mg 100 g(-1)) as well as considerable amount of volatile compounds (35) with desirable attributes, which were scored high by a trained panel. Cultivars from the Morus nigra species seem to provide fruits with higher content of bioactive compounds and better aptitude for fresh consumption than Morus alba. Differences among the species should be attributed to genetics because they were cultivated under same conditions.

Determination of phenolic compounds derived from hydrolysable tannins in biological matrices by RP-HPLC.

PubMed

Díez, María Teresa; García del Moral, Pilar; Resines, José Antonio; Arín, María Jesús

2008-08-01

An RP-HPLC method for the determination of four phenolic compounds: gallic acid (GA), pyrogallol (PY), resorcinol (RE) and ellagic acid (EA), derived from hydrolysable tannins is reported. Separation was achieved on a SunFire C18 (250 x 4.6 mm id, 5 microm) column at 40 degrees C with gradient elution. UV detection at 280 nm was applied. The developed method was validated in terms of linearity, accuracy and precision. Satisfactory repeatability and between day precision were noticed with RSD values lower than 3%. Recoveries from different biological samples ranged from 91.50 to 105.25%. The LODs were estimated as 1.70 mg/L for PY, 1.68 mg/L for GA, 1.52 mg/L for RE and 0.98 mg/L for EA with a 20 microL injection volume. The method was applied for the determination of these compounds in oak leaves and in ruminal fluid and urine samples taken from beef cattle fed with oak leaves. The proposed method could be used in ruminant nutrition studies to verify the effect that a diet rich in tannins have on ruminal fermentation and to determine the toxicity of these compounds.

Walnut Phenolic Extract and Its Bioactive Compounds Suppress Colon Cancer Cell Growth by Regulating Colon Cancer Stemness.

PubMed

Lee, Jisoo; Kim, Yoo-Sun; Lee, JaeHwan; Heo, Seung Chul; Lee, Kook Lae; Choi, Sang-Woon; Kim, Yuri

2016-07-21

Walnut has been known for its health benefits, including anti-cardiovascular disease and anti-oxidative properties. However, there is limited evidence elucidating its effects on cancer stem cells (CSCs) which represent a small subset of cancer cells that provide resistance against chemotherapy. This study aimed to evaluate the anti-CSCs potential of walnut phenolic extract (WPE) and its bioactive compounds, including (+)-catechin, chlorogenic acid, ellagic acid, and gallic acid. In the present study, CD133⁺CD44⁺ cells were isolated from HCT116 cells using fluorescence-activated cell sorting (FACS) and then treated with WPE. As a result, survival of the CD133⁺CD44⁺ HCT116 cells was inhibited and cell differentiation was induced by WPE. In addition, WPE down-regulated the CSC markers, CD133, CD44, DLK1, and Notch1, as well as the β-catenin/p-GSK3β signaling pathway. WPE suppressed the self-renewal capacity of CSCs. Furthermore, the WPE exhibited stronger anti-CSC effects than its individual bioactive compounds. Finally, the WPE inhibited specific CSC markers in primary colon cancer cells isolated from primary colon tumor. These results suggest that WPE can suppress colon cancer by regulating the characteristics of colon CSCs.

Constituents and antimicrobial properties of blue honeysuckle: a novel source for phenolic antioxidants.

PubMed

Palíková, Irena; Heinrich, Jan; Bednár, Petr; Marhol, Petr; Kren, Vladimír; Cvak, Ladislav; Valentová, Katerina; Růzicka, Filip; Holá, Veronika; Kolár, Milan; Simánek, Vilím; Ulrichová, Jitka

2008-12-24

The fruit of Lonicera caerulea L. (blue honeysuckle; Caprifoliaceae) and its phenolic fraction were analyzed for nutrients and micronutrients. The phenolic fraction was prepared from berries percolated with 0.1% H3PO4 and SPE using Sepabeads SP207. The sugar and lipid content was analyzed by HPLC and GC-MS. The total content of anthocyanins was determined using the pH differential absorbance method and aliphatic acids by capillary electrophoresis. MicroLC-MS/MS was used for determination of cyanidin-3-glucoside (the predominant anthocyanin), 3,5-diglucoside, and 3-rutinoside, paeonidin-3-glucoside, 3,5-diglucoside, and 3-rutinoside, delphinidin-3-glucoside and 3-rutinoside, pelargonidin-3-glucoside, 3,5-diglucoside, and 3-rutinoside, quercetin, its 3-glucoside, and 3-rutinoside, epicatechin, protocatechuic, gentisic, ellagic, ferulic, caffeic, chlorogenic, and coumaric acids. The phenolic fraction displayed Folin-Ciocalteu reagent reducing (335 +/- 15 microg of gallic acid equivalent/mg) and DPPH and superoxide scavenging activity (IC50 12.1 +/- 0.1 and 115.5 +/- 6.4 microg/mL) and inhibited rat liver microsome peroxidation (IC50 160 +/- 20 microg/mL). The freeze-dried fruit and its phenolic fraction reduced the biofilm formation and adhesion to the artificial surface of Candida parapsilosis, Staphylococcus epidermidis, Escherichia coli, Enterococcus faecalis, and Streptococcus mutans.

Walnut Phenolic Extract and Its Bioactive Compounds Suppress Colon Cancer Cell Growth by Regulating Colon Cancer Stemness

PubMed Central

Lee, Jisoo; Kim, Yoo-Sun; Lee, JaeHwan; Heo, Seung Chul; Lee, Kook Lae; Choi, Sang-Woon; Kim, Yuri

2016-01-01

Walnut has been known for its health benefits, including anti-cardiovascular disease and anti-oxidative properties. However, there is limited evidence elucidating its effects on cancer stem cells (CSCs) which represent a small subset of cancer cells that provide resistance against chemotherapy. This study aimed to evaluate the anti-CSCs potential of walnut phenolic extract (WPE) and its bioactive compounds, including (+)-catechin, chlorogenic acid, ellagic acid, and gallic acid. In the present study, CD133+CD44+ cells were isolated from HCT116 cells using fluorescence-activated cell sorting (FACS) and then treated with WPE. As a result, survival of the CD133+CD44+ HCT116 cells was inhibited and cell differentiation was induced by WPE. In addition, WPE down-regulated the CSC markers, CD133, CD44, DLK1, and Notch1, as well as the β-catenin/p-GSK3β signaling pathway. WPE suppressed the self-renewal capacity of CSCs. Furthermore, the WPE exhibited stronger anti-CSC effects than its individual bioactive compounds. Finally, the WPE inhibited specific CSC markers in primary colon cancer cells isolated from primary colon tumor. These results suggest that WPE can suppress colon cancer by regulating the characteristics of colon CSCs. PMID:27455311

Effects of gallic acid on delta - aminolevulinic dehydratase activity and in the biochemical, histological and oxidative stress parameters in the liver and kidney of diabetic rats.

PubMed

de Oliveira, Lizielle Souza; Thomé, Gustavo Roberto; Lopes, Thauan Faccin; Reichert, Karine Paula; de Oliveira, Juliana Sorraila; da Silva Pereira, Aline; Baldissareli, Jucimara; da Costa Krewer, Cristina; Morsch, Vera Maria; Chitolina Schetinger, Maria Rosa; Spanevello, Roselia Maria

2016-12-01

Diabetes mellitus (DM) is characterised by hyperglycaemia associated with the increase of oxidative stress. Gallic acid has potent antioxidant properties. The aim of this study was to evaluate the effect of gallic acid on the biochemical, histological and oxidative stress parameters in the liver and kidney of diabetic rats. Male rats were divided in groups: control, gallic acid, diabetic and diabetic plus gallic acid. DM was induced in the animals by intraperitoneal injection of streptozotocin (65mg/kg). Gallic acid (30mg/kg) was administered orally for 21days. Our results showed an increase in reactive species levels and lipid peroxidation, and a decrease in activity of the enzymes superoxide dismutase and delta-aminolevulinic acid dehydratase in the liver and kidney of the diabetic animals (P<0.05). Gallic acid treatment showed protective effects in these parameters evaluated, and also prevented a decrease in the activity of catalase and glutathione S-transferase, and vitamin C levels in the liver of diabetic rats. In addition, gallic acid reduced the number of nuclei and increased the area of the core in hepatic tissue, and increased the glomerular area in renal tissue. These results indicate that gallic acid can protect against oxidative stress-induced damage in the diabetic state. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

Antibacterial, antioxidant and tyrosinase-inhibition activities of pomegranate fruit peel methanolic extract

PubMed Central

2012-01-01

Background This study evaluated, using in vitro assays, the antibacterial, antioxidant, and tyrosinase-inhibition activities of methanolic extracts from peels of seven commercially grown pomegranate cultivars. Methods Antibacterial activity was tested on Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli and Klebsiella pneumonia) using a microdilution method. Several potential antioxidant activities, including radical-scavenging ability (RSA), ferrous ion chelating (FIC) and ferric ion reducing antioxidant power (FRAP), were evaluated. Tyrosinase enzyme inhibition was investigated against monophenolase (tyrosine) and diphenolase (DOPA), with arbutin and kojic acid as positive controls. Furthermore, phenolic contents including total flavonoid content (TFC), gallotannin content (GTC) and total anthocyanin content (TAC) were determined using colourimetric methods. HPLC-ESI/MSn analysis of phenolic composition of methanolic extracts was also performed. Results Methanolic peel extracts showed strong broad-spectrum activity against Gram-positive and Gram-negative bacteria, with the minimum inhibitory concentrations (MIC) ranging from 0.2 to 0.78 mg/ml. At the highest concentration tested (1000 μg/ml), radical scavenging activities were significantly higher in Arakta (83.54%), Ganesh (83.56%), and Ruby (83.34%) cultivars (P< 0.05). Dose dependent FIC and FRAP activities were exhibited by all the peel extracts. All extracts also exhibited high inhibition (>50%) against monophenolase and diphenolase activities at the highest screening concentration. The most active peel extract was the Bhagwa cultivar against monophenolase and the Arakta cultivar against diphenolase with IC50 values of 3.66 μg/ml and 15.88 μg/ml, respectively. High amounts of phenolic compounds were found in peel extracts with the highest and lowest total phenolic contents of 295.5 (Ganesh) and 179.3 mg/g dry extract (Molla de Elche), respectively. Catechin, epicatechin, ellagic acid and gallic acid were found in all cultivars, of which ellagic acid was the most abundant comprising of more than 50% of total phenolic compounds detected in each cultivar. Conclusions The present study showed that the tested pomegranate peels exhibited strong antibacterial, antioxidant and tyrosinase-inhibition activities. These results suggest that pomegranate fruit peel could be exploited as a potential source of natural antimicrobial and antioxidant agents as well as tyrosinase inhibitors. PMID:23110485

Design of biodegradable nanoparticles: a novel approach to encapsulating poorly soluble phytochemical ellagic acid

NASA Astrophysics Data System (ADS)

Bala, I.; Bhardwaj, V.; Hariharan, S.; Sitterberg, J.; Bakowsky, U.; Kumar, M. N. V. Ravi

2005-12-01

Nanosizing of poorly water soluble drugs or incorporating them into nanoparticles to increase their solubility and thereby the bioavailability has become a favoured approach today. This work describes a novel method for encapsulating poorly water soluble phytochemical ellagic acid that is also sparingly soluble/insoluble in routine solvents used to prepare nanoparticles.

Organic Materials as Electrodes for Li-ion Batteries

DTIC Science & Technology

2015-09-04

Various macrocycles, their synthesis, characterization and subsequent use in lithium - ion batteries were attempted. Ellagic acid, alizarin and...Various macrocycles, their synthesis, characterization and subsequent use in lithium - ion batteries were attempted. Ellagic acid, alizarin and...characterization and subsequent use in lithium - ion batteries have been attempted to. Lithium -based batteries are at the forefront of battery

Effect of pomegranate powder on the heat inactivation of Escherichia coli O157:H4 in ground chicken

USDA-ARS?s Scientific Manuscript database

Health concerns have led to a search for natural plant-based antimicrobials. Ellagic acid has been shown to have antimicrobial activity against foodborne pathogens. The objective of this study was to assess the effect of a high-ellagic acid commercial pomegranate on the heat resistance of Escherich...

Agdc1p – a Gallic Acid Decarboxylase Involved in the Degradation of Tannic Acid in the Yeast Blastobotrys (Arxula) adeninivorans

PubMed Central

Meier, Anna K.; Worch, Sebastian; Böer, Erik; Hartmann, Anja; Mascher, Martin; Marzec, Marek; Scholz, Uwe; Riechen, Jan; Baronian, Kim; Schauer, Frieder; Bode, Rüdiger; Kunze, Gotthard

2017-01-01

Tannins and hydroxylated aromatic acids, such as gallic acid (3,4,5-trihydroxybenzoic acid), are plant secondary metabolites which protect plants against herbivores and plant-associated microorganisms. Some microbes, such as the yeast Arxula adeninivorans are resistant to these antimicrobial substances and are able to use tannins and gallic acid as carbon sources. In this study, the Arxula gallic acid decarboxylase (Agdc1p) which degrades gallic acid to pyrogallol was characterized and its function in tannin catabolism analyzed. The enzyme has a higher affinity for gallic acid (Km −0.7 ± 0.2 mM, kcat −42.0 ± 8.2 s−1) than to protocatechuic acid (3,4-dihydroxybenzoic acid) (Km −3.2 ± 0.2 mM, kcat −44.0 ± 3.2 s−1). Other hydroxylated aromatic acids, such as 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid and 2,5-dihydroxybenzoic acid are not gallic acid decarboxylase substrates. A. adeninivorans G1212/YRC102-AYNI1-AGDC1, which expresses the AGDC1 gene under the control of the strong nitrate inducible AYNI1 promoter achieved a maximum gallic acid decarboxylase activity of 1064.4 U/l and 97.5 U/g of dry cell weight in yeast grown in minimal medium with nitrate as nitrogen source and glucose as carbon source. In the same medium, gallic acid decarboxylase activity was not detected for the control strain G1212/YRC102 with AGDC1 expression under the control of the endogenous promoter. Gene expression analysis showed that AGDC1 is induced by gallic acid and protocatechuic acid. In contrast to G1212/YRC102-AYNI1-AGDC1 and G1212/YRC102, A. adeninivorans G1234 [Δagdc1] is not able to grow on medium with gallic acid as carbon source but can grow in presence of protocatechuic acid. This confirms that Agdc1p plays an essential role in the tannic acid catabolism and could be useful in the production of catechol and cis,cis-muconic acid. However, the protocatechuic acid catabolism via Agdc1p to catechol seems to be not the only degradation pathway. PMID:28966611

Agdc1p - a Gallic Acid Decarboxylase Involved in the Degradation of Tannic Acid in the Yeast Blastobotrys (Arxula) adeninivorans.

PubMed

Meier, Anna K; Worch, Sebastian; Böer, Erik; Hartmann, Anja; Mascher, Martin; Marzec, Marek; Scholz, Uwe; Riechen, Jan; Baronian, Kim; Schauer, Frieder; Bode, Rüdiger; Kunze, Gotthard

2017-01-01

Tannins and hydroxylated aromatic acids, such as gallic acid (3,4,5-trihydroxybenzoic acid), are plant secondary metabolites which protect plants against herbivores and plant-associated microorganisms. Some microbes, such as the yeast Arxula adeninivorans are resistant to these antimicrobial substances and are able to use tannins and gallic acid as carbon sources. In this study, the Arxula gallic acid decarboxylase (Agdc1p) which degrades gallic acid to pyrogallol was characterized and its function in tannin catabolism analyzed. The enzyme has a higher affinity for gallic acid (K m -0.7 ± 0.2 mM, k cat -42.0 ± 8.2 s -1 ) than to protocatechuic acid (3,4-dihydroxybenzoic acid) (K m -3.2 ± 0.2 mM, k cat -44.0 ± 3.2 s -1 ). Other hydroxylated aromatic acids, such as 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid and 2,5-dihydroxybenzoic acid are not gallic acid decarboxylase substrates. A. adeninivorans G1212/YRC102-AYNI1-AGDC1, which expresses the AGDC1 gene under the control of the strong nitrate inducible AYNI1 promoter achieved a maximum gallic acid decarboxylase activity of 1064.4 U/l and 97.5 U/g of dry cell weight in yeast grown in minimal medium with nitrate as nitrogen source and glucose as carbon source. In the same medium, gallic acid decarboxylase activity was not detected for the control strain G1212/YRC102 with AGDC1 expression under the control of the endogenous promoter. Gene expression analysis showed that AGDC1 is induced by gallic acid and protocatechuic acid. In contrast to G1212/YRC102-AYNI1-AGDC1 and G1212/YRC102, A. adeninivorans G1234 [Δ agdc1 ] is not able to grow on medium with gallic acid as carbon source but can grow in presence of protocatechuic acid. This confirms that Agdc1p plays an essential role in the tannic acid catabolism and could be useful in the production of catechol and cis,cis -muconic acid. However, the protocatechuic acid catabolism via Agdc1p to catechol seems to be not the only degradation pathway.

Use of Gallic Acid to Enhance the Antioxidant and Mechanical Properties of Active Fish Gelatin Film.

PubMed

Limpisophon, Kanokrat; Schleining, Gerhard

2017-01-01

This study explores the potential roles of gallic acid in fish gelatin film for improving mechanical properties, UV barrier, and providing antioxidant activities. Glycerol, a common used plasticizer, also impacts on mechanical properties of the film. A factorial design was used to investigate the effects of gallic acid and glycerol concentrations on antioxidant activities and mechanical properties of fish gelatin film. Increasing the amount of gallic acid increased the antioxidant capacities of the film measured by radical scavenging assay and the ferric reducing ability of plasma assay. The released antioxidant power of gallic acid from the film was not reduced by glycerol. The presence of gallic acid not only increased the antioxidant capacity of the film, but also increased the tensile strength, elongation at break, and reduced UV absorption due to interaction between gallic acid and protein by hydrogen bonding. Glycerol did not affect the antioxidant capacities of the film, but increased the elasticity of the films. Overall, this study revealed that gallic acid entrapped in the fish gelatin film provided antioxidant activities and improved film characteristics, namely UV barrier, strength, and elasticity of the film. © 2016 Institute of Food Technologists®.

Protective effect of gallic acid in experimental model of ketamine-induced psychosis: possible behaviour, biochemical, neurochemical and cellular alterations.

PubMed

Yadav, Monu; Jindal, Deepak Kumar; Dhingra, Mamta Sachdeva; Kumar, Anil; Parle, Milind; Dhingra, Sameer

2018-04-01

Gallic acid has been reported to possess a number of psychopharmacological activities. These activities are attributed to the antioxidant potential due to the presence of phenolic moeity. The present study was carried out to investigate the protective effects of gallic acid in an experimental model of ketamine-induced psychosis in mice. Ketamine (50 mg/kg, i.p.) was used to induce stereotyped psychotic behavioural symptoms in mice. Behavioural studies (locomotor activity, stereotype behaviour, immobility duration and memory retention) were carried out to investigate the protective of gallic acid on ketamine-induced psychotic symptoms, followed by biochemical and neurochemical changes and cellular alterations in the brain. Chronic treatment with gallic acid for 15 consecutive days significantly attenuated stereotyped behavioural symptoms in mice. Biochemical estimations revealed that gallic acid reduced the lipid peroxidation and restored the total brain proteins. Furthermore, gallic acid remarkably reduced the dopamine levels, AChE activity and inflammatory surge (serum TNF-α), and increased the levels of GABA and increased glutathione in mice. The study revealed that gallic acid could ameliorate psychotic symptoms and biochemical changes in mice, indicating protective effects in psychosis.

Gallic Acid Attenuates Platelet Activation and Platelet-Leukocyte Aggregation: Involving Pathways of Akt and GSK3β

PubMed Central

Chang, Shih-Sheng; Lee, Viola S. Y.; Tseng, Yu-Lun; Chang, Kuan-Cheng; Chen, Kuen-Bao; Chen, Yuh-Lien; Li, Chi-Yuan

2012-01-01

Platelet activation and its interaction with leukocytes play an important role in atherothrombosis. Cardiovascular diseases resulted from atherothrombosis remain the major causes of death worldwide. Gallic acid, a major constituent of red wine and tea, has been believed to have properties of cardiovascular protection, which is likely to be related to its antioxidant effects. Nonetheless, there were few and inconsistent data regarding the effects of gallic acid on platelet function. Therefore, we designed this in vitro study to determine whether gallic acid could inhibit platelet activation and the possible mechanisms. From our results, gallic acid could concentration-dependently inhibit platelet aggregation, P-selectin expression, and platelet-leukocyte aggregation. Gallic acid prevented the elevation of intracellular calcium and attenuated phosphorylation of PKCα/p38 MAPK and Akt/GSK3β on platelets stimulated by the stimulants ADP or U46619. This is the first mechanistic explanation for the inhibitory effects on platelets from gallic acid. PMID:22811749

Inhibition of protein glycation, antioxidant and antiproliferative activities of Carpobrotus edulis extracts.

PubMed

Hafsa, Jawhar; Hammi, Khaoula Mkadmini; Khedher, Med Raâfet Ben; Smach, Med Ali; Charfeddine, Bassem; Limem, Khalifa; Majdoub, Hatem

2016-12-01

Carpobrotus edulis is an important South African medicinal plants used as a food and therapeutic agent in traditional medicine. The aim of this study was to determine the phytochemical content, antioxidant, antiglycation and cytotoxic effect against Human Colon Cancer Cell Line (HCT-116) of aqueous and ethanol-water (1:1v/v) extracts of Carpobrotus edulis.The content of total phenolics and flavonoids in aqueous and ethanol-water extract were 151.99μg and 66.35μg gallic acid equivalents/mg of dry extract, and 38.84μg and 21.96μg quercetin/mg of dry extract, respectively. Furthermore, phenolic compositions analysis indicated the presence of seven majority compounds including sinapic acid, ferulic acid, luteolin7-o-glucoside, hyperoside, isoquercitrin, ellagic acid and isorhamnetin 3-O-rutinoside. The ethanol-water extract (100-1000μg/mL) showed better antioxidant activity than aqueous extract. Furthermore, Carpobrotus edulis extracts, especially ethanol-water extract significantly inhibited the formation of fluorescent advanced glycation end products, prevented oxidation-induced protein damage and exhibited a cytotoxic effect against HCT116 cells, with a significant decrease in cell viability after 24h of incubation. The results obtained suggest that the Carpobrotus edulis extracts could be used as an easily accessible source of natural antioxidants and as potential phytochemicals against protein glycation and colon cancer. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

Gallic acid attenuates pulmonary fibrosis in a mouse model of transverse aortic contraction-induced heart failure.

PubMed

Jin, Li; Piao, Zhe Hao; Sun, Simei; Liu, Bin; Ryu, Yuhee; Choi, Sin Young; Kim, Gwi Ran; Kim, Hyung-Seok; Kee, Hae Jin; Jeong, Myung Ho

2017-12-01

Gallic acid, a trihydroxybenzoic acid found in tea and other plants, attenuates cardiac hypertrophy, fibrosis, and hypertension in animal models. However, the role of gallic acid in heart failure remains unknown. In this study, we show that gallic acid administration prevents heart failure-induced pulmonary fibrosis. Heart failure induced in mice, 8weeks after transverse aortic constriction (TAC) surgery, was confirmed by echocardiography. Treatment for 2weeks with gallic acid but not furosemide prevented cardiac dysfunction in mice. Gallic acid significantly inhibited TAC-induced pathological changes in the lungs, such as increased lung mass, pulmonary fibrosis, and damaged alveolar morphology. It also decreased the expression of fibrosis-related genes, including collagen types I and III, fibronectin, connective tissue growth factor (CTGF), and phosphorylated Smad3. Further, it inhibited the expression of epithelial-mesenchymal transition (EMT)-related genes, such as N-cadherin, vimentin, E-cadherin, SNAI1, and TWIST1. We suggest that gallic acid has therapeutic potential for the treatment of heart failure-induced pulmonary fibrosis. Copyright © 2017 Elsevier Inc. All rights reserved.

Inhibition of Melanogenesis by Gallic Acid: Possible Involvement of the PI3K/Akt, MEK/ERK and Wnt/β-Catenin Signaling Pathways in B16F10 Cells

PubMed Central

Su, Tzu-Rong; Lin, Jen-Jie; Tsai, Chi-Chu; Huang, Tsu-Kei; Yang, Zih-Yan; Wu, Ming-O; Zheng, Yu-Qing; Su, Ching-Chyuan; Wu, Yu-Jen

2013-01-01

Gallic acid is one of the major flavonoids found in plants. It acts as an antioxidant, and seems to have anti-inflammatory, anti-viral, and anti-cancer properties. In this study, we investigated the effects of gallic acid on melanogenesis, including the activation of melanogenesis signaling pathways. Gallic acid significantly inhibited both melanin synthesis and tyrosinase activity in a dose- and time-dependent manner, and decreased the expression of melanogenesis-related proteins, such as microphthalmia-associated transcription factor (MITF), tyrosinase, tyrosinase-related protein-1 (TRP1), and dopachrome tautomerase (Dct). In addition, gallic acid also acts by phosphorylating and activating melanogenesis inhibitory proteins such as Akt and mitogen-activated protein kinase (MEK)/extracellular signal-regulated kinase (ERK). Using inhibitors against PI3K/Akt (LY294002) or MEK/ERK-specific (PD98059), the hypopigmentation effect was suppressed, and the gallic acid-initiated activation of MEK/ERK and PI3K/Akt was also revoked. Gallic acid also increased GSK3β and p-β-catenin expression but down-regulated p-GSK3β. Moreover, GSK3β-specific inhibitor (SB216763) restored gallic acid-induced melanin reduction. These results suggest that activation of the MEK/ERK, PI3K/Akt, and inhibition of Wnt/β-catenin signaling pathways is involved in the melanogenesis signaling cascade, and that activation by gallic acid reduces melanin synthesis via down-regulation of MITF and its downstream signaling pathway. In conclusion, gallic acid may be a potentially agent for the treatment of certain skin conditions. PMID:24129178

Gallic acid attenuates type I diabetic nephropathy in rats.

PubMed

Garud, Mayuresh Sudamrao; Kulkarni, Yogesh Anant

2018-02-25

Literature suggests that TGF-β1 has a central role in the progression of diabetic nephropathy and its down regulation can improve the disease condition. Oxidative stress, generation of advanced glycation end products and activation of renin angiotensin system are the connecting links between hyperglycemia and TGF-β1 over expression. Gallic acid is a phytochemical having wide range of biological activities. Gallic acid is reported to have antioxidant and advanced glycation inhibitory activity. It has also shown inhibitory effects on angiotensin converting enzyme. Gallic acid qualifies as a drug candidate to be tested in the diabetic nephropathy, one of the important complication of diabetes. Streptozotocin (55 mg/kg body weight, i.p.) induced diabetic nephropathy was used as an experimental model. Gallic acid was evaluated for its possible effect at the dose of 20 and 40 mg/kg body weight. Gallic acid treatment significantly lowered plasma levels of the creatinine and blood urea nitrogen and elevated the levels of the protein and albumin. Gallic acid also improved creatinine clearance. Determination of oxidative stress parameters showed that the oxidative stress in kidney tissues was reduced significantly in gallic acid treated animals. Results of the plasma, urine and oxidative stress parameters were also reflected in the histopathological evaluation showing improvement in kidney pathophysiology. ELISA assay for circulating TGF-β1 evaluation and immunohistochemical study for determination of kidney expression of TGF-β1 revealed that gallic acid significantly lowered both the circulating and tissue levels of TGF-β1. Results support the hypothesis that gallic acid can be effectively used in the treatment of diabetic nephropathy. Copyright © 2018 Elsevier B.V. All rights reserved.

The Influence of Prefermentative Addition of Gallic Acid on the Phenolic Composition and Chromatic Characteristics of Cabernet Sauvignon Wines.

PubMed

Liu, Yue; Zhang, Bo; He, Fei; Duan, Chang-Qing; Shi, Ying

2016-07-01

In this study, the prefermentative addition of gallic acid in Cabernet Sauvignon red winemaking was performed. The influence of gallic acid addition on wine phenolic composition, the ratio of copigmentation, and the color parameters were monitored throughout the winemaking process. The results showed that the prefermentative addition of gallic acid enhanced the extraction of total anthocyanins and the copigmentation effect, producing wines with more darkness, redness, yellowness, and saturation. Moreover, the addition of gallic acid contributed to the concentration of total phenolic acids. However, it had a negative effect on the concentrations of flavonols and flavan-3-ols in the final wines. Thus, the prefermentative addition of gallic acid at appropriate levels might be a promising enological technology to obtain wines with high color quality and aging potential. © 2016 Institute of Food Technologists®

Time-dependent inhibition of CYP3A4 by gallic acid in human liver microsomes and recombinant systems.

PubMed

Pu, Qiang-Hong; Shi, Liang; Yu, Chao

2015-03-01

1.Gallic acid is a main polyphenol in various fruits and plants. Inhibitory characteristics of gallic acid on CYP3A4 were still unclear. The objective of this work is hence to investigate inhibitory characteristics of gallic acid on CYP3A4 using testosterone as the probe substrate in human liver microsomes (HLMs) and recombinant CYP3A4 (rCYP3A4) systems. 2.Gallic acid caused concentration-dependent loss of CYP3A4 activity with IC50 values of 615.2 μM and 669.5 μM in HLM and rCYP3A4 systems, respectively. IC50-shift experiments showed that pre-incubation with gallic acid in the absence of NADPH contributed to 12- or 14-fold reduction of IC50 in HLM and rCYP3A4 systems, respectively, supporting a time-dependent inhibition. In HLM, time-dependent inactivation variables KI and Kinact were 485.8 μM and 0.05 min(-1), respectively. 3.Compared with the presence of NADPH, pre-incubation of gallic acid in the absence of NADPH markedly increased its inhibitory effects in HLM and rCYP3A4 systems. Those results indicate that CYP3A4 inactivation by gallic acid was independent on NADPH and was mainly mediated its oxidative products. 4.In conclusion, we showed that gallic acid weakly and time-dependently inactivated CYP3A4 via its oxidative products.

Prophylactic Antioxidant Potential of Gallic Acid in Murine Model of Sepsis

PubMed Central

Maurya, Harikesh; Mangal, Vaishali; Gandhi, Sanjay; Prabhu, Kathiresan; Ponnudurai, Kathiresan

2014-01-01

Present study is to investigate the effect of Gallic acid pretreatment on survival of septic animals and oxidative stress in different organs like lungs, liver, kidney, spleen, and vascular dysfunction of mice. Sepsis was induced by cecal ligation and puncture (CLP) in healthy adult male albino mice (25–30 g) and was divided into 3 groups each consisting of 6 animals, that is, sham-operated (SO group (Group I), SO + sepsis (Group II), and Gallic acid + sepsis (Group III)). Group III animals were pretreated with Gallic acid at the dose rate of 20 mg/kg body weight for 2 days before induction of sepsis. Animals were sacrificed on 8th day and the tissue samples were obtained for further investigation on lipid peroxidation (LPO), malondialdehyde (MDA), superoxide dismutase (SOD), catalase (CAT), and glutathione reductase (GSH). Gallic acid pretreatment significant (P < 0.05) reduces kidney, spleen, liver, and lungs' malondialdehyde level in septic mice. However, it fails to improve reduced glutathione level in all given organs, while, Gallic acid pretreated mice showed significant improvement in SOD activity of kidney and spleen when compared to septic mice. Finally, the beneficial effects of Gallic acid pretreatment in sepsis are evident from the observations that Gallic acid partially restored SOD and catalase activity and completely reversed lipid peroxidation. Further studies are required to find out the possible mechanisms underlying the beneficial effects of Gallic acid on large population. PMID:25018890

The anti-inflammatory and anti-apoptotic effects of gallic acid against mucosal inflammation- and erosions-induced by gastric ischemia-reperfusion in rats

PubMed Central

Mard, Seyyed Ali; Mojadami, Shahnaz; Farbood, Yaghoob; Gharib Naseri, Mohammad Kazem

2015-01-01

The present study aimed to evaluate the protective effect of gallic acid on gastric mucosal lesions caused by ischemia-reperfusion (I/R) injury in rat. Forty male rats were randomly divided into sham, control (I/R injury) and three gallic acid-pretreated groups. To induce I/R lesions, the celiac artery was clamped for 30 min and then the clamp was removed to allow reperfusion for 6 hr. Pretreated rats received gallic acid (15, 30 or 60 mg kg-1, intraperitoneally) 30 min prior to the induction of I/R injury. Macroscopic and microscopic evaluations of the areas of ulceration were compared. Samples of gastric mucosa were collected to evaluate the protein expression of pro-apoptotic factor, caspase-3, and pro-inflammatory enzyme, inducible nitric oxide synthase (iNOS) using western blot. Pretreatment with gallic acid decreased the total area of gastric lesions. Gallic acid at 30 mg kg-1 decreased the levels of protein expression of caspase-3 and iNOS induced by I/R injury. Our findings showed the protective effect of gallic acid on gastric mucosa against ischemia-reperfusion injury. This effect of gallic acid was mainly mediated by reducing protein expression of iNOS and caspase-3. PMID:26973766

The anti-inflammatory and anti-apoptotic effects of gallic acid against mucosal inflammation- and erosions-induced by gastric ischemia-reperfusion in rats.

PubMed

Mard, Seyyed Ali; Mojadami, Shahnaz; Farbood, Yaghoob; Gharib Naseri, Mohammad Kazem

2015-01-01

The present study aimed to evaluate the protective effect of gallic acid on gastric mucosal lesions caused by ischemia-reperfusion (I/R) injury in rat. Forty male rats were randomly divided into sham, control (I/R injury) and three gallic acid-pretreated groups. To induce I/R lesions, the celiac artery was clamped for 30 min and then the clamp was removed to allow reperfusion for 6 hr. Pretreated rats received gallic acid (15, 30 or 60 mg kg(-1), intraperitoneally) 30 min prior to the induction of I/R injury. Macroscopic and microscopic evaluations of the areas of ulceration were compared. Samples of gastric mucosa were collected to evaluate the protein expression of pro-apoptotic factor, caspase-3, and pro-inflammatory enzyme, inducible nitric oxide synthase (iNOS) using western blot. Pretreatment with gallic acid decreased the total area of gastric lesions. Gallic acid at 30 mg kg(-1) decreased the levels of protein expression of caspase-3 and iNOS induced by I/R injury. Our findings showed the protective effect of gallic acid on gastric mucosa against ischemia-reperfusion injury. This effect of gallic acid was mainly mediated by reducing protein expression of iNOS and caspase-3.

Effect of gallic acid/chitosan coating on fresh pork quality in modified atmosphere packaging.

PubMed

Fang, Zhongxiang; Lin, Daniel; Warner, Robyn Dorothy; Ha, Minh

2018-09-15

Fresh meat safety and quality is a major concern of consumers in the current food market. The objective of this research was to investigate a newly developed gallic acid/chitosan edible coating on the preservation of fresh pork quality in modified atmosphere package (MAP) stored at 4 °C. The pork loins were coated with 2% chitosan (CHI), 0.2% gallic acid in 2% chitosan (CHI/0.2G), or 0.4% gallic acid in 2% chitosan (CHI/0.4G). Results showed that the antimicrobial activity of the chitosan coating was increased with the incorporation of gallic acid. The CHI/0.2G and CHI/0.4G pork loins also had lower lipid oxidation and myoglobin oxidation. However, the CHI/0.4G sample exhibited a pro-protein oxidation effect, suggesting an optimal concentration of gallic acid should be incorporated. This research provides a practical method in application of gallic acid/chitosan coatings on preservation of fresh pork to improve the safety and quality in MAP environment. Copyright © 2018 Elsevier Ltd. All rights reserved.

Gallic Acid Decreases Inflammatory Cytokine Secretion Through Histone Acetyltransferase/Histone Deacetylase Regulation in High Glucose-Induced Human Monocytes.

PubMed

Lee, Wooje; Lee, Sang Yeol; Son, Young-Jin; Yun, Jung-Mi

2015-07-01

Hyperglycemia contributes to diabetes and several diabetes-related complications. Gallic acid is a polyhydroxy phenolic compound found in various natural products. In this study, we investigated the effects and mechanism of gallic acid on proinflammatory cytokine secretion in high glucose-induced human monocytes (THP-1 cells). THP-1 cells were cultured under normoglycemic or hyperglycemic conditions, in the absence or presence of gallic acid. Hyperglycemic conditions significantly induced histone acetylation, nuclear factor-κB (NF-κB) activation, and proinflammatory cytokine release from THP-1 cells, whereas gallic acid suppressed NF-κB activity and cytokine release. It also significantly reduced CREB-binding protein/p300 (CBP/p300, a NF-κB coactivator) gene expression, acetylation levels, and CBP/p300 histone acetyltransferase (HAT) activity. In addition, histone deacetylase 2 (HDAC2) expression was significantly induced. These results suggest that gallic acid inhibits hyperglycemic-induced cytokine production in monocytes through epigenetic changes involving NF-κB. Therefore, gallic acid may have potential for the treatment and prevention of diabetes and its complications.

Gallic acid inhibits vascular calcification through the blockade of BMP2-Smad1/5/8 signaling pathway.

PubMed

Kee, Hae Jin; Cho, Soo-Na; Kim, Gwi Ran; Choi, Sin Young; Ryu, Yuhee; Kim, In Kyeom; Hong, Young Joon; Park, Hyung Wook; Ahn, Youngkeun; Cho, Jeong Gwan; Park, Jong Chun; Jeong, Myung Ho

2014-11-01

Vascular calcification is associated with increased risk of morbidity and mortality in patients with cardiovascular diseases, chronic kidney diseases, and diabetes. Gallic acid, a natural compound found in gallnut and green tea, is known to be antifungal, antioxidant, and anticancer. Here we investigated the effect of gallic acid on vascular smooth muscle cell (VSMC) calcification and the underlying mechanism. Gallic acid inhibited inorganic phosphate-induced osteoblast differentiation markers as well as calcification phenotypes (as determined by calcium deposition, Alizarin Red, and Von Kossa staining). Knockdown of BMP2 or Noggin blocked phosphate-induced calcification. Gallic acid suppressed phosphorylation of Smad1/5/8 protein induced by inorganic phosphate. Taken together, we suggest that gallic acid acts as a novel therapeutic agent of vascular calcification by mediating BMP2-Smad1/5/8 signaling pathway. Copyright © 2014 Elsevier Inc. All rights reserved.

A Novel Ellagic Acid Derivative from Desbordesia glaucescens.

PubMed

DongmoMafodong, Faustine L; Tsopmo, Apollinaire; Awouafack, Maurice D; Roland, Tchuenguem T; Dzoyem, Jean P; Tane, Pierre

2015-10-01

One novel ellagic acid derivative, desglauside (1), was isolated from the leaves of Desbordesia glaucescens together with three known compounds [3',4'-di-O-methylellagic acid (2), oleanolic acid (3) and β-sitosterol-3-O-β-D-glucopyranoside (4)]. Their structures were elucidated on the basis of NMR spectroscopic and MS analysis, and by comparison with related published data. The crude extract, fractions and isolated compounds showed no activity against four yeast strains [Candida albicans (ATCC 9002), C. parapsilopsis (ATCC22019), C. tropicalis (ATCC750), Cryptococcus neoformans (IP95026) and one isolate of Candida guilliermondii].

Ellagic acid ameliorates learning and memory deficits in a rat model of Alzheimer's disease: an exploration of underlying mechanisms.

PubMed

Kiasalari, Zahra; Heydarifard, Rana; Khalili, Mohsen; Afshin-Majd, Siamak; Baluchnejadmojarad, Tourandokht; Zahedi, Elham; Sanaierad, Ashkan; Roghani, Mehrdad

2017-06-01

Alzheimer's disease (AD) is a neurodegenerative disorder with irreversible loss of intellectual abilities. Current therapies for AD are still insufficient. In this study, the effect of ellagic acid on learning and memory deficits was evaluated in intrahippocampal amyloid beta (Aβ 25-35 )-microinjected rats and its modes of action were also explored. AD rat model was induced by bilateral intrahippocampal microinjection of Aβ 25-35 and ellagic acid was daily administered (10, 50, and 100 mg/kg), and learning, recognition memory, and spatial memory were evaluated in addition to histochemical assessment, oxidative stress, cholinesterases activity, and level of nuclear factor-kappaB (NF-κB), Toll-like receptor 4 (TLR4), and nuclear factor (erythroid-derived 2)-like 2 (Nrf2). The amyloid beta-microinjected rats showed a lower discrimination ratio in novel object and alternation score in Y maze tasks and exhibited an impairment of retention and recall capability in passive avoidance paradigm and higher working and reference memory errors in radial arm maze (RAM). In addition, amyloid beta group showed a lower number of Nissl-stained neurons in CA1 area in addition to enhanced oxidative stress, higher activity of cholinesterases, greater level of NF-κB and TLR4, and lower level of nuclear/cytoplasmic ratio for Nrf2 and ellagic acid at a dose of 100 mg/kg significantly prevented most of these abnormal alterations. Ellagic acid pretreatment of intrahippocampal amyloid beta-microinjected rats could dose-dependently improve learning and memory deficits via neuronal protection and at molecular level through mitigation of oxidative stress and acetylcholinesterase (AChE) activity and modulation of NF-κB/Nrf2/TLR4 signaling pathway.

Inhibitory effect of leaves extracts of Ocimum basilicum and Ocimum gratissimum on two key enzymes involved in obesity and hypertension in vitro

PubMed Central

Irondi, Emmanuel Anyachukwu; Agboola, Samson Olalekan; Oboh, Ganiyu; Boligon, Aline Augusti

2016-01-01

Aim: To evaluate the phenolics composition and inhibitory effect of the leaves extracts of Ocimum basilicum and Ocimum gratissimum on two key enzymes (pancreatic lipase [PL] and angiotensin 1-converting enzyme [ACE]) involved in obesity and hypertension in vitro. Materials and Methods: The phenolics (flavonoids and phenolic acids) were quantified using high-performance liquid chromatography coupled with diode array detection. PL and ACE inhibitory effects; DPPH* and ABTS*+ scavenging activities of the extracts were tested using spectrophotometric methods. Results: O. basilicum had the following major phenolics: Rutin, quercetin, and quercitrin (flavonoids); caffeic, chlorogenic, and gallic acids (phenolic acids); while O. gratissimum had the following major phenolics: Rutin, quercitrin, and luteolin (flavonoids); ellagic and chlorogenic acids (phenolic acids). “Extracts of both plants inhibited PL and ACE; scavenged DPPH* in a dose-dependent manner”. O. gratissimum extract was more potent in inhibiting PL (IC50: 20.69 µg/mL) and ACE (IC50: 29.44 µg/mL) than O. basilicum (IC50: 52.14 µg/mL and IC50: 64.99 µg/mL, against PL and ACE, respectively). O. gratissimum also scavenged DPPH* and ABTS*+ more than O. basilicum. Conclusion: O. basilicum and O. gratissimum leaves could be used as functional foods for the management of obesity and obesity-related hypertension. However, O. gratissimum may be more effective than O. basilicum. PMID:27757270

Evaluation of Antioxidant, Anticholinesterase, and Antidiabetic Potential of Dry Leaves and Stems in Tamarix aphylla Growing Wild in Tunisia.

PubMed

Mahfoudhi, Adel; Grosso, Clara; Gonçalves, Rui F; Khelifi, Eltaief; Hammami, Saoussen; Achour, Sami; Trabelsi-Ayadi, Malika; Valentão, Patrícia; Andrade, Paula B; Mighri, Zine

2016-12-01

Tamarix aphylla (L.) Karst. has a wide geographic distribution and was employed in traditional medicine as astringent, anti-rheumatic and to treat fever. T. aphylla leaves and stems extracts were studied from both chemical and biological points of view to assess the antidiabetic, anticholinesterase and antioxidant potential of this species. The HPLC/Diode Array Detector (DAD) analysis showed the presence of 14 phenolic compounds (gallic, caffeic, p-coumaric, ferulic and ellagic acids, kaempferol, quercetin, quercetin 3-O-galactoside and six flavonol derivatives). This is the first study reporting a comparative study of the biological activities of different extracts from T. aphylla. High activities were obtained against DPPH radical, superoxide anion radical (O2∙-) and nitric oxide radical ( • NO) in a concentration-dependent manner, the most active extracts being the polar ones. T. aphylla also showed moderate protective effects against acetylcholinesterase, but no effects were observed against butyrylcholinesterase. Against α-glucosidase the MeOH extracts displayed IC 50 values from 8.41 to 24.81 μg/ml. © 2016 Wiley-VHCA AG, Zurich, Switzerland.

Improved method for the extraction and chromatographic analysis on a fused-core column of ellagitannins found in oak-aged wine.

PubMed

Navarro, María; Kontoudakis, Nikolaos; Canals, Joan Miquel; García-Romero, Esteban; Gómez-Alonso, Sergio; Zamora, Fernando; Hermosín-Gutiérrez, Isidro

2017-07-01

A new method for the analysis of ellagitannins observed in oak-aged wine is proposed, exhibiting interesting advantages with regard to previously reported analytical methods. The necessary extraction of ellagitannins from wine was simplified to a single step of solid phase extraction (SPE) using size exclusion chromatography with Sephadex LH-20 without the need for any previous SPE of phenolic compounds using reversed-phase materials. The quantitative recovery of wine ellagitannins requires a combined elution with methanol and ethyl acetate, especially for increasing the recovery of the less polar acutissimins. The chromatographic method was performed using a fused-core C18 column, thereby avoiding the coelution of main ellagitannins, such as vescalagin and roburin E. However, the very polar ellagitannins, namely, the roburins A, B and C, still partially coeluted, and their quantification was assisted by the MS detector. This methodology also enabled the analysis of free gallic and ellagic acids in the same chromatographic run. Copyright © 2017 Elsevier Ltd. All rights reserved.

Gallic Acid Attenuates Postoperative Intra-Abdominal Adhesion by Inhibiting Inflammatory Reaction in a Rat Model

PubMed Central

Wei, Guangbing; Wu, Yunhua; Gao, Qi; Shen, Cong; Chen, Zilu; Wang, Kang; Yu, Junhui

2018-01-01

Background Intra-abdominal adhesion is one of the most common complications after abdominal surgery. The efficacy of current treatments for intra-abdominal adhesion is unsatisfactory. In this study, we investigated the effect of gallic acid on the prevention and treatment of intra-abdominal adhesions after abdominal surgery using an intra-abdominal adhesion rat model. Material/Methods The experimental rats were randomly divided into the sham operation group, the control group, the chitosan group, and 3 gallic acid groups of different concentrations. All rats except those in the sham operation group received cecal abrasion to induce adhesion. From the first postoperative day, the rats in the gallic acid groups were administered different concentrations of gallic acid in a 2-ml gavage daily. All rats were sacrificed on postoperative day 7, and the degree of intra-abdominal adhesion was evaluated by the naked eye. The amount of collagen deposited between the injured peritoneal tissues was assessed by Sirius red staining. Serum levels of interleukin-6 (IL-6), tumor necrosis factor (TNF-α), and transforming growth factor-β (TGF-β) were measured by ELISA. Western blot was used to detect the level of NF-κB phosphorylation in the injured peritoneal or adhesion tissues of the rats. Results Compared with the control group, the scores of intra-abdominal adhesions in the rats treated with larger doses of gallic acid were significantly decreased, and the degree of inflammation and fibrosis was also significantly decreased. Gallic acid significantly reduced IL-6, TNF-α, and TGF-β1 serum levels. NF-κB phosphorylation in the higher gallic acid groups was significantly reduced. Conclusions Gallic acid inhibits the formation of postoperative intra-abdominal adhesions in rats by inhibiting the inflammatory reaction and fibrogenesis. Gallic acid is a promising drug for preventing intra-abdominal adhesions. PMID:29429982

Gallic Acid: Review of the Methods of Determination and Quantification.

PubMed

Fernandes, Felipe Hugo Alencar; Salgado, Hérida Regina Nunes

2016-05-03

Gallic acid (3,4,5 trihydroxybenzoic acid) is a secondary metabolite present in most plants. This metabolite is known to exhibit a range of bioactivities including antioxidant, antimicrobial, anti-inflammatory, and anticancer. There are various methods to analyze gallic acid including spectrometry, chromatography, and capillary electrophoresis, among others. They have been developed to identify and quantify this active ingredient in most biological matrices. The aim of this article is to review the available information on analytical methods for gallic acid, as well as presenting the advantages and limitations of each technique.

Characterisation of galloylated cyanogenic glucosides and hydrolysable tannins from leaves of Phyllagathis rotundifolia by LC-ESI-MS/MS.

PubMed

Hooi Poay, Tan; Sui Kiong, Ling; Cheng Hock, Chuah

2011-01-01

Phyllagathis rotundifolia (Jack) Bl. (Melastomataceae) is a creeping herb found in Peninsular Malaysia and Sumatra. Traditionally, a decoction of the leaves is used in the treatment of malaria, fever and stomach ache. To provide ESI-MS(n) data which are applicable for chemical fingerprinting of P. rotundifolia to obviate laborious isolation and purification steps. The mass spectral data for the compounds isolated from the leaves of P. rotundifolia were obtained by liquid chromatography-electrospray ionisation tandem mass spectrometry. The MS fragmentation patterns were obtained for galloylated cyanogenic glucosides based on prunasin (prunasin 6′‐O‐gallate 1, prunasin 2′,6′‐di‐O‐gallate 2, prunasin 3′,6′‐di‐O‐gallate 3, prunasin 4′,6′‐di‐O‐gallate 4, prunasin 2′,3′,6′‐tri‐Ogallate 5, prunasin 3′,4′,6′‐tri‐O‐gallate 6 and prunasin 2′,3′,4′,6′‐tetra‐O‐gallate 7), gallotannins (6‐O‐galloyl‐D‐glucose 8, 3,6‐di‐O‐galloyl‐D‐glucose 9, 1,2,3‐tri‐O‐galloyl‐β‐D‐glucose 10, 1,4,6‐tri‐O‐galloyl‐β‐D‐glucose 11, 3,4,6‐tri‐O‐galloyl‐D‐glucose 12, 1,2,3,6‐tetra‐O‐galloyl‐β‐D‐glucose 13 and 1,2,3,4,6‐penta‐O‐galloyl‐β‐D‐glucose 14), ellagitannins [6‐O‐galloyl‐2,3‐O‐(S)‐hexahydroxy‐diphenoyl‐D‐glucose 15, praecoxin B 16 and pterocarinin C 17], ellagic acid derivatives (3′‐O‐methyl‐3,4‐methylenedioxyellagic acid 4′‐O‐β‐D‐glucopyranoside 18 and 3,3′,4‐tri‐O‐methylellagic acid 4′‐O‐β‐D‐glucopyranoside 19) and gallic acid 20 that were isolated from the leaves of P. rotundifolia. The ESI-MS(n) technique facilitates identification of galloylated cyanogenic glucosides, hydrolysable tannins and ellagic acid derivatives that were isolated from the leaves of P. rotundifolia. It yields MS(n) spectra that are useful for identification of these compounds in complex samples and permit more complete fingerprinting of plant materials. Copyright © 2011 John Wiley & Sons, Ltd.

Protective effects of gallic acid against spinal cord injury-induced oxidative stress.

PubMed

Yang, Yong Hong; Wang, Zao; Zheng, Jie; Wang, Ran

2015-08-01

The present study aimed to investigate the role of gallic acid in oxidative stress induced during spinal cord injury (SCI). In order to measure oxidative stress, the levels of lipid peroxide, protein carbonyl, reactive oxygen species and nitrates/nitrites were determined. In addition, the antioxidant status during SCI injury and the protective role of gallic acid were investigated by determining glutathione levels as well as the activities of catalase, superoxide dismutase, glutathione peroxidase and glutathione-S-transferase. Adenosine triphophatase (ATPase) enzyme activities were determined to evaluate the role of gallic acid in SCI-induced deregulation of the activity of enzymes involved in ion homeostasis. The levels of inflammatory markers such as nuclear factor (NF)-κB and cycloxygenase (COX)-2 were determined by western blot analysis. Treatment with gallic acid was observed to significantly mitigate SCI-induced oxidative stress and the inflammatory response by reducing the oxidative stress, decreasing the expression of NF-κB and COX-2 as well as increasing the antioxidant status of cells. In addition, gallic acid modulated the activity of ATPase enzymes. Thus the present study indicated that gallic acid may have a role as a potent antioxidant and anti-inflammatory agent against SCI.

Synthesis, structure, antitumor activity of novel pharmaceutical co-crystals based on bispyridyl-substituted α, β-unsaturated ketones with gallic acid

NASA Astrophysics Data System (ADS)

Liu, Lian-Dong; Liu, Shu-Lian; Liu, Zhi-Xian; Hou, Gui-Ge

2016-05-01

Three novel pharmaceutical co-crystals, (A)·(gallic acid) (1), (B)·(gallic acid) (2), and (C)·(gallic acid) (3) were generated based on 2,6-bis((pyridin-4-yl)methylene)cyclohexanone (A), N-methyl-3,5-bis((pyridin-3-yl)methylene)-4-piperidone (B), N-methyl-3,5-bis((pyridin-4-yl)methylene)-4-piperidone (C) with gallic acid, respectively. They are characterized by elemental analysis, FTIR spectroscopy, 1H NMR and single-crystal X-ray diffraction. Structural analysis reveals that two pharmaceutical ingredients link each other into H-bonding-driven 3D network in 1, 2, or 2D plane in 3. In addition, their antitumor activities against human neoplastic cell lines A549, SGC-7901, MCF-7, OVCA-433, HePG2 and cytotoxicity for HUVEC cell lines by CCK-8 method were evaluated primarily. Compared with gallic acid and free A, B and C, their antitumor activities have improved distinctly, while cytotoxicities have reduced markedly, especially for co-crystal 1. This is mainly because of the synergistic effect between pharmaceutical ingredients A, B, and C and gallic acid.

Quercetin, a Natural Flavonoid Interacts with DNA, Arrests Cell Cycle and Causes Tumor Regression by Activating Mitochondrial Pathway of Apoptosis

PubMed Central

Srivastava, Shikha; Somasagara, Ranganatha R.; Hegde, Mahesh; Nishana, Mayilaadumveettil; Tadi, Satish Kumar; Srivastava, Mrinal; Choudhary, Bibha; Raghavan, Sathees C.

2016-01-01

Naturally occurring compounds are considered as attractive candidates for cancer treatment and prevention. Quercetin and ellagic acid are naturally occurring flavonoids abundantly seen in several fruits and vegetables. In the present study, we evaluate and compare antitumor efficacies of quercetin and ellagic acid in animal models and cancer cell lines in a comprehensive manner. We found that quercetin induced cytotoxicity in leukemic cells in a dose-dependent manner, while ellagic acid showed only limited toxicity. Besides leukemic cells, quercetin also induced cytotoxicity in breast cancer cells, however, its effect on normal cells was limited or none. Further, quercetin caused S phase arrest during cell cycle progression in tested cancer cells. Quercetin induced tumor regression in mice at a concentration 3-fold lower than ellagic acid. Importantly, administration of quercetin lead to ~5 fold increase in the life span in tumor bearing mice compared to that of untreated controls. Further, we found that quercetin interacts with DNA directly, and could be one of the mechanisms for inducing apoptosis in both, cancer cell lines and tumor tissues by activating the intrinsic pathway. Thus, our data suggests that quercetin can be further explored for its potential to be used in cancer therapeutics and combination therapy. PMID:27068577

Effect of Gallic acid on mechanical and water barrier properties of zein-oleic acid composite films.

PubMed

Masamba, Kingsley; Li, Yue; Hategekimana, Joseph; Liu, Fei; Ma, Jianguo; Zhong, Fang

2016-05-01

In this study, the effect of gallic acid on mechanical and water barrier properties of zein-oleic acid 0-4 % composite films was investigated. Molecular weight distribution analysis was carried out to confirm gallic acid induced cross linking through change in molecular weight in fraction containing zein proteins. Results revealed that gallic acid treatment increased tensile strength from 17.9 MPa to 26.0 MPa, decreased water vapour permeability from 0.60 (g mm m(-2) h(-1) kPa(-1)) to 0.41 (g mm m(-2) h(-1) kPa(-1)), increased solubility from 6.3 % to 10.2 % and marginally increased elongation at break from 3.7 % to 4.2 % in zein films only. However, gallic acid treatment in zein-oleic composite films did not significantly influence mechanical and water barrier properties and in most instances irrespective of oleic acid concentration, the properties were negatively affected. Results from scanning electron microscopy showed that both gallic acid treated and untreated zein films and composite films containing 3 % oleic acid had a compact and homogeneous structure while those containing 4 % oleic acid had inhomogeneous structure. The findings have demonstrated that gallic acid treatment can significantly improve mechanical and water barrier properties especially in zein films only as opposed to when used in composite films using zein and oleic acid.

Physicochemical Properties, Antioxidant and Anti-proliferative Capacities of Dried Leaf and Its Extract from Xao tam phan (Paramignya trimera).

PubMed

Nguyen, Van Tang; Sakoff, Jennette A; Scarlett, Christopher J

2017-06-01

Xao tam phan (Paramignya trimera) has been used for the treatment of cancer and cancer-like aliments. Among different parts of the P. trimera plant, leaf is considered as a residual part after harvesting of the root. This study aimed to determine the physiochemical properties and the antioxidant and anti-proliferative capacities of P. trimera leaf (PTL) using microwave drying for the preparation of dry sample; MeOH and microwave-assisted extraction for the preparation of crude extract; and freeze-drying for the preparation of powdered extract. The results showed that total phenolic, total flavonoid, proanthocyanidin, and saponin contents of PTL prepared by microwave drying at 450 W were 25.4 mg gallic acid equiv. (GAE), 86.3 mg rutin equiv. (RE), 5.6 mg catechin equiv. (CE), and 702.1 mg escin equiv. (EE) per gram dried sample, respectively. Gallic acid, protocatechuic acid, ellagic acid, rutin, and quercetin were identified in the PTL MeOH extract. Dried PTL displayed potent antioxidant activity, while the powdered PTL extract exhibited great anti-proliferative capacity on various cancer cell lines including MiaPaCa-2 (pancreas), HT29 (colon), A2780 (ovarian), H460 (lung), A431 (skin), Du145 (prostate), BE2-C (neuroblastoma), MCF-7 (breast), MCF-10A (normal breast), and U87, SJ-G2, and SMA (glioblastoma). Anti-proliferative capacity on pancreatic cancer cells (MiaCaPa2, BxPc3, and CFPAC1) of PTL extract (200 μg/ml) was significantly higher (P < 0.05) than those of ostruthin (20 μg/ml) and gemcitabine (50 nm), and to be comparable to the powdered P. trimera root extract and a saponin-enriched extract from quillajia bark (a commercial product). The findings from this study allow us to conclude that the PTL is a rich source of phytochemicals that possess promising antioxidant and anti-proliferative activities, therefore it shows potential as lead compounds for application in the nutraceutical, medicinal and pharmaceutical industries. © 2017 Wiley-VHCA AG, Zurich, Switzerland.

Antioxidant activity, phenolic-flavonoid content and high-performance liquid chromatography profiling of three different variants of Syzygium cumini seeds: A comparative study.

PubMed

Priya, Syama Hari; Prakasan, Nisha; Purushothaman, Jayamurthy

2017-01-01

The medicinally important phytochemicals present in Syzygium cumini seeds probably accounts for its wide use in traditional systems of medicines in India, like Ayurveda, Unani, and Siddha. The aim of the study was to determine the antioxidant potential of three different geographical variants of S. cumini seeds and to compare the phenolic profiling to know the effect of geographical variation in phenolic composition. Total phenolic and flavonoid content of S. cumini seeds were analyzed. Antioxidant activities in terms of 2,2-diphenyl-1-picrylhydrazyl, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid), nitric oxide and superoxide radical scavenging assays were performed. The most active fractions were subjected to high-performance liquid chromatography (HPLC) profiling to identify the phenolic composition. Among all the fractions, 70% methanol fraction of S. cumini seed showed significant antioxidant potential. There existed a linear correlation between phenolic content and antioxidant activity. HPLC profiling of 70% methanol (ME) fractions of all the variants revealed the presence of phenolic compounds with high concentrations of ellagic acid and gallic acid. The differences in phenolic concentration due to geographical changes might be the reason for higher antioxidant potential showed by 70% ME of Trivandrum variant. 70% methanolic fraction of S. cumini can act as a novel source of natural antioxidant.

Gallic Acid Induces a Reactive Oxygen Species-Provoked c-Jun NH2-Terminal Kinase-Dependent Apoptosis in Lung Fibroblasts

PubMed Central

Chen, Chiu-Yuan; Chen, Kun-Chieh; Yang, Tsung-Ying; Liu, Hsiang-Chun; Hsu, Shih-Lan

2013-01-01

Idiopathic pulmonary fibrosis is a chronic lung disorder characterized by fibroblasts proliferation and extracellular matrix accumulation. Induction of fibroblast apoptosis therefore plays a crucial role in the resolution of this disease. Gallic acid (3,4,5-trihydroxybenzoic acid), a common botanic phenolic compound, has been reported to induce apoptosis in tumor cell lines and renal fibroblasts. The present study was undertaken to examine the role of mitogen-activated protein kinases (MAPKs) in lung fibroblasts apoptosis induced by gallic acid. We found that treatment with gallic acid resulted in activation of c-Jun NH2-terminal kinase (JNK), extracellular signal-regulated kinase (ERK), and protein kinase B (PKB, Akt), but not p38MAPK, in mouse lung fibroblasts. Inhibition of JNK using pharmacologic inhibitor (SP600125) and genetic knockdown (JNK specific siRNA) significantly inhibited p53 accumulation, reduced PUMA and Fas expression, and abolished apoptosis induced by gallic acid. Moreover, treatment with antioxidants (vitamin C, N-acetyl cysteine, and catalase) effectively diminished gallic acid-induced hydrogen peroxide production, JNK and p53 activation, and cell death. These observations imply that gallic acid-mediated hydrogen peroxide formation acts as an initiator of JNK signaling pathways, leading to p53 activation and apoptosis in mouse lung fibroblasts. PMID:23533505

Propyl gallate synthesis using acidophilic tannase and simultaneous production of tannase and gallic acid by marine Aspergillus awamori BTMFW032.

PubMed

Beena, P S; Basheer, Soorej M; Bhat, Sarita G; Bahkali, Ali H; Chandrasekaran, M

2011-07-01

Marine Aspergillus awamori BTMFW032, recently reported by us, produce acidophilic tannase as extracellular enzyme. Here, we report the application of this enzyme for synthesis of propyl gallate by direct transesterification of tannic acid and in tea cream solubilisation besides the simultaneous production of gallic acid along with tannase under submerged fermentation by this fungus. This acidophilic tannase enabled synthesis of propyl gallate by direct transesterification of tannic acid using propanol as organic reaction media under low water conditions. The identity of the product was confirmed with thin layer chromatography and Fourier transform infrared spectroscopy. It was noted that 699 U/ml of enzyme could give 60% solubilisation of tea cream within 1 h. Enzyme production medium was optimized adopting Box-Behnken design for simultaneous synthesis of tannase and gallic acid. Process variables including tannic acid, sodium chloride, ferrous sulphate, dipotassium hydrogen phosphate, incubation period and agitation were recognized as the critical factors that influenced tannase and gallic acid production. The model obtained predicted 4,824.61 U/ml of tannase and 136.206 μg/ml gallic acid after 48 h of incubation, whereas optimized medium supported 5,085 U/ml tannase and 372.6 μg/ml of gallic acid production after 36 and 84 h of incubation, respectively, with a 15-fold increase in both enzyme and gallic acid production. Results indicated scope for utilization of this acidophilic tannase for transesterification of tannic acid into propyl gallate, tea cream solubilisation and simultaneous production of gallic acid along with tannase.

Thermal stability of liquid antioxidative extracts from pomegranate peel.

PubMed

Qu, Wenjuan; Li, Pingping; Hong, Jihua; Liu, Zhiling; Chen, Yufang; Breksa, Andrew P; Pan, Zhongli

2014-03-30

Liquid extracts from pomegranate peel have the potential for use as natural antioxidant products. This study investigates the quality changes of liquid extracts before and after thermal treatment during sterilization and storage. Liquid pomegranate peel extracts were prepared, sterilized under ultra-high temperature (UHT) at 121 °C for 10 s and then stored at three temperatures (4, 25 and 37 °C) for up to 180 days. The industrial, color, UV-visible spectrum profile and antioxidant (phenolics) characteristics were measured. Thermal sterilization treatment had no negative effects on the industrial, color, spectral and antioxidant characteristics of the extracts. After 180 days, the extracts stored at 4 °C retained 67% of the initial total soluble phenolic content and 58% of the original scavenging activity. The major antioxidant components in the extracts (stored at 4 °C for 180 days) were gallic acid, punicalagin A, punicalagin B and ellagic acid having concentrations of 19.3, 197.2, 221.1 and 92.4 mg L⁻¹, respectively. The results show that liquid pomegranate peel extracts had acceptable thermal stability after sterilization and storage. The recommended storage condition of this product was low temperature. © 2013 Society of Chemical Industry.

Purification of a water extract of Chinese sweet tea plant (Rubus suavissimus S. Lee) by alcohol precipitation

PubMed Central

Koh, Gar Yee; Chou, Guixin; Liu, Zhijun

2009-01-01

The aqueous extraction process of the leaves of Rubus suavissimus often brings in a large amount of non-active polysaccharides as part of the constituents. To purify this water extract for potential elevated bioactivity, alcohol precipitation (AP) consisting of gradient regimens was applied, and its resultants were examined through colorimetric and HPLC analyses. AP was effective in partitioning the aqueous crude extract into a soluble supernatant and an insoluble precipitant, and its effect varied significantly with alcohol regimens. Generally, the higher the alcohol concentration, the purer was the resultant extract. At its maximum, approximately 36% (w/w) of the crude extract, of which 23% was polysaccharides, was precipitated and removed, resulting in a purified extract consisting of over 20% bioactive marker compounds (gallic acid, ellagic acid, rutin, rubusoside, and steviol monoside). The removal of 11% polysaccharides from the crude water extract by using alcohol precipitation was complete at 70% alcohol regimen. Higher alcohol levels resulted in even purer extracts, possibly by removing some compounds of uncertain bioactivity. Alcohol precipitation is an effective way of removing polysaccharides from the water extract of sweet tea plant and could be used as an initial simple purification tool for many water plant extracts that contain large amounts of polysaccharides. PMID:19419169

Induction of murine embryonic stem cell differentiation by medicinal plant extracts

DOE Office of Scientific and Technical Information (OSTI.GOV)

Reynertson, Kurt A.; Department of Pharmacology, Weill Cornell Medical College, 1300 York Avenue, New York, NY 10065; Charlson, Mary E.

Epidemiological evidence indicates that diets high in fruits and vegetables provide a measure of cancer chemoprevention due to phytochemical constituents. Natural products are a rich source of cancer chemotherapy drugs, and primarily target rapidly cycling tumor cells. Increasing evidence indicates that many cancers contain small populations of resistant, stem-like cells that have the capacity to regenerate tumors following chemotherapy and radiation, and have been linked to the initiation of metastases. Our goal is to discover natural product-based clinical or dietary interventions that selectively target cancer stem cells, inducing differentiation. We adapted an alkaline phosphatase (AP) stain to assay plant extractsmore » for the capacity to induce differentiation in embryonic stem (ES) cells. AP is a characteristic marker of undifferentiated ES cells, and this represents a novel approach to screening medicinal plant extracts. Following a survey of approximately 100 fractions obtained from 12 species of ethnomedically utilized plants, we found fractions from 3 species that induced differentiation, decreasing AP and transcript levels of pluripotency markers (Nanog, Oct-4, Rex-1). These fractions affected proliferation of murine ES, and human embryonal, prostate, and breast carcinoma cells in a dose-dependent manner. Several phytochemical constituents were isolated; the antioxidant phytochemicals ellagic acid and gallic acid were shown to affect viability of cultured breast carcinoma cells.« less

Anticancer and antioxidant tannins from Pimenta dioica leaves.

PubMed

Marzouk, Mohamed S A; Moharram, Fatma A; Mohamed, Mona A; Gamal-Eldeen, Amira M; Aboutabl, Elsayed A

2007-01-01

Two galloylglucosides, 6-hydroxy-eugenol 4-O-(6'-O-galloyl)-beta-D-4C1-glucopyranoside (4) and 3-(4-hydroxy-3-methoxyphenyl)-propane-1,2-diol-2-O-(2',6'-di-O-galloyl)-beta-D -4C1-glucopyranoside (7), and two C-glycosidic tannins, vascalaginone (10) and grandininol (14), together with fourteen known metabolites, gallic acid (1), methyl gallate (2), nilocitin (3), 1-O-galloyl-4,6-(S)-hexahydroxydiphenoyl-(alpha/beta)-D-glucopyranose (5), 4,6-(S)-hexahydroxydiphenoyl-(alpha/beta)-D-glucopyranose (6), 3,4,6-valoneoyl-(alpha/beta)-D-glucopyranose (8), pedunculagin (9), casuariin (11), castalagin (12), vascalagin (13), casuarinin (15), grandinin (16), methyl-flavogallonate (17) and ellagic acid (18), were identified from the leaves of Pimenta dioica (Merr.) L. (Myrtaceae) on the basis of their chemical and physicochemical analysis (UV, HRESI-MS, 1D and 2D NMR). It was found that 9 is the most cytotoxic compound against solid tumour cancer cells, the most potent scavenger against the artificial radical DPPH and physiological radicals including ROO*, OH*, and O2-*, and strongly inhibited the NO generation and induced the proliferation of T-lymphocytes and macrophages. On the other hand, 3 was the strongest NO inhibitor and 16 the highest stimulator for the proliferation of T-lymphocytes, while 10 was the most active inducer of macrophage proliferation.

Induction of murine embryonic stem cell differentiation by medicinal plant extracts

PubMed Central

Reynertson, Kurt A.; Charlson, Mary E.; Gudas, Lorraine J.

2010-01-01

Epidemiological evidence indicates that diets high in fruits and vegetables provide a measure of cancer chemoprevention due to phytochemical constituents. Natural products are a rich source of cancer chemotherapy drugs, and primarily target rapidly-cycling tumor cells. Increasing evidence indicates that many cancers contain small populations of resistant, stem-like cells that have the capacity to regenerate tumors following chemotherapy and radiation, and have been linked to the initiation of metastases. Our goal is to discover natural product-based clinical or dietary interventions that selectively target cancer stem cells, inducing differentiation. We adapted an alkaline phosphatase (AP) stain to assay plant extracts for the capacity to induce differentiation in embryonic stem (ES) cells. AP is a characteristic marker of undifferentiated ES cells, and this represents a novel approach to screening medicinal plant extracts. Following a survey of approximately 100 fractions obtained from twelve species of ethnomedically utilized plants, we found fractions from three species that induced differentiation, decreasing AP and transcript levels of pluripotency markers (Nanog, Oct-4, Rex-1). These fractions affected proliferation of murine ES, and human embryonal, prostate, and breast carcinoma cells in a dose-dependent manner. Several phytochemical constituents were isolated; the antioxidant phytochemicals ellagic acid and gallic acid were shown to affect viability of cultured breast carcinoma cells. PMID:20955699

Antimicrobial activity of gallic acid against thermophilic Campylobacter is strain specific and associated with a loss of calcium ions.

PubMed

Sarjit, Amreeta; Wang, Yi; Dykes, Gary A

2015-04-01

Gallic acid has been suggested as a potential antimicrobial for the control of Campylobacter but its effectiveness is poorly studied. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of gallic acid against Campylobacter jejuni (n = 8) and Campylobacter coli (n = 4) strains was determined. Gallic acid inhibited the growth of five C. jejuni strains and three C. coli strains (MIC: 15.63-250 μg mL(-1)). Gallic acid was only bactericidal to two C. coli strains (MBC: 125 and 62.5 μg mL(-1)). The mechanism of the bactericidal effect against these two strains (and selected non-susceptible controls) was investigated by determining decimal reduction times and by monitoring the loss of cellular content and calcium ions, and changes in cell morphology. Gallic acid did not result in a loss of cellular content or morphological changes in the susceptible strains as compared to the controls. Gallic acid resulted in a loss of calcium ions (0.58-1.53 μg mL(-1) and 0.54-1.17 μg mL(-1), respectively, over a 180 min period) from the susceptible strains but not the controls. Gallic acid is unlikely to be an effective antimicrobial against Campylobacter in a practical sense unless further interventions to ensure an effective bactericidal mode of action against all strains are developed. Copyright © 2014 Elsevier Ltd. All rights reserved.

Two shikimate dehydrogenases, VvSDH3 and VvSDH4, are involved in gallic acid biosynthesis in grapevine

PubMed Central

Bontpart, Thibaut; Marlin, Thérèse; Vialet, Sandrine; Guiraud, Jean-Luc; Pinasseau, Lucie; Meudec, Emmanuelle; Sommerer, Nicolas; Cheynier, Véronique; Terrier, Nancy

2016-01-01

In plants, the shikimate pathway provides aromatic amino acids that are used to generate numerous secondary metabolites, including phenolic compounds. In this pathway, shikimate dehydrogenases (SDH) ‘classically’ catalyse the reversible dehydrogenation of 3-dehydroshikimate to shikimate. The capacity of SDH to produce gallic acid from shikimate pathway metabolites has not been studied in depth. In grapevine berries, gallic acid mainly accumulates as galloylated flavan-3-ols. The four grapevine SDH proteins have been produced in Escherichia coli. In vitro, VvSDH1 exhibited the highest ‘classical’ SDH activity. Two genes, VvSDH3 and VvSDH4, mainly expressed in immature berry tissues in which galloylated flavan-3-ols are accumulated, encoded enzymes with lower ‘classical’ activity but were able to produce gallic acid in vitro. The over-expression of VvSDH3 in hairy-roots increased the content of aromatic amino acids and hydroxycinnamates, but had little or no effect on molecules more distant from the shikimate pathway (stilbenoids and flavan-3-ols). In parallel, the contents of gallic acid, β-glucogallin, and galloylated flavan-3-ols were increased, attesting to the influence of this gene on gallic acid metabolism. Phylogenetic analysis from dicotyledon SDHs opens the way for the examination of genes from other plants which accumulate gallic acid-based metabolites. PMID:27241494

Gallic acid-capped gold nanoparticles inhibit EGF-induced MMP-9 expression through suppression of p300 stabilization and NFκB/c-Jun activation in breast cancer MDA-MB-231 cells

DOE Office of Scientific and Technical Information (OSTI.GOV)

Chen, Ying-Jung; Lee, Yuan-Chin; Huang, Chia-Hui

Triple-negative breast cancers (TNBCs) are highly invasive and have a higher rate of distant metastasis. Matrix metalloproteinase-9 (MMP-9) plays a crucial role in EGF/EGFR-mediated malignant progression and metastasis of TNBCs. Various studies have revealed that treatment with gallic acid down-regulates MMP-9 expression in cancer cells, and that conjugation of phytochemical compounds with gold nanoparticles (AuNPs) increases the anti-tumor activity of the phytochemical compounds. Thus, the effect of gallic acid-capped AuNPs (GA-AuNPs) on MMP-9 expression in EGF-treated TNBC MDA-MB-231 cells was analyzed in the present study. The so-called green synthesis of AuNPs by means of gallic acid was performed at pHmore » 10, and the resulting GA-AuNPs had spherical shape with an average diameter of approximately 50 nm. GA-AuNPs notably suppressed migration and invasion of EGF-treated cells, and inhibited EGF-induced MMP-9 up-regulation. GA-AuNPs abrogated EGF-induced Akt/p65 and ERK/c-Jun phosphorylation, leading to down-regulation of MMP-9 mRNA and protein expression in EGF-treated cells. Meanwhile, EGF-induced p300 stabilization was found to be involved in MMP-9 expression, whereas GA-AuNPs inhibited the EGF-promoted stability of the p300 protein. Although GA-AuNPs and gallic acid suppressed EGF-induced MMP-9 up-regulation via the same signaling pathway, the effective concentration of gallic acid was approximately 100-fold higher than that of GA-AuNPs for inhibition of MMP-9 expression in EGF-treated cells to a similar extent. Collectively, our data indicate that, in comparison with gallic acid, GA-AuNPs have a superior ability to inhibit EGF/EGFR-mediated MMP-9 expression in TNBC MDA-MB-231 cells. Our findings also point to a way to improve the anti-tumor activity of gallic acid. - Highlights: • Gallic acid-capped gold nanoparticles inhibit EGF-induced MMP-9 expression. • EGF-induced MMP-9 expression via p300 stabilization and NFκB/c-Jun activation. • Gallic acid-capped gold nanoparticles inhibit EGF-modulated p300 stabilization. • Gallic acid-capped gold nanoparticles abrogate EGF-induced NFκB/c-Jun activation.« less

Complexation and molecular modeling studies of europium(III)-gallic acid-amino acid complexes.

PubMed

Taha, Mohamed; Khan, Imran; Coutinho, João A P

2016-04-01

With many metal-based drugs extensively used today in the treatment of cancer, attention has focused on the development of new coordination compounds with antitumor activity with europium(III) complexes recently introduced as novel anticancer drugs. The aim of this work is to design new Eu(III) complexes with gallic acid, an antioxida'nt phenolic compound. Gallic acid was chosen because it shows anticancer activity without harming health cells. As antioxidant, it helps to protect human cells against oxidative damage that implicated in DNA damage, cancer, and accelerated cell aging. In this work, the formation of binary and ternary complexes of Eu(III) with gallic acid, primary ligand, and amino acids alanine, leucine, isoleucine, and tryptophan was studied by glass electrode potentiometry in aqueous solution containing 0.1M NaNO3 at (298.2 ± 0.1) K. Their overall stability constants were evaluated and the concentration distributions of the complex species in solution were calculated. The protonation constants of gallic acid and amino acids were also determined at our experimental conditions and compared with those predicted by using conductor-like screening model for realistic solvation (COSMO-RS) model. The geometries of Eu(III)-gallic acid complexes were characterized by the density functional theory (DFT). The spectroscopic UV-visible and photoluminescence measurements are carried out to confirm the formation of Eu(III)-gallic acid complexes in aqueous solutions. Copyright © 2016 Elsevier Inc. All rights reserved.

Antiulcerogenic Effect of Gallic Acid in Rats and its Effect on Oxidant and Antioxidant Parameters in Stomach Tissue

PubMed Central

Sen, S.; Asokkumar, K.; Umamaheswari, M.; Sivashanmugam, A. T.; Subhadradevi, V.

2013-01-01

In the present study, we investigate the antiulcerogenic effect of gallic acid against aspirin plus pyrolus ligation-induced gastric ulcer in rats. Rats were treated with gallic acid (100 and 200 mg/kg) and famotidine (20 mg/kg) for 1 week, followed by induction of gastric ulcer using the aspirin plus pyrolus ligation model. At the end of 4 h after ligation, the rats were sacrificed and ulcer index, gastric juice volume, pH and other biochemical parameter of gastric juice were evaluated. Stomachs of rats were evaluated biochemically to determine oxidant and antioxidant parameters. Pretreatment with gallic acid significantly decreased ulcer index, gastric juice volume, free and total acidity, total protein, DNA content and increased pH and carbohydrates concentration. Gallic acid at a dose of 100 and 200 mg/kg exerted 69.7 and 78.9% ulcer inhibition, respectively. The levels of superoxide dismutase, catalase, reduced glutathione, glutathione reductase, glutathione peroxidise, glucose-6-phosphate dehydrogenase were increased while reduction in myeloperoxidase and lipid peroxidation were observed in the stomach tissues of the drug treated rats. The histopathological studies further confirmed the antiulcer activity of gallic acid. We conclude that the gallic acid possesses antiulcer effect and that these occur by a mechanism that involves attenuation of offensive factors, improvement of mucosal defensive with activation of antioxidant parameters and inhibition of some toxic oxidant parameters. PMID:24019562

Gallic acid, a phenolic compound isolated from Mimosa bimucronata (DC.) Kuntze leaves, induces diuresis and saluresis in rats.

PubMed

Schlickmann, Fabile; Boeing, Thaise; Mariano, Luisa Nathália Bolda; da Silva, Rita de Cássia Melo Vilhena de Andrade Fonseca; da Silva, Luisa Mota; de Andrade, Sérgio Faloni; de Souza, Priscila; Cechinel-Filho, Valdir

2018-06-01

Although present in the leaves of Mimosa bimucronata (DC.) and many other medicinal plants commonly used to augment urinary volume excretion, the effects of gallic acid as a diuretic agent remain to be studied. Wistar rats were orally treated with vehicle, hydrochlorothiazide, or gallic acid. The effects of gallic acid in the presence of hydrochlorothiazide, furosemide, amiloride, L-NAME, atropine, and indomethacin were also investigated. Diuretic index, pH, conductivity, and electrolyte excretion were evaluated at the end of the experiment (after 8 or 24 h). Gallic acid induced diuretic and saluretic (Na + and Cl - ) effects, without interfering with K + excretion, when orally given to female and male rats at a dose of 3 mg/kg. These effects were associated with increased creatinine and conductivity values while pH was unaffected by any of the treatments. Plasma Na + , K + , and Cl - levels were not affected by any of the acute treatments. The combination with hydrochlorothiazide or furosemide was unable to intensify the effects of gallic acid when compared with the response obtained with each drug alone. On the other hand, the treatment with amiloride plus gallic acid amplified both diuresis and saluresis, besides to a marked potassium-sparing effect. Its diuretic action was significantly prevented in the presence of indomethacin, a cyclooxygenase inhibitor, but not with the pretreatments with L-NAME or atropine. Although several biological activities have already been described for gallic acid, this is the first study demonstrating its potential as a diuretic agent.

Synthesis and application of in-situ molecularly imprinted silica monolithic in pipette-tip solid-phase microextraction for the separation and determination of gallic acid in orange juice samples.

PubMed

Arabi, Maryam; Ghaedi, Mehrorang; Ostovan, Abbas

2017-03-24

A novel strategy was presented for the synthesis and application of functionalized silica monolithic as artificial receptor of gallic acid at micro-pipette tip. A sol-gel process was used to prepare the sorbent. In this in-situ polymerization reaction, tetraethyl orthosilicate (TEOS), 3-aminopropyl trimethoxysilane (APTMS), gallic acid and thiourea were used, respectively, as cross-linker, functionalized monomer, template and precursor to make crack-free and non-fragile structure. Such durable and inexpensive in-situ monolithic was successfully employed as useful tool for highly efficient extraction of gallic acid from orange juice samples. The effective parameters in extraction recovery were investigated and optimum conditions were obtained using experimental design methodology. Applying HPLC-UV for separation quantification at optimal conditions, the gallic acid was efficiently extracted without significant matrix interference. Good linearity for gallic acid in the range of 0.02-5.0mgL -1 with correlation coefficients of R 2 >0.999 revealed well applicability of the method for trace analysis. Copyright © 2017. Published by Elsevier B.V.

Interactive effects of gallic/ferulic/caffeic acids and anthocyanins on pigment thermal stabilities.

PubMed

Qian, Bing-Jun; Liu, Jian-Hua; Zhao, Shu-Juan; Cai, Jian-Xiong; Jing, Pu

2017-06-01

The data presented in this article are related to the research article entitled "The effects of gallic/ferulic/caffeic acids on colour intensification and anthocyanin stability" (Qian et al., 2017) [1]. This paper described preparation and isolation of anthocyanins from purple sweet potatoes (PSP) and the time-course of anthocyanin profiles treated with gallic, ferulic, or caffeic acids at 95 °C. The color appearance of PSPanthocyanins alone, or with gallic, ferulic, or caffeic acids was described after the 15 h of thermal treatment. The high resolution mass spectrographs of PSP anthocyanins were determined using UPLC-ESI-HRMS. The spatial interaction of peonidin 3-O-(2-O-β-D-glucopyranocyl-β-D-glucopyranoide)-5-O-β-D-glucopyranoside and gallic/ferulic/caffeic acids was illustrated by molecular dynamic simulation.

Gallic Acid Is an Antagonist of Semen Amyloid Fibrils That Enhance HIV-1 Infection.

PubMed

LoRicco, Josephine G; Xu, Changmingzi Sherry; Neidleman, Jason; Bergkvist, Magnus; Greene, Warner C; Roan, Nadia R; Makhatadze, George I

2016-07-01

Recent in vitro studies have demonstrated that amyloid fibrils found in semen from healthy and HIV-infected men, as well as semen itself, can markedly enhance HIV infection rates. Semen fibrils are made up of multiple naturally occurring peptide fragments derived from semen. The best characterized of these fibrils are SEVI (semen-derived enhancer of viral infection), made up of residues 248-286 of prostatic acidic phosphatase, and the SEM1 fibrils, made up of residues 86-107 of semenogelin 1. A small molecule screen for antagonists of semen fibrils identified four compounds that lowered semen-mediated enhancement of HIV-1 infectivity. One of the four, gallic acid, was previously reported to antagonize other amyloids and to exert anti-inflammatory effects. To better understand the mechanism by which gallic acid modifies the properties of semen amyloids, we performed biophysical measurements (atomic force microscopy, electron microscopy, confocal microscopy, thioflavin T and Congo Red fluorescence assays, zeta potential measurements) and quantitative assays on the effects of gallic acid on semen-mediated enhancement of HIV infection and inflammation. Our results demonstrate that gallic acid binds to both SEVI and SEM1 fibrils and modifies their surface electrostatics to render them less cationic. In addition, gallic acid decreased semen-mediated enhancement of HIV infection but did not decrease the inflammatory response induced by semen. Together, these observations identify gallic acid as a non-polyanionic compound that inhibits semen-mediated enhancement of HIV infection and suggest the potential utility of incorporating gallic acid into a multicomponent microbicide targeting both the HIV virus and host components that promote viral infection. © 2016 by The American Society for Biochemistry and Molecular Biology, Inc.

One-Pot Procedure for Recovery of Gallic Acid from Wastewater and Encapsulation within Protein Particles.

PubMed

Nourbakhsh, Himan; Madadlou, Ashkan; Emam-Djomeh, Zahra; Wang, Yi-Cheng; Gunasekaran, Sundaram; Mousavi, Mohammad E

2016-02-24

A whey protein isolate solution was heat-denatured and treated with the enzyme transglutaminase, which cross-linked ≈26% of the amino groups and increased the magnitude of the ζ-potential value. The protein solution was microemulsified, and then the resulting water-in-oil microemulsion was dispersed within a gallic acid-rich model wastewater. Gallic acid extraction by the outlined microemulsion liquid membrane (MLM) from the exterior aqueous phase (wastewater) and accumulation within the internal aqueous nanodroplets induced protein cold-set gelation and resulted in the formation of gallic acid-enveloping nanoparticles. Measurements with a strain-controlled rheometer indicated a progressive increase in the MLM viscosity during gallic acid recovery corresponding to particle formation. The mean hydrodynamic size of the nanoparticles made from the heat-denatured and preheated enzymatically cross-linked proteins was 137 and 122 nm, respectively. The enzymatic cross-linking of whey proteins led to a higher gallic acid recovery yield and increased the glass transition enthalpy and temperature. A similar impact on glass transition indices was observed by the gallic acid-induced nanoparticulation of proteins. Scanning electron microscopy showed the existence of numerous jammed/fused nanoparticles. It was suggested on the basis of the results of Fourier transform infrared spectroscopy that the in situ nanoparticulation of proteins shifted the C-N stretching and C-H bending peaks to higher wavenumbers. X-ray diffraction results proposed a decreased β-sheet content for proteins because of the acid-induced particulation. The nanoparticles made from the enzymatically cross-linked protein were more stable against the in vitro gastrointestinal digestion and retained almost 19% of the entrapped gallic acid after 300 min sequential gastric and intestinal digestions.

Gallic Acid Is an Antagonist of Semen Amyloid Fibrils That Enhance HIV-1 Infection*

PubMed Central

LoRicco, Josephine G.; Xu, Changmingzi Sherry; Neidleman, Jason; Bergkvist, Magnus; Greene, Warner C.; Roan, Nadia R.; Makhatadze, George I.

2016-01-01

Recent in vitro studies have demonstrated that amyloid fibrils found in semen from healthy and HIV-infected men, as well as semen itself, can markedly enhance HIV infection rates. Semen fibrils are made up of multiple naturally occurring peptide fragments derived from semen. The best characterized of these fibrils are SEVI (semen-derived enhancer of viral infection), made up of residues 248–286 of prostatic acidic phosphatase, and the SEM1 fibrils, made up of residues 86–107 of semenogelin 1. A small molecule screen for antagonists of semen fibrils identified four compounds that lowered semen-mediated enhancement of HIV-1 infectivity. One of the four, gallic acid, was previously reported to antagonize other amyloids and to exert anti-inflammatory effects. To better understand the mechanism by which gallic acid modifies the properties of semen amyloids, we performed biophysical measurements (atomic force microscopy, electron microscopy, confocal microscopy, thioflavin T and Congo Red fluorescence assays, zeta potential measurements) and quantitative assays on the effects of gallic acid on semen-mediated enhancement of HIV infection and inflammation. Our results demonstrate that gallic acid binds to both SEVI and SEM1 fibrils and modifies their surface electrostatics to render them less cationic. In addition, gallic acid decreased semen-mediated enhancement of HIV infection but did not decrease the inflammatory response induced by semen. Together, these observations identify gallic acid as a non-polyanionic compound that inhibits semen-mediated enhancement of HIV infection and suggest the potential utility of incorporating gallic acid into a multicomponent microbicide targeting both the HIV virus and host components that promote viral infection. PMID:27226574

Two shikimate dehydrogenases, VvSDH3 and VvSDH4, are involved in gallic acid biosynthesis in grapevine.

PubMed

Bontpart, Thibaut; Marlin, Thérèse; Vialet, Sandrine; Guiraud, Jean-Luc; Pinasseau, Lucie; Meudec, Emmanuelle; Sommerer, Nicolas; Cheynier, Véronique; Terrier, Nancy

2016-05-01

In plants, the shikimate pathway provides aromatic amino acids that are used to generate numerous secondary metabolites, including phenolic compounds. In this pathway, shikimate dehydrogenases (SDH) 'classically' catalyse the reversible dehydrogenation of 3-dehydroshikimate to shikimate. The capacity of SDH to produce gallic acid from shikimate pathway metabolites has not been studied in depth. In grapevine berries, gallic acid mainly accumulates as galloylated flavan-3-ols. The four grapevine SDH proteins have been produced in Escherichia coli In vitro, VvSDH1 exhibited the highest 'classical' SDH activity. Two genes, VvSDH3 and VvSDH4, mainly expressed in immature berry tissues in which galloylated flavan-3-ols are accumulated, encoded enzymes with lower 'classical' activity but were able to produce gallic acid in vitro The over-expression of VvSDH3 in hairy-roots increased the content of aromatic amino acids and hydroxycinnamates, but had little or no effect on molecules more distant from the shikimate pathway (stilbenoids and flavan-3-ols). In parallel, the contents of gallic acid, β-glucogallin, and galloylated flavan-3-ols were increased, attesting to the influence of this gene on gallic acid metabolism. Phylogenetic analysis from dicotyledon SDHs opens the way for the examination of genes from other plants which accumulate gallic acid-based metabolites. © The Author 2016. Published by Oxford University Press on behalf of the Society for Experimental Biology.

Antidiabetic and antioxidant functionality associated with phenolic constituents from fruit parts of indigenous black jamun (Syzygium cumini L.) landraces.

PubMed

Gajera, H P; Gevariya, Shila N; Hirpara, Darshna G; Patel, S V; Golakiya, B A

2017-09-01

Fruit phenolics are important dietary antioxidant and antidiabetic constituents. The fruit parts (pulp, seed, seed coat, kernel) of underutilized indigenous six black jamun landraces ( Syzygium cumini L.), found in Gir forest region of India and differed in their fruit size, shape and weight, are evaluated and correlated with antidiabetic, DPPH radical scavenging and phenolic constituents. The α-amylase inhibitors propose an efficient antidiabetic strategy and the levels of postprandial hyperglycemia were lowered by restraining starch breakdown. The sequential solvent systems with ascending polarity-petroleum ether, ethyl acetate, methanol and water were performed for soxhlet extraction by hot percolation method and extractive yield was found maximum with methanolic fruit part extracts of six landraces. The methanolic extracts of fruit parts also evidenced higher antidiabetic activity and hence utilized for further characterization. Among the six landraces, pulp and kernel of BJLR-6 (very small, oblong fruits) evidenced maximum 53.8 and 98.2% inhibition of α-amylase activity, respectively. The seed attained inhibitory activity mostly contributed by the kernel fraction. The inhibition of DPPH radical scavenging activity was positively correlated with phenol constituents. An HPLC-PDA technique was used to quantify the seven individual phenolics. The seed and kernel of BJLR-6 exhibited higher individual phenolics-gallic, catechin, ellagic, ferulic acids and quercetin, whereas pulp evidenced higher with gallic acid and catechin as α-amylase inhibitors. The IC 50 value indicates concentration of fruit extracts exhibiting ≥50% inhibition on porcine pancreatic α-amylase (PPA) activity. The kernel fraction of BJLR6 evidenced lowest (8.3 µg ml -1 ) IC 50 value followed by seed (12.9 µg ml -1 ), seed coat (50.8 µg ml -1 ) and pulp (270 µg ml -1 ). The seed and kernel of BJLR-6 inhibited PPA at much lower concentrations than standard acarbose (24.7 µg ml -1 ) considering good candidates for antidiabetic herbal formulations.

Effects of Gallic Acid and Cyclosporine A on Antioxidant Capacity and Cardiac Markers of Rat Isolated Heart After Ischemia/Reperfusion

PubMed Central

Badavi, Mohammad; Sadeghi, Najmeh; Dianat, Mahin; Samarbafzadeh, Alireza

2014-01-01

Background: Myocardial infarction is one of the important causes of death during old ages. Gallic acid as an antioxidant or cyclosporine A (CsA) as inhibitor of mitochondrial permeability transition pore (mPTP) alone could prevent these complications to some extent, but their combination effect has not been investigated. Objectives: The aim of this study was to determine the combined effect of gallic acid and CsA on antioxidant capacity of isolated heart tissues during ischemia reperfusion. Materials and Methods: Eighty male Wistar rats were randomly assigned to different groups: sham, control (Ca, received saline, 1 mL/kg); 3 groups were pretreated with gallic acid (G1a: 7.5, G2a: 15, G3a: 30 mg/kg) for 10 days, and the other 3 groups were pretreated with gallic acid and received CsA (0.2 µM) for 10 minutes before induction of ischemia and during the first 10 minutes of reperfusion (G1b, G2b and G3b) and the last group received CsA alone (Cb). After 10 days of pretreatment, the heart was isolated and transferred to the Langendorff apparatus and exposed to 30 minutes ischemia followed by 60 minutes of reperfusion. After that cardiac markers and antioxidant enzymes were assessed in cardiac tissues. Results: Lactate dehydrogenase (LDH), Superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GPX) activity increased and malondialdehyde (MDA) decreased in animals pretreated with gallic acid significantly. However, pretreatment with gallic acid followed by CsA during reperfusion improved the antioxidant capacity and cardiac marker enzymes and restored the lipid peroxidation more effective than gallic acid or CsA alone. Nevertheless, CsA did not change the cardiac marker enzymes significantly. Conclusions: Gallic acid and CsA combination improved antioxidant capacity and cell membrane integrity more than each one alone. Therefore, it can be a therapeutic approach to reduce the I/R injury. PMID:25068044

Statistical optimization of bioprocess parameters for enhanced gallic acid production from coffee pulp tannins by Penicillium verrucosum.

PubMed

Bhoite, Roopali N; Navya, P N; Murthy, Pushpa S

2013-01-01

Gallic acid (3,4,5-trihydroxybenzoic acid) was produced by microbial biotransformation of coffee pulp tannins by Penicillium verrucosum. Gallic acid production was optimized using response surface methodology (RSM) based on central composite rotatable design. Process parameters such as pH, moisture, and fermentation period were considered for optimization. Among the various fungi isolated from coffee by-products, Penicillium verrucosum produced 35.23 µg/g of gallic acid on coffee pulp as sole carbon source in solid-state fermentation. The optimum values of the parameters obtained from the RSM were pH 3.32, moisture 58.40%, and fermentation period of 96 hr. Gallic acid production with an increase of 4.6-fold was achieved upon optimization of the process parameters. The results optimized could be translated to 1-kg tray fermentation. High-performance liquid chromatography (HPLC) analysis and spectral studies such as mass spectroscopy (MS) and (1)H-nuclear magnetic resonance (NMR) confirmed that the bioactive compound isolated was gallic acid. Thus, coffee pulp, which is available in enormous quantity, could be used for the production of value-added products that can find avenues in food, pharmaceutical, and chemical industries.

Gallic acid against hepatocellular carcinoma: An integrated scheme of the potential mechanisms of action from in vivo study.

PubMed

Aglan, Hadeer A; Ahmed, Hanaa H; El-Toumy, Sayed A; Mahmoud, Nadia S

2017-06-01

The global burden of hepatocellular carcinoma is increasing; actually, it is estimated as 750,000 new cases annually. This study was initiated to emphasize the possibility that gallic acid could alleviate hepatocarcinogenesis in vivo. In this study, 40 rats were enrolled and distributed as follows; group 1 was set as negative control, while all of groups 2, 3, and 4 were orally received N-nitrosodiethylamine for hepatocellular carcinoma induction. Group 2 was left untreated, whereas groups 3 and 4 were orally treated with gallic acid and doxorubicin, respectively. The current data indicated that gallic acid administration in hepatocellular carcinoma bearing rats yielded significant decline in serum levels of alpha-fetoprotein, glypican-3, and signal transducer and activator of transcription 3 along with significant enhancement in serum suppressors of cytokine signaling 3 level. Also, gallic acid-treated group displayed significant downregulation in the gene expression levels of hepatic gamma glutamyl transferase and heat shock protein gp96. Intriguingly, treatment with gallic acid remarkably ameliorated the destabilization of liver tissue architecture caused by N-nitrosodiethylamine intoxication as evidenced by histopathological investigation. In conclusion, this study demonstrates that the hepatocarcinogenic effect of N-nitrosodiethylamine can be abrogated by gallic acid supplementation owing to its affinity to regulate signal transducer and activator of transcription 3 signaling pathway through its outstanding bioactivities including antioxidant, anti-inflammatory, apoptotic, and antitumor effects.

Gallic acid modulates phenotypic behavior and gene expression in oral squamous cell carcinoma cells by interfering with leptin pathway.

PubMed

Santos, Eliane Macedo Sobrinho; da Rocha, Rogério Gonçalves; Santos, Hércules Otacílio; Guimarães, Talita Antunes; de Carvalho Fraga, Carlos Alberto; da Silveira, Luiz Henrique; Batista, Paulo Ricardo; de Oliveira, Paulo Sérgio Lopes; Melo, Geraldo Aclécio; Santos, Sérgio Henrique; de Paula, Alfredo Maurício Batista; Guimarães, André Luiz Sena; Farias, Lucyana Conceição

2018-01-01

Gallic acid is a polyphenolic compost appointed to interfere with neoplastic cells behavior. Evidence suggests an important role of leptin in carcinogenesis pathways, inducing a proliferative phenotype. We investigated the potential of gallic acid to modulate leptin-induced cell proliferation and migration of oral squamous cell carcinoma cell lines. The gallic acid effect on leptin secretion by oral squamous cell carcinoma cells, as well as the underlying molecular mechanisms, was also assessed. For this, we performed proliferation, migration, immunocytochemical and qPCR assays. The expression levels of cell migration-related genes (MMP2, MMP9, Col1A1, and E-cadherin), angiogenesis (HIF-1α, mir210), leptin signaling (LepR, p44/42 MAPK), apoptosis (casp-3), and secreted leptin levels by oral squamous cell carcinoma cells were also measured. Gallic acid decreased proliferation and migration of leptin-treated oral squamous cell carcinoma cells, and reduced mRNA expression of MMP2, MMP9, Col1A1, mir210, but did not change HIF-1α. Gallic acid decreased levels of leptin secreted by oral squamous cell carcinoma cells, accordingly with downregulation of p44/42 MAPK expression. Thus, gallic acid appears to break down neoplastic phenotype of oral squamous cell carcinoma cells by interfering with leptin pathway. Copyright © 2017 Elsevier GmbH. All rights reserved.

Exogenous application of rutin and gallic acid regulate antioxidants and alleviate reactive oxygen generation in Oryza sativa L.

PubMed

Singh, Akanksha; Gupta, Rupali; Pandey, Rakesh

2017-04-01

The effect of rutin and gallic acid on growth, phytochemical and defense gene activation of rice ( Oryza sativa L.) was investigated. The seeds of rice were primed with different concentrations of rutin and gallic acid (10-60 µg mL -1 ) to explicate the effect on germination on water agar plates. Further, to study the effect of most effective concentrations of gallic acid (60 µg mL -1 ) and rutin (50 µg mL -1 ), greenhouse pot experiment was set up to determine the changes in growth, antioxidant and defense parameters. The results revealed more pronounced effect of gallic acid on total chlorophyll and carotenoids as well as on total flavonoid content and free radical scavenging activities. Gene expression analysis of OsWRKY71, PAL, CHS and LOX genes involved in strengthening the plant defense further validated the results obtained from the biochemical analysis. Microscopic analysis also confirmed reduction in total reactive oxygen species, free radicals like H 2 O 2 and O 2 - by exogenous application of gallic acid and rutin. The data obtained thus suggest that both gallic acid and rutin can affect the growth and physiology of rice plants and therefore can be used to develop effective plant growth promoters and as substitute of biofertilizers for maximizing their use in field conditions.

Biodegradable in situ gelling system for subcutaneous administration of ellagic acid and ellagic acid loaded nanoparticles: evaluation of their antioxidant potential against cyclosporine induced nephrotoxicity in rats.

PubMed

Sharma, G; Italia, J L; Sonaje, K; Tikoo, K; Ravi Kumar, M N V

2007-03-12

Ellagic acid (EA) is a potent antioxidant marketed as a nutritional supplement. Its pharmacological activity has been reported in wide variety of disease models; however its use has been limited owing to its poor biopharmaceutical properties, thereby poor bioavailability. The objective of the current study was to develop chitosan-glycerol phosphate (C-GP) in situ gelling system for sustained delivery of ellagic acid (EA) via subcutaneous route. EA was incorporated in the system employing propylene glycol (PG) and triethanolamine (TEA) as co-solvents; on the other hand EA loaded PLGA nanoparticles (np) were dispersed in the gelling system using water. These in situ gelling systems were thoroughly characterized for mechanical, rheological and swelling properties. These systems are liquid at room temperature and gels at 37 degrees C. The EA C-GP system showed an initial burst release in vitro with about 85% drug released in 12 h followed by a steady release till 160 h, on the other hand EA nanoparticles entrapped in the C-GP system displayed sustained release till 360 h. The histopathological analysis indicates the absence of inflammation on administration, suggesting that these formulations are safe during the studied period. Furthermore, the antioxidant potential of EA C-GP and EA np C-GP gels has been evaluated against cyclosporine induced nephrotoxicity in rats. The data indicates that formulations were effective against cyclosporine induced nephrotoxicity, where the EA C-GP gels showed activity at 10 times lower dose and the EA np C-GP gels at 150 times lower dose when compared to orally given EA. Formulating nanoparticles of EA and incorporating them in C-GP system results in 15 times lowering of dose in comparison EA C-GP gels which is quite significant. Together, these results indicate that the bioavailability of ellagic acid can be improved by subcutaneous formulations administered as simple EA or EA nps.

Gallic acid attenuates hypertension, cardiac remodeling, and fibrosis in mice with NG-nitro-L-arginine methyl ester-induced hypertension via regulation of histone deacetylase 1 or histone deacetylase 2.

PubMed

Jin, Li; Lin, Ming Quan; Piao, Zhe Hao; Cho, Jae Yeong; Kim, Gwi Ran; Choi, Sin Young; Ryu, Yuhee; Sun, Simei; Kee, Hae Jin; Jeong, Myung Ho

2017-07-01

Gallic acid, a natural chemical found in plants, has been reported to show antioxidant, anticancer, and anti-inflammatory effects. We investigated the efficacy of a short-term or long-term treatment with gallic acid in N-nitro-L-arginine methyl ester (L-NAME)-induced hypertensive mice and the underlying regulatory mechanism. Hypertension was sufficiently induced after 2 weeks of L-NAME administration. Cardiac remodeling was assessed by echocardiography. Hypertrophic markers, transcription factors, and fibrosis-related gene expression were evaluated by quantitative real-time polymerase chain reaction and western blotting. Gallic acid effectively lowered SBP, regardless of the administration route (intraperitoneal or oral). L-NAME increased the left ventricular (LV) thickness without an increase in the total heart weight. Weekly echocardiography demonstrated that gallic acid significantly reduced LV posterior wall and septum thickness in chronic L-NAME mice from 3 to 7 weeks. The administration of gallic acid to mice showed a dual preventive and therapeutic effect on the L-NAME-induced LV remodeling. The effect was associated with the suppression of the gene expression of hypertrophy markers and the GATA-binding factor 6 (GATA6) transcription factor. Short-term or long-term treatment with gallic acid attenuated cardiac fibrosis and reduced the expression of histone deacetylase 1 and 2 in H9c2 cells and in rat primary cardiac fibroblasts, as well as in vivo. Small interfering RNA knockdown confirmed the association of these enzymes with L-NAME-induced cardiac remodeling and fibrosis. These results suggested that gallic acid may be a potential therapeutic agent for the treatment of cardiovascular diseases with hypertension and cardiac fibrosis.

Tuning stable and unstable aggregates of gallic acid capped gold nanoparticles using Mg2+ as coordinating agent.

PubMed

Kim, Dae-Young; Shinde, Surendra; Ghodake, Gajanan

2017-05-15

High reducibility of gallic acid allows synthesis of small sized monodisperse gold nanoparticles (GNPs) at ambient temperature (25°C). Mg 2+ rapidly interacts with the gallic acid ligands and suppresses the dispersion of GNPs therefore, causing a decrease in UV-vis absorbance intensity, and color change from red to blue. Thus, the colorimetric response of GNPs with Mg 2+ was investigated by observing temporal quenching of UV-vis absorbance and precise tuning of fractal growth of GNP aggregates. Moreover, Mg 2+ at concentrations as low as 200ppb can be detected using gallic acid ligand-mediated coordination chemistry which results quenching in UV-vis absorbance proportional to the exposure time. This gallic acid-based colorimetric sensor shown a great potential for the selective detection of pathologically important electrolyte Mg 2+ without any interference from other cations Ca 2+ and K + . Copyright © 2017 Elsevier Inc. All rights reserved.

The fifth solvatomorph of gallic acid with a supramolecular channel structure: Structural complexity and phase transitions

NASA Astrophysics Data System (ADS)

Thomas, Sajesh P.; Kaur, Ramanpreet; Kaur, Jassjot; Sankolli, Ravish; Nayak, Susanta K.; Guru Row, Tayur N.

2013-01-01

A new solvatomorph of gallic acid was generated using chiral additive technique and characterized by single crystal and powder X-ray diffraction, C-13 NMR, IR spectroscopic techniques and thermal analysis. The supramolecular channels formed by hexameric motifs of gallic acid and solvent molecules contain highly disordered solvent molecules with fractional occupancies.

Investigation into structure and dehydration dynamic of gallic acid monohydrate: A Raman spectroscopic study.

PubMed

Cai, Qiang; Xue, Jiadan; Wang, Qiqi; Du, Yong

2018-05-02

The dehydration process of gallic acid monohydrate was carried out by heating method and characterized using Raman spectroscopic technique. Density functional theory calculation with B3LYP function is applied to simulate optimized structures and vibrational frequencies of anhydrous gallic acid and its corresponding monohydrated form. Different vibrational modes are assigned by comparison between experimental and theoretical Raman spectra of above two polymorphs. Raman spectra show that vibrational modes of the monohydrate are distinctively different from those of anhydrous one. Meanwhile, the dynamic information about dehydration process of gallic acid monohydrate could also be observed and monitored directly with the help of Raman spectral analysis. The decay rate of the characteristic band from gallic acid monohydrate and the growth rate of anhydrous one are pretty consistent with each other. It indicates that there is no intermediate present during the dehydration process of gallic acid monohydrate. The results could offer us benchmark works for identifying both anhydrous and hydrated pharmaceutical compounds, characterizing their corresponding molecular conformation within various crystalline forms, and also providing useful information about the process of dehydration dynamic at the microscopic molecular level. Copyright © 2018 Elsevier B.V. All rights reserved.

Synthesis of molecular imprinting polymers for extraction of gallic acid from urine.

PubMed

Bhawani, Showkat Ahmad; Sen, Tham Soon; Ibrahim, Mohammad Nasir Mohammad

2018-02-21

The molecularly imprinted polymers for gallic acid were synthesized by precipitation polymerization. During the process of synthesis a non-covalent approach was used for the interaction of template and monomer. In the polymerization process, gallic acid was used as a template, acrylic acid as a functional monomer, ethylene glycol dimethacrylate as a cross-linker and 2,2'-azobisisobutyronitrile as an initiator and acetonitrile as a solvent. The synthesized imprinted and non-imprinted polymer particles were characterized by using Fourier-transform infrared spectroscopy and scanning electron microscopy. The rebinding efficiency of synthesized polymer particles was evaluated by batch binding assay. The highly selective imprinted polymer for gallic acid was MIPI1 with a composition (molar ratio) of 1:4:20, template: monomer: cross-linker, respectively. The MIPI1 showed highest binding efficiency (79.50%) as compared to other imprinted and non-imprinted polymers. The highly selective imprinted polymers have successfully extracted about 80% of gallic acid from spiked urine sample.

Aronia melanocarpa and its components demonstrate antiviral activity against influenza viruses.

PubMed

Park, Sehee; Kim, Jin Il; Lee, Ilseob; Lee, Sangmoo; Hwang, Min-Woong; Bae, Joon-Yong; Heo, Jun; Kim, Donghwan; Han, Sang-Zin; Park, Man-Seong

2013-10-11

The influenza virus is highly contagious in human populations around the world and results in approximately 250,000-500,000 deaths annually. Vaccines and antiviral drugs are commonly used to protect susceptible individuals. However, the antigenic mismatch of vaccines and the emergence of resistant strains against the currently available antiviral drugs have generated an urgent necessity to develop a novel broad-spectrum anti-influenza agent. Here we report that Aronia melanocarpa (black chokeberry, Aronia), the fruit of a perennial shrub species that contains several polyphenolic constituents, possesses in vitro and in vivo efficacy against different subtypes of influenza viruses including an oseltamivir-resistant strain. These anti-influenza properties of Aronia were attributed to two constituents, ellagic acid and myricetin. In an in vivo therapeutic mouse model, Aronia, ellagic acid, and myricetin protected mice against lethal challenge. Based on these results, we suggest that Aronia is a valuable source for antiviral agents and that ellagic acid and myricetin have potential as influenza therapeutics. Copyright © 2013 Elsevier Inc. All rights reserved.

Plant Natural Products Calycosin and Gallic Acid Synergistically Attenuate Neutrophil Infiltration and Subsequent Injury in Isoproterenol-Induced Myocardial Infarction: A Possible Role for Leukotriene B4 12-Hydroxydehydrogenase?

PubMed Central

Cheng, Yuanyuan; Tse, Hung Fat; Le, X. Chris; Rong, Jianhui

2015-01-01

Leukotriene B4 12-hydroxydehydrogenase (LTB4DH) catalyzes the oxidation of proinflammatory LTB4 into less bioactive 12-oxo-LTB4. We recently discovered that LTB4DH was induced by two different natural products in combination. We previously isolated gallic acid from Radix Paeoniae through a bioactivity-guided fractionation procedure. The purpose of this study is to test the hypothesis that LTB4DH inducers may suppress neutrophil-mediated inflammation in myocardial infarction. We first isolated the active compound(s) from another plant, Radix Astragali, by the similar strategy. By evaluating LTB4DH induction, we identified calycosin and formononetin from Radix Astragali by HPLC-ESI-MS technique. We confirmed that gallic acid and commercial calycosin or formononetin could synergistically induce LTB4DH expression in HepG2 cells and human neutrophils. Moreover, calycosin and gallic acid attenuated the effects of LTB4 on the survival and chemotaxis of neutrophil cell culture. We further demonstrated that calycosin and gallic acid synergistically suppressed neutrophil infiltration and protected cardiac integrity in the isoproterenol-induced mice model of myocardial infarction. Calycosin and gallic acid dramatically suppressed isoproterenol-induced increase in myeloperoxidase (MPO) activity and malondialdehyde (MDA) level. Collectively, our results suggest that LTB4DH inducers (i.e., calycosin and gallic acid) may be a novel combined therapy for the treatment of neutrophil-mediated myocardial injury. PMID:26265982

Alterations in the lenticular protein profile in experimental selenite-induced cataractogenesis and prevention by ellagic acid.

PubMed

Sakthivel, Muniyan; Geraldine, Pitchairaj; Thomas, Philip A

2011-08-01

Accumulating evidence suggests that oxidative stress underlies age-related formation of cataract, and that antioxidants retard cataractogenesis. This study aimed to evaluate whether ellagic acid, a natural polyphenol with antioxidant properties, prevents alterations in the lenticular protein profile in an experimental model of selenite cataract. Alterations in lenticular protein were determined by two-dimensional electrophoresis (2DE) and image analysis. Eluted αA-crystallin spots were analyzed by mass spectrometry. Western blot analysis was also performed to confirm the differential expression of certain crystallins and cytoskeletal proteins. In cataractous lenses, 2DE and image analysis revealed approximately 45 and 60 prominent spots in soluble and insoluble protein fractions respectively. Analysis of the pI and molecular weight of protein spots revealed differences in the expression of crystallin proteins in soluble and insoluble fractions. Western blot analysis confirmed changes in the expression of αA- and βB1- crystallins in both soluble and insoluble protein fractions, while mass spectrometry confirmed the degradation of αA-crystallin in selenite cataractous lenses. Western blot analysis also confirmed the occurrence of altered expression of certain cytoskeletal proteins in insoluble fractions. However, the lenticular protein profile in lenses from selenite-challenged, ellagic acid-treated rats was essentially similar to that noted in lenses from normal rats. The present study confirms the importance of structural and cytoskeletal proteins in the maintenance of lenticular transparency; the results also suggest that ellagic acid prevents lenticular protein alterations induced by selenite in an experimental setting.

Antioxidant, Antinociceptive and CNS Activities of Viscum orientale and High Sensitive Quantification of Bioactive Polyphenols by UPLC

PubMed Central

Khatun, Amina; Rahman, Mahmudur; Rahman, Md. Mahfizur; Hossain, Hemayet; Jahan, Ismet A.; Nesa, Mst. Luthfun

2016-01-01

Viscum orientale Willd. (Loranthaceae) has long been used in traditional medicine to treat pain, neuropharmacological disorders and various forms of tumor but not yet been reported. The aim of this study is to rationalize the traditional medicinal use of this plant by evaluating the methanol extract of V. orientale leaves (MEVOL) for anti-nociceptive, CNS depressant and antioxidant activities and to quantify the bioactive polyphenols present in this plant. Five polyphenolic compounds namely gallic acid, vanillic acid, caffeic acid, ellagic acid, and quercetin (17.54, 8.99, 99.61, 4523.31, and 100.15 mg/100 g of dry weight, respectively) have been identified in MEVOL using Ultra Performance Liquid Chromatography. Qualitative antioxidant activity determined by Thin Layer Chromatography indicated the presence of antioxidants. In quantitative antioxidant test using 2,2-diphenyl 1-picrylhydrazyl, MEVOL exhibited strong free antioxidant activity in a dose dependant manner (IC50 = 6.63 μg/ml) compared with ascorbic acid (IC50 = 1.91 μg/ml) and butylatedhydroxyanisole (IC50 = 2.27 μg/ml) controls. Total phenolic content determined using Folin Ciocaltu reagent was found to be 73.4 mg gallic acid equivalent/g of extract, while flavonoid content estimated using aluminum chloride colorimetric method was 170.7 mg quercetin equivalent/g of extract. Anti-nociceptive activity of MEVOL measured using acetic acid and formalin induced pain models in mice was significant (p < 0.001). MEVOL showed 65.6 and 88.8% writhing inhibition at 300 and 500 mg/kg body weight, respectively, comparing with standard diclofenac-Na (75.2% inhibition) at 25 mg/kg body weight in acetic acid induced pain model. In formalin induced pain model, paw licking was inhibited 45.93 and 56.4% in early phase and 55.66 and 72.64% in late phase at 300 and 500 mg/kg body weight, respectively, while diclofenac-Na inhibited 60.47 and 61.32% in early and late phase at 10 mg/kg body weight, respectively. In neuropharmacological activity test, overall behavioral test significantly reinforced CNS depressant activity. Spontaneous motor activities were reduced (p < 0.05) in both hole cross and open field tests compared with diazepam. Antioxidant activity of MEVOL is likely due to the phenolic and flavonoid compounds present within the leaf tissues. This study reveals significant in vivo anti-nociceptive and CNS depressant activities which justifies traditional medicinal applications of V. orientale. PMID:27445814

Antioxidative, Antiproliferative and Antimicrobial Activities of Phenolic Compounds from Three Myrcia Species.

PubMed

Dos Santos, Catarina; Galaverna, Renan S; Angolini, Celio F F; Nunes, Vania V A; de Almeida, Luiz F R; Ruiz, Ana L T G; de Carvalho, João E; Duarte, Regina M T; Duarte, Marta C T; Eberlin, Marcos N

2018-04-24

Myrcia bella Cambess., Myrcia fallax (Rich.) DC. and Myrcia guianensis (Aubl.) DC. (Myrtaceae) are trees found in Brazilian Cerrado. They have been widely used in folk medicine for the treatment of gastrointestinal disorders, hemorrhagic and infectious diseases. Few reports have been found in the literature connecting their phenolic composition and biological activities. In this regard, we have profiled the main phenolic constituents of Myrcia spp. leaves extracts by ESI(−)Q-TOF-MS. The main constituents found were ellagic acid ( M. bella ), galloyl glucose isomers ( M. guianensis ) and hexahydroxydiphenic (HHDP) acid derivatives ( M. fallax ). In addition, quercetin and myricetin derivatives were also found in all Myrcia spp. extracts. The most promising antioxidant activity, measured by 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity, was found for M. fallax extracts (EC 50 8.61 ± 0.22 µg·mL −1 ), being slightly less active than quercetin and gallic acid (EC 50 2.96 ± 0.17 and 2.03 ± 0.02 µg·mL −1 , respectively). For in vitro antiproliferative activity, M. guianensis showed good activity against leukemia (K562 TGI = 7.45 µg·mL −1 ). The best antimicrobial activity was observed for M. bella and M. fallax to Escherichia coli (300 and 250 µg·mL −1 , respectively). In conclusion, the activities found are closely related to the phenolic composition of these plants.

Preparation of Fe3O4 magnetic nanoparticles coated with gallic acid for drug delivery

PubMed Central

Dorniani, Dena; Hussein, Mohd Zobir Bin; Kura, Aminu Umar; Fakurazi, Sharida; Shaari, Abdul Halim; Ahmad, Zalinah

2012-01-01

Background and methods Magnetic iron oxide nanoparticles were prepared using a sonochemical method under atmospheric conditions at a Fe2+ to Fe3+ molar ratio of 1:2. The iron oxide nanoparticles were subsequently coated with chitosan and gallic acid to produce a core-shell structure. Results X-ray diffraction demonstrated that the magnetic nanoparticles were pure Fe3O4 with a cubic inverse spinel structure. Transmission electron microscopy showed that the Fe3O4 nanoparticles were of spherical shape with a mean diameter of 11 nm, compared with 13 nm for the iron oxide-chitosan-gallic acid (FCG) nanocarriers. Conclusion The magnetic nanocarrier enhanced the thermal stability of the drug, gallic acid. Release of the active drug from the FCG nanocarrier was found to occur in a controlled manner. The gallic acid and FCG nanoparticles were not toxic in a normal human fibroblast (3T3) line, and anticancer activity was higher in HT29 than MCF7 cell lines. PMID:23166439

Gallic acid-based indanone derivative interacts synergistically with tetracycline by inhibiting efflux pump in multidrug resistant E. coli.

PubMed

Dwivedi, Gaurav Raj; Tiwari, Nimisha; Singh, Aastha; Kumar, Akhil; Roy, Sudeep; Negi, Arvind Singh; Pal, Anirban; Chanda, Debabrata; Sharma, Ashok; Darokar, Mahendra P

2016-03-01

The purpose of the present study was to study the synergy potential of gallic acid-based derivatives in combination with conventional antibiotics using multidrug resistant cultures of Escherichia coli. Gallic acid-based derivatives significantly reduced the MIC of tetracycline against multidrug resistant clinical isolate of E. coli. The best representative, 3-(3',4,'5'-trimethoxyphenyl)-4,5,6-trimethoxyindanone-1, an indanone derivative of gallic acid, was observed to inhibit ethidium bromide efflux and ATPase which was also supported by in silico docking. This derivative extended the post-antibiotic effect and decreased the mutation prevention concentration of tetracycline. This derivative in combination with TET was able to reduce the concentration of TNFα up to 18-fold in Swiss albino mice. This derivative was nontoxic and well tolerated up to 300 mg/kg dose in subacute oral toxicity study in mice. This is the first report of gallic acid-based indanone derivative as drug resistance reversal agent acting through ATP-dependent efflux pump inhibition.

Aldose reductase inhibitors from the leaves of Myrciaria dubia (H. B. & K.) McVaugh.

PubMed

Ueda, H; Kuroiwa, E; Tachibana, Y; Kawanishi, K; Ayala, F; Moriyasu, M

2004-11-01

Ellagic acid (1) and its two derivatives, 4-O-methylellagic acid (2) and 4-(alpha-rhamnopyranosyl)ellagic acid (3) were isolated as inhibitors of aldose reductase (AR) from Myrciaria dubia (H. B. & K.) McVaugh. Compound 2 was the first isolated from the nature. Compound 3 showed the strongest inhibition against human recombinant AR (HRAR) and rat lens AR (RLAR). Inhibitory activity of compound 3 against HRAR (IC50 value = 4.1 x 10(-8) M) was 60 times more than that of quercetin (2.5 x 10(-6) M). The type of inhibition against HRAR was uncompetitive.

Carbon molecular sieve based micro-matrix-solid-phase dispersion for the extraction of polyphenols in pomegranate peel by UHPLC-Q-TOF/MS.

PubMed

Du, Li-Jing; Huang, Jian-Ping; Wang, Bin; Wang, Chen-Hui; Wang, Qiu-Yan; Hu, Yu-Han; Yi, Ling; Cao, Jun; Peng, Li-Qing; Chen, Yu-Bo; Zhang, Qi-Dong

2018-06-04

A rapid, simple and efficient sample extraction method based on micro-matrix-solid-phase dispersion (micro-MSPD) was applied to the extraction of polyphenols from pomegranate peel. Five target analytes were determined by ultra-high-performance liquid chromatography coupled with quadrupole-time-of-flight mass spectrometry. Carbon molecular sieve (CMS) was firstly used as dispersant to improve extraction efficiency in micro-MSPD. The major micro-MSPD parameters, such as type of dispersant, amount of dispersant, grinding time and the type and the volume of elution solvents, were studied and optimized. Under optimized conditions, 26 mg of pomegranate peel was dispersed with 32.5 mg of CMS, the grinding time was selected as 90 s, the dispersed sample was eluted with 100 μL of methanol. Results showed that the proposed method was of good linearity for concentrations of analytes against their peak areas (coefficient of determination r 2 >0.990), the limit of the detection was as low as 3.2 ng/mL, and the spiking recoveries were between 88.1% and 106%. Satisfactory results were obtained for the extraction of gallic acid, punicalagin A, punicalagin B, catechin and ellagic acid from pomegranate peel sample, which demonstrated nice reliability and high sensitivity of this approach. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.

Valorization of solid wastes from chestnut industry processing: Extraction and optimization of polyphenols, tannins and ellagitannins and its potential for adhesives, cosmetic and pharmaceutical industry.

PubMed

Aires, Alfredo; Carvalho, Rosa; Saavedra, Maria José

2016-02-01

The aim of the current study was to evaluate the potential of chestnut peels to produce pomaces enhanced with tannins to be used in the formulations of wood adhesives, leather tanning or as natural antioxidants in food, cosmetic and pharmaceutical industry. An analytical procedure was planned as 2 factorial design to analyze the influence of solvent (water, Na2SO3 and NaOH at different concentrations of 1, 2, 4, and 8% in water) and extraction time (30, 60, and 120, 240, 480 and 960min) on extraction yield, pH, Stiasny index, and tannins. HPLC-diode array detector equipped with an ionization mass spectrophotometer was used to assess the polyphenol composition. Our results showed that both extraction properties and phytochemicals were significantly affected (P<0.001) by all independent factors. The main tannins identified were the hydrolyzable gallic acid, vescalagin castalagin and ellagic acid, and the condensed epigallocatechin, catechin and epicatechin. The solvent 1% Na2SO3 was more effective to extract the condensed tannins whilst hydrolyzable tannins were extracted efficiently by 1% NaOH. The multivariable analysis and the Pearson's correlation coefficients showed a direct association between Stiasny number and the average levels of condensed tannins. Copyright © 2015 Elsevier Ltd. All rights reserved.

Induction of murine embryonic stem cell differentiation by medicinal plant extracts.

PubMed

Reynertson, Kurt A; Charlson, Mary E; Gudas, Lorraine J

2011-01-01

Epidemiological evidence indicates that diets high in fruits and vegetables provide a measure of cancer chemoprevention due to phytochemical constituents. Natural products are a rich source of cancer chemotherapy drugs, and primarily target rapidly cycling tumor cells. Increasing evidence indicates that many cancers contain small populations of resistant, stem-like cells that have the capacity to regenerate tumors following chemotherapy and radiation, and have been linked to the initiation of metastases. Our goal is to discover natural product-based clinical or dietary interventions that selectively target cancer stem cells, inducing differentiation. We adapted an alkaline phosphatase (AP) stain to assay plant extracts for the capacity to induce differentiation in embryonic stem (ES) cells. AP is a characteristic marker of undifferentiated ES cells, and this represents a novel approach to screening medicinal plant extracts. Following a survey of approximately 100 fractions obtained from 12 species of ethnomedically utilized plants, we found fractions from 3 species that induced differentiation, decreasing AP and transcript levels of pluripotency markers (Nanog, Oct-4, Rex-1). These fractions affected proliferation of murine ES, and human embryonal, prostate, and breast carcinoma cells in a dose-dependent manner. Several phytochemical constituents were isolated; the antioxidant phytochemicals ellagic acid and gallic acid were shown to affect viability of cultured breast carcinoma cells. Copyright © 2010 Elsevier Inc. All rights reserved.

Gallic acid abolishes the EGFR/Src/Akt/Erk-mediated expression of matrix metalloproteinase-9 in MCF-7 breast cancer cells.

PubMed

Chen, Ying-Jung; Lin, Ku-Nan; Jhang, Li-Mei; Huang, Chia-Hui; Lee, Yuan-Chin; Chang, Long-Sen

2016-05-25

Several studies have revealed that natural compounds are valuable resources to develop novel agents against dysregulation of the EGF/EGFR-mediated matrix metalloproteinase-9 (MMP-9) expression in cancer cells. In view of the findings that EGF/EGFR-mediated MMP-9 expression is closely related to invasion and metastasis of breast cancer. To determine the beneficial effects of gallic acid on the suppression of breast cancer metastasis, we explored the effect of gallic acid on MMP-9 expression in EGF-treated MCF-7 breast cancer cells. Treatment with EGF up-regulated MMP-9 mRNA and protein levels in MCF-7 cells. EGF treatment induced phosphorylation of EGFR and elicited Src activation, subsequently promoting Akt/NFκB (p65) and ERK/c-Jun phosphorylation in MCF-7 cells. Activation of Akt/p65 and ERK/c-Jun was responsible for the MMP-9 up-regulation in EGF-treated cells. Gallic acid repressed the EGF-induced activation of EGFR and Src; furthermore, inactivation of Akt/p65 and ERK/c-Jun was a result of the inhibitory effect of gallic acid on the EGF-induced MMP-9 up-regulation. Over-expression of constitutively active Akt and MEK1 or over-expression of constitutively active Src eradicated the inhibitory effect of gallic acid on the EGF-induced MMP-9 up-regulation. A chromosome conformation capture assay showed that EGF induced a chromosomal loop formation in the MMP-9 promoter via NFκB/p65 and AP-1/c-Jun activation. Treatment with gallic acid, EGFR inhibitor, or Src inhibitor reduced DNA looping. Taken together, our data suggest that gallic acid inhibits the activation of EGFR/Src-mediated Akt and ERK, leading to reduced levels of p65/c-Jun-mediated DNA looping and thus inhibiting MMP-9 expression in EGF-treated MCF-7 cells. Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

Determination of gallic acid with rhodanine by reverse flow injection analysis using simplex optimization.

PubMed

Phakthong, Wilaiwan; Liawruangrath, Boonsom; Liawruangrath, Saisunee

2014-12-01

A reversed flow injection (rFI) system was designed and constructed for gallic acid determination. Gallic acid was determined based on the formation of chromogen between gallic acid and rhodanine, resulting in a colored product with a λmax at 520 nm. The optimum conditions for determining gallic acid were also investigated. Optimizations of the experimental conditions were carried out based on the so-call univariate method. The conditions obtained were 0.6% (w/v) rhodanine, 70% (v/v) ethanol, 0.9 mol L(-1) NaOH, 2.0 mL min(-1) flow rate, 75 μL injection loop and 600 cm mixing tubing length, respectively. Comparative optimizations of the experimental conditions were also carried out by multivariate or simplex optimization method. The conditions obtained were 1.2% (w/v) rhodanine, 70% (v/v) ethanol, 1.2 mol L(-1) NaOH, flow rate 2.5 mL min(-1), 75 μL injection loop and 600 cm mixing tubing length, respectively. It was found that the optimum conditions obtained by the former optimization method were mostly similar to those obtained by the latter method. The linear relationship between peak height and the concentration of gallic acid was obtained over the range of 0.1-35.0 mg L(-1) with the detection limit 0.081 mg L(-1). The relative standard deviations were found to be in the ranges 0.46-1.96% for 1, 10, 30 mg L(-1) of gallic acid (n=11). The method has the advantages of simplicity extremely high selectivity and high precision. The proposed method was successfully applied to the determination of gallic acid in longan samples without interferent effects from other common phenolic compounds that might be present in the longan samples collected in northern Thailand. Copyright © 2014 Elsevier B.V. All rights reserved.

DOE Office of Scientific and Technical Information (OSTI.GOV)

Eler, Gabrielle Jacklin; Santos, Israel Souza; Giaretta de Moraes, Amarilis

n-Propyl gallate and its analogs are used in foods and other products to prevent oxidation. In the liver the compound exerts several harmful effects, especially gluconeogenesis inhibition. The mode of transport and distribution of n-propyl gallate and its kinetics of biotransformation have not yet been investigated. To fill this gap the transformation, transport and distribution of n-propyl gallate and two analogs were investigated in the rat liver. Isolated perfused rat liver was used. n-Propyl gallate, methyl gallate, n-octyl gallate and transformation products were quantified by high pressure-liquid chromatography coupled to fluorescence detection. The interactions of n-propyl gallate and analogs withmore » the liver presented three main characteristics: (1) the hydrolytic release of gallic acid from n-propyl gallate and methyl gallate was very fast compared with the subsequent transformations of the gallic acid moiety; (2) transport of the esters was very fast and flow-limited in contrast to the slow and barrier-limited transport of gallic acid; (3) the apparent distribution volume of n-propyl gallate, but probably also of methyl gallate and n-octyl gallate, greatly exceeded the water space in the liver, contrary to the gallic acid space which is smaller than the water space. It can be concluded that at low portal concentrations (< 50 μM) the gallic acid esters are 100% extracted during a single passage through the liver, releasing mainly gallic acid into the systemic circulation. For the latter a considerable time is required until complete biotransformation. The exposure of the liver to the esters, however, is quite prolonged due to extensive intracellular binding. - Highlights: • The liver binds very strongly n-propyl gallate and releases basically gallic acid. • n-propyl gallate and analogs undergo concentrative flow-limited distribution. • Gallic acid undergoes barrier-limited distribution and is slowly transformed. • The long residence time of n-propyl gallate and analogs increases toxicity.« less

Simultaneous determination of gallic acid and gentisic acid in organic anion transporter expressing cells by liquid chromatography-tandem mass spectrometry.

PubMed

Wang, Li; Halquist, Matthew S; Sweet, Douglas H

2013-10-15

In order to elucidate the role of organic anion transporters (OATs) in the renal elimination of gallic acid and gentisic acid, a new, rapid, and sensitive liquid chromatography-tandem mass spectrometry (LC-MS/MS) method has been developed and validated for the simultaneous determination of gallic acid and gentisic acid in cell lysate, using Danshensu as the internal standard (IS). After a simple liquid-liquid extraction, the analytes were detected in negative ESI mode using selected reaction monitoring. The precursor-to-product ion transitions (m/z) were 169.0→125.0, 153.1→108.0, and 196.8→135.2 for gallic acid, gentisic acid, and the IS, respectively. Chromatographic separation was achieved on a C18 column using mobile phases consisting of water with 0.1% acetic acid (A) and acetonitrile with 0.05% formic acid. (B) The total run time was 3min and calibration curves were linear over the concentrations of 0.33-2400ng/mL for both compounds (r(2)>0.995). Good precision (between 3.11% and 14.1% RSD) and accuracy (between -12.7% and 11% bias) was observed for quality controls at concentrations of 0.33 (lower limit of quantification), 1, 50, and 2000ng/mL. The mean extraction recovery of gallic acid and gentisic acid was 80.7% and 83.5%, respectively. Results from post-column infusion and post-extraction methods indicated that the analytical method exhibited negligible matrix effects. Finally, this validated assay was successfully applied in a cellular uptake study to determine the intracellular concentrations of gallic acid and gentisic acid in OAT expressing cells. Copyright © 2013 Elsevier B.V. All rights reserved.

Gallic acid prevents isoproterenol-induced cardiac hypertrophy and fibrosis through regulation of JNK2 signaling and Smad3 binding activity

PubMed Central

Ryu, Yuhee; Jin, Li; Kee, Hae Jin; Piao, Zhe Hao; Cho, Jae Yeong; Kim, Gwi Ran; Choi, Sin Young; Lin, Ming Quan; Jeong, Myung Ho

2016-01-01

Gallic acid, a type of phenolic acid, has been shown to have beneficial effects in inflammation, vascular calcification, and metabolic diseases. The present study was aimed at determining the effect and regulatory mechanism of gallic acid in cardiac hypertrophy and fibrosis. Cardiac hypertrophy was induced by isoproterenol (ISP) in mice and primary neonatal cardiomyocytes. Gallic acid pretreatment attenuated concentric cardiac hypertrophy. It downregulated the expression of atrial natriuretic peptide, brain natriuretic peptide, and beta-myosin heavy chain in vivo and in vitro. Moreover, it prevented interstitial collagen deposition and expression of fibrosis-associated genes. Upregulation of collagen type I by Smad3 overexpression was observed in cardiac myoblast H9c2 cells but not in cardiac fibroblasts. Gallic acid reduced the DNA binding activity of phosphorylated Smad3 in Smad binding sites of collagen type I promoter in rat cardiac fibroblasts. Furthermore, it decreased the ISP-induced phosphorylation of c-Jun N-terminal kinase (JNK) and extracellular signal regulated kinase (ERK) protein in mice. JNK2 overexpression reduced collagen type I and Smad3 expression as well as GATA4 expression in H9c2 cells and cardiac fibroblasts. Gallic acid might be a novel therapeutic agent for the prevention of cardiac hypertrophy and fibrosis by regulating the JNK2 and Smad3 signaling pathway. PMID:27703224

Relative content of gallic acid over 5-galloylquinic acid as an index for the baking intensity of oolong teas.

PubMed

Wang, Miki Mei-Chi; Yeh, Yun; Shih, Yu-En; Tzen, Jason Tze-Cheng

2018-04-01

Phenolic compounds in a series of old oolong teas prepared by baking annually were monitored and compared. The results showed that the relative content of gallic acid over 5-galloylquinic acid was subsequently elevated during this preparatory process. To reveal the effect was mainly resulted from baking or aging, two sets of oolong teas were collected and examined; one set was generated from fresh oolong tea via continually daily baking and the other set was composed of aged oolong teas with no or light baking in the storage period. The relative content of gallic acid over 5-galloylquinic acid was observed to be subsequently elevated when oolong tea was continually baked at 90, 100, 110, and 120 °C for 8 h day after day. In contrast, the relative contents of gallic acid over 5-galloylquinic acid in aged oolong teas with no or light baking were found to be similar to or slightly higher than that in fresh oolong tea. The results suggest that the relative content of gallic acid over 5-galloylquinic acid seems to be a suitable index for the baking intensity of oolong tea in different preparations. Copyright © 2017. Published by Elsevier B.V.

Chemical composition, antioxidant and antibacterial activities of two Spondias species from Northeastern Brazil.

PubMed

da Silva, Ana Raquel Araújo; de Morais, Selene Maia; Marques, Márcia Maria Mendes; de Oliveira, Danielle Ferreira; Barros, Caroline Costa; de Almeida, Raimundo Rafael; Vieira, Ícaro Gusmão Pinto; Guedes, Maria Izabel Florindo

2012-06-01

The leaves of Spondias tuberosa Arr. Cam. (Anacardiaceae) and Spondias mombin L. have been traditionally used for medicinal purposes. Some studies reveal their antibacterial, antimicrobial, and antiviral properties. Determine the chemical composition, antioxidant, and antimicrobial activities of Spondias species to justify its ethnopharmacological use. Spondias species extracts were prepared with methanol:water 80:20 and analyzed by silica gel column chromatography and reversed phase liquid chromatography (HPLC). The antioxidant activity was evaluated by scavenging the radicals 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and 2,2-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS•+) and measuring antimicrobial activity (agar well diffusion method, minimum inhibitory concentration and minimum bactericidal concentrations). The HPLC analysis of Spondias extracts demonstrated the occurrence of high yield of flavonoids. Found in S. mombin were quercetin (2.36 ± 0.01 mg/g) and ellagic acid (41.56 ± 0.01 mg/g) and in S. tuberosa species rutin (53.38 ± 1.71 mg/g), quercetin (24.46 ± 0.87 mg/g), and ellagic acid (169.76 ± 0.17 mg/g). The antibacterial activity of the extracts against the various bacteria strains varied from 8.8 to 20.1 mm. MIC values from 62.5 to 125 µg/mL were satisfactory when compared with other plant products. Medium DPPH scavenging activity IC₅₀ for Spondias extracts varied from 0.042 to 0.558 mg/mL and for ABTS from 0.089 to 0.465 mg/mL. DPPH scavenging activity for constituent ellagic acid IC₅₀ = 0.042 mg/mL and for quercetin IC₅₀ = 0.081 mg/mL. The chemical study of Spondias leaf extracts showed the occurrence of quercetin, rutin and ellagic acid, substances with relevant antioxidant and antimicrobial activities.

Molecular mechanics and dynamics studies on the interaction of gallic acid with collagen-like peptides

NASA Astrophysics Data System (ADS)

Madhan, B.; Thanikaivelan, P.; Subramanian, V.; Raghava Rao, J.; Unni Nair, Balachandran; Ramasami, T.

2001-10-01

Molecular modelling approaches have been used to understand the interaction of collagen-like peptides with gallic acid, which mimic vegetable tanning processes involved in protein stabilization. Several interaction sites have been identified and the binding energies of the complexes have been calculated. The calculated binding energies for various geometries are in the range 6-13 kcal/mol. It is found that some complexes exhibit hydrogen bonding, and electrostatic interaction plays a dominant role in the stabilization of the peptide by gallic acid. The π-OH type of interaction is also observed in the peptide stabilization. Molecular dynamics (MD) simulation for 600 ps revealed the possibility of hydrogen bonding between the collagen-like peptide and gallic acid.

Effects of polyurethane matrices on fungal tannase and gallic acid production under solid state culture*

PubMed Central

Treviňo, Lucia; Contreras-Esquivel, Juan C.; Rodríguez-Herrera, Raul; Aguilar, Cristóbal Noé

2007-01-01

The influence of the physical structure of polyurethane matrix as a support in a solid state culture in tannase production and gallic acid accumulation by Aspergillus niger Aa-20 was evaluated. Three different polyurethane matrices were used as the support: continuous, semi-discontinuous and discontinuous. The highest tannase production at 2479.59 U/L during the first 12 h of culture was obtained using the discontinuous matrix. The gallic acid was accumulated at 7.64 g/L at the discontinuous matrix. The results show that the discontinuous matrix of polyurethane is better for tannase production and gallic acid accumulation in a solid state culture bioprocess than the continuous and semi-discontinuous matrices. PMID:17910122

Rise in the pH of an unfrozen solution in ice due to the presence of NaCl and promotion of decomposition of gallic acids owing to a change in the pH.

PubMed

Takenaka, Norimichi; Tanaka, Masayuki; Okitsu, Kenji; Bandow, Hiroshi

2006-09-14

Oxidative decomposition of gallic acid occurs in alkaline solutions but hardly arises in acidic solutions. We have found that the addition of sodium chloride promotes the decomposition of gallic acid caused by freezing even under neutral and acidic conditions. Even at pH 4.5, gallic acid was decomposed by freezing in the presence of NaCl; however, in the absence of NaCl, it was hardly decomposed by freezing at pH lower than 7. Chloride ions are more easily incorporated in ice than sodium ions when the NaCl solution is frozen. The unfrozen solution in ice becomes positively charged, and as a result, protons transfer from the unfrozen solution to the ice. We measured the pH in the unfrozen solution which coexists with single-crystal ice formed from a 5 mmol dm(-3) NaCl solution and determined the pH to be 8.6 at equilibrium with CO(2) of 380 ppm or 11.3 in the absence of CO(2) compared to pH 5.6 in the original solution. From the model calculation performed for gallic acid solution in the presence of 5 mmol dm(-3) NaCl, it can be estimated that the amount of OH(-) transferred from the ice to the solution corresponds to 1.26 x 10(-5) mol dm(-3). The amount of OH(-) transferred is concentrated into the unfrozen solution and affects the pH of the unfrozen solution. Therefore, the pH in an unfrozen gallic acid solution in ice becomes alkaline, and the decomposition of gallic acid proceeds. It is expected that other base-catalyzed reactions in weakly acidic solutions also proceed by freezing in the presence of NaCl without the need for any alkaline reagents.

Non-toxic agarose/gelatin-based microencapsulation system containing gallic acid for antifungal application.

PubMed

Lam, P-L; Gambari, R; Kok, S H-L; Lam, K-H; Tang, J C-O; Bian, Z-X; Lee, K K-H; Chui, C-H

2015-02-01

Aspergillus niger (A. niger) is a common species of Aspergillus molds. Cutaneous aspergillosis usually occurs in skin sites near intravenous injection and approximately 6% of cutaneous aspergillosis cases which do not involve burn or HIV-infected patients are caused by A. niger. Biomaterials and biopharmaceuticals produced from microparticle-based drug delivery systems have received much attention as microencapsulated drugs offer an improvement in therapeutic efficacy due to better human absorption. The frequently used crosslinker, glutaraldehyde, in gelatin-based microencapsulation systems is considered harmful to human beings. In order to tackle the potential risks, agarose has become an alternative polymer to be used with gelatin as wall matrix materials of microcapsules. In the present study, we report the eco-friendly use of an agarose/gelatin-based microencapsulation system to enhance the antifungal activity of gallic acid and reduce its potential cytotoxic effects towards human skin keratinocytes. We used optimal parameter combinations, such as an agarose/gelatin ratio of 1:1, a polymer/oil ratio of 1:60, a surfactant volume of 1% w/w and a stirring speed of 900 rpm. The minimum inhibitory concentration of microencapsulated gallic acid (62.5 µg/ml) was significantly improved when compared with that of the original drug (>750 µg/ml). The anti-A. niger activity of gallic acid -containing microcapsules was much stronger than that of the original drug. Following 48 h of treatment, skin cell survival was approximately 90% with agarose/gelatin microcapsules containing gallic acid, whereas cell viability was only 25-35% with free gallic acid. Our results demonstrate that agarose/gelatin-based microcapsules containing gallic acid may prove to be helpful in the treatment of A. niger-induced skin infections near intravenous injection sites.

Gallic acid attenuates high-fat diet fed-streptozotocin-induced insulin resistance via partial agonism of PPARγ in experimental type 2 diabetic rats and enhances glucose uptake through translocation and activation of GLUT4 in PI3K/p-Akt signaling pathway.

PubMed

Gandhi, Gopalsamy Rajiv; Jothi, Gnanasekaran; Antony, Poovathumkal James; Balakrishna, Kedike; Paulraj, Michael Gabriel; Ignacimuthu, Savarimuthu; Stalin, Antony; Al-Dhabi, Naif Abdullah

2014-12-15

In this study, the therapeutic efficacy of gallic acid from Cyamopsis tetragonoloba (L.) Taub. (Fabaceae) beans was examined against high-fat diet fed-streptozotocin-induced experimental type 2 diabetic rats. Molecular-dockings were done to determine the putative binding modes of gallic acid into the active sites of key insulin-signaling markers. Gallic acid (20 mg/kg) given to high-fat diet fed-streptozotocin-induced rats lowered body weight gain, fasting blood glucose and plasma insulin in diabetic rats. It further restored the alterations of biochemical parameters to near normal levels in diabetic treated rats along with cytoprotective action on pancreatic β-cell. Histology of liver and adipose tissues supported the biochemical findings. Gallic acid significantly enhanced the level of peroxisome proliferator-activated receptor γ (PPARγ) expression in the adipose tissue of treated rat compared to untreated diabetic rat; it also slightly activated PPARγ expressions in the liver and skeletal muscle. Consequently, it improved insulin-dependent glucose transport in adipose tissue through translocation and activation of glucose transporter protein 4 (GLUT4) in phosphatidylinositol 3-kinase (PI3K)/phosphorylated protein kinase B (p-Akt) dependent pathway. Gallic acid docked with PPARγ; it exhibited promising interactions with the GLUT4, glucose transporter protein 1 (GLUT1), PI3K and p-Akt. These findings provided evidence to show that gallic acid could improve adipose tissue insulin sensitivity, modulate adipogenesis, increase adipose glucose uptake and protect β-cells from impairment. Hence it can be used in the management of obesity-associated type 2 diabetes mellitus. Copyright © 2014 Elsevier B.V. All rights reserved.

Gallic acid indanone and mangiferin xanthone are strong determinants of immunosuppressive anti-tumour effects of Mangifera indica L. bark in MDA-MB231 breast cancer cells.

PubMed

García-Rivera, Dagmar; Delgado, René; Bougarne, Nadia; Haegeman, Guy; Berghe, Wim Vanden

2011-06-01

Vimang is a standardized extract derived from Mango bark (Mangifera Indica L.), commonly used as anti-inflammatory phytomedicine, which has recently been used to complement cancer therapies in cancer patients. We have further investigated potential anti-tumour effects of glucosylxanthone mangiferin and indanone gallic acid, which are both present in Vimang extract. We observed significant anti-tumour effects of both Vimang constituents in the highly aggressive and metastatic breast cancer cell type MDA-MB231. At the molecular level, mangiferin and gallic acid both inhibit classical NFκB activation by IKKα/β kinases, which results in impaired IκB degradation, NFκB translocation and NFκB/DNA binding. In contrast to the xanthone mangiferin, gallic acid further inhibits additional NFκB pathways involved in cancer cell survival and therapy resistance, such as MEK1, JNK1/2, MSK1, and p90RSK. This results in combinatorial inhibition of NFκB activity by gallic acid, which results in potent inhibition of NFκB target genes involved in inflammation, metastasis, anti-apoptosis and angiogenesis, such as IL-6, IL-8, COX2, CXCR4, XIAP, bcl2, VEGF. The cumulative NFκB inhibition by gallic acid, but not mangiferin, is also reflected at the level of cell survival, which reveals significant tumour cytotoxic effects in MDA-MB231 cells. Altogether, we identify gallic acid, besides mangiferin, as an essential anti-cancer component in Vimang extract, which demonstrates multifocal inhibition of NFκB activity in the cancer-inflammation network. Copyright © 2011 Elsevier Ireland Ltd. All rights reserved.

Bioavailable Concentrations of Delphinidin and Its Metabolite, Gallic Acid, Induce Antioxidant Protection Associated with Increased Intracellular Glutathione in Cultured Endothelial Cells

PubMed Central

Goszcz, Katarzyna; Deakin, Sherine J.; Duthie, Garry G.; Stewart, Derek

2017-01-01

Despite limited bioavailability and rapid degradation, dietary anthocyanins are antioxidants with cardiovascular benefits. This study tested the hypothesis that the antioxidant protection conferred by the anthocyanin, delphinidin, is mediated by modulation of endogenous antioxidant defences, driven by its degradation product, gallic acid. Delphinidin was found to degrade rapidly (t1/2 ~ 30 min), generating gallic acid as a major degradation product. Both delphinidin and gallic acid generated oxygen-centred radicals at high (100 μM) concentrations in vitro. In a cultured human umbilical vein endothelial cell model of oxidative stress, the antioxidant protective effects of both delphinidin and gallic acid displayed a hormesic profile; 100 μM concentrations of both were cytotoxic, but relatively low concentrations (100 nM–1 μM) protected the cells and were associated with increased intracellular glutathione. We conclude that delphinidin is intrinsically unstable and unlikely to confer any direct antioxidant activity in vivo yet it offered antioxidant protection to cells at low concentrations. This paradox might be explained by the ability of the degradation product, gallic acid, to confer benefit. The findings are important in understanding the mode of protection conferred by anthocyanins and reinforce the necessity to conduct in vitro experiments at biologically relevant concentrations. PMID:29081896

Protective activity of hamamelitannin on cell damage of murine skin fibroblasts induced by UVB irradiation.

PubMed

Masaki, H; Atsumi, T; Sakurai, H

1995-07-01

The protective activities of hamamelitannin (2',5-di-O-galloyl-hamamelose) in Hamamelis virginiana L. and its related compound, gallic acid, on damaged murine skin fibroblasts induced by UVB irradiation were investigated. In order to exclude the UV absorbing effect of the compounds, the protection study was performed such that the fibroblasts were pretreated with hamamelitannin or gallic acid for 24 h before UVB irradiation. At 200 microM concentration, hamamelitannin gave the higher survival of 72.6 +/- 0.4% in comparison with that of gallic acid (35.5 +/- 1.0%), while UVB absorbers such as 2-ethylhexyl p-methoxycinnamate and hexylbenzoate did not show such protection. The scavenging activities of hamamelitannin and gallic acid against active oxygens such as superoxide anion radicals, hydroxyl radicals and singlet oxygens were evaluated using electron spin resonance (ESR-spin trapping method). Hamamelitannin and gallic acid showed potent scavenging activities against all active oxygens tested. Furthermore, the association of hamamelitannin to fibroblasts was examined by comparing it with that of gallic acid, and the following results were obtained: (1) hamamelitannin reduces the reaction rate of liposome entrapped-nitroblue tetrazolium (NBT) with external superoxide anions, and (2) several glycosides associate with fibroblasts. From these results, it was concluded that hamamelitannin protects murine fibroblasts against external active oxygens by associating with the cell surface through its sugar moiety.

Anti-Acne Activity of Italian Medicinal Plants Used for Skin Infection

PubMed Central

Nelson, Kate; Lyles, James T.; Li, Tracy; Saitta, Alessandro; Addie-Noye, Eugenia; Tyler, Paula; Quave, Cassandra L.

2016-01-01

Propionibacterium acnes is implicated in the pathogenesis of acne vulgaris, which impacts >85% of teenagers. Novel therapies are in high demand and an ethnopharmacological approach to discovering new plant sources of anti-acne therapeutics could contribute to filling this void in effective therapies. The aims of our study were two-fold: (1) To determine if species identified in ethnopharmacological field studies as having traditional uses for skin and soft tissue infection (SSTI) exhibit significantly more activity against P. acnes than species with no such reported use; and (2) Chemically characterize active extracts and assess their suitability for future investigation. Extracts of Italian medicinal (for acne and other skin infection) and randomly collected plants and fungi were screened for growth-inhibitory and anti-biofilm activity in P. acnes using broth microdilution methods. Bioactive extracts were chemically characterized by HPLC and examined for cytotoxicity against human keratinocytes (HaCaTs). Following evaluation of 157 extracts from 10 fungi and 58 plants, we identified crude extracts from seven species exhibiting growth inhibitory activity (MICs 64–256 μg mL−1). All active extracts were examined for cytotoxicity against HaCaTs; extracts from one fungal and one plant species were toxic (IC50 256 μg mL−1). HPLC analysis with chemical standards revealed many of these extracts contained chlorogenic acid, p-coumaric acid, ellagic acid, gallic acid, and tannic acid. In conclusion, species used in traditional medicine for the skin exhibited significantly greater (p < 0.05) growth inhibitory and biofilm eradication activity than random species, supporting the validity of an ethnobotanical approach to identifying new therapeutics. The anti-acne activity of three extracts is reported for the first time: Vitis vinifera leaves, Asphodelus microcarpus leaves, and Vicia sativa aerial parts. PMID:27891094

Antioxidant activity of gallic acid and methyl gallate in triacylglycerols of Kilka fish oil and its oil-in-water emulsion.

PubMed

Asnaashari, Maryam; Farhoosh, Reza; Sharif, Ali

2014-09-15

The anti-DPPH radical effect as well as anti-peroxide activity of gallic acid, methyl gallate, and α-tocopherol in a bulk Kilka fish oil and its oil-in-water emulsion stabilized by soy protein isolate at 55°C were investigated. Gallic acid with the lowest hydrophobicity (log P=-0.28) was found to be the most active antiradical agent (IC50=29.5 μM), followed by methyl gallate (IC50=38.0 μM, log P=-0.23) and α-tocopherol (IC50=105.3 μM, log P=0.70). The anti-peroxide activity in the bulk oil system decreased in the order of methyl gallate>gallic acid>α-tocopherol. In the emulsion system, methyl gallate still behaved better than gallic acid, but the highest activity belonged to α-tocopherol. Based on the calculation of a number of kinetic parameters, the antioxidants, in general, showed better performances in the bulk oil system than in the emulsion system. Copyright © 2014 Elsevier Ltd. All rights reserved.

Antidiabetic Activity from Gallic Acid Encapsulated Nanochitosan

NASA Astrophysics Data System (ADS)

Purbowatiningrum; Ngadiwiyana; Ismiyarto; Fachriyah, E.; Eviana, I.; Eldiana, O.; Amaliyah, N.; Sektianingrum, A. N.

2017-02-01

Diabetes mellitus (DM) has become a health problem in the world because it causes death. One of the phenolic compounds that have antidiabetic activity is gallic acid. However, the use of this compound still provides unsatisfactory results due to its degradation during the absorption process. The solution offered to solve the problem is by encapsulated it within chitosan nanoparticles that serve to protect the bioactive compound from degradation, increases of solubility and delivery of a bioactive compound to the target site by using freeze-drying technique. The result of chitosan nanoparticle’s Scanning Electron Microscopy (SEM) showed that chitosan nanoparticle’s size is uniform and it is smaller than chitosan. The value of encapsulation efficiency (EE) of gallic acid which encapsulated within chitosan nanoparticles is about 50.76%. Inhibition test result showed that gallic acid-chitosan nanoparticles at 50 ppm could inhibite α-glucosidase activity in 28.87% with 54.94 in IC50. So it can be concluded that gallic acid can be encapsulated in nanoparticles of chitosan and proved that it could inhibit α-glucosidase.

Gallic acid as a protective antioxidant against anthocyanin degradation and color loss in vitamin-C fortified cranberry juice.

PubMed

Roidoung, Sunisa; Dolan, Kirk D; Siddiq, Muhammad

2016-11-01

The objective of this study was to evaluate different antioxidants for anthocyanin (ACY) retention in vitamin C fortified cranberry juice and assess its quality. Cranberry juice was fortified with 40-80mg/100mL vitamin C and added hesperidin, catechin, and gallic acid at different concentrations. Juice was pasteurized at 85°C for 1min and stored at 23°C for 16days. ACYs, vitamin C, color intensity, and browning index (BI) were evaluated at 2-day intervals. Gallic acid was found to be the most effective antioxidant against ACYs degradation and significantly (p<0.05) increased red color intensity by 37% and ACY concentration by 41%, compared to the control. After 16-day storage, the BI of gallic acid-added juice was significantly lower (0.80 vs 1.00) than the control juice. The outcome of this research provided a potential solution of using gallic acid to preserve a health-beneficial component (ACYs), and endogenous red color in cranberry juice. Copyright © 2016 Elsevier Ltd. All rights reserved.

[Ecology suitability of Polygonum capitatum in Guizhou province based on topographical conditions].

PubMed

Zhang, Xiaobo; Zhou, Tao; Guo, Lanping; Zhu, Shoudong; Huang, Luqi

2011-02-01

To study ecology suitability rank dividing of Polygonum capitatum for selecting artificial planting base and high-quality industrial raw material in Guizhou province. Based on the investigation of PCB and DEM data of Guizhou province, the relationship between the gallic acid content in P. capitatum and topographical conditions was analyzed by statistical analysis. The geographic information systems (GIS)-based assessment and landscape ecological principles were applied to assess ecology suitability areas of P. capitatum in Guizhou. slope, aspect and altitude are main topographical factors that affect the content of gallic acid in P. capitatum. The gallic acid content of P. capitatum is higher in the lower altitude, shady slope and smaller slope areas. The gallic acid content is higher in the eastern areas of Guizhou province.

Allelopathic potential and ecotoxicity evaluation of gallic and nonanoic acids to prevent cyanobacterial growth in lentic systems: A preliminary mesocosm study.

PubMed

Techer, Didier; Fontaine, Pascal; Personne, Aline; Viot, Sandrine; Thomas, Marielle

2016-03-15

The increase in anthropogenic nutrient loading affecting many freshwater ecosystems combined with global warming may lead to cyanobacterial blooms on an increasingly frequent basis. Among the various physicochemical and biological methods which have been proposed to rapidly control blue-green algae growth, the use of plant-derived substances such as allelochemicals has gained great interest as an environment-friendly approach. The primary aim of this work was to evaluate the efficiency of gallic and nonanoic acid application to preemptively inhibit cyanobacterial growth in lentic hydrosystems. In order to address the process feasibility under realistic exposure scenarios, thirteen outdoor freshwater mesocosms (unit volume: 3m(3)) were designed, each containing phytoplankton (including local blue-green algae species) and various non-target organisms from higher trophic levels (Physa, Lymnaea, Gammarus, and Scardinius erythrophthalmus). After an 8-week mesocosm stabilization period, a full factorial design based on the presence/absence of gallic acid (GA) and nonanoic acid (NA) (including a control group) was implemented into the exposure tanks. Regular monitoring of major phytoplankton taxa was conducted during a 28-day experiment using an on-line fluorometer. The main results suggested that gallic acid was more efficient than nonanoic acid at limiting cyanobacterial growth at concentrations as low as 1 mg L(-1). Successive gallic acid applications (at 1, 2 and 4 mg L(-1)) at the early stages of cyanobacterial growth did not allow the complete elimination of blue-green algae from the mesocosms. However, the specificity of the allelopathic effect of gallic acid towards cyanobacteria was compatible with the maintenance of a primary productivity in the treated tanks as indicated by the photoautotrophic growth of other algal taxa. Finally, no biomarker induction signal could be reported in non-target species. Further gallic acid application trials in lentic systems such as small freshwater ponds may help to design innovative allelopathy-based aquatic ecotechnologies. Copyright © 2016 Elsevier B.V. All rights reserved.

[Simultaneous isolation and purification of gallic acid and brevifolincarboxylic acid from Polygonum capitatum by high-speed counter-current chromatography].

PubMed

Chen, Xinxia; Zhang, Liyan; Wan, Jinzhi; Liang, Bin; Xie, Yu

2010-08-01

To isolate and purify gallic acid and brevifolincarboxylic acid simultaneously by high-speed counter-current chromatography (HSCCC) from a crude extract of Polygonum capitatum. The biphasic solvent system composed of ethyl acetate-n-butanol-0.44% acetic acid (3:1:5) was used at a flow rate of 2.0 mL x min(-1), while the aqueous phase was selected as the mobile phase and the apparatus was rotated at 860 r x min(-1). The effluent was detected at 272 nm. 51.5 mg of gallic acid and 5.9 mg of brevifolincarboxylic acid were separated from 1.07 g of the crude extract with the purities of 99.7% and 97.5%, respectively, while brevifolincarboxylic acid was obtained firstly from the genus Polygonum. The structures of the compounds were identified by ultraviolet spectrometry (UV), infra-red spectrometry (IR), liquid chromatography/mass spectrometry (LC/MS), time-of-flight mass spectrometry( TOF-MS), 1H-nuclear magnetic resonance (NMR) and 13C-NMR. This method is feasible and rapid for isolation and purification of gallice acid and brevifolincarboxylil acid.

Identification of protoxins and a microbial basis for red maple (Acer rubrum) toxicosis in equines.

PubMed

Agrawal, Karan; Ebel, Joseph G; Altier, Craig; Bischoff, Karyn

2013-01-01

The leaves of Acer rubrum (red maple), especially when wilted in the fall, cause severe oxidative damage to equine erythrocytes, leading to potentially fatal methemoglobinemia and hemolytic anemia. Gallic acid and tannins from A. rubrum leaves have been implicated as the toxic compounds responsible for red maple toxicosis, but the mechanism of action and toxic principle(s) have not been elucidated to date. In order to investigate further how red maple toxicosis occurs, aqueous solutions of gallic acid, tannic acid, and ground dried A. rubrum leaves were incubated with contents of equine ileum, jejunum, cecum, colon, and liver, and then analyzed for the metabolite pyrogallol, as pyrogallol is a more potent oxidizing agent. Gallic acid was observed to be metabolized to pyrogallol maximally in equine ileum contents in the first 24 hr. Incubation of tannic acid and A. rubrum leaves, individually with ileum contents, produced gallic acid and, subsequently, pyrogallol. Ileum suspensions, when passed through a filter to exclude microbes but not enzymes, formed no pyrogallol, suggesting a microbial basis to the pathway. Bacteria isolated from ileum capable of pyrogallol formation were identified as Klebsiella pneumoniae and Enterobacter cloacae. Therefore, gallotannins and free gallic acid are present in A. rubrum leaves and can be metabolized by K. pneumoniae and E. cloacae found in the equine ileum to form pyrogallol either directly or through a gallic acid intermediate (gallotannins). Identification of these compounds and their physiological effects is necessary for the development of effective treatments for red maple toxicosis in equines.

Synthesis of Gallic Acid Analogs as Histamine and Pro-Inflammatory Cytokine Inhibitors for Treatment of Mast Cell-Mediated Allergic Inflammation.

PubMed

Fei, Xiang; Je, In-Gyu; Shin, Tae-Yong; Kim, Sang-Hyun; Seo, Seung-Yong

2017-05-29

Gallic acid (3,4,5-trihydroxybenzoic acid), is a natural product found in various foods and herbs that are well known as powerful antioxidants. Our previous report demonstrated that it inhibits mast cell-derived inflammatory allergic reactions by blocking histamine release and pro-inflammatory cytokine expression. In this report, various amide analogs of gallic acid have been synthesized by introducing different amines through carbodiimide-mediated amide coupling and Pd/C-catalyzed hydrogenation. These compounds showed a modest to high inhibitory effect on histamine release and pro-inflammatory cytokine expression. Among them, the amide bearing ( S )-phenylglycine methyl ester 3d was found to be more active than natural gallic acid. Further optimization yielded several ( S )- and ( R )-phenylglycine analogs that inhibited histamine release in vitro. Our findings suggest that some gallamides could be used as a treatment for allergic inflammatory diseases.

Protective effect of gallic acid against cisplatin-induced ototoxicity in rats.

PubMed

Kilic, Korhan; Sakat, Muhammed Sedat; Akdemir, Fazile Nur Ekinci; Yildirim, Serkan; Saglam, Yavuz Selim; Askin, Seda

2018-04-07

Cisplatin is an antineoplastic agent widely used in the treatment of a variety of cancers. Ototoxicity is one of the main side-effects restricting the use of cisplatin. The purpose of this study was to investigate the protective efficacy of gallic acid, in biochemical, functional and histopathological terms, against ototoxicity induced by cisplatin. Twenty-eight female Sprague Dawley rats were included. Rats were randomly assigned into four groups of seven animals each. Cisplatin group received a single intraperitoneal dose of 15mg/kg cisplatin. Gallic acid group received intraperitoneal gallic acid at 100mg/kg for five consecutive days. Cisplatin+Gallic acid group received intraperitoneal gallic acid at 100mg/kg for five consecutive days and a single intraperitoneal dose of 15mg/kg cisplatin at 3rd day. A control group received 1mL intraperitoneal saline solution for five consecutive days. Prior to drug administration, all rats were exposed to the distortion product otoacoustic emissions test. The test was repeated on the 6th day of the study. All rats were then sacrificed; the cochleas were removed and set aside for biochemical and histopathological analyses. In Cisplatin group, Day 6 signal noise ratio values were significantly lower than those of the other groups. Also, malondialdehyde levels in cochlear tissues were significantly higher, superoxide dismutase and glutathione peroxidase activities were significantly lower compared to the control group. Histopathologic evaluation revealed erosion in the stria vascularis, degeneration and edema in the connective tissue layer in endothelial cells, impairment of outer hair cells and a decrease in the number of these calls. In the Cisplatin+Gallic acid group, this biochemical, histopathological and functional changes were reversed. In the light of our findings, we think that gallic acid may have played a protective role against cisplatin-induced ototoxicity in rats, as indicated by the distortion product otoacoustic emissions test results, biochemical findings and immunohistochemical analyses. Copyright © 2018 Associação Brasileira de Otorrinolaringologia e Cirurgia Cérvico-Facial. Published by Elsevier Editora Ltda. All rights reserved.

Gallic acid-capped gold nanoparticles inhibit EGF-induced MMP-9 expression through suppression of p300 stabilization and NFκB/c-Jun activation in breast cancer MDA-MB-231 cells.

PubMed

Chen, Ying-Jung; Lee, Yuan-Chin; Huang, Chia-Hui; Chang, Long-Sen

2016-11-01

Triple-negative breast cancers (TNBCs) are highly invasive and have a higher rate of distant metastasis. Matrix metalloproteinase-9 (MMP-9) plays a crucial role in EGF/EGFR-mediated malignant progression and metastasis of TNBCs. Various studies have revealed that treatment with gallic acid down-regulates MMP-9 expression in cancer cells, and that conjugation of phytochemical compounds with gold nanoparticles (AuNPs) increases the anti-tumor activity of the phytochemical compounds. Thus, the effect of gallic acid-capped AuNPs (GA-AuNPs) on MMP-9 expression in EGF-treated TNBC MDA-MB-231 cells was analyzed in the present study. The so-called green synthesis of AuNPs by means of gallic acid was performed at pH10, and the resulting GA-AuNPs had spherical shape with an average diameter of approximately 50nm. GA-AuNPs notably suppressed migration and invasion of EGF-treated cells, and inhibited EGF-induced MMP-9 up-regulation. GA-AuNPs abrogated EGF-induced Akt/p65 and ERK/c-Jun phosphorylation, leading to down-regulation of MMP-9 mRNA and protein expression in EGF-treated cells. Meanwhile, EGF-induced p300 stabilization was found to be involved in MMP-9 expression, whereas GA-AuNPs inhibited the EGF-promoted stability of the p300 protein. Although GA-AuNPs and gallic acid suppressed EGF-induced MMP-9 up-regulation via the same signaling pathway, the effective concentration of gallic acid was approximately 100-fold higher than that of GA-AuNPs for inhibition of MMP-9 expression in EGF-treated cells to a similar extent. Collectively, our data indicate that, in comparison with gallic acid, GA-AuNPs have a superior ability to inhibit EGF/EGFR-mediated MMP-9 expression in TNBC MDA-MB-231 cells. Our findings also point to a way to improve the anti-tumor activity of gallic acid. Copyright © 2016 Elsevier Inc. All rights reserved.

Characterization of phenolic compounds of thorny and thornless blackberries.

PubMed

Kolniak-Ostek, Joanna; Kucharska, Alicja Z; Sokół-Łętowska, Anna; Fecka, Izabela

2015-03-25

The aim of this study was to identify and compare the contents of phenolic acids, tannins, anthocyanins, and flavonoid glycosides in thorny and thornless blackberries. Five thorny and nine thornless cultivars were used for this study. Thirty-five phenolic compounds were determined in the examined fruits, and one phenolic acid, three ellagic acid derivatives, one anthocyanin, and six flavonols were characterized for the first time in blackberries. The thornless fruits were characterized by a higher content of anthocyanins (mean = 171.23 mg/100 g FW), ellagitannins (mean = 3.65 mg/100 g FW), and ellagic acid derivatives (mean = 2.49 mg/100 g FW), in comparison to thorny ones. At the same time, in thorny fruits, the contents of hydroxycinnamic acids (mean = 1.42 mg/100 g FW) and flavonols (mean = 5.70 mg/100 g FW) were higher.

[Gallic acid inhibits inflammatory response of RAW264.7 macrophages by blocking the activation of TLR4/NF-κB induced by LPS].

PubMed

Huang, Lihua; Hou, Lin; Xue, Hainan; Wang, Chunjie

2016-12-01

Objective To observe the influence of gallic acid on Toll-like receptor 4/nuclear factor-κB (TLR4/NF-κB) pathway in the RAW264.7 macrophages stimulated by lipopolysaccharide (LPS). Methods RAW264.7 macrophages were divided into the following groups: control group, LPS group, LPS combined with gallic acid group, LPS combined with pyrrolidine dithiocarbamate (PDTC) group and LPS combined with dexamethasone (DM) group. RAW264.7 cells were cultured for 24 hours after corresponding treatments. The levels of tumor necrosis factor α (TNF-α), interleukin-1 (IL-1) and IL-6 were detected by ELISA. The levels of TLR4 and NF-κB mRNAs were tested by real-time PCR. The levels of p-IκBα, p65, p-p65 and TLR4 proteins were examined by Western blotting. Results The expression levels of TNF-α, IL-1 and IL-6 were up-regulated in the RAW264.7 macrophages after stimulated by LPS. Gallic acid could reduce the elevated expression levels of TNF-α, IL-1 and IL-6 induced by LPS. The expression of TLR4 significantly increased after stimulated by LPS and NF-κB was activated. Gallic acid could reverse the above changes and prevent the activation of NF-κB. Conclusion Gallic acid could inhibit LPS-induced inflammatory response in RAW264.7 macrophages via TLR4/NF-κB pathway.

Effect of the structure of gallic acid and its derivatives on their interaction with plant ferritin.

PubMed

Wang, Qunqun; Zhou, Kai; Ning, Yong; Zhao, Guanghua

2016-12-15

Gallic acid and its derivatives co-exist with protein components in foodstuffs, but there is few report on their interaction with proteins. On the other hand, plant ferritin represents not only a novel class of iron supplement, but also a new nanocarrier for encapsulation of bioactive nutrients. However, plant ferritin is easy to be degraded by pepsin in the stomach, thereby limiting its application. Herein, we investigated the interaction of gallic acid and its derivatives with recombinant soybean seed H-2 ferritin (rH-2). We found that these phenolic acids interacted with rH-2 in a structure-dependent manner; namely, gallic acid (GA), methyl gallate (MEGA) and propyl gallate (PG) having three HO groups can bind to rH-2, while their analogues with two HO groups cannot. Consequently, such binding largely inhibited ferritin degradation by pepsin. These findings advance our understanding of the relationship between the structure and function of phenolic acids. Copyright © 2016 Elsevier Ltd. All rights reserved.

Root-secreted allelochemical in the noxious weed Phragmites australis deploys a reactive oxygen species response and microtubule assembly disruption to execute rhizotoxicity.

PubMed

Rudrappa, Thimmaraju; Bonsall, Justin; Gallagher, John L; Seliskar, Denise M; Bais, Harsh P

2007-10-01

Phragmites australis is considered the most invasive plant in marsh and wetland communities in the eastern United States. Although allelopathy has been considered as a possible displacing mechanism in P. australis, there has been minimal success in characterizing the responsible allelochemical. We tested the occurrence of root-derived allelopathy in the invasiveness of P. australis. To this end, root exudates of two P. australis genotypes, BB (native) and P38 (an exotic) were tested for phytotoxicity on different plant species. The treatment of the susceptible plants with P. australis root exudates resulted in acute rhizotoxicity. It is interesting to note that the root exudates of P38 were more effective in causing root death in susceptible plants compared to the native BB exudates. The active ingredient in the P. australis exudates was identified as 3,4,5-trihydroxybenzoic acid (gallic acid). We tested the phytotoxic efficacy of gallic acid on various plant systems, including the model plant Arabidopsis thaliana. Most tested plants succumbed to the gallic acid treatment with the exception of P. australis itself. Mechanistically, gallic acid treatment generated elevated levels of reactive oxygen species (ROS) in the treated plant roots. Furthermore, the triggered ROS mediated the disruption of the root architecture of the susceptible plants by damaging the microtubule assembly. The study also highlights the persistence of the exuded gallic acid in P. australis's rhizosphere and its inhibitory effects against A. thaliana in the soil. In addition, gallic acid demonstrated an inhibitory effect on Spartina alterniflora, one of the salt marsh species it successfully invades.

Emblica officinalis (Amla): A review for its phytochemistry, ethnomedicinal uses and medicinal potentials with respect to molecular mechanisms.

PubMed

Variya, Bhavesh C; Bakrania, Anita K; Patel, Snehal S

2016-09-01

Medicinal plants, having great elementary and therapeutic importance, are the gift to mankind to acquire healthy lifestyle. Emblica officinalis Gaertn. or Phyllanthus emblica Linn. (Euphorbeaceae), commonly known as Indian gooseberry or Amla, has superior value in entirely indigenous traditional system of medicine, including folklore Ayurveda, for medicinal and nutritional purposes to build up lost vitality and vigor. In this article, numerous phytochemicals isolated from E. officinalis and its ethnomedical and pharmacological potentials with molecular mechanisms are briefly deliberated and recapitulated. The information documented in the present review was collected from more than 270 articles, published or accepted in the last five to six decades, and more than 20 e-books using various online database. Additional information was obtained from various botanical books and dissertations. The extracts from various parts of E. officinalis, especially fruit, contain numerous phytoconstituents viz. higher amount of polyphenols like gallic acid, ellagic acid, different tannins, minerals, vitamins, amino acids, fixed oils, and flavonoids like rutin and quercetin. The extract or plant is identified to be efficacious against diversified ailments like inflammation, cancer, osteoporosis, neurological disorders, hypertension together with lifestyle diseases, parasitic and other infectious disorders. These actions are attributed to either regulation of various molecular pathway involved in several pathophysiologies or antioxidant property which prevents the damage of cellular compartments from oxidative stress. However, serious efforts are required in systemic research to identify, isolate and evaluate the chemical constituents for nutritional and therapeutic potentials. Copyright © 2016 Elsevier Ltd. All rights reserved.

Gallic acid and p-coumaric acid attenuate type 2 diabetes-induced neurodegeneration in rats.

PubMed

Abdel-Moneim, Adel; Yousef, Ahmed I; Abd El-Twab, Sanaa M; Abdel Reheim, Eman S; Ashour, Mohamed B

2017-08-01

The brain of diabetics revealed deterioration in many regions, especially the hippocampus. Hence, the present study aimed to evaluate the effects of gallic acid and p-coumaric acid against the hippocampal neurodegeneration in type 2 diabetic rats. Adult male albino rats were randomly allocated into four groups: Group 1 served as control ones and others were induced with diabetes. Group 2 considered as diabetic, and groups 3 and 4 were further orally treated with gallic acid (20 mg/kg b.wt./day) and p-coumaric acid (40 mg/kg b.wt./day) for six weeks. Diabetic rats revealed significant elevation in the levels of serum glucose, blood glycosylated hemoglobin and serum tumor necrosis factor-α, while the level of serum insulin was significantly declined. Furthermore, the brain of diabetic rats showed a marked increase in oxidative stress and a decrease of antioxidant parameters as well as upregulation the protein expression of Bax and downregulation the protein expression of Bcl-2 in the hippocampus. Treatment of diabetic rats with gallic acid and p-coumaric acid significantly ameliorated glucose tolerance, diminished the brain oxidative stress and improved antioxidant status, declined inflammation and inhibited apoptosis in the hippocampus. The overall results suggested that gallic acid and p-coumaric acid may inhibit hippocampal neurodegeneration via their potent antioxidant, anti-inflammatory and anti-apoptotic properties. Therefore, both compounds can be recommended as hopeful adjuvant agents against brain neurodegeneration in diabetics.

Preparation and bactericide activity of gallic acid stabilized gold nanoparticles

NASA Astrophysics Data System (ADS)

Moreno-Álvarez, S. A.; Martínez-Castañón, G. A.; Niño-Martínez, N.; Reyes-Macías, J. F.; Patiño-Marín, N.; Loyola-Rodríguez, J. P.; Ruiz, Facundo

2010-10-01

In this work, gold nanoparticles with three different sizes (13.7, 39.4, and 76.7 nm) were prepared using a simple aqueous method with gallic acid as the reducing and stabilizing agent, the different sizes were obtained varying some experimental parameters as the pH of the reaction and the amount of the gallic acid. The prepared nanoparticles were characterized using X-ray diffraction, transmission electron microscopy, dynamic light scattering, and UV-Vis spectroscopy. Samples were identified as elemental gold and present spherical morphology, a narrow size distribution and good stabilization according to TEM and DLS results. The antibacterial activity of this gallic acid stabilized gold nanoparticles against S. mutans (the etiologic agent of dental caries) was assessed using a microdilution method obtaining a minimum inhibitory concentration of 12.31, 12.31, and 49.25 μg/mL for 13.7, 39.4, and 76.7 nm gold nanoparticles, respectively. The antibacterial assay showed that gold nanoparticles prepared in this work present a bactericide activity by a synergistic action with gallic acid. The MIC found for this nanoparticles are much lower than those reported for mixtures of gold nanoparticles and antibiotics.

Computational study of molecular electrostatic potential, docking and dynamics simulations of gallic acid derivatives as ABL inhibitors.

PubMed

Raghi, K R; Sherin, D R; Saumya, M J; Arun, P S; Sobha, V N; Manojkumar, T K

2018-04-05

Chronic myeloid leukemia (CML), a hematological malignancy arises due to the spontaneous fusion of the BCR and ABL gene, resulting in a constitutively active tyrosine kinase (BCR-ABL). Pharmacological activity of Gallic acid and 1,3,4-Oxadiazole as potential inhibitors of ABL kinase has already been reported. Objective of this study is to evaluate the ABL kinase inhibitory activity of derivatives of Gallic acid fused with 1,3,4-Oxadiazole moieties. Attempts have been made to identify the key structural features responsible for drug likeness of the Gallic acid and the 1,3,4-Oxadiazole ring using molecular electrostatic potential maps (MESP). To investigate the inhibitory activity of Gallic acid derivatives towards the ABL receptor, we have applied molecular docking and molecular dynamics (MD) simulation approaches. A comparative study was performed using Bosutinib as the standard which is an approved CML drug acting on the same receptor. Furthermore, the novel compounds designed and reported here in were evaluated for ADME properties and the results indicate that they show acceptable pharmacokinetic properties. Accordingly these compounds are predicted to be drug like with low toxicity potential. Copyright © 2018 Elsevier Ltd. All rights reserved.

EGFR-dependent signalling reduced and p38 dependent apoptosis required by Gallic acid in Malignant Mesothelioma cells.

PubMed

Demiroglu-Zergeroglu, Asuman; Candemir, Gulsife; Turhanlar, Ebru; Sagir, Fatma; Ayvali, Nurettin

2016-12-01

The unrestrained EGFR signalling contributes to malignant phenotype in a number of cancers including Malignant Mesotheliomas. Present study was designed to evaluate EGFR-dependent anti-proliferative and apoptotic effects of Gallic acid in transformed Mesothelial (MeT-5A) and Malignant Mesothelioma (SPC212) cells. Gallic acid reduced the viability of Malignant Mesothelioma cells in a concentration and time-dependent manner. However, viability of mesothelial cells reduced only at high concentration and longer time periods. Gallic acid restrained the activation of EGFR, ERK1/2 and AKT proteins and down regulated expression of Cyclin D and Bcl-2 genes, but upregulated the expression of p21 gene in EGF-induced SPC212 cells. GA-induced transitory G1 arrest and triggered mitochondrial and death receptor mediated apoptosis, which requires p38MAPK activation. The data provided here indicate that GA is able to inhibit EGFR dependent proliferation and survival signals and induces p38 pathway dependent apoptosis in Malignant Mesothelioma cells. On the basis of these experimental findings it is worthwhile to investigate further the biological activity of Gallic acid on other Mesothelioma cell lines harbouring aberrant EGFR signals. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

Polyphenols of Salix aegyptiaca modulate the activities of drug metabolizing and antioxidant enzymes, and level of lipid peroxidation.

PubMed

Nauman, Mohd; Kale, R K; Singh, Rana P

2018-03-07

Salix aegyptiaca is known for its medicinal properties mainly due to the presence of salicylate compounds. However, it also contains other beneficial phytochemicals such as gallic acid, quercetin, rutin and vanillin. The aim of the study was to examine the redox potential, antioxidant and anti-inflammatory activity of these phytochemicals along with acetylsalicylic acid. The redox potential and antioxidant activity of gallic acid, quercetin, rutin, vanillin and acetylsalicylic acid were determined by oxidation-reduction potential electrode method and 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay, respectively. In ex vivo studies, antioxidant activity of these phytochemicals was determined by lipid peroxidation and carbonyl content assay in the liver of mice. Anti-inflammatory activity was determined by protein denaturation method. Six-week old C57BL/6 mice treated with gallic acid (100 mg/kg body weight) and acetylsalicylic acid (25 and 50 mg/kg body weight) to investigate their in vivo modulatory effects on the specific activities of drug metabolizing phase I and phase II enzymes, antioxidant enzymes and level of lipid peroxidation in liver. The order of ability to donate electron and antioxidant activity was found to be: gallic acid > quercetin > rutin > vanillin > acetylsalicylic acid. In ex vivo studies, the similar pattern and magnitude of inhibitory effects of these phytochemicals against peroxidative damage in microsomes and protein carbonyl in cytosolic fraction were observed. In in vivo studies, gallic acid and acetylsalicylic acid alone or in combination, enhanced the specific activities of drug metabolizing phase I and phase II enzymes as well as antioxidant enzymes and also inhibited lipid peroxidation in liver. These findings show a close link between the electron donation and antioxidation potential of these phytochemicals, and in turn their biological activity. Gallic acid, quercetin, rutin and vanillin were found to be better electron donors and antioxidants and therefore, might be mainly responsible for the antioxidant properties of S. aegyptiaca, while acetylsalicylic acid provided its maximum anti-inflammatory activity.

Plant Natural compounds with antibacterial activity towards common pathogens of pond-cultured channel catfish (Ictalurus punctatus).

PubMed

Schrader, Kevin K

2010-07-01

The bacteria Edwardsiella ictaluri and Flavobacterium columnare cause enteric septicemia and columnaris disease, respectively, in channel catfish (Ictalurus punctatus). Natural therapeutants may provide an alternative to current management approaches used by producers. In this study, a rapid bioassay identified plant compounds as potential therapeutants. Chelerythrine chloride and ellagic acid were the most toxic toward E. ictaluri, with 24-h IC50 of 7.3 mg/L and 15.1 mg/L, respectively, and MIC of 2.1 mg/L and 6.5 mg/L, respectively. Chelerythrine chloride, ellagic acid, β-glycyrrhetinic acid, sorgoleone, and wogonin were the most toxic towards two genomovars of F. columnare, and wogonin had the strongest antibacterial activity (MIC = 0.3 mg/L).

Improved Anticancer Effect of Magnetite Nanocomposite Formulation of GALLIC Acid (Fe₃O₄-PEG-GA) Against Lung, Breast and Colon Cancer Cells.

PubMed

Rosman, Raihana; Saifullah, Bullo; Maniam, Sandra; Dorniani, Dena; Hussein, Mohd Zobir; Fakurazi, Sharida

2018-02-02

Lung cancer, breast cancer and colorectal cancer are the most prevalent fatal types of cancers globally. Gallic acid (3,4,5-trihydroxybenzoic acid) is a bioactive compound found in plants and foods, such as white tea, witch hazel and it has been reported to possess anticancer, antioxidant and anti-inflammatory properties. In this study we have redesigned our previously reported anticancer nanocomposite formulation with improved drug loading based on iron oxide magnetite nanoparticles coated with polyethylene glycol and loaded with anticancer drug gallic acid (Fe₃O₄-PEG-GA). The in vitro release profile and percentage drug loading were found to be better than our previously reported formulation. The anticancer activity of pure gallic acid (GA), empty carrier (Fe₃O₄-PEG) nanocarrier and of anticancer nanocomposite (Fe₃O₄-PEG-GA) were screened against human lung cancer cells (A549), human breast cancer cells (MCF-7), human colon cancer cells (HT-29) and normal fibroblast cells (3T3) after incubation of 24, 48 and 72 h using (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) MTT assay. The designed formulation (Fe₃O₄-PEG-GA) showed better anticancer activity than free gallic acid (GA). The results of the in vitro studies are highly encouraging to conduct the in vivo studies.

Phenolic Extracts from Clerodendrum volubile Leaves Inhibit Cholinergic and Monoaminergic Enzymes Relevant to the Management of Some Neurodegenerative Diseases.

PubMed

Oboh, Ganiyu; Ogunruku, Omodesola O; Oyeleye, Sunday I; Olasehinde, Tosin A; Ademosun, Ayokunle O; Boligon, Aline Augusti

2017-05-04

This study investigated the inhibitory effects of phenolic-rich extracts from Clerodendrum volubile leaves on cholinergic [acetylcholinesterase (AChE) and butyrylcholinesterase (BChE)] and monoaminergic [monoamine oxidase (MAO)] enzymes' activities and pro-oxidants [Fe 2+ and quinolinic acid-(QA)] induced lipid peroxidation in rats brain homogenates in vitro. Free phenolic extracts (FPE) and bound phenolic extracts (BPE) were obtained via solvent extraction, and the total phenol and flavonoid contents were evaluated. The phenolic constituents of the extracts were also determined using high performance liquid chromatography coupled with diode array detector (HPLC-DAD). Our findings revealed that FPE had higher AChE (2.06 μg/mL), BChE (2.79 μg/mL), and MAO (2.81 μg/mL) inhibitory effects than BPE [AChE, 2.80 μg/mL; BChE, 3.40 μg/mL; MAO, 3.39 μg/mL]. Furthermore, FPE also had significantly (P < 0.05) higher inhibitory effects on Fe 2+ and QA-induced lipid peroxidation compared to BPE. FPE (162.61 mg GAE/g) had higher total phenol content than BPE. However, BPE (18.65 mg QE/g) had significantly higher total flavonoid content than FPE (13.32 mg QE/g). Phenolic acids (such as gallic acid, catechin, chlorogenic, caffeic, ellagic, p-Coumaric acids) and flavonoids (catechins, rutin and quercetin) were present in both extracts. This study revealed that the enzymes' inhibitory activities and antioxidant potentials of phenolic-rich extracts from C. volubile could be part of the mechanism of actions behind its use for memory/cognitive function as obtained in folklore. However, FPE exhibited significantly higher enzymes, inhibitory and antioxidant potentials than BPE.

Antimicrobial activity of pomegranate peel extracts as affected by cultivar.

PubMed

Rosas-Burgos, Ema C; Burgos-Hernández, Armando; Noguera-Artiaga, Luis; Kačániová, Miroslava; Hernández-García, Francisca; Cárdenas-López, José L; Carbonell-Barrachina, Ángel A

2017-02-01

Some studies have reported that different parts of the pomegranate fruit, especially the peel, may act as potential antimicrobial agents and thus might be proposed as a safe natural alternative to synthetic antimicrobial agents. The high tannin content, especially punicalagin, found in pomegranate extracts, has been reported as the main compound responsible for such antimicrobial activity. Because the pomegranate peel chemical composition may vary with the type of cultivar (sweet, sour-sweet and sour), pomegranates may also differ with respect to their antimicrobial capacity. The extract from PTO8 pomegranate cultivar peel had the highest antimicrobial activity, as well as the highest punicalagins (α and β) and ellagic acid concentrations. In the results obtained from both antibacterial and antifungal activity studies, the sour-sweet pomegranate cultivar PTO8 showed the best antimicrobial activity, and the highest ellagic acid concentrations. The results of the present study suggest that ellagic acid content has a significant influence on the antimicrobial activity of the pomegranate extracts investigated. The pomegranate peel of the PTO8 cultivar is a good source of antifungal and antibacterial compounds, and may represent an alternative to antimicrobial agents of synthetic origin. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

Sea Buckthorn Leaf Extract Protects Jejunum and Bone Marrow of (60)Cobalt-Gamma-Irradiated Mice by Regulating Apoptosis and Tissue Regeneration.

PubMed

Bala, Madhu; Gupta, Manish; Saini, Manu; Abdin, M Z; Prasad, Jagdish

2015-01-01

A single dose (30 mg/kg body weight) of standardized sea buckthorn leaf extract (SBL-1), administered 30 min before whole body (60)Co-gamma-irradiation (lethal dose, 10 Gy), protected >90% of mice population. The purpose of this study was to investigate the mechanism of action of SBL-1 on jejunum and bone marrow, quantify key bioactive compounds, and analyze chemical composition of SBL-1. Study with 9-week-old inbred male Swiss albino Strain 'A' mice demonstrated that SBL-1 treatment before (60)Co-gamma-irradiation (10 Gy) significantly (p < 0.05) countered radiation induced decreases in jejunum crypts (1.27-fold), villi number (1.41-fold), villus height (1.25-fold), villus cellularity (2.27-fold), cryptal Paneth cells (1.89-fold), and Bcl2 level (1.54-fold). It countered radiation induced increases in cryptal apoptotic cells (1.64-fold) and Bax levels (1.88-fold). It also countered radiation (2 Gy and 3 Gy) induced bone marrow apoptosis (1.59-fold and 1.85-fold) and micronuclei frequency (1.72-fold and 2.6-fold). SBL-1 rendered radiation protection by promoting cryptal stem cells proliferation, by regulating apoptosis, and by countering radiation induced chromosomal damage. Quercetin, Ellagic acid, Gallic acid, high contents polyphenols, tannins, and thiols detected in SBL-1 may have contributed to radiation protection by neutralization of radiation induced oxidative species, supporting stem cell proliferation and tissue regeneration.

Unique bioactive polyphenolic profile of guava (Psidium guajava) budding leaf tea is related to plant biochemistry of budding leaves in early dawn.

PubMed

Chang, Chi-Huang; Hsieh, Chiu-Lan; Wang, Hui-Er; Peng, Chiung-Chi; Chyau, Charng-Cherng; Peng, Robert Y

2013-03-15

Guava leaf tea (GLT), exhibiting a diversity of medicinal bioactivities, has become a popularly consumed daily beverage. To improve the product quality, a new process was recommended to the Ser-Tou Farmers' Association (SFA), who began field production in 2005. The new process comprised simplified steps: one bud-two leaves were plucked at 3:00-6:00 am, in the early dawn period, followed by withering at ambient temperature (25-28 °C), rolling at 50 °C for 50-70 min, with or without fermentation, then drying at 45-50 °C for 70-90 min, and finally sorted. The product manufactured by this new process (named herein GLTSF) exhibited higher contents (in mg g(-1), based on dry ethyl acetate fraction/methanolic extract) of polyphenolics (417.9 ± 12.3) and flavonoids (452.5 ± 32.3) containing a compositional profile much simpler than previously found: total quercetins (190.3 ± 9.1), total myricetin (3.3 ± 0.9), total catechins (36.4 ± 5.3), gallic acid (8.8 ± 0.6), ellagic acid (39.1 ± 6.4) and tannins (2.5 ± 9.1). We have successfully developed a new process for manufacturing GLTSF with a unique polyphenolic profile. Such characteristic compositional distribution can be ascribed to the right harvesting hour in the early dawn and appropriate treatment process at low temperature, avoiding direct sunlight. © 2012 Society of Chemical Industry.

Evaluation of acute and subacute toxicity and mutagenic activity of the aqueous extract of pecan shells [Carya illinoinensis (Wangenh.) K. Koch].

PubMed

Porto, Luiz Carlos Santos; da Silva, Juliana; Ferraz, Alexandre de Barros Falcão; Corrêa, Dione Silva; dos Santos, Marcela Silva; Porto, Caroline Dalla Lana; Picada, Jaqueline Nascimento

2013-09-01

The infusion of pecan shells has been used to prevent and control hypercholesterolemia, diabetes and toxicological diseases. The aim of the present study was to evaluate toxicity and mutagenic effects of pecan shells aqueous extract (PSAE). Wistar rats were treated with a single dose of 300 or 2000 mg/kg of PSAE in the acute toxicity test. For the subacute test, the animals received 10 or 100 mg/kg of PSAE for 28 days. The mutagenicity was evaluated using Salmonella/microsome assay in TA1535, TA1537, TA98, TA100 and TA102 S. typhimurium strains in the presence and absence of metabolic activation (S9 mix) and micronucleus test in bone marrow. HPLC analyses indicated the presence of tannins, flavonoids, gallic and ellagic acids. Except for triglycerides, all treated groups presented normal hematological and biochemical parameters. Lower levels of triglycerides and weight loss were observed in the 100 mg/kg group. Mutagenic activities were not detected in S. typhimurium strains and by the micronucleus test. Based on these results, PSAE was not able to induce chromosomal or point mutations, under the conditions tested. The 100mg/kg dose showed significant antihyperlipidemic action, with no severe toxic effects. Copyright © 2013 Elsevier Ltd. All rights reserved.

Highly selective and efficient imprinted polymers based on carboxyl-functionalized magnetic nanoparticles for the extraction of gallic acid from pomegranate rind.

PubMed

Zhang, Junjie; Li, Benqiang; Yue, Huijuan; Wang, Jing; Zheng, Yuansuo

2018-01-01

With the combined surface imprinting technique and immobilized template strategy, molecularly imprinted magnetic nanoparticles were successfully prepared and coupled with high-performance liquid chromatography to selectively separate and determine gallic acid from the pomegranate rind. On the surface of carboxyl-functionalized magnetic nanospheres, thin imprinting shells were formed using dopamine as monomer and crosslinker. The characteristics, polymerization conditions, and adsorption performances of the resultant nanomaterials were investigated in detail. In addition of good crystallinity, satisfactory magnetism, and uniform morphology of the obtained polymers, they had rapid binding kinetics, high adsorption capacity, and favorable reusability. In the mixed solution of four hydroxybenzoic acids, the prepared nanomaterials have an excellent selectivity to gallic acid with an imprinting factor of as high as 17.5. Therefore, the polymers have great potentials in specific extraction and enrichment of gallic acid from the complex natural resources. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Gallic Acid Content in Taiwanese Teas at Different Degrees of Fermentation and Its Antioxidant Activity by Inhibiting PKCδ Activation: In Vitro and in Silico Studies.

PubMed

Kongpichitchoke, Teeradate; Chiu, Ming-Tzu; Huang, Tzou-Chi; Hsu, Jue-Liang

2016-10-12

Teas can be classified according to their degree of fermentation, which has been reported to affect both the bioactive components in the teas and their antioxidative activity. In this study, four kinds of commercial Taiwanese tea at different degrees of fermentation, which include green (non-fermented), oolong (semi-fermented), black (fully fermented), and Pu-erh (post-fermented) tea, were profiled for catechin levels by using high performance liquid chromatography (HPLC). The result indicated that the gallic acid content in tea was directly proportional to the degree of fermentation in which the lowest and highest gallic acid content were 1.67 and 21.98 mg/g from green and Pu-erh tea, respectively. The antioxidative mechanism of the gallic acid was further determined by in vitro and in silico analyses. In vitro assays included the use of phorbol ester-induced macrophage RAW264.7 cell model for determining the inhibition of reactive oxygen species (ROS) production, and PKCδ and nicotinamide adenine dinucleotide phosphate (NADPH) oxidase subunit (p47) activations. The results showed that only at a concentration of 5.00 μM could gallic acid significantly ( p < 0.05) reduce ROS levels in phorbol ester-activated macrophages. Moreover, protein immunoblotting expressed similar results in which activations of PKCδ and p47 were only significantly ( p < 0.05) attenuated by 5.00 μM treatment. Lastly, in silico experiments further revealed that gallic acid could block PKCδ activation by occupying the phorbol ester binding sites of the protein.

Proceedings of the Natick Science Symposium (4th) Held in Natick, Massachusetts on 9-10 June 1992

DTIC Science & Technology

1992-09-01

HQ - hydroquinone; MG - methyl gallate; CA - caffeic acid ; CHIA - chlorogenic acid ; GA - gallic acid ; FOLY - polymeric antioxidant. Values shown...examples 268 FQRrER & BIACK (qu~tin, hydroquinone, caffeic acid , chlorogenic acid and gallic acid ) , these are relatively ineffective in HSV...unless covalently bonded to the membrane. 279 SENECAL & RAND A membrane lactase reactor, modelled after the mammalian small intestine, has been

Gallic acid reduces cell growth by induction of apoptosis and reduction of IL-8 in HepG2 cells.

PubMed

Lima, Kelly Goulart; Krause, Gabriele Catyana; Schuster, Aline Daniele; Catarina, Anderson Velasque; Basso, Bruno Souza; De Mesquita, Fernanda Cristina; Pedrazza, Leonardo; Marczak, Elisa Simon; Martha, Bianca Andrade; Nunes, Fernanda Bordignon; Chiela, Eduardo Cremonese Filippi; Jaeger, Natália; Thomé, Marcos Paulo; Haute, Gabriela Viegas; Dias, Henrique Bregolin; Donadio, Márcio Vinícius Fagundes; De Oliveira, Jarbas Rodrigues

2016-12-01

Hepatocellular carcinoma is the most prevalent primary liver tumor and is among the top ten cancer that affect the world population. Its development is related, in most cases, to the existence of chronic liver injury, such as in cirrhosis. The knowledge about the correlation between chronic inflammation and cancer has driven new researches with anti-inflammatory agents that have potential for the development of antitumor drugs. Gallic acid is a phenolic acid found in many natural products and have shown anti-inflammatory, anti-tumor, anti-mutagenic and antioxidant actions. The purpose of this study was to investigate the effect of gallic acid on acute and chronic cell proliferation and inflammatory parameters of hepatocellular carcinoma cells (HepG2), as well as to investigate the mechanisms involved. Results showed that the gallic acid decreased the proliferation of HepG2 cells in a dose-dependent manner (Trypan blue exclusion assay), without causing necrosis (LDH assay). We observed a significant increase in the percentage of small and regular nuclei (Nuclear Morphometric Analysis assay), a significant induction of apoptosis by Annexin V-FITC and PI assay and no interference with the cell cycle using the FITC BrdU Flow Kit. We observed a significant reduction in the levels of IL-8 and increased levels of IL-10 and IL-12 (Cytometric Bead Array Human Inflammation Assay). Furthermore, gallic acid caused no cancer cells regrowth at a long term (Cumulative Population Doubling assay). According to these results, gallic acid showed a strong potential as an anti-tumor agent in hepatocellular carcinoma cells. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

Synergistic effect of the combination of gallic acid and famotidine in protection of rat gastric mucosa.

PubMed

Asokkumar, K; Sen, Saikat; Umamaheswari, M; Sivashanmugam, A T; Subhadradevi, V

2014-08-01

Antioxidant supplements with existing drugs may confer better therapeutic efficacy in oxidative stress related diseases. The purpose of the present work was to characterize the interaction and investigate the protective effect of H2 blocker famotidine and gallic acid in combination against experimentally induced peptic ulcer. Preventive effect of gallic acid and famotidine in different combinations was investigated against aspirin plus pyloric ligation induced ulcer in rat. Ulcer index, gastric juice volume, pH, other biochemical parameters of gastric juice and antioxidant activity using stomach tissue were estimated. Pretreatment with gallic acid and famotidine in combinations for 7 days, protected the gastric mucosa significantly (p<0.05, 0.01), which was evidenced by decrease in ulcer index, gastric juice volume, free and total acidity, total protein, pepsin and DNA content, and increase in pH, carbohydrates concentration in gastric juice. Combination treatment increases levels of superoxide dismutase, catalase, reduced glutathione, glutathione reductase and glucose-6-phosphate dehydrogenase, and decreases lipid peroxidation, myloperoxidase in stomach tissue. Along with higher dose combination, lower dose combinations like gallic acid (50mg/kg) plus famotidine (10mg/kg) also offered better antiulcer activity than their individual effect. Histopathological studies confirmed their antiulcer activity. Combination treatments confer synergistic protective effect against peptic ulcer in rats, which was related to the gastroprotective, antisecratory and antioxidant activity of combination treatment. Results proved that use of gallic acid with existing antiulcer drug will be more useful in the prevention/management of peptic ulcer. Copyright © 2014 Institute of Pharmacology, Polish Academy of Sciences. Published by Elsevier Urban & Partner Sp. z o.o. All rights reserved.

The effects of gallic/ferulic/caffeic acids on colour intensification and anthocyanin stability.

PubMed

Qian, Bing-Jun; Liu, Jian-Hua; Zhao, Shu-Juan; Cai, Jian-Xiong; Jing, Pu

2017-08-01

The mechanism by which copigments stabilize colour, by protecting anthocyanin chromophores from nucleophilic attack, seems well accepted. This study was to determine effects of gallic/ferulic/caffeic acids on colour intensification and anthocyanin stability. Molecular dynamics simulations were applied to explore molecular interactions. Phenolic acids intensified the colour by 19%∼27%. Colour fading during heating followed first-order reactions with half-lives of 3.66, 9.64, 3.50, and 3.39h, whereas anthocyanin degradation, determined by the pH differential method (or HPLC-PDA), followed second-order reactions with half-lives of 3.29 (3.40), 3.43 (3.39), 2.29 (0.39), and 2.72 (0.32)h alone or with gallic/ferulic/caffeic acids, respectively, suggesting that anthocyanin degradation was faster than the colour fading. The strongest protection of gallic acids might be attributed to the shortest distance (4.37Å) of its aromatic ring to the anthocyanin (AC) panel. Hyperchromic effects induced by phenolic acids were pronounced and they obscured the accelerated anthocyanin degradation due to self-association interruption. Copyright © 2017 Elsevier Ltd. All rights reserved.

Two choices for the functionalization of silica nanoparticles with gallic acid: characterization of the nanomaterials and their antimicrobial activity against Paenibacillus larvae

NASA Astrophysics Data System (ADS)

Vico, Tamara A.; Arce, Valeria B.; Fangio, María F.; Gende, Liesel B.; Bertran, Celso A.; Mártire, Daniel O.; Churio, María S.

2016-11-01

Silica nanoparticles attached to gallic acid were synthesized from 7-nm diameter fumed silica particles by different functionalization methods involving the condensation of hydroxyl or carboxyl groups. The particles were characterized by thermal analyses and UV-vis, FTIR, NMR, and EPR spectroscopies. In comparison to free gallic acid, enhanced stability and increased antimicrobial activity against Paenibacillus larvae were found for the functionalized nanoparticles. Thus, both derivatization strategies result in improved properties of the natural polyphenol as antimicrobial agent for the treatment of honeybee pathologies.

A C8-Modified Graphene@mSiO2 Composites Based Method for Quantification of Gallic Acid in Rat Plasma after Oral Administration of Changtai Granule and Its Application to Pharmacokinetics.

PubMed

Xu, Chen; Yu, Yingjia; Ling, Li; Wang, Yang; Zhang, Jundong; Li, Yan; Duan, Gengli

2017-01-01

A rapid, effective extraction technique has been established for measuring the gallic acid in rat plasma by using sandwich-structured graphene/mesoporous silica composites with C 8 -modified interior pore-walls as adsorbent. The unique characteristics of the graphene-silica composites excluded large molecules, like proteins, from the mesopore channels as a result of size exclusion effect, leading to a direct extraction of drug molecules from protein-rich biological samples such as plasma without any other pretreatment procedure. Followed by elution and centrifugation, the gallic acid-absorbed composites were rapidly isolated before LC-MS/MS. Serving as a reliable tool for analysis of Traditional Chinese Medicine: Changtai Granule, the newly developed method was fully validated and successfully applied in the pharmacokinetic study of gallic acid in rat plasma. Extraction recovery, matrix effect and stability were satisfactory in rat plasma. According to the results of pharmacokinetic studies, Changtai Granule exhibited greater adsorption, distribution and clearance properties of gallic acid in the treatment of ulcerative colitis. Hence, this study may offer a valuable alternative to simplify and speed up sample preparation, and be useful for clinical studies of related preparations.

Storage of Fruits and Vegetables in Refrigerator Increases their Phenolic Acids but Decreases the Total Phenolics, Anthocyanins and Vitamin C with Subsequent Loss of their Antioxidant Capacity

PubMed Central

Patel, Nilesh J.; Talati, Jayant G.

2017-01-01

It is of paramount importance for consumers, scientists and industrialists to understand how low-temperature storage of food items affects their bioactive compounds and properties. This study evaluated the effects of cold storage on total phenolics (TP), phenolic acids profile (PA), total anthocyanins (TA), total ascorbic acid (Vit. C) and antioxidant activity (AA) of 19 fruits and vegetables, collected from local Indian markets and stored in refrigerator (4 °C) during 15 days. Content of TP was highest in dill and amaranth and decreased (up to 29.67%) with storage. Leafy vegetables (amaranth, dill, onion, fenugreek and spinach) contained higher amounts of the 12 PA revealed by UPLC-UV; ellagic, gallic, sinapic and vanillic acids levels were the highest; chlorogenic acid (ρ = 0.423), syringic acid (ρ = 0.403) and sinapic acid (ρ = 0.452) mostly correlated with TP; and the PA increased during storage. Highest contents of Vit C estimated by AOAC, DCPIP and DNP methods were found in amaranth, dill and pomegranate, and decreased with storage. Pomegranate showed highest TA levels and low-temperature storage did not significantly increase TA, which was the largest contributor of TP in fruits and vegetables (ρ = 0.661). Storage induced a drastic decrease of AA, which mostly correlated with TP (ρ = 0.808, 0.690 and 0.458 for DPPH, ABTS and FRAP assays, respectively). Spearman’s correlation confirmed by principal component analysis demonstrated that dill, pomegranate and amaranth had the highest overall antioxidant capacity, whereas orange juice and carrot showed the lowest. The results provide support for a key-role of TP, followed by Vit. C and TA in antioxidant capacity of fruits and vegetables, which could be interesting dietary sources of natural antioxidants for prevention of diseases caused by oxidative stress. PMID:28737734

Storage of Fruits and Vegetables in Refrigerator Increases their Phenolic Acids but Decreases the Total Phenolics, Anthocyanins and Vitamin C with Subsequent Loss of their Antioxidant Capacity.

PubMed

Galani, Joseph H Y; Patel, Jalpesh S; Patel, Nilesh J; Talati, Jayant G

2017-07-24

It is of paramount importance for consumers, scientists and industrialists to understand how low-temperature storage of food items affects their bioactive compounds and properties. This study evaluated the effects of cold storage on total phenolics (TP), phenolic acids profile (PA), total anthocyanins (TA), total ascorbic acid (Vit. C) and antioxidant activity (AA) of 19 fruits and vegetables, collected from local Indian markets and stored in refrigerator (4 °C) during 15 days. Content of TP was highest in dill and amaranth and decreased (up to 29.67%) with storage. Leafy vegetables (amaranth, dill, onion, fenugreek and spinach) contained higher amounts of the 12 PA revealed by UPLC-UV; ellagic, gallic, sinapic and vanillic acids levels were the highest; chlorogenic acid (ρ = 0.423), syringic acid (ρ = 0.403) and sinapic acid (ρ = 0.452) mostly correlated with TP; and the PA increased during storage. Highest contents of Vit C estimated by AOAC, DCPIP and DNP methods were found in amaranth, dill and pomegranate, and decreased with storage. Pomegranate showed highest TA levels and low-temperature storage did not significantly increase TA, which was the largest contributor of TP in fruits and vegetables (ρ = 0.661). Storage induced a drastic decrease of AA, which mostly correlated with TP (ρ = 0.808, 0.690 and 0.458 for DPPH, ABTS and FRAP assays, respectively). Spearman's correlation confirmed by principal component analysis demonstrated that dill, pomegranate and amaranth had the highest overall antioxidant capacity, whereas orange juice and carrot showed the lowest. The results provide support for a key-role of TP, followed by Vit. C and TA in antioxidant capacity of fruits and vegetables, which could be interesting dietary sources of natural antioxidants for prevention of diseases caused by oxidative stress.

Anti-inflammatory and ameliorative effects of gallic acid on fluoxetine-induced oxidative stress and liver damage in rats.

PubMed

Karimi-Khouzani, Omid; Heidarian, Esfandiar; Amini, Sayed Asadollah

2017-08-01

Fluoxetine-induced liver damage is a cause of chronic liver disease. In the present study the hepatoprotective effects of gallic acid against fluoxetine-induced liver damage were examined. Forty-eight male rats were divided into six groups as follow: group 1, the control group; group 2, rats receiving fluoxetine (24mg/kg bw daily, po) without treatment; group 3, rats receiving 24mg/kg bw fluoxetine, treated with 50mg/kg bw silymarin and groups 4, 5, and 6 in which gallic acid (50, 100, and 200mg/kg bw, po, respectively) was prescribed after the consumption of fluoxetine. The histopathological changes of hepatic tissues were checked out. Fluoxetine caused a significant increase in the levels of serum glutamate oxaloacetate transaminase (GOT), serum glutamate pyruvate transaminase (GPT), lipid profiles, urea, fasting blood sugar (FBS), creatinine (Cr), protein carbonyl (PC) content, malondialdehyde (MDA), and liver TNF-α as an inflammatory element. Also, the obtained results of group 2 revealed a significant decline in ferric reducing ability of plasma (FRAP), liver catalase (CAT), superoxide dismutase (SOD), and vitamin C levels. The treatment with gallic acid showed significant ameliorations in abnormalities of fluoxetine-induced liver injury as represented by the improvement of hepatic CAT, SOD activities, vitamin C levels, serum biochemical parameters, and histopathological changes, in addition to the recovery of antioxidant defense system status. Gallic acid has inhibitory effects on fluoxetine-induced liver damage. The effect of gallic acid is derived from free radical scavenging properties and the anti-inflammatory effect related to TNF-α. Copyright © 2017. Published by Elsevier Urban & Partner Sp. z o.o.

Ellagic acid, sulforaphane, and ursolic acid in the prevention and therapy of breast cancer: current evidence and future perspectives.

PubMed

Jaman, Md Sadikuj; Sayeed, Md Abu

2018-05-03

Globally, breast cancer is the most common cancer and the second leading cause of cancer-related death among women. Surgery, chemotherapy, hormonal therapy, and radiotherapy are currently available treatment options for breast cancer therapy. However, chemotherapy, hormonal therapy, and radiotherapy are often associated with side effects and multidrug resistance, recurrence, and lack of treatment in metastasis are the major problems in the treatment of breast cancer. Recently, dietary phytochemicals have emerged as advantageous agents for the prevention and therapy of cancer due to their safe nature. Ellagic acid (EA), sulforaphane (SF), and ursolic acid (UA), which are found in widely consumed fruits and vegetables, have been shown to inhibit breast cancer cell proliferation and to induce apoptosis. This review encompasses the role of EA, SF, and UA in the fight against breast cancer. Both in vitro and in vivo effects of these agents are presented.

Phenolic Modified Ceramic Coating on Biodegradable Mg Alloy: The Improved Corrosion Resistance and Osteoblast-Like Cell Activity.

PubMed

Lee, Hung-Pang; Lin, Da-Jun; Yeh, Ming-Long

2017-06-25

Magnesium alloys have great potential for developing orthopedic implants due to their biodegradability and mechanical properties, but the rapid corrosion rate of the currently-available alloys limits their clinical applications. To increase the corrosion resistance of the substrate, a protective ceramic coating is constructed by a micro-arc oxidation (MAO) process on ZK60 magnesium alloy. The porous ceramic coating is mainly composed of magnesium oxide and magnesium silicate, and the results from cell cultures show it can stimulate osteoblastic cell growth and proliferation. Moreover, gallic acid, a phenolic compound, was successfully introduced onto the MAO coating by grafting on hydrated oxide and chelating with magnesium ions. The gallic acid and rough surface of MAO altered the cell attachment behavior, making it difficult for fibroblasts to adhere to the MAO coating. The viability tests showed that gallic acid could suppress fibroblast growth and stimulate osteoblastic cell proliferation. Overall, the porous MAO coating combined with gallic acid offered a novel strategy for increasing osteocompatibility.

Phenolic Modified Ceramic Coating on Biodegradable Mg Alloy: The Improved Corrosion Resistance and Osteoblast-Like Cell Activity

PubMed Central

Lee, Hung-Pang; Lin, Da-Jun; Yeh, Ming-Long

2017-01-01

Magnesium alloys have great potential for developing orthopedic implants due to their biodegradability and mechanical properties, but the rapid corrosion rate of the currently-available alloys limits their clinical applications. To increase the corrosion resistance of the substrate, a protective ceramic coating is constructed by a micro-arc oxidation (MAO) process on ZK60 magnesium alloy. The porous ceramic coating is mainly composed of magnesium oxide and magnesium silicate, and the results from cell cultures show it can stimulate osteoblastic cell growth and proliferation. Moreover, gallic acid, a phenolic compound, was successfully introduced onto the MAO coating by grafting on hydrated oxide and chelating with magnesium ions. The gallic acid and rough surface of MAO altered the cell attachment behavior, making it difficult for fibroblasts to adhere to the MAO coating. The viability tests showed that gallic acid could suppress fibroblast growth and stimulate osteoblastic cell proliferation. Overall, the porous MAO coating combined with gallic acid offered a novel strategy for increasing osteocompatibility. PMID:28773055

Polyphenols in red wine inhibit the proliferation and induce apoptosis of LNCaP cells.

PubMed

Romero, I; Páez, A; Ferruelo, A; Luján, M; Berenguer, A

2002-06-01

To assess the effect of five polyphenol constituents of red wine (quercetin, morin, rutin, gallic acid and tannic acid) on the proliferation of LNCaP cells, and to quantify the extent of apoptosis with each polyphenol. LNCaP cells (500) were cultured in microtitre plates and treated with gallic acid, tannic acid, quercetin (1, 5 and 10 micromol/L), rutin and morin (25, 50 and 75 micromol/L). A colorimetric immunoassay was then used to determine the extent of proliferation at 24, 48, 72 and 96 h, and a cell-death detection assay to assess apoptosis at 24, 48 and 72 h. Gallic and tannic acid (5 and 10 micromol/L), morin (50 and 75 micromol/L), quercetin (5 and 10 micromol/L) and rutin (50 and 75 micromol/L) all significantly inhibited (P<0.05) cell proliferation compared with the control. Apoptotic indexes were significantly greater (P<0.01) in the presence of gallic (5 and 10 micromol/L) and tannic acid (5 and 10 micromol/L), and rutin (75 micromol/L, P<0.05) than in the control. The apoptotic effect of morin (75 micromol/L), although significant (P<0.01), only appeared at 72 h. Conversely, while significant (P<0.05) quercetin (5 and 10 micromol/L) had a transient (first 48 h) apoptotic effect compared with the control. Quercetin, rutin, morin, gallic acid and tannic acid inhibited the growth of LNCaP cells at different concentrations, and induced apoptosis. The results provide a strong rationale for studying the in vivo effects of these compounds.

The antimicrobial activity of fruits from some cultivar varieties of Rubus idaeus and Rubus occidentalis.

PubMed

Krauze-Baranowska, M; Majdan, M; Hałasa, R; Głód, D; Kula, M; Fecka, I; Orzeł, A

2014-10-01

Raspberries, derived from different cultivar varieties, are a popular ingredient of everyday diet, and their biological activity is a point of interest for researchers. The ethanol-water extracts from four varieties of red (Rubus idaeus'Ljulin', 'Veten', 'Poranna Rosa') and black (Rubus occidentalis'Litacz') raspberries were evaluated in the range of their antimicrobial properties as well as phenolic content - sanguiin H-6, free ellagic acid and anthocyanins. The antimicrobial assay was performed with the use of fifteen strains of bacteria, both Gram-negative and Gram-positive. The antimicrobial activity of the extracts varied and depended on the analysed strain of bacteria and cultivar variety, with the exception of Helicobacter pylori, towards which the extracts displayed the same growth inhibiting activity. Two human pathogens Corynebacterium diphtheriae and Moraxella catarrhalis proved to be the most sensitive to raspberry extracts. Contrary to the extracts, sanguiin H-6 and ellagic acid were only active against eight and nine bacterial strains, respectively. The determined MIC and MBC values of both compounds were several times lower than the tested extracts. The highest sensitivity of Corynebacterium diphtheriae to extracts from both black and red raspberries may be due to its sensitivity to sanguiin H-6 and ellagic acid.

Metabolic profiling and correlation analysis for the determination of killer compounds of proliferating and clonogenic HRT-18 colon cancer cells from Lafoensia pacari.

PubMed

Reichert, Cristiane Loiva; da Silva, Denise Brentan; Carollo, Carlos Alexandre; Weffort-Santos, Almeriane Maria; de Moraes Santos, Cid Aimbiré

2018-06-18

Lafoensia pacari A. St.-Hil., belonging to the family Lythraceae and popularly known as 'dedaleira' and 'mangava-brava,' is a native tree of the Brazilian Cerrado, and its barks have been traditionally used as a tonic to treat inflammatory conditions, particularly related to gastric ulcers, wounds or fevers and various types of cancer. We have previously demonstrated the apoptogenic effects of the methanolic extract of L. pacari using various cancer cell lines. In the present study, this extract has been partitioned into fractions to identify the components that might be responsible for the apoptogenic effects using HRT-18 cells, which have been previously demonstrated to be sensitive to this extract. A standard methanolic extract was prepared and fractionated by centrifugal partition chromatography. The fractions were submitted to cytotoxicity and clonogenic assays to monitor the effects in parallel with LC-DAD-MS and statistical analyses to suggest the potential bioactive compounds. Besides ellagic acid, the primary constituent of the plant and also the biomarker of the species, one punicalin isomer, three pedunculagin I isomers, two castalagin isomers, three punicalagin HHDP-gallagyl-hexoside isomers, one ellagic acid deoxyhexose conjugate and one methyl ellagic acid deoxyhexose conjugate were putatively identified. The barks of L. pacari are rich in ellagic acid and various hydrolysable tannins, some of which were reported for the first time in this species, such as punicalagin and ellagitannins. This mixture of substances had the ability to kill proliferating cells and abrogate the growth of clonogenic cells in a similar manner shown by the methanolic extract of our previous study. The collective data reported herein suggest that the biological activities of the L. pacari barks used by the Cerrado's population to treat cancer conditions are due to the apoptogenic effects promoted by a mixed content of ellagitannins. Copyright © 2018. Published by Elsevier B.V.

Acute toxicity and sublethal effects of gallic and pelargonic acids on the zebrafish Danio rerio.

PubMed

Techer, Didier; Milla, Sylvain; Fontaine, Pascal; Viot, Sandrine; Thomas, Marielle

2015-04-01

Gallic and pelargonic acids are naturally found in a variety of plants and food products. Despite their extensive use in man-made applications, little is known regarding their potential risks to aquatic vertebrates. The aim of this work was to assess the acute toxicity of these polyphenolic and fatty acid compounds to the zebrafish. In order to get insights into sublethal effects, the enzyme activity of usual biomarkers related to oxidative stress and biotransformation were also assessed in fish. These latter included total superoxide dismutase, catalase as well as total glutathione peroxidase for antioxidant defence mechanisms and glutathione S-transferase for biotransformation related enzyme. Gallic acid was practically non-toxic (96-h lethal concentration (LC50) > 100 mg/L) whereas pelargonic acid was slightly toxic (96-h LC50 of 81.2 mg/L). Moreover, biomarker analyses indicated enhanced superoxide dismutase activity in fish exposed to 20, 40 and 100 mg/L of gallic acid compared to control. A dose-dependent induction of glutathione peroxidase and glutathione S-transferase was reported following gallic acid exposure at the tested concentrations of 10, 20 and 40 mg/L, with the exception of 100 mg/L of substance where basal activity levels were reported. In the case of pelargonic acid, there was no change in antioxidant enzyme activity while an inhibition of glutathione S-transferase was observed from organisms exposed to 45, 58 and 76 mg/L of test solution. The results concerning sublethal effects on biological parameters of zebrafish highlighted thereby the need for further investigations following chronic exposure to both organic acids.

Free radicals produced by the oxidation of gallic acid: An electron paramagnetic resonance study.

PubMed

Eslami, Angelique C; Pasanphan, Wanvimol; Wagner, Brett A; Buettner, Garry R

2010-08-05

Gallic acid (3,4,5-trihydroxybenzoic acid) is found in a wide variety of plants; it is extensively used in tanning, ink dyes, as well as in the manufacturing of paper. The gallate moiety is a key component of many functional phytochemicals. In this work electron paramagnetic spectroscopy (EPR) was used to detect the free radicals generated by the air-oxidation of gallic acid. We found that gallic acid produces two different radicals as a function of pH. In the pH range between 7-10, the spectrum of the gallate free radical is a doublet of triplets (aH = 1.00 G, aH = 0.23 G, aH = 0.28 G). This is consistent with three hydrogens providing hyperfine splitting. However, in a more alkaline environment, pH >10, the hyperfine splitting pattern transforms into a 1:2:1 pattern (aH (2) = 1.07 G). Using D2O as a solvent, we demonstrate that the third hydrogen (i.e. aH = 0.28 G) at lower pH is a slowly exchanging hydron, participating in hydrogen bonding with two oxygens in ortho position on the gallate ring. The pKa of this proton has been determined to be 10. This simple and novel approach permitted the understanding of the prototropic equilibrium of the semiquinone radicals generated by gallic acid, a ubiquitous compound, allowing new insights into its oxidation and subsequent reactions.

Analysis of Phenolic Compounds and Antioxidant Activity in Wild Blackberry Fruits

PubMed Central

Oszmiański, Jan; Nowicka, Paulina; Teleszko, Mirosława; Wojdyło, Aneta; Cebulak, Tomasz; Oklejewicz, Krzysztof

2015-01-01

Twenty three different wild blackberry fruit samples were assessed regarding their phenolic profiles and contents (by LC/MS quadrupole time-of-flight (QTOF) and antioxidant activity (ferric reducing ability of plasma (FRAP) and 2,2-azinobis (3-ethyl-benzothiazoline-6-sulfonic acid) (ABTS)) by two different extraction methods. Thirty four phenolic compounds were detected (8 anthocyanins, 15 flavonols, 3 hydroxycinnamic acids, 6 ellagic acid derivatives and 2 flavones). In samples, where pressurized liquid extraction (PLE) was used for extraction, a greater increase in yields of phenolic compounds was observed, especially in ellagic acid derivatives (max. 59%), flavonols (max. 44%) and anthocyanins (max. 29%), than after extraction by the ultrasonic technique extraction (UAE) method. The content of phenolic compounds was significantly correlated with the antioxidant activity of the analyzed samples. Principal component analysis (PCA) revealed that the PLE method was more suitable for the quantitative extraction of flavonols, while the UAE method was for hydroxycinnamic acids. PMID:26132562

The anti-oncogenic influence of ellagic acid on colon cancer cells in leptin-enriched microenvironment.

PubMed

Yousef, Amany I; El-Masry, Omar S; Yassin, Eman H

2016-10-01

Ellagic acid (EA) has been proposed as a promising candidate for therapeutic use in colon cancer. Investigation of the effectiveness of EA in a leptin-enriched model might have been given a little interest. Here in, we investigated the anti-tumor effect of EA in the presence of leptin to reflect on therapeutic use of EA in obesity-linked colon cancer. Proven effective in leptin-enriched microenvironment, EA inhibited cell proliferation of HCT-116 and CaCo-2 cell lines, modulated cell cycle, translocated Bax to the mitochondrial fraction of cells, activated caspase-8, and reduced PCNA expression. The current study findings cast a beam of light on the potential therapeutic use of EA in obesity-related colon carcinogenesis.

Crystal water as the mol-ecular glue for obtaining different co-crystal ratios: the case of gallic acid tris-caffeine hexa-hydrate.

PubMed

Vella-Zarb, L; Baisch, U

2018-04-01

The crystal structure of the hexa-hydrate co-crystal of gallic acid and caffeine, C 7 H 6 O 5 ·3C 8 H 10 N 4 O 2 ·6H 2 O or GAL3CAF·6H 2 O , is a remarkable example of the importance of hydrate water acting as structural glue to facilitate the crystallization of two components of different stoichiometries and thus to compensate an imbalance of hydrogen-bond donors and acceptors. The water mol-ecules provide the additional hydrogen bonds required to form a crystalline solid. Whereas the majority of hydrogen bonds forming the inter-molecular network between gallic acid and caffeine are formed by crystal water, only one direct classical hydrogen bond between two mol-ecules is formed between the carb-oxy-lic oxygen of gallic acid and the carbonyl oxygen of caffeine with d ( D ⋯ A ) = 2.672 (2) Å. All other hydrogen bonds either involve crystal water or utilize protonated carbon atoms as donors.

In Vitro Sustained Release Study of Gallic Acid Coated with Magnetite-PEG and Magnetite-PVA for Drug Delivery System

PubMed Central

Kura, Aminu Umar; Hussein-Al-Ali, Samer Hasan; Bin Hussein, Mohd Zobir; Fakurazi, Sharida; Shaari, Abdul Halim; Ahmad, Zalinah

2014-01-01

The efficacy of two nanocarriers polyethylene glycol and polyvinyl alcohol magnetic nanoparticles coated with gallic acid (GA) was accomplished via X-ray diffraction, infrared spectroscopy, magnetic measurements, thermal analysis, and TEM. X-ray diffraction and TEM results showed that Fe3O4 nanoparticles were pure iron oxide having spherical shape with the average diameter of 9 nm, compared with 31 nm and 35 nm after coating with polyethylene glycol-GA (FPEGG) and polyvinyl alcohol-GA (FPVAG), respectively. Thermogravimetric analyses proved that after coating the thermal stability was markedly enhanced. Magnetic measurements and Fourier transform infrared (FTIR) revealed that superparamagnetic iron oxide nanoparticles could be successfully coated with two polymers (PEG and PVA) and gallic acid as an active drug. Release behavior of gallic acid from two nanocomposites showed that FPEGG and FPVAG nanocomposites were found to be sustained and governed by pseudo-second-order kinetics. Anticancer activity of the two nanocomposites shows that the FPEGG demonstrated higher anticancer effect on the breast cancer cell lines in almost all concentrations tested compared to FPVAG. PMID:24737969

Quercetin and gallic acid mediated synthesis of bimetallic (silver and selenium) nanoparticles and their antitumor and antimicrobial potential.

PubMed

Mittal, Amit Kumar; Kumar, Sanjay; Banerjee, Uttam Chand

2014-10-01

In this study a synthetic approach for the stable, mono-dispersed high yielding bimetallic (Ag-Se) nanoparticles by quercetin and gallic acid is described. The bimetallic nanoparticles were synthesized at room temperature. Different reaction parameters (concentration of quercetin, gallic acid and Ag/Se salt, pH, temperature and reaction time) were optimized to control the properties of nanoparticles. The nanoparticles were characterized by various analytical techniques and their size was determined to be 30-35 nm. Our findings suggest that both the reduction as well as stabilization of nanoparticles were achieved by the flavonoids and phenolics. This study describes the efficacy of quercetin and gallic acid mediated synthesis of bimetallic (Ag-Se) nanoparticles and their in vitro antioxidant, antimicrobial (Gram-positive and Gram-negative bacteria) and antitumor potentials. The synthesized Ag-Se nanoparticles were used as anticancer agents for Dalton lymphoma (DL) cells and in in vitro 80% of its viability was reduced at 50 μg/mL. Copyright © 2014 Elsevier Inc. All rights reserved.

Comparison of anti-inflammatory mechanisms of mango (Mangifera Indica L.) and pomegranate (Punica Granatum L.) in a preclinical model of colitis.

PubMed

Kim, Hyemee; Banerjee, Nivedita; Ivanov, Ivan; Pfent, Catherine M; Prudhomme, Kalan R; Bisson, William H; Dashwood, Roderick H; Talcott, Stephen T; Mertens-Talcott, Susanne U

2016-09-01

Tannin-rich fruits have been evaluated as alternative prevention strategies for colorectal cancer based on their anti-inflammatory properties. This study compared tannin-rich preparations from mango (rich in gallotannins) and pomegranate (rich in ellagitannins) in the dextran sodium sulfate-induced colitis model. In rats, mango and pomegranate beverages decreased intestinal inflammation and the levels of pro-inflammatory cytokines in mucosa and serum. The mango beverage suppressed the ratio of phosphorylated/total protein expression of the IGF-1R-AKT/mTOR axis and downregulated mRNA expression of Igf1, Insr, and pik3cv. Pomegranate decreased p70S6K and RPS6, as well as Rps6ka2, Map2k2, and Mapk1 mRNA. In silico modeling indicated a high binding of docked of gallic acid to the catalytic domain of IGF-1R, which may suppress the activity of the enzyme. Ellagic acid docked effectively into the catalytic domains of both IGF-1R and EGFR. In vitro assays with lipopolysaccharide-treated CCD-18Co cells using polyphenolic extracts from each beverage, as well as pure compounds, corroborated the predictions made in silico. Mango polyphenols inhibited the IGF-1R- AKT/mTOR axis, and pomegranate polyphenols downregulate the mTOR downstream pathway through reductions in ERK1/2. These results suggest that extracts rich in gallo- and ellagitannins act on different molecular targets in the protection against ulcerative colitis. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Comparison of anti-inflammatory mechanisms of mango (Mangifera Indica L.) and pomegranate (Punica Granatum L.) in a preclinical model of colitis

PubMed Central

Kim, Hyemee; Banerjee, Nivedita; Ivanov, Ivan; Pfent, Catherine M.; Prudhomme, Kalan R.; Bisson, William H.; Dashwood, Rodrick H.; Talcott, Stephen T.; Mertens-Talcott, Susanne U.

2016-01-01

Scope Tannin-rich fruits have been evaluated as alternative prevention strategies for colorectal cancer based on their anti-inflammatory properties. This study compared tannin-rich preparations from mango (rich in gallotannins) and pomegranate (rich in ellagitannins) in the dextran sodium sulfate-induced colitis model. Methods and results In rats, mango and pomegranate beverages decreased intestinal inflammation and the levels of pro-inflammatory cytokines in mucosa and serum. The mango beverage suppressed the ratio of phosphorylated/total protein expression of the IGF-1R-AKT/mTOR axis and down-regulated mRNA expression of Igf1, Insr, and pik3cv. Pomegranate decreased p70S6K and RPS6, as well as Rps6ka2, Map2k2, and Mapk1 mRNA. In silico modeling indicated a high binding-docked of gallic acid to the catalytic domain of IGF-1R, which may suppress the activity of the enzyme. Ellagic acid docked effectively into the catalytic domains of both IGF-1R and EGFR. In vitro assays with lipopolysaccharide-treated CCD-18Co cells using polyphenolic extracts from each beverage, as well as pure compounds, corroborated the predictions made in silico. Conclusion Mango polyphenols inhibited the IGF-1R- AKT/mTOR axis, and pomegranate polyphenols downregulate the mTOR downstream pathway through reductions in ERK1/2. These results suggest that extracts rich in gallo- and ellagitannins act on different molecular targets in the protection against ulcerative colitis. PMID:27028006

Inhibitory Activities of Butanol Fraction from Butea monosperma (Lam.) Taub. Bark Against Free Radicals, Genotoxins and Cancer Cells.

PubMed

Kaur, Varinder; Kumar, Manish; Kaur, Paramjeet; Kaur, Sandeep; Kaur, Satwinderjeet

2017-06-01

The present study was undertaken to investigate antioxidant, antigenotoxic, and antiproliferative activity of butanol fraction (Bmbu) from bark of medicinal plant Butea monosperma. Antioxidant potency of Bmbu was examined by various in vitro assays. It was also investigated for antigenotoxic activity using Escherichia coli. PQ37 employing SOS chromotest. Further, cytotoxic and apoptosis inducing activity of Bmbu was evaluated in MCF-7 breast cancer cells. Bmbu showed potent free radical scavenging ability in ABTS assay (IC 50 56.70 μg/ml) and anti-lipid peroxidation ability (IC 50 40.39 μg/ml). 4NQO and H 2 O 2 induced genotoxicity was suppressed by Bmbu in SOS chromotest by 74.26% and 82.02% respectively. It also inhibited the growth of MCF-7 cells with GI 50 value of 158.71 μg/ml. Induction of apoptosis in MCF-7 cells by Bmbu treatment was deciphered using confocal microscopy, flow cytometry, and neutral comet assay. Bmbu treatment increased cell population in sub-G 1 phase (69.6%) indicating apoptotic cells. Further, Bmbu treatment resulted in increased reactive oxygen species generation and decreased mitochondrial membrane potential indicating involvement of mitochondrial dependent pathway of apoptosis. HPLC profiling showed the presence of polyphenols such as ellagic acid, catechin, quercetin, and gallic acid as its major constituents. Consequently, it is suggested that the phytoconstituents from this plant may be further exploited for development of novel drug formulation with possible therapeutic implication. © 2017 Wiley-VHCA AG, Zurich, Switzerland.

Optimization of simultaneous microwave/ultrasonic-assisted extraction of phenolic compounds from walnut flour using response surface methodology.

PubMed

Luo, Yan; Wu, Wanxing; Chen, Dan; Lin, Yuping; Ma, Yage; Chen, Chaoyin; Zhao, Shenglan

2017-12-01

Walnut is a traditional food as well as a traditional medicine recorded in the Chinese Pharmacopoeia; however, the large amounts of walnut flour (WF) generated in walnut oil production have not been well utilized. This study maximized the total polyphenolic yield (TPY) from the walnut flour (WF) by optimizing simultaneous ultrasound/microwave-assisted hydroalcoholic extraction (SUMAE). Response surface methodology was used to optimize the processing parameters for the TPY, including microwave power (20-140 W), ultrasonic power (75-525 W), extraction temperature (25-55 °C), and time (0.5-9.5 min). The polyphenol components were analysed by LC-MS. A second-order polynomial model satisfactorily fit the experimental TPY data (R 2  = 0.9932, P < 0.0001 and R adj 2     = 0.9868). The optimized quick extraction conditions were microwave power 294.38 W, ultrasonic power 93.5 W, temperature 43.38 °C and time 4.33 min, with a maximum TPY of 34.91 mg GAE/g, which was a rapid extraction. The major phenolic components in the WF extracts were glansreginin A, ellagic acid, and gallic acid with peak areas of 22.15%, 14.99% and 10.96%, respectively, which might be used as functional components for health food, cosmetics and medicines. The results indicated that walnut flour, a waste product from the oil industry, was a rich source of polyphenolic compounds and thus could be used as a high-value functional food ingredient.

Sea Buckthorn Leaf Extract Protects Jejunum and Bone Marrow of 60Cobalt-Gamma-Irradiated Mice by Regulating Apoptosis and Tissue Regeneration

PubMed Central

Gupta, Manish; Saini, Manu; Abdin, M. Z.; Prasad, Jagdish

2015-01-01

A single dose (30 mg/kg body weight) of standardized sea buckthorn leaf extract (SBL-1), administered 30 min before whole body 60Co-gamma-irradiation (lethal dose, 10 Gy), protected >90% of mice population. The purpose of this study was to investigate the mechanism of action of SBL-1 on jejunum and bone marrow, quantify key bioactive compounds, and analyze chemical composition of SBL-1. Study with 9-week-old inbred male Swiss albino Strain ‘A' mice demonstrated that SBL-1 treatment before 60Co-gamma-irradiation (10 Gy) significantly (p < 0.05) countered radiation induced decreases in jejunum crypts (1.27-fold), villi number (1.41-fold), villus height (1.25-fold), villus cellularity (2.27-fold), cryptal Paneth cells (1.89-fold), and Bcl2 level (1.54-fold). It countered radiation induced increases in cryptal apoptotic cells (1.64-fold) and Bax levels (1.88-fold). It also countered radiation (2 Gy and 3 Gy) induced bone marrow apoptosis (1.59-fold and 1.85-fold) and micronuclei frequency (1.72-fold and 2.6-fold). SBL-1 rendered radiation protection by promoting cryptal stem cells proliferation, by regulating apoptosis, and by countering radiation induced chromosomal damage. Quercetin, Ellagic acid, Gallic acid, high contents polyphenols, tannins, and thiols detected in SBL-1 may have contributed to radiation protection by neutralization of radiation induced oxidative species, supporting stem cell proliferation and tissue regeneration. PMID:26421051

Wines in contact with oak wood: the impact of the variety (Carménère and Cabernet Sauvignon), format (barrels, chips and staves) and aging time on the phenolic composition.

PubMed

Laqui-Estaña, Jaime; López-Solís, Remigio; Peña-Neira, Álvaro; Medel-Marabolí, Marcela; Obreque-Slier, Elías

2018-06-13

This study characterized the flavonoid and non-flavonoid phenolic composition of Carménère and Cabernet Sauvignon wines that were in contact with barrels, chips and staves during a 12-month aging period. The wines were evaluated by spectrophotometric (for total phenols, anthocyanins and tannins, colorant intensity, hue, CIElab parameters and fractionation into mono-, oligo- and polymer of proanthocyanidins) and HPLC-DAD analyses (for ellagitannins, gallotannins, anthocyanins and low molecular weight phenols). Wines in contact with oak wood presented a strong enrichment with non-flavonoid compounds, such as caffeic, gallic, ellagic acids and ellagitannins. Wines in contact with staves stood out for the increased presence of total phenols, vanillic acid and higher color intensity, while wines aged in contact with chips showed large contents of proanthocyanidin gallates. Wines aged in barrels exhibited high contents of ellagitannins and ethyl gallates. The effect of wood on the phenolic composition was mostly associated to the original and intrinsic characteristics of each grape variety. Extraction of phenolic compounds from oak wood during wine aging is closely related to the wood format, grape variety (Carménère or Cabernet Sauvignon) and aging time. The final effect of wood on wine would be related not just to the transference of polyphenols from wood but also to structural modifications of grape polyphenols. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.

Galloylglucoses of low molecular weight as mordant in electron microscopy. II. The moiety and functional groups possibly involved in the mordanting effect

PubMed Central

1976-01-01

Synthetic pentamonogalloylglucose applied to fixed tissues acts as a mordant, inducing high and diversified contrast similar to that obtained with natural gallotannins of low molecular weight (LMGG). By the separate use of each of the two moieties of the galloylglucose molecule, it was found that gallic acid is the mordanting agent. Glucose may contribute, however, to the effect by increasing the solubility and cross-linking potential of the compound, since the mordanting induced by gallic acid alone is weaker than that produced by its hexose esters. As suggested by results obtained with various phenolics and benzoic acid derivatives, the functional groups required for the mordanting effect of such agents are the carboxyl group, and at least one hydroxyl group concomitantly present on the benzene ring. In the case of galloylglucoses, it is assumed that the effect is due to hydrolysis products (gallic, digallic, or trigallic acids) or to the multiple hydroxyl groups of the intact molecule. Esters of gallic acid (propyl- and methylgallate), as well as pyrogallol, produce a "reversed staining" of all membranes, except for those of communicating (gap) junctions. PMID:783173

HPLC profiling, antioxidant and in vivo anti-inflammatory activity of the ethanol extract of Syzygium jambos available in Bangladesh.

PubMed

Hossain, Hemayet; Rahman, Shaikh Emdadur; Akbar, Proity Nayeeb; Khan, Tanzir Ahmed; Rahman, Md Mahfuzur; Jahan, Ismet Ara

2016-03-28

Syzygium jambos has been used as a traditional medicine for the treatment of inflammatory diseases in Bangladesh. The study investigates the high performance liquid chromatography (HPLC) profiling of phenolic compounds, and evaluates the antioxidant and anti-inflammatory activities of ethanol extract of S. jambos available in Bangladesh. The extract was subjected to HPLC for the identification and quantification of the major bioactive polyphenols present in S. jambos. Antioxidant activity was determined using 2, 2'-azino bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radical scavenging, reducing power assay, total antioxidant capacity, total phenolic and flavonoid content. Furthermore, the anti-inflammatory effect of the extract in rats for two different test models: carrageenan and histamine-induced paw edema was inspected. High levels of catechin hydrate and rutin hydrate (99.00 and 79.20 mg/100 g extract, respectively) and moderate amounts of ellagic acid and quercetin (59.40 and 69.30 mg/100 g extract, respectively) were quantified in HPLC. Catechin hydrate from this plant extract was determined for the first time through HPLC. For ABTS scavenging assay, the median inhibition concentration (IC50) value of S. jambos was 57.80 µg/ml, which was significant to that of ascorbic acid (12.01 µg/ml). The maximum absorbance for reducing power assay was found to be 0.4934. The total antioxidant capacity, phenolic and flavonoid contents were calculated to be 628.50 mg/g of ascorbic acid, 230.82 mg/g of gallic acid and 11.84 mg/g of quercetin equivalent, respectively. At a dose of 400 mg/kg, a significant acute anti-inflammatory activity (P < 0.01) was observed in rats for both the test models with a reduction in the paw volume of 58.04 and 53.95 %, in comparison to those of indomethacin (62.94 and 65.79 %), respectively. The results suggest that the phenolic and flavonoid compounds are responsible for acute anti-inflammatory and antioxidant activities of S. jambos.

Ficus carica aqueous extract alleviates delayed gastric emptying and recovers ulcerative colitis-enhanced acute functional gastrointestinal disorders in rats.

PubMed

Rtibi, Kaïs; Grami, Dhekra; Wannes, Dalanda; Selmi, Slimen; Amri, Mohamed; Sebai, Hichem; Marzouki, Lamjed

2018-06-02

Ficus carica fruit, a source of bioactive functional ingredients, have been traditionally long time used for its medicinal benefits as they improve the digestive system, treating constipation and used as a natural laxative. The recent study was investigated the ameliorative effect of Ficus carica L. aqueous extract (FCAE) on delayed gastric emptying and ulcerative colitis-improved motility disturbances in dextran sulfate sodium (DSS)-induced acute colitis in rats. Wistar rats were assigned randomly and received 5% DSS for seven days. Ulcerative colitis diagnosis was confirmed by clinical signs, visible fecal blood and histopatological evaluation. The estimation of the action of colitis on TGI and constipation as well as the protective effect of extract, the intestinal biochemical and physiological parameters were measured using the charcoal meal test, loperamide (Lop)-induced constipation as well as spectrophotometric assays. FCAE (150 and 300 mg kg -1 ) was administered orally once per day for seven days 1 h after the loperamide treatment. Phenol-red colorimetric method was used to explore the action of FCAE on gastric emptying process. Ulcerative colitis caused a significantly gastrointestinal motility inhibition in normal rats and notably aggravated the constipation in LOP group. Oppositely, FCAE oral intake significantly increased levels of the gastrointestinal transit ratio and gastric emptying by accelerating of their times. Moreover, constipation severity induced by colitis was remarkably reduced in the FCAE treatment group, as demonstrated by a marked management of fecal parameters, water content, oxidative stress indicators, lipid metabolism, and intracellular mediators. Phytochemical analysis of FCAE revealed the presence of carbohydrates, polysaccharides, phenolic acids as gallic acid, chlorogenic acid, syringic acid and ellagic acid, and flavonoids (e.g. rutin, catechin, epicatechin and apeginine). The obtained results indicated that FCAE exhibits a natural laxative effect without provoking diarrhea and ameliorates functional gastrointestinal (GI) and motility disorders thus justifying its traditional usage. Copyright © 2018 Elsevier B.V. All rights reserved.

Induction of Biofilm Formation in the Betaproteobacterium Burkholderia unamae CK43B Exposed to Exogenous Indole and Gallic Acid

PubMed Central

Kim, Dongyeop; Sitepu, Irnayuli R.

2013-01-01

Burkholderia unamae CK43B, a member of the Betaproteobacteria that was isolated from the rhizosphere of a Shorea balangeran sapling in a tropical peat swamp forest, produces neither indole nor extracellular polymeric substances associated with biofilm formation. When cultured in a modified Winogradsky's medium supplemented with up to 1.7 mM indole, B. unamae CK43B maintains its planktonic state by cell swelling and effectively degrades exogenous indole. However, in medium supplemented with 1.7 mM exogenous indole and 1.0 mM gallic acid, B. unamae CK43B produced extracellular polymeric substances and formed a biofilm. The concentration indicated above of gallic acid alone had no effect on either the growth or the differentiation of B. unamae CK43B cells above a certain concentration threshold, whereas it inhibited indole degradation by B. unamae CK43B to 3-hydroxyindoxyl. In addition, coculture of B. unamae CK43B with indole-producing Escherichia coli in nutrient-rich Luria-Bertani medium supplemented with 1.0 mM gallic acid led to the formation of mixed cell aggregates. The viability and active growth of B. unamae CK43B cells in a coculture system with Escherichia coli were evidenced by fluorescence in situ hybridization. Our data thus suggest that indole facilitates intergenus communication between indole-producing gammaproteobacteria and some indole-degrading bacteria, particularly in gallic acid-rich environments. PMID:23747701

Cardioprotective effects of gallic acid in diabetes-induced myocardial dysfunction in rats

PubMed Central

Patel, Snehal S.; Goyal, Ramesh K.

2011-01-01

Background: Normalization of hyperglycemia, hyperlipidemia, and oxidative stress is an important objective in preventing diabetes-induced cardiac dysfunction. Objective: This study was undertaken to examine the effects of gallic acid in myocardial dysfunctions associated with type-1 diabetes. Materials and Methods: Diabetes was induced by single intravenous injection of streptozotocin (STZ, 50 mg/kg i.v.). Gallic acid was administered daily at three different doses (100, 50, and 25 mg/kg p.o.) for 8 weeks at the end of which blood samples were collected and analyzed for various biochemical parameters. Results: Injection of STZ produced significant loss of body weight (BW), polyphagia, polydypsia, hyperglycemia, hypoinsulinemia, hyperlipidemia, hypertension, bradycardia, and myocardial functional alterations. Treatment with gallic acid significantly lowered fasting glucose, the AUCglucose level in a dose-dependent manner; however, the insulin level was not increased significantly at same the dose and prevented loss of BW, polyphagia, and polydypsia in diabetic rats. It also prevented STZ-induced hyperlipidemia, hypertension, bradycardia, structural alterations in cardiac tissue such as increase in force of contraction, left ventricular weight to body weight ratio, collagen content, protein content, serum lactate dehydrogenase, and creatinine kinase levels in a dose-dependent manner. Further, treatment also produced reduction in lipid peroxidation and increase in antioxidant parameters in heart of diabetic rats. Conclusion: The results of this study suggest that gallic acid to be beneficial for the treatment of myocardial damage associated with type-1 diabetes. PMID:22224046

Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2)

PubMed Central

Salucci, M; Stivala, L A; Maiani, G; Bugianesi, R; Vannini, V

2002-01-01

Green tea, mainly through its constituents epigallocatechin gallate, epigallocatechin, epicatechin gallate and epicatechin, has demonstrated anticarcinogenic activity in several animal models, including those for skin, lung and gastro-intestinal tract cancer, although less is known about colorectal cancer. Quercetin, the major flavonoid present in vegetables and fruit, exerts potential anticarcinogenic effects in animal models and cell cultures, but less is known about quercetin glucosides. The objectives of this study were to investigate (i) the antioxidant activity of the phenolic compounds epicatechin, epigallocatechin gallate, gallic acid and quercetin-3-glucoside; (ii) the cytotoxicity of different concentrations of epicatechin, epigallocatechin gallate, and gallic acid; (iii) the cellular uptake of epicatechin, epigallocatechin gallate, gallic acid and quercetin-3-glucoside and (iv) their effect on the cell cycle. Human colon adenocarcinoma cells were used as experimental model. The results of this study indicate that all dietary flavonoids studied (epicatechin, epigallocatechin gallate, gallic acid and quercetin-3-glucoside) show a significant antioxidant effect in a chemical model system, but only epigallocatechin gallate or gallic acid are able to interfere with the cell cycle in Caco2 cell lines. These data suggest that the antioxidant activity of flavonoids is not related to the inhibition of cellular growth. From a structural point of view, the galloyl moiety appears to be required for both the antioxidant and the antiproliferative effects. British Journal of Cancer (2002) 86, 1645–1651. DOI: 10.1038/sj/bjc/6600295 www.bjcancer.com © 2002 Cancer Research UK PMID:12085217

Antioxidant multi-walled carbon nanotubes by free radical grafting of gallic acid: new materials for biomedical applications.

PubMed

Cirillo, Giuseppe; Hampel, Silke; Klingeler, Rüdiger; Puoci, Francesco; Iemma, Francesca; Curcio, Manuela; Parisi, Ortensia Ilaria; Spizzirri, Umile Gianfranco; Picci, Nevio; Leonhardt, Albrecht; Ritschel, Manfred; Büchner, Bernd

2011-02-01

To prove the possibility of covalently functionalizing multi-walled carbon nanotubes (CNTs) by free radical grafting of gallic acid on their surface with the subsequent synthesis of materials with improved biological properties evaluated by specific in-vitro assays. Antioxidant CNTs were synthesized by radical grafting of gallic acid onto pristine CNTs. The synthesis of carbon nanotubes was carried out in a fixed-bed reactor and, after the removal of the amorphous carbon, the grafting process was performed. The obtained materials were characterized by fluorescence and Fourier transform infrared spectroscopy (FT-IR) analyses. After assessment of the biocompatibility and determination of the disposable phenolic group content, the antioxidant properties were evaluated in terms of total antioxidant activity and scavenger ability against 2,2'-diphenyl-1-picrylhydrazyl (DPPH), hydroxyl and peroxyl radicals. Finally the inhibition activity on acetylcholinesterase was evaluated.   The covalent functionalization of CNTs with gallic acid was confirmed and the amount of gallic acid bound per g of CNTs was found to be 2.1±0.2 mg. Good antioxidant and scavenging properties were recorded in the functionalized CNTs, which were found to be able to inhibit the acetylcholinesterase with potential improved activity for biomedical and pharmaceutical applications. For the first time, a free radical grafting procedure was proposed as a synthetic approach for the covalent functionalization of CNTs with an antioxidant polyphenol. © 2010 The Authors. JPP © 2010 Royal Pharmaceutical Society.

Effect of fractionated extracts and isolated pure compounds of Spondias mombin (L. Anacardiaceae) leaves on novelty-induced rearing and grooming behaviours in mice.

PubMed

Ayoka, Abiodun O; Owolabi, Rotimi A; Bamitale, Samuel K; Akomolafe, Rufus O; Aladesanmi, Joseph A; Ukponmwan, Eghe O

2013-01-01

This study attempted to elucidate the neurotransmitter systems involved in the neurophysiological properties of ethanolic extract, fractions and pure isolates of Spondias mombin leaves in mice (n = 6) after intraperitoneal (i.p.) route of administration.The crude ethanolic extract of Spondian mombin leaves was fractionated using the partitioning method to obtain the ethylacetate, butanolic and aqueous fractions. Open column chromatographic fractionation of the ethylacetate fraction yielded seven sub-fractions, out of which the pure coumaroyl, quercetin and gallic acid derivatives were obtained after purification on Sephadex LH 20. The ethanolic extract, butanolic fraction, ethylacetate subfractions and pure isolates of the Spondian mombin leaves were tested on novelty-induced rearing and grooming behaviours in mice with standard pharmacological tools using the open field method. The extract and its fractions decreased novelty-induced rearing in a dose-dependent manner. While the Coumaroyl derivative had no effect on novelty-induced rearing, it significantly reversed the inhibitory effect of yohimbine, propranolol and haloperidol on novelty-induced rearing. Quercetin significantly potentiated the inhibitory effect of yohimbine on novelty-induced rearing. Naloxone significantly potentiated the quercetin-induced suppression of novelty-induced rearing. Gallic acid derivative significantly potentiated the inhibitory effect of yohimbine on novelty-induced rearing. Naloxone, atropine and haloperidol pretreatments significantly potentiated gallic acid derivative-induced suppression of novelty-induced rearing.The extract and its fractions had biphasic effect on novelty-induced grooming in mice. Coumaroyl derivative significantly increased novelty-induced grooming, while quercetin and gallic acid derivative decreased novelty-induced grooming significantly. The three pure isolates significantly reversed the effects of yohimbine and atropine on the novelty-induced grooming in mice. Propranolol-induced increase in novelty-induced grooming was significantly reversed by coumaroyl and gallic acid derivatives. Pre-treatment with naloxone significantly increased the gallic acid derivative-induced suppression of novelty-induced grooming. Pre-treatment with haloperidol reversed the effect of coumaroyl derivative and potentiated the inhibitory effect of quercetin derivative and gallic acid derivative significantly. This study suggested that adrenergic and dopaminergic neuro-transmissions are strongly involved in the neural mechanisms of the effect of the three pure isolates derivative, while opioid neuro-transmission is strongly linked with the neural mechanism of behavioural effect of coumaroyl derivative.

Effect of oak wood barrel capacity and utilization time on phenolic and sensorial profile evolution of an Encruzado white wine.

PubMed

Nunes, Paulo; Muxagata, Sara; Correia, Ana C; Nunes, Fernando M; Cosme, Fernanda; Jordão, António M

2017-11-01

Several studies have reported the influence of diverse winemaking technologies in white wine characteristics. However, the impact of the use of different oak wood barrel capacities and utilization time on the evolution of white wine phenolic content and sensorial characteristics are not usually considered. Thus the aim of this work was to evaluate the effect of oak wood barrel capacity and utilization time on the evolution of phenolic compounds, browning potential index and sensorial profile of an Encruzado white wine. For the 180 aging days considered, the use of new oak wood barrels induced a greater increase in global phenolic composition, including several individual compounds, such as gallic and ellagic acid, independently of the barrel capacity. Tendency for a lesser increase of the browning potential index values was detected for white wines aged in new oak wood barrels. The sensorial profile evolution, showed significant differences only for the aroma descriptors, namely for 'wood aroma' and 'aroma intensity', white wine aged in 225 L new oak wood barrels being the highest scored. The results show that, in general, the use of different capacities and utilization time of oak wood barrels used for white wine aging could play an important role in white wine quality. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

Antioxidant activity of oak (Quercus) leaves infusions against free radicals and their cardioprotective potential.

PubMed

Rivas-Arreola, M J; Rocha-Guzmán, N E; Gallegos-Infante, J A; González-Laredo, R F; Rosales-Castro, M; Bacon, J R; Cao, Rong; Proulx, A; Intriago-Ortega, P

2010-06-01

The aim of present study was to evaluate antioxidant capacity and cardioprotective potential of leaves infusions and partially purified fractions of Quercus sideroxyla and Q. eduardii (red oaks) and Q. resinosa (white oak). Consumption of polyphenol-rich beverages derived from plants, such as oak may represent a beneficial diet in terms of cardiovascular protection. Infusions from Oak leaves were obtained and probed for total phenolics by Folin-Ciocalteu, DPPH and hydroxyl radicals scavenging by DPPH test and Deoxy-D-ribose method, the antioxidant capacity was evaluated by FRAP and ORAC tests, inhibitions of Low Density Lipoproteins (LDL) oxidation and Angiotensin Converting Enzyme (ACE) activity were measured. A HPLC analysis was performed by HPLC-MS. Bioactive polyphenols such as gallic and ellagic acids, catechin, quercetin and derivatives: naringenin and naringin were detected in Quercus infusions. A distinctive HPLC profile was observed among the red and white oak samples. Q. resinosa infusions have exhibited the highest antioxidant activity in comparison with the other species, although in the inhibition of LDL oxidation no differences were observed. In the inhibition of the ACE, Q. resinosa was more effective (IC50, 18 ppm) than Q. sideroxyla, showing same effect as the control Captopril. From the results it is possible to postulate that not only chelating activity is important in these infusions, especially in Q. resinosa.

Antistaphylococcal and biofilm inhibitory activities of gallic, caffeic, and chlorogenic acids.

PubMed

Luís, Ângelo; Silva, Filomena; Sousa, Sónia; Duarte, Ana Paula; Domingues, Fernanda

2014-01-01

Staphylococcus aureus is a Gram-positive pathogen which is able to form biofilms, exhibiting a more pronounced resistance to antibiotics and disinfectants. The hurdles posed in eradicating biofilms have driven the search for new compounds able to fight these structures. Phenolic compounds constitute one of the most numerous and ubiquitous group of plant secondary metabolites with many biological activities. The aim of the present work was to study the potential antimicrobial and antibiofilm properties of gallic, caffeic, and chlorogenic acids against S. aureus as well to elucidate its mechanism of action. It was concluded that the phenolic acids studied in this work have antistaphylococcal properties. For instance, gallic acid is able to influence the adhesion properties of S. aureus. The phenolic acids tested were also able to inhibit the production of α-hemolysin by this microorganism, with the exception of chlorogenic acid. Regarding its mechanism of action, caffeic acid interferes with the stability of the cell membrane and with the metabolic activity of the cells of S. aureus.

Interaction of KRAS G-quadruplex with natural polyphenols: A spectroscopic analysis with molecular modeling.

PubMed

Pattanayak, Rudradip; Basak, Pijush; Sen, Srikanta; Bhattacharyya, Maitree

2016-08-01

Researchers are endeavoring to find out new therapeutics for curing cancer and G-quadruplex DNA has already been identified as a prospective one in this venture. Stabilizing G-quadruplex structures of telomere has emerged to be an important strategy in this context. Mutation in KRAS is mostly responsible for pancreatic, lung and colon cancer. In this present study we explored binding and conformational behaviour of G-quadruplex with different ligands by utilizing several biophysical techniques. Natural polyphenols like Curcumin and Ellagic acid were observed to bind with the G-quadruplex and enhance the melting temperature significantly indicating higher stability. UV-vis spectroscopy confirms formation of G quadruplex-ligand complex for both the compounds with specific binding affinity. Fluorimetric studies revealed that Ellagic acid had stronger binding affinity, 1.10×10(5)M(-1) compared to Curcumin, 1.6×10(4)M(-1) towards G-quadruplex. Interestingly, Curcumin provides greater stability by stacking on the top of the quadruplex structure with the help of the loops compared to Ellagic acid as is evident by docking studies. The keto form of curcumin showed stronger affinity than the enol form. We have developed a general model to estimate the influence of the ligands towards stabilizing the G-quadruplex subsequently characterizing the binding profile to enlighten prospective therapeutics. Copyright © 2016. Published by Elsevier B.V.

A chitosan/beta-glycerophosphate thermo-sensitive gel for the delivery of ellagic acid for the treatment of brain cancer.

PubMed

Kim, Sungwoo; Nishimoto, Satoru K; Bumgardner, Joel D; Haggard, Warren O; Gaber, M Waleed; Yang, Yunzhi

2010-05-01

We report here the development of a chitosan/beta-glycerophosphate(Ch/beta-GP) thermo-sensitive gel to deliver ellagic acid (EA) for cancer treatment. The properties of the Ch/beta-GP gels were characterized regarding chemical structure, surface morphology, and viscoelasticity. In vitro EA release rate from the EA loaded Ch/beta-GP gel and chitosan degradation rate were investigated. The anti-tumor effect of the EA loaded Ch/beta-GP gel on brain cancer cells (human U87 glioblastomas and rat C6 glioma cells) was evaluated by examining cell viability. Cell number and activity were monitored by the MTS assay. The Ch/beta-GP solution formed a heat-induced gel at body temperature, and the gelation temperature and time were affected by the final pH of the Ch/beta-GP solution. The lysozyme increased the EA release rate by 2.5 times higher than that in the absence of lysozyme. Dialyzed chitosan solution with final pH 6.3 greatly reduced the beta-GP needed for gelation, thereby significantly improving the biocompatibility of gel (p < 0.001). The chitosan gels containing 1% (w/v) of ellagic acid significantly reduced viability of U87 cells and C6 cells compared with the chitosan gels at 3 days incubation (p < 0.01, and p < 0.001, respectively). Copyright 2010 Elsevier Ltd. All rights reserved.

Fabrication and characterization of electrospun gelatin nanofibers crosslinked with oxidized phenolic compounds.

PubMed

Tavassoli-Kafrani, Elham; Goli, Sayed Amir Hossein; Fathi, Milad

2017-10-01

In this study, the ability of oxidized phenolic compounds of tannic, gallic, ferulic and caffeic acids to crosslink gelatin (G) was investigated. The electrospun crosslinked gelatin nanofibers were assessed in terms of gelatin solution properties, fiber morphology, thermal properties, FTIR spectra, XRD pattern and antioxidant activity. Tannic acid showed the most crosslinking activity towards gelatin (13.3 vs 7.44, 4.65, and 3.45% for caffeic, gallic and ferulic, respectively). Crosslinking enhanced roughly electrical conductivity of gelatin solution while the surface tension and viscosity reduced. According to scanning electron microscopy (SEM) results, the fibrous structure of crosslinked gelatin nanofibers didn't change while their diameter increased to the highest value of 280nm for gelatin-tannic. Gelatin-gallic sample showed the highest total phenolic content (86.3mg gallic acid equivalent/g) and antioxidant activity (86.5%). Surprisingly, from differential scanning calorimetry (DSC) curves, it was found that crosslinking led to the reduction of thermal stability of gelatin nanofibers. Copyright © 2017 Elsevier B.V. All rights reserved.

Assay Dilution Factors Confound Measures of Total Antioxidant Capacity in Polyphenol-Rich Juices

PubMed Central

Bolling, Bradley W.; Chen, Ya-Yen; Kamil, Alison G.; Chen, C-Y. Oliver

2016-01-01

The extent to which sample dilution factor (DF) affects total antioxidant capacity (TAC) values is poorly understood. Thus, we examined the impact of DF on the ORAC, FRAP, DPPH, and total phenols (TP) assays using pomegranate juice (PJ), grape juice (GJ), selected flavonoids, ascorbic acid, and ellagic acid. For ORAC, GJ was comparable to PJ at DF 750, but at DF 2000, the ORAC value of GJ was 40% more than PJ. Increasing DF increased GJ and PJ, DPPH, TP, and FRAP values 11% and 14%, respectively. Increased test concentrations of quercetin and catechin resulted in 51% and 126% greater ORAC values, but decreased naringenin by 68%. Flavonoids, but not ellagic acid or ascorbic acid, may contribute to the dilution effect on the variation of final TAC values. Thus, reporting TAC or TP using a single DF may introduce uncertainty about the confidence of TAC assay values, especially when comparing different juices. These results underscore the importance of using compatible test standards for reporting TAC values. PMID:22251245

Total phenolics and total flavonoids in selected Indian medicinal plants.

PubMed

Sulaiman, C T; Balachandran, Indira

2012-05-01

Plant phenolics and flavonoids have a powerful biological activity, which outlines the necessity of their determination. The phenolics and flavonoids content of 20 medicinal plants were determined in the present investigation. The phenolic content was determined by using Folin-Ciocalteu assay. The total flavonoids were measured spectrophotometrically by using the aluminium chloride colorimetric assay. The results showed that the family Mimosaceae is the richest source of phenolics, (Acacia nilotica: 80.63 mg gallic acid equivalents, Acacia catechu 78.12 mg gallic acid equivalents, Albizia lebbeck 66.23 mg gallic acid equivalents). The highest total flavonoid content was revealed in Senna tora which belongs to the family Caesalpiniaceae. The present study also shows the ratio of flavonoids to the phenolics in each sample for their specificity.

Thermally and vibrationally induced conformational isomerizations, infrared spectra, and photochemistry of gallic acid in low-temperature matrices

NASA Astrophysics Data System (ADS)

Justino, Licínia L. G.; Reva, Igor; Fausto, Rui

2016-07-01

Near-infrared (near-IR) narrowband selective vibrational excitation and annealing of gallic acid (3,4,5-trihydroxybenzoic acid) isolated in cryogenic matrices were used to induce interconversions between its most stable conformers. The isomerizations were probed by infrared spectroscopy. An extensive set of quantum chemical calculations, carried out at the DFT(B3LYP)/6-311++G(d,p) level of approximation, was used to undertake a detailed analysis of the ground state potential energy surface of the molecule. This investigation of the molecule conformational space allowed extracting mechanistic insights into the observed annealing- or near-IR-induced isomerization processes. The infrared spectra of the two most stable conformers of gallic acid in N2, Xe, and Ar matrices were fully assigned. Finally, the UV-induced photochemistry of the matrix isolated compound was investigated.

Influence of waterborne gallic and pelargonic acid exposures on biochemical and reproductive parameters in the zebrafish (Danio rerio).

PubMed

Techer, Didier; Milla, Sylvain; Fontaine, Pascal; Viot, Sandrine; Thomas, Marielle

2017-01-01

Gallic and pelargonic acids are biologically derived substances receiving a growing interest as eco-friendly biocides with potential applications in freshwater system management. However, some data gaps remain to address their chronic ecotoxicity issue, particularly for fish. This work aimed at investigating the sublethal effects of a long-term waterborne exposure of zebrafish to these compounds. Mature fish were exposed to gallic or pelargonic acid at the concentrations of 0, 0.05, 0.5 and 5 mg/L during one month under semi-static conditions. Fecundity, hatching rate and median hatching time were regularly evaluated. Circulating sex hormone levels (11 ketotestosterone -11 KT, 17 βestradiol -E2-), plasma vitellogenin (Vtg), and gonad histology were monitored in males and females after exposure. Lactate dehydrogenase (LDH), total glutathione peroxydase (GPx) and glutathione-S transferase (GST) activities were assessed as enzymatic biomarkers of exposure in fish liver. Significant increases of GPx activity were reported in females exposed to both type of chemicals regardless the contamination level. Moreover, 5 mg/L gallic acid induced a decrease in 11-KT levels for males. For fish exposed to pelargonic acid, decreases in circulating hormone levels were reported respectively at 0.05 and 5 mg/L for 11-KT in males, and at 0.5 mg/L for E2 in females. However, no histological alteration in gonads neither significant variation in reproductive performances were detected following zebrafish exposure to gallic or pelargonic acid. Additional investigations concerning the mode of application and the environmental fate of these substances may warrant their further use in freshwater systems at concentrations compatible with biocidal/allelochemical effects. © 2015 Wiley Periodicals, Inc. Environ Toxicol 32: 227-240, 2017. © 2015 Wiley Periodicals, Inc.

Nutritional potential, chemical profile and antioxidant activity of Chichá (Sterculia striata) nuts and its by-products.

PubMed

de Britto Policarpi, Priscila; Turcatto, Leticia; Demoliner, Fernanda; Ferrari, Roseli Aparecida; Bascuñan, Vera Lúcia Azzolin Frescura; Ramos, Juliano Carvalho; Jachmanián, Iván; Vitali, Luciano; Micke, Gustavo Amadeu; Block, Jane Mara

2018-04-01

The Sterculia striata nut commonly known as chichá is consumed raw or toasted inBrazil but information on its chemical composition and antioxidant activity are scarce in the literature. In this work, the nutritional composition, minerals profile, lipid composition and phenolic compounds profile of chichá nuts and its by-products (pellicle and shell) were determined. The results showed that the nuts and the cake contain considerable amount of fibers and proteins and are rich in minerals (Fe, Mn and Cu). Oleic acid was the main fatty acid (37.8%), and PPO (36.0%) and POP (15.6%) were the main triacylglycerides present in the chichá oil. The phytosterols β-sitosterol, stigmasteroland campesterol (1848.5μgg -1 , 542.2μgg -1 and 186.3μgg -1 , respectively), and the γ-, δ-, α- and β-tocopherol (8.85; 2.10; 1.64, and 0.11mg100g -1 , respectively) were identified in the oil. The antioxidant activity (ABTS and FRAP assays) followed the order pellicle>shell>nuts (13.25 and 84.65; 8.71 and 64.3; 5.85 and 36.79μmolTEACg -1 , respectively). The main phenolic compounds identified in the extracts were ellagic and ferulic acids; ellagic and protocatechuic acids; and protocatechuic, ellagic and methoxyphenylacetic acids for the nuts, shells and pellicle, respectively. A strong positive correlation was observed between total phenolic content and antioxidant activity determined by ABTS and FRAP assays (r=0.9067, p<0.01; and r=0.9584, p<0.01; respectively). Collectively, the results showed that the chichá is a nut of high nutritional value, rich in bioactive compounds. Copyright © 2018 Elsevier Ltd. All rights reserved.

Effects and interactions of gallic acid, eugenol and temperature on thermal inactivation of Salmonella spp. in ground chicken

USDA-ARS?s Scientific Manuscript database

The combined effects of heating temperature (55 to 65C), gallic acid (0 to 2.0%), and eugenol (0 to 2.0%) on thermal inactivation of Salmonella in ground chicken were assessed. Thermal death times were determined in bags submerged in a heated water bath maintained at various set temperatures, follo...

In Vitro Antioxidant-Activity Evaluation of Gallic-Acid-Grafted Chitosan Conjugate Synthesized by Free-Radical-Induced Grafting Method.

PubMed

Hu, Qiaobin; Wang, Taoran; Zhou, Mingyong; Xue, Jingyi; Luo, Yangchao

2016-07-27

The major objective of this work was to develop a green and facile process to prepare gallic acid-chitosan conjugate and comprehensively evaluate the physicochemical properties and biological activities of an as-prepared water-soluble chitosan derivative. A free-radical-induced grafting approach using an ascorbic acid-hydrogen peroxide redox pair was adopted. The obtained conjugate was characterized by Fourier transform infrared spectroscopy, UV-vis, X-ray diffraction, and pKa analysis. The antioxidant activities were evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline-6)-sulphonic acid (ABTS), reducing power, and oxygen-radical antioxidant-capacity assays. The results showed that the mass ratio of gallic acid to chitosan played a vital role in determining the grafting degree and ζ potential of the conjugates, with the ratio of 0.5:1 being the optimal ratio that resulted in the highest grafting degree. The antioxidant assays demonstrated that conjugation significantly improved the antioxidant activities, being dramatically higher than that of free chitosan. It was notable that the DPPH- and ABTS-scavenging activities of conjugate at 0.4 mg/mL reached the same level as the free gallic acid at the equivalent concentration. Our study demonstrated a green and facile synthesis approach to preparing a novel water-soluble chitosan derivative that may have promising potentials in the food industry.

Thermally and vibrationally induced conformational isomerizations, infrared spectra, and photochemistry of gallic acid in low-temperature matrices

DOE Office of Scientific and Technical Information (OSTI.GOV)

Justino, Licínia L. G., E-mail: liciniaj@ci.uc.pt; Reva, Igor; Fausto, Rui

2016-07-07

Near-infrared (near-IR) narrowband selective vibrational excitation and annealing of gallic acid (3,4,5-trihydroxybenzoic acid) isolated in cryogenic matrices were used to induce interconversions between its most stable conformers. The isomerizations were probed by infrared spectroscopy. An extensive set of quantum chemical calculations, carried out at the DFT(B3LYP)/6-311++G(d,p) level of approximation, was used to undertake a detailed analysis of the ground state potential energy surface of the molecule. This investigation of the molecule conformational space allowed extracting mechanistic insights into the observed annealing- or near-IR-induced isomerization processes. The infrared spectra of the two most stable conformers of gallic acid in N{sub 2},more » Xe, and Ar matrices were fully assigned. Finally, the UV-induced photochemistry of the matrix isolated compound was investigated.« less

Total Phenolics and Total Flavonoids in Selected Indian Medicinal Plants

PubMed Central

Sulaiman, C. T.; Balachandran, Indira

2012-01-01

Plant phenolics and flavonoids have a powerful biological activity, which outlines the necessity of their determination. The phenolics and flavonoids content of 20 medicinal plants were determined in the present investigation. The phenolic content was determined by using Folin-Ciocalteu assay. The total flavonoids were measured spectrophotometrically by using the aluminium chloride colorimetric assay. The results showed that the family Mimosaceae is the richest source of phenolics, (Acacia nilotica: 80.63 mg gallic acid equivalents, Acacia catechu 78.12 mg gallic acid equivalents, Albizia lebbeck 66.23 mg gallic acid equivalents). The highest total flavonoid content was revealed in Senna tora which belongs to the family Caesalpiniaceae. The present study also shows the ratio of flavonoids to the phenolics in each sample for their specificity. PMID:23439764

Ellagic acid derivatives, ellagitannins, proanthocyanidins and other phenolics, vitamin C and antioxidant capacity of two powder products from camu-camu fruit (Myrciaria dubia).

PubMed

Fracassetti, Daniela; Costa, Carlos; Moulay, Leila; Tomás-Barberán, Francisco A

2013-08-15

The aims of this study were the evaluation of polyphenols and vitamin C content, and antioxidant capacity of dehydrated pulp powder and the dried flour obtained from the skin and seeds residue remaining after pulp preparation from camu-camu (Myrciaria dudia). Fifty-three different phenolics were characterised by HPLC-DAD-ESI-MS-MS and UPLC-HR-QTOF-MS-MS. The phenolic content of camu-camu flour was higher than that of the pulp powder (4007.95 mg/100 g vs. 48.54 mg/100 g). In both products the flavonol myricetin and conjugates, ellagic acid and conjugates and ellagitannins were detected. Cyanidin 3-glucoside, and quercetin and its glycosides were only found in the pulp powder, while proanthocyanidins were only present in the flour (3.5 g/100 g, mean degree of polymerisation 3). The vitamin C content was lower in pulp powder (3.5%) than in the flour (9.1%). The radical-scavenging capacity of both powders was determined by the DPPH, ABTS and ORAC assays, and was higher for camu-camu flour as could be expected for its higher phenolics and vitamin C content. Comparative analyses with fresh camu-camu berries indicate that some transformations occur during processing. Analysis of fresh berries showed that ellagic acid derivatives and ellagitannins were mainly present in the seeds, while proanthocyanidins were present both in the seeds and skin. Copyright © 2013 Elsevier Ltd. All rights reserved.

Ellagic Acid-Changed Epigenome of Ribosomal Genes and Condensed RPA194-Positive Regions of Nucleoli in Tumour Cells.

PubMed

Legartová, S; Sbardella, G; Kozubek, S; Bártová, E

2015-01-01

We studied the effect of ellagic acid (EA) on the morphology of nucleoli and on the pattern of major proteins of the nucleolus. After EA treatment of HeLa cells, we observed condensation of nucleoli as documented by the pattern of argyrophilic nucleolar organizer regions (AgNORs). EA also induced condensation of RPA194-positive nucleolar regions, but no morphological changes were observed in nucleolar compartments positive for UBF1/2 proteins or fibrillarin. Studied morphological changes induced by EA were compared with the morphology of control, non-treated cells and with pronounced condensation of all nucleolar domains caused by actinomycin D (ACT-D) treatment. Similarly as ACT-D, but in a lesser extent, EA induced an increased number of 53BP1-positive DNA lesions. However, the main marker of DNA lesions, γH2AX, was not accumulated in body-like nuclear structures. An increased level of γH2AX was found by immunofluorescence and Western blots only after EA treatment. Intriguingly, the levels of fibrillarin, UBF1/2 and γH2AX were increased at the promoters of ribosomal genes, while 53BP1 and CARM1 levels were decreased by EA treatment at these genomic regions. In the entire genome, EA reduced H3R17 dimethylation. Taken together, ellagic acid is capable of significantly changing the nucleolar morphology and protein levels inside the nucleolus.

Effects of ellagic acid pretreatment on renal functions disturbances induced by global cerebral ischemic-reperfusion in rat.

PubMed

Nejad, Khojasteh Hoseiny; Gharib-Naseri, Mohammad Kazem; Sarkaki, Alireza; Dianat, Mahin; Badavi, Mohammad; Farbood, Yaghoub

2017-01-01

Global cerebral ischemia-reperfusion (GCIR) causes disturbances in brain functions as well as other organs such as kidney. Our aim was to evaluate the protective effects of ellagic acid (EA) on certain renal disfunction after GCIR. Adult male Wistar rats (n=32, 250-300 g) were used. GCIR was induced by bilateral vertebral and common carotid arteries occlusion (4-VO). Animal groups were: 1) received DMSO/saline (10%) as solvent of EA, 2) solvent + GCIR, 3) EA + GCIR, and 4) EA. Under anesthesia with ketamine/xylazine, GCIR was induced (20 and 30 min respectively) in related groups. EA (100 mg/kg, dissolved in DMSO/saline (10%) or solvent was administered (1.5 ml/kg) orally for 10 consecutive days to the related groups. EEG was recorded from NTS in GCIR treated groups. Our data showed that: a) EEG in GCIR treated groups was flattened. b) GCIR reduced GFR ( P <0.01) and pretreatment with EA attenuated this reduction. c) BUN was increased by GCIR ( P <0.001) and pretreatment with EA improved the BUN to normal level. d) Serum creatinine concentration was elevated by GCIR but not significantly, however, in EA+GCIR group serum creatinine was reduced ( P <0.05). e) GCIR induced proteinuria ( P <0.05) but, EA was unable to reduced proteinuria. Results indicate that GCIR impairs certain renal functions and EA as an antioxidant can improve these functions. Our results suggest the possible usefulness of ellagic acid in patients with brain stroke.

Anti-pandemic influenza A (H1N1) virus potential of catechin and gallic acid.

PubMed

You, Huey-Ling; Huang, Chao-Chun; Chen, Chung-Jen; Chang, Cheng-Chin; Liao, Pei-Lin; Huang, Sheng-Teng

2018-05-01

The pandemic influenza A (H1N1) virus has spread worldwide and infected a large proportion of the human population. Discovery of new and effective drugs for the treatment of influenza is a crucial issue for the global medical community. According to our previous study, TSL-1, a fraction of the aqueous extract from the tender leaf of Toonasinensis, has demonstrated antiviral activities against pandemic influenza A (H1N1) through the down-regulation of adhesion molecules and chemokine to prevent viral attachment. The aim of the present study was to identify the active compounds in TSL-1 which exert anti-influenza A (H1N1) virus effects. XTT assay was used to detect the cell viability. Meanwhile, the inhibitory effect on the pandemic influenza A (H1N1) virus was analyzed by observing plaque formation, qRT-PCR, neuraminidase activity, and immunofluorescence staining of influenza A-specific glycoprotein. Both catechin and gallic acid were found to be potent inhibitors in terms of influenza virus mRNA replication and MDCK plaque formation. Additionally, both compounds inhibited neuraminidase activities and viral glycoprotein. The 50% effective inhibition concentration (EC 50 ) of catechin and gallic acid for the influenza A (H1N1) virus were 18.4 μg/mL and 2.6 μg/mL, respectively; whereas the 50% cytotoxic concentrations (CC 50 ) of catechin and gallic acid were >100 μg/mL and 22.1 μg/mL, respectively. Thus, the selectivity indexes (SI) of catechin and gallic acid were >5.6 and 22.1, respectively. The present study demonstrates that catechin might be a safe reagent for long-term use to prevent influenza A (H1N1) virus infection; whereas gallic acid might be a sensitive reagent to inhibit influenza virus infection. We conclude that these two phyto-chemicals in TSL-1 are responsible for exerting anti-pandemic influenza A (H1N1) virus effects. Copyright © 2017. Published by Elsevier Taiwan LLC.

Inhibition of class IIa histone deacetylase activity by gallic acid, sulforaphane, TMP269, and panobinostat.

PubMed

Choi, Sin Young; Kee, Hae Jin; Jin, Li; Ryu, Yuhee; Sun, Simei; Kim, Gwi Ran; Jeong, Myung Ho

2018-05-01

Histone deacetylase (HDAC) inhibitors are gaining increasing attention as potential therapeutics for cardiovascular diseases as well as cancer. We recently reported that the class II HDAC inhibitor, MC1568, and the phytochemical, gallic acid, lowered high blood pressure in mouse models of hypertension. We hypothesized that class II HDACs may be involved in the regulation of hypertension. The aim of this study was to determine and compare the effects of well-known HDAC inhibitors (TMP269, panobinostat, and MC1568), phytochemicals (gallic acid, sulforaphane, and piceatannol), and anti-hypertensive drugs (losartan, carvedilol, and furosemide) on activities of class IIa HDACs (HDAC4, 5, 7, and 9). The selective class IIa HDAC inhibitor, TMP269, and the pan-HDAC inhibitor, panobinostat, but not MC1568, clearly inhibited class IIa HDAC activities. Among the three phytochemicals, gallic acid showed remarkable inhibition, whereas sulforaphane presented mild inhibition of class IIa HDACs. Piceatannol inhibited only HDAC7 activity. As expected, the anti-hypertensive drugs losartan, carvedilol, and furosemide did not affect the activity of any class IIa HDAC. In addition, we evaluated the inhibitory effect of several compounds on the activity of class l HDACs (HDAC1, 2, 3, and 8) and class IIb HDAC (HDAC6). MC1568 did not affect the activities of HDAC1, HDAC2, and HDAC3, but it reduced the activity of HDAC8 at concentrations of 1 and 10 μM. Gallic acid weakly inhibited HDAC1 and HDAC6 activities, but strongly inhibited HDAC8 activity with effectiveness comparable to that of trichostatin A. Inhibition of HDAC2 activity by sulforaphane was stronger than that by piceatnnaol. These results indicated that gallic acid is a powerful dietary inhibitor of HDAC8 and class IIa/b HDAC activities. Sulforaphane may also be used as a dietary inhibitor of HDAC2 and class IIa HDAC. Our findings suggest that the class II HDAC inhibitor, MC1568, does not inhibit class IIa HDAC, but inhibits HDAC8. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

Effect of antioxidants on the quality of irradiated sausages prepared with turkey thigh meat.

PubMed

Du, M; Ahn, D U

2002-08-01

The effects of antioxidants on the flavor and color of electron-beam-irradiated turkey sausages were studied. Sausages were prepared from turkey thigh meat, NaCl (2.0%), phosphate (0.5%), water (10%), and one of five antioxidant treatments (none, vitamin E, sesamol, rosemary extract, or gallic acid at 0.02%). Sausages were stuffed and cooked in an 85 C smokehouse to an internal temperature of 74 C, then chilled and sliced to 1.5-cm thickness, and vacuum-packaged. Packaged sausages were randomly divided into three groups and irradiated at 0, 1.5 or 3.0 kGy, using an electron beam. Volatiles, color, 2-TBA-reactive substances values, and sensory characteristics were analyzed. The antioxidant effect of sesamol was the highest, followed by vitamin E and gallic acid; rosemary extract had the weakest antioxidant effect. Irradiation induced red color in sausages, but addition of gallic acid, rosemary extract, or sesamol reduced it. Gallic acid was very effective in lowering the redness of irradiated and nonirradiated sausages. The redness (a*) values of sausages with added gallic acid that were irradiated at 0, 1.5, and 3.0 kGy were 1.49,2.03, and 2.29, respectively, whereas those of control sausages under the same irradiation conditions were 2.58, 2.81, and 3.25, respectively. The reduction of redness in irradiated sausages by antioxidants was not related to CO, because antioxidants had no effect on CO production by irradiation. The amount of total volatiles was decreased significantly by antioxidants, but antioxidants had minimal effect on the off-flavor of turkey sausages induced by irradiation.

Potential for food-drug interactions by dietary phenolic acids on human organic anion transporters 1 (SLC22A6), 3 (SLC22A8), and 4 (SLC22A11).

PubMed

Wang, Li; Sweet, Douglas H

2012-10-15

Phenolic acids exert beneficial health effects such as anti-oxidant, anti-carcinogenic, and anti-inflammatory activities and show systemic exposure after consumption of common fruits, vegetables, and beverages. However, knowledge regarding which components convey therapeutic benefits and the mechanism(s) by which they cross cell membranes is extremely limited. Therefore, we determined the inhibitory effects of nine food-derived phenolic acids, p-coumaric acid, ferulic acid, gallic acid, gentisic acid, 4-hydroxybenzoic acid, protocatechuic acid, sinapinic acid, syringic acid, and vanillic acid, on human organic anion transporter 1 (hOAT1), hOAT3, and hOAT4. In the present study, inhibition of OAT-mediated transport of prototypical substrates (1 μM) by phenolic acids (100 μM) was examined in stably expressing cell lines. All compounds significantly inhibited hOAT3 transport, while just ferulic, gallic, protocatechuic, sinapinic, and vanillic acid significantly blocked hOAT1 activity. Only sinapinic acid inhibited hOAT4 (~35%). For compounds exhibiting inhibition > ~60%, known clinical plasma concentration levels and plasma protein binding in humans were examined to select compounds to evaluate further with dose-response curves (IC(50) values) and drug-drug interaction (DDI) index determinations. IC(50) values ranged from 1.24 to 18.08 μM for hOAT1 and from 7.35 to 87.36 μM for hOAT3. Maximum DDI indices for gallic and gentisic acid (≫0.1) indicated a very strong potential for DDIs on hOAT1 and/or hOAT3. This study indicates that gallic acid from foods or supplements, or gentisic acid from salicylate-based drug metabolism, may significantly alter the pharmacokinetics (efficacy and toxicity) of concomitant therapeutics that are hOAT1 and/or hOAT3 substrates. Copyright © 2012 Elsevier Inc. All rights reserved.

Synthesis and spectroscopic characterization of gallic acid and some of its azo complexes

NASA Astrophysics Data System (ADS)

Masoud, Mamdouh S.; Hagagg, Sawsan S.; Ali, Alaa E.; Nasr, Nessma M.

2012-04-01

A series of gallic acid and azo gallic acid complexes were prepared and characterized by elemental analysis, IR, electronic spectra and magnetic susceptibility. The complexes were of different geometries: Octahedral, Tetrahedral and Square Planar. ESR was studied for copper complexes. All of the prepared complexes were of isotropic nature. The thermal analyses of the complexes were studied by DTA and DSC techniques. The thermodynamic parameters and the thermal transitions, such as glass transitions, crystallization and melting temperatures for some ligands and their complexes were evaluated and discussed. The entropy change values, ΔS#, showed that the transition states are more ordered than the reacting complexes. The biological activities of some ligands and their complexes are tested against Gram positive and Gram negative bacteria. The results showed that some complexes have a well considerable activity against different organisms.

African crocus (Curculigo pilosa) and wonderful kola (Buchholzia coriacea) seeds modulate critical enzymes relevant to erectile dysfunction and oxidative stress.

PubMed

Adefegha, Stephen A; Oyeleye, Sunday I; Oboh, Ganiyu

2018-05-23

Background The seeds of African crocus (AC) (Curculigo pilosa) and wonderful kola (WK) (Buchholzia coriacea) are commonly used in folklore medicine in managing erectile dysfunction (ED) without the full understanding of the possible mechanism of actions. This study investigated and compared the effects of aqueous extracts from the seeds of AC and WK on arginase and acetylcholinesterase (AChE) activities and some pro-oxidant [FeSO4 and sodium nitroprusside (SNP)]-induced lipid peroxidation in rat penile homogenate in vitro. Method Aqueous extracts of AC and WK were prepared, and their effects on arginase and AChE activities as well as FeSO4- and SNP-induced lipid peroxidation in rat penile homogenate were assessed. Furthermore, phenolic constituents of the extract were determined using high-performance liquid chromatography coupled with diode-array detector (HPLC-DAD). Results Both extracts exhibited concentration-dependent inhibition on arginase (AC, IC50=0.05 mg/mL; WK, IC50=0.22 mg/mL) and AChE (AC, IC50=0.68 mg/mL; WK, IC50=0.28 mg/mL) activities. The extracts also inhibited FeSO4- and SNP-induced lipid peroxidation in rat penile homogenate. HPLC-DAD analysis revealed the presence of phenolic acids (gallic, caffeic, ellagic and coumaric acids) and flavonoids (catechin, quercetin and apigenin) in AC and WK. AC had higher arginase inhibitory and antioxidative activities but lower AChE inhibitory properties when compared with WK. Conclusions These effects could explain the possible mechanistic actions of the seeds in the management/treatment of ED and could be as a result of individual and/or synergistic effect of the constituent phenolic compounds of the seeds.

Bifunctional viscous nanovesicles co-loaded with resveratrol and gallic acid for skin protection against microbial and oxidative injuries.

PubMed

Vitonyte, Justina; Manca, Maria Letizia; Caddeo, Carla; Valenti, Donatella; Peris, Josè Esteban; Usach, Iris; Nacher, Amparo; Matos, Maria; Gutiérrez, Gemma; Orrù, Germano; Fernàndez-Busquets, Xavier; Fadda, Anna Maria; Manconi, Maria

2017-05-01

Resveratrol and gallic acid were co-loaded in phospholipid vesicles aiming at protecting the skin from external injuries, such as oxidative stress and microbial infections. Liposomes were prepared using biocompatible phospholipids dispersed in water. To improve vesicle stability and applicability, the phospholipids and the phenols were dispersed in water/propylene glycol or water/glycerol, thus obtaining PEVs and glycerosomes, respectively. The vesicles were characterized by size, morphology, physical stability, and their therapeutic efficacy was investigated in vitro. The vesicles were spherical, unilamellar and small in size: liposomes and glycerosomes were around 70nm in diameter, while PEVs were larger (∼170nm). The presence of propylene glycol or glycerol increased the viscosity of the vesicle systems, positively affecting their stability. The ability of the vesicles to promote the accumulation of the phenols (especially gallic acid) in the skin was demonstrated, as well as their low toxicity and great ability to protect keratinocytes and fibroblasts from oxidative damage. Additionally, an improvement of the antimicrobial activity of the phenols was shown against different skin pathogens. The co-loading of resveratrol and gallic acid in modified phospholipid vesicles represents an innovative, bifunctional tool for preventing and treating skin affections. Copyright © 2017 Elsevier B.V. All rights reserved.

Protective activity of hamamelitannin on cell damage induced by superoxide anion radicals in murine dermal fibroblasts.

PubMed

Masaki, H; Atsumi, T; Sakurai, H

1995-01-01

Previously we demonstrated that hamamelitannin (2',5-di-O-galloyl hamamelose) in Hamamelis virginiana L. exhibits potent superoxide-anion scavenging activity. We then examined the physiological and pharmacological activities of hamamelitannin as well as its functional homologues, gallic acid and syringic acid. The following results were obtained: (1) Hamamelitannin has a higher protective activity against cell damages induced by superoxide anions than gallic acid which is the functional moiety of hamamelitannin. The protective activity of hamamelitannin on murine fibroblast-damage induced by superoxide anions was found at a minimum concentration of 50 microM, while the corresponding figure for gallic acid was 100 microM. (2) Pre-treatment of fibroblasts with hamamelitannin enhances cell survival. (3) The superoxide-anion scavenging activity of the compound in terms of its IC50 value (50% inhibition concentration of superoxide anion radicals generated) was evaluated by ESR spin-trapping. Both hamamelitannin (IC50 = 1.31 +/- 0.06 microM) and gallic acid (IC50 = 1.01 +/- 0.03 microM) exhibited high superoxide-anion scavenging activity followed by syringic acid (IC50 = 13.90 +/- 2.38 microM). (4) When hamamelitannin was treated with superoxide anions generated by a KO2-crown ether system, HPLC analysis showed the disappearance of hamamelitannin and the concomitant formation of hamamelitannin-derived radicals (g = 2.005, delta H1 = 2.16 G, delta H2 = 4.69 G) was detected by ESR spectrometry.(ABSTRACT TRUNCATED AT 250 WORDS)

Anti-Inflammatory Effect of Gallic Acid-Eluting Stent in a Porcine Coronary Restenosis Model

PubMed Central

Seob Lim, Kyung; Park, Jun-Kyu; Ho Jeong, Myung; Ho Bae, In; Sung Park, Dae; Won Shim, Jae; Ha Kim, Jung; Kuk Kim, Hyun; Soo Kim, Sung; Sun Sim, Doo; Joon Hong, Young; Han Kim, Ju; Ahn, Youngkeun

2018-01-01

Background Gallic acid (3,4,5-trihydroxybenzoic acid) is a natural polyphenol and strong natural antioxidant found abundantly in red wine and green tea. The aim of this study was to examine the anti-inflammatory effect of a novel gallic acid-eluting stent in a porcine coronary restenosis model. Methods Fifteen pigs were randomized into three groups; in which a total of 30 coronary arteries (10 in each group) were implanted with gallic acid-eluting stents (GESs, n = 10), gallic acid and sirolimus-eluting stents (GSESs, n = 10), or sirolimus-eluting stents (SESs, n = 10). Histopathologic analysis was performed 28 days after stenting. Results There were no significant differences in injury score and fibrin score among the groups, however there were significant differences in the internal elastic lamina (4.0 ± 0.83 mm2 in GES vs. 3.0 ± 0.53 mm2 in GSES vs. 4.6 ± 1.43 mm2 in SES, p < 0.0001), lumen area (2.3 ± 0.49 mm2 in GES vs. 1.9 ± 0.67 mm2 in GSES vs. 2.9 ± 0.56 mm2 in SES, p < 0.0001), neointimal area (1.7 ± 0.63 mm2 in GES vs. 1.1 ± 0.28 mm2 in GSES vs. 1.7 ± 1.17 mm2 in SES, p < 0.05), and percent area of stenosis (42.4% ± 9.22% in GES vs. 38.2% ± 12.77% in GSES vs. 33.9% ± 15.64% in SES, p < 0.05). The inflammation score was significantly lower in the GES and GSES groups compared to that in the SES group [1.0 (range: 1.0 to 2.0) in GES vs. 1.0 (range: 1.0 to 1.0) in GSES vs. 1.5 (range: 1.0 to 3.0) in SES, p < 0.05]. Conclusions The GES group had a greater percent area of stenosis than the SES group. Although gallic acid in the GES and GSES groups did not show a synergistic effect in suppressing neointimal hyperplasia, it resulted in greater inhibition of the inflammatory reaction in the porcine coronary restenosis model than in the SES group. PMID:29844643

Quantitative analysis of rutin, quercetin, naringenin, and gallic acid by validated RP- and NP-HPTLC methods for quality control of anti-HBV active extract of Guiera senegalensis.

PubMed

Alam, Perwez; Parvez, Mohammad K; Arbab, Ahmed H; Al-Dosari, Mohammed S

2017-12-01

Guiera senegalensis J.F. Gmel (Combretaceae) is a folk medicinal plant used in various metabolic and infectious diseases. In addition to its antiviral activities against herpes and fowlpox, the anti-HBV efficacy is very recently reported. To develop and validate simple, sensitive RP-/NP-HPTLC methods for quantitative determination of biomarkers rutin, quercetin, naringenin, and gallic acid in the anti-HBV active G. senegalensis leaves ethanol-extract. RP-HPTLC (rutin & quercetin; phase- acetonitrile:water, 4:6) and NP-HPTLC (naringenin & gallic acid; phase- toluene:ethyl acetate:formic acid, 6:4:0.8) were performed on glass-backed silica gel plates 60F 254 -RP18 and 60F 254 , respectively. The methods were validated according to the ICH guidelines. Well-separated and compact spots (R f ) of rutin (0.52 ± 0.006), quercetin (0.23 ± 0.005), naringenin (0.56 ± 0.009) and gallic acid (0.28 ± 0.006) were detected. The regression equations (Y) were 12.434x + 443.49, 10.08x + 216.85, 11.253x + 973.52 and 11.082x + 446.41 whereas the coefficient correlations (r 2 ) were 0.997 ± 0.0004, 0.9982 ± 0.0001, 0.9974 ± 0.0004 and 0.9981 ± 0.0001, respectively. The linearity ranges (ng/spot) were 200-1400 (RP-HPTLC) and 100-1200 (NP-HPTLC). The LOD/LOQ (ng/band) were 33.03/100.1 (rutin), 9.67/29.31 (quercetin), 35.574/107.8 (naringenin), and 12.32/37.35 (gallic acid). Gallic acid (7.01 μg/mg) was the most abundant biomarker compared to rutin (2.42 μg/mg), quercetin (1.53 μg/mg) and naringenin (0.14 μg/mg) in the extract. The validated NP-/RP-HPTLC methods were simple, accurate, and sensitive for separating and quantifying antiviral biomarkers in G. senegalensis, and endorsed its anti-HBV activity. The developed methods could be further employed in the standardization and quality-control of herbal formulations.

Tyrosinase inhibitory constituents from a polyphenol enriched fraction of rose oil distillation wastewater.

PubMed

Solimine, Jessica; Garo, Eliane; Wedler, Jonas; Rusanov, Krasimir; Fertig, Orlando; Hamburger, Matthias; Atanassov, Ivan; Butterweck, Veronika

2016-01-01

During the water steam distillation process of rose flowers, the non-volatile phenolic compounds remain in the waste. We recently developed a strategy to separate rose oil distillation water (RODW) into a polyphenol depleted water fraction and a polyphenol enriched fraction (RF20-SP207). Bioassay-guided investigation of RF20-SP207 led to the isolation of quercetin, kaempferol and ellagic acid. Their structures were elucidated by spectroscopic analysis as well as by comparison with literature data. Tyrosinase inhibition studies were performed with RF20-SP207, fractions I-IV, and the isolated compounds of the most active fraction. RF20-SP207 strongly inhibited the enzyme with an IC50 of 0.41 μg/mL. From the tested fractions only fraction IV (IC50=5.81 μg/mL) exhibited strong anti-tyrosinase activities. Quercetin, kaempferol and ellagic acid were identified in fraction IV and inhibited mushroom tyrosinase with IC50 values of 4.2 μM, 5.5 μM and 5.2 μM, respectively, which is approximately 10 times more potent than that of the positive control kojic acid (56.1μM). The inhibition kinetics, analyzed by Lineweaver-Burk plots, indicated that RF20-SP207 and fraction IV are uncompetitive inhibitors of tyrosinase when l-tyrosine is used as a substrate. A mixed inhibition was determined for ellagic acid, and a competitive inhibition for quercetin and kaempferol. In conclusion, the recovered polyphenol fraction RF20-SP207 from RODW was found to be a potent tyrosinase inhibitor. This value-added product could be used as an active ingredient in cosmetic products related to hyperpigmentation. Copyright © 2015 Elsevier B.V. All rights reserved.

The Secondary Structure of Human Hageman Factor (Factor XII) and its Alteration by Activating Agents

PubMed Central

McMillin, Carl R.; Saito, Hidehiko; Ratnoff, Oscar D.; Walton, Alan G.

1974-01-01

Hageman factor (factor XII) is activated by exposure to surfaces such as glass or by solutions of certain compounds, notably ellagic acid. Changes in the structure of Hageman factor accompanying activation have been examined in this study by circular dichroism spectroscopy. The spectrum of unactivated Hageman factor in aqueous solutions suggests that its conformation is mainly aperiodic. Various perturbants altered the conformation of Hageman factor in differing ways, demonstrating the sensitivity of Hageman factor to its environment. After activation of Hageman factor with solutions of ellagic acid, a negative trough appeared in the region of the circular dichroism spectrum commonly assigned to tyrosine residues, along with other minor changes in the peptide spectral region. Some of these changes are similar to changes that occurred upon partial neutralization of the basic residues at alkali pH. Activation of Hageman factor by adsorption to quartz surfaces (in an aqueous environment) also produced changes similar to those in the ellagic acid-activated Hageman factor, including the negative ellipticity in the tyrosine region. These observations suggest that the activation process may be related to a change in status of some of the basic amino acid residues, coupled with a specific change in the environment of some tyrosine residues. The importance of these changes during the activation process remains to be determined. The sensitivity of Hageman factor to its environment is consistent with the view that the initiation of clotting by exposure of plasma to appropriate agents is brought about by alterations in the conformation of Hageman factor that occur in the apparent absence of Fletcher factor or other recognized clotting factors. Images PMID:4373492

Antioxidants, low molecular weight carbohydrates, and total antioxidant capacity in strawberries (Fragaria x ananassa): effects of cultivar, ripening, and storage.

PubMed

Olsson, Marie E; Ekvall, Jimmy; Gustavsson, Karl-Erik; Nilsson, Jessica; Pillai, Deepa; Sjöholm, Ingegerd; Svensson, Ulla; Akesson, Björn; Nyman, Margareta G L

2004-05-05

Four cultivars of strawberries (Senga Sengana, BFr77111, Elsanta, and Honeoye) were studied for their content of antioxidants, total antioxidant capacity, and low molecular weight carbohydrates in relation to harvest year, ripening stage, and cold storage. For ascorbic acid, chlorogenic acid, ellagic acid, and total antioxidative capacity, measured in both water-soluble and water-insoluble extracts, there was a 2-5-fold variation among cultivars. Unripe berries contained lower concentrations of chlorogenic acid and p-coumaric acid and also quercetin and kaempferol compared with riper berries. During cold storage for up to 3 days, relatively few changes in the concentration of the different antioxidants occurred. The concentrations of several investigated parameters were interrelated, for example, for ascorbic acid and water-soluble antioxidant capacity and for ellagic acid and water-insoluble antioxidant capacity. The dominating sugars in strawberries were fructose and glucose, but considerable amounts of sucrose were also present, and their contents varied among cultivars, giving a predicted glycemic index of approximately 81. Verbascose, raffinose, and stachyose were found in only minor amounts. The study shows that the concentration of a number of bioactive compounds in strawberries varied according to cultivar, ripening stage, and storage. This information should make it possible to select strawberries with an optimal content of bioactive compounds.

Regulation of microRNA using promising dietary phytochemicals: Possible preventive and treatment option of malignant mesothelioma.

PubMed

Sayeed, Md Abu; Bracci, Massimo; Lucarini, Guendalina; Lazzarini, Raffaella; Di Primio, Roberto; Santarelli, Lory

2017-10-01

Malignant mesothelioma (MM) is a very aggressive, lethal cancer, and its incidence is increasing worldwide. Development of multi-drug resistance, therapy related side-effects, and disease recurrence after therapy are the major problems for the successful treatment of MM. Emerging evidence indicates that dietary phytochemicals can exert anti-cancer activities by regulating microRNA expression. Until now, only one dietary phytochemical (ursolic acid) has been reported to have MM microRNA regulatory ability. A large number of dietary phytochemicals still remain to be tested. In this paper, we have introduced some dietary phytochemicals (curcumin, epigallocatechin gallate, quercetin, genistein, pterostilbene, resveratrol, capsaicin, ellagic acid, benzyl isothiocyanate, phenethyl isothiocyanate, sulforaphane, indole-3-carbinol, 3,3'-diindolylmethane, diallyl disulphide, betulinic acid, and oleanolic acid) which have shown microRNA regulatory activities in various cancers and could regulate MM microRNAs. In addition to microRNA regulatory activities, curcumin, epigallocatechin gallate, quercetin, genistein, resveratrol, phenethyl isothiocyanate, and sulforaphane have anti-mesothelioma potentials, and pterostilbene, capsaicin, ellagic acid, benzyl isothiocyanate, indole-3-carbinol, 3,3'-diindolylmethane, diallyl disulphide, betulinic acid, and oleanolic acid have potentials to inhibit cancer by regulating the expression of various genes which are also known to be aberrant in MM. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

Phenolic composition and antioxidant activities in flesh and achenes of strawberries (Fragaria ananassa).

PubMed

Aaby, Kjersti; Skrede, Grete; Wrolstad, Ronald E

2005-05-18

High performance liquid chromatography coupled with diode array and coulometric array detectors were used to characterize and quantify phenolic compounds in achenes and flesh of ripe strawberries (cv Totem and Puget Reliance). Total phenolics and total monomeric anthocyanins were measured and antioxidant activities were evaluated by the FRAP and the ORAC assays. Strawberries contained 1% achenes on a fresh weight basis; however, they contributed to about 11% of total phenolics and 14% of antioxidant activities in strawberries. Ellagic acid, ellagic acid glycosides, and ellagitannins were the main contributors to the antioxidant activities of achenes. The major anthocyanin in flesh was pelargonidin-3-glucoside, whereas achenes consisted of nearly equal amounts of cyanidin-3-glucoside and pelargonidin-3-glucoside. Phenolic content and antioxidant activity of strawberry achenes were reduced by industrial processing. However, the levels were still high and strawberry waste byproduct could thus be a possible source of nutraceuticals or natural antioxidants.

UHPLC/HRMS Analysis of African Mango (Irvingia gabonensis) Seeds, Extract and Related Dietary Supplements

PubMed Central

Sun, Jianghao; Chen, Pei

2012-01-01

Dietary Supplements based on an extract from Irvingia gabonensis (African Mango, AM for abbreviation) seeds are one of the popular herbal weight loss dietary supplements in the US market. The extract is believed to be a natural and healthy way to lose weight and improve overall health. However, the chemical composition of African mango based-dietary supplements (AMDS) has never been reported. In this study, the chemical constituents of African mango seeds, African mango seeds extract (AMSE), and different kinds of commercially available African mango based dietary supplements (AMDS) have been investigated using an ultra high-performance liquid chromatography with high resolution mass spectrometry (UHPLC-HRMS) method. Ellagic acid, mono, di, tri-O methyl-ellagic acids and their glycosides were found as major components in African Mango seeds. These compounds may be used for quality control of African Mango extract and related dietary supplements. PMID:22880691

Antidepressant-like effect of gallic acid in mice: Dual involvement of serotonergic and catecholaminergic systems.

PubMed

Can, Özgür Devrim; Turan, Nazlı; Demir Özkay, Ümide; Öztürk, Yusuf

2017-12-01

This study was planned to examine the antidepressant potency of gallic acid (30 and 60mg/kg), a phenolic acid widely distributed in nature, together with its possible underlying monoaminergic mechanisms. Antidepressant-like activity was assessed using the tail suspension (TST) and the modified forced swimming tests (MFST). Locomotor activity was evaluated in an activity cage. Administration of gallic acid at 60mg/kg reduced the immobility duration of mice in both the TST and MFST without any changes in the locomotor activity. The anti-immobility effect observed in the TST was abolished with pre-treatment of p-chlorophenylalanine methyl ester (an inhibitor of serotonin synthesis; 100mg/kg i.p. administered for 4-consecutive days), ketanserin (a 5-HT2A/2C antagonist; 1mg/kg i.p.), ondansetron (a 5-HT3 antagonist; 0.3mg/kg i.p.), α-methyl-para-tyrosine methyl ester (an inhibitor of catecholamine synthesis; 100mg/kg i.p.), phentolamine (non-selective alpha-adrenoceptor antagonist; 5mg/kg i.p.), SCH 23390 (a dopamine D1 antagonist; 0.05mg/kg s.c.), and sulpiride (a dopamine D2/D3 antagonist; 50mg/kg i.p.). However, NAN 190 (a 5-HT1A antagonist; 0.5mg/kg i.p.) and propranolol (a non-selective β-adrenoceptor antagonist; 5mg/kg i.p.) pre-treatments were ineffective at reversing the antidepressant-like effects of gallic acid. The results of the present study indicate that gallic acid seems to have a dual mechanism of action by increasing not only serotonin but also catecholamine levels in synaptic clefts of the central nervous system. Further alpha adrenergic, 5-HT2A/2C and 5-HT3 serotonergic, and D1, D2, and D3 dopaminergic receptors also seem to be involved in this antidepressant-like activity. Copyright © 2017 Elsevier Inc. All rights reserved.

Relationship between the lipophilicity of gallic acid n-alquil esters' derivatives and both myeloperoxidase activity and HOCl scavenging.

PubMed

Rosso, Rober; Vieira, Tiago O; Leal, Paulo C; Nunes, Ricardo J; Yunes, Rosendo A; Creczynski-Pasa, Tânia B

2006-09-15

The gallic acid and several n-alkyl gallates, with the same number of hydroxyl substituents, varying only in the side carbonic chain length, with respective lipophilicity defined through the C log P, were studied. It evidenced the structure-activity relationship of the myeloperoxidase activity inhibition and the hypochlorous acid scavenger property, as well as its low toxicity in rat hepatic tissue. The gallates with C log P below 3.0 (compounds 2-7) were more active against the enzyme activity, what means that the addition of 1-6 carbons (C log P between 0.92 and 2.92) at the side chain increased approximately 50% the gallic acid effect. However, a relationship between the HOCl scavenging capability and the lipophilicity was not observed. With these results it is possible to suggest that the gallates protect the HOCl targets through two mechanisms: inhibiting its production by the enzyme and scavenging the reactive specie.

Influence of phenolic compounds on the growth and arginine deiminase system in a wine lactic acid bacterium

PubMed Central

Alberto, María R.; de Nadra, María C. Manca; Arena, Mario E.

2012-01-01

The influence of seven phenolic compounds, normally present in wine, on the growth and arginine deiminase system (ADI) of Lactobacillus hilgardii X1B, a wine lactic acid bacterium, was established. This system provides energy for bacterial growth and produces citrulline that reacts with ethanol forming the carcinogen ethyl carbamate (EC), found in some wines. The influence of phenolic compounds on bacterial growth was compound dependent. Growth and final pH values increased in presence of arginine. Arginine consumption decreased in presence of protocatechuic and gallic acids (31 and 17%, respectively) and increased in presence of quercetin, rutin, catechin and the caffeic and vanillic phenolic acids (between 10 and 13%, respectively). ADI enzyme activities varied in presence of phenolic compounds. Rutin, quercetin and caffeic and vanillic acids stimulated the enzyme arginine deiminase about 37–40%. Amounts of 200 mg/L gallic and protocatechuic acids inhibited the arginine deiminase enzyme between 53 and 100%, respectively. Ornithine transcarbamylase activity was not modified at all concentrations of phenolic compounds. As gallic and protocatechuic acids inhibited the arginine deiminase enzyme that produces citrulline, precursor of EC, these results are important considering the formation of toxic compounds. PMID:24031815

[Studies on chemical constituents from seeds of Euryale ferox].

PubMed

Sun, Hai-lin; Zhang, Ya-qiong; Xie, Xiao-yan; Che, Yan-yun

2014-11-01

To study the chemical constituents from the seeds of Euryale ferox. The chemical constituents were isolated by silica gel column, Sephadex LH-20 and their structures were identified by physico-chemical and spectral analysis. Seven compounds were purified from the 95% ethanol extract. These constituents were elucidated as protocatechuic acid (1), gallic acid (2), gallic acid ethyl ester(3),5 ,7-dihydroxychromone(4), β-sitosterol(5), daucosterol(6), and 5,7-dihydroxy-6,4'-dimethoxyflavone(7), respectively. All compounds are isolated from this plant for the first time.

Effect of phenolic compounds, ethyl alcohol, and sodium metabisulphite on the lytic activity of phage PL-1 on a Lactobacillus casei S strain.

PubMed

Lee, A; Eschenbruch, R; Waller, J

1985-09-01

The effect of phenolic compounds, ethyl alcohol, and sodium metabisulphite on the lytic activity of virulent bacteriophage PL-1 on a Lactobacillus casei S strain isolated from a lactic acid beverage fermentation was investigated. Catechin, caffeic, and gallic acids, commercially produced red, white, and champagne tannins, ethyl alcohol, and sodium metabisulphite inhibited plaque formation. Catechin, caffeic, and gallic acids were the most effective inhibitors of plaque formation. Commercially supplied oenocyanin was not effective.

EPR spectral investigation of radiation-induced radicals of gallic acid.

PubMed

Tuner, Hasan

2017-11-01

In the present work, spectroscopic features of the radiation-induced radicals of gallic acid compounds were investigated using electron paramagnetic resonance (EPR) spectroscopy. While un-irradiated samples presented no EPR signal, irradiated samples exhibited an EPR spectrum consisting of an intense resonance line at the center and weak lines on both sides. Detailed microwave saturation investigations were carried out to determine the origin of the experimental EPR lines. It is concluded that the two side lines of the triplet satellite originate from forbidden "spin-flip" transitions. The spectroscopic and structural features of the radiation-induced radicals were determined using EPR spectrum fittings. The experimental EPR spectra of the two gallic acid compounds were consistent with the calculated EPR spectroscopic features of the proposed radicals. It is concluded that the most probable radicals are the cyclohexadienyl-type, [Formula: see text] radicals for both compounds.

Gastroprotective Effect of Ginger Rhizome (Zingiber officinale) Extract: Role of Gallic Acid and Cinnamic Acid in H+, K+-ATPase/H. pylori Inhibition and Anti-Oxidative Mechanism

PubMed Central

Nanjundaiah, Siddaraju M.; Annaiah, Harish Nayaka Mysore; Dharmesh, Shylaja M.

2011-01-01

Zinger officinale has been used as a traditional source against gastric disturbances from time immemorial. The ulcer-preventive properties of aqueous extract of ginger rhizome (GRAE) belonging to the family Zingiberaceae is reported in the present study. GRAE at 200 mg kg−1 b.w. protected up to 86% and 77% for the swim stress-/ethanol stress-induced ulcers with an ulcer index (UI) of 50 ± 4.0/46 ± 4.0, respectively, similar to that of lansoprazole (80%) at 30 mg kg−1 b.w. Increased H+, K+-ATPase activity and thiobarbituric acid reactive substances (TBARS) were observed in ulcer-induced rats, while GRAE fed rats showed normalized levels and GRAE also normalized depleted/amplified anti-oxidant enzymes in swim stress and ethanol stress-induced animals. Gastric mucin damage was recovered up to 77% and 74% in swim stress and ethanol stress, respectively after GRAE treatment. GRAE also inhibited the growth of H. pylori with MIC of 300 ± 38 μg and also possessed reducing power, free radical scavenging ability with an IC50 of 6.8 ± 0.4 μg mL−1 gallic acid equivalent (GAE). DNA protection up to 90% at 0.4 μg was also observed. Toxicity studies indicated no lethal effects in rats fed up to 5 g kg−1 b.w. Compositional analysis favored by determination of the efficacy of individual phenolic acids towards their potential ulcer-preventive ability revealed that between cinnamic (50%) and gallic (46%) phenolic acids, cinnamic acid appear to contribute to better H+, K+-ATPase and Helicobacter pylori inhibitory activity, while gallic acid contributes significantly to anti-oxidant activity. PMID:19570992

Separation and purification of hydrolyzable tannin from Geranium wilfordii Maxim by reversed-phase and normal-phase high-speed counter-current chromatography.

PubMed

Liu, Dan; Su, Zhiguo; Wang, Changhai; Gu, Ming; Xing, Siliang

2010-08-01

Three hydrolyzable tannins, geraniin, corilagin and gallic acid, main active components of Geranium wilfordii Maxim, have been separated and purified in one-step by both reversed-phase and normal-phase high-speed counter-current chromatography. Gallic acid, corilagin and geraniin were purified from 70% aqueous acetone extract of G. wilfordii Maxim with solvent system n-hexane-ethyl acetate-methanol-acetic acid-water (1:10:0.2:0.2:20) by reversed-phase high-speed counter-current chromatography at purities of 94.2, 91.0 and 91.3%, at yields of 89.3, 82.9 and 91.7%, respectively. Gallic acid, corilagin and geraniin were purified with solvent system n-hexane-ethyl acetate-methanol-acetic acid-water (0.2:10:2:1:5) by normal-phase high-speed counter-current chromatography at purities of 85.9, 92.2 and 87.6%, at yields of 87.4, 94.6 and 94.3%, respectively. It was successful for both reversed-phase and normal-phase high-speed counter-current chromatography to separate high-polarity of low-molecular-weight substances.

In Vitro Effect of Activated Recombinant Factor VII (rFVIIa) on Coagulation Properties of Human Blood at Hypothermic Temperatures

DTIC Science & Technology

2007-11-01

purified soy phosphatides in ellagic acid (Actin FS Activated PTT Reagent, Dade Behring, Marburg, Germany) was added to plasma samples in a 1:1 volume...acetylsali- cylic acid or any other nonsteroidal anti-inflammatory drugs for the 7 days before blood sampling. A smooth cubital venipuncture was

Pomegranate polyphenols and urolithin A inhibit α-glucosidase, dipeptidyl peptidase-4, lipase, triglyceride accumulation and adipogenesis related genes in 3T3-L1 adipocyte-like cells.

PubMed

Les, Francisco; Arbonés-Mainar, José Miguel; Valero, Marta Sofía; López, Víctor

2018-06-28

Pomegranate fruit is considered an antidiabetic medicine in certain systems of traditional medicine. In addition, pomegranate polyphenols are known as powerful antioxidants with beneficial effects such as the reduction of oxidative / inflammatory stress and the increase of protective signalling such as antioxidant enzymes, neurotrophic factors and cytoprotective proteins. This work evaluates the effects of pomegranate juice, its main polyphenols known as ellagic acid and punicalagin, as well as its main metabolite urolithin A, on physiological and pharmacological targets of metabolic diseases such as obesity and diabetes. For this purpose, enzyme inhibition bioassays of lipase, α-glucosidase and dipeptidyl peptidase-4 were carried out in cell-free systems. Similarly, adipocytes derived from 3T3-L1 cells were employed to study the effects of ellagic acid, punicalagin and urolithin A on adipocyte differentiation and triglyceride (TG) accumulation. Pomegranate juice, ellagic acid, punicalagin and urolithin A were able to inhibit lipase, α-glucosidase and dipeptidyl peptidase-4. Furthermore, all tested compounds but significantly the metabolite urolithin A displayed anti-adipogenic properties in a dose-dependent manner as they significantly reduced TG accumulation and gene expression related to adipocyte formation such as adiponectin, PPARγ, GLUT4, and FABP4 in 3T3-L1 adipocytes. These results may explain from a molecular perspective the beneficial effects and traditional use of pomegranate in the prevention of metabolic-associated disorders such as obesity, diabetes and related complications. Copyright © 2018 Elsevier B.V. All rights reserved.

Strecker Aldehyde Formation in Wine: New Insights into the Role of Gallic Acid, Glucose, and Metals in Phenylacetaldehyde Formation.

PubMed

Monforte, Ana Rita; Martins, Sara I F S; Silva Ferreira, Antonio C

2018-03-14

Strecker degradation (SD) leading to the formation of phenylacetaldehyde (PA) was studied in wine systems. New insights were gained by using two full factorial designs focusing on the effects of (1) pH and (2) temperature. In each design of experiments (DoE) three factors, glucose, gallic acid, and metals at two levels (present or absence), were varied while phenylalanine was kept constant. The obtained results gave a clear indication, with statistical significance, that in wine conditions, the SD occurs in the presence of metals preferentially via the phenolic oxidation independent of the temperature (40 or 80 °C). The reaction of the amino acid with the o-quinone formed by the oxidation of the gallic acid seems to be favored when compared with the SD promoted by the reaction with α-dicarbonyls formed by MR between glucose and phenylalanine. In fact, kinetics results showed that the presence of glucose had an inhibitory effect on PA rate of formation. PA formation was 4 times higher in the control wine when compared to the same wine with 10 g/L glucose added. By gallic acid quinone quantitation it is shown that glucose affects directly the concentration of the quinone. decreasing the rate of quinone formation. This highlights the role of sugar in o-quinone concentration and consequently in the impact on Strecker aldehyde formation, a promising new perspective regarding wine shelf-life understanding.

Study on the mechanism of allelopathic influence on cyanobacteria and chlorophytes by submerged macrophyte (Myriophyllum spicatum) and its secretion.

PubMed

Zhu, Junying; Liu, Biyun; Wang, Jing; Gao, Yunni; Wu, Zhenbin

2010-06-10

For revealing the mechanism of allelopathic influence on phytoplankton by aquatic macrophytes, the growth and photosynthetic activities of cyanobacteria Microcystis aeruginosa and the chlorophyte Selenastrum capricornutum were investigated when they coexisted with submerged macrophyte Myriophyllum spicatum and were exposed to allelopathic polyphenols: pyrogallic acid (PA), gallic acid (GA), ellagic acid (EA) and (+)-catechin (CA). According to the results of coexistence assays, the non-photochemical quenching (NPQ) and effective quantum efficiency (YII) of M. aeruginosa were affected earlier and more rapidly than the cell density. However, the influence of M. spicatum on S. capricornutum was not found. When the Toxicity Index (TI) was applied to evaluate the combined effects of binary and multiple mixtures of polyphenols, it was found that the four tested polyphenols with the proportion identified in the M. spicatum-cultured solution were observed to present synergistic effect (0.36-0.49) according to the cell density, NPQ and YII of M. aeruginosa. With the combined effects of polyphenols on S. capricornutum, only additive action (0.52-1.62) was found. On the other hand, PA (2.97mgL(-1)), GA (2.65mgL(-1)) caused significant reductions of photosystem II (PSII) and whole electron transport chain activities of M. aeruginosa by 71.43 and 18.37%, 70.95 and 40.77% (P<0.05), respectively, after 24-h exposure, but no inhibition effect was found in S. capricornutum. The dark respiration and photosystem I (PSI) activities of M. aeruginosa were significantly increased by exposure to PA and GA (P<0.05). Nevertheless, EA and CA had no influence on the electron transport activities of the tested organisms. These results indicate that the reduction in photosynthetic activity of M. aeruginosa and the synergistic effect of allelochemicals may be two important causes for the inhibition of undesired phytoplankton by submersed macrophytes in natural aquatic ecosystems, and PSII in cyanobacteria is considered to be one of the target sites attacked by allelopathic polyphenols.

Energetic and biochemical valorization of cork boiling wastewater by anaerobic digestion.

PubMed

Marques, Isabel Paula; Gil, Luís; La Cara, Francesco

2014-01-01

In addition to energy benefits, anaerobic digestion offers other interesting advantages. The cork industry is of great environmental, economic and social significance in the western Mediterranean region, with Portugal being the world-leading producer and exporter. Cork boiling wastewater (CBW) is a toxic and recalcitrant organic effluent produced by this sector, which constitutes a serious environmental hazard. However, there is no documented research on anaerobic treatment/valorization performed with this effluent. The work presented here was developed with the aim to use the anaerobic digestion process to convert the CBW polluting organic load into an energy carrier gas and valuable molecules for industry. No lag phases were observed and a methane yield of 0.126 to 0.142 m(3) kg(-1) chemical oxygen demand (COD)added was registered in the mesophilic consortium experiments carried out in batch flasks at 37 ± 1°C. Anaerobic digestion can be advantageously connected to ultrafiltration or electrochemical processes, due to the following: 1) reduction of ellagic acid content and consequent decrease of CBW viscosity; and 2) increase in conductivity after the anaerobic process, avoiding the electrolyte application of the electrochemical process. The improvement of several CBW biochemical features shows that anaerobic digestion may provide additionally useful molecules. The rise in concentration of some of these compounds, belonging to the benzoic acid family (gallic, protocatechuic, vanillic and syringic acids), is responsible for the increase of antiradical activity of the phenolic fraction. Additionally, some enzymatic activity was also observed and while the laccase activity increased in the digested effluent by anaerobiosis, xylanase was formed in the process. The multidisciplinary approach adopted allowed the valorization of CBW in terms of energy and valuable biomolecules. By exploiting the anaerobic digestion process potential, a novel methodology to toxic and recalcitrant cork processing wastewater was developed.

Energetic and biochemical valorization of cork boiling wastewater by anaerobic digestion

PubMed Central

2014-01-01

Background In addition to energy benefits, anaerobic digestion offers other interesting advantages. The cork industry is of great environmental, economic and social significance in the western Mediterranean region, with Portugal being the world-leading producer and exporter. Cork boiling wastewater (CBW) is a toxic and recalcitrant organic effluent produced by this sector, which constitutes a serious environmental hazard. However, there is no documented research on anaerobic treatment/valorization performed with this effluent. The work presented here was developed with the aim to use the anaerobic digestion process to convert the CBW polluting organic load into an energy carrier gas and valuable molecules for industry. Results No lag phases were observed and a methane yield of 0.126 to 0.142 m3 kg-1 chemical oxygen demand (COD)added was registered in the mesophilic consortium experiments carried out in batch flasks at 37 ± 1°C. Anaerobic digestion can be advantageously connected to ultrafiltration or electrochemical processes, due to the following: 1) reduction of ellagic acid content and consequent decrease of CBW viscosity; and 2) increase in conductivity after the anaerobic process, avoiding the electrolyte application of the electrochemical process. The improvement of several CBW biochemical features shows that anaerobic digestion may provide additionally useful molecules. The rise in concentration of some of these compounds, belonging to the benzoic acid family (gallic, protocatechuic, vanillic and syringic acids), is responsible for the increase of antiradical activity of the phenolic fraction. Additionally, some enzymatic activity was also observed and while the laccase activity increased in the digested effluent by anaerobiosis, xylanase was formed in the process. Conclusions The multidisciplinary approach adopted allowed the valorization of CBW in terms of energy and valuable biomolecules. By exploiting the anaerobic digestion process potential, a novel methodology to toxic and recalcitrant cork processing wastewater was developed. PMID:24847378

Effect of harvest, drying and storage on the bitterness, moisture, sugars, free amino acids and phenolic compounds of jujube fruit (Zizyphus jujuba cv. Junzao).

PubMed

Pu, Yunfeng; Ding, Tian; Wang, Wenjun; Xiang, Yanju; Ye, Xingqian; Li, Mei; Liu, Donghong

2018-01-01

The taste of dried jujube fruit when compared with fresh ones is less palatable, as it develops bitterness during drying and storage. Therefore, identifying the methods by which bitterness occurs is essential for developing strategies for processing and storage. Bitterness in fresh jujube fruit was negligible; however, it increased by 0.9-, 1.5- and 1.8-fold during drying and storage over 6 and 12 months. The moisture significantly decreased during harvesting and drying. Free amino acids, except proline and tyrosine, significantly decreased during drying and storage. Fructose, glucose and sucrose hardly changed during harvest, drying and storage. Titratable acidity, total phenolic and total flavonoids contents were stable during harvest and drying, but increased upon storage. Additionally, protocatechuic and ellagic acids were not detected in fresh jujube fruit, however, were found to increase during drying and storage. Bitterness in fresh jujube fruit tasted negligible because of meagre amount of phytochemicals, while the condensation effect of moisture reduction, the loss of free amino acids, and the formation of protocatechuic and ellagic acids could aggravate the bitterness of jujube fruit during drying and storage. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

Simultaneous analysis of tea catechins, caffeine, gallic acid, theanine and ascorbic acid by micellar electrokinetic capillary chromatography.

PubMed

Aucamp, J P; Hara, Y; Apostolides, Z

2000-04-21

A micellar electrokinetic capillary chromatography (MEKC) method for the simultaneous analysis of five tea catechins, theanine, caffeine, gallic acid and ascorbic acid has been developed. The catechins are (-)-epicatechin, (+)-catechin, (-)-epigallocatechin, (-)-epicatechin gallate and (-)-epigallocatechin gallate. p-Nitrophenol serves as both reference and internal standard. All the components are separated within 13 min with a 57 cm uncoated fused-silica column. On-column detection was carried out at 200 nm. This method has been used to measure these compounds in fresh tea leaves and tea liquor. The limit of detection for all analytes ranged from 1 to 20 microg/ml.

Intestinal Permeability and Cellular Antioxidant Activity of Phenolic Compounds from Mango (Mangifera indica cv. Ataulfo) Peels.

PubMed

Pacheco-Ordaz, Ramón; Antunes-Ricardo, Marilena; Gutiérrez-Uribe, Janet A; González-Aguilar, Gustavo A

2018-02-08

Mango ( Mangifera indica cv. Ataulfo) peel contains bound phenolics that may be released by alkaline or acid hydrolysis and may be converted into less complex molecules. Free phenolics from mango cv. Ataulfo peel were obtained using a methanolic extraction, and their cellular antioxidant activity (CAA) and permeability were compared to those obtained for bound phenolics released by alkaline or acid hydrolysis. Gallic acid was found as a simple phenolic acid after alkaline hydrolysis along with mangiferin isomers and quercetin as aglycone and glycosides. Only gallic acid, ethyl gallate, mangiferin, and quercetin were identified in the acid fraction. The acid and alkaline fractions showed the highest CAA (60.5% and 51.5%) when tested at 125 µg/mL. The value of the apparent permeability coefficient (Papp) across the Caco-2/HT-29 monolayer of gallic acid from the alkaline fraction was higher (2.61 × 10 -6 cm/s) than in the other fractions and similar to that obtained when tested pure (2.48 × 10 -6 cm/s). In conclusion, mango peels contain bound phenolic compounds that, after their release, have permeability similar to pure compounds and exert an important CAA. This finding can be applied in the development of nutraceuticals using this important by-product from the mango processing industry.

The modulating effect of Persea americana fruit extract on the level of expression of fatty acid synthase complex, lipoprotein lipase, fibroblast growth factor-21 and leptin--A biochemical study in rats subjected to experimental hyperlipidemia and obesity.

PubMed

Monika, Padmanabhan; Geetha, Arumugam

2015-09-15

Obesity is a multifactorial disorder which is closely associated with hyperlipidemia. Avocados are edible fruits traditionally consumed for various health benefits including body weight reduction. To determine the hypolipidemic and anti-obesity effect of hydro-alcoholic fruit extract of avocado (HFEA) in rats fed with high fat diet (HFD). Male Sprague Dawley rats were divided into four groups. Groups 1 and 2 rats were fed with normal diet. Groups 3 and 4 rats were fed with HFD for 14 weeks. In addition, Groups 2 and 4 rats were co-administered with 100 mg/kg body weight of HFEA from 3rd week onwards. The HFEA was subjected to HPLC to quantify the major phytonutrients. Body mass index (BMI), adiposity index (ADI), total fat pad mass (TFP), blood lipid levels were determined in all the groups of rats. The mRNA expression of fatty acid synthase (FASN), lipoprotein lipase (LPL), fibroblast growth factor 21 (FGF21) and leptin was also assessed. HFEA was found to contain flavonoids: rutin-141.79, quercetin-5.25, luteolin-165, phenolic compounds: gallic acid-198.57, ellagic acid-238.22, vanillic acid-4.79 and phytosterols: betasitosterol-70, stigmasterol-12.5 (mg/100 g). HFEA reduced BMI, ADI, TFP, blood cholesterol, triglycerides, and LDL in rats fed with HFD. Serum leptin was found reduced in HFEA co-administered rats. The mRNA expression of FASN, LPL, and leptin in subcutaneous and visceral adipose tissue was found to be significantly reduced in HFEA co-administered rats. The gene expression of fibroblast growth factor-21 (FGF21) was found to be significantly increased in HFEA treated rats when compared to HFD control rats. The hypolipidemic effect of HFEA may be partly due to its modulating effect on endogenous fat synthesis and adiponectin formation through the transcription factor FGF21. The results also show that avocado fruit extract has profound influence on leptin activity, which controls satiety and hunger to regulate the food intake. Copyright © 2015 Elsevier GmbH. All rights reserved.

Alterations in blood pressure, antioxidant status and caspase 8 expression in cobalt chloride-induced cardio-renal dysfunction are reversed by Ocimum gratissimum and gallic acid in Wistar rats.

PubMed

Akinrinde, A S; Oyagbemi, A A; Omobowale, T O; Asenuga, E R; Ajibade, T O

2016-07-01

The protective abilities of the chloroform extract of Ocimum gratissimum (COG) and gallic acid against cobalt chloride (CoCl2) - induced cardiac and renal toxicity were evaluated. Rats were exposed to CoCl2 (350ppm) for 7 days, either alone, or in combination with COG (100 and 200mg/kg) or gallic acid (120mg/kg). CoCl2 given alone, caused significant increases (p<0.05) in oxidative stress parameters (hydrogen peroxide, H2O2 and malondialdehyde, MDA) and increased expression of the apoptotic initiator caspase 8 in the heart and kidneys. There was significant reduction (p<0.05) in reduced glutathione (GSH) in cardiac and renal tissues; reduction in superoxide dismutase (SOD) activity in the kidneys and adaptive increases in Glutathione S-transferase (GST) and catalase (CAT). CoCl2 also produced significant reduction (p<0.05) in systolic (SBP), diastolic (DBP) and mean arterial (MAP) blood pressures. Oral COG and gallic acid treatment significantly reduced (p<0.05) the levels of H2O2 and MDA; with reduced expression of caspase 8 and restoration of GSH levels, GPx, SOD and CAT activities, howbeit, to varying degrees in the heart and kidneys. COG (200mg/kg) was most effective in restoring the blood pressures in the rats to near control levels. CoCl2-induced histopathological lesions including myocardial infarction and inflammation and renal tubular necrosis and inflammation were effectively ameliorated by the treatments administered. This study provides evidence for the protective roles of O. gratissimum and gallic acid by modulation of CoCl2-induced alterations in blood pressure, antioxidant status and pro-apoptotic caspase 8 in Wistar rats. Copyright © 2016 Elsevier GmbH. All rights reserved.

Analysis of Phenolic Compounds and Antioxidant Abilities of Extracts from Germinating Vitis californica Seeds Submitted to Cold Stress Conditions and Recovery after the Stress

PubMed Central

Weidner, Stanisław; Chrzanowski, Sebastian; Karamać, Magdalena; Król, Angelika; Badowiec, Anna; Mostek, Agnieszka; Amarowicz, Ryszard

2014-01-01

The material for this study consisted of stratified seeds of Vitis californica submitted to germination under optimum conditions (+25 °C) or under chill stress (+10 °C), also followed by recovery. It has been determined that the germinating seeds contain considerable amounts of tannins, catechins as well as phenolic acids such as gallic, p-coumaric, caffeic and ferulic acids. Gallic acid appeared in the highest amount in the germinating seeds (from 42.40–204.00 µg/g of fresh weight (FW)), followed by caffeic acid (from 6.62–20.13 µg/g FW), p-coumaric acid (from 2.59–5.41 µg/g FW), and ferulic acid (from 0.56–0.92 µg/g FW). The phenolic acids occurred mostly in the ester form. Under chill stress, the germinating seeds were determined to contain an elevated total amount of phenolics, as well as raised levels of condensed tannins, catechins, gallic acid, and gafeic acid. The levels of p-coumoric and ferulic acids were found to have decreased. In extracts isolated from a sample exposed to low temperature, increased antioxidant activity and reduction potential were also demonstrated. Tissue of the germinating seeds which underwent post-stress recovery was found to have less total phenolics. PMID:25222557

Visual Reading Method for Detection of Bacterial Tannase

PubMed Central

Osawa, R.; Walsh, T. P.

1993-01-01

Tannase activity of bacteria capable of degrading tannin-protein complexes was determined by a newly developed visual reading method. The method is based on two phenomena: (i) the ability of tannase to hydrolyze methyl gallate to release free gallic acid and (ii) the green to brown coloration of gallic acid after prolonged exposure to oxygen in an alkaline condition. The method has been successfully used to detect the presence of tannase in the cultures of bacteria capable of degrading tannin-protein complexes. PMID:16348918

Protection capacity against low-density lipoprotein oxidation and antioxidant potential of some organic and non-organic wines.

PubMed

Kalkan Yildirim, Hatice; Delen Akçay, Yasemin; Güvenç, Ulgar; Yildirim Sözmen, Eser

2004-08-01

Current research suggests that phenolics from wine may play a positive role against oxidation of low-density lipoprotein (LDL), which is a key step in the development of atherosclerosis. Considering the effects of different wine-making techniques on phenols and the wine consumption preference influencing the benefical effects of the product, organically and non-organically produced wines were obtained from the grapes of Vitis vinifera origin var: Carignan, Cabernet Sauvignon, Merlot, Grenache, Columbard and Semillon. Levels of total phenols [mg/l gallic acid equivalents (GAE)], antioxidant activity (%) and inhibition of LDL oxidation [%, inhibition of diene and malondialdehyde (MDA) formation] were determined. Some phenolic acids (gallic acid, p-hydroxybenzoic acid, syringic acid, 2,3-dihydroxybenzoic acid, ferulic acid, p-coumaric acid and vanillic acid) were quantified by high-performance liquid chromatography equipped with an electrochemical detection carried at +0.65 V (versus Ag/AgCl, 0.5 microA full scale). The highest concentrations of gallic, syringic and ferulic acids were found in organic Cabernet Sauvignon; 2,3-dihydroxybenzoic acid in organic Carignan and p-coumaric and vanillic acids in non-organic Merlot wine. High levels of antioxidant activity (AOA), inhibition of LDL oxidation and total phenol levels were found in non-organic Merlot (101.950% AOA; 88.570% LDL-diene; 41.000% LDL-MDA; 4700.000 mg/l GAE total phenol) and non-organic Cabernet Sauvignon (92.420% AOA; 91.430% LDL-diene; 67.000% LDL-MDA; 3500.000 mg/l GAE total phenol) grape varieties. Concentrations of some individual phenolic constituents (ferulic, p-coumaric, vanillic) are correlated with high antioxidant activity and inhibition of LDL oxidation. The best r value for all examined characteristics was determined for gallic acid, followed by 2,3-dihydroxybenzoic, syringic, ferulic and p-coumaric acids. Negative correlation of vanillic with MDA and p-hydroxybenzoic acid with LDL were confirmed by principal component analysis (PCA) analyses. Red wines display a higher antioxidant activity (81.110% AOA) than white ones (19.512% AOA). The average level of LDL inhibition capacity in red wine was determined as 87.072% and for the white as 54.867%.

Luminescent behavior of cadmium sulfide quantum dots for gallic acid estimation

NASA Astrophysics Data System (ADS)

Singh, Suman; Garg, Sourav; Chahal, Jitender; Raheja, Khushboo; Singh, Deepak; Singla, M. L.

2013-03-01

Thioglycolic acid capped cadmium sulfide (CdS/T) quantum dots have been synthesized using wet chemistry and their optical behavior has been investigated using UV-visible absorption and fluorescence spectroscopy. The role of the capping agent, sulfide source concentration, pH and temperature has been studied and discussed. Studies showed that alkaline pH leads to a decrease in the size of quantum dots and reflux temperature above 70 °C resulted in red-shift of emission spectra which is due to narrowing of the bandgap. Further, to reduce the toxicity and photochemical instability of quantum dots, the quantum dots have been functionalized with polyethylene glycol (PEG), which resulted in a 20% enhancement of the fluorescence intensity. The application potential of CdS/T-PEG quantum dots was further studied using gallic acid as a model compound. The sensing is based on fluorescence quenching of quantum dots in the presence of gallic acid, and this study showed linearity in the range from 1.3 × 10-8 to 46.5 × 10-8 mM, with a detection limit of 3.6 × 10-8 mM.

Spectroscopic studies on the antioxidant activity of ellagic acid

NASA Astrophysics Data System (ADS)

Kilic, Ismail; Yeşiloğlu, Yeşim; Bayrak, Yüksel

2014-09-01

Ellagic acid (EA, C14H6O8) is a natural dietary polyphenol whose benefits in a variety of diseases shown in epidemiological and experimental studies involve anti-inflammation, anti-proliferation, anti-angiogenesis, anticarcinogenesis and anti-oxidation properties. In vitro radical scavenging and antioxidant capacity of EA were clarified using different analytical methodologies such as total antioxidant activity determination by ferric thiocyanate, hydrogen peroxide scavenging, 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH) scavenging, 2,2‧-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging activity and superoxide anion radical scavenging, ferrous ions (Fe2+) chelating activity and ferric ions (Fe3+) reducing ability. EA inhibited 71.2% lipid peroxidation of a linoleic acid emulsion at 45 μg/mL concentration. On the other hand, butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), α-tocopherol and ascorbic acid displayed 69.8%, 66.8%, 64.5% and 59.7% inhibition on the peroxidation of linoleic acid emulsion at the same concentration, respectively. In addition, EA had an effective DPPH• scavenging, ABTSrad + scavenging, superoxide anion radical scavenging, hydrogen peroxide scavenging, ferric ions (Fe3+) reducing power and ferrous ions (Fe2+) chelating activities. Also, those various antioxidant activities were compared to BHA, BHT, α-tocopherol and ascorbic acid as references antioxidant compounds. These results suggested that EA can be used in the pharmacological, food industry and medicine because of these properties.

The effects of antioxidants and shelf life conditions on oxidation markers in a sunflower oil salad dressing emulsion (SOSDE).

PubMed

Sainsbury, Jeanine; Grypa, Roman; Ellingworth, John; Duodu, Kwaku G; De Kock, Henriëtta L

2016-12-15

The effects of levels of antioxidant [gallic acid or ethylene diamine tetraacetate (EDTA)] in a sunflower oil salad dressing emulsion (SOSDE) and shelf life affecting conditions on aroma, anisidine values (AV) and peroxide values (PV) were determined. Aroma differences between products with different concentrations of antioxidants were more apparent for ambient than accelerated stored SOSDEs. Aroma differences were more noted between SOSDEs with different antioxidants than antioxidant concentrations per se. PV differences between accelerated stored SOSDEs with high and low EDTA concentrations were found. AV differences existed between SOSDEs with different gallic acid concentrations for both storage conditions, and for accelerated stored SOSDEs with different EDTA concentrations. The accelerated storage model is more suitable for SOSDEs with metal chelator antioxidants e.g. EDTA, than free radical scavenging antioxidants e.g. gallic acid. PV, AV and aroma of accelerated stored SOSDEs do not clearly predict ambient shelf life. Copyright © 2016 Elsevier Ltd. All rights reserved.

Crude ethanol extracts from grape seeds and peels exhibit anti-tyrosinase activity.

PubMed

Hsu, Cheng-Kuang; Chou, Su-Tze; Huang, Pai-Jane; Mong, Mei-Chin; Wang, Chien-Kuo; Hsueh, Yu-Pin; Jhan, Jyun-Kai

2012-01-01

This study aimed to evaluate the anti-tyrosinase activities of ethanol extracts from the peels and the seeds of Kyoho grapes and Red Globe grapes (KG-PEE, KG-SEE, RGG-PEE, and RGG-SEE). The total phenolic content in KG-SEE and RGG-SEE was 400 +/- 11 and 339 +/- 7 mg gallic acid equivalent/g, respectively, about 22 times and 13 times that in KG-PEE and RGG-PEE, respectively. Both seed extracts showed significantly higher anti-tyrosinase activity than the peel extracts due to their high total phenolic content. The gallic acid content in RGG-SEE was twice that in KG-SEE, and gallic acid showed high anti-tyrosinase activity; thus, RGG-SEE had higher anti-tyrosinase activity than KG-SEE. Lineweaver-Burk plots revealed that the inhibitory mechanism of the ethanol extracts from the grapes was a mix-type inhibition. Grape seed has a greater total phenolic content and has potential as a skin-lighting agent.

Evaluation of gallic acid loaded zein sub-micron electrospun fibre mats as novel active packaging materials.

PubMed

Neo, Yun Ping; Swift, Simon; Ray, Sudip; Gizdavic-Nikolaidis, Marija; Jin, Jianyong; Perera, Conrad O

2013-12-01

The applicability of gallic acid loaded zein (Ze-GA) electrospun fibre mats towards potential active food packaging material was evaluated. The surface chemistry of the electrospun fibre mats was determined using X-ray photon spectroscopy (XPS). The electrospun fibre mats showed low water activity and whitish colour. Thermogravimetric analysis (TGA) and Attenuated Total Reflectance-Fourier Transform Infrared (ATR-FTIR) spectroscopy revealed the stability of the fibre mats over time. The Ze-GA fibre mats displayed similar rapid release profiles, with Ze-GA 20% exhibiting the fastest release rate in water as compared to the others. Gallic acid diffuses from the electrospun fibres in a Fickian diffusion manner and the data obtained exhibited a better fit to Higuchi model. L929 fibroblast cells were cultured on the electrospun fibres to demonstrate the absence of cytotoxicity. Overall, the Ze-GA fibre mats demonstrated antibacterial activity and properties consistent with those considered desirable for active packaging material in the food industry. Copyright © 2013 Elsevier Ltd. All rights reserved.

Biotechnological procedures to select white rot fungi for the degradation of PAHs.

PubMed

Lee, Hwanhwi; Jang, Yeongseon; Choi, Yong-Seok; Kim, Min-Ji; Lee, Jaejung; Lee, Hanbyul; Hong, Joo-Hyun; Lee, Young Min; Kim, Gyu-Hyeok; Kim, Jae-Jin

2014-02-01

White rot fungi are essential in forest ecology and are deeply involved in wood decomposition and the biodegradation of various xenobiotics. The fungal ligninolytic enzymes involved in these processes have recently become the focus of much attention for their possible biotechnological applications. Successful bioremediation requires the selection of species with desirable characteristics. In this study, 150 taxonomically and physiologically diverse white rot fungi, including 55 species, were investigated for their performance in a variety of biotechnological procedures, such as dye decolorization, gallic acid reaction, ligninolytic enzymes, and tolerance to four PAHs, phenanthrene, anthracene, fluoranthene, and pyrene. Among these fungi, six isolates showed the highest (>90%) tolerance to both individual PAH and mixed PAHs. And six isolates oxidized gallic acid with dark brown color and they rapidly decolorized RBBR within ten days. These fungi revealed various profiles when evaluated for their biotechnological performance to compare the capability of degradation of PAHs between two groups selected. As the results demonstrated the six best species selected from gallic acid more greatly degraded four PAHs than the other isolates selected via tolerance test. It provided that gallic acid reaction test can be performed to rank the fungi by their ability to degrade the PAHs. Most of all, Peniophora incarnata KUC8836 and Phlebia brevispora KUC9033 significantly degraded the four PAHs and can be considered prime candidates for the degradation of xenobiotic compounds in environmental settings. Copyright © 2013 Elsevier B.V. All rights reserved.

Intestinal Permeability and Cellular Antioxidant Activity of Phenolic Compounds from Mango (Mangifera indica cv. Ataulfo) Peels

PubMed Central

Pacheco-Ordaz, Ramón; González-Aguilar, Gustavo A.

2018-01-01

Mango (Mangifera indica cv. Ataulfo) peel contains bound phenolics that may be released by alkaline or acid hydrolysis and may be converted into less complex molecules. Free phenolics from mango cv. Ataulfo peel were obtained using a methanolic extraction, and their cellular antioxidant activity (CAA) and permeability were compared to those obtained for bound phenolics released by alkaline or acid hydrolysis. Gallic acid was found as a simple phenolic acid after alkaline hydrolysis along with mangiferin isomers and quercetin as aglycone and glycosides. Only gallic acid, ethyl gallate, mangiferin, and quercetin were identified in the acid fraction. The acid and alkaline fractions showed the highest CAA (60.5% and 51.5%) when tested at 125 µg/mL. The value of the apparent permeability coefficient (Papp) across the Caco-2/HT-29 monolayer of gallic acid from the alkaline fraction was higher (2.61 × 10−6 cm/s) than in the other fractions and similar to that obtained when tested pure (2.48 × 10−6 cm/s). In conclusion, mango peels contain bound phenolic compounds that, after their release, have permeability similar to pure compounds and exert an important CAA. This finding can be applied in the development of nutraceuticals using this important by-product from the mango processing industry. PMID:29419800

Quantum chemical density functional theory studies on the molecular structure and vibrational spectra of Gallic acid imprinted polymers

NASA Astrophysics Data System (ADS)

Pardeshi, Sushma; Dhodapkar, Rita; Kumar, Anupama

2013-12-01

Gallic acid (GA) is known by its antioxidant, anticarcinogenic properties and scavenger activity against several types of harmful free radicals. Molecularly imprinted polymers (MIPs) are used in separation of a pure compound from complex matrices. A stable template-monomer complex generates the MIPs with the highest affinity and selectivity for the template. The quantum chemical computations based on density functional theory (DFT) was used on the template Gallic acid (GA), monomer acrylic acid (AA) and GA-AA complex to study the nature of interactions involved in the GA-AA complex. B3LYP/6-31+G(2d,2p) model chemistry was used to optimize their structures and frequency calculations. The effect of porogen acetonitrile (ACN) on complex formation was included by using polarizable continuum model (PCM). The results demonstrated the formation of a stable GA-AA complex through the intermolecular hydrogen bonding between carboxylic acid groups of GA and AA. The Mulliken atomic charge analysis and simulated vibrational spectra also supported the stable hydrogen bonding interaction between the carboxylic acid groups of GA and AA with minimal interference of porogen ACN. Further, simulations on GA-AA mole ratio revealed that 1:4 GA-AA was optimum for synthesis of MIP for GA.

Fermentation and dry fractionation increase bioactivity of cloudberry (Rubus chamaemorus).

PubMed

Puupponen-Pimiä, Riitta; Nohynek, Liisa; Juvonen, Riikka; Kössö, Tuija; Truchado, Pilar; Westerlund-Wikström, Benita; Leppänen, Tiina; Moilanen, Eeva; Oksman-Caldentey, Kirsi-Marja

2016-04-15

Phenolic composition and bioactivity of cloudberry was modified by bioprocessing, and highly bioactive fractions were produced by dry fractionation of the press cake. During fermentation polymeric ellagitannins were partly degraded into ellagic acid derivatives. Phenolic compounds were differentially distributed in seed coarse and fine fractions after dry fractionation process. Tannins concentrated in fine fraction, and flavonol derivatives were mainly found in coarse fraction. Ellagic acid derivatives were equally distributed between the dry fractions. Fermentation and dry fractionation increased statistically significantly anti-adhesion and anti-inflammatory activity of cloudberry. The seed fine fraction showed significant inhibition of P fimbria-mediated haemagglutination assay of uropathogenic Escherichia coli. The seed coarse fraction significantly reduced NO and IL-6 production and iNOS expression in activated macrophages. Fermentation did not affect antimicrobial activity, but slight increase in activity was detected in dry fractions. The results indicate the potential of cloudberry in pharma or health food applications. Copyright © 2015 Elsevier Ltd. All rights reserved.

Evaluation of different extraction methods from pomegranate whole fruit or peels and the antioxidant and antiproliferative activity of the polyphenolic fraction.

PubMed

Masci, Alessandra; Coccia, Andrea; Lendaro, Eugenio; Mosca, Luciana; Paolicelli, Patrizia; Cesa, Stefania

2016-07-01

Pomegranate is a functional food of great interest, due to its multiple beneficial effects on human health. This fruit is rich in anthocyanins and ellagitannins, which exert a protective role towards degenerative diseases. The aim of the present work was to optimize the extraction procedure, from different parts of the fruit, to obtain extracts enriched in selected polyphenols while retaining biological activity. Whole fruits or peels of pomegranate cultivars, with different geographic origin, were subjected to several extraction methods. The obtained extracts were analyzed for polyphenolic content, evaluated for antioxidant capacity and tested for antiproliferative activity on human bladder cancer T24 cells. Two different extraction procedures, employing ethyl acetate as a solvent, were useful in obtaining extracts enriched in ellagic acid and/or punicalagins. Antioxidative and antiproliferative assays demonstrated that the antioxidant capability is directly related to the phenolic content, whereas the antiproliferative activity is to be mainly attributed to ellagic acid. Copyright © 2016 Elsevier Ltd. All rights reserved.

Improvements in Metabolic Health with Consumption of Ellagic Acid and Subsequent Conversion into Urolithins: Evidence and Mechanisms12

PubMed Central

Kang, Inhae; Buckner, Teresa; Gu, Liwei

2016-01-01

Ellagic acid (EA) is a naturally occurring polyphenol found in some fruits and nuts, including berries, pomegranates, grapes, and walnuts. EA has been investigated extensively because of its antiproliferative action in some cancers, along with its anti-inflammatory effects. A growing body of evidence suggests that the intake of EA is effective in attenuating obesity and ameliorating obesity-mediated metabolic complications, such as insulin resistance, type 2 diabetes, nonalcoholic fatty liver disease, and atherosclerosis. In this review, we summarize how intake of EA regulates lipid metabolism in vitro and in vivo, and delineate the potential mechanisms of action of EA on obesity-mediated metabolic complications. We also discuss EA as an epigenetic effector, as well as a modulator of the gut microbiome, suggesting that EA may exert a broader spectrum of health benefits than has been demonstrated to date. Therefore, this review aims to suggest the potential metabolic benefits of consumption of EA-containing fruits and nuts against obesity-associated health conditions. PMID:27633111

Both plants Sebastiania chamaelea from Niger and Chrozophora senegalensis from Senegal used in African traditional medicine in malaria treatment share a same active principle.

PubMed

Garcia-Alvarez, M-C; Moussa, I; Njomnang Soh, P; Nongonierma, R; Abdoulaye, A; Nicolau-Travers, M-L; Fabre, A; Wdzieczak-Bakala, J; Ahond, A; Poupat, C; Ikhiri, K; Benoit-Vical, F

2013-10-07

Based on ethnobotanical data obtained from Nigerien and Senegalese traditional healers, two Euphorbiaceae plants, Sebastiania chamaelea and Chrozophora senegalensis, traditionally used to treat malaria, were selected for further investigations. Plant extracts were prepared with different solvents and tested both in vitro on several strains of Plasmodium falciparum, and in vivo to evaluate their antiplasmodial properties and isolate their active principles. With IC50 values around 6.5µg/ml and no significant cytotoxicity (>50µg/ml), the whole plant aqueous extract from S. chamaelea showed the best in vitro results. In vitro potentiation assays showed strong synergistic activity of S. chamaelea extract with the antiplasmodial drug chloroquine on the chloroquine-resistant P. falciparum strain W2-Indochina. In other respects, the aqueous crude extract of C. senegalensis leaves showed the most significant antiplasmodial activity in vitro (IC50 values less than 2µg/ml). We also demonstrated the prophylactic activity of C. senegalensis in vivo in a murine malaria model. Bioassay-guided fractionation of aqueous extracts of these plants enabled the isolation and identification of ellagic acid (EA, 1) as the main compound responsible for their antiplasmodial activity. Together with EA, other derivatives belonging to different chemical groups were isolated but showed moderate antimalarial activity: gallic acid (2), brevifolin carboxylic acid (3), protocatechuic acid (4), corillagin (5), rutin (6) and 3,4,8,9,10-pentahydroxy-dibenzo(b,d)pyran-6-one (7). The structures were determined by the usual spectroscopic methods and by comparison with published data. Furthermore, we report here the quantification of compound 1 (EA) by RP-HPLC in the dried extracts of these plants, reported for the first time in both these species, and possessing the highest in vitro antiplasmodial activity with IC50 values from 180 to 330nm. These in vitro and in vivo results support the traditional use in Africa of crude extracts of both S. chamaelea and C. senegalensis as an antimalarial treatment and prove the significant antiplasmodial property of EA. © 2013 Elsevier Ireland Ltd. All rights reserved.

Wheat germ oil enrichment in broiler feed with α-lipoic acid to enhance the antioxidant potential and lipid stability of meat.

PubMed

Arshad, Muhammad Sajid; Anjum, Faqir Muhammad; Khan, Muhammad Issa; Shahid, Muhammad; Akhtar, Saeed; Sohaib, Muhammad

2013-11-04

Lipid peroxidation is the cause of declining the meat quality. Natural antioxidants plays a vital role in enhancing the stability and quality of meat. The supplementation of natural antioxidants in feed decreases lipid peroxidation and improves the stability of meat. The present research was conducted to determine the effect of α-lipoic acid, α-tocopherol and wheat germ oil on the status of antioxidants, quality and lipid stability of broiler meat. One day old male broilers were fed with different feeds containing antioxidants i.e. natural (wheat germ oil) and synthetic α-tocopherol and α-lipoic acid during the two experimental years. The feed treatments have significant variation on the body weight and feed conversion ratio (FCR) while having no influence on the feed intake. The broilers fed on wheat germ oil (natural α-tocopherol) gained maximum body weight (2451.97 g & 2466.07 g) in the experimental years 2010-11 & 2011-12, respectively. The higher total phenolic contents were found in the broilers fed on wheat germ oil plus α-lipoic acid in breast (162.73±4.8 mg Gallic acid equivalent/100 g & 162.18±4.5 mg Gallic acid equivalent/100 g) and leg (149.67±3.3 mg Gallic acid equivalent/100 g & 146.07±3.2 mg Gallic acid equivalent/100 g) meat during both experimental years. Similar trend was observed for the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing antioxidant power assay (FRAP). The production of malondialdehydes in the breast and leg meat increased with progressive increase in the time period. The deposition of α-tocopherol (AT) and α-lipoic acid (ALA) contents were found to be higher in the broilers fed on wheat germ oil plus α-lipoic acid in breast and leg meat during the both experimental years. In conclusion, the combination of wheat germ oil and α-lipoic acid has more beneficial for stability and the quality of the broiler meat and more work should be needed in future for the bio-evaluation of this kind of functional meat in humans.

Comparison of the Composition and Antioxidant Activities of Phenolics from the Fruiting Bodies of Cultivated Asian Culinary-Medicinal Mushrooms.

PubMed

Lin, Shaoling; Ching, Lai Tsz; Ke, Xinxin; Cheung, Peter Chi Keung

2016-01-01

The composition profile and the antioxidant properties of phenolics in water extracts obtained from the fresh fruiting bodies of 4 common cultivated Asian edible mushrooms-Agrocybe aegerita, Pleurotus ostreatus, P. eryngii, and Pholiota nameko were compared. The water extract from A. aegerita (AaE) had the highest total phenolic content (TPC) at 54.18 ± 0.27 gallic acid equivalents (μmol/L)/mg extract (P < 0.05), as measured by the Folin-Ciocalteu method, and consisted of the largest number (including gallic acid, protocatechuic acid, chlorogenic acid, ferulic acid, and sinapic acid) and total amounts of phenolic acids identified by Fourier transform-ion cyclotron resonance mass spectrometry. The water extract of Ph. nameko was found to have the second-highest TPC (43.55 ± 0.10 gallic acid equivalents [μmol/L]/mg extract), followed by the water extract of P. eryngii and the water extract of P. ostreatus (39.55 ± 0.25 and 39.02 ± 0.30 gallic acid equivalents/mg extract, respectively). The scavenging activities of the water extracts from these mushrooms were evaluated against 2,2-diphenyl-l-(2,4,6-trinitrophenyl) hydrazyl diphenylpicrylhydrazyl (DPPH), superoxide anion radicals, hydroxyl radicals, and hydrogen peroxide. Based on halfmaximal effective concentrations, AaE was more effective in scavenging hydrogen peroxide (<0.05), followed by DPPH (0.51 mg/mL), superoxide anion radicals (0.85 mg/mL) and hydroxyl radicals (5.94 mg/mL), then the other mushroom water extracts. The differences in the half-maximal effective concentrations of individual mushroom water extracts were probably the result of the different numbers and amounts of individual phenolic acids in the extracts. The antioxidant activities of the mushroom water extracts were correlated with their TPC. The strongest antioxidant properties of AaE were consistent with its highest TPC and with the largest number and amount of phenolics identified in the extract. These results indicated that cultivated edible mushrooms could be a potential source of natural antioxidants with free radical scavenging properties for application as a functional food ingredient.

Are Natural Ingredients Effective in the Management of Hyperpigmentation? A Systematic Review

PubMed Central

Angra, Kunal; Halder, Rebat M.

2018-01-01

BACKGROUND: Hyperpigmentation disorders are commonly encountered in dermatology clinics. Botanical and natural ingredients have gained popularity as alternative depigmenting products. OBJECTIVE: We sought to review clinical studies evaluating the use of different natural products in treating hyperpigmentation so clinicians are better equipped to educate their patients. Specific ingredients reviewed include azelaic acid, aloesin, mulberry, licorice extracts, lignin peroxidase, kojic acid, niacinamide, ellagic acid, arbutin, green tea, turmeric, soy, and ascorbic acid. METHODS: Systematic searches of PubMed and SCOPUS databases were performed in March 2016 using the various ingredient names, “melasma”and “hyperpigmentation.” Two reviewers independently screened titles, leading to the selection of 30 clinical studies. RESULTS: Review of the literature revealed few clinical trials that evaluated the treatment of hyperpigmentation with natural ingredients. Despite the limited evidence-based research, several natural ingredients did show efficacy as depigmenting agents, including azelaic acid, soy, lignin peroxidase, ascorbic acid iontophoresis, arbutin, ellagic acid, licorice extracts, niacinamide, and mulberry. CONCLUSION: The aforementioned ingredients show promise as natural treatments for patients with hyperpigmentation disorders. These agents might also provide clinicians and researchers with a way to further characterize the pathogenesis of dyschromia. However, the paucity of clinical studies is certainly a limitation. Additionally, many of the in-vivo studies are limited by the short length of the trials, and questions remain about the long-term efficacy and safety of the ingredients used in these studies. Lastly, we suggest a standardized objective scoring system be implemented in any further comparative studies. PMID:29552273

Changes on indigenous microbiota, colour, bioactive compounds and antioxidant activity of pasteurised pomegranate juice.

PubMed

Mena, Pedro; Vegara, Salud; Martí, Nuria; García-Viguera, Cristina; Saura, Domingo; Valero, Manuel

2013-12-01

Juices prepared from arils of 'Mollar' pomegranates were analysed for naturally occurring microorganisms, CIE Lab colour parameters, total phenols, anthocyanins and punicalagins, ellagic acid content and antioxidant capacity before and after low-, mild- and high-temperature pasteurisations (LTPs, MTPs and HTPs): 65, 80 and 90 °C for 30 or 60s. Mean aerobic plate count (APC), yeast and mold count (YMC), and lactic acid bacteria (LAB) for fresh juices were 5.7, 5.36 and 4.0 log CFU/mL, respectively. MTPs and HTPs were sufficiently effective to decrease APCs to nil or negligible levels. An increase in CIE a values and decrease in CIE b values were the characteristic colour changes in heat-treated juices. The effect of pasteurisations showed that total phenols, punicalagins and ellagic acid were not much affected by thermal processing. Total anthocyanin content and antioxidant capacity were substantially and significantly influenced by the heat treatment applied. A linear relationship was observed between Trolox equivalent antioxidant capacity (TEAC) values and total anthocyanins, suggesting that they contributed strongly to the antioxidant capacity of pomegranate juice. Copyright © 2013 Elsevier Ltd. All rights reserved.

Isoniazid cocrystals with anti-oxidant hydroxy benzoic acids

NASA Astrophysics Data System (ADS)

Mashhadi, Syed Muddassir Ali; Yunus, Uzma; Bhatti, Moazzam Hussain; Tahir, Muhammad Nawaz

2014-11-01

Isoniazid is the primary constituent of “triple therapy” used to effectively treat tuberculosis. In tuberculosis and other diseases, tissue inflammation and free radical burst from macrophages results in oxidative stress. These free radicals cause pulmonary inflammation if not countered by anti-oxidants. Therefore, in the present study cocrystals of isoniazid with four anti-oxidant hydroxy benzoic acids have been reported. Gallic acid, 2,3-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, and 3-hydroxybenzoic acid resulted in the formation of cocrystals when reacted with isoniazid. Cocrystal structure analysis confirmed the existence of pyridine-carboxylic acid synthon in the cocrystals of isoniazid with Gallic acid, 2,3-dihydroxybenzoic acid and 3-hydroxybenzoic acid. While cocrystal of 3,5-dihydroxybenzoic acid formed the pyridine-hydroxy group synthon. Other synthons of different graph sets are formed between hydrazide group of isoniazid and coformers involving Nsbnd H⋯O and Osbnd H⋯N bonds. All the cocrystals were in 1:1 stoichiometric ratio.

Production of propyl gallate in nonaqueous medium using cell-associated tannase of Bacillus massiliensis: effect of various parameters and statistical optimization.

PubMed

Aithal, Mahesh; Belur, Prasanna D

2013-01-01

Enzymatic synthesis of propyl gallate in an organic solvent was studied using cell-associated tannase (E.C. 3.1.1.20) of Bacillus massiliensis. Lyophilized biomass showing tannase activity was used as a biocatalyst. The influence of buffer pH and strength, water activity, temperature, biocatalyst loading, gallic acid concentration, and 1-propanol concentration was studied by the one-factor-at-a-time method. Subsequently, response surface methodology was applied based on a central composite design to determine the effects of three independent variables (biocatalyst loading, gallic acid concentration, and 1-propanol concentration) and their mutual interactions. A total of 20 experiments were conducted, and a statistical model was developed, which predicted the maximum propyl gallate yield of 20.28 μg/mL in the reaction mixture comprising 40.4 mg biocatalyst, 0.4 mM gallic acid, and 6.52 % (v/v) 1-propanol in 9.5 mL benzene at 30°C. The subsequent verification experiments established the validity of the model. Under optimal conditions, 25% conversion of gallic acid to propyl gallate was achieved on a molar basis. The absence of the need for enzyme purification and subsequent immobilization steps and good conversion efficiency makes this enzyme system an interesting one. Reports on the applications of bacterial whole cell systems for synthetic reactions in organic solvents are scarce, and perhaps this is the first report on bacterial cell-associated tannase-mediated esterification in a nonaqueous medium. © 2013 International Union of Biochemistry and Molecular Biology, Inc.

Gallic acid ameliorates hyperglycemia and improves hepatic carbohydrate metabolism in rats fed a high-fructose diet.

PubMed

Huang, Da-Wei; Chang, Wen-Chang; Wu, James Swi-Bea; Shih, Rui-Wen; Shen, Szu-Chuan

2016-02-01

Herein, we investigated the hypoglycemic effect of plant gallic acid (GA) on glucose uptake in an insulin-resistant cell culture model and on hepatic carbohydrate metabolism in rats with a high-fructose diet (HFD)-induced diabetes. Our hypothesis is that GA ameliorates hyperglycemia via alleviating hepatic insulin resistance by suppressing hepatic inflammation and improves abnormal hepatic carbohydrate metabolism by suppressing hepatic gluconeogenesis and enhancing the hepatic glycogenesis and glycolysis pathways in HFD-induced diabetic rats. Gallic acid increased glucose uptake activity by 19.2% at a concentration of 6.25 μg/mL in insulin-resistant FL83B mouse hepatocytes. In HFD-induced diabetic rats, GA significantly alleviated hyperglycemia, reduced the values of the area under the curve for glucose in an oral glucose tolerance test, and reduced the scores of the homeostasis model assessment of insulin resistance index. The levels of serum C-peptide and fructosamine and cardiovascular risk index scores were also significantly decreased in HFD rats treated with GA. Moreover, GA up-regulated the expression of hepatic insulin signal transduction-related proteins, including insulin receptor, insulin receptor substrate 1, phosphatidylinositol-3 kinase, Akt/protein kinase B, and glucose transporter 2, in HFD rats. Gallic acid also down-regulated the expression of hepatic gluconeogenesis-related proteins, such as fructose-1,6-bisphosphatase, and up-regulated expression of hepatic glycogen synthase and glycolysis-related proteins, including hexokinase, phosphofructokinase, and aldolase, in HFD rats. Our findings indicate that GA has potential as a health food ingredient to prevent diabetes mellitus. Copyright © 2016 Elsevier Inc. All rights reserved.

Mitigation of diazinon-induced cardiovascular and renal dysfunction by gallic acid

PubMed Central

Ajibade, Temitayo Olabisi; Omobowale, Temidayo Olutayo; Asenuga, Ebunoluwa Racheal; Afolabi, Jeremiah Moyinoluwa; Adedapo, Adeolu Alex

2016-01-01

Studies of the link between environmental pollutants and cardiovascular dysfunction, neglected for decades, have recently provided new insights into the pathology and consequences of these killers. In this study, rats were divided into four groups, each containing 10 rats. The rats in group one served as controls and were administered normal saline, whereas the rats in group two were orally gavaged with 3 mg/kg of diazinon (DZN) alone for twenty one consecutive days. The rats in groups 3 and 4 were administered respective 60 mg/kg and 120 mg/kg gallic acid (GA) in addition to DZN for twenty one consecutive days. Exposure of rats to diazinon significantly (p<0.05) reduced the activities of superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GPx), glutathione-S-transferase (GST) and reduced glutathione (GSH) content. Malondialdehyde, hydrogen peroxide (H2O2) and nitric oxide (NO) contents were also significantly (p<0.05) elevated following DZN exposure. DZN further caused a significant (p<0.05) decrease of heart rate and QT interval prolongation. Hematologic analysis revealed significant reduction (p<0.05) in packed cell volume (PCV), hemoglobin concentration (Hb), red blood cell (RBC) count, and total white blood cell count of rats administered only DZN. Observations in this study suggest a modulatory role of gallic acid in diazinon-induced anemia and associated cardiovascular dysfunction in rats. Treatment with gallic acid reversed the oxidative stress markers studied, increased the antioxidant defence system and reduced deleterious effects on hematological parameters in rats. Pathologic findings of the heart and kidney were also found to be lessened. PMID:28652848

Stability of Pycnogenol® as an ingredient in fruit juices subjected to in vitro gastrointestinal digestion.

PubMed

Frontela, Carmen; Ros, Gaspar; Martínez, Carmen; Sánchez-Siles, Luis M; Canali, Raffaella; Virgili, Fabio

2011-01-30

The enrichment of fruit juices with concentrated polyphenolic extracts is an expedient strategy to compensate possible phenolic loss through gastrointestinal processing. Pycnogenol, a standardised procyanidin-rich extract from pine bark, has been proposed as a potential candidate for polyphenol enrichment of foods. In this study the effects of in vitro digestion on the phenolic profile of fruit juices enriched with Pycnogenol were investigated. After in vitro digestion the level of detectable total phenolic compounds (expressed as gallic acid equivalent) was higher in both pineapple and red fruit juices enriched with Pycnogenol than in non-enriched commercial juices. Five phenolic monomeric compounds were identified by high-performance liquid chromatography, namely chlorogenic acid, caffeic acid, ferulic acid, gallic acid and taxifolin, the last two being predominant. In vitro digestion of both Pycnogenol-enriched pineapple and red fruit juices led to a significant (P < 0.05) increase in detectable chlorogenic and ferulic acids, indicating that hydrolysis of more complex molecules occurs. On the other hand, in vitro digestion of non-enriched juices was associated with a decrease in gallic and caffeic acids in pineapple juice and with a decrease in ferulic acid in red fruit juice. In no case did in vitro digestion increase the amount of detectable phenolic compounds in non-enriched juices. The stability of Pycnogenol after in vitro gastrointestinal digestion makes it a good choice for phenolic enrichment of fruit juices. 2010 Society of Chemical Industry.

A novel, eco-friendly technique for covalent functionalization of graphene nanoplatelets and the potential of their nanofluids for heat transfer applications

NASA Astrophysics Data System (ADS)

Sadri, Rad; Hosseini, Maryam; Kazi, S. N.; Bagheri, Samira; Zubir, Nashrul; Ahmadi, Goodarz; Dahari, Mahidzal; Zaharinie, Tuan

2017-05-01

In this study, a facile and eco-friendly covalent functionalization technique is developed to synthesize highly stable graphene nanoplatelets (GNPs) in aqueous media. This technique involves free radical grafting of gallic acid onto the surface of GNPs rather than corrosive inorganic acids. Raman spectroscopy, X-ray photoelectron spectroscopy and transmission electron microscopy are used to confirm the covalent functionalization of GNPs with gallic acid (GAGNPs). The solubility of the GAGNPs in aqueous media is verified using zeta potential and UV-vis spectra measurements. The nanofluid shows significant improvement in thermo-physical properties, indicating its superb potential for various thermal applications.

[Studies on the phenolic acids from Sarcopyramis bodinieri var. delicata].

PubMed

Yang, Jia-Yong; Wan, Chun-Peng; Qiu, Yan

2010-04-01

To study the chemical constituents from Sarcopyramis bodinieri var. delicata. These compounds were isolated and purified by chromatography with silica gel column combined with Sephadex LH-20 column from high polar extracts. The structures were identified on the basis of extensive spectroscopic data analysis, and by comparison of their spectral data with those reported. Seven compounds were isolated as 3, 3'-di-O-methylellagic acid-4'-O-alpha-L-rhamnopyranoside (I), ellagic acid (II), ferulic acid (III), isoferulic acid (IV), caffeic acid (V), 3, 4-di-hydroxybenzoic acid (VI), p-hydroxycinnamic acid (VII). Compound I, III, VI, VII are isolated from the genus for the first time.

Antioxidant compounds, antioxidant activity and phenolic content in peel from three tropical fruits from Yucatan, Mexico.

PubMed

Moo-Huchin, Víctor M; Moo-Huchin, Mariela I; Estrada-León, Raciel J; Cuevas-Glory, Luis; Estrada-Mota, Iván A; Ortiz-Vázquez, Elizabeth; Betancur-Ancona, David; Sauri-Duch, Enrique

2015-01-01

The aim of this study was to determine the antioxidant compounds, antioxidant activity and content of individual phenolic compounds of freeze-dried peel from three tropical fruits grown in Yucatan, México: purple star apple (Chrysophyllum cainito L.), yellow cashew and red cashew (Anacardium occidentale). The freeze-dried peels were good source of antioxidant compounds. ABTS and DPPH values in the peel from each fruit were 3050.95-3322.31 μM Trolox/100g dry weight (DW) or 890.19-970.01 mg of vitamin C/100 g DW, and 1579.04-1680.90 μM Trolox/100 g DW or 340.18-362.18 mg of vitamin C/100 g DW, respectively. Six phenolic compounds were identified in the peel from the tropical fruits studied: ferulic, caffeic, sinapic, gallic, ellagic and myricetin. This study demonstrated that freeze-dried peels from purple star apple, yellow cashew and red cashew, could serve as potential sources of antioxidants for use in food and pharmaceutical industries. Copyright © 2014 Elsevier Ltd. All rights reserved.

Ancient Seed for Modern Cure - Pomegranate Review of Therapeutic Applications in Periodontics.

PubMed

Thangavelu, Arthiie; Elavarasu, Sugumari; Sundaram, Rajasekar; Kumar, Tamilselvan; Rajendran, Dhivya; Prem, Fairlin

2017-11-01

Punica granatum (pomegranate), the member of Punicaceae family, is used in the prevention and treatment of health disorders. P. granatum contains diverse range of phytochemicals including ellagic acid, punicalagin, pedunculagin, quercetin, rutin, tannic acid, polyphenol, anthocyanins, and catechins. This review aims at providing an overview of the chemical constituents, antibacterial, anti-inflammatory, and antioxidant properties of P. granatum , and its role in the prevention and treatment of gingival and periodontal diseases.

Phenolic acids, syringaldehyde, and juglone in fruits of different cultivars of Juglans regia L.

PubMed

Colaric, Mateja; Veberic, Robert; Solar, Anita; Hudina, Metka; Stampar, Franci

2005-08-10

Phenolic acids (chlorogenic, caffeic, p-coumaric, ferulic, sinapic, ellagic, and syringic acid) as well as syringaldehyde and juglone were identified in ripe fruits of 10 walnut cultivars: Adams, Cisco, Chandler, Franquette, Lara, Fernor, Fernette, Alsoszentivani 117 (A-117), Rasna, and Elit. Analyses were done using a high-performance liquid chromatograph equipped with a diode array detector. Significant differences in the contents of identified phenolics were observed among cultivars. Phenolics were determined separately in the kernel and in the thin skin of the walnut, termed the pellicle. Not only in the kernel but also in the pellicle did syringic acid, juglone, and ellagic acid predominate (average values of 33.83, 11.75, and 5.90 mg/100 g of kernel; and 1003.24, 317.90, and 128.98 mg/100 g of pellicle, respectively), and the contents of ferulic and sinapic acid (average values of 0.06 and 0.05 mg/100 g of kernel and 2.93 and 2.17 mg/100 g of pellicle, respectively) were the lowest in all cultivars. The highest differences in the sum of all identified phenolics were observed between Rasna and Fernette fruits; in Rasna there were >2-fold higher contents of identified phenolics in both kernel and pellicle. It was found that the walnut pellicle is the most important source of walnut phenolics. The ratio between the contents in pellicle and kernel varied by at least 14.8-fold for caffeic acid (cv. Adams) and by up to 752.0-fold for p-coumaric acid (cv. Elit).

Oenothera paradoxa defatted seeds extract and its bioactive component penta-O-galloyl-β-D-glucose decreased production of reactive oxygen species and inhibited release of leukotriene B4, interleukin-8, elastase, and myeloperoxidase in human neutrophils.

PubMed

Kiss, Anna K; Filipek, Agnieszka; Czerwińska, Monika; Naruszewicz, Marek

2010-09-22

In this study, we analyzed ex vivo the effect of an aqueous extract of Oenothera paradoxa defatted seeds on the formation of neutrophil-derived oxidants. For defining active compounds, we also tested lypophilic extract constituents such as gallic acid, (+)-catechin, ellagic acid, and penta-O-galloyl-β-D-glucose and a hydrophilic fraction containing polymeric procyanidins. The anti-inflammatory potential of the extract and compounds was tested by determining the release from activated neutrophils of elastase, myeloperoxidase, interleukin-8 (IL-8), and leukotriene B4 (LTB4), which are considered relevant for the pathogenesis of cardiovascular diseases. The extract of O. paradoxa defatted seeds displays potent antioxidant effects against both 4β-phorbol-12β-myristate-α13-acetate- and formyl-met-leu-phenylalanine-induced reactive oxygen species production in neutrophils with IC50 values around 0.2 μg/mL. All types of polyphenolics present in the extract contributed to the extract antioxidant activity. According to their IC50 values, penta-O-galloyl-β-D-glucose was the more potent constituent of the extract. In cell-free assays, we demonstrated that this effect is partially due to the scavenging of O2- and H2O2 oxygen species. The extract and especially penta-O-galloyl-β-D-glucose significantly inhibit elastase, myeloperoxidase IL-8, and LTB4 release with an IC50 for penta-O-galloyl-β-D-glucose of 17±1, 15±1, 6.5±2.5, and around 20 μM, respectively. The inhibition of penta-O-galloyl-β-D-glucose on reactive oxygen species and especially on O2- production, myeloperoxidase, and chemoattractant release may reduce the interaction of polymorphonuclear leukocyte with the vascular endothelium and by that potentially diminish the risk of progression of atherosclerosis development.

Crude extract and fractions from Eugenia uniflora Linn leaves showed anti-inflammatory, antioxidant, and antibacterial activities.

PubMed

Falcão, Tamires Rocha; de Araújo, Aurigena Antunes; Soares, Luiz Alberto Lira; de Moraes Ramos, Rhayanne Thaís; Bezerra, Isabelle Cristinne Ferraz; Ferreira, Magda Rhayanny Assunção; de Souza Neto, Manoel André; Melo, Maria Celeste Nunes; de Araújo, Raimundo Fernandes; de Aguiar Guerra, Andreza Conceição Véras; de Medeiros, Juliana Silva; Guerra, Gerlane Coelho Bernardo

2018-03-09

This study showed phytochemical composition and evaluates the anti-inflammatory, and analgesic activities of crude extract (CE) and fractions from E. uniflora Linn leaves. Polyphenols present in crude extract (CE), in aqueous fraction (AqF), and ethyl acetate (EAF) treated fractions from E. uniflora Linn leaves were shown by chromatographic analysis in order to conduct a phytochemical characterization. Antibacterial activity was evaluated based on minimum inhibitory concentrations (MICs) determined using the agar dilution method. Doses of 50, 100, and 200 mg/kg of the CE and fractions were applied for conducting in vivo models (male Swiss mice, 8-10 weeks old). The peritonitis experimental model was induced by carrageenan following of Myeloperoxidase activity (MPO), Total glutathione and malondialdehyde (MDA), IL-1β and TNF-α levels by spectroscopic UV/VIS analysis. Antinociceptive activity was evaluated based on an abdominal writhing model and hot plate test. The results were statistically evaluated using one-way analysis of variance (ANOVA), followed by Bonferroni's post-hoc test. The level of statistical significance was p < 0.05. High-performance liquid chromatography with photodiode array detection (HPLC-DAD) detected varying concentrations of gallic acid, ellagic acid, and myricitrin in the CE and fractions obtained from E. uniflora Linn leaves (0.05-0.87%w/w, 0.20-0.32%w/w, and 1.71-6.56%w/w, respectively). In general, the CE had lower MIC values than the fractions, including the lowest MIC against the MRSA strain. The CE and AqF also significantly reduced leukocyte migration and MPO activity (p < 0.05). In addition, AqF significantly reduced IL-1β and TNF-α levels (p < 0.05). Furthermore, the CE and fractions exhibited an antioxidant effect (p < 0.05) and peripheral analgesic activity (p < 0.05). The CE and fractions from the studied E. uniflora Linn leaves exhibited antibacterial, anti-inflammatory, antioxidant, and analgesic activity in the performed assays.

Preliminary phytochemical screening and in vitro antioxidant activities of the aqueous extract of Helichrysum longifolium DC.

PubMed

Aiyegoro, Olayinka A; Okoh, Anthony I

2010-05-14

Many oxidative stress related diseases are as a result of accumulation of free radicals in the body. A lot of researches are going on worldwide directed towards finding natural antioxidants of plants origins. The aims of this study were to evaluate in vitro antioxidant activities and to screen for phytochemical constituents of Helichrysum longifolium DC. [Family Asteraceae] aqueous crude extract. We assessed the antioxidant potential and phytochemical constituents of crude aqueous extract of Helichrysum longifolium using tests involving inhibition of superoxide anions, DPPH, H2O2, NO and ABTS. The flavonoid, proanthocyanidin and phenolic contents of the extract were also determined using standard phytochemical reaction methods. Phytochemical analyses revealed the presence of tannins, flavonoids, steroids and saponins. The total phenolic content of the aqueous leaf extract was 0.499 mg gallic acid equivalent/g of extract powder. The total flavonoid and proanthocyanidin contents of the plant were 0.705 and 0.005 mg gallic acid equivalent/g of extract powder respectively. The percentage inhibition of lipid peroxide at the initial stage of oxidation showed antioxidant activity of 87% compared to those of BHT (84.6%) and gallic acid (96%). Also, the percentage inhibition of malondialdehyde by the extract showed percentage inhibition of 78% comparable to those of BHT (72.24%) and Gallic (94.82%). Our findings provide evidence that the crude aqueous extract of H. longifolium is a potential source of natural antioxidants, and this justified its uses in folkloric medicines.

Is the solubilized product from the degradation of lignocellulose by actinomycetes a precursor of humic substances?

PubMed

Trigo, C; Ball, A S

1994-11-01

Three actinomycetes (Streptomyces sp. EC22, Streptomyces viridosporus T7A and Thermomonospora fusca BD25) were assessed for their ability to degrade ball-milled wheat straw. All gave maximum levels of solubilized lignocellulose products (APPL) at the beginning of the stationary phase of growth (72-96 h). Low-molecular-mass aromatic compounds extracted from the APPL were analysed by reverse-phase and gas chromatography. Although the number of chromatographic peaks detected made identification of the products difficult, p-coumaric acid (4-hydroxycinnamic acid), protocatechuic acid (3,4-dihydroxybenzoic acid), gallic acid (3,4,5-trihydroxybenzoic acid), gallic acid methyl ester (methyl-3,4,5-trihydroxybenzoate) and 4-methoxyphenol were recognized. The infrared spectra of the three strains were similar to the spectra of humic acids, with all APPL extracts showing carbonyl, amino, carboxyl, aliphatic and aromatic group vibrations. Also detected were peptide linkages of proteins. The results suggest a role for actinomycetes in the formation of humic substances in soils and composts.

Ellagic acid promotes A{beta}42 fibrillization and inhibits A{beta}42-induced neurotoxicity

DOE Office of Scientific and Technical Information (OSTI.GOV)

Feng, Ying; Tsinghua University School of Medicine, Haidian District, Beijing 100084; Yang, Shi-gao

Smaller, soluble oligomers of {beta}-amyloid (A{beta}) play a critical role in the pathogenesis of Alzheimer's disease (AD). Selective inhibition of A{beta} oligomer formation provides an optimum target for AD therapy. Some polyphenols have potent anti-amyloidogenic activities and protect against A{beta} neurotoxicity. Here, we tested the effects of ellagic acid (EA), a polyphenolic compound, on A{beta}42 aggregation and neurotoxicity in vitro. EA promoted A{beta} fibril formation and significant oligomer loss, contrary to previous results that polyphenols inhibited A{beta} aggregation. The results of transmission electron microscopy (TEM) and Western blot displayed more fibrils in A{beta}42 samples co-incubated with EA in earlier phasesmore » of aggregation. Consistent with the hypothesis that plaque formation may represent a protective mechanism in which the body sequesters toxic A{beta} aggregates to render them harmless, our MTT results showed that EA could significantly reduce A{beta}42-induced neurotoxicity toward SH-SY5Y cells. Taken together, our results suggest that EA, an active ingredient in many fruits and nuts, may have therapeutic potential in AD.« less

Physical and Bioactive Properties of Muffins Enriched with Raspberry and Cranberry Pomace Powder: A Promising Application of Fruit By-Products Rich in Biocompounds.

PubMed

Mildner-Szkudlarz, Sylwia; Bajerska, Joanna; Górnaś, Paweł; Segliņa, Dalija; Pilarska, Agnieszka; Jesionowski, Teofil

2016-06-01

The objective of this study was to determine the effects on quality of incorporating raspberry and cranberry pomaces into American-style muffins prepared under various baking conditions. The different baking conditions did not affect the texture or microstructure of the control muffins. The enhanced samples baked at 140 °C for 30 min were characterized by a harder texture than the control muffins and by a distributed protein matrix and distorted starch granules, while those baked at 240 °C for 15 min had a moist texture and showed incomplete starch gelatinization. The mean percent recovery of ellagic acid, flavonols, tocopherols, tocotrienols, and anthocyanins after baking were 156, 53, 48, 43, and 22 %, respectively. Lower baking temperature was better for ellagic acid and tocotrienols, but worse for flavonols, tocopherols, and anthocyanins. It seems that, for the enhanced samples, the intermediate baking conditions (180 °C for 20 min) guarantee the best microstructure and texture and the appropriate retention of phytochemicals in muffins.

A combination of ellagic acid and tetracycline inhibits biofilm formation and the associated virulence of Propionibacterium acnes in vitro and in vivo.

PubMed

Sivasankar, Chandran; Maruthupandiyan, Shanmugam; Balamurugan, Krishnaswamy; James, Prabhanand Bhaskar; Krishnan, Venkat; Pandian, Shunmugiah Karutha

2016-01-01

Propionibacterium acnes is an opportunistic pathogen which has become notorious owing to its ability to form a recalcitrant biofilm and to develop drug resistance. The current study aimed to develop anti-biofilm treatments against clinical isolates of P. acnes under in vitro and in vivo conditions. A combination of ellagic acid and tetracycline (ETC; 250 μg ml(-1) + 0.312 μg ml(-1)) was determined to effectively inhibit biofilm formation by P. acnes (80-91%) without affecting its growth, therefore potentially limiting the possibility of the bacterium attaining resistance. In addition, ETC reduced the production of extracellular polymeric substances (EPS) (20-26%), thereby making P. acnes more susceptible to the human immune system and antibiotics. The anti-biofilm potential of ETC was further substantiated under in vivo conditions using Caenorhabditis elegans. This study reports a novel anti-biofilm combination that could be developed as an ideal therapeutic agent with broad cosmeceutical and pharmaceutical applicability in the era of antibiotic resistance.

Radioprotective Efficacy of Lutein in Ameliorating Electron Beam Radiation-induced Oxidative Injury in Swiss Albino Mice

PubMed Central

Vasudeva, Vidya; Tenkanidiyoor, Yogish Somayaji; Peter, Alex John; Shetty, Jayaram; Lakshman, Srikant Patil; Fernandes, Ronald; Patali, Krishna Ananthapura

2018-01-01

Background: Lutein, a carotenoid compound, has previously been studied for its antioxidant and medicinal properties as well as the moderate protection it confers against gamma radiation. This study aimed at evaluating the effects of lutein against radiation-induced hematological and biochemical changes in mice. Methods: The optimized dose of the compound was orally administered for 15 days, and the mice were irradiated (6 Gy) on day 15 after the administration of the compound. The groups were divided (6 mice in each group) into normal control, radiation control, gallic acid control, 10% DMSO control, lutein control, and irradiated groups pretreated with gallic acid, 10% DMSO, and lutein. Gallic acid was used to maintain a standard since it is a proven radioprotector. Within 24 hours post irradiation, the animals were anesthetized and sacrificed. The hematological, biochemical, and antioxidant changes were determined using suitable methods. Data were analyzed by the Kaplan–Meier curve (log-rank test) and ANOVA (the Tukey test). The independent t test was used to compare the independent groups. SPSS (ver. 16) was employed. Results: Maximum survival was observed with a dose of 250 mg/kg b.wt lutein. The total leukocyte count and the percentage lymphocyte count exhibited a significant decline in the irradiated groups pretreated with gallic acid and lutein in comparison to their controls, whereas the percentage granulocyte count showed a significant rise. Antioxidant activity had markedly declined in the irradiated groups, indicating oxidative stress. Lutein pretreatment reduced the damage and maintained the antioxidant system. Conclusion: The present study suggests a protective role for lutein in palliating radiation-induced oxidative changes and maintaining the antioxidant system in vivo. PMID:29398751

Prediction of oxidation parameters of purified Kilka fish oil including gallic acid and methyl gallate by adaptive neuro-fuzzy inference system (ANFIS) and artificial neural network.

PubMed

Asnaashari, Maryam; Farhoosh, Reza; Farahmandfar, Reza

2016-10-01

As a result of concerns regarding possible health hazards of synthetic antioxidants, gallic acid and methyl gallate may be introduced as natural antioxidants to improve oxidative stability of marine oil. Since conventional modelling could not predict the oxidative parameters precisely, artificial neural network (ANN) and neuro-fuzzy inference system (ANFIS) modelling with three inputs, including type of antioxidant (gallic acid and methyl gallate), temperature (35, 45 and 55 °C) and concentration (0, 200, 400, 800 and 1600 mg L(-1) ) and four outputs containing induction period (IP), slope of initial stage of oxidation curve (k1 ) and slope of propagation stage of oxidation curve (k2 ) and peroxide value at the IP (PVIP ) were performed to predict the oxidation parameters of Kilka oil triacylglycerols and were compared to multiple linear regression (MLR). The results showed ANFIS was the best model with high coefficient of determination (R(2)  = 0.99, 0.99, 0.92 and 0.77 for IP, k1 , k2 and PVIP , respectively). So, the RMSE and MAE values for IP were 7.49 and 4.92 in ANFIS model. However, they were to be 15.95 and 10.88 and 34.14 and 3.60 for the best MLP structure and MLR, respectively. So, MLR showed the minimum accuracy among the constructed models. Sensitivity analysis based on the ANFIS model suggested a high sensitivity of oxidation parameters, particularly the induction period on concentrations of gallic acid and methyl gallate due to their high antioxidant activity to retard oil oxidation and enhanced Kilka oil shelf life. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

The Microbiota Is Essential for the Generation of Black Tea Theaflavins-Derived Metabolites

PubMed Central

Chen, Huadong; Hayek, Saeed; Rivera Guzman, Javier; Gillitt, Nicholas D.; Ibrahim, Salam A.; Jobin, Christian; Sang, Shengmin

2012-01-01

Background Theaflavins including theaflavin (TF), theaflavin-3-gallate (TF3G), theaflavin-3′-gallate (TF3′G), and theaflavin-3,3′-digallate (TFDG), are the most important bioactive polyphenols in black tea. Because of their poor systemic bioavailability, it is still unclear how these compounds can exert their biological functions. The objective of this study is to identify the microbial metabolites of theaflavins in mice and in humans. Methods and Findings In the present study, we gavaged specific pathogen free (SPF) mice and germ free (GF) mice with 200 mg/kg TFDG and identified TF, TF3G, TF3′G, and gallic acid as the major fecal metabolites of TFDG in SPF mice. These metabolites were absent in TFDG- gavaged GF mice. The microbial bioconversion of TFDG, TF3G, and TF3′G was also investigated in vitro using fecal slurries collected from three healthy human subjects. Our results indicate that TFDG is metabolized to TF, TF3G, TF3′G, gallic acid, and pyrogallol by human microbiota. Moreover, both TF3G and TF3′G are metabolized to TF, gallic acid, and pyrogallol by human microbiota. Importantly, we observed interindividual differences on the metabolism rate of gallic acid to pyrogallol among the three human subjects. In addition, we demonstrated that Lactobacillus plantarum 299v and Bacillus subtilis have the capacity to metabolize TFDG. Conclusions The microbiota is important for the metabolism of theaflavins in both mice and humans. The in vivo functional impact of microbiota-generated theaflavins-derived metabolites is worthwhile of further study. PMID:23227227

Enhanced anticancer effect of fabricated gallic acid/CdS on the rGO nanosheets on human glomerular mesangial (IP15) and epithelial proximal (HK2) kidney cell lines - Cytotoxicity investigations.

PubMed

Peng, Wei; Luo, Pengcheng; Gui, Dingwen; Jiang, Weidong; Wu, Haixia; Zhang, Jie

2018-01-01

In spite of the technological innovation in the biomedical science, cancer remains a critical disease. In this study, we designed a gallic acid/cadmium sulfide (GA/CdS) nanocomposite fabricated on the reduced graphene oxide (GA/CdS-rGO) nanosheets for the treatment system of human kidney cancer cells. The GA/CdS-rGO nanosheets have been prepared using gallic acid as a reducing agent. The characterization of nanocomposites was studied using UV-Vis spectroscope, FT-IR, XRD, SEM and TEM. The microscopic images showed the spherical shape and nano-scaled CdS nanoparticles on the sheet like rGO nanomaterials. These structural and morphology investigations show that excellent properties of as-prepared GA/CdS-rGO has ability to treat the human glomerular mesangial (IP15) cancer cells at 50μg/ml as an IC 50 value, without affecting the epithelial proximal (HK-2) normal cells. In vitro cytotoxicity results showed that the variability of toxic effects after CdS exposure was strongly associated to the cellular Cd content. Release of Cd 2+ from nanocomposites depended to solubility and particle degradation of CdS nanoparticles were considered to be the main cause of these cytotoxicity. The in vitro analysis results indicated that heterogeneity of Cd and gallic acid toxicity that was highly dependent on the physico-chemical properties of the nanocomposites. The cytotoxicity results suggested that the prepared nanomaterials were toxic and inhibitory efficiency to human kidney cancer cells. Copyright © 2017 Elsevier B.V. All rights reserved.

Wheat germ oil enrichment in broiler feed with α-lipoic acid to enhance the antioxidant potential and lipid stability of meat

PubMed Central

2013-01-01

Background Lipid peroxidation is the cause of declining the meat quality. Natural antioxidants plays a vital role in enhancing the stability and quality of meat. The supplementation of natural antioxidants in feed decreases lipid peroxidation and improves the stability of meat. Methods The present research was conducted to determine the effect of α-lipoic acid, α-tocopherol and wheat germ oil on the status of antioxidants, quality and lipid stability of broiler meat. One day old male broilers were fed with different feeds containing antioxidants i.e. natural (wheat germ oil) and synthetic α-tocopherol and α-lipoic acid during the two experimental years. Results The feed treatments have significant variation on the body weight and feed conversion ratio (FCR) while having no influence on the feed intake. The broilers fed on wheat germ oil (natural α-tocopherol) gained maximum body weight (2451.97 g & 2466.07 g) in the experimental years 2010–11 & 2011–12, respectively. The higher total phenolic contents were found in the broilers fed on wheat germ oil plus α-lipoic acid in breast (162.73±4.8 mg Gallic acid equivalent/100 g & 162.18±4.5 mg Gallic acid equivalent/100 g) and leg (149.67±3.3 mg Gallic acid equivalent/100 g & 146.07±3.2 mg Gallic acid equivalent/100 g) meat during both experimental years. Similar trend was observed for the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing antioxidant power assay (FRAP). The production of malondialdehydes in the breast and leg meat increased with progressive increase in the time period. The deposition of α-tocopherol (AT) and α-lipoic acid (ALA) contents were found to be higher in the broilers fed on wheat germ oil plus α-lipoic acid in breast and leg meat during the both experimental years. Conclusion In conclusion, the combination of wheat germ oil and α-lipoic acid has more beneficial for stability and the quality of the broiler meat and more work should be needed in future for the bio-evaluation of this kind of functional meat in humans. PMID:24499336

Synthesis and structure identification of 2-amino-4, 6- dimethyl pyrimidine with gallic acid and pimelic acid

NASA Astrophysics Data System (ADS)

Mekala, R.; Jagdish, P.; Mathammal, R.

2018-07-01

Reaction of 2-amino-4, 6- dimethyl pyrimidine with carboxylic acid such as gallic acid and pimelic acid, yielded a salt and co-crystal, respectively. The new crystal forms were obtained from slow evaporation technique. The crystal structure and hydrogen bond interaction of the two crystals were determined by single X-ray diffraction analysis. Inter molecular interactions of the compounds were investigated using the 3D Hirshfeld surfaces and the associated 2D fingerprint plots. The functional groups were identified by the FTIR, FT-Raman spectral studies. The presence of carbon and hydrogen in the two samples were identified by the 1H and 13C NMR analysis. The excited energy was observed using UV-Visible spectral analysis. The fluorescence spectra revealed the emission state of the two samples. The thermal behaviour and stability of the two compounds were evaluated by the TGA-DSC analysis.

Variations in antioxidant properties of strawberries grown in Brazilian savannah and harvested in different seasons.

PubMed

Pineli, Lívia de L de O; Moretti, Celso L; Rodrigues, Juliana S Q; Ferreira, Danielle B; Chiarello, Marileusa D

2012-03-15

Strawberries are nutritive fruits and a source of antioxidants. We evaluated antioxidant properties of 'Camino Real' strawberries grown in the Brazilian savannah, harvested in different seasons. Analytical and meteorological data were analyzed by partial least squares regression. Fruits from May showed the lowest contents of total phenolics (1789.78 mg kg⁻¹ fresh weight (FW)), catechin (21.37 mg kg⁻¹ FW), quercetins (4.89 mg kg⁻¹ FW) and total ellagic acid (208.68 mg kg⁻¹ FW) and the lowest antioxidant activity by 2,2-diphenyl-1-picrylhydrazyl (DPPH) (11.39 mg Butylated hydroxytoluene (BHT) eq. g⁻¹ FW) and ferric reducing antioxidant power (FRAP) (22.01 mg ferrous sulfate eq. g⁻¹ FW) assays. Strawberries harvested in July presented the lowest concentrations of total (190.61 mg kg⁻¹ FW) and individual anthocyanins (73.88 mg kg⁻¹ FW and 5.96 mg kg⁻¹ FW for pelargonidin-3-glucoside and cyanidin-3-glucoside, respectively), but the highest contents of vitamin C (685.47 mg kg⁻¹ FW), DPPH (18.87 mg BHT eq. g⁻¹ FW) and FRAP (39.30 mg ferrous sulfate eq. g⁻¹ FW). The highest contents of free ellagic acid (26.11 mg kg⁻¹ FW), pelargonidin-3-glucoside (291.82 mg kg⁻¹ FW) and cyanidin-3-glucoside (11.84 mg kg⁻¹ FW) were found in strawberries from September. Rain in the previous 30 days to harvest influenced negatively many phenolics and antioxidant activity of strawberries harvested in May. In July, longer photoperiod and lower temperature at 30 days previous to harvest probably led to higher antioxidant activity and vitamin C. Increased photoperiod and temperature at the final stage of maturation seem to raise pigments and free ellagic acid in strawberries. It was possible to observe significant relationships among meteorological and antioxidant variables for strawberries grown in the Brazilian savannah. Copyright © 2011 Society of Chemical Industry.

Ellagic acid impedes carbontetrachloride-induced liver damage in rats through suppression of NF-kB, Bcl-2 and regulating Nrf-2 and caspase pathway.

PubMed

Aslan, Abdullah; Gok, Ozlem; Erman, Orhan; Kuloglu, Tuncay

2018-06-11

The use of natural antioxidants instead of conventional treatments is considered effective and safe alternative therapy for hepatotoxicity. Ellagic acid (EA) is a strong antioxidant matter having protecting effect particularly on the liver. Hepatotoxic compounds can cause very heavy damage. Among these chemical hepatotoxins, CCl 4 are responsible for the trichloromethyl radical resulting from biotransformation of the liver. The aim of this study was to examine whether EA plays a protective role against to liver damage induced with carbon tetrachloride (CCl 4 ) in rats. In this study, 36 male wistar albino (n = 36, 8 weeks old) rats were used. The rats were distributed into 4 groups, and 9 rats involved in each group. The groups were: (i) Control Group: Fed with standard diet; (ii) EA Group: Fed with standard diet + EA; (iii) CCl 4 Group: Fed with standard diet + CCl 4 ; (iv) CCl 4 + EA Group: Fed with standard diet + CCl 4 + EA. After 8 weeks, the rats were decapitated and the liver tissue were examined. As a result; EA application created a significant difference (p < 0.05) on caspase-3, bcl-2, NF-kB and Nrf-2 expression in the CCl 4 + EA group in comparison to CCl 4 group. Caspase-3 and Nrf-2 expression levels were increased in the CCl 4 + EA group in comparison to CCl 4 group, but bcl-2 and NF-kB expression levels were decreased. In TUNEL assay examinations, apoptotic index ratio was decreased in the CCl 4 + EA group in comparison to CCl 4 group. These results show that EA reduce liver damage ratio at wistar albino rats and also these results suggest that ellagic acid may be a potentially protective drug against to liver damage in future. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

Fungal pretreatment of sweet sorghum bagasse with supplements: improvement in lignin degradation, selectivity and enzymatic saccharification.

PubMed

Mishra, Vartika; Jana, Asim K; Jana, Mithu Maiti; Gupta, Antriksh

2017-06-01

Sweet sorghum bagasse (SSB) from food processing and agricultural industry has attracted the attention for uses in production of biofuel, enzymes and other products. The alteration in lignocellulolytic enzymes by use of supplements in fungal pretreatment of SSB to achieve higher lignin degradation, selectivity value and enzymatic hydrolysis to fermentable sugar was studied. Fungal strain Coriolus versicolor was selected for pretreatment due to high ligninolytic and low cellulolytic enzyme production resulting in high lignin degradation and selectivity value. SSB was pretreated with supplements of veratryl alcohol, syringic acid, catechol, gallic acid, vanillin, guaiacol, CuSO 4 and MnSO 4 . The best results were obtained with CuSO 4 , gallic acid and syringic acid supplements. CuSO 4 increased the activities of laccase (4.9-fold) and polyphenol oxidase (1.9-fold); gallic acid increased laccase (3.5-fold) and manganese peroxidase (2.5-fold); and syringic acid increased laccase (5.6-fold), lignin peroxidase (13-fold) and arylalcohol oxidase (2.8-fold) resulting in enhanced lignin degradations and selectivity values than the control. Reduced cellulolytic enzyme activities resulted in high cellulose recovery. Enzymatic hydrolysis of pretreated SSB yielded higher sugar due to degradation of lignin and reduced the crystallinity of cellulose. The study showed that supplements could be used to improve the pretreatment process. The results were confirmed by scanning electron microscopy, X-ray diffraction, Fourier transform infrared spectroscopy and thermogravimetric/differential thermogravimetric analysis of SSB.

Ancient Seed for Modern Cure – Pomegranate Review of Therapeutic Applications in Periodontics

PubMed Central

Thangavelu, Arthiie; Elavarasu, Sugumari; Sundaram, Rajasekar; Kumar, Tamilselvan; Rajendran, Dhivya; Prem, Fairlin

2017-01-01

Punica granatum (pomegranate), the member of Punicaceae family, is used in the prevention and treatment of health disorders. P. granatum contains diverse range of phytochemicals including ellagic acid, punicalagin, pedunculagin, quercetin, rutin, tannic acid, polyphenol, anthocyanins, and catechins. This review aims at providing an overview of the chemical constituents, antibacterial, anti-inflammatory, and antioxidant properties of P. granatum, and its role in the prevention and treatment of gingival and periodontal diseases. PMID:29284927

Quantification of tannins and related polyphenols in commercial products of tormentil (Potentilla tormentilla).

PubMed

Fecka, Izabela; Kucharska, Alicja Zofia; Kowalczyk, Adam

2015-01-01

Potentilla tormentilla has many biological and pharmacological properties and can be used as an ingredient of some herbal medicines or beverages. The aim of this study was to evaluate the content of individual polyphenols, especially condensed and hydrolysable tannins in commercially available tormentil rhizomes and tinctures using chromatographic methods. A quantitative analysis (HPLC-PDA) was preceded by qualitative studies (UPLC-qTOF-MS/MS) and the isolation (CC) of the major tannin compounds. The tested plant material is characterised by a high content of tannins and related polyphenols, i.e. in rhizomes even at the level above 20% and in tinctures above 2%. The main components of tormentil rhizomes are procyanidin B3 (mean ~ 3.6%), procyanidin C2 (mean ~ 2.8%), agrimoniin (mean ~ 2.5%), 3-O-galloylquinic acid (mean ~ 1.7%), catechin (mean ~ 1.6%), other flavan-3-ol oligomers (mean ~ 0.5-1.1) and laevigatins (mean ~ 0.2-0.6%). Free ellagic acid and glycosides of ellagic and methylellagic acids are secondary components. Underground parts of tormentil are a source of oligomeric proanthocyanidins and ellagitannins, but in smaller quantity of gallotannins. Monogalloylquinic acids are new identified compounds, which had not been described in Potentilla tormentilla before we started our research. In the analysed tormentil tinctures agrimoniin concentration is lower in relation to other tannins. Copyright © 2015 John Wiley & Sons, Ltd.

Protective Effects of Triphala on Dermal Fibroblasts and Human Keratinocytes

PubMed Central

Varma, Sandeep R.; Sivaprakasam, Thiyagarajan O.; Mishra, Abheepsa; Kumar, L. M. Sharath; Prakash, N. S.; Prabhu, Sunil; Ramakrishnan, Shyam

2016-01-01

Human skin is body’s vital organ constantly exposed to abiotic oxidative stress. This can have deleterious effects on skin such as darkening, skin damage, and aging. Plant-derived products having skin-protective effects are well-known traditionally. Triphala, a formulation of three fruit products, is one of the most important rasayana drugs used in Ayurveda. Several skin care products based on Triphala are available that claim its protective effects on facial skin. However, the skin protective effects of Triphala extract (TE) and its mechanistic action on skin cells have not been elucidated in vitro. Gallic acid, ellagic acid, and chebulinic acid were deduced by LC-MS as the major constituents of TE. The identified key compounds were docked with skin-related proteins to predict their binding affinity. The IC50 values for TE on human dermal fibroblasts (HDF) and human keratinocytes (HaCaT) were 204.90 ± 7.6 and 239.13 ± 4.3 μg/mL respectively. The antioxidant capacity of TE was 481.33 ± 1.5 mM Trolox equivalents in HaCaT cells. Triphala extract inhibited hydrogen peroxide (H2O2) induced RBC haemolysis (IC50 64.95 μg/mL), nitric oxide production by 48.62 ± 2.2%, and showed high reducing power activity. TE also rescued HDF from H2O2-induced damage; inhibited H2O2 induced cellular senescence and protected HDF from DNA damage. TE increased collagen-I, involucrin and filaggrin synthesis by 70.72 ± 2.3%, 67.61 ± 2.1% and 51.91 ± 3.5% in HDF or HaCaT cells respectively. TE also exhibited anti-tyrosinase and melanin inhibition properties in a dose-dependent manner. TE increased the mRNA expression of collagen-I, elastin, superoxide dismutase (SOD-2), aquaporin-3 (AQP-3), filaggrin, involucrin, transglutaminase in HDF or HaCaT cells, and decreased the mRNA levels of tyrosinase in B16F10 cells. Thus, Triphala exhibits protective benefits on skin cells in vitro and can be used as a potential ingredient in skin care formulations. PMID:26731545

Prescription Proportion of Pomegranate Extract Gallic Acid Gel by Orthogonal Design

NASA Astrophysics Data System (ADS)

Fan, Gaofu; Liu, Xiushu; Tang, Jie; Gong, Jumei; Fu, Entao; Cai, Yuhua; Xu, Zhenguo

2018-05-01

The aim of the present work was to optimize the formulation of pomegranate extract gallic acid gel by orthogonal design. Using orthogonal design, propylene glycol, carbomer-940 and gel pH level as influencing factors, the evaluation key index was external apearance malleability, uniformity, and eccentric for gel, and the optimum formula was selected. The present findings suggest that 10% propylene glycol, 1.5% Carbopol-940, and gel pH in the range of 4.5∼5.5, and the indexes of the optimal. The inclusion complexes showed that after the orthogonal design, the preparation process was simple, stable and controllable quality, with production feasibility.

A phytochemical study of the Cuphea glutinosa from Southern Brazil: Na+,K+-ATPase activity inhibition and antioxidant properties.

PubMed

Zago, Adriana M; Carvalho, Fabiano B; Gutierres, Jessié Martins; Bohnert, Crystiani; Fernandes, Marilda da Cruz; Morandini, Liziane M; Coelho, Helena S; Fogaça, Aline O; Andrade, Cinthia M; Mostardeiro, Marco A; Dalcol, Ionara I; Morel, Ademir F

2018-05-21

This study investigated the antioxidant activity of Cuphea glutinosa (CG) and its effect on Na + , K + -ATPase from cardiac muscle. The ethanolic extract showed higher antioxidant capacity compared to aqueous and ethyl acetate fraction. Ethyl acetate fraction showed β-sitosterol-3-O-β-glucoside, kaempferol, quercetin, isoquercetin, gallic acid methyl ester, and gallic acid. The ethanolic extract also reduced the Na + ,K + -ATPase activity. CG presented a promising antioxidant activity and inhibitory effect on the Na + , K + -ATPase activity, supporting biochemical evidences the popular use of this plant in the treatment of heart failure.

Intermolecular interactions in aqueous solutions of gallic acid at 296-306 K according to spectrofluorimetry and densimetry data

NASA Astrophysics Data System (ADS)

Grigoryan, K. R.; Sargsyan, L. S.

2015-12-01

Features of intermolecular interactions in aqueous solutions of gallic acid (GA) are studied by means of densimetry and fluorescence spectroscopy (intrinsic fluorescence, 2D spectra, and excitation/ emission matrix fluorescence spectra, 3D) at 296.15, 301.15, and 306.15 K in the concentration range of 5.88 × 10-4-5.88 × 10-2 mol L-1. It is shown by analyzing the concentration and temperature dependences of the apparent molar volumes and fluorescence parameters of GA that the equilibrium between nonassociated and associated species in the solution and the hydration of these species undergo changes.

Gallic acid is an active component for the anticarcinogenic action of grape seed procyanidins in pancreatic cancer cells.

PubMed

Cedó, Lídia; Castell-Auví, Anna; Pallarès, Victor; Macià, Alba; Blay, Mayte; Ardévol, Anna; Motilva, Maria-José; Pinent, Montserrat

2014-01-01

The aim of the present work was to evaluate the effects of a grape seed procyanidin extract (GSPE) on proliferation and apoptosis in the pancreatic adenocarcinoma cell line MIA PaCa-2 and identify the components of the extract with higher activity. The effects of the extract were analyzed on the proliferation and apoptosis processes in MIA PaCa-2 cells, as well as in the levels of the apoptosis markers Bcl-2 and Bax, the mitochondrial membrane potential, and reactive oxygen species levels. Finally, the components of the extract with higher effects were elucidated using enriched fractions of the extract and pure compounds. The results showed that GSPE inhibits cell proliferation and increases apoptosis in MIA PaCa-2 cells, which is primarily mediated by the downregulation of the antiapoptotic protein Bcl-2 and the depolarization of the mitochondrial membrane. GSPE also reduced the formation of reactive oxygen species. The component of the extract that possesses the highest antiproliferative and proapoptotic activity was gallic acid. In conclusion, GSPE acts as anticarcinogenic in MIA PaCa-2 cells, with gallic acid as the major single active constituent of the extract.

Dinuclear copper(II) octaazamacrocyclic complex in a PVC coated GCE and graphite as a voltammetric sensor for determination of gallic acid and antioxidant capacity of wine samples.

PubMed

Petković, B B; Stanković, D; Milčić, M; Sovilj, S P; Manojlović, D

2015-01-01

A novel efficient differential pulse voltammetric (DPV) method for determination gallic acid (GA) was developed by using an electrochemical sensor based on [Cu2tpmc](ClO4)4 immobilized in PVC matrix and coated on graphite (CGE) or classy carbon rod (CGCE). The proposed method is based on the gallic acid oxidation process at formed [Cu2tpmcGA](3+) complex at the electrode surface. The complexation was explored by molecular modeling and DFT calculations. Voltammograms for both sensors, recorded in a HNO3 as a supporting electrolyte at pH 2 and measured in 2.5×10(-7) to 1.0×10(-4) M of GA, resulted with two linear calibration curves (for higher and lower GA concentration range). The detection limit at CGE was 1.48×10(-7) M, while at CGCE was 4.6×10(-6) M. CGE was successfully applied for the determination of the antioxidant capacity based on GA equivalents for white, rosé and red wine samples. Copyright © 2014 Elsevier B.V. All rights reserved.

21 CFR 184.1097 - Tannic acid.

Code of Federal Regulations, 2013 CFR

2013-04-01

... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Tannic acid. 184.1097 Section 184.1097 Food and... Substances Affirmed as GRAS § 184.1097 Tannic acid. (a) Tannic acid (CAS Reg. No. 1401-55-4), or hydrolyzable gallotannin, is a complex polyphenolic organic structure that yields gallic acid and either glucose or quinic...

21 CFR 184.1097 - Tannic acid.

Code of Federal Regulations, 2012 CFR

2012-04-01

... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Tannic acid. 184.1097 Section 184.1097 Food and... Substances Affirmed as GRAS § 184.1097 Tannic acid. (a) Tannic acid (CAS Reg. No. 1401-55-4), or hydrolyzable gallotannin, is a complex polyphenolic organic structure that yields gallic acid and either glucose or quinic...

Chemical constituents and antibacterial activity of Melastoma malabathricum L.

PubMed

Wong, Keng-Chong; Hag Ali, Dafaalla Mohamed; Boey, Peng-Lim

2012-01-01

The aqueous methanolic extracts of Melastoma malabathricum L. exhibited antibacterial activity when assayed against seven microorganisms by the agar diffusion method. Solvent fractionation afforded active chloroform and ethyl acetate fractions from the leaves and the flowers, respectively. A phytochemical study resulted in the identification of ursolic acid (1), 2α-hydroxyursolic acid (2), asiatic acid (3), β-sitosterol 3-O-β-D-glucopyranoside (4) and the glycolipid glycerol 1,2-dilinolenyl-3-O-β-D-galactopyanoside (5) from the chloroform fraction. Kaempferol (6), kaempferol 3-O-α-L-rhamnopyranoside (7), kaempferol 3-O-β-D-glucopyranoside (8), kaempferol 3-O-β-D-galactopyranoside (9), kaempferol 3-O-(2″,6″-di-O-E-p-coumaryl)-β-D-galactopyranoside (10), quercetin (11) and ellagic acid (12) were found in the ethyl acetate fraction. The structures of these compounds were determined by chemical and spectral analyses. Compounds 1-4, the flavonols (6 and 11) and ellagic acid (12) were found to be active against some of the tested microorganisms, while the kaempferol 3-O-glycosides (7-9) did not show any activity, indicating the role of the free 3-OH for antibacterial activity. Addition of p-coumaryl groups results in mild activity for 10 against Staphylococcus aureus and Bacillus cereus. Compounds 2-5, 7 and 9-12 are reported for the first time from M. malabathricum. Compound 10 is rare, being reported only once before from a plant, without assignment of the double bond geometry in the p-coumaryl moiety.

Dietary phenolic acids reverse insulin resistance, hyperglycaemia, dyslipidaemia, inflammation and oxidative stress in high-fructose diet-induced metabolic syndrome rats.

PubMed

Ibitoye, Oluwayemisi B; Ajiboye, Taofeek O

2017-12-20

This study investigated the influence of caffeic, ferulic, gallic and protocatechuic acids on high-fructose diet-induced metabolic syndrome in rats. Oral administration of the phenolic acids significantly reversed high-fructose diet-mediated increase in body mass index and blood glucose. Furthermore, phenolic acids restored high-fructose diet-mediated alterations in metabolic hormones (insulin, leptin and adiponectin). Similarly, elevated tumour necrosis factor-α, interleukin-6 and -8 were significantly lowered. Administration of phenolic acids restored High-fructose diet-mediated increase in the levels of lipid parameters and indices of atherosclerosis, cardiac and cardiovascular diseases. High-fructose diet-mediated decrease in activities of antioxidant enzymes (superoxide dismutase, catalase, glutathione peroxidase, glutathione reductase and glucose 6-phosphate dehydrogenase) and increase in oxidative stress biomarkers (reduced glutathione, lipid peroxidation products, protein oxidation and fragmented DNA) were significantly restored by the phenolic acids. The result of this study shows protective influence of caffeic acid, ferulic acid, gallic acid and protocatechuic acid in high-fructose diet-induced metabolic syndrome.

Specific phenolic compounds and sensory properties of a new dealcoholized red wine with pomegranate (Punica granatum L.) extract.

PubMed

Tárrega, Maria Amparo; Varela, Paula; Fromentin, Emilie; Feuillère, Nicolas; Issaly, Nicolas; Roller, Marc; Sanz-Buenhombre, Marisa; Villanueva, Sonia; Moro, Carlos; Guadarrama, Alberto; Fiszman, Susana

2014-09-01

The pomegranate (Punica granatum L.) fruit has a long history of human consumption and possesses notable antioxidant and cardiovascular properties. This work evaluated the feasibility to provide a new functional beverage based on a dealcoholized red wine matrix supplemented by a pomegranate extract. The potential bioactive compounds in the pomegranate extract, punicalagin A and B and ellagic acid, were analyzed during the downstream process in order to evaluate the functional dose in the final beverage. The addition of pomegranate extract to the dealcoholized red wine resulted in a product with more intense yeast odor, acidity, yeast flavor, and astringency and with a less intense berry flavor. Consumer acceptance of the product was also investigated and the results revealed the existence of a niche of consumers willing to consume dealcoholized wine enriched with pomegranate extract. After tasting, 50% and 40% of those consumers initially interested by this product concept declared to be interested to purchase the control sample and the functional beverage, respectively. The daily consumption of two servings of 250 mL of this new pomegranate-enriched dealcoholized wine provides 82 mg of total ellagitannins, corresponding to the sum of punicalagin A and B and ellagic acid. © The Author(s) 2013 Reprints and permissions: sagepub.co.uk/journalsPermissions.nav.

Antioxidant and Cytoprotective Effects of Tibetan Tea and Its Phenolic Components.

PubMed

Xie, Hong; Li, Xican; Ren, Zhenxing; Qiu, Weimin; Chen, Jianlan; Jiang, Qian; Chen, Ban; Chen, Dongfeng

2018-01-24

Tibetan tea (Kangzhuan) is an essential beverage of the Tibetan people. In this study, a lyophilized aqueous extract of Tibetan tea ( LATT ) was prepared and analyzed by HPLC. The results suggested that there were at least five phenolic components, including gallic acid, and four catechins (i.e., (+)-catechin, (-)-catechin gallate ( CG ), (-)-epicatechin gallate ( ECG ), and (-)-epigallocatechin gallate). Gallic acid, the four catechins, and LATT were then comparatively investigated by four antioxidant assays: ferric reducing antioxidant power, 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radical (PTIO•) scavenging, 1,1-diphenyl-2-picryl-hydrazl radical scavenging, and 2,2'-azino-bis(3-ethylbenzo-thiazoline-6-sulfonic acid) radical scavenging assays. In these assays, LATT, along with the five phenolic components, increased their antioxidant effects in a concentration-dependent manner; however, the half maximal scavenging concentrations of ECG were always lower than those of CG . Gallic acid and the four catechins were also suggested to chelate Fe 2+ based on UV-visible spectral analysis. Ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS/MS) analysis suggested that, when mixed with PTIO•, the five phenolic components could yield two types of radical adduct formation (RAF) products (i.e., tea phenolic dimers and tea phenolic-PTIO• adducts). In a flow cytometry assay, (+)-catechin and LATT was observed to have a cytoprotective effect towards oxidative-stressed bone marrow-derived mesenchymal stem cells. Based on this evidence, we concluded that LATT possesses antioxidative or cytoprotective properties. These effects may mainly be attributed to the presence of phenolic components, including gallic acid and the four catechins. These phenolic components may undergo electron transfer, H⁺-transfer, and Fe 2+ -chelating pathways to exhibit antioxidative or cytoprotective effects. In these effects, two diastereoisomeric CG and ECG showed differences to which a steric effect from the 2-carbon may contribute. Phenolic component decay may cause RAF in the antioxidant process.

Antioxidant and α-glucosidase inhibitory activities of 40 tropical juices from Malaysia and identification of phenolics from the bioactive fruit juices of Barringtonia racemosa and Phyllanthus acidus.

PubMed

Sulaiman, Shaida Fariza; Ooi, Kheng Leong

2014-10-01

The present study compared pH, total soluble solids, vitamin C, and total phenolic contents, antioxidant activities, and α-glucosidase inhibitory activities of 40 fresh juices. The juice of Baccaurea polyneura showed the highest yield (74.17 ± 1.44%) and total soluble solids (32.83 ± 0.27 °Brix). The highest and lowest pH values were respectively measured from the juices of Dimocarpus longan (6.87 ± 0.01) and Averrhoa bilimbi (1.67 ± 0.67). The juice of Psidium guajava gave the highest total phenolic (857.24 ± 12.65 μg GAE/g sample) and vitamin C contents (590.31 ± 7.44 μg AAE/g sample). The juice of Phyllanthus acidus with moderate contents of total phenolics and vitamin C was found to exhibit the greatest scavenging (613.71 ± 2.59 μg VCEAC/g sample), reducing (2784.89 ± 3.93 μg TEAC/g sample), and α-glucosidase inhibitory activities (95.37 ± 0.15%). The juice of Barringtonia racemosa was ranked second in the activities and total phenolic content. Gallic and ellagic acids, which were quantified as the major phenolics of the respective juices, are suggested to be the main contributors to the antioxidant activities. The α-glucosidase inhibitory activity of the juices could be derived from myricetin and quercetin (that were previously reported as potent α-glucosidase inhibitors) in the hydrolyzed juice extracts. The juice of Syzygium samarangense, which was found to be highest in metal chelating activity (82.28 ± 0.10%), also was found to have these phenolics.

Preliminary phytochemical screening and In vitro antioxidant activities of the aqueous extract of Helichrysum longifolium DC

PubMed Central

2010-01-01

Background Many oxidative stress related diseases are as a result of accumulation of free radicals in the body. A lot of researches are going on worldwide directed towards finding natural antioxidants of plants origins. The aims of this study were to evaluate in vitro antioxidant activities and to screen for phytochemical constituents of Helichrysum longifolium DC. [Family Asteraceae] aqueous crude extract. Methods We assessed the antioxidant potential and phytochemical constituents of crude aqueous extract of Helichrysum longifolium using tests involving inhibition of superoxide anions, DPPH, H2O2, NO and ABTS. The flavonoid, proanthocyanidin and phenolic contents of the extract were also determined using standard phytochemical reaction methods. Results Phytochemical analyses revealed the presence of tannins, flavonoids, steroids and saponins. The total phenolic content of the aqueous leaf extract was 0.499 mg gallic acid equivalent/g of extract powder. The total flavonoid and proanthocyanidin contents of the plant were 0.705 and 0.005 mg gallic acid equivalent/g of extract powder respectively. The percentage inhibition of lipid peroxide at the initial stage of oxidation showed antioxidant activity of 87% compared to those of BHT (84.6%) and gallic acid (96%). Also, the percentage inhibition of malondialdehyde by the extract showed percentage inhibition of 78% comparable to those of BHT (72.24%) and Gallic (94.82%). Conclusions Our findings provide evidence that the crude aqueous extract of H. longifolium is a potential source of natural antioxidants, and this justified its uses in folkloric medicines. PMID:20470421

Proanthocyanidin Characterization, Antioxidant and Cytotoxic Activities of Three Plants Commonly Used in Traditional Medicine in Costa Rica: Petiveria alliaceae L., Phyllanthus niruri L. and Senna reticulata Willd.

PubMed Central

Navarro, Mirtha; Moreira, Ileana; Arnaez, Elizabeth; Quesada, Silvia; Azofeifa, Gabriela; Alvarado, Diego; Monagas, Maria J.

2017-01-01

The phenolic composition of aerial parts from Petiveria alliaceae L., Phyllanthus niruri L. and Senna reticulata Willd., species commonly used in Costa Rica as traditional medicines, was studied using UPLC-ESI-TQ-MS on enriched-phenolic extracts. Comparatively, higher values of total phenolic content (TPC), as measured by the Folin-Ciocalteau method, were observed for P. niruri extracts (328.8 gallic acid equivalents/g) than for S. reticulata (79.30 gallic acid equivalents/g) whereas P. alliaceae extract showed the lowest value (13.45 gallic acid equivalents/g). A total of 20 phenolic acids and proanthocyanidins were identified in the extracts, including hydroxybenzoic acids (benzoic, 4-hydroxybenzoic, gallic, prochatechuic, salicylic, syringic and vanillic acids); hydroxycinnamic acids (caffeic, ferulic, and p-coumaric acids); and flavan-3-ols monomers [(+)-catechin and (−)-epicatechin)]. Regarding proanthocyanidin oligomers, five procyanidin dimers (B1, B2, B3, B4, and B5) and one trimer (T2) are reported for the first time in P. niruri, as well as two propelargonidin dimers in S. reticulata. Additionally, P. niruri showed the highest antioxidant DPPH and ORAC values (IC50 of 6.4 μg/mL and 6.5 mmol TE/g respectively), followed by S. reticulata (IC50 of 72.9 μg/mL and 2.68 mmol TE/g respectively) and P. alliaceae extract (IC50 >1000 μg/mL and 1.32 mmol TE/g respectively). Finally, cytotoxicity and selectivity on gastric AGS and colon SW20 adenocarcinoma cell lines were evaluated and the best values were also found for P. niruri (SI = 2.8), followed by S. reticulata (SI = 2.5). Therefore, these results suggest that extracts containing higher proanthocyanidin content also show higher bioactivities. Significant positive correlation was found between TPC and ORAC (R2 = 0.996) as well as between phenolic content as measured by UPLC-DAD and ORAC (R2 = 0.990). These findings show evidence for the first time of the diversity of phenolic acids in P. alliaceae and S. reticulata, and the presence of proanthocyanidins as minor components in latter species. Of particular relevance is the occurrence of proanthocyanidin oligomers in phenolic extracts from P. niruri and their potential bioactivity. PMID:29048336

[Polyphenol compounds from Hamamelis virginiana L].

PubMed

Kostálová, D; Misíková, E; Gáborová, G

2001-01-01

Two phenolic acids and two flavone aglycones were isolated from the aboveground part of Hamamelis virginiana L. and identified with the use of thin-layer chromatography, melting points, and spectroscopic methods as gallic acid, ethyl gallate, quercetin, and kaempferol.

Surfactant-enhanced disinfection of the human norovirus surrogate, Tulane virus, with organic acids and surfactant

USDA-ARS?s Scientific Manuscript database

Combination treatments of surfactants and phenolic or short-chained organic acids (SCOA) may act synergistically or additively as sanitizers to inactive foodborne viruses and prevent outbreaks. The purpose of this study was to investigate the effect of gallic acid (GA), tannic acid (TA), p-coumaric ...

Peroxidase-like activity of the Co3O4 nanoparticles used for biodetection and evaluation of antioxidant behavior

NASA Astrophysics Data System (ADS)

Jia, Huimin; Yang, Dongfang; Han, Xiangna; Cai, Junhui; Liu, Haiying; He, Weiwei

2016-03-01

Nanostructured enzyme mimics are of great interest as promising alternatives to artificial enzymes for biomedical and catalytic applications. Studying the chemical interactions between antioxidants and nano-enzymes may result in a better understanding of the antioxidant capability of antioxidants and may help improve the function of artificial enzymes to better mimic natural enzymes. In this study, using Co3O4 nanoparticles (NPs) as peroxidase mimics to catalyze the oxidation of chromophoric substrates by H2O2, we developed a platform that acts as a biosensor for hydrogen peroxide and glucose and that can study the inhibitory effects of natural antioxidants on peroxidase mimics. This method can be applied specifically to glucose detection in real samples. Three natural antioxidants, gallic acid (GA), tannic acid (TA), and ascorbic acid (AA), were compared for their antioxidant capabilities. We found that these three antioxidants efficiently inhibit peroxidase-like activity with concentration dependence. The antioxidants showed different efficiencies, in the following order: tannic acid > gallic acid > ascorbic acid. They also showed distinct modes of inhibition based on different interaction mechanisms. This study serves as a proof-of-concept that nano-enzyme mimics can be used to evaluate antioxidant capabilities and to screen enzyme inhibitors.Nanostructured enzyme mimics are of great interest as promising alternatives to artificial enzymes for biomedical and catalytic applications. Studying the chemical interactions between antioxidants and nano-enzymes may result in a better understanding of the antioxidant capability of antioxidants and may help improve the function of artificial enzymes to better mimic natural enzymes. In this study, using Co3O4 nanoparticles (NPs) as peroxidase mimics to catalyze the oxidation of chromophoric substrates by H2O2, we developed a platform that acts as a biosensor for hydrogen peroxide and glucose and that can study the inhibitory effects of natural antioxidants on peroxidase mimics. This method can be applied specifically to glucose detection in real samples. Three natural antioxidants, gallic acid (GA), tannic acid (TA), and ascorbic acid (AA), were compared for their antioxidant capabilities. We found that these three antioxidants efficiently inhibit peroxidase-like activity with concentration dependence. The antioxidants showed different efficiencies, in the following order: tannic acid > gallic acid > ascorbic acid. They also showed distinct modes of inhibition based on different interaction mechanisms. This study serves as a proof-of-concept that nano-enzyme mimics can be used to evaluate antioxidant capabilities and to screen enzyme inhibitors. Electronic supplementary information (ESI) available: Fig. S1-S6. See DOI: 10.1039/c6nr00860g

Flow injection chemiluminescence determination of the total phenolics levels in plant-derived beverages using soluble manganese(IV).

PubMed

Nalewajko-Sieliwoniuk, Edyta; Tarasewicz, Iwona; Kojło, Anatol

2010-05-23

This study established a flow injection (FI) methodology for the determination of the total phenolic content in plant-derived beverages based on soluble manganese(IV) chemiluminescence (CL) detection. It was found that mixing polyphenols with acidic soluble manganese(IV) in the presence of formaldehyde evoked chemiluminescence. Based on this finding, a new FI-CL method was developed for the estimation of the total content of phenolic compounds (expressed as milligrams of gallic acid equivalent per litre of drink) in a variety of wine, tea and fruit juice samples. The proposed method is sensitive with a detection limit of 0.02 ng mL(-1) (gallic acid), offers a wide linear dynamic range (0.5-400 ng mL(-1)) and high sample throughput (247 samples h(-1)). The relative standard deviation for 15 measurements was 3.8% for 2 ng mL(-1) and 0.45% for 10 ng mL(-1) of gallic acid. Analysis of 36 different samples showed that the results obtained by the proposed FI-CL method correlate highly with those obtained by spectrophotometric methods commonly used for the evaluation of the total phenolic/antioxidant level. However, the FI-CL method was found to be far simpler, more rapid and selective, with almost no interference from non-phenolic components of the samples examined. Copyright 2010 Elsevier B.V. All rights reserved.

Potential of endophytic fungus Phomopsis liquidambari for transformation and degradation of recalcitrant pollutant sinapic acid.

PubMed

Xie, Xing-Guang; Huang, Chun-Yan; Fu, Wan-Qiu; Dai, Chuan-Chao

2016-03-01

The biodegradation potential of sinapic acid, one of the most representative methoxy phenolic pollutants presented in industrial wastewater, was first studied using an endophytic fungus called Phomopsis liquidambari. This strain can effectively degrade sinapic acid in flasks and in soil and the possible biodegradation pathway was first systematically proposed on the basis of the metabolite production patterns and the identification of the metabolites by GC-MS and HPLC-MS. Sinapic acid was first transformed to 2,6-dimethoxy-4-vinylphenol that was further degraded via 4-hydroxy-3,5-dimethoxybenzaldehyde, syringic acid, gallic acid, and citric acid which involved in the continuous catalysis by phenolic acid decarboxylase, laccase, and gallic acid dioxygenase. Moreover, their activities and gene expression levels exhibited a 'cascade induction' response with the changes in metabolic product concentrations and the generation of fungal laccase significantly improved the degradation process. This study is the first report of an endophytic fungus that has great potential to degrade xenobiotic sinapic acid, and also provide a basis for practical application of endophytic fungus in the bioremediation of sinapic acid-contaminated industrial wastewater and soils. Copyright © 2015 The British Mycological Society. Published by Elsevier Ltd. All rights reserved.

Augmenting the activity of antifungal agents against aspergilli using structural analogues of benzoic acid as chemosensitizing agents

USDA-ARS?s Scientific Manuscript database

Several benzoic acid analogs showed antifungal activity against strains of Aspergillus flavus, A. fumigatus and A. terreus, causative agents of human aspergillosis. Structure-activity analysis revealed that antifungal activities of benzoic and gallic acids increased by addition of a methyl, methoxyl...

Phenolic compounds and fatty acid composition of organic and conventional grown pecan kernels

USDA-ARS?s Scientific Manuscript database

In this study, differences in contents of phenolic compounds and fatty acids in pecan kernels of organically versus conventionally grown pecan cultivars (‘Desirable’, ‘Cheyenne’, and ‘Wichita’) were evaluated. Although we were able to identify nine phenolic compounds (gallic acid, catechol, catechin...

Gontscharovia popovii, a new source of carvacrol, its polyphenolic constituents, essential oil analysis, total phenolic content and antioxidant activity.

PubMed

Zareiyan, Faraneh; Rowshan, Vahid; Bahmanzadegan, Atefeh; Hatami, Ahmad

2017-09-28

The experiment was carried out using the shadow-dried aerial parts including leaves and shoots of Gontscharovia popovii collected in Fars province in order to investigate the polyphenolic compositions, antioxidant activity, total phenolic content and essential oil constituents. The result showed IC 50 of 395.77 μg mL -1 and total phenolic content of about 20.01 mg g -1 gallic acid equivalent dry weight. It also showed a wild range of polyphenols such as; Gallic acid, catechin, chloregenic acid, rutin, vanillin, trans-Ferulic acid, sinapic acid, coumarin, hesperedin, quercetin, hesperetin, eugenol and carvacrol as the main detected polyphenols. Some major compounds were also detected through essential oil analysis, such as; 76.7% carvacrol, 4.25% γ-Terpinene, 3.8% p-Cymene and 2.4% (E)-Caryophyllene. Qualitative and quantitative analyses of chemical compounds of G. popovii was performed using HPLC, GC, GC/MS and microplate reader.

Gallic Acid Grafted Chitosan Has Enhanced Oxidative Stability in Bulk Oils.

PubMed

Gim, Seo Yeong; Hong, Seungmi; Kim, Mi-Ja; Lee, JaeHwan

2017-07-01

Gallic acid (GA) was grafted in chitosan and the effects of GA grafted chitosan (GA-g-CS) on the oxidative stability in bulk oil was tested at 60 and 140 °C. To text oxidative stability in oils, headspace oxygen content, conjugated dienoic acid (CDA) value, p-anisidine value (p-AV), and acid value were determined. Chitosan itself did not show antioxidative or prooxidative effects in oils at 60 °C. However, GA-g-CS and GA acted as antioxidants at 60 °C. At 140 °C heating with moisture supplied condition, different results were observed. GA-g-CS acted as antioxidants based on the results of CDA and p-AV. However, chitosan showed the highest oxidative stability based on results of acid value and brown color formation at 140 °C. This could be due to reduction of moisture content by chitosan. GA was continuously released from GA-g-CS in bulk oil. This might have provided extra antioxidant activities to oils. © 2017 Institute of Food Technologists®.

Ellagic Acid Enhances the Efficacy of PI3K Inhibitor GDC-0941 in Breast Cancer Cells.

PubMed

Shi, L; Gao, X; Li, X; Jiang, N; Luo, F; Gu, C; Chen, M; Cheng, H; Liu, P

2015-01-01

The fact that the phosphatidylinositol 3 kinase (PI3K) signaling pathway is one of the most frequently deregulated signaling networks has triggered intensive efforts in the development of PI3K pathway inhibitors. However, recent clinical trial data have shown only limited activity of PI3K inhibitors at tolerated doses. Thus, there is an urgent need to identify rational combination therapy to improve the efficacy of PI3K-targeted cancer treatment. In this study, we investigated if dietary compound ellagic acid (EA) could improve the therapeutic efficacy of PI3K inhibitor GDC-0941 in breast cancer. Specifically, using a panel of breast cancer cell lines, we showed that combined use of EA and GDC-0941 significantly inhibited cell growth under attached and detached conditions, blocked migration and invasion in vitro as well as tumor initiation and metastasis in vivo. Furthermore, we found that EA promoted apoptosis and further reduced AKT/mTOR activation in GDC-0941- treated breast cancer cells. Together, our data suggest that EA may be a safe and effective agent to boost the efficacy of PI3K-directed breast cancer therapy and that such drug combination may merit further clinical investigation.

Hydrolyzable tannins from the fruits of Terminalia chebula Retz and their α-glucosidase inhibitory activities.

PubMed

Lee, Dong Young; Kim, Hyun Woo; Yang, Heejung; Sung, Sang Hyun

2017-05-01

Nine hydrolyzable tannins, including three previously unknown and six artifacts, were isolated, together with thirty-nine known ones, from the fruits of Terminalia chebula Retz. (Combretaceae). They were identified as 1,2,3-tri-O-galloyl-6-O-cinnamoyl-β-d-glucose, 1,2,3,6-tetra-O-galloyl-4-O-cinnamoyl-β-d-glucose, 4-O-(2″,4″-di-O-galloyl-α-l-rhamnosyl)ellagic acid, 1'-O-methyl neochebulanin, dimethyl neochebulinate, 6'-O-methyl neochebulagate, dimethyl neochebulagate, dimethyl 4'-epi-neochebulagate, and methyl chebulagate by the spectroscopic interpretation. After evaluation for α-glucosidase inhibition of all isolated compounds, 1,2,3,6-tetra-O-galloyl-4-O-cinnamoyl-β-d-glucose and 4-O-(2″,4″-di-O-galloyl-α-l-rhamnosyl)ellagic acid showed significant inhibitory activities with IC 50 values of 2.9 and 6.4 μM, respectively. In addition, inhibition kinetic studies showed that both compounds have mixed-type inhibitory activities with the inhibition constants (Ki) of 1.9 and 4.0 μM, respectively. Copyright © 2017 Elsevier Ltd. All rights reserved.

Development of antiproliferative nanohybrid compound with controlled release property using ellagic acid as the active agent

PubMed Central

Hussein, Mohd Zobir; Al Ali, Samer Hasan; Zainal, Zulkarnain; Hakim, Muhammad Nazrul

2011-01-01

An ellagic acid (EA)–zinc layered hydroxide (ZLH) nanohybrid (EAN) was synthesized under a nonaqueous environment using EA and zinc oxide (ZnO) as the precursors. Powder X-ray diffraction showed that the basal spacing of the nanohybrid was 10.4 Å, resulting in the spatial orientation of EA molecules between the interlayers of 22.5° from z-axis with two negative charges at 8,8′ position of the molecules pointed toward the ZLH interlayers. FTIR study showed that the intercalated EA spectral feature is generally similar to that of EA, but with bands slightly shifted. This indicates that some chemical bonding of EA presence between the nanohybrid interlayers was slightly changed, due to the formation of host–guest interaction. The nanohybrid is of mesopores type with 58.8% drug loading and enhanced thermal stability. The release of the drug active, EA from the nanohybrid was found to be sustained and therefore has good potential to be used as a drug controlled-release formulation. In vitro bioassay study showed that the EAN has a mild effect on the hepatocytes cells, similar to its counterpart, free EA. PMID:21796241

Uncovering the Lactobacillus plantarum WCFS1 Gallate Decarboxylase Involved in Tannin Degradation

PubMed Central

Jiménez, Natalia; Curiel, José Antonio; Reverón, Inés; de las Rivas, Blanca

2013-01-01

Lactobacillus plantarum is a lactic acid bacterium able to degrade tannins by the subsequent action of tannase and gallate decarboxylase enzymes. The gene encoding tannase had previously been identified, whereas the gene encoding gallate decarboxylase is unknown. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) of gallic-acid induced L. plantarum extracts showed a 54-kDa protein which was absent in the uninduced cells. This protein was identified as Lp_2945, putatively annotated UbiD. Homology searches identified ubiD-like genes located within three-gene operons which encoded the three subunits of nonoxidative aromatic acid decarboxylases. L. plantarum is the only bacterium in which the lpdC (lp_2945) gene and the lpdB and lpdD (lp_0271 and lp_0272) genes are separated in the chromosome. Combination of extracts from recombinant Escherichia coli cells expressing the lpdB, lpdC, and lpdC genes demonstrated that LpdC is the only protein required to yield gallate decarboxylase activity. However, the disruption of these genes in L. plantarum revealed that the lpdB and lpdC gene products are essential for gallate decarboxylase activity. Similar to L. plantarum tannase, which exhibited activity only in esters derived from gallic and protocatechuic acids, purified His6-LpdC protein from E. coli showed decarboxylase activity against gallic and protocatechuic acids. In contrast to the tannase activity, gallate decarboxylase activity is widely present among lactic acid bacteria. This study constitutes the first genetic characterization of a gallate decarboxylase enzyme and provides new insights into the role of the different subunits of bacterial nonoxidative aromatic acid decarboxylases. PMID:23645198

A characterization of the antimalarial activity of the bark of Cylicodiscus gabunensis Harms.

PubMed

Aldulaimi, Omar; Uche, Fidelia I; Hameed, Hamza; Mbye, Haddijatou; Ullah, Imran; Drijfhout, Falko; Claridge, Timothy D W; Horrocks, Paul; Li, Wen-Wu

2017-02-23

A decoction of the bark of Cylicodiscus gabunensis Harms is used as a traditional medicine in the treatment of malaria in Nigeria. This study aims to validate the antimalarial potency of this decoction in vitro against Plasmodium falciparum and define potential bioactive constituents within the C. gabunensis bark. A bioassay-guided separation and fractionation protocol was applied to C. gabunensis extracts, exploiting the use of a Malaria Sybr Green I Fluorescence assay method to monitor antiproliferative effects on parasites as well as define 50% inhibition concentrations. Spectroscopic techniques, including GC-MS, TOF LC-MS and 1 H NMR were used to identify phytochemicals present in bioactive fractions. Analogues of gallic acid were synthesized de novo to support the demonstration of the antimalarial action of phenolic acids identified in C. gabunensis bark. In vitro cytotoxicity of plant extracts, fractions and gallate analogues was evaluated against the HepG2 cell line. The antimalarial activity of ethanolic extracts of C. gabunensis bark was confirmed in vitro, with evidence for phenolic acids, primarily gallic acid and close analogues such as ethyl gallate, likely providing this effect. Further fractionation produced the most potent fraction with a 50% inhibitory concentration of 4.7µg/ml. Spectroscopic analysis, including 1 H NMR, LC-MS and GC-MS analysis of this fraction and its acid hydrolyzed products, indicated the presence of conjugates of gallic acid with oligosaccharides. The extracts/fractions and synthetic alkyl and alkenyl gallates showed moderate selectivity against P. falciparum. These results support the use of the bark of C. gabunensis as a traditional medicine in the treatment of human malaria, with phenolic acid oligosaccharide complexes evident in the most bioactive fractions. Copyright © 2017 Elsevier Ireland Ltd. All rights reserved.

Functional Characterization of Epitheaflagallin 3-O-Gallate Generated in Laccase-Treated Green Tea Extracts in the Presence of Gallic Acid.

PubMed

Itoh, Nobuya; Kurokawa, Junji; Isogai, Yasuhiro; Ogasawara, Masaru; Matsunaga, Takayuki; Okubo, Tsutomu; Katsube, Yuji

2017-12-06

Epitheaflagallin (ETFG) and epitheaflagallin 3-O-gallate (ETFGg) are minor polyphenols in black tea extract that are enzymatically synthesized from epigallocatechin (EGC) and epigallocatechin gallate (EGCg), respectively, in green tea extract via laccase oxidation in the presence of gallic acid. The constituents of laccase-treated green tea extract in the presence of gallic acid are thus quite different from those of nonlaccase-treated green tea extract: EGC and EGCg are present in lower concentrations, and ETFG and ETFGg are present in higher concentrations. Additionally, laccase-treated green tea extract contains further polymerized catechin derivatives, comparable with naturally fermented teas such as oolong tea and black tea. We found that ETFGg and laccase-treated green tea extracts exhibit versatile physiological functions in vivo and in vitro, including antioxidative activity, pancreatic lipase inhibition, Streptococcus sorbinus glycosyltransferase inhibition, and an inhibiting effect on the activity of matrix metalloprotease-1 and -3 and their synthesis by human gingival fibroblasts. We confirmed that these inhibitory effects of ETFGg in vitro match well with the results obtained by docking simulations of the compounds with their target enzymes or noncatalytic protein. Thus, ETFGg and laccase-treated green tea extracts containing ETFGg are promising functional food materials with potential antiobesity and antiperiodontal disease activities.

Native Plant and Microbial Contributions to a Negative Plant-Plant Interaction1[OA

PubMed Central

Bains, Gurdeep; Sampath Kumar, Amutha; Rudrappa, Thimmaraju; Alff, Emily; Hanson, Thomas E.; Bais, Harsh P.

2009-01-01

A number of hypotheses have been suggested to explain why invasive exotic plants dramatically increase their abundance upon transport to a new range. The novel weapons hypothesis argues that phytotoxins secreted by roots of an exotic plant are more effective against naïve resident competitors in the range being invaded. The common reed Phragmites australis has a diverse population structure including invasive populations that are noxious weeds in North America. P. australis exudes the common phenolic gallic acid, which restricts the growth of native plants. However, the pathway for free gallic acid production in soils colonized by P. australis requires further elucidation. Here, we show that exotic, invasive P. australis contain elevated levels of polymeric gallotannin relative to native, noninvasive P. australis. We hypothesized that polymeric gallotannin can be attacked by tannase, an enzymatic activity produced by native plant and microbial community members, to release gallic acid in the rhizosphere and exacerbate the noxiousness of P. australis. Native plants and microbes were found to produce high levels of tannase while invasive P. australis produced very little tannase. These results suggest that both invasive and native species participate in signaling events that initiate the execution of allelopathy potentially linking native plant and microbial biochemistry to the invasive traits of an exotic species. PMID:19776161

Dynamic calibration approach for determining catechins and gallic acid in green tea using LC-ESI/MS.

PubMed

Bedner, Mary; Duewer, David L

2011-08-15

Catechins and gallic acid are antioxidant constituents of Camellia sinensis, or green tea. Liquid chromatography with both ultraviolet (UV) absorbance and electrospray ionization mass spectrometric (ESI/MS) detection was used to determine catechins and gallic acid in three green tea matrix materials that are commonly used as dietary supplements. The results from both detection modes were evaluated with 14 quantitation models, all of which were based on the analyte response relative to an internal standard. Half of the models were static, where quantitation was achieved with calibration factors that were constant over an analysis set. The other half were dynamic, with calibration factors calculated from interpolated response factor data at each time a sample was injected to correct for potential variations in analyte response over time. For all analytes, the relatively nonselective UV responses were found to be very stable over time and independent of the calibrant concentration; comparable results with low variability were obtained regardless of the quantitation model used. Conversely, the highly selective MS responses were found to vary both with time and as a function of the calibrant concentration. A dynamic quantitation model based on polynomial data-fitting was used to reduce the variability in the quantitative results using the MS data.

Radiation induced chemical changes of phenolic compounds in strawberries

NASA Astrophysics Data System (ADS)

Breitfellner, F.; Solar, S.; Sontag, G.

2003-06-01

In unirradiated strawberries four phenolic acids (gallic acid, p-coumaric acid, caffeic acid and 4-hydroxybenzoic acid), the flavonoids (+)-catechin, (-)-epicatechin and glycosides from kaempferol and quercetin were determined by reversed phase chromatography with diode array detection. Characteristic linear dose/concentration relationships were found for 4-hydroxybenzoic acid and two unidentified compounds. One of them may be usable as marker to prove an irradiation treatment.

Development of new antioxidant active packaging films based on ethylene vinyl alcohol copolymer (EVOH) and green tea extract.

PubMed

Lopez de Dicastillo, Carol; Nerin, Cristina; Alfaro, Pilar; Catala, Ramon; Gavara, Rafael; Hernandez-Munoz, Pilar

2011-07-27

Ethylene vinyl alcohol copolymer (EVOH) films containing green tea extract were successfully produced by extrusion. The films were brown and translucent, and the addition of the extract increased the water and oxygen barrier at low relative humidity but increased the water sensitivity, the glass transition temperature, and the crystallinity of the films and improved their thermal resistance. An analysis by HPLC revealed that the antioxidant components of the extract suffered partial degradation during extrusion, reducing the content of catechin gallates and increasing the concentration of free gallic acid. Exposure of the films to various food simulants showed that the liquid simulants increased their capacity to reduce DPPH(•) and ABTS(•+) radicals. The release of green tea extract components into the simulant monitored by HPLC showed that all compounds present in the green tea extract were partially released, although the extent and kinetics of release were dependent on the type of food. In aqueous food simulants, gallic acid was the main antioxidant component released with partition coefficient values ca. 200. In 95% ethanol (fatty food simulant) the K value for gallic acid decreased to 8 and there was a substantial contribution of catechins (K in the 1000 range) to a greatly increased antioxidant efficiency. Kinetically, gallic acid was released more quickly than catechins, owing to its faster diffusivity in the polymer matrix as a consequence of its smaller molecular size, although the most relevant effect is the plasticization of the matrix by alcohol, increasing the diffusion coefficient >10-fold. Therefore, the materials here developed with the combination of antioxidant substances that constitute the green tea extract could be used in the design of antioxidant active packaging for all type of foods, from aqueous to fatty products, the compounds responsible for the protection being those with the higher compatibility with the packaged product.

Antifungal Activity of Gallic Acid In Vitro and In Vivo.

PubMed

Li, Zhi-Jian; Liu, Meng; Dawuti, Gulina; Dou, Qin; Ma, Yu; Liu, Heng-Ge; Aibai, Silafu

2017-07-01

Gallic acid (GA) is a polyphenol natural compound found in many medicinal plant species, including pomegranate rind (Punica granatum L.), and has been shown to have antiinflammatory and antibacterial properties. Pomegranate rind is used to treat bacterial and fungal pathogens in Uyghur and other systems of traditional medicine, but, surprisingly, the effects of GA on antifungal activity have not yet been reported. In this study, we aimed to investigate the inhibitory effects of GA on fungal strains both in vitro and in vivo. The minimal inhibitory concentration (MIC) was determined by the NCCLS (M38-A and M27-A2) standard method in vitro, and GA was found to have a broad spectrum of antifungal activity, with MICs for all the tested dermatophyte strains between 43.75 and 83.33 μg/mL. Gallic acid was also active against three Candida strains, with MICs between 12.5 and 100.0 μg/mL. The most sensitive Candida species was Candida albicans (MIC = 12.5 μg/mL), and the most sensitive filamentous species was Trichophyton rubrum (MIC = 43.75 μg/mL), which was comparable in potency to the control, fluconazole. The mechanism of action was investigated for inhibition of ergosterol biosynthesis using an HPLC-based assay and an enzyme linked immunosorbent assay. Gallic acid reduced the activity of sterol 14α-demethylase P450 (CYP51) and squalene epoxidase in the T. rubrum membrane, respectively. In vivo model demonstrated that intraperitoneal injection administration of GA (80 mg/kg d) significantly enhanced the cure rate in a mice infection model of systemic fungal infection. Overall, our results confirm the antifungal effects of GA and suggest a mechanism of action, suggesting that GA has the potential to be developed further as a natural antifungal agent for clinical use. Copyright © 2017 John Wiley & Sons, Ltd. Copyright © 2017 John Wiley & Sons, Ltd.

Therapeutic potentials of Crataegus azarolus var. eu- azarolus Maire leaves and its isolated compounds.

PubMed

Abu-Gharbieh, Eman; Shehab, Naglaa Gamil

2017-04-18

Hyperglycemia is a complicated condition accompanied with high incidence of infection and dyslipidemia. This study aimed to explore the phyto-constituents of Crataegus azarolus var. eu- azarolus Maire leaves, and to evaluate the therapeutic potentials particularly antimicrobial, antihyperglycemic and antihyperlipidemic of the extract and the isolated compound (3β-O-acetyl ursolic acid). Total phenolics and flavonoidal contents were measured by RP-HPLC analysis. Free radicals scavenging activity of different extraction solvents was tested in-vitro on DPPH free radicals. The antimicrobial activity of the ethanolic extract and its fractions as well as the isolated compounds were evaluated in-vitro on variable microorganisms. Animal models were used to evaluate the antihyperglycemic and antihyperlipidemic activities of the ethanolic extract along with the isolated compound (3β-O acetyl ursolic acid). RP- HPLC analysis of the phenolics revealed high content of rutin, salicylic and ellagic acids. Six compounds belonging to triterpenes and phenolics were isolated from chloroform and n-butanol fractions namely: ursolic acid, 3β-O-acetyl ursolic acid, ellagic acid, quercetin 3-O-β methyl ether, rutin and apigenin7-O-rutinoside. Ethanolic extract showed the highest DPPH radical scavenger activity compared to other solvents. Ethanolic extract, hexane fraction, ursolic acid, 3β-O acetyl ursolic acid and quercetin 3-O-methyl ether showed variable antimicrobial activity against E. coli, P. aeruginosa, S. aureus, and C. albicans. Administration of the ethanolic extract or 3β-O acetyl ursolic acid orally to the mice reduced blood glucose significantly in a time- and dose-dependent manner. Ethanolic extract significantly reduced LDL-C, VLDL-C, TC and TG and increased HDL-C in rats. Ethanolic extract and 3β-O acetyl ursolic acid reduced in-vitro activity of pancreatic lipase. This study reveals that Crataegus azarolus var. eu- azarolus Maire has the efficiency to control hyperglycemia with its associated complications. This study is the first to evaluate antihyperglycemic and antihyperlipidemic potentials of 3β-O acetyl ursolic acid.

Beneficial influence of ellagic acid on biochemical indexes associated with experimentally induced colon carcinogenesis.

PubMed

Syed, Umesalma; Ganapasam, Sudhandiran

2017-01-01

To elucidate the key biochemical indexes associated with 1, 2-dimethylhydrazine (DMH)-induced colon carcinogenesis and the modulatory efficacy of a dietary polyphenol, ellagic acid (EA). Wistar rats were chosen to study objective, and were divided into 4 groups; Group 1-control rats; Group 2-rats received EA (60 mg/kg body weight/day, orally); rats in Group 3-induced with DMH (20 mg/kg body weight) subcutaneously for 15 weeks; DMH-induced Group 4 rats were initiated with EA treatment. We examined key citric acid cycle enzymes such as isocitrate dehydrogenase, alpha-ketoglutarate dehydrogenase, succinate dehydrogenase, malate dehydrogenase and the activities of respiratory chain enzymes NADH dehydrogenase and Cytochrome-C-oxidase and membrane-bound enzyme profiles (Na +/K + ATPase, Ca 2+ ATPase and Mg 2+ ATPase), activities of lysosomal proteases such as β-D-glucuronidase, β-galactosidase and N-acety-β-D-glucosaminidase and cellular thiols (oxidized glutathione, protein thiols, and total thiols). It was found that administration of DMH to rats decreased both mitochondrial and membrane-bound enzymes activities, increased activities of lysosomal enzymes and further modulates cellular thiols levels. Treatment with EA significantly restored the mitochondrial and ATPases levels and further reduced lysosomal enzymes to near normalcy thereby restoring harmful effects induced by DMH. EA treatment was able to effectively restore the detrimental effects induced by DMH, which proves the chemoprotective function of EA against DMH-induced experimental colon carcinogenesis.

Enhanced functional properties of tannic acid after thermal hydrolysis

USDA-ARS?s Scientific Manuscript database

Thermal hydrolysis processing of fresh tannic acid was carried out in a closed reactor at four different temperatures (65, 100, 150 and 200°C). Pressures reached in the system were 1.3 and 4.8 MPa at 150 and 200°C, respectively. Hydrolysis products (gallic acid and pyrogallol) were separated and qua...

Antioxidant properties and phenolic profile characterization by LC-MS/MS of selected Tunisian pomegranate peels.

PubMed

Abid, Mouna; Yaich, Héla; Cheikhrouhou, Salma; Khemakhem, Ibtihel; Bouaziz, Mohamed; Attia, Hamadi; Ayadi, M A

2017-08-01

Antioxidant contents and activities of different extracts from four Tunisian pomegranate peels, locally called "Acide", "Gabsi", "Nebli" and "Tounsi", were studied. Peels samples were extracted with three solvents (water, ethanol and acetone). For each extract, the total phenol contents and antioxidant activity were evaluated. The highest values of polyphenol, tannins, flavonoids and anthocyanins were recorded in the acetone extract of Acide ecotype with 304.6 mg gallic acid equivalent/g; 292.23 mg gallic acid equivalent/g; 15.46 mg Quercetin/g and 54.51 mg cy-3-glu/100 g, respectively. The acetone extract of Acide ecotype also showed the highest free radical-scavenging and reducing power activity compared to other extracts. Besides, the phytochemical analysis by LC-MS/MS revealed a high content of ellagitannins with punicalagin and punicalagin derivatives as the major compounds that might be responsible for promising antioxidant activity of pomegranate peel extracts. Two compounds (Castalagin derivative and Galloyl-bis-HHDP-hex derivative) were detected only in "Acide" ecotype in important contents.

Role of gallic and p-coumaric acids in the AHL-dependent expression of flgA gene and in the process of biofilm formation in food-associated Pseudomonas fluorescens KM120.

PubMed

Myszka, Kamila; Schmidt, Marcin T; Białas, Wojciech; Olkowicz, Mariola; Leja, Katarzyna; Czaczyk, Katarzyna

2016-09-01

In the process of Pseudomonas fluorescens biofilm formation, N-acyl-l-homoserine lactone (AHL)-mediated flagella synthesis plays a key role. Inhibition of AHL production may attenuate P. fluorescens biofilm on solid surfaces. This work validated the anti-biofilm properties of p-coumaric and gallic acids via the ability of phenolics to suppress AHL synthesis in P. fluorescens KM120. The dependence between synthesis of AHL molecules, expression of flagella gene (flgA) and the ability of biofilm formation by P. fluorescens KM120 on a stainless steel surface (type 304L) was also investigated. Research was carried out in a purpose-built flow cell device. Limitations on AHL synthesis in P. fluorescens KM120 were observed at concentrations of 120 and 240 µmol L(-1) of phenolic acids in medium. At such levels of gallic and p-coumaric acids the ability of P. fluorescens KM120 to synthesize 3-oxo-C6-homoserine lactone (HSL) was not observed. These concentrations caused decreased expression of flgA gene in P. fluorescens KM120. The changes in expression of AHL-dependent flgA gene significantly decreased the rate of microorganism colonization on the stainless steel surface. Phenolic acids are able to inhibit biofilm formation. The results obtained in the work may help to develop alternative techniques for anti-biofilm treatment in the food industry. © 2015 Society of Chemical Industry. © 2015 Society of Chemical Industry.

Antioxidant and Nephroprotective Activities of the Extract and Fractions of Homonoia riparia Lour.

PubMed

Xavier, Seena Kanniparambil; Haneefa, Shoja Muhammed; Anand, Devkar Raviraj; Polo, Picheswara Rao; Maheshwari, Rajalekshmi; Shreedhara, Chandrashekara Shastry; Setty, Manganahalli Manjunath

2017-01-01

Homonoia riparia is a plant, which is widely used in the indigenous system of medicine for the treatment of urolithiasis, renal disorders and inflammatory conditions. This is the first report on the antioxidant and nephroprotective activities of whole plant of H. riparia . The present study aims at investigating the in vitro antioxidant and nephroprotective activity of the methanol extract and its different fractions of H. riparia . Petroleum ether (HRPE), Ethyl acetate (HREA), Butanol (HRBU), aqueous fractions (HRAQ) were prepared from the crude methanol extract of H. riparia (HRM) using liquid partitioning. Total phenolic content, flavonoid content and antioxidant activity assay were performed according to suitable methods. Nephroprotective activities were evaluated by MTT assay using Human Embryonic Kidney cells against cisplatin induced toxicity. Quantification of gallic acid was performed using validated HPTLC method. The studies showed that extract and fractions possess significant nephroprotective activity against cisplatin induced renal toxicity. All the extracts/fractions of whole plant of Homonoia riparia was found to be significantly reducing cisplatin induced toxicity (< 0.05). The highest activity was observed with HRBU and HRAQ with a percentage viability of 293.09 ± 4.3 and 345.07 ± 3.2 at a concentration of 200 µg/ml. Gallic acid was detected in the HRM/fractions using HPTLC. Cisplatin (8 μg/ml) exhibited 50 % inhibition in cell viability in HEK 293 cellsButanol and aqueous fractions of Homonoia riparia showed significant nephroprotective activity against cisplatin induced cell damage in HEK cells.Gallic acid was detected and quantified in the extract and fractions of whole plant of Homonoia riparia Abbreviations used: HPTLC: High Performance Thin Layer Chromatography, DPPH: 1,1-diphenyl-2-picrylhydrazyl, ABTS: 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt, MTT: 3-(4,5-dimethylthiazolyl-2-yl)-2,5- diphenyl tetrazolium bromide, GAE: Gallic acid equivalents, QE: Quercetin equivalents, HEK: Human Embryonic Kidney, HRM: Methanol extract of H. riparia, HRPE: Petroleum ether fraction of H. riparia, HREA: ethyl acetate fraction of H. riparia, HRBU: Butanol fraction of H. riparia, HRAQ: Aqueous fraction of H. riparia, DMEM: Dulbecco's minimum essential medium, FBS: Foetal bovine serum, DMSO: Dimethyl sulfoxide, ANOVA: One way analysis of variance.

HPLC-ED Analysis of Phenolic Compounds in Three Bosnian Crataegus Species.

PubMed

Čulum, Dušan; Čopra-Janićijević, Amira; Vidic, Danijela; Klepo, Lejla; Tahirović, Azra; Bašić, Neđad; Maksimović, Milka

2018-04-24

The aim of this work was the qualitative and quantitative determination of selected phenolic compounds in three Crataegus species grown in Bosnia. Crataegus plants are consumed for medicinal purposes and as foodstuff in the form of canned fruit, jam, jelly, tea, and wine. Two samples of plant material, dry leaves with flowers, and berries of three Crataegus species— Crataegus rhipidophylla Gand., Crataegus x subsphaericea Gand., and Crataegus x macrocarpa Hegetschw.—were analyzed. Twelve ethanolic extracts were isolated from the selected plant material using Soxhlet and ultrasound extraction, respectively. Soxhlet extraction proved to be more effective than ultrasound extraction. A simple and sensitive method, high-performance liquid chromatography with electrochemical detection, HPLC-ED, was used for the simultaneous determination of phenolic acids and flavonoids in Crataegus species. The content of gallic acid in the extracts ranged from 0.001 to 0.082 mg/g dry weight (DW), chlorogenic acid from 0.19 to 8.70 mg/g DW, and rutin from 0.03 to 13.49 mg/g DW. Two flavonoids, vitexin and hyperoside, commonly found in chemotaxonomic investigations of Crataegus species, were not detected in the examined extracts. In general, leaves with flowers samples are richer in gallic acid and rutin, whereas the berries samples are richer in chlorogenic acid. Distinct similarities were found in the relative distribution of gallic acid among the three species. Extracts of C. x macrocarpa had the highest content of all detected compounds, while significant differences were found in rutin content, depending on the plant organ. To the best of our knowledge, this is the first study reporting content of phenolic compounds in Crataegus rhipidophylla Gand., Crataegus x subsphaericea , and Crataegus x macrocarpa from Bosnia.

HPLC-ED Analysis of Phenolic Compounds in Three Bosnian Crataegus Species

PubMed Central

Čulum, Dušan; Vidic, Danijela; Klepo, Lejla; Tahirović, Azra; Bašić, Neđad; Maksimović, Milka

2018-01-01

The aim of this work was the qualitative and quantitative determination of selected phenolic compounds in three Crataegus species grown in Bosnia. Crataegus plants are consumed for medicinal purposes and as foodstuff in the form of canned fruit, jam, jelly, tea, and wine. Two samples of plant material, dry leaves with flowers, and berries of three Crataegus species—Crataegus rhipidophylla Gand., Crataegus x subsphaericea Gand., and Crataegus x macrocarpa Hegetschw.—were analyzed. Twelve ethanolic extracts were isolated from the selected plant material using Soxhlet and ultrasound extraction, respectively. Soxhlet extraction proved to be more effective than ultrasound extraction. A simple and sensitive method, high-performance liquid chromatography with electrochemical detection, HPLC-ED, was used for the simultaneous determination of phenolic acids and flavonoids in Crataegus species. The content of gallic acid in the extracts ranged from 0.001 to 0.082 mg/g dry weight (DW), chlorogenic acid from 0.19 to 8.70 mg/g DW, and rutin from 0.03 to 13.49 mg/g DW. Two flavonoids, vitexin and hyperoside, commonly found in chemotaxonomic investigations of Crataegus species, were not detected in the examined extracts. In general, leaves with flowers samples are richer in gallic acid and rutin, whereas the berries samples are richer in chlorogenic acid. Distinct similarities were found in the relative distribution of gallic acid among the three species. Extracts of C. x macrocarpa had the highest content of all detected compounds, while significant differences were found in rutin content, depending on the plant organ. To the best of our knowledge, this is the first study reporting content of phenolic compounds in Crataegus rhipidophylla Gand., Crataegus x subsphaericea, and Crataegus x macrocarpa from Bosnia. PMID:29695058

Anti-Inflammatory Activities of Pentaherbs Formula, Berberine, Gallic Acid and Chlorogenic Acid in Atopic Dermatitis-Like Skin Inflammation.

PubMed

Tsang, Miranda S M; Jiao, Delong; Chan, Ben C L; Hon, Kam-Lun; Leung, Ping C; Lau, Clara B S; Wong, Eric C W; Cheng, Ling; Chan, Carmen K M; Lam, Christopher W K; Wong, Chun K

2016-04-20

Atopic dermatitis (AD) is a common allergic skin disease, characterized by dryness, itchiness, thickening and inflammation of the skin. Infiltration of eosinophils into the dermal layer and presence of edema are typical characteristics in the skin biopsy of AD patients. Previous in vitro and clinical studies showed that the Pentaherbs formula (PHF) consisting of five traditional Chinese herbal medicines, Flos Lonicerae, Herba Menthae, Cortex Phellodendri, Cortex Moutan and Rhizoma Atractylodis at w/w ratio of 2:1:2:2:2 exhibited therapeutic potential in treating AD. In this study, an in vivo murine model with oxazolone (OXA)-mediated dermatitis was used to elucidate the efficacy of PHF. Active ingredients of PHF water extract were also identified and quantified, and their in vitro anti-inflammatory activities on pruritogenic cytokine IL-31- and alarmin IL-33-activated human eosinophils and dermal fibroblasts were evaluated. Ear swelling, epidermis thickening and eosinophils infiltration in epidermal and dermal layers, and the release of serum IL-12 of the murine OXA-mediated dermatitis were significantly reduced upon oral or topical treatment with PHF (all p < 0.05). Gallic acid, chlorogenic acid and berberine contents (w/w) in PHF were found to be 0.479%, 1.201% and 0.022%, respectively. Gallic acid and chlorogenic acid could suppress the release of pro-inflammatory cytokine IL-6 and chemokine CCL7 and CXCL8, respectively, in IL-31- and IL-33-treated eosinophils-dermal fibroblasts co-culture; while berberine could suppress the release of IL-6, CXCL8, CCL2 and CCL7 in the eosinophil culture and eosinophils-dermal fibroblasts co-culture (all p < 0.05). These findings suggest that PHF can ameliorate allergic inflammation and attenuate the activation of eosinophils.

Biosynthesis of flat silver nanoflowers: from Flos Magnoliae Officinalis extract to simulation solution

NASA Astrophysics Data System (ADS)

Jing, Xiaolian; Huang, Jiale; Wu, Lingfeng; Sun, Daohua; Li, Qingbiao

2014-03-01

Flat Ag nanoflowers were directly synthesized from the bioreduction of AgNO3 using Flos Magnoliae Officinalis extract without any additional stabilizer or protective agent at room temperature. Effects of concentrations of the Flos Magnoliae Officinalis extract on the Ag nanostructures were investigated. The main components containing flavone, polyphenol, protein, and reducing sugar in the plant extract were thoroughly determined before and after the reaction, and the dialysis experiments were also conducted. The results of components analysis and dialysis showed that gallic acid representing polyphenols played an important role in the biosynthesis of silver nanoplates. Trisodium citrate combined gallic acid solution, instead of Flos Magnoliae Officinalis extract, was employed and successfully simulated the biosynthesis process of the flat Ag nanoflowers.

Phenolic constituents of shea (Vitellaria paradoxa) kernels.

PubMed

Maranz, Steven; Wiesman, Zeev; Garti, Nissim

2003-10-08

Analysis of the phenolic constituents of shea (Vitellaria paradoxa) kernels by LC-MS revealed eight catechin compounds-gallic acid, catechin, epicatechin, epicatechin gallate, gallocatechin, epigallocatechin, gallocatechin gallate, and epigallocatechin gallate-as well as quercetin and trans-cinnamic acid. The mean kernel content of the eight catechin compounds was 4000 ppm (0.4% of kernel dry weight), with a 2100-9500 ppm range. Comparison of the profiles of the six major catechins from 40 Vitellaria provenances from 10 African countries showed that the relative proportions of these compounds varied from region to region. Gallic acid was the major phenolic compound, comprising an average of 27% of the measured total phenols and exceeding 70% in some populations. Colorimetric analysis (101 samples) of total polyphenols extracted from shea butter into hexane gave an average of 97 ppm, with the values for different provenances varying between 62 and 135 ppm of total polyphenols.

Bioactives of coffee cherry pulp and its utilisation for production of Cascara beverage.

PubMed

Heeger, Andrea; Kosińska-Cagnazzo, Agnieszka; Cantergiani, Ennio; Andlauer, Wilfried

2017-04-15

Coffee cherry pulp is a by-product obtained during coffee production. Coffee cherry pulp contains considerable amounts of phenolic compounds and caffeine. An attempt to produce Cascara, a refreshing beverage, has been made. Six dried coffee pulp samples and a beverage called Cascara produced in Switzerland out of one of those samples were investigated. Aqueous extraction of coffee pulps revealed a content of total polyphenols between 4.9 and 9.2mg gallic acid equivalents (GAE)/gDM. The antioxidant capacity was between 51 and 92μmol Trolox equivalents (TE)/gDM as measured by the assay with ABTS radical. Bourbon variety from Congo and maragogype variety showed highest caffeine contents with 6.5 and 6.8mg/gDM. In all samples chlorogenic acid, protocatechuic acid, gallic acid and rutin were present. The beverage Cascara contained 226mg/L of caffeine and 283mgGAE/L of total polyphenols whereas antioxidant capacity amounted to 8.9mmol TE/L. Copyright © 2016 Elsevier Ltd. All rights reserved.

Phenolic compounds from the flowers of Nepalese medicinal plant Aconogonon molle and their DPPH free radical-scavenging activities.

PubMed

Joshi, Khem Raj; Devkota, Hari Prasad; Watanabe, Takashi; Yahara, Shoji

2014-01-01

Eleven phenolic compounds, quercetin (1), quercetin 3-O-β-d-galactopyranoside (2), quercetin 3-O-(6″-O-galloyl)-β-d-galactopyranoside (3), quercetin 3-O-(6″-O-caffeoyl)-β-d-galactopyranoside (4), quercetin 3-O-β-d-glucopyranoside (5), rutin (6) quercetin 3-O-α-l-arabinopyranoside (7), quercetin 3-O-α-l-arabinofuranoside (8), protocatechulic acid (9), gallic acid (10) and chlorogenic acid (11), were isolated from the flowers of Aconogonon molle, a Nepalese medicinal plant. Structures of these compounds were elucidated on the basis of spectroscopic methods. All these compounds were isolated for the first time from flowers, and five compounds (4, 5, 8, 9 and 11) were isolated for the first time from A. molle. All of these isolated compounds were evaluated for their in vitro antioxidant activity by using the 1,1-diphenyl-2-picrylhydrazyl radical-scavenging method. Quercetin (1), quercetin glycosides (2-8) and gallic acid (10) exhibited potent antioxidant activity.

Flexible graphene/carbon nanotube hybrid papers chemical-reduction-tailored by gallic acid for high-performance electrochemical capacitive energy storages

NASA Astrophysics Data System (ADS)

Yao, Lu; Zhou, Chao; Hu, Nantao; Hu, Jing; Hong, Min; Zhang, Liying; Zhang, Yafei

2018-03-01

Mechanically robust graphene papers with both high gravimetric and volumetric capacitances are desired for high-performance energy storages. However, it's still a challenge to tailor the structure of graphene papers in order to meet this requirement. In this work, a kind of chemical-reduction-tailored mechanically-robust reduced graphene oxide/carbon nanotube hybrid paper has been reported for high-performance electrochemical capacitive energy storages. Gallic acid (GA), as an excellent reducing agent, was used to reduce graphene oxide. Through vacuum filtration of gallic acid reduced graphene oxide (GA-rGO) and carboxylic multiwalled carbon nanotubes (MWCNTs) aqueous suspensions, mechanically robust GA-rGO/MWCNTs hybrid papers were obtained. The resultant hybrid papers showed high gravimetric capacitance of 337.6 F g-1 (0.5 A g-1) and volumetric capacitance of 151.2 F cm-3 (0.25 A cm-3). In addition, the assembled symmetric device based on the hybrid papers exhibited high gravimetric capacitance of 291.6 F g-1 (0.5 A g-1) and volumetric capacitance of 136.6 F cm-3 (0.25 A cm-3). Meanwhile, it exhibited excellent rate capability and cycling stability. Above all, this chemical reduction tailoring technique and the resultant high-performance GA-rGO/MWCNTs hybrid papers give an insight for designing high-performance electrodes and hold a great potential in the field of energy storages.

A cellular uptake and cytotoxicity properties study of gallic acid-loaded mesoporous silica nanoparticles on Caco-2 cells

NASA Astrophysics Data System (ADS)

Rashidi, Ladan; Vasheghani-Farahani, Ebrahim; Soleimani, Masoud; Atashi, Amir; Rostami, Khosrow; Gangi, Fariba; Fallahpour, Masoud; Tahouri, Mohammad Taher

2014-03-01

In this study, the effects of intracellular delivery of various concentrations of gallic acid (GA) as a semistable antioxidant, gallic acid-loaded mesoporous silica nanoparticles (MSNs-GA), and cellular uptake of nanoparticles into Caco-2 cells were investigated. MSNs were synthesized and loaded with GA, then characterized using transmission electron microscopy (TEM), scanning electron microscopy (SEM), Fourier transform infrared spectroscopy, N2 adsorption isotherms, X-ray diffraction, and thermal gravimetric analysis. The cytotoxicity of MSNs and MSNs-GA at low and high concentrations were studied by means of 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) test and flow cytometry. MSNs did not show significant toxicity in various concentrations (0-500 μg/ml) on Caco-2 cells. For MSNs-GA, cell viability was reduced as a function of incubation time and different concentrations of nanoparticles. The in vitro GA release from MSNs-GA exhibited the same antitumor properties as free GA on Caco-2 cells. Flow cytometry results confirmed those obtained using MTT assay. TEM and fluorescent microscopy confirmed the internalization of MSNs by Caco-2 cells through nonspecific cellular uptake. MSNs can easily internalize into Caco-2 cells without deleterious effects on cell viability. The cell viability of Caco-2 cells was affected during MSNs-GA uptake. MSNs could be designed as suitable nanocarriers for antioxidants delivery.

Enhancement of periodate-hydrogen peroxide chemiluminescence by nitrogen doped carbon dots and its application for the determination of pyrogallol and gallic acid.

PubMed

Shah, Syed Niaz Ali; Li, Haifang; Lin, Jin-Ming

2016-06-01

A new sensitized chemiluminescence (CL) was developed to broaden the analytical application of KIO4-H2O2 system. The nitrogen doped carbon dots (N-CDs) dramatically boosted the CL intensity of KIO4-H2O2 system which was further enriched by basic medium. In light of EPR analysis, free radical scavenging studies and CL spectra the detail mechanism for the enhancement was conferred in the presence of N-CDs and NaOH. The results suggested that CL of KIO4-H2O2 system in the presence and absence of N-CDs and NaOH proceeds via radical pathway. The enhanced CL was used for the determination of pyrogallol and gallic acid in range of 1.0×10(-4)-1.0×10(-7)M with 4.6×10(-8) and 6.1×10(-8)M limit of detection respectively. The relative standard deviation (RSD) at a concentration of 10(-5) for gallic acid and pyrogallol was 1.4% and 2.3% respectively (n=11). The attained results unveil that the present method is sensitive, faster, simpler and less costly compared to other methods and could be applied to determine polyphenols in real samples. Copyright © 2016 Elsevier B.V. All rights reserved.

Analysis of polyphenols in white wine by CZE with amperometric detection using carbon nanotube-modified electrodes.

PubMed

Moreno, Mónica; Arribas, Alberto Sánchez; Bermejo, Esperanza; Zapardiel, Antonio; Chicharro, Manuel

2011-04-01

A method for the simultaneous detection of five polyphenols (caffeic, chlorogenic, ferulic and gallic acids and (+)-catechin) by CZE with electrochemical detection was developed. Separation of these polyphenols was performed in a 100 mM borate buffer (pH 9.2) within 15 min. Under optimized separation conditions, the performance of glassy carbon (GC) electrodes modified with multiwalled carbon nanotube layer obtained from different dispersions was examined. GC electrode modified with a dispersion of multi-walled carbon nanotubes (CNT) in polyethylenimine has proven to be the most suitable CNT-based electrode for its application as amperometric detector for the CZE separation of the studied compounds. The excellent electrochemical properties of this electrode allowed the detection of the selected polyphenols at +200 mV and improved the efficiency and the resolution of their CZE separation. Limits of detection below 3.1 μM were obtained with linear ranges covering the 10⁻⁵ to 10⁻⁴  M range. The proposed method has been successfully applied for the detection (ferulic, caffeic and gallic acids and (+)-catechin) and the quantification (gallic acid and (+)-catechin) of polyphenols in two different white wines without any preconcentration step. A remarkable signal stability was observed on the electrode performance despite the presence of potential fouling substances in wine. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Estimation of kinetic parameters of anthocyanins and color degradation in vitamin C fortified cranberry juice during storage.

PubMed

Roidoung, Sunisa; Dolan, Kirk D; Siddiq, Muhammad

2017-04-01

Color degradation in cranberry juice during storage is the most common consumer complaint. To enhance nutritional quality, juice is typically fortified with vitamin C. This study determined effect of gallic acid, a natural antioxidant, for the preservation of anthocyanins (ACYs) and color, and estimated kinetics of ACYs and color degradation. Juice, fortified with 40-80mg/100mL vitamin C and 0-320mg/100mL gallic acid, was pasteurized at 85°C for 1min and stored at 23°C for 16days. Total monomeric anthocyanins and red color intensity were evaluated spectrophotometrically and data were used to determine degradation rate constants (k values) and order of reaction (n) of ACYs and color. Due to high correlation, k and n could not be estimated simultaneously. To overcome this difficulty, both n and k were held at different constant values in separate analyses to allow accurate estimation of each. Parameters n and k were modeled empirically as functions of vitamin C, and of vitamin C and gallic acid, respectively. Reaction order n ranged from 1.2 to 4.4, and decreased with increasing vitamin C concentration. The final model offers an effective tool that could be used for predicting ACYs and color retention in cranberry juice during storage. Copyright © 2017. Published by Elsevier Ltd.

A 1H NMR Investigation of the Interaction between Phenolic Acids Found in Mango (Manguifera indica cv Ataulfo) and Papaya (Carica papaya cv Maradol) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) Free Radicals

PubMed Central

López-Martínez, Luis M.; Santacruz-Ortega, Hisila; Navarro, Rosa-Elena; Sotelo-Mundo, Rogerio R.; González-Aguilar, Gustavo A.

2015-01-01

The benefits of phenolic acids on human health are very often ascribed to their potential to counteract free radicals to provide antioxidant protection. This potential has been attributed to their acidic chemical structure, which possesses hydroxyl groups in different positions. Phenolic acids can interact between themselves and exhibit an additive, antagonistic or synergistic effect. In this paper, we used 1H NMR to analyze the interactions and mechanisms that are present in major phenolic acids found in mango (gallic, protocatechuic, chlorogenic and vanillic acids) and papaya (caffeic, ferulic and p-coumaric acids), and the DPPH radical was used to evaluate the effect of the antioxidant mixtures. The interactions were found to occur via hydrogen bonds between the -OH and -COOH groups. Moreover, the phenolic acids exhibit two types of mechanisms for the neutralization of the DPPH radical. According to the results, these two mechanisms are Hydrogen Atom Transfer (HAT) and Single Electron Transfer (SET). The ability of the phenolic acid to neutralize the DPPH radical decreases in the following order in mango: gallic > chlorogenic > protocatechuic > vanillic. Moreover, within the acids found in papaya, the order was as follows: caffeic > p-coumaric > ferulic. PMID:26559189

A ¹H NMR Investigation of the Interaction between Phenolic Acids Found in Mango (Manguifera indica cv Ataulfo) and Papaya (Carica papaya cv Maradol) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) Free Radicals.

PubMed

López-Martínez, Luis M; Santacruz-Ortega, Hisila; Navarro, Rosa-Elena; Sotelo-Mundo, Rogerio R; González-Aguilar, Gustavo A

2015-01-01

The benefits of phenolic acids on human health are very often ascribed to their potential to counteract free radicals to provide antioxidant protection. This potential has been attributed to their acidic chemical structure, which possesses hydroxyl groups in different positions. Phenolic acids can interact between themselves and exhibit an additive, antagonistic or synergistic effect. In this paper, we used 1H NMR to analyze the interactions and mechanisms that are present in major phenolic acids found in mango (gallic, protocatechuic, chlorogenic and vanillic acids) and papaya (caffeic, ferulic and p-coumaric acids), and the DPPH radical was used to evaluate the effect of the antioxidant mixtures. The interactions were found to occur via hydrogen bonds between the -OH and -COOH groups. Moreover, the phenolic acids exhibit two types of mechanisms for the neutralization of the DPPH radical. According to the results, these two mechanisms are Hydrogen Atom Transfer (HAT) and Single Electron Transfer (SET). The ability of the phenolic acid to neutralize the DPPH radical decreases in the following order in mango: gallic > chlorogenic > protocatechuic > vanillic. Moreover, within the acids found in papaya, the order was as follows: caffeic > p-coumaric > ferulic.

Ellagic acid protects against neuron damage in ischemic stroke through regulating the ratio of Bcl-2/Bax expression.

PubMed

Liu, Qing-Shan; Deng, Ran; Li, Shuran; Li, Xu; Li, Keqin; Kebaituli, Gulibanumu; Li, Xueli; Liu, Rui

2017-08-01

An oxygen-glucose deprivation and reoxygenation model in primary cultured rat cortical neurons was developed for this study to investigate the effects of ellagic acid (EA), a low-molecular-weight polyphenol, on neuron cells and their function, and to evaluate whether EA can be safely utilized by humans as a functional food or therapeutic agent. Administration of EA significantly decreased the volume of cerebrum infarction and the neurological deficit scores of the rats; EA treatment also increased the number of Bcl-2-positive cells and the ratio of Bcl-2-positive to Bax-positive neurons in the semidarkness zone near the brain ischemic focus in the photothrombotic cerebral ischemia model. Treatment of EA resulted in increased neuron viability, cell nuclear integrity, and the ratio of Bcl-2/Bax expression in the primary cultured neuron model; EA treatment also lead to a decrease in the number of apoptotic cells. Our results therefore suggest a specific mechanism for the beneficial effects of EA, providing new insights into how it provides neuroprotection. To the best of our knowledge, these results represent new insights on the mechanisms of the brain cell protective activity of EA. Thus, EA may be used in functional foods or medicines to help treat nerve dysfunction, neurodegenerative disease, and aging.

Radiosensitizing effect of ellagic acid on growth of Hepatocellular carcinoma cells: an in vitro study.

PubMed

Das, Ujjal; Biswas, Sushobhan; Chattopadhyay, Sreya; Chakraborty, Anindita; Dey Sharma, Rakhi; Banerji, Asoke; Dey, Sanjit

2017-10-25

Failure of treatment for cancer in clinic by radio/chemotherapy is generally attributed to tumour resistance. Therefore, it is important to develop strategies to increase the cytotoxicity of tumour cells by radiation in combination with unique tumour selective cytotoxic agents. We evaluated the potential of ellagic acid (EA) as an enhancer of oxidative stress in cancer cells. HepG2 cells were treated with EA (10 µM) for 12 h prior to exposure of single 7.5 Gy dose of irradiation. Treatment of HepG2 cells with EA and gamma radiation showed increased reactive oxygen species generation, up regulation of p53 protein expression, decreased survival markers level like p-Akt, p-NF-kB and p-STAT3 which were significantly higher after radiation treatment alone. We also found that combination treatment increased G2/M phase cell population, decreased IL-6, COX-2 and TNF-α expression and caused a loss in mitochondrial membrane potential with decreased level of angiogenesis marker MMP-9. Over expression of Bax and activation of caspase 3 indicated the apoptosis of the cells. The results provided a strong unique strategy to kill cancer cells HepG2, using less radiation dose along with effective pro-oxidant dose of EA.

Hepatoprotective influence of quercetin and ellagic acid on thioacetamide-induced hepatotoxicity in rats.

PubMed

Afifi, Nehal A; Ibrahim, Marwa A; Galal, Mona K

2018-06-01

Despite all the studies performed to date, therapy choices for liver injuries are very few. Therefore, the search for a new treatment that could safely and effectively block or reverse liver injuries remains a challenge. Quercetin (QR) and ellagic acid (EA) had potent antioxidant and anti-inflammatory activities. The current study aimed at evaluating the potential hepatoprotective influence of QR and EA against thioacetamide (TAA)-induced liver toxicity in rats and the underlying mechanism using silymarin as a reference drug. Fifty mature male rats were orally treated daily with EA and QR in separate groups for 45 consecutive days, and then were injected with TAA twice with 24 h intervals in the last 2 days of the experiment. Administration of TAA resulted in marked elevation of liver indices, alteration in oxidative stress parameters, and significant elevation in expression level of fibrosis-related genes (MMP9 and MMP2). Administration of QR and EA significantly attenuated the hepatic toxicity through reduction of liver biomarkers, improving the redox status of the tissue, as well as hampering the expression level of fibrosis-related genes. In this study, QR and EA were proved to attenuate the hepatotoxicity through their antioxidant, metal-chelating capacity, and anti-inflammatory effects.

Phytochemical composition, antioxidant and anti-bacterial activity of Syzygium calophyllifolium Walp. fruit.

PubMed

Sathyanarayanan, Saikumar; Chandran, Rahul; Thankarajan, Sajeesh; Abrahamse, Heidi; Thangaraj, Parimelazhagan

2018-01-01

Syzygium calophyllifolium fruits are among the important wild edibles used by the tribes of Western Ghats. However, this underutilized fruit remained unnoticed for its medicinal properties. Hence, the present study was undertaken to evaluate the antioxidant activity by DPPH · , ABTS ·+ , FRAP assays and antibacterial efficacy by well diffusion method. GC-MS and HPLC profiles of crude extract and column chromatographic fractions were also determined. The methanolic extract of fruit (MFE) showed high total phenolics, tannins and flavonoids. The faction H (FH) displayed significant antioxidant property in DPPH · (IC 50 2.1 µg/ml), ABTS ·+ (19483.29 μM Trolox equivalents/g extract) and FRAP (65.5 mM Fe(II)/mg extract) assays over MFE. Moreover, FH also exhibited good antibacterial activity against Escherichia coli (32.0 mm), Salmonella typhi (27.0 mm), Staphylococcus aureus (27.3 mm) at 100 mg/ml concentration. GC-MS revealed 12 major compounds in MFE, HPLC analysis of MFE and FH depicted the presence of rutin and ellagic acid. This study suggested that FH could have high concentration of bioactive compounds like rutin and ellagic acid or its analogues compared to MFE which may be responsible for its strong antioxidant and antibacterial activity.

Biomimetic growth of gallic acid-ZnO hybrid assemblies and their applications

NASA Astrophysics Data System (ADS)

Sarker, Nazmul H.; Barnaby, Stacey N.; Fath, Karl R.; Frayne, Stephen H.; Nakatsuka, Nako; Banerjee, Ipsita A.

2012-03-01

In this study, we probed the biomimetic formation of gallic acid (GA)-ZnO nanoparticle hybrids. It was found that the morphologies formed were dependent upon pH values, resulting in GA-ZnO hybrids of varying shapes such as micro or nanoplates or fibers. The formed supramolecular GA-ZnO hybrids were found to be luminescent as indicated by confocal microscopy and were utilized for the photocatalytic degradation of the organic dye methylene blue. We also explored the bactericidal effects of the hybrids on Staphylococcus aureus ( S. aureus) as well as Escherichia Coli ( E. Coli). Thus, we have developed a new class of shape-controlled nanohybrid assemblies via mild, green synthetic methods that may be utilized for photocatalytic degradation for environmental remediation as well as for antibacterial applications.

Pomegranate extract exhibits in vitro activity against Clostridium difficile.

PubMed

Finegold, Sydney M; Summanen, Paula H; Corbett, Karen; Downes, Julia; Henning, Susanne M; Li, Zhaoping

2014-10-01

To determine the possible utility of pomegranate extract in the management or prevention of Clostridium difficile infections or colonization. The activity of pomegranate was tested against 29 clinical C. difficile isolates using the Clinical and Laboratory Standards Institute-approved agar dilution technique. Total phenolics content of the pomegranate extract was determined by Folin-Ciocalteau colorimetric method and final concentrations of 6.25 to 400 μg/mL gallic acid equivalent were achieved in the agar. All strains had MICs at 12.5 to 25 mg/mL gallic acid equivalent range. Our results suggest antimicrobial in vitro activity for pomegranate extract against toxigenic C. difficile. Pomegranate extract may be a useful contributor to the management and prevention of C. difficile disease or colonization. Copyright © 2014 Elsevier Inc. All rights reserved.

Cerumen of Australian stingless bees ( Tetragonula carbonaria): gas chromatography-mass spectrometry fingerprints and potential anti-inflammatory properties

NASA Astrophysics Data System (ADS)

Massaro, Flavia Carmelina; Brooks, Peter Richard; Wallace, Helen Margaret; Russell, Fraser Donald

2011-04-01

Cerumen, or propolis, is a mixture of plant resins enriched with bee secretions. In Australia, stingless bees are important pollinators that use cerumen for nest construction and possibly for colony's health. While extensive research attests to the therapeutic properties of honeybee ( Apis mellifera) propolis, the biological and medicinal properties of Australian stingless bee cerumen are largely unknown. In this study, the chemical and biological properties of polar extracts of cerumen from Tetragonula carbonaria in South East Queensland, Australia were investigated using gas chromatography-mass spectrometry (GC-MS) analyses and in vitro 5-lipoxygenase (5-LOX) cell-free assays. Extracts were tested against comparative (commercial tincture of A. mellifera propolis) and positive controls (Trolox and gallic acid). Distinct GC-MS fingerprints of a mixed diterpenic profile typical of native bee cerumen were obtained with pimaric acid (6.31 ± 0.97%, w/w), isopimaric acid (12.23 ± 3.03%, w/w), and gallic acid (5.79 ± 0.81%, w/w) tentatively identified as useful chemical markers. Characteristic flavonoids and prenylated phenolics found in honeybee propolis were absent. Cerumen extracts from T. carbonaria inhibited activity of 5-LOX, an enzyme known to catalyse production of proinflammatory mediators (IC50 19.97 ± 2.67 μg/ml, mean ± SEM, n = 4). Extracts had similar potency to Trolox (IC50 12.78 ± 1.82 μg/ml), but were less potent than honeybee propolis (IC50 5.90 ± 0.62 μg/ml) or gallic acid (IC50 5.62 ± 0.35 μg/ml, P < 0.001). These findings warrant further investigation of the ecological and medicinal properties of this stingless bee cerumen, which may herald a commercial potential for the Australian beekeeping industry.

Crystal structure of tannase from Lactobacillus plantarum.

PubMed

Ren, Bin; Wu, Mingbo; Wang, Qin; Peng, Xiaohong; Wen, Hua; McKinstry, William J; Chen, Qianming

2013-08-09

Tannins are water-soluble polyphenolic compounds in plants. Hydrolyzable tannins are derivatives of gallic acid (3,4,5-trihydroxybenzoic acid) or its meta-depsidic forms that are esterified to polyol, catechin, or triterpenoid units. Tannases are a family of esterases that catalyze the hydrolysis of the galloyl ester bond in hydrolyzable tannins to release gallic acid. The enzymes have found wide applications in food, feed, beverage, pharmaceutical, and chemical industries since their discovery more than a century ago, although little is known about them at the molecular level, including the details of the catalytic and substrate binding sites. Here, we report the first three-dimensional structure of a tannase from Lactobacillus plantarum. The enzyme displays an α/β structure, featured by a large cap domain inserted into the classical serine hydrolase fold. A catalytic triad was identified in the structure, which is composed of Ser163, His451, and Asp419. During the binding of gallic acid, the carboxyl group of the molecule forges hydrogen-bonding interactions with the catalytic triad of the enzyme while the three hydroxyl groups make contacts with Asp421, Lys343, and Glu357 to form another hydrogen-bonding network. Mutagenesis studies demonstrated that these residues are indispensable for the activity of the enzyme. Structural studies of the enzyme in complex with a number of substrates indicated that the interactions at the galloyl binding site are the determinant force for the binding of substrates. The single galloyl binding site is responsible for the esterase and depsidase activities of the enzyme. Copyright © 2013 Elsevier Ltd. All rights reserved.

Dosimetry Evolution in Teletherapy: Polimer Gel

NASA Astrophysics Data System (ADS)

Hamann, J. H.; Peixoto, J. G. P.

2018-03-01

Polymer gels evolution and chemical composition used in dosimetry. Type Composition First gels Folin’s Phenol or Gallic Acid Polymer Gel Agarose and N,N’-methylene-bis-acrylamide BANANA Bis, acrylamide, nitrous oxide and agarose BANG-1TM Bis, acrylamide, nitrogen and gelatin BANG-2TM Bis, acrylic acid, sodium hydroxide, nitrogen and gelatin BANG-3TM Bis, methacrylate acid, sodium hydroxide, nitrogen and gelatin MAGIC Methacrylate acid, ascorbic acid, gelatin and copper sulphate

Cocrystals of a 1,2,4-thiadiazole-based potent neuroprotector with gallic acid: solubility, thermodynamic stability relationships and formation pathways.

PubMed

Surov, Artem O; Churakov, Andrei V; Proshin, Alexey N; Dai, Xia-Lin; Lu, Tongbu; Perlovich, German L

2018-05-30

Three distinct solid forms, namely anhydrous cocrystals with 2 : 1 and 1 : 1 drug/acid ratios ([TDZ : GA] (2 : 1), [TDZ : GA] (1 : 1)), and a hydrated one having 1 : 1 : 1 drug/acid/water stoichiometry ([TDZ : GA : H2O] (1 : 1 : 1)), have been formed by cocrystallization of the biologically active 1,2,4-thiadiazole derivative (TDZ) with gallic acid (GA). The thermodynamic stability relationships between the cocrystals were rationalized in terms of Gibbs energies of the formation reactions and further verified by performing a set of competitive and exchange mechanochemical reactions. Interestingly, competitive grinding in the presence of the structurally related vanillic acid led to the formation of a new polymorphic form of the [TDZ : Vanillic acid] (1 : 1) cocrystal, which was promoted by gallic acid. The mechanochemical method was also applied to elucidate the alternative pathways of the [TDZ : GA : H2O] (1 : 1 : 1) cocrystal formation. Direct cocrystallization of TDZ with GA monohydrate was found to proceed much faster than the reaction of TDZ and anhydrous GA in the presence of an acetonitrile/water mixture, which may indicate the presence of a transitional stage. According to dissolution studies, the [TDZ : GA : H2O] (1 : 1 : 1) cocrystal was ca. 6.6 times more soluble than the parent 1,2,4-thiadiazole at pH 2.0 and 25.0 °C. The apparent two-step dehydration behavior of the [TDZ : GA : H2O] (1 : 1 : 1) cocrystal monohydrate was clarified by analyzing the intermolecular interactions of water molecules with the crystalline environment derived from solid state DFT calculations.

Comparative study on anti-oxidant and anti-inflammatory activities of Caesalpinia crista and Centella asiatica leaf extracts

PubMed Central

Ramesh, B. N.; Girish, T. K.; Raghavendra, R. H.; Naidu, K. Akhilender; Rao, U. J. S. Prasada; Rao, K. S.

2014-01-01

Background: Amyloidosis, oxidative stress and inflammation have been strongly implicated in neurodegenerative disorders like Alzheimer's disease. Traditionally, Caesalpinia crista and Centella asiatica leaf extracts are used to treat brain related diseases in India. C. crista is used as a mental relaxant drink as well as to treat inflammatory diseases, whereas C. asiatica is reported to be used to enhance memory and to treat dementia. Objective: The present study is aimed to understand the anti-oxidant and anti-inflammatory potential of C. asiatica and C. crista leaf extracts. Materials and Methods: Phenolic acid composition of the aqueous extracts of C. crista and C. asiatica were separated on a reverse phase C18 column (4.6 x 250 mm) using HPLC system. Antioxidant properties of the leaf extracts were determined by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay and the reducing potential assay. The anti-inflammatory activities of aqueous extracts of C. crista and C. asiatica were studied using 5-lipoxygenase assay. Polymorphonuclear leukocytes (PMNLs) were isolated from blood by Ficoll-Histopaque density gradient followed by hypotonic lysis of erythrocytes. Results: Gallic, protocatechuic, gentisic, chlorogenic, caffeic, p-coumaric and ferulic acids were the phenolic acids identified in C. crista and C. asiatica leaf aqueous extracts. However, gallic acid and ferulic acid contents were much higher in C. crista compared to C. asiatica. Leaf extracts of C. asiatica and C. crista exhibited antioxidant properties and inhibited 5-lipoxygenase (anti-inflammatory) in a dose dependent manner. However, leaf extracts of C. crista had better antioxidant and anti-inflammatory activity compared to that of C. asiatica. The better activity of C. crista is attributed to high gallic acid and ferulic acid compared to C. asiatica. Conclusions: Thus, the leaf extract of C. crista can be a potential therapeutic role for Alzheimer's disease. PMID:24741275

Effect of Various Food Additives on the Levels of 4(5)-Methylimidazole in a Soy Sauce Model System.

PubMed

Lee, Sumin; Lee, Jung-Bin; Hwang, Junho; Lee, Kwang-Geun

2016-01-01

In this study, the effect of food additives such as iron sulfate, magnesium sulfate, zinc sulfate, citric acid, gallic acid, and ascorbic acid on the reduction of 4(5)-methylimidazole (4(5)-MI) was investigated using a soy sauce model system. The concentration of 4(5)-MI in the soy sauce model system with 5% (v/v) caramel colorant III was 1404.13 μg/L. The reduction rate of 4(5)-MI level with the addition of 0.1M additives followed in order: iron sulfate (81%) > zinc sulfate (61%) > citric acid (40%) > gallic acid (38%) > ascorbic acid (24%) > magnesium sulfate (13%). Correlations between 4(5)-MI levels and the physicochemical properties of soy sauce, including the amount of caramel colorant, pH value, and color differences, were determined. The highest correlations were found between 4(5)-MI levels and the amount of caramel colorant and pH values (r(2) = 0.9712, r(2) = 0.9378). The concentration of caramel colorants in 8 commercial soy sauces were estimated, and ranged from 0.01 to 1.34% (v/v). © 2015 Institute of Food Technologists®

Utilization of aromatic compounds by the Penicillium strain Bi 7/2.

PubMed

Hofrichter, M; Scheibner, K

1993-01-01

The Penicillium strain Bi 7/2 utilized phenol, catechol, resorcinol, hydroquinone, pyrogallol, hydroxyhydroquinone, phloroglucinol, m- and p-cresol, orcinol, 4-methylcatechol, 4-methoxyphenol, 4-aminophenol, benzyl alcohol, benzoic acid, 2-, 3- and 4-hydroxybenzoic acid, anthranilic acid, protocatechuic acid and gallic acid as sole sources of carbon and energy. The central metabolites catechol, protocatechuic acid and hydroxyquinone could be determined by HPLC with diode-array detection. Pathways for the degradation of aromatic substances were proposed.

Chemometrics-enhanced high performance liquid chromatography-diode array detection strategy for simultaneous determination of eight co-eluted compounds in ten kinds of Chinese teas using second-order calibration method based on alternating trilinear decomposition algorithm.

PubMed

Yin, Xiao-Li; Wu, Hai-Long; Gu, Hui-Wen; Zhang, Xiao-Hua; Sun, Yan-Mei; Hu, Yong; Liu, Lu; Rong, Qi-Ming; Yu, Ru-Qin

2014-10-17

In this work, an attractive chemometrics-enhanced high performance liquid chromatography-diode array detection (HPLC-DAD) strategy was proposed for simultaneous and fast determination of eight co-eluted compounds including gallic acid, caffeine and six catechins in ten kinds of Chinese teas by using second-order calibration method based on alternating trilinear decomposition (ATLD) algorithm. This new strategy proved to be a useful tool for handling the co-eluted peaks, uncalibrated interferences and baseline drifts existing in the process of chromatographic separation, which benefited from the "second-order advantages", making the determination of gallic acid, caffeine and six catechins in tea infusions within 8 min under a simple mobile phase condition. The average recoveries of the analytes on two selected tea samples ranged from 91.7 to 103.1% with standard deviations (SD) ranged from 1.9 to 11.9%. Figures of merit including sensitivity (SEN), selectivity (SEL), root-mean-square error of prediction (RMSEP) and limit of detection (LOD) have been calculated to validate the accuracy of the proposed method. To further confirm the reliability of the method, a multiple reaction monitoring (MRM) method based on LC-MS/MS was employed for comparison and the obtained results of both methods were consistent with each other. Furthermore, as a universal strategy, this new proposed analytical method was applied for the determination of gallic acid, caffeine and catechins in several other kinds of Chinese teas, including different levels and varieties. Finally, based on the quantitative results, principal component analysis (PCA) was used to conduct a cluster analysis for these Chinese teas. The green tea, Oolong tea and Pu-erh raw tea samples were classified successfully. All results demonstrated that the proposed method is accurate, sensitive, fast, universal and ideal for the rapid, routine analysis and discrimination of gallic acid, caffeine and catechins in Chinese tea samples. Copyright © 2014 Elsevier B.V. All rights reserved.

Gallic acid grafting effect on delivery performance and antiglaucoma efficacy of antioxidant-functionalized intracameral pilocarpine carriers.

PubMed

Chou, Shih-Feng; Luo, Li-Jyuan; Lai, Jui-Yang

2016-07-01

Functionalization of therapeutic carrier biomaterials can potentially provide additional benefits in drug delivery for disease treatment. Given that this modification determines final therapeutic efficacy of drug carriers, here, we investigate systematically the role of grafting amount of antioxidant gallic acid (GA) onto GN in situ gelling copolymers made of biodegradable gelatin and thermo-responsive poly(N-isopropylacrylamide) for intracameral delivery of pilocarpine in antiglaucoma treatment. As expected, increasing redox reaction time increased total antioxidant activities and free radical scavenging abilities of synthesized carrier biomaterials. The hydrophilic nature of antioxidant molecules strongly affected physicochemical properties of carrier materials with varying GA grafting amounts, thereby dictating in vitro release behaviors and mechanisms of pilocarpine. In vitro oxidative stress challenges revealed that biocompatible carriers with high GA content alleviated lens epithelial cell damage and reduced reactive oxygen species. Intraocular pressure and pupil diameter in glaucomatous rabbits showed correlations with GA-mediated release of pilocarpine. Additionally, enhanced pharmacological treatment effects prevented corneal endothelial cell loss during disease progression. Increasing GA content increased total antioxidant level and decreased nitrite level in the aqueous humor, suggesting a much improved antioxidant status in glaucomatous eyes. This work significantly highlights the dependence of physicochemical properties, drug release behaviors, and bioactivities on intrinsic antioxidant capacities of therapeutic carrier biomaterials for glaucoma treatment. Development of injectable biodegradable polymer depots and functionalization of carrier biomaterials with antioxidant can potentially provide benefits such as improved bioavailability, controlled release pattern, and increased therapeutic effect in intracameral pilocarpine administration for glaucoma treatment. For the first time, this study demonstrated that the biodegradable in situ gelling copolymers can incorporate different levels of antioxidant gallic acid to tailor the structure-property-function relationship of the intracameral drug delivery system. The systematic evaluation fully verified the dependence of phase transition, degradation behavior, drug release mechanism, and antiglaucoma efficacy on intrinsic antioxidant capacities of carrier biomaterials. The report highlights the significant role of grafting amount of gallic acid in optimizing performance of antioxidant-functionalized polymer therapeutics as new drug delivery platforms in disease treatment. Copyright © 2016 Acta Materialia Inc. Published by Elsevier Ltd. All rights reserved.

Determination of Phenolic Acids in Sugarcane Vinasse by HPLC with Pulse Amperometry

PubMed Central

Freitas, P. V.; Beluomini, M. A.; da Silva, J. L.; Stradiotto, N. R.

2018-01-01

A reversed-phase liquid chromatographic separation with pulsed amperometric detection of phenolic acids at a glassy carbon electrode is described. Chromatographic separation was carried out in isocratic conditions using 0.20 mol·L−1 acetic acid (pH 5.0)/water (80 : 20, v/v) as mobile phase under constant working potential mode of 0.80 V. Chromatographic peaks presented high resolution and separation. Calibration curves exhibited excellent correlation coefficients, above 0.995. Linear ranges of the analytes, in mg L−1, were of 0.018–18 (gallic acid), 0.146–19 (vanillic acid), 0.13–17 (caffeic acid), 0.016–16 (ferulic acid), and 0.008–17 (p-coumaric acid), respectively. Limits of detection ranged from 1.6 to 97 μg·L−1 and precision varied in 1.73–3.78% interval. Concentrations of 19 ± 0.51 mg·L−1 and 7.8 ± 2.5 mg·L−1 were found for vanillic and caffeic acids, respectively, in a sugarcane vinasse sample. Gallic, ferulic, and p-coumaric acids were not detected. Recovery results demonstrated that the proposed method is accurate, and it can be used to detect and quantify phenolic acids in sugarcane vinasse without any influence of interferents. PMID:29600112

Exploratory Characterization of Phenolic Compounds with Demonstrated Anti-Diabetic Activity in Guava Leaves at Different Oxidation States

PubMed Central

Díaz-de-Cerio, Elixabet; Verardo, Vito; Gómez-Caravaca, Ana María; Fernández-Gutiérrez, Alberto; Segura-Carretero, Antonio

2016-01-01

Psidium guajava L. is widely used like food and in folk medicine all around the world. Many studies have demonstrated that guava leaves have anti-hyperglycemic and anti-hyperlipidemic activities, among others, and that these activities belong mainly to phenolic compounds, although it is known that phenolic composition in guava tree varies throughout seasonal changes. Andalusia is one of the regions in Europe where guava is grown, thus, the aim of this work was to study the phenolic compounds present in Andalusian guava leaves at different oxidation states (low, medium, and high). The phenolic compounds in guava leaves were determined by HPLC-DAD-ESI-QTOF-MS. The results obtained by chromatographic analysis reported that guava leaves with low degree of oxidation had a higher content of flavonols, gallic, and ellagic derivatives compared to the other two guava leaf samples. Contrary, high oxidation state guava leaves reported the highest content of cyanidin-glucoside that was 2.6 and 15 times higher than guava leaves with medium and low oxidation state, respectively. The QTOF platform permitted the determination of several phenolic compounds with anti-diabetic properties and provided new information about guava leaf phenolic composition that could be useful for nutraceutical production. PMID:27187352

Exploratory Characterization of Phenolic Compounds with Demonstrated Anti-Diabetic Activity in Guava Leaves at Different Oxidation States.

PubMed

Díaz-de-Cerio, Elixabet; Verardo, Vito; Gómez-Caravaca, Ana María; Fernández-Gutiérrez, Alberto; Segura-Carretero, Antonio

2016-05-11

Psidium guajava L. is widely used like food and in folk medicine all around the world. Many studies have demonstrated that guava leaves have anti-hyperglycemic and anti-hyperlipidemic activities, among others, and that these activities belong mainly to phenolic compounds, although it is known that phenolic composition in guava tree varies throughout seasonal changes. Andalusia is one of the regions in Europe where guava is grown, thus, the aim of this work was to study the phenolic compounds present in Andalusian guava leaves at different oxidation states (low, medium, and high). The phenolic compounds in guava leaves were determined by HPLC-DAD-ESI-QTOF-MS. The results obtained by chromatographic analysis reported that guava leaves with low degree of oxidation had a higher content of flavonols, gallic, and ellagic derivatives compared to the other two guava leaf samples. Contrary, high oxidation state guava leaves reported the highest content of cyanidin-glucoside that was 2.6 and 15 times higher than guava leaves with medium and low oxidation state, respectively. The QTOF platform permitted the determination of several phenolic compounds with anti-diabetic properties and provided new information about guava leaf phenolic composition that could be useful for nutraceutical production.

Augmenting the activity of antifungal agents against aspergilli using structural analogues of benzoic acid as chemosensitizing agents

USDA-ARS?s Scientific Manuscript database

Structure-activity analysis revealed that antifungal activities of benzoic and gallic acids were increased against strains of Aspergillus flavus, A. fumigatus and A. terreus, causative agents of human aspergillosis, by addition of a methyl, methoxyl or a chloro group at position 4 of the aromatic ri...

Development and validation of a simple high performance thin layer chromatography method combined with direct 1,1-diphenyl-2-picrylhydrazyl assay to quantify free radical scavenging activity in wine.

PubMed

Agatonovic-Kustrin, Snezana; Morton, David W; Yusof, Ahmad P

2016-04-15

The aim of this study was to: (a) develop a simple, high performance thin layer chromatographic (HPTLC) method combined with direct 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay to rapidly assess and compare free radical scavenging activity or anti-oxidant activity for major classes of polyphenolics present in wines; and (b) to investigate relationship between free radical scavenging activity to the total polyphenolic content (TPC) and total antioxidant capacity (TAC) in the wine samples. The most potent free radical scavengers that we tested for in the wine samples were found to be resveratrol (polyphenolic non-flavonoid) and rutin (flavonoid), while polyphenolic acids (caffeic acid and gallic acid) although present in all wine samples were found to be less potent free radical scavengers. Therefore, the total antioxidant capacity was mostly affected by the presence of resveratrol and rutin, while total polyphenolic content was mostly influenced by the presence of the less potent free radical scavengers gallic and caffeic acids. Copyright © 2015 Elsevier Ltd. All rights reserved.

Metabolic variation and antioxidant potential of Malus prunifolia (wild apple) compared with high flavon-3-ol containing fruits (apple, grapes) and beverage (black tea).

PubMed

Maria John, K M; Enkhtaivan, Gansukh; Kim, Ju Jin; Kim, Doo Hwan

2014-11-15

Secondary metabolic variation of wild apple (Malus prunifolia) was compared with fruits that contained high flavan-3-ol like grapes (GR), apple (App) and the beverage, black tea (BT). The polyphenol contents in wild apple was higher than in GR and App but less than BT. The identified phenolic acids (gallic, protocatechuic, chlorogenic, p-coumaric and ferulic acids) and flavonoids (quercetin and myricetin) indicate that wild apple was higher than that of App. Among all the samples, BT had highest antioxidant potential in terms of 2,2'-Azinobis (3-thylbenzothiazoline-6-sulfonic acid) diammonium salt (95.36%), metal chelating (45.36%) and phosphomolybdenum activity (95.8 mg/g) because of the high flavan-3-ol content. The gallic acid and epigallocatechin gallate were highly correlated with antioxidant potential and these metabolites levels are higher in wild apple than that of App. Wild apples being a non-commercial natural source, a detailed study of this plant will be helpful for the food additive and preservative industry. Copyright © 2014 Elsevier Ltd. All rights reserved.

A computational investigation on the structure, global parameters and antioxidant capacity of a polyphenol, Gallic acid.

PubMed

Rajan, Vijisha K; Muraleedharan, K

2017-04-01

A computational DFT-B3LYP structural analysis of a poly phenol, Gallic acid (GA) has been performed by using 6-311++ G (df, p) basis set. The GA is a relatively stable molecule with considerable radical scavenging capacity. It is a well known antioxidant. The NBO analysis shows that the aromatic system is delocalized. The results reveal that the most stable radical is formed at O 3 -atom upon scavenging the free radicals. Global descriptive parameters show that GA acts as an acceptor center in charge transfer complex formation which is supported by ESP and contour diagrams and also by Q max value. The GA is a good antioxidant and it can be better understood by HAT and TMC mechanisms as it has low BDE, ΔH acidity and ΔG acidity values. The ΔBDE and ΔAIP values also confirm that the antioxidant capacity of GA can be explained through HAT rather than the SET-PT mechanism. Copyright © 2016 Elsevier Ltd. All rights reserved.

The antioxidant and radical scavenging activities of black pepper (Piper nigrum) seeds.

PubMed

Gülçin, Ilhami

2005-11-01

Water and ethanol crude extracts from black pepper (Piper nigrum) were investigated for their antioxidant and radical scavenging activities in six different assay, namely, total antioxidant activity, reducing power, 1,1-Diphenyl-2-picryl-hydrazyl (DPPH) free radical scavenging, superoxide anion radical scavenging, hydrogen peroxide scavenging, and metal chelating activities. Both water extract (WEBP) and ethanol extract (EEBP) of black pepper exhibited strong total antioxidant activity. The 75 microg/ml concentration of WEBP and EEBP showed 95.5% and 93.3% inhibition on peroxidation of linoleic acid emulsion, respectively. On the other hand, at the same concentration, standard antioxidants such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and alpha-tocopherol exhibited 92.1%, 95.0%, and 70.4% inhibition on peroxidation of linoleic acid emulsion, respectively. Also, total phenolic content in both WEBP and EEBP were determined as gallic acid equivalents. The total phenolics content of water and ethanol extracts were determined by the Folin-Ciocalteu procedure and 54.3 and 42.8 microg gallic acid equivalent of phenols was detected in 1 mg WEBP and EEBP.

Effect of tannic and gallic acids alone or in combination with carbenicillin or tetracycline on Chromobacterium violaceum CV026 growth, motility, and biofilm formation.

PubMed

Dusane, Devendra H; O'May, Che; Tufenkji, Nathalie

2015-07-01

Chromobacterium violaceum is an opportunistic pathogen that causes infections that are difficult to treat. The goal of this research was to evaluate the effect of selected tannins (tannic acid (TA) and gallic acid (GA)) on bacterial growth, motility, antibiotic (carbenicillin, tetracycline) susceptibility, and biofilm formation. Both tannins, particularly TA, impaired bacterial growth levels and swimming motilities at sub-minimum inhibitory concentrations (sub-MICs). In combination with tannins, antibiotics showed increased MICs, suggesting that tannins interfered with antibacterial activity. Sub-MICs of tetracycline or TA alone enhanced biofilm formation of C. violaceum; however, in combination, these compounds inhibited biofilm formation. In contrast, carbenicillin at sub-MICs was effective in inhibiting C. violaceum biofilm formation; however, in combination with lower concentrations of TA or GA, biofilms were enhanced. These results provide insights into the effects of tannins on C. violaceum growth and their varying interaction with antibiotics used to target C. violaceum infections.

Docking analysis of gallic acid derivatives as HIV-1 protease inhibitors.

PubMed

Singh, Anjali; Pal, Tapan Kumar

2015-01-01

HIV-1 Protease (HIV-1 PR) enzymes are essential for accurate assembly and maturation of infectious HIV retroviruses. The significant role of HIV-1 protease in viral replication has made it a potential drug target. In the recent past, phytochemical Gallic Acid (GA) derivatives have been screened for protease inhibitor activity. The present work aims to design and evaluate potential GA-based HIV-1 PR phytoinhibitors by docking approach. The ligands were prepared by ChemDraw and docking was performed in HEX software. In this present study, one of the GA analogues (GA4) emerged as a potent drug candidate for HIV-1 PR inhibition, and docking results showed it to be comparable with anti-HIV drugs, darunavir and amprenavir. The GA4 derivative provided a lead for designing more effective HIV-1 PR inhibitors.

Green technology approach towards herbal extraction method

NASA Astrophysics Data System (ADS)

Mutalib, Tengku Nur Atiqah Tengku Ab; Hamzah, Zainab; Hashim, Othman; Mat, Hishamudin Che

2015-05-01

The aim of present study was to compare maceration method of selected herbs using green and non-green solvents. Water and d-limonene are a type of green solvents while non-green solvents are chloroform and ethanol. The selected herbs were Clinacanthus nutans leaf and stem, Orthosiphon stamineus leaf and stem, Sesbania grandiflora leaf, Pluchea indica leaf, Morinda citrifolia leaf and Citrus hystrix leaf. The extracts were compared with the determination of total phenolic content. Total phenols were analyzed using a spectrophotometric technique, based on Follin-ciocalteau reagent. Gallic acid was used as standard compound and the total phenols were expressed as mg/g gallic acid equivalent (GAE). The most suitable and effective solvent is water which produced highest total phenol contents compared to other solvents. Among the selected herbs, Orthosiphon stamineus leaves contain high total phenols at 9.087mg/g.

Anti-tumour potential of a gallic acid-containing phenolic fraction from Oenothera biennis.

PubMed

Pellegrina, Chiara Dalla; Padovani, Giorgia; Mainente, Federica; Zoccatelli, Gianni; Bissoli, Gaetano; Mosconi, Silvia; Veneri, Gianluca; Peruffo, Angelo; Andrighetto, Giancarlo; Rizzi, Corrado; Chignola, Roberto

2005-08-08

A phenolic fraction purified form defatted seeds of Oenothera biennis promoted selective apoptosis of human and mouse bone marrow-derived cell lines following first-order kinetics through a caspase-dependent pathway. In non-leukemia tumour cell lines, such as human colon carcinoma CaCo(2) cells and mouse fibrosarcoma WEHI164 cells, this fraction inhibited (3)H-thymidine incorporation but not cell death or cell cycle arrest. Human peripheral blood mononuclear cells showed low sensitivity to treatment. Single bolus injection of the phenolic fraction could delay the growth of established myeloma tumours in syngeneic animals. HPLC and mass spectrometry analysis revealed that the fraction contains gallic acid. However, the biological activity of the fraction differs from the activity of this phenol and hence it should be attributed to other co-purified molecules which remain still unidentified.

Effective protection of biological membranes against photo-oxidative damage: Polymeric antioxidant forming a protecting shield over the membrane.

PubMed

Mertins, Omar; Mathews, Patrick D; Gomide, Andreza B; Baptista, Mauricio S; Itri, Rosangela

2015-10-01

We have prepared a chitosan polymer modified with gallic acid in order to develop an efficient protection strategy biological membranes against photodamage. Lipid bilayers were challenged with photoinduced damage by photosensitization with methylene blue, which usually causes formation of hydroperoxides, increasing area per lipid, and afterwards allowing leakage of internal materials. The damage was delayed by a solution of gallic acid in a concentration dependent manner, but further suppressed by the polymer at very low concentrations. The membrane of giant unilamellar vesicles was covered with this modified macromolecule leading to a powerful shield against singlet oxygen and thus effectively protecting the lipid membrane from oxidative stress. The results have proven the discovery of a promising strategy for photo protection of biological membranes. Copyright © 2015 Elsevier B.V. All rights reserved.

[Determination of total tannins in the roots, branches, leaves and pericarps of Juglans mandshurica].

PubMed

Wang, Tianmin; Sun, Xiaoli; Peng, Xue; Zhai, Yanjun; Chu, Zhengyun; Zhang, Hui; Kang, Tingguo; Chen, Hubiao

2011-01-01

The roots, barks, branches and pericarps of Juglans mandshurica were used as folk medicine in China and reputed for its treatment of several cancers, such as gastric cancer, liver cancer and leukemia. The extracts of the roots, branches, leaves and pericarps of J. mandshurica have been experimentally proved to show anti-tumor activities. Tannins, which exhibited antioxidant and anti-tumor activities, were the main constituents in J. mandshurica. In this paper, a simple spectrophotometric method was developed for the determination of total tannins in the roots, branches, leaves and pericarps of J. mandshurica collected in Dalian and Anshan of Liaoning Province. Gallic acid was used as standard compound and the content of total tannins was calculated as gallic acid equivalent. As a result of the method validation, a good linearity (r = 0.9997, n = 5) and a high recovery of gallic acid (99.02%, RSD 3.7%, n = 9) was achieved. Eight samples including four parts of J. mandshurica collected in two places were analyzed for their total tannins with the established method. In the corresponding parts of J. mandshurica, except the pericarps, the contents of total tannins showed no significant difference between samples collected in Dalian and Anshan, while the content of total tannins in different parts of J. mandshurica were significantly different. The average content of total tannins in the roots, branches, leaves and pericarps of samples collected in Dalian and Anshan was 45.66, 23.40, 58.24, 3.58 mg g(-1), respectively.

Galloyl-RGD as a new cosmetic ingredient

PubMed Central

2014-01-01

Background The cosmetics market has rapidly increased over the last years. For example, in 2011 it reached 242.8 billion US dollars, which was a 3.9% increase compared to 2010. There have been many recent trials aimed at finding the functional ingredients for new cosmetics. Gallic acid is a phytochemical derived from various herbs, and has anti-fungal, anti-viral, and antioxidant properties. Although phytochemicals are useful as cosmetic ingredients, they have a number of drawbacks, such as thermal stability, residence time in the skin, and permeability through the dermal layer. To overcome these problems, we considered conjugation of gallic acid with a peptide. Results We synthesized galloyl-RGD, which represents a conjugate of gallic acid and the peptide RGD, purified it by HPLC and characterized by MALDI-TOF with the aim of using it as a new cosmetic ingredient. Thermal stability of galloyl-RGD was tested at alternating temperatures (consecutive 4°C, 20°C, or 40°C for 8 h each) on days 2, 21, 41, and 61. Galloyl-RGD was relatively safe to HaCaT keratinocytes, as their viability after 48 h incubation with 500 ppm galloyl-RGD was 93.53%. In the group treated with 50 ppm galloyl-RGD, 85.0% of free radicals were removed, whereas 1000 ppm galloyl-RGD suppressed not only L-DOPA formation (43.8%) but also L-DOPA oxidation (54.4%). Conclusions Galloyl-RGD is a promising candidate for a cosmetic ingredient. PMID:25103826

Fungal Pretreatment of Sweet Sorghum Bagasse with Combined CuSO4-Gallic Acid Supplement for Improvement in Lignin Degradation, Selectivity, and Enzymatic Saccharification.

PubMed

Mishra, Vartika; Jana, Asim K

2017-09-01

Sweet sorghum (Sorghum sp.) has high biomass yield. Hydrolysis of lignocellulosic sweet sorghum bagasse (SSB) to fermentable sugar could be useful for manufacture of biofuel or other fermentation products. Pretreatment of lignocellulosic biomass to degrade lignin before enzymatic hydrolysis is a key step. Fungal pretreatment of SSB with combined CuSO 4 -gallic acid supplements in solid-state fermentation (SSF) to achieve higher lignin degradation, selectivity value (SV), and enzymatic hydrolysis to sugar was studied. Coriolus versicolor was selected due to high activities of ligninolytic enzymes laccase, lignin peroxidase (LiP), manganese peroxidase (MnP), polyphenol oxidase (PPO), and arylalcohol oxidase (AAO) and low activities of cellulolytic enzymes CMCase, FPase, and β-glucosidase with high lignin degradation and SV in 20 days. CuSO 4 /gallic acid increased the activities of ligninolytic enzymes resulting in enhanced lignin degradations and SVs. Cumulative/synergistic effect of combined supplements further increased the activities of laccase, LiP, MnP, PPO, and AAO by 7.6, 14.6, 2.67, 2.06, and 2.15-folds, respectively (than control), resulting in highest lignin degradation 31.1 ± 1.4% w/w (1.56-fold) and SV 2.33 (3.58-fold). Enzymatic hydrolysis of pretreated SSB yielded higher (~2.2 times) fermentable sugar. The study showed combined supplements can improve fungal pretreatment of lignocellulosic biomass. XRD, SEM, FTIR, and TGA/DTG of SSB confirmed the results.

Two UGT84 Family Glycosyltransferases Catalyze a Critical Reaction of Hydrolyzable Tannin Biosynthesis in Pomegranate (Punica granatum)

PubMed Central

Ono, Nadia N.; Qin, Xiaoqiong; Wilson, Alexander E.; Li, Gang

2016-01-01

Hydrolyzable tannins (HTs) play important roles in plant herbivore deterrence and promotion of human health. A critical step in HT production is the formation of 1-O-galloyl-β-D-glucopyranoside (β-glucogallin, ester-linked gallic acid and glucose) by a UDP-glucosyltransferase (UGT) activity. We cloned and biochemically characterized four candidate UGTs from pomegranate (Punica granatum), of which only UGT84A23 and UGT84A24 exhibited β-glucogallin forming activities in enzyme assays. Although overexpression and single RNAi knockdown pomegranate hairy root lines of UGT84A23 or UGT84A24 did not lead to obvious alterations in punicalagin (the prevalent HT in pomegranate) accumulation, double knockdown lines of the two UGTs resulted in largely reduced levels of punicalagins and bis-hexahydroxydiphenyl glucose isomers. An unexpected accumulation of galloyl glucosides (ether-linked gallic acid and glucose) was also detected in the double knockdown lines, suggesting that gallic acid was utilized by an unidentified UGT activity for glucoside formation. Transient expression in Nicotiana benthamiana leaves and immunogold labeling in roots of pomegranate seedlings collectively indicated cytosolic localization of UGT84A23 and UGT84A24. Overall, functional characterization and localization of UGT84A23 and UGT84A24 open up opportunities for further understanding the regulatory control of HT metabolism in plants and its coordination with other biochemical pathways in the metabolic network. PMID:27227328

Galloyl-RGD as a new cosmetic ingredient.

PubMed

Park, Dae-Hun; Jung, Dae Hyun; Kim, Soo Jung; Kim, Sung Han; Park, Kyung Mok

2014-08-08

The cosmetics market has rapidly increased over the last years. For example, in 2011 it reached 242.8 billion US dollars, which was a 3.9% increase compared to 2010. There have been many recent trials aimed at finding the functional ingredients for new cosmetics. Gallic acid is a phytochemical derived from various herbs, and has anti-fungal, anti-viral, and antioxidant properties. Although phytochemicals are useful as cosmetic ingredients, they have a number of drawbacks, such as thermal stability, residence time in the skin, and permeability through the dermal layer. To overcome these problems, we considered conjugation of gallic acid with a peptide. We synthesized galloyl-RGD, which represents a conjugate of gallic acid and the peptide RGD, purified it by HPLC and characterized by MALDI-TOF with the aim of using it as a new cosmetic ingredient. Thermal stability of galloyl-RGD was tested at alternating temperatures (consecutive 4°C, 20°C, or 40°C for 8 h each) on days 2, 21, 41, and 61. Galloyl-RGD was relatively safe to HaCaT keratinocytes, as their viability after 48 h incubation with 500 ppm galloyl-RGD was 93.53%. In the group treated with 50 ppm galloyl-RGD, 85.0% of free radicals were removed, whereas 1000 ppm galloyl-RGD suppressed not only L-DOPA formation (43.8%) but also L-DOPA oxidation (54.4%). Galloyl-RGD is a promising candidate for a cosmetic ingredient.

Comparison of Antioxidant Evaluation Assays for Investigating Antioxidative Activity of Gallic Acid and Its Alkyl Esters in Different Food Matrices.

PubMed

Phonsatta, Natthaporn; Deetae, Pawinee; Luangpituksa, Pairoj; Grajeda-Iglesias, Claudia; Figueroa-Espinoza, Maria Cruz; Le Comte, Jérôme; Villeneuve, Pierre; Decker, Eric A; Visessanguan, Wonnop; Panya, Atikorn

2017-08-30

The addition of antioxidants is one of the strategies to inhibit lipid oxidation, a major cause of lipid deterioration in foods leading to rancidity development and nutritional losses. However, several studies have been reported that conventional antioxidant assays, e.g., TPC, ABTS, FRAP, and ORAC could not predict antioxidant performance in several foods. This study aimed to investigate the performance of two recently developed assays, e.g., the conjugated autoxidizable triene (CAT) and the apolar radical-initiated conjugated autoxidizable triene (ApoCAT) assays to predict the antioxidant effectiveness of gallic acid and its esters in selected food models in comparison with the conventional antioxidant assays. The results indicated that the polarities of the antioxidants have a strong impact on antioxidant activities. In addition, different oxidant locations demonstrated by the CAT and ApoCAT assays influenced the overall antioxidant performances of the antioxidants with different polarities. To validate the predictability of the assays, the antioxidative performance of gallic acid and its alkyl esters was investigated in oil-in-water (O/W) emulsions, bulk soybean oils, and roasted peanuts as the lipid food models. The results showed that only the ApoCAT assay could be able to predict the antioxidative performances in O/W emulsions regardless of the antioxidant polarities. This study demonstrated that the relevance of antioxidant assays to food models was strongly dependent on physical similarities between the tested assays and the food structure matrices.

Two UGT84 Family Glycosyltransferases Catalyze a Critical Reaction of Hydrolyzable Tannin Biosynthesis in Pomegranate (Punica granatum).

PubMed

Ono, Nadia N; Qin, Xiaoqiong; Wilson, Alexander E; Li, Gang; Tian, Li

2016-01-01

Hydrolyzable tannins (HTs) play important roles in plant herbivore deterrence and promotion of human health. A critical step in HT production is the formation of 1-O-galloyl-β-D-glucopyranoside (β-glucogallin, ester-linked gallic acid and glucose) by a UDP-glucosyltransferase (UGT) activity. We cloned and biochemically characterized four candidate UGTs from pomegranate (Punica granatum), of which only UGT84A23 and UGT84A24 exhibited β-glucogallin forming activities in enzyme assays. Although overexpression and single RNAi knockdown pomegranate hairy root lines of UGT84A23 or UGT84A24 did not lead to obvious alterations in punicalagin (the prevalent HT in pomegranate) accumulation, double knockdown lines of the two UGTs resulted in largely reduced levels of punicalagins and bis-hexahydroxydiphenyl glucose isomers. An unexpected accumulation of galloyl glucosides (ether-linked gallic acid and glucose) was also detected in the double knockdown lines, suggesting that gallic acid was utilized by an unidentified UGT activity for glucoside formation. Transient expression in Nicotiana benthamiana leaves and immunogold labeling in roots of pomegranate seedlings collectively indicated cytosolic localization of UGT84A23 and UGT84A24. Overall, functional characterization and localization of UGT84A23 and UGT84A24 open up opportunities for further understanding the regulatory control of HT metabolism in plants and its coordination with other biochemical pathways in the metabolic network.

Analysis of Antibacterial Activity and Bioactive Compounds of the Giant Mushroom, Macrocybe gigantea (Agaricomycetes), from India.

PubMed

Gaur, Tanvi; Rao, P B

2017-01-01

The antibacterial activity, phenolic profile, and bioactive compounds of fruiting bodies from 2 strains (MA1 and MA2) of the giant mushroom Macrocybe gigantea were evaluated to access their nutraceutical efficacy. The antibacterial activity was higher in MA2 against all selected pathogenic bacteria. Selected phenolics were analyzed by high-performance liquid chromatography coupled with ultraviolet-visible detection. Gallic acid, ferulic acid, quercetin, p-hydroxy benzoic acid, cinnamic acid, and rutin contents (micrograms per gram dry weight) were quantified. Quercetin and rutin were absent in both strains of M. gigantea. M. gigantea MA2 showed relatively higher phenolic content (915.8 μg/g dry weight) than M. gigantea MA1 (854.4 μg/g dry weight). Among the phenolics, gallic acid is found in the largest amount; in M. gigantea MA2, it was 847.9 ± 2.67 μg/g dry weight. Gas chromatography-mass spectrometry analysis showed the presence of bioactive compounds in both strains; most compounds were antibacterial. Thus, the selected strains of M. gigantea can combat oxidative damage and can be used in foods, pharmaceuticals, and cosmetics because of their antioxidant potential.

Assessment of Antioxidant Properties in Fruits of Myrica esculenta: A Popular Wild Edible Species in Indian Himalayan Region

PubMed Central

Rawat, Sandeep; Jugran, Arun; Giri, Lalit; Bhatt, Indra D.; Rawal, Ranbeer S.

2011-01-01

Crude extract of Myrica esculenta fruits, a wild edible species of Indian Himalayan Region, was evaluated for phenolic compounds and antioxidant properties. Results revealed significant variation in total phenolic and flavonoid contents across populations. Among populations, total phenolic content varied between 1.78 and 2.51 mg gallic acid equivalent/g fresh weight (fw) of fruits and total flavonoids ranged between 1.31 and 1.59 mg quercetin equivalent/g fw. Antioxidant activity determined by 2,2′-azinobis(3-ethylbenzothiazoline-6-sulphonic acid) radical scavenging, 1,1-diphenyl-2-picrylhydrazyl radical scavenging and ferric reducing antioxidant power (FRAP) exhibited considerable antioxidant potential and showed significant positive correlation with total phenolic and total flavonoids content. High performance liquid chromatography analysis revealed significant variation (P <  .01) in phenolic compounds (i.e., gallic acid, catechin, hydroxybenzioc acid and ρ-coumaric acid) across populations. This study provides evidences to establish that consumption of M. esculenta fruits while providing relished taste would also help in reduction of free radicals. Therefore, this wild edible species deserves promotion in the region through horticulture and forestry interventions. PMID:21785629

HPLC profiling of phenolics and flavonoids of Adonidia merrillii fruits and their antioxidant and cytotoxic properties.

PubMed

Vafaei, Ali; Bin Mohamad, Jamaludin; Karimi, Ehsan

2018-03-12

In this study the antioxidant and cytotoxicity activity of the Adonidia merrillii fruits were investigated using different solvent polarities (methanol, ethyl acetate and water). The results showed that the total phenolic and flavonoid contents of the methanolic extract was higher compare with other extract with respective values of 17.80 ± 0.45 mg gallic acid equivalents/g dry weight (DW) and 5.43 ± 0.33 mg rutin equivalents/g DW. Beside that The RP-HPLC analyses indicated the presence of gallic acid, pyrogallol, caffeic acid, vanillic acid, syringic acid, naringin and rutin. In the DPPH, NO2 and ABTS scavenging assays, the methanolic extract exhibited higher antioxidant activity as compared to the ethyl acetate and water extracts. The extracts exhibited moderate to weak cytotoxic activity in the assays using human hepatocytes (Chang liver cells) and NIH/3T3 (fibroblasts cell) cell lines. The findings showed the Adonidia merrillii fruit extracts to possess considerable antioxidant and cytotoxicity properties. The fruit, therefore, is a potential candidate for further work to discover antioxidant and cytotoxic drugs from natural sources.

Simulated Gastrointestinal Digestion, Bioaccessibility and Antioxidant Capacity of Polyphenols from Red Chiltepin (Capsicum annuum L. Var. glabriusculum) Grown in Northwest Mexico.

PubMed

Ovando-Martínez, Maribel; Gámez-Meza, Nohemí; Molina-Domínguez, Claudia Celeste; Hayano-Kanashiro, Corina; Medina-Juárez, Luis Angel

2018-06-01

Chiltepin, a wild chili mostly used in different traditional foods and traditional medicine in Northwest Mexico, represents a source of polyphenols. However, studies about the bioaccessibility of polyphenols as a parameter to measure the nutritional quality and bioefficacy of them in the fruit after consumption are scarce. Chiltepin showed phenolic acids and flavonoids contents between 387 and 65 μg/g, respectively. Nevertheless, these values decreased after the digestion process. Before digestion, gallic acid, 4-hydroxibenzoinc acid, chlorogenic acid, caffeic acid, p-coumaric acid, quercetin and luteolin were the main polyphenols found in chiltepin by HPLC-DAD and confirmed by FIA-ESI-IT-MS/MS. Gallic and chlorogenic acids were non-detected in the gastric phase, while only p-coumaric acid (5.35 ± 3.89 μg/g), quercetin (5.91 ± 0.92 μg/g) and luteolin (2.86 ± 0.62 μg/g) were found in the intestinal phase. The bioaccessibility of phenolic acids, flavonoids, and total polyphenols after the intestinal phase was around 24, 17 and 23%, respectively. Overall, results indicated that release of polyphenols from chiltepin fruit might be affected by the food matrix and gastrointestinal conditions due to the low bioaccessibility values observed.

Insulin-secretagogue, antihyperlipidemic and other protective effects of gallic acid isolated from Terminalia bellerica Roxb. in streptozotocin-induced diabetic rats.

PubMed

Latha, R Cecily Rosemary; Daisy, P

2011-01-15

Diabetes mellitus causes derangement of carbohydrate, protein and lipid metabolism which eventually leads to a number of secondary complications. Terminalia bellerica is widely used in Indian medicine to treat various diseases including diabetes. The present study was carried out to isolate and identify the putative antidiabetic compound from the fruit rind of T. bellerica and assess its chemico-biological interaction in experimental diabetic rat models. Bioassay guided fractionation was followed to isolate the active compound, structure was elucidated using (1)H and (13)C NMR, IR, UV and mass spectrometry and the compound was identified as gallic acid (GA). GA isolated from T. bellerica and synthetic GA was administered to streptozotocin (STZ)-induced diabetic male Wistar rats at different doses for 28 days. Plasma glucose level was significantly (p<0.05) reduced in a dose-dependent manner when compared to the control.Histopathological examination of the pancreatic sections showed regeneration of β-cells of islets of GA-treated rats when compared to untreated diabetic rats. In addition, oral administration of GA (20mg/kg bw) significantly decreased serum total cholesterol, triglyceride, LDL-cholesterol, urea, uric acid, creatinine and at the same time markedly increased plasma insulin, C-peptide and glucose tolerance level. Also GA restored the total protein, albumin and body weight of diabetic rats to near normal. Thus our findings indicate that gallic acid present in fruit rind of T. bellerica is the active principle responsible for the regeneration of β-cells and normalizing all the biochemical parameters related to the patho-biochemistry of diabetes mellitus and hence it could be used as a potent antidiabetic agent. Copyright © 2010 Elsevier Ireland Ltd. All rights reserved.

Green synthesis of gold and silver nanoparticles using gallic acid: catalytic activity and conversion yield toward the 4-nitrophenol reduction reaction

NASA Astrophysics Data System (ADS)

Park, Jisu; Cha, Song-Hyun; Cho, Seonho; Park, Youmie

2016-06-01

In the present report, gallic acid was used as both a reducing and stabilizing agent to synthesize gold and silver nanoparticles. The synthesized gold and silver nanoparticles exhibited characteristic surface plasmon resonance bands at 536 and 392 nm, respectively. Nanoparticles that were approximately spherical in shape were observed in high-resolution transmission electron microscopy and atomic force microscopy images. The hydrodynamic radius was determined to be 54.4 nm for gold nanoparticles and 33.7 nm for silver nanoparticles in aqueous medium. X-ray diffraction analyses confirmed that the synthesized nanoparticles possessed a face-centered cubic structure. FT-IR spectra demonstrated that the carboxylic acid functional groups of gallic acid contributed to the electrostatic binding onto the surface of the nanoparticles. Zeta potential values of -41.98 mV for the gold nanoparticles and -53.47 mV for the silver nanoparticles indicated that the synthesized nanoparticles possess excellent stability. On-the-shelf stability for 4 weeks also confirmed that the synthesized nanoparticles were quite stable without significant changes in their UV-visible spectra. The synthesized nanoparticles exhibited catalytic activity toward the reduction reaction of 4-nitrophenol to 4-aminophenol in the presence of sodium borohydride. The rate constant of the silver nanoparticles was higher than that of the gold nanoparticles in the catalytic reaction. Furthermore, the conversion yield (%) of 4-nitrophenol to 4-aminophenol was determined using reversed-phase high-performance liquid chromatography with UV detection at 254 nm. The silver nanoparticles exhibited an excellent conversion yield (96.7-99.9 %), suggesting that the synthesized silver nanoparticles are highly efficient catalysts for the 4-nitrophenol reduction reaction.

Biopesticides from plants: Calceolaria integrifolia s.l.

PubMed

Céspedes, Carlos L; Salazar, Juan R; Ariza-Castolo, Armando; Yamaguchi, Lydia; Avila, José G; Aqueveque, Pedro; Kubo, Isao; Alarcón, Julio

2014-07-01

The effects of persistent organic pollutants (POPs) on humans and biodiversity are multiple and varied. Nowadays environmentally-friendly pesticides are strongly preferred to POPs. It is noteworthy that the crop protection role of pesticides and other techniques, i.e. biopesticides, plant extracts, prevention methods, organic methods, evaluation of plant resistance to certain pests under an integrated pest management (IPM), could improve the risks and benefits which must be assessed on a sound scientific basis. For this directive it is crucial to bring about a significant reduction in the use of chemical pesticides, not least through the promotion of sustainable alternative solutions such as organic farming and IPM. Biopesticides are derived from natural materials such as animals, plants, bacteria, and certain minerals. Most of them are biodegradable in relatively short periods of time. On this regard, substances from Calceolaria species emerge as a strong alternative to the use of POPs. The American genus Calceolaria species are regarded both as a notorious weeds and popular ornamental garden plants. Some have medicinal applications. Other taxa of Calceolaria are toxic to insects and resistant to microbial attack. These properties are probably associated with the presence of terpenes, iridoids, flavonoids, naphthoquinones and phenylpropanoids previously demonstrated to have interesting biological activities. In this article a comprehensive evaluation of the potential utilization of Calceolaria species as a source of biopesticides is made. The chemical profile of selected members of the Chilean Calceolaria integrifolia sensu lato complex represents a significant addition to previous studies. New secondary metabolites were isolated, identified and tested for their antifeedant, insect growth regulation and insecticidal activities against Spodoptera frugiperda and Drosophila melanogaster. These species serve as a model of insect pests using conventional procedures. Additionally, bactericidal and fungicidal activity were determined. Dunnione mixed with gallic acid was the most active fungistatic and fungicidal combination encountered. Several compounds as isorhamnetin, combined with ferulic and gallic acid quickly reduced cell viability, but cell viability was recovered quickly and did not differ from that of the control. The effect of these mixtures on cultures of Aspergillus niger, Fusarium moniliforme, Fusarium sporotrichum, Rhizoctonia solani, and Trichophyton mentagrophytes, was sublethal. However, when fungistatic isorhamnetin and dunnione were combined with sublethal amounts of both ferulic and gallic acid, respectively, strong fungicidal activity against theses strains was observed. Thus, dunnione combined with gallic acid completely restricted the recovery of cell viability. This apparent synergistic effect was probably due to the blockade of the recovery process from induced-stress. The same series of phenolics (iridoids, flavonoids, naphthoquinones and phenylpropanoids) were also tested against the Gram-negative bacteria Escherichia coli, Enterobacter agglomerans, and Salmonella typhi, and against the Gram-positive bacteria Bacillus subtilis, Sarcinia lutea, and Staphylococcus aureus and their effects compared with those that of kanamycin. Mixtures of isorhamnetin/dunnione/kaempferol/ferulic/gallic acid in various combinations were found to have the most potent bactericidal and fungicidal activity with MFC between 10 and 50 μg/ml. Quercetin was found to be the most potent fungistatic single compound with an MIC of 15 µg/ml. A time-kill curve study showed that quercetin was fungicidal against fungi assayed at any growth stage. This antifungal activity was slightly enhanced by combination with gallic acid. The primary antifungal action of the mixtures assayed likely comes from their ability to act as nonionic surfactants that disrupt the function of native membrane-associated proteins. Hence, the antifungal activity of isorhamnetin and other O-methyl flavonols appears to be mediated by biophysical processes. Maximum activity is obtained when the balance between hydrophilic and hydrophobic portions of the molecules of the mixtures becomes the most appropriate. Diterpenes, flavonoids, phenylpropanoids, iridoids and phenolic acids were identified by chromatographic procedures (HPLC-DAD), ESI-MS, and NMR hyphenated techniques. Copyright © 2014 Elsevier Inc. All rights reserved.

Anti-ulcer mechanisms of polyphenols extract of Euphorbia umbellata (Pax) Bruyns (Euphorbiaceae).

PubMed

Minozzo, Bruno Rodrigo; Lemes, Bruna Mikulis; Justo, Aline da Silva; Lara, Jheniffer Ellen; Petry, Victor Emanuel Kubaski; Fernandes, Daniel; Belló, Caroline; Vellosa, José Carlos Rebuglio; Campagnoli, Eduardo Bauml; Nunes, Otalíbio Castiglione; Kitagawa, Rodrigo Rezende; Avula, Bharathi; Khan, Ikhlas Ahmad; Beltrame, Flávio Luis

2016-09-15

Euphorbia umbellata (leitosinha) is used in southern Brazilian folk medicine to treat gastric problems, as well as for its analgesic and anti-inflammatory properties. To evaluate the anti-ulcer effects of methanolic bark fraction (MF) against in vivo and in vitro assays, as well as an antioxidant, antibacterial and chromatographic study of this fraction. In vivo anti-ulcer activity was performed using ethanol and indomethacin models with different MF concentrations (50, 100 or 200mg/Kg). The stomachs of the animals were applied to histological evaluation, and the serum to evaluate the ABTS(•+) radical capture. The 200mg/Kg dose was used to analyze the mechanisms involved in antiulcerogenic properties of methanolic fraction. The in vitro activity was performed using several different antioxidant assays, in addition to anti-Helicobacter pylori and anti-urease experiments. The chromatographic study was carried out by LC-MS analysis. Pharmacological investigation of the MF showed an anti-ulcer potential in ethanol and indomethacin in vivo assays. The material presented a high antioxidant activity for several oxidant in vitro systems (DPPH(•), ABTS(•+), O2(•-), HOCl, TauCl and HRP), as well as an ABTS(•+) capture increasing (7.5%) by the treated animals serum (when compared to the negative control). Prostaglandins, nitric oxide/ cyclic guanosine monophosphate pathway and involvement of the protein components of the glutathione complex are some of the mechanisms related with this potential anti-ulcer action. The histological examination of the stomachs of the animals showed that the MF also prevents local action of offensive agents. Chemical analysis using LC-QTOF-MS revealed the presence of ellagic and gallic acid derivatives and flavonols. The findings provide scientific basis to the ethnopharmacological purpose of the studied plant and the biological activities of MF of E. umbellata stem bark may be due to the presence of phenolic compounds. Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

E-cinnamic acid derivatives and phenolics from Chilean strawberry fruits, Fragaria chiloensis ssp. chiloensis.

PubMed

Cheel, José; Theoduloz, Cristina; Rodríguez, Jaime; Saud, Guillermo; Caligari, Peter D S; Schmeda-Hirschmann, Guillermo

2005-11-02

Three E-cinnamic acid glycosides, tryptophan, and cyanidin-3-O-beta-D-glucopyranoside were isolated from ripe fruits of the Chilean strawberry Fragaria chiloensis ssp. chiloensis. 1-O-E-Cinnamoyl-beta-D-xylopyranoside, 1-O-E-cinnamoyl-beta-D-rhamnopyranoside, and 1-O-E-cinnamoyl-alpha-xylofuranosyl-(1-->6)-beta-D-glucopyranose are reported for the first time. The cinnamic acid glycosides and aromatic compound patterns in F. chiloensis fruits were determined by high-performance liquid chromatography (HPLC). HPLC analyses of extracts showed that cyanidin-3-O-beta-D-glucopyranoside and free ellagic acid are present in achenes while the E-cinnamoyl derivatives and tryptophan were identified only in the thalamus. The free radical scavenging effect of the fruit extract can be associated with the anthocyanin content.

Ellagic acid inhibits iron-mediated free radical formation

NASA Astrophysics Data System (ADS)

Dalvi, Luana T.; Moreira, Daniel C.; Andrade, Roberto; Ginani, Janini; Alonso, Antonio; Hermes-Lima, Marcelo

2017-02-01

Polyphenols are reported to have some health benefits, which are link to their antioxidant properties. In the case of ellagic acid (EA), there is evidence that it has free radical scavenger properties and that it is able to form complexes with metal ions. However, information on a possible link between the formation of iron-EA complexes and their interference in Haber-Weiss/Fenton reactions was not yet determined. Thus, the present study investigated the in vitro antioxidant mechanism of EA in a system containing ascorbate, Fe(III) and different iron ligands (EDTA, citrate and NTA). Iron-mediated oxidative degradation of 2-deoxyribose was poorly inhibited (by 12%) in the presence of EA (50 μM) and EDTA. When citrate or NTA - which form weak iron complexes - were used, the 2-deoxyribose protection increased to 89-97% and 45%, respectively. EA also presented equivalent inhibitory effects on iron-mediated oxygen uptake and ascorbyl radical formation. Spectral analyses of iron-EA complexes show that EA removes Fe(III) from EDTA within hours, and from citrate within 1 min. This difference in the rate of iron-EA complex formation may explain the antioxidant effects of EA. Furthermore, the EA antioxidant effectiveness was inversely proportional to the Fe(III) concentration, suggesting a competition with EDTA. In conclusion, the results indicate that EA may prevent in vitro free radical formation when it forms a complex with iron ions.

Impact of ellagic acid in bone formation after tooth extraction: an experimental study on diabetic rats.

PubMed

Al-Obaidi, Mazen M Jamil; Al-Bayaty, Fouad Hussain; Al Batran, Rami; Hussaini, Jamal; Khor, Goot Heah

2014-01-01

To estimate the impact of ellagic acid (EA) towards healing tooth socket in diabetic animals, after tooth extraction. Twenty-four Sprague Dawley male rats weighing 250-300 g were selected for this study. All animals were intraperitoneally injected with 45 mg/kg (b.w.) of freshly prepared streptozotocin (STZ), to induce diabetic mellitus. Then, the animals were anesthetized, and the upper left central incisor was extracted and the whole extracted sockets were filled with Rosuvastatin (RSV). The rats were separated into three groups, comprising 8 rats each. The first group was considered as normal control group and orally treated with normal saline. The second group was regarded as diabetic control group and orally treated with normal saline, whereas the third group comprised diabetic rats, administrated with EA (50 mg/kg) orally. The maxilla tissue stained by eosin and hematoxylin (H&E) was used for histological examinations and immunohistochemical technique. Fibroblast growth factor (FGF-2) and alkaline phosphatase (ALP) were used to evaluate the healing process in the extracted tooth socket by immunohistochemistry test. The reactions of immunohistochemistry for FGF-2 and ALP presented stronger expression, predominantly in EA treated diabetic rat, than the untreated diabetic rat. These findings suggest that the administration of EA combined with RSV may have accelerated the healing process of the tooth socket of diabetic rats, after tooth extraction.

Chemical Composition and Bioactivities of Two Common Chaenomeles Fruits in China: Chaenomeles speciosa and Chaenomeles sinensis.

PubMed

Miao, Jing; Zhao, Chengcheng; Li, Xia; Chen, Xuetao; Mao, Xinhui; Huang, Hanhan; Wang, Tingting; Gao, Wenyuan

2016-08-01

Contents of total flavonoids, total phenolics, total triterpenes, total condensed tannin and total saponins in peels, flesh and endocarps of Chaenomeles speciosa (CSP) and Chaenomeles sinensis (CSS) were determined by colorimetric method, while 5 phenolics (vanillic, gallic, chlorogenic, ferulic and p-coumaric acids), 2 triterpenes (oleanolic and ursolic acids), and 3 flavonoids (rutin, catechin and epicatechin) were identified and quantified by high-performance liquid chromatography-mass spectrometry (HPLC-MS) and HPLC, and antioxidant and α-glucosidase inhibitory activities of them also were evaluated as well as their digestive characteristics. In the correlation analysis, total phenolics, vanillic acid, catechin, ursolic acid and oleanolic acid all contribute to DPPH(·) scavenge capacity, gallic acid contributes to total ferric reducing antioxidant power, while total triterpenes, total saponins, chlorogenic acid and ferullic acid contribute to α-glucosidase inhibitory activity. In the principal component analysis, endocarps of CSP and CSS both show better quality than their peels and flesh, respectively. In vitro digestion can increase contents of total flavonoids, total condensed tannin and total saponins, while contents of total phenolics and total triterpenes decreased greatly. Our study would contribute to the full use of discarded parts of the 2 Chaenomeles and be helpful to establish a good foundation for further research of CSP and CSS. © 2016 Institute of Food Technologists®

Cranberries (Vaccinium macrocarpon) and cardiovascular disease risk factors.

PubMed

McKay, Diane L; Blumberg, Jeffrey B

2007-11-01

The American cranberry (Vaccinium macrocarpon) is one of the three commercially important fruits native to North America. Cranberries are a particularly rich source of phenolic phytochemicals, including phenolic acids (benzoic, hydroxycinnamic, and ellagic acids) and flavonoids (anthocyanins, flavonols, and flavan-3-ols). A growing body of evidence suggests that polyphenols, including those found in cranberries, may contribute to reducing the risk of cardiovascular disease (CVD) by increasing the resistance of LDL to oxidation, inhibiting platelet aggregation, reducing blood pressure, and via other anti-thrombotic and anti-inflammatory mechanisms. Research regarding the bioactivity of cranberries and their constituents on risk factors for CVD is reviewed.

Graphene Oxide-Gallic Acid Nanodelivery System for Cancer Therapy

NASA Astrophysics Data System (ADS)

Dorniani, Dena; Saifullah, Bullo; Barahuie, Farahnaz; Arulselvan, Palanisamy; Hussein, Mohd Zobir Bin; Fakurazi, Sharida; Twyman, Lance J.

2016-11-01

Despite the technological advancement in the biomedical science, cancer remains a life-threatening disease. In this study, we designed an anticancer nanodelivery system using graphene oxide (GO) as nanocarrier for an active anticancer agent gallic acid (GA). The successful formation nanocomposite (GOGA) was characterized using XRD, FTIR, HRTEM, Raman, and UV/Vis spectroscopy. The release study shows that the release of GA from the designed anticancer nanocomposite (GOGA) occurs in a sustained manner in phosphate-buffered saline (PBS) solution at pH 7.4. In in vitro biological studies, normal fibroblast (3T3) and liver cancer cells (HepG2) were treated with different concentrations of GO, GOGA, and GA for 72 h. The GOGA nanocomposite showed the inhibitory effect to cancer cell growth without affecting normal cell growth. The results of this research are highly encouraging to go further for in vivo studies.

Evaluation of antioxidant activity and characterization of phenolic constituents of Phyllanthus amarus root.

PubMed

Maity, Soumya; Chatterjee, Suchandra; Variyar, Prasad Shekhar; Sharma, Arun; Adhikari, Soumyakanti; Mazumder, Santasree

2013-04-10

The antioxidant property of the 70% aqueous ethanol extract of Phyllanthus amarus roots and its ether-soluble, ethyl acetate-soluble, and aqueous fractions were investigated by various in vitro assays. The root extracts showed higher DPPH, hydroxyl, superoxide, and nitric oxide radical scavenging and reducing power activity. Among all the samples, the ethyl acetate-soluble fraction demonstrated highest radical scavenging activity and total phenolics content. Twenty-eight different phenolic compounds were identified by LCMS/MS analysis of the ethyl acetate-soluble fraction. The majority of the compounds were found to exist as their glycosides, and many of these were gallic acid derivatives. Free epicatechin and gallic acid were also identified in the ethyl acetate-soluble fraction. The present investigation suggested that P. amarus root is a potent antioxidant and can be used for the prevention of diseases related to oxidative stress.

Dye ingredients and energy conversion efficiency at natural dye sensitized solar cells

NASA Astrophysics Data System (ADS)

Özbay Karakuş, Mücella; Koca, İrfan; Er, Orhan; Çetin, Hidayet

2017-04-01

In this work, natural dyes extracted from the same genus but different species flowers were used as sensitizer in Dye Sensitized Solar Cell (DSSC). To clearly show dye ingredients effect on electrical characteristics, the same genus flowers were selected. The dye ingredients were analyzed by Gas Chromatography Mass Spectrometer (GC-MS). The dyes were modified by a procedure that includes refluxing in acetone. All results indicate a relationship between gallic acid quantity in dyes and solar cell efficiency. To gain further insight, the solar cell parameters were obtained by using the single-diode and double-diode models and they were compared to each other. It was observed that the applied process causes a decrease in series resistance. How the modification process and gallic acid affect energy conversion efficiency were argued in detail in the frame of results that were obtained from solar cell models.

Comparative study of the antioxidant capacity and polyphenol content of Douro wines by chemical and electrochemical methods.

PubMed

Rebelo, M J; Rego, R; Ferreira, M; Oliveira, M C

2013-11-01

A comparative study of the antioxidant capacity and polyphenols content of Douro wines by chemical (ABTS and Folin-Ciocalteau) and electrochemical methods (cyclic voltammetry and differential pulse voltammetry) was performed. A non-linear correlation between cyclic voltammetric results and ABTS or Folin-Ciocalteau data was obtained if all types of wines (white, muscatel, ruby, tawny and red wines) are grouped together in the same correlation plot. In contrast, a very good linear correlation was observed between the electrochemical antioxidant capacity determined by differential pulse voltammetry and the radical scavenging activity of ABTS. It was also found that the antioxidant capacity of wines evaluated by the electrochemical methods (expressed as gallic acid equivalents) depend on background electrolyte of the gallic acid standards, type of electrochemical signal (current or charge) and electrochemical technique. Copyright © 2013 Elsevier Ltd. All rights reserved.

Enhancement of nutritionally significant constituents of black currant seeds by chemical elicitor application.

PubMed

Flores, Gema; Ruiz del Castillo, María Luisa

2016-03-01

Black currant seeds are obtained as a residue during juice production. Black currant seed oil contains high amounts of nutritionally desirable constituents such as γ-linolenic acid (GLA), α-linolenic acid (ALA) and stearidonic acid (SA), as well as certain phenolic acids, which act as natural antioxidants. Fatty acids and phenolic acids of seeds from black currant cultivars after elicitation with methyl jasmonate (MJ) were examined. GLA contents around 25% with respect to total fatty acid content were measured in seeds after pre-harvest treatment of black currants with 0.02mM MJ in 0.05% Tween-20. High GLA samples also exhibited high SA content (higher than 10% with respect to total fatty acid content); however, ALA dropped (from 16% to 10%). High GLA content seeds also showed increased contents of gallic, caffeic, p-coumaric and ferulic acids. In particular, seeds from 0.02mM MJ treated Ben Hope black currants exerted contents of gallic, caffeic, p-coumaric and ferulic acids of 201.4, 125.9, 201.3 and 112.5μgg(-1)vs 124.3, 58.6, 165.4 and 95.8μgg(-1) measured in seeds from untreated Ben Hope black currants. Comparable results were obtained for Ben Alder and Ben Gairn berries. Chemical elicitation with 0.02 MJ is proposed as an industrial practice in such a way that, after consideration of quality issues, it would be obtained high added value black currant seeds. Copyright © 2015 Elsevier Ltd. All rights reserved.

The effect of heat treatment on phenolic compounds and fatty acid composition of Brazilian nut and hazelnut.

PubMed

Özcan, Mehmet Musa; Juhaimi, Fahad Al; Uslu, Nurhan

2018-01-01

Brazilian peanut oil content increased with oven heating (65.08%) and decreased with microwave heating process (61.00%). While the phenolic content of untreated Brazilian nut was the highest of 68.97 mg GAE/100 g. Hazelnut (Sivri) contained the highest antioxidant activity (86.52%, untreated). Results reflected significantly differences between the antioxidant effect and total phenol contents of Brazilian nut and hazelnut (Sivri) kernels heated in the oven and microwave. Microwave heating caused a decrease in antioxidant activity of hazelnut. Gallic acid, 3,4-dihydroxybenzoic acid and (+)- and catechin were the main phenolic compounds of raw Brazilian nut with the value of 5.33, 4.33 and 4.88 mg/100 g, respectively, while the dominant phenolics of raw hazelnut (Sivri) kernels were gallic acid (4.81 mg/100 g), 3,4-dihydroxybenzoic acid (4.61 mg/100 g), (+)-catechin (6.96 mg/100 g) and 1,2-dihydroxybenzene (4.14 mg/100 g). Both conventional and microwave heating caused minor reduction in phenolic compounds. The main fatty acids of Brazilian nut oil were linoleic (44.39-48.18%), oleic (27.74-31.74%), palmitic (13.09-13.70%) and stearic (8.20-8.91%) acids, while the dominant fatty acids of hazelnut (Sivri) oil were oleic acid (80.84%), respectively. The heating process caused noticeable change in fatty acid compositions of both nut oils.

Resolving Identification Issues of Saraca asoca from Its Adulterant and Commercial Samples Using Phytochemical Markers

PubMed Central

Hegde, Satisha; Hegde, Harsha Vasudev; Jalalpure, Sunil Satyappa; Peram, Malleswara Rao; Pai, Sandeep Ramachandra; Roy, Subarna

2017-01-01

Saraca asoca (Roxb.) De Wilde (Ashoka) is a highly valued endangered medicinal tree species from Western Ghats of India. Besides treating cardiac and circulatory problems, S. asoca provides immense relief in gynecological disorders. Higher price and demand, in contrast to the smaller population size of the plant, have motivated adulteration with other plants such as Polyalthia longifolia (Sonnerat) Thwaites. The fundamental concerns in quality control of S. asoca arise due to its part of medicinal value (Bark) and the chemical composition. Phytochemical fingerprinting with proper selection of analytical markers is a promising method in addressing quality control issues. In the present study, high-performance liquid chromatography of phenolic compounds (gallic acid, catechin, and epicatechin) coupled to multivariate analysis was used. Five samples each of S. asoca, P. longifolia from two localities alongside five commercial market samples showed evidence of adulteration. Subsequently, multivariate hierarchical cluster analysis and principal component analysis was established to discriminate the adulterants of S. asoca. The proposed method ascertains identification of S. asoca from its putative adulterant P. longifolia and commercial market samples. The data generated may also serve as baseline data to form a quality standard for pharmacopoeias. SUMMARY Simultaneous quantification of gallic acid, catechin, epicatechin from Saraca asoca by high-performance liquid chromatographyDetection of S. asoca from adulterant and commercial samplesUse of analytical method along with a statistical tool for addressing quality issues. Abbreviations used: HPLC: High Performance Liquid Chromatography; RP-HPLC: Reverse Phase High Performance Liquid Chromatography; CAT: Catechin; EPI: Epicatechin; GA: Gallic acid; PCA: Principal Component Analysis. PMID:28808391

Application of α-aminoisobutyric acid and β-aminoisobutyric acid inhibits pericarp browning of harvested longan fruit.

PubMed

Wang, Hui; Zhi, Wei; Qu, Hongxia; Lin, Hetong; Jiang, Yueming

2015-12-01

Pericarp browning is a critical problem resulting in reduced commercial value and shelf life of longan fruit. Two non-protein amino acids, α-aminoisobutyric acid (AIB) and β-aminoisobutyric acid (BAIB) at 100 and 1 mM were applied to longan fruit prior to storage for up to 8 days at 25 °C respectively. Contents of the major five phenolics (gallic acid, catechin, corilagin, epicatechin and gallocatechin gallate) were assayed by high-performance liquid chromatography (HPLC). Physiological properties related to pericarp browning of longan fruit were investigated during storage. Respiration rate, membrane permeability, malondialdehyde (MDA) content, and activities of polyphenol oxidase (PPO) and peroxidase (POD) were down-regulated by AIB or BAIB treatments, with significantly lower pericarp browning index and higher proportion of edible fruit than the control. Moreover, exogenous application of AIB and BAIB maintained higher contents of catechin, corilagin, epicatechin and gallocatechin gallate, but lower content of gallic acid compared to the control in the pericarp of longan fruit during storage, which was associated with the oxidation of browning substrate. Pericarp browning was inhibited and storage life of longan fruit was extended effectively by AIB and BAIB treatments with AIB treatment being more significant than BAIB. The findings may provide a new strategy for controlling pericarp browning of harvested longan fruit.

The dopant type and amount governs the electrochemical performance of graphene platforms for the antioxidant activity quantification

NASA Astrophysics Data System (ADS)

Hui, Kai Hwee; Ambrosi, Adriano; Sofer, Zdeněk; Pumera, Martin; Bonanni, Alessandra

2015-05-01

Graphene doped with heteroatoms can show new or improved properties as compared to the original undoped material. It has been reported that the type of heteroatoms and the doping conditions can have a strong influence on the electronic and electrochemical properties of the resulting material. Here, we wish to compare the electrochemical behavior of two n-type and two p-type doped graphenes, namely boron-doped graphenes and nitrogen-doped graphenes containing different amounts of heteroatoms. We show that the boron-doped graphene containing a higher amount of dopants provides the best electroanalytical performance in terms of calibration sensitivity, selectivity and linearity of response for the detection of gallic acid normally used as the standard probe for the quantification of antioxidant activity of food and beverages. Our findings demonstrate that the type and amount of heteroatoms used for the doping have a profound influence on the electrochemical detection of gallic acid rather than the structural properties of the materials such as amounts of defects, oxygen functionalities and surface area. This finding has a profound influence on the application of doped graphenes in the field of analytical chemistry.Graphene doped with heteroatoms can show new or improved properties as compared to the original undoped material. It has been reported that the type of heteroatoms and the doping conditions can have a strong influence on the electronic and electrochemical properties of the resulting material. Here, we wish to compare the electrochemical behavior of two n-type and two p-type doped graphenes, namely boron-doped graphenes and nitrogen-doped graphenes containing different amounts of heteroatoms. We show that the boron-doped graphene containing a higher amount of dopants provides the best electroanalytical performance in terms of calibration sensitivity, selectivity and linearity of response for the detection of gallic acid normally used as the standard probe for the quantification of antioxidant activity of food and beverages. Our findings demonstrate that the type and amount of heteroatoms used for the doping have a profound influence on the electrochemical detection of gallic acid rather than the structural properties of the materials such as amounts of defects, oxygen functionalities and surface area. This finding has a profound influence on the application of doped graphenes in the field of analytical chemistry. Electronic supplementary information (ESI) available. See DOI: 10.1039/c5nr01045d

Characterization And Application Of Tannase Produced By Aspergillus Niger ITCC 6514.07 On Pomegranate Rind

PubMed Central

Srivastava, Anita; Kar, Rita

2009-01-01

Extracellular tannase and gallic acid were produced optimally under submerged fermentation at 37 0C, 72 h, pH 5.0, 10 %(v/v) inoculum and 4 %(w/v) of the agroresidue pomegranate rind (PR) powder by an Aspergillus niger isolate. Tannic acid (1 %) stimulated the enzyme production by 245.9 % while with 0.5 % glucose, increase was marginal. Tannase production was inhibited by gallic acid and nitrogen sources such as NH4NO3, NH4Cl, KNO3, asparatic acid, urea and EDTA. The partially purified enzyme showed temperature and pH optima of 35 0C and 6.2 respectively which shifted to 40 0C and 5.8 on immobilization in alginate beads. Activity of the enzyme was inhibited by Zn+2, Ca+, Mn+2, Mg+2, Ba+2and Ag+. The immobilized enzyme removed 68.8 % tannin from juice of aonla/myrobalan (Phyllanthus emblica), a tropical fruit, rich in vitamin C and other essential nutrients. The enzymatic treatment of the juice with minimum reduction in vitamin C is encouraging as non enzymatic treatments of myrobalan juice results in vitamin C removal. PMID:24031425