Analysis of Organic Acids, Deacetyl Asperulosidic Acid and Polyphenolic Compounds as a Potential Tool for Characterization of Noni (Morinda citrifolia) Products.

PubMed

Bittová, Miroslava; Hladůkova, Dita; Roblová, Vendula; Krácmar, Stanislav; Kubán, Petr; Kubán, Vlastimil

2015-11-01

Organic acids, deacetyl asperulosidic acid (DAA) and polyphenolic compounds in various noni (Morinda citrifolia L.) products (4 juices, 4 dry fruit powders and 2 capsules with dry fruit powder) were analyzed. Reversed-phase high-performance liquid chromatography (RP-HPLC) coupled with a variable wavelength detector (VWD) and electrospray ionization time-of-flight mass spectrometer (ESI-TOF MS) was applied for simultaneous analysis of organic acids (malic, lactic, citric and succinic acid) and DAA. An RP-HPLC method with diode-array detector (DAD) was developed for the analysis of polyphenolic compound content (rutin, catechin, quercitrin, kaempferol, gallic acid, caffeic acid and p-coumaric acid). The developed methods can contribute to better characterization of available noni products that is required from the consumers. In our study, we discovered significant dissimilarities in the content of DAA, citric acid and several phenolic compounds in some samples.

Gastroprotective effects and antimicrobial activity of Lithraea molleoides and isolated compounds against Helicobacter pylori.

PubMed

Garro, María Filomena; Salinas Ibáñez, Angel Gabriel; Vega, Alba Edith; Arismendi Sosa, Andrea Celeste; Pelzer, Lilian; Saad, José Roberto; Maria, Alejandra Olivia

2015-12-24

Lithraea molleoides (Vell.) Engl. (Anacardiaceae) is a medicinal plant traditionally used in South America to treat various ailments, including diseases of the digestive system. To evaluate the in vivo antiulcer and antimicrobial activities against Helicobacter pylori of L. molleoides and its isolated compounds. Methanolic extract 250 and 500 mg/kg, (LmE 250 and LmE 500, respectively) and infusions, 10 g and 20 g en 100mL (LmI 10 and LmI 20, respectively) of L. molleoides was evaluated for antiulcer activity against 0.6N HCl, 0.2N NaOH, 200mg/kg acetilsalicilic acid and absolute ethanol-induced gastric ulcers in rats. The degree of erosion in the glandular part of the stomach was assessed from a scoring system. Acute toxicity in mice was also evaluated. The antiulcer effect of the isolated compounds (catechol, mannitol, rutin, gallic acid, ferulic acid and caffeic acid, 100mg/kg) was evaluated against absolute ethanol-induced gastric ulcers in rats. The anti-Helicobacter pylori activity of L. molleoides and isolated compounds was performed using broth dilution methods. The LmE 250, LmE 500, LmI 10 and LmI 20 produced significant inhibition on the ulcer index in 0.6N HCl, 0.2N NaOH, 200mg/kg acetilsalicilic acid and absolute ethanol- induced gastric ulcers in rats. The isolated compounds, catechol, mannitol, rutin, ferulic acid and caffeic acid were active in absolute ethanol- induced gastric ulcers in rats. L. molleoides and different compounds showed antimicrobial activity in all strains tested. The lowest MIC value (0. 5 μg/mL) was obtained with catechol in six of eleven strains assayed. No signs of toxicity were observed with doses up to 2g/kg in an acute toxicity assay. These findings indicate that L. molleoides displays potential antiulcerogenic and antimicrobial activities and the identification of active principles could support the use of this plant for the treatment of digestive affections. Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.

Antiprotozoal Constituents from Annona cherimola Miller, a Plant Used in Mexican Traditional Medicine for the Treatment of Diarrhea and Dysentery

PubMed Central

Calzada, Fernando; Correa-Basurto, Jose; Barbosa, Elizabeth; Mendez-Luna, David; Yepez-Mulia, Lilian

2017-01-01

Background: Annona cherimola Miller (Annonaceae) is a medicinal plant frequently recommended in Mexican traditional medicine for the treatment of gastrointestinal disorders such as diarrhea and dysentery. Objective: This work was undertaken to obtain information that support the traditional use of A. cherimola, on pharmacological basis using in vitro and computational experiments. Material and Methods: Bioassay-guided fractionation of the ethanol extract of the leaves of A. cherimola afforded five phenolic compounds: caffeic acid, quercetin, kaempferol, nicotinflorin, and rutin. Results: The in vitro antiprotozoal assay showed that kaempferol was the most potent antiamoebic and antigiardial compound with IC50 values of 7.9 μg/mL for Entamoeba histolytica and 8.7 μg/mL for Giardia lamblia. Computational molecular docking study showed that kaempferol interacted in a region different than metronidazole in the enzyme pyruvate: ferredoxin oxidoreductase (PFOR). Conclusion: Considering that PFOR is a target of metronidazole; kaempferol may be a lead compound for the development of novel antiprotozoal agent. Also, these findings give support to the use of A. cherimola in the traditional medicine from México for the treatment of diarrhea and dysentery. SUMMARY Bioassay-guided fractionation of the ethanol extract of the leaves of Annona cherimola afforded five phenolic compounds: caffeic acid, quercetin, kaempferol, nicotinflorin and rutin. The in vitro antiprotozoal assay showed that kaempferol was the most potent antiamoebic and antigiardial compound with IC50 values of 7.9 μg/mL for Entamoeba histolytica and 8.7 μg/mL for Giardia lamblia. Computational molecular docking study showed that kaempferol interacted in a region different that metronidazole in the enzyme pyruvate: ferredoxin oxidoreductase. Abbreviations used: PFOR:Pyruvate:ferredoxin oxidoreductase, G: lamblia: Giardia lamblia, E: histolytica: Entamoeba histolytica PMID:28216899

Effects of low nitrogen supply on tomato (Solanum lycopersicum) fruit yield and quality with special emphasis on sugars, acids, ascorbate, carotenoids, and phenolic compounds.

PubMed

Bénard, Camille; Gautier, Hélène; Bourgaud, Frédéric; Grasselly, Dominique; Navez, Brigitte; Caris-Veyrat, Catherine; Weiss, Marie; Génard, Michel

2009-05-27

The objective of this study was to determine the impact of lowering nitrogen supply from 12 to 6 or 4 mM NO(3)(-) on tomato fruit yield and quality during the growing season. Lowering nitrogen supply had a low impact on fruit commercial yield (-7.5%), but it reduced plant vegetative growth and increased fruit dry matter content, improving consequently fruit quality. Fruit quality was improved due to lower acid (10-16%) and increased soluble sugar content (5-17%). The content of some phenolic compounds (rutin, a caffeic acid glycoside, and a caffeic acid derivate) and total ascorbic acid tended to be higher in fruit with the lowest nitrogen supply, but differences were significant in only a few cases (trusses). With regard to carotenoids, data did not show significant and univocal differences related to different levels of nitrogen supply. Thus, reducing nitrogen fertilization limited environmental pollution, on the one hand, and may improve, on the other hand, both growers' profits, by limiting nitrogen inputs, and fruit quality for consumers, by increasing tomato sugars content. It was concluded that primary and secondary metabolites could be affected as a result of a specific response to low nitrogen, combined with a lower degree of vegetative development, increasing fruit irradiance, and therefore modifying fruit composition.

Comparative polyphenolic content and antioxidant activities of Genista tinctoria L. and Genistella sagittalis (L.) Gams (Fabaceae).

PubMed

Hanganu, Daniela; Olah, Neli Kinga; Benedec, Daniela; Mocan, Andrei; Crisan, Gianina; Vlase, Laurian; Popica, Iulia; Oniga, Ilioara

2016-01-01

The aim of this study was focused on the polyphenolic composition and antioxidant capacity of Genista tinctoria L. and Genistella sagittalis (L.) Gams. A qualitative and quantitative characterization of the main phenolic compounds from the extracts were carried out using a HPLC-MS method. The total polyphenolic and flavonoid content was spectrophotometrically determined. The antioxidant activity towards various radicals generated in different systems was evaluated usingDPPH bleaching method, Trolox equivalent antioxidant capacity assay (TEAC) and Oxygen radical absorbance capacity (ORAC), and all indicated that G. tinctoria extract was more antioxidant than G. sagittalis extract.That was in good agreement with the total polyphenolic and flavonoidic content.Chlorogenic acid, p-coumaric acid, isoquercitrin and apigenin were identified in bothspecies. Caffeic acid, ferulic acid, hyperoside, rutin, quercitrin and luteolin were found only in G. tinctoria, while quercetin was determined in G. sagittalis.

Phenolics content and antioxidant activity of tartary buckwheat from different locations.

PubMed

Guo, Xu-Dan; Ma, Yu-Jie; Parry, John; Gao, Jin-Ming; Yu, Liang-Li; Wang, Min

2011-11-25

Two tartary buckwheat samples (Xingku No.2 and Diqing) grown at three locations were analyzed for free and bound phenolic content and antioxidant properties. Moreover, the relative contributions of variety and growing environment to phenolic content and antioxidant properties were determined, as well as correlations of these properties to growing conditions. The total phenolic contents varied from 5,150 to 9,660 μmol of gallic acid equivalents per 100 gram of dry weight (DW) of tartary buckwheat and the free phenolics accounted for 94% to 99%. Rutin content was in the range from 518.54 to 1,447.87 mg per 100 gram of DW of tartary buckwheat. p-Hydroxybenzoic, ferulic and protocatechuic acids were the prominent phenolic acids and other phenolics, including p-coumaric, gallic, caffeic, vanillic and syringic acids were also detected. Tartary buckwheat exhibited higher DPPH· and ABTS·+ scavenging activities and was more effective at preventing the bleaching of β-carotene in comparison with reference antioxidant and plant phenolics constituents. Additionally, growing conditions and the interaction between variety and environment may have more contribution than variety to individual phenolics and antioxidant properties of tartary buckwheat. Environmental parameters such as higher altitudes may also have an increasing effect on rutin and phenolic acids. This study suggests that tartary buckwheat has potential health benefits because of its high phenolic content and antioxidant properties. These components could also be enhanced by optimizing the growing conditions of a selected variety.

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

Active compounds, antioxidant activity and α-glucosidase inhibitory activity of different varieties of Chaenomeles fruits.

PubMed

Miao, Jing; Li, Xia; Zhao, Chengcheng; Gao, Xiaoxiao; Wang, Ying; Gao, Wenyuan

2018-05-15

Chaenomeles is an important source for food industry in China, and its planting area is expanding year by year. This study was conducted to evaluate different varieties of Chaenomeles by comparing the chemical compositions, antioxidant activity and α-glucosidase inhibitory activity of peels and fleshes from twelve varieties of Chaenomeles. In the results, peels of Chaenomeles contain more phenolics, flavonoids and triterpenes, and show better antioxidant activity and α-glucosidase inhibitory activity than their fleshes. All varieties of Chaenomeles perform different depend on cultivar and climatic conditions. Oleanolic acid, ursolic acid, protocatechuic acid, rutin, catechin, caffeic acid, syringic acid, epicatechin, hyperin, quercetin, kaempferol and chlorogenic acid are main active compounds in Chaenomeles. Zheng'an, Liufu, Zimugua1, Qijiang and Changjun get Top five scores. This is the first study on the peels and fleshes of twelve varieties of Chaenomeles, and it gives insights into variety selection in the planting and production of Chaenomeles. Copyright © 2017 Elsevier Ltd. All rights reserved.

Anti-inflammatory activity of flavonoids from Eupatorium arnottianum.

PubMed

Clavin, M; Gorzalczany, S; Macho, A; Muñoz, E; Ferraro, G; Acevedo, C; Martino, V

2007-07-25

Three anti-inflammatory compounds: nepetin, jaceosidin and hispidulin have been isolated and identified from Eupatorium arnottianum Griseb. dichloromethane extract. Nepetin reduced the TPA mouse ear edema by 46.9% and jaceosidin by 23.2% (1mg/ear). Both compounds inhibited the NF kappaB induction by 91 and 77%, respectively. Furthermore phytochemical analysis of the ethanol extract has led to the identification of eriodictyol, hyperoside, rutin, caffeic and chlorogenic acids. All these compounds are reported for the first time in this species. The finding of topical antiinflammatory activity exerted by Eupatorium arnottianum extract and the identification of active principles could support the use of this plant for the treatment of inflammatory affections.

Determination of Flavonoids, Phenolic Acids, and Xanthines in Mate Tea (Ilex paraguariensis St.-Hil.)

PubMed Central

Bojić, Mirza; Simon Haas, Vicente; Maleš, Željan

2013-01-01

Raw material, different formulations of foods, and dietary supplements of mate demands control of the content of bioactive substances for which high performance thin layer chromatography (TLC), described here, presents simple and rapid approach for detections as well as quantification. Using TLC densitometry, the following bioactive compounds were identified and quantified: chlorogenic acid (2.1 mg/g), caffeic acid (1.5 mg/g), rutin (5.2 mg/g), quercetin (2.2 mg/g), and kaempferol (4.5 mg/g). The results obtained with TLC densitometry for caffeine (5.4 mg/g) and theobromine (2.7 mg/g) show no statistical difference to the content of total xanthines (7.6 mg/g) obtained by UV-Vis spectrophotometry. Thus, TLC remains a technique of choice for simple and rapid analysis of great number of samples as well as a primary screening technique in plant analysis. PMID:23841023

Measurement of Antioxidant Capacity by Electron Spin Resonance Spectroscopy Based on Copper(II) Reduction.

PubMed

Li, Dan; Jiang, Jia; Han, Dandan; Yu, Xinyu; Wang, Kun; Zang, Shuang; Lu, Dayong; Yu, Aimin; Zhang, Ziwei

2016-04-05

A new method is proposed for measuring the antioxidant capacity by electron spin resonance spectroscopy based on the loss of electron spin resonance signal after Cu(2+) is reduced to Cu(+) with antioxidant. Cu(+) was removed by precipitation in the presence of SCN(-). The remaining Cu(2+) was coordinated with diethyldithiocarbamate, extracted into n-butanol and determined by electron spin resonance spectrometry. Eight standards widely used in antioxidant capacity determination, including Trolox, ascorbic acid, ferulic acid, rutin, caffeic acid, quercetin, chlorogenic acid, and gallic acid were investigated. The standard curves for determining the eight standards were plotted, and results showed that the linear regression correlation coefficients were all high enough (r > 0.99). Trolox equivalent antioxidant capacity values for the antioxidant standards were calculated, and a good correlation (r > 0.94) between the values obtained by the present method and cupric reducing antioxidant capacity method was observed. The present method was applied to the analysis of real fruit samples and the evaluation of the antioxidant capacity of these fruits.

HPLC-DAD phenolic profile, cytotoxic and anti-kinetoplastidae activity of Melissa officinalis.

PubMed

Cunha, Francisco; Tintino, Saulo R; Figueredo, Fernando; Barros, Luiz; Duarte, Antonia E; Vega Gomez, Maria Celeste; Coronel, Cathia Cecilia; Rolón, Mírian; Leite, Nadghia; Sobral-Souza, Celestina E; Brito, S V; Waczuc, Emily Pansera; Boligon, Aline Augusti; Athayde, Margareth; Kamdem, Jean Paul; Coutinho, Henrique Douglas Melo; Franco, Jéferson

2016-09-01

Context Melissa officinalis subsp. inodora Bornm. (Lamiaceae) has been used since ancient times in folk medicine against various diseases, but it has not been investigated against protozoa. Objective To evaluate the activities of M. officinalis against Leishmania braziliensis, Leishmania infantum and Trypanosoma cruzi as well as its cytotoxicity in fibroblast cell line. Materials and methods The fresh leaves were chopped into 1 cm(2) pieces, washed and macerated with 99.9% of ethanol for 72 h at room temperature. Antiparasitic activity of M. officinalis was accessed by direct counting of cells after serial dilution, while the cytotoxicity of M. officinalis was evaluated in fibroblast cell line (NCTC929) by measuring the reduction of resazurin. The test duration was 24 h. High-performance liquid chromatography (HPLC) was used to characterise the extract. Results The extract at concentrations of 250 and 125 μg/mL inhibited 80.39 and 54.27% of promastigote (LC50  value = 105.78 μg/mL) form of L. infantum, 80.59 and 68.61% of L. brasiliensis (LC50 value  = 110.69 μg/mL) and against epimastigote (LC50 value  = 245.23 μg/mL) forms of T. cruzi with an inhibition of 54.45 and 22.26%, respectively, was observed. The maximum toxicity was noted at 500 μg/mL with 95.41% (LC50  value = 141.01 μg/mL). The HPLC analysis identified caffeic acid and rutin as the major compounds. Discussion The inhibition of the parasites is considered clinically relevant (< 500 μg/mL). Rutin and caffeic acids may be responsible for the antiprotozoal effect of the extract. Conclusion The ethanol extract of M. officinalis can be considered a potential alternative source of natural products with antileishmania and antitrypanosoma activities.

Phytochemical Composition, Antifungal and Antioxidant Activity of Duguetia furfuracea A. St.-Hill

PubMed Central

Pinho, Francisca Valéria Soares de Araújo; da Cruz, Litiele Cezar; Rodrigues, Nathane Rosa; Waczuk, Emily Pansera; Souza, Celestina Elba Sobral; da Costa, José Galberto Martins; Athayde, Margareth Linde; de Menezes, Irwin Rose Alencar

2016-01-01

Background. Duguetia furfuracea is popular plant used in popular medicine. Hypothesis/Purpose. This claim evaluated the phytochemical composition of the hydroethanolic extract (HEDF), fractions of Duguetia furfuracea, and antioxidant and antifungal activity. Methods. The chemical profile was carried out by HPLC-DAD. The total phenolic contents and flavonoid components were determined by Folin-Ciocalteu and aluminium chloride reaction. The antioxidant activity was measured by scavenging of 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical and ferric reducing ability of plasma (FRAP) methods. The antifungal activity was determined by microdilution assay. Results. HPLC analysis revealed caffeic acid and rutin as major compounds (HEDF), caffeic acid and quercitrin (Mt-OH fraction), and quercitrin and isoquercitrin (Ac-OEt fraction). The highest levels of phenols and total flavonoids were found for Ac-OEt fraction, and the crude extract showed higher in vitro antioxidant potential. The antifungal activity showed synergic effect with fluconazole and EHDF against C. krusei, fluconazole and Mt-OH against C. krusei and C. tropicalis, and Ac-OE and fluconazole against C. albicans. Conclusion. The highest levels of phenols and total flavonoids were marked with antioxidant effect. This is the first report of bioactivity of the synergic effect of HEDF and fractions. More studies would be required to better clarify its mechanism of synergic action. PMID:27127550

Rapid and quantitative determination of 10 major active components in Lonicera japonica Thunb. by ultrahigh pressure extraction-HPLC/DAD

NASA Astrophysics Data System (ADS)

Fan, Li; Lin, Changhu; Duan, Wenjuan; Wang, Xiao; Liu, Jianhua; Liu, Feng

2015-01-01

An ultrahigh pressure extraction (UPE)-high performance liquid chromatography (HPLC)/diode array detector (DAD) method was established to evaluate the quality of Lonicera japonica Thunb. Ten active components, including neochlorogenic acid, chlorogenic acid, 4-dicaffeoylquinic acid, caffeic acid, rutin, luteoloside, isochlorogenic acid B, isochlorogenic acid A, isochlorogenic acid C, and quercetin, were qualitatively evaluated and quantitatively determined. Scanning electron microscope images elucidated the bud surface microstructure and extraction mechanism. The optimal extraction conditions of the UPE were 60% methanol solution, 400 MPa of extraction pressure, 3 min of extraction time, and 1:30 (g/mL) solid:liquid ratio. Under the optimized conditions, the total extraction yield of 10 active components was 57.62 mg/g. All the components showed good linearity (r2 ≥ 0.9994) and recoveries. This method was successfully applied to quantify 10 components in 22 batches of L. japonica samples from different areas. Compared with heat reflux extraction and ultrasonic-assisted extraction, UPE can be considered as an alternative extraction technique for fast extraction of active ingredient from L. japonica.

Phenolic compounds, organic acids and antioxidant activity of grape juices produced from new Brazilian varieties planted in the Northeast Region of Brazil.

PubMed

Lima, Marcos Dos Santos; Silani, Igor de Souza Veras; Toaldo, Isabela Maia; Corrêa, Luiz Claudio; Biasoto, Aline Camarão Telles; Pereira, Giuliano Elias; Bordignon-Luiz, Marilde T; Ninow, Jorge Luiz

2014-10-15

The phenolic compounds, organic acids and the antioxidant activity were determined for grape juice samples from new Brazilian varieties grown in the Sub-middle São Francisco Valley in the Northeast Region of Brazil. The results showed that the Brazilian grape juices have high antioxidant activity, which was significantly correlated with the phenolic compounds catechin, epicatechin gallate, procyanidin B1, rutin, gallic acid, caffeic acid, p-coumaric acid, pelargonidin-3-glucoside, cyanidin-3-glucoside, cyaniding-3,5-diglucoside and delphinidin-3-glucoside. The produced juice samples showed higher concentrations of trans-resveratrol than those observed in juices made from different varieties of grapes from traditional growing regions. Organic acids concentrations were similar to those of juices produced from other classical varieties. It was demonstrated that it is possible to prepare juices from grapes of new varieties grown in the Northeast of Brazil containing a high content of bioactive compounds and typical characteristics of the tropical viticulture practised in the Sub-middle São Francisco Valley. Copyright © 2014 Elsevier Ltd. All rights reserved.

Characterization of phenolic profile and antioxidant capacity of different fruit part from lemon (Citrus limon Burm.) cultivars.

PubMed

Xi, Wanpeng; Lu, Juanfang; Qun, Junping; Jiao, Bining

2017-04-01

Phenolic composition and antioxidant capacity of different fruit part including peel, pulp, juice, whole fruit and seed from five lemon cultivars (Feiminailao, Cuningmeng Limeng, Pangdelusaningmeng, Beijingningmeng) were investigated. Caffeic acid (9.31-741.4 μg/g FW) and chlorogenic acid (2.7-527.5 μg/g FW) were the dominant phenolic acid in fruit tested, Pangdelusaningmeng (PD) and Limeng peels with the highest contents, respectively. Hesperidin was the predominant flavanone (10.27-3315 μg/g FW), Cuningmeng (CN) peels with the highest level. PD peels had rich rutin, CN seeds had rich eriocitrin. Nobiletin was the main polymethoxylated flavonoids identified, PD with the highest level. CN peels contained rich tangeretin. Overall, peels and whole fruit had significantly higher level of phenolics than other fruit parts, and seeds were good source of flavonoids. PD and CN not only contained higher level of phenolic, but also presented higher antioxidant capacity than other cultivars tested, and are of great value for human nutrition.

Preparative isolation and purification of seven main antioxidants from Eucommia ulmoides Oliv. (Du-zhong) leaves using HSCCC guided by DPPH-HPLC experiment.

PubMed

Dai, Xingping; Huang, Qiong; Zhou, Boting; Gong, Zhicheng; Liu, Zhaoqian; Shi, Shuyun

2013-08-15

Seven antioxidants were purified from Eucommia ulmoides Oliv. leaves using HSCCC guided by DPPH-HPLC experiment. HSCCC was successfully used to separate target antioxidants by three runs with different solvent systems after D101 column chromatography fractionation. Ethyl acetate-n-butanol-water (1:2:3, v/v/v) was selected as the optimum solvent system to purify geniposidic acid. Ethyl acetate-ethanol-water (4:1:5, v/v/v) was used to isolate caffeic acid, chlorogenic acid and ferulic acid. While three flavonoids, quercetin-3-O-sambubioside, rutin and isoquercitrin were purified by petroleum ether-ethyl acetate-methanol-water (1:5:1:5, v/v/v/v). The structures were identified by MS and NMR. Antioxidant activities were assessed, and compounds 2-7 showed strong antioxidant activities. This is the first report about separation of antioxidants from E. ulmoides leaves by HSCCC. The results indicated that the combinative methods using DPPH-HPLC and HSCCC could be widely applied for screening and isolation of antioxidants from complex extracts. Copyright © 2013 Elsevier Ltd. All rights reserved.

Evaluation of synergistic antioxidant potential of complex mixtures using oxygen radical absorbance capacity (ORAC) and electron paramagnetic resonance (EPR).

PubMed

Parker, Tory L; Miller, Samantha A; Myers, Lauren E; Miguez, Fernando E; Engeseth, Nicki J

2010-01-13

Previous research has demonstrated that certain combinations of compounds result in a decrease in toxic or pro-oxidative effects, previously noted when compounds were administered singly. Thus, there is a need to study many complex interactions further. Two in vitro techniques [electron paramagnetic resonance (EPR) and oxygen radical absorbance capacity (ORAC) assays] were used in this study to assess pro- and antioxidant capacity and synergistic potential of various compounds. Rutin, p-coumaric acid, abscisic acid, ascorbic acid, and a sugar solution were evaluated individually at various concentrations and in all 26 possible combinations at concentrations found in certain foods (honey or papaya), both before and after simulated digestion. EPR results indicated sugar-containing combinations provided significantly higher antioxidant capacity; those combinations containing sugars and ascorbic acid demonstrated synergistic potential. The ORAC assay suggested additive effects, with some combinations having synergistic potential, although fewer combinations were significantly synergistic after digestion. Finally, ascorbic acid, caffeic acid, quercetin, and urate were evaluated at serum-achievable levels. EPR analysis did not demonstrate additive or synergistic potential, although ORAC analysis did, principally in combinations containing ascorbic acid.

Caffeic acid treatment alters the extracellular adenine nucleotide hydrolysis in platelets and lymphocytes of adult rats.

PubMed

Anwar, Javed; Spanevello, Roselia Maria; Pimentel, Victor Camera; Gutierres, Jessié; Thomé, Gustavo; Cardoso, Andreia; Zanini, Daniela; Martins, Caroline; Palma, Heloisa Einloft; Bagatini, Margarete Dulce; Baldissarelli, Jucimara; Schmatz, Roberta; Leal, Cláudio Alberto Martins; da Costa, Pauline; Morsch, Vera Maria; Schetinger, Maria Rosa Chitolina

2013-06-01

This study evaluated the effects of caffeic acid on ectonucleotidase activities such as NTPDase (nucleoside triphosphate diphosphohydrolase), Ecto-NPP (nucleotide pyrophosphatase/phosphodiesterase), 5'-nucleotidase and adenosine deaminase (ADA) in platelets and lymphocytes of rats, as well as in the profile of platelet aggregation. Animals were divided into five groups: I (control); II (oil); III (caffeic acid 10 mg/kg); IV (caffeic acid 50 mg/kg); and V (caffeic acid 100 mg/kg). Animals were treated with caffeic acid diluted in oil for 30 days. In platelets, caffeic acid decreased the ATP hydrolysis and increased ADP hydrolysis in groups III, IV and V when compared to control (P<0.05). The 5'-nucleotidase activity was decreased, while E-NPP and ADA activities were increased in platelets of rats of groups III, IV and V (P<0.05). Caffeic acid reduced significantly the platelet aggregation in the animals of groups III, IV and V in relation to group I (P<0.05). In lymphocytes, the NTPDase and ADA activities were increased in all groups treated with caffeic acid when compared to control (P<0.05). These findings demonstrated that the enzymes were altered in tissues by caffeic acid and this compound decreased the platelet aggregation suggesting that caffeic acid should be considered a potentially therapeutic agent in disorders related to the purinergic system. Copyright © 2013 Elsevier Ltd. All rights reserved.

MONITORING OF SYNERGISTIC ENHANCEMENT OF CAFFEIC ACID ON ESCHERICHIA COLI K-12 RECA::GFP STRAIN TREATED WITH DACARBAZINE.

PubMed

Matejczyk, Marzena; Swislocka, Renata; Kalinowska, Monika; Swidersk, Grzegorz; Lewandowsk, Wlodzimierz; Jablonska-Trypuo, Agata

2017-05-01

Caffeic acid and its derivatives because of its biological activities, including antioxidants, antithrombosis, antihypertensive, antifibrosis, antiviral, and anti-tumor properties are good candidates as adjuvants in anticancer therapy. The aim of this study was the examination of cyto- and genotoxic effect of caffeic acid on Escherichia coli K-12 recA::gfp strain treated with dacarbazine. Obtained results indicate that dacarbazine and caffeic acid influenced the reactivity of recA promoter and modulate the level of gfp expression in genetic construct rrcA::gfpmut2 in E. coli K-12. Simultaneuos administration of dacarbazine with caffeic acid caused the stronger inhibition of the bacteria growth than the dacarbazine and caffeic acid separated administration to bacteria cells. The simultaneous effect of the both tested chemicals - dacarbazine and caffeic acid indicated (cytostatic effect) anticancer activity in relation to bacteria cells. It suggests, that combination of known anticancer drug - dacarbazine w ith caffeic acid exerted synergistic cytotoxic and genotoxic effects toward E. coli K- 12 cells and indicated the possibility of usefulness of caffeic acid as a natural adjuvant in anticancer therapy.

Chemical and botanical characterization of Chilean propolis and biological activity on cariogenic bacteria Streptococcus mutans and Streptococcus sobrinus.

PubMed

Barrientos, Leticia; Herrera, Christian L; Montenegro, Gloria; Ortega, Ximena; Veloz, Jorge; Alvear, Marysol; Cuevas, Alejandro; Saavedra, Nicolás; Salazar, Luis A

2013-01-01

Propolis is a non-toxic natural substance with multiple pharmacological properties including anti-cancer, antioxidant, fungicidal, antibacterial, antiviral, and anti-inflammatory among others. The aim of this study was to determine the chemical and botanical characterization of Chilean propolis samples and to evaluate their biological activity against the cariogenic bacteria Streptococcus mutans and Streptococcus sobrinus. Twenty propolis samples were obtained from beekeeping producers from the central and southern regions of Chile. The botanical profile was determined by palynological analysis. Total phenolic contents were determined using colorimetric assays. Reverse phase HPLC and HPLC-MS were used to determine the chemical composition. The minimum inhibitory concentration (MIC) was determined on S. mutans and S. sobrinus. All propolis samples were dominated by structures from native plant species. The characterization by HPLC/MS, evidenced the presence of quercetin, myricetin, kaempferol, rutine, pinocembrin, coumaric acid, caffeic acid and caffeic acid phenethyl ester, that have already been described in these propolis with conventional HPLC. Although all propolis samples inhibited the mutans streptococci growth, it was observed a wide spectrum of action (MIC 0.90 to 8.22 μg mL(-1)). Given that results it becomes increasingly evident the need of standardization procedures, where we combine both the determination of botanical and the chemical characterization of the extracts. Research conducted to date, describes a promising effectiveness of propolis in the prevention of caries and other diseases of the oral cavity, making it necessary to develop studies to identify and understand the therapeutic targets or mechanisms of molecular action of the various compounds present on them.

The Phenolic Contents and Antioxidant Activities of Infusions of Sambucus nigra L.

PubMed

Viapiana, Agnieszka; Wesolowski, Marek

2017-03-01

The aim of this work was to evaluate the antioxidant potential of teas prepared from twenty-four commercially available berries and flowers of Sambucus nigra L. in relation to their phenolic profile, as reflected by the most representative phenolic acids (caffeic, chlorogenic, p-coumaric, ferulic, gallic and syringic acids); flavonols (quercetin, kaempferol, myricetin and rutin); and total phenolic (TPC), phenolic acid (TAC) and flavonoid (TFC) contents. The infusions prepared from elderflowers contained more abundant phenolic compounds than the elderberry infusions. The TPC of these infusions ranged from 19.81 to 23.90 mg of gallic acid equivalents/g dry weight of sample (GAE/g DW) for elderberries and from 15.23 to 35.57 mg GAE/g DW for elderflowers, whereas the TFC ranged from 2.60 to 4.49 mg of rutin equivalents/g dry weight of sample (RUTE/g DW) in elderberry infusions and from 5.27 to 13.19 mg RUTE/g DW in elderflower infusions. Among the phenolic compounds quantified in this study, quercetin (2.07-9.48 mg/g DW) and myricetin (1.17-9.62 mg/g DW) had the highest concentrations in the teas prepared from berries and flowers, respectively. Moreover, the antioxidant potential of elder infusions assessed by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and ferric reducing antioxidant power (FRAP) assays revealed that the teas prepared from flowers had higher mean DPPH and FRAP activities than the teas prepared from berries. Therefore, elder beverages could be important dietary sources of natural antioxidants that contribute to the prevention of diseases caused by oxidative stress.

Antioxidant activity of phenolic acids and their metabolites: synthesis and antioxidant properties of the sulfate derivatives of ferulic and caffeic acids and of the acyl glucuronide of ferulic acid.

PubMed

Piazzon, A; Vrhovsek, U; Masuero, D; Mattivi, F; Mandoj, F; Nardini, M

2012-12-19

The main metabolites of caffeic and ferulic acids (ferulic acid-4'-O-sulfate, caffeic acid-4'-O-sulfate, and caffeic acid-3'-O-sulfate), the most representative phenolic acids in fruits and vegetables, and the acyl glucuronide of ferulic acid were synthesized, purified, and tested for their antioxidant activity in comparison with those of their parent compounds and other related phenolics. Both the ferric reducing antioxidant power (FRAP) assay and the 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging method were used. Ferulic acid-4'-O-sulfate and ferulic acid-4'-O-glucuronide exhibited very low antioxidant activity, while the monosulfate derivatives of caffeic acid were 4-fold less efficient as the antioxidant than caffeic acid. The acyl glucuronide of ferulic acid showed strong antioxidant action. The antioxidant activity of caffeic acid-3'-O-glucuronide and caffeic acid-4'-O-glucuronide was also studied. Our results demonstrate that some of the products of phenolic acid metabolism still retain strong antioxidant properties. Moreover, we first demonstrate the ex vivo synthesis of the acyl glucuronide of ferulic acid by mouse liver microsomes, in addition to the phenyl glucuronide.

Plant phenolics decrease intestinal tumors in an animal model of familial adenomatous polyposis.

PubMed

Mahmoud, N N; Carothers, A M; Grunberger, D; Bilinski, R T; Churchill, M R; Martucci, C; Newmark, H L; Bertagnolli, M M

2000-05-01

Epidemiological studies consistently indicate that consumption of fruits and vegetables lowers cancer risk in humans and suggest that certain dietary constituents may be effective in preventing colon cancer. Plant-derived phenolic compounds manifest many beneficial effects and can potentially inhibit several stages of carcinogenesis in vivo. In this study, we investigated the efficacy of several plant-derived phenolics, including caffeic acid phenethyl ester (CAPE), curcumin, quercetin and rutin, for the prevention of tumors in C57BL/6J-Min/+ (Min/+) mice. These animals bear a germline mutation in the Apc gene and spontaneously develop numerous intestinal adenomas by 15 weeks of age. At a dietary level of 0.15%, CAPE decreased tumor formation in Min/+ mice by 63%. Curcumin induced a similar tumor inhibition. Quercetin and rutin, however, both failed to alter tumor formation at dietary levels of 2%. Examination of intestinal tissue from the treated animals showed that tumor prevention by CAPE and curcumin was associated with increased enterocyte apoptosis and proliferation. CAPE and curcumin also decreased expression of the oncoprotein beta-catenin in the enterocytes of the Min/+ mouse, an observation previously associated with an antitumor effect. These data place the plant phenolics CAPE and curcumin among a growing list of anti-inflammatory agents that suppress Apc-associated intestinal carcinogenesis.

Effect of three edible oils on the intestinal absorption of caffeic acid: An in vivo and in vitro study

PubMed Central

Prasadani, W. Chaturi; Senanayake, Chaturi M.; Jayathilaka, Nimanthi; Ekanayake, Sagarika

2017-01-01

Polyphenolic antioxidants are mainly absorbed through passive paracellular permeation regulated by tight junctions. Some fatty acids are known to modulate tight junctions. Fatty acids resulting from the digestion of edible oils may improve the absorption of polyphenolic antioxidants. Therefore, we explored the effect of three edible oils on the intestinal absorption of caffeic acid. Rats were fed with soybean oil and caffeic acid dissolved in distilled water. Caffeic acid contents in the plasma collected up to 1 hr were quantified. The experiment was repeated with coconut oil and olive oil. Component fatty acids of the oils were individually tested in vitro for their effect on permeability of caffeic acid using Caco-2 cell monolayers. Highest absorption of caffeic acid was observed in animals fed with coconut oil. In vitro transport percentages of caffeic acid in 2.5 mmol/L solutions of fatty acids were 22.01±0.12 (lauric), 15.30 ± 0.25 (myristic acid), 13.59 ± 0.35 (linoleic acid), 3.70 ± 0.09 (oleic acid) and 0.10–2.0 (all other fatty acids). Lauric acid and myristic acid are the two major fatty acids present in coconut oil. Therefore, these fatty acids may contribute to the higher absorption of caffeic acid in the presence of coconut oil. PMID:28617858

Biochemical Characterization of Ferulic Acid and Caffeic Acid Which Effectively Inhibit Melanin Synthesis via Different Mechanisms in B16 Melanoma Cells.

PubMed

Maruyama, Hiroko; Kawakami, Fumitaka; Lwin, Thet-Thet; Imai, Motoki; Shamsa, Fazel

2018-01-01

In this study, we examined the inhibitory effects of ferulic acid and caffeic acid on melanin production using a murine B16 melanoma cell line. The mechanisms by which the two acids inhibit melanin production were investigated by evaluating their effects on the activity of tyrosinase, which is involved is the first step of melanin biosynthesis. Ferulic acid showed no toxicity against the melanoma cells at any dose, whereas caffeic acid exerted cellular toxicity at concentrations higher than 0.35 mM. Both ferulic and caffeic acids effectively inhibited melanin production in the B16 melanoma cells. Ferulic acid reduced tyrosinase activity by directly binding to the enzyme, whereas no binding was observed between caffeic acid and tyrosinase. Both ferulic acid and caffeic acid inhibited casein kinase 2 (CK2)-induced phosphorylation of tyrosinase in a dose-dependent manner in vitro. Ferulic acid was found to be a more effective inhibitor of melanin production than caffeic acid; this difference in the inhibitory efficacy between the two substances could be attributable to the difference in their tyrosine-binding activity. Our analysis revealed that both substances also inhibited the CK2-mediated phosphorylation of tyrosinase.

In vitro antiviral efficacy of caffeic acid against canine distemper virus.

PubMed

Wu, Zong-Mei; Yu, Zhen-Jiang; Cui, Zhen-Qiang; Peng, Lu-Yuan; Li, Hao-Ran; Zhang, Chun-Lei; Shen, Hai-Qing; Yi, Peng-Fei; Fu, Ben-Dong

2017-09-01

Canine distemper (CD) is a highly contagious disease caused by the canine distemper virus (CDV), and mortality can be as high as 100%. However, there is no specific treatment for CD. In this study, the antiviral activity of the caffeic acid against CDV was evaluated in vitro. The results showed that the IC 50 of the caffeic acid against CDV at 1 and 2 h post infection (PI) is 23.3 and 32.3 μg/mL, respectively. Consistently, at 1 and 2 h PI, the caffeic acid exhibited a reduced (23.3-57.0% and 37.2-38.1%) viral inhibitory effect in vero cells. Furthermore, the caffeic acid plus Ribavirin (RBV) has greater antiviral activity against CDV than the caffeic acid or RBV individually. In addition, the caffeic acid reduced the total viral RNA synthesis by 59-86% at 24-72 h. Therefore, our data provided the experimental evidence that the caffeic acid effectively inhibited CDV infection in vero cells, which may potentially be used to treat clinical disease associated with CDV infection. Copyright © 2017. Published by Elsevier Ltd.

Influence of Various Phenolic Compounds on Properties of Gelatin Film Prepared from Horse Mackerel Trachurus japonicus Scales.

PubMed

Le, Thuy; Maki, Hiroki; Okazaki, Emiko; Osako, Kazufumi; Takahashi, Kigen

2018-06-15

Influence of various phenolic compounds on physical properties and antioxidant activity of gelatin film from horse mackerel Trachurus japonicus scales was investigated. Tensile strength (TS) of the film was enhanced whereas elongation at break was declined by adding 1% to 5% phenolic compounds. Rutin was the most effective to improve the TS compared to the other tested phenolic compounds including ferulic acid, caffeic acid, gallic acid, and catechin. Gelatin films with the phenolic compounds showed the excellent UV barrier properties. FTIR spectra exhibited that wavenumber of amide-A band of films decreased with formation of hydrogen bonding between amino groups of gelatin and hydroxyl groups of the phenolic compounds. Gelatin film incorporated with rutin which has the largest number of hydroxyl groups among the tested compounds demonstrated the lowest wavenumber for the amide-A peak. It is indicated that hydroxyl groups contained in the phenolic compounds contribute to formation of hydrogen bonds involved in improvement of the mechanical properties of the films. The incorporation of the phenolic compounds with gelatin films also led to the increasing of total phenolic contents and DPPH radical scavenging activities. Thus, it is concluded that phenolic compounds can promote the quality of gelatin film. Properties of gelatin film derived from horse mackerel scales can be improved by adding of phenolic compounds. Phenolic compounds containing a large number of hydroxyl groups should be selected to enhance physical properties of the gelatin film. A biodegradable film prepared from horse mackerel gelatin incorporated with phenolic compounds, which has good physical properties and antioxidant properties, can solve environmental problems caused by synthetic plastic materials. © 2018 Institute of Food Technologists®.

Caffeic acid as active principle from the fruit of Xanthium strumarium to lower plasma glucose in diabetic rats.

PubMed

Hsu, F L; Chen, Y C; Cheng, J T

2000-04-01

The antihyperglycemic effect of caffeic acid, one of the phenolic compounds contained in the fruit of Xanthium strumarium, was investigated. After an intravenous injection of caffeic acid into diabetic rats of both streptozotocin-induced and insulin-resistant models, a dose-dependent decrease of plasma glucose was observed. However, a similar effect was not produced in normal rats. An insulin-independent action of caffeic acid can thus be considered. Otherwise, this compound reduced the elevation of plasma glucose level in insulin-resistant rats receiving a glucose challenge test. Also, glucose uptake into the isolated adipocytes was raised by caffeic acid in a concentration-dependent manner. Increase of glucose utilization by caffeic acid seems to be responsible for the lowering of plasma glucose.

Caffeic acid, a phenolic phytochemical in coffee, directly inhibits Fyn kinase activity and UVB-induced COX-2 expression

PubMed Central

Kang, Nam Joo; Lee, Ki Won; Shin, Bong Jik; Jung, Sung Keun; Hwang, Mun Kyung; Bode, Ann M.; Heo, Yong-Seok; Dong, Zigang

2009-01-01

Caffeic acid (3,4-dihydroxycinnamic acid) is a well-known phenolic phytochemical present in many foods, including coffee. Recent studies suggested that caffeic acid exerts anticarcinogenic effects, but little is known about the underlying molecular mechanisms and specific target proteins. In this study, we found that Fyn, one of the members of the non-receptor protein tyrosine kinase family, was required for ultraviolet (UV) B-induced cyclooxygenase-2 (COX-2) expression, and caffeic acid suppressed UVB-induced skin carcinogenesis by directly inhibiting Fyn kinase activity. Caffeic acid more effectively suppressed UVB-induced COX-2 expression and subsequent prostaglandin E2 production in JB6 P+ mouse skin epidermal (JB6 P+) cells compared with chlorogenic acid (5-O-caffeoylquinic acid), an ester of caffeic acid with quinic acid. Data also revealed that caffeic acid more effectively induced the downregulation of COX-2 expression at the transcriptional level mediated through the inhibition of activator protein-1 (AP-1) and nuclear factor-κB transcription activity compared with chlorogenic acid. Fyn kinase activity was suppressed more effectively by caffeic acid than by chlorogenic acid, and downstream mitogen-activated protein kinases (MAPKs) were subsequently blocked. Pharmacological Fyn kinase inhibitor (3-(4-chlorophenyl)1-(1,1-dimethylethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine and leflunomide) data also revealed that Fyn is involved in UVB-induced COX-2 expression mediated through the phosphorylation of MAPKs in JB6 P+ cells. Pull-down assays revealed that caffeic acid directly bound with Fyn and non-competitively with adenosine triphosphate. In vivo data from mouse skin also supported the idea that caffeic acid suppressed UVB-induced COX-2 expression by blocking Fyn kinase activity. These results suggested that this compound could act as a potent chemopreventive agent against skin cancer. PMID:19073879

Chemical and botanical characterization of Chilean propolis and biological activity on cariogenic bacteria Streptococcus mutans and Streptococcus sobrinus

PubMed Central

Barrientos, Leticia; Herrera, Christian L.; Montenegro, Gloria; Ortega, Ximena; Veloz, Jorge; Alvear, Marysol; Cuevas, Alejandro; Saavedra, Nicolás; Salazar, Luis A.

2013-01-01

Propolis is a non-toxic natural substance with multiple pharmacological properties including anti-cancer, antioxidant, fungicidal, antibacterial, antiviral, and anti-inflammatory among others. The aim of this study was to determine the chemical and botanical characterization of Chilean propolis samples and to evaluate their biological activity against the cariogenic bacteria Streptococcus mutans and Streptococcus sobrinus. Twenty propolis samples were obtained from beekeeping producers from the central and southern regions of Chile. The botanical profile was determined by palynological analysis. Total phenolic contents were determined using colorimetric assays. Reverse phase HPLC and HPLC-MS were used to determine the chemical composition. The minimum inhibitory concentration (MIC) was determined on S. mutans and S. sobrinus. All propolis samples were dominated by structures from native plant species. The characterization by HPLC/MS, evidenced the presence of quercetin, myricetin, kaempferol, rutine, pinocembrin, coumaric acid, caffeic acid and caffeic acid phenethyl ester, that have already been described in these propolis with conventional HPLC. Although all propolis samples inhibited the mutans streptococci growth, it was observed a wide spectrum of action (MIC 0.90 to 8.22 μg mL−1). Given that results it becomes increasingly evident the need of standardization procedures, where we combine both the determination of botanical and the chemical characterization of the extracts. Research conducted to date, describes a promising effectiveness of propolis in the prevention of caries and other diseases of the oral cavity, making it necessary to develop studies to identify and understand the therapeutic targets or mechanisms of molecular action of the various compounds present on them. PMID:24294257

Boronic acid based imprinted electrochemical sensor for rutin recognition and detection.

PubMed

Wang, Chunlei; Wang, Qi; Zhong, Min; Kan, Xianwen

2016-10-21

Multi-walled carbon nanotubes (MWNTs) and boronic acid based molecular imprinting polymer (MIP) were successively modified on a glassy carbon electrode surface to fabricate a novel electrochemical sensor for rutin recognition and detection. 3-Aminophenylboronic acid (APBA) was chosen as a monomer for the electropolymerization of MIP film in the presence of rutin. In addition to the imprinted cavities in MIP film to complement the template molecule in shape and functional groups, the high affinity between the boronic acid group of APBA and vicinal diols of rutin also enhanced the selectivity of the sensor, which made the sensor display a good selectivity to rutin. Moreover, the modified MWNTs improved the sensitivity of the sensor for rutin detection. The mole ratios of rutin and APBA, electropolymerized scan cycles and rates, and pH value of the detection solution were optimized. Under optimal conditions, the sensor was used to detect rutin in a linear range from 4.0 × 10 -7 to 1.0 × 10 -5 mol L -1 with a detection limit of 1.1 × 10 -7 mol L -1 . The sensor has also been applied to assay rutin in tablets with satisfactory results.

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

Microbial Biotransformation of a Polyphenol-Rich Potato Extract Affects Antioxidant Capacity in a Simulated Gastrointestinal Model

PubMed Central

Khairallah, Joelle; Sadeghi Ekbatan, Shima; Sabally, Kebba; Iskandar, Michèle M.; Hussain, Raza; Sleno, Lekha; Rodes, Laetitia; Prakash, Satya

2018-01-01

A multistage human gastrointestinal model was used to digest a polyphenol-rich potato extract containing chlorogenic acid, caffeic acid, ferulic acid, and rutin as the primary polyphenols, to assess for their microbial biotransformation and to measure changes in antioxidant capacity in up to 24 h of digestion. The biotransformation of polyphenols was assessed by liquid chromatography–mass spectrometry. Antioxidant capacity was measured by the ferric reducing antioxidant power (FRAP) assay. Among the colonic reactors, parent (poly)phenols were detected in the ascending (AC), but not the transverse (TC) or descending (DC) colons. The most abundant microbial phenolic metabolites in all colonic reactors included derivatives of propionic acid, acetic acid, and benzoic acid. As compared to the baseline, an earlier increase in antioxidant capacity (T = 8 h) was seen in the stomach and small intestine vessels as compared to the AC (T = 16 h) and TC and DC (T = 24 h). The increase in antioxidant capacity observed in the DC and TC can be linked to the accumulation of microbial smaller-molecular-weight phenolic catabolites, as the parent polyphenolics had completely degraded in those vessels. The colonic microbial digestion of potato-based polyphenols could lead to improved colonic health, as this generates phenolic metabolites with significant antioxidant potential. PMID:29558385

Caffeic acid protects rat heart mitochondria against isoproterenol-induced oxidative damage

PubMed Central

Kumaran, Kandaswamy Senthil

2010-01-01

Cardiac mitochondrial dysfunction plays an important role in the pathology of myocardial infarction. The protective effects of caffeic acid on mitochondrial dysfunction in isoproterenol-induced myocardial infarction were studied in Wistar rats. Rats were pretreated with caffeic acid (15 mg/kg) for 10 days. After the pretreatment period, isoproterenol (100 mg/kg) was subcutaneously injected to rats at an interval of 24 h for 2 days to induce myocardial infarction. Isoproterenol-induced rats showed considerable increased levels of serum troponins and heart mitochondrial lipid peroxidation products and considerable decreased glutathione peroxidase and reduced glutathione. Also, considerably decreased activities of isocitrate, succinate, malate, α-ketoglutarate, and NADH dehydrogenases and cytochrome-C-oxidase were observed in the mitochondria of myocardial-infarcted rats. The mitochondrial calcium, cholesterol, free fatty acids, and triglycerides were considerably increased and adenosine triphosphate and phospholipids were considerably decreased in isoproterenol-induced rats. Caffeic acid pretreatment showed considerable protective effects on all the biochemical parameters studied. Myocardial infarct size was much reduced in caffeic acid pretreated isoproterenol-induced rats. Transmission electron microscopic findings also confirmed the protective effects of caffeic acid. The possible mechanisms of caffeic acid on cardiac mitochondria protection might be due to decreasing free radicals, increasing multienzyme activities, reduced glutathione, and adenosine triphosphate levels and maintaining lipids and calcium. In vitro studies also confirmed the free-radical-scavenging activity of caffeic acid. Thus, caffeic acid protected rat’s heart mitochondria against isoproterenol-induced damage. This study may have a significant impact on myocardial-infarcted patients. PMID:20376586

Caffeic acid protects rat heart mitochondria against isoproterenol-induced oxidative damage.

PubMed

Kumaran, Kandaswamy Senthil; Prince, Ponnian Stanely Mainzen

2010-11-01

Cardiac mitochondrial dysfunction plays an important role in the pathology of myocardial infarction. The protective effects of caffeic acid on mitochondrial dysfunction in isoproterenol-induced myocardial infarction were studied in Wistar rats. Rats were pretreated with caffeic acid (15 mg/kg) for 10 days. After the pretreatment period, isoproterenol (100 mg/kg) was subcutaneously injected to rats at an interval of 24 h for 2 days to induce myocardial infarction. Isoproterenol-induced rats showed considerable increased levels of serum troponins and heart mitochondrial lipid peroxidation products and considerable decreased glutathione peroxidase and reduced glutathione. Also, considerably decreased activities of isocitrate, succinate, malate, α-ketoglutarate, and NADH dehydrogenases and cytochrome-C-oxidase were observed in the mitochondria of myocardial-infarcted rats. The mitochondrial calcium, cholesterol, free fatty acids, and triglycerides were considerably increased and adenosine triphosphate and phospholipids were considerably decreased in isoproterenol-induced rats. Caffeic acid pretreatment showed considerable protective effects on all the biochemical parameters studied. Myocardial infarct size was much reduced in caffeic acid pretreated isoproterenol-induced rats. Transmission electron microscopic findings also confirmed the protective effects of caffeic acid. The possible mechanisms of caffeic acid on cardiac mitochondria protection might be due to decreasing free radicals, increasing multienzyme activities, reduced glutathione, and adenosine triphosphate levels and maintaining lipids and calcium. In vitro studies also confirmed the free-radical-scavenging activity of caffeic acid. Thus, caffeic acid protected rat's heart mitochondria against isoproterenol-induced damage. This study may have a significant impact on myocardial-infarcted patients.

Ex-vivo in-vitro inhibition of lipopolysaccharide stimulated tumor necrosis factor-alpha and interleukin-1 beta secretion in human whole blood by extractum urticae dioicae foliorum.

PubMed

Obertreis, B; Ruttkowski, T; Teucher, T; Behnke, B; Schmitz, H

1996-04-01

An extract of Urtica dioica folium (IDS 23, Rheuma-Hek), monographed positively for adjuvant therapy of rheumatic diseases and with known effects in partial inhibition of prostaglandin and leukotriene synthesis in vitro, was investigated with respect to effects of the extract on the lipopolysaccharide (LPS) stimulated secretion of proinflammatory cytokines in human whole blood of healthy volunteers. In the assay system used, LPS stimulated human whole blood showed a straight increase of tumor necrosis factor-alpha (TNF-alpha) and interleukin-1 beta (IL-1 beta) secretion reaching maximum concentrations within 24 h following a plateau and slight decrease up to 65 h, respectively. The concentrations of these cytokines was strongly positively correlated with the number of monocytes/macrophages of each volunteer. TNF-alpha and IL-1 beta concentration after LPS stimulation was significantly reduced by simultaneously given IDS 23 in a strictly dose dependent manner. At time 24 h these cytokine concentrations were reduced by 50.8% and 99.7%, respectively, using the highest test IDS 23 assay concentration of 5 mg/ml (p < 0.001). After 65 h the corresponding inhibition was 38.9% and 99.9%, respectively (p < 0.001). On the other hand IDS 23 showed no inhibition but stimulated IL-6 secretion in absence of LPS alone. Simultaneously given LPS and IDS 23 resulted in no further increase. In contrast to described effects on arachidonic acid cascade in vitro, tested Urtica dioica phenol carbon acid derivates and flavonoides such as caffeic malic acid, caffeic acid, chlorogenic acid, quercetin and rutin did not influence LPS stimulated TNF-alpha, IL-1 beta and IL-6 secretion in tested concentrations up to 5 x 10(-5) mol/l. These further findings on the pharmacological mechanism of action of Urticae dioica folia may explain the positive effects of this extract in the treatment of rheumatic diseases.

Synthesis of a Series of Caffeic Acid Phenethyl Amide (CAPA) Fluorinated Derivatives: Comparison of Cytoprotective Effects to Caffeic Acid Phenethyl Ester (CAPE)

DTIC Science & Technology

2010-06-11

the cinnamic acid phenyl ring. Although compound 4c proved to be very cytotoxic in HUVEC over a 24 h period, the toxicity is less apparent over a 5 h...drug development process, as it determines how much of the initial dose actually reaches the target site. Cinnamic acid -derived amides are known to...Synthesis of a series of caffeic acid phenethyl amide (CAPA) fluorinated derivatives: Comparison of cytoprotective effects to caffeic acid phenethyl

Caffeic acid production by simultaneous saccharification and fermentation of kraft pulp using recombinant Escherichia coli.

PubMed

Kawaguchi, Hideo; Katsuyama, Yohei; Danyao, Du; Kahar, Prihardi; Nakamura-Tsuruta, Sachiko; Teramura, Hiroshi; Wakai, Keiko; Yoshihara, Kumiko; Minami, Hiromichi; Ogino, Chiaki; Ohnishi, Yasuo; Kondo, Ahikiko

2017-07-01

Caffeic acid (3,4-dihydroxycinnamic acid) serves as a building block for thermoplastics and a precursor for biologically active compounds and was recently produced from glucose by microbial fermentation. To produce caffeic acid from inedible cellulose, separate hydrolysis and fermentation (SHF) and simultaneous saccharification and fermentation (SSF) reactions were compared using kraft pulp as lignocellulosic feedstock. Here, a tyrosine-overproducing Escherichia coli strain was metabolically engineered to produce caffeic acid from glucose by introducing the genes encoding a 4-hydroxyphenyllactate 3-hydroxylase (hpaBC) from Pseudomonas aeruginosa and tyrosine ammonia lyase (fevV) from Streptomyces sp. WK-5344. Using the resulting recombinant strain, the maximum yield of caffeic acid in SSF (233 mg/L) far exceeded that by SHF (37.9 mg/L). In the SSF with low cellulase loads (≤2.5 filter paper unit/g glucan), caffeic acid production was markedly increased, while almost no glucose accumulation was detected, indicating that the E. coli cells experienced glucose limitation in this culture condition. Caffeic acid yield was also negatively correlated with the glucose concentration in the fermentation medium. In SHF, the formation of by-product acetate and the accumulation of potential fermentation inhibitors increased significantly with kraft pulp hydrolysate than filter paper hydrolysate. The combination of these inhibitors had synergistic effects on caffeic acid fermentation at low concentrations. With lower loads of cellulase in SSF, less potential fermentation inhibitors (furfural, 5-hydroxymethyfurfural, and 4-hydroxylbenzoic acid) accumulated in the medium. These observations suggest that glucose limitation in SSF is crucial for improving caffeic acid yield, owing to reduced by-product formation and fermentation inhibitor accumulation.

Effects of caffeic acid on cisplatin-induced hair cell damage in HEI-OC1 auditory cells.

PubMed

Choi, June; Kim, Shin Hye; Rah, Yoon Chan; Chae, Sung Won; Lee, Jong Dae; Md, Byung Don Lee; Park, Moo Kyun

2014-12-01

Cisplatin is a widely used anticancer chemotherapeutic agent. However, it is notorious for its ototoxicity and nephrotoxicity due to induction of reactive oxygen species (ROS). Caffeic acid is a naturally occurring polyphenol present in honey that is known to reduce the generation of oxygen-derived free radicals. The objective of the present study was to evaluate the protective effects and mechanism underlying the effect of caffeic acid on cisplatin-induced ototoxicity in HEI-OC1 auditory cell lines. Cell viability was measured using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Apoptosis was determined by Hoechst 33258 staining and Annexin V-fluorescein isothiocyanate/propidium iodide double staining. Cell cycle stages were analyzed by flow cytometry. The radical-scavenging activity of caffeic acid was assessed using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. The expression levels of caspase-3, -8, and -9, as well as the activity of caspase-3, were evaluated. Caffeic acid showed a protective effect against cisplatin-induced HEI-OC1 cell damage as demonstrated by the MTT assay. Caffeic acid decreased cell death by apoptosis and necrosis. Caffeic acid showed strong scavenging activity against the radical DPPH and decreased intracellular ROS production. Caffeic acid decreased the expression of caspase-3 and -8 and increased the activity of caspase-3. Caffeic acid attenuated cisplatin-induced hair cell loss in HEI-OC1 cell lines; these effects were mediated by its radical scavenging activity and inhibition of apoptosis. Copyright © 2014 Elsevier Ireland Ltd. All rights reserved.

Grape skins (Vitis vinifera L.) catalyze the in vitro enzymatic hydroxylation of p-coumaric acid to caffeic acid.

PubMed

Arnous, Anis; Meyer, Anne S

2009-12-01

The ability of grape skins to catalyze in vitro conversion of p-coumaric acid to the more potent antioxidant caffeic acid was studied. Addition of different concentrations of p-coumaric to red grape skins (Cabernet Sauvignon) resulted in formation of caffeic acid. This caffeic acid formation (Y) correlated positively and linearly to p-coumaric acid consumption (X): Y = 0.5 X + 9.5; R (2) = 0.96, P < 0.0001. The kinetics of caffeic acid formation with time in response to initial p-coumaric acid levels and at different grape skin concentrations, indicated that the grape skins harboured an o-hydroxylation activity, proposedly a monophenol- or a flavonoid 3'-monooxygenase activity (EC 1.14.18.1 or EC 1.14.13.21). The K (m) of this crude o-hydroxylation activity in the red grape skin was 0.5 mM with p-coumaric acid.

Thermal transformation of bioactive caffeic acid on fumed silica seen by UV-Vis spectroscopy, thermogravimetric analysis, temperature programmed desorption mass spectrometry and quantum chemical methods.

PubMed

Kulik, Tetiana V; Lipkovska, Natalia O; Barvinchenko, Valentyna M; Palyanytsya, Borys B; Kazakova, Olga A; Dudik, Olesia O; Menyhárd, Alfréd; László, Krisztina

2016-05-15

Thermochemical studies of hydroxycinnamic acid derivatives and their surface complexes are important for the pharmaceutical industry, medicine and for the development of technologies of heterogeneous biomass pyrolysis. In this study, structural and thermal transformations of caffeic acid complexes on silica surfaces were studied by UV-Vis spectroscopy, thermogravimetric analysis, temperature programmed desorption mass spectrometry (TPD MS) and quantum chemical methods. Two types of caffeic acid surface complexes are found to form through phenolic or carboxyl groups. The kinetic parameters of the chemical reactions of caffeic acid on silica surface are calculated. The mechanisms of thermal transformations of the caffeic chemisorbed surface complexes are proposed. Thermal decomposition of caffeic acid complex chemisorbed through grafted ester group proceeds via three parallel reactions, producing ketene, vinyl and acetylene derivatives of 1,2-dihydroxybenzene. Immobilization of phenolic acids on the silica surface improves greatly their thermal stability. Copyright © 2016 Elsevier Inc. All rights reserved.

The impact of high pressure processing on the phenolic profile, hydrophilic antioxidant and reducing capacity of purée obtained from commercial tomato varieties.

PubMed

Jeż, Maja; Wiczkowski, Wiesław; Zielińska, Danuta; Białobrzewski, Ireneusz; Błaszczak, Wioletta

2018-09-30

The effect of high hydrostatic pressure (HHP) (450-550-650 MPa/5-10-15 min) on polyphenols profile of purée obtained from commercial tomato varieties (Maliniak, Cerise, Black Prince and Lima) was investigated. Individual polyphenols, total phenolic index (TPI) were quantified using a mass spectrometer (HPLC-MS/MS). Photochemiluminescence (PCLACW), cyclic voltammetry (CV) and ferric reducing antioxidant power (FRAP) assays were used to determine the antioxidant capacity of the hydrophilic extract. The results demonstrated that at certain processing conditions, HHP may enhance or decrease the nutritional quality of tomato purée. However, the tomato variety was a key factor influencing the polyphenols profile and the antioxidant capacity. A significant positive correlation was found among TPI, FRAP or CV parameters and the concentration of caffeic, ferulic, sinapic and p-coumaric acids, and epicatechin. On the other hand, significant positive correlation was observed among antioxidant capacity (PCLACW), TPC, rutin and naringenin concentration as well as chlorogenic and isochlorogenic acids. Copyright © 2018 Elsevier Ltd. All rights reserved.

Reactivity of food phenols with iron and copper ions: binding, dioxygen activation and oxidation mechanisms.

PubMed

Nkhili, Ezzohra; Loonis, Michèle; Mihai, Simona; El Hajji, Hakima; Dangles, Olivier

2014-06-01

In this work, the affinity of common dietary phenols (gallic acid, caffeic acid, catechin, and rutin) for iron and copper ions was quantitatively investigated in neutral phosphate buffer as well as the reactivity of the complexes toward dioxygen. Contrasting behaviors were observed: because of the competing phosphate ions, Fe(III) binding is much slower than Fe(II) binding, which is rapidly followed by autoxidation of Fe(II) into Fe(III). With both ions, O2 consumption and H2O2 production are modest and the phenolic ligands are only slowly oxidized. By contrast, metal-phenol binding is fast with both Cu(I) and Cu(II). With Cu(I), O2 consumption and H2O2 production are very significant and the phenolic ligands are rapidly oxidized into a complex mixture of oligomers. The corresponding mechanism with Cu(II) is hampered by the preliminary rate-determining step of Cu(II) reduction by the phenols. The consequences of these findings for the stability and antioxidant activity of plant phenols are discussed.

Elderberry and Elderflower Extracts, Phenolic Compounds, and Metabolites and Their Effect on Complement, RAW 264.7 Macrophages and Dendritic Cells

PubMed Central

Ho, Giang Thanh Thi; Wangensteen, Helle; Barsett, Hilde

2017-01-01

Modulation of complement activity and inhibition of nitric oxide (NO) production by macrophages and dendritic cells may have therapeutic value in inflammatory diseases. Elderberry and elderflower extracts, constituents, and metabolites were investigated for their effects on the complement system, and on NO production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages and murine dendritic D2SC/I cells. The EtOH crude extracts from elderberry and elderflower and the isolated anthocyanins and procyanidins possessed strong complement fixating activity and strong inhibitory activity on NO production in RAW cells and dendritic cells. Phenolic compounds in the range of 0.1–100 µM showed a dose-dependent inhibition of NO production, with quercetin, rutin, and kaempferol as the most potent ones. Among the metabolites, caffeic acid and 3,4-dihydroxyphenylacetic acid showed the strongest inhibitory effects on NO production in both cell lines, without having cytotoxic effect. Only 4-methylcatechol was cytotoxic at the highest tested concentration (100 µM). Elderberry and elderflower constituents may possess inflammatory modulating activity, which increases their nutritional value. PMID:28282861

Elderberry and Elderflower Extracts, Phenolic Compounds, and Metabolites and Their Effect on Complement, RAW 264.7 Macrophages and Dendritic Cells.

PubMed

Ho, Giang Thanh Thi; Wangensteen, Helle; Barsett, Hilde

2017-03-08

Modulation of complement activity and inhibition of nitric oxide (NO) production by macrophages and dendritic cells may have therapeutic value in inflammatory diseases. Elderberry and elderflower extracts, constituents, and metabolites were investigated for their effects on the complement system, and on NO production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages and murine dendritic D2SC/I cells. The EtOH crude extracts from elderberry and elderflower and the isolated anthocyanins and procyanidins possessed strong complement fixating activity and strong inhibitory activity on NO production in RAW cells and dendritic cells. Phenolic compounds in the range of 0.1-100 µM showed a dose-dependent inhibition of NO production, with quercetin, rutin, and kaempferol as the most potent ones. Among the metabolites, caffeic acid and 3,4-dihydroxyphenylacetic acid showed the strongest inhibitory effects on NO production in both cell lines, without having cytotoxic effect. Only 4-methylcatechol was cytotoxic at the highest tested concentration (100 µM). Elderberry and elderflower constituents may possess inflammatory modulating activity, which increases their nutritional value.

Phenolic composition and antiparasitic activity of plants from the Brazilian Northeast "Cerrado".

PubMed

Calixto Júnior, João Tavares; de Morais, Selene Maia; Gomez, Celeste Vega; Molas, Cathia Coronel; Rolon, Miriam; Boligon, Aline Augusti; Athayde, Margareth Linde; de Morais Oliveira, Cícera Datiane; Tintino, Saulo Relison; Henrique Douglas, Melo Coutinho

2016-05-01

This work describes the antiparasitic and cytotoxic activities of three plant species from the Cerrado biome, Northeastern Brazil. Significant antiparasitic inhibition was observed against Trypanosoma cruzi (63.86%), Leishmania brasiliensis (92.20%) and Leishmania infantum (95.23%) when using ethanol extract from leaves of Guazuma ulmifolia Lam. (Malvaceae), at a concentration of 500 μg/mL. However, low levels of inhibition were observed when assessing leishmanicidal and trypanocidal (Clone CL-B5) activities of crude ethanol extracts from leaves and bast tissue of Luehea paniculata (Malvaceae) and leaves and bark of Prockia crucis (Salicaceae) at a concentration of 500 μg/mL. The extracts revealed the presence of phenolic acids such as gallic acid, chlorogenic acid, caffeic acid and rosmarinic acid, as well as flavonoids such as rutin, luteolin, apigenin and quercetin - the latter detected only in G. ulmifolia. G. ulmifolia extract displayed higher leishmanicidal activity probably due to the presence of quercetin, a potent known leishmanicidal compound. A cytotoxicity test indicated values over 50% at the highest concentration (1000 μg/mL) for all natural products, which were considered cytotoxic. This points out the need for further tests to enable future in vivo trials, including antineoplastic activity on human tumor cells.

Phenolic composition and antiparasitic activity of plants from the Brazilian Northeast “Cerrado”

PubMed Central

Calixto Júnior, João Tavares; de Morais, Selene Maia; Gomez, Celeste Vega; Molas, Cathia Coronel; Rolon, Miriam; Boligon, Aline Augusti; Athayde, Margareth Linde; de Morais Oliveira, Cícera Datiane; Tintino, Saulo Relison; Henrique Douglas, Melo Coutinho

2015-01-01

This work describes the antiparasitic and cytotoxic activities of three plant species from the Cerrado biome, Northeastern Brazil. Significant antiparasitic inhibition was observed against Trypanosoma cruzi (63.86%), Leishmania brasiliensis (92.20%) and Leishmania infantum (95.23%) when using ethanol extract from leaves of Guazuma ulmifolia Lam. (Malvaceae), at a concentration of 500 μg/mL. However, low levels of inhibition were observed when assessing leishmanicidal and trypanocidal (Clone CL-B5) activities of crude ethanol extracts from leaves and bast tissue of Luehea paniculata (Malvaceae) and leaves and bark of Prockia crucis (Salicaceae) at a concentration of 500 μg/mL. The extracts revealed the presence of phenolic acids such as gallic acid, chlorogenic acid, caffeic acid and rosmarinic acid, as well as flavonoids such as rutin, luteolin, apigenin and quercetin – the latter detected only in G. ulmifolia. G. ulmifolia extract displayed higher leishmanicidal activity probably due to the presence of quercetin, a potent known leishmanicidal compound. A cytotoxicity test indicated values over 50% at the highest concentration (1000 μg/mL) for all natural products, which were considered cytotoxic. This points out the need for further tests to enable future in vivo trials, including antineoplastic activity on human tumor cells. PMID:27081371

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

Effects of caffeic and chlorogenic acids on the rat skeletal system.

PubMed

Folwarczna, J; Pytlik, M; Zych, M; Cegieła, U; Nowinska, B; Kaczmarczyk-Sedlak, I; Sliwinski, L; Trzeciak, H; Trzeciak, H I

2015-02-01

Caffeic acid, predominantly as esters linked to quinic acid (chlorogenic acids), is a phenolic acid present at high levels in coffee. The aim of the study was to investigate effects of caffeic and chlorogenic acids on the skeletal system of female rats with normal estrogen levels and estrogen-deficient. Caffeic acid (5 and 50 mg/kg p.o. daily) and chlorogenic acid (100 mg/kg p.o. daily) were administered for 4 weeks to non-ovariectomized and bilaterally ovariectomized mature Wistar rats, and their effects were compared with appropriate controls. Moreover, estradiol (0.2 mg/kg p.o. daily) was administered to ovariectomized rats. Bone turnover markers, mass, mineralization and mechanical properties were examined. Although caffeic acid at a low dose exerted some unfavorable effects on the skeletal system, at high doses, caffeic and chlorogenic acids slightly increased mineralization in the tibia and improved mechanical properties of the femoral diaphysis (compact bone). Unlike estradiol, they did not counteract the worsening of the tibial metaphysis bone strength (cancellous bone) and increases in osteocalcin concentration induced by estrogen deficiency. High doses of the phenolic acids slightly favorably affected the rat skeletal system independently of the estrogen status.

Inhibitory Effects of Caffeic Acid, a Coffee-Related Organic Acid, on the Propagation of Hepatitis C Virus.

PubMed

Tanida, Isei; Shirasago, Yoshitaka; Suzuki, Ryosuke; Abe, Ryo; Wakita, Takaji; Hanada, Kentaro; Fukasawa, Masayoshi

2015-01-01

Multipurpose cohort studies have demonstrated that coffee consumption reduces the risk of hepatocellular carcinoma (HCC). Given that one of the main causes of HCC is hepatitis C virus (HCV) infection, we examined the effect of caffeic acid, a major organic acid derived from coffee, on the propagation of HCV using an in vitro naïve HCV particle-infection and production system within human hepatoma-derived Huh-7.5.1-8 cells. When cells were treated with 1% coffee extract or 0.1% caffeic acid for 1-h post HCV infection, the amount of HCV particles released into the medium at 3 and 4 days post-infection considerably decreased. In addition, HCV-infected cells cultured with 0.001% caffeic acid for 4 days, also released less HCV particles into the medium. Caffeic acid treatment inhibited the initial stage of HCV infection (i.e., between virion entry and the translation of the RNA genome) in both HCV genotypes 1b and 2a. These results suggest that the treatment of cells with caffeic acid may inhibit HCV propagation.

Phenolic Content of Hypodaphnis Zenkeri and Its Antioxidant Effects against Fenton Reactions’ Mediated Oxidative Injuries on Liver Homogenate

PubMed Central

Moukette Moukette, Bruno; Pieme, Constant Anatole; Nya Biapa, Prosper Cabral; Njimou, Jacques Romain; Ama Moor, Vicky Jocelyne; Stoller, Marco; Bravi, Marco; Ngogang, Jeanne Yonkeu

2014-01-01

Under oxidative stress conditions, endogenous antioxidant defenses are unable to completely inactivate the free radicals generated by an excessive production of reactive oxygen species (ROS). This state causes serious cell damage leading to a variety of human diseases. Natural antioxidants can protect cells against oxidative stress. Hypaodaphnis zenkeri (H. zenkiri) is a plant consumed as a spice in the Cameroonian diet, and its bark has been used in traditional medicine for the treatment of several diseases. The present study aims at investigating the antioxidant activity, which includes free radical scavenging and protective properties of an extract from H. Zenkiri against oxidative damage on a liver homogenate. The free radical assays determined the scavenging activities of 2,2-diphenyl-1-picrylhydrazyl (DPPH), hydroxyl (OH), nitrite oxide (NO) and 2,2-azinobis(3-ethylbenzthiazoline)-6-sulfonic acid (ABTS) radicals and the enzymes, whose protection was to be considered in the liver homogenate, including superoxide dismutase, catalase, and peroxidase. The antioxidative activities were studied using the ferric reducing antioxidant power (FRAP), reductive activity, and phosphomolybdenum antioxidant power (PAP) methods. In addition, the phenolic contents of the extracts were examined. The results showed that these extracts demonstrated significant scavenging properties and antioxidant activities, with the hydro-ethanolic extract of the bark of H. zenkeri (EEH) being the most potent. This extract had the highest total polyphenol (21.77 ± 0.05 mg caffeic acid (CAE)/g dried extract (DE)) and flavonoids (3.34 ± 0.13 mg quercetin (QE)/g dried extract) content. The same extract had significantly greater protective effects on enzyme activities compared to other extracts. The high performance liquied chromatography (HPLC) profile showed higher levels of caffeic acid, OH-tyrosol acid, and rutin in the leaves compared to the bark of H. zenkeri. In conclusion, the ethanolic and hydro-ethanolic extracts of the bark and leaves from H. zenkeri showed an antioxidant and protective potential against oxidative damage. PMID:26785245

Absorption and Metabolism of Phenolics from Digests of Polyphenol-Rich Potato Extracts Using the Caco-2/HepG2 Co-Culture System

PubMed Central

Sadeghi Ekbatan, Shima; Iskandar, Michele M.; Sleno, Lekha; Sabally, Kebba; Khairallah, Joelle; Prakash, Satya

2018-01-01

The bioactivity of dietary polyphenols depends upon gastrointestinal and hepatic metabolism of secondary microbial phenolic metabolites generated via colonic microbiota-mediated biotransformation. A polyphenol-rich potato extract (PRPE) containing chlorogenic, caffeic, and ferulic acids and rutin was digested in a dynamic multi-reactor gastrointestinal simulator of the human intestinal microbial ecosystem (GI model). Simulated digestion showed extensive degradation of the parent compounds and the generation of microbial phenolic metabolites. To characterize the transport and metabolism of microbial phenolic metabolites following digestion, a co-culture of intestinal Caco-2 and hepatic HepG2 cells was exposed to the PRPE-derived digests obtained from the colonic vessels. Following a 2 h incubation of the digesta with the Caco-2/HepG2 co-cultures, approximately 10–15% of ferulic, dihydrocaffeic, and dihydroferulic acids and 3–5% of 3-hydroxybenzoic, 3-hydroxyphenylpropionic, and coumaric acids were observed in the basolateral side, whereas 3-hydroxyphenylacetic acid, phenylpropanoic acid, and cinnamic acid were not detected. Subsequent HepG2 cellular metabolism led to major increases in ferulic, dihydrocaffeic, 3-hydroxyphenylpropionic, and coumaric acids ranging from 160–370%. These findings highlight the importance of hepatic metabolism towards the generation of secondary metabolites of polyphenols despite low selective Caco-2 cellular uptake of microbial phenolic metabolites. PMID:29329242

Combined treatment with caffeic and ferulic acid from Baccharis uncinella C. DC. (Asteraceae) protects against metabolic syndrome in mice.

PubMed

Bocco, B M; Fernandes, G W; Lorena, F B; Cysneiros, R M; Christoffolete, M A; Grecco, S S; Lancellotti, C L; Romoff, P; Lago, J H G; Bianco, A C; Ribeiro, M O

2016-03-01

Fractionation of the EtOH extract from aerial parts of Baccharis uncinella C. DC. (Asteraceae) led to isolation of caffeic and ferulic acids, which were identified from spectroscopic and spectrometric evidence. These compounds exhibit antioxidant and anti-inflammatory properties and have been shown to be effective in the prevention/treatment of metabolic syndrome. This study investigated whether the combined treatment of caffeic and ferulic acids exhibits a more significant beneficial effect in a mouse model with metabolic syndrome. The combination treatment with caffeic and ferulic acids was tested for 60 days in C57 mice kept on a high-fat (40%) diet. The data obtained indicated that treatment with caffeic and ferulic acids prevented gain in body weight induced by the high-fat diet and improved hyperglycemia, hypercholesterolemia and hypertriglyceridemia. The expression of a number of metabolically relevant genes was affected in the liver of these animals, showing that caffeic and ferulic acid treatment results in increased cholesterol uptake and reduced hepatic triglyceride synthesis in the liver, which is a likely explanation for the prevention of hepatic steatosis. In conclusion, the combined treatment of caffeic and ferulic acids displayed major positive effects towards prevention of multiple aspects of the metabolic syndrome and liver steatosis in an obese mouse model.

Caffeic and chlorogenic acids inhibit key enzymes linked to type 2 diabetes (in vitro): a comparative study.

PubMed

Oboh, Ganiyu; Agunloye, Odunayo M; Adefegha, Stephen A; Akinyemi, Ayodele J; Ademiluyi, Adedayo O

2015-03-01

Chlorogenic acid is a major phenolic compound that forms a substantial part of plant foods and is an ester of caffeic acid and quinic acid. However, the effect of the structures of both chlorogenic and caffeic acids on their antioxidant and antidiabetic potentials have not been fully understood. Thus, this study sought to investigate and compare the interaction of caffeic acid and chlorogenic acid with α-amylase and α-glucosidase (key enzymes linked to type 2 diabetes) activities in vitro. The inhibitory effect of the phenolic acids on α-amylase and α-glucosidase activities was evaluated. Thereafter, their antioxidant activities as typified by their 1,1-diphenyl-2 picrylhydrazyl radical scavenging ability and ferric reducing antioxidant properties were determined. The results revealed that both phenolic acids inhibited α-amylase and α-glucosidase activities in a dose-dependent manner (2-8 μg/mL). However, caffeic acid had a significantly (p<0.05) higher inhibitory effect on α-amylase [IC50 (concentration of sample causing 50% enzyme inhibition)=3.68 μg/mL] and α-glucosidase (IC50=4.98 μg/mL) activities than chlorogenic acid (α-amylase IC50=9.10 μg/mL and α-glucosidase IC50=9.24 μg/mL). Furthermore, both phenolic acids exhibited high antioxidant properties, with caffeic acid showing higher effects. The esterification of caffeic acid with quinic acid, producing chlorogenic acid, reduces their ability to inhibit α-amylase and α-glucosidase activities. Thus, the inhibition of α-amylase and α-glucosidase activities by the phenolic acids could be part of the possible mechanism by which the phenolic acids exert their antidiabetic effects.

Extraction of polyphenols in Himanthalia elongata and determination by high performance liquid chromatography with diode array detector prior to its potential use against oxidative stress.

PubMed

Belda, Mariola; Sanchez, Desiré; Bover, Elena; Prieto, Beatriz; Padrón, Carolina; Cejalvo, Dolores; Lloris, Jose Miguel

2016-10-15

Several studies have demonstrated the antioxidant capacity of seaweeds, which can be used for the development of biopharmaceuticals with extensive medical application. Antioxidant therapies appear to attenuate the organic deterioration originated by an excessive oxidative stress, which could prevent the harmful effects of various injuries such as ischemia-reperfusion (I/R) among others. Marine brown seaweeds play a significant role, as they are the only organisms on earth producing phlorotannins, which are polyphenols that exhibit important biological activity. To ensure obtaining an extract with the greatest antioxidant activity, some variables that affect the extraction of polyphenols are optimized, including seaweed amount, type of solvent, and time and temperature of extraction. Subsequently, the total phenolic content (TPC) and the antioxidant activity have been determined. The optimized condition was obtained for 6g of seaweed, ethanol: water proportion of 60:40 and 2h/60°C, achieving 548.33mg AG/100g seaweed and 76% of antioxidant activity. The characterization of the extracted polyphenols was made by HPLC/DAD. 11 polyphenols were identified in the extract: Phloroglucinol, Gallic Acid, Catechin, Rutin, Gentisic Acid, Chlorogenic Acid, Caffeic Acid, Coumaric, Ferulic, Myricetin and Quercetin. Copyright © 2016 Elsevier B.V. All rights reserved.

Colonic fermentation of polyphenolics from Sea buckthorn (Hippophae rhamnoides) berries: Assessment of effects on microbial diversity by Principal Component Analysis.

PubMed

Attri, Sampan; Sharma, Kavita; Raigond, Pinky; Goel, Gunjan

2018-03-01

The present study investigates the stability of polyphenolic in Sea buckthorn berries juice (SBJ) during different phases of digestion and its effect on colonic microbial diversity. At each stage, the Total polyphenolic content (TPC), Total antioxidant activity (TAA) and polyphenolic profile was determined. A 1.64 and 2.20 folds increase in TPC with 4.88 and 9.61 folds increase in TAA were observed during gastric and small intestine digestion (p<0.05) with the release of quercetin from food matrix. The digestion resulted in deformation of intact crystalline structure as indicated by scanning electron micrographs. The colonic fermentation resulted in an increase in quercetin, caffeic acid with decrease in rutin and chlorogenic acid after 36h of fermentation (p<0.05). The Shannon diversity index (H) of beneficial groups including Lactic acid bacteria (LAB), Bacteroides/Prevotella and Bifidobacteria was increased by 35%, 71% and 17%, respectively (p<0.05). The PCA analysis indicated that the presence and digestion of polyphenolics promote the proliferation of Bacteroides/Prevotella group as well as Lactic acid bacteria and Bifidobacteria. The results suggest that SBJ is good source of prebiotic substrate in terms of the proliferation of beneficial gut microbiota. Copyright © 2017 Elsevier Ltd. All rights reserved.

Cyanobacteria-mediated phenylpropanoids and phytohormones in rice (Oryza sativa) enhance plant growth and stress tolerance.

PubMed

Singh, Dhananjaya P; Prabha, Ratna; Yandigeri, Mahesh S; Arora, Dilip K

2011-11-01

Phenylpropanoids, flavonoids and plant growth regulators in rice (Oryza sativa) variety (UPR 1823) inoculated with different cyanobacterial strains namely Anabaena oryzae, Anabaena doliolum, Phormidium fragile, Calothrix geitonos, Hapalosiphon intricatus, Aulosira fertilissima, Tolypothrix tenuis, Oscillatoria acuta and Plectonema boryanum were quantified using HPLC in pot conditions after 15 and 30 days. Qualitative analysis of the induced compounds using reverse phase HPLC and further confirmation with LC-MS/MS showed consistent accumulation of phenolic acids (gallic, gentisic, caffeic, chlorogenic and ferulic acids), flavonoids (rutin and quercetin) and phytohormones (indole acetic acid and indole butyric acid) in rice leaves. Plant growth promotion (shoot, root length and biomass) was positively correlated with total protein and chlorophyll content of leaves. Enzyme activity of peroxidase and phenylalanine ammonia lyase and total phenolic content was fairly high in rice leaves inoculated with O. acuta and P. boryanum after 30 days. Differential systemic accumulation of phenylpropanoids in plant leaves led us to conclude that cyanobacterial inoculation correlates positively with plant growth promotion and stress tolerance in rice. Furthermore, the study helped in deciphering possible mechanisms underlying plant growth promotion and stress tolerance in rice following cyanobacterial inoculation and indicated the less explored avenue of cyanobacterial colonization in stress tolerance against abiotic stress.

Antioxidant Potential, DNA Protection, and HPLC-DAD Analysis of Neglected Medicinal Jurinea dolomiaea Roots

PubMed Central

Shah, Naseer Ali; Khan, Muhammad Rashid; Naz, Kiran; Khan, Mubarak Ali

2014-01-01

Jurinea dolomiaea Boiss., family Compositae, is a medicinally important plant of alpine region. Its tuberous roots are used in various ailments in folk medicine. This study was undertaken to estimate total phenolic (TPC) and total flavonoid contents (TFC) and to determine anti-free radical potential by diverse in vitro antioxidant assays. Crude methanol extract (JDME) was fractionated into n-hexane (JDHE), chloroform (JDCE), ethyl acetate (JDEE), n-butanol (JDBE), and aqueous (JDAE) fractions. The results indicated that JDEE and JDCE constituted the highest amount of TFC (807 ± 7.2 mg rutin equivalent/g sample) and TPC (757 ± 9.4 mg gallic acid equivalent/g sample), respectively. Significant correlation of TFC with IC50 values was recorded for •OH (R 2 = 0.91), H2O2 (R 2 = 0.82), and ABTS (R 2 = 0.82) assay. It could be made clear that JDEE was the most potent in antioxidant activity as compared to others, with generally lower IC50 values for DPPH (41.1 ± 1.0 μg/mL), ABTS (46.7 ± 0.6 μg/mL), H2O2 (42.2 ± 0.9 μg/mL), •OH (61.1 ± 1.1 μg/mL), O2 − (152 ± 1.1 μg/mL), and antilipid peroxidation (54.3 ± 1.6 μg/mL). HPLC chromatogram of JDEE revealed the presence of catechin, caffeic acid, and rutin. The results indicated the antioxidant activities of J. dolomiaea roots and merit further investigations for their use in oxidative stress related disorders. PMID:24982907

Fungal biotransformation of chlorogenic and caffeic acids by Fusarium graminearum: New insights in the contribution of phenolic acids to resistance to deoxynivalenol accumulation in cereals.

PubMed

Gauthier, Léa; Bonnin-Verdal, Marie-Noelle; Marchegay, Gisèle; Pinson-Gadais, Laetitia; Ducos, Christine; Richard-Forget, Florence; Atanasova-Penichon, Vessela

2016-03-16

Fusarium Head Blight and Gibberella Ear Rot, mainly caused by the fungi Fusarium graminearum and Fusarium culmorum, are two of the most devastating diseases of small-grain cereals and maize. In addition to yield loss, these diseases frequently result in contamination of kernels with toxic type B trichothecenes. The potential involvement of chlorogenic acid in cereal resistance to Fusarium Head Blight and Gibberella Ear Rot and to trichothecene accumulation was the focus of this study. The effects of chlorogenic acid and one of its hydrolyzed products, caffeic acid, on fungal growth and type B trichothecenes biosynthesis were studied using concentrations close to physiological amounts quantified in kernels and a set of F. graminearum and F. culmorum strains. Both chlorogenic and caffeic acids negatively impact fungal growth and mycotoxin production, with caffeic acid being significantly more toxic. Inhibitory efficiencies of both phenolic acids were strain-dependent. To further investigate the antifungal and anti "mycotoxin" effect of chlorogenic and caffeic acids, the metabolic fate of these two phenolic acids was characterized in supplemented F. graminearum broths. For the first time, our results demonstrated the ability of F. graminearum to degrade chlorogenic acid into caffeic, hydroxychlorogenic and protocatechuic acids and caffeic acid into protocatechuic and hydroxycaffeic acids. Some of these metabolic products can contribute to the inhibitory efficiency of chlorogenic acid that, therefore, can be compared as a "pro-drug". As a whole, our data corroborate the contribution of chlorogenic acid to the chemical defense that cereals employ to counteract F. graminearum and its production of mycotoxins. Copyright © 2016 Elsevier B.V. All rights reserved.

Design, synthesis, and evaluation of caffeic acid amides as synergists to sensitize fluconazole-resistant Candida albicans to fluconazole.

PubMed

Dai, Li; Zang, Chengxu; Tian, Shujuan; Liu, Wei; Tan, Shanlun; Cai, Zhan; Ni, Tingjunhong; An, Maomao; Li, Ran; Gao, Yue; Zhang, Dazhi; Jiang, Yuanying

2015-01-01

A series of caffeic acid amides were designed, synthesized, and their synergistic activity with fluconazole against fluconazole-resistant Candida albicans was evaluated in vitro. The title caffeic acid amides 3-30 except 26 exhibited potent activity, and the subsequent SAR study was conducted. Compound 3, 5, 21, and 34c, at a concentration of 1.0 μg/ml, decreased the MIC₈₀ of fluconazole from 128.0 μg/ml to 1.0-0.5 μg/ml against the fluconazole-resistant C. albicans. This result suggests that the caffeic acid amides, as synergists, can sensitize drug-resistant fungi to fluconazole. The SAR study indicated that the dihydroxyl groups and the amido groups linking to phenyl or heterocyclic rings are the important pharmacophores of the caffeic acid amides.

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.

In vitro antioxidant properties, free radicals scavenging activities of extracts and polyphenol composition of a non-timber forest product used as spice: Monodora myristica.

PubMed

Moukette, Bruno Moukette; Pieme, Constant Anatole; Njimou, Jacques Romain; Biapa, Cabral Prosper Nya; Marco, Bravi; Ngogang, Jeanne Yonkeu

2015-03-14

Excessive production of free radicals causes direct damage to biological molecules such as DNA, proteins, lipids, carbohydrates leading to tumor development and progression. Natural antioxidant molecules from phytochemicals of plant origin may directly inhibit either their production or limit their propagation or destroy them to protect the system. In the present study, Monodora myristica a non-timber forest product consumed in Cameroon as spice was screened for its free radical scavenging properties, antioxidant and enzymes protective activities. Its phenolic compound profile was also realized by HPLC. This study demonstrated that M. myristica has scavenging properties against DPPH(•), OH(•), NO(•), and ABTS(•) radicals which vary in a dose depending manner. It also showed an antioxidant potential that was comparable with that of Butylated Hydroxytoluene (BHT) and vitamin C used as standard. The aqueous ethanol extract of M. myristica barks (AEH); showed a significantly higher content in polyphenolic compounds (21.44 ± 0.24 mg caffeic acid/g dried extract) and flavonoid (5.69 ± 0.07 quercetin equivalent mg/g of dried weight) as compared to the other studied extracts. The HPLC analysis of the barks and leaves revealed the presence of several polyphenols. The acids (3,4-OH-benzoic, caffeic, gallic, O- and P- coumaric, syringic, vanillic), alcohols (tyrosol and OH-tyrosol), theobromine, quercetin, rutin, catechine and apigenin were the identified and quantified polyphenols. All the tested extracts demonstrated a high protective potential on the superoxide dismutase (SOD), catalase and peroxidase activities. Finally, the different extracts from M. myristica and specifically the aqueous ethanol extract reveal several properties such as higher free radical scavenging properties, significant antioxidant capacities and protective potential effects on liver enzymes.

Caffeic acid attenuates lipopolysaccharide-induced sickness behaviour and neuroinflammation in mice.

PubMed

Basu Mallik, Sanchari; Mudgal, Jayesh; Nampoothiri, Madhavan; Hall, Susan; Dukie, Shailendra Anoopkumar-; Grant, Gary; Rao, C Mallikarjuna; Arora, Devinder

2016-10-06

Accumulating data links inflammation, oxidative stress and immune system in the pathophysiology of major depressive disorders. Sickness behaviour is a set of behavioural changes that develop during infection, eventually leading to decrease in mobility and depressed behaviour. Lipopolysaccharide (LPS) induces a depression-like state in animals that mimics sickness behaviour. Caffeic acid, a naturally occurring polyphenol, possesses antioxidant and anti-inflammatory properties. The present study was designed to explore the potential of caffeic acid against LPS-induced sickness behaviour in mice. Caffeic acid (30mg/kg) and imipramine (15mg/kg) were administered orally one hour prior to LPS (1.5mg/kg) challenge. Behavioural assessment was carried out between 1 and 2h and blood samples were collected at 3h post-LPS injection. Additionally, cytokines (brain and serum) and brain oxidative stress markers were estimated. LPS increased the systemic and brain cytokine levels, altered the anti-oxidant defence and produced key signs of sickness behaviour in animals. Caffeic acid treatment significantly reduced the LPS-induced changes, including reduced expression of inflammatory markers in serum and whole brain. Caffeic acid also exerted an anti-oxidant effect, which was evident from the decreased levels of oxidative stress markers in whole brain. Our data suggests that caffeic acid can prevent the neuroinflammation-induced acute and probably the long term neurodegenerative changes. Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

Home Cooking and Phenolics: Effect of Thermal Treatment and Addition of Extra Virgin Olive Oil on the Phenolic Profile of Tomato Sauces.

PubMed

Vallverdú-Queralt, Anna; Regueiro, Jorge; Rinaldi de Alvarenga, José Fernando; Torrado, Xavier; Lamuela-Raventos, Rosa M

2014-04-09

Tomato products are a key component of the Mediterranean diet, which is strongly related to a reduced risk of cardiovascular events. The effect of cooking time (15, 30, 45, and 60 min) and the addition of extra virgin olive oil (5 and 10%) on the phenolic content of tomato sauces was monitored using liquid chromatography coupled to tandem mass spectrometry. Concentration of phenolics in the tomato sauces decreased during the cooking process, with the exception of caffeic acid and tyrosol. The main degradation observed was the oxidation of quercetin, since the hydroxy-function at the C-ring of this flavonoid is not blocked by a sugar moiety, unlike rutin. Higher levels of virgin olive oil in tomato sauce seemed to enhance the extraction of phenolic compounds from the tomato, leading to higher phenolic contents in the sauces. Thus, the food matrix containing the phenolic compounds plays a crucial role in determining their accessibility.

Gender difference following high cholesterol diet induced renal injury and the protective role of rutin and ascorbic acid combination in Wistar albino rats

PubMed Central

2012-01-01

Background An increased interest is given to the impact of high fat diet on health worldwide. Abnormalities in lipid metabolism induced by high cholesterol diet (HCD) were reported to exacerbate renal diseases via oxidative stress pathways. Rutin and ascorbic acid showed a protective role against oxidative stress-mediated diseases. Furthermore, both lipid metabolism and tissue response to oxidative stress damage was found to vary according to animal gender. Thus, the objective of this work was to examine possible gender-related differences and the possible protective effects of rutin and ascorbic acid supplementation on high cholesterol diet induced nephrotoxicity. Methods 96 young male and female Wistar albino rats were used. HCD supplemented animals were treated with rutin alone or in combination with ascorbic acid for 6 weeks. Creatinine plasma level was estimated. Furthermore, kidney levels of nucleic acids, total protein, malondialdehyde (MDA), reduced glutathione (GSH), total cholesterol, and triglycerides were determined. Finally, kidney tissues were used for histopathological examination. Results HCD supplementation decreased kidney level of nucleic acids, which was more prominent in female animals. Both vitamin combination significantly attenuated HCD induced decrease in nucleic acids. Moreover, kidney level of MDA was significantly altered by HCD in both genders, which was inhibited by rutin and ascorbic acid alone or in combination in male groups and by both vitamins in female groups. There was a reduction in kidney level of GSH by HCD, especially in male groups, which was attenuated by rutin and ascorbic acid combination. Kidney levels of total cholesterol and triglycerides were significantly increased by HCD supplementation in both genders. Coadministration with rutin and/or ascorbic acid protected from such increase, which was more obvious in both vitamins combination. Histopathological investigation supported vitamins protective effect, which was more prominent in male vitamins combination group. Conclusions HCD-induced renal injury in female was higher than in male animals, suggesting a better anti-oxidative stress defense response in male's kidney. Moreover, the antioxidant and reno-protective effects of rutin and ascorbic acid were augmented following their combination. PMID:22423898

Gender difference following high cholesterol diet induced renal injury and the protective role of rutin and ascorbic acid combination in Wistar albino rats.

PubMed

Al-Rejaie, Salim Salih; Abuohashish, Hatem Mustafa; Alkhamees, Osama Abdelrahman; Aleisa, Abdulaziz Mohammed; Alroujayee, Abdulaziz S

2012-03-16

An increased interest is given to the impact of high fat diet on health worldwide. Abnormalities in lipid metabolism induced by high cholesterol diet (HCD) were reported to exacerbate renal diseases via oxidative stress pathways. Rutin and ascorbic acid showed a protective role against oxidative stress-mediated diseases. Furthermore, both lipid metabolism and tissue response to oxidative stress damage was found to vary according to animal gender. Thus, the objective of this work was to examine possible gender-related differences and the possible protective effects of rutin and ascorbic acid supplementation on high cholesterol diet induced nephrotoxicity. 96 young male and female Wistar albino rats were used. HCD supplemented animals were treated with rutin alone or in combination with ascorbic acid for 6 weeks. Creatinine plasma level was estimated. Furthermore, kidney levels of nucleic acids, total protein, malondialdehyde (MDA), reduced glutathione (GSH), total cholesterol, and triglycerides were determined. Finally, kidney tissues were used for histopathological examination. HCD supplementation decreased kidney level of nucleic acids, which was more prominent in female animals. Both vitamin combination significantly attenuated HCD induced decrease in nucleic acids. Moreover, kidney level of MDA was significantly altered by HCD in both genders, which was inhibited by rutin and ascorbic acid alone or in combination in male groups and by both vitamins in female groups. There was a reduction in kidney level of GSH by HCD, especially in male groups, which was attenuated by rutin and ascorbic acid combination. Kidney levels of total cholesterol and triglycerides were significantly increased by HCD supplementation in both genders. Coadministration with rutin and/or ascorbic acid protected from such increase, which was more obvious in both vitamins combination. Histopathological investigation supported vitamins protective effect, which was more prominent in male vitamins combination group. HCD-induced renal injury in female was higher than in male animals, suggesting a better anti-oxidative stress defense response in male's kidney. Moreover, the antioxidant and reno-protective effects of rutin and ascorbic acid were augmented following their combination.

Mathematical evaluation of the amino acid and polyphenol content and antioxidant activities of fruits from different apricot cultivars.

PubMed

Sochor, Jiri; Skutkova, Helena; Babula, Petr; Zitka, Ondrej; Cernei, Natalia; Rop, Otakar; Krska, Boris; Adam, Vojtech; Provazník, Ivo; Kizek, Rene

2011-09-01

Functional foods are of interest because of their significant effects on human health, which can be connected with the presence of some biologically important compounds. In this study, we carried out complex analysis of 239 apricot cultivars (Prunus armeniaca L.) cultivated in Lednice (climatic area T4), South Moravia, Czech Republic. Almost all previously published studies have focused only on analysis of certain parameters. However, we focused on detection both primary and secondary metabolites in a selection of apricot cultivars with respect to their biological activity. The contents of thirteen biogenic alpha-L-amino acids (arginine, asparagine, isoleucine, lysine, serine, threonine, valine, leucine, phenylalanine, tryptophan, tyrosine, proline and alanine) were determined using ion exchange chromatography with UV-Vis spectrometry detection. Profile of polyphenols, measured as content of ten polyphenols with significant antioxidant properties (gallic acid, procatechinic acid, p-aminobenzoic acid, chlorogenic acid, caffeic acid, vanillin, p-coumaric acid, rutin, ferrulic acid and quercetrin), was determined by high performance liquid chromatography with spectrometric/electrochemical detection. Moreover, content of total phenolics was determined spectrophotometrically using the Folin-Ciocalteu method. Antioxidant activity was determined using five independent spectrophotometric methods: DPPH assay, DMPD method, ABTS method, FRAP and Free Radicals methods. Considering the complexity of the obtained data, they were processed and correlated using bioinformatics techniques (cluster analysis, principal component analysis). The studied apricot cultivars were clustered according to their common biochemical properties, which has not been done before. The observed similarities and differences were discussed.

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.

[Determination of chlorogenic acid, caffeic acid and linarin in Flos Chrysanthemi Indici from different places by RP-hPLC].

PubMed

Guo, Qiaosheng; Fang, Hailing; Shen, Haijin

2010-05-01

To evaluate the quality of Flos Chrysanthemi Indici which produced in twenty-two different producing places. Chlorogenic acid and caffeic acid were analyzed on a Shim-pack C8 colunm (4.6 mm x 250 mm, 5 microm) eluted with the mobile phase consisted of acetonitrile-0.5% phosphoric acid( 19:81). The detection wavelength was set at 326 nm. Linarin were eluted with the mobile phase consisted of methanol-water-acetic acid(26: 23: 1). The detection wavelength was set at 334 nm. The column temperature was 25 degrees C. The flow rate was 1.0 mL x min . The linear response ranged within 2.5-50 microg for chlorogenic acid (r = 0.998), 2.5-25 microg for caffeic acid (r = 0.998) and 4.97-41.47 microg for linarin (r = 0.999), respectively. Recoveries were 100.8% with RSD 2.1% for chlorogenic acid, 96.2% with RSD 2.3% for caffeic acid and 103.7% with RSD 1.8% for linarin. There was a significant difference in the content of chlorogenic acid, caffeic acid, linarin among the samples. The content of chlorogenic in the sample from Fengdou Chongqing city was the highest in those from other places. The content of caffeic acid in the all samples is very low. The content of linarin in the samples from Jiangsu province and Anhui province almost reached the national standard in pharmacopoeia.

Polydopamine-coated magnetic molecularly imprinted polymer for the selective solid-phase extraction of cinnamic acid, ferulic acid and caffeic acid from radix scrophulariae sample.

PubMed

Yin, Yuli; Yan, Liang; Zhang, Zhaohui; Wang, Jing; Luo, Ningjing

2016-04-01

We describe novel cinnamic acid polydopamine-coated magnetic imprinted polymers for the simultaneous selective extraction of cinnamic acid, ferulic acid and caffeic acid from radix scrophulariae sample. The novel magnetic imprinted polymers were synthesized by surface imprinting polymerization using magnetic multi-walled carbon nanotubes as the support material, cinnamic acid as the template and dopamine as the functional monomer. The magnetic imprinted polymers were characterized by transmission electron microscopy, scanning electron microscopy, Fourier transform infrared spectroscopy and vibrating sample magnetometry. The results revealed that the magnetic imprinted polymers had outstanding magnetic properties, high adsorption capacity, selectivity and fast kinetic binding toward cinnamic acid, ferulic acid and caffeic acid. Coupled with high-performance liquid chromatography, the extraction conditions of the magnetic imprinted polymers as a magnetic solid-phase extraction sorbent were investigated in detail. The proposed imprinted magnetic solid phase extraction procedure has been used for the purification and enrichment of cinnamic acid, ferulic acid and caffeic acid successfully from radix scrophulariae extraction sample with recoveries of 92.4-115.0% for cinnamic acid, 89.4-103.0% for ferulic acid and 86.6-96.0% for caffeic acid. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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.

Anti-inflammatory and anti-angiogenic effects of flavonoids isolated from Lycium barbarum Linnaeus on human umbilical vein endothelial cells.

PubMed

Wu, Wen-Bin; Hung, Dian-Kun; Chang, Fung-Wei; Ong, Eng-Thaim; Chen, Bing-Huei

2012-10-01

Anti-inflammatory and anti-angiogenic effects of flavonoids isolated from Lycium barbarum fruits, a traditional Chinese medicine, on human umbilical vein endothelial cells (HUVECs) were investigated. Initially, flavonoids were extracted with 80% ethanol and separated using a Cosmosil 140 C18-OPN column, with the acidic fraction eluted with deionized water being composed of chlorogenic acid, caffeoyl quinic acid, caffeic acid and p-coumaric acid and the neutral fraction eluted with methanol composed of quercetin-diglycoside, rutin and kaempferol-O-rutinoside. Flavonoid extract was effective in inhibiting expression of intercellular adhesion molecule-1 (ICAM-1) and vascular cell adhesion molecule (VCAM-1) induced by TNF-α in HUVECs. The RT-PCR analysis indicated that ICAM-1 mRNA induced by TNF-α was inhibited by flavonoid extract. The flavonoid extract attenuated TNF-α-induced IκB phosphorylation as well as NF-κB, p65 and p50 translocation from cytosol to nucleus, through inhibition on TNF-α- and H(2)O(2)-induced intracellular reactive oxygen species (ROS) production. For the anti-angiogenic study, the flavonoid extract inhibited vascular endothelial growth factor (VEGF)-induced cell proliferation and migration in HUVECs, as well as angiogenesis. However, the flavonoid extract did not inhibit VEGF signaling. Surprisingly, HUVECs adhesion to the extracellular matrix was compromised and adhesion-induced signaling was retarded by the flavonoid extract.

Comparative study on the inhibitory effect of caffeic and chlorogenic acids on key enzymes linked to Alzheimer's disease and some pro-oxidant induced oxidative stress in rats' brain-in vitro.

PubMed

Oboh, Ganiyu; Agunloye, Odunayo M; Akinyemi, Ayodele J; Ademiluyi, Adedayo O; Adefegha, Stephen A

2013-02-01

This study sought to investigate and compare the interaction of caffeic acid and chlorogenic acid on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), and some pro-oxidants (FeSO(4), sodium nitroprusside and quinolinic acid) induced oxidative stress in rat brain in vitro. The result revealed that caffeic acid and chlorogenic acid inhibited AChE and BChE activities in dose-dependent manner; however, caffeic acid had a higher inhibitory effect on AChE and BChE activities than chlorogenic acid. Combination of the phenolic acids inhibited AChE and BChE activities antagonistically. Furthermore, pro-oxidants such as, FeSO(4), sodium nitroprusside and quinolinic acid caused increase in the malondialdehyde (MDA) contents of the brain which was significantly decreased dose-dependently by the phenolic acids. Inhibition of AChE and BChE activities slows down acetylcholine and butyrylcholine breakdown in the brain. Therefore, one possible mechanism through which the phenolic acids exert their neuroprotective properties is by inhibiting AChE and BChE activities as well as preventing oxidative stress-induced neurodegeneration. However, esterification of caffeic acid with quinic acid producing chlorogenic acid affects these neuroprotective properties.

The effects of caffeic, coumaric and ferulic acids on proliferation, superoxide production, adhesion and migration of human tumor cells in vitro.

PubMed

Nasr Bouzaiene, Nouha; Kilani Jaziri, Soumaya; Kovacic, Hervé; Chekir-Ghedira, Leila; Ghedira, Kamel; Luis, José

2015-11-05

Reactive oxygen species are well-known mediators of various biological responses. In this study, we examined the effect of three phenolic acids, caffeic, coumaric and ferulic acids, on superoxide anion production, adhesion and migration of human lung (A549) and colon adenocarcinoma (HT29-D4) cancer cell lines. Proliferation of both tumor cells was inhibited by phenolic acids. Caffeic, coumaric and ferulic acids also significantly inhibited superoxide production in A549 and HT29-D4 cells. Superoxide anion production decreased by 92% and 77% at the highest tested concentration (200 µM) of caffeic acid in A549 and HT29-D4 cell lines respectively. Furthermore, A549 and HT29-D4 cell adhesion was reduced by 77.9% and 79.8% respectively at the higher tested concentration of ferulic acid (200 µM). Migration assay performed towards A549 cell line, revealed that tested compounds reduced significantly cell migration. At the highest concentration tested (200 µM), the covered surface was 7.7%, 9.5% and 35% for caffeic, coumaric or ferulic acids, respectively. These results demonstrate that caffeic, coumaric and ferulic acids may participate as active ingredients in anticancer agents against lung and colon cancer development, at adhesion and migration steps of tumor progression. Copyright © 2015 Elsevier B.V. All rights reserved.

Cytoprotective Effect of Caffeic Acid Phenethyl Ester (CAPE) and Catechol Ring-Fluorinated CAPE Derivatives Against Menadione-Induced Oxidative Stress in Human Endothelial Cells

DTIC Science & Technology

2006-03-31

chlorogenic acid , and rosmari- nic acid did not display any cytoprotective effect in this assay at 15 lM (data not shown). Within the same pas- sage of HUVEC...Cytoprotective effect of caffeic acid phenethyl ester (CAPE) and catechol ring-fluorinated CAPE derivatives against menadione-induced oxidative...accepted 13 March 2006 Available online 31 March 2006 Abstract—Caffeic acid phenethyl ester (CAPE), a natural polyphenolic compound with many

Evaluation of phenolic compounds and lipid-lowering effect of Morus nigra leaves extract.

PubMed

Zeni, Ana Lúcia B; Moreira, Tatianne D; Dalmagro, Ana Paula; Camargo, Anderson; Bini, Larissa A; Simionatto, Edésio L; Scharf, Dilamara R

2017-01-01

Morus nigra L. (Moraceae) is a tree known as black mulberry and the leaves are used in folk medicine in the treatment of diabetes, high cholesterol and menopause symptoms. The aim of this study was to evaluate the M. nigra leaves phytochemical profile in different extractions and the hypolipidemic effect of the infusion comparing to the fenofibrate. Morus nigra infusion (MN) showed higher amounts of phenolics and flavonoids (83.85 mg/g and 79.96 µg/g, respectively), as well as antioxidant activity (83.85%) than decoction or hydromethanolic extracts. Although, decoction showed the best result for ascorbic acid (4.35 mg/100 g) than hydromethanolic or infusion (2.51 or 2.13 mg/100 g, respectively). The phenolic acids gallic, chlorogenic and caffeic and the flavonoids quercetin, rutin and catechin were found in the M. nigra extracts. Hyperlipidemic rats treated with 100, 200 or 400 mg/kg of MN decreased serum cholesterol, triglycerides and normalized lipoproteins. Furthermore, MN inhibited lipid peroxidation in liver, kidney and brain of hyperlipidemic rats. This study provides evidence that M. nigra leaves extracts are rich in polyphenols, mainly chlorogenic acid, which normalized hyperlipidemic disturbance. The results suggest a potential therapeutic effect of the M. nigra leaves infusion on dislipidemic condition and related oxidative stress.

A network pharmacology-integrated metabolomics strategy for clarifying the difference between effective compounds of raw and processed Farfarae flos by ultra high-performance liquid chromatography-quadrupole-time of flight mass spectrometry.

PubMed

Ding, Mingya; Li, Zhen; Yu, Xie-An; Zhang, Dong; Li, Jin; Wang, Hui; He, Jun; Gao, Xiu-Mei; Chang, Yan-Xu

2018-07-15

This study aimed to clarify the difference between the effective compounds of raw and processed Farfarae flos using a network pharmacology-integrated metabolomics strategy. First, metabolomics data were obtained by ultra high-performance liquid chromatography-quadrupole-time of flight mass spectrometry (UHPLC-Q-TOF/MS). Then, metabolomics analysis was developed to screen for the influential compounds that were different between raw and processed Farfarae flos. Finally, a network pharmacology approach was applied to verify the activity of the screened compounds. As a result, 4 compounds (chlorogenic acid, caffeic acid, rutin and isoquercitrin) were successfully screened, identified, quantified and verified as the most influential effective compounds. They may synergistically inhibit the p38, JNK and ERK-mediated pathways, which would induce the inhibition of the expression of the IFA virus. The results revealed that the proposed network pharmacology-integrated metabolomics strategy was a powerful tool for discovering the effective compounds that were responsible for the difference between raw and processed Chinese herbs. Copyright © 2018 Elsevier B.V. All rights reserved.

In vitro investigation of the potential health benefits of wild Mediterranean dietary plants as anti-obesity agents with α-amylase and pancreatic lipase inhibitory activities.

PubMed

Marrelli, Mariangela; Loizzo, Monica Rosa; Nicoletti, Marcello; Menichini, Francesco; Conforti, Filomena

2014-08-01

Inhibition of digestive enzymes is one of the most widely studied mechanisms used to determine the potential efficacy of natural products as anti-obesity agents. In vitro studies reported here were performed to evaluate the inhibitory activity of formulations of edible plants from Italy on amylase and lipase by monitoring the hydrolysis of nitrophenyl caprilate and the hydrolysis of glycoside bonds in digestible carbohydrate foods. The formulation obtained from Capparis sicula exhibited the strongest inhibitory effect on pancreatic lipase (IC50 = 0.53 mg mL(-1) ) while the Borago officinalis formulation exhibited the strongest inhibitory effect on α-amylase (IC50 = 31.61 µg mL(-1) ). In order to characterise the extracts, high-performance thin-layer chromatography analysis of the formulations was performed, revealing the predominance of (±)-catechin in Mentha aquatica formulation, rutin in C. sicula, and caffeic acid and chlorogenic acid in Echium vulgare. The results obtained indicated that the extracts of C. sicula and B. officinalis could be good candidates for further studies to isolate pancreatic lipase and α-amylase inhibitors, respectively. © 2013 Society of Chemical Industry.

Determination of phenolic compounds content and antioxidant activity in skin, pulp, seed, cane and leaf of five native grape cultivars in West Azerbaijan province, Iran.

PubMed

Farhadi, Khalil; Esmaeilzadeh, Forough; Hatami, Mehdi; Forough, Mehrdad; Molaie, Rahim

2016-05-15

In the present work, the phenolic compounds content and antioxidant activity in the skin, pulp, seed, cane and leaf of one international (Muscat) and five native (Hosseini, Ghara Shira, Agh Shani, Ghara Shani and Ghara Ghandome) grape cultivated in West Azerbaijan, Iran were investigated. Ghara Shani grape skin was found to contain the highest content of total phenolic and anthocyanin and cane of Ghara Shani contains the highest amount of flavonoid. A remarkable DPPH radical scavenging activity up to 95% and consequently, the lowest IC50 was found for skin of Ghara Shani. According to RP-HPLC experiments, the highest concentration of phenolic compounds was identified as catechin (945 μg/g), epicatechin (482 μg/g), gallic acid (319 μg/g) and resveratrol (29.8 μg/g) in skin of Ghara Shani, quercetin in cane of Ghara Shani (956 μg/g), rutin in skin of Ghara Shira (298 μg/g) and caffeic acid in cane of Ghara Shira (17.4 μg/g). Copyright © 2015 Elsevier Ltd. All rights reserved.

Antioxidant and hepatoprotective activity of vitex honey against paracetamol induced liver damage in mice.

PubMed

Wang, Yuan; Li, Dan; Cheng, Ni; Gao, Hui; Xue, Xiaofeng; Cao, Wei; Sun, Liping

2015-07-01

Fourteen vitex honeys from China were investigated to evaluate its antioxidant and hepatoprotective activity against paracetamol-induced liver damage. All honey samples exhibited high total phenolic content (344-520 mg GAE per kg), total flavonoid content (19-31 mg Rutin per kg), and strong antioxidant activity in DPPH radical scavenging, ferric reducing antioxidant power and Ferrous ion-chelating ability. Nine phenolic acids were detected in vitex honey samples, in which caffeic acid was the main compound. Honey from Heibei Zanhuang (S2) ranked the highest antioxidant activity was orally administered to mice (5 g kg(-1), 20 g kg(-1)) for 70 days. In high-dose (20 g kg(-1)), vitex honey pretreatment resulting in significant increase in serum oxygen radical absorbance capacity (15.07%) and decrease in Cu(2+)-mediate lipoprotein oxidation (80.07%), and suppression in alanine aminotransferase (75.79%) and aspartate aminotransferase (74.52%), enhancement in the superoxide dismutase and glutathione peroxidase activities and reduction in malondialdehyde (36.15%) and 8-hydroxy-2'-deoxyguanosine (19.6%) formation compared with paracetamol-intoxicated group. The results demonstrated the hepatoprotection of vitex honey against paracetamol-induced liver damage might attribute to its antioxidant and/or perhaps pro-oxidative property.

Rutin, quercetin, and free amino acid analysis in buckwheat (Fagopyrum) seeds from different locations.

PubMed

Bai, C Z; Feng, M L; Hao, X L; Zhong, Q M; Tong, L G; Wang, Z H

2015-12-29

In this study, five common buckwheats and nine tartary buckwheats grown at different locations were analyzed for the contents of rutin, quercetin, and amino acids by high-performance liquid chromatography and spectrophotometry. The rutin content was higher than quercetin in buckwheat seeds. Rutin content was in the range from 0.05 (0.05 g per 100 g dry seeds) to 1.35% of buckwheat seeds. Quercetin content varied from 0.01 to 0.17% and in some common buckwheats it was even difficult to detect. Comparatively, tartary buckwheat seeds contained more rutin and quercetin than common buckwheat seeds. Meanwhile, the bran has higher rutin content than the farina in tartary buckwheat seeds, with a respective content of 0.45 to 1.19% and 0.14 to 0.67%. It was found that amino acid contents were around 1.79 to 12.65% (farina) and 5.74 to 7.89% (bran) in common buckwheats, and 1.73 to 5.63% (farina) and 2.64 to 16.78% (bran) in tartary buckwheat seeds. The highest total rutin content was found to be 1.35% in tartary buckwheat seeds from Sichuan, China. The highest total amounts of amino acid were detected to be 20.13% in tartary buckwheat seeds from Changzhi, Shanxi Province (China). Our results suggested that food products made of whole-buckwheat flour are healthier than those made of fine white flour.

The modulatory effects of caffeic acid on human monocytes and its involvement in propolis action.

PubMed

Búfalo, Michelle Cristiane; Sforcin, José Maurício

2015-05-01

Researchers have been interested in investigating the mechanisms of action of propolis and the compounds involved in its biological activity; however, the effect of its isolated constituents on human immune cells still deserves investigation. Thus, this study aimed to verify the action of caffeic acid on human monocytes in an attempt to verify its effects on the innate immunity, and to analyse its participation in propolis activity. Monocytes viability was assessed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide method after incubation with caffeic acid. Cell markers expression by monocytes (Toll-like receptors (TLR)-2, TLR-4, human leukocyte antigen (HLA)-DR and CD80) was analysed by flow cytometry. TNF-α and IL-10 production was determined by enzyme-linked immunosorbent assay and the activity of monocytes against Candida albicans was investigated after incubation with different concentrations of caffeic acid. Caffeic acid downregulated TLR-2 and HLA-DR expression and inhibited cytokine production whereas it upregulated the fungicidal activity of monocytes, without affecting cell viability. Caffeic acid exerted an immunomodulatory action in human monocytes in the evaluated parameters depending on concentration, with no cytotoxic effects. Moreover, it was partially involved in propolis action. © 2015 Royal Pharmaceutical Society.

Effect of caffeine, caffeic acid and their various combinations on enzymes of cholinergic, monoaminergic and purinergic systems critical to neurodegeneration in rat brain-In vitro.

PubMed

Akomolafe, S F; Akinyemi, A J; Ogunsuyi, O B; Oyeleye, S I; Oboh, G; Adeoyo, O O; Allismith, Y R

2017-09-01

Caffeine and caffeic acid are two bioactive compounds that are present in plant foods and are major constituent of coffee, cocoa, tea, cola drinks and chocolate. Although not structurally related, caffeine and caffeic acid has been reported to elicit neuroprotective properties. However, their different proportional distribution in food sources and possible effect of such interactions are not often taken into consideration. Therefore, in this study, we investigated the effect of caffeine, caffeic acid and their various combinations on activities of some enzymes [acetylcholinesterase (AChE), monoamine oxidase (MAO) ecto-nucleoside triphosphate diphosphohydrolase (E-NTPase), ecto-5 1 -nucleotidase (E-NTDase) and Na + /K + ATPase relevant to neurodegeneration in vitro in rat brain. The stock concentration of caffeine and caffiec acid and their various proportional combinations were prepared and their interactions with the activities of these enzymes were assessed (in vitro) in different brain structures. The Fe 2+ and Cu 2+ chelating abilities of the samples were also investigated. The results revealed that caffeine, caffeic acid and their various combinations exhibited inhibitory effect on activities of AChE, MAO, E-NTPase and E-NTDase, but stimulatory effect on Na + /K + ATPase activity. The combinations also exhibited Fe 2+ and Cu 2+ chelating abilities. Considering the various combinations, a higher caffeine to caffeic acid ratio produced significantly highest enzyme modulatory effects; these were significantly lower to the effect of caffeine alone but significantly higher than the effect of caffeic acid alone. These findings may provide new insight into the effect of proportional combination of these bioactive compounds as obtained in many foods especially with respect to their neuroprotective effects. Copyright © 2017 Elsevier B.V. All rights reserved.

Secondary metabolites of seven Hypericum species growing in Turkey.

PubMed

Cirak, Cuneyt; Radusiene, Jolita; Jakstas, Valdas; Ivanauskas, Liudas; Seyis, Fatih; Yayla, Fatih

2016-10-01

Context The genus Hypericum (Hypericaceae) has attracted remarkable scientific interest as its members have yielded many bioactive compounds. Objective The current study presents investigations on the accumulation of hypericin, pseudohypericin, hyperforin, adhyperforin, chlorogenic acid, neochlorogenic acid, caffeic acid, 2,4-dihydroxybenzoic acid, 13,118-biapigenin, hyperoside, isoquercitrin, quercitrin, quercetin, avicularin, rutin, (+)-catechin and (-)-epicatechin in seven Hypericum (Hypericaceae) species growing wild in Turkey, namely, H. aviculariifolium Jaup. and Spach subsp. aviculariifolium (Freyn and Bornm.) Robson var. albiflorum (endemic), H. bithynicum Boiss., H. calycinum L., H. cardiophyllum Boiss., H. elongatum L. subsp. microcalycinum (Boiss. and Heldr.) Robson, H. hirsutum L. and H. xylosteifolium (Spach) N. Robson. Materials and methods The plant materials were collected at flowering period and dissected in different tissues. Air-dried plant material including stems, leaves and flowers was mechanically powdered with a laboratory mill and samples (0.1 g) were extracted in 10 mL of 100% methanol by ultrasonication at 40 °C for 30 min for HPLC-PDA analyses. Results Accumulation levels of the investigated compounds varied greatly depending on species and plant part. Discussion For the first time, the detailed chemical profiles of corresponding Turkish Hypericum species were reported and the results were discussed from a phytochemical point of view. Conclusions The present data have importance in evaluation of plant resources of Hypericum genus in selecting the new potential sources of bioactive compounds.

Anti-inflammatory effects of the roots of Alpinia pricei Hayata and its phenolic compounds.

PubMed

Yu, Yu-Shan; Hsu, Chin-Lin; Yen, Gow-Chin

2009-09-09

Alpinia pricei Hayata is cultivated throughout Asia and is an endemic plant in Taiwan. The leaf and root of this plant are used for traditional wrapping of food and as a cooking substitute for fresh ginger. The aim of this work was to study the in vitro anti-inflammatory effects of ethanol extracts from A. pricei Hayata (EEAP) and its phenolic compounds. High-performance liquid chromatography (HPLC) profiling indicated that EEAP contained caffeic acid, chlorogenic acid, ferulic acid, p-hydroxybenzoic acid, rutin, apigenin, curcumin and pinocembrin. EEAP and its phenolic compounds, apigenin, curcumin, and pinocembrin, inhibited lipopolysaccharide (LPS)-stimulated nitric oxide (NO) and prostaglandin E(2) (PGE(2)) production in RAW 264.7 cells. Furthermore, EEAP, apigenin, curcumin, and pinocembrin decreased LPS-mediated induction of protein and mRNA expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in RAW 264.7 cells. In addition, EEAP and its major active compound pinocembrin inhibited LPS-induced nuclear translocation of nuclear factor-kappaB (NF-kappaB) and NF-kappaB-mediated reporter gene expression. EEAP and pinocembrin also significantly inhibited LPS-induced intracellular reactive oxygen species (ROS) production in RAW 264.7 cells. When these results are taken together, they indicate that EEAP and pinocembrin suppressed LPS-induced NO and PGE(2) production by inhibition of NF-kappaB nuclear translocation and ROS generation.

Topical anti-inflammatory activity of Solanum corymbiflorum leaves.

PubMed

Piana, Mariana; Camponogara, Camila; Boligon, Aline Augusti; Machado, Michel Mansur; de Brum, Thiele Faccim; Oliveira, Sara Marchesan; de Freitas Bauermann, Liliane

2016-02-17

Solanum corymbiflorum is popularly known as "baga-de-veado" and its leaves are applied on inflamed legs, scabies, tick bite, boils, mastitis, low back pain and otitis. The aim of this study was evaluate anti-inflammatory in vivo activity and relate this activity with antioxidant compounds present in the extract of S. corymbiflorum leaves. The extract from S. corymbiflorum leaves topically applied was able to reduce the croton oil-induced ear edema and myeloperoxidase (MPO) activity with maximum inhibition of 87±3% and 45±7%, rescpectively in the dose of 1mg/ear. Similar results were found for positive control dexamethasone, which presented inhibitions of ear edema and MPO activity of 89±3% and 50±3%, respectively in a dose of 0.1mg/ear. These findings are due, at least in part, the presence of polyphenols (195.28mg GAE/g) and flavonoids, as chlorogenic acid (59.27mg/g), rutin (12.72mg/g), rosmarinic acid, caffeic acid and gallic acid found by high performance liquid chromatography (HPLC) analysis. This species showed potencial antioxidant by 1,1-diphenyl-2-picrylhydrazyl (DPPH), and carbonyl groups in proteins methods which may be related with the presence of this compounds. This species possess anti-inflammatory activity confirming their popular use for the local treatment of skin inflammatory disorders. Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.

The effect of greenhouse covering materials on phytochemical composition and antioxidant capacity of tomato cultivars.

PubMed

Ahmadi, Latifeh; Hao, Xiuming; Tsao, Rong

2018-02-13

The effect of light transmission (direct and diffuse) on the phenolic compounds of five tomato cultivars was investigated under controlled conditions in greenhouses covered with different covering materials. The type of covering material and type of diffusion of light simultaneously affected the reducing power of cultivars. Two-way analysis of variance showed statistically significant differences in total phenolic content for the different cultivars (P < 0.05) but not for the covering materials. Analysis by ultrahigh-performance liquid chromatography with diode array detection and liquid chromatography/tandem mass spectrometry showed the presence of major phenolic acid compounds such as chlorogenic acid, hydroxycinnamic acid/rutin, caffeic acid, ferulic acid and coumaric acid as well as flavonoid compounds such as myricetin, quercetin and naringenin. Most of the identified compounds showed a significant difference in different treatments due to both cultivar and covering material (P < 0.05). Statistical analysis showed that the type of covering material used influenced the total carotenoid and lycopene content (P < 0.05); however, the amount of lutein was not influenced by the type of covering material (P > 0.05). This study showed that the use of solar energy transmission could positively affect the reducing power of cultivars and alter the biosynthesis of certain phytochemicals that are health-beneficial. Further study could lead to applications for producing greenhouse vegetables with greater health attributes. © 2018 Society of Chemical Industry. © 2018 Society of Chemical Industry.

Simultaneous determination of phenolic acids and flavonoids in rice using solid-phase extraction and RP-HPLC with photodiode array detection.

PubMed

Irakli, Maria N; Samanidou, Victoria F; Biliaderis, Costas G; Papadoyannis, Ioannis N

2012-07-01

An analytical method based on an optimized solid-phase extraction procedure and followed by high-performance liquid chromatography (HPLC) separation with diode array detection was developed and validated for the simultaneous determination of phenolic acids (gallic, protocatechuic, 4-hydroxy-benzoic, vanillic, caffeic, syringic, p-coumaric, ferulic, sinapic, and cinnamic acids), flavanols (catechin and epicatechin), flavonols (myricetin, quercetin, kaempferol, quercetin-3-O-glucoside, hyperoside, and rutin), flavones (luteolin and apigenin) and flavanones (naringenin and hesperidin) in rice flour (Oryza sativa L.). Chromatographic separation was carried out on a PerfectSil Target ODS-3 (250 mm × 4.6 mm, 3 μm) column at temperature 25°C using a mobile phase, consisting of 0.5% (v/v) acetic acid in water, methanol, and acetonitrile at a flow rate 1 mL min(-1) , under gradient elution conditions. Application of optimum extraction conditions, elaborated on both Lichrolut C(18) and Oasis HLB cartridges, have led to extraction of phenolic acids and flavonoids from rice flour with mean recoveries 84.3-113.0%. The developed method was validated in terms of linearity, accuracy, precision, stability, and sensitivity. Repeatability (n = 5) and inter-day precision (n = 4) revealed relative standard deviation (RSD) <13%. The optimized method was successfully applied to the analysis of phenolic acids and flavonoids in pigmented (red and black rice) and non-pigmented rice (brown rice) samples. © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Polyphenol fatty acid esters as serine protease inhibitors: a quantum-chemical QSAR analysis.

PubMed

Viskupicova, Jana; Danihelova, Martina; Majekova, Magdalena; Liptaj, Tibor; Sturdik, Ernest

2012-12-01

We investigated the ability of polyphenol fatty acid esters to inhibit the activity of serine proteases trypsin, thrombin, elastase and urokinase. Potent protease inhibition in micromolar range was displayed by rutin and rutin derivatives esterified with medium and long chain, mono- and polyunsaturated fatty acids (1e-m), followed by phloridzin and esculin esters with medium and long fatty acid chain length (2a-d, 3a-d), while unmodified compounds showed only little or no effect. QSAR study of the compounds tested provided the most significant parameters for individual inhibition activities, i.e. number of hydrogen bond donors for urokinase, molecular volume for thrombin, and solvation energy for elastase. According to the statistical analysis, the action of elastase inhibitors is opposed to those of urokinase and thrombin. Cluster analysis showed two groups of compounds: original polyphenols together with rutin esters with short fatty acid chain length and rutin esters with long fatty acid chain length.

Rutin suppresses palmitic acids-triggered inflammation in macrophages and blocks high fat diet-induced obesity and fatty liver in mice.

PubMed

Gao, Mingming; Ma, Yongjie; Liu, Dexi

2013-11-01

To elucidate the mechanism of rutin in blocking macrophage-mediated inflammation and high fat diet-induced obesity and fatty liver. Both in vitro and in vivo approaches were taken in evaluating the effects of rutin on palmitic acids-triggered inflammation in cultured macrophages, and on weight gain and development of fatty liver of mice fed a high fat diet. Palmitic acids increase mRNA levels of pro-inflammatory cytokines, and elevate the production of TNFα in cultured macrophages. Pre-exposure of rutin to cells greatly suppressed these elevations. The suppressed inflammation by rutin was correlated with a decrease in transcription of genes responsible for ER stress and production of reactive oxygen species. In vivo, rutin protects mice from high fat diet-induced obesity, fatty liver and insulin resistance. The protective effects were associated with lack of hypertrophy and crown-like structures in the white adipose tissue, decreased mRNA levels of marker genes for macrophages including F4/80, Cd11c and Cd68, and repressed transcription of genes involved in chronic inflammation such as Mcp1 and Tnfα in white adipose tissue. In addition, rutin increases the expression of genes responsible for energy expenditure in brown adipose tissue including Pgc1α and Dio2. Furthermore, rutin suppresses transcription of Srebp1c and Cd36 in the liver, leading to a blockade of fatty liver development. These results suggest that supplementation of rutin is a promising strategy for blocking macrophage-mediated inflammation and inflammation-induced obesity and its associated complications.

Reduction of the DNA damages, Hepatoprotective Effect and Antioxidant Potential of the Coconut Water, ascorbic and Caffeic Acids in Oxidative Stress Mediated by Ethanol.

PubMed

Bispo, Vanderson S; Dantas, Lucas S; Chaves, Adriano B; Pinto, Isabella F D; Silva, Railmara P DA; Otsuka, Felipe A M; Santos, Rodrigo B; Santos, Aline C; Trindade, Danielle J; Matos, Humberto R

2017-01-01

Hepatic disorders such as steatosis and alcoholic steatohepatitis are common diseases that affect thousands of people around the globe. This study aims to identify the main phenol compounds using a new HPLC-ESI+-MS/MS method, to evaluate some oxidative stress parameters and the hepatoprotective action of green dwarf coconut water, caffeic and ascorbic acids on the liver and serum of rats treated with ethanol. The results showed five polyphenols in the lyophilized coconut water spiked with standards: chlorogenic acid (0.18 µM), caffeic acid (1.1 µM), methyl caffeate (0.03 µM), quercetin (0.08 µM) and ferulic acid (0.02 µM) isomers. In the animals, the activity of the serum γ-glutamyltranspeptidase (γ-GT) was reduced to 1.8 I.U/L in the coconut water group, 3.6 I.U/L in the ascorbic acid group and 2.9 I.U/L in the caffeic acid groups, when compared with the ethanol group (5.1 I.U/L, p<0.05). Still in liver, the DNA analysis demonstrated a decrease of oxidized bases compared to ethanol group of 36.2% and 48.0% for pretreated and post treated coconut water group respectively, 42.5% for the caffeic acid group, and 34.5% for the ascorbic acid group. The ascorbic acid was efficient in inhibiting the thiobarbituric acid reactive substances (TBARS) in the liver by 16.5% in comparison with the ethanol group. These data indicate that the green dwarf coconut water, caffeic and ascorbic acids have antioxidant, hepatoprotective and reduced DNA damage properties, thus decreasing the oxidative stress induced by ethanol metabolism.

Ameliorative Effect of Caffeic Acid on Capecitabine-Induced Hepatic and Renal Dysfunction: Involvement of the Antioxidant Defence System

PubMed Central

Olayinka, Ebenezer Tunde; Ore, Ayokanmi; Adeyemo, Oluwatobi Adewumi

2017-01-01

Background: It has been postulated that during liver and kidney damage there is a decreased in the antioxidant status associated with a simultaneous increase in the reactive oxygen species and lipid peroxidation. In consonant with this, Capecitabine, an oral chemotherapy and inactive non-cytotoxic fluoropyrimidine considered for the treatment of advance colorectal cancer, has also been shown to induce oxidative stress in liver tissues. Caffeic acid, a typical hydroxycinnamic, has been claimed to be effective against oxidative stress. Therefore, this present work studied the protective effect of caffeic acid on oxidative stress-induced liver and kidney damage by the administration of capecitabine. Methods: Twenty-four male Wistar strain rats were randomly divided into four treatment groups: A. control, B. capecitabine (CPTB)-treated group (30 mg/kg b.w. CPTB), C. caffeic acid (CFA)-treated group (100 mg/kg b.w. CFA) and D. co-treated group with CFA (100 mg/kg b.w.) and CPTB (30 mg/kg b.w.). Results: Caffeic acid administration significantly ameliorated the elevated plasma biomarkers of hepatic and renal tissue damage induced by the capecitabine and improved enzymatic and non-enzymatic antioxidant levels in liver organ. Conclusions: The protective effect of caffeic acid could be attributed to its ability to boost the antioxidant defence system and reduce lipid peroxidation. PMID:29068374

Genomic study of the absorption mechanism of p-coumaric acid and caffeic acid of extract of Ananas comosus L. leaves.

PubMed

Dang, Yun-jie; Zhu, Chun-yan

2015-03-01

Cardiac disease has emerged as the leading cause of death worldwide, and food rich in phenolic acids has drawn much attention as sources of active substances of hypolipidemic drug. Ananas comosus L. (pineapple) is one of the most popular tropical and subtropical fruits. Isolated from pineapple leaves, EAL(Extract of Ananas Comosus L. Leaves) is rich in phenolic acids, such as p-coumaric acid, caffeic acid, and other phenolics, highly relevant to the putative cardiovascular-protective effects, which suggests its potential to be a new plant medicine for treatment of cardiac disease, but little is known about absorption, distribution, metabolism, and excretion of EAL in animals or human beings. In this study, we employed cDNA microarray, Caco-2 cell lines, and rat intestinal model to explore the absorption behavior of p-coumaric acid and caffeic acid in EAL. The permeation of 2 substances was concentration and time dependent. Results also indicated that monocarboxylic acid transporter was involved in the transepithelial transport of p-coumaric acid and caffeic acid. © 2015 Institute of Food Technologists®

Caffeic acid and quercetin protect erythrocytes against the oxidative stress and the genotoxic effects of lambda-cyhalothrin in vitro.

PubMed

Abdallah, Fatma Ben; Fetoui, H; Fakhfakh, F; Keskes, L

2012-01-01

Lambda-cyhalothrin (LTC) is a synthetic pyrethroid with a broad spectrum of insecticidal and acaricidal activities used to control wide range of insect pests in a variety of applications. The aim of this study was to examine (i) the potency of LTC to induce oxidative stress response in rat erythrocytes in vitro and (ii) the role of caffeic acid (20 μM) and/or quercetin (10 μM) in preventing the cytotoxic effects. Erythrocytes were divided into four portions. The erythrocytes of the first portion were incubated for 4 h at 37°C with different concentrations (0, 50 and 100 μM) of LTC. The others portions were pretreated with caffeic acid and/or quercetin for 30 min prior to LTC incubation. Lipid peroxidation, protein oxidation, antioxidant enzyme activities and DNA damage were examined. LTC at different concentrations causes increased levels of lipid peroxidation, protein oxidation, DNA damage and decreased antioxidant enzyme activities. Combined caffeic acid and quercetin pretreatments significantly reduced the levels of lipid peroxidation markers, that is thiobarbituric acid reactive substance (TBARS), protein carbonyls (PCO) and decreased DNA damage in LTC portion. Further, combined caffeic acid and quercetin pretreatment maintain antioxidant enzyme activities and glutathione content near to normal values. These results suggest that LTC exerts its toxic effect by increasing lipid peroxidation, altering the antioxidant enzyme activities and DNA damage. Caffeic acid and quercetin pretreatments prevent the toxic effects of LTC, suggesting their role as a potential antioxidant.

Survival of Escherichia coli O157:H7 ATCC 43895 in a Model Apple Juice Medium with Different Concentrations of Proline and Caffeic Acid

PubMed Central

Reinders, Robert D.; Biesterveld, Steef; Bijker, Peter G. H.

2001-01-01

The effects of proline and caffeic acid on the survival of Shiga toxin-producing Escherichia coli (STEC) O157:H7 strain ATCC 43895 in a model apple juice medium were studied. It is hypothesized that the inhibitory effect of caffeic acid may explain why almost all outbreaks of STEC O157:H7 infections linked to apple juice or cider have occurred in October or November. PMID:11375209

Pharmacokinetics of Caffeic Acid, Ferulic Acid, Formononetin, Cryptotanshinone, and Tanshinone IIA after Oral Administration of Naoxintong Capsule in Rat by HPLC-MS/MS.

PubMed

Li, Jin; Bai, Yang; Bai, Yun; Zhu, Ruichao; Liu, Wei; Cao, Jun; An, Mingrui; Tan, Zhijing; Chang, Yan-Xu

2017-01-01

Naoxintong capsule (NXTC) was a famous patent medicine of Traditional Chinese Medicine (TCM) to treat cerebrovascular diseases in China. An LC-MS/MS method was developed for simultaneous determination of 11 major ingredients (paeoniflorin, ecdysterone, amygdalin, mulberroside A, caffeic acid, ferulic acid, salvianolic acid B, astragaloside IV, formononetin, cryptotanshinone, and tanshinone IIA) in NXTC in rat plasma. All analytes were separated on an Eclipse plus C 18 column using a gradient mobile phase system of acetonitrile-0.1% formic acid aqueous solution. The lower limits of quantification of 11 ingredients were between 0.075 and 10 ng mL -1 . The precision was less than 15% and the accuracies were between 85% and 115%. The results showed that caffeic acid, ferulic acid, formononetin, cryptotanshinone, and tanshinone IIA could be detected after oral administration of NXTC. The validated method was successfully applied to pharmacokinetic study of the caffeic acid, ferulic acid, formononetin, cryptotanshinone, and tanshinone IIA in rats after oral administration of NXTC at single and triple dose.

Antibacterial Efficacy of Dihydroxylated Chalcones in Binary and Ternary Combinations with Nalidixic Acid and Nalidix Acid-Rutin Against Escherichia coli ATCC 25 922.

PubMed

Talia, Juan Manuel; Tonn, Carlos Eugenio; Debattista, Nora Beatriz; Pappano, Nora Beatriz

2012-12-01

In order to determine the existence of synergism, the bacteriostatic action of flavonoids against Escherichia coli ATCC 25 922 between dihydroxylated chalcones and a clinically interesting conventional antibiotic, binary combinations of 2',3-dihydroxychalcone, 2',4-dihydroxychalcone and 2',4'-dihydroxychalcone with nalidixic acid and its ternary combinations with rutin (inactive flavonoid) were assayed against this Gram negative bacterium. Using a kinetic-turbidimetric method, growth kinetics were monitored in broths containing variable amounts of dihydroxychalcone alone, combinations of dihydroxychalcone variable concentration-nalidixic acid constant concentration and dihydroxychalcone variable concentration-nalidixic acid constant concentration-rutin constant concentration, respectively. The minimum inhibitory concentrations of dihydroxychalcones alone and its binary and ternary combinations were evaluated. All chalcones, and their binary and ternary combinations showed antibacterial activity, being rutin an excellent synergizing for the dihydroxychalcone-nalidixic acid binary combination against E. coli ATCC 25 922. Thus, this synergistic effect is an important way that could lead to the development of new combination antibiotics against infections caused by E. coli.

Square-wave stripping voltammetric determination of caffeic acid on electrochemically reduced graphene oxide-Nafion composite film.

PubMed

Filik, Hayati; Çetintaş, Gamze; Avan, Asiye Aslıhan; Aydar, Sevda; Koç, Serkan Naci; Boz, İsmail

2013-11-15

An electrochemical sensor composed of Nafion-graphene nanocomposite film for the voltammetric determination of caffeic acid (CA) was studied. A Nafion graphene oxide-modified glassy carbon electrode was fabricated by a simple drop-casting method and then graphene oxide was electrochemically reduced over the glassy carbon electrode. The electrochemical analysis method was based on the adsorption of caffeic acid on Nafion/ER-GO/GCE and then the oxidation of CA during the stripping step. The resulting electrode showed an excellent electrocatalytical response to the oxidation of caffeic acid (CA). The electrochemistry of caffeic acid on Nafion/ER-GO modified glassy carbon electrodes (GCEs) were studied by cyclic voltammetry and square-wave adsorption stripping voltammetry (SW-AdSV). At optimized test conditions, the calibration curve for CA showed two linear segments: the first linear segment increased from 0.1 to 1.5 and second linear segment increased up to 10 µM. The detection limit was determined as 9.1×10(-8) mol L(-1) using SW-AdSV. Finally, the proposed method was successfully used to determine CA in white wine samples. Copyright © 2013 Elsevier B.V. All rights reserved.

Antibacterial, Antibiofilm Effect of Burdock (Arctium lappa L.) Leaf Fraction and Its Efficiency in Meat Preservation.

PubMed

Lou, Zaixiang; Li, Cheng; Kou, Xingran; Yu, Fuhao; Wang, Hongxin; Smith, Gary M; Zhu, Song

2016-08-01

First, the antibacterial, antibiofilm effect and chemical composition of burdock (Arctium lappa L.) leaf fractions were studied. Then, the efficiency of burdock leaf fractions in pork preservation was evaluated. The results showed that burdock leaf fraction significantly inhibited the growth and biofilm development of Escherichia coli and Salmonella Typhimurium. MICs of burdock leaf fractions on E. coli and Salmonella Typhimurium were both 2 mg/ml. At a concentration of 2.0 mg/ml, the inhibition rates of the fraction on growth and development of E. coli and Salmonella Typhimurium biofilms were 78.7 and 69.9%, respectively. During storage, the log CFU per gram of meat samples treated with burdock leaf fractions decreased 2.15, compared with the samples without treatment. The shelf life of pork treated with burdock leaf fractions was extended 6 days compared with the pork without treatment, and the sensory property was obviously improved. Compared with the control group, burdock leaf fraction treatment significantly decreased the total volatile basic nitrogen value and pH of the meat samples. Chemical composition analysis showed that the burdock leaf fraction consisted of chlorogenic acid, caffeic acid, p-coumaric acid, rutin, cynarin, crocin, luteolin, arctiin, and quercetin. As a vegetable with an abundant source, burdock leaf is safe, affordable, and efficient in meat preservation, indicating that burdock leaf fraction is a promising natural preservative for pork.

Simultaneous determination of phenolic acids and flavonoids in Chenopodium formosanum Koidz. (djulis) by HPLC-DAD-ESI-MS/MS.

PubMed

Hsu, B Y; Lin, S W; Inbaraj, B Stephen; Chen, B H

2017-01-05

A high performance liquid chromatography-diode array detection-tandem mass spectrometry method (HPLC-DAD-MS/MS) was developed for simultaneous determination of phenolic acids and flavonoids in djulis (Chenopodium formosanum Koidz.), a traditional Chinese herb reported to possess vital biological activities. A high yield of phenolic acids and flavonoids was attained by employing 50% ethanol in water as the extraction solvent and shaking in a 60°C water bath for 3h. A total of 8 phenolic acids and 14 flavonoids were separated and identified within 55min by using a Poroshell 120 EC-C18 column with detection at 280nm, flow rate at 0.8mL/min, column temperature at 35°C, and a gradient solvent system of 0.1% formic acid in water and acetonitrile. Two internal standards caffeic acid and kaempferol-3-O-rutinoside were used for quantitation of phenolic acids and flavonoids in djulis respectively. The amounts of phenolic acids ranged from 11.5±0.8μg/g (caffeoyl-putrescine-derivative (2)) to 1855.3±16.9μg/g (hydroxylphenylacetic acid pentoside), while the flavonoids ranged from 19.93±2.29μg/g (quercetin-3-O-(coumaryl)-rutinoside-pentoside (1)) to 257.3±2.05μg/g (rutin-O-pentoside (2)). A high recovery (89.68-97.20%) and high reproducibility was obtained for both phenolic acids and flavonoids with the relative standard deviation (RSD) for the latter ranging from 0.09-8.22% (intra-day variability) and 0.80-8.48% (inter-day variability). This method may be applied to determination of both phenolic acids and flavonoids in food products and Chinese herbs. Copyright © 2016 Elsevier B.V. All rights reserved.

Caffeic Acid Derivatives in Dried Lamiaceae and Echinacea purpurea Products

USDA-ARS?s Scientific Manuscript database

The concentrations of caffeic acid derivatives within Lamiaceae and Echinacea (herb, spice, tea, and dietary supplement forms) readily available in the U.S. marketplace (n=72) were determined. After the first identification of chicoric acid in Ocimum basilicum (basil), the extent to which chicoric a...

Nine Different Chemical Species and Action Mechanisms of Pancreatic Lipase Ligands Screened Out from Forsythia suspensa Leaves All at One Time.

PubMed

Chen, Tinggui; Li, Yayun; Zhang, Liwei

2017-05-12

It is difficult to screen out as many active components as possible from natural plants all at one time. In this study, subfractions of Forsythia suspensa leaves were firstly prepared; then, their inhibitive abilities on pancreatic lipase were tested; finally, the highest inhibiting subfraction was screened by self-made immobilized pancreatic lipase. Results showed that nine ligands, including eight inhibitors and one promotor, were screened out all at one time. They were three flavonoids (rutin, IC 50 : 149 ± 6.0 μmol/L; hesperidin, 52.4 μmol/L; kaempferol-3- O -rutinoside, isolated from F. suspensa leaves for the first time, IC 50 notably reached 2.9 ± 0.5 μmol/L), two polyphenols (chlorogenic acid, 3150 ± 120 μmol/L; caffeic acid, 1394 ± 52 μmol/L), two lignans (phillyrin, promoter; arctigenin, 2129 ± 10.5 μmol/L), and two phenethyl alcohol (forsythiaside A, 2155 ± 8.5 μmol/L; its isomer). Their action mechanisms included competitive inhibition, competitive promotion, noncompetitive inhibition, and uncompetitive inhibition. In sum, using the appropriate methods, more active ingredients can be simply and quickly screened out all at one time from a complex natural product system. In addition, F. suspensa leaves contain numerous inhibitors of pancreatic lipase.

Synaptophysin and the dopaminergic system in hippocampus are involved in the protective effect of rutin against trimethyltin-induced learning and memory impairment.

PubMed

Zhang, Lei; Zhao, Qi; Chen, Chun-Hai; Qin, Qi-Zhong; Zhou, Zhou; Yu, Zheng-Ping

2014-09-01

This study aimed to investigate the protective effect of rutin against trimethyltin-induced spatial learning and memory impairment in mice. This study focused on the role of synaptophysin, growth-associated protein 43 and the action of the dopaminergic system in mechanisms associated with rutin protection and trimethyltin-induced spatial learning and memory impairment. Cognitive learning and memory was measured by Morris Water Maze. The expression of synaptophysin and growth-associated protein 43 in hippocampus was analyzed by western blot. The concentrations of dopamine, homovanillic acid, and dihyroxyphenylacetic acid in hippocampus were detected using reversed phase high-performance liquid chromatography with electrochemical detection. Trimethyltin-induced spatial learning impairment showed a dose-dependent mode. Synaptophysin but not growth-associated protein 43 was decreased in the hippocampus after trimethyltin administration. The concentration of dopamine decreased, while homovanillic acid increased in the hippocampus after trimethyltin administration. Mice pretreated with 20 mg/kg of rutin for 7 consecutive days exhibited improved water maze performance. Moreover, rutin pretreatment reversed the decrease of synaptophysin expression and dopamine alteration. These results suggest that rutin may protect against spatial memory impairment induced by trimethyltin. Synaptophysin and the dopaminergic system may be involved in trimethyltin-induced neuronal damage in hippocampus.

Synergism between Naproxen and Rutin in a Mouse Model of Visceral Pain.

PubMed

Alonso-Castro, Angel Josabad; Rangel-Velázquez, Joceline Estefanía; Isiordia-Espinoza, Mario A; Villanueva-Solís, Luis Enrique; Aragon-Martinez, Othoniel H; Zapata-Morales, Juan Ramón

2017-08-01

Preclinical Research The aim of the present study was to evaluate the antinociceptive interaction between naproxen and the glycoside flavonoid, rutin in the acetic acid-induced writhing test in mice. Naproxen (5, 20, 50, and 100 mg/kg p.o.) or rutin (10, 25, 50, and 100mg/kg p.o.) were administered 60 min before the intraperitoneal administration with acetic acid. The dose-response curve of each individual compound and the experimental effective dose 50 (ED 50 ) value were obtained to determinate different proportions of the combinations between the two compounds (naproxen-rutin 1:1, 3:1, and 3:1) in the writhing test. The results indicated a synergistic antinociceptive interaction between two drugs with different mechanism of action, naproxen and rutin in all the combinations. Drug Dev Res 78 : 184-188, 2017. © 2017 Wiley Periodicals, Inc. © 2017 Wiley Periodicals, Inc.

Degradation of caffeic acid in subcritical water and online HPLC-DPPH assay of degradation products.

PubMed

Khuwijitjaru, Pramote; Suaylam, Boonyanuch; Adachi, Shuji

2014-02-26

Caffeic acid was subjected to degradation under subcritical water conditions within 160-240 °C and at a constant pressure of 5 MPa in a continuous tubular reactor. Caffeic acid degraded quickly at these temperatures; the main products identified by liquid chromatography-diode array detection/mass spectrometry were hydroxytyrosol, protocatechuic aldehyde, and 4-vinylcatechol. The reaction rates for the degradation of caffeic acid and the formation of products were evaluated. Online high-performance liquid chromatography/2,2-diphenyl-1-picryhydrazyl assay was used to determine the antioxidant activity of each product in the solution. It was found that the overall antioxidant activity of the treated solution did not change during the degradation process. This study showed a potential of formation of antioxidants from natural phenolic compounds under these subcritical water conditions, and this may lead to a discovering of novel antioxidants compounds during the extraction by this technique.

The components of Melissa officinalis L. that influence protein biosynthesis in-vitro.

PubMed

Chlabicz, J; Gałasiński, W

1986-11-01

An investigation of an inhibiting activity of a substance(s) in a tanninless extract from Melissa officinalis leaves on protein biosynthesis in-vitro has been made. At least two components which inhibited protein biosynthesis were present in the extract; these were caffeic acid and an unidentified glycoside. Freshly prepared buffered solutions of caffeic acid inhibited protein biosynthesis less than solutions stored for several days at room temperature (20 degrees C). In this case derivatives of caffeic acid were formed, which may be responsible for the increase in the inhibitory effect of stored caffeic acid solution. An inhibitor, in the homogeneous state, was also isolated from the glycoside fraction of M. officinalis. Studies on the mechanism of the action of this inhibitor revealed its effect is to use the result of a direct interaction with elongation factor EF-2, and the blocking of the binding reaction of EF-2 with ribosomes.

In vitro Inhibition of Pancreatic Lipase by Polyphenols:
A Kinetic, Fluorescence Spectroscopy and Molecular Docking Study

PubMed Central

2017-01-01

Summary The inhibitory activity and binding characteristics of caffeic acid, p-coumaric acid, quercetin and capsaicin, four phenolic compounds found in hot pepper, against porcine pancreatic lipase activity were studied and compared to hot pepper extract. Quercetin was the strongest inhibitor (IC50=(6.1±2.4) µM), followed by p-coumaric acid ((170.2±20.6) µM) and caffeic acid ((401.5±32.1) µM), while capsaicin and a hot pepper extract had very low inhibitory activity. All polyphenolic compounds showed a mixed-type inhibition. Fluorescence spectroscopy studies showed that polyphenolic compounds had the ability to quench the intrinsic fluorescence of pancreatic lipase by a static mechanism. The sequence of Stern-Volmer constant was quercetin, followed by caffeic and p-coumaric acids. Molecular docking studies showed that caffeic acid, quercetin and p-coumaric acid bound near the active site, while capsaicin bound far away from the active site. Hydrogen bonds and π-stacking hydrophobic interactions are the main pancreatic lipase-polyphenolic compound interactions observed. PMID:29540986

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.

Chemical profile and antioxidant capacity verification of Psidium guajava (Myrtaceae) fruits at different stages of maturation

PubMed Central

Araújo, Heverton M.; Rodrigues, Fabíola F. G.; Costa, Wégila D.; Nonato, Carla de F. A.; Rodrigues, Fábio F. G.; Boligon, Aline A.; Athayde, Margareth L.; Costa, José G. M.

2015-01-01

Psidium guajava (Myrtaceae), a common plant in Cariri region, Ceara, Brazil, as well as in various parts of the world, contains high concentrations of bioactive compounds and in many communities its parts are used for therapeutic purposes. Studies describe antioxidant, antimicrobial and anti-diarrheal actions from extracts obtained from leaves, but information about the activities of the fruits and comparison of these at different maturity stages (immature, partially mature and mature) are scarce. This study aims to evaluate the antioxidant properties by quantifying the levels of phenolic and flavonoid compounds, carotenoids and vitamin C of P. guajava fruits at different stages of maturation. The content of phenolic compounds for the immature fruit, partially mature and mature were: 22.41; 34.61 and 32.92 mg of AG/g fraction. The flavonoid content for immature fruits, intermediate and mature were: 2.83; 5.10 and 5.65 mg RUT/g fraction, respectively. Following the same standards of maturation stages, the ascorbic acid content was determined with values of 0.48; 0.38 and 0.21 mg AA/g fraction, respectively. HPLC analysis identified and quantified the presence of gallic acid, catechin, chlorogenic acid, caffeic acid, epicatechin, rutin, quercitrin, isoquercitrin, quercetin, kaempferol, glycosylated campeferol, tocopherol, β-carotene and lycopene. The antioxidant activity carried out by DPPH method showed the mature fruits bearing the best results, whereas chelation of Fe2+ ions showed higher percentage for the immature fruit. The results obtained by lipidic peroxidation were not satisfactory. PMID:26933403

Antibacterial and antioxidant properties of grape stem extract applied as disinfectant in fresh leafy vegetables.

PubMed

Vázquez-Armenta, F J; Silva-Espinoza, B A; Cruz-Valenzuela, M R; González-Aguilar, G A; Nazzaro, F; Fratianni, F; Ayala-Zavala, J F

2017-09-01

In the present study total phenolic content (TPC), total flavonoid content (TFC), antioxidant activity and antimicrobial properties of grape (Vitis vinifera var. Red Globe) stem extract is reported. Also, the identification of main phenolic compounds was carried out by UPLC-PAD analysis. TPC and TFC of extract were 37.25 g GAE kg -1 and 98.07 g QE kg -1 , respectively. Extract showed an antioxidant capacity of 132.60 and 317 g TE kg -1 for DPPH and ABTS radical scavenging capacity, respectively. The main phenolic compounds identified were rutin, gallic acid, chlorogenic acid, caffeic acid, catechin and ferulic acid. Extract inhibited the growth of Listeria monocytogenes , Staphylococcus aureus , Salmonella enterica subsp. enterica serovar Typhimurium, and Escherichia coli O157: H7 at MIC range 16-18 g L -1 . Extract affected the different phases of bacterial growth. In addition, application of Extract (25 g L -1 ) as a sanitizer was effective to reduce the populations of all bacteria inoculated in lettuce (0.859-1.884 log reduction) and spinach (0.843-2.605 log reduction). This study emphasizes the potential of grape processing byproducts as an emergent and attractive source of bioactive compounds with antioxidant properties and antimicrobial activity against important foodborne pathogens. The study demonstrated that stem extract could be used to control the presence of human pathogenic bacteria in fresh leafy vegetables.

Characterization and quantification of flavonoids and hydroxycinnamic acids in curly kale (Brassica oleracea L. Convar. acephala Var. sabellica) by HPLC-DAD-ESI-MSn.

PubMed

Olsen, Helle; Aaby, Kjersti; Borge, Grethe Iren A

2009-04-08

Kale is a leafy green vegetable belonging to the Brassicaceae family, a group of vegetables including cabbage, broccoli, cauliflower, and Brussels sprouts, with a high content of health-promoting phytochemicals. The flavonoids and hydroxycinammic acids of curly kale ( Brassica oleracea L. ssp. oleracea convar. acephala (DC.) Alef. var. sabellica L.), a variety of kale, were characterized and identified primarily through HPLC-DAD-ESI-MS(n) analysis. Thirty-two phenolic compounds including glycosides of quercetin and kaempferol and derivatives of p-coumaric, ferulic, sinapic, and caffeic acid were tentatively identified, providing a more complete identification of phenolic compounds in curly kale than previously reported. Moreover, three hydroxycinnamic acids and one flavonoid with an unusual high grade of glycosylation, quercetin-3-disinapoyl-triglucoside-7-diglucoside, have been tentatively identified for the first time. The influence of different extraction conditions (extraction method, solvent type, solvent/solid ratio, and duration of extraction) was investigated. The total flavonol and hydroxycinnamic acid contents in curly kale determined as rutin equivalents (RE) were 646 and 204 mg of RE/100 g of fresh weight (fw), respectively. The contents of individual flavonoids ranged from 2 to 159 mg of RE/100 g of fw, with main compounds kaempferol-3-sinapoyl-diglucoside-7-diglucoside (18.7%) and quercetin-3-sinapoyl-diglucoside-7-diglucoside (16.5%). After acidic hydrolysis, two flavonol aglycones were identified in curly kale, quercetin and kaempferol, with total contents of 44 and 58 mg/100 g of fw, respectively.

Effects of blending wheatgrass juice on enhancing phenolic compounds and antioxidant activities of traditional kombucha beverage.

PubMed

Sun, Tzu-Ying; Li, Jia-Shiun; Chen, Chinshuh

2015-12-01

Traditional kombucha is a fermented black tea extract and sugar. Sweetened black tea (10% w/v) and wheatgrass juice (WGJ) were mixed in various ratios and used as fermentation substrate for enhancing phenolic compounds and antioxidant activity. Starter, comprising of yeast (Dekkera bruxellensis) and acetic acid bacteria (Gluconacetobacter rhaeticus and Gluconobacter roseus), was inoculated at 20% (v/v), and fermented statically at 29 ± 1°C for 12 days. The results showed that the total phenolic and flavonoid contents and antioxidant activity of the modified kombucha were higher than those of traditional preparations. All WGJ-blended kombucha preparations were characterized as having higher concentrations of various phenolic compounds such as gallic acid, catechin, caffeic acid, ferulic acid, rutin, and chlorogenic acid as compared to traditional ones. Addition of WGJ resulted in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging ability of kombucha being > 90%, while the oxygen radical absorbance capacity increased from 5.0 μmol trolox equivalents/mL to 12.8 μmol trolox equivalents/mL as the ratio of WGJ increased from 0% to 67% (v/v). The highest antioxidant activity was obtained using a 1:1 (v/v) black tea decoction to WGJ ratio and 3 days of fermentation, producing various types of phenolic acids. These results suggest that intake of fermented black tea enhanced with wheatgrass juice is advantageous over traditional kombucha formulas in terms of providing various complementary phenolics and might have more potential to reduce oxidative stress. Copyright © 2015. Published by Elsevier B.V.

Guava leaves polyphenolics-rich extract inhibits vital enzymes implicated in gout and hypertension in vitro.

PubMed

Irondi, Emmanuel Anyachukwu; Agboola, Samson Olalekan; Oboh, Ganiyu; Boligon, Aline Augusti; Athayde, Margareth Linde; Shode, Francis O

2016-01-01

Elevated uric acid level, an index of gout resulting from the over-activity of xanthine oxidase (XO), increases the risk of developing hypertension. However, research has shown that plant-derived inhibitors of XO and angiotensin 1-converting enzyme (ACE), two enzymes implicated in gout and hypertension, respectively, can prevent or ameliorate both diseases, without noticeable side effects. Hence, this study characterized the polyphenolics composition of guava leaves extract and evaluated its inhibitory effect on XO and ACE in vitro. The polyphenolics (flavonoids and phenolic acids) were characterized using high-performance liquid chromatography (HPLC) coupled with diode array detection (DAD). The XO, ACE, and Fe(2+)-induced lipid peroxidation inhibitory activities, and free radicals (2,2-diphenylpicrylhydrazyl [DPPH]* and 2,2´-azino-bis-3-ethylbenzthiazoline-6-sulphonic [ABTS]*(+)) scavenging activities of the extract were determined using spectrophotometric methods. Flavonoids were present in the extract in the order of quercetin > kaempferol > catechin > quercitrin > rutin > luteolin > epicatechin; while phenolic acids were in the order of caffeic acid > chlorogenic acid > gallic acids. The extract effectively inhibited XO, ACE and Fe(2+)-induced lipid peroxidation in a dose-dependent manner; having half-maximal inhibitory concentrations (IC50) of 38.24 ± 2.32 μg/mL, 21.06 ± 2.04 μg/mL and 27.52 ± 1.72 μg/mL against XO, ACE and Fe(2+)-induced lipid peroxidation, respectively. The extract also strongly scavenged DPPH* and ABTS*(+). Guava leaves extract could serve as functional food for managing gout and hypertension and attenuating the oxidative stress associated with both diseases.

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

Aqueous extract from Ipomoea asarifolia (Convolvulaceae) leaves and its phenolic compounds have anti-inflammatory activity in murine models of edema, peritonitis and air-pouch inflammation.

PubMed

Furtado, Allanny A; Torres-Rêgo, Manoela; Lima, Maíra C J S; Bitencourt, Mariana A O; Estrela, Andréia Bergamo; Souza da Silva, Nayara; da Silva Siqueira, Emerson Michell; Tomaz, José Carlos; Lopes, Norberto Peporine; Silva-Júnior, Arnóbio Antônio; Zucolotto, Silvana M; Fernandes-Pedrosa, Matheus F

2016-11-04

Ipomoea asarifolia (Desr.) Roem. and Schult.(Convolvulaceae), popularly known as salsa or salsa-brava, is a plant of which the decoction of leaves is used in folk medicine to treat various inflammatory disorders such of dermatitis, scabies, symptoms of syphilis, skin ulcers and external wounds. However, little is known about possible compounds and mechanisms of action of the plant to support the activities reported by popular use. The study aimed to identify bioactive molecules present in the crude extract of I. asarifolia leaves and investigate the anti-inflammatory potential of this extract in different experimental in vivo models to improve the understanding on that activity. Aqueous extract of I. asarifolia leaves was prepared by decoction (1:10 m/v) and its chromatographic profile was obtained by high performance liquid chromatography coupled with diode array detector (HPLC-DAD) and liquid chromatography diode array detector coupled with mass spectrometry (LC-DAD-MS). The potential anti-inflammatory activity of the extract was assessed using the following in vivo models: xylene-induced ear edema (20, 30 and 40mg/kg), evaluating the degree of edema formation; carrageenan-induced peritonitis (10, 20 and 30mg/kg), evaluating leukocyte migration and cytokine levels (IL-1β, IL-6, IL-12 and TNF-α) at 4h; zymosan-induced air pouch inflammation (20, 30 and 40mg/kg), evaluating the kinetics of leukocyte migration by total and differential counts at 6, 24 and 48h. The same tests were conducted using pure compounds identified in the aqueous extract from I. asarifolia leaves in different doses for each experimental model. The compounds identified in the aqueous extract of I. asarifolia leaves by HPLC-DAD and LC-DAD-MS were rutin, chlorogenic acid and caffeic acid. The extract significantly reduced ear edema induced by xylene (81%, 85% and 86% for doses of 20, 30 and 40mg/kg, respectively, p<0.001), as well as cell migration in experimental models of peritonitis (70%, 78% and 83% for doses of 10, 20 and 30mg/kg, respectively, p<0.001) and air pouch inflammation (58%, 67% and 53% for doses of 20, 30 and 40mg/kg, respectively, p<0.001). In addition, the extract demonstrated the ability to significantly inhibit the production of cytokines IL-1β, IL-6, IL-12 and TNF-α (p<0.001). The secondary metabolites tested (rutin, chlorogenic acid and caffeic acid) also showed the ability to significantly (p<0.001) decrease the parameters analyzed above. This is the first study to identify and confirm these phenolic compounds in I. asarifolia leaves extract and to suggest that these compounds contribute to the anti-inflammatory activity in vivo, as reported by ethnomedicinal use of this plant. Through the different experimental models performed, we can conclude that the results obtained with the aqueous extract from I. asarifolia leaves support its popular use for the treatment of inflammatory disorders. Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

Enhanced lignin monomer production caused by cinnamic Acid and its hydroxylated derivatives inhibits soybean root growth.

PubMed

Lima, Rogério Barbosa; Salvador, Victor Hugo; dos Santos, Wanderley Dantas; Bubna, Gisele Adriana; Finger-Teixeira, Aline; Soares, Anderson Ricardo; Marchiosi, Rogério; Ferrarese, Maria de Lourdes Lucio; Ferrarese-Filho, Osvaldo

2013-01-01

Cinnamic acid and its hydroxylated derivatives (p-coumaric, caffeic, ferulic and sinapic acids) are known allelochemicals that affect the seed germination and root growth of many plant species. Recent studies have indicated that the reduction of root growth by these allelochemicals is associated with premature cell wall lignification. We hypothesized that an influx of these compounds into the phenylpropanoid pathway increases the lignin monomer content and reduces the root growth. To confirm this hypothesis, we evaluated the effects of cinnamic, p-coumaric, caffeic, ferulic and sinapic acids on soybean root growth, lignin and the composition of p-hydroxyphenyl (H), guaiacyl (G) and syringyl (S) monomers. To this end, three-day-old seedlings were cultivated in nutrient solution with or without allelochemical (or selective enzymatic inhibitors of the phenylpropanoid pathway) in a growth chamber for 24 h. In general, the results showed that 1) cinnamic, p-coumaric, caffeic and ferulic acids reduced root growth and increased lignin content; 2) cinnamic and p-coumaric acids increased p-hydroxyphenyl (H) monomer content, whereas p-coumaric, caffeic and ferulic acids increased guaiacyl (G) content, and sinapic acid increased sinapyl (S) content; 3) when applied in conjunction with piperonylic acid (PIP, an inhibitor of the cinnamate 4-hydroxylase, C4H), cinnamic acid reduced H, G and S contents; and 4) when applied in conjunction with 3,4-(methylenedioxy)cinnamic acid (MDCA, an inhibitor of the 4-coumarate:CoA ligase, 4CL), p-coumaric acid reduced H, G and S contents, whereas caffeic, ferulic and sinapic acids reduced G and S contents. These results confirm our hypothesis that exogenously applied allelochemicals are channeled into the phenylpropanoid pathway causing excessive production of lignin and its main monomers. By consequence, an enhanced stiffening of the cell wall restricts soybean root growth.

Antihypertensive effect of caffeic acid and its analogs through dual renin-angiotensin-aldosterone system inhibition.

PubMed

Bhullar, Khushwant S; Lassalle-Claux, Grégoire; Touaibia, Mohamed; Rupasinghe, H P Vasantha

2014-05-05

Hypertension is a crucial risk factor for cardiovascular diseases and contributes to one third of global mortality. In addition to conventional antihypertensive drugs such as captopril, naturally occurring phytochemicals and their analogs are used for reducing the risk and occurrence of hypertension. Herein, we demonstrate the possible use of caffeic acid and its derivatives in the treatment of hypertension through multi-target modulation of renin-angiotensin-aldosterone system (RAAS). Caffeic acid along with its nineteen novel derivatives, chlorogenic acid, quercetin and captopril were all investigated for the inhibition of renin and angiotensin converting enzyme (ACE) activities and production of aldosterone. Compound 22 with CH2CH(Ph)2 moiety exhibited the strongest renin inhibition (IC50=229µM) among all compounds tested (P≤0.05). Caffeic acid was the weakest renin inhibitor (IC50=5704µM) among all the compounds assayed. Similar to renin inhibition, compound 22 (IC50=9.1µM) also exhibited about 47 times stronger ACE inhibition compared to the parent compound. Analysis of aldosterone revealed that compound 8 with n-Pr moiety was the strongest modulator of aldosterone production among all the derivatives (P≤0.05). Toxicity analysis using human fibroblasts (WI-38 cells) confirmed the non-toxic manifestations of caffeic acid and its derivatives in comparison to clinically used drug captopril. Copyright © 2014 Elsevier B.V. All rights reserved.

Biotechnological production of caffeic acid derivatives from cell and organ cultures of Echinacea species.

PubMed

Murthy, Hosakatte Niranjana; Kim, Yun-Soo; Park, So-Young; Paek, Kee-Yoeup

2014-09-01

Caffeic acid derivatives (CADs) are a group of bioactive compounds which are produced in Echinacea species especially Echinacea purpurea, Echinacea angustifolia, and Echinacea pallida. Echinacea is a popular herbal medicine used in the treatment of common cold and it is also a prominent dietary supplement used throughout the world. Caffeic acid, chlorogenic acid (5-O-caffeoylquinic acid), caftaric acid (2-O-caffeoyltartaric acid), cichoric acid (2, 3-O-dicaffeoyltartaric acid), cynarin, and echinacoside are some of the important CADs which have varied pharmacological activities. The concentrations of these bioactive compounds are species specific and also they vary considerably with the cultivated Echinacea species due to geographical location, stage of development, time of harvest, and growth conditions. Due to these reasons, plant cell and organ cultures have become attractive alternative for the production of biomass and caffeic acid derivatives. Adventitious and hairy roots have been induced in E. pupurea and E. angustifolia, and suspension cultures have been established from flask to bioreactor scale for the production of biomass and CADs. Tremendous progress has been made in this area; various bioprocess methods and strategies have been developed for constant high-quality productivity of biomass and secondary products. This review is aimed to discuss biotechnological methods and approaches employed for the sustainable production of CADs.

Biotechnological Production of Caffeic Acid by Bacterial Cytochrome P450 CYP199A2

PubMed Central

Arai, Yuka; Kino, Kuniki

2012-01-01

Caffeic acid is a biologically active molecule that has various beneficial properties, including antioxidant, anticancer, and anti-inflammatory activities. In this study, we explored the catalytic potential of a bacterial cytochrome P450, CYP199A2, for the biotechnological production of caffeic acid. When the CYP199A2 enzyme was reacted with p-coumaric acid, it stoichiometrically produced caffeic acid. The crystal structure of CYP199A2 shows that Phe at position 185 is situated directly above, and only 6.35 Å from, the heme iron. This F185 residue was replaced with hydrophobic or hydroxylated amino acids using site-directed mutagenesis to create mutants with novel and improved catalytic properties. In whole-cell assays with the known substrate of CYP199A2, 2-naphthoic acid, only the wild-type enzyme hydroxylated 2-naphthoic acid at the C-7 and C-8 positions, whereas all of the active F185 mutants exhibited a preference for C-5 hydroxylation. Interestingly, several F185 mutants (F185V, F185L, F185I, F185G, and F185A mutants) also acquired the ability to hydroxylate cinnamic acid, which was not hydroxylated by the wild-type enzyme. These results demonstrate that F185 is an important residue that controls the regioselectivity and the substrate specificity of CYP199A2. Furthermore, Escherichia coli cells expressing the F185L mutant exhibited 5.5 times higher hydroxylation activity for p-coumaric acid than those expressing the wild-type enzyme. By using the F185L whole-cell catalyst, the production of caffeic acid reached 15 mM (2.8 g/liter), which is the highest level so far attained in biotechnological production of this compound. PMID:22729547

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.

Ultrasensitive detection of phenolic antioxidants by surface enhanced Raman spectroscopy

NASA Astrophysics Data System (ADS)

Ornelas-Soto, N.; Aguilar-Hernández, I. A.; Afseth, N.; López-Luke, T.; Contreras-Torres, F. F.; Wold, J. P.

2017-08-01

Surface-Enhanced Raman Spectroscopy (SERS) is a powerful surface-sensitive technique to study the vibrational properties of analytes at very low concentrations. In this study, ferulic acid, p-coumaric acid, caffeic acid and sinapic acid were analyzed by SERS using Ag colloids. Analytes were detected up to 2.5x10-9M. For caffeic acid and coumaric acid, this detection limit has been reached for the first time, as well as the SERS analysis of sinapic acid using silver colloids.

Accumulation of Rutin and Betulinic Acid and Expression of Phenylpropanoid and Triterpenoid Biosynthetic Genes in Mulberry (Morus alba L.).

PubMed

Zhao, Shicheng; Park, Chang Ha; Li, Xiaohua; Kim, Yeon Bok; Yang, Jingli; Sung, Gyoo Byung; Park, Nam Il; Kim, Soonok; Park, Sang Un

2015-09-30

Mulberry (Morus alba L.) is used in traditional Chinese medicine and is the sole food source of the silkworm. Here, 21 cDNAs encoding phenylpropanoid biosynthetic genes and 21 cDNAs encoding triterpene biosynthetic genes were isolated from mulberry. The expression levels of genes involved in these biosynthetic pathways and the accumulation of rutin, betulin, and betulinic acid, important secondary metabolites, were investigated in different plant organs. Most phenylpropanoid and triterpene biosynthetic genes were highly expressed in leaves and/or fruit, and most genes were downregulated during fruit ripening. The accumulation of rutin was more than fivefold higher in leaves than in other organs, and higher levels of betulin and betulinic acid were found in roots and leaves than in fruit. By comparing the contents of these compounds with gene expression levels, we speculate that MaUGT78D1 and MaLUS play important regulatory roles in the rutin and betulin biosynthetic pathways.

Chlorogenic acid, rutin and hyperoside content in Fragaria vesca, F. viridis and F. moschata in Lithuania.

PubMed

Bagdonaite, Edita; Jakstas, Valdas; Raudonis, Raimondas; Janulis, Valdimaras

2013-01-01

In Lithuania, two species of the genus Fragaria L. (Rosaceae), F. vesca L. and F. viridis Weston, occur naturally in the wild and two others, F. moschata Weston and F. × ananassa Duchesne ex Rozier are found escaped from cultivation. The main objective of this study was to establish the variation pattern in the content of chlorogenic acid, rutin and hyperoside in leaves and fruits of the native Lithuanian species. In this work, the chemical polymorphisms of different Fragaria species were studied by growing plants side by side under the same cultivated field conditions. F. vesca fruits had the highest rutin (1.38 ± 0.19 mg g(-1) DM), hyperoside (0.69 ± 0.10 mg g(-1) DM) and chlorogenic acid (2.25 ± 0.34 mg g(-1) DM) content, followed by F. viridis and F. moschata. Our results showed that the leaves should be taken into account as important rutin and hyperoside contributors for strawberries.

Antibacterial potential of rutin conjugated with thioglycolic acid capped cadmium telluride quantum dots (TGA-CdTe QDs)

NASA Astrophysics Data System (ADS)

Ananth, Devanesan Arul; Rameshkumar, Angappan; Jeyadevi, Ramachandran; Jagadeeswari, Sivanadanam; Nagarajan, Natarajan; Renganathan, Rajalingam; Sivasudha, Thilagar

2015-03-01

Quantum dots not only act as nanocarrier but also act as stable and resistant natural fluorescent bio markers used in various in vitro and in vivo photolabelling and biological applications. In this study, the antimicrobial potential of TGA-CdTe QDs and commercial phenolics (rutin and caffeine) were investigated against Escherichiacoli. UV absorbance and fluorescence quenching study of TGA-CdTe QDs with rutin and caffeine complex was measured by spectroscopic technique. QDs-rutin conjugate exhibited excellent quenching property due to the -OH groups present in the rutin structure. But the same time caffeine has not conjugated with QDs because of lacking of -OH group in its structure. Photolabelling of E. coli with QDs-rutin and QDs-caffeine complex was analyzed by fluorescent microscopic method. Microbe E. coli cell membrane damage was assessed by atomic force (AFM) and confocal microscopy. Based on the results obtained, it is suggested that QDs-rutin conjugate enhance the antimicrobial activity more than the treatment with QDs, rutin and caffeine alone.

Effect of acyl donor chain length and substitutions pattern on the enzymatic acylation of flavonoids.

PubMed

Ardhaoui, M; Falcimaigne, A; Ognier, S; Engasser, J M; Moussou, P; Pauly, G; Ghoul, M

2004-06-10

Rutin and esculin were enzymatically acylated with different aliphatic acids as acyl donors (fatty acids, dicarboxylic acids and omega-substituted fatty acids) by an immobilized lipase from Candida antarctica. The effect of the water content and the acyl donors pattern on the flavonoid initial acylation rate and conversion yield were investigated. The obtained results indicated that the water content of the medium has a strong effect on the performance of these reactions. The best conversion yields were reached when the water content was kept lower than 200 ppm. At low water content of the medium, these syntheses are influenced by carbon chain length and substitution pattern of the acyl donors. Higher conversion yields of esculin and rutin (>70%) were obtained with aliphatic acids having high carbon chain length (>12). Moreover, it has been found that the amine and thiol groups on omega-substituted fatty acid chain were unfavourable to these reactions. The 1H NMR and 13C NMR analyses of some synthesized esters (esculin and rutin palmitate) show that only monoesters were produced and that the esterification takes place on the primary OH of glucose moiety of the esculin and on the secondary 4"'-OH of the rhamnose residue of rutin. Copyright 2004 Elsevier B.V.

Co-administration of caffeine and caffeic acid alters some key enzymes linked with reproductive function in male rats.

PubMed

Akomolafe, S F; Akinyemi, A J; Oboh, G; Oyeleye, S I; Ajayi, O B; Omonisi, A E; Owolabi, F L; Atoyebi, D A; Ige, F O; Atoki, V A

2018-03-01

This study assessed the effects of caffeine combined with caffeic acid on some biomarkers of male reproductive function using normal albino Wistar rats. Rats were divided into four groups (n = 6) and treated for seven successive days; group 1 represents the control rats; group 2 rats were treated with 50 mg/kg body weight (BW) of caffeine only; group 3 rats were treated with 50 mg/kg BW of caffeic acid, while the rats in group 4 were cotreated with an equal combination of caffeine and caffeic acid. The results revealed significant increase in reproductive hormone, testicular and epididymal nitric oxide levels of the rats. Moreover, decreased oxidative stress in the testes and epididymides of the treated rats was evidenced by significant increase in total and nonprotein thiol levels, catalase and superoxide dismutase activities. Similarly, decreased testicular cholesterol level with concomitant elevation in testicular steroidogenic enzyme activities, glycogen and zinc levels were observed in the treated rats. No morphological changes were observed as revealed by the photomicrographs from light microscopy in treated rats. Nevertheless, the combination therapy exhibited additive/synergistic effect on these biochemical indices than when they were administered singly. This study suggests the combination therapy of caffeine and caffeic acid at the dose tested for improving male reproductive function. © 2017 Blackwell Verlag GmbH.

A Continuous, Quantitative Fluorescent Assay for Plant Caffeic acid O-Methyltransferases

USDA-ARS?s Scientific Manuscript database

Plant caffeic acid O-methyltransferases (COMTs) use s-adenosylmethionine (ado-met), as a methyl donor to transmethylate their preferred (phenolic) substrates in-vivo, and will generally utilize a range of phenolic compounds in-vitro. Collazo et al. (2005; Analytical Biochemistry 342: 86-92) have pu...

Identification, quantification of bioactive constituents, evaluation of antioxidant and in vivo acute toxicity property from the methanol extract of Vernonia cinerea leaf extract.

PubMed

Rajamurugan, R; Selvaganabathy, N; Kumaravel, S; Ramamurthy, Ch; Sujatha, V; Suresh Kumar, M; Thirunavukkarasu, C

2011-12-01

Vernonia cinerea (L.) Less [Compositae (Asteraceae)] is used traditionally for several medical purposes such as inflammation, pain, fever, and cancer. The present study identified the bioactive constituents in the methanol extract of Vernonia cinerea leaf and evaluated its antioxidant activity and acute toxicity. The identification of phytochemicals was accomplished by GC-MS and the major antioxidant phenolic compounds in the extract were quantified by HPTLC analysis. To quantify the essential elements, atomic absorption spectrophotometeric analysis was carried out. Total phenol and flavonoid content was measured by Folin-Ciocalteau reagent and 2% aluminium chloride, respectively. GC-MS analysis identified the presence of 27 phytoconstituents. The predominant phenolic compound in the extract as quantified by HPTLC was gallic acid (1.92 mg/g) followed by rutin (0.705 mg/g), quercetin (0.173 mg/g), caffeic acid (0.082 mg/g) and ferulic acid (0.033 mg/g). The following elements were quantified: Fe (0.050 ppm), Mn (0.022 ppm), Co (0.0180 ppm), Pb (0.029 ppm), Hg (3.885 ppm) and Se (4.5240 ppm). The antioxidant activity of the extract increased with increasing concentration and the correlation (r²) for all in vitro assays were satisfactory. V. cinerea extract has significant (p < 0.05) antiradical activity. Hence, V. cinerea may have potential medicinal value and can be used in the formulation of pharmacological products for degenerative diseases.

Preparation, characterisation and antioxidant activities of rutin-loaded zein-sodium caseinate nanoparticles.

PubMed

Zhang, Shuangling; Han, Yue

2018-01-01

Novel rutin-loaded zein-sodium caseinate nanoparticles (ZP) with antioxidant activity in aqueous medium were investigated. The results showed that the sodium caseinate concentrations, dosages of rutin and ethanol volume fractions significantly affected the zein nanoparticles' characteristics. Concerning the antioxidant properties, the highest values of rutin loaded ZP obtained using 2, 2-diphenyl-1-picrylhydrazyl scavenging and 2 and 2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) decolourisation assays were 52.7% and 71.2%, respectively, and the total antioxidant capacity was 0.40 nmol g-1. The results suggest that zein-sodium caseinate nanoparticles can be used as a new nano carrier system for rutin or other water insoluble active ingredients.

Preparation, characterisation and antioxidant activities of rutin-loaded zein-sodium caseinate nanoparticles

PubMed Central

Han, Yue

2018-01-01

Novel rutin-loaded zein-sodium caseinate nanoparticles (ZP) with antioxidant activity in aqueous medium were investigated. The results showed that the sodium caseinate concentrations, dosages of rutin and ethanol volume fractions significantly affected the zein nanoparticles’ characteristics. Concerning the antioxidant properties, the highest values of rutin loaded ZP obtained using 2, 2-diphenyl-1-picrylhydrazyl scavenging and 2 and 2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) decolourisation assays were 52.7% and 71.2%, respectively, and the total antioxidant capacity was 0.40 nmol g-1. The results suggest that zein-sodium caseinate nanoparticles can be used as a new nano carrier system for rutin or other water insoluble active ingredients. PMID:29579133

Enhanced Lignin Monomer Production Caused by Cinnamic Acid and Its Hydroxylated Derivatives Inhibits Soybean Root Growth

PubMed Central

Lima, Rogério Barbosa; Salvador, Victor Hugo; dos Santos, Wanderley Dantas; Bubna, Gisele Adriana; Finger-Teixeira, Aline; Soares, Anderson Ricardo; Marchiosi, Rogério; Ferrarese, Maria de Lourdes Lucio; Ferrarese-Filho, Osvaldo

2013-01-01

Cinnamic acid and its hydroxylated derivatives (p-coumaric, caffeic, ferulic and sinapic acids) are known allelochemicals that affect the seed germination and root growth of many plant species. Recent studies have indicated that the reduction of root growth by these allelochemicals is associated with premature cell wall lignification. We hypothesized that an influx of these compounds into the phenylpropanoid pathway increases the lignin monomer content and reduces the root growth. To confirm this hypothesis, we evaluated the effects of cinnamic, p-coumaric, caffeic, ferulic and sinapic acids on soybean root growth, lignin and the composition of p-hydroxyphenyl (H), guaiacyl (G) and syringyl (S) monomers. To this end, three-day-old seedlings were cultivated in nutrient solution with or without allelochemical (or selective enzymatic inhibitors of the phenylpropanoid pathway) in a growth chamber for 24 h. In general, the results showed that 1) cinnamic, p-coumaric, caffeic and ferulic acids reduced root growth and increased lignin content; 2) cinnamic and p-coumaric acids increased p-hydroxyphenyl (H) monomer content, whereas p-coumaric, caffeic and ferulic acids increased guaiacyl (G) content, and sinapic acid increased sinapyl (S) content; 3) when applied in conjunction with piperonylic acid (PIP, an inhibitor of the cinnamate 4-hydroxylase, C4H), cinnamic acid reduced H, G and S contents; and 4) when applied in conjunction with 3,4-(methylenedioxy)cinnamic acid (MDCA, an inhibitor of the 4-coumarate:CoA ligase, 4CL), p-coumaric acid reduced H, G and S contents, whereas caffeic, ferulic and sinapic acids reduced G and S contents. These results confirm our hypothesis that exogenously applied allelochemicals are channeled into the phenylpropanoid pathway causing excessive production of lignin and its main monomers. By consequence, an enhanced stiffening of the cell wall restricts soybean root growth. PMID:24312480

The suppression of the N-nitrosating reaction by chlorogenic acid.

PubMed Central

Kono, Y; Shibata, H; Kodama, Y; Sawa, Y

1995-01-01

N-Nitrosation of a model aromatic amine (2,3-diamino-naphthalene) by the N-nitrosating agent produced by nitrite in acidic solution was inhibited by a polyphenol, chlorogenic acid, which is an ester of caffeic acid quinic acid. Caffeic acid also inhibited the N-nitrosation, but quinic acid did not. 1,2-Benzenediols and 3,4-dihydroxybenzoic acid had inhibitory activities. Chlorogenic acid, caffeic acid, 1,2-benzenediols and 3,4-dihydroxybenzoic acid were able to scavenge the stable free radical, 1,1-diphenyl-2-picrylhydrazyl. Chlorogenic acid was found to be nitrated by acidic nitrite. The kinetic studies and the nitration observed only by bubbling of nitric oxide plus nitrogen dioxide gases indicated that the nitrating agent was nitrogen sesquioxide. The observations showed that the mechanism by which chlorogenic acid inhibited N-nitrosation of 2,3-diamino-naphthalene is due to its ability to scavenge the nitrosating agent, nitrogen sesquioxide. Chlorogenic acid may be effective not only in protecting against oxidative damage but also in inhibiting potentially mutagenic and carcinogenic reactions in vivo. PMID:8554543

Development and validation of an high-performance liquid chromatography-diode array detector method for the simultaneous determination of six phenolic compounds in abnormal savda munziq decoction

PubMed Central

Tian, Shuge; Liu, Wenxian; Liu, Feng; Zhang, Xuejia; Upur, Halmuart

2015-01-01

Aims: Given the high-effectiveness and low-toxicity of abnormal savda munziq (ASMQ), its herbal formulation has long been used in traditional Uyghur medicine to treat complex diseases, such as cancer, diabetes, and cardiovascular diseases. Settings and Design: ASMQ decoction by reversed-phase high-performance liquid chromatography coupled with a diode array detector was successfully developed for the simultaneous quality assessment of gallic acid, protocatechuic acid, caffeic acid, rutin, rosmarinic acid, and luteolin. The six phenolic compounds were separated on an Agilent TC-C18 reversed-phase analytical column (4.6 × 250 mm, 5 μm) by gradient elution using 0.3% aqueous formic acid (v/v) and 0.3% methanol formic acid (v/v) at 1.0 mL/min. Materials and Methods: The plant material was separately ground and mixed at the following ratios (10): Cordia dichotoma (10.6), Anchusa italic (10.6), Euphorbia humifusa (4.9), Adiantum capillus-veneris (4.9), Ziziphus jujube (4.9), Glycyrrhiza uralensis (7.1), Foeniculum vulgare (4.9), Lavandula angustifolia (4.9), Dracocephalum moldavica L. (4.9), and Alhagi pseudoalhagi (42.3). Statistical Analysis Used: The precisions of all six compounds were <0.60%, and the average recoveries ranged from 99.39% to 104.85%. Highly significant linear correlations were found between component concentrations and specific chromatographic peak areas (R2 > 0.999). Results: The proposed method was successfully applied to determine the levels of six active components in ASMQ. Conclusions: Given the simplicity, precision, specificity, and sensitivity of the method, it can be utilized as a quality control approach to simultaneously determining the six phenolic compounds in AMSQ. PMID:25709227

Guava leaves polyphenolics-rich extract inhibits vital enzymes implicated in gout and hypertension in vitro

PubMed Central

Irondi, Emmanuel Anyachukwu; Agboola, Samson Olalekan; Oboh, Ganiyu; Boligon, Aline Augusti; Athayde, Margareth Linde; Shode, Francis O.

2016-01-01

Background/Aim: Elevated uric acid level, an index of gout resulting from the over-activity of xanthine oxidase (XO), increases the risk of developing hypertension. However, research has shown that plant-derived inhibitors of XO and angiotensin 1-converting enzyme (ACE), two enzymes implicated in gout and hypertension, respectively, can prevent or ameliorate both diseases, without noticeable side effects. Hence, this study characterized the polyphenolics composition of guava leaves extract and evaluated its inhibitory effect on XO and ACE in vitro. Materials and Methods: The polyphenolics (flavonoids and phenolic acids) were characterized using high-performance liquid chromatography (HPLC) coupled with diode array detection (DAD). The XO, ACE, and Fe2+-induced lipid peroxidation inhibitory activities, and free radicals (2,2-diphenylpicrylhydrazyl [DPPH]* and 2,2´-azino-bis-3-ethylbenzthiazoline-6-sulphonic [ABTS]*+) scavenging activities of the extract were determined using spectrophotometric methods. Results: Flavonoids were present in the extract in the order of quercetin > kaempferol > catechin > quercitrin > rutin > luteolin > epicatechin; while phenolic acids were in the order of caffeic acid > chlorogenic acid > gallic acids. The extract effectively inhibited XO, ACE and Fe2+-induced lipid peroxidation in a dose-dependent manner; having half-maximal inhibitory concentrations (IC50) of 38.24 ± 2.32 μg/mL, 21.06 ± 2.04 μg/mL and 27.52 ± 1.72 μg/mL against XO, ACE and Fe2+-induced lipid peroxidation, respectively. The extract also strongly scavenged DPPH* and ABTS*+. Conclusion: Guava leaves extract could serve as functional food for managing gout and hypertension and attenuating the oxidative stress associated with both diseases. PMID:27104032

Simultaneous determination of chlorogenic acid, caffeic acid, alantolactone and isoalantolactone in Inula helenium by HPLC.

PubMed

Wang, Jin; Zhao, Yong-ming; Zhang, Man-li; Shi, Qing-wen

2015-04-01

A rapid and sensitive high-performance liquid chromatographic (HPLC) method was developed for the simultaneous separation and determination of chlorogenic acid, caffeic acid, alantolactone and isoalantolactone in Inula helenium. The HPLC separation was performed on an Elite Hypersil C18 column (200 × 4.6 mm i.d., 5 µm particle size) with a gradient elution of solvent A (acetonitrile) and solvent B (0.1% phosphoric acid in water) at a flow rate of 1.0 mL/min. Detection was monitored at 225 nm. The recovery of chlorogenic acid ranged from 95.6 to 107.7%, the recovery of caffeic acid ranged from 95.4 to 104.2%, the recovery of alantolactone ranged from 95.8 to 100.8% and the recovery of isoalantolactone ranged from 96.5 to 102.3%. The retention times for chlorogenic acid, caffeic acid, alantolactone and isoalantolactone were 5.2, 7.1, 25.6 and 26.6 min with the limits of detection of 0.069, 0.021, 0.039 and 0.051 µg/mL, respectively. Relative standard deviation for the intra-day and inter-day was ≤2.5%. The validated method is reliable for the routine control of these four compounds in I. helenium. © The Author 2014. Published by Oxford University Press. All rights reserved. For Permissions, please email: journals.permissions@oup.com.

Engineering alfalfa to accumulate useful caffeic acid derivatives and characterization of hydroxycinnamoyl-CoA transferases from legumes

USDA-ARS?s Scientific Manuscript database

Some forages crops, such as red clover, accumulate high levels of caffeic acid derivatives. Oxidation of these o-diphenols to quinones by endogenous polyphenol oxidases (PPOs) and the subsequent reactions of these quinones (probably with endogenous plant proteases) result in a significant reduction ...

Molecular cloning, characterization and expression of the caffeic acid O-methyltransferase (COMT) ortholog from kenaf (Hibiscus cannabinus)

USDA-ARS?s Scientific Manuscript database

We cloned the full-length of the gene putatively encoding caffeic acid O-methyltransferase (COMT) from kenaf (Hibiscus cannabinus L.) using degenerate primers and the RACE (rapid amplification of cDNA ends) method. Kenaf is an herbaceous and rapidly growing dicotyledonous plant with great potential ...

Role of O-methyltransferase in the lignification of Douglas-fir cultured tissue

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

Monroe, S.H.

1983-01-01

O-methyltransferase (OMT) is a key enzyme in the biosynthesis of lignin. This enzyme was isolated and characterized in an effort to understand why Douglas-fir (Pseudotsuga menziesii (Mirb.) Franco) callus tissue does not form appreciable amounts of lignin yet does form large amounts of the related flavonoids and tannins. It was shown that the OMT in the callus tissue is a cell wall associated, membrane-bound enzyme, in contrast to that of all reported plant species and to Douglas-fir seedlings, which have either a microsomal or soluble OMT. The effect this had on the OMT kinetic constants was studied. It was foundmore » that the callus OMT had much higher K/sub m/ constants for caffeic acid in both the membrane-bound and free forms compared with seedlings. The callus membrane-bound K/sub m/ for caffeic acid is 333 ..mu..M. The callus membrane-free K/sub m/ for caffeic acid is 250 ..mu..M. The seedling K/sub m/ for caffeic acid is 90 ..mu..M.« less

Microencapsulation of caffeic acid phenethyl ester and caffeic acid phenethyl amide by inclusion in hydroxypropyl-β-cyclodextrin.

PubMed

Garrido, E Manuela P J; Cerqueira, Ana S; Chavarria, Daniel; Silva, Tiago; Borges, Fernanda; Garrido, Jorge M P J

2018-07-15

Caffeic acid phenethyl ester (CAPE) is a bioactive polyphenolic compound obtained from propolis extract. Although it has a broad therapeutic potential, the bioavailability of CAPE is limited, due to reduced solubility and poor plasmatic stability. Efforts to reduce these pharmacokinetic drawbacks resulted in the synthesis of caffeic acid phenethyl amide (CAPA). Cyclodextrins have been proved as promising excipients for the formulation of active ingredients. Herein, we report the inclusion complexation behavior and binding ability of CAPE and CAPA with hydroxypropyl-β-cyclodextrin (HP-β-CD). The supramolecular interactions were examined through UV and FTIR spectroscopy, DSC, 1 H NMR and 2D ROESY. The CAPE/HP-β-CD and CAPA/HP-β-CD inclusion complexes stability constants were determined to be, respectively, 2911.6 and 584.6 M -1 in water and 2866.2 and 700.1 M -1 at physiological pH. The aqueous solubility increased notably, proving that HP-β-CD can be potentially useful to improve the biological, chemical and physical properties of CAPE and CAPA. Copyright © 2018 Elsevier Ltd. All rights reserved.

Plant secondary metabolite-induced shifts in bacterial community structure and degradative ability in contaminated soil.

PubMed

Uhlik, Ondrej; Musilova, Lucie; Ridl, Jakub; Hroudova, Miluse; Vlcek, Cestmir; Koubek, Jiri; Holeckova, Marcela; Mackova, Martina; Macek, Tomas

2013-10-01

The aim of the study was to investigate how selected natural compounds (naringin, caffeic acid, and limonene) induce shifts in both bacterial community structure and degradative activity in long-term polychlorinated biphenyl (PCB)-contaminated soil and how these changes correlate with changes in chlorobiphenyl degradation capacity. In order to address this issue, we have integrated analytical methods of determining PCB degradation with pyrosequencing of 16S rRNA gene tag-encoded amplicons and DNA-stable isotope probing (SIP). Our model system was set in laboratory microcosms with PCB-contaminated soil, which was enriched for 8 weeks with the suspensions of flavonoid naringin, terpene limonene, and phenolic caffeic acid. Our results show that application of selected plant secondary metabolites resulted in bacterial community structure far different from the control one (no natural compound amendment). The community in soil treated with caffeic acid is almost solely represented by Proteobacteria, Acidobacteria, and Verrucomicrobia (together over 99 %). Treatment with naringin resulted in an enrichment of Firmicutes to the exclusion of Acidobacteria and Verrucomicrobia. SIP was applied in order to identify populations actively participating in 4-chlorobiphenyl catabolism. We observed that naringin and limonene in soil foster mainly populations of Hydrogenophaga spp., caffeic acid Burkholderia spp. and Pseudoxanthomonas spp. None of these populations were detected among 4-chlorobiphenyl utilizers in non-amended soil. Similarly, the degradation of individual PCB congeners was influenced by the addition of different plant compounds. Residual content of PCBs was lowest after treating the soil with naringin. Addition of caffeic acid resulted in comparable decrease of total PCBs with non-amended soil; however, higher substituted congeners were more degraded after caffeic acid treatment compared to all other treatments. Finally, it appears that plant secondary metabolites have a strong effect on the bacterial community structure, activity, and associated degradative ability.

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.

Effect of high pressure on peanut allergens in the presence of polyphenol oxidase and caffeic acid

USDA-ARS?s Scientific Manuscript database

High pressure (HP) enhances enzymatic reactions. Because polyphenol oxidase (PPO) is an enzyme, and reduces IgE binding of peanut allergens in presence of caffeic acid (CA), we postulated that a further reduction in IgE binding can be achieved, using HP together with PPO and CA. Peanut extracts cont...

Catalytic activity of the two-component flavin-dependent monooxygenase from Pseudomonas aeruginosa toward cinnamic acid derivatives.

PubMed

Furuya, Toshiki; Kino, Kuniki

2014-02-01

4-Hydroxyphenylacetate 3-hydroxylases (HPAHs) of the two-component flavin-dependent monooxygenase family are attractive enzymes that possess the catalytic potential to synthesize valuable ortho-diphenol compounds from simple monophenol compounds. In this study, we investigated the catalytic activity of HPAH from Pseudomonas aeruginosa strain PAO1 toward cinnamic acid derivatives. We prepared Escherichia coli cells expressing the hpaB gene encoding the monooxygenase component and the hpaC gene encoding the oxidoreductase component. E. coli cells expressing HpaBC exhibited no or very low oxidation activity toward cinnamic acid, o-coumaric acid, and m-coumaric acid, whereas they rapidly oxidized p-coumaric acid to caffeic acid. Interestingly, after p-coumaric acid was almost completely consumed, the resulting caffeic acid was further oxidized to 3,4,5-trihydroxycinnamic acid. In addition, HpaBC exhibited oxidation activity toward 3-(4-hydroxyphenyl)propanoic acid, ferulic acid, and coniferaldehyde to produce the corresponding ortho-diphenols. We also investigated a flask-scale production of caffeic acid from p-coumaric acid as the model reaction for HpaBC-catalyzed syntheses of hydroxycinnamic acids. Since the initial concentrations of the substrate p-coumaric acid higher than 40 mM markedly inhibited its HpaBC-catalyzed oxidation, the reaction was carried out by repeatedly adding 20 mM of this substrate to the reaction mixture. Furthermore, by using the HpaBC whole-cell catalyst in the presence of glycerol, our experimental setup achieved the high-yield production of caffeic acid, i.e., 56.6 mM (10.2 g/L) within 24 h. These catalytic activities of HpaBC will provide an easy and environment-friendly synthetic approach to hydroxycinnamic acids.

Chitosan-caffeic acid-genipin films presenting enhanced antioxidant activity and stability in acidic media.

PubMed

Nunes, Cláudia; Maricato, Élia; Cunha, Ângela; Nunes, Alexandra; da Silva, José A Lopes; Coimbra, Manuel A

2013-01-02

The use of chitosan films has been limited due to their high degradability in aqueous acidic media. In order to produce chitosan films with high antioxidant activity and insoluble in acid solutions caffeic acid was grafted to chitosan by a radical mechanism using ammonium cerium (IV) nitrate (60 mM). Genipin was used as cross-linker. This methodology originated films with 80% higher antioxidant activity than the pristine film. Also, these films only lost 11% of their mass upon seven days immersion into an aqueous solution at pH 3.5 under stirring. The films surface wettability (contact angle 105°), mechanical properties (68 MPa of tensile strength and 4% of elongation at break), and thermal stability for temperatures lower than 300 °C were not significantly influenced by the covalent linkage of caffeic acid and genipin to chitosan. Due to their characteristics, mainly higher antioxidant activity and lower solubility, these are promising materials to be used as active films. Copyright © 2012 Elsevier Ltd. All rights reserved.

Determination of the structure and catalytic mechanism of Sorghum bicolor caffeic acid O-methyltransferase and the structural impact of three brown midrib12 mutations

USDA-ARS?s Scientific Manuscript database

With S-adenosylmethionine (SAM) acting as the methyl donor, caffeic acid O-methyltransferase from Sorghum bicolor (SbCOMT) methylates the 5-hydroxyl group of its preferred substrate, 5-hydroxyconiferaldehyde, to form sinapaldehyde. In order to determine the mechanism of SbCOMT and understand the red...

Phenolic composition and radical scavenging activity of sweetpotato-derived shochu distillery by-products treated with koji.

PubMed

Yoshimoto, Makoto; Kurata-Azuma, Rie; Fujii, Makoto; Hou, De-Xing; Ikeda, Kohji; Yoshidome, Tomohisa; Osako, Miho

2004-12-01

Phenolic composition and radical scavenging activity in the shochu distillery by-products of sweetpotato (Ipomoea batatas L.) treated with koji (Aspergillus awamori mut.) and cellulase (Cellulosin T2) were investigated to develop new uses. Koji and Cellulosin T2 treatment of shochu distillery by-products from sweetpotatoes, rice, and barley increased phenolic content. Caffeic acid was identified as a dominant phenolic component in the shochu distillery by-products of the sweetpotato. Adding koji and/or Cellulosin T2 to the shochu distillery by-product indicated that koji was involved in caffeic acid production. Caffeic acid was not detected in raw or steamed roots of "Koganesengan", the material of sweetpotato for shochu production, suggesting that it is produced during shochu fermentation. The phenolic content and radical scavenging activity the shochu distillery by-product treated with koji and Cellulosin T2 were superior to those of commercial vinegar. These results suggest that koji treatment of sweetpotato-derived shochu distillery by-products has potential for food materials with physiological functions. Further koji treatment of sweetpotato shochu-distillery by-products may be applicable to mass production of caffeic acid.

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.

Spectroscopic studies on the interaction of cinnamic acid and its hydroxyl derivatives with human serum albumin

NASA Astrophysics Data System (ADS)

Min, Jiang; Meng-Xia, Xie; Dong, Zheng; Yuan, Liu; Xiao-Yu, Li; Xing, Chen

2004-04-01

Cinnamic acid and its derivatives possess various biological effects in remedy of many diseases. Interaction of cinnamic acid and its hydroxyl derivatives, p-coumaric acid and caffeic acid, with human serum albumin (HSA), and concomitant changes in its conformation were studied using fluorescence and Fourier transform infrared spectroscopic methods. Fluorescence data revealed the presence of one binding site on HSA for cinnamic acid and its hydroxyl derivatives, and their binding constants ( KA) are caffeic acid> p-coumaric acid> cinnamic acid when Cdrug/ CHSA ranging from 1 to 10. The changes of the secondary structure of HSA after interacting with the three drugs are estimated, respectively by combining the curve-fitting results of amid I and amid III bands. The α-helix structure has a decrease of ≈9, 5 and 3% after HSA interacted with caffeic acid, p-coumaric acid and cinnamic acid, respectively. It was found that the hydroxyls substituted on aromatic ring of the drugs play an important role in the changes of protein's secondary structure. Combining the result of fluorescence quenching and the changes of secondary structure of HSA after interaction with the three drugs, the drug-HSA interaction mode was discussed.

Rutin exhibits hepatoprotective effects in a mouse model of non-alcoholic fatty liver disease by reducing hepatic lipid levels and mitigating lipid-induced oxidative injuries.

PubMed

Liu, Qingsheng; Pan, Ran; Ding, Lei; Zhang, Fuli; Hu, Linfeng; Ding, Bin; Zhu, Linwensi; Xia, Yongliang; Dou, Xiaobing

2017-08-01

Nonalcoholic fatty liver disease (NAFLD) is characterized by excessive accumulation of hepatic lipids and oxidative injury of hepatocytes. Rutin is a natural flavonoid with significant roles in combating cellular oxidative stress and regulating lipid metabolism. The current study aims to investigate the molecular mechanisms underlying rutin's hypolipidemic and hepatoprotective effects in nonalcoholic fatty liver disease. Rutin treatment was applied to male C57BL/6 mice maintained on a high-fat diet and HepG2 cells challenged with oleic acid. Hepatic lipid accumulation was evaluated by triglyceride assay and Oil Red O staining. Oxidative hepatic injury was assessed by malondialdehyde assay, superoxide dismutase assay and reactive oxygen species assay. The expression levels of various lipogenic and lipolytic genes were determined by quantitative real-time polymerase chain reactions. In addition, liver autophagy was investigated by enzyme-linked immunosorbent assay. In both fat-challenged murine liver tissues and HepG2 cells, rutin treatment was shown to significantly lower triglyceride content and the abundance of lipid droplets. Rutin was also found to reduce cellular malondialdehyde level and restore superoxide dismutase activity in hepatocytes. Among the various lipid-related genes, rutin treatment was able to restore the expression of peroxisome proliferator-activated receptor alpha (PPAR-α) and its downstream targets, carnitine palmitoyltransferase 1 and 2 (CPT-1 and CPT-2), while suppressing those of sterol regulatory element-binding protein 1c (SREBP-1c), diglyceride acyltransfase 1 and 2 (DGAT-1 and 2), as well as acyl-CoA carboxylase (ACC). In addition, rutin was shown to repress the autophagic function of liver tissues by down-regulating key autophagy biomarkers, including tumor necrosis factor alpha (TNF-α), interleukin 1 beta (IL-1β). The experimental data demonstrated that rutin could reduce triglyceride content and mitigate oxidative injuries in fat-enriched hepatocytes. The hypolipidemic properties of rutin could be attributed to its ability to simultaneously facilitate fatty acid metabolism and inhibit lipogenesis. Copyright © 2017 Elsevier B.V. All rights reserved.

A Thick-film Sensor as a Novel Device for Determination of Polyphenols and Their Antioxidant Capacity in White Wine

PubMed Central

Photinon, Kanokorn; Chalermchart, Yongyuth; Khanongnuch, Chartchai; Wang, Shih-Han; Liu, Chung-Chiun

2010-01-01

A thick-film electrochemical sensor with an iridium-carbon working electrode was used for determining polyphenols and their antioxidant capacity in white wine. Caffeic acid was used as a model species because it has the ability to produce the highest oxidation current. The correlation coefficient of 0.9975 was obtained between sensor response and caffeic acid content. The total phenolic content (TPC) and scavenging activity on 1,1-diphenyl-2-pycrylhydrazyl (DPPH·) radical were also found to be strongly correlated with the concentration of caffeic acid, with a correlation coefficient of 0.9823 and 0.9958, respectively. The sensor prototype was proven to be a simple, efficient and cost effective device to evaluate the antioxidant capacity of substances. PMID:22294893

A thick-film sensor as a novel device for determination of polyphenols and their antioxidant capacity in white wine.

PubMed

Photinon, Kanokorn; Chalermchart, Yongyuth; Khanongnuch, Chartchai; Wang, Shih-Han; Liu, Chung-Chiun

2010-01-01

A thick-film electrochemical sensor with an iridium-carbon working electrode was used for determining polyphenols and their antioxidant capacity in white wine. Caffeic acid was used as a model species because it has the ability to produce the highest oxidation current. The correlation coefficient of 0.9975 was obtained between sensor response and caffeic acid content. The total phenolic content (TPC) and scavenging activity on 1,1-diphenyl-2-pycrylhydrazyl (DPPH·) radical were also found to be strongly correlated with the concentration of caffeic acid, with a correlation coefficient of 0.9823 and 0.9958, respectively. The sensor prototype was proven to be a simple, efficient and cost effective device to evaluate the antioxidant capacity of substances.

Synthesis, Anti-HCV, Antioxidant and Reduction of Intracellular Reactive Oxygen Species Generation of a Chlorogenic Acid Analogue with an Amide Bond Replacing the Ester Bond.

PubMed

Wang, Ling-Na; Wang, Wei; Hattori, Masao; Daneshtalab, Mohsen; Ma, Chao-Mei

2016-06-08

Chlorogenic acid is a well known natural product with important bioactivities. It contains an ester bond formed between the COOH of caffeic acid and the 3-OH of quinic acid. We synthesized a chlorogenic acid analogue, 3α-caffeoylquinic acid amide, using caffeic and quinic acids as starting materials. The caffeoylquinc acid amide was found to be much more stable than chlorogenic acid and showed anti-Hepatitis C virus (anti-HCV) activity with a potency similar to chlorogenic acid. The caffeoylquinc acid amide potently protected HepG2 cells against oxidative stress induced by tert-butyl hydroperoxide.

Dietary Consumption of Phenolic Acids and Prostate Cancer: A Case-Control Study in Sicily, Southern Italy.

PubMed

Russo, Giorgio Ivan; Campisi, Daniele; Di Mauro, Marina; Regis, Federica; Reale, Giulio; Marranzano, Marina; Ragusa, Rosalia; Solinas, Tatiana; Madonia, Massimo; Cimino, Sebastiano; Morgia, Giuseppe

2017-12-05

Dietary polyphenols gained the interest of the scientific community due to their wide content in a variety of plant-derived foods and beverages commonly consumed, such as fruits, vegetables, coffee, tea, and cocoa . We aimed to investigate whether there was an association between dietary phenolic acid consumption and prostate cancer (PCa) in South Italy. We conducted a population-based case-control study from January 2015 to December 2016 in a single institution of the municipality of Catania, southern Italy (Registration number: 41/2015). Patients with elevated PSA and/or suspicious PCa underwent transperineal prostate biopsy. A total of 118 histopathological-verified PCa cases were collected and a total of 222 controls were selected from a sample of 2044 individuals. Dietary data were collected by using two food frequency questionnaires and data on the phenolic acids content in foods was obtained from the Phenol-Explorer database (www.phenol-explorer.eu). Association between dietary intake of phenolic acids and PCa was calculated through logistic regression analysis. We found lower levels of caffeic acid (2.28 mg/day vs. 2.76 mg/day; p < 0.05) and ferulic acid (2.80 mg/day vs. 4.04 mg/day; p < 0.01) in PCa when compared to controls. The multivariate logistic regression showed that both caffeic acid (OR = 0.32; p < 0.05) and ferulic acid (OR = 0.30; p < 0.05) were associated with reduced risk of PCa. Higher intake of hydroxybenzoic acids and caffeic acids were associated with lower risk of advanced PCa. High intake of caffeic acid and ferulic acid may be associated with reduced risk of PCa.

In vitro biological screening of the anticholinesterase and antiproliferative activities of medicinal plants belonging to Annonaceae

PubMed Central

Formagio, A.S.N.; Vieira, M.C.; Volobuff, C.R.F.; Silva, M.S.; Matos, A.I.; Cardoso, C.A.L.; Foglio, M.A.; Carvalho, J.E.

2015-01-01

The aim of this research was to investigate the antiproliferative and anticholinesterase activities of 11 extracts from 5 Annonaceae species in vitro. Antiproliferative activity was assessed using 10 human cancer cell lines. Thin-layer chromatography and a microplate assay were used to screen the extracts for acetylcholinesterase (AchE) inhibitors using Ellman's reagent. The chemical compositions of the active extracts were investigated using high performance liquid chromatography. Eleven extracts obtained from five Annonaceae plant species were active and were particularly effective against the UA251, NCI-470 lung, HT-29, NCI/ADR, and K-562 cell lines with growth inhibition (GI50) values of 0.04-0.06, 0.02-0.50, 0.01-0.12, 0.10-0.27, and 0.02-0.04 µg/mL, respectively. In addition, the Annona crassiflora and A. coriacea seed extracts were the most active among the tested extracts and the most effective against the tumor cell lines, with GI50 values below 8.90 µg/mL. The A. cacans extract displayed the lowest activity. Based on the microplate assay, the percent AchE inhibition of the extracts ranged from 12 to 52%, and the A. coriacea seed extract resulted in the greatest inhibition (52%). Caffeic acid, sinapic acid, and rutin were present at higher concentrations in the A. crassiflora seed samples. The A. coriacea seeds contained ferulic and sinapic acid. Overall, the results indicated that A. crassiflora and A. coriacea extracts have antiproliferative and anticholinesterase properties, which opens up new possibilities for alternative pharmacotherapy drugs. PMID:25714885

In vitro biological screening of the anticholinesterase and antiproliferative activities of medicinal plants belonging to Annonaceae.

PubMed

Formagio, A S N; Vieira, M C; Volobuff, C R F; Silva, M S; Matos, A I; Cardoso, C A L; Foglio, M A; Carvalho, J E

2015-04-01

The aim of this research was to investigate the antiproliferative and anticholinesterase activities of 11 extracts from 5 Annonaceae species in vitro. Antiproliferative activity was assessed using 10 human cancer cell lines. Thin-layer chromatography and a microplate assay were used to screen the extracts for acetylcholinesterase (AchE) inhibitors using Ellman's reagent. The chemical compositions of the active extracts were investigated using high performance liquid chromatography. Eleven extracts obtained from five Annonaceae plant species were active and were particularly effective against the UA251, NCI-470 lung, HT-29, NCI/ADR, and K-562 cell lines with growth inhibition (GI50) values of 0.04-0.06, 0.02-0.50, 0.01-0.12, 0.10-0.27, and 0.02-0.04 µg/mL, respectively. In addition, the Annona crassiflora and A. coriacea seed extracts were the most active among the tested extracts and the most effective against the tumor cell lines, with GI50 values below 8.90 µg/mL. The A. cacans extract displayed the lowest activity. Based on the microplate assay, the percent AchE inhibition of the extracts ranged from 12 to 52%, and the A. coriacea seed extract resulted in the greatest inhibition (52%). Caffeic acid, sinapic acid, and rutin were present at higher concentrations in the A. crassiflora seed samples. The A. coriacea seeds contained ferulic and sinapic acid. Overall, the results indicated that A. crassiflora and A. coriacea extracts have antiproliferative and anticholinesterase properties, which opens up new possibilities for alternative pharmacotherapy drugs.

Phenolic compounds participating in mulberry juice sediment formation during storage.

PubMed

Zou, Bo; Xu, Yu-Juan; Wu, Ji-Jun; Yu, Yuan-Shan; Xiao, Geng-Sheng

The stability of clarified juice is of great importance in the beverage industry and to consumers. Phenolic compounds are considered to be one of the main factors responsible for sediment formation. The aim of this study is to investigate the changes in the phenolic content in clarified mulberry juice during storage. Hence, separation, identification, quantification, and analysis of the changes in the contents of phenolic compounds, both free and bound forms, in the supernatant and sediments of mulberry juice, were carried out using high performance liquid chromatographic system, equipped with a photo-diode array detector (HPLC-PDA) and HPLC coupled with quadrupole-time of flight mass spectrometric (HPLC-QTOF-MS/MS) techniques. There was an increase in the amount of sediment formed over the period of study. Total phenolic content of supernatant, as well as free phenolic content in the extracts of the precipitate decreased, whereas the bound phenolic content in the sediment increased. Quantitative estimation of individual phenolic compounds indicated high degradation of free anthocyanins in the supernatant and sediment from 938.60 to 2.30 mg/L and 235.60 to 1.74 mg/g, respectively. A decrease in flavonoids in the supernatant was also observed, whereas the contents of bound forms of gallic acid, protocatechuic acid, caffeic acid, and rutin in the sediment increased. Anthocyanins were the most abundant form of phenolics in the sediment, and accounted for 67.2% of total phenolics after 8 weeks of storage. These results revealed that phenolic compounds, particularly anthocyanins, were involved in the formation of sediments in mulberry juice during storage.

Sensitive Determination of 6-Thioguanine Using Caffeic Acid-functionalized Fe3O4 Nanoparticles as an Electrochemical Sensor

NASA Astrophysics Data System (ADS)

Amir, Md.; Tunesi, Mawada M.; Soomro, Razium A.; Baykal, Abdülhadi; Kalwar, Nazar H.

2018-04-01

The study demonstrates the potential application of caffeic acid-functionalized magnetite nanoparticles (CA-Fe3O4 NPs) as an effective electrode modifying material for the electrochemical oxidation of the 6-thioguanine (6-TG) drug. The functionalized Fe3O4 NPs were prepared using simple wet-chemical methodology where the used caffeic acid acted simultaneously as growth controlling and functionalizing agent. The study discusses the influence of an effective functionalization on the signal sensitivity observed for the electro-oxidation of 6-TG over CA-Fe3O4 NPs in comparison to a glassy carbon electrode modified with bare and nicotinic acid (NA)-functionalized Fe3O4 NPs. The experiment results provided sufficient evidence to support the importance of favorable functionality to achieve higher signal sensitivity for the electro-oxidation of 6-TG. The presence of favorable interactions between the active functional moieties of caffeic acid and 6-TG synergized with the greater surface area of magnetic NPs produces a stable electro-oxidation signal within the working range of 0.01-0.23 μM with sensitive up to 0.001 μM. Additionally, the sensor showed the strong anti-interference potential against the common co-existing drug molecules such as benzoic acid, acetaminophen, epinephrine, norepinephrine, glucose, ascorbic acid and l-cysteine. In addition, the successful quantification of 6-TG from the commercial tablets obtained from local pharmacy further signified the practical capability of the discussed sensor.

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.

Interaction of hydrated electron with dietary flavonoids and phenolic acids: rate constants and transient spectra studied by pulse radiolysis.

PubMed

Cai, Z; Li, X; Katsumura, Y

1999-10-01

The reaction rate constants and transient spectra of 11 flavonoids and 4 phenolic acids reacting with e(aq)- at neutral pH were measured. Absorption bands of the transients of e(aq)- reacting with the above compounds all located at a wavelength shorter than 400 nm. The e(aq)- scavenging abilities were divided into three groups: (+)catechin ((1.2 +/-0.1) x 10(8) M(-1)s(-1)) < 4-chromanol ((4.4 +/- 0.4) x 10(8) M(-1)s(-1)) < genistein ((6.2+/-0.4) x 10(9) M (-1) s(-1) approximately genistin ((8 +/- 1) x 10(9) M(-1)s(-1)) approximately rutin ((7.6 +/- 0.4) x M(-1)s(-1) approximately caffeic acid ((8.3 +/- 0.5) x 10(9)M(-1)s(-1)) < transcinnamic acid((1.1 +/- 0.1) x 10(10) M(-1)s(-1)) approximately p-coumaric acid ((1.1 +/- 0.1) x 10(10) M(-1)s(-1) approximately 2,4,6-trihydroxylbenzoic acid((1.1 +/- 0.1) x 10(10) M(-1)s(-1)) approximately baicalein ((1.1 +/- 0.5) x 10(10) M(-1)s(-1)) approximately baicalin((1.3 + 0.1) X 10(10) M(-1)s(-1)) approximately naringenin ((1.2 +/- 0.1) x 10(10) M(-1)s(-1)) approximately naringin ((1.0 +/- 0.1) x 10(10) M(-1)s(-1)) approximately gossypin((1.2 +/- 0.1) x 10(10) M(-1)s(-1)) approximately quercetin((1.3 +/- 0.5) x 10(10) M(-1)s(-1)). These results suggested that C4 keto group is the active site for e(aq)- to attack on flavonoids and phenolic acids, whereas the o-dihydroxy structure in B ring, the C2,3 double bond, the C3-OH group, and glucosylation, which are key structures that influence the antioxidant activities of flavonoids and phenolic acids, have little effects on the e(aq)- scavenging activities.

Analysis of Ethyl Acetate Extract of Enzymatic Hydrolysate from High Purity Oleuropein and DPPH Radical Scavenging Capacity

NASA Astrophysics Data System (ADS)

Yuan, Jiaojiao; Li, Bing; Qin, Frank G. F.; Tu, Junling

2018-01-01

High purify oleuropein (81.04% OL) was hydrolyzed by hemicellulase and phenols was existed in the ethyl acetate extract of enzymatic hydrolysate (EAE). The results presented that there were hydroxytyrosol (HT), tyrosol, caffeic acid, 3,4-dihydroxybenzoic acid, 3,4-dihydroxy phenylacetic acid in EAE by HPLC, and HT content was 19.36%. Antioxidant activities (DPPH radical scavenging capacity) were all added as the samples concentration increased, and dose-effect relationships also existed. HT possessed the highest DPPH radical scavenging capacity, followed by Vc, and eugenol, OL, caffeic acid, 3,4-dihydroxy phenylacetic acid and 3,4-dihydroxybenzoic acid.

Interactions between polyphenols in thinned young apples and porcine pancreatic α-amylase: Inhibition, detailed kinetics and fluorescence quenching.

PubMed

Sun, Lijun; Chen, Weiqi; Meng, Yonghong; Yang, Xingbin; Yuan, Li; Guo, Yurong; Warren, Frederick J; Gidley, Michael J

2016-10-01

Young apple polyphenols (YAP) and nine types of phenolic compounds were investigated regarding the inhibitory activity against porcine pancreatic α-amylase (PPA) in vitro. Tannic acid, chlorogenic acid and caffeic acid in YAP showed relatively high inhibition with the IC50 values of 0.30, 1.96 and 3.69mg/mL, respectively. A detailed kinetics of inhibition study revealed that YAP and tannic acid were competitive inhibitors of PPA, whereas chlorogenic acid and caffeic acid were mixed inhibitors, exhibiting both competitive and uncompetitive characteristics. The fluorescence of PPA could be significantly quenched by YAP and the three polyphenols, and their quenching constants were determined. The results showed that for the polyphenols investigated, the order of the apparent static quenching constants (KFQ) was in agreement with that of the reciprocal competitive inhibition constants (1/Kic) (tannic acid>chlorogenic acid>caffeic acid>epicatechin); both of the parameters were contrary to the order of the IC50 values. Thus, combining detailed kinetics and fluorescence quenching studies can be applied to characterise the interactions between polyphenols in young apples and α-amylase. Copyright © 2016 Elsevier Ltd. All rights reserved.

Chlorogenic Acid and Rutin Play a Major Role in the In Vivo Anti-Diabetic Activity of Morus alba Leaf Extract on Type II Diabetic Rats

PubMed Central

Hunyadi, Attila; Martins, Ana; Hsieh, Tusty-Jiuan; Seres, Adrienn; Zupkó, István

2012-01-01

The leaves of the white mulberry tree (Morus alba L.) are used worldwide in traditional medicine as anti-diabetics. Various constituents of mulberry leaves, such as iminosugars (i.e. 1-deoxynojirimicin), flavonoids and related compounds, polysaccharides, glycopeptides and ecdysteroids, have been reported to exert anti-diabetic activity, but knowledge about their contribution to the overall activity is limited. The objective of the present work was to determine the in vivo anti-diabetic activity of an extract of mulberry leaves (MA), and to examine to what extent three major constituents, chlorogenic acid, rutin and isoquercitrin, might contribute to the observed activity. Quantities of the three constituents of interest in the extract were determined by using HPLC-DAD. Activity was determined by using a type II diabetic rat model. After 11 days of per os administration of 250 or 750 mg/kg of MA or the corresponding amounts of each individual compound, a dose dependent decrease of non-fasting blood glucose levels were found for MA, chlorogenic acid and rutin, but not for isoquercitrin. Based on our results, chlorogenic acid and rutin might account for as much as half the observed anti-diabetic activity of MA, hence they can be considered as excellent markers for the quality control of mulberry products. PMID:23185641

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.

In vivo genotoxicity evaluation of an artichoke (Cynara scolymus L.) aqueous extract.

PubMed

Zan, Meriele A; Ferraz, Alexandre B F; Richter, Marc F; Picada, Jaqueline N; de Andrade, Heloisa H R; Lehmann, Mauricio; Dihl, Rafael R; Nunes, Emilene; Semedo, Juliane; Da Silva, Juliana

2013-02-01

The Cynara scolymus (artichoke) is widely consumed as tea or food and shows important therapeutic properties. However, few studies have assessed the possible toxic effects of artichoke extracts. This study evaluates genotoxic and mutagenic activities of artichoke leaf aqueous extract in mice using the comet assay and the micronucleus test. Leaf extracts were given by gavage (500 mg/kg, 1000 mg/kg, and 2000 mg/kg) for 3 consecutive days. Extract composition was investigated using phytochemical screening and high-performance liquid chromatography (HPLC). In addition, antioxidant capacity was analyzed through the diphenyl-picrylhydrazyl (DPPH) and xanthine oxidase assay. Phytochemical screening detected the presence of phenolic compounds, flavonoids, and saponins. HPLC analyses indicated the presence of chlorogenic acid, caffeic acid, isoquercetrin, and rutin. Extracts showed a dose-dependent free radical scavenging effect of DPPH and an inhibitory effect of xanthine oxidase. The genotoxic results showed that leaf extracts did not increase micronuclei in peripheral blood cells. Compared to the control group, a significant increase in comet assay values was observed only in bone marrow of group treated with 2000 mg/kg, the highest dose tested, indicating that artichoke tea should be consumed with moderation. This is the first report of in vivo mutagenic and genotoxic evaluation with C. scolymus. The present study revealed leaf aqueous extract from artichoke shows lack of mutagenicity in vivo, and low genotoxicity and antioxidant activity; indicating that artichoke tea should be consumed with moderation. © 2013 Institute of Food Technologists®

Anti-Wrinkle and Anti-Inflammatory Effects of Active Garlic Components and the Inhibition of MMPs via NF-κB Signaling

PubMed Central

Kim, So Ra; Jung, Yu Ri; An, Hye Jin; Kim, Dae Hyun; Jang, Eun Ji; Choi, Yeon Ja; Moon, Kyoung Mi; Park, Min Hi; Park, Chan Hum; Chung, Ki Wung; Bae, Ha Ram; Choi, Yung Whan; Kim, Nam Deuk; Chung, Hae Young

2013-01-01

Skin aging is a multisystem degenerative process caused by several factors, such as, UV irradiation, stress, and smoke. Furthermore, wrinkle formation is a striking feature of photoaging and is associated with oxidative stress and inflammatory response. In the present study, we investigated whether caffeic acid, S-allyl cysteine, and uracil, which were isolated from garlic, modulate UVB-induced wrinkle formation and effect the expression of matrix-metalloproteinase (MMP) and NF-κB signaling. The results obtained showed that all three compounds significantly inhibited the degradation of type І procollagen and the expressions of MMPs in vivo and attenuated the histological collagen fiber disorder and oxidative stress in vivo. Furthermore, caffeic acid and S-allyl cysteine were found to decrease oxidative stress and inflammation by modulating the activities of NF-κB and AP-1, and uracil exhibited an indirect anti-oxidant effect by suppressing cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) expressions levels and downregulating transcriptional factors. These results suggest that the anti-wrinkle effects of caffeic acid, S-allyl cysteine, and uracil are due to anti-oxidant and/or anti-inflammatory effects. Summarizing, caffeic acid, S-allyl cysteine, and uracil inhibited UVB-induced wrinkle formation by modulating MMP via NF-κB signaling. PMID:24066081

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.

Metabolomic profiling of the phytomedicinal constituents of Carica papaya L. leaves and seeds by 1H NMR spectroscopy and multivariate statistical analysis.

PubMed

Gogna, Navdeep; Hamid, Neda; Dorai, Kavita

2015-11-10

Extracts from the Carica papaya L. plant are widely reported to contain metabolites with antibacterial, antioxidant and anticancer activity. This study aims to analyze the metabolic profiles of papaya leaves and seeds in order to gain insights into their phytomedicinal constituents. We performed metabolite fingerprinting using 1D and 2D 1H NMR experiments and used multivariate statistical analysis to identify those plant parts that contain the most concentrations of metabolites of phytomedicinal value. Secondary metabolites such as phenyl propanoids, including flavonoids, were found in greater concentrations in the leaves as compared to the seeds. UPLC-ESI-MS verified the presence of significant metabolites in the papaya extracts suggested by the NMR analysis. Interestingly, the concentration of eleven secondary metabolites namely caffeic, cinnamic, chlorogenic, quinic, coumaric, vanillic, and protocatechuic acids, naringenin, hesperidin, rutin, and kaempferol, were higher in young as compared to old papaya leaves. The results of the NMR analysis were corroborated by estimating the total phenolic and flavonoid content of the extracts. Estimation of antioxidant activity in leaves and seed extracts by DPPH and ABTS in-vitro assays and antioxidant capacity in C2C12 cell line also showed that papaya extracts exhibit high antioxidant activity. Copyright © 2015 Elsevier B.V. All rights reserved.

Phytochemical evaluation of Lythrum salicaria extracts and their effects on guinea-pig ileum.

PubMed

Bencsik, Tímea; Barthó, Loránd; Sándor, Viktor; Papp, Nóra; Benkó, Rita; Felinger, Attila; Kilár, Ferenc; Horváth, Györgyi

2013-09-01

n-Hexane, chloroform, ethyl acetate and 50% ethanol in water extracts prepared from the air-dried flowering parts of Lythrum salicaria L. were tested for in vitro pharmacological properties on Guinea-pig ileum, which is suitable for detecting a whole range of neuronal and smooth muscle effects. UHPLC-MS was used to evaluate polyphenol components of the extracts. In the ileum, the most prominent response (46.4% related to 0.5 microM histamine) of the extracts causing smooth muscle contractions were triggered by the 50% ethanol in water extract in a concentration-dependent manner. Atropine, indomethacin and PPADS plus suramin significantly reduced the contractile response caused by this extract. The strongest inhibition was due to atropine. The results suggest that L. salicaria extracts have a moderate muscarinic receptor agonist effect in Guinea-pig ileum and that prostanoids and purinoceptor mechanisms are involved to some extent. Therefore diluted extracts of L. salicaria p.o. could be used as a mild stimulant of gastrointestinal motility. The 50% ethanol in water extract was rich in polyphenols. n-Hexane, chloroform and ethyl acetate extracts failed to contain catechin, caffeic acid, quercetin-3-D-galactoside and rutin, but they all showed spasmogenic effects, and, therefore we do not think that these compounds could be involved in the spasmogenic activity.

Antineurodegenerative effect of phenolic extracts and caffeic acid derivatives in romaine lettuce on neuron-like PC-12 cells.

PubMed

Im, Sung-Eun; Yoon, Hyungeun; Nam, Tae-Gyu; Heo, Ho Jin; Lee, Chang Yong; Kim, Dae-Ok

2010-08-01

In recent decades, romaine lettuce has been one of the fastest growing vegetables with respect to its consumption and production. An understanding is needed of the effect of major phenolic phytochemicals from romaine lettuce on biological protection for neuron-like PC-12 cells. Phenolics in fresh romaine lettuce were extracted, and then its total phenolics and total antioxidant capacity were measured spectrophotometrically. Neuroprotective effects of phenolic extract of romaine lettuce and its pure caffeic acid derivatives (caffeic, chicoric, chlorogenic, and isochlorogenic acids) in PC-12 cells were evaluated using two different in vitro methods: lactate dehydrogenase release and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide reduction assays. Total phenolics and total antioxidant capacity of 100 g of fresh romaine lettuce averaged 22.7 mg of gallic acid equivalents and 31.0 mg of vitamin C equivalents, respectively. The phenolic extract of romaine lettuce protected PC-12 cells against oxidative stress caused by H(2)O(2) in a dose-dependent manner. Isochlorogenic acid, one of the phenolics in romaine lettuce, showed stronger neuroprotection than the other three caffeic acid derivatives also found in the lettuce. Although romaine lettuce had lower levels of phenolics and antioxidant capacity compared to other common vegetables, its contribution to total antioxidant capacity and antineurodegenerative effect in human diets would be higher because of higher amounts of its daily per capita consumption compared to other common vegetables.

Synthesis, Characterization, Antioxidant Status, and Toxicity Study of Vanadium-Rutin Complex in Balb/c Mice.

PubMed

Roy, Souvik; Majumdar, Sumana; Singh, Amit Kumar; Ghosh, Balaram; Ghosh, Nilanjan; Manna, Subhadip; Chakraborty, Tania; Mallick, Sougato

2015-08-01

A new trend was developed for the formation of a complex between vanadium and flavonoid derivatives in order to increase the intestinal absorption and to reduce the toxicity of vanadium compounds. The vanadium-rutin complex was characterized by several spectroscopic techniques like ultraviolet (UV)-visible, Fourier transform infrared (FTIR), NMR, mass spectrometry, and microscopic evaluation by scanning electron microscopy. The mononuclear complex was formed by the interaction between vanadium and rutin with 1:2 metal to ligand stoichiometry. Antioxidant activity of the complex was evaluated by 1,1-diphenyl-2 picrylhydrazyl, ferric-reducing power, and 2,2'-azin-obis 3-ethylbenzothiazoline-6-sulphonic acid methods. It was shown that radical scavenging activity and ferric-reducing potential of free rutin was lower as compared with vanadium-rutin complex. The study was also investigated for oral acute toxicity and 28 days repeated oral subacute toxicity study of vanadium-rutin complex in balb/c mice. The vanadium-rutin complex showed mortality at a dose of 120 mg/kg in the balb/c mice. In 28 days repeated oral toxicity study, vanadium-rutin complex was administered to both sex of balb/c mice at dose levels of 90, 45, and 20 ppm, respectively. In addition, subacute toxicity study of vanadium-rutin complex (at 90 ppm dose level) showed increase levels of white blood cell (WBC), total bilirubin, alanine aminotransferase (ALT), alkaline phosphatase (ALP), aspartate aminotransferase (AST), creatinine, and blood urea nitrogen and decrease level of total protein (TP) as compared with control group. Histopathological study of vanadium-rutin showed structural alteration in the liver, kidney, and stomach at 90 ppm dose level. No observed toxic level of vanadium-rutin complex at 20 ppm dose level could be good for further study.

Production of caffeoylmalic acid from glucose in engineered Escherichia coli.

PubMed

Li, Tianzhen; Zhou, Wei; Bi, Huiping; Zhuang, Yibin; Zhang, Tongcun; Liu, Tao

2018-07-01

To achieve biosynthesis of caffeoylmalic acid from glucose in engineered Escherichia coli. We constructed the biosynthetic pathway of caffeoylmalic acid in E. coli by co-expression of heterologous genes RgTAL, HpaBC, At4CL2 and HCT2. To enhance the production of caffeoylmalic acid, we optimized the tyrosine metabolic pathway of E. coli to increase the supply of the substrate caffeic acid. Consequently, an E. coli-E. coli co-culture system was used for the efficient production of caffeoylmalic acid. The final titer of caffeoylmalic acid reached 570.1 mg/L. Microbial production of caffeoylmalic acid using glucose has application potential. In addition, microbial co-culture is an efficient tool for producing caffeic acid esters.

[The effects of the combined use of mineral water with ascorbic acid and rutin experimentally and clinically].

PubMed

Polushina, N D; Kartazaeva, V A; Botvineva, L A; Kozhevnikov, S A

2000-01-01

Effects of a single and course intake of glucose, ascorbic acid and rutin in combination with mineral water Essentuki N17 on blood levels of glucose, hydrocortisone, ACTH, insulin were studied in 336 Wistar male rats. 80 patients with diabetes mellitus type I and II received a course of ascorutin and mineral water. Mineral water proved able to reduce a hyperglycemic effect of vitamins. A course of mineral water and ascorutin promotes improvement of carbohydrate, lipid metabolism, elevates plasma content of ascorbic acid, diminishes the need in sugar-reducing drugs.

Characterization of putative receptors specific for quercetin on bovine aortic smooth-muscle cells

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

Yu, S.C.; Becker, C.G.

The authors have reported that tobacco glycoprotein (TGP), rutin-bovine serum albumin conjugates (R-BSA), quercetin, and chlorogenic acid are mitogenic for bovine aortic smooth-muscle cells (SMC). To investigate whether there are binding sites or receptors for these polyphenol-containing molecules on SMC, the authors have synthesized /sup 125/I-labeled rutin-bovine serum albumin ((/sup 125/I)R-BSA) of high specific activity (20 Ci/mmol). SMC were isolated from a bovine thoracic aorta and maintained in Eagle's minimum essential medium with 10% calf serum in culture. These SMC at early subpassages were suspended (3-5 x 10/sup 7/ cells/ml) in phosphate-buffered saline and incubated with (/sup 125/I)R-BSA (10 pmol)more » in the presence or absence of 200-fold unlabeled R-BSA, TGP, BSA, rutin, quercetin or related polyphenols, and catecholamines. Binding of (/sup 125/I)R-BSA to SMC was found to be reproducible and the radioligand was displaced by R-BSA, and also by TGP, rutin, quercetin, and chlorogenic acid, but not by BSA, ellagic acid, naringin, hesperetin, dopamine, epinephrine, or isoproterenol. The binding was saturable, reversible, and pH-dependent. These results demonstrate the presence of specific binding sites for quercetinon arterial SMC.« less

Impact of functional properties and release kinetics on antioxidant activity of biopolymer active films and coatings.

PubMed

Benbettaïeb, Nasreddine; Tanner, Cadhla; Cayot, Philippe; Karbowiak, Thomas; Debeaufort, Frédéric

2018-03-01

This work deals with the study of the release kinetics of some natural antioxidants (ferulic acid, caffeic acid and tyrosol) from chitosan-fish gelatin edible films immersed ethanol at 96%, as well as the kinetics of their antioxidant activity using the DPPH assay. The aim was to determine how film functional properties influence the release kinetic and antioxidant activity. The addition of antioxidants to chitosan-fish gelatin matrix decreased the water vapour permeability by more than 30%. The tensile strength (TS) increased up to 50% after the incorporation of antioxidants. Some molecular interactions between polymer chains and antioxidants were confirmed by FTIR where spectra displayed a shift of the amide-III peak. Films containing caffeic acid or a caffeic-ferulic acid mixture exhibited the highest radical scavenging activity, leading to a 90% antioxidant activity at equilibrium but the release rate controlled the efficacy of the system. Copyright © 2017 Elsevier Ltd. All rights reserved.

Role of the cultivar in choosing Clementine fruits with a high level of health-promoting compounds.

PubMed

Milella, Luigi; Caruso, Marisa; Galgano, Fernanda; Favati, Fabio; Padula, Maria Carmela; Martelli, Giuseppe

2011-05-25

Thirteen cultivars and two hybrids of Clementine fruits (Citrus clementina Hort. Ex. Tan) cultivated in Italy were characterized according to pH, titratable acidity, total soluble solids, total polyphenols, carotenoids, vitamin C, hesperidin, rutin, narirutin and naringin and radical scavenging activity. The presence of rutin in Clementine fruit juice is reported for the first time here. The results indicated that all chemical parameters statistically differentiated each cultivar (P < 0.001). In particular, principal component analysis showed a clear discrimination of five cultivars from all the other varieties based on vitamin C and total polyphenols for the Caffin cultivar, which showed also the highest antioxidant activity; narirutin for the Etna hybrid cultivar; hesperidin, rutin and total soluble solids for the SRA 89 cultivar; and naringin, hesperidin and rutin for the Esbal cultivar. Moreover, the Mandalate hybrid cultivar showed the lowest antioxidant activity as well as vitamin C and total polyphenols content, while titratable acidity and naringin level were the highest. The antioxidant activity assessed in all the fruits was closely correlated with vitamin C and total polyphenols content, rather than with the flavonoid compounds.

Preventive Role of Specific Dietary Factors and Natural Compounds Against DNA Damage and Oxidative Stress.

DTIC Science & Technology

1998-08-01

vitamins (C and E) and natural compounds (caffeic acid phenethyl ester [CAPE] and epigallocatechin gallate [ EGCG ] may be protective against mammary...caffeic acid phenethyl ester (CAPE), and epigallocatechin gallate ( EGCG ) in inhibiting DNA damage. These antioxidants are found in natural products such...as fruits and vegetables (vitamins C and E), the popular medicine honeybee propolis (CAPE), or green tea ( EGCG ). Studies carried out to date suggest

The role of cyclodextrins in ORAC-fluorescence assays. antioxidant capacity of tyrosol and caffeic acid with hydroxypropyl-β-cyclodextrin.

PubMed

García-Padial, Marcos; Martínez-Ohárriz, María Cristina; Navarro-Blasco, Iñigo; Zornoza, Arantza

2013-12-18

Tyrosol and caffeic acid are biophenols that contribute to the beneficial properties of virgin olive oil. The influence of hydroxypropyl-β-cyclodextrin (HPβ-CD) on their respective antioxidant capacities was analyzed. The ORAC antioxidant activity of tyrosol (expressed as μM Trolox equivalents/μM Tyrosol) was 0.83 ± 0.03 and it increased up to 1.20 ± 0.11 in the presence of 0.8 mM HPβ-CD. However, the ORAC antioxidant activity of caffeic acid experienced no change. The different effect of HPβ-CD on each compound was discussed. In addition, the effect of increasing concentrations of different cyclodextrins in the development of ORAC-fluorescence (ORAC-FL) assays was studied. The ORAC signal was higher for HPβ-CD, followed by Mβ-CD, β-CD, γ-CD and finally α-CD. These results could be explained by the formation of inclusion complexes with fluorescein.

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.

Binding of caffeine with caffeic acid and chlorogenic acid using fluorescence quenching, UV/vis and FTIR spectroscopic techniques.

PubMed

Belay, Abebe; Kim, Hyung Kook; Hwang, Yoon-Hwae

2016-03-01

The interactions of caffeine (CF) with chlorogenic acid (CGA) and caffeic acid (CFA) were investigated by fluorescence quenching, UV/vis and Fourier transform infrared (FTIR) spectroscopic techniques. The results of the study indicated that the fluorescence quenching between caffeine and hydroxycinnamic acids could be rationalized in terms of static quenching or the formation of non-fluorescent CF-CFA and CF-CGA complexes. From fluorescence quenching spectral analysis, the quenching constant (KSV), quenching rate constant (kq), number of binding sites (n), thermodynamic properties and conformational changes of the interaction were determined. The quenching constants (KSV) between CF and CGA, CFA are 1.84 × 10(4) and 1.04 × 10(4) L/mol at 298 K and their binding site n is ~ 1. Thermodynamic parameters determined using the Van't Hoff equation indicated that hydrogen bonds and van der Waal's forces have a major role in the reaction of caffeine with caffeic acid and chlorogenic acid. The 3D fluorescence, UV/vis and FTIR spectra also showed that the binding of CF with CFA and CGA induces conformational changes in CFA and CGA. Copyright © 2015 John Wiley & Sons, Ltd.

Effects of the Aqueous Extract from Tabebuia roseoalba and Phenolic Acids on Hyperuricemia and Inflammation

PubMed Central

Ferraz-Filha, Zilma Schimith; Ferrari, Fernanda Cristina; Araújo, Marcela Carolina de Paula Michel; Bernardes, Ana Catharina Fernandes P. F.

2017-01-01

Tabebuia species (Bignoniaceae) have long been used in folk medicine as anti-inflammatory, antirheumatic, antimicrobial, and antitumor. The aim of this study was to investigate if aqueous extract from the leaves (AEL) of Tabebuia roseoalba (Ridl.) Sandwith, Bignoniaceae, and its constituents could be useful to decrease serum uric acid levels and restrain the gout inflammatory process. HPLC analysis identified caffeic acid and chlorogenic acid in AEL. Antihyperuricemic effects and inhibition of liver XOD (xanthine oxidoreductase) by AEL and identified compounds were evaluated in hyperuricemic mice. Anti-inflammatory activity was evaluated on MSU (monosodium urate) crystal-induced paw edema. In addition, AEL antioxidant activity in vitro was evaluated. AEL, caffeic, and chlorogenic acids were able to reduce serum uric acid levels in hyperuricemic mice probably through inhibition of liver xanthine oxidase activity and significantly decreased the paw edema induced by MSU crystals. AEL showed significant antioxidant activity in all evaluated assays. The results show that the AEL of Tabebuia roseoalba can be a promising agent for treatment for gout and inflammatory diseases. We suggest that caffeic and chlorogenic acids may be responsible for the activities demonstrated by the species. PMID:29375639

Silicon-Induced Changes in Antifungal Phenolic Acids, Flavonoids, and Key Phenylpropanoid Pathway Genes during the Interaction between Miniature Roses and the Biotrophic Pathogen Podosphaera pannosa1[W

PubMed Central

Shetty, Radhakrishna; Fretté, Xavier; Jensen, Birgit; Shetty, Nandini Prasad; Jensen, Jens Due; Jørgensen, Hans Jørgen Lyngs; Newman, Mari-Anne; Christensen, Lars Porskjær

2011-01-01

Application of 3.6 mm silicon (Si+) to the rose (Rosa hybrida) cultivar Smart increased the concentration of antimicrobial phenolic acids and flavonoids in response to infection by rose powdery mildew (Podosphaera pannosa). Simultaneously, the expression of genes coding for key enzymes in the phenylpropanoid pathway (phenylalanine ammonia lyase, cinnamyl alcohol dehydrogenase, and chalcone synthase) was up-regulated. The increase in phenolic compounds correlated with a 46% reduction in disease severity compared with inoculated leaves without Si application (Si−). Furthermore, Si application without pathogen inoculation induced gene expression and primed the accumulation of several phenolics compared with the uninoculated Si− control. Chlorogenic acid was the phenolic acid detected in the highest concentration, with an increase of more than 80% in Si+ inoculated compared with Si− uninoculated plants. Among the quantified flavonoids, rutin and quercitrin were detected in the highest concentrations, and the rutin concentration increased more than 20-fold in Si+ inoculated compared with Si− uninoculated plants. Both rutin and chlorogenic acid had antimicrobial effects on P. pannosa, evidenced by reduced conidial germination and appressorium formation of the pathogen, both after spray application and infiltration into leaves. The application of rutin and chlorogenic acid reduced powdery mildew severity by 40% to 50%, and observation of an effect after leaf infiltration indicated that these two phenolics can be transported to the epidermal surface. In conclusion, we provide evidence that Si plays an active role in disease reduction in rose by inducing the production of antifungal phenolic metabolites as a response to powdery mildew infection. PMID:22021421

Phenolic Acid Composition, Antiatherogenic and Anticancer Potential of Honeys Derived from Various Regions in Greece

PubMed Central

Spilioti, Eliana; Jaakkola, Mari; Tolonen, Tiina; Lipponen, Maija; Virtanen, Vesa; Chinou, Ioanna; Kassi, Eva; Karabournioti, Sofia; Moutsatsou, Paraskevi

2014-01-01

The phenolic acid profile of honey depends greatly on its botanical and geographical origin. In this study, we carried out a quantitative analysis of phenolic acids in the ethyl acetate extract of 12 honeys collected from various regions in Greece. Our findings indicate that protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid and p-coumaric acid are the major phenolic acids of the honeys examined. Conifer tree honey (from pine and fir) contained significantly higher concentrations of protocatechuic and caffeic acid (mean: 6640 and 397 µg/kg honey respectively) than thyme and citrus honey (mean of protocatechuic and caffeic acid: 437.6 and 116 µg/kg honey respectively). p-Hydroxybenzoic acid was the dominant compound in thyme honeys (mean: 1252.5 µg/kg honey). We further examined the antioxidant potential (ORAC assay) of the extracts, their ability to influence viability of prostate cancer (PC-3) and breast cancer (MCF-7) cells as well as their lowering effect on TNF- α-induced adhesion molecule expression in endothelial cells (HAEC). ORAC values of Greek honeys ranged from 415 to 2129 µmol Trolox equivalent/kg honey and correlated significantly with their content in protocatechuic acid (p<0.001), p-hydroxybenzoic acid (p<0.01), vanillic acid (p<0.05), caffeic acid (p<0.01), p-coumaric acid (p<0.001) and their total phenolic content (p<0.001). Honey extracts reduced significantly the viability of PC-3 and MCF-7 cells as well as the expression of adhesion molecules in HAEC. Importantly, vanillic acid content correlated significantly with anticancer activity in PC-3 and MCF-7 cells (p<0.01, p<0.05 respectively). Protocatechuic acid, vanillic acid and total phenolic content correlated significantly with the inhibition of VCAM-1 expression (p<0.05, p<0.05 and p<0.01 respectively). In conclusion, Greek honeys are rich in phenolic acids, in particular protocatechuic and p-hydroxybenzoic acid and exhibit significant antioxidant, anticancer and antiatherogenic activities which may be attributed, at least in part, to their phenolic acid content. PMID:24752205

Antimicrobial and enhancement of the antibiotic activity by phenolic compounds: Gallic acid, caffeic acid and pyrogallol.

PubMed

Lima, Valéria N; Oliveira-Tintino, Cícera D M; Santos, Enaide S; Morais, Luís P; Tintino, Saulo R; Freitas, Thiago S; Geraldo, Yuri S; Pereira, Raimundo L S; Cruz, Rafael P; Menezes, Irwin R A; Coutinho, Henrique D M

2016-10-01

The indiscriminate use of antimicrobial drugs has increased the spectrum of exposure of these organisms. In our studies, these phenolic compounds were evaluated: gallic acid, caffeic acid and pyrogallol. The antibacterial, antifungal and modulatory of antibiotic activities of these compounds were assayed using microdilution method of Minimum Inhibitory Concentration (MIC) to bacteria and Minimum Fungicide Concentration (MFC) to fungi. The modulation was made by comparisons of the MIC and MFC of the compounds alone and combined with drugs against bacteria and fungi respectively, using a sub-inhibitory concentration of 128 μg/mL of substances (MIC/8). All substances not demonstrated clinically relevant antibacterial activity with a MIC above ≥1024 μg/mL. As a result, we observed that the caffeic acid presented a potentiating antibacterial effect over the 3 groups of bacteria studied. Pyrogallol showed a synergistic effect with two of the antibiotics tested, but only against Staphylococcus aureus. In general, caffeic acid was the substance that presented with the greatest number of antibiotics and with the greatest number of bacteria. In relation to the antifungal activity of all the compounds, the verified results were ≥1024 μg/mL, not demonstrating significant activity. Regarding potentiation of the effect of fluconazole, was observed synergistic effect only when assayed against Candida tropicalis, with all substances. Therefore, as can be seen, the compounds presented as substances that can be promising potentiating agents of antimicrobial drugs, even though they do not have direct antibacterial and antifungal action. Copyright © 2016 Elsevier Ltd. All rights reserved.

The adsorption interaction of a rutin-biopolymer complex with nanosized silica particles

NASA Astrophysics Data System (ADS)

Fedyanina, T. V.; Barvinchenko, V. N.; Lipkovskaya, N. A.; Pogorelyi, V. K.

2008-10-01

The influence of complex formation with biopolymers on the optical and acid properties of natural flavonoid rutin was studied. The adsorption interaction of biologically active flavonoids from officinal plants with the surface of nanosized silica particles was found to depend on the chemical nature of the biopolymer and adsorbate and solution properties.

Antioxidant and prooxidant nature of hydroxycinnamic acid derivatives ferulic and caffeic acids.

PubMed

Maurya, Dharmendra Kumar; Devasagayam, Thomas Paul Asir

2010-12-01

Dietary polyphenols are beneficial to human health by exerting various biological effects. Ferulic and caffeic acids are hydroxycinnamic acid derivatives widely distributed in plant-derived food products. Studies indicate that some dietary compounds may have concentration-dependent antioxidant or prooxidant activities. The present study concerns such activities of ferulic and caffeic acids. They have concentration-dependent antioxidant effects in terms of inhibition of lipid peroxidation and reactive oxygen species-scavenging after 2,2'-azobis-amidinopropane dihydrochloride-induced damage in mouse liver microsomes and splenic lymphocytes respectively. They also show differential scavenging of nitric oxide, superoxide and 2,2'-azino-bis-3-ethylbenzthiazoline-6-sulfonic acid radical (ABTS*(+)). In DPPH (1,1-diphenyl picrylhydrazyl) assay above 20 μM the absorbance start increasing due to the formation of an unknown adduct which has a shoulder at 517 nm. However, in Fenton reaction, above 5 μM, they behave as prooxidants and the possible mechanisms responsible for their prooxidant property may be related to their ferric reducing ability. These findings may have significant health implications where these natural compounds are being used/consumed. Copyright © 2010 Elsevier Ltd. All rights reserved.

Modulation of phenytoin teratogenicity and embryonic covalent binding by acetylsalicylic acid, caffeic acid, and alpha-phenyl-N-t-butylnitrone: implications for bioactivation by prostaglandin synthetase

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

Wells, P.G.; Zubovits, J.T.; Wong, S.T.

1989-02-01

Teratogenicity of the anticonvulsant drug phenytoin is thought to involve its bioactivation by cytochromes P-450 to a reactive arene oxide intermediate. We hypothesized that phenytoin also may be bioactivated to a teratogenic free radical intermediate by another enzymatic system, prostaglandin synthetase. To evaluate the teratogenic contribution of this latter pathway, an irreversible inhibitor of prostaglandin synthetase, acetylsalicylic acid (ASA), 10 mg/kg intraperitoneally (ip), was administered to pregnant CD-1 mice at 9:00 AM on Gestational Days 12 and 13, 2 hr before phenytoin, 65 mg/kg ip. Other groups were pretreated 2 hr prior to phenytoin administration with either the antioxidant caffeicmore » acid or the free radical spin trapping agent alpha-phenyl-N-t-butylnitrone (PBN). Caffeic acid and PBN were given ip in doses that respectively were up to 1.0 to 0.05 molar equivalents to the dose of phenytoin. Dams were killed on Day 19 and the fetuses were assessed for teratologic anomalies. A similar study evaluated the effect of ASA on the in vivo covalent binding of radiolabeled phenytoin administered on Day 12, in which case dams were killed 24 hr later on Day 13. ASA pretreatment produced a 50% reduction in the incidence of fetal cleft palates induced by phenytoin (p less than 0.05), without significantly altering the incidence of resorptions or mean fetal body weight. Pretreatment with either caffeic acid or PBN resulted in dose-related decreases in the incidence of fetal cleft palates produced by phenytoin, with maximal respective reductions of 71 and 82% at the highest doses of caffeic acid and PBN (p less than 0.05).« less

Immunomodulatory and cellular anti-oxidant activities of caffeic, ferulic, and p-coumaric phenolic acids: a structure-activity relationship study.

PubMed

Kilani-Jaziri, Soumaya; Mokdad-Bzeouich, Imen; Krifa, Mounira; Nasr, Nouha; Ghedira, Kamel; Chekir-Ghedira, Leila

2017-10-01

Many studies have been performed to assess the potential utility of natural products as immunomodulatory agents to enhance host responses and to reduce damage to the human body. To determine whether phenolic compounds (caffeic, ferulic, and p-coumaric acids) have immunomodulatory effects and clarify which types of immune effector cells are stimulated in vitro, we evaluated their effect on splenocyte proliferation and lysosomal enzyme activity. We also investigated the activity of natural killer (NK) cells and cytotoxic T lymphocytes (CTL). In addition, induction of the cellular antioxidant activity in splenocytes, macrophages, and red blood cells was determined by measuring the fluorescence of the DCF product. The study first results indicated that caffeic, ferulic, and p-coumaric acids significantly promote LPS-stimulated splenocyte proliferation, suggesting a potential activation of B cells, and enhanced humoral immune response in hosts treated by the tested natural products. Phenolic acids significantly enhanced the killing activity of isolated NK and CTL cells but had negligible effects on mitogen-induced proliferation of splenic T cells. We showed that caffeic acid enhances lysosomal enzyme activity in murine peritoneal macrophages, suggesting a potential role in activating such cells. Immunomodulatory activity was concomitant with the cellular antioxidant effect in macrophages and splenocytes of caffeic and ferulic acids. We conclude from this study that caffeic, ferulic, and p-coumaric acids exhibited an immunomodulatory effect which could be ascribed, in part, to their cytoprotective effect via their antioxidant capacity. Furthermore, these results suggest that these natural products could be potentially used to modulate immune cell functions in physiological and pathological conditions.

Induction of nodD Gene in a Betarhizobium Isolate, Cupriavidus sp. of Mimosa pudica, by Root Nodule Phenolic Acids.

PubMed

Mandal, Santi M; Chakraborty, Dipjyoti; Dutta, Suhrid R; Ghosh, Ananta K; Pati, Bikas R; Korpole, Suresh; Paul, Debarati

2016-06-01

A range of phenolic acids, viz., p-coumaric acid, 4-hydroxybenzaldehyde, 4-hydroxybenzoic acid, protocatechuic acid, caffeic acid, ferulic acid, and cinnamic acid have been isolated and identified by LC-MS analysis in the roots and root nodules of Mimosa pudica. The effects of identified phenolic acids on the regulation of nodulation (nod) genes have been evaluated in a betarhizobium isolate of M. pudica root nodule. Protocatechuic acid and p-hydroxybenzoic acid were most effective in inducing nod gene, whereas caffeic acid had no significant effect. Phenylalanine ammonia lyase, peroxidase, and polyphenol oxidase activities were estimated, indicating regulation and metabolism of phenolic acids in root nodules. These results showed that nodD gene expression of betarhizobium is regulated by simple phenolic acids such as protocatechuic acid and p-hydroxybenzoic acid present in host root nodule and sustains nodule organogenesis.

EFFECTS OF DIFFERENT HYDROPONIC SUBSTRATE COMBINATIONS AND WATERING REGIMES ON PHYSIOLOGICAL AND ANTI-FUNGAL PROPERTIES OF SIPHONOCHILUS AETHIOPICUS

PubMed Central

S, Xego; L, Kambizi; F, Nchu

2017-01-01

Background: Production of medicinal plants in controlled environments, particularly hydroponic technology, provides opportunities for high quality biomass accumulation and optimizes production of secondary metabolites. Applying special watering regimes in combination with efficient soil draining is an encouraging new tool for the production of pharmaceutical relevant plants. The purpose of this paper was to evaluate the effect of substrate combinations and watering regimes on nutrient uptake, anti-F. oxysporum activity and secondary metabolite profile of S. aethiopicus. Materials and Methods: Coir was used as the main component for the preparation of media in different combinations; TI (Coir + vermiculite + perlite + bark), T2 (Coir + bark), T3 (Coir + perlite) and T4 (Coir + vermiculite). Plants in different treatments were grown under two watering regimes: 3 and 5-days watering intervals. At 9 weeks post treatment, plants were harvested, oven dried and tissue nutrient content, anti-F. oxysporum activity and secondary metabolites were analyzed. Results: The results showed that there were significant differences (P < 0.05) on the uptake of P, K, N, Mg, Fe, Cu, B and NH4-.The highest mean values for most nutrients were obtained in treatments under 3-days interval. Acetone extracts of S. aethiopicus under 5-days interval were the most bioactive against F. oxysporum. The MIC values obtained are relatively lower for the rhizomes, ranging from 0.078 - 0.3125 mg/ml compared to the higher MIC values (0.375 - 0.75 mg/ml) obtained in the leaves. LC-MS analysis of acetone extracts revealed the presence of phytochemicals such as caffeic acid, quercetin, p-hydroxybenzoic acid, rutin, kaempferol, epicatechin, naringenin, hesperetin and protocatechuic acid. Conclusion: The antimicrobial activity and/or the phytochemical profile of the crude extracts were affected by watering regimes. PMID:28480420

Elevated CO2 and salinity are responsible for phenolics-enrichment in two differently pigmented lettuces.

PubMed

Sgherri, Cristina; Pérez-López, Usue; Micaelli, Francesco; Miranda-Apodaca, Jon; Mena-Petite, Amaia; Muñoz-Rueda, Alberto; Quartacci, Mike Frank

2017-06-01

Both salt stress and high CO 2 level, besides influencing secondary metabolism, can affect oxidative status of plants mainly acting in an opposite way with salinity provoking oxidative stress and elevated CO 2 alleviating it. The aim of the present work was to study the changes in the composition of phenolic acids and flavonoids as well as in the antioxidant activity in two differently pigmented lettuce cvs (green or red leaf) when submitted to salinity (200 mM NaCl) or elevated CO 2 (700 ppm) or to their combination in order to evaluate how a future global change can affect lettuce quality. Following treatments, the red cv. always maintained higher levels of antioxidant secondary metabolites as well as antioxidant activity, proving to be more responsive to altered environmental conditions than the green one. Overall, these results suggest that the application of moderate salinity or elevated CO 2 , alone or in combination, can induce the production of some phenolics that increase the health benefits of lettuce. In particular, moderate salinity was able to induce the synthesis of the flavonoids quercetin, quercetin-3-O-glucoside, quercetin-3-O-glucuronide and quercitrin. Phenolics-enrichment as well as a higher antioxidant capacity were also observed under high CO 2 with the red lettuce accumulating cyanidin, free chlorogenic acid, conjugated caffeic and ferulic acid as well as quercetin, quercetin-3-O-glucoside, quercetin-3-O-glucuronide, luteolin-7-O-glucoside, rutin, quercitrin and kaempferol. When salinity was present in combination with elevated CO 2 , reduction in yield was prevented and a higher presence of phenolic compounds, in particular luteolin, was observed compared to salinity alone. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

EFFECTS OF DIFFERENT HYDROPONIC SUBSTRATE COMBINATIONS AND WATERING REGIMES ON PHYSIOLOGICAL AND ANTI-FUNGAL PROPERTIES OF SIPHONOCHILUS AETHIOPICUS.

PubMed

S, Xego; L, Kambizi; F, Nchu

2017-01-01

Production of medicinal plants in controlled environments, particularly hydroponic technology, provides opportunities for high quality biomass accumulation and optimizes production of secondary metabolites. Applying special watering regimes in combination with efficient soil draining is an encouraging new tool for the production of pharmaceutical relevant plants. The purpose of this paper was to evaluate the effect of substrate combinations and watering regimes on nutrient uptake, anti- F. oxysporum activity and secondary metabolite profile of S. aethiopicus . Coir was used as the main component for the preparation of media in different combinations; TI (Coir + vermiculite + perlite + bark), T2 (Coir + bark), T3 (Coir + perlite) and T4 (Coir + vermiculite). Plants in different treatments were grown under two watering regimes: 3 and 5-days watering intervals. At 9 weeks post treatment, plants were harvested, oven dried and tissue nutrient content, anti- F. oxysporum activity and secondary metabolites were analyzed. The results showed that there were significant differences ( P < 0.05) on the uptake of P, K, N, Mg, Fe, Cu, B and NH4 - .The highest mean values for most nutrients were obtained in treatments under 3-days interval. Acetone extracts of S. aethiopicus under 5-days interval were the most bioactive against F. oxysporum . The MIC values obtained are relatively lower for the rhizomes, ranging from 0.078 - 0.3125 mg/ml compared to the higher MIC values (0.375 - 0.75 mg/ml) obtained in the leaves. LC-MS analysis of acetone extracts revealed the presence of phytochemicals such as caffeic acid, quercetin, p-hydroxybenzoic acid, rutin, kaempferol, epicatechin, naringenin, hesperetin and protocatechuic acid. The antimicrobial activity and/or the phytochemical profile of the crude extracts were affected by watering regimes.

African eggplant (Solanum anguivi Lam.) fruit with bioactive polyphenolic compounds exerts in vitro antioxidant properties and inhibits Ca(2+)-induced mitochondrial swelling.

PubMed

Elekofehinti, Olusola Olalekan; Kamdem, Jean Paul; Bolingon, Aline Augusti; Athayde, Margareth Linde; Lopes, Seeger Rodrigo; Waczuk, Emily Pansera; Kade, Ige Joseph; Adanlawo, Isaac Gbadura; Rocha, Joao Batista Teixeira

2013-10-01

To evaluate the antioxidant and radical scavenging activities of Solanum anguivi fruit (SAG) and its possible effect on mitochondrial permeability transition pore as well as mitochondrial membrane potential (ΔΨm) isolated from rat liver. Antioxidant activity of SAG was assayed by using 2,2-diphenyl-1-picrylhydrazyl (DPPH), reducing power, iron chelation and ability to inhibit lipid peroxidation in both liver and brain homogenate of rats. Also, the effect of SAG on mitochondrial membrane potential and mitochondrial swelling were determined. Identification and quantification of bioactive polyphenolics was done by HPLC-DAD. SAG exhibited potent and concentration dependent free radical-scavenging activity (IC50/DPPH=275.03±7.8 μg/mL). Reductive and iron chelation abilities also increase with increase in SAG concentration. SAG also inhibited peroxidation of cerebral and hepatic lipids subjected to iron oxidative assault. SAG protected against Ca(2+) (110 μmol/L)-induced mitochondrial swelling and maintained the ΔΨm. HPLC analysis revealed the presence of gallic acid [(17.54±0.04) mg/g], chlorogenic acid (21.90±0.02 mg/g), caffeic acid (16.64±0.01 mg/g), rutin [(14.71±0.03) mg/g] and quercetin [(7.39±0.05) mg/g]. These effects could be attributed to the bioactive polyphenolic compounds present in the extract. Our results suggest that SAG extract is a potential source of natural antioxidants that may be used not only in pharmaceutical and food industry but also in the treatment of diseases associated with oxidative stress. Copyright © 2013 Asian Pacific Tropical Biomedical Magazine. Published by Elsevier B.V. All rights reserved.

Protective Effects of Chlorogenic Acid and its Metabolites on Hydrogen Peroxide-Induced Alterations in Rat Brain Slices: A Comparative Study with Resveratrol.

PubMed

Gul, Zulfiye; Demircan, Celaleddin; Bagdas, Deniz; Buyukuysal, Rifat Levent

2016-08-01

The effectiveness of chlorogenic acid and its main metabolites, caffeic and quinic acids, against oxidative stress was investigated. Resveratrol, another natural phenolic compound, was also tested for comparison. Rat cortical slices were incubated with 200 μM H2O2 for 1 h, and alterations in oxidative stress parameters, such as 2, 3, 5-triphenyltetrazolium chloride (TTC) staining and the production of both malondialdehyde (MDA) and reactive oxygen species (ROS), were assayed in the absence or presence of phenolic compounds. Additionally, the effectiveness of chlorogenic acid and other compounds on H2O2-induced increases in fluorescence intensities were also compared in slice-free incubation medium. Although quinic acid failed, chlorogenic and caffeic acids significantly ameliorated the H2O2-induced decline in TTC staining intensities. Although resveratrol also caused an increase in staining intensity, its effect was not dose-dependent; the high concentrations of resveratrol tested in the present study (10 and 100 μM) further lessened the staining of the slices. Additionally, all phenolic compounds significantly attenuated the H2O2-induced increases in MDA and ROS levels in cortical slices. When the IC50 values were compared to H2O2-induced alterations, chlorogenic acid was more potent than either its metabolites or resveratrol for all parameters studied under these experimental conditions. In slice-free experimental conditions, on the other hand, chlorogenic and caffeic acids significantly attenuated the fluorescence emission enhanced by H2O2 with a similar order of potency to that obtained in slice-containing physiological medium. These results indicate that chlorogenic acid is a more potent phenolic compound than resveratrol and its main metabolites caffeic and quinic acids against H2O2-induced alterations in oxidative stress parameters in rat cortical slices.

Rutin-Mediated Priming of Plant Resistance to Three Bacterial Pathogens Initiating the Early SA Signal Pathway

PubMed Central

Li, Yang; Wang, Yingzi; Li, Ming; Wang, Yong; Ding, Xinhua; Chu, Zhaohui

2016-01-01

Flavonoids are ubiquitous in the plant kingdom and have many diverse functions, including UV protection, auxin transport inhibition, allelopathy, flower coloring and insect resistance. Here we show that rutin, a proud member of the flavonoid family, could be functional as an activator to improve plant disease resistances. Three plant species pretreated with 2 mM rutin were found to enhance resistance to Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, and Pseudomonas syringae pv. tomato strain DC3000 in rice, tobacco and Arabidopsis thaliana respectively. While they were normally propagated on the cultural medium supplemented with 2 mM rutin for those pathogenic bacteria. The enhanced resistance was associated with primed expression of several pathogenesis-related genes. We also demonstrated that the rutin-mediated priming resistance was attenuated in npr1, eds1, eds5, pad4-1, ndr1 mutants, and NahG transgenic Arabidopsis plant, while not in either snc1-11, ein2-5 or jar1 mutants. We concluded that the rutin-priming defense signal was modulated by the salicylic acid (SA)-dependent pathway from an early stage upstream of NDR1 and EDS1. PMID:26751786

Effects of plant phenols of performance of southern armyworm larvae.

PubMed

Lindroth, R L; Peterson, S S

1988-03-01

We evaluated the effects of two classes of phenols on performance of penultimate instar southern armyworms, Spodoptera eridania. One class consisted of phenols containing a catechol (ortho-dihydroxybenzene) moiety and included chlorogenic acid, quercetin, rutin, and rhamnetin. A second group consisted of the phenolic glycoside salicin and its derivatives salicortin and tremulacin. The compounds were painted onto lima bean (Phaseolus lunatus) leaves and fed to larvae for the duration of the fifth instar. Chlorogenic acid and rhamnetin had no deleterious effects; rutin and quercetin caused some mortality and rutin reduced growth rates by decreasing consumption and digestion efficiency. Results showed that ortho-dihydroxybenzene groups may be necessary, but are not sufficient for biological activity. Salicin did not affect larvae; salicortin and tremulacin reduced growth rates primarily by decreasing consumption. These two compounds also caused degenerative lesions in midgut tissues. The presence of a benzoyl ester group in tremulacin accentuates its toxicity, relative to that of salicortin.

Simultaneous determination of rutin and ascorbic acid in a sequential injection lab-at-valve system.

PubMed

Al-Shwaiyat, Mohammed Khair E A; Miekh, Yuliia V; Denisenko, Tatyana A; Vishnikin, Andriy B; Andruch, Vasil; Bazel, Yaroslav R

2018-02-05

A green, simple, accurate and highly sensitive sequential injection lab-at-valve procedure has been developed for the simultaneous determination of ascorbic acid (Asc) and rutin using 18-molybdo-2-phosphate Wells-Dawson heteropoly anion (18-MPA). The method is based on the dependence of the reaction rate between 18-MPA and reducing agents on the solution pH. Only Asc is capable of interacting with 18-MPA at pH 4.7, while at pH 7.4 the reaction with both Asc and rutin proceeds simultaneously. In order to improve the precision and sensitivity of the analysis, to minimize reagent consumption and to remove the Schlieren effect, the manifold for the sequential injection analysis was supplemented with external reaction chamber, and the reaction mixture was segmented. By the reduction of 18-MPA with reducing agents one- and two-electron heteropoly blues are formed. The fraction of one-electron heteropoly blue increases at low concentrations of the reducer. Measurement of the absorbance at a wavelength corresponding to the isobestic point allows strictly linear calibration graphs to be obtained. The calibration curves were linear in the concentration ranges of 0.3-24mgL -1 and 0.2-14mgL -1 with detection limits of 0.13mgL -1 and 0.09mgL -1 for rutin and Asc, respectively. The determination of rutin was possible in the presence of up to a 20-fold molar excess of Asc. The method was applied to the determination of Asc and rutin in ascorutin tablets with acceptable accuracy and precision (1-2%). Copyright © 2017 Elsevier B.V. All rights reserved.

Comparison of different immobilized systems in the removal of peanut allergens from peanut extracts.

USDA-ARS?s Scientific Manuscript database

The objective of this study was to determine which of the magnetic-bead systems (Ca2+, Fe3+, caffeic acid, hydrophobic) would bind and separate peanut allergens from other proteins in a peanut extract more efficiently. Commercial Ca2+ and hydrophobic magnetic beads, and caffeic-beads (prepared by at...

Substituted Caffeic and Ferulic Acid Phenethyl Esters: Synthesis, Leukotrienes Biosynthesis Inhibition, and Cytotoxic Activity.

PubMed

Morin, Pier; St-Coeur, Patrick-Denis; Doiron, Jérémie A; Cormier, Marc; Poitras, Julie J; Surette, Marc E; Touaibia, Mohamed

2017-07-06

Glioblastoma multiforme (GBM) is an aggressive brain tumor that correlates with short patient survival and for which therapeutic options are limited. Polyphenolic compounds, including caffeic acid phenethyl ester (CAPE, 1a ), have been investigated for their anticancer properties in several types of cancer. To further explore these properties in brain cancer cells, a series of caffeic and ferulic acid esters bearing additional oxygens moieties (OH or OCH₃) were designed and synthesized. (CAPE, 1a ), but not ferulic acid phenethyl ester (FAPE, 1b ), displayed substantial cytotoxicity against two glioma cell lines. Some but not all selected compounds derived from both (CAPE, 1a ) and (FAPE, 1b ) also displayed cytotoxicity. All CAPE-derived compounds were able to significantly inhibit 5-lipoxygenase (5-LO), however FAPE-derived compounds were largely ineffective 5-LO inhibitors. Molecular docking revealed new hydrogen bonds and π-π interactions between the enzyme and some of the investigated compounds. Overall, this work highlights the relevance of exploring polyphenolic compounds in cancer models and provides additional leads in the development of novel therapeutic strategies in gliomas.

Population Variability of Main Secondary Metabolites in Hypericum lydium Boiss. (Hypericaceae)

PubMed Central

Çirak, Cüneyt; Radusiene, Jolita; Ivanauskas, Liudas; Jakstas, Valdas; Çamaş, Necdet

2015-01-01

In the present study, we investigated the variation in the content of naphthodianthrones hypericin and pseudohypericin, phloroglucinol derivatives hyperforin and adhyperforin, the phenolic acids as chlorogenic acid, neochlorogenic acid, 2,4-dihydroxybenzoic acid, and the flavonols, namely, hyperoside, isoquercitrin, quercitrin, quercetin, avicularin, rutin, (+)-catechin and (-)-epicatechin, and biflavonoid amentoflavone among wild H. lydium Boiss. populations from five different growing sites of Turkey for the first time. The aerial parts representing a total of 30 individuals were collected at full flowering and dissected into floral, leaf and stem tissues. After dried at room temperature, the plant materials were assayed for chemical contents by HPLC. The populations varied significantly in the content of chemical compounds. Among different plant parts, flowers were found to be main repository site of hyperforin, adhyperforin, hypericin, pseudohypericin, amentoflavone, quercetin, avicularin, rutin and (+)-catechin accumulations whereas rest of the compounds tested were accumulated primarily in leaves in all growing localities. The stems were the least accumulative organ that did not yield hyperforin, adhyperforin and rutin. The chemical diversity among the populations and plant parts is discussed as being possibly the result of different environmental, morphological and genetic factors. PMID:26330888

Antioxidative effect of lipophilized caffeic acid in fish oil enriched mayonnaise and milk.

PubMed

Alemán, Mercedes; Bou, Ricard; Guardiola, Francesc; Durand, Erwann; Villeneuve, Pierre; Jacobsen, Charlotte; Sørensen, Ann-Dorit Moltke

2015-01-15

The antioxidative effect of lipophilized caffeic acid was assessed in two different fish oil enriched food products: mayonnaise and milk. In both emulsion systems, caffeic acid esterified with fatty alcohols of different chain lengths (C1-C20) were better antioxidants than the original phenolic compound. The optimal chain length with respect to protection against oxidation was, however, different for the two food systems. Fish oil enriched mayonnaise with caffeates of medium alkyl chain length (butyl, octyl and dodecyl) added resulted in a better oxidative stability than caffeates with shorter (methyl) or longer (octadecyl) alkyl chains. Whereas in fish oil enriched milk emulsions the most effective caffeates were those with shorter alkyl chains (methyl and butyl) rather than the ones with medium and long chains (octyl, dodecyl, hexadecyl and eicosyl). These results demonstrate that there might be an optimum alkyl chain length for each phenolipid in each type of emulsion systems. Copyright © 2014 Elsevier Ltd. All rights reserved.

Determination of total antioxidant capacity by a new spectrophotometric method based on Ce(IV) reducing capacity measurement.

PubMed

Ozyurt, Dilek; Demirata, Birsen; Apak, Resat

2007-02-28

Dietary antioxidants widely found in fruits and vegetables may serve the task of reducing oxidative damage in humans induced by free radicals and reactive oxygen species under 'oxidative stress' conditions. The aim of this work is to develop a simple, low-cost, sensitive, and diversely applicable indirect spectrophotometric method for the determination of total antioxidant capacity of several plants. The method is based on the oxidation of antioxidants with cerium(IV) sulfate in dilute sulfuric acid at room temperature. The Ce(IV) reducing capacity of the sample is measured under carefully adjusted conditions of oxidant concentration and pH such that only antioxidants and not other organic compounds would be oxidized. The spectrophotometric determination of the remaining Ce(IV) was performed after completion of reaction with antioxidants. Quercetin and gallic acid were used as standards for flavonoids and phenolic acids, respectively, and results of antioxidant measurements were reported as trolox equivalents. The developed procedure was successfully applied to the assay of total antioxidant capacity due to simple compounds such as trolox, quercetin, gallic acid, ascorbic acid, catechin, naringin, naringenin, caffeic acid, chlorogenic acid, ferulic acid, and p-coumaric acid, and due to phenolic acids and flavonoids in the arieal parts of nettle (Urtica Dioica L.). Blank correction of significantly absorbing plant extracts at 320nm could be made with the aid of spectrophotometric titration. Plant selection was made in respect to high antioxidant content, and extraction was made with water. The proposed method was reproducible, and the trolox equivalent antioxidant capacities (TEAC coefficients) of the tested antioxidant compounds were correlated to those found by reference methods such as ABTS and CUPRAC. Since the TEAC coefficients found with the proposed method of naringin-naringenin and rutin-catechin pairs were close to each other, this Ce(IV)-based assay probably caused the simultaneous hydrolysis of flavonoid glycosides to the corresponding aglycones and their subsequent oxidation such that the hydrolysis products exhibed antioxidant capacities roughly proportional the number of -OH groups contained in a molecule.

Synergetic effects of 5-aminolevulinic acid and Ascophyllum nodosum seaweed extracts on Asparagus phenolics and stress related genes under saline irrigation.

PubMed

Al-Ghamdi, Abdullah A; Elansary, Hosam O

2018-06-09

Salinity is one of the major agricultural problems that may threat food security and limit the agricultural lands expansion worldwide. Exploring novel tools controlling saline conditions and increase valuable secondary metabolites in the horticultural crops might have outstanding results that serve humanity in the current century. The current study explores the effects of weekly seaweed extracts (7 mL   L -1 ) and/or 5-aminolevulinic acid (3, 5 and 10 ppm) sprays on Asparagus aethiopicus plants subjected to saline stress conditions (2000 and 4000 ppm) for 6 weeks in two consecutive seasons of 2016 and 2017. Under saline conditions, there were stimulatory synergetic effects of seaweed extracts (SWE) and 5-aminolevulinic acid (ALA) on branch length and number of treated plants. Similar increases were also found in fresh and the dry weight of treated plants compared to control. These morphological improvements associated with increased accumulation of specific phenols (robinin, rutin, apigein, chlorogenic acid and caffeic acid) as revealed by High-Performance Liquid Chromatography with Diode-Array Detection (HPLC-DAD). There were increases in the antioxidant activities of leaf extracts, chlorophyll content and sugars and proline accumulation. The transpiration and photosynthetic rates as well as the stomatal conductance were enhanced. The morphological and physiological improvements associated with increased expression of several genes responsible for water management (ANN1, ANN2 and PIP1), secondary metabolite production (P5CS1 and CHS) and antioxidants accumulation (APX1 and GPX3) in plants. Our findings indicate that SWE + ALA had stimulatory synergetic effects on the growth and secondary metabolites of A. aethiopicus subjected to saline conditions. Several mechanisms are involved in such effects including gas exchange control, sugar buildup, increasing non-enzymatic and enzymatic antioxidants control of reactive oxygen species accumulation as well as transcriptional and metabolic regulation of environmental stress. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

Time-dependent effect of rutin on skin fibroblasts membrane disruption following UV radiation.

PubMed

Gęgotek, Agnieszka; Bielawska, Katarzyna; Biernacki, Michał; Dobrzyńska, Izabela; Skrzydlewska, Elżbieta

2017-08-01

Chronic exposure of the skin to solar UV radiation induces a number of biological alterations, including a redox imbalance; therefore, there is an urgent need for skin cells protective compounds. The aim of this study was to determine the effects of natural, previously extensively examined, polyphenol with antioxidant properties - rutin, on UV-induced skin fibroblasts membrane disruption. Accordingly, fibroblasts exposed to UVA and UVB irradiation were incubated with rutin (12h before and/or up to 24h after irradiation), and the structural and metabolic changes were examined. Rutin penetration through the fibroblast phospholipid bilayer was aided by UVA-induced bilitranslocase activity 2-4h after irradiation, while UVB irradiation led to enhanced phospholipid peroxidation and higher membrane permeability to facilitate the interaction of rutin with phospholipids. Lipidomic analysis revealed that 4h of rutin treatment also partially prevented UVA/B-induced increase in phosphatidylethanolamine and phosphatidylcholine level, as well as their membrane localization, which resulted in an enhanced zeta potential in the cells and liposomes. Moreover, rutin 2h following irradiation, in a various degree, prevented the increased in phospholipase A2 activity and ROS generation, and partially protected against the reduction of arachidonic and linoleic acids level and the lipid peroxidation product 4-hydroxynonenal level increase. Rutin effectively prevented against decrease in glutathione peroxidase, glutathione and vitamins E and C activities/levels, particularly 2h following UVA irradiation. In conclusion, highest skin fibroblasts membrane level of rutin occurred in 2-4h following UVA/B-radiation results in its strongest effect on biomembrane structure and functions and cellular antioxidant system irrespective of the radiation type. Copyright © 2017 The Authors. Published by Elsevier B.V. All rights reserved.

Rutin, a Flavonoid and Principal Component of Saussurea Involucrata, Attenuates Physical Fatigue in a Forced Swimming Mouse Model

PubMed Central

Su, Kang-Yi; Yu, Chao Yuan; Chen, Yue-Wen; Huang, Yi-Tsau; Chen, Chun-Ting; Wu, Hsueh-Fu; Chen, Yi-Lin Sophia

2014-01-01

This study investigated the antifatigue effects of rutin, a flavonoid extracted from the ethyl acetate extract of S. involucrata. Mice were subjected to a weight-loaded forced swim test (WFST) on alternate days for 3 wk. Rutin was administered orally to the mice for 7 days in dosages of 15, 30, and 60 mg/kg body weight, and several biomarkers of physical fatigue were evaluated: swimming time, change in body weight, lipid peroxidation, lactic acid (LA), glycogen, and the activities of the antioxidant enzymes superoxide dismutase (SOD) and glutathione peroxidase (GPx). On Day 7, the rutin-treated mice had a 3-fold longer exhaustive swimming time than the control mice, as well as significantly reduced blood LA concentrations. The 15, 30, and 60 mg/kg body weight rutin-supplemented groups displayed 11.2%, 22.5%, and 37.7% reduced malondialdehyde (MDA) concentrations, respectively, in brain and muscle tissues compared with the control exercised group. Our results indicated that the administration of rutin protected the mice against the depletion of SOD and GPx activities significantly. Following 7 days of rutin treatment, we sacrificed the mice and analyzed their soleus muscle and brain for peroxisome proliferator-activated receptor-α coactivator (PGC-1α) and sirtuin 1 (SIRT1) mRNA expression. We observed that rutin treatment increased PGC-1α and SIRT1 mRNA and protein expression. The changes in these markers of mitochondrial biogenesis were associated with increased maximal endurance capacity. The application of 2D gel electrophoresis to analyze the rutin-responsive protein profiles in the WFST mouse brain further revealed the upregulation of the CB1 cannabinoid receptor-interacting protein 1, myelin basic protein, Rho GDP dissociation inhibitor (GDI) alpha, and TPI, indicating that rutin might inhibit anxiety through the upregulation of the expression of anxiety-associated proteins. Western blot analysis of MAPK expression further confirmed the antianxiety effects of rutin. Our study results thus indicate that rutin treatment ameliorates the various impairments associated with physical fatigue. PMID:24693223

Rutin, a flavonoid and principal component of saussurea involucrata, attenuates physical fatigue in a forced swimming mouse model.

PubMed

Su, Kang-Yi; Yu, Chao Yuan; Chen, Yue-Wen; Huang, Yi-Tsau; Chen, Chun-Ting; Wu, Hsueh-Fu; Chen, Yi-Lin Sophia

2014-01-01

This study investigated the antifatigue effects of rutin, a flavonoid extracted from the ethyl acetate extract of S. involucrata. Mice were subjected to a weight-loaded forced swim test (WFST) on alternate days for 3 wk. Rutin was administered orally to the mice for 7 days in dosages of 15, 30, and 60 mg/kg body weight, and several biomarkers of physical fatigue were evaluated: swimming time, change in body weight, lipid peroxidation, lactic acid (LA), glycogen, and the activities of the antioxidant enzymes superoxide dismutase (SOD) and glutathione peroxidase (GPx). On Day 7, the rutin-treated mice had a 3-fold longer exhaustive swimming time than the control mice, as well as significantly reduced blood LA concentrations. The 15, 30, and 60 mg/kg body weight rutin-supplemented groups displayed 11.2%, 22.5%, and 37.7% reduced malondialdehyde (MDA) concentrations, respectively, in brain and muscle tissues compared with the control exercised group. Our results indicated that the administration of rutin protected the mice against the depletion of SOD and GPx activities significantly. Following 7 days of rutin treatment, we sacrificed the mice and analyzed their soleus muscle and brain for peroxisome proliferator-activated receptor-α coactivator (PGC-1α) and sirtuin 1 (SIRT1) mRNA expression. We observed that rutin treatment increased PGC-1α and SIRT1 mRNA and protein expression. The changes in these markers of mitochondrial biogenesis were associated with increased maximal endurance capacity. The application of 2D gel electrophoresis to analyze the rutin-responsive protein profiles in the WFST mouse brain further revealed the upregulation of the CB1 cannabinoid receptor-interacting protein 1, myelin basic protein, Rho GDP dissociation inhibitor (GDI) alpha, and TPI, indicating that rutin might inhibit anxiety through the upregulation of the expression of anxiety-associated proteins. Western blot analysis of MAPK expression further confirmed the antianxiety effects of rutin. Our study results thus indicate that rutin treatment ameliorates the various impairments associated with physical fatigue.

Photoprotection by dietary phenolics against melanogenesis induced by UVA through Nrf2-dependent antioxidant responses

PubMed Central

Chaiprasongsuk, Anyamanee; Onkoksoong, Tasanee; Pluemsamran, Thanyawan; Limsaengurai, Saowalak; Panich, Uraiwan

2015-01-01

Dietary phenolics may play a protective role in UV-mediated skin pigmentation through their antioxidant and UV-absorbing actions. In this study, we investigated whether genetic silencing of Nrf2, regulating the transcription of antioxidant genes, affected melanogenesis in primary human epidermal melanocytes (HEMn) and B16F10 melanoma cells subjected to UVA (8 J/cm2) exposure. Then, we explored the antimelanogenic actions of phenolics; caffeic acid (CA) and ferulic acid (FA) providing partial UVA protection; quercetin (QU) and rutin (RU) providing strong UVA protection and; avobenzone (AV), an efficient UVA filter, in association with modulation of Nrf2-mediated antioxidant defenses in response to UVA insults in B16F10 cells. Upon oxidative insults, Nrf2 silencing promoted melanogenesis in both HEMn and B16F10 cells irradiated with UVA. Stimulation of melanogenesis by UVA correlated with increased ROS and oxidative DNA damage (8-OHdG), GSH depletion as well as a transient downregulation of Nrf2 nuclear translocation and of Nrf2-ARE signaling in B16F10 cells. All test compounds exerted antimelanogenic effects with respect to their abilities to reverse UVA-mediated oxidative damage as well as downregulation of Nrf2 activity and its target antioxidants (GCLC, GST and NQO1) in B16F10 cells. In conclusion, defective Nrf2 may promote melanogenesis under UVA irradiation through oxidative stress mechanisms. Compounds with antioxidant and/or UVA absorption properties could protect against UVA-induced melanogenesis through indirect regulatory effect on Nrf2-ARE pathway. PMID:26765101

Growth, hydrolases and ultrastructure of Fusarium oxysporum as affected by phenolic rich extracts from several xerophytic plants.

PubMed

Mohamed, Mahmoud S M; Saleh, Ahmed M; Abdel-Farid, Ibrahim B; El-Naggar, Sabry A

2017-09-01

Fusarium oxysporum, the causal agent of rot and wilt diseases, is one of the most detrimental phytopathogens for the productivity of many economic crops. The present study was conducted to evaluate the potentiality of some xerophytic plants as eco-friendly approach for management of F. oxysporum. Phenolic rich extracts from five plants namely: Horwoodia dicksoniae, Citrullus colocynthis, Gypsophila capillaris, Pulicaria incisa and Rhanterium epapposum were examined in vitro. The different extracts showed high variability in their phenolic and flavonoid contents as well as total antioxidant capacity. A strong positive correlation existed between the antifungal activity of the tested extracts and their contents of both total phenolics and flavonoids (r values are 0.91 and 0.82, respectively). Extract of P. incisa was the most effective in reducing the mycelial growth (IC 50 =0.92mg/ml) and inhibiting the activities of CMCase, pectinase, amylase and protease by 36, 42, 58 and 55%, respectively. The high performance liquid chromatography analysis of P. incisa extract revealed the presence of eight phenolic acids along with five polyphenolic compounds. The flavonol, quercetin and its glycosides rutin and quercetrin were the most abundant followed by the phenolic acids, t-cinnamic, caffeic, ferulic and vanillic. P. incisa extract not only affects the growth and hydrolases of F. oxysporum but also induces ultrastructure changes in the mycelium, as revealed by transmission electron microscopy. To our knowledge, this is the first study to investigate the mechanisms underlying the antifungal activity of P. incisa. Copyright © 2016 Elsevier Inc. All rights reserved.

Sensitive determination of rutin by spectrofluorimetry using carbon dots synthesized from a non-essential amino acid

NASA Astrophysics Data System (ADS)

Sinduja, B.; Abraham John, S.

2018-03-01

The present study describes the synthesis of carbon dots (CDs) using a non-essential amino acid, asparagine as a precursor. The HR-TEM image shows that the size of the prepared CDs was 2.9 ± 0.2 nm with a spherical morphology. The UV-visible spectrum of CDs exhibits a major band at 307 nm along with a shoulder band around 207 nm corresponding to n-π* and π-π* transitions, respectively. Further, the CDs show emission maximum at 441 nm when excited at 348 nm. The synthesized CDs were then exploited for the determination of rutin by spectrofluorimetry based on the decrease in emission intensity at 441 nm. It was found that emission intensity of CDs at 441 nm was decreased while adding 0.5 μM rutin to CDs. On the other hand, addition of other metal ions and anions including 5 mM Mg2 +, K+, Ca2 +, Na+, NO3- and oxalate, 2.5 mM Cu2 + and Fe3 + and 3 mM glycine, glucose, histidine, proline and cysteine does not affect the emission intensity at 441 nm. A good linearity was observed for the emission intensity against 0.5-15 μM rutin with a correlation coefficient of 0.997 and the limit of detection was found to be 1 × 10- 7 M (61 μg/L) (S/N = 3). The real sample analysis was done by determining rutin in a pharmaceutical sample.

OH-radical induced degradation of hydroxybenzoic- and hydroxycinnamic acids and formation of aromatic products—A gamma radiolysis study

NASA Astrophysics Data System (ADS)

Krimmel, Birgit; Swoboda, Friederike; Solar, Sonja; Reznicek, Gottfried

2010-12-01

The OH-radical induced degradation of hydroxybenzoic acids (HBA), hydroxycinnamic acids (HCiA) and methoxylated derivatives, as well as of chlorogenic acid and rosmarinic acid was studied by gamma radiolysis in aerated aqueous solutions. Primary aromatic products resulting from an OH-radical attachment to the ring (hydroxylation), to the position occupied by the methoxyl group (replacement -OCH 3 by -OH) as well as to the propenoic acid side chain of the cinnamic acids (benzaldehyde formations) were analysed by HPLC-UV and LC-ESI-MS. A comparison of the extent of these processes is given for 3,4-dihydroxybenzoic acid, vanillic acid, isovanillic acid, syringic acid, cinnamic acid, 4-hydroxycinnamic acid, caffeic acid, ferulic acid, isoferulic acid, chlorogenic acid, and rosmarinic acid. For all cinnamic acids and derivatives benzaldehydes were significant oxidation products. With the release of caffeic acid from chlorogenic acid the cleavage of a phenolic glycoside could be demonstrated. Reaction mechanisms are discussed.

Green synthesis of gold-chitosan nanocomposites for caffeic acid sensing.

PubMed

Di Carlo, Gabriella; Curulli, Antonella; Toro, Roberta G; Bianchini, Chiara; De Caro, Tilde; Padeletti, Giuseppina; Zane, Daniela; Ingo, Gabriel M

2012-03-27

In this work, colloidal gold nanoparticles (AuNPs) stabilized into a chitosan matrix were prepared using a green route. The synthesis was carried out by reducing Au(III) to Au(0) in an aqueous solution of chitosan and different organic acids (i.e., acetic, malonic, or oxalic acid). We have demonstrated that by varying the nature of the acid it is possible to tune the reduction rate of the gold precursor (HAuCl(4)) and to modify the morphology of the resulting metal nanoparticles. The use of chitosan, a biocompatible and biodegradable polymer with a large number of amino and hydroxyl functional groups, enables the simultaneous synthesis and surface modification of AuNPs in one pot. Because of the excellent film-forming capability of this polymer, AuNPs-chitosan solutions were used to obtain hybrid nanocomposite films that combine highly conductive AuNPs with a large number of organic functional groups. Herein, Au-chitosan nanocomposites are successfully proposed as sensitive and selective electrochemical sensors for the determination of caffeic acid, an antioxidant that has recently attracted much attention because of its benefits to human health. A linear response was obtained over a wide range of concentration from 5.00 × 10(-8) M to 2.00 × 10(-3) M, and the limit of detection (LOD) was estimated to be 2.50 × 10(-8) M. Moreover, further analyses have demonstrated that a high selectivity toward caffeic acid can be achieved without interference from catechin or ascorbic acid (flavonoid and nonphenolic antioxidants, respectively). This novel synthesis approach and the high performances of Au-chitosan hybrid materials in the determination of caffeic acid open up new routes in the design of highly efficient sensors, which are of great interest for the analysis of complex matrices such as wine, soft drinks, and fruit beverages. © 2012 American Chemical Society

Quantitative Determination of Fluorinated Caffeic Acid Phenethyl Ester Derivative From Rat Blood Plasma by Liquid Chromatography-Electrospray Ionization Tandem Mass Spectrometry

DTIC Science & Technology

2008-03-06

Caffeic acid phenethyl ester (CAPE), a plant-derived polyphenolic compound (Fig. 1), is a component of bee propolis . Propolis has been used as a folk...analytical methods have been documented. These include an HPLC-UV determination of CAPE from a propolis -containing gel [13], HPLC-ESI-MS measurement...of CAPE from crude propolis [14], and HPLC- ESI-MS/MS analysis of CAPE in biological samples [15]. In this paper, we developed a method using ultra

Effect of dietary supplementation of rutin on lactation performance, ruminal fermentation and metabolism in dairy cows.

PubMed

Cui, K; Guo, X D; Tu, Y; Zhang, N F; Ma, T; Diao, Q Y

2015-12-01

The effect of long-term dietary supplementation with rutin on the lactation performance, ruminal fermentation and metabolism of dairy cows were investigated in this study. Twenty multiparous Chinese Holstein cows were randomly divided into four groups, and each was offered a basal diet supplemented with 0, 1.5, 3.0 or 4.5 mg rutin/kg of diet. The milk yield of the cows receiving 3.0 and 4.5 mg rutin/kg was higher than that of the control group, and the milk yield was increased by 10.06% and 3.37% (p < 0.05). On the basis of that finding, the cows supplemented with 0 or 3.0 mg rutin/kg of diet were used to investigate the effect of rutin supplementation on blood metabolites and hormone levels. Compared with the control group, the serum blood urea nitrogen (BUN) concentration of the 3.0 mg rutin/kg group is significantly decreased (p < 0.05). In another trial, four adult cows with permanent rumen fistula and duodenal cannulae were attributed in a self-control design to investigate the peak occurrence of rutin and quercetin in different parts of the gastrointestinal tract, ruminal fermentation and microbial population in dairy cows. The cows supplemented with 3.0 mg rutin/kg in the diet differed from the control period. Samples of rumen fluid, duodenal fluid and blood were collected at 1, 2, 3, 4, 5, 6, 7 and 8 h after morning feeding. Compared to the control group, the pH, ammonia nitrogen concentration, number and protein content of rumen protozoa and blood urea nitrogen were lower, but the concentration of total volatile fatty acid (TVFA), microbial crude protein (MCP) and serum lysozyme content were higher for the cows fed the rutin diets. The addition of 3.0 mg rutin/kg to diets for a long term tended to increase the milk yield and improve the metabolism and digestibility of the dairy cows. Journal of Animal Physiology and Animal Nutrition © 2015 Blackwell Verlag GmbH.

Free radical scavengers and antioxidants from Lemongrass (Cymbopogon citratus (DC.) Stapf.).

PubMed

Cheel, José; Theoduloz, Cristina; Rodríguez, Jaime; Schmeda-Hirschmann, Guillermo

2005-04-06

Methanol, MeOH/water extracts, infusion, and decoction of Cymbopogon citratus were assessed for free radical scavenging effects measured by the bleaching of the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical, scavenging of the superoxide anion, and inhibition of the enzyme xanthine oxidase (XO) and lipid peroxidation in human erythrocytes. The extracts presented effect in the DPPH and superoxide anion assay, with values ranging between 40 and 68% and 15-32% at 33 and 50 microg/mL, respectively, inhibited lipid peroxidation in erythrocytes by 19-71% at 500 microg/mL and were inactive toward the XO at 50 microg/mL. Isoorientin, isoscoparin, swertiajaponin, isoorientin 2' '-O-rhamnoside, orientin, chlorogenic acid, and caffeic acid were isolated and identified by spectroscopic methods. Isoorientin and orientin presented similar activities toward the DPPH (IC(50): 9-10 microM) and inhibited lipid peroxidation by 70% at 100 microg/mL. Caffeic and chlorogenic acid were active superoxide anion scavengers with IC(50) values of 68.8 and 54.2 microM, respectively, and a strong effect toward DPPH. Caffeic acid inhibited lipid peroxidation by 85% at 100 microg/mL.

Chemical Properties of Caffeic and Ferulic Acids in Biological System: Implications in Cancer Therapy. A Review.

PubMed

Damasceno, Sarah S; Dantas, Bruna B; Ribeiro-Filho, Jaime; Antônio M Araújo, Demetrius; Galberto M da Costa, José

2017-01-01

The antioxidant properties of caffeic and ferulic acids in biological systems have been extensively demonstrated. As antioxidants, these compounds prevent the production of reactive oxygen species (ROS), which cause cell lesions that are associated with the development of several diseases, including cancer. Recent findings suggest that the chemoprotective action of these phenolic acids occurs through the following mechanisms: regulation of gene expression, chelation and / or reduction of transition metals, formation of covalent adducts and direct toxicity. The biological efficacy of these promising chemoprotective agents is strongly related with their chemical structure. Therefore, in this study, we discuss the structural characteristics of ferulic and caffeic acids that are responsible for their biological activities, as well as the mechanisms of action involved with the anti-cancer activity. Several reports indicated that the antioxidant effect of these phenylpropanoids results from reactions with free radicals with formation of stable products in the cells. The chelating effect of these compounds was also reported as an important protective mechanism against oxidative. Finally, the lipophilicity of these agents facilitates their entry into the cells, and thus, contributes to the anticancer activity. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

Chlorogenic acid supplementation during in vitro maturation improves maturation, fertilization and developmental competence of porcine oocytes.

PubMed

Nguyen, T-V; Tanihara, F; Do, Ltk; Sato, Y; Taniguchi, M; Takagi, M; Van Nguyen, T; Otoi, T

2017-12-01

Chlorogenic acid (CGA) is a quinic acid conjugate of caffeic acid, and a phytochemical found in many fruits and beverages that acts as an antioxidant. The present study investigated the effects of CGA supplementation during in vitro maturation (IVM), on in vitro development of porcine oocytes, to improve the porcine in vitro production (IVP) system. Oocytes were matured either without (control) or with CGA (10, 50, 100 and 200 μM). Subsequently, the matured oocytes were fertilized and cultured in vitro for 7 day. The rates of maturation, fertilization and blastocyst formation of oocytes matured with 50 μM CGA were significantly (p < .05) higher than those of the control oocytes. Hydrogen peroxide (H 2 O 2 ) is one of the reactive oxygen species and induces DNA damage in porcine oocytes. When oocytes were matured with 1 mM H 2 O 2 to assess the protective effect of CGA, 50 μM CGA supplementation improved the maturation rate and the proportion of DNA-fragmented nuclei in oocytes compared with control oocytes matured without CGA. Moreover, when oocytes were matured with either 50 μM CGA (control) or caffeic acid (10, 50 and 100 μM), the rates of maturation, fertilization and the blastocyst formation of oocytes matured with 50 μM CGA were similar to those of oocytes matured with 10 and 50 μM caffeic acid. Our results suggest that CGA has comparable effects to caffeic acid, and IVM with 50 μM CGA is particularly beneficial to IVP of porcine embryos and protects oocytes from DNA damage induced by oxidative stress. Supplementation of CGA to the maturation medium has a potential to improve porcine IVP system. © 2017 Blackwell Verlag GmbH.

Reducing effects of polyphenols on metmyoglobin and the in vitro regeneration of bright meat color by polyphenols in the presence of cysteine.

PubMed

Miura, Yukari; Inai, Miyuki; Honda, Sari; Masuda, Akiko; Masuda, Toshiya

2014-10-01

The effect of polyphenols and related phenolic compounds on the reduction of metmyoglobin (MetMb) to oxymyoglobin (MbO2), in the presence of cysteine, was investigated. Caffeic acid, dihydrocaffeic acid, and hydroxtyrosol (600 μmol/L) did not show any reducing activity individually. However, their highly potent activity in the reduction of MetMb to MbO2 was observed in the presence of equimolar amounts of cysteine. On the basis of the analytical results for the redox reaction products generated during the MetMb-reducing reaction of caffeic acid, we proposed a mechanism for the polyphenol-mediated reduction of MetMb. As per the proposed mechanism, the antioxidant polyphenols having a catechol substructure can effectively reduce MetMb to MbO2 with chemical assistance from nucleophilic reactive thiol compounds such as cysteine. Moreover, cysteine-coupled polyphenols such as cysteinylcaffeic acids (which are coupling products of caffeic acid and cysteine) can be used as preserving agents for retaining the fresh meat color, because of their powerful reducing effect on MetMb. The reduction of MetMb to MbO2 changes the color of meat from brown to the more desirable bright red.

Comparison of bee products based on assays of antioxidant capacities.

PubMed

Nakajima, Yoshimi; Tsuruma, Kazuhiro; Shimazawa, Masamitsu; Mishima, Satoshi; Hara, Hideaki

2009-02-26

Bee products (including propolis, royal jelly, and bee pollen) are popular, traditional health foods. We compared antioxidant effects among water and ethanol extracts of Brazilian green propolis (WEP or EEP), its main constituents, water-soluble royal jelly (RJ), and an ethanol extract of bee pollen. The hydrogen peroxide (H2O2)-, superoxide anion (O2.-)-, and hydroxyl radical (HO.)- scavenging capacities of bee products were measured using antioxidant capacity assays that employed the reactive oxygen species (ROS)-sensitive probe 5-(and-6)-chloromethyl-2',7'-dichlorodihydrofluorescein diacetate, acetyl ester (CM-H2DCFDA) or aminophenyl fluorescein (APF). The rank order of antioxidant potencies was as follows: WEP > EEP > pollen, but neither RJ nor 10-hydroxy-2-decenoic acid (10-HDA) had any effects. Concerning the main constituents of WEP, the rank order of antioxidant effects was: caffeic acid > artepillin C > drupanin, but neither baccharin nor coumaric acid had any effects. The scavenging effects of caffeic acid were as powerful as those of trolox, but stronger than those of N-acetyl cysteine (NAC) or vitamin C. On the basis of the present assays, propolis is the most powerful antioxidant of all the bee product examined, and its effect may be partly due to the various caffeic acids it contains. Pollen, too, exhibited strong antioxidant effects.

Metabolism of hydroxycinnamic acids and esters by Brettanomyces in different red wines

USDA-ARS?s Scientific Manuscript database

Depending on the cultivars and other factors, differing concentrations of hydroxycinnamic acids (caffeic, p-coumaric, and ferulic acids) and their corresponding tartaric acid esters (caftaric, coutaric, and fertaric acid, respectively) are found in red wines. Hydroxycinnamic acids are metabolized by...

[Determination of plasma concentration of five phenolic acid by LC-MS/MS and study of pharmacokinetics in rats after Mailuoning injection].

PubMed

Wu, Ting; Zhang, Jun; Tan, Heng-Shan; Ju, Wen-Zheng; Xu, Xiang-Yang

2014-05-01

To establish a LC-MS/MS method for quantification of chlorogenic acid, caffeic acid, 3,4-DCQA, ferulic acid and cinnamic acid in rats plasma and study its pharmacokinetics after administration of Mailuoning injection at a single dose to rats. Plasma samples were acidified with hydrochloric acid and extracted with ethyl acetate. The analytes were determined by LC-MS-MS using a ZOBAX SB C18 column with a mobile phase of methanol-water (containing 2 mmol x L(-1) ammonium acetic) (60:40)at a flow rate of 0.5 mL x min(-1) and detected using ESI with negative ionization mode. Ions monitored in the multiple reaction monitoring (MRM) mode were m/z 353.1/191.0 [M-H]- for chlorogenic acid, m/z 178.9/134.9 [M-H]- for caffeic acid, m/z 515.2/353.0 [M-H]-for 3,4-DCQA, m/z 193.0/133.9 [M-H]-for ferulic acid, m/z 146.9/102.9 [M-H]- for cinnamic acid and m/z 246.0/125.8 [M-H]- for tinidazole (IS). After administration of Mailuoning injection at a single dose to eight Sprague-Dawley rats, the concentrations of chlorogenic acid, caffeic acid, 3,4-DCQA, ferulic acid and cinnamic acid in plasma were determined by LC-MS/MS method. The main pharmacokinetics parameters of measured data were caluculated by using DASver 1.0 software. The linear concentration ranges of the calibration curves for chlorogenic acid, caffeic acid, 3,4-DCQA and cinnamic acid were 2.006-1,027 microg x L(-1) (r = 0.999 6), 1.953-1,000 microg x L(-1) (r = 0.999 7), 28.51-1.459 x 10(4) microg x L(-1) (r = 0.998 9), 1.836-940.0, g x L(-1) (r = 0.997 7) and 4.780-2,447 microg x L(-1) (r = 0.998 6) respectively. The inner and inter-days relative standard deviations were both less than 5.0%, indicating legitimate precise and accuracy to the requirement of biological sample analysis. For chlorogenic acid, the pharmacokinetic parameter t1/2, AUC0-t, and CL were (49.78 +/- 12.81) min, (123.55 +/- 14.82) mg x min x L(-1) and (0.004 3 +/- 0.000 5) L x min(-1), respectively. For caffeic acid, the pharmacokinetic parameter t1/2, AUC0-t, and CL were (36.65 +/- 10.59) min, (91.67 +/- 11.77) mg x min L(-1) and (0.005 7 +/- 0.000 7) L x min(-1), respectively. For 3,4-DCQA, the pharmacokinetic parameter t1/2, AUC0-t, and CL were (50.08 +/- 13.78) min, (278.34 +/- 31.82) mg x min x L-1 and (0.001 6 +/- 0.000 2) L x min(-1), respectively. For ferulic acid, the pharmacokinetic parameter t1/2, AUC0-t, and CL were (51.39 +/- 15.52) min, (34.72 +/- 4.67) mg x min x L(-1) and (0.000 4 +/- 0.0001) L x min(-1), respectively. For cinnamic acid, the pharmacokinetic parameter t1/2, AUCo-t, and CL were (74.42 +/- 18.32) min, (34.63 +/- 4.82) mg x min x L(-1) and (0.007 7 +/- 0.001 1) L x min-', respectively. The assay method is proved to be sensitive, accurate and convenient. It can be applied to the pharmacokinetic study of chlorogenic acid, caffeic acid, 3,4-DCQA, ferulic acid and cinnamic acid.

Comparative studies on the interaction of caffeic acid, chlorogenic acid and ferulic acid with bovine serum albumin

NASA Astrophysics Data System (ADS)

Li, Shuang; Huang, Kelong; Zhong, Ming; Guo, Jun; Wang, Wei-zheng; Zhu, Ronghua

2010-10-01

The substitution of the hydrogen on aromatic and esterification of carboxyl group of the phenol compounds plays an important role in their bio-activities. In this paper, caffeic acid (CaA), chlorogenic acid (ChA) and ferulic acid (FA) were selected to investigate the binding to bovine serum albumin (BSA) using UV absorption spectroscopy, fluorescence spectroscopy and synchronous fluorescence spectroscopy. It was found that the methoxyl group substituting for the 3-hydroxyl group of CaA decreased the affinity for BSA and the esterification of carboxyl group of CaA with quinic acid increased the affinities. The affinities of ChA and FA with BSA were more sensitive to the temperature than that of CaA with BSA. Synchronous fluorescence spectroscopy and time-resolved fluorescence indicated that the Stern-Volmer plots largely deviated from linearity at high concentrations and were caused by complete quenching of the tyrosine fluorescence of BSA.

Chicoric Acid Found in Basil (Ocimum basilicum L.) Leaves

USDA-ARS?s Scientific Manuscript database

This is the first report to identify the presence of chicoric acid (cichoric acid; also known as dicaffeoyltartaric acid) in basil leaves. Rosmarinic acid, chicoric acid, and caftaric acid (in the order of most abundant to least; all derivatives of caffeic acid) were identified in fresh basil leaves...

A novel continuous flow biosynthesis of caffeic acid phenethyl ester from alkyl caffeate and phenethanol in a packed bed microreactor.

PubMed

Wang, Jun; Gu, Shuang-Shuang; Cui, Hong-Sheng; Wu, Xiang-Yang; Wu, Fu-An

2014-04-01

Caffeic acid phenethyl ester (CAPE) is a rare natural ingredient with several biological activity, but the industrial production of CAPE using lipase-catalyzed esterification of caffeic acid (CA) and 2-phenylethanol (PE) in ionic liquids is hindered by low substrate concentrations and a long reaction time. To establish a high-efficiency bioprocess for obtaining CAPE, a novel continuous flow biosynthesis of CAPE from alkyl caffeate and PE in [Bmim][Tf2N] using a packed bed microreactor was successfully carried out. Among the tested alkyl caffeates and lipases, methyl caffeate and Novozym 435, respectively, were selected as the suitable substrate and biocatalyst. Under the optimum conditions selected using response surface methodology, a 93.21% CAPE yield was achieved in 2.5h using a packed bed microreactor, compared to 24h using a batch reactor. The reuse of Novozym 435 for 20 cycles and continuous reaction for 9 days did not result in any decrease in activity. Copyright © 2014 Elsevier Ltd. All rights reserved.

Induction of antioxidant flavonol biosynthesis in fresh-cut potatoes. Effect of domestic cooking.

PubMed

Tudela, Juan A; Cantos, Emma; Espín, Juan C; Tomás-Barberán, Francisco A; Gil, María I

2002-10-09

The effect of fresh-cutting and subsequent cold storage on phenolic compounds from five long-term-stored potato cultivars (Agria, Cara, Liseta, Monalisa, and Spunta) was studied. Fresh-cutting induced the biosynthesis of three flavonols, which were identified by HPLC-DAD-ESIMS as quercetin 3-rutinoside, quercetin 3-diglucoside, and quercetin 3-glucosylrutinoside. The flavonols were detected after a lag period of 3 days of cold storage. The content ranged from 6 to 14 mg/100 g of fresh weight depending on the cultivar after 6 days of storage. Chlorogenic acid as the main caffeic acid derivative and the amino acids tyrosine and tryptophan were also quantified. The effect of cold storage under light or in dark was studied with new-season-harvested Monalisa potatoes. The flavonol induction was higher in fresh-cut potatoes stored under light than in the dark. However, caffeic acid derivatives were not affected. Domestic cooking such as boiling, microwaving, and frying provoked a partial loss of the flavonols, which were retained in the range of 4-16 mg per serving (213 g). Steam-cooking resulted in the highest retention of caffeic acid derivatives and aromatic amino acids compared with the other cooking methods studied. This means that due to the large amount of potatoes consumed in the Western diet, fresh-cut potatoes can be a significant source of health-promoting phenolics.

Site-specific hydrolysis of chlorogenic acids by selected Lactobacillus species.

PubMed

Aguirre Santos, Elsa Anaheim; Schieber, Andreas; Weber, Fabian

2018-07-01

Hydroxycinnamic acids are a major group of phenolic compounds widely distributed in plants. Among them, chlorogenic acids and caffeic acid have been in the focus of interest due to their impact on food quality and their putative health benefits. Numerous microorganisms like lactic acid bacteria are able to hydrolyze chlorogenic acids by cinnamoyl esterase enzymes. Data on the specificity of theses enzymes regarding the cleavage of distinct isomers of mono- or dichlorogenic acids is lacking. Lactobacillus reuteri, Lactobacillus helveticus, and Lactobacillus fermentum were screened for their ability to hydrolyze chlorogenic acid isomers in culture medium. Concentrations of chlorogenic acids and the released caffeic acid were determined by UHPLC-ESI-MS. The highest hydrolysis rate (100%) was observed for the hydrolysis of 5-CQA by Lactobacillus helveticus. A so far unknown metabolic pathway for the cleavage of 4-CQA is proposed including isomerization to 5-CQA and 3-CQA followed by hydrolysis. Copyright © 2018 Elsevier Ltd. All rights reserved.

Metabolism of nonesterified and esterified hydroxycinnamic acids in red wines by Brettanomyces bruxellensis.

PubMed

Schopp, Lauren M; Lee, Jungmin; Osborne, James P; Chescheir, Stuart C; Edwards, Charles G

2013-11-27

While Brettanomyces can metabolize nonesterified hydroxycinnamic acids found in grape musts/wines (caffeic, p-coumaric, and ferulic acids), it was not known whether this yeast could utilize the corresponding tartaric acid esters (caftaric, p-coutaric, and fertaric acids, respectively). Red wines from Washington and Oregon were inoculated with B. bruxellensis, while hydroxycinnamic acids were monitored by HPLC. Besides consuming p-coumaric and ferulic acids, strains I1a, B1b, and E1 isolated from Washington wines metabolized 40-50% of caffeic acid, a finding in contrast to strains obtained from California wines. Higher molar recoveries of 4-ethylphenol and 4-ethylguaiacol synthesized from p-coumaric and ferulic acids, respectively, were observed in Washington Cabernet Sauvignon and Syrah but not Merlot. This finding suggested that Brettanomyces either (a) utilized vinylphenols formed during processing of some wines or (b) metabolized other unidentified phenolic precursors. None of the strains of Brettanomyces studied metabolized caftaric or p-coutaric acids present in wines from Washington or Oregon.

Synthesis and Biological Evaluation of New Natural Phenolic (2E,4E,6E)-Octa-2,4,6-trienoic Esters.

PubMed

Gandolfi, Raffaella; Contini, Alessandro; Pinto, Daniela; Marzani, Barbara; Pandini, Stefano; Nava, Donatella; Pini, Elena

2017-12-01

In the present study the esterification of the OH groups of resveratrol, caffeic acid, ferulic acid, and β-sitosterol with an antioxidant polyconjugated fatty acid, (2E,4E,6E)-octa-2,4,6-trienoic acid, was achieved. As the selective esterification of OH groups of natural compounds can affect their biological activity, a selective esterification of resveratrol and caffeic acid was performed by an enzymatic approach. The new resulting compounds were characterized spectroscopically (FT-IR, NMR mono, and bidimensional techniques); when necessary the experimental data were integrated by quantum chemical calculations. The antioxidant, anti-inflammatory and proliferative activity was evaluated. The good results encourage the use of these molecules as antioxidant and/or anti-inflammatory agents in dermocosmetic application. © 2017 Wiley-VHCA AG, Zurich, Switzerland.

AM symbiosis alters phenolic acid content in tomato roots

PubMed Central

Flors, Victor; García, Juan M; Pozo, Maria J

2010-01-01

Arbuscular mycorrhizal (AM) fungi colonize the roots of most plants to establish a mutualistic symbiosis leading to important benefits for plant health. We have recently shown that AM symbiosis alters both transcriptional and hormonal profiles in tomato roots, many of these changes related to plant defense. Here, we analytically demonstrate that the levels of other important defense-related compounds as phenolic acids are also altered in the symbiosis. Both caffeic and chlorogenic acid levels significantly decreased in tomato roots upon mycorrhization, while ferulic acid increased. Moreover, in the case of caffeic acid a differential reduction was observed depending on the colonizing AM fungus. The results confirm that AM associations imply the regulation of plant defense responses, and that the host changes may vary depending on the AM fungus involved. The potential implications of altered phenolic acid levels on plant control over mycorrhizal colonization and in the plant resistance to pathogens is discussed. PMID:21490421

Caffeoyl triterpenes from pear (Pyrus pyrifolia Nakai) fruit peels and their antioxidative activities against oxidation of rat blood plasma.

PubMed

Cho, Jeong-Yong; Kim, Chan Mi; Lee, Hyoung Jae; Lee, Sang-Hyun; Cho, Jeong-An; Kim, Wol-Soo; Park, Keun-Hyung; Moon, Jae-Hak

2013-05-15

Six triterpenes, including three caffeoyl triterpenes, were purified and isolated from pear fruit ( Pyrus pyrifolia Nakai cv. Chuwhangbae) peel extracts using various column chromatography techniques with a guided 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay. The isolated compounds were identified as betulinic aldehyde (1), lupeol (2), betulinic acid (3), 3-O-cis-caffeoylbetulinic acid (4), 3-O-trans-caffeoylbetulinic acid (5), and 3-O-trans-caffeoyloleanolic acid (6) on the basis of nuclear magnetic resonance spectroscopy and electrospray ionization mass spectrometry. Four compounds (1, 4-6) were identified from Asian pear fruit for the first time. In addition, compounds 4-6, containing a caffeic acid moiety, showed higher DPPH radical-scavenging and suppression effects against copper ion-induced oxidation of rat blood plasma than other compounds without a caffeic acid moiety.

Differential metabolism of hydroxycinnamic acids by two Brettanomyces bruxellensis strains grown in red wines

USDA-ARS?s Scientific Manuscript database

Hydroxycinnamic acids (caffeic, p-coumaric, and ferulic acids) and their corresponding tartaric acid esters (caftaric, coutaric, and fertaric acids, respectively) are found in red wines in varying concentrations depending on cultivars and other factors. While some Brettanomyces form volatile phenols...

Antioxidant and Anti-Inflammatory Activity Determination of One Hundred Kinds of Pure Chemical Compounds Using Offline and Online Screening HPLC Assay.

PubMed

Lee, Kwang Jin; Oh, You Chang; Cho, Won Kyung; Ma, Jin Yeul

2015-01-01

This study investigated the antioxidant activity of one hundred kinds of pure chemical compounds found within a number of natural substances and oriental medicinal herbs (OMH). Three different methods were used to evaluate the antioxidant activity of DPPH radical-scavenging activity, ABTS radical-scavenging activity, and online screening HPLC-ABTS assays. The results indicated that 17 compounds exhibited better inhibitory activity against ABTS radical than DPPH radical. The IC50 rate of a more practical substance is determined, and the ABTS assay IC50 values of gallic acid hydrate, (+)-catechin hydrate, caffeic acid, rutin hydrate, hyperoside, quercetin, and kaempferol compounds were 1.03 ± 0.25, 3.12 ± 0.51, 1.59 ± 0.06, 4.68 ± 1.24, 3.54 ± 0.39, 1.89 ± 0.33, and 3.70 ± 0.15 μg/mL, respectively. The ABTS assay is more sensitive to identifying the antioxidant activity since it has faster reaction kinetics and a heightened response to antioxidants. In addition, there was a very small margin of error between the results of the offline-ABTS assay and those of the online screening HPLC-ABTS assay. We also evaluated the effects of 17 compounds on the NO secretion in LPS-stimulated RAW 264.7 cells and also investigated the cytotoxicity of 17 compounds using a cell counting kit (CCK) in order to determine the optimal concentration that would provide an effective anti-inflammatory action with minimum toxicity. These results will be compiled into a database, and this method can be a powerful preselection tool for compounds intended to be studied for their potential bioactivity and antioxidant activity related to their radical-scavenging capacity.

Anti-inflammatory activity of Theobroma cacao L. stem bark ethanol extract and its fractions in experimental models.

PubMed

Oyeleke, Sabitiu A; Ajayi, Abayomi M; Umukoro, Solomon; Aderibigbe, A O; Ademowo, Olusegun George

2018-08-10

The stem bark of Theobroma cacao L. have been used for the treatment of inflammation, toothache, measles and malaria in ethnomedicine. However, the anti-inflammatory activity of Theobroma cacao stem bark has not been fully elucidated. The anti-inflammatory activity of Theobroma cacao stem bark ethanol extract and its fractions was investigated in this study. The anti-inflammatory effect of ethanol extract of Theobroma cacao stem bark (EETc) and its dichloromethane (DCMF), ethylacetate (EAF) and aqueous (AQF) fractions was investigated in erythrocytes membrane stabilizing assay and carrageenan-induced paw oedema. The anti-inflammatory activity of the EAF and EETc was investigated in carrageenan induced-granuloma air pouch models. The extract and fractions showed significant membrane stabilizing action on rat erythrocytes cell membrane. The oral administration of DCMF, EAF and AQF (250 mg/kg) significantly inhibited paw oedema induced by carrageenan (41.3%, 55.0% and 45.0%, respectively) compared to control group. The EAF (62.5, 125 and 250 mg/kg) and EETc (250 mg/kg) significantly inhibited exudates formation in carrageenan air pouch by (63.8, 71.5, 74.5, 64.3%) at 24 h and by (69.4%, 75.7%, 77.1% and 68.4%) at 72 h respectively. The EETc and EAF significantly reduced neutrophil counts, protein, nitrite, Tumor necrosis factor (TNF-α) and malondialdehyde (MDA) but increased reduced glutathione (GSH) levels compared to control in pouch exudates. The HPLC fingerprint of EAF revealed presence of caffeic acid, rutin, ferulic acid and morin. Ethanol extract of Theobroma cacao and its ethylacetate fraction demonstrated anti-inflammatory activity partly by reducing neutrophil migration and inflammatory mediator production. Copyright © 2018 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.

Free radicals quenching potential, protective properties against oxidative mediated ion toxicity and HPLC phenolic profile of a Cameroonian spice: Piper guineensis.

PubMed

Moukette Moukette, Bruno; Constant Anatole, Pieme; Nya Biapa, Cabral Prosper; Njimou, Jacques Romain; Ngogang, Jeanne Yonkeu

2015-01-01

Considerations on antioxidants derived from plants have continuously increased during this decade because of their beneficial effects on human health. In the present study we investigated the free radical scavenging properties of extracts from Piper guineense ( P. guineense ) and their inhibitory potentials against oxidative mediated ion toxicity. The free radical quenching properties of the extracts against [1,1-diphenyl-2-picrylhydrazyl (DPPH•), 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS•), hydroxyl radical (HO•), nitric oxide (NO•)] radical and their antioxidant potentials by FRAP and phosphomolybdenum were determined as well as their protective properties on liver enzymes. The phenolic profile was also investigated by HPLC. The results obtained, revealed that the extracts significantly inhibited the DPPH, NO, HO and ABTS radicals in a concentration depending manner. They also showed a significant ferrous ion chelating ability through FRAP and phosphomolybdenum antioxidant potential. Their polyphenol contents varied depending on the type of extracts and the solvent used. The hydroethanolic extracts (FFH) and the ethanolic extracts (FFE) of P. guineense leaves showed the higher level of phenolic compounds respectively of 21.62 ± 0.06 mg caffeic acid/g dried extract (CAE/g DE) and 19.01 ± 0.03 CAE/g DE. The HPLC phenolic compounds profile revealed a higher quantity of Eugenol, quercetin, rutin and catechin in the stem than in the leaves. The presence of these molecules could be responsible of the protective potentials of P. guineense extracts against lipid peroxidation and SOD, catalase and peroxidase. In conclusion, P. guineense extracts demonstrated significant antioxidant property and may be used as a prospective protector against metal related toxicity.

Migration Rate Inhibition of Breast Cancer Cells Treated by Caffeic Acid and Caffeic Acid Phenethyl Ester: An In Vitro Comparison Study.

PubMed

Kabała-Dzik, Agata; Rzepecka-Stojko, Anna; Kubina, Robert; Jastrzębska-Stojko, Żaneta; Stojko, Rafał; Wojtyczka, Robert Dariusz; Stojko, Jerzy

2017-10-19

One of the deadliest cancers among women is a breast cancer. Research has shown that two natural substances occurring in propolis, caffeic acid (CA) and caffeic acid phenethyl ester (CAPE), have significant anticancer effects. The purpose of our in vitro study was to compare cytotoxic activity and migration rate inhibition using CA and CAPE (doses of 50 and 100 µm) against triple-negative, MDA-MB-231 breast adenocarcinoma line cells, drawn from Caucasian women. Viability was measured by XTT-NR-SRB assay (Tetrazolium hydroxide-Neutral Red-Sulforhodamine B) for 24 h and 48 h periods. Cell migration for wound healing assay was taken for 0 h, 8 h, 16 h, and 24 h periods. CAPE displayed more than two times higher cytotoxicity against MDA-MB-231 cells. IC 50 values for the XTT assay were as follows: CA for 24 h and 48 h were 150.94 µM and 108.42 µM, respectively, while CAPE was 68.82 µM for 24 h and 55.79 µM for 48 h. For the NR assay: CA was 135.85 µM at 24 h and 103.23 µM at 48 h, while CAPE was 64.04 µM at 24 h and 53.25 µM at 48 h. For the SRB assay: CA at 24 h was 139.80 µM and at 48 h 103.98 µM, while CAPE was 66.86 µM at 24 h and 47.73 µM at 48 h. Both agents suspended the migration rate; however, CAPE displayed better activity. Notably, for the 100 µM CAPE dose, motility of the tested breast carcinoma cells was halted.

Interaction of cinnamic acid derivatives with β-cyclodextrin in water: experimental and molecular modeling studies.

PubMed

Liu, Benguo; Zeng, Jie; Chen, Chen; Liu, Yonglan; Ma, Hanjun; Mo, Haizhen; Liang, Guizhao

2016-03-01

Cyclodextrins (CDs) can be used to improve the solubility and stability of cinnamic acid derivatives (CAs). However, there was no detailed report about understanding the effects of the substituent groups in the benzene ring on the inclusion behavior between CAs and CDs in aqueous solution. Here, the interaction of β-CD with CAs, including caffeic acid, ferulic acid, and p-coumaric acid, in water was investigated by phase-solubility method, UV, fluorescence, and (1)H NMR spectroscopy, together with ONIOM (our Own N-layer Integrated Orbital molecular Mechanics)-based QM/MM (Quantum Mechanics/Molecular Mechanics) calculations. Experimental results demonstrated that CAs could form 1:1 stoichiometric inclusion complex with β-CD by non-covalent bonds, and that the maximum apparent stability constants were found in caffeic acid (176M(-1)) followed by p-coumaric acid (160M(-1)) and ferulic acid (133M(-1)). Moreover, our calculations reasonably illustrated the binding orientations of β-CD with CAs determined by experimental observations. Copyright © 2015. Published by Elsevier Ltd.

Antifungal activity of secondary plant metabolites from potatoes (Solanum tuberosum L.): Glycoalkaloids and phenolic acids show synergistic effects.

PubMed

Sánchez-Maldonado, A F; Schieber, A; Gänzle, M G

2016-04-01

To study the antifungal effects of the potato secondary metabolites α-solanine, α-chaconine, solanidine and caffeic acid, alone or combined. Resistance to glycoalkaloids varied among the fungal species tested, as derived from minimum inhibitory concentrations assays. Synergistic antifungal activity between glycoalkaloids and phenolic compounds was found. Changes in the fluidity of fungal membranes caused by potato secondary plant metabolites were determined by calculation of the generalized polarization values. The results partially explained the synergistic effect between caffeic acid and α-chaconine and supported findings on membrane disruption mechanisms from previous studies on artificial membranes. LC/MS analysis was used to determine variability and relative amounts of sterols in the different fungal species. Results suggested that the sterol pattern of fungi is related to their resistance to potato glycoalkaloids and to their taxonomy. Fungal resistance to α-chaconine and possibly other glycoalkaloids is species dependent. α-Chaconine and caffeic acid show synergistic antifungal activity. The taxonomic classification and the sterol pattern play a role in fungal resistance to glycoalkaloids. Results improve the understanding of the antifungal mode of action of potato secondary metabolites, which is essential for their potential utilization as antifungal agents in nonfood systems. © 2016 The Society for Applied Microbiology.

Synthesis and antioxidant properties of caffeic acid corn bran arabinoxylan esters.

PubMed

Li, Y; Zhu, Y; Liang, R; Yang, C

2017-08-01

As a potential of bioactive additives, corn bran arabinoxylan (CAX) was prominent in its probiotic benefits and immuno-enhancing activities. To improve the antioxidant ability of CAX, naturally occurring caffeic acid (CA) was covalently attached to CAX by esterification to generate caffeic acid corn bran arabinoxylan esters (CA-CAX) with various degrees of substitution (DS). The structure of CA-CAX was analysed by NMR, and the DS was determined by HPLC. The antioxidant activity of CA-CAX was investigated on scavenging the 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical and autoxidazing methyl linoleate, and an aqueous linolenic acid dispersion was also used as an in vitro test system to examine the inhibition effect of CA-CAX on the lipid peroxidation level after UV exposure. The ability of CA-CAX to prevent H 2 O 2 -induced oxidative damage of cell was studied by reducing MDA levels and increasing SOD and GSH-Px activities in human hepatocarcinoma (HepG2) cell. The results certificated that CA was linked to CAX successfully with various DS. Compared with CAX, the antioxidant capacity of CA-CAX was improved significantly and enhanced with the increasing concentration and DS. © 2017 Society of Cosmetic Scientists and the Société Française de Cosmétologie.

Metabolism of hydroxycinnamic acids and their tartaric acid esters by Brettanomyces and Pediococcus in red wines.

USDA-ARS?s Scientific Manuscript database

Caffeic, p-coumaric, and ferulic acids and their corresponding tartaric acid esters (caftaric, coutaric, and fertaric, respectively) are found in wines in varying concentrations. While Brettanomyces and Pediococcus can utilize the free acids, it is not known whether they can metabolize the correspon...

Metabolism of nonesterified and esterified hydroxycinnamic acids in red wines by Brettanomyces bruxellensis

USDA-ARS?s Scientific Manuscript database

While Brettanomyces can metabolize non–esterified hydroxycinnamic acids found in grape musts/wines (caffeic, p–coumaric, and ferulic acids), it was not known whether this yeast could utilize the corresponding tartaric acid esters (caftaric, p–coutaric, and fertaric acids, respectively). Red wines fr...

Effect of variety on content of bioactive phenolic compounds in common elder (Sambucus nigra L.).

PubMed

Vrchotová, Naděžda; Dadáková, Eva; Matějíček, Aleš; Tříska, Jan; Kaplan, Jiří

2017-03-01

The inflorescence of common elder (Sambucus nigra L., Adoxaceae) is known to be rich in phenolic compounds. The content of five selected phenolic compounds (rutin, chlorogenic acid, isoquercitrin, isorhamnetin-3-O- rutinoside and dicaffeoylquinic acid) was determined in methanolic extracts from flowers and floral stems by HPLC in samples obtained from 20 varieties of S. nigra cultivated in Czech Republic. In all samples, there were determined rutin (11-54 mg/g), chlorogenic acid (23-46 mg/g), isoquercitrin (0.6-18 mg/g), isorhamnetin-3-O-rutinoside (3-10 mg/g), calculated on air-dried material. The content of dicaffeoylquinic acid was 0-13 mg/g of air-dried material. The amount of the analysed compounds in floral stems was lower than the flowers. The results are a unique set of information on the content of main phenolics in the inflorescence of cultured elderberry varieties.

Effects of rutin on the physicochemical properties of skin fibroblasts membrane disruption following UV radiation.

PubMed

Dobrzyńska, Izabela; Gęgotek, Agnieszka; Gajko, Ewelina; Skrzydlewska, Elżbieta; Figaszewski, Zbigniew A

2018-02-25

Human skin provides the body's first line of defense against physical and environmental assaults. This study sought to determine how rutin affects the membrane electrical properties, sialic acid content, and lipid peroxidation levels of fibroblast membranes after disruption by ultraviolet (UV) radiation. Changes in cell function may affect the basal electrical surface properties of cell membranes, and changes can be detected by electrokinetic measurements. The charge density of the fibroblast membrane surface was measured as a function of pH. A four-component equilibrium model was used to describe the interaction between ions in solution and ions on the membrane surface. Agreement was found between experimental and theoretical charge variation curves of fibroblast cells between pH 2.5 and 8. Sialic acid content was determined by Svennerholm's resorcinol method, and lipid peroxidation was estimated by measuring the malondialdehyde level. Compared to untreated cells, ultraviolet A (UVA)- or ultraviolet B (UVB)-treated skin cell membranes exhibited higher concentrations of acidic functional groups and higher average association constants with hydroxyl ions, but lower average association constants with hydrogen ions. Moreover, our results showed that UVA and UVB radiation is associated with increased levels of sialic acid and lipid peroxidation products in fibroblasts. Rutin protected cells from some deleterious UV-associated membrane changes, including changes in electrical properties, oxidative state, and biological functions. Copyright © 2018 Elsevier B.V. All rights reserved.

Molecularly imprinted polymer for caffeic acid by precipitation polymerization and its application to extraction of caffeic acid and chlorogenic acid from Eucommia ulmodies leaves.

PubMed

Miura, Chitose; Matsunaga, Hisami; Haginaka, Jun

2016-08-05

Molecularly imprinted polymers (MIPs) for caffeic acid (CA) were prepared using 4-vinylpyridine and methacrylamide (MAM) as functional monomers, divinylbenzene as a crosslinker and acetonitrile-toluene (3:1, v/v) as a porogen by precipitation polymerization. The use of MAM as the co-monomer resulted in the formation of microsphere MIPs and non-imprinted polymers (NIPs) with ca. 3- and 5-μm particle diameters, respectively. Binding experiments and Scatchard analyses revealed that the binding capacity and affinity of the MIP to CA are higher than those of the NIP. The retention and molecular-recognition properties of the prepared MIPs were evaluated using water-acetonitrile and sodium phosphate buffer-acetonitrile as mobile phases in hydrophilic interaction chromatography (HILIC) and reversed-phase chromatography, respectively. In HILIC mode, the MIP showed higher molecular-recognition ability for CA than in reversed-phase mode. In addition to shape recognition, hydrophilic interactions seem to work for the recognition of CA on the MIP in HILIC mode, while hydrogen bonding and hydrophobic interactions seem to work for the recognition of CA in reversed-phase mode. The MIP had a specific molecular-recognition ability for CA in HILIC mode, while other structurally related compounds, such as chlorogenic acid （CGA), gallic acid, protocatechuic acid and vanillic acid, could not be recognized by the MIP. Furthermore, the MIP was successfully applied for extraction of CA and CGA in the leaves of Eucommia ulmodies in HILIC mode. Copyright © 2015 Elsevier B.V. All rights reserved.

Optimization of Extraction Conditions for Phenolic Acids from the Leaves of Melissa officinalis L. Using Response Surface Methodology

PubMed Central

Yoo, Guijae; Lee, Il Kyun; Park, Seonju; Kim, Nanyoung; Park, Jun Hyung; Kim, Seung Hyun

2018-01-01

Background: Melissa officinalis L. is a well-known medicinal plant from the family Lamiaceae, which is distributed throughout Eastern Mediterranean region and Western Asia. Objective: In this study, response surface methodology (RSM) was utilized to optimize the extraction conditions for bioactive compounds from the leaves of M. officinalis L. Materials and Methods: A Box–Behnken design (BBD) was utilized to evaluate the effects of three independent variables, namely extraction temperature (°C), methanol concentration (%), and solvent-to-material ratio (mL/g) on the responses of the contents of caffeic acid and rosmarinic acid. Results: Regression analysis showed a good fit of the experimental data. The optimal condition was obtained at extraction temperature 80.53°C, methanol concentration 29.89%, and solvent-to-material ratio 30 mL/g. Conclusion: These results indicate the suitability of the model employed and the successful application of RSM in optimizing the extraction conditions. This study may be useful for standardizing production quality, including improving the efficiency of large-scale extraction systems. SUMMARY The optimum conditions for the extraction of major phenolic acids from the leaves of Melissa officinalis L. were determined using response surface methodologyBox–Behnken design was utilized to evaluate the effects of three independent variablesQuadratic polynomial model provided a satisfactory description of the experimental dataThe optimized condition for simultaneous maximum contents of caffeic acid and rosmarinic acid was determined. Abbreviations used: RSM: Response surface methodology, BBD: Box–Behnken design, CA: Caffeic acid, RA: Rosmarinic acid, HPLC: High-performance liquid chromatography. PMID:29720824

Caffeic Acid Derivatives in Market Available Lamiaceae and Echinacea purpurea Products

USDA-ARS?s Scientific Manuscript database

Fresh basil leaves contain chicoric acid, the principal phenolic compound of Echinacea purpurea and purportedly the active ingredient in its dietary supplements. Our group discovered and first reported chicoric acid in basil. This following study examined the distribution of chicoric acid within the...

Synthesis and evaluation of multifunctional ferulic and caffeic acid dimers for Alzheimer's disease.

PubMed

He, Xi-Xin; Yang, Xiao-Hong; Ou, Rui-Ying; Ouyang, Ying; Wang, Sheng-Nan; Chen, Zi-Wei; Wen, Shi-Jun; Pi, Rong-Biao

2017-03-01

In this study, a series of novel ferulic and caffeic acid dimers was designed and synthesised, and their multifunctional properties against Alzheimer's disease (AD) were evaluated. Results showed that our multifunctional strategy was great supported by enhancing the inhibition of Aβ 1-42 self-induced aggregation. Moreover, 7b also had potent protective effects against glutamate-induced cell death without significant cell toxicity in mouse hippocampal neuronal HT22 cells and 10c effectively scavenged diphenylpicrylhydrazyl free radicals. Collectively, these data strongly encourage further optimisation of 7b as a new hit to develop multifunctional agents for the treatment of AD.

A simple method for enzymatic synthesis of unlabeled and radiolabeled Hydroxycinnamate-CoA

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

Rautergarten, Carsten; Baidoo, Edward; Keasling, Jay

Hydroxycinnamate coenzyme A (CoA) thioesters are substrates for biosynthesis of lignin and hydroxycinna- mate esters of polysaccharides and other polymers. Hence, a supply of these substrates is essential for investigation of cell wall biosynthesis. In this study, three recombinant enzymes, caffeic acid 3-O-methyltransferase, 4-coumarate- CoA ligase 1, and 4-coumarate-CoA ligase 5, were cloned from wheat, tobacco, and Arabidopsis, respectively, and were used to synthesize {sup 14}C-feruloyl-CoA, caffeoyl-CoA, p-coumaroyl-CoA, feruloyl-CoA, and sinapoyl-CoA. The corresponding hydroxycinnamoyl-CoA thioesters were high-performance liquid chromatography purified, the only extraction/purification step necessary, with total yields between 88-95%. Radiolabeled {sup 14}C-feruloyl-CoA was generated from caffeic acid and S-adenosyl-{supmore » 14}C-methionine under the combined action of caffeic acid 3-O-methyltransferase and 4-coumarate-CoA ligase 1. About 70% of {sup 14}C-methyl groups from S-adenosyl methionine were incorporated into the final product. The methods presented are simple, fast, and efficient for the preparation of the hydroxycinnamate thioesters.« less

Enzymatic Browning in Sugar Beet Leaves (Beta vulgaris L.): Influence of Caffeic Acid Derivatives, Oxidative Coupling, and Coupled Oxidation.

PubMed

Vissers, Anne; Kiskini, Alexandra; Hilgers, Roelant; Marinea, Marina; Wierenga, Peter Alexander; Gruppen, Harry; Vincken, Jean-Paul

2017-06-21

Sugar beet (Beta vulgaris L.) leaves of 8 month (8 m ) plants showed more enzymatic browning than those of 3 month (3 m ). Total phenolic content increased from 4.6 to 9.4 mg/g FW in 3 m and 8 m , respectively, quantitated by reverse-phase-ultrahigh-performance liquid chromatography-ultraviolet-mass spectrometry (RP-UHPLC-UV-MS). The PPO activity was 6.7 times higher in extracts from 8 m than from 3 m leaves. Substrate content increased from 0.53 to 2.45 mg/g FW in 3 m and 8 m , respectively, of which caffeic acid glycosyl esters were most important, increasing 10-fold with age. Caffeic acid glycosides and vitexin derivatives were no substrates. In 3 m and 8 m, nonsubstrate-to-substrate ratios were 8:1 and 3:1, respectively. A model system showed browning at 3:1 ratio due to formation of products with extensive conjugated systems through oxidative coupling and coupled oxidation. The 8:1 ratio did not turn brown as oxidative coupling occurred without much coupled oxidation. We postulate that differences in nonsubstrate-to-substrate ratio and therewith extent of coupled oxidation explain browning.

Enzymatic Browning in Sugar Beet Leaves (Beta vulgaris L.): Influence of Caffeic Acid Derivatives, Oxidative Coupling, and Coupled Oxidation

PubMed Central

2017-01-01

Sugar beet (Beta vulgaris L.) leaves of 8 month (8m) plants showed more enzymatic browning than those of 3 month (3m). Total phenolic content increased from 4.6 to 9.4 mg/g FW in 3m and 8m, respectively, quantitated by reverse-phase-ultrahigh-performance liquid chromatography–ultraviolet-mass spectrometry (RP-UHPLC–UV-MS). The PPO activity was 6.7 times higher in extracts from 8m than from 3m leaves. Substrate content increased from 0.53 to 2.45 mg/g FW in 3m and 8m, respectively, of which caffeic acid glycosyl esters were most important, increasing 10-fold with age. Caffeic acid glycosides and vitexin derivatives were no substrates. In 3m and 8m, nonsubstrate-to-substrate ratios were 8:1 and 3:1, respectively. A model system showed browning at 3:1 ratio due to formation of products with extensive conjugated systems through oxidative coupling and coupled oxidation. The 8:1 ratio did not turn brown as oxidative coupling occurred without much coupled oxidation. We postulate that differences in nonsubstrate-to-substrate ratio and therewith extent of coupled oxidation explain browning. PMID:28570816

Carcinogenicity of antioxidants BHA, caffeic acid, sesamol, 4-methoxyphenol and catechol at low doses, either alone or in combination, and modulation of their effects in a rat medium-term multi-organ carcinogenesis model.

PubMed

Hirose, M; Takesada, Y; Tanaka, H; Tamano, S; Kato, T; Shirai, T

1998-01-01

The carcinogenicity of low dietary levels of the antioxidants butylated hydroxyanisole (BHA), caffeic acid, sesamol, 4-methoxyphenol (4-MP) and catechol, known to target the forestomach or glandular stomach, were examined alone or in combination in a 2-year long-term experiment and their modifying effects assessed in a medium-term multiorgan model. In the carcinogenicity study, groups of 30-31 male F344 rats were treated with 0.4% BHA, 0.4% caffeic acid, 0.4% sesamol, 0.4% 4-MP and 0.16% catechol either alone or in combination for up to 104 weeks and then killed. In the medium-term multi-organ model, groups of 10 to 15 male F344 rats were given diethylnitrosamine (DEN), N-methylnitrosourea (MNU), 1,2-dimethylhydrazine (DMH), N-butyl-N-(4-hydroxybutyl)nitrosamine (BBN) and 2,2'-dihydroxy-di-n-propylnitrosamine (DHPN) for a total multiple initiation period of 4 weeks (DMBDD treatment). BHA, caffeic acid, sesamol and 4-MP, each at doses of 0.4% or 0.08%, and catechol at doses of 0.16% or 0.032% were administered in the diet either alone or in combination after completion of the initiation regimen. All surviving animals were killed at the end of week 28, and major organs were examined histopathologically. In the carcinogenicity study, slightly increased incidences of forestomach papillomas were found in the sesamol- (15.8%), caffeic acid- (14.8%), catechol- (3%) and 4-MP- (11.5%) treated groups as compared with basal diet (0%), and a significant increase was observed with the five antioxidants in combination (42.9%, P < 0.001). In a medium-term multiorgan carcinogenesis model, incidences of forestomach papillomas and/or carcinomas were increased in each high dose group, but additive or synergistic effects were not found in the combination group. In the low dose case, the incidence of forestomach papillomas was significantly increased only in the combination group. With regard to other organs, the incidence of colon tumors was significantly decreased only in the high dose combination group. The results indicate that even at low dose levels phenolic compounds can exert additive/synergistic effect on carcinogenesis.

Optimizing the models for rapid determination of chlorogenic acid, scopoletin and rutin in plant samples by near-infrared diffuse reflectance spectroscopy

NASA Astrophysics Data System (ADS)

Mao, Zhiyi; Shan, Ruifeng; Wang, Jiajun; Cai, Wensheng; Shao, Xueguang

2014-07-01

Polyphenols in plant samples have been extensively studied because phenolic compounds are ubiquitous in plants and can be used as antioxidants in promoting human health. A method for rapid determination of three phenolic compounds (chlorogenic acid, scopoletin and rutin) in plant samples using near-infrared diffuse reflectance spectroscopy (NIRDRS) is studied in this work. Partial least squares (PLS) regression was used for building the calibration models, and the effects of spectral preprocessing and variable selection on the models are investigated for optimization of the models. The results show that individual spectral preprocessing and variable selection has no or slight influence on the models, but the combination of the techniques can significantly improve the models. The combination of continuous wavelet transform (CWT) for removing the variant background, multiplicative scatter correction (MSC) for correcting the scattering effect and randomization test (RT) for selecting the informative variables was found to be the best way for building the optimal models. For validation of the models, the polyphenol contents in an independent sample set were predicted. The correlation coefficients between the predicted values and the contents determined by high performance liquid chromatography (HPLC) analysis are as high as 0.964, 0.948 and 0.934 for chlorogenic acid, scopoletin and rutin, respectively.

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.

Differential Molecular Targets for Neuroprotective Effect of Chlorogenic Acid and its Related Compounds Against Glutamate Induced Excitotoxicity and Oxidative Stress in Rat Cortical Neurons.

PubMed

Rebai, Olfa; Belkhir, Manel; Sanchez-Gomez, María Victoria; Matute, Carlos; Fattouch, Sami; Amri, Mohamed

2017-12-01

The present study has been designed to explore the molecular mechanism and signaling pathway targets of chlorogenic acid (CGA) and its main hydrolysates, caffeic (CA) and quinic acid in the protective effect against glutamate-excitotoxicity. For this purpose 8-DIV cortical neurons in primary culture were exposed to 50 μM L-glutamic acid plus 10 µM glycine, with or without 10-100 μM tested compounds. Chlorogenic acid and caffeic acid via their antioxidant properties inhibited cell death induced by glutamate in dose depended manner. However, quinic acid slightly protects neurons at a higher dose. DCF, JC-1 and Ca 2+ sensitive fluorescent dye fura-2, were used to measure intracellular ROS accumulation, mitochondrial membrane potential integration and intracellular calcium concentration [Ca 2+ ] i . Results indicate that similarly, CGA acts as a protective agent against glutamate-induced cortical neurons injury by suppressing the accumulation of endogenous ROS and restore the mitochondrial membrane potential, activate the enzymatic antioxidant system by the increase levels of SOD activity and modulate the rise of intracellular calcium levels by increasing the rise of intracellular concentrations of Ca 2+ caused by glutamate overstimulation. PKC signaling cascade appear to be engaged in this protective mechanism. Interseling, CGA and CA also exhibit antiapoptotic properties against glutamate-induced cleaved activation of pro-caspases; caspase 1,8 and 9 and calpain (PD 150606,Calpeptin and MDL 28170).These data suggest that neuroprotective activity of CGA ester may occurs throught its hydrolysate,the caffeic acid and its interaction with intracellular molecules suggesting that CGA exert its neuroprotection via its caffeoly acid group that might potentially be used as a therapeutic agent in neurodegeneratives disorders associated with glutamate excitotoxicity.

Antihypertensive effect of Carica papaya via a reduction in ACE activity and improved baroreflex.

PubMed

Brasil, Girlandia Alexandre; Ronchi, Silas Nascimento; do Nascimento, Andrews Marques; de Lima, Ewelyne Miranda; Romão, Wanderson; da Costa, Helber Barcellos; Scherer, Rodrigo; Ventura, José Aires; Lenz, Dominik; Bissoli, Nazaré Souza; Endringer, Denise Coutinho; de Andrade, Tadeu Uggere

2014-11-01

The aims of this study were to evaluate the antihypertensive effects of the standardised methanolic extract of Carica papaya, its angiotensin converting enzyme inhibitory effects in vivo, its effect on the baroreflex and serum angiotensin converting enzyme activity, and its chemical composition. The chemical composition of the methanolic extract of C. papaya was evaluated by liquid chromatography-mass/mass and mass/mass spectrometry. The angiotensin converting enzyme inhibitory effect was evaluated in vivo by Ang I administration. The antihypertensive assay was performed in spontaneously hypertensive rats and Wistar rats that were treated with enalapril (10 mg/kg), the methanolic extract of C. papaya (100 mg/kg; twice a day), or vehicle for 30 days. The baroreflex was evaluated through the use of sodium nitroprusside and phenylephrine. Angiotensin converting enzyme activity was measured by ELISA, and cardiac hypertrophy was evaluated by morphometric analysis. The methanolic extract of C. papaya was standardised in ferulic acid (203.41 ± 0.02 µg/g), caffeic acid (172.60 ± 0.02 µg/g), gallic acid (145.70 ± 0.02 µg/g), and quercetin (47.11 ± 0.03 µg/g). The flavonoids quercetin, rutin, nicotiflorin, clitorin, and manghaslin were identified in a fraction of the extract. The methanolic extract of C. papaya elicited angiotensin converting enzyme inhibitory activity. The antihypertensive effects elicited by the methanolic extract of C. papaya were similar to those of enalapril, and the baroreflex sensitivity was normalised in treated spontaneously hypertensive rats. Plasma angiotensin converting enzyme activity and cardiac hypertrophy were also reduced to levels comparable to the enalapril-treated group. These results may be associated with the chemical composition of the methanolic extract of C. papaya, and are the first step into the development of a new phytotherapic product which could be used in the treatment of hypertension. Georg Thieme Verlag KG Stuttgart · New York.

The role of artichoke leaf tincture (Cynara scolymus) in the suppression of DNA damage and atherosclerosis in rats fed an atherogenic diet.

PubMed

Bogavac-Stanojevic, Natasa; Kotur Stevuljevic, Jelena; Cerne, Darko; Zupan, Janja; Marc, Janja; Vujic, Zorica; Crevar-Sakac, Milkica; Sopic, Miron; Munjas, Jelena; Radenkovic, Miroslav; Jelic-Ivanovic, Zorana

2018-12-01

Polyphenols and flavonoids in artichoke leaf tincture (ALT) protect cells against oxidative damage. We examined ALT effects on deoxyribonucleic acid (DNA) damage and lipid profiles in rat plasma and gene expression in rat aorta [haemeoxygenase-1 (HO1), haemeoxygenase-2 (HO2), NADPH oxidase 4 (NOX-4), monocyte chemoattractant protein-1 (MCP-1) and nuclear factor (erythroid-derived 2)-like 2 (Nrf2)]. Eighteen male Wistar albino rats were divided into three groups (n = 6/group): The control group (CG) was fed with standard pellet chow for 11 weeks; the AD group was fed for a similar period of time with pellet chow supplemented with 2% cholesterol, 3% sunflower oil and 1% sodium cholate. The ADA group was fed with pellet chow (for 1 week), the atherogenic diet (see above) for the following 4 weeks and then with ALT (0.1 mL/kg body weight) and atherogenic diet for 6 weeks. According to HPLC analysis, the isolated main compounds in ALT were chlorogenic acid, caffeic acid, isoquercitrin and rutin. Normalized HO-1 [0.11 (0.04-0.24)] and MCP-1 [0.29 (0.21-0.47)] mRNA levels and DNA scores [12.50 (4.50-36.50)] were significantly lower in the ADA group than in the AD group [0.84 (0.35-2.51)], p = 0.021 for HO-1 [0.85 (0.61-3.45)], p = 0.047 for MCP-1 and [176.5 (66.50-221.25)], p = 0.020 for DNA scores. HO-1 mRNA was lower in the ADA group than in the CG group [0.30 (0.21-0.71), p = 0.049]. Supplementation with ALT limited the effects of the atherogenic diet through reduced MCP-1 expression, thereby preventing oxidative damage.

Maillard reaction and enzymatic browning affect the allergenicity of Pru av 1, the major allergen from cherry (Prunus avium).

PubMed

Gruber, Patrick; Vieths, Stefan; Wangorsch, Andrea; Nerkamp, Jörg; Hofmann, Thomas

2004-06-16

The influence of thermal processing and nonenymatic as well as polyphenoloxidase-catalyzed browning reaction on the allergenicity of the major cherry allergen Pru av 1 was investigated. After thermal treatment of the recombinant protein rPru av 1 in the absence or presence of carbohydrates, SDS-PAGE, enzyme allergosorbent tests, and inhibition assays revealed that thermal treatment of rPru av 1 alone did not show any influence on the IgE-binding activity of the protein at least for 30 min, thus correlating well with the refolding of the allergen in buffer solution as demonstrated by CD spectroscopic experiments. Incubation of the protein with starch and maltose also showed no effect on IgE-binding activity, whereas reaction with glucose and ribose and, even more pronounced, with the carbohydrate breakdown products glyceraldehyde and glyoxal induced a strong decrease of the IgE-binding capacity of rPru av 1. In the second part of the study, the effect of polyphenoloxidase-catalyzed oxidation of polyphenols on food allergen activity was investigated. Incubation of rPru av 1 with epicatechin in the presence of tyrosinase led to a drastic decrease in IgE-binding activity of the protein. Variations of the phenolic compound revealed caffeic acid and epicatechin as the most active inhibitors of the IgE-binding activity of rPru av 1, followed by catechin and gallic acid, and, finally, by quercetin and rutin, showing significantly lower activity. On the basis of these data, reactive intermediates formed during thermal carbohydrate degradation as well as during enzymatic polyphenol oxidation are suggested as the active chemical species responsible for modifying nucleophilic amino acid side chains of proteins, thus inducing an irreversible change in the tertiary structure of the protein and resulting in a loss of conformational epitopes of the allergen.

Permeability of rosmarinic acid in Prunella vulgaris and ursolic acid in Salvia officinalis extracts across Caco-2 cell monolayers

USDA-ARS?s Scientific Manuscript database

Rosmarinic acid (RA), a caffeic acid derivative found in high concentrations in Prunella vulgaris (self-heal), and ursolic acid (UA), a pentacyclic triterpene acid concentrated in Salvia officinalis (sage), have been traditionally used to treat inflammation in the mouth, and may also be of benefit t...

Wheat bread enriched with green coffee - In vitro bioaccessibility and bioavailability of phenolics and antioxidant activity.

PubMed

Świeca, Michał; Gawlik-Dziki, Urszula; Dziki, Dariusz; Baraniak, Barbara

2017-04-15

The potential bioaccessibility and bioavailability of phenolics, caffeine and antioxidant activity of wheat bread enriched with green coffee were studied. Supplementation enhanced nutraceutical potential by improving phenolic content and lipid protecting capacity. The simulated-digestion-released phenolics (mainly caffeic acid, syringic acid and vanillic acid) from bread, also caused significant qualitative changes (chlorogenic acids were cleaved and significant amounts of caffeic acid and ferulic acid were determined). Compared to the control, for the bread with 1% and 5% of the functional component the contents of phenolics were 1.6 and 3.33 times higher. Also, an approximately 2.3-fold increase in antioxidant activity was found in bread containing 5% of the supplement. The compounds responsible for antioxidant potential have high bioaccessibility but poor bioavailability. The qualitative composition of the phenolic fraction has a key role in developing the antioxidant potential of bread; however, caffeine and synergism between antioxidants are also important considerations. Copyright © 2016 Elsevier Ltd. All rights reserved.

Purple corn (Zea mays L.) phenolic compounds profile and its assessment as an agent against oxidative stress in isolated mouse organs.

PubMed

Ramos-Escudero, Fernando; Muñoz, Ana María; Alvarado-Ortíz, Carlos; Alvarado, Ángel; Yáñez, Jaime A

2012-02-01

This study was designed to determine the contents of total polyphenols, flavonoids, flavonols, flavanols, and anthocyanins of purple corn (Zea mays L.) extracts obtained with different methanol:water concentrations, acidified with 1% HCl (1 N). Another objective was to determine the antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), ferric reducing antioxidant power (FRAP), and deoxyribose assay, individual phenolic compounds by high-performance liquid chromatography (HPLC), and endogenous antioxidant enzyme (superoxide dismutase [SOD], catalase [CAT], and total peroxidase [TPX]) activity and lipid peroxidation activity (thiobarbituric acid-reactive substances [TBARS] assay) in isolated mouse organs. Overall, the highest total content of polyphenols, anthocyanins, flavonoids, flavonols, and flavanols was obtained with the 80:20 methanol:water extract, acidified with 1% HCl (1 N). The 50% inhibitory concentration values obtained by the DPPH and ABTS assays with this extract were 66.3 μg/mL and 250 μg/mL, respectively. The antioxidant activity by the FRAP assay was 26.1 μM Trolox equivalents/g, whereas the deoxyribose assay presented 93.6% inhibition. Because of these results, the 80:20 methanol:water extract, acidified with 1% HCl (1 N), was used for the remaining tests. Eight phenolic compounds were identified by HPLC: chlorogenic acid, caffeic acid, rutin, ferulic acid, morin, quercetin, naringenin, and kaempferol. Furthermore, it was observed that the purple corn extract was capable of significantly reducing lipid peroxidation (lower malondialdehyde [MDA] concentrations by the TBARS assay) and at the same time increasing endogenous antioxidant enzyme (CAT, TPX, and SOD) activities in isolated mouse kidney, liver, and brain. On the basis of the results, it was concluded that the purple corn extract contained various bioactive phenolic compounds that exhibited considerable in vitro antioxidant activity, which correlated well with the decreased MDA formation and increase in activity of endogenous antioxidant enzymes observed in the isolated mouse organs. This warrants further in vivo studies with purple corn extracts to assess its antioxidant activity and other bioactivities.

Isocratic RP-HPLC method for rutin determination in solid oral dosage forms.

PubMed

Kuntić, Vesna; Pejić, Natasa; Ivković, Branka; Vujić, Zorica; Ilić, Katarina; Mićić, Svetlana; Vukojević, Vladana

2007-01-17

A rapid and sensitive assay for quantitative determination of rutin in oral dosage forms based on isocratic reversed phase high performance liquid chromatography (RP-HPLC) was developed and validated. Using a C(18) reverse-phase analytical column, the following conditions were chosen as optimal: mobile phase methanol-water 1:1 (v/v), pH 2.8 (adjusted with phosphoric acid), flow rate=1 mL min(-1) and temperature T=40.0 degrees C. Linearity was observed in the concentration range 8-120 microg mL(-1) with a correlation coefficient of 0.99982 and the limit of detection (LOD)=2.6 microg mL(-1), and limit of quantification (LOQ)=8.0 microg mL(-1). Intra- and inter-day precision were within acceptable limits. Robustness test indicated that the mobile phase composition and pH influence mainly the separation. The proposed method allowed direct determination of rutin in pharmaceutical dosage forms in the presence of excipients, but is not suitable for preparations where compounds structurally/chemically related to rutin may be present.

Biological, chemical and in silico fingerprints of Dianthus calocephalus Boiss.: A novel source for rutin.

PubMed

Uysal, Sengul; Aktumsek, Abdurrahman; Picot-Allain, Carene M N; Unuvar, Hamiyet; Mollica, Adriano; Georgiev, Milen I; Zengin, Gokhan; Mahomoodally, Mohamad Fawzi

2018-03-01

Extracts (methanol, ethyl acetate, and water) from Dianthus calocephalus Boiss. prepared by different extraction techniques (maceration, Soxhlet, and ultrasonication) were studied for possible inhibitory action against key enzymes (α-amylase, α-glucosidase, acetyl cholinesterase, butyryl cholinesterase, and tyrosinase). Antioxidant potential was established using a battery of assays and phenolic compounds profiled by RP-HPLC. Binding pose of tyrosinase with rutin was studied by means of molecular docking. Methanol extracts showed the highest phenolic (39.35-40.25 mgGAE/g) content and rich in rutin (61.38-72.07 mg/g extract). Ethyl acetate extracts of D. calocephalus were potent inhibitors of acetyl (1.45-1.48 mgGALAE/g) and butyryl (2.44-2.74 mgGALAE/g) cholinesterases. Docking studies showed that rutin interacts with the side chains of the key amino acid residues and to the copper atom found at the active site of tyrosinase. Methanol extracts showed highest antioxidant capacity. D. calocephalus showed interesting biological properties that could be further studied to manage diabetes, neurodegenerative diseases, Alzheimer's disease, and hyperpigmentation. Copyright © 2018 Elsevier Ltd. All rights reserved.

Neurotoxic effects of silver nanoparticles and the protective role of rutin.

PubMed

Ahmed, Mona M; Hussein, Mohamed M A

2017-06-01

The toxicological studies on silver nanoparticles (Ag-NPs) have become a hot topic over the past few decades due to their unique properties on the nanoscale and widespread in many commercial products that launched into the market recently. This study was undertaken to shed light on Ag-NPs toxicity on neurotransmitters with special emphasis on the impact of concurrent administration of rutin with Ag-NPs in the experimental rats. The oral administration of Ag-NPs in rats induced brain oxidative stress, significant alterations in neurotransmitters and amino acids. Furthermore, transcriptional levels of glutamatergic N-methyl-d-aspartate (NMDA) receptors, monoamino oxidases (MAO-A, MAO-B) and metallothionein-III (MT-III) showed a significant elevation in Ag-NPs intoxicated rats. Moreover, histological examinations revealed astrogliosis and demyelination of neurons concomitant with neuronal degeneration and vacuolation. Strikingly, oral administration of rutin counterbalanced the toxic effects triggered by Ag-NPs. Taken together, our findings suggested that oral administration of Ag-NPs induced neurotoxicity in rats and rutin mitigates these effects. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

Lactobacillus acidophilus—Rutin Interplay Investigated by Proteomics

PubMed Central

Mazzeo, Maria Fiorella; Lippolis, Rosa; Sorrentino, Alida; Liberti, Sarah; Fragnito, Federica; Siciliano, Rosa Anna

2015-01-01

Dietary polyphenols are bioactive molecules that beneficially affect human health, due to their anti-oxidant, anti-inflammatory, cardio-protective and chemopreventive properties. They are absorbed in a very low percentage in the small intestine and reach intact the colon, where they are metabolized by the gut microbiota. Although it is well documented a key role of microbial metabolism in the absorption of polyphenols and modulation of their biological activity, molecular mechanisms at the basis of the bacteria-polyphenols interplay are still poorly understood. In this context, differential proteomics was applied to reveal adaptive response mechanisms that enabled a potential probiotic Lactobacillus acidophilus strain to survive in the presence of the dietary polyphenol rutin. The response to rutin mainly modulated the expression level of proteins involved in general stress response mechanisms and, in particular, induced the activation of protein quality control systems, and affected carbohydrate and amino acid metabolism, protein synthesis and cell wall integrity. Moreover, rutin triggered the expression of proteins involved in oxidation-reduction processes.This study provides a first general view of the impact of dietary polyphenols on metabolic and biological processes of L. acidophilus. PMID:26544973

Lactobacillus acidophilus-Rutin Interplay Investigated by Proteomics.

PubMed

Mazzeo, Maria Fiorella; Lippolis, Rosa; Sorrentino, Alida; Liberti, Sarah; Fragnito, Federica; Siciliano, Rosa Anna

2015-01-01

Dietary polyphenols are bioactive molecules that beneficially affect human health, due to their anti-oxidant, anti-inflammatory, cardio-protective and chemopreventive properties. They are absorbed in a very low percentage in the small intestine and reach intact the colon, where they are metabolized by the gut microbiota. Although it is well documented a key role of microbial metabolism in the absorption of polyphenols and modulation of their biological activity, molecular mechanisms at the basis of the bacteria-polyphenols interplay are still poorly understood. In this context, differential proteomics was applied to reveal adaptive response mechanisms that enabled a potential probiotic Lactobacillus acidophilus strain to survive in the presence of the dietary polyphenol rutin. The response to rutin mainly modulated the expression level of proteins involved in general stress response mechanisms and, in particular, induced the activation of protein quality control systems, and affected carbohydrate and amino acid metabolism, protein synthesis and cell wall integrity. Moreover, rutin triggered the expression of proteins involved in oxidation-reduction processes.This study provides a first general view of the impact of dietary polyphenols on metabolic and biological processes of L. acidophilus.

Monolignol biosynthesis in microsomal preparations from lignifying stems of alfalfa (Medicago sativa L.).

PubMed

Guo, Dianjing; Chen, Fang; Dixon, Richard A

2002-11-01

Microsomal preparations from lignifying stems of alfalfa (Medicago sativa L.) contained coniferaldehyde 5-hydroxylase activity and immunodetectable caffeic acid 3-O-methyltransferase (COMT), and catalyzed the S-adenosyl L-methionine (SAM) dependent methylation of caffeic acid, caffeyl aldehyde and caffeyl alcohol. When supplied with NADPH and SAM, the microsomes converted caffeyl aldehyde to coniferaldehyde, 5-hydroxyconiferaldehyde, and traces of sinapaldehyde. Coniferaldehyde was a better precursor of sinapaldehyde than was 5-hydroxyconiferaldehyde. The alfalfa microsomes could not metabolize 4-coumaric acid, 4-coumaraldehyde, 4-coumaroyl CoA, or ferulic acid. No metabolism of monolignol precursors was observed in microsomal preparations from transgenic alfalfa down-regulated in COMT expression. In most microsomal preparations, the level of the metabolic conversions was independent of added recombinant COMT. Taken together, the data provide only limited support for the concept of metabolic channeling in the biosynthesis of S monolignols via coniferaldehyde.

Hydroxycinnamic acids in cooked potato tubers from Solanum tuberosum group Phureja.

PubMed

Piñeros-Niño, Clara; Narváez-Cuenca, Carlos-Eduardo; Kushalappa, Ajjamada C; Mosquera, Teresa

2017-05-01

Hydroxycinnamic acids are phenolic compounds and are considered to have health promotion properties due to their antioxidant activity. Potato tubers of 113 genotypes of Solanum tuberosum group Phureja belonging to the Colombian Central Collection, landraces of potatoes, and commercial cultivars were evaluated for their hydroxycinnamic acids content. The composition of these compounds was analyzed using cooked tubers in two different agro-climatic conditions. The genotypes were analyzed for chlorogenic acid, neo -chlorogenic acid, crypto -chlorogenic acid, and caffeic acid by ultrahigh-performance liquid chromatography (UHPLC). Chlorogenic acid was the major representative and varied between 0.77 to 7.98 g kg -1  DW (dry weight) followed by crypto -chlorogenic acid (from 0.09 to 1.50 g kg -1  DW). Under moorland agro-climatic conditions even though the chlorogenic acid levels increased with respect to flatland agro-climatic conditions, the related isomer neo -chlorogenic acid decreased as compared to flatland conditions. The correlation between chlorogenic acid with the isomers, and with caffeic acid was positive. This study demonstrated that there is a wide variation in hydroxycinnamic acids contents in the germplasm studied, which can be exploited in breeding programs to contribute to human health.

Effect of lemongrass water extract supplementation on atherogenic index and antioxidant status in rats.

PubMed

Somparn, Nuntiya; Saenthaweeuk, Suphaket; Naowaboot, Jarinyaporn; Thaeomor, Atcharaporn; Kukongviriyapan, Veerapol

2018-06-01

Cymbopogon citratus (DC) Stapf., commonly known as lemongrass, possesses strong antioxidant and cardiotonic properties. Lemongrass water extract contains several polyphenolic compounds including gallic acid, isoquercetin, quercetin, rutin, catechin and tannic acid. Rutin, isoquercetin catechin and quercetin are the flavonoids most abundantly found in the extract. The extract significantly decreased total cholesterol, low-density lipoprotein and atherogenic index in rats after treatment (p < 0.05). Expression of genes and protein of sterol regulatory element binding protein-1c (SREBP1c) and HMG-CoA reductase (HMGR) was also lowered significantly in treated groups (p < 0.05). Moreover, serum antioxidant capacity increased in treated rats in comparison with untreated ones (p < 0.05) and was associated with decreased serum lipid peroxidation.

Ilex paraguariensis crude extract acts on protection and reversion from damage induced by t-butyl hydroperoxide in human erythrocytes: a comparative study with isolated caffeic and/or chlorogenic acids.

PubMed

Portela, José Luiz; Soares, Deividi; Rosa, Hemerson; Roos, Daniel Henrique; Pinton, Simone; Ávila, Daiana Silva; Puntel, Robson L

2017-05-01

Studies comparing the effects of phytochemicals under different regimens of exposure are necessary to give a better indication about their mechanism(s) of protection. Hence, in the present study, we investigated the preventive (pre-incubation), protective (co-incubation) and/or remediative (post-incubation) activity of chlorogenic acid and caffeic acids, in comparison with Ilex paraguariensis crude extract, against t-butyl hydroperoxide (t-BHP)-induced damage to human erythrocytes. We found that both caffeic and chlorogenic acids were able to prevent and revert the hemolysis associated with t-BHP exposure. By contrast, isolated compounds (alone or in combination) presented no effect on basal and/or t-BHP-induced non-protein thiol (NPSH) oxidation or production of thiobarbituric acid reactive substances (TBBARS). In turn, I. paraguariensis extract was effective to prevent, protect and revert the hemolysis associated with t-BHP exposure. Moreover, I. paraguariensis significantly protects and reverts t-BHP-induced NPSH oxidation and TBARS production. We have found that I. paraguariensis extract acts better with respect to the protection and reversion of t-BHP-associated changes, whereas isolated compounds are more active in preventing and reverting t-BHP pro-hemolytic action. Moreover, our data suggest that the pro-hemolytic activity of t-BHP may occur via mechanism(s) other(s) than lipid peroxidation and/or NPSH oxidation. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

Biomarkers of Exposure to Toxic Substances. Volume 1. Global Experimental Design: Biomarker Discovery for Early Prediction of Organ-Selective Toxicity

DTIC Science & Technology

2009-05-30

in the polyphenols chlorogenic acid , quinic acid and caffeic acid ). It appears in variable concentrations in urine and at much lower concentrations...liver, kidney, toxicity, gene, expression, nephrotoxin, D-serine, hippuric acid , Puromycin, Amphotericin B 16. SECURITY CLASSIFICATION OF: 17...6 1.4.4. Hippuric Acid

Antiproliferative activity and SARs of caffeic acid esters with mono-substituted phenylethanols moiety.

PubMed

Xie, Jin; Yang, Fengzhi; Zhang, Man; Lam, Celine; Qiao, Yixue; Xiao, Jia; Zhang, Dongdong; Ge, Yuxuan; Fu, Lei; Xie, Dongsheng

2017-01-15

A series of CAPE derivatives with mono-substituted phenylethanols moiety were synthesized and evaluated by MTT assay on growth of 4 human cancer cell lines (Hela, DU-145, MCF-7 and ECA-109). The substituent effects on the antiproliferative activity were systematically investigated for the first time. It was found that electron-donating and hydrophobic substituents at 2'-position of phenylethanol moiety could significantly enhance CAPE's antiproliferative activity. 2'-Propoxyl derivative, as a novel caffeic acid ester, exhibited exquisite potency (IC 50 =0.4±0.02 & 0.6±0.03μM against Hela and DU-145 respectively). Copyright © 2016 Elsevier Ltd. All rights reserved.

Determination of caffeic acid in wine using PEDOT film modified electrode.

PubMed

Bianchini, C; Curulli, A; Pasquali, M; Zane, D

2014-08-01

A novel method using PEDOT (poly(3,4-ethylenedioxy) thiophene) modified electrode was developed for the determination of caffeic acid (CA) in wine. Cyclic voltammetry (CV) with the additions standard method was used to quantify the analyte at PEDOT modified electrodes. PEDOT films were electrodeposited on Platinum electrode (Pt) in aqueous medium by galvanostatic method using sodium poly(styrene-4-sulfonate) (PSS) as electrolyte and surfactant. CV allows detecting the analyte over a wide concentration range (10.0nmoll(-1)-6.5mmoll(-1)). The electrochemical method proposed showed good statistical and analytical parameters as linearity range, LOD, LOQ and sensitivity. Copyright © 2014 Elsevier Ltd. All rights reserved.

Neuraminidase inhibition of Dietary chlorogenic acids and derivatives - potential antivirals from dietary sources.

PubMed

Gamaleldin Elsadig Karar, Mohamed; Matei, Marius-Febi; Jaiswal, Rakesh; Illenberger, Susanne; Kuhnert, Nikolai

2016-04-01

Plants rich in chlorogenic acids (CGAs), caffeic acids and their derivatives have been found to exert antiviral effects against influenza virus neuroaminidase. In this study several dietary naturally occurring chlorogenic acids, phenolic acids and derivatives were screened for their inhibitory activity against neuroaminidases (NAs) from C. perfringens, H5N1 and recombinant H5N1 (N-His)-Tag using a fluorometric assay. There was no significant difference in inhibition between the different NA enzymes. The enzyme inhibition results indicated that chlorogenic acids and selected derivatives, exhibited high activities against NAs. It seems that the catechol group from caffeic acid was important for the activity. Dietary CGA therefore show promise as potential antiviral agents. However, caffeoyl quinic acids show low bioavailibility and are intensly metabolized by the gut micro flora, only low nM concentrations are observed in plasma and urine, therefore a systemic antiviral effect of these compounds is unlikely. Nevertheless, gut floral metabolites with a catechol moiety or structurally related dietary phenolics with a catechol moiety might serve as interesting compounds for future investigations.

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

Molecular and biochemical characterization of a benzenoid/phenylpropanoid meta/para-O-methyltransferase from Rauwolfia serpentina roots.

PubMed

Wiens, Brent; De Luca, Vincenzo

2016-12-01

The monoterpenoid indole alkaloids, reserpine and rescinnamine contain 3, 4, 5-trimethoxybenzoate or 3, 4, 5-trimethoxycinnamate, respectively, within their structures and they accumulate in different plant organs and particularly within roots of Rauwolfia serpentina. This plant also accumulates acylated sugars substituted with 3, 4, 5-trimethoxybenzoate and 3, 4, 5-trimethoxycinnamate. In the present study, transcriptome and metabolome analyses of R. serpentina roots allowed the identification of 7 candidate O-methytransferase (OMT) genes that might be associated with the formation of 3, 4, 5-trimethoxybenzoate and 3, 4, 5-trimethoxycinnamate and led to the molecular cloning of 4 genes for functional expression and analysis. Two candidate genes were expressed in E. coli and were shown to use different phenolics as methyl acceptors. RsOMT1, a member of the caffeoyl CoA-OMT-like family of genes, converted 3, 5 dimethoxy-4-hydroxycinnamic, caffeic and 3, 4, 5 trihydroxybenzoic acids to trimethoxycinnamic-, ferulic/isoferulic- and 3-methoxy, 4, 5 dihydroxybenzoic or 4-methoxy, 3, 5 dihydroxybenzoic acids, respectively, when supplied with these substrates. RsOMT3, a member of the caffeic acid-OMT-like family of genes, only converted caffeic acid to ferulic acid. Both enzymes showed considerable promiscuity with respect to various flavonoid substrates that they accepted. The para-O-methylation activity of RsOMT1 is quite rare and unusual for plant OMTs. The involvement of RsOMT1 and RsOMT3 in the assembly of trimethoxybenzoic and trimethoxycinnamic acids is discussed. Copyright © 2016 Elsevier Ltd. All rights reserved.

Spectroscopic (FT-IR, FT-Raman, UV absorption, 1H and 13C NMR) and theoretical (in B3LYP/6-311++G** level) studies on alkali metal salts of caffeic acid.

PubMed

Świsłocka, Renata

2013-01-01

The effect of some metals on the electronic system of benzoic and nicotinic acids has recently been investigated by IR, Raman and UV spectroscopy [1-3]. Benzoic and nicotinic acids are regarded model systems representing a wide group of aromatic ligands which are incorporated into enzymes. In this work the FT-IR (in solid state and in solution), FT-Raman, UV absorption and (1)H and (13)C NMR spectra of caffeic acid (3,4-dihydroxycinnamic acid) and its salts with lithium, sodium, potassium, rubidium and caesium were registered, assigned and analyzed. The effect of alkali metals on the electronic system of ligands was discussed. Studies of differences in the number and position of bands from the IR, Raman, UV absorption spectra and chemical shifts from NMR spectra allowed to conclude on the distribution of electronic charge in the molecules, the delocalization energy of π electrons and the reactivity of ligands in metal complexes. Optimized geometrical structures of studied compounds were calculated by B3LYP method using 6-311++G** basis set. Bond lengths, angles and dipole moments for the optimized structures of caffeic acid and lithium, sodium, potassium caffeinates were also calculated. The theoretical wavenumbers and intensities of IR spectra were obtained. The calculated parameters were compared to the experimental characteristics of investigated compounds. Microbial activity of studied compounds was tested against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Proteus vulgaris. Copyright © 2012 Elsevier B.V. All rights reserved.

The Contribution of Buckwheat Genetic Resources to Health and Dietary Diversity

PubMed Central

Sytar, Oksana; Brestic, Marian; Zivcak, Marek; Tran, Lam-Son Phan

2016-01-01

Despite several reports on the beneficial effects of buckwheat in prevention of human diseases, little attention has been devoted to the variability of biochemical and physiological traits in different buckwheat genetic resources. This review describes the biochemical evaluation of buckwheat genetic resources and the identification of elite genotypes for plant breeding and exploitation. The various types of bioactive compounds present in different varieties provide basic background information needed for the efficient production of buckwheat foods with added value. In this review, we will provide an integrated view of the biochemistry of bioactive compounds of buckwheat plants of different origin, especially of fagopyrin, proteins and amino acids, as well as of other phenolic compounds including rutin and chlorogenic acid. In addition to the genetic background, the effect of different growth conditions is discussed. The health effects of fagopyrin, phenolic acids, specific proteins and rutin are also presented. PMID:27252586

Crystallization and preliminary X-ray diffraction analysis of a Lys49-phospholipase A2 complexed with caffeic acid, a molecule with inhibitory properties against snake venoms

PubMed Central

Shimabuku, Patrícia S.; Fernandes, Carlos A. H.; Magro, Angelo J.; Costa, Tássia R.; Soares, Andreimar M.; Fontes, Marcos R. M.

2011-01-01

Phospholipases A2 (PLA2s) are one of the main components of bothropic venoms; in addition to their phospholipid hydrolysis action, they are involved in a wide spectrum of pharmacological activities, including neurotoxicity, myo­toxicity and cardiotoxicity. Caffeic acid is an inhibitor that is present in several plants and is employed for the treatment of ophidian envenomations in the folk medicine of many developing countries; as bothropic snake bites are not efficiently neutralized by conventional serum therapy, it may be useful as an antivenom. In this work, the cocrystallization and preliminary X-ray diffraction analysis of the Lys49-PLA2 piratoxin I from Bothrops pirajai venom in the presence of the inhibitor caffeic acid (CA) are reported. The crystals diffracted X-rays to 1.65 Å resolution and the structure was solved by molecular-replacement techniques. The electron-density map unambiguously indicated the presence of three CA molecules that interact with the C-terminus of the protein. This is the first time a ligand has been observed bound to this region and is in agreement with various experiments previously reported in the literature. PMID:21301098

Phenolic compounds, organic acids and antioxidant activity of grape juices produced in industrial scale by different processes of maceration.

PubMed

Lima, Marcos dos Santos; da Conceição Prudêncio Dutra, Maria; Toaldo, Isabela Maia; Corrêa, Luiz Claudio; Pereira, Giuliano Elias; de Oliveira, Débora; Bordignon-Luiz, Marilde Terezinha; Ninow, Jorge Luiz

2015-12-01

The effect of maceration process on the profile of phenolic compounds, organic acids composition and antioxidant activity of grape juices from new varieties of Vitis labrusca L. obtained in industrial scale was investigated. The extraction process presented a high yield without pressing the grapes. The use of a commercial pectinase resulted in an increase on extraction yield and procyanidins B1 and B2 concentrations and a decrease on turbidity and concentration of catechins. The combination of 60 °C and 3.0 mL 100 kg(-1) of enzyme resulted in the highest extraction of phenolic compounds, reducing the content of acetic acid. The juices presented high antioxidant activity, related to the great concentration of malvidin, cyanidin, catechin and caffeic, cinnamic and gallic acids. Among the bioactive compounds, the juices presented high concentration of procyanidin B1, caffeic acid and trans-resveratrol, with higher levels compared to those reported in the literature. Copyright © 2015 Elsevier Ltd. All rights reserved.

Determination of rutin in rat plasma by ultra performance liquid chromatography tandem mass spectrometry and application to pharmacokinetic study.

PubMed

Chen, Mengchun; Zhang, Xiaoqian; Wang, Hao; Lin, Baoli; Wang, Shuanghu; Hu, Guoxin

2015-04-01

A sensitive and rapid ultra performance liquid chromatography tandem mass spectrometry (UPLC-MS-MS) method for the determination of rutin in rat plasma was developed and validated. After addition of tolbutamide as internal standard (IS), protein precipitation by acetonitrile was used as sample preparation. The chromatographic separation was performed on an Acquity UPLC BEH C18 column (2.1 × 50 mm, 1.7 μm particle size), using acetonitrile-0.1% formic acid as the mobile phase with gradient elution, delivered at a flow-rate of 0.4 mL/min. Mass spectrometric analysis was performed using a XEVO TQD mass spectrometer coupled with an electro-spray ionization (ESI) source in the positive ion mode. The MRM transitions of m/z 610.91→302.98 and m/z 271.2→155.1 were used to quantify for rutin and tolbutamide, respectively. This assay method has been fully validated in terms of specificity, linearity, recovery and matrix effect, accuracy, precision and stability. Calibration curves were linear in the concentration ranges of 25-2000 ng/mL for rutin. Only 3 min was needed for an analytical run. This developed method was successfully used for determination of rutin in rat plasma for pharmacokinetic study. © The Author 2014. Published by Oxford University Press. All rights reserved. For Permissions, please email: journals.permissions@oup.com.

Antihyperglycemic Activity of the Leaves from Annona cherimola Miller and Rutin on Alloxan-induced Diabetic Rats

PubMed Central

Calzada, Fernando; Solares-Pascasio, Jesús Iván; Ordoñez-Razo, R. M.; Velazquez, Claudia; Barbosa, Elizabeth; García-Hernández, Normand; Mendez-Luna, David; Correa-Basurto, José

2017-01-01

Background: Annona cherimola, known as “chirimoya” has been reported in Mexican traditional medicine for the treatment of diabetes. Objective: The aims of the present study were to validate and assess the traditional use of A. cherimola as an antidiabetic agent. Materials and Methods: The ethanol extract from A. cherimola (300 mg/kg, EEAc), subsequent fractions (100 mg/kg), and rutin (30 mg/kg) were studied on alloxan-induced type 2 diabetic (AITD) and normoglycemic rats. In addition, oral glucose tolerance test (OGTT) and oral sucrose tolerance test (OSTT) were performed in normoglycemic rats. Molecular docking technique was used to conduct the computational study. Results: Bioassay-guided fractionation of EEAc afforded as major antihyperglycemic compound, rutin. EEAc attenuated postprandial hyperglycemia in acute test using AITD rats (331.5 mg/dL) carrying the glycemic levels to 149.2 mg/dL. Rutin after 2 h, attenuated postprandial hyperglycemia in an acute assay using AITD rats such as EEAc, with maximum effect (150.0 mg/dL) being seen at 4 h. The antihyperglycemic activities of EEAc and rutin were comparable with acarbose (151.3 mg/dL). In the subchronic assay on AITD rats, the EEAc and rutin showed a reduction of the blood glucose levels since the 1st week of treatment, reaching levels similar to normoglycemic state (116.9 mg/kg) that stayed constant for the rest of the assay. OGTT and OSTT showed that EEAc and rutin significantly lowered blood glucose levels in normoglycemic rats at 2 h after a glucose or sucrose load such as acarbose. Computational molecular docking showed that rutin interacted with four amino acids residues in the enzyme α-glucosidase. Conclusion: The results suggest that rutin an α-glucosidase inhibitor was responsible in part of the antihyperglycemic activity of A. cherimola. Its in vivo antihyperglycemic activity is in good agreement with the traditional use of A. cherimola for the treatment of diabetes. SUMMARY The ethanol extract from Annona cherimola (300 mg/kg, EEAc), subsequent fractions (100 mg/kg) and rutin (30 mg/kg) were studied on alloxan-induced type 2 diabetic (AITD) and normoglycemic rats. The results suggest that rutin; an α-glucosidase inhibitor was responsible in part of the antihyperglycemic activity of A. cherimola. Its in vivo antihyperglycemic activity is in good agreement with the traditional use of A. cherimola for the treatment of diabetes. Abbreviations Used: EEAc: The ethanol extract from Annona cherimola, AITD: Alloxan-induced type 2 diabetic rats, OGTT: Oral glucose tolerance test, OSTT: Oral sucrose tolerance test, DM: Diabetes mellitus PMID:28250646

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.

Enzymatic acylation of flavonoid glycosides by a carbohydrate esterase of family 16.

PubMed

Biely, Peter; Cziszárová, Mária; Wong, Ken K Y; Fernyhough, Alan

2014-11-01

The acetyl esterase of Trichoderma reesei belonging to carbohydrate esterase (CE) family 16 catalyzes transacylations to carbohydrate moieties of flavonoid glycosides, esculin and rutin. The enzyme recognizes as acyl donors vinyl esters of short carboxylic acids. Esculin was acylated at position 3 of the glucosyl residue in aqueous solutions saturated with vinyl acetate and vinyl propionate. The yields of esculin monoacetate and monopropionate of esculin in aqueous medium (esculin 40 mM, enzyme 40 µg/ml, 40 °C, 3 days) were 67 and 55 %, respectively. Replacement of water by 2-propanol was required for a similar acylation of rutin at 4 mM concentration. The yields of rutin monoacetate and propionate were 60 and 30 %, respectively. The results indicate that the enzyme could be used for an easy modification of solubility and hydrophobicity of glycosylated compounds, including drugs and functional food additives.

Stabilization effects of naringenin and caffeic acid on γ-irradiatedEPDM

NASA Astrophysics Data System (ADS)

Zaharescu, T.; Jipa, S.; Mantsch, A.; Henderson, D.

2013-03-01

The stabilization of ethylene-propylene diene rubber (EPDM) with naringenin and caffeic acid is studied. The selected concentrations were 0.25, 0.50 and 1 phr. The degradation was performed by γ-irradiation. The protective effect of these antioxidants was investigated by isothermal chemiluminescence at 170 °C and FTIR spectroscopy. The synergetic action of these compounds and metallic selenium was also revealed. The exceptional contribution provided by these phenolic stabilizers is characterized by three kinetic parameters: initial CL intensity, oxidation induction time and maximum period of degradation. The radiation stability of stabilized EPDM is efficiently depicted by induction periods which are the minimum 6times longer for unirradiated samples and 2-50 times longer for 50 kGy-irradiated specimens than pristineEPDM.

Synthesis, antifungal activity of caffeic acid derivative esters, and their synergism with fluconazole and nystatin against Candida spp.

PubMed

Sardi, Janaína de Cássia Orlandi; Gullo, Fernanda Patrícia; Freires, Irlan Almeida; Pitangui, Nayla de Souza; Segalla, Maicon Petrônio; Fusco-Almeida, Ana Marisa; Rosalen, Pedro Luiz; Regasini, Luís Octávio; Mendes-Giannini, Maria José Soares

2016-12-01

We tested the antifungal potential of caffeic acid and 8 of its derivative esters against Candidaalbicans ATCC 90028 and 9 clinical isolatesand carried out a synergism assay with fluconazole and nystatin. Propyl caffeate (C3) showed the best antifungal activity against the tested strains. When in combination, C3 markedly reduced the MIC of fluconazole and nystatin with synergistic effect up to 64-fold. Finally, C3 showed a high IC 50 value and selective indexagainst oral keratinocytes, demonstrating low toxicity against this cell type and selectivity for yeast cells. Further research should confirm its antifungal potential for development of combined therapy to treat C. albicans infections. Copyright © 2016 Elsevier Inc. All rights reserved.

Chromatographic methods for metabolite profiling of virus- and phytoplasma-infected plants of Echinacea purpurea.

PubMed

Pellati, Federica; Epifano, Francesco; Contaldo, Nicoletta; Orlandini, Giulia; Cavicchi, Lisa; Genovese, Salvatore; Bertelli, Davide; Benvenuti, Stefania; Curini, Massimo; Bertaccini, Assunta; Bellardi, Maria Grazia

2011-10-12

This study was focused on the effects of virus and phytoplasma infections on the production of Echinacea purpurea (L.) Moench secondary metabolites, such as caffeic acid derivatives, alkamides, and essential oil. The identification of caffeic acid derivatives and alkamides was carried out by means of high-performance liquid chromatography-diode array detection (HPLC-DAD), HPLC-electrospray ionization-mass spectrometry (ESI-MS), and MS(2). Quantitative analysis of these compounds was carried out using HPLC-DAD. The results indicated that the presence of the two pathogens significantly decreases (P < 0.05) the content of cichoric acid, the main caffeic acid derivative. Regarding the main alkamide, dodeca-2E,4E,8Z,10E/Z-tetraenoic acid isobutylamide, a significant decrease (P < 0.05) in the content of this secondary metabolite was observed in virus-infected plants in comparison with healthy plants, while in the phytoplasma-infected sample the variation of this secondary metabolite was not appreciable. The % relative area of the E/Z isomers of this alkamide was also found to change in infected samples. The gas chromatography (GC) and GC-MS analysis of E. purpurea essential oil enabled the identification of 30 compounds. The main significant differences (P < 0.05) in the semiquantitative composition were observed for three components: limonene, cis-verbenol, and verbenone. The results indicate that the presence of virus and phytoplasma has an appreciable influence on the content of E. purpurea secondary metabolites, which is an important issue in defining the commercial quality, market value, and therapeutic efficacy of this herbal drug.

Purple Corn (Zea mays L.) Phenolic Compounds Profile and Its Assessment as an Agent Against Oxidative Stress in Isolated Mouse Organs

PubMed Central

Ramos-Escudero, Fernando; Muñoz, Ana María; Alvarado-Ortíz, Carlos; Alvarado, Ángel

2012-01-01

Abstract This study was designed to determine the contents of total polyphenols, flavonoids, flavonols, flavanols, and anthocyanins of purple corn (Zea mays L.) extracts obtained with different methanol:water concentrations, acidified with 1% HCl (1 N). Another objective was to determine the antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), ferric reducing antioxidant power (FRAP), and deoxyribose assay, individual phenolic compounds by high-performance liquid chromatography (HPLC), and endogenous antioxidant enzyme (superoxide dismutase [SOD], catalase [CAT], and total peroxidase [TPX]) activity and lipid peroxidation activity (thiobarbituric acid–reactive substances [TBARS] assay) in isolated mouse organs. Overall, the highest total content of polyphenols, anthocyanins, flavonoids, flavonols, and flavanols was obtained with the 80:20 methanol:water extract, acidified with 1% HCl (1 N). The 50% inhibitory concentration values obtained by the DPPH and ABTS assays with this extract were 66.3 μg/mL and 250 μg/mL, respectively. The antioxidant activity by the FRAP assay was 26.1 μM Trolox equivalents/g, whereas the deoxyribose assay presented 93.6% inhibition. Because of these results, the 80:20 methanol:water extract, acidified with 1% HCl (1 N), was used for the remaining tests. Eight phenolic compounds were identified by HPLC: chlorogenic acid, caffeic acid, rutin, ferulic acid, morin, quercetin, naringenin, and kaempferol. Furthermore, it was observed that the purple corn extract was capable of significantly reducing lipid peroxidation (lower malondialdehyde [MDA] concentrations by the TBARS assay) and at the same time increasing endogenous antioxidant enzyme (CAT, TPX, and SOD) activities in isolated mouse kidney, liver, and brain. On the basis of the results, it was concluded that the purple corn extract contained various bioactive phenolic compounds that exhibited considerable in vitro antioxidant activity, which correlated well with the decreased MDA formation and increase in activity of endogenous antioxidant enzymes observed in the isolated mouse organs. This warrants further in vivo studies with purple corn extracts to assess its antioxidant activity and other bioactivities. PMID:22082063

Constituents of Propolis: Chrysin, Caffeic Acid, p-Coumaric Acid, and Ferulic Acid Induce PRODH/POX-Dependent Apoptosis in Human Tongue Squamous Cell Carcinoma Cell (CAL-27).

PubMed

Celińska-Janowicz, Katarzyna; Zaręba, Ilona; Lazarek, Urszula; Teul, Joanna; Tomczyk, Michał; Pałka, Jerzy; Miltyk, Wojciech

2018-01-01

Propolis evokes several therapeutic properties, including anticancer activity. These activities are attributed to the action of polyphenols. Previously it has been demonstrated, that one of the most abundant polyphenolic compounds in ethanolic extracts of propolis are chrysin, caffeic acid, p -coumaric acid, and ferulic acid. Although their pro-apoptotic activity on human tongue squamous cell carcinoma cells (CAL-27) was established previously, the detailed mechanism of this process remains unclear. Considering the crucial role of proline metabolism and proline dehydrogenase/proline oxidase (PRODH/POX) in the regulation of cancer cell survival/apoptosis, we studied these processes in polyphenol-treated CAL-27 cells. All studied polyphenols evoked anti-proliferative activity, accompanied by increased PRODH/POX, P53, active caspases-3 and -9 expressions and decreased collagen biosynthesis, prolidase activity and proline concentration in CAL-27 cells. These data suggest that polyphenols of propolis induce PRODH/POX-dependent apoptosis through up-regulation of mitochondrial proline degradation and down-regulation of proline utilization for collagen biosynthesis.

Constituents of Propolis: Chrysin, Caffeic Acid, p-Coumaric Acid, and Ferulic Acid Induce PRODH/POX-Dependent Apoptosis in Human Tongue Squamous Cell Carcinoma Cell (CAL-27)

PubMed Central

Celińska-Janowicz, Katarzyna; Zaręba, Ilona; Lazarek, Urszula; Teul, Joanna; Tomczyk, Michał; Pałka, Jerzy; Miltyk, Wojciech

2018-01-01

Propolis evokes several therapeutic properties, including anticancer activity. These activities are attributed to the action of polyphenols. Previously it has been demonstrated, that one of the most abundant polyphenolic compounds in ethanolic extracts of propolis are chrysin, caffeic acid, p-coumaric acid, and ferulic acid. Although their pro-apoptotic activity on human tongue squamous cell carcinoma cells (CAL-27) was established previously, the detailed mechanism of this process remains unclear. Considering the crucial role of proline metabolism and proline dehydrogenase/proline oxidase (PRODH/POX) in the regulation of cancer cell survival/apoptosis, we studied these processes in polyphenol-treated CAL-27 cells. All studied polyphenols evoked anti-proliferative activity, accompanied by increased PRODH/POX, P53, active caspases-3 and -9 expressions and decreased collagen biosynthesis, prolidase activity and proline concentration in CAL-27 cells. These data suggest that polyphenols of propolis induce PRODH/POX-dependent apoptosis through up-regulation of mitochondrial proline degradation and down-regulation of proline utilization for collagen biosynthesis. PMID:29681859

Development of a PEGylated-Based Platform for Efficient Delivery of Dietary Antioxidants Across the Blood-Brain Barrier.

PubMed

Fernandes, Carlos; Pinto, Miguel; Martins, Cláudia; Gomes, Maria João; Sarmento, Bruno; Oliveira, Paulo J; Remião, Fernando; Borges, Fernanda

2018-05-16

The uptake and transport of dietary antioxidants remains the most important setback for their application in therapy. To overcome the limitations, a PEGylated-based platform was developed to improve the delivery properties of two dietary hydroxycinnamic (HCA) antioxidants-caffeic and ferulic acids. The antioxidant properties of the new polymer-antioxidant conjugates (PEGAntiOxs), prepared by linking poly(ethylene glycol) (PEG) to the cinnamic acids by a one-step Knovenagel condensation reaction, were evaluated. PEGAntiOxs present a higher lipophilicity than the parent compounds (caffeic and ferulic acids) and similar, or higher, antioxidant properties. PEGAntiOxs were not cytotoxic at the tested concentrations in SH-SY5Y, Caco-2, and hCMEC/D3 cells. By contrast, cytotoxic effects in hCMEC/D3 and SH-SY5Y cells were observed, at 50 and 100 μM, for caffeic and ferulic acids. PEGAntiOxs operate as antioxidants against several oxidative stress-cellular inducers in a neuronal cell-based model, and were able to inhibit glycoprotein-P in Caco-2 cells. PEGAntiOxs can cross hCMEC/D3 monolayer cells, a model of the blood-brain barrier (BBB) endothelial membrane. In summary, PEGAntiOxs are valid antioxidant prototypes that can uphold the antioxidant properties of HCAs, reduce their cytotoxicity, and improve their BBB permeability. PEGAntiOxs can be used in the near future as drug candidates to prevent or slow oxidative stress associated with neurodegenerative diseases.

Effect of glutathione during bottle storage of sparkling wine.

PubMed

Webber, Vanessa; Dutra, Sandra Valduga; Spinelli, Fernanda Rodrigues; Carnieli, Gilberto João; Cardozo, Alejandro; Vanderlinde, Regina

2017-02-01

Reduced glutathione (GSH) is an efficient antioxidant on limiting browning, losing varietal aromas and off-flavor formation. Therefore, this study aims to evaluate the effect of GSH addition (10, 20 and 30mgL(-1)) after the disgorging of the sparkling wine during storage. The sparkling wines were analyzed at 1, 6, 12 and 18months of storage according to the color index, concentration of the free SO2, phenolic compounds, catechin, epicatechin, caffeic acid, coumaric acid, acetaldehyde, total and reduced glutathione. The results show that GSH concentration decreased to the level of the control sparkling wine during the first 6months, and the total glutathione gradually declined up to 12months. The GSH reduces browning and acetaldehyde formation for up to 12months. However, the presence of glutathione had low or no influence on the concentration of free SO2, total phenolics, catechin, epicatechin, caffeic and coumaric acids. Copyright © 2016 Elsevier Ltd. All rights reserved.

Antioxidants and Antioxidant Capacity of Biofortified Carrots (Daucus Carota, L.) of Various Colors

USDA-ARS?s Scientific Manuscript database

Antioxidants and antioxidant capacity of seven colored carrots were determined. Five anthocyanins, chlorogenic acid, caffeic acid, and four carotenoids, were quantified by HPLC. Total phenolic content was determined by the Folin-Ciocalteau method. Antioxidant capacities of the hydrophilic and hyd...

Phenylethanoid Glycoside Profiles and Antioxidant Activities of Osmanthus fragrans Lour. Flowers by UPLC/PDA/MS and Simulated Digestion Model.

PubMed

Jiang, Yirong; Mao, Shuqin; Huang, Weisu; Lu, Baiyi; Cai, Zengxuan; Zhou, Fei; Li, Maiquan; Lou, Tiantian; Zhao, Yajing

2016-03-30

Variations of phenylethanoid glycoside profiles and antioxidant activities in Osmanthus fragrans flowers through the digestive tract were evaluated by a simulated digestion model and UPLC/PDA/MS. Major phenylethanoid glycosides and phenolic acids, namely, salidroside, acteoside, isoacteoside, chlorogenic acid, and caffeic acid, were identified in four cultivars of O. fragrans flowers, and the concentration of acteoside was the highest, being up to 71.79 mg/g dry weight. After simulated digestion, total phenylethanoid glycoside contents and antioxidant activities were significantly decreased. Acteoside was identified as decomposing into caffeic acid, whereas salidroside was found to be stable during simulated digestion. According to Pearson's correlation analysis, acteoside contents showed good correlations with antioxidant activities during simulated digestion (R(2) = 0.994, P < 0.01). In conclusion, acteoside was the major contributor to the antioxidant activity of O. fragrans flowers, and salidroside was considered as the major antioxidant compound of O. fragrans flowers in vivo.

Augmentation of ferulic acid-induced vasorelaxation with aging and its structure importance in thoracic aorta of spontaneously hypertensive rats.

PubMed

Fukuda, Toshihiko; Kuroda, Takahiro; Kono, Miki; Hyoguchi, Mai; Tanaka, Mitsuru; Matsui, Toshiro

2015-10-01

Aging deteriorates vascular functions such as vascular reactivity and stiffness. Thus far, various reports suggest that bioactive compounds can improve vascular functions. However, few age-related studies of natural bioactive compounds are available. The present study attempted to evaluate age-related vasorelaxation of bioactive cinnamic acids, caffeic acid, and ferulic acid using aged rat thoracic aorta. Vasorelaxation was evaluated in thoracic aorta from both 8, 18, and 40 weeks old Wistar-Kyoto rats (WKY) and spontaneously hypertensive rats (SHR) respectively. The result indicated that caffeic acid possessed the vasorelaxation regardless of aging in WKY and SHR. Moreover, the vasorelaxation of ferulic acid enhanced with aging in SHR. The vasorelaxation behavior was acted in an endothelium-independent manner. To access structure importance of enhanced vasorelaxation, analogues of ferulic acid were tested. In 40 weeks old SHR, 3,4-dimethoxycinnamic acid and coniferyl alcohol exhibited equivalent vasorelaxation activity with ferulic acid, providing the structural importance of methoxy-modified 3-position on the phenyl ring and 2-propenoic moiety. These results firstly demonstrated that enhanced vasorelaxation of ferulic acid with aging and 3,4-dimethoxycinnamic acid and coniferyl alcohol, along with ferulic acid, might exhibit the therapeutic potential of vasoactive power with aging.

Secondary Metabolites of Hypericum leptophyllum Hochst., an Endemic Turkish Species

PubMed Central

Camas, Necdet; Radusiene, Jolita; Stanius, Zydrunas; Caliskan, Omer; Cirak, Cuneyt

2012-01-01

In the present study, the presence of the phloroglucinol derivative hyperforin, the naphthodianthrones hypericin and pseudohypericin, the phenylpropane chlorogenic acid and the flavonoids rutin, hyperoside, kaempferol, isoquercetine, quercitrine, and quercetine was investigated in Hypericum leptophyllum Hochst., an endemic Turkish species for the first time. The aerial parts representing a total of 30 individuals were collected at full flowering and dissected into floral, leaf, and stem tissues. After being dried at room temperature, the plant materials were assayed for secondary metabolite concentrations by HPLC. Aerial plant parts accumulated chlorogenic acid, hyperoside, isoquercetine, quercitrine, and quercetine, but they did not accumulate hyperforin, hypericin, pseudohypericin, rutin, and kaempferol. Accumulation levels of the detected compounds varied with plant tissues. Such kind of data could be useful for elucidation of the chemotaxonomical significance of the corresponding compounds and phytochemical evaluation of this endemic species. PMID:22649295

Ferulic acid enhances IgE binding to peanut allergens in western blots.

USDA-ARS?s Scientific Manuscript database

Phenolic compounds at high concentrations are known to form insoluble complexes with proteins. We hypothesized that this complex formation could interfere with Western blot and ELISA assays for peanut allergens. To verify this, three simple phenolic compounds (ferulic, caffeic, and chlorogenic acids...

Antihyperglycemic effect of a natural chicoric acid extract of chicory (Cichorium intybus L.): a comparative in vitro study with the effects of caffeic and ferulic acids.

PubMed

Azay-Milhau, Jacqueline; Ferrare, Karine; Leroy, Jeremy; Aubaterre, Jordan; Tournier, Michel; Lajoix, Anne-Dominique; Tousch, Didier

2013-11-25

In Eurasia folk medicine, roots of chicory (Cichorium intybus L.) have been reported to exert antidiabetic benefits. In vitro, a natural chicoric acid extract (NCRAE) from Cichorium intybus root has been shown to increase insulin secretion by pancreatic β-cells and glucose uptake by muscle cells. In vitro experiments were designed to compare the effects of two hydroxycinnamic acids, caffeic and ferulic acids, to those obtained with NCRAE (50 and 100 µg.mL(-1)) on the three major tissues implicated in glycemic regulation (pancreas, muscle and liver). In vivo experiments were performed in Wistar rats submitted to a daily intraperitoneal injection of NCRAE (3, 15 or 30 mg kg(-1)) for 4 days. On the fourth day, an intraperitoneal glucose tolerance test (IPGTT; 1 g kg(-1)) was carried out. Our results show that the three compounds we used are able each to induce an original response. Caffeic acid mainly promotes a decrease in hepatic glycogenolysis. Ferulic acid elicits a clear increase of insulin release and a reduction of hepatic glycogenolysis. However, this compound induces an inhibition of muscle glucose uptake. NCRAE provokes an increase of insulin release and glucose uptake without any effect on hepatic glycogenolysis. We could also show that none of these compounds implicates hepatic glucose 6-phosphatase in contrast to chlorogenic acid, known as an inhibitor of glucose 6-phosphatase and which is able to decrease glucose output from hepatocytes. Our results point out that NCRAE is able to decrease blood glucose without any effect hepatic effect. Our in vivo experiments bring evidence that 4 daily IP administrations of NCRAE improve IP glucose tolerance in a dose-dependent manner and mainly via an insulin sensitizing effect. We conclude that NCRAE presents an antihyperglycemic effect essentially due to a peripheral effect on muscle glucose uptake. © 2013 Elsevier Ireland Ltd. All rights reserved.

Multi-site modulation of flux during monolignol formation in loblolly pine (Pinus taeda)

NASA Technical Reports Server (NTRS)

Anterola, A. M.; van Rensburg, H.; van Heerden, P. S.; Davin, L. B.; Lewis, N. G.

1999-01-01

Loblolly pine (Pinus taeda L.) cell suspension cultures secrete monolignols when placed in 8% sucrose/20 mM KI solution, and these were used to identify phenylpropanoid pathway flux-modulating steps. When cells were provided with increasing amounts of either phenylalanine (Phe) or cinnamic acid, cellular concentrations of immediate downstream products (cinnamic and p-coumaric acids, respectively) increased, whereas caffeic and ferulic acid pool sizes were essentially unaffected. Increasing Phe concentrations resulted in increased amounts of p-coumaryl alcohol relative to coniferyl alcohol. However, exogenously supplied cinnamic, p-coumaric, caffeic, and ferulic acids resulted only in increases in their intercellular concentrations, but not that of downstream cinnamyl aldehydes and monolignols. Supplying p-coumaryl and coniferyl aldehydes up to 40, 000-320,000-fold above the detection limits resulted in rapid, quantitative conversion into the monolignols. Only at nonphysiological concentrations was transient accumulation of intracellular aldehydes observed. These results indicate that cinnamic and p-coumaric acid hydroxylations assume important regulatory positions in phenylpropanoid metabolism, whereas cinnamyl aldehyde reduction does not serve as a control point. Copyright 1999 Academic Press.

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.

Dietary Phenolic Acids Act as Effective Antioxidants in Membrane Models and in Cultured Cells, Exhibiting Proapoptotic Effects in Leukaemia Cells

PubMed Central

Zambonin, Laura; Caliceti, Cristiana; Vieceli Dalla Sega, Francesco; Fiorentini, Diana; Hrelia, Silvana; Landi, Laura; Prata, Cecilia

2012-01-01

Caffeic, syringic, and protocatechuic acids are phenolic acids derived directly from food intake or come from the gut metabolism of polyphenols. In this study, the antioxidant activity of these compounds was at first evaluated in membrane models, where caffeic acid behaved as a very effective chain-breaking antioxidant, whereas syringic and protocatechuic acids were only retardants of lipid peroxidation. However, all three compounds acted as good scavengers of reactive species in cultured cells subjected to exogenous oxidative stress produced by low level of H2O2. Many tumour cells are characterised by increased ROS levels compared with their noncancerous counterparts. Therefore, we investigated whether phenolic acids, at low concentrations, comparable to those present in human plasma, were able to decrease basal reactive species. Results show that phenolic acids reduced ROS in a leukaemia cell line (HEL), whereas no effect was observed in normal cells, such as HUVEC. The compounds exhibited no toxicity to normal cells while they decreased proliferation in leukaemia cells, inducing apoptosis. In the debate on optimal ROS-manipulating strategies in cancer therapy, our work in leukaemia cells supports the antioxidant ROS-depleting approach. PMID:22792417

Caffeic acid, tyrosol and p-coumaric acid are potent inhibitors of 5-S-cysteinyl-dopamine induced neurotoxicity.

PubMed

Vauzour, David; Corona, Giulia; Spencer, Jeremy P E

2010-09-01

Parkinson's disease is characterized by a progressive and selective loss of dopaminergic neurons in the substantia nigra. Recent investigations have shown that conjugates such as the 5-S-cysteinyl-dopamine, possess strong neurotoxicity and may contribute to the underlying progression of the disease pathology. Although the neuroprotective actions of flavonoids are well reported, that of hydroxycinnamates and other phenolic acids is less established. We show that the hydroxycinnamates caffeic acid and p-coumaric acid, the hydroxyphenethyl alcohol, tyrosol, and a Champagne wine extract rich in these components protect neurons against injury induced by 5-S-cysteinyl-dopamine in vitro. The protection induced by these polyphenols was equal to or greater than that observed for the flavonoids, (+)-catechin, (-)-epicatechin and quercetin. For example, p-coumaric acid evoked significantly more protection at 1muM (64.0+/-3.1%) than both (-)-epicatechin (46.0+/-4.1%, p<0.05) and (+)-catechin (13.1+/-3.0%, p<0.001) at the same concentration. These data indicate that hydroxycinnamates, phenolic acids and phenolic alcohol are also capable of inducing neuroprotective effects to a similar extent to that seen with flavonoids. Copyright © 2010. Published by Elsevier Inc.

HPLC-PDA analysis and anti-inflammatory effects of Mori Cortex Radicis.

PubMed

Seo, Chang-Seob; Lim, Hye-Sun; Jeong, Soo-Jin; Ha, Hyekyung; Shin, Hyeun-Kyoo

2013-10-01

Mori Cortex Radicis (MCR, Moraceae) is used traditionally in the treatment ofjaundice, hematemesis, edema, and pollakisuria in Korea. In this study, the antiinflammatory effects of MCR extract were investigated using RAW 264.7 cells. The simultaneous analysis of five components present (neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid, caffeic acid, and p-coumaric acid) in the MCR extract was performed using high-performance liquid chromatography (HPLC) coupled with photodiode array (PDA) detection. We determined the effects of MCR extract and its components on the production of nitric oxide (NO), prostaglandin E2 (PGE2), and mRNA expression of cyclooxygenase-2 (COX-2) in RAW 264.7 cells. MCR extract suppressed the production of NO and PGE2 in RAW 264.7 cells in a dose-dependent manner. None of the five components of the MCR extract had any influence on the production of NO. However, caffeic acid and p-coumaric acid inhibited the production of PGE2 and mRNA expression of COX-2 in RAW 264.7 cells. Our results suggest that MCR extract may offer potential as a therapeutic agent for the treatment of inflammation. The method we have established will help to improve the quality control of MCR extracts.

Equilibrium adsorption of caffeic, chlorogenic and rosmarinic acids on cationic cross-linked starch with quaternary ammonium groups.

PubMed

Simanaviciute, Deimante; Klimaviciute, Rima; Rutkaite, Ramune

2017-02-01

In the present study, the equilibrium adsorption of caffeic acid (CA) and its derivatives, namely, chlorogenic (CGA) and rosmarinic (RA) acids on cationic cross-linked starch (CCS) with degree of substitution of quaternary ammonium groups of 0.42 have been investigated in relation to the structure and acidity of phenolic acids. The Langmuir, Freundlich and Dubinin-Radushkevich adsorption models have been used to describe the equilibrium adsorption of CA, CGA and RA from their initial solutions and solutions having the equimolar amount of NaOH at different temperatures. In the case of adsorption from the initial solutions of acids the values of adsorption parameters were closely related to the dissociation constants of investigated acids. According to the increasing effectiveness of adsorption, phenolic acids could be arranged in the following order: CA

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.

Antinociceptive and antiedematogenic effect of pecan (Carya illinoensis) nut shell extract in mice: a possible beneficial use for a by-product of the nut industry.

PubMed

Trevisan, Gabriela; Rossato, Mateus F; Hoffmeister, Carin; Müller, Liz G; Pase, Camila; Córdova, Marina M; Rosa, Fernanda; Tonello, Raquel; Hausen, Bruna S; Boligon, Aline A; Moresco, Rafael N; Athayde, Margareth L; Burguer, Marilise E; Santos, Adair R; Ferreira, Juliano

2014-01-27

Abstract Background: Interest in pecan (Carya illinoensis) nut shells, a by-product of the nut industry, has increased due to its anti-inflammatory and antioxidant activities. The goal of this study was to evaluate the antinociceptive and antiedematogenic activity and the mechanisms of the pecan shell aqueous extract (AE). Methods: First, we performed fingerprinting of C. illinoensis AE. The antinociceptive and antiedematogenic effects of AE intragastric (i.g.) administration in mice (male Swiss mice 20-30 g) were evaluated using the acetic acid test or after subcutaneous (s.c.) paw injection of diverse transient receptor potential ankyrin 1 (TRPA1) agonists, including hydrogen peroxide (H2O2), allyl isothiocyanate, or cinnamaldehyde. We also observed AE antinociceptive and antiedematogenic effects after carrageenan s.c. paw injection and measured H2O2 production. Moreover, we observed the development of adverse effects after AE i.g. treatment. Results: The high-performance liquid chromatography fingerprinting of AE showed the presence of rutin. AE or rutin i.g. treatment produced antinociception in the acetic acid test and reduced the nociception and edema mediated by H2O2 s.c. hind paw injection or nociception induced by other TRPA1 agonists. Moreover, AE or rutin reduced the hyperalgesia, edema, and H2O2 production induced by carrageenan s.c. paw injection. No motor, gastric, or toxicological alterations were observed after AE administration. Conclusions: Collectively, the present results show that AE and its constituent rutin produced antinociceptive and antiedematogenic action in models of acute and persistent inflammatory nociception and it seems to be related to the inhibition of TRPA1 receptor activation.

Ferulic acid enhances IgE binding to peanut allergens in western blots.

USDA-ARS?s Scientific Manuscript database

Because phenolic compounds can precipitate or complex with proteins, we postulated that interactions of phenolics with IgE antibodies help enhance IgE binding to peanut allergens in Western blots. Three different phenolics, such as, ferulic, caffeic and chlorogenic acids were examined. Each was mixe...

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.

Phenolic compounds increase the transcription of mouse intestinal maltase-glucoamylase and sucrase-isomaltase.

PubMed

Simsek, Meric; Quezada-Calvillo, Roberto; Nichols, Buford L; Hamaker, Bruce R

2017-05-24

Diverse natural phenolic compounds show inhibition activity of intestinal α-glucosidases, which may constitute the molecular basis for their ability to control systemic glycemia. Additionally, phenolics can modify mRNA expression for proteins involved in nutritional, metabolic or immune processes. To explore the possibility that phenolics can regulate the mRNA expression, enzymatic activity, and protein synthesis/processing of intestinal Maltase-Glucoamylase (MGAM) and Sucrase-Isomaltase (SI), small intestinal explants from Balb/c mice were cultured for 24 h in the presence or absence of gallic acid, caffeic acid, and (+)-catechin at 0.1, 0.5, and 1 mM. We measured the levels of MGAM and SI mRNA expression by qRT-PCR, maltase and sucrase activities by a standard colorimetric method and the molecular size distribution of MGAM and SI proteins by western blotting. mRNA expression for MGAM was induced by the three phenolic compounds at 0.1 mM. mRNA expression for SI was induced by caffeic and gallic acids, but not by (+)-catechin. Caffeic acid was the most effective inducer of mRNA expression of these enzymes. Total maltase and sucrase activities were not affected by treatment with phenolics. The proportion of high molecular size forms of MGAM was significantly increased by two of the three phenolic compounds, but little effect was observed on SI proteins. Thus, changes in the protein synthesis/processing, affecting the proportions of the different molecular forms of MGAM, may account for the lack of correlation between mRNA expression and enzymatic activity.

High-performance thin-layer chromatography and three-dimensional image analysis for the determination of rutin in pharmaceutical preparations.

PubMed

Soponar, Florin; Moţ, Augustin C; Sârbu, Costel

2010-01-01

A novel HPTLC method was developed for fast and simple quantitative determination of rutin in pharmaceutical preparations. The proposed method combines the advantages of HPTLC with the comfort and the convenience of digital processing of images. For the separation of rutin, silica gel with attached amino groups was used as the stationary phase and ethyl acetate-formic acid-methanol-water (10 + 0.9 + 1.1 + 1.7, v/v/v/v) as the mobile phase. The chromatographic plate was sprayed with 2-aminoethyldiphenyl borate solution for visual detection of the spots. For the construction of a three-dimensional chromatogram, Melanie 7.0 software was used together with an HP flatbed scanner that allowed capture of the images on chromatographic plates. The calibration curve was linear within the range of 0.95-4.78 microg/spot with an r value of 0.9984. The RSD for six replicates at three concentration levels was less than 3%, while the recovery was between 97.28 and 103.27%. The proposed method was found to be simple, precise, sensitive, and accurate and has been applied for the determination of rutin in two commercial drugs. The results were compared with the results of other techniques that generate bidimensional chromatograms and validated by UV-Vis spectrophotometry.

Thermally Induced Encapsulation of Food Nutrients into Phytoferritin through the Flexible Channels without Additives.

PubMed

Yang, Rui; Tian, Jing; Liu, Yuqian; Yang, Zhiying; Wu, Dandan; Zhou, Zhongkai

2017-11-22

The cavity of phytoferritin provides a nanospace to encapsulate and deliver food nutrient molecules. However, tranditional methods to prepare the ferritin-nutrient complexes must undergo acid/alkaline conditions or apply additives. In this work, we provide a novel guideline that thermal treatment at 60 °C can expand ferritin channels by uncoiling the surrounding α-helix. Upon reduction of the temperature to 20 °C, food nutrient rutin can be encapsulated in apo-soybean seed ferritin (apoSSF) at pH 7.0 through channels without disassembly of the protein cage and with no addition of additives. Results indicated that one apoSSF could encapsulate about 10.5 molecules of rutin, with an encapsulation ratio of 8.08% (w/w). In addition, the resulting rutin-loaded SSF complexes were monodispersed in a size of 12 nm in aqueous solution. This work provides a novel pathway for the encapsulation of food nutrient molecules into the nanocavity of ferritin under a neutral pH condition induced by thermal treatment.

Pseudomonas putida F1 uses energy taxis to sense hydroxycinnamic acids

PubMed Central

Hughes, Jonathan G.; Zhang, Xiangsheng; Parales, Juanito V.; Ditty, Jayna L.; Parales, Rebecca E.

2017-01-01

Soil bacteria such as pseudomonads are widely studied due to their diverse metabolic capabilities, particularly the ability to degrade both naturally occurring and xenobiotic aromatic compounds. Chemotaxis, the directed movement of cells in response to chemical gradients, is common in motile soil bacteria and the wide range of chemicals detected often mirrors the metabolic diversity observed. Pseudomonas putida F1 is a soil isolate capable of chemotaxis toward, and degradation of, numerous aromatic compounds. We showed that P. putida F1 is capable of degrading members of a class of naturally occurring aromatic compounds known as hydroxycinnamic acids, which are components of lignin and are ubiquitous in the soil environment. We also demonstrated the ability of P. putida F1 to sense three hydroxycinnamic acids: p-coumaric, caffeic and ferulic acids. The chemotaxis response to hydroxycinnamic acids was induced during growth in the presence of hydroxycinnamic acids and was negatively regulated by HcaR, the repressor of the hydroxycinnamic acid catabolic genes. Chemotaxis to the three hydroxycinnamic acids was dependent on catabolism, as a mutant lacking the gene encoding feruloyl-CoA synthetase (Fcs), which catalyzes the first step in hydroxycinnamic acid degradation, was unable to respond chemotactically toward p-coumaric, caffeic, or ferulic acids. We tested whether an energy taxis mutant could detect hydroxycinnamic acids and determined that hydroxycinnamic acid sensing is mediated by the energy taxis receptor Aer2. PMID:28954643

Enzymatic modification of chitosan by cinnamic acids: Antibacterial activity against Ralstonia solanacearum.

PubMed

Yang, Caifeng; Zhou, Yu; Zheng, Yu; Li, Changlong; Sheng, Sheng; Wang, Jun; Wu, Fuan

2016-06-01

This study aimed to identify chitosan polymers that have antibacterial activity against the bacterial wilt pathogen. The chitosan polymers were enzymatically synthesized using chitosan and five cinnamic acids (CADs): caffeic acid (CA), ferulic acid (FA), cinnamic acid (CIA), p-coumaric acid (COA) and chlorogenic acid (CHA), using laccase from Pleurotus ostreatus as a catalyst. The reaction was performed in a phosphate buffered solution under heterogenous reaction conditions. The chitosan derivatives (CTS-g-CADs) were characterized by FT-IR, XRD, TGA and SEM. FT-IR demonstrated that the reaction products bound covalently to the free amino groups or hydroxyl groups of chitosan via band of amide I or ester band. XRD showed a reduced packing density for grafted chitosan comparing to original chitosan. TGA demonstrated that CTS-g-CADs have a higher thermostability than chitosan. Additionally, chitosan and its derivatives showed similar antibacterial activity. However, the IC50 value of the chitosan-caffeic acid derivative (CTS-g-CA) against the mulberry bacterial wilt pathogen RS-5 was 0.23mg/mL, which was two-fifths of the IC50 value of chitosan. Therefore, the enzymatically synthesized chitosan polymers can be used to control plant diseases in biotechnological domains. Copyright © 2016 Elsevier B.V. All rights reserved.

trans-Cinnamic and Chlorogenic Acids Affect the Secondary Metabolic Profiles and Ergosterol Biosynthesis by Fusarium culmorum and F. graminearum Sensu Stricto

PubMed Central

Kulik, Tomasz; Stuper-Szablewska, Kinga; Bilska, Katarzyna; Buśko, Maciej; Ostrowska-Kołodziejczak, Anna; Załuski, Dariusz; Perkowski, Juliusz

2017-01-01

Plant-derived compounds limiting mycotoxin contamination are currently of major interest in food and feed production. However, their potential application requires an evaluation of their effects on fungal secondary metabolism and membrane effects. In this study, different strains of Fusarium culmorum and F. graminearum sensu stricto were exposed to trans-cinnamic and chlorogenic acids on solid YES media. Fusaria produced phenolic acids, whose accumulation was lowered by exogenous phenolic compounds. In addition, fungi reduced exogenous phenolic acids, leading either to their conversion or degradation. trans-Cinnamic acid was converted to caffeic and ferulic acids, while chlorogenic acid was degraded to caffeic acid. The latter underwent further degradation to protocatechuic acid. Fungal-derived trans-cinnamic acid, as the first intermediate of the shikimate pathway, increased after chlorogenic acid treatment, presumably due to the further inhibition of the conversion of trans-cinnamic acid. Exogenous trans-cinnamic and chlorogenic acid displayed the inhibition of mycotoxin production by Fusaria, which appeared to be largely dependent on the phenolic compound and its concentration and the assayed strain. Exogenous phenolic acids showed different effects on ergosterol biosynthesis by fungi. It was found that the production of this membrane sterol was stimulated by trans-cinnamic acid, while chlorogenic acid negatively impacted ergosterol biosynthesis, suggesting that phenolic acids with stronger antifungal activities may upregulate ergosterol biosynthesis by Fusaria. This paper reports on the production of phenolic acids by Fusaria for the first time. PMID:28640190

trans-Cinnamic and Chlorogenic Acids Affect the Secondary Metabolic Profiles and Ergosterol Biosynthesis by Fusarium culmorum and F. graminearum Sensu Stricto.

PubMed

Kulik, Tomasz; Stuper-Szablewska, Kinga; Bilska, Katarzyna; Buśko, Maciej; Ostrowska-Kołodziejczak, Anna; Załuski, Dariusz; Perkowski, Juliusz

2017-06-22

Plant-derived compounds limiting mycotoxin contamination are currently of major interest in food and feed production. However, their potential application requires an evaluation of their effects on fungal secondary metabolism and membrane effects. In this study, different strains of Fusarium culmorum and F. graminearum sensu stricto were exposed to trans -cinnamic and chlorogenic acids on solid YES media. Fusaria produced phenolic acids, whose accumulation was lowered by exogenous phenolic compounds. In addition, fungi reduced exogenous phenolic acids, leading either to their conversion or degradation. trans -Cinnamic acid was converted to caffeic and ferulic acids, while chlorogenic acid was degraded to caffeic acid. The latter underwent further degradation to protocatechuic acid. Fungal-derived trans -cinnamic acid, as the first intermediate of the shikimate pathway, increased after chlorogenic acid treatment, presumably due to the further inhibition of the conversion of trans -cinnamic acid. Exogenous trans -cinnamic and chlorogenic acid displayed the inhibition of mycotoxin production by Fusaria, which appeared to be largely dependent on the phenolic compound and its concentration and the assayed strain. Exogenous phenolic acids showed different effects on ergosterol biosynthesis by fungi. It was found that the production of this membrane sterol was stimulated by trans -cinnamic acid, while chlorogenic acid negatively impacted ergosterol biosynthesis, suggesting that phenolic acids with stronger antifungal activities may upregulate ergosterol biosynthesis by Fusaria. This paper reports on the production of phenolic acids by Fusaria for the first time.

Researching on new species of "Mate": Ilex brevicuspis: phytochemical and pharmacology study.

PubMed

Filip, R; Ferraro, G E

2003-01-01

Ilex paraguariensis St. Hilaire (Aquifoliaceae) ("Mate" or "Yerba mate") is one of the most commercialized plants of South America which grows naturally in NE Argentina, Uruguay, SE Brazil and E Paraguay, where it is also cultivated. It is used to prepare a tea-like beverage (infusions or decoctions) appreciated for its peculiar flavor, stimulation and nutritional properties. Ilex brevicuspis Reisseck grows in the same habitat and is widely used as a substitute or adulterant of Ilex paraguariensis. In a previous work, methylxanthines (caffeine, theobromine and theophylline) were not detected in it by HPLC. This study was undertaken in order to isolate, identify and quantify the polyphenolic compounds (caffeoyl derivatives and flavonoids) and to investigate some of the pharmacological activities of I. brevicuspis, related with the traditional use of the "Mate" (choleretic, intestinal propulsion and antioxidant activities). Acute toxicity was also investigated. Decoctions, like extracts, were prepared in order to compare the results with preparations commonly used by the local people. For the phytochemical analysis, the extracts were analyzed by HPLC with a diode array detector. Choleretic and intestinal propulsion activities were assayed in rats. Sodium dehydrocholate (DHC) was used as a choleretic reference standard. Antioxidant activity was tested in liposomes that were oxidized by the free radical generator 2,2'-azobis [amidinopropane] chloride (AAPH). For the first time in I. brevicuspis the following compounds were isolated and quantified: A) caffeoyl derivative compounds (chlorogenic acid; caffeic acid; 3,4-dicaffeoylquinic acid; 3,5-dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid. B) flavonoids (rutin, quercetin and kaempferol). Biological activity assays demonstrated that I. brevicuspis extracts produced a significant increase of bile flow (BF) in rats in the first 30 min period and in the percentage of BF increase accumulated at 120 min. It also produced an increase in the intestinal propulsion activity. Moreover, this species showed a high antioxidant activity. The acute toxicity test showed that Ilex brevicuspis did not produce any sign of toxicity at the analyzed doses. An Argentinean Ilex specie ( I. brevicuspis) has choleretic, intestinal propulsion, antioxidant activities and these results may lead to the potential development of a new "Yerba Mate" and/or phytopharmaceutical products, without central nervous system (CNS) stimulant activity.

The amylase inhibitor montbretin A reveals a new glycosidase inhibition motif.

PubMed

Williams, Leslie K; Zhang, Xiaohua; Caner, Sami; Tysoe, Christina; Nguyen, Nham T; Wicki, Jacqueline; Williams, David E; Coleman, John; McNeill, John H; Yuen, Violet; Andersen, Raymond J; Withers, Stephen G; Brayer, Gary D

2015-09-01

The complex plant flavonol glycoside montbretin A is a potent (Ki = 8 nM) and specific inhibitor of human pancreatic α-amylase with potential as a therapeutic for diabetes and obesity. Controlled degradation studies on montbretin A, coupled with inhibition analyses, identified an essential high-affinity core structure comprising the myricetin and caffeic acid moieties linked via a disaccharide. X-ray structural analyses of the montbretin A-human α-amylase complex confirmed the importance of this core structure and revealed a novel mode of glycosidase inhibition wherein internal π-stacking interactions between the myricetin and caffeic acid organize their ring hydroxyls for optimal hydrogen bonding to the α-amylase catalytic residues D197 and E233. This novel inhibitory motif can be reproduced in a greatly simplified analog, offering potential for new strategies for glycosidase inhibition and therapeutic development.

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

Cells Deficient in the Fanconi Anemia Protein FANCD2 are Hypersensitive to the Cytotoxicity and DNA Damage Induced by Coffee and Caffeic Acid

PubMed Central

Burgos-Morón, Estefanía; Calderón-Montaño, José Manuel; Orta, Manuel Luis; Guillén-Mancina, Emilio; Mateos, Santiago; López-Lázaro, Miguel

2016-01-01

Epidemiological studies have found a positive association between coffee consumption and a lower risk of cardiovascular disorders, some cancers, diabetes, Parkinson and Alzheimer disease. Coffee consumption, however, has also been linked to an increased risk of developing some types of cancer, including bladder cancer in adults and leukemia in children of mothers who drink coffee during pregnancy. Since cancer is driven by the accumulation of DNA alterations, the ability of the coffee constituent caffeic acid to induce DNA damage in cells may play a role in the carcinogenic potential of this beverage. This carcinogenic potential may be exacerbated in cells with DNA repair defects. People with the genetic disease Fanconi Anemia have DNA repair deficiencies and are predisposed to several cancers, particularly acute myeloid leukemia. Defects in the DNA repair protein Fanconi Anemia D2 (FANCD2) also play an important role in the development of a variety of cancers (e.g., bladder cancer) in people without this genetic disease. This communication shows that cells deficient in FANCD2 are hypersensitive to the cytotoxicity (clonogenic assay) and DNA damage (γ-H2AX and 53BP1 focus assay) induced by caffeic acid and by a commercial lyophilized coffee extract. These data suggest that people with Fanconi Anemia, or healthy people who develop sporadic mutations in FANCD2, may be hypersensitive to the carcinogenic activity of coffee. PMID:27399778

Cells Deficient in the Fanconi Anemia Protein FANCD2 are Hypersensitive to the Cytotoxicity and DNA Damage Induced by Coffee and Caffeic Acid.

PubMed

Burgos-Morón, Estefanía; Calderón-Montaño, José Manuel; Orta, Manuel Luis; Guillén-Mancina, Emilio; Mateos, Santiago; López-Lázaro, Miguel

2016-07-08

Epidemiological studies have found a positive association between coffee consumption and a lower risk of cardiovascular disorders, some cancers, diabetes, Parkinson and Alzheimer disease. Coffee consumption, however, has also been linked to an increased risk of developing some types of cancer, including bladder cancer in adults and leukemia in children of mothers who drink coffee during pregnancy. Since cancer is driven by the accumulation of DNA alterations, the ability of the coffee constituent caffeic acid to induce DNA damage in cells may play a role in the carcinogenic potential of this beverage. This carcinogenic potential may be exacerbated in cells with DNA repair defects. People with the genetic disease Fanconi Anemia have DNA repair deficiencies and are predisposed to several cancers, particularly acute myeloid leukemia. Defects in the DNA repair protein Fanconi Anemia D2 (FANCD2) also play an important role in the development of a variety of cancers (e.g., bladder cancer) in people without this genetic disease. This communication shows that cells deficient in FANCD2 are hypersensitive to the cytotoxicity (clonogenic assay) and DNA damage (γ-H2AX and 53BP1 focus assay) induced by caffeic acid and by a commercial lyophilized coffee extract. These data suggest that people with Fanconi Anemia, or healthy people who develop sporadic mutations in FANCD2, may be hypersensitive to the carcinogenic activity of coffee.

Suppression of skin inflammation in keratinocytes and acute/chronic disease models by caffeic acid phenethyl ester.

PubMed

Lim, Kyung-Min; Bae, SeungJin; Koo, Jung Eun; Kim, Eun-Sun; Bae, Ok-Nam; Lee, Joo Young

2015-04-01

Skin inflammation plays a central role in the pathophysiology and symptoms of diverse chronic skin diseases including atopic dermatitis (AD). In this study, we examined if caffeic acid phenethyl ester (CAPE), a skin-permeable bioactive compound from propolis, was protective against skin inflammation using in vitro cell system and in vivo animal disease models. CAPE suppressed TNF-α-induced NF-κB activation and expression of inflammatory cytokines in human keratinocytes (HaCaT). The potency and efficacy of CAPE were superior to those of a non-phenethyl derivative, caffeic acid. Consistently, topical treatment of CAPE (0.5 %) attenuated 12-O-tetradecanoylphorbol-13-acetate(TPA)-induced skin inflammation on mouse ear as CAPE reduced ear swelling and histologic inflammation scores. CAPE suppressed increased expression of pro-inflammatory molecules such as TNF-α, cyclooxygenase-2 and inducible NO synthase in TPA-stimulated skin. TPA-induced phosphorylation of IκB and ERK was blocked by CAPE suggesting that protective effects of CAPE on skin inflammation is attributed to inhibition of NF-κB activation. Most importantly, in an oxazolone-induced chronic dermatitis model, topical application of CAPE (0.5 and 1 %) was effective in alleviating AD-like symptoms such as increases of trans-epidermal water loss, skin thickening and serum IgE as well as histologic inflammation assessment. Collectively, our results propose CAPE as a promising candidate for a novel topical drug for skin inflammatory diseases.

Antioxidant Potential and Antibacterial Efficiency of Caffeic Acid-Functionalized ZnO Nanoparticles

PubMed Central

Choi, Kyong-Hoon; Nam, Ki Chang; Lee, Sang-Yoon; Cho, Guangsup; Jung, Jin-Seung; Kim, Ho-Joong; Park, Bong Joo

2017-01-01

We report a novel zinc oxide (ZnO) nanoparticle with antioxidant properties, prepared by immobilizing the antioxidant 3-(3,4-dihydroxyphenyl)-2-propenoic acid (caffeic acid, CA) on the surfaces of micro-dielectric barrier discharge (DBD) plasma-treated ZnO nanoparticles. The microstructure and physical properties of ZnO@CA nanoparticles were characterized by field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), infrared spectroscopy, and steady state spectroscopic methods. The antioxidant activity of ZnO@CA nanoparticles was evaluated using an ABTS (3-ethyl-benzothiazoline-6-sulfonic acid) radical cation decolorization assay. ZnO@CA nanoparticles exhibited robust antioxidant activity. Moreover, ZnO@CA nanoparticles showed strong antibacterial activity against Gram-positive bacteria (Staphylococcus aureus) including resistant bacteria such as methicillin-resistant S. aureus and against Gram-negative bacteria (Escherichia coli). Although Gram-negative bacteria appeared to be more resistant to ZnO@CA nanoparticles than Gram-positive bacteria, the antibacterial activity of ZnO@CA nanoparticles was dependent on particle concentration. The antioxidant and antibacterial activity of ZnO@CA may be useful for various biomedical and nanoindustrial applications. PMID:28621707

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.

An enhanced cerium(IV)-rhodamine 6G chemiluminescence system using guest-host interactions in a lab-on-a-chip platform for estimating the total phenolic content in food samples.

PubMed

Al Haddabi, Buthaina; Al Lawati, Haider A J; Suliman, FakhrEldin O

2016-04-01

Two chemiluminescence-microfluidic (CL-MF) systems, e.g., Ce(IV)-rhodamine B (RB) and Ce(IV)-rhodamine 6G (R6G), for the determination of the total phenolic content in teas and some sweeteners were evaluated. The results indicated that the Ce(IV)-R6G system was more sensitive in comparison to the Ce(IV)-RB CL system. Therefore, a simple (CL-MF) method based on the CL of Ce(IV)-R6G was developed, and the sensitivity, selectivity and stability of this system were evaluated. Selected phenolic compounds (PCs), such as quercetin (QRC), catechin (CAT), rutin (RUT), gallic acid (GA), caffeic acid (CA) and syringic acid (SA), produced analytically useful chemiluminescence signals with low detection limits ranging from 0.35 nmol L(-1) for QRC to 11.31 nmol L(-1) for SA. The mixing sequence and the chip design were crucial, as the sensitivity and reproducibility could be substantially affected by these two factors. In addition, the anionic surfactant (i.e., sodium dodecyl sulfate (SDS)) can significantly enhance the CL signal intensity by as much as 300% for the QRC solution. Spectroscopic studies indicated that the enhancement was due to a strong guest-host interaction between the cationic R6G molecules and the anionic amphiphilic environment. Other parameters that could affect the CL intensities of the PCs were carefully optimized. Finally, the method was successfully applied to tea and sweetener samples. Six different tea samples exhibited total phenolic/antioxidant levels from 7.32 to 13.5 g per 100g of sample with respect to GA. Four different sweetener samples were also analyzed and exhibited total phenolic/antioxidant levels from 500.9 to 3422.9 mg kg(-1) with respect to GA. The method was selective, rapid and sensitive when used to estimate the total phenolic/antioxidant level, and the results were in good agreement with those reported for honey and tea samples. Copyright © 2015 Elsevier B.V. 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

Rapid assessment of bioactive phenolics and methylxanthines in spent coffee grounds by FT-NIR spectroscopy.

PubMed

Magalhães, Luís M; Machado, Sandia; Segundo, Marcela A; Lopes, João A; Páscoa, Ricardo N M J

2016-01-15

Spent coffee grounds (SCGs) are a great source of bioactive compounds with interest to pharmaceutical and cosmetic industries. Phenolics and methylxanthines are the main health related compounds present in SCG samples. Content estimation of these compounds in SCGs is of upmost importance in what concerns their profitable use by waste recovery industries. In the present work, near-infrared spectroscopy (NIRS) was proposed as a rapid and non-destructive technique to assess the content of three main phenolics (caffeic acid, (+)-catechin and chlorogenic acid) and three methylxanthines (caffeine, theobromine and theophylline) in SCG samples obtained from different coffee brands and diverse coffee machines. The content of these compounds was determined for 61 SCG samples by HPLC coupled with diode-array detection. Partial least squares (PLS) regression based models were calibrated to correlate diffuse reflectance NIR spectra against the reference data for the six parameters obtained by HPLC. Spectral wavelength selection and number of latent variables were optimized by minimizing the cross-validation error. PLS models showed good linearity with a coefficient of determination for the prediction set (Rp(2)) of 0.95, 0.92, 0.88, 071 and 0.84 for caffeine, caffeic acid, (+)-catechin, chlorogenic acid and theophylline, respectively. The range error ratio (RER) was higher for caffeine (17.8) when compared to other compounds (12.0, 10.1, 7.6 and 9.2, respectively for caffeic acid, (+)-catechin, chlorogenic acid and theophylline). Moreover, the content of caffeine could be used to predict the antioxidant properties of SCG samples (R=0.808, n=61), despite not presenting this property itself. The results obtained confirmed that NIRS is a suitable technique to screen SCG samples unveiling those with high content of bioactive compounds, which are interesting for subsequent extraction procedures. Copyright © 2015 Elsevier B.V. All rights reserved.

Study of the interaction of flavonoids with 3-mercaptopropionic acid modified CdTe quantum dots mediated by cetyltrimethyl ammonium bromide in aqueous medium

NASA Astrophysics Data System (ADS)

Aucelio, Ricardo Q.; Carvalho, Juliana M.; Real, Juliana T.; Maqueira-Espinosa, Luis; Pérez-Gramatges, Aurora; da Silva, Andrea R.

2017-02-01

Flavonoids are polyphenols that help the maintenance of health, aiding the prevention of diseases. In this work, CdTe QDs coated with 3-mercaptopropionic acid (3MPA), with an average size of 2.7 nm, were used as photoluminescence probe for flavonoids in different conditions. The interaction between 14 flavonoids and QDs was evaluated in aqueous dispersions in the absence and in the presence of cetyltrimethylammonium bromide (CTAB). To establish a relationship between photoluminescence quenching and the concentration of flavonoids, the Stern-Volmer model was used. In the absence of CTAB, the linear ranges for quercetin, morin and rutin were from 5.0 × 10- 6 mol L- 1 to 6.0 × 10- 5 mol L- 1 and from 1.0 × 10- 5 mol L- 1 to 6.0 × 10- 4 mol L- 1 for kaempferol. The sensibility of the Stern-Volmer curves (Ks) indicated that quercetin interacts more strongly with the probe: Ks quercetin > Ks kaempferol > Ks rutin > Ks morin. The conjugation extension in the 3 rings, and the acidic hydroxyl groups (positions 3ʹand 4ʹ) in the B-ring enhanced the interaction with 3MPA-CdTe QDs. The other flavonoids do not interact with the probe at 10- 5 mol L- 1 level. In CTAB organized dispersions, Ks 3-hydroxyflavone > Ks 7-hydroxyflavone > Ks flavona > Ks rutin in the range from 1.0 × 10- 6 mol L- 1 to 1.2 × 10- 5 mol L- 1 for flavones and of 1.0 × 10- 6 mol L- 1 to 1.0 × 10- 5 mol L- 1 for rutin. Dynamic light scattering, conductometric measurements and microenvironment polarity studies were employed to elucidate the QDs-flavonoids interaction in systems containing CTAB. The quenching can be attributed to the preferential solubility of hydrophobic flavonoid in the palisade layer of the CTAB aggregates adsorbed on the surface of the 3MPA CdTe QDs.

Specific recognition of polyphenols by molecularly imprinted polymers based on a ternary deep eutectic solvent.

PubMed

Fu, Najing; Li, Liteng; Liu, Xiao; Fu, Nian; Zhang, Chenchen; Hu, Liandong; Li, Donghao; Tang, Baokun; Zhu, Tao

2017-12-29

Typically, a target compound is selected as a template for a molecularly imprinted polymer (MIP); however, some target compounds are not suitable as templates because of their poor solubility. Using the tailoring properties of a deep eutectic solvent (DES), the insoluble target compound caffeic acid was transformed into a ternary choline chloride-caffeic acid-ethylene glycol (ChCl-CA-EG) DES, which was then employed as a template to prepare MIPs. The ternary DES-based MIPs were characterized by Fourier transform infrared spectroscopy, elemental analysis, scanning electron microscopy, and atomic force microscopy. The effects of time, temperature, ionic strength, and pH on the recognition processes for four polyphenols (caffeic acid, protocatechuic acid, catechin, and epicatechin) by 13 ChCl-CA-EG ternary DES-based MIPs was investigated using high-performance liquid chromatography. The recognition specificity of the MIPs for CA was significantly better than that for the other polyphenols, and the MIPs exhibited obvious characteristics of chromatographic packing materials. In addition, the recognition processes mainly followed a second-order kinetics model and the Freundlich isotherm model, which together indicated that the MIPs mainly recognized the polyphenols by chemical interactions including ion exchange, electron exchange, and new bond formation. Furthermore, the specific recognition ability of the MIPs for polyphenols, which was better than those of C 18 , C 8 , or non-molecularly imprinted polymer adsorbents, was successfully applied to the recognition of polyphenols in a Radix asteris sample. The transformation of an insoluble target compound in a polymeric DES for MIP preparation and recognition is a novel and feasible strategy suitable for use in further MIP research developments. Copyright © 2017 Elsevier B.V. All rights reserved.

Phenylpropanoid composition in fig (Ficus carica L.) leaves.

PubMed

Takahashi, Toru; Okiura, Aya; Kohno, Masahiro

2017-10-01

The leaves of fig (Ficus carica L.) have been used for traditional and Chinese medicine. We determined the composition of phenylpropanoids (polyphenols and furanocoumarins) as a functional agent in the leaves of 37 cultivars of fig. The most abundant polyphenol was caffeoylmalic acid (12.0-26.6 mg/g dry weight), followed by rutin (4.7-14.6 mg/g dry weight) and isoschaftoside (2.5-6.4 mg/g dry weight). Psoralen (3.8-23.0 mg/g dry weight) was dominant in the furanocoumarins. In molar amounts, psoralic acid glucoside (PAG), a precursor of psoralen, was equivalent to psoralen. Furanocoumarins and PAG were not detected in the leaves of only one cultivar, Grise de Tarascon. Fig leaves are potentially an excellent source of polyphenols such as caffeoylmalic acid and rutin. From the result of cluster analysis, some cultivars that contained large amount of polyphenols, and a small amount (e.g., Grise de Saint Jean) or no (Grise de Tarascon) furanocoumarins, were found. These cultivars are considered suitable for functional foods or medicinal products.

Reduction of rutin loss in buckwheat noodles and their physicochemical characterization

USDA-ARS?s Scientific Manuscript database

Rutin in buckwheat flour is converted into quercetin by rutin-degrading enzymes when water is added. Thus, buckwheat was subjected to hydrothermal treatments for minimizing the rutin loss in buckwheat-based foods by water addition. When native buckwheat flour was mixed with water, the rutin conten...

Bioavailability of chlorogenic acids following acute ingestion of coffee by humans with an ileostomy.

PubMed

Stalmach, Angélique; Steiling, Heike; Williamson, Gary; Crozier, Alan

2010-09-01

The intestinal absorption and metabolism of 385 micromol chlorogenic acids following a single intake of 200 mL of instant coffee by human volunteers with an ileostomy was investigated. HPLC-MS(3) analysis of 0-24h post-ingestion ileal effluent revealed the presence of 274+/-28 micromol of chlorogenic acids and their metabolites accounting for 71+/-7% of intake. Of the compounds recovered, 78% comprised parent compounds initially present in the coffee, and 22% were metabolites including free and sulfated caffeic and ferulic acids. Over a 24h period after ingestion of the coffee, excretion of chlorogenic acid metabolites in urine accounted for 8+/-1% of intake, the main compounds being ferulic acid-4-O-sulfate, caffeic acid-3-O-sulfate, isoferulic acid-3-O-glucuronide and dihydrocaffeic acid-3-O-sulfate. In contrast, after drinking a similar coffee, urinary excretion by humans with an intact colon corresponded to 29+/-4% of chlorogenic acid intake. This difference was due to the excretion of higher levels of dihydroferulic acid and feruloylglycine together with sulfate and glucuronide conjugates of dihydrocaffeic and dihydroferulic acids. This highlights the importance of colonic metabolism. Comparison of the data obtained in the current study with that of Stalmach et al. facilitated elucidation of the pathways involved in post-ingestion metabolism of chlorogenic acids and also helped distinguish between compounds absorbed in the small and the large intestine. Copyright © 2010 Elsevier Inc. All rights reserved.

New steroidal saponin and antiulcer activity from Solanum paniculatum L.

PubMed

Vieira Júnior, Gerardo Magela; da Rocha, Cláudia Quintino; de Souza Rodrigues, Tamires; Hiruma-Lima, Clélia Akiko; Vilegas, Wagner

2015-11-01

Solanum paniculatum L. (Solanaceae) is a plant species widespread throughout tropical America, especially in the Brazilian Savanna region. It is used in Brazil for culinary purposes and in folk medicine to treat liver and gastric dysfunctions, as well as hangovers. Fractionation of the ethanolic extracts (70%) from aerial parts (leaves and twigs) of S. paniculatum led to the isolation of the two new saponins (22R, 23S, 25R)-3β, 6α, 23-trihydroxy-5α-spirostane 6-O-β-D-xylopyranosyl-(1" → 3"')-O-[β-D-quinovopyranosyl(1″' → 2')]-O-[α-L-rhamnopyranosyl(1" → 3')]-O-β-D-quinovopyranoside (1) and diosgenin 3-O-β-D-glucopyranosyl(1" → 6')-O-β-D-glucopyranoside (2) together with four know compounds: caffeic acid (3), diosgenin β-D-glucopyranoside (4), rutin (5), and quercetin 3-O-α-L-rhamnopyranosyl (1"' → 6 ″)-O-β-D-galactopyranoside (6). The structures of these compounds were elucidated by extensive use of 1D and 2D NMR experiments along with HRESIMS analyses. Different doses (31.25-500 mg/kg) of ethanolic extract of leaves from S. paniculatum were evaluated against gastric ulcer induced by ethanol in rats. The lower dose of extract able to promote antiulcer effect was 125 mg/kg. The treatment with S. paniculatum by oral route was able to decrease gastric lesion area and also reduced levels of myeloperoxidase (MPO) in the gastric mucosa. Our results reveal for the first time, steroidal saponins from S. paniculatum and the antiulcer effect of this species at this lower dose. Copyright © 2014 Elsevier Ltd. All rights reserved.

Phenolic acids in the flowers of Althaea rosea var. nigra.

PubMed

Dudek, Marlena; Matławska, Irena; Szkudlarek, Maurycy

2006-01-01

Distribution of phenolic acids in the flowers of Althaea rosea var. nigra has been studied by 2D-TLC and HPLC methods. The phenolic acids occurring in these fractions have been identified as ferulic, vanillic, syringic, p-coumaric, p-hydroxybenzoic, p-hydroxyphenylacetic and caffeic acids. By means of the HPLC methods the contents of major phenolic acids were estimated. From among the phenolic acids analyzed the syringic, p-hydroxybenzoic and p-coumaric acids are dominant. Total content of phenolic acids was determined by the Arnov's method.

Accumulation of Phenolic Compounds and Expression Profiles of Phenolic Acid Biosynthesis-Related Genes in Developing Grains of White, Purple, and Red Wheat.

PubMed

Ma, Dongyun; Li, Yaoguang; Zhang, Jian; Wang, Chenyang; Qin, Haixia; Ding, Huina; Xie, Yingxin; Guo, Tiancai

2016-01-01

Polyphenols in whole grain wheat have potential health benefits, but little is known about the expression patterns of phenolic acid biosynthesis genes and the accumulation of phenolic acid compounds in different-colored wheat grains. We found that purple wheat varieties had the highest total phenolic content (TPC) and antioxidant activity. Among phenolic acid compounds, bound ferulic acid, vanillic, and caffeic acid levels were significantly higher in purple wheat than in white and red wheat, while total soluble phenolic acid, soluble ferulic acid, and vanillic acid levels were significantly higher in purple and red wheat than in white wheat. Ferulic acid and syringic acid levels peaked at 14 days after anthesis (DAA), whereas p-coumaric acid and caffeic acid levels peaked at 7 DAA, and vanillic acid levels gradually increased during grain filling and peaked near ripeness (35 DAA). Nine phenolic acid biosynthesis pathway genes (TaPAL1, TaPAL2, TaC3H1, TaC3H2, TaC4H, Ta4CL1, Ta4CL2, TaCOMT1, and TaCOMT2) exhibited three distinct expression patterns during grain filling, which may be related to the different phenolic acids levels. White wheat had higher phenolic acid contents and relatively high gene expression at the early stage, while purple wheat had the highest phenolic acid contents and gene expression levels at later stages. These results suggest that the expression of phenolic acid biosynthesis genes may be closely related to phenolic acids accumulation.

Accumulation of Phenolic Compounds and Expression Profiles of Phenolic Acid Biosynthesis-Related Genes in Developing Grains of White, Purple, and Red Wheat

PubMed Central

Ma, Dongyun; Li, Yaoguang; Zhang, Jian; Wang, Chenyang; Qin, Haixia; Ding, Huina; Xie, Yingxin; Guo, Tiancai

2016-01-01

Polyphenols in whole grain wheat have potential health benefits, but little is known about the expression patterns of phenolic acid biosynthesis genes and the accumulation of phenolic acid compounds in different-colored wheat grains. We found that purple wheat varieties had the highest total phenolic content (TPC) and antioxidant activity. Among phenolic acid compounds, bound ferulic acid, vanillic, and caffeic acid levels were significantly higher in purple wheat than in white and red wheat, while total soluble phenolic acid, soluble ferulic acid, and vanillic acid levels were significantly higher in purple and red wheat than in white wheat. Ferulic acid and syringic acid levels peaked at 14 days after anthesis (DAA), whereas p-coumaric acid and caffeic acid levels peaked at 7 DAA, and vanillic acid levels gradually increased during grain filling and peaked near ripeness (35 DAA). Nine phenolic acid biosynthesis pathway genes (TaPAL1, TaPAL2, TaC3H1, TaC3H2, TaC4H, Ta4CL1, Ta4CL2, TaCOMT1, and TaCOMT2) exhibited three distinct expression patterns during grain filling, which may be related to the different phenolic acids levels. White wheat had higher phenolic acid contents and relatively high gene expression at the early stage, while purple wheat had the highest phenolic acid contents and gene expression levels at later stages. These results suggest that the expression of phenolic acid biosynthesis genes may be closely related to phenolic acids accumulation. PMID:27148345

Bacterial Cinnamoyl Esterase Activity Screening for the Production of a Novel Functional Food Product▿ †

PubMed Central

Guglielmetti, Simone; De Noni, Ivano; Caracciolo, Federica; Molinari, Francesco; Parini, Carlo; Mora, Diego

2008-01-01

Lactobacillus helveticus MIMLh5 was selected for its strong cinnamoyl esterase activity on chlorogenic acid and employed for the preparation of a food product containing a high concentration of free caffeic acid. The novel food product was demonstrated to display high total antioxidant power and potential probiotic properties. PMID:18165367

Inhibition of Oral Pathogens Adhesion to Human Gingival Fibroblasts by Wine Polyphenols Alone and in Combination with an Oral Probiotic.

PubMed

Esteban-Fernández, Adelaida; Zorraquín-Peña, Irene; Ferrer, Maria D; Mira, Alex; Bartolomé, Begoña; González de Llano, Dolores; Moreno-Arribas, M Victoria

2018-03-07

Several benefits have been described for red wine polyphenols and probiotic strains in the promotion of colonic metabolism and health. On the contrary, knowledge about their role in the management of oral health is still scarce. In this work, the antiadhesive capacity of selected red wine polyphenols and oenological extracts against the oral pathogens Porphyromonas gingivalis, Fusobacterium nucleatum, and Streptococcus mutans in an in vitro model of human gingival fibroblasts has been explored as well as their complementary action with the candidate oral probiotic Streptococcus dentisani. Results highlighted the antiadhesive capacity of caffeic and p-coumaric acids as well as grape seed and red wine oenological extracts. Both, caffeic and p-coumaric acids increased their inhibition potential against S. mutans adhesion when combined with S. dentisani. Additionally, UHPLC-MS/MS analysis demonstrated the oral metabolism of wine phenolics due to both, cellular and bacterial activity.

Electrochemical oxidation of wine polyphenols in the presence of sulfur dioxide.

PubMed

Makhotkina, Olga; Kilmartin, Paul A

2013-06-12

Electrochemical oxidation of three representative wine polyphenols (catechin, caffeic acid, and quercetin) in the presence of sulfur dioxide in a model wine solution (pH = 3.3) was investigated. The oxidation was undertaken using chronoamperometry at a rotating glassy carbon rod electrode, and the reaction products were characterized by HPLC-MS. The mechanism of electrochemical oxidation of polyphenols in the presence of sulfur dioxide was proposed to be an ECEC mechanism. The polyphenols first underwent a one-electron oxidation to a semiquinone radical, which can be reduced back to the original polyphenol by sulfur dioxide, or further oxidized to the quinone form. In the cases of caffeic acid and catechin, the quinone combined with sulfur dioxide and produced new derivatives. The quercetin quinone underwent further chemical transformations, producing several new compounds. The proposed mechanisms were confirmed by digital simulation of cyclic voltammograms.

Extraction of rutin from Tartary buckwheat milling fractions and evaluation of its thermal stability in an instant fried noodle system.

PubMed

Cho, Yong Jin; Lee, Suyong

2015-06-01

Extraction conditions of rutin from buckwheat milling fractions were established and a rutin-enriched material (REM, 31.8g/100g of rutin) was successfully obtained by the ultrasonic-assisted ethanol method (steaming, 16-150 mesh particle size, 70% ethanol, and ultrasonication at 40°C for 30min). When REM was applied to instant fried noodles (1% and 2% by weight of wheat flour) for rutin fortification, the levels of rutin in the noodles were determined to be about 250-500mg/100g which corresponded to the recommended daily dose of rutin. While frying temperatures (150-190°C) and times (1-3min) did not negatively affect the level of rutin in the instant fried noodles, the distinct loss of rutin was observed after cooking. Furthermore, REM did not significantly affect the oil uptake and mechanical property of instant fried noodles. The strong antioxidant activity of rutin in REM contributed to retarding the oxidative deterioration of the noodles during storage. Copyright © 2014 Elsevier Ltd. All rights reserved.

Rutin inhibits B[a]PDE-induced cyclooxygenase-2 expression by targeting EGFR kinase activity.

PubMed

Choi, Seunghwan; Lim, Tae-Gyu; Hwang, Mun Kyung; Kim, Yoon-A; Kim, Jiyoung; Kang, Nam Joo; Jang, Tae Su; Park, Jun-Seong; Yeom, Myeong Hun; Lee, Ki Won

2013-11-15

Rutin is a well-known flavonoid that exists in various natural sources. Accumulative studies have represented the biological effects of rutin, such as anti-oxidative and anti-inflammatory effects. However, the underlying mechanisms of rutin and its direct targets are not understood. We investigated whether rutin reduced B[a]PDE-induced-COX-2 expression. The transactivation of AP-1 and NF-κB were inhibited by rutin. Rutin also attenuated B[a]PDE-induced Raf/MEK/ERK and Akt activation, but had no effect on the phosphorylation of EGFR. An in vitro kinase assay revealed rutin suppressed EGFR kinase activity. We also confirmed direct binding between rutin and EGFR, and found that the binding was regressed by ATP. The EGFR inhibitor also inhibited the B[a]PDE-induced MEK/ERK and Akt signaling pathways and subsequently, suppressed COX-2 expression and promoter activity, in addition to suppressing the transactivation of AP-1 and NF-κB. In EGFR(-/-)mouse embryonic fibroblast cells, B[a]PDE-induced COX-2 expression was also diminished. Collectively, rutin inhibits B[a]PDE-induced COX-2 expression by suppressing the Raf/MEK/ERK and Akt signaling pathways. EGFR appeared to be the direct target of rutin. Copyright © 2013 Elsevier Inc. All rights reserved.

A UPLC-MS/MS method for qualification of quercetin-3-O-β-D-glucopyranoside-(4→1)-α-L-rhamnoside in rat plasma and application to pharmacokinetic studies.

PubMed

Yao, Xin; Zhou, Guisheng; Tang, Yuping; Li, Zhenhao; Su, Shulan; Qian, Dawei; Duan, Jin-Ao

2013-03-07

A sensitive and accurate ultra-performance liquid chromatography coupled with triple quadrupole mass (UPLC-MS/MS) method was developed for the determination of quercetin-3-O-β-D-glucopyranoside-(4→1)-α-L-rhamnoside (QGR) in rat plasma using rutin as internal standard. Chromatographic separation was achieved on a Acquity BEH C18 column (100 mm × 2.1 mm, 1.7 μm) with a gradient elution of acetonitrile and 0.10% formic acid (v/v) at a flow rate of 0.4 mL/min. QGR and rutin were detected using electrospray negative ionization mass spectrometry in the multiple reaction monitoring (MRM) mode. The method demonstrated good linearity and did not show any endogenous interference with the QGR and rutin peaks. This method was successfully applied to a pharmacokinetic study of QGR in rats after intravenous (20 mg/kg) and oral (40 mg/kg) administration, and the results showed that the compound was poorly absorbed, with an absolute bioavailability of approximately 3.41%.

Hormetic efficacy of rutin to promote longevity in Drosophila melanogaster.

PubMed

Chattopadhyay, Debarati; Chitnis, Atith; Talekar, Aishwarya; Mulay, Prajakta; Makkar, Manyata; James, Joel; Thirumurugan, Kavitha

2017-06-01

Hormetins are compounds that mediate hormesis by being beneficial at low doses but detrimental at high doses. Recent studies have highlighted that many compounds that extended lifespan in model organisms did so by mediating hormesis. Rutin is a glycosylate conjugate of quercetin and rutinose and is abundant in citrus fruits and buckwheat seeds. Rutin possess ROS scavenging, anti-cancer, cardio-protective, skin-regenerative and neuro-protective properties. Drosophila melanogaster is an attractive model organism for longevity studies owing to its homology of organ and cellular-pathways with mammals. In this study, we aimed to understand the effect of rutin on extending longevity in Drosophila melanogaster. Male and female flies were administered with a range of rutin doses (100-800 µM) to analyse whether rutin mediated lifespan-extension by hormesis. Effect of rutin on physiological parameters like food intake, fecundity, climbing activity, development and resistance to various stresses was also studied. Lifespan assays showed that rutin at 200 and 400 µM significantly extended median lifespan in both male and female flies beyond which flies exhibited drastically reduced longevity. Increase in survival at 400 µM was associated with reduced food intake and fecundity. Flies exhibited improved climbing capability with both 200 and 400 µM rutin. Flies fed with 100 and 200 µM rutin exhibited enhanced survival upon exposure to oxidative stress with 400 µM rutin exhibiting no improvement in median lifespan following oxidative stress. Analysis of endogenous peroxide upon treatment with rutin (100-400 µM) with or without 5% H 2 O 2 showed elevated levels of endogenous peroxide with 400 µM rutin whereas no increase in hydrogen peroxide level was observed with rutin at 100 and 200 µM. Finally, gene expression studies in male flies revealed that rutin treatment at 200 and/or 400 µM elevated transcript levels of dFoxO, MnSod, Cat, dTsc1, dTsc2, Thor, dAtg1, dAtg5 and dAtg7 and reduced transcript levels of dTor. Collectively, rutin at 200 and 400 µM improved longevity in flies; 200 µM rutin acted as a mild stressor to prolong lifespan in flies by mediating hormesis whereas 400 µM, being a high dose for best positive effects.

Anti-inflammatory activity of aqueous extract and bioactive compounds identified from the fruits of Hancornia speciosa Gomes (Apocynaceae).

PubMed

Torres-Rêgo, Manoela; Furtado, Allanny Alves; Bitencourt, Mariana Angélica Oliveira; Lima, Maira Conceição Jerônimo de Souza; Andrade, Rafael Caetano Lisbôa Castro de; Azevedo, Eduardo Pereira de; Soares, Thaciane da Cunha; Tomaz, José Carlos; Lopes, Norberto Peporine; da Silva-Júnior, Arnóbio Antônio; Zucolotto, Silvana Maria; Fernandes-Pedrosa, Matheus de Freitas

2016-08-05

Hancornia speciosa Gomes (Apocynaceae), popularly known as "mangabeira," has been used in folk medicine to treat inflammatory disorders, hypertension, dermatitis, diabetes, liver diseases and gastric disorders. Although the ethnobotany indicates that its fruits can be used for the treatment of ulcers and inflammatory disorders, only few studies have been conducted to prove such biological activities. This study investigated the anti-inflammatory properties of the aqueous extract of the fruits of H. speciosa Gomes as well as its bioactive compounds using in vivo experimental models. The bioactive compounds were identified by High Performance Liquid Chromatography coupled with diode array detector (HPLC-DAD) and Liquid Chromatography coupled with Mass Spectrometry (LC-MS). The anti-inflammatory properties were investigated through in vivo tests, which comprised xylene-induced ear edema, carrageenan-induced peritonitis and zymosan-induced air pouch. The levels of IL-1β, IL-6, IL-12 and TNF-α were determined using ELISA. Rutin and chlorogenic acid were identified in the extract as the main secondary metabolites. In addition, the extract as well as rutin and chlorogenic acid significantly inhibited the xilol-induced ear edema and also reduced the cell migration in both carrageenan-induced peritonitis and zymosan-induced air pouch models. Reduced levels of cytokines were also observed. This is the first study that demonstrated the anti-inflammatory activity of the extract of H. speciosa fruits against different inflammatory agents in animal models, suggesting that its bioactive molecules, especially rutin and chlorogenic acid are, at least in part, responsible for such activity. These findings support the widespread use of Hancornia speciosa in popular medicine and demonstrate that its aqueous extract has therapeutical potential for the development of herbal drugs with anti-inflammatory properties.

Modification of lignin content and composition in plants

DOEpatents

Ye, Zheng-Hua

2002-01-01

Plants and methods of preparing plants having reduced lignin content and/or altered lignin composition are provided. The activities of caffeoyl-CoA O-methyltransferase and/or caffeic acid O-methyltransferase enzymes in the modified plants are reduced.

Effects of rutin on acrylamide-induced neurotoxicity

PubMed Central

2014-01-01

Background Rutin is an important flavonoid that is consumed in the daily diet. The cytoprotective effects of rutin, including antioxidative, and neuroprotective have been shown in several studies. Neurotoxic effects of acrylamide (ACR) have been established in humans and animals. In this study, the protective effects of rutin in prevention and treatment of neural toxicity of ACR were studied. Results Rutin significantly reduced cell death induced by ACR (5.46 mM) in time- and dose-dependent manners. Rutin treatment decreased the ACR-induced cytotoxicity significantly in comparison to control (P <0.01, P < 0.001). Rutin (100 and 200 mg/kg) could prevent decrease of body weight in rats. In combination treatments with rutin (50, 100 and 200 mg/kg), vitamin E (200 mg/kg) and ACR, gait abnormalities significantly decreased in a dose-dependent manner (P < 0.01 and P < 0.001). The level of malondialdehyde significantly decreased in the brain tissue of rats in both preventive and therapeutic groups that received rutin (100 and 200 mg/kg). Conclusion It seems that rutin could be effective in reducing neurotoxicity and the neuroprotective effect of it might be mediated via antioxidant activity. PMID:24524427

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.

[Study on chemical constituents of Orobanche coerulescens].

PubMed

Zhao, Jun; Yan, Ming; Huang, Yi; He, Wen-yi; Zhao, Yu

2007-10-01

Six compounds were isolated and purified from Orobanche coerulescens by extraction and different kinds of column chromatography. The structures were determined on the basis of spectral analysis. The structures were elucidated as D-mannitol(I), beta-sitosterol(II), succinic acid(III), caffeic acid(IV), protocatechuic aldehyde(V) and daucosterol(VI). All compounds are obtained from this plant for the first time.

Profile and antioxidant activity of phenolic extracts from 10 crabapples (Malus wild species).

PubMed

Li, Nan; Shi, Junling; Wang, Kun

2014-01-22

Phenolic products are highly demanded by the food and cosmetics industries and consumers due to their high antioxidant activities. To evaluate the potential of crabapples (Malus wild species) in preparing phenolic extracts, fruits of 10 crabapples grown in China were separately extracted with 80% (v/v) ethanol and ethyl acetate and the phenolic profiles, polyphenol (PC) and flavonoid contents (FC), and antioxidant activities of the extracts were analyzed. Chlorogenic acid, (-)-epicatechin, rutin, hyperin, and phlorizin appeared as the major phenolic compounds in all phenolic extracts. Ethanol extracts had PC of 302.83-1265.94 mg GAE/100g and FC of 352.45-2351.74 mg RE/100g, being 4.17 and 4.49 times those obtained in ethyl acetate extracts and much higher than those previously reported in apples. Malus wild species appeared as rich sources of phenolic compounds with high antioxidant activity, especially when high chlorogenic acid and rutin contents are emphasized.

Influence of LOX/COX inhibitors on cell differentiation induced by all-trans retinoic acid in neuroblastoma cell lines.

PubMed

Redova, Martina; Chlapek, Petr; Loja, Tomas; Zitterbart, Karel; Hermanova, Marketa; Sterba, Jaroslav; Veselska, Renata

2010-02-01

We investigated the possible modulation by LOX/ COX inhibitors of all-trans retinoic acid (ATRA)-induced cell differentiation in two established neuroblastoma cell lines, SH-SY5Y and SK-N-BE(2). Caffeic acid, as an inhibitor of 5-lipoxygenase, and celecoxib, as an inhibitor of cyclooxygenase-2, were chosen for this study. The effects of the combined treatment with ATRA and LOX/COX inhibitors on neuroblastoma cells were studied using cell morphology assessment, detection of differentiation markers by immunoblotting, measurement of proliferation activity, and cell cycle analysis and apoptosis detection by flow cytometry. The results clearly demonstrated the potential of caffeic acid to enhance ATRA-induced cell differentiation, especially in the SK-N-BE(2) cell line, whereas application of celecoxib alone or with ATRA led predominantly to cytotoxic effects in both cell lines. Moreover, the higher sensitivity of the SK-N-BE(2) cell line to combined treatment with ATRA and LOX/COX inhibitors suggests that cancer stem cells are a main target for this therapeutic approach. Nevertheless, further detailed study of the phenomenon of enhanced cell differentiation by expression profiling is needed.

Enhancement of caffeic acid phenethyl ester on all-trans retinoic acid-induced differentiation in human leukemia HL-60 cells

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

Kuo, H.-C.; Kuo, W.-H.; Lee, Y.-J.

2006-10-01

All-trans retinoic acid (ATRA) induces complete remission in a high proportion of patients with acute promyelocytic leukemia (APL); however, the response is sometimes very slow. Furthermore, relapse and resistance to treatment often occur despite continued treatment with ATRA. Thereafter, combination treatment strategies have been suggested to circumvent these problems. The present study demonstrates that caffeic acid phenethyl ester (CAPE), a major component of honeybee propolis, enhanced ATRA-induced granulocytic differentiation in HL-60, a human promyelocytic cell line. The differentiation was assessed by Wright-Giemsa stain, nitroblue tetrazolium reduction, and membrane differentiation marker CD11b. In addition, CAPE enhanced ATRA-induced cell cycle arrest atmore » the G1 phase by decreasing the association of cdk2-cyclin E complex. Finally, it was demonstrated that CAPE promoted the ATRA-mediated nuclear transcription activation of RAR{alpha} assessed by EMSA assay and enhanced the expression of target genes including RAR{alpha}, C/EBP{epsilon}, and p21 protein resulting in the differentiation development of leukemia. It is suggested that CAPE possesses the potential to enhance the efficiency of ATRA in the differentiation therapy of APL.« less

Development and validation of High-performance Thin-layer Chromatography Method for Simultaneous Determination of Polyphenolic Compounds in Medicinal Plants.

PubMed

Jayachandran Nair, C V; Ahamad, Sayeed; Khan, Washim; Anjum, Varisha; Mathur, Rajani

2017-12-01

Quantitative standardization of plant-based products is challenging albeit essential to maintain their quality. This study aims to develop and validate high-performance thin-layer chromatography (HPTLC) method for the simultaneous determination of rutin (Ru), quercetin (Qu), and gallic acid (Ga) from Psidium guajava Linn. (PG) and Aegle marmelos (L.) Correa. (AM) and correlate with antioxidant activity. The stock solution (1 mg/mL) of standard Ru, Qu, and Ga in methanol: Water (1:1) was serially diluted and spotted (5 μL) on slica gel 60 F 254 thin-layer chromatography plates. Toluene: Ethyl acetate: Formic acid: Methanol (3:4:0.8:0.7, v/v/v) was selected as mobile phase for analysis at 254 nm. Hydroalcoholic (1:1) extracts of leaves of PG and AM were fractionated and similarly analyzed. Antioxidant activity was also determined using 2, 2-diphenyl-1-picrylhydrazyl assay. The developed method was robust and resolved Ru, Qu, and Ga at R f 0.08 ± 0.02, 0.76 ± 0.01, and 0.63 ± 0.02, respectively. The intra-day, interday precision, and interanalyst were <2% relative standard deviation. The limit of detection and limit of quantification for Ru, Qu, and Ga were 4.51, 4.2, 5.27, and 13.67, 12.73, 15.98 ng/spot, respectively. Antioxidant activity (Log 50% inhibition) of PG and AM was 4.947 ± 0.322 and 6.498 ± 0.295, respectively. The developed HPTLC method was rapid, accurate, precise, reproducible, and specific for the simultaneous estimation of Ru, Qu, and Ga. HPTLC method for simultaneous determination and quantification of Rutin, Quercetin and Gallic acid, is reported for quality control of herbal drugs. Abbreviations Used: A: Aqueous fraction; AM: Aegle marmelos L. Correa; B: Butanol fraction; C: Chloroform fraction; EA: Ethyl acetate fraction; Ga: Gallic acid; H: Hexane fraction; HA: Hydroalcoholic extract; HPTLC: High-performance thin-layer chromatography; PG: Psidium guajava ; Qu: Quercetin; Ru: Rutin.

Catechol Groups Enable Reactive Oxygen Species Scavenging-Mediated Suppression of PKD-NFkappaB-IL-8 Signaling Pathway by Chlorogenic and Caffeic Acids in Human Intestinal Cells.

PubMed

Shin, Hee Soon; Satsu, Hideo; Bae, Min-Jung; Totsuka, Mamoru; Shimizu, Makoto

2017-02-20

Chlorogenic acid (CHA) and caffeic acid (CA) are phenolic compounds found in coffee, which inhibit oxidative stress-induced interleukin (IL)-8 production in intestinal epithelial cells, thereby suppressing serious cellular injury and inflammatory intestinal diseases. Therefore, we investigated the anti-inflammatory mechanism of CHA and CA, both of which inhibited hydrogen peroxide (H₂O₂)-induced IL-8 transcriptional activity. They also significantly suppressed nuclear factor kappa-light-chain-enhancer of activated B cells ( NF-κB ) transcriptional activity, nuclear translocation of the p65 subunit, and phosphorylation of IκB kinase (IKK). Additionally, upstream of IKK, protein kinase D (PKD) was also suppressed. Finally, we found that they scavenged H₂O₂-induced reactive oxygen species (ROS) and the functional moiety responsible for the anti-inflammatory effects of CHA and CA was the catechol group. Therefore, we conclude that the presence of catechol groups in CHA and CA allows scavenging of intracellular ROS, thereby inhibiting H₂O₂-induced IL-8 production via suppression of PKD-NF-κB signaling in human intestinal epithelial cells.

Wine phenolic compounds influence the production of volatile phenols by wine-related lactic acid bacteria.

PubMed

Silva, I; Campos, F M; Hogg, T; Couto, J A

2011-08-01

To evaluate the effect of wine phenolic compounds on the production of volatile phenols (4-vinylphenol [4VP] and 4-ethylphenol [4EP]) from the metabolism of p-coumaric acid by lactic acid bacteria (LAB). Lactobacillus plantarum, Lactobacillus collinoides and Pediococcus pentosaceus were grown in MRS medium supplemented with p-coumaric acid, in the presence of different phenolic compounds: nonflavonoids (hydroxycinnamic and benzoic acids) and flavonoids (flavonols and flavanols). The inducibility of the enzymes involved in the p-coumaric acid metabolism was studied in resting cells. The hydroxycinnamic acids tested stimulated the capacity of LAB to synthesize volatile phenols. Growth in the presence of hydroxycinnamic acids, especially caffeic acid, induced the production of 4VP by resting cells. The hydroxybenzoic acids did not significantly affect the behaviour of the studied strains. Some of the flavonoids showed an effect on the production of volatile phenols, although strongly dependent on the bacterial species. Relatively high concentrations (1 g l(-1) ) of tannins inhibited the synthesis of 4VP by Lact. plantarum. Hydroxycinnamic acids were the main compounds stimulating the production of volatile phenols by LAB. The results suggest that caffeic and ferulic acids induce the synthesis of the cinnamate decarboxylase involved in the metabolism of p-coumaric acid. On the other hand, tannins exert an inhibitory effect. This study highlights the capacity of LAB to produce volatile phenols and that this activity is markedly influenced by the phenolic composition of the medium. © 2011 The Authors. Journal of Applied Microbiology © 2011 The Society for Applied Microbiology.

Structure Properties and Mechanisms of Action of Naturally Originated Phenolic Acids and Their Derivatives against Human Viral Infections.

PubMed

Wu, Yi-Hang; Zhang, Bing-Yi; Qiu, Li-Peng; Guan, Rong-Fa; Ye, Zi-Hong; Yu, Xiao-Ping

2017-01-01

A great effort has been made to develop efficacious antiviral drugs, but many viral infections are still lack of efficient antiviral therapies so far. The related exploration of natural products to fight viruses has been raised in recent years. Natural compounds with structural diversity and complexity offer a great chance to find new antiviral agents. Particularly, phenolic acids have attracted considerable attention owing to their potent antiviral abilities and unique mechanisms. The aim of this review is to report new discoveries and updates pertaining to antiviral phenolic acids. The relevant references on natural phenolic acids were searched. The antiviral phenolic acids were classified according to their structural properties and antiviral types. Meanwhile, the antiviral characteristics and structure-activity relationships of phenolic acids and their derivatives were summarized. The review finds that natural phenolic acids and their derivatives possessed potent inhibitory effects on multiple virus in humans such as human immunodeficiency virus, hepatitis C virus, hepatitis B virus, herpes simplex virus, influenza virus and respiratory syncytial virus. In particular, caffeic acid/gallic acid and their derivatives exhibited outstanding antiviral properties by a variety of modes of action. Naturally derived phenolic acids especially caffeic acid/gallic acid and their derivatives may be regarded as novel promising antiviral leads or candidates. Additionally, scarcely any of these compounds has been used as antiviral treatment in clinical practice. Therefore, these phenolic acids with diverse skeletons and mechanisms provide us an excellent resource for finding novel antiviral drugs. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

Metabolic and microbial signatures in rat hepatocellular carcinoma treated with caffeic acid and chlorogenic acid.

PubMed

Zhang, Zhan; Wang, Di; Qiao, Shanlei; Wu, Xinyue; Cao, Shuyuan; Wang, Li; Su, Xiaojian; Li, Lei

2017-07-03

Hepatocellular carcinoma (HCC) treatment remains lack of effective chemopreventive agents, therefore it is very attractive and urgent to discover novel anti-HCC drugs. In the present study, the effects of chlorogenic acid (ChA) and caffeic acid (CaA) on HCC induced by diethylnitrosamine (DEN) were evaluated. ChA or CaA could reduce the histopathological changes and liver injury markers, such as alanine transarninase, aspartate aminotransferase, alkaline phosphatase, total bile acid, total cholesterol, high density lipoprotein cholesterol and low density lipoprotein cholesterol. The underlying mechanisms were investigated by a data integration strategy based on correlation analyses of metabonomics data and 16 S rRNA gene sequencing data. ChA or CaA could inhibit the increase of Rumincoccaceae UCG-004 and reduction of Lachnospiraceae incertae sedis, and Prevotella 9 in HCC rats. The principal component analysis and partial least squares discriminant analysis were applied to reveal the metabolic differences among these groups. 28 different metabolites showed a trend to return to normal in both CaA and ChA treatment. Among them, Bilirubin, L-Tyrosine, L-Methionine and Ethanolamine were correlated increased Rumincoccaceae UCG-004 and decreased of Lachnospiraceae incertae sedis and Prevotella 9. These correlations could be identified as metabolic and microbial signatures of HCC onset and potential therapeutic targets.

Enhanced Bioaccessibility of Crocetin Sugar Esters from Saffron in Infusions Rich in Natural Phenolic Antioxidants.

PubMed

Ordoudi, Stella A; Kyriakoudi, Anastasia; Tsimidou, Maria Z

2015-09-25

The present study aims to examine whether and to what extent the bioaccessibility of the major saffron apocarotenoids, namely crocetin sugar esters (CRTSEs), is affected by the presence of strong water-soluble antioxidants, ingredients of the herbs found in commercial tea blends with saffron. An in vitro digestion model was applied to infusions from these products to investigate the possible changes. All of the studied infusions were rich in total phenols (9.9-22.5 mg caffeic acid equivalents/100 mg dry infusion) and presented strong DPPH radical scavenging activity regardless of the composition of the corresponding herbal blends. RP-HPLC-DAD and LC-MS analysis enabled the grouping of the infusions into hydroxycinnamic acid-rich and in flavan-3-ol-rich ones. CRTSEs in herbal tea infusions were found to be significantly more bioaccessible (66.3%-88.6%) than those in the reference saffron infusion (60.9%). The positive role of strong phenolic antioxidants (caffeic acid, rosmarinic acid) on the stability of CRTSEs was also evidenced in model binary mixtures. On the contrary, cinnamic acid, exerting no antioxidant activity, did not have such an effect. Our findings suggest that strong radical scavengers may protect the crocetin sugar esters from oxidation during digestion when present in excess.

Neuroprotective effect of antioxidants on ischaemia and reperfusion-induced cerebral injury.

PubMed

Gupta, Ram; Singh, Manjeet; Sharma, Ajay

2003-08-01

The present study is designed to investigate the effect of dietary flavanoid rutin, micronutrient selenium and garlic oil on ischaemia and reperfusion-induced cerebral injury. Global cerebral ischaemia was induced by occluding right and left common carotid arteries for 10min followed by reperfusion for 24h. Cerebral infarct size was estimated using triphenyltetrazolium chloride staining. Elevated plus maze was employed to estimate short-term memory. Degree of motor incoordination was evaluated using inclined beam-walking test and lateral push test. Mitochondrial thiobarbituric acid reactive substances (TBARS) assay was employed as an index of oxidative stress. Global cerebral ischaemia followed by reperfusion produced a significant impairment in short-term memory and motor coordination and produced a notable increase in mitochondrial TBARS. Administration of rutin and garlic oil before global cerebral ischaemia markedly reduced cerebral infarct size and attenuated impairment in short-term memory and motor coordination. Administration of sodium selenite either before or after global cerebral ischaemia markedly reduced cerebral infarct size and attenuated impairment in short-term memory and motor coordination. The protective effect of rutin, sodium selenite and garlic oil was accompanied by a marked decrease in mitochondrial TBARS. On the basis of these results, it may be suggested that rutin and garlic oil administrated before cerebral ischaemia may scavenge reactive oxygen species and consequently attenuate global cerebral ischaemia and reperfusion-induced cerebral injury. Sodium selenite administrated before and after cerebral ischaemia may be neuroprotective due to its antioxidant effect.

Graphene oxide for solid-phase extraction of bioactive phenolic acids.

PubMed

Hou, Xiudan; Wang, Xusheng; Sun, Yingxin; Wang, Licheng; Guo, Yong

2017-05-01

A solid-phase extraction (SPE) method for the efficient analysis of trace phenolic acids (PAs, caffeic acid, ferulic acid, protocatechuic acid, cinnamic acid) in urine was established. In this work, a graphene oxide (GO) coating was grafted onto pure silica to be investigated as SPE material. The prepared GO surface had a layered and wrinkled structure that was rough and well organized, which could provide more open adsorption sites. Owing to its hydrophilicity and polarity, GO showed higher extraction efficiency toward PAs than reduced GO did, in agreement with the theoretical calculation results performed by Gaussian 09 software. The adsorption mechanism of PAs on GO@Sil was also investigated through static state and kinetic state adsorption experiments, which showed a monolayer surface adsorption. Extraction capacity of the as-prepared material was optimized using the response surface methodology. Under the optimized conditions, the as-established method provided wide linearity range (2-50 μg L -1 for protocatechuic acid and 1-50 μg L -1 for caffeic acid, ferulic acid, and cinnamic acid) and low limits of detection (0.25-1 μg L -1 ). Finally, the established method was applied for the analysis of urine from two healthy volunteers. The results indicate that the prepared material is a practical, cost-effective medium for the extraction and determination of phenolic acids in complex matrices. Graphical Abstract A graphene oxide coating was grafted onto pure silica as the SPE material for the extraction of phenolic acids in urines and the extraction mechanism was also mainly investigated.

Antioxidant activity of leaf extracts from different Hibiscus sabdariffa accessions and simultaneous determination five major antioxidant compounds by LC-Q-TOF-MS.

PubMed

Wang, Jin; Cao, Xianshuang; Jiang, Hao; Qi, Yadong; Chin, Kit L; Yue, Yongde

2014-12-17

Hibiscus sabdariffa has gained attention for its antioxidant activity. There are many accessions of H. sabdariffa in the world. However, information on the quantification of antioxidant compounds in different accessions is rather limited. In this paper, a liquid chromatography/quadrupole-time-of-flight mass spectrometry (LC-Q-TOF-MS) method for simultaneous determination of five antioxidant compounds (neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid, rutin, and isoquercitrin) in H. sabdariffa leaves was developed. The method was validated for linearity, sensitivity, precision, repeatability and accuracy. The validated method has been successfully applied for determination of the five analytes in eight accessions of H. sabdariffa. The eight accessions of H. sabdariffa were evaluated for their antioxidant activities by DPPH free radical scavenging assay. The investigated accessions of H. sabdariffa were rich in rutin and exhibited strong antioxidant activity. The two accessions showing the highest antioxidant activities were from Cuba (No. 2) and Taiwan (No. 5). The results indicated that H. sabdariffa leaves could be considered as a potential antioxidant source for the food industry. The developed LC-Q-TOF-MS method is helpful for quality control of H. sabdariffa.

Solubilizing properties of new surface-active agents, products of catalytic oxyethylation of cholic acid.

PubMed

Kołodziejczyk, Michał Krzysztof; Nachajski, Michal Jakub; Lukosek, Marek; Zgoda, Marian Mikołaj

2013-01-01

Solubilizing properties of aqueous solutions of a series of surface-active agents, products of oxyethylation of cholic acid, were examined in the present study. The content of oxyethylated segments determined by means of the 1H NMR method enabled the verification of the molecular mass of surfactants along with the calculation of the structural hydrophilic-lipophilic balance (HLB), the solubility parameter delta1/2, and the required solubility level of balance HLB(R). Viscosimetric measurements enabled the calculation of the limiting viscosity number, the content-average molecular mass, the effective volume, the hydrodynamic radius of the surfactant micelle and their equilibrium adducts with rutin, diclofenac and loratadine (BCS Class II and III). By means of the spectrophotometric method (UV) the amount of the solubilized diclofenac, loratadine and rutin (rutoside) was determined in the equilibrium system (saturated solution) in the environment of aqueous solutions of cholic acid derivatives of n(TE) = 20-70. The obtained results serve as a basis for determining the solubilization mechanism of lipophilic therapeutic products and indirectly for estimating the influence of the above process on pharmaceutical as well as biological availability of a micellar adduct from model drug forms (Lindbladt lithogenolitic index).

Biosynthesis of hydroxycinnamoyl esters and amides in legume species

USDA-ARS?s Scientific Manuscript database

In forage crops, protein that is degraded following harvest is poorly utilized by ruminant animals, resulting in both economic and environmental consequences. In red clover, secondary reactions of quinones resulting from polyphenol oxidase (PPO)-mediated oxidation of the caffeic acid derivatives pha...

Stilbene content and expression of stilbene synthase genes in cell cultures of Vitis amurensis treated with cinnamic and caffeic acids.

PubMed

Tyunin, Alexey P; Nityagovsky, Nikolay N; Grigorchuk, Valeria P; Kiselev, Konstantin V

2018-03-01

It has previously been shown that exogenous application of p-coumaric acid (CA), a precursor of phenolic compounds, improved stilbene production in cell cultures of Vitis amurensis. This study examines the effect of cinnamic (Cin) and caffeic (Caf) acids, which are also phenolic precursors, on stilbene biosynthesis in the cell cultures. Five stilbenes, t-resveratrol diglucoside, t-piceid (t-resveratrol glucoside), t-resveratrol, t-ε-viniferin, and t-δ-viniferin, were found in the treated and untreated cells. Cin acid increased the total stilbene production in the grape cell cultures 2.3-3.5 times in comparison with that in the untreated cells. Caf acid increased the total stilbene production by 1.8- to 1.9-fold, but this increase was not considerably different from stilbene production in the untreated cells. Cin acid affected the total stilbene production via a marked increase in the content of t-resveratrol diglucoside (up to 2.2 times), t-piceid (up to three times), t-resveratrol (up to 5.1 times), t-ε-viniferin (up to eight times), and t-δ-viniferin (up to 9.2 times). Transcription levels of VaSTS5, 6, 7, 8, and 10 genes considerably increased under 0.1, 0.25, and 0.5 mM Cin acid. These results indicate that Cin acid increased stilbene production in V. amurensis calli via a selective enhancement of STS gene expression. © 2017 International Union of Biochemistry and Molecular Biology, Inc.

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.

Antioxidant effect of mono- and dihydroxyphenols in sunflower oil with different levels of naturally present tocopherols

PubMed Central

Hrádková, Iveta; Merkl, Roman; Šmidrkal, Jan; Kyselka, Jan; Filip, Vladimír

2013-01-01

Antioxidant properties of mono- and dihydroxyphenolic acids and their alkyl esters were examined, with emphasis on the relationship between their molecular structure and antioxidant activity. Test media with different tocopherol level were used for determining the oxidative stability: original refined sunflower oil (total tocopherols 149.0 mg/kg), partially tocopherol-stripped sunflower oil (total tocopherols 8.7 mg/kg) and distilled fatty acid methyl esters (FAME) as a tocopherol-free medium. The chemical reaction of tocopherols with diazomethane tested for the purpose to eliminate their antioxidant activity failed due to the negligible degree of methylation of hydroxyl group in the tocopherol molecule. Caffeic acid and protocatechuic acid (3,4-dihydroxyphenolic acids) and their alkyl esters were found to be more active antioxidants than monohydroxyphenolic acid (p-hydroxybenzoic acid), 2,5-dihydroxyphenolic acid (gentisic acid), 3-methoxy-4-hydroxyphenolic acids (vanillic and ferulic acids) and their corresponding alkyl esters. Naturally present tocopherols in refined sunflower oil proved to have a synergistic effect on gentisic acid but not on its alkyl esters. In contrast, tocopherols showed an antagonistic effect on alkyl esters of caffeic acid, because their protection factors decreased with increasing level of tocopherols in the test medium. Moreover, the antioxidant activity of these alkyl esters decreased with increasing length of their alkyl chain in conformity with the polar paradox hypothesis. Practical applications: Tocopherols as naturally present antioxidants influence considerably the antioxidant activity of other antioxidants added to plant oils used as a test medium. Distilled fatty acid methyl esters prepared from refined sunflower oil may serve as an optimal tocopherol-free test medium. Some alkyl esters of phenolic acids were evaluated to be applicable as natural more lipophilic antioxidants in comparison with phenolic acids. PMID:23997655

Absorption and metabolism of bioactive molecules after oral consumption of cooked edible heads of Cynara scolymus L. (cultivar Violetto di Provenza) in human subjects: a pilot study.

PubMed

Azzini, E; Bugianesi, R; Romano, F; Di Venere, D; Miccadei, S; Durazzo, A; Foddai, M S; Catasta, G; Linsalata, V; Maiani, G

2007-05-01

The current growing interest for natural antioxidants has led to a renewed scientific attention for artichoke, due not only to its nutritional value, but, overall, to its polyphenolic content, showing strong antioxidant properties. The major constituents of artichoke extracts are hydroxycinnamic acids such as chlorogenic acid, dicaffeoylquinic acids caffeic acid and ferulic acid, and flavonoids such as luteolin and apigenin glycosides. In vitro studies, using cultured rat hepatocytes, have shown its hepatoprotective functions and in vivo studies have shown the inhibition of cholesterol biosynthesis in human subjects. Several studies have shown the effect on animal models of artichoke extracts, while information on human bioavailability and metabolism of hydroxycinnamates derivatives is still lacking. Results showed a plasma maximum concentration of 6.4 (SD 1.8) ng/ml for chlorogenic acid after 1 h and its disappearance within 2 h (P< 0.05). Peak plasma concentrations of 19.5 (SD 6.9) ng/ml for total caffeic acid were reached within 1 h, while ferulic acid plasma concentrations showed a biphasic profile with 6.4 (SD1.5) ng/ml and 8.4 (SD4.6) ng/ml within 1 h and after 8 h respectively. We observed a significant increase of dihydrocaffeic acid and dihydroferulic acid total levels after 8 h (P<0.05). No circulating plasma levels of luteolin and apigenin were present. Our study confirms the bioavailability of metabolites of hydroxycinnamic acids after ingestion of cooked edible Cynara scolymus L. (cultivar Violetto di Provenza).

Protective effect of rutin against carbon tetrachloride-induced oxidative stress, inflammation and apoptosis in mouse kidney associated with the ceramide, MAPKs, p53 and calpain activities.

PubMed

Ma, Jie-Qiong; Liu, Chan-Min; Yang, Wei

2018-04-25

Rutin, a natural flavonoid, possess beneficial health effects. However, its renoprotective effect against carbon tetrachloride (CCl 4 ) induced injury and the underlying mechanism is not clarified. The current study aims is to identify the therapeutic effects of rutin on oxidative stress, inflammation and apoptosis in mouse kidney exposed to CCl 4 . ICR mice received CCl 4 with or without rutin co-administration for one week. Compared with the control group, mice receiving CCl 4 alone showed kidney injury as evidenced by elevation in serum biochemical markers, inflammation, caspase-3 activity and apoptosis in kidney, while rutin administration significantly attenuated these pathophysiological changes. Exploration of the underlying mechanisms of its action demonstrated that rutin reduced the ROS, calpain and ceramide levels in mouse kidneys. Rutin significantly decreased the p53, TNF-α, IL-1β activities and mitogen-activated protein kinase (MAPK) phosphorylation in the kidneys. In addition, rutin increased the levels of Bcl-2 protein and reduced levels protein of Bax. Rutin also inhibited the release of cytochrome C from mitochondria in kidneys of the CCl 4 -treated mice. Taken together, rutin ameliorates CCl 4 -induced oxidative stress, inflammation and apoptosis through regulating the ceramide, MAPK, p53 and calpain activities and thereby suppressing apoptosis by the mitochondrial pathway. Copyright © 2018 Elsevier B.V. All rights reserved.

Inhibition of Procarcinogen Activating Enzyme CYP1A2 Activity and Free Radical Formation by Caffeic Acid and its Amide Analogues.

PubMed

Narongchai, Paitoon; Niwatananun, Kanokporn; Narongchai, Siripun; Kusirisin, Winthana; Jaikang, Churdsak

2016-01-01

Caffeic acid (CAF) and its amide analogues, ethyl 1-(3',4'-dihydroxyphenyl) propen amide (EDPA), phenethyl 1-(3',4'-dihydroxyphenyl) propen amide (PEDPA), phenmethyl 1- (3',4'-dihydroxyphenyl) propen amide (PMDPA) and octyl 1-(3',4'-dihydroxyphenyl) propen amide (ODPA) were investigated for the inhibition of procarcinogen activating enzyme. CYP1A2 and scavenging activity on formation of nitric oxide, superoxide anion, DPPH radical and hydroxyl radical. It was found that they inhibited CYP1A2 enzyme by uncompetitive inhibition. Apparent Ki values of CAF, EDPA, PEDPA, PMDPA and ODPA were 0.59, 0.39, 0.45, 0.75 and 0.80 µM, respectively suggesting potent inhibitors of CYP1A2. Moreover, they potentially scavenged nitric oxide radical with IC 50 values of 0.12, 0.22, 0.28, 0.22 and 0.51 mM, respectively. The IC50 values of superoxide anion scavenging were 0.20, 0.22, 0.44, 2.18 and 2.50 mM, respectively. 1, 1- diphenyl-2- picrylhydrazyl (DPPH) radical-scavenging ability, shown as IC50 values, were 0.41, 0.29, 0.30, 0.89 and 0.84 mM, respectively. Moreover, the hydroxyl radical scavenging in vitro model was shown as IC50 values of 23.22, 21.06, 17.10, 17.21 and 15.81 µM, respectively. From our results, caffeic acid and its amide analogues are in vitro inhibitors of human CYP1A2 catalytic activity and free radical formation. They may be useful to be developed as potential chemopreventive agents that block CYP1A2-mediated chemical carcinogenesis.

Feeding-induced phenol production in Capsicum annuum L. influences Spodoptera litura F. larval growth and physiology.

PubMed

Movva, Vijaya; Pathipati, Usha Rani

2017-05-01

We studied the role of induced plant phenols as a defense response to insect herbivory. Phenolic compounds were induced in Capsicum annuum L., the source of many culinary peppers, after feeding by different stages of the insect pest, Spodoptera litura F. The phenols were identified and quantified using high performance liquid chromatography (HPLC) and effects produced by these phenols on larval development were studied. Vanillic acid was identified in plants challenged by second, fourth, and fifth instar larvae, but not in plants challenged by third instar nor unchallenged plants. Syringic acid production was induced in chili plants infested with second (0.429 ± 0.003 μg/g fresh weight, fourth (0.396 ± 0.01 μg/g fresh weight), and fifth instar (5.5 ± 0.06 μg/g fresh weight) larvae, compared to untreated plants (0.303 ± 0.01 μg/g fresh weight) plants. Leaves surface treated with the rutin deterred oviposition. Dietary exposure to chlorogenic acid, vanillic acid, syringic acid, sinapic acid, and rutin led to enhanced activities of detoxifying enzymes, β-glucosidase, carboxyl esterase, glutathione S-transferase, and glutathione reductase in the midgut tissues of all the larval instars, indicating the toxic nature of these compounds. Protein carbonyl content and acetylcholinesterase activity was analyzed to appreciate the role of induced plant phenols in insect protein oxidation and terminating nerve impulses. © 2017 Wiley Periodicals, Inc.

Ameliorating role of rutin on oxidative stress induced by iron overload in hepatic tissue of rats.

PubMed

Aziza, Samy Ali Hussein; Azab, Mohammed El-Said; El-Shall, Soheir Kamal

2014-08-01

Iron is an essential element that participates in several metabolic activities of cells; however, excess iron is a major cause of iron-induced oxidative stress and several human diseases. Natural flavonoids, as rutin, are well-known antioxidants and could be efficient protective agents. Therefore, the present study was undertaken to evaluate the protective influence of rutin supplementation to improve rat antioxidant systems against IOL-induced hepatic oxidative stress. Sixty male albino rats were randomly divided to three equal groups. The first group, the control, the second group, iron overload group, the third group was used as iron overload+rutin group. Rats received six doses of ferric hydroxide polymaltose (100 mg kg(-1) b.wt.) as one dose every two days, by intraperitoneal injections (IP) and administrated rutin (50 mg kg(-1) b.wt.) as one daily oral dose until the sacrificed day. Blood samples for serum separation and liver tissue specimens were collected three times, after three, four and five weeks from the onset of the experiment. Serum iron profiles total iron, Total Iron Binding Capacity (TIBC), Unsaturated Iron Binding Capacity (UIBC), transferrin (Tf) and Transferrin Saturation% (TS%)}, ferritin, albumin, total Protein, total cholesterol, triacylglycerols levels and aspartate aminotransferase (AST) and alanine aminotransferase (ALT) activities were determined. Moreover, total iron in the liver, L-malondialdehyde (L-MDA), glutathione (GSH), Nitric Oxide (NO) and Total Nucleic Acid (TNA) levels and glutathione peroxidase (GPx), catalase (CAT) and superoxide dismutase (SOD) activities were also determined. The obtained results revealed that, iron overload (IOL) resulted in significant increase in serum iron, TIBC, Tf, TS% and ferritin levels and AST and ALT activities and also increased liver iron, L-MDA and NO levels. Meanwhile, it decreased serum UIBC, total cholesterol, triacylglycerols, albumin, total protein and liver GSH, TNA levels and Gpx, CAT and SOD activities when compared with the control group. Rutin administration to iron-overloaded rats resulted in significant decrease in serum total iron, TIBC, Tf, TS%, ferritin levels and AST and ALT activities and liver total iron, L-MDA and NO levels with significant increases in serum UIBC, albumin, total protein and total cholesterol levels and in liver GSH, CAT and SOD activities compared with the IOL group. This study provides in vivo evidence that rutin administration can improve the antioxidant defense systems against IOL-induced hepatic oxidative stress in rats. This protective effect in liver of iron-loaded rats may be due to both antioxidant and metal chelation activities.

Novel Phenolic Inhibitors of Small/Intermediate-Conductance Ca2+-Activated K+ Channels, KCa3.1 and KCa2.3

PubMed Central

Oliván-Viguera, Aida; Valero, Marta Sofía; Murillo, María Divina; Wulff, Heike; García-Otín, Ángel-Luis; Arbonés-Mainar, José-Miguel; Köhler, Ralf

2013-01-01

Background KCa3.1 channels are calcium/calmodulin-regulated voltage-independent K+ channels that produce membrane hyperpolarization and shape Ca2+-signaling and thereby physiological functions in epithelia, blood vessels, and white and red blood cells. Up-regulation of KCa3.1 is evident in fibrotic and inflamed tissues and some tumors rendering the channel a potential drug target. In the present study, we searched for novel potent small molecule inhibitors of KCa3.1 by testing a series of 20 selected natural and synthetic (poly)phenols, synthetic benzoic acids, and non-steroidal anti-inflammatory drugs (NSAIDs), with known cytoprotective, anti-inflammatory, and/or cytostatic activities. Methodology/Principal Findings In electrophysiological experiments, we identified the natural phenols, caffeic acid (EC50 1.3 µM) and resveratrol (EC50 10 µM) as KCa3.1 inhibitors with moderate potency. The phenols, vanillic acid, gallic acid, and hydroxytyrosol had weak or no blocking effects. Out of the NSAIDs, flufenamic acid was moderately potent (EC50 1.6 µM), followed by mesalamine (EC50≥10 µM). The synthetic fluoro-trivanillic ester, 13b ([3,5-bis[(3-fluoro-4-hydroxy-benzoyl)oxymethyl]phenyl]methyl 3-fluoro-4-hydroxy-benzoate), was identified as a potent mixed KCa2/3 channel inhibitor with an EC50 of 19 nM for KCa3.1 and 360 pM for KCa2.3, which affected KCa1.1 and Kv channels only at micromolar concentrations. The KCa3.1/KCa2-activator SKA-31 antagonized the 13b-blockade. In proliferation assays, 13b was not cytotoxic and reduced proliferation of 3T3 fibroblasts as well as caffeic acid. In isometric vessel myography, 13b increased contractions of porcine coronary arteries to serotonin and antagonized endothelium-derived hyperpolarization-mediated vasorelaxation to pharmacological KCa3.1/KCa2.3 activation. Conclusions/Significance We identified the natural phenols, caffeic acid and resveratrol, the NSAID, flufenamic acid, and the polyphenol 13b as novel KCa3.1 inhibitors. The high potency of 13b with pan-activity on KCa3.1/KCa2 channels makes 13b a new pharmacological tool to manipulate inflammation and cancer growth through KCa3.1/KCa2 blockade and a promising template for new drug design. PMID:23516517

[Synthesis and physico-chemical characterisation of some new derivatives of rutoside and clofibric acid].

PubMed

Lupaşcu, D; Profire, Lenuţa; Dănilă, Gh

2006-01-01

Fibrates are drugs with efficacy in reducing blood cholesterol levels and especially, triglyceride plasma levels. Unfortunately, fibrates have a poor water-solubility and showed some adverse reactions at long treatment. The objective of this study was to obtain some new clofibric acid derivatives with rutin; some of these compounds contain a guanidine moiety, known as effective at cardiovascular level. All the compounds are soluble in water.

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.

Evolution of novel O-methyltransferases from the Vanilla planifolia caffeic acid O-methyltransferase.

PubMed

Li, Huaijun Michael; Rotter, David; Hartman, Thomas G; Pak, Fulya E; Havkin-Frenkel, Daphna; Belanger, Faith C

2006-06-01

The biosynthesis of many plant secondary compounds involves the methylation of one or more hydroxyl groups, catalyzed by O-methyltransferases (OMTs). Here, we report the characterization of two OMTs, Van OMT-2 and Van OMT-3, from the orchid Vanilla planifolia Andrews. These enzymes catalyze the methylation of a single outer hydroxyl group in substrates possessing a 1,2,3-trihydroxybenzene moiety, such as methyl gallate and myricetin. This is a substrate requirement not previously reported for any OMTs. Based on sequence analysis these enzymes are most similar to caffeic acid O-methyltransferases (COMTs), but they have negligible activity with typical COMT substrates. Seven of 12 conserved substrate-binding residues in COMTs are altered in Van OMT-2 and Van OMT-3. Phylogenetic analysis of the sequences suggests that Van OMT-2 and Van OMT-3 evolved from the V. planifolia COMT. These V. planifolia OMTs are new instances of COMT-like enzymes with novel substrate preferences.

A voltammetric determination of caffeic acid in red wines based on the nitrogen doped carbon modified glassy carbon electrode.

PubMed

Karikalan, Natarajan; Karthik, Raj; Chen, Shen-Ming; Chen, Hsi-An

2017-04-05

We reported an electrochemical determination of caffeic acid (CA) based on the nitrogen doped carbon (NDC). The described sensor material was prepared by the flame synthesis method, which gave an excellent platform for the synthesis of carbon nanomaterials with the hetero atom dopant. The synthesized material was confirmed by various physical characterizations and it was further characterized by different electrochemical experiments. The NDC modified glassy carbon electrode (NDC/GCE) shows the superior electrocatalytic performance towards the determination of CA with the wide linear concentration range from 0.01 to 350 μM. It achieves the lowest detection limit of 0.0024 μM and the limit of quantification of 0.004 μM. The NDC/GCE-CA sensor reveals the good selectivity, stability, sensitivity and reproducibility which endorsed that the NDC is promising electrode for the determination of CA. In addition, NDC modified electrode is applied to the determination of CA in red wines and acquired good results.

Plant-derived phenolic compounds prevent the DNA single-strand breakage and cytotoxicity induced by tert-butylhydroperoxide via an iron-chelating mechanism.

PubMed Central

Sestili, Piero; Diamantini, Giuseppe; Bedini, Annalida; Cerioni, Liana; Tommasini, Ilaria; Tarzia, Giorgio; Cantoni, Orazio

2002-01-01

The protective effects of selected members from a series of caffeic acid esters and flavonoids were tested in various toxicity paradigms using U937 cells, previously shown to be sensitive to either iron chelators or bona fide radical scavengers or to both classes of compounds. It was found that all the protective polyphenols were active at very low concentrations and that their effects were observed only under those conditions in which iron chelators also afforded protection. Consistently, active polyphenolic compounds, unlike the inactive ones, effectively chelated iron in an in vitro system. It follows that, at least under the experimental conditions utilized in the present study, the most prominent activity of these polyphenolic compounds resides in their ability to chelate iron. Further studies revealed that the protective effects afforded by the caffeic acid esters and flavonoids were largely mediated by the catechol moiety and that the relative biological potency of these compounds was a direct function of their lipophilicity. PMID:11988084

The principal phenolic and alcoholic components of wine protect human lymphocytes against hydrogen peroxide- and ionizing radiation-induced DNA damage in vitro.

PubMed

Greenrod, William; Fenech, Michael

2003-03-01

We have tested the hypothesis that the alcoholic and phenolic components of wine are protective against the DNA-damaging and cytotoxic effects of hydrogen peroxide and gamma-radiation in vitro. The components of wine tested were ethanol, glycerol, a mixture of the phenolic compounds catechin and caffeic acid and tartaric acid, all at concentrations that were 2.5 or 10.0% of the concentration in a typical Australian white wine (Riesling). These components were tested individually or combined as a mixture and compared to a white wine stripped of polyphenols, as well as a Hanks balanced salt solution control, which was the diluent for the wine components. The effect of the components was tested in lymphocytes, using the cytokinesis-block micronucleus assay, after 30 min incubation in plasma or whole blood for the hydrogen peroxide or gamma-radiation challenge, respectively. The results obtained showed that ethanol, glycerol, the catechin-caffeic acid mixture, the mixture of all components and the stripped white wine significantly reduced the DNA-damaging effects of hydrogen peroxide and gamma-radiation (P = 0.043-0.001, ANOVA). The strongest protective effect against DNA damage by gamma-irradiation was observed for the catechin-caffeic acid mixture and the mixture of all components (30 and 32% reduction, respectively). These two treatments as well as ethanol produced the strongest protective effects against DNA damage by hydrogen peroxide (24, 25 and 18%, respectively). The protection provided by the mixture did not account for the expected additive protective effects of the individual components. Ethanol was the only component that significantly increased baseline DNA damage rate, however, this effect was negated in the mixture. In conclusion, our results suggest that the main phenolic and alcoholic components of wine can reduce the DNA-damaging effects of two important oxidants, i.e. hydrogen peroxide and ionizing radiation, in this physiologically relevant in vitro system.

Caffeic acid phenethyl ester protects against glucocorticoid-induced osteoporosis in vivo: Impact on oxidative stress and RANKL/OPG signals

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

Tolba, Mai F.

Glucocorticoid-induced osteoporosis (GIO) is one of the most common causes of secondary osteoporosis. Given that glucocorticoids are considered as a main component of the treatment protocols for a variety of inflammation and immune-mediated diseases besides its use as adjuvant to several chemotherapeutic agents, it is crucial to find ways to overcome this critical adverse effect. Caffeic acid phenethyl ester (CAPE), which is a natural compound derived from honeybee propolis displayed promising antiosteoporotic effects against mechanical bone injury in various studies. The current work aimed at investigating the potential protective effect of CAPE against GIO in vivo with emphasis on themore » modulation of oxidative status and receptor activator of NF-kB ligand (RANKL)/osteoprotegrin (OPG) signaling. The results showed that CAPE opposed dexamethasone (DEX)-mediated alterations in bone histology and tartarate-resistant acid phosphatase (TRAP) activity. In addition, CAPE restored oxidative balance, Runt-related transcription factor 2 (RunX2) expression and reduced caspase-3 activity in femur tissues. Co-administration of CAPE with DEX normalized RANKL/OPG ratio and Akt activation indicating a reduction in DEX-osteoclastogenesis. In conclusion, concurrent treatment of CAPE with DEX exhibited promising effects in the protection against DEX-induced osteoporosis through opposing osteoclastogenesis and protecting osteoblasts. The potent antioxidant activity of CAPE is, at least in part, involved in its anti-apoptotic effects and modulation of RunX2 and RANKL/OPG signals. The use of CAPE-enriched propolis formulas is strongly recommended for patients on chronic glucocorticoid therapy to help in the attenuation of GIO. - Highlights: • Caffeic acid phenethyl ester (CAPE) counteracts DEX-induced osteoporosis. • CAPE hinders DEX-induced alterations in oxidation parameters as GSH, SOD and MDA. • CAPE opposes osteoclastogenesis via suppressing RANL/OPG ratio and Akt signals. • CAPE supports the osteoblasts via modulating caspase-3 and RUNX2 signals.« less

Rapid determination of hydrophilic phenols in olive oil by vortex-assisted reversed-phase dispersive liquid-liquid microextraction and screen-printed carbon electrodes.

PubMed

Fernández, Elena; Vidal, Lorena; Canals, Antonio

2018-05-01

A novel approach is presented to determine hydrophilic phenols in olive oil samples, employing vortex-assisted reversed-phase dispersive liquid-liquid microextraction (RP-DLLME) for sample preparation and screen-printed carbon electrodes for voltammetric analysis. The oxidation of oleuropein, hydroxytyrosol, caffeic acid, ferulic acid and tyrosol was investigated, being caffeic acid and tyrosol selected for quantification. A matrix-matching calibration using sunflower oil as analyte-free sample diluted with hexane was employed to compensate matrix effects. Samples were analyzed under optimized RP-DLLME conditions, i.e., extractant phase, 1M HCl; extractant volume, 100µL; extraction time, 2min; centrifugation time, 10min; centrifugation speed, 4000rpm. The working range showed a good linearity between 0.075 and 2.5mgL -1 (r = 0.998, N = 7) for caffeic acid, and between 0.075 and 3mgL -1 (r = 0.999, N = 8) for tyrosol. The methodological limit of detection was empirically established at 0.022mgL -1 for both analytes, which is significantly lower than average contents found in olive oil samples. The repeatability was evaluated at two different spiking levels (i.e., 0.5mgL -1 and 2mgL -1 ) and coefficients of variation ranged from 8% to 11% (n = 5). The applicability of the proposed method was tested in olive oil samples of different quality (i.e., refined olive oil, virgin olive oil and extra virgin olive oil). Relative recoveries varied between 83% and 108% showing negligible matrix effects. Finally, fifteen samples were analyzed by the proposed method and a high correlation with the traditional Folin-Ciocalteu spectrophotometric method was obtained. Thereafter, the concentrations of the fifteen oil samples were employed as input variables in linear discriminant analysis in order to distinguish between olive oils of different quality. Copyright © 2017 Elsevier B.V. All rights reserved.

Separation and simultaneous determination of rutin, puerarin, daidzein, esculin and esculetin in medicinal preparations by non-aqueous capillary.

PubMed

Li, Cunhong; Chen, Anjia; Chen, Xiaofeng; Chen, Xingguo; Hu, Zhide

2005-09-01

A simple method for the simultaneous determination of five bioactive components (rutin, puerarin, daidzein esculin and esculetin) in traditional medicinal preparations by non-aqueous capillary electrophoresis with UV detection has been developed for the first time. A running buffer composed of 15% acetonitrile, 2.5% acetic acid and 90 mM sodium cholate in methanol was found to be the most suitable for this separation. The limits of detection for five analytes were over the range of 0.050-1.216 microg ml(-1). The relative standard deviations (R.S.Ds.) of the migration times and the peak areas of the analytes were in the range of 1.3-2.9% and 2.2-2.7% (intraday), 1.7-1.9% and 2.8-3.6% (interday), respectively. In the tested concentration range, linear relationships (correlation coefficients: 0.9974 for rutin, 0.9976 for puerarin, 0.9981 for daidzein, 0.9972 for esculin and 0.9929 for esculetin) between peak areas and concentrations of the analytes were obtained. This method has been successfully applied to simultaneous determination of the five bioactive components with recoveries over the range of 89.4-107.4%.

[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.

Autophagy inhibition enhances anticancer efficacy of artepillin C, a cinnamic acid derivative in Brazilian green propolis.

PubMed

Endo, Satoshi; Hoshi, Manami; Matsunaga, Toshiyuki; Inoue, Takahiro; Ichihara, Kenji; Ikari, Akira

2018-02-26

Propolis, a resinous substance produced by honeybees, possesses various biological actions including anticancer activity towards tumor cells. Recently, the ethanol extract of Brazilian green propolis has been shown to induce autophagy, which is known to be induced in treatment of cancer cells with anticancer drugs, leading to cancer cell survival and decreased sensitivity to anticancer agents. In this study, we aimed to identify autophagy-inducing components of the propolis and elucidated the reciprocal relationship between anticancer cytotoxicity and protective autophagy in prostate cancer CWR22Rv1 cells. Among eight cinnamic acid derivatives [chlorogenic acid, p-coumaric acid, caffeic acid, 3,4-caffeoylquinic acid, artepillin C (ArtC), baccharin, drupanin and caffeic acid phenethyl ester] in propolis, only ArtC showed high autophagy-inducing activity accompanying LC3-II upregulation. ArtC was also induced apoptosis as revealed by DNA fragmentation and increases in cleaved caspase-3 and poly ADP-ribose polymerase. The apoptosis induced by ArtC was exacerbated by cotreatment with autophagy inhibitors (chloroquine, wortmannin and U0126). The cotreatment further induced necroptosis accompanying increased expression of receptor-interacting serine/threonine protein kinases 1 and 3. These data indicate that cytotoxicity of ArtC to the prostate cancer cells is dampened by induced autophagy, but is markedly augmented by inhibition of autophagy. Therefore, the combination of ArtC and autophagy inhibitors may be a novel complementary-alternative treatment for prostate cancer. Copyright © 2018 Elsevier Inc. All rights reserved.

Phytochemical Analysis on Quantification and the Inhibitory Effects on Inflammatory Responses from the Fruit of Xanthii fructus

PubMed Central

Yoo, Sae-Rom; Seo, Chang-Seob; Lee, Na-Ri; Shin, Hyeun-Kyoo; Jeong, Soo-Jin

2015-01-01

Objective: Xanthii fructus (Compositae) is a traditional herbal medicine used for treating headache, toothache, pruritus, empyema, and rhinitis. In this study of the quality control of X. fructus, we performed simultaneous analysis of nine marker compounds: Protocatechuic acid (1), chlorogenic acid (2), caffeic acid (3), 4,5-dicaffeoylquinic acid (4), ferulic acid (5), 3,5-dicaffeoylquinic acid (6), 1,3-dicaffeoylquinic acid (7), 1,4-dicaffeoylquinic acid (8), and 4,5-dicaffeoylquinic acid (9). Materials and Methods: Nine components were separated using reversed-phase SunFire™ C18 analytical column and analyzed using high-performance liquid chromatography. We examined the biological effects of the nine marker compounds by determining their anti-inflammatory activities in the murine macrophage cell line RAW 264.7. Results: Among the nine marker compounds, eight significantly inhibited lipopolysaccharide (LPS)-stimulated tumor necrosis factor-alpha (TNF-α) production. 1, 3, 5 had significant inhibitory effects on LPS-induced prostaglandin E2 (PGE2) production in RAW 264.7 cells. None of the tested marker compounds had a significant effect on interleukin-6 production in LPS-treated RAW 264.7 cells. Our data demonstrated that each marker compound from X. fructus exerts anti-inflammatory activity by targeting different inflammation-related pathways such as the TNF-α or PGE2 pathway. Conclusion: Further experiments using in vitro and in vivo models are needed to identify the mechanisms responsible for the anti-inflammatory properties of each marker compound. SUMMARY Simultaneous analysis of nine phenylpropanoids in the Xanthii fructus was established using HPLC-PDA system.1,4-dicaffeoylquinic acid significantly inhibited LPS-stimulated TNF-a production.Protocatechuic acid, caffeic acid and ferulic acid had significant inhibitory effects on LPS-induced PGE2 production in RAW 264.7 cells. PMID:27013799

Effects of rutin and buckwheat seeds on energy metabolism and methane production in dairy cows.

PubMed

Stoldt, Ann-Kathrin; Derno, Michael; Das, Gürbüz; Weitzel, Joachim M; Wolffram, Siegfried; Metges, Cornelia C

2016-03-01

Flavonoids are secondary plant metabolites with several health promoting effects. As dairy cows often suffer from metabolic imbalance and health problems, interest is growing in health improvements by plant substances such as flavonoids. Our group has recently shown that the flavonoids quercetin and rutin (a glucorhamnoside of quercetin) are bioavailable in cows when given via a duodenal fistula or orally, respectively, affect glucose metabolism, and have beneficial effects on liver health. Furthermore, flavonoids may reduce rumen methane production in vitro through their antibacterial properties. To test the hypothesis that rutin has effects on energy metabolism, methane production, and production performance in dairy cows, we fed rutin trihydrate at a dose of 100mg/kg of body weight to a group of 7 lactating dairy cows for 2 wk in a crossover design. In a second experiment, 2 cows were fed the same ration but were supplemented with buckwheat seeds (Fagopyrum tartaricum), providing rutin at a dose comparable to the first experiment. Two other cows receiving barley supplements were used as controls in a change-over mode. Blood samples were taken weekly and respiration measurements were performed at the end of each treatment. Supplementation of pure rutin, but not of rutin contained in buckwheat seeds, increased the plasma quercetin content. Methane production and milk yield and composition were not affected by rutin treatment in either form. Plasma glucose, β-hydroxybutyrate, and albumin were increased by pure rutin treatment, indicating a possible metabolic effect of rutin on energy metabolism of dairy cows. In addition, we did not show that in vivo ruminal methane production was reduced by rutin. In conclusion, we could not confirm earlier reports on in vitro methane reduction by rutin supplementation in dairy cows in established lactation. Copyright © 2016 American Dairy Science Association. Published by Elsevier Inc. All rights reserved.

Statistical optimization of an RP-HPLC method for the determination of selected flavonoids in berry juices and evaluation of their antioxidant activities.

PubMed

Ciric, Andrija; Jelikic-Stankov, Milena; Cvijovic, Milica; Djurdjevic, Predrag

2018-04-01

An isocratic RP-HPLC method for the separation and identification of selected flavonoids (quercetin, rutin, luteolin-7-O-glucoside, kaempferol and kaempferol-3-O-glucoside) in commercial berry juices (blackcurrant, blueberry, red raspberry and cherry) was developed with the aid of central composite design and response surface methodology. The optimal separation conditions were a mobile phase of 85:15 (% v/v) water-acetonitrile, pH 2.8 (adjusted with formic acid), flow rate 0.5 mL min -1 and column temperature 35°C. The obtained levels of bioflavonoids (mg per 100 mL of juice) were as follows: for quercetin, ca. 0.21-5.12; for kaempferol, ca. 0.05-1.2; for rutin, ca. 0.4-6.5; for luteolin-7-O-glucoside, ca. 5.6-10.2; and for kaempferol-3-O-glucoside, ca. 0.02-0.12. These are considerably lower than the values in fresh fruits. Total phenolic, flavonoid and anthocyanin contents were determined spectrophotometrically. Total flavonoid content varied as follows: blackcurrant > blueberry > red raspberry > cherry. The antioxidant activity of juice extracts (DPPH and ABTS methods) expressed as IC 50 values varied from 8.56 to 14.05 mg L -1 . These values are ~2.5-3 times lower than quercetin, ascorbic acid and Trolox®, but compared with rutin and butylhydroxytoluene, berries show similar or better antioxidant activity by both the DPPH and ABTS methods. Copyright © 2017 John Wiley & Sons, Ltd.

Protection of Flos Lonicerae against acetaminophen-induced liver injury and its mechanism.

PubMed

Jiang, Ping; Sheng, Yu-chen; Chen, Yu-hao; Ji, Li-li; Wang, Zheng-tao

2014-11-01

This study aims to observe the protective action of Flos Lonicerae (FL) aqueous extract against acetaminophen (AP)-induced liver injury and its mechanism. Results show that FL decreases AP-increased serum alanine/aspartate transaminases (ALT/AST) activity, as well as total bilirubin (TB) amount, in mice. Histological evaluation of the liver further confirms the protection of FL against AP-induced hepatotoxicity. TdT-mediated biotin-dUTP nick-end labeling (TUNEL) assay shows that FL reduces AP-increased apoptotic cells. Furthermore, AP-decreased liver glutamate-cysteine ligase (GCL) enzymatic activity and glutathione (GSH) amount are both reversed by FL because of the increased expression of the catalytic subunit of GCL (GCLC) protein. The amount of chlorogenic acid (CGA), caffeic acid, and luteolin, the main active compounds in FL, is detected by high-performance liquid chromatography (HPLC). In addition, cell viability assay demonstrates that polyphenols in FL, such as CGA, caffeic acid, as well as isochlorogenic acids A, B, and C, can reverse AP-induced cytotoxicity. In conclusion, FL can prevent AP-induced liver injury by inhibiting apoptosis. The cellular antioxidant enzyme GCL is also involved in such protection. Polyphenols may be the main active hepato-protective ingredients in FL. Copyright © 2014 Elsevier B.V. All rights reserved.

Effects of solvent polarity on the absorption and fluorescence spectra of chlorogenic acid and caffeic acid compounds: determination of the dipole moments.

PubMed

Belay, Abebe; Libnedengel, Ermias; Kim, Hyung Kook; Hwang, Yoon-Hwae

2016-02-01

The effects of solvent polarity on absorption and fluorescence spectra of biologically active compounds (chlorogenic acid (CGA) and caffeic acids (CA)) have been investigated. In both spectra pronounced solvatochromic effects were observed with shift of emission peaks larger than the corresponding UV-vis electronic absorption spectra. From solvatochromic theory the ground and excited-state dipole moments were determined experimentally and theoretically. The differences between the excited and ground state dipole moment determined by Bakhshiev, Kawski-Chamma-Viallet and Reichardt equations are quite similar. The ground and excited-state dipole moments were determined by theoretical quantum chemical calculation using density function theory (DFT) method (Gaussian 09) and were also similar to the experimental results. The HOMO-LUMO energy band gaps for CGA and CFA were calculated and found to be 4.1119 and 1.8732 eV respectively. The results also indicated the CGA molecule is more stable than that of CFA. It was also observed that in both compounds the excited state possesses a higher dipole moment than that of the ground state. This confirms that the excited state of the hydroxycinnamic compounds is more polarized than that of the ground state and therefore is more sensitive to the solvent. Copyright © 2015 John Wiley & Sons, Ltd.

Evaluation of chemical constituents and antioxidant activity of coconut water (Cocus nucifera L.) and caffeic acid in cell culture.

PubMed

Santos, João L A; Bispo, Vanderson S; Filho, Adriano B C; Pinto, Isabella F D; Dantas, Lucas S; Vasconcelos, Daiane F; Abreu, Fabíula F; Melo, Danilo A; Matos, Isaac A; Freitas, Florêncio P; Gomes, Osmar F; Medeiros, Marisa H G; Matos, Humberto R

2013-01-01

Coconut water contains several uncharacterized substances and is widely used in the human consumption. In this paper we detected and quantified ascorbic acid and caffeic acid and total phenolics in several varieties of coconut using HPLS/MS/MS (25.8 ± 0.6 µg/mL and 1.078 ± 0.013 µg/mL and 99.7 µg/mL, respectively, in the green dwarf coconut water, or 10 mg and 539 µg and 39.8 mg for units of coconut consumed, 500 ± 50 mL). The antioxidant potential of four coconut varieties (green dwarf, yellow dwarf, red dwarf and yellow Malaysian) was compared with two industrialized coconut waters and the lyophilized water of the green dwarf variety. All varieties were effective in scavenging the DPPH radical (IC₅₀=73 µL) and oxide nitric (0.1 mL with an IP of 29.9%) as well as in inhibiting the in vitro production of thiobarbituric acid reactive substances (1 mL with an IP of 34.4%), highlighting the antioxidant properties of the green dwarf which it is the most common used. In cell culture, the green dwarf water was efficient in protecting against oxidative damages induced by hydrogen peroxide.

Metabolomics driven analysis of artichoke leaf and its commercial products via UHPLC-q-TOF-MS and chemometrics.

PubMed

Farag, Mohamed A; El-Ahmady, Sherweit H; Elian, Fatma S; Wessjohann, Ludger A

2013-11-01

The demand to develop efficient and reliable analytical methods for the quality control of herbal medicines and nutraceuticals is on the rise, together with an increase in the legal requirements for safe and consistent levels of active principles. Here, we describe an ultra-high performance liquid chromatography method (UHPLC) coupled with quadrupole high resolution time of flight mass spectrometry (qTOF-MS) analysis for the comprehensive measurement of metabolites from three Cynara scolymus (artichoke) cultivars: American Green Globe, French Hyrious, and Egyptian Baladi. Under optimized conditions, 50 metabolites were simultaneously quantified and identified including: eight caffeic acid derivatives, six saponins, 12 flavonoids and 10 fatty acids. Principal component analysis (PCA) was used to define both similarities and differences among the three artichoke leaf cultivars. In addition, batches from seven commercially available artichoke market products were analysed and showed variable quality, particularly in caffeic acid derivatives, flavonoid and fatty acid contents. PCA analysis was able to discriminate between various preparations, including differentiation between various batches from the same supplier. To the best of our knowledge, this study provides the first approach utilizing UHPLC-MS based metabolite fingerprinting to reveal secondary metabolite compositional differences in artichoke leaf extracts. Copyright © 2013 Elsevier Ltd. All rights reserved.

Propolis Extracted from the Stingless Bee Trigona sirindhornae Inhibited S. mutans Activity In Vitro.

PubMed

Utispan, Kusumawadee; Chitkul, Bordin; Monthanapisut, Paopanga; Meesuk, Ladda; Pugdee, Kamolparn; Koontongkaew, Sittichai

The aim of this study was to determine the antimicrobial effects of propolis extracted from an endemic species of stingless bee, T. sirindhornae, on the cariogenic bacterium Streptococcus mutans. Dichloromethane extracts (DME) of propolis (DMEP) were prepared and analysed by reverse-phase high-performance liquid chromatography. The antibacterial growth and antibiofilm formation effects of DMEP on S. mutans were compared with those of apigenin, a commercial propolis product. The effects of DMEP and apigenin on glucosyltransferase (gtf) B expression in S. mutans were investigated using real-time polymerase chain reaction. Chlorhexidine (CHX) was used as a positive control in the experiments. Apigenin, pinocembrin, p-coumaric acid, and caffeic acid were not detected in the propolis extracts. DMEP and apigenin significantly inhibited S. mutans growth (IC50 = 43.5 and 17.36 mg/ml, respectively). DMEP and apigenin also exhibited antiadherence effects on S. mutans as shown by reduced biofilm formation. Furthermore, a significant inhibition in gtfB expression was observed in DMEP and apigenin treated S. mutans. Propolis produced by T. sirindhornae demonstrated antibacterial and antibiofilm effects, and reduced gtfB expression in S. mutans. The antibacterial activities of propolis observed were not due to apigenin, pinocembrin, p-coumaric acid, or caffeic acid.

Separation of chlorogenic acid and concentration of trace caffeic acid from natural products by pH-zone-refining countercurrent chromatography.

PubMed

Lu, Yuanyuan; Dong, Genlai; Gu, Yanxiang; Ito, Yoichiro; Wei, Yun

2013-07-01

Chlorogenic acid and caffeic acid were selected as test samples for separation by the pH-zone-refining countercurrent chromatography (CCC). The separation of these test samples was performed with a two-phase solvent system composed of methyl-tert-butyl-ether/acetonitrile/water at a volume ratio of 4:1:5 v/v/v where trifluoroacetic acid (TFA; 8 mM) was added to the organic stationary phase as a retainer and NH4 OH (10 mM) to the aqueous mobile phase as an eluter. Chlorogenic acid was successfully separated from Flaveria bidentis (L.) Kuntze (F. bidentis) and Lonicerae Flos by pH-zone-refining CCC, a slightly polar two-phase solvent system composed of methyl-tert-butyl-ether/acetonitrile/n-butanol/water at a volume ratio of 4:1:1:5 v/v/v/v was selected where TFA (3 mM) was added to the organic stationary phase as a retainer and NH4 OH (3 mM) to the aqueous mobile phase as an eluter. A 16.2 mg amount of chlorogenic acid with the purity of 92% from 1.4 g of F. bidentis, and 134 mg of chlorogenic acid at the purity of 99% from 1.3 g of crude extract of Lonicerae Flos have been obtained. These results suggest that pH-zone-refining CCC is suitable for the isolation of the chlorogenic acid from the crude extracts of F. bidentis and Lonicerae Flos. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Simultaneous determination of vitexin-2"-O-glucoside, vitexin-2"-O-rhamnoside, rutin, and hyperoside in the extract of hawthorn (Crataegus pinnatifida Bge.) leaves by RP-HPLC with ultraviolet photodiode array detection.

PubMed

Cheng, Shan; Qiu, Feng; Huang, Jia; He, Junqi

2007-03-01

RP-HPLC with UV photodiode array detection (UV-DAD) was developed and validated for the simultaneous determination of vitexin-2"-O-glucoside, vitexin-2"-O-rhamnoside, rutin, and hyperoside in the extract of hawthorn (Crataegus pinnatifida Bge.) leaves. The analytes of interest were separated on a Diamonsil C18 column (250 x 4.6 mm id, 5 microm) with the mobile phase consisting of THF/ACN/methanol/ 0.05% phosphoric acid solution (pH 5.0) (18:1:1:80 v/vl/v). The flow rate was set at 1.0 mL/min and the eluent was detected at 340 nm for the four flavonoids. The method was linear over the studied range of 1.00-100 microg/mL for the four analytes of interest with the correlation coefficient for each analyte greater than 0.999. The LOD and LOQwere 0.03 and 0.10 microg/mL, 0.03 and 0.10 microg/mL, 0.05 and 0.15 pg/mL, 0.10 and 0.30 microg/mL for vitexin-2"-O-glucoside, vitexin-2"-0-rhamnoside, rutin, and hyperoside, respectively. The optimized method was successfully applied to the analysis of four important flavonoids in the extract of hawthorn leaves. The total amounts of the four flavonoids were 22.2, 62.3, 4.27, and 8.24 mg/g dry weight for vitexin-2"-O-glucoside, vitexin-2"-O-rhamnoside, rutin, and hyperoside in the extract of hawthorn leaves, respectively.

[Simultaneous determination of four compounds in Sanjing Shuanghuanglian Oral Liquid by high performance liquid chromatography-diode array detection-electrochemical detection].

PubMed

Liu, Lin; Suo, Zhirong; Zheng, Jianbin

2006-05-01

Chlorogenic acid, caffeic acid, baicalin and luteolin in Sanjing Shuanghuanglian Oral Liquid were simultaneously detected and identified using a high performance liquid chromatography coupled with diode array detection and electrochemical detection (HPLC-DAD-ECD). The separation was performed on a Zorbax SB-C18 column (150 mm x 4.6 mm i. d., 5.0 microm). The mobile phase consisted of (A) methanol and (B) methanol-water-acetic acid (50: 50: 1, v/v/v) using a linear gradient elution of 2%A-3%A at 0-3 min, 3%A-25%A at 3-15 min, 25%A-80%A at 15-20 min. The flow rate was 0.8 mL/min. The DAD detection was used at 275 nm. The ECD detection was done at 0.7 V. The column thermostat set at 30 degrees C. The limits of detection of the 4 compounds were 1 mg/L for chlorogenic acid, 0.2 mg/L for caffeic acid, 9 mg/L for baicalin, 7 mg/L for luteolin. The average recoveries were between 96.6%-99.6% with relative standard deviations (RSDs) of 2.5%-4.1%. The method is simple, rapid, reproducible and accurate. It can be used for the routine analysis of the four compounds in Shuanghuanglian Oral Liquid.

Chlorogenic acid in a Nicotiana plumbaginifolia cell suspension.

PubMed

Gillet; Mesnard; Fliniaux; Monti; Fliniaux

1999-11-01

A phenylpropanoid compound has been characterized in a Nicotiana plumbaginifolia cell suspension. This compound has been isolated and purified by semi-preparative reverse phase-high performance liquid chromatography. Its structure has been identified by NMR spectroscopy as 5-O-caffeoylquinic acid, which is chlorogenic acid (CA). The influence of culture conditions on the accumulation of this metabolite by N. plumbaginifolia cell suspensions has been studied. Darkness strongly inhibits the CA accumulation. Moreover, it has been shown that feeding experiments with caffeic acid had a deleterious effect upon the CA content. This one was not influenced by a supplementation with quinic acid.

Activity of chalcones derived from 2,4,5-trimethoxybenzaldehyde against Meloidogyne exigua and in silico interaction of one chalcone with a putative caffeic acid 3-O-methyltransferase from Meloidogyne incognita.

PubMed

Nunes, Alexandro Silva; Campos, Vicente Paulo; Mascarello, Alessandra; Stumpf, Taisa Regina; Chiaradia-Delatorre, Louise Domenghini; Machado, Alan Rodrigues Teixeira; Santos Júnior, Helvécio Martins; Yunes, Rosendo Augusto; Nunes, Ricardo José; Oliveira, Denilson Ferreira

2013-12-01

Meloidogyne exigua is a parasitic nematode of plants that causes great losses to coffee farmers. In an effort to develop parasitic controls, 154 chalcones were synthesized and screened for activity against this nematode. The best results were obtained with (2E)-1-(4'-nitrophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one (6) with a 50% lethal concentration (LC50) of 171 μg/ml against M. exigua second-stage juveniles, in comparison to the commercially-available nematicide carbofuran which had an LC50 of 260 μg/ml under the same conditions. When coffee plants were used, 6 reduced the nematode population to ~50% of that observed in control plants. To investigate the mechanism of action of 6, an in silico study was carried out, which indicated that 6 may act against M. exigua through inhibition of a putative caffeic acid 3-O-methyltransferase homodimer, the amino acid sequence of which was determined by examining the genome of Meloidogyne incognita. Copyright © 2013 Elsevier Inc. All rights reserved.

Caffeic acid phenethyl ester downregulates phospholipase D1 via direct binding and inhibition of NFκB transactivation

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

Park, Mi Hee; Kang, Dong Woo; Jung, Yunjin

2013-12-06

Highlights: •We found CAFÉ, a natural product that suppresses expression and activity of PLD1. •CAPE decreased PLD1 expression by inhibiting NFκB transactivation. •CAPE rapidly inhibited PLD activity via its binding to a Cys837 of PLD1. •PLD1 downregulation by CAPE inhibited invasion and proliferation of glioma cells. -- Abstract: Upregulation of phospholipase D (PLD) is functionally linked with oncogenic signals and tumorigenesis. Caffeic acid phenethyl ester (CAPE) is an active compound of propolis extract that exhibits anti-proliferative, anti-inflammatory, anti-oxidant, and antineoplastic properties. In this study, we demonstrated that CAPE suppressed the expression of PLD1 at the transcriptional level via inhibition ofmore » binding of NFκB to PLD1 promoter. Moreover, CAPE, but not its analogs, bound to a Cys837 residue of PLD1 and inhibited enzymatic activity of PLD. CAPE also decreased activation of matrix metalloproteinases-2 induced by phosphatidic acid, a product of PLD activity. Ultimately, CAPE-induced downregulation of PLD1 suppressed invasion and proliferation of glioma cells. Taken together, the results of this study indicate that CAPE might contribute to anti-neoplastic effect by targeting PLD1.« less

Catechol Groups Enable Reactive Oxygen Species Scavenging-Mediated Suppression of PKD-NFkappaB-IL-8 Signaling Pathway by Chlorogenic and Caffeic Acids in Human Intestinal Cells

PubMed Central

Shin, Hee Soon; Satsu, Hideo; Bae, Min-Jung; Totsuka, Mamoru; Shimizu, Makoto

2017-01-01

Chlorogenic acid (CHA) and caffeic acid (CA) are phenolic compounds found in coffee, which inhibit oxidative stress-induced interleukin (IL)-8 production in intestinal epithelial cells, thereby suppressing serious cellular injury and inflammatory intestinal diseases. Therefore, we investigated the anti-inflammatory mechanism of CHA and CA, both of which inhibited hydrogen peroxide (H2O2)-induced IL-8 transcriptional activity. They also significantly suppressed nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) transcriptional activity, nuclear translocation of the p65 subunit, and phosphorylation of IκB kinase (IKK). Additionally, upstream of IKK, protein kinase D (PKD) was also suppressed. Finally, we found that they scavenged H2O2-induced reactive oxygen species (ROS) and the functional moiety responsible for the anti-inflammatory effects of CHA and CA was the catechol group. Therefore, we conclude that the presence of catechol groups in CHA and CA allows scavenging of intracellular ROS, thereby inhibiting H2O2-induced IL-8 production via suppression of PKD-NF-κB signaling in human intestinal epithelial cells. PMID:28230729

Inhibitory Activities of Phenolic Compounds Isolated from Adina rubella Leaves Against 5α-Reductase Associated with Benign Prostatic Hypertrophy.

PubMed

Yin, Jun; Heo, Jun Hyeok; Hwang, Yoon Jeong; Le, Thi Tam; Lee, Min Won

2016-07-07

Adina rubella Hance (AR), a plant native to Korea, has been used as traditional medicine for dysentery, eczema, intoxication, and external hemorrhages. Previous phytochemical studies of AR have reported several components, including terpenoids, phenolics, and alkaloids. The current study evaluated the anti-oxidative and anti-inflammatory activities and 5α-reductase inhibition of isolated compounds of AR leaves to find a potential therapeutic agent for benign prostatic hypertrophy (BPH). Repeated chromatographic isolation of an 80% acetone extract of AR leaves yielded seven phenolic compounds: caffeic acid (1), chlorogenic acid (2), methyl chlorogenate (3), quercetin-3-rutinoside (4), kaempferol-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (5), hyperoside (6), and grandifloroside (7). Compound 7 is a novel compound in AR. Caffeoyl derivatives 1-3 and 7 showed good anti-oxidative activities. In particular, caffeic acid (1) and grandifloroside (7) showed potent anti-inflammatory activities, and 7 also exhibited potent inhibitory activity against TNF-α and 5α-reductase. Our results show that the extract and grandifloroside (7) from leaves of AR might be developed as a source of potent anti-oxidative and anti-inflammatory agents and therapeutic agent for BPH.

Investigation into the antioxidant and antidiabetic potential of Moringa stenopetala: identification of the active principles.

PubMed

Habtemariam, Solomon

2015-03-01

The fresh leaves of Moringa stenopetala (family, Moringaceae) are commonly eaten as cabbage while dried leaves are used as nutritional supplement and for treating a variety of disease conditions including diabetes. The present investigation into the therapeutic potential of the leaves and seeds of the plant revealed no inhibitory effect against α-glucosidase enzyme up to the concentration of 200 μg/mL but the leaves extract displayed potent DPPH (1,1-diphenyl-2- picrylhydrazyl) radical scavenging effect (IC50, 59.5 ± 4.1 μg/mL). An activity directed fractionation and isolation procedure resulted in the identification of the major antioxidant compound as rutin and minor active component, neochlorogenic acid. Both the crude extract (0.8-200 μg/mL) and rutin (0.8-200 μM) but not neochlorogenic acid displayed a concentration-dependent protection of human pancreatic β-cells (1.4E7 cells) from oxidant-induced cell death. The identification of these compounds along with their potential role in the nutritional and medicinal significance of the plant is discussed.

Rutin protects against cognitive deficits and brain damage in rats with chronic cerebral hypoperfusion.

PubMed

Qu, Jie; Zhou, Qiong; Du, Ying; Zhang, Wei; Bai, Miao; Zhang, Zhuo; Xi, Ye; Li, Zhuyi; Miao, Jianting

2014-08-01

Chronic cerebral hypoperfusion is a critical causative factor for the development of cognitive decline and dementia in the elderly, which involves many pathophysiological processes. Consequently, inhibition of several pathophysiological pathways is an attractive therapeutic strategy for this disorder. Rutin, a biologically active flavonoid, protects the brain against several insults through its antioxidant and anti-inflammatory properties, but its effect on cognitive deficits and brain damage caused by chronic cerebral hypoperfusion remains unknown. Here, we investigated the neuroprotective effect of rutin on cognitive impairments and the potential mechanisms underlying its action in rats with chronic cerebral hypoperfusion. We used Sprague-Dawley rats with permanent bilateral common carotid artery occlusion (BCCAO), a well-established model of chronic cerebral hypoperfusion. After rutin treatment for 12 weeks, the neuroprotective effect of rutin in rats was evaluated by behavioural tests, biochemical and histopathological analyses. BCCAO rats showed marked cognitive deficits, which were improved by rutin treatment. Moreover, BCCAO rats exhibited central cholinergic dysfunction, oxidative damage, inflammatory responses and neuronal damage in the cerebral cortex and hippocampus, compared with sham-operated rats. All these effects were significantly alleviated by treatment with rutin. Our results provide new insights into the pharmacological actions of rutin and suggest that rutin has multi-targeted therapeutical potential on cognitive deficits associated with conditions with chronic cerebral hypoperfusion such as vascular dementia and Alzheimer's disease. © 2014 The British Pharmacological Society.

Utilization of tartary buckwheat bran as a source of rutin and its effect on the rheological and antioxidant properties of wheat-based products

USDA-ARS?s Scientific Manuscript database

Tartary buckwheat bran, a by-product of buckwheat flour production was utilized as a source of rutin, and the extracted rutin-enriched material (REM) was used to fortify wheat-based foods of which rheological and antioxidant properties were characterized. REM contained a high content of rutin (29.6 ...

Subcritical Water Induced Complexation of Soy Protein and Rutin: Improved Interfacial Properties and Emulsion Stability.

PubMed

Chen, Xiao-Wei; Wang, Jin-Mei; Yang, Xiao-Quan; Qi, Jun-Ru; Hou, Jun-Jie

2016-09-01

Rutin is a common dietary flavonoid with important antioxidant and pharmacological activities. However, its application in the food industry is limited mainly because of its poor water solubility. The subcritical water (SW) treatment provides an efficient technique to solubilize and achieve the enrichment of rutin in soy protein isolate (SPI) by inducing their complexation. The physicochemical, interfacial, and emulsifying properties of the complex were investigated and compared to the mixtures. SW treatment had much enhanced rutin-combined capacity of SPI than that of conventional method, ascribing to the well-contacted for higher water solubility of rutin with stronger collision-induced hydrophobic interactions. Compared to the mixtures of rutin with proteins, the complex exhibited an excellent surface activity and improved the physical and oxidative stability of its stabilized emulsions. This improving effect could be attributed to the targeted accumulation of rutin at the oil-water interface accompanied by the adsorption of SPI resulting in the thicker interfacial layer, as evidenced by higher interfacial protein and rutin concentrations. This study provides a novel strategy for the design and enrichment of nanovehicle providing water-insoluble hydrophobic polyphenols for interfacial delivery in food emulsified systems. © 2016 Institute of Food Technologists®

Cutaneous biocompatible rutin-loaded gelatin-based nanoparticles increase the SPF of the association of UVA and UVB filters.

PubMed

Oliveira, Camila Areias de; Peres, Daniela D'Almeida; Graziola, Fabiana; Chacra, Nádia Araci Bou; Araújo, Gabriel Lima Barros de; Flórido, Ana Catarina; Mota, Joana; Rosado, Catarina; Velasco, Maria Valéria Robles; Rodrigues, Luís Monteiro; Fernandes, Ana Sofia; Baby, André Rolim

2016-01-01

The encapsulation of natural ingredients, such as rutin, can offer improvements in sun protection effectiveness. This strategy can provide enhanced flavonoid content and produces an improved bioactive compound with new physical and functional characteristics. As an alternative to common synthetic-based sunscreens, rutin-entrapped gelatin nanoparticles (GNPs) were designed and associated with ethylhexyl dimethyl PABA (EHDP), ethylhexyl methoxycinnamate (EHMC) and methoxydibenzoylmethane (BMDBM) in sunscreen formulations. The purpose of this study was to develop rutin-loaded gelatin nanoparticles and characterize their physicochemical, thermal, functional and safety properties. Rutin-loaded gelatin nanoparticles increased antioxidant activity by 74% relative to free-rutin (FR) solution. Also, this new ingredient upgraded the Sun Protection Factor (SPF) by 48%, indicating its potential as a raw material for bioactive sunscreens. The safety profile indicated that GNPs and glutaraldehyde (GTA) decreased HaCaT cell viability in a concentration/time-dependent manner. However, both blank nanoparticles (B-NC) and rutin-loaded nanoparticles (R-NC) had good performance on skin compatibility tests. These results functionally characterized rutin-loaded nanoparticles as a safe SPF enhancer in sunscreens, especially in association with UV filters. Copyright © 2015 Elsevier B.V. All rights reserved.

Epigallocatechin Gallate (EGCG) Decorating Soybean Seed Ferritin as a Rutin Nanocarrier with Prolonged Release Property in the Gastrointestinal Tract.

PubMed

Yang, Rui; Sun, Guoyu; Zhang, Min; Zhou, Zhongkai; Li, Quanhong; Strappe, Padraig; Blanchard, Chris

2016-09-01

The instability and low bioavailability of polyphenols limit their applications in food industries. In this study, epigallocatechin gallate (EGCG) and soybean seed ferritin deprived of iron (apoSSF) were fabricated as a combined double shell material to encapsulate rutin flavonoid molecules. Firstly, due to the reversible assembly characteristics of phytoferritin, rutin was successfully encapsulated within apoSSF to form a ferritin-rutin complex (FR) with an average molar ratio of 28.2: 1 (rutin/ferritin). The encapsulation efficiency and loading capacity of rutin were 18.80 and 2.98 %, respectively. EGCG was then bound to FR to form FR-EGCG composites (FRE), and the binding number of EGCG was 27.30 ± 0.68 with a binding constant K of (2.65 ± 0.11) × 10(4) M(-1). Furthermore, FRE exhibited improved rutin stability, and displayed prolonged release of rutin in simulated gastrointestinal tract fluid, which may be attributed to the external attachment of EGCG to the ferritin cage potentially reducing enzymolysis in GI fluid. In summary, this work demonstrates a novel nanocarrier for stabilization and sustained release of bioactive polyphenols.

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

Increase of rutin antioxidant activity by generating Maillard reaction products with lysine.

PubMed

Zhang, Ru; Zhang, Bian-Ling; He, Ting; Yi, Ting; Yang, Ji-Ping; He, Bin

2016-06-01

Rutin exists in medicinal herbs, fruits, vegetables, and a number of plant-derived sources. Dietary sources containing rutin are considered beneficial because of their potential protective roles in multiple diseases related to oxidative stresses. In the present study, the change and antioxidation activity of rutin in Maillard reaction with lysine through a heating process were investigated. There is release of glucose and rhamnose that interact with lysine to give Maillard reaction products (MRPs), while rutin is converted to less-polar quercetin and a small quantity of isoquercitrin. Because of their high cell-membrane permeability, the rutin-lysine MRPs increase the free radical-scavenging activity in HepG2 cells, showing cellular antioxidant activity against Cu(2+)-induced oxidative stress higher than that of rutin. Furthermore, the MRPs significantly increased the Cu/Zn SOD (superoxide dismutase) activity and Cu/Zn SOD gene expression of HepG2 cells, consequently enhancing antioxidation activity. Copyright © 2016 Elsevier Ltd. All rights reserved.

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).

Chemical constituents from Tillandsia recurvata.

PubMed

de Queiroga, Marcos Aurélio; de Andrade, Lucimara Mariano; Florêncio, Karina Chagas; de Fátima Agra, Maria; da Silva, Marcelo Sobral; Barbosa-Filho, José Maria; da-Cunha, Emidio Vasconcelos Leitão

2004-06-01

The CHCl3 extract of Tillandsia recurvata yielded 5,3'-dihydroxy-6,7,8,4'-tetramethoxyflavanone (1), 1,3-di-O-cinnamoyl-glycerol (2) and ethyl ester of caffeic acid. Their structures were elucidated by means of spectroscopic methods such as mass spectroscopy and 1 and 2D-NMR. Copyright 2004 Elsevier B.V.

Reducing the allergenic capacity of peanut extracts and liquid peanut butter by phenolic compounds.

USDA-ARS?s Scientific Manuscript database

Phenolic compounds are known to form soluble and insoluble complexes with proteins. The objective of this study was to determine if phenolics, such as, caffeic, chlorogenic, and ferulic acids form insoluble and irreversible complexes with major peanut allergens. We also tested whether such complexat...

Hybridization of downregulated-COMT transgenic switchgrass lines with field selected switchgrass for improved biomass traits

USDA-ARS?s Scientific Manuscript database

Transgenic switchgrass (Panicum virgatum L.) has been produced for improved cell walls for biofuels. Downregulated caffeic acid 3-O-methyltransferase (COMT) switchgrass produced significantly more biomass and biofuel than the non-transgenic progenitor line. In the present study we sought to further...

Chlorogenic Acid Biosynthesis Appears Linked with Suberin Production in Potato Tuber (Solanum tuberosum).

PubMed

Valiñas, Matías Ariel; Lanteri, María Luciana; ten Have, Arjen; Andreu, Adriana Balbina

2015-05-20

Potato (Solanum tuberosum L.) is a good source of dietary antioxidants. Chlorogenic acid (CGA) and caffeic acid (CA) are the most abundant phenolic acid antioxidants in potato and are formed by the phenylpropanoid pathway. A number of CGA biosynthetic routes that involve hydroxycinnamoyl-CoA quinate hydroxycinnamoyl transferase (HQT) and/or hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase (HCT) have been proposed, but little is known about their path in potato. CA production requires a caffeoyl shikimate esterase (CSE), and CA serves as a substrate of lignin precursor ferulic acid via the action of caffeic/5-hydroxyferulic acid O-methyltransferase (COMT I). CGA is precursor of caffeoyl-CoA and, via caffeoyl-CoA O-methyltransferase (CCoAOMT), of feruloyl-CoA. Feruloyl-CoA is required for lignin and suberin biosynthesis, crucial for tuber development. Here, metabolite and transcript levels of the mentioned and related enzymes, such as cinnamate 4-hydroxylase (C4H), were determined in the flesh and skin of fresh and stored tubers. Metabolite and transcript levels were higher in skin than in flesh, irrespective of storage. CGA and CA production appear to occur via p-coumaroyl-CoA, using HQT and CSE, respectively. HCT is likely involved in CGA remobilization toward suberin. The strong correlation between CGA and CA, the correspondence with C4H, HQT, CCoAOMT2, and CSE, and the negative correlation of HCT and COMT I in potato tubers suggest a major flux toward suberin.

An unusual caffeic acid derived bicyclic [2.2.2] octane lignan and other constituents from Cordia rufescens.

PubMed

do Vale, Ademir E; David, Jorge M; dos Santos, Edlene O; David, Juceni P; e Silva, Lidercia C R C; Bahia, Marcus V; Brandão, Hugo N

2012-04-01

This work reports isolation of an unusual lignan with a bicyclic [2.2.2] octene skeleton, named rufescenolide (1), from stems of Cordia rufescens, along with β-sitosterol, stigmasterol, syringaldehyde, 3-β-O-D-glucopyranosyl-sitosterol, methyl caffeate, 4-methoxy-protocatechuic acid and methyl rosmarinate. Structural characterizations employed IR spectroscopic, ESIHRMS and mono and dimensional NMR spectroscopy. Copyright © 2011 Elsevier Ltd. All rights reserved.

High Performance Liquid Chromatography-Diode Array Detector Method for the Simultaneous Determination of Five Compounds in the Pulp and Seed of Sea Buckthorn.

PubMed

Zhao, Lu; Wen, E; Upur, Halmuart; Tian, Shuge

2017-01-01

Sea buckthorn ( Hippophae rhamnoides L.) as a traditional Chinese medicinal plant has various uses in Xinjiang. A reversed-phase rapid-resolution liquid-chromatography method with diode array detector was developed for simultaneous determination of protocatechuic acid, rutin, quercetin, kaempferol, and isorhamnetin in the pulp and seed of sea buckthorn, a widely used traditional Chinese medicine for promoting metabolism and treating scurvy and other diseases. Compounds were separated on an Agilent ZORBAX SB-C18 column (4.6 mm × 250 mm, 5 μm; USA) with gradient elution using methanol and 0.4% phosphoric acid (v/v) at 1.0 mL/min. Detection wavelength was set at 280 nm. The fruits of wild sea buckthorn were collected from Wushi County in Aksu, Xinjiang Province. The RSD of precision test of the five compounds were in the range of 0.60-2.22%, and the average recoveries ranged from 97.36% to 101.19%. Good linearity between specific chromatographic peak and component qualities were observed in the investigated ranges for all the analytes ( R 2 > 0.9997). The proposed method was successfully applied to determine the levels of five active components in sea buckthorn samples from Aksu in Xinjiang. The proposed method is simple, fast, sensitive, accurate, and suitable for quantitative assessment of the pulp and seed of sea buckthorn. Quantitative analysis method of protocatechuic acid, rutin, quercetin, kaempferol, and isorhamnetin in the extract of sea buckthorn pulp and seed is developed by high-performance liquid chromatography (HPLC) diode array detection.This method is simple and accurate; has strong specificity, good precision, and high recovery rate; and provides a reliable basis for further development of the substances in the pulp and seed of sea buckthorn.The method is widely used for content determination of active ingredients or physiologically active components in traditional Chinese medicine and its preparation Abbreviation used: PR: protocatechuic acid, RU: rutin, QU: quercetin, KA: kaempferol, IS: isorhamnetin, HPLC: high-performance liquid chromatography, HPLC-DAD: high performance liquid chromatographydiode array detector, LOD: linearity and limit of detection, LOQ: limit of quantitation, RSD: relative standard deviation.

Protective effects of ferulic acid and related polyphenols against glyoxal- or methylglyoxal-induced cytotoxicity and oxidative stress in isolated rat hepatocytes.

PubMed

Maruf, Abdullah Al; Lip, HoYin; Wong, Horace; O'Brien, Peter J

2015-06-05

Glyoxal (GO) and methylglyoxal (MGO) cause protein and nucleic acid carbonylation and oxidative stress by forming reactive oxygen and carbonyl species which have been associated with toxic effects that may contribute to cardiovascular disease, complications associated with diabetes mellitus, Alzheimer's and Parkinson's disease. GO and MGO can be formed through oxidation of commonly used reducing sugars e.g., fructose under chronic hyperglycemic conditions. GO and MGO form advanced glycation end products which lead to an increased potential for developing inflammatory diseases. In the current study, we have investigated the protective effects of ferulic acid and related polyphenols e.g., caffeic acid, p-coumaric acid, methyl ferulate, ethyl ferulate, and ferulaldehyde on GO- or MGO-induced cytotoxicity and oxidative stress (ROS formation, protein carbonylation and mitochondrial membrane potential maintenance) in freshly isolated rat hepatocytes. To investigate and compare the protective effects of ferulic acid and related polyphenols against GO- or MGO-induced toxicity, five hepatocyte models were used: (a) control hepatocytes, (b) GSH-depleted hepatocytes, (c) catalase-inhibited hepatocytes, (d) aldehyde dehydrogenase (ALDH2)-inhibited hepatocytes, and (e) hepatocyte inflammation system (a non-toxic H2O2-generating system). All of the polyphenols tested significantly decreased GO- or MGO-induced cytotoxicity, ROS formation and improved mitochondrial membrane potential in these models. The rank order of their effectiveness was caffeic acid∼ferulaldehyde>ferulic acid>ethyl ferulate>methyl ferulate>p-coumaric acid. Ferulic acid was found to decrease protein carbonylation in GSH-depleted hepatocytes. This study suggests that ferulic acid and related polyphenols can be used therapeutically to inhibit or decrease GO- or MGO-induced hepatotoxicity. Copyright © 2014 Elsevier Ireland Ltd. All rights reserved.

Antimicrobial activity of natural products from the flora of Northern Ontario, Canada.

PubMed

Vandal, Janique; Abou-Zaid, Mamdouh M; Ferroni, Garry; Leduc, Leo G

2015-06-01

The number of multidrug resistant (MDR) microorganisms is increasing and the antimicrobial resistance expressed by these pathogens is generating a rising global health crisis. In fact, there are only a few antimicrobial agents left that can be used against MDR bacteria and fungi. In this study, the antimicrobial activities of selected natural products from the flora of Northern Ontario against selected microorganisms are reported. Plants were collected from Sault Ste. Marie, Ontario, Canada, and ethanol extracts were prepared using EtOH:H2O (1:1, v/v). Fungal cultures used in this study were Candida albicans ATCC 10231 and Schizosaccharomyces octosporus. Bacterial cultures employed included Staphylococcus aureus ATCC 29213, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Mycobacterium phlei ATCC 11758, and Streptococcus lactis ATCC 19435. The microplate resazurin assay was used to screen for antimicrobial activity. Extracts of four plant species Chimaphila umbellata L. (Pyrolaceae), Betula papyrifera Marshall (Betulaceae), Rhus typhina L. (Anacardiaceae), and Fraxinus pennsylvanica Marshall (Oleaceae), and six compounds (gallic acid, ethyl gallate, caffeic acid, sinapic acid, gentisic acid, and chlorogenic acid) demonstrated antibacterial or antifungal activities with MICs ranging from 62.5 to 1000 µg/mL, respectively, for a chemical fraction of an extract from Betula papyrifera against the bacterium S. aureus. The present study has shown that certain plant extracts and select fractions and standard chemical compounds exhibit antimicrobial effects. Prince's Pine, Chimaphila umbellate, White Birch, Betula papyrifera, Staghorn Sumac, Rhus typhina, and Green Ash, Fraxinus pennsylvanica were the principal extracts exhibiting notable antibacterial and/or antifungal activities; while gallic acid, ethyl gallate, and caffeic acid demonstrated antibacterial activities and sinapic acid, gentisic acid, and chlorogenic acid demonstrated antifungal activities.

Safety and Antioxidant Efficacy Profiles of Rutin-Loaded Ethosomes for Topical Application.

PubMed

Cândido, Thalita Marcílio; De Oliveira, Camila Areias; Ariede, Maíra Bueno; Velasco, Maria Valéria Robles; Rosado, Catarina; Baby, André Rolim

2018-05-01

Topical application of dermocosmetics containing antioxidant and/or the intake of antioxidants through diet or supplementation are remarkable tools in an attempt to slow down some of the harmful effects of free radicals. Rutin is a strong antioxidant compound used in food and pharmaceutical industries. It was established that rutin presents a low skin permeation rate, a property that could be considered an inconvenience to the satisfactory action for a dermocosmetic formulation to perform its antioxidant activity onto the skin. Therefore, it is indispensable to improve its delivery, aiming at increasing its antioxidant capacity in deeper layers of the epidermis, being a possibility to associate the rutin to liposomal vesicles, such as ethosomes. Thus, in this work, the pre-clinical safety of rutin-loaded ethosomes was investigated employing an in vitro method, and the clinical safety and efficacy were also assessed. Rutin-loaded ethosomes were efficaciously obtained in a nanoscale dimension with a relevant bioactive compound loading (80.2%) and provided antioxidant in vitro activity in comparison with the blank sample. Pre-clinical and clinical safety assays assured the innocuous profile of the rutin-loaded ethosomes. The ethosomes containing the bioactive compound accomplished a more functional delivery system profile, since in the tape stripping assay, the deeper layers presented higher rutin amounts than the active delivered in its free state. However, the ex vivo antioxidant efficacy test detected no positive antioxidant activity from the rutin-loaded ethosomes, even though the in vitro assay demonstrated an affirmative antioxidant action.

Investigation on the interaction of Rutin with serum albumins: Insights from spectroscopic and molecular docking techniques.

PubMed

Sengupta, Priti; Sardar, Pinki Saha; Roy, Pritam; Dasgupta, Swagata; Bose, Adity

2018-06-01

The binding interaction of Rutin, a flavonoid, with model transport proteins, bovine serum albumin (BSA) and human serum albumin (HSA), were investigated using different spectroscopic techniques, such as fluorescence, time-resolved single photon counting (TCSPC) and circular dichroism (CD) spectroscopy as well as molecular docking method. The emission studies revealed that the fluorescence quenching of BSA/HSA by Rutin occurred through a simultaneous static and dynamic quenching process, and we have evaluated both the quenching constants individually. The binding constants of Rutin-BSA and Rutin-HSA system were found to be 2.14 × 10 6  M -1 and 2.36 × 10 6  M -1 at 298 K respectively, which were quite high. Further, influence of some biologically significant metal ions (Ca 2+ , Zn 2+ and Mg 2+ ) on binding of Rutin to BSA and HSA were also investigated. Thermodynamic parameters justified the involvement of hydrogen bonding and weak van der Waals forces in the interaction of Rutin with both BSA and HSA. Further a site-marker competitive experiment was performed to evaluate Rutin binding site in the albumins. Additionally, the CD spectra of BSA and HSA revealed that the secondary structure of the proteins was perturbed in the presence of Rutin. Finally protein-ligand docking studies have also been performed to determine the probable location of the ligand molecule. Copyright © 2018 Elsevier B.V. All rights reserved.

Dietary supplementation with rutin has pro-/anti-inflammatory effects in the liver of juvenile GIFT tilapia, Oreochromis niloticus.

PubMed

Zheng, Yao; Zhao, Zhixiang; Fan, Limin; Meng, Shunlong; Song, Chao; Qiu, Liping; Xu, Pao; Chen, Jiazhang

2017-05-01

Dietary supplementation with rutin may have some pharmacological qualities including anti-inflammatory effects. Kupffer cell activation resulted in increased transcription of pro- and anti-inflammatory cytokines. The main purpose of this study was to investigate the pro- and anti-inflammatory activities in juvenile freshwater tilapia, Oreochromis niloticus, in response to 0.1 or 0.3 g/kg dietary supplementation of rutin. Results showed that hepatic IgM, anti-inflammatory-cytokines, and pro-inflammatory cytokines were significantly decreased in groups treated with high doses of rutin. Hepatic IgM and anti-inflammatory cytokines (IL-10 and IFN-γ) transcripts were significantly decreased, whereas the transcripts of the pro-inflammatory cytokines, TNFα and IL-1β were significantly decreased, whereas IL-8 was significantly increased. The number of Kupffer cells in rutin-treated groups was significantly decreased, and scanning electron micrographs showed that rutin enriched the number of gut microvilli and secretion pits. With the phenomena of cell apoptosis occurred in the rutin groups, the present study demonstrated that optimum levels of rutin may be beneficial but excessive level may cause liver impairment, which may be absorbed by the gut and then transported to the liver. Copyright © 2017 Elsevier Ltd. All rights reserved.

[Chemical constituents of the roots of Vaccinium bracteatum].

PubMed

Lv, Xiao-Lan; Mai, Xi; Guo, Hui; Lai, Xiao-Ping

2012-06-01

To study the chemical constituents of the roots of Vaccinium bracteatum. The constituents were separated and purified with chromatographic methods (including silica gel, Sephadex LH-20 and RP-18 column chromatography), and their structures were determined by spectroscopic methods (including MS, 1H-NMR and 13C-NMR). 10 compounds were isolated from the roots of Vaccinium bracteatu and were elucidated as chlorogenic acid (1), pinoresinol (2), ferulic acid (3), kaempferol (4), trans-caffeic acid (5), beta-sitosterol (6), quercetin (7), oleanolic acid (8), apigenin (9) and luteolin (10). Compounds 1 -3 are obtained from this plant for the first time.

[Studies on chemical constituents of Taxillus sutchuenenisis].

PubMed

Chen, Jiang-tao; Feng, Feng

2007-11-01

To study the chemical constituents of Taxillus sutchuenenisis (Lecomte) Danser. Chromatography and spectrum analysis were employed to isolated and elucidate the chemical constituents in the plant. 9 compounds were isolated and identified as quercetin (I), quervetin 3-O-beta-D-galactoside (II), isoquercitrin (III), quercitrin (IV), rutin (V), gallic acid (VI), ferulic acid (VII), beta-sitosterol (VIII), daucosterol (IX), respectively. Compounds III-IX are isolated from this plant for the first time. The work provide evidence for the exploitation and utilization of this plant resouce.

Simultaneous qualitative and quantitative analysis of phenolic acids and flavonoids for the quality control of Apocynum venetum L. leaves by HPLC-DAD-ESI-IT-TOF-MS and HPLC-DAD.

PubMed

An, Haijuan; Wang, Hong; Lan, Yuexiang; Hashi, Yuki; Chen, Shizhong

2013-11-01

A reliable method based on high performance liquid chromatography-diode array detector-electrospray ionization-ion trap-time of flight-mass spectrometry (HPLC-DAD-ESI-IT-TOF-MS) was developed for the identification of phenolic acids and flavonoids in Apocynum venetum L. leaves and its adulterant, Pocynum hendersonii (Hook. f.) Woodson leaves. A total of 21 compounds were identified or tentatively identified, including 4 phenolic acids and 17 flavonoids. 3-O-caffeoylquinic acid (3-CQA) and caffeic acid were detected for the first time in A. venetum leaves; 4-O-caffeoylquinic acid (4-CQA), 3-CQA, caffeic acid, quercetin-3-O-(6"-O-malonyl)-galactoside, quercetin-3-O-(6"-O-malonyl)-glucoside, kaempferol-3-O-(6"-O-malonyl)-glucoside, kaempferol-3-O-(6"-O-acetyl)-glucoside, and kaempferol-3-O-dihexoside were detected for the first time in P. hendersonii leaves. Cluster analysis was employed to analyze 24 batches of A. venetum leaves and 5 batches of P. hendersonii leaves collected from various regions in China. The analysis, which was based on the 21 compounds, indicated that profiles of these compounds were distinct between the two species, and among A. venetum leaf samples from different origins. 18 of these 21 compounds were selected as the markers and simultaneously analyzed by HPLC-DAD for the first time. The quantitative analytical method was validated and subsequently applied to the comprehensive quality evaluation of 24 batches of A. venetum leaves. © 2013 Elsevier B.V. All rights reserved.

An innovative monolithic zwitterionic stationary phase for the separation of phenolic acids in coffee bean extracts by capillary electrochromatography.

PubMed

Murauer, Adele; Bakry, Rania; Schottenberger, Herwig; Huck, Christian; Ganzera, Markus

2017-04-22

A methacrylate based monolith, containing the innovative zwitterionic monomer (3-allyl-1-imidazol)propane sulfonate, was prepared in 100 μm I.D. silica capillaries by UV initiated photo-polymerization. Composition of the porogen, i.e. a mixture of 1-propanol, 1,4 butanediol and water, was of great importance to obtain a homogeneous monolith with satisfactory permeability and good electrochromatographic performance. Morphology of the stationary phase was studied in Scanning Electron Microscopy and IR experiments, which revealed a good attachment to the capillary wall, flowthrough-pores in the range of 0.5-2 μm, and a continuous monolithic structure. The developed material was well suited for the analysis of six common phenolic acids (salicylic, cinnamic, syringic, rosmarinic, caffeic and chlorogenic acid) by CEC. Their separation was possible in less than 8 min with a mobile phase comprising a 12 mM aqueous ammonium acetate solution with pH 8.5 and acetonitrile, at an applied voltage of - 20 kV. The developed method was validated (R 2  ≥ 0.995; LOD ≤ 3.9 μg mL -1 , except for salicylic acid; recovery rates from 94 to 104%) and successfully used for the determination of phenolic acids in Coffea arabica samples. All of them contained cinnamic, syringic and caffeic acid, however only in unroasted coffee beans chlorogenic acid (0.06%) was found. The quantitative results were in good agreement to reported literature data. Copyright © 2017 The Author(s). Published by Elsevier B.V. All rights reserved.

Enzymatic oxidation of rutin by horseradish peroxidase: kinetic mechanism and identification of a dimeric product by LC-Orbitrap mass spectrometry.

PubMed

Savic, Sasa; Vojinovic, Katarina; Milenkovic, Sanja; Smelcerovic, Andrija; Lamshoeft, Marc; Petronijevic, Zivomir

2013-12-15

Flavonoid oxidation is important issue in food processing and quality. The kinetic mechanism of enzymatic oxidation of rutin by horseradish peroxidase (HRP) was studied. Rutin oxidation reaction was followed by recording of spectral changes over the time at 360 nm. The studied oxidation is mostly enzymatic and less part non-enzymatic. The reaction with HRP has a higher rate compared with the reaction without of HRP, whereby is part of non-enzymatic reaction about 10% of the total reaction. Kinetic parameters were determined from graphics of linear Michaelis-Menten equation, and it was found that investigated reactions of rutin oxidation by HRP take place in a ping-pong kinetic mechanism. High resolution HPLC-MS analysis of the mixture of oxidized products of rutin revealed the presence of rutin dimer. Because of widely distribution of rutin as well as presence of peroxidases and hydrogen peroxide in fresh foods identification of this enzymatic modification product can be beneficial for foods quality and safety. Copyright © 2013 Elsevier Ltd. All rights reserved.

Effects of rutin on the redox reactions of hemoglobin.

PubMed

Lu, Naihao; Ding, Yun; Yang, Zhen; Gao, Pingzhang

2016-08-01

Flavonoids are widely used to attenuate oxidative damage in vitro and in vivo. In this study, we investigated the influence of rutin (quercetin-3-rhamnosylglucoside) on hemoglobin (Hb)- dependent redox reactions, i.e. oxidative stability of Hb and its cytotoxic ferryl intermediate. It was found that rutin induced generation of H2O2, which in turn oxidized Hb rapidly. Meanwhile, rutin exhibited anti-oxidant effect by effectively reducing ferryl intermediate back to ferric Hb at physiological pH. In comparison with quercetin, rutin had stronger capability on reducing ferryl species while lesser pro-oxidant effect on H2O2 generation, thus it exhibited more protective effect on H2O2-induced Hb oxidation. Circular dichroism spectrum showed no significant change in the secondary structure of Hb after flavonoid addition, while molecular docking revealed different binding modes of quercetin and rutin with Hb. These results might provide new insights into the potential nutritional and physiological implications of rutin and quercetin with redox active heme proteins regarding their ani- and pro-oxidant effects. Copyright © 2016 Elsevier B.V. All rights reserved.

Solicitation of HPLC and HPTLC Techniques for Determination of Rutin from Polyalthia longifolia Thwaites

PubMed Central

Doshi, Gaurav Mahesh; Zine, Sandeep Prabhakar; Chaskar, Pratip Kashinath; Une, Hemant Devidas

2014-01-01

Background: Polyalthia longifolia Thwaites is an important traditional plant in India. Rutin, an active constituent has been reported to possess good amount of pharmacological as well as therapeutic potential. Objective: The aim of the present study was to find out by analytical techniques how much percentage of rutin is present in the plant leaves’ ethanolic extract by analytical techniques. Materials and Methods: Shade dried leaves of Polyalthia longifolia were subjected to cold ethanolic extraction followed by monitoring the isolated rutin high-pressure liquid chromatography (HPLC) and high performance thin layer chromatography (HPTLC) after carrying out preliminary phytochemical screening. Results: Extraction yield was found to be 13.94% w/w. Phytochemical screening of the extract showed the presence of flavonoids, steroids, diterpenoids, alkaloids, saponins, tannins and phenolic compounds and mucilage. From the Rf value, the ethanolic extract was found to be having constituent identical to rutin. By HPTLC and HPLC the amount of rutin was found to be 11.60% w/w and 4.03% w/v, respectively. Conclusion: The active constituent isolated was found to be equal to rutin. PMID:25002804

Ilex paraguariensis and its main component chlorogenic acid inhibit fructose formation of advanced glycation endproducts with amino acids at conditions compatible with those in the digestive system.

PubMed

Bains, Yasmin; Gugliucci, Alejandro

2017-03-01

We have previously shown that Ilex paraguariensis extracts have potent antiglycation actions. Associations of excess free fructose consumption with inflammatory diseases have been proposed to be mediated through in situ enteral formation of fructose AGEs, which, after being absorbed may contribute to inflammatory diseases via engagement of RAGE. In this proof of principle investigation we show fluorescent AGE formation between amino acids (Arg, Lys, Gly at 10-50mM) and fructose (10-50mM) under time, temperature, pH and concentrations compatible with the digestive system lumen and its inhibition by Ilex paraguariensis extracts. Incubation of amino acids with fructose (but not glucose) leads to a time dependent formation of AGE fluorescence, already apparent after just 1h incubation, a time frame well compatible with the digestive process. Ilex paraguariensis (mate tea) inhibited AGE formation by 83% at 50μl/ml (p<0.001). Its main phenolics, caffeic acid and cholorogenic acid were as potent as aminoguanidine-a specific antiglycation agent: IC50 of 0.9mM (p<0.001). Our results suggest that AGE adducts form between fructose and amino acids at times and concentrations plausibly found in the intestines. The reaction is inhibited by mate tea and its individual phenolics (caffeic acid and chlorogenic acids). The study provides the first evidence for the proposed mechanism to explain epidemiological correlations between excess fructose consumption and inflammatory diseases. Enteral fructose-AGE formation would be inhibited by co-intake of Ilex paraguariensis, and potentially other beverages, fruits and vegetables that contain comparable concentrations of phenolics as in IP (mate tea). Copyright © 2016 Elsevier B.V. All rights reserved.

Novel stilbenoids, including cannabispiradienone glycosides, from Tragopogon tommasinii (Asteraceae, Cichorieae) and their potential anti-inflammatory activity.

PubMed

Granica, Sebastian; Piwowarski, Jakub P; Randazzo, Antonio; Schneider, Peter; Żyżyńska-Granica, Barbara; Zidorn, Christian

2015-09-01

A phytochemical investigation of Tragopogon tommasinii Sch.Bip. (Asteraceae, Cichorieae) yielded a total of 21 natural products, two simple phenolic acids (4-hydroxybenzoic acid and p-coumaric acid), four caffeic acid derivatives (chlorogenic acid, 3-O-caffeoylquinic acid, 3,5-O-dicaffeoylquinic acid, and 4,5-O-dicaffeoylquinic acid), six flavonoids (luteolin, luteolin 7-O-glucoside, vitexin, orientin, quercetin 3-O-glucoside, and isorhamnetin 3-O-glucoside), three simple bibenzyls [2-carboxyl-5-hydroxy-3-methoxy-4'-β-glucopyranosyl-oxybibenzyl, 3-caffeoyl-(9→5)-β-apiosyl-(1→6)-β-glucopyranosyloxy-5,4'-dihydroxy-3'-methoxybibenzyl, 3-caffeoyl-(9→5)-β-apiosyl-(1→6)-β-glucopyranosyloxy-4'-dihydroxy-5,3'-dimethoxybibenzyl], three phtalides [3-(4-β-glucopyranosyloxybenzyl)-7-hydroxy-5-methoxyphtalide, 7-β-glucopyranosyloxy-(S)-3-(4-hydroxybenzyl)-5-methoxyphtalide, and 7-(1→6)-α-rhamnosyl-β-glucopyranosyloxy-(S)-3-(4-hydroxybenzyl)-5-methoxyphtalide], two cannabispiradienone derivatives [3-O-β-glucopyranosyldemethoxycannabispiradienone and 3-caffeoyl-(9→5)-β-apiosyl-(1→6)-β-glucopyranosyloxydemethoxycannabispiradienone], and tetra-N-coumaroyl spermine. The three bibenzyls, the latter two benzylphthalides, and both cannabispiradienone derivatives represent new natural compounds and all compounds, except the caffeic acid derivatives and the flavonoids were new for T. tommasinii. The structures were established by HR mass spectrometry, extensive 1D and 2D NMR spectroscopy, and CD spectroscopy. Moreover, the potential anti-inflammatory activities of the new compounds were assayed using human neutrophils and their production of IL-1b, IL-8, TNF-α and MMP-9 as well as the expression of TLR-4, respectively. Copyright © 2015 Elsevier Ltd. All rights reserved.

Metabolism of rutin and poncirin by human intestinal microbiota and cloning of their metabolizing α-L-rhamnosidase from Bifidobacterium dentium.

PubMed

Bang, Seo-Hyeon; Hyun, Yang-Jin; Shim, Juwon; Hong, Sung-Woon; Kim, Dong-Hyun

2015-01-01

To understand the metabolism of flavonoid rhamnoglycosides by human intestinal microbiota, we measured the metabolic activity of rutin and poncirin (distributed in many functional foods and herbal medicine) by 100 human stool specimens. The average α-Lrhamnosidase activities on the p-nitrophenyl-α-L-rhamnopyranoside, rutin, and poncirin subtrates were 0.10 ± 0.07, 0.25 ± 0.08, and 0.15 ± 0.09 pmol/min/mg, respectively. To investigate the enzymatic properties, α-L-rhamnosidase-producing bacteria were isolated from the specimens, and the α-L-rhamnosidase gene was cloned from a selected organism, Bifidobacterium dentium, and expressed in E. coli. The cloned α-L-rhamnosidase gene contained a 2,673 bp sequcence encoding 890 amino acid residues. The cloned gene was expressed using the pET 26b(+) vector in E. coli BL21, and the expressed enzyme was purified using Ni(2+)-NTA and Q-HP column chromatography. The specific activity of the purified α-L-rhamnosidase was 23.3 μmol/min/mg. Of the tested natural product constituents, the cloned α-L-rhamnosidase hydrolyzed rutin most potently, followed by poncirin, naringin, and ginsenoside Re. However, it was unable to hydrolyze quercitrin. This is the first report describing the cloning, expression, and characterization of α-L-rhamnosidase, a flavonoid rhamnoglycosidemetabolizing enzyme, from bifidobacteria. Based on these findings, the α-L-rhamnosidase of intestinal bacteria such as B. dentium seem to be more effective in hydrolyzing (1-->6) bonds than (1-->2) bonds of rhamnoglycosides, and may play an important role in the metabolism and pharmacological effect of rhamnoglycosides.

Extraction and Purification of Quercitrin, Hyperoside, Rutin, and Afzelin from Zanthoxylum Bungeanum Maxim Leaves Using an Aqueous Two-Phase System.

PubMed

He, Fengyuan; Li, Dengwu; Wang, Dongmei; Deng, Ming

2016-07-01

In this study, an aqueous two-phase system (ATPS) based on ethanol/NaH2 PO4 was developed for the extraction and purification of quercitrin, hyperoside, rutin, and afzelin from Zanthoxylum bungeanum Maxim leaves. These 4 flavonoids were 1st extracted from dried Z. bungeanum leaves using a 60% ethanol solution and subsequently added to the ATPS for further purification. The partition behavior of the 4 flavonoids in ATPS was investigated. The optimal ATPS conditions were: 29% (w/w) NaH2 PO4 , 25% (w/w) ethanol concentration, 1% (w/w) added amount of leaf extracts, no pH adjustment, and repeated 1 h extractions at 25 °C. Under the optimal conditions for the 10 g ATPS, the absolute recovery of quercitrin, hyperoside, rutin, and afzelin reached 90.3%, 83.5%, 92.3%, and 89.1%, respectively. Compared to the 60% ethanol extracts, the content of quercitrin (44.8 mg/g), hyperoside (65.6 mg/g), rutin (56.4 mg/g), and afzelin (6.84 mg/g) in the extracts increased by 49.9%, 38.8%, 45.6%, and 36.8% respectively. The extracts after ATPS also exhibited stronger antioxidant activities, the 2,2-diphenyl-1-picrylhydrazyl IC50 value (10.5 μg/mL) decreased by 41.8%, and the 2,2-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt value (966 μmol Trolox/g) and ferric reducing power value (619 μmol Trolox/g) increased by 29.8% and 53.7%, respectively. Furthermore, scale-up experiments indicated that a larger scale experiment was feasible for the purification of the 4 flavonoids. © 2016 Institute of Food Technologists®

Development of a validated HPLC method for the simultaneous determination of flavonoids in Cuscuta chinensis Lam. by ultra-violet detection

PubMed Central

2012-01-01

Background Cuscuta species known as dodder, have been used in traditional medicine of eastern and southern Asian countries as liver and kidney tonic. Flavonoids are considered as the main biologically active constituents in Cuscuta plants especially in C. chinensis Lam. Objective In the present study, a fast, simple and reliable method for the simultaneous determination and quantization of C. chinensis flavonols including hyperoside, rutin, isorhamnetin and kaempferol has been developed. Materials and methods The chromatographic separation was carried out on a reversed phase ACE 5 C18 with eluting at a flow rate of 1 ml/min using a gradient with O-phosphoric acid 0.25% : acetonitrile for 42 min. UV spectra were collected across the range of 200–900 nm, extracting 360 nm for the chromatograms. The method was validated according to linearity, selectivity, precision, recovery, LOD and LOQ. Results The method was selective for determination of rutin, hyperoside, isorhamnetin and kampferol. The calibration graphs of flavonols were linear with r2 > 0.999. RSDs% of intra- and inter-day precisions were found 1.3&3.4 for rutin, 1.5&2.8 for hyperoside, 1.3&3.3 for isorhamnetin and 1.7 & 2.9 for kaempferol which were satisfactory. LODs and LOQs were calculated as 1.73 & 8.19 for rutin, 0.09 & 4.19 for hyperoside, 2.09 & 6.3 for isorhamnetin and 0.18 & 0.56 for kaempferol. The recovery averages of above-mentioned flavonols were 90.3%, 97.4%, 98.7% and 90.0%, respectively. Conclusion The simplicity of the method makes it highly valuable for quality control of C. chinensis according to quantization of flavonols. PMID:23352257

Quantification of Quercetin and Rutin from Benincasa hispida Seeds and Carissa Congesta Roots by High-performance Thin Layer Chromatography and High-performance Liquid Chromatography.

PubMed

Doshi, Gaurav Mahesh; Une, Hemant Devidas

2016-01-01

In Indian Ayurvedic system, Benincasa hispida (BH) and Carissa congesta (CC) are well-known plants used for major and minor ailments. BH has been regarded as Kushmanda, whereas CC has been used in immune-related disorders of the human system. Quercetin and rutin identified from the vast plethora of plant extracts have proved to possess ethnopharmacological relevance. In present studies, we have determined quercetin and rutin in terms of percentage in BH seeds and CC roots by high-performance thin layer chromatography (HPTLC) and high-performance liquid chromatography (HPLC). After extraction and phytochemical screening, the extracts were subjected to quantification for the presence of quercetin and rutin by HPTLC and HPLC. HPTLC showed quercetin as 44.60, 27.13% and rutin as 32.00, 36.31% w/w, whereas HPLC revealed quercetin as 34.00, 35.00% and rutin as 21.99, 45.03% w/v in BH and CC extracts, respectively. The BH and CC extracts have elucidated peaks that were corresponding with standard peaks on undertaking chromatographic studies. Quercetin and rutin are isolated from BH seeds and CC roots by High Performance. Thin Layer Chromatography and High Performance Liquid Chromatography. HPTLC revealed presence of quercetin as 44.60, 27.13 % and rutin as 32.00, 36.31 % w/w. HPLC revealed presence of quercetin as 34.00, 35.00 % and rutin as 21.99, 45.03 % w/v. Abbreviation Used: HPTLC: High Performance Thin Layer Chromatography; HPLC: High Pressure Liquid Chromatography, UV: Ultraviolet, CC: Carissa congesta, BH: Benincasa hispida.

Preventive effects of rutin on lysosomal enzymes in isoproterenol induced cardio toxic rats: biochemical, histological and in vitro evidences.

PubMed

Stanely Mainzen Prince, Ponnian; Priya, Shanmuga

2010-12-15

This study was aimed to evaluate the preventive effect of rutin on lysosomal enzymes in isoproterenol induced cardio toxic rats. Male albino Wistar rats were pretreated with rutin (80 mg/kg) daily for a period of 42 days. After the pretreatment period, isoproterenol (100 mg/kg) was subcutaneously injected to rats at an interval of 24 h for two days. The activity of serum creatine kinase-MB and the levels of serum troponins T and I and the activities of serum and heart lysosomal enzymes (β-glucuronidase, β-N-acetylglucosaminidase, β-galactosidase, cathepsin-B and D) were increased significantly (P<0.05) in isoproterenol induced cardio toxic rats. Isoproterenol induced cardio toxic rats also resulted in decreased stability of membranes, which was reflected by decreased activities of β-glucuronidase and cathepsin-D in mitochondrial, nuclear, lysosomal and microsomal fractions. Pretreatment with rutin daily for a period of 42 days to isoproterenol induced cardio toxic rats prevented the changes in the activities of these enzymes. Oral treatment with rutin (80 mg/kg) to normal rats did not show any significant effect in all the biochemical parameters studied. Histopathology of myocardium showed the preventive effects of rutin in isoproterenol induced cardio toxic rats. In vitro study also confirmed the mechanism of action of rutin. Thus, the results of our study show that rutin protects the lysosomal membrane against isoproterenol induced cardiac damage. The observed effects are due to the free radical scavenging, antioxidant and membrane stabilizing properties of rutin. Copyright © 2010 Elsevier B.V. All rights reserved.

Ameliorative effects of rutin against metabolic, biochemical and hormonal disturbances in polycystic ovary syndrome in rats.

PubMed

Jahan, Sarwat; Munir, Faryal; Razak, Suhail; Mehboob, Anam; Ain, Qurat Ul; Ullah, Hizb; Afsar, Tayyaba; Shaheen, Ghazala; Almajwal, Ali

2016-12-07

Polycystic ovary syndrome (PCOS) is the most prevalent endocrinopathy in women of reproductive age. The study was commenced to assess the favorable effects of Rutin against metabolic, biochemical, histological, and androgenic aspects of polycystic ovary syndrome in rats. Female Sprague-Dawley rats were administered letrozole (1 mg/kg) per orally (p.o) for a period of 21 days for the induction of PCOS, followed by dose of rutin (100 mg/kg and 150 mg/kg, p.o) for 15 days using 0.5% w/v CMC as vehicle. Metformin was also given as a standard control to one of the rat groups. Serum estradiol, progesterone, testosterone, serum lipid parameters, CRP and glucose levels were evaluated. Furthermore, antioxidant activity was tested using superoxide dismutase, catalase, glutathione per-oxidase and reactive-oxygen species level. Rutin flavonoid had a dose-dependent effect on androgenic levels depicting more recovery in the rutin-I treated group, while rutin-II treated groups showed better antioxidant and lipid profiles as compared with PCOS groups. A decrease in the value of C reactive protein (CRP) and a restoration in the proportion of estrous phase smears were observed in the rutin treated groups. Histopathological examination of ovary revealed a significant decrease in the number of cystic follicles in post treated groups. The effects observed with rutin were moderately similar to that with standard metformin, a widely used treatment drug for PCOS. The study provides evidence for the potential ameliorative effects of rutin against clinical and biochemical features of PCOS.

Lignin and Fiber digestibility in Caffeic Acid 3-O-Methyltransferase and Caffeoyl CoA 3-O-Methyltransferase Downregulated Alfalfa

USDA-ARS?s Scientific Manuscript database

Alfalfa (Medicago sativa L.) is one of the most important forages in the United States. Increasing alfalfa fiber digestibility would improve forage management and ration formulation flexibility. Currently, growers and breeders rely on near infrared spectroscopy (NIRS) to predict forage quality tra...

Cytoprotection of Human Endothelial Cells From Menadione Cytotoxicity by Caffeic Acid Phenethyl Ester: The Role of Heme Oxygenase-1

DTIC Science & Technology

2008-06-08

reported here show that CAPE induces HO-1 in human endothelial cells. The major signaling transduction involved in HO-1 induction by those electrophilic ...phenethyl ester (CAPE) and catechol ring- fluorinated CAPE derivatives against menadione-induced oxidative stress in human endothelial cells. Bioorganic

Caffeic Acid Phenethyl Ester: A Review of Its Antioxidant Activity, Protective Effects against Ischemia-reperfusion Injury and Drug Adverse Reactions.

PubMed

Tolba, Mai F; Omar, Hany A; Azab, Samar S; Khalifa, Amani E; Abdel-Naim, Ashraf B; Abdel-Rahman, Sherif Z

2016-10-02

Propolis, a honey bee product, has been used in folk medicine for centuries for the treatment of abscesses, canker sores and for wound healing. Caffeic acid phenethyl ester (CAPE) is one of the most extensively investigated active components of propolis which possess many biological activities, including antibacterial, antiviral, antioxidant, anti-inflammatory, and anti-cancer effects. CAPE is a polyphenolic compound characterized by potent antioxidant and cytoprotective activities and protective effects against ischemia-reperfusion (I/R)-induced injury in multiple tissues such as brain, retina, heart, skeletal muscles, testis, ovaries, intestine, colon, and liver. Furthermore, several studies indicated the protective effects of CAPE against chemotherapy-induced adverse drug reactions (ADRs) including several antibiotics (streptomycin, vancomycin, isoniazid, ethambutol) and chemotherapeutic agents (mitomycin, doxorubicin, cisplatin, methotrexate). Due to the broad spectrum of pharmacological activities of CAPE, this review makes a special focus on the recently published data about CAPE antioxidant activity as well as its protective effects against I/R-induced injury and many adverse drug reactions.

Caffeic acid phenethyl ester suppresses monocyte adhesion to the endothelium by inhibiting NF-κB/NOX2-derived ROS signaling

PubMed Central

Nakahara, Risa; Makino, Junya; Kamiya, Tetsuro; Hara, Hirokazu; Adachi, Tetsuo

2016-01-01

Caffeic acid phenethyl ester (CAPE), one of the major polyphenols, exhibits anti-oxidative, anti-bacterial, and anti-cancer properties. Atherosclerosis is a chronic inflammatory disease, the progression of which is closely related to the accumulated adhesion of inflammatory monocytes/macrophages to the endothelium. We herein determined whether CAPE and its derivatives suppressed THP-1 cell adhesion to human umbilical vein endothelial cells (HUVEC). Of the four polyphenols tested, CAPE significantly suppressed the 12-O-tetradecanoylphorbol 13-acetate (TPA)-elicited expression of cluster for differentiation (CD) 11b, 14, and 36, and this was accompanied by the inhibition of THP-1 cell adhesion to HUVEC. CAPE also suppressed the activation of TPA-elicited nuclear factor-κB (NF-κB) and accumulation of NADPH oxidase 2 (NOX2)-derived reactive oxygen species (ROS), but did not affect extracellular signal-regulated kinase (ERK) phosphorylation. Taken together, these results demonstrated that CAPE suppressed THP-1 cell adhesion to HUVEC through, at least in part, the NF-κB, NOX2, and ROS-derived signaling axis. PMID:27257341

Phenolic Acid Content and Antioxidant Properties of Extruded Corn Snacks Enriched with Kale

PubMed Central

Kasprzak, Kamila; Oniszczuk, Tomasz; Waksmundzka-Hajnos, Monika; Nowak, Renata; Polak, Renata

2018-01-01

Prohealth food contains specific components which have positive influence on the health and well-being of the consumer. An important position among bioactive compounds occurs for polyphenols. Many results have indicated that an increased intake of phenolic compounds may reduce the risk of cardiovascular diseases and type 2 diabetes. The objective of the study was production of extruded corn snacks with addition (0, 2, 4, 6, and 8%) of kale (Brassica oleracea L. var. sabellica)—a polyphenol-rich plant. Afterwards, high-performance liquid chromatography-mass spectrometry (LC-ESI-MS/MS) and antioxidant activity analyses of snack extracts were performed. In the corn snacks enriched with kale, fifteen phenolic acids were indicated. These were protocatechuic, 4-OH-benzoic, vanillic, trans-caffeic, cis-caffeic, trans-p-coumaric, cis-p-coumaric, trans-ferulic, cis-ferulic, salicylic, gentisic, syringic, 3-OH-cinnamic, trans-sinapic, and cis-sinapic acids. Both the qualitative and quantitative content of polyphenols increased with the addition of B. oleracea. Data from spectrophotometric analyses of the samples showed high DPPH radical scavenging potential of snacks enriched with 4, 6, and 8% of kale. Snacks enriched with kale contain high level of phenolic acids and, therefore, have great potential to make a valuable source of natural antioxidants. High-temperature short-time extrusion-cooking process had no negative impact on polyphenol's activity. PMID:29507816

Phenolic Acid Content and Antioxidant Properties of Extruded Corn Snacks Enriched with Kale.

PubMed

Kasprzak, Kamila; Oniszczuk, Tomasz; Wójtowicz, Agnieszka; Waksmundzka-Hajnos, Monika; Olech, Marta; Nowak, Renata; Polak, Renata; Oniszczuk, Anna

2018-01-01

Prohealth food contains specific components which have positive influence on the health and well-being of the consumer. An important position among bioactive compounds occurs for polyphenols. Many results have indicated that an increased intake of phenolic compounds may reduce the risk of cardiovascular diseases and type 2 diabetes. The objective of the study was production of extruded corn snacks with addition (0, 2, 4, 6, and 8%) of kale ( Brassica oleracea L. var. sabellica )-a polyphenol-rich plant. Afterwards, high-performance liquid chromatography-mass spectrometry (LC-ESI-MS/MS) and antioxidant activity analyses of snack extracts were performed. In the corn snacks enriched with kale, fifteen phenolic acids were indicated. These were protocatechuic, 4-OH-benzoic, vanillic, trans -caffeic, cis -caffeic, trans -p-coumaric, cis -p-coumaric, trans -ferulic, cis -ferulic, salicylic, gentisic, syringic, 3-OH-cinnamic, trans -sinapic, and cis -sinapic acids. Both the qualitative and quantitative content of polyphenols increased with the addition of B. oleracea . Data from spectrophotometric analyses of the samples showed high DPPH radical scavenging potential of snacks enriched with 4, 6, and 8% of kale. Snacks enriched with kale contain high level of phenolic acids and, therefore, have great potential to make a valuable source of natural antioxidants. High-temperature short-time extrusion-cooking process had no negative impact on polyphenol's activity.

Ab initio study of potential ultrafast internal conversion routes in oxybenzone, caffeic acid, and ferulic acid: implications for sunscreens.

PubMed

Karsili, Tolga N V; Marchetti, Barbara; Ashfold, Michael N R; Domcke, Wolfgang

2014-12-26

Oxybenzone (OB) and ferulic acid (FA) both find use in commercial sunscreens; caffeic acid (CA) differs from FA by virtue of an -OH group in place of a -OCH3 group on the aromatic ring. We report the results of ab initio calculations designed to explore the excited state nonradiative relaxation pathways that provide photostability to these molecules and the photoprotection they offer toward UV-A and UV-B radiation. In the case of OB, internal conversion (IC) is deduced to occur on ultrafast time scales, via a barrierless electron-driven H atom transfer pathway from the S1(1(1)nπ*) state to a conical intersection (CI) with the ground (S0) state potential energy surface (PES). The situation with respect to CA and FA is somewhat less clear-cut, with low energy CIs identified by linking excited states to the S0 state following photoexcitation and subsequent evolution along (i) a ring centered out-of-plane deformation coordinate, (ii) the E/Z isomerism coordinate and, in the case of CA, (iii) an O-H stretch coordinate. Analogy with catechol suggests that the last of these processes (if active) would lead to radical formation (and thus potential phototoxicity), encouraging a suggestion that FA might be superior to CA as a sunscreen ingredient.

Improved Stability of Tuberculosis Drug Fixed-Dose Combination Using Isoniazid-Caffeic Acid and Vanillic Acid Cocrystal.

PubMed

Battini, Swapna; Mannava, M K Chaitanya; Nangia, Ashwini

2018-06-01

The classic fixed-dose combination (FDC) of 4 tuberculosis drugs, namely rifampicin (RIF), isoniazid (INH), pyrazinamide (PZA), and ethambutol dihydrochloride (EDH) has the twin issues of physical stability and RIF cross-reaction in the 4-FDC. The major reason for these quality issues is the interaction between RIF and INH to yield isonicotinyl hydrazone in drug tablets. Pharmaceutical cocrystals of INH with caffeic acid (CFA) (PZA + EDH + RIF + INH-CFA cocrystal) and vanillic acid (VLA) (PZA + EDH + RIF + INH-VLA cocrystal) are able to stabilize the FDC formulation compared with the reference batch (PZA + EDH + RIF + INH). Stability studies under accelerated humidity and temperature stress conditions of 40°C and 75% relative humidity showed that the physical stability of the cocrystal formulation was superior by powder X-ray diffraction and scanning electron microscopy analysis, and chemical purity was analyzed by high-performance liquid chromatography. Changes in the composition and structure were monitored on samples drawn at 7, 15, 22, and 30 days of storage. FDC-INH-CFA cocrystal batch exhibited greater stability compared with FDC-INH-VLA cocrystal and FDC reference drug batches. The superior stability of INH-CFA cocrystal is attributed to the presence of stronger hydrogen bonds and cyclic O-H⋯O synthon in the crystal structure. Copyright © 2018 American Pharmacists Association®. Published by Elsevier Inc. All rights reserved.

Mechanisms involved in the cytotoxic action of Brazilian propolis and caffeic acid against HEp-2 cells and modulation of P-glycoprotein activity.

PubMed

da Silva, Lívia M; Frión-Herrera, Yahima; Bartolomeu, Ariane R; Gorgulho, Carolina Mendonça; Sforcin, José M

2017-11-01

The effects of propolis and phenolic compounds (caffeic acid - Caf; dihydrocinnamic acid - Cin; p-coumaric acid - Cou) in the same quantity found in our propolis sample were investigated on human laryngeal epidermoid carcinoma (HEp-2) cells. Cell viability, apoptosis/necrosis and cell cycle arrest, P53 and CASPASE-3 gene expression, generation of reactive oxygen species (ROS) and the ability of propolis to induce doxorubicin (DOX) efflux using a P-glycoprotein (P-gp) inhibitor (verapamil) were assayed. Propolis exerted a cytotoxic effect on HEp-2 cells, whereas isolated compounds had no effect on cell viability. Higher concentrations were tested and Caf induced late apoptosis or necrosis in HEp-2 cells, while propolis induced apoptosis, both probably due to ROS generation. P53 expression was downregulated by propolis but not by Caf. CASPASE-3 expression was correlated with induction of both early and late apoptosis, with both propolis and Caf alone upregulating its expression. Propolis induced cell cycle arrest at G2/M phase and Caf at S phase. Propolis but not Caf may act as a P-gp inhibitor by modulating P-gp activity and inhibiting DOX efflux. Propolis exerted cytotoxic effects on HEp-2 cells, and the mechanisms are discussed, showing its potential as an antitumour drug. © 2017 Royal Pharmaceutical Society.

[Studies on chemical constituents from herbs of Taraxacum mongolicum].

PubMed

Shi, Shu-Yun; Zhou, Chang-Xin; Xu, Yan; Tao, Qiao-Feng; Bai, Hua; Lu, Fu-Sheng; Lin, Wen-Yan; Chen, Hai-Yong; Zheng, Wei; Wang, Li-Wei; Wu, Yi-Hang; Zeng, Su; Huang, Ke-Xin; Zhao, Yu; Li, Xiao-Kun; Qu, Jia

2008-05-01

To investigate the chemical constituents of the herbs of Taraxacum mongolicum. The chemical constituents were isolated by various column chromatographic methods and their structures elucidated mainly by NMR and MS evidences. Forty-four components were obtained and identified were as artemetin (1), quercetin (2), quercetin-3', 4', 7-trime-thyl ether (3), luteolin (4), luteolin-7-O-beta-D-glucopyranoside (5), luteolin-7-O-beta-D-galactopyranoside (6), genkwanin (7), isoetin (8), hesperetin (9), genkwanin-4'-O-beta-D-lutinoside (10), hesperidin (11), quercetin-7-O-[beta-D-glucopyranosyl (1-->6) -beta-D-glucopyranoside (12), quercetin-3, 7-O-beta-D-diglucopyranoside (13), isoetin-7-O-beta-D-glucopyranosyl- 2'-O-alpha-L-arabinopyranoside (14), isoetin-7-O-beta-D-glucopyranosyl-2'-O-alpha-D-glucopyranoside (15), isoetin-7- O-beta-D-glucopyranosyl-2'-O-beta-D-xyloypyranoside (16), caffeic acid (17), furulic acid (18), 3-O-caffeoylquinic acid (19), 3, 5-di-O-caffeoylquinic acid (20), 3, 4-di-O-caffeoylquinic acid (21), 4, 5-di-O-caffeoylquinic acid (22), 1-hydroxymethyl-5-hydroxy-phenyl-2-O-beta-D-glucopyranoside (23), p-hydroxybenzoic acid (24), p-coumaric acid (25), 3, 5-dihydroxylbenzoic acid (26), gallic acid (27), gallicin (28), syringic acid (29), 3, 4-dihydroxybenzoic acid (30), caffeic acid ethyl ester (31), esculetin (32), rufescidride (33), mongolicumin A [6, 9, 10-trihydroxy-benzoxanthene-1, 2-dicarboxylic acid] (34), mongolicumin B [1 l-hydroxy-2-oxo-guaia-1 (10), 3, 5-trien-8, 12-lactone] (35), isodonsesquitin A (36), taraxacin (37), sesquiterpene ketolactone (38), taraxasteryl acetate (39), phi-taraxasteryl acetate (40) and lupenol acetate (41), palmitic acid (42), beta-sitosterol (43), and stigmasterol (44). Four compounds (14, 15, 34 and 35) were new compounds, compounds 1, 3, 6-13, 20-22, 30 and 31 were isolated from this genus for the first time, while compounds 18, 23-29, 32 and 37-42 were obtained from this species for the first time.

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.

Polyphenols from artichoke heads (Cynara cardunculus (L.) subsp. scolymus Hayek): in vitro bio-accessibility, intestinal uptake and bioavailability.

PubMed

D'Antuono, Isabella; Garbetta, Antonella; Linsalata, Vito; Minervini, Fiorenza; Cardinali, Angela

2015-04-01

Artichoke is a rich source of health promoting compounds such as polyphenols, important for their pharmaceutical and nutritional properties. In this study, the potential for bioavailability of the artichoke polyphenols was estimated by using both in vitro digestion and Caco-2 human intestinal cell models. In vitro digestive recoveries (bio-accessibility) were found to be 55.8% for total artichoke phenolics and in particular, 70.0% for chlorogenic acid, 41.3% for 3,5-O-dicaffeoylquinic acid, and 50.3% for 1,5-O-dicaffeoylquinic acid, highlighting potential sensitivity of these compounds to gastric and small intestinal digestive conditions. Uptake of artichoke polyphenols was rapid with peak accumulation occurring after 30 min with an efficiency of 0.16%, according to the poor uptake of dietary polyphenols. Some compounds, such as coumaric acid, caffeic acid and caffeic acid derivatives, were also detected in the basolateral side assuming extra and intracellular esterase activities on chlorogenic acid. Only apigenin-7-O-glucoside was transported through the Caco-2 monolayer demonstrating its bioavailability to the extent of 1.15% at 60 min. In addition, permeability coefficient (Papp = 2.29 × 10(-5) cm s(-1)), involving apical to basolateral transport of apigenin 7-O-glucoside, was calculated to facilitate estimation of transport through the Caco-2 monolayer. Finally, the mono and dicaffeoylquinic acids present in artichoke heads exert an antioxidant activity on the human low density lipoprotein system correlated to their chemical structure. In conclusion, the utilized in vitro models, although not fully responding to the morphological and physiological features of human in vivo conditions, could be a useful tool for investigating mechanistic effects of polyphenols released from the food matrix.

From the X-rays to a reliable “low cost” computational structure of caffeic acid: DFT, MP2, HF and integrated molecular dynamics-X-ray diffraction approach to condensed phases

NASA Astrophysics Data System (ADS)

Lombardo, Giuseppe M.; Portalone, Gustavo; Colapietro, Marcello; Rescifina, Antonio; Punzo, Francesco

2011-05-01

The ability of caffeic acid to act as antioxidant against hyperoxo-radicals as well as its recently found therapeutic properties in the treatment of hepatocarcinoma, still make this compound, more than 20 years later the refinement of its crystal structure, object of study. It belongs to the vast family of humic substances, which play a key role in the biodegradation processes and easily form complexes with ions widely diffused in the environment. This class of compounds is therefore interesting for potential environmental chemistry applications concerning the possible complexation of heavy metals. Our study focused on the characterization of caffeic acid as a starting necessary step, which will be followed in the future by the application of our findings on the study of the properties of caffeate anion interaction with heavy metal ions. To reach this goal, we applied a low cost approach - in terms of computational time and resources - aimed at the achievement of a high resolution, robust and trustable structure using the X-ray single crystal data, recollected with a higher resolution, as touchstone for a detailed check. A comparison between the calculations carried out with density functional theory (DFT), Hartree-Fock (HF) method and post SCF second order Møller-Plesset perturbation method (MP2), at the 6-31G ** level of the theory, molecular mechanics (MM) and molecular dynamics (MD) was performed. As a consequence we explained on one hand the possible reasons for the pitfalls of the DFT approach and on the other the benefits of using a good and robust force field developed for condensed phases, as AMBER, with MM and MD. The reliability of the latter, highlighted by the overall agreement extended up to the anisotropic displacement parameters calculated by means of MD and the ones gathered by X-ray measurements, makes it very promising for the above-mentioned goals.

Biotransformation of rutin to isoquercitrin using recombinant α-L-rhamnosidase from Bifidobacterium breve.

PubMed

Zhang, Ru; Zhang, Bian-Ling; Xie, Tao; Li, Gu-Cai; Tuo, Yi; Xiang, Yu-Ting

2015-06-01

To biotransform rutin into isoquercitrin. A α-L-rhamnosidase from Bifidobacterium breve was produced by using Escherichia coli BL21 for biotransformation of rutin to isoquercitrin. The enzyme was purified by Ni(2+)-NTA chromatography to yield a soluble protein with a specific activity of 56 U protein mg(-1). The maximum enzyme activities were at pH 6.5, 55 °C, 20 mM rutin, and 1.2 U enzyme ml(-1). Under optimal conditions, the half-life of the enzyme was 96 h. The K m and V max values were 2.2 mM, 56.4 μmol mg(-1) min(-1) and 2.1 mM, 57.5 μmol mg(-1) min(-1) using pNP-Rha and rutin as substrates, respectively. The kinetic behavior indicated that the recombinant α-L-rhamnosidase has good catalytic performance for producing isoquercitrin. 20 mM rutin was biotransformed into 18.25 and 19.87 mM isoquercitrin after 60 and 240 min. The specific biotransformation of rutin to isoquercitrin using recombinant α-L-rhamnosidase from B. breve is a feasible method for use in industrial processes.

Rutin protects rat articular chondrocytes against oxidative stress induced by hydrogen peroxide through SIRT1 activation.

PubMed

Na, Ji-Young; Song, Kibbeum; Kim, Sokho; Kwon, Jungkee

2016-05-13

The progressive degeneration and ossification of articular chondrocytes are main symptoms in the pathogenesis of osteoarthritis (OA). Several flavonoids may provide an adjunctive alternative for the management of moderate OA in humans. Rutin, a natural flavone derivative (quercetin-3-rhamnosylglucoside), is well known for its potent anti-inflammatory and anti-oxidant properties against oxidative stress. However, the protective function of rutin related to OA, which is characterized by deterioration of articular cartilage, remains unclear. The present study investigated the protective effects of rutin, an activator of silent information regulator 1 (SIRT1), involved in the inhibition of NF-κB/MAPK signaling pathway in hydrogen peroxide (H2O2)-induced oxidative stress in rat chondrocytes. SIRT1 activation by rutin attenuated levels of inflammatory cytokines and NF-κB/MAPK signaling, whereas the inhibition of SIRT1 by sirtinol counteracted the beneficial effects of rutin in H2O2-treated chondrocytes. The findings of these studies suggested the potential involvement of SIRT1 in the pathogenesis of OA, and indicated that rutin is a possible therapeutic option for OA. Copyright © 2016 Elsevier Inc. All rights reserved.

Anticancer activity of rhamnoallosan against DU-145 cells is kinetically complementary to coexisting Polyphenolics in Psidium guajava budding leaves.

PubMed

Chen, Kuan-Chou; Hsieh, Chiu-Lan; Huang, Kuan-Dar; Ker, Yaw-Bee; Chyau, Charng-Cherng; Peng, Robert Y

2009-07-22

Psidium guajava L. is a valuable farm fruit plant having many medicinal uses. Previously its budding leaves (PE) were shown to contain huge amounts of soluble polyphenolics (SP) including (in mg/g) gallic acid (348), catechin (102), epicatechin (60), rutin (100), quercetin (102), and rutin (100) and to exhibit potent anticancer activity. However, reconstitution of these polyphenolics recovered only 40% of the original bioactivity, and the soluble carbohydrate (SC) portion in PE was suspected to contribute the remaining. PE contained a novel rhamnoallosan, which had a carbohydrate/protein (w/w) ratio = 29.06%/10.27% (=2.83, average molecular mass of 5029 kDa), characteristically evidencing a peptidoglycan, consisting of a composition (mole % ratio) of rhamnose/allose/arabinose/tallose/xylose/fucose/glucose/mannose/galactose = 36.05:24.24:8.76:7.95:7.37:5.90:3.69:3.19:2.85 and of amino acid (in wt %) glycine/leucine/proline/alanine/methionine/isoleucine/valine/histidine/tyrosine/phenylalanine/cysteine/aspartic acid/lysine/glutamic acid = 37.12:12.68:10.05:8.97:5.99:4.89:4.83:4.25:4.05:2.78:1.86:1.10:0.73:0.70. Kinetic analysis showed comparable apparent cell-killing rate coefficients (k(app)) to be 4.03 x 10(3) and 2.92 x 10(3) cells mg(-1) h(-1), respectively, by SP and SC, evidencing the complementary anti-DU-145 bioactivity in nature.

Enhanced and green extraction polyphenols and furanocoumarins from Fig (Ficus carica L.) leaves using deep eutectic solvents.

PubMed

Wang, Tong; Jiao, Jiao; Gai, Qing-Yan; Wang, Peng; Guo, Na; Niu, Li-Li; Fu, Yu-Jie

2017-10-25

Nowadays, green extraction of bioactive compounds from medicinal plants has gained increasing attention. As green solvent, deep eutectic solvent (DES) have been highly rated to replace toxic organic solvents in extraction process. In present study, to simultaneous extraction five main bioactive compounds from fig leaves, DES was tailor-made. The tailor-made DES composed of a 3:3:3 molar ratio of glycerol, xylitol and D-(-)-Fructose showed enhanced extraction yields for five target compounds simultaneously compared with traditional methanol and non-tailor DESs. Then, the tailor-made DES based extraction methods have compared and microwave-assisted extraction was selected and optimized due to its high extraction yields with lower time consumption. The influencing parameters including extraction temperature, liquid-solid ratio, and extraction time were optimized using response surface methodology (RSM). Under optimal conditions the extraction yield of caffeoylmalic acid, psoralic acid-glucoside, rutin, psoralen and bergapten was 6.482mg/g, 16.34mg/g, 5.207mg/g, 15.22mg/g and 2.475mg/g, respectively. Macroporous resin D101 has been used to recovery target compounds with recovery yields of 79.2%, 83.4%, 85.5%, 81.2% and 75.3% for caffeoylmalic acid, psoralic acid-glucoside, rutin, psoralen and bergapten, respectively. The present study suggests that DESs are truly designer and efficient solvents and the method we developed was efficient and sustainable for extraction main compounds from Fig leaves.mg/g. Copyright © 2017 Elsevier B.V. All rights reserved.

The use of factorial design to evaluate the oxidation of oils containing different types of omega-3 fatty acids.

PubMed

Agnes Dias Fabiano, Thamyris; Grassmann Roschel, Gabriela; Alves Castro, Inar

2018-05-01

Omega-3 fatty acids (n3 FA) promote beneficial effects on cardiovascular diseases, but they are highly susceptible to oxidation, which leads to the formation of potentially toxic secondary products. In this study, the antioxidant capacity of natural compounds (sinapic acid and rutin) was evaluated using an accelerated model to oxidize the oils. Five inducers (temperature, Fe 2+ , 2,2'-azobis(2-amidinopropane) dihydrochloride, ascorbyl palmitate and the hydrophobic 2,2'-azobis-2,4-dimethylvaleronitrile (AMVN)) were combined in a factorial design to accelerate the oxidation of three oils (flaxseed, echium and fish) containing different sources of n3 FA. Lipid hydroperoxide (LOOH) and thiobarbituric acid reactive substance (TBARS) concentrations estimated using the regression models did not differ from the observed values. AMVN + Fe 2+ increased TBARS in all samples. The values for the oxidative markers obtained 48 h after induction were similar to those obtained when the oils were heated at 60 ° C for 15 days. Of a number of volatile compounds formed from the oxidation of different n3 FA sources, (E,E)-2,4-heptadienal, (E,E)-2,4-decadienal, decanal, undecanal and (E)-2-undecenal were identified in all samples and could be used as more specific oxidative markers. Using the accelerated model, rutin improved the oxidative stability of fish oil, probably due to the presence of a catechol group in its chemical structure. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

Diagnostic medium containing inositol, urea, and caffeic acid for selective growth of Cryptococcus neoformans.

PubMed Central

Healy, M E; Dillavou, C L; Taylor, G E

1977-01-01

An agar medium containing inositol and urea as sole carbon and nitrogen sources, caffeic acid and ferric citrate as agents for the selective pigmentation of Cryptococcus neoformans, gentamicin as a broad-spectrum bacterial antibiotic, and yeast nitrogen base without amino acids and ammonium sulfate (Difco) was tested against 137 clinical isolates, 4 survey specimens, and 11 ATCC yeast and yeast-like strains. All 28 strains of C. neoformans showed heavy growth and dark brown pigmentation after 36 h. All other tested species of Cryptococcus showed heavy growth after 36 h but only light brown pigmentation after 48 h. No growth was observed in any tested strains of Geotrichum, Pityrosporum, Rhodotorula, Saccharomyces, and Torulopsis. Only the Cryptococcus-like Candida humicola grew of the 8 species and 62 strains of Candida tested. Six of 15 strains of Trichosporon cutaneum and 1 of 2 strains of Trichosporon pullulans showed moderate growth after 48 h. Very different colonial and microscopic morphology and/or the absence of brown pigmentation easily differentiated these strains of T. cutaneum, T. pullulans, and C. humicola from C. neoformans. The growth- and pigmentation-providing characteristics of the medium were unaffected by 2 h of exposure to 254 nm of ultraviolet light. PMID:334795

The Quality Changes of Postharvest Mulberry Fruit Treated by Chitosan-g-Caffeic Acid During Cold Storage.

PubMed

Yang, Caifeng; Han, Beibei; Zheng, Yu; Liu, Lili; Li, Changlong; Sheng, Sheng; Zhang, Jian; Wang, Jun; Wu, Fuan

2016-04-01

This study aimed to characterize the effects of chitosan-g-caffeic acid (CTS-g-CA) on improving the quality and extending the shelf life of postharvest mulberry fruit during storage at 4 °C for 18 d. CTS-g-CA was enzymatically synthesized using laccase from Pleurotus ostreatus as a catalyst. The synergistic effects of CTS-g-CA treatment on mulberry fruit were evaluated using a co-toxicity factor (cf). The results showed that the rotting rate of CTS-g-CA-treated fruit was 37.67% (compared with that of the control at 97.67%) on day 18. The weight loss and malondialdehyde (MDA) contents of the CTS-g-CA-treated mulberry fruit were significantly lower (P < 0.05) than those of the control, CA, CTS, and CA+CTS treatments. Moreover, the DPPH and ABTS radical scavenging activities of the CTS-g-CA treatment were both higher than those of the control. Furthermore, the CTS-g-CA treatment also maintained higher levels of main active substances, such as anthocyanins, ascorbic acid, polyphenols and flavones, in mulberry fruit than the other treatments. Therefore, CTS-g-CA could be used to improve the quality and extend the shelf life of postharvest mulberry fruit during cold storage. © 2016 Institute of Food Technologists®

Structural Alterations of Lignins in Transgenic Poplars with Depressed Cinnamyl Alcohol Dehydrogenase or Caffeic Acid O-Methyltransferase Activity Have an Opposite Impact on the Efficiency of Industrial Kraft Pulping1

PubMed Central

Lapierre, Catherine; Pollet, Brigitte; Petit-Conil, Michel; Toval, Gabriel; Romero, Javier; Pilate, Gilles; Leplé, Jean-Charles; Boerjan, Wout; Ferret, Valérie; De Nadai, Véronique; Jouanin, Lise

1999-01-01

We evaluated lignin profiles and pulping performances of 2-year-old transgenic poplar (Populus tremula × Populus alba) lines severely altered in the expression of caffeic acid/5-hydroxyferulic acid O-methyltransferase (COMT) or cinnamyl alcohol dehydrogenase (CAD). Transgenic poplars with CAD or COMT antisense constructs showed growth similar to control trees. CAD down-regulated poplars displayed a red coloration mainly in the outer xylem. A 90% lower COMT activity did not change lignin content but dramatically increased the frequency of guaiacyl units and resistant biphenyl linkages in lignin. This alteration severely lowered the efficiency of kraft pulping. The Klason lignin level of CAD-transformed poplars was slightly lower than that of the control. Whereas CAD down-regulation did not change the frequency of labile ether bonds or guaiacyl units in lignin, it increased the proportion of syringaldehyde and diarylpropane structures and, more importantly with regard to kraft pulping, of free phenolic groups in lignin. In the most depressed line, ASCAD21, a substantially higher content in free phenolic units facilitated lignin solubilization and fragmentation during kraft pulping. These results point the way to genetic modification of lignin structure to improve wood quality for the pulp industry. PMID:9880356

Insights on the chemical basis of the astringency of Spanish red wines.

PubMed

Sáenz-Navajas, María-Pilar; Avizcuri, José-Miguel; Ferreira, Vicente; Fernández-Zurbano, Purificación

2012-10-01

The main goal of the present study is to provide an insight on the role played by non-volatile molecules on the different in-mouth attributes, particularly astringency. For achieving such goal, the main in-mouth sensory attributes of 34 oaked Spanish red wines were measured by a trained panel. The wine content in 30 sensory-active molecules was analysed by different HPLC based methodologies together with classical enological parameters and two proanthocyanidin indexes. Fourteen compounds (aconitic acids, polymeric proanthocyanidins, caftaric, caffeic and coutaric acids and seven quercetins) were found to be at concentrations above reported taste thresholds and to have a reasonably high range of occurrence. Two highly statistically significant models for astringency were built with those compounds. Even if the models could not be fully validated by sensory addition experiments, the research has demonstrated that wine astringency is driven by polymeric proanthocyanidins and by certain phenolic acids, the rate trans/cis-aconitic acid and flavonol profiles. The research has highlighted the existence of extremely complex interactions between non-volatile compounds on the in-mouth sensory perception. Particularly remarkable is the lack of additivity and potential antagonism found between the pairs cis/trans-aconitic acids, between aconitic and caffeic acids and between quercetin-3-O-galactoside and quercetin-3-O-glucoside. Also remarkable was the sweetness×astringent interaction and the matrix-dependence of the sensory responses elicited by flavonols. These results suggest the need for new paradigms and experimental procedures for fully decoding the real sensory relevance of individual non-volatile compounds in the overall wine flavour. Copyright © 2012 Elsevier Ltd. All rights reserved.

Rhizophagus irregularis as an elicitor of rosmarinic acid and antioxidant production by transformed roots of Ocimum basilicum in an in vitro co-culture system.

PubMed

Srivastava, Shivani; Conlan, Xavier A; Cahill, David M; Adholeya, Alok

2016-11-01

Arbuscular mycorrhiza is a symbiotic association formed between plant roots and soil borne fungi that alter and at times improve the production of secondary metabolites. Detailed information is available on mycorrhizal development and its influence on plants grown under various edapho-climatic conditions, however, very little is known about their influence on transformed roots that are rich reserves of secondary metabolites. This raises the question of how mycorrhizal colonization progresses in transformed roots grown in vitro and whether the mycorrhizal fungus presence influences the production of secondary metabolites. To fully understand mycorrhizal ontogenesis and its effect on root morphology, root biomass, total phenolics, rosmarinic acid, caffeic acid and antioxidant production under in vitro conditions, a co-culture was developed between three Agrobacterium rhizogenes-derived, elite-transformed root lines of Ocimum basilicum and Rhizophagus irregularis. We found that mycorrhizal ontogenesis in transformed roots was similar to mycorrhizal roots obtained from an in planta system. Mycorrhizal establishment was also found to be transformed root line-specific. Colonization of transformed roots increased the concentration of rosmarinic acid, caffeic acid and antioxidant production while no effect was observed on root morphological traits and biomass. Enhancement of total phenolics and rosmarinic acid in the three mycorrhizal transformed root lines was found to be transformed root line-specific and age dependent. We reveal the potential of R. irregularis as a biotic elicitor in vitro and propose its incorporation into commercial in vitro secondary metabolite production via transformed roots.

Simultaneous metabolite fingerprinting of hydrophilic and lipophilic compounds in Echinacea pallida by high-performance liquid chromatography with diode array and electrospray ionization-mass spectrometry detection.

PubMed

Pellati, Federica; Orlandini, Giulia; Benvenuti, Stefania

2012-06-15

In this study, a detailed phytochemical characterization of Echinacea pallida (Nutt.) Nutt. root extracts and dietary supplements was carried out for the first time by developing advanced chromatographic techniques, based on HPLC with diode array (DAD) and electrospray ionization-mass spectrometry (ESI-MS) detection (with ion trap and triple quadrupole mass analyzers), for the simultaneous analysis of hydrophilic and lipophilic secondary metabolites. The HPLC analyses were carried out on an Ascentis C(18) column (250 mm × 4.6 mm I.D., 5 μm), with a mobile phase composed by H(2)O and ACN both containing 0.1% formic acid, under gradient elution. The UV spectra, in combination with MS and MS/MS data, allowed the identification of fourteen compounds, including caffeic acid derivatives, polyacetylenes and polyenes, in the analyzed samples. MS and MS/MS data were discussed in detail and the typical fragmentation patterns of each class of secondary metabolites were identified. For the first time, a hydroperoxide intermediate was characterized as an oxidation product of one of E. pallida monocarbonylic acetylenes, providing a confirmation of the mechanism that leads to the generation of hydroxylated derivatives. The HPLC method was fully validated in agreement with ICH guidelines and then applied to real samples. The quantitative analysis indicated that there was a great variability in the amount of the active compounds in the dietary supplements containing E. pallida root extracts: the content of total caffeic acid derivatives ranged from 2.31 to 11.45 mg/g and the amount of total polyacetylenes and polyenes from 6.38 to 30.54 mg/g. In the analyzed samples, the most abundant caffeic acid derivative was found to be echinacoside. Regarding polyacetylenes and polyenes, the most representative compounds were found to be tetradec-(8Z)-ene-11,13-diyn-2-one, pentedeca-(8Z,11Z)-dien-2-one and pentadec-(8Z)-en-2-one. The developed method can be considered suitable for metabolite fingerprinting and quality control of E. pallida plant material and natural products. Copyright © 2012 Elsevier B.V. All rights reserved.

Oxygen radical-mediated mutagenic effect of asbestos on human lymphocytes: suppression by oxygen radical scavengers.

PubMed

Korkina, L G; Durnev, A D; Suslova, T B; Cheremisina, Z P; Daugel-Dauge, N O; Afanas'ev, I B

1992-02-01

The mutagenic effect of chrysotile asbestos fibers and zeolite and latex particles on human lymphocytes in whole blood has been studied. It was concluded that their mutagenic activities were mediated by oxygen radicals because they were inhibited by antioxidant enzymes (SOD and catalase) and oxygen radical scavengers (rutin, ascorbic acid, and bemitil). It was proposed that oxygen radicals were released by phagocytes activated upon exposure to mineral dusts and fibers. The study of lucigenin- and luminol-amplified chemiluminescence of peritoneal macrophages stimulated by chrysotile fibers and zeolite and latex particles has shown that their mutagenic action is probably mediated by different oxygen species, namely, by the iron-oxygen complexes (perferryl ions) plus hydrogen peroxide, hydrogen peroxide, and superoxide ion, respectively. From the oxygen radical scavengers studied, rutin was the most effective inhibitor of the mutagenic effect of mineral fibers and dusts.

Phenolic compounds and biological effects of edible Rumex scutatus and Pseudosempervivum sempervivum: potential sources of natural agents with health benefits.

PubMed

Savran, Ahmet; Zengin, Gokhan; Aktumsek, Abdurrahman; Mocan, Andrei; Glamoćlija, Jasmina; Ćirić, Ana; Soković, Marina

2016-07-13

The present study outlines a chemical characterization and further effects beneficial to health of edible Rumex scutatus and Pseudosempervivum sempervivum, in addition to presenting the antioxidant, enzyme inhibitory effects and antimicrobial properties of different extracts. The phenolic compounds composition of the extracts was assessed by RP-HPLC-DAD, outlining benzoic acid and rutin as major constituents in P. sempervivum and rutin and hesperidin in R. scutatus. Moreover, further biological effects were tested on key enzymes involved in diabetes mellitus, Alzheimer's disease and skin melanogenesis revealing an important tyrosinase inhibitory effect of Pseudosempervivum water extract. Moreover, both species possessed antimicrobial properties towards bacteria and fungi relevant to public health. Accordingly, we find that R. scutatus and P. sempervivum can be considered as novel functional foods because they are rich sources of biologically active compounds that provide health benefits.

Quantification of Quercetin and Rutin from Benincasa hispida Seeds and Carissa Congesta Roots by High-performance Thin Layer Chromatography and High-performance Liquid Chromatography

PubMed Central

Doshi, Gaurav Mahesh; Une, Hemant Devidas

2016-01-01

Objective: In Indian Ayurvedic system, Benincasa hispida (BH) and Carissa congesta (CC) are well-known plants used for major and minor ailments. BH has been regarded as Kushmanda, whereas CC has been used in immune-related disorders of the human system. Quercetin and rutin identified from the vast plethora of plant extracts have proved to possess ethnopharmacological relevance. Materials and Methods: In present studies, we have determined quercetin and rutin in terms of percentage in BH seeds and CC roots by high-performance thin layer chromatography (HPTLC) and high-performance liquid chromatography (HPLC). After extraction and phytochemical screening, the extracts were subjected to quantification for the presence of quercetin and rutin by HPTLC and HPLC. Results: HPTLC showed quercetin as 44.60, 27.13% and rutin as 32.00, 36.31% w/w, whereas HPLC revealed quercetin as 34.00, 35.00% and rutin as 21.99, 45.03% w/v in BH and CC extracts, respectively. Conclusion: The BH and CC extracts have elucidated peaks that were corresponding with standard peaks on undertaking chromatographic studies. SUMMARY Quercetin and rutin are isolated from BH seeds and CC roots by High Performance. Thin Layer Chromatography and High Performance Liquid Chromatography. HPTLC revealed presence of quercetin as 44.60, 27.13 % and rutin as 32.00, 36.31 % w/w. HPLC revealed presence of quercetin as 34.00, 35.00 % and rutin as 21.99, 45.03 % w/v. Abbreviation Used: HPTLC: High Performance Thin Layer Chromatography; HPLC: High Pressure Liquid Chromatography, UV: Ultraviolet, CC: Carissa congesta, BH: Benincasa hispida PMID:26941534

Microwave-Assisted Drying for the Conservation of Honeybee Pollen.

PubMed

Canale, Angelo; Benelli, Giovanni; Castagna, Antonella; Sgherri, Cristina; Poli, Piera; Serra, Andrea; Mele, Marcello; Ranieri, Annamaria; Signorini, Francesca; Bientinesi, Matteo; Nicolella, Cristiano

2016-05-12

Bee pollen is becoming an important product thanks to its nutritional properties, including a high content of bioactive compounds such as essential amino acids, antioxidants, and vitamins. Fresh bee pollen has a high water content (15%-30% wt %), thus it is a good substrate for microorganisms. Traditional conservation methods include drying in a hot air chamber and/or freezing. These techniques may significantly affect the pollen organoleptic properties and its content of bioactive compounds. Here, a new conservation method, microwave drying, is introduced and investigated. The method implies irradiating the fresh pollen with microwaves under vacuum, in order to reduce the water content without reaching temperatures capable of thermally deteriorating important bioactive compounds. The method was evaluated by taking into account the nutritional properties after the treatment. The analyzed parameters were phenols, flavonoids, with special reference to rutin content, and amino acids. Results showed that microwave drying offers important advantages for the conservation of bee pollen. Irrespective of microwave power and treatment time, phenol and flavonoid content did not vary over untreated fresh pollen. Similarly, rutin content was unaffected by the microwave drying, suggesting that the microwave-assisted drying could be a powerful technology to preserve bioprotective compounds in fresh pollen.

In vitro bioaccessibility, transepithelial transport and antioxidant activity of Urtica dioica L. phenolic compounds in nettle based food products.

PubMed

Bonetti, Gianpiero; Tedeschi, Paola; Meca, Giuseppe; Bertelli, Davide; Mañes, Jordi; Brandolini, Vincenzo; Maietti, Annalisa

2016-10-12

Nettle (Urtica dioica L.) is a well-known plant with a wide historical background use of stems, roots and leaves. Nettle leaves are an excellent source of phenolic compounds, principally 3-caffeoylquinic acid (3-CQA), caffeoylmalic acid (CMA) and rutin. The aim of this work was to evaluate the bioaccessibility (BAC), the bioavailability (BAV) and the antioxidant activity of nettle phenolic compounds present in foods and supplements. The BAC of nettle phenolics was evaluated with an in vitro dynamic digestion of real food matrices: the type of food matrix and chemical characteristic affected the kinetics of release and solubilization, with the highest BAC after duodenal digestion. A study of duodenal trans epithelial transport evidenced low bioavailability of native forms of 3-CQA, CMA and rutin. Simulation of colonic metabolism confirmed that phenolic compounds are fermented by gut microflora, confirming the need for further investigations on the impact of phenolic compounds at the large intestine level. Photochemiluminescence assay of the simulated digestion fluids demonstrated that ingestion of Urtica based foods contributes to create an antioxidant environment against superoxide anion radicals in the entire gastrointestinal tract (GIT).

Comparative Study of Novel Ratio Spectra and Isoabsorptive Point Based Spectrophotometric Methods: Application on a Binary Mixture of Ascorbic Acid and Rutin.

PubMed

Darwish, Hany W; Bakheit, Ahmed H; Naguib, Ibrahim A

2016-01-01

This paper presents novel methods for spectrophotometric determination of ascorbic acid (AA) in presence of rutin (RU) (coformulated drug) in their combined pharmaceutical formulation. The seven methods are ratio difference (RD), isoabsorptive_RD (Iso_RD), amplitude summation (A_Sum), isoabsorptive point, first derivative of the ratio spectra ((1)DD), mean centering (MCN), and ratio subtraction (RS). On the other hand, RU was determined directly by measuring the absorbance at 358 nm in addition to the two novel Iso_RD and A_Sum methods. The work introduced in this paper aims to compare these different methods, showing the advantages for each and making a comparison of analysis results. The calibration curve is linear over the concentration range of 4-50 μg/mL for AA and RU. The results show the high performance of proposed methods for the analysis of the binary mixture. The optimum assay conditions were established and the proposed methods were successfully applied for the assay of the two drugs in laboratory prepared mixtures and combined pharmaceutical tablets with excellent recoveries. No interference was observed from common pharmaceutical additives.

Comparative Study of Novel Ratio Spectra and Isoabsorptive Point Based Spectrophotometric Methods: Application on a Binary Mixture of Ascorbic Acid and Rutin

PubMed Central

Darwish, Hany W.; Bakheit, Ahmed H.; Naguib, Ibrahim A.

2016-01-01

This paper presents novel methods for spectrophotometric determination of ascorbic acid (AA) in presence of rutin (RU) (coformulated drug) in their combined pharmaceutical formulation. The seven methods are ratio difference (RD), isoabsorptive_RD (Iso_RD), amplitude summation (A_Sum), isoabsorptive point, first derivative of the ratio spectra (1DD), mean centering (MCN), and ratio subtraction (RS). On the other hand, RU was determined directly by measuring the absorbance at 358 nm in addition to the two novel Iso_RD and A_Sum methods. The work introduced in this paper aims to compare these different methods, showing the advantages for each and making a comparison of analysis results. The calibration curve is linear over the concentration range of 4–50 μg/mL for AA and RU. The results show the high performance of proposed methods for the analysis of the binary mixture. The optimum assay conditions were established and the proposed methods were successfully applied for the assay of the two drugs in laboratory prepared mixtures and combined pharmaceutical tablets with excellent recoveries. No interference was observed from common pharmaceutical additives. PMID:26885440

Rutin, a quercetin glycoside, alleviates acute endotoxemic kidney injury in C57BL/6 mice via suppression of inflammation and up-regulation of antioxidants and SIRT1.

PubMed

Khajevand-Khazaei, Mohammad-Reza; Mohseni-Moghaddam, Parvaneh; Hosseini, Marjan; Gholami, Leila; Baluchnejadmojarad, Tourandokht; Roghani, Mehrdad

2018-06-16

Acute kidney injury (AKI) is a common complication following severe sepsis, its incidence is increasing, and it is associated with a high rate of morbidity and mortality. Rutin is a glycoside of the bioflavonoid quercetin with various protective effects due to its antioxidant and anti-inflammatory potential. In this research, we tried to assess the protective effect of rutin administration in a model of AKI in C57BL/6 mice. For induction of AKI, lipopolysaccharide (LPS) was injected once (10mg/kg, i.p.) and rutin was p.o. given at doses of 50 or 200mg/kg. Treatment of LPS-challenged group with rutin lowered serum level of creatinine and blood urea nitrogen (BUN), restored to some extent renal oxidative stress-related indices such as malondialdehyde (MDA), glutathione (GSH), and activity of superoxide dismutase (SOD) and catalase. In addition, rutin brought back renal nuclear factor-kappaB (NF-κB), toll-like receptor 4 (TLR4), cyclooxygenase-2 (COX2), sirtuin 1 (SIRT1), tumor necrosis factor α (TNFα), interleukin-6, and caspase 3 activity to their control levels. Moreover, protective effect of rutin was in accordance to a dose-dependent manner. Collectively, rutin is capable to mitigate LPS-induced AKI via appropriate modulation of renal oxidative stress, inflammation, and apoptosis. Copyright © 2018. Published by Elsevier B.V.

Neuro-protective effect of rutin against Cisplatin-induced neurotoxic rat model.

PubMed

Almutairi, Mashal M; Alanazi, Wael A; Alshammari, Musaad A; Alotaibi, Moureq Rashed; Alhoshani, Ali R; Al-Rejaie, Salim Salah; Hafez, Mohamed M; Al-Shabanah, Othman A

2017-09-29

Cisplatin is widely used chemotherapeutic agent for cancer treatment with limited uses due to its neurotoxic side effect. The aim of this study was to determine the potential preventive effects of rutin on the brain of cisplatin- neurotoxic rat model. Forty rats were divided into four groups. Group-1 (control group) was intra-peritoneal (IP) injected with 2.5 ml/kg saline. Group-2 (rutin group) was orally administrated 30 mg/kg rutin dissolved in water for 14 days. Group-3 (cisplatin group) was IP received 5 mg/kg cisplatin single dose. Group-4 (rutin and cisplatin group) was orally administrated 30 mg/kg rutin dissolved in water for 14 days with a single dose of 5 mg/kg cisplatin IP on day ten. Brain tissues from frontal cortex was used to extract RNA, the gene expression levels of paraoxonase-1 (PON-1), PON-2, PON-3, peroxisome proliferator-activated receptor delta (PPAR-δ), and glutathione peroxidase (GPx) was investigated by Real-time PCR. Cisplatin significantly decreased the expression levels of PON-1, PON-3, PPAR-δ and GPX whereas significantly increased PON-2 expression levels. Co-administration of Rutin prevented the cisplatin-induced toxicity by restoring the alteration in the studied genes to normal values as in the control group. This study showed that Rutin has neuroprotective effect and reduces cisplatin- neurotoxicity with possible mechanism via the antioxidant pathway.

ENZYMATIC COUPLING OF THE HERBICIDE BENTAZON WITH HUMUS MONOMERS AND CHARACTERIZATION OF REACTION PRODUCTS (R823847)

EPA Science Inventory

To elucidate the binding mechanism of the herbicide bentazon
(3-isopropyl-1H-2,1,3-benzothiadiazine-4(3H)-one 2,2-dioxide) with
humic monomers in the presence of an oxidative enzyme, the reaction of bentazon
with catechol, caffeic acid, protocatechuic...

Distribution of Major Chlorogenic Acids and Related Compounds in Brazilian Green and Toasted Ilex paraguariensis (Maté) Leaves.

PubMed

Lima, Juliana de Paula; Farah, Adriana; King, Benjamin; de Paulis, Tomas; Martin, Peter R

2016-03-23

Ilex paraguariensis (maté) is one of the best sources of chlorogenic acids (CGA) in nature. When leaves are toasted, some isomers are partly transformed into 1,5-γ-quinolactones (CGL). Both CGA and CGL are important contributors to the brew's flavor and are thought to contribute to human health. In this study, we quantified 9 CGA, 2 CGL, and caffeic acid in 20 samples of dried green and toasted maté that are commercially available in Brazil. Total CGA content in green maté varied from 8.7 to 13.2 g/100 g, dry weight (dw). Caffeic acid content varied from 10.8 to 13.5 mg/100 g dw, respectively. Content in toasted maté varied from 1.5 to 4.6 g/100 g and from 1.5 to 7.2 mg/100 g dw, respectively. Overall, caffeoylquinic acid isomers (CQA) were the most abundant CGA in both green and toasted maté, followed by dicaffeoylquinic acids (diCQA) and feruloylquinic acids (FQA). These classes accounted for 58.5%, 40.0%, and 1.5% of CGA, respectively, in green maté and 76.3%, 20.7%, and 3.0%, respectively, in toasted maté. Average contents of 3-caffeoylquinolactone (3-CQL) and 4-caffeoylquinolactone (4-CQL) in commercial toasted samples were 101.5 mg/100 g and 61.8 mg/100 g dw, respectively. These results show that, despite overall losses during the toasting process, CGA concentrations are still substantial in toasted leaves, compared to other food sources of CGA and phenolic compounds in general. In addition to evaluating commercial samples, investigation of changes in CGA profile and formation of 1,5-γ-quinolactones was performed in experimental maté toasting.

Direct detection of rutin-degrading isozymes with polyacrylamide gel electrophoresis.

PubMed

Li, Yuping; Deng, Dandan; Zhang, Xuebin; Zhang, Haina; Wang, Cong; Chen, Peng

2013-12-15

Rutin-degrading enzymes (RDEs) specifically hydrolyze the glycosidic linkages of rutin, producing quercetin and rutinose. Here we report a reliable and sensitive polyacrylamide gel electrophoresis and staining method for the detection of RDE isozymes, which is based on the aqueous solubility difference between rutin and quercetin, as well as the ultraviolet absorbance of quercetin. With this novel method, we achieved a detection limit of 12 ng with 107 U of RDE activity, enabling us to detect at least five RDE isozymes in tartary buckwheat seeds. Copyright © 2013 Elsevier Inc. All rights reserved.

The effect of Cu 2+ or Fe 3+ on the noncovalent binding of rutin with bovine serum albumin by spectroscopic analysis

NASA Astrophysics Data System (ADS)

Li, Daojin; Zhu, Mei; Xu, Chen; Chen, Jianjun; Ji, Baoming

2011-01-01

The interaction of rutin to bovine serum albumin (BSA) in aqueous solution was investigated by fluorescence spectra and ultraviolet-visible (UV-vis) spectra at pH 7.40. There are also some metal ions present in blood plasma, thus the research about the effect of metal ions on the interaction of drugs with proteins is crucial. Therefore, we have studied the effect of Cu 2+ or Fe 3+ on the interaction between rutin and BSA by using spectroscopic technique at pH 7.40, for the first time. The results of fluorescence titration indicated that rutin could quench the intrinsic fluorescence of BSA in a static quenching way. The binding sites number ( n), the binding constant ( K) and the spatial-distance ( r) of rutin with BSA without or with Cu 2+ or Fe 3+ at 310 K were calculated. The result showed that the presence of Cu 2+ or Fe 3+ increased the binding constant and changed the binding distance between the acceptor and the donor, which possibly results from the formation of metal ions-BSA complex. The effect of rutin on the conformation of BSA was also analyzed using UV under experimental conditions. Furthermore, the fluorescence displacement experiments indicated that rutin is situated within subdomain IIA of BSA.

Chemical characterization and cytotoxic, genotoxic, and mutagenic properties of Baccharis trinervis (Lam, Persoon) from Colombia and Brazil.

PubMed

Jaramillo-García, Victoria; Trindade, Cristiano; Lima, Elisiane; Guecheva, Temenouga N; Villela, Izabel; Martinez-Lopez, Wilner; Corrêa, Dione S; Ferraz, Alexandre de B F; Moura, Sidnei; Sosa, Milton Quintana; Da Silva, Juliana; Henriques, João Antônio Pegas

2018-03-01

Baccharis trinervis (Lam, Persoon) leaves are used in the traditional medicine for the treatment of high fevers, edema, inflammation, sores and muscle cramps, snakebites and as antiseptic. To investigate the cytotoxic, genotoxic, and mutagenic effects of extracts and fractions of B. trinervis from Brazil and Colombia in Chinese Hamster Ovary (CHO) cells, and to examine the mutagenic activity in Salmonella typhimurium. Aqueous extracts (AE) of aerial parts of B. trinervis from Brazil (B) and Colombia (C) were fractioned in ethyl acetate fraction (EAF), butanol extract (BF), and aqueous residue fraction (ARF). Qualitative chemical screening and determination of total flavonoid content were made. Identification of chemical constituents was performed by High Performance Liquid Chromatography (HPLC) and High Resolution Mass Spectrometry (HRMS). For the in vitro tests, CHO cells were treated for 3h with extracts and fractions. The cytotoxic activity was evaluated by clonal survival and 3-(4.5-dimethylthiazole-2-yl)-2.5-biphenyl tetrazolium bromide reduction assay (MTT). Genotoxic and mutagenic effects were evaluated by the alkaline comet assay and Cytokinesis-blockage micronucleus test (CBMN), respectively. Additionally, Salmonella/microsome assay was carried out to determinate the mutagenic effects in EAF from Brazil and Colombia. Phytochemical analyses indicated the presence of saponins and flavonoids. AE and EAF were the samples with the highest quantity of total flavonoids. HPLC showed the presence of luteolin only in AEC, and caffeic acid, ellagic acid, rosmarinic acid, and rutin were identified in AEB and AEC (AEC>AEB). The HRMS in positive mode of EAFB and EAFC showed presence of two carboxylic acids, coumarin, and two terpenoids. In addition, were identified one terpenoid and two carboxylic acids in AE, BF and ARF of B. trinervis from both countries in negative mode. Dose-dependent cytotoxic effects were observed in CHO cells treated with B. trinervis extracts and fractions by using clonal survival and MTT at concentrations higher than 0.05mg/mL. All the extracts and fractions induced DNA strand breaks in CHO cells with dose-dependent response, mostly EAFB and EAFC. The EAF from Brazil and Colombia showed mutagenic effect at 0.5mg/mL, while the other fractions did not show a significant difference in relation to the control. No mutagenic effects were found in EAF from both countries by the Salmonella/microsome assay. Cytotoxic and genotoxic effects were demonstrated in all extracts and fractions used, although only EAF showed mutagenic effects by CBMN, but not by Salmonella/microsome assay. Our results suggest that flavonoids, phenylpropanoids, coumarins, and diterpenes may be responsible for the cytotoxic, genotoxic and mutagenic effects observed. Copyright © 2017 Elsevier B.V. All rights reserved.

Argpyrimidine-tagged rutin-encapsulated biocompatible (ethylene glycol dimers) nanoparticles: Synthesis, characterization and evaluation for targeted drug delivery.

PubMed

Bhattacherjee, Abhishek; Dhara, Kaliprasanna; Chakraborti, Abhay Sankar

2016-07-25

Diabetes mellitus represents a major metabolic disorder affecting millions of people all over the world. Currently available therapeutic treatments are not good enough to control the long-term complications of diabetes. Active targeting via inclusion of a specific ligand on the nanoparticles provides effective therapeutic approach in different diseases. However, such specific drug delivery systems have not been explored much in diabetes due to lack of suitable biological targets in this disorder. Our objective is to synthesize a ligand-tagged drug-loaded nanoparticle for delivery of the drug at specific sites to enhance its therapeutic efficiency in diabetic condition. The nanoparticles have been prepared by using biocompatible ethylene glycol-bis (succinic acid N-hydroxysuccinimide ester) dimers. Although advanced glycation end products (AGEs) are the root causes of diabetic complications, argpyrimidine, an AGE, possesses antioxidant and reducing activities. AGE interacts selectively with its cell surface receptors (RAGE), which are significantly increased in diabetic condition. We have selected RAGE as the target of argpyrimidine, which is tagged on the nanoparticles as a ligand. Rutin, having anti-hyperglycemic and anti-glycating activities, has been used for nanoencapsulation. Rutin-loaded argpyrimidine-tagged nanoparticles have been synthesized and characterized. We have demonstrated the drug releasing capacity and target specificity of the synthesised drug delivery system under ex vivo and in vivo conditions. Copyright © 2016 Elsevier B.V. All rights reserved.

Investigation into the Emerging Role of the Basic Amino Acid L-Lysine in Enhancing Solubility and Permeability of BCS Class II and BCS Class IV Drugs.

PubMed

Abdelkader, Hamdy; Fathalla, Zeinab

2018-06-18

The search for a simple and scalable approach that can improve the two key biopharmaceutical processes (solubility and permeability) for BCS Class II and BCS Class IV has still been unmet need. In this study, L-lysine was investigated as a potential excipient to tackle problems with solubility and permeability. Bendazac (Class II); quercetin and rutin (Class IV) were employed. Drugs-lysine complexes in 1:1 M ratios were prepared by co-precipitation and co-grinding; characterized for solubility, partition coefficient, DSC, FTIR, SEM, dissolution rate and permeability. Chemical stability of quercetin-lysine and rutin-lysine was studied by assessing antioxidant capacity using Trolox and CUPRAC assays. Drugs-lysine salt/complexes were confirmed. Solubility enhancement factors ranged from 68- to 433-fold increases and dissolution rates were also significantly enhanced by up to 6-times, compared with drugs alone. With the exception of rutin-lysine, P app for bendazac-lysine and quercetin-lysine enhanced by 2.3- to 4-fold. P app for quercetin (Class IV) benefited more than bendazac (Class II) when complexed with lysine. This study warrants the use of L-lysine as a promising excipient for enhanced solubility and permeability of Class II and Class IV, providing that the solubility of the drug is ensured at 'the door step' of absorption sites.

Analysis of the relationship between Chalcone Isomerase gene expression level and rutin production in Ficus deltoidea var. deltoidea and F. deltoidea var. angustifolia

NASA Astrophysics Data System (ADS)

Najid, Najihah Mohd; Zain, Che Radziah Che Mohd; Zainal, Zamri

2016-11-01

Ficus deltoidea (moraceae) is a herbal plant with medicinal values. Previous studies reported that the F. deltoidea contains a high level of bioactive compounds such as flavonoids. A cDNA encodes for chalcone isomerase was identified from F. deltoidea, designated as FdCHI, which involved in the isomerization of naringenin chalcone to naringenin. Naringenin is a key branch point for the synthesis of rutin, which is believed involved in defense mechanism in the plant. Therefore, we hypothesized that there might be a direct relationship between FdCHI expression level and rutin production in leaves of F. deltoidea var. deltoidea (FDD) and F. deltoidea var. angustifolia (FDA). Our result showed that expression level of FdCHI in leaves FDD was greater than FDA. Analysis of High Performance Liquid Chromatography (HPLC) revealed that rutin was only detected in FDA leaves. Based on the results between FdCHI expression and rutin production, this study concluded that there is no relationship between FdCHI expression and rutin production in leaves of FDA and FDD.

Effects of rutin supplementation on antioxidant status and iron, copper, and zinc contents in mouse liver and brain.

PubMed

Gao, Zhonghong; Xu, Huibi; Huang, Kaixun

2002-09-01

The effect of rutin on total antioxidant status as well as on trace elements such as iron, copper, and zinc in mouse liver and brain were studied. Mice were administrated with 0.75 g/kg or 2.25 g/kg P. O. of rutin for 30 d consecutively. Following the treatment, the activity of total antioxidant status, catalase, Cu,Zn-superoxide dismutase, Mn-superoxide dismutase, zinc, copper, and iron were measured in mouse liver and brain. The results showed that rutin significantly increased the antioxidant status and Mn-superoxide dismutase activities in mouse liver, but it had no effect on these variables in the brain. Treatment with a higher concentration of rutin significantly decreased catalase activity and iron, zinc, and copper contents in mouse liver; it also resulted in a slower weight gain for the first 20 d. These results indicate that rutin taken in proper amount can effectively improve antioxidant status, whereas at an increased dosage, it may cause trace element (such as iron, zinc, and copper) deficiencies and a decrease in the activities of related metal-containing enzymes.

Properties of active gelatin films incorporated with rutin-loaded nanoemulsions.

PubMed

Dammak, Ilyes; de Carvalho, Rosemary Aparecida; Trindade, Carmen Sílvia Fávaro; Lourenço, Rodrigo Vinicius; do Amaral Sobral, Paulo José

2017-05-01

Physico-chemical, mechanical, barrier, release profiles and antioxidant properties of composite gelatin based-films incorporated with rutin-loaded oil-in-water nanoemulsion, at various concentrations (5, 10, 15, or 20% (based on the weight of the gelatin powder)) were studied. All the gelatin/rutin-loaded nanoemulsion films displayed higher tensile strength and higher elongation at break than the gelatin control film. The composite films did not show significant differences in thickness, color, brightness and transparency. The structural properties evaluated by FTIR showed that the rutin-loaded nanoemulsion achieved complete miscibility within the gelatin matrix. All the gelatin/nanoemulsion films exhibited compact and homogenous microstructure. In addition, these films showed high antioxidant activities monitored by DPPH radical scavenging and reducing power activities. The Korsmeyer-Peppas model described well the rutin release profile. Rutin release was mainly governed by Fickian diffusion with simultaneous interfering swelling and disintegration phenomena. These results indicate that nanoemulsions-in-gelatin systems can function as potential active packaging systems to enhance shelf life of food products and then to provide a high-quality products (fresh/safe). Copyright © 2017 Elsevier B.V. All rights reserved.

Quercetin and rutin as potential agents antifungal against Cryptococcus spp.

PubMed

Oliveira, V M; Carraro, E; Auler, M E; Khalil, N M

2016-01-01

Amphotericin B is a fungicidal substance that is treatment of choice for most systemic fungal infections affecting as cryptococcosis the immunocompromised patients. However, severe side effects have limited the utility of this drug. The aim of this study was to evaluate the antifungal effect of the combination of amphotericin B with quercetin or rutin and as a protective of citotoxic effect. The antifungal activity to amphotericin B, quercetin and rutin alone and in combination was determined in Candida sp and Cryptococcus neoformans strains. Cytotoxicity test on erythrocytes was performed by spectrophotometric absorbance of hemoglobin. The amphotericin B MIC was reduced when used in combination with quercetin or rutin to C. neoformans ATCC strain and reduced when combined with rutin to a clinical isolate of C. neoformans. In addition, the combination of quercetin with amphotericin B may reduce the toxicity of amphotericin B to red blood cells. Our results suggest that quercetin and rutin are potential agents to combine with amphotericin B in order to reduce the amphotericin dose to lessen side effects and improve antifungal efficacy.

High Performance Liquid Chromatography-Diode Array Detector Method for the Simultaneous Determination of Five Compounds in the Pulp and Seed of Sea Buckthorn

PubMed Central

Zhao, Lu; Wen, E; Upur, Halmuart; Tian, Shuge

2017-01-01

Context: Sea buckthorn (Hippophae rhamnoides L.) as a traditional Chinese medicinal plant has various uses in Xinjiang. Objective: A reversed-phase rapid-resolution liquid-chromatography method with diode array detector was developed for simultaneous determination of protocatechuic acid, rutin, quercetin, kaempferol, and isorhamnetin in the pulp and seed of sea buckthorn, a widely used traditional Chinese medicine for promoting metabolism and treating scurvy and other diseases. Settings and design: Compounds were separated on an Agilent ZORBAX SB-C18 column (4.6 mm × 250 mm, 5 μm; USA) with gradient elution using methanol and 0.4% phosphoric acid (v/v) at 1.0 mL/min. Detection wavelength was set at 280 nm. Materials and Methods: The fruits of wild sea buckthorn were collected from Wushi County in Aksu, Xinjiang Province. Statistical performances: The RSD of precision test of the five compounds were in the range of 0.60-2.22%, and the average recoveries ranged from 97.36% to 101.19%. Good linearity between specific chromatographic peak and component qualities were observed in the investigated ranges for all the analytes (R2 > 0.9997). Results: The proposed method was successfully applied to determine the levels of five active components in sea buckthorn samples from Aksu in Xinjiang. Conclusions: The proposed method is simple, fast, sensitive, accurate, and suitable for quantitative assessment of the pulp and seed of sea buckthorn. SUMMARY Quantitative analysis method of protocatechuic acid, rutin, quercetin, kaempferol, and isorhamnetin in the extract of sea buckthorn pulp and seed is developed by high-performance liquid chromatography (HPLC) diode array detection.This method is simple and accurate; has strong specificity, good precision, and high recovery rate; and provides a reliable basis for further development of the substances in the pulp and seed of sea buckthorn.The method is widely used for content determination of active ingredients or physiologically active components in traditional Chinese medicine and its preparation Abbreviation used: PR: protocatechuic acid, RU: rutin, QU: quercetin, KA: kaempferol, IS: isorhamnetin, HPLC: high-performance liquid chromatography, HPLC-DAD: high performance liquid chromatographydiode array detector, LOD: linearity and limit of detection, LOQ: limit of quantitation, RSD: relative standard deviation PMID:28216897

Reaction Mechanisms and Structural and Physicochemical Properties of Caffeic Acid Grafted Chitosan Synthesized in Ascorbic Acid and Hydroxyl Peroxide Redox System.

PubMed

Liu, Jun; Pu, Huimin; Chen, Chong; Liu, Yunpeng; Bai, Ruyu; Kan, Juan; Jin, Changhai

2018-01-10

The ascorbic acid (AA) and hydroxyl peroxide (H 2 O 2 ) redox pair induced free radical grafting reaction is a promising approach to conjugate phenolic groups with chitosan (CS). In order to reveal the exact mechanisms of the AA/H 2 O 2 redox pair induced grafting reaction, free radicals generated in the AA/H 2 O 2 redox system were compared with hydroxyl radical ( • OH) produced in the Fe 2+ /H 2 O 2 redox system. Moreover, the structural and physicochemical properties of caffeic acid grafted CS (CA-g-CS) synthesized in these two redox systems were compared. Results showed that only ascorbate radical (Asc •- ) was produced in the AA/H 2 O 2 system. The reaction between Asc •- and CS produced novel carbon-centered radicals, whereas no new free radicals were detected when • OH reacted with CS. Thin layer chromatography, UV-vis, Fourier transform infrared, and nuclear magnetic resonance spectroscopic analyses all confirmed that CA was successfully grafted onto CS through Asc •- . However, CA could be hardly grafted onto CS via • OH. CA-g-CS synthesized through Asc •- exhibited lower thermal stability and crystallinity than the reaction product obtained through • OH. For the first time, our results demonstrated that the synthesis of CA-g-CS in the AA/H 2 O 2 redox system was mediated by Asc •- rather than • OH.

Effect of high hydrostatic pressure treatment on isoquercetin production from rutin by commercial α-L-rhamnosidase.

PubMed

Kim, Do-Yeon; Yeom, Soo-Jin; Park, Chang-Su; Kim, Yeong-Su

2016-10-01

To optimize conversion of rutin to isoquercetin by commercial α-L-rhamnosidase using high hydrostatic pressure (HHP). The de-rhamnosylation activity of α-L-rhamnosidase for isoquercetin production was maximal at pH 6.0 and 50 °C using HHP (150 MPa). The enzyme showed high specificity for rutin. The specific activity for rutin at HHP was 1.5-fold higher than that at atmospheric pressure. The enzyme completely hydrolysed 20 mM rutin in tartary buckwheat extract after 2 h at HHP, with a productivity of 10 mM h(-1). The productivity and conversion were 2.2- and 1.5-fold higher at HHP than at atmospheric pressure, respectively. This is the first report concerning the enzymatic hydrolysis of isoquercetin in tartary buckwheat at HHP.

Identification of rutin deglycosylated metabolites produced by human intestinal bacteria using UPLC-Q-TOF/MS.

PubMed

Yang, Jing; Qian, Dawei; Jiang, Shu; Shang, Er-xin; Guo, Jianming; Duan, Jin-ao

2012-06-01

In this paper, rutin was metabolized by human intestinal bacteria and five isolated strains including Bacillus sp. 52, Bacteroides sp. 45, 42, 22 and Veillonella sp. 32, the metabolites were identified using ultra performance liquid chromatography/quadrupole-time-of-flight mass spectrometry (UPLC-Q-TOF/MS). As a result, Bacillus sp. 52 and Bacteroides sp. 45 could metabolize rutin to quercetin 3-O-glucoside and leucocyanidin. Bacteroides sp. 42 and Veillonella sp. 32 could convert rutin to leucocyanidin. Bacteroides sp. 22 could hydrolyze rutin to quercetin-3-O-glucoside. In order to further explain the metabolism pathway of rutin, the β-D-glucosidase and α-L-rhamnosidase activities of five strains were determined. Bacteroides sp. 22 could produce α-L-rhamnosidase but did not produce β-D-glucosidase or β-D-glucosidase activity was too low to be detected. The other four strains all demonstrated α-L-rhamnosidase and β-D-glucosidase activities. Furthermore, α-L-rhamnosidase and β-D-glucosidase activities of Veillonella sp. 32 and Bacteroides sp. 42 were higher than those of Bacteroides sp. 45 and Bacillus sp. 52. Based on these results, we can propose the deglycosylated rout of rutin: rutin was metabolized to be quercetin-3-O-glucoside by α-L-rhamnosidase produced from these bacteria, thereafter, quercetin-3-O-glucoside was further metabolized by β-D-glucosidase to form leucocyanidin. Because of the higher enzyme activity in Veillonella sp. 32 and Bacteroides sp. 42, quercetin-3-O-glucoside was completely metabolized to leucocyanidin by these two bacteria. Due to the lack of β-D-glucosidase activity, Bacteroides sp. 22 could not further metabolize quercetin-3-O-glucoside to leucocyanidin. This study will be helpful for understanding the deglycosylated rout of rutin and the role of different intestinal bacteria on the metabolism of natural compounds. Copyright © 2012 Elsevier B.V. All rights reserved.