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Sample records for iridoid glucoside aucubin

  1. Bis-iridoid glucosides from Abelia chinensis.

    PubMed

    Tomassini, L; Foddai, S; Serafini, M; Cometa, M F

    2000-07-01

    Seven bis-iridoid glucosides have been isolated from Abelia chinensis and were characterized by having a secoiridoid residue as unit A esterifying a C(10)-iridoid or a delta-lactone iridoid as unit B. Among these, compounds 1-3 are new and correspond to 7-O-acetyllaciniatoside IV, 7-O-acetyllaciniatoside V, and 7-O-acetylabelioside B, respectively. The structures of 1-3 were elucidated by spectral methods. PMID:10924185

  2. Two new iridoid glucosides from Hedyotis diffusa.

    PubMed

    Zhang, Yongyong; Chen, Yan; Fan, Chunlin; Ye, Wencai; Luo, Jiabo

    2010-09-01

    Two new iridoid glucosides, named diffusosides A and B, were isolated from the aerial part of Hedyotis diffusa Willd. Their structures were elucidated by 1D-, 2D-NMR spectroscopic analysis and HRESIMS. These two compounds showed no cytotoxic activity against SMMC-7721, SW480, SW620, Bel7402, and HepG2 cells. PMID:20080156

  3. An Iridoid Glucoside and the Related Aglycones from Cornus florida

    PubMed Central

    2015-01-01

    A new iridoid glucoside, cornusoside A (1), and four new natural product iridoid aglycones, cornolactones A–D (2–5), together with 10 known compounds were isolated from the leaves of Cornus florida. The structures of compounds 1–5 were established by interpretation of their spectroscopic data. Cornolactone B (3) is the first natural cis-fused tricyclic dilactone iridoid containing both a five- and a six-membered lactone ring. A biosynthesis pathway is proposed for cornolactones C (4) and D (5), the C-6 epimers of compounds 1–3. PMID:25141901

  4. New iridoid glucosides from the aerial parts of Verbena brasiliensis.

    PubMed

    Ono, Masateru; Oishi, Kanna; Abe, Hiroaki; Masuoka, Chikako; Okawa, Masafumi; Ikeda, Tsuyoshi; Nohara, Toshihiro

    2006-10-01

    Two new iridoid glucosides, verbenabraside A (1) and verbenabraside B (2), were isolated from the aerial parts of Verbena brasiliensis VELL., along with six known iridoid glucosides, gelsemiol 3-O-beta-D-glucoside (3), verbraside (4), 9-hydroxysemperoside (5), griselinoside (6), aralidioside (7), and 6alpha-hydroxyforsythide dimethyl ester (8), three known phenylethanoid glycosides, 2-phenylethyl O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (9), acteoside (10), and leucosceptoside A (11), two known lignan glucosides, dihydroxymethyl-bis(3,5-dimethoxy-4-hydroxyphenyl) tetrahydrofuran-9 (or 9')-O-beta-glucopyranoside (12) and (+)-lyoniresinol 3alpha-O-beta-D-glucopyranoside (13), a known methyl salicylate glucoside, methyl 2-O-beta-D-glucopyranosylbenzoate (14), and two known sterols, beta-sitosterol 3-O-beta-D-glucopyranoside (15) and beta-sitosterol (16). Their chemical structures were determined on the basis of spectroscopic data. Compound 1 exhibited stronger scavenging effect on the stable free radical 1,1-diphenyl-2-picrylhydrazyl than that of alpha-tocopherol. PMID:17015981

  5. Iridoid glucosides with insecticidal activity from Galium melanantherum.

    PubMed

    Tzakou, Olga; Mylonas, Philippos; Vagias, Constantinos; Petrakis, Panos V

    2007-01-01

    The insecticidal activity of the endemic species Galium melanantherum was evaluated against Crematogaster scutellaris ants and Kalotermes flavicollis termites. Iridoid glucosides 1-7 were isolated for the first time as metabolites of the investigated plant, along with the coumarin scopolin. The main components of the extract were found to be the non-acetylated iridoids: geniposidic acid (1), 10-hydroxyloganin (2), deacetyldaphylloside (3), monotropein (4), deacetylasperulosidic acid (5) and scandoside (6), while asperulosidic acid (7) was present only in minute quantities. All isolated metabolites were identified on the basis of their spectral data. Laboratory bioassays revealed significant levels of toxicity for 1-4 against Kalotermes flavicollis termites and Crematogaster scutellaris ants. PMID:17913079

  6. Iridoid glucosides from leaves and stem barks of Parkia javanica.

    PubMed

    Dinda, Biswanath; Chandra Mohanta, Bikas; Debnath, Sudhan; Ghosh, Biplab; Arima, Shiho; Sato, Noriko; Harigaya, Yoshihiro

    2009-01-01

    Two new iridoid glucosides, javanicosides A (1) and B (2) along with the known compounds, ursolic acid and beta-sitosterol were isolated from the leaf and stem bark of Parkia javanica and the structures were established on the basis of detailed spectroscopic analysis (MS, 1D, and 2D NMR experiments). The new compounds were identified as 8-O-p-hydroxybenzoyl-6'-O-p-coumaroyl-mussaenosidic acid (1) and 7-O-E-3,4-dimethoxycinnamoyl-6'-O-beta-D-glucopyranosylloganic acid (2). PMID:19408146

  7. Iridoid glucosides in the endemic Picconia azorica (Oleaceae).

    PubMed

    Gousiadou, Chrysoula; Kokubun, Tetsuo; Martins, José; Gotfredsen, Charlotte H; Jensen, Søren R

    2015-07-01

    In our continued investigation of plants from the family Oleaceae we have now investigated Picconia azorica endemic to the Azores. Like most species within the family it contains the oleoside-based secoiridoid glucosides ligstroside and oleuropein as the main compounds and in addition verbascoside and echinacoside. As with the previously investigated Picconia excelsa, it also contained the carbocyclic iridoid glucosides involved in the biosynthetic pathway to the oleoside derivatives. However, while P. excelsa contained loganin esterified with some monoterpenoid acids, P. azorica contains similar esters of 7-epi-loganic acid named Picconioside A and B. In addition were found the two 7-O-E/Z-cinnamoyl esters of 7-epi-loganic acid named Picconioside C and D. PMID:25687603

  8. Dipasperoside A, a novel pyridine alkaloid-coupled iridoid glucoside from the roots of Dipsacus asper.

    PubMed

    Li, Feng; Tanaka, Ken; Watanabe, Shiro; Tezuka, Yasuhiro; Saiki, Ikuo

    2013-01-01

    A new pyridine alkaloid-coupled iridoid glucoside, dipasperoside A (1), and 20 known compounds (2–21) were isolated from a water extract of Dipsacus asper roots. Compound 1 possessed a unique structural feature with a nicotinic acid nucleus coupled through C-5 with C-7 of a secoiridoid/iridoid glucoside dimer, and esterified with a C-7 hydroxyl group of an iridoid glucoside monomer. All isolates were evaluated for their inhibitory activity against nitric oxide (NO) production in a lipopolysaccharide (LPS)-activated murine macrophage cell line, RAW264.7. PMID:24436964

  9. [Selective enrichment of iridoid glucosides in Hedyotis diffusa Willd. by tandem solid phase extraction].

    PubMed

    Zhang, Feng; Guo, Zhimou; Zhang, Feifang; Xue, Xingya; Liang, Xinmiao

    2009-07-01

    A method for selective enrichment of iridoid glucosides in Hedyotis diffusa Willd. by tandem solid phase extraction (SPE) was developed. Oligo(ethylene glycol) (OEG) is a novel type of separation material made in this laboratory. The differences of the surface chemical structures between OEG material and ODS material resulted in their different retention capabilities for iridoid glucosides. Based on the differences, an OEG-ODS solid phase extraction method was designed for selective enrichment of iridoid glucosides. The water extract (150.28 mg) of Hedyotis diffusa Willd. was precipitated by ethanol, and an aliquot (27.03 mg) of the product from the supernatant solution was loaded onto an OEG cartridge and rinsed by 5 mL water. Then, the rinsing solution was loaded onto an ODS cartridge. After it was washed by 5 mL water and eluted by 5 mL methanol, 4.01 mg final product was obtained from the methanol eluent. All the products were characterized by ultra performance liquid chromatography (UPLC), and 14 representative peaks of iridoid glucosides were found. The enrichment results were proved effective by directly comparing the chromatograms each step. To further characterize the enrichment efficiency, the changes of the peak area of iridoid glucosides were investigated. The results showed that the content of 14 iridoid glucosides in the final product reached 6.10 times its original proportion in water extraction product and their recovery was 50.1% on average. Therefore, the iridoid glucosides can be enriched by the tandem solid phase extraction method from water extracting-ethanol precipitating solution of Hedyotis diffusa Willd. with a good selectivity and an acceptable recovery. The proposed method has the advantages of high enrichment efficiency and simple operation. PMID:19938499

  10. Analysis of iridoid glucosides from Paederia scandens using HPLC-ESI-MS/MS.

    PubMed

    Wu, Zhi-Jun; Wang, Jian-Hua; Fang, Dong-Mei; Zhang, Guo-Lin

    2013-04-01

    Iridoid glycosides are an important class of natural products and have many biological activities. Iridoid glucosides in an extract of the plant species Paederia scandens were investigated using reversed-phase high performance liquid chromatography and electrospray quadrupole time-of-flight-type tandem mass spectrometry. The elemental composition of most of the compounds was determined by accurate mass and relative isotopic abundance (RIA) measurements. In positive ion mode, the fragmentation of [M+NH4](+) precursor ions was carried out using low energy collision-induced electrospray ionization tandem spectrometry. The neutral losses of NH3, H2O, Glc, and the side chain of the iridoid moiety were the main fragmentation patterns observed. For simple iridoid glycosides, the main differences were related to the side chains. Fragmentation of the [M-H](-)precursor ions was achieved for the compounds possibly having phenolic acid group. The connection order of the iridoid, sugar, and phenolic acid moieties, and the linkage of the 6-OH group of the sugar to the phenolic acid were unambiguously confirmed using a combination of MS/MS spectra in both positive and negative ion modes, and our previous work. For some trace dimeric iridoid glucosides, the connection order between the asperuloside and paederoside moieties was determined by the characteristic product ions; this was supported by D-labeling experiments. A total of 24 iridoid glucosides, including 14 new species, were identified or tentatively characterized based on exact mass, RIA values, tandem mass spectra, and D-labeling experiments. PMID:23466447

  11. Three new iridoid glucoside salts from Hedyotis tenelliflora Growing in Vietnam.

    PubMed

    Van Long, Luu H; Nga, Vo Thi; Dam, Nguyen Phuc; Hung, Mai Anh; Dung, Tu Duc; Quang, Ton That; Phung, Nguyen K Phi

    2013-11-01

    Three new sodium salts of iridoid acids, deacetylasperulosidic acid sodium salt (1), teneoside D (2), and teneoside E (3) were isolated from the leaves of Hedyotis tenelliflora Blume (Rubiaceae), together with seven known iridoids, 6alpha-hydroxygeniposide (4), 6beta-hydroxygeniposide (5), 6-O-methyldeacetylasperulosidic acid methyl ester (6), 6-O-methylscandoside methyl ester (7), 6alpha-methoxygeniposidic acid (8), daphylloside (9), and mollugoside methyl ester (10). Their chemical structures were elucidated by 1D and 2D NMR spectroscopy, as well as HR-ESI-MS analysis. PMID:24427927

  12. Analysis of iridoid glucosides in Hedyotis diffusa by high-performance liquid chromatography/electrospray ionization tandem mass spectrometry.

    PubMed

    Li, Cunman; Xue, Xingya; Zhou, Dayong; Zhang, Feifang; Xu, Qing; Ren, Lingling; Liang, Xinmiao

    2008-09-10

    An HPLC-DAD-ESI-MS/MS method was developed for analysis of iridoid glucosides (IGs) from Hedyotis diffusa Willd. The optimized separation condition was achieved with the Complex Sample Analysis Software System (CSASS) software, under which the whole analytes were achieved complete resolution especially for some isomeric IGs. Based on the UV and fragmentations, eleven IGs were detected. According to the fragmentation patterns of the three standard IGs, especially those of the isomeric standards, seven IGs including three pairs of isomers were unambiguous/tentatively identified. For the isomeric IGs with methyl ester or carboxyl group at C-4, the extents of the losses of CH3OH and/or H2O from their molecular and/or the aglycone adducts are useful for the differentiation of the stereoisomers in positive ion (PI) mode, which depends on the stereochemistry of the hydroxyl group on the cyclopentanoid unit. PMID:18579330

  13. Characterization and identification of iridoid glucosides, flavonoids and anthraquinones in Hedyotis diffusa by high-performance liquid chromatography/electrospray ionization tandem mass spectrometry.

    PubMed

    Liu, E-Hu; Zhou, Ting; Li, Guo-Bin; Li, Jing; Huang, Xiu-Ning; Pan, Feng; Gao, Ning

    2012-01-01

    The multiple bioactive constituents in Hedyotis diffusa Willd. (H. diffusa) were extracted and characterized by high-performance liquid chromatography/electrospray ionization tandem mass spectrometry (HPLC-ESI-MS(n)). The optimized separation condition was obtained using an Agilent ZorBax SB-C18 column (4.6×150 mm, 5 μm) and gradient elution with water (containing 0.1% formic acid) and acetonitrile (containing 0.1% formic acid), under which baseline separation for the majority of compounds was achieved. Among the compounds detected, 14 iridoid glucosides, 10 flavonoids, 7 anthraquinones, 1 coumarin and 1 triterpene were unambiguously identified or tentatively characterized based on their retention times and mass spectra in comparison with the data from standards or references. The fragmentation behavior for different types of constituents was also investigated, which could contribute to the elucidation of these constituents in H. diffusa. The present study reveals that even more iridoid glycosides were found in H. diffusa than hitherto assumed. The occurrence of two iridoid glucosides and five flavonoids in particular has not yet been described. This paper marks the first report on the structural characterization of chemical compounds in H. diffusa by a developed HPLC-ESI-MS(n) method. PMID:25940590

  14. Occurrence of iridoid glycosides in in vitro cultures and intact plants of Scrophularia nodosa L.

    PubMed

    Sesterhenn, Katja; Distl, Melanie; Wink, Michael

    2007-03-01

    Shoot, root, and callus cultures of Scrophularia nodosa L. (Scrophulariaceae) were established and cultivated in vitro. Iridoid glycosides, such as harpagoside, aucubin, and catalpol were identified by LC-ESI-MS and their contents determined by HPLC. For comparison intact plants of S. nodosa were analysed. In shoot cultures slightly lower amounts of detectable iridoid glycosides (4.36% dry weight) were determined than in the field grown plants (4.88%). Concentration of harpagoside was highest in leaves of field plants (1.05%) and in flowers of in vitro plantlets (1.10%). For aucubin the highest amount was found in the leaves of in vitro plantlets (1.67%) whereas the levels of aucubin in the leaves of field plants were remarkably lower. Catalpol was produced as a trace compound in intact plants and shoot cultures. Callus and root cultures were apparently not able to synthesise iridoid glycosides. PMID:16972093

  15. Host dependent iridoid glycoside sequestration patterns in Cionus hortulanus.

    PubMed

    Baden, Christian Ulrich; Franke, Stephan; Dobler, Susanne

    2013-08-01

    Weevils of the genus Cionus (Curculionidae, Mecininae) sequester the iridoid glycosides (IGs) aucubin and catalpol from their host plants Scrophularia or Verbascum (Scrophulariaceae). Cionus hortulanus is the only member of the genus that feeds on both plant genera. We previously showed that sequestration patterns in C. hortulanus depend on the local host. To investigate whether IG patterns are driven by their availability in the hosts or genetic differences between populations, we collected C. hortulanus from S. nodosa in the field and reared them either on S. nodosa or on V. nigrum. The differences in IG concentrations were specific for the host plant upon which the weevils developed. Similar to monophagous species of the Cionini, individuals from S. nodosa had more aucubin than catalpol and mirrored the concentrations of their host plants. Specimens from V. nigrum, on the other hand, had higher concentrations of aucubin and of catalpol than their host. On V. nigrum, the ratio of catalpol to aucubin differed significantly between plant and beetle samples due to much higher catalpol concentrations in the weevils. Our data thus contradict genetically fixed differences between populations living on either plant but rather document the host plants' influence on the beetles' metabolism. PMID:23846185

  16. Simultaneous Determination of Catalpol, Aucubin, and Geniposidic Acid in Different Developmental Stages of Rehmannia glutinosa Leaves by High Performance Liquid Chromatography

    PubMed Central

    Wang, Yanjie; Liao, Dengqun; Qin, Minjian

    2016-01-01

    Although R. glutinosa roots are currently the only organ source in clinics, its leaves are a potential supplement for the roots especially in extraction of some important bioactive compounds. Our early work found that the contents of catalpol and total iridoid glycosides varied among different developmental stages of R. glutinosa leaves. Aucubin and geniposidic acid, the abundant major bioactive compounds in Eucommia ulmoides and Gardenia jasminoides, respectively, were found present in R. glutinosa roots, however, and have not been analyzed in its leaves. In this paper, we aimed to determine contents of these three iridoid glycosides in different developmental stages of R. glutinosa leaves using the optimized HPLC-UV conditions. Our results showed that aucubin and GPA in R. glutinosa leaves were much lower than catalpol and showed the increasing trend with the leaf development, which was different from catalpol. This work provided the important information for future exploitation of R. glutinosa leaves as a potential supplement for its roots in extraction of some important bioactive compounds and studying the relationship of aucubin and catalpol metabolism. PMID:27429834

  17. Liver-protective activities of aucubin derived from traditional oriental medicine.

    PubMed

    Chang, I M

    1998-11-01

    The iridoid glycosides including aucubin (AU), catalpol (CA), swertimarin (SW), and gardenoside (GA) are frequently found as natural constituents of many traditional oriental medicinal plants including Chinese herbs. Among these iridoid glycosides, AU was systematically studied for its potent liver-protective activities using experimental systems of hepatic damage. AU showed high liver-protective activity against carbon tetrachloride-induced hepatic damage in mice. Also AU showed significant protective activity against alpha-amanitin-induced hepatic damage in mice, and it prevented a depression of liver RNA biosynthesis caused by alpha-amanitin administration. Potent antidotal effects on mushroom poisoning in beagle dogs ingested with aqueous extract of Amanita virosa was observed; beagle dogs completely survived, even when AU administration was withheld for half an hour after mushroom poisoning. In addition, AU was found to suppress hepatitis B viral DNA replication in vitro. Conversion of AU to its aglycone form appeared to be a prerequisite step for an exhibition of such antiviral activity. PMID:10100510

  18. Iridoid biosynthesis in Chrysomelina larvae: Fat body produces early terpenoid precursors.

    PubMed

    Burse, Antje; Schmidt, Axel; Frick, Sindy; Kuhn, Jürgen; Gershenzon, Jonathan; Boland, Wilhelm

    2007-03-01

    Larvae of the Chrysomelina species Phaedon cochleariae and Gastrophysa viridula produce monoterpenoids (iridoids) to defend themselves against predatory attacks by presenting the toxins upon attack as droplets on the top of nine pairs of dorsal glands. Although the conversion of 8-hydroxygeraniol-8-O-beta-d-glucoside into the iridoids in the glandular reservoir has been studied in detail, the synthesis of the glucosidically bound precursor received only limited attention. We compared larvae of the two iridoid producing species with those of Chrysomela populi, a sequestering species producing salicylaldehyde, in terms of the key enzymes 3-hydroxy-3-methylglutaryl-CoA reductase (HMGR) and isoprenyl diphosphate synthases involved in the biosynthesis of the iridoid precursor. Increased HMGR transcript abundance, high HMGR activity and accumulation of geraniol indicating geranyl diphosphate synthase activity was observed only in the fat body of the iridoid producing larvae in comparison to other larval tissues and to the tested tissues of C. populi. These results correlate with the identification of glucosidically bound 8-hydroxygeraniol in the fat body of the iridoid producers. We suggest that in P. cochleariae and G. viridula glucosidically bound 8-hydroxygeraniol is produced by the fat body and transferred via the hemolymph into the glandular reservoir for further conversion into iridoids. PMID:17296500

  19. New iridoid diesters of glucopyranose from Linaria canadensis (L.) Dum.

    PubMed

    Mizuochi, Kouichi; Tanaka, Takashi; Kouno, Isao; Fujioka, Toshihiro; Yoshimura, Yuki; Ishimaru, Kanji

    2011-01-01

    Two new iridoid diesters of glucopyranose were isolated from the aerial part of Linaria canadensis (L.) Dum. Eight known flavones, apigenin, diosmetin, genkwanin, luteolin, luteolin 7-O-glucoside, luteolin 7-O-glucuronide, genkwanin 4'-O-rutinoside, and quercetin 7-O-rutinoside were also isolated. The chemical structures of the isolated compounds were elucidated based on the analyses of the spectroscopic data. PMID:20635154

  20. Role of plant β-glucosidases in the dual defense system of iridoid glycosides and their hydrolyzing enzymes in Plantago lanceolata and Plantago major.

    PubMed

    Pankoke, Helga; Buschmann, Torsten; Müller, Caroline

    2013-10-01

    The typical defense compounds of Plantaginaceae are the iridoid glycosides, which retard growth and/or enhance mortality of non-adapted herbivores. In plants, glycosidic defense compounds and hydrolytic enzymes often form a dual defense system, in which the glycosides are activated by the enzymes to exert biological effects. Yet, little is known about the activating enzymes in iridoid glycoside-containing plants. To examine the role of plant-derived β-glucosidases in the dual defense system of two common plantain species, Plantago lanceolata and Plantago major, we determined the concentration of iridoid glycosides as well as the β-glucosidase activity in leaves of different age. To investigate the presence of other leaf metabolites potentially involved in plant defense, we used a metabolic fingerprinting approach with ultra-high performance liquid chromatography coupled with time-of-flight-mass spectrometry. According to the optimal defense hypothesis, more valuable parts such as young leaves should be better protected than less valuable parts. Therefore, we expected that both, the concentrations of defense compounds as well as the β-glucosidase activity, should be highest in younger leaves and decrease with increasing leaf age. Both species possessed β-glucosidase activity, which hydrolyzed aucubin, one of the two most abundant iridoid glycosides in both plant species, with high activity. In line with the optimal defense hypothesis, the β-glucosidase activity in both Plantago species as well as the concentration of defense-related metabolites such as iridoid glycosides correlated negatively to leaf age. When leaf extracts were incubated with bovine serum albumin and aucubin, SDS-PAGE revealed a protein-denaturing effect of the leaf extracts of both plantain species, suggesting that iridoid glycosides and plant β-glucosidase interact in a dual defense system. PMID:23773298

  1. A new iridoid glycoside from the roots of Dipsacus asper.

    PubMed

    Ji, De; Zhang, Chunfeng; Li, Jingzhi; Yang, Haowei; Shen, Jingyang; Yang, Zhonglin

    2012-01-01

    A new iridoid glycoside, named loganic acid ethyl ester (1), together with five known compounds: chlorogenic acid (2), caffeic acid (3), loganin (4), cantleyoside (5) and syringaresinol-4',4''-O-bis-β-D-glucoside (6) were isolated from the roots of Dipsacus asper. The structure of compound 1 was elucidated on the basis of detailed spectroscopic analyses. Lignan is isolated from Dipsacaceae species for the first time. Compounds 1, 4 and 5 had moderate neuroprotective effects against the Aβ₂₅₋₃₅ induced cell death in PC12 cells. PMID:22306831

  2. Iridoid glycosides from Barleria lupulina.

    PubMed

    Kim, Ki Hyun; Park, Yong Joo; Chung, Kyu Hyuck; Yip, M L Richard; Clardy, Jon; Senger, Donald; Cao, Shugeng

    2015-02-27

    Phytochemical investigation of an extract of the aerial part of Barleria lupulina resulted in the identification of four new iridoid glycosides (1-4), together with 14 known analogues (5-18). The structures of 1-4 were determined through 1D and 2D NMR spectroscopic data analysis, HRMS, and acid hydrolysis. This is the first report of iridoid glycosides with a formate group. The free-radical scavenging activity of compounds 9, 12, and 15-17 was assessed using the DPPH assay. Compounds 16 and 17 scavenged DPPH radicals weakly with IC50 values of 97.5 and 78.6 μg/mL, respectively. PMID:25611215

  3. Determination of phenylethanoid glycosides and iridoid glycosides from therapeutically used Plantago species by CE-MEKC.

    PubMed

    Gonda, Sándor; Nguyen, Nhat Minh; Batta, Gyula; Gyémánt, Gyöngyi; Máthé, Csaba; Vasas, Gábor

    2013-09-01

    CE methods are valuable tools for medicinal plant quality management, screening, and analysis. Therefore, the aim of the current study was to optimize and validate a CE-MEKC method for simultaneous quantification of four chief bioactive metabolites from Plantago species. The two most important secondary metabolite groups were aimed to be separated. Different electrolyte and surfactant types were tested. Surfactant concentration, BGE pH, electrolyte concentration, and buffering capacity were optimized. The final BGE consisted of 15 mM sodium tetraborate, 20 mM TAPS, and 250 mM DOC at pH 8.50. Acceptable precision, good stability, and accuracy were achieved, with high resolution for phenylethanoid glycosides. Analytes were separated within 20 min. The method was shown to be suitable for the quantification of the iridoid glycosides aucubin and catalpol, and the phenylethanoid glycosides acteoside (verbascoside) and plantamajoside from water extracts of different samples. The method was shown to be applicable to leaf extracts of Plantago lanceolata, Plantago major, and Plantago asiatica, the main species with therapeutic applications, and a biotechnological product, plant tissue cultures (calli) of P. lanceolata. Baseline separation of the main constituents from minor peaks was achieved, regardless of the matrix type. PMID:23784714

  4. Two new bioactive iridoids from Rothmannia wittii.

    PubMed

    Chaipukdee, Nattapong; Kanokmedhakul, Kwanjai; Kanokmedhakul, Somdej; Lekphrom, Ratsami; Pyne, Stephen G

    2016-09-01

    The first reported study of the isolation and identification of compounds from the bark and fruit of Rothmannia wittii yielded two new iridoids, 6β-hydroxy-10-O-acetylgenipin (1) and 10-O-acetylmacrophyllide (2) together with six known iridoids; 6β-hydroxygenipin (3), genipin (4), garjasmine (5), cerbinal (6), and mixture of β-gardiol (7) and α-gardiol (8); benzoic acid (9); vanillic acid (10); and stigmasterol (11). Their structures were elucidated by spectroscopic methods. Iridoid 1 showed antimycobacterial activity against Mycobacterium tuberculosis with a MIC value of 12.50μg/mL. Iridoid 2 showed cytotoxicity against the NCI-H187 cancer cell line with an IC50 value of 6.82μg/mL. In addition, 2 and 5 exhibited weak cytotoxic activity against KB and MCF-7 cell lines, while 4 was active against the NCI-H187 cancer cell line. PMID:27431771

  5. Aucubin prevents interleukin-1 beta induced inflammation and cartilage matrix degradation via inhibition of NF-κB signaling pathway in rat articular chondrocytes.

    PubMed

    Wang, Sheng-Nan; Xie, Guo-Ping; Qin, Cheng-He; Chen, Yi-Rong; Zhang, Kai-Rui; Li, Xue; Wu, Qian; Dong, Wei-Qiang; Yang, Jun; Yu, Bin

    2015-02-01

    Proinflammatory cytokine interleukin-1β (IL-1β) plays a crucial role in the pathogenesis of Osteoarthritis (OA) by stimulating several mediators contributed to cartilage degradation. Aucubin, a natural compound derived from plants which has been shown to possess diverse biological activities including anti-inflammatory property, may benefit the IL-1β stimulated chondrocytes. The present study was aimed to investigate the effects of Aucubin on IL-1β stimulated rat chondrocytes. Rat chondrocytes were cultured and pretreated with Aucubin (1, 10, 20, 50μM), and then stimulated with or without IL-1β (10ng/ml). Gene and protein expression of MMP-3, MMP-9, MMP-13, cyclooxygenase-2 (COX-2), inducible nitric oxide synthase (iNOS) was determined by real-time PCR and Western blotting respectively. Nitric oxide (NO) production was quantified by Griess reagent. Phosphorylation and nuclear translocation of p65 were detected by western blotting and immunofluorescence, respectively. We found that Aucubin significantly reversed the elevated gene and protein expression of MMP-3, MMP-9, MMP-13, iNOS, COX-2 and the production of NO induced by IL-1β challenge in rat chondrocytes. Furthermore, Aucubin was able to suppress the IL-1β-mediated phosphorylation and nuclear translocation of p65, indicating Aucubin may possibly act via the NF-κB signaling pathway. The present study proposes that Aucubin may be a potential therapeutic choice in the treatment of OA due to its anti-inflammatory and chondroprotective features. PMID:25576403

  6. Selective transport systems mediate sequestration of plant glucosides in leaf beetles: A molecular basis for adaptation and evolution

    PubMed Central

    Kuhn, Jürgen; Pettersson, Eva M.; Feld, Birte K.; Burse, Antje; Termonia, Arnaud; Pasteels, Jacques M.; Boland, Wilhelm

    2004-01-01

    Chrysomeline larvae respond to disturbance and attack by everting dorsal glandular reservoirs, which release defensive secretions. The ancestral defense is based on the de novo synthesis of monoterpene iridoids. The catabolization of the host-plant O-glucoside salicin into salicylaldehyde is a character state that evolved later in two distinct lineages, which specialized on Salicaceae. By using two species producing monoterpenes (Hydrothassa marginella and Phratora laticollis) and two sequestering species (Chrysomela populi and Phratora vitellinae), we studied the molecular basis of sequestration by feeding the larvae structurally different thioglucosides resembling natural O-glucosides. Their accumulation in the defensive systems demonstrated that the larvae possess transport systems, which are evolutionarily adapted to the glycosides of their host plants. Minor structural modifications in the aglycon result in drastically reduced transport rates of the test compounds. Moreover, the ancestral iridoid-producing leaf beetles already possess a fully functional import system for an early precursor of the iridoid defenses. Our data confirm an evolutionary scenario in which, after a host-plant change, the transport system of the leaf beetles may play a pivotal role in the adaptation on new hosts by selecting plant-derived glucosides that can be channeled to the defensive system. PMID:15365181

  7. Two new iridoids from Verbena officinalis L.

    PubMed

    Shu, Jicheng; Chou, Guixin; Wang, Zhengtao

    2014-01-01

    Two new iridoids, 3-(5-(methoxycarbonyl)-2-oxo-2H-pyran-3-yl)butanoic acid, named verbeofflin I (1), and 7-hydroxydehydrohastatoside (2), were isolated from the aerial part of Verbena officinalis L, along with three known iridoids, verbenalin (3), 3,4-dihydroverbenalin (4), hastatoside (5) by means of various column chromatography steps. The structures of these compounds were elucidated through analysis of their spectroscopic data obtained using 1D and 2D NMR and MS techniques. Verbeofflin I (1) is the new class of secoiridoid in the family Verbenaceae. PMID:25045888

  8. Anti-inflammatory iridoids of botanical origin.

    PubMed

    Viljoen, A; Mncwangi, N; Vermaak, I

    2012-01-01

    Inflammation is a manifestation of a wide range of disorders which include; arthritis, atherosclerosis, Alzheimer's disease, inflammatory bowel syndrome, physical injury and infection amongst many others. Common treatment modalities are usually nonsteroidal anti-inflammatory drugs (NSAIDs) such as aspirin, paracetamol, indomethacin and ibuprofen as well as corticosteroids such as prednisone. These however, may be associated with a host of side effects due to non-selectivity for cyclooxygenase (COX) enzymes involved in inflammation and those with selectivity may be highly priced. Thus, there is a continuing search for safe and effective antiinflammatory molecules from natural sources. Research has confirmed that iridoids exhibit promising anti-inflammatory activity which may be beneficial in the treatment of inflammation. Iridoids are secondary metabolites present in various plants, especially in species belonging to the Apocynaceae, Lamiaceae, Loganiaceae, Rubiaceae, Scrophulariaceae and Verbenaceae families. Many of these ethnobotanicals have an illustrious history of traditional use alluding to their use to treat inflammation. Although iridoids exhibit a wide range of pharmacological activities such as cardiovascular, hepatoprotection, hypoglycaemic, antimutagenic, antispasmodic, anti-tumour, antiviral, immunomodulation and purgative effects this review will acutely focus on their anti-inflammatory properties. The paper aims to present a summary for the most prominent iridoid-containing plants for which anti-inflammatory activity has been demonstrated in vitro and / or in vivo. PMID:22414102

  9. Anti-Inflammatory Iridoids of Botanical Origin

    PubMed Central

    Viljoen, A; Mncwangi, N; Vermaak, I

    2012-01-01

    Inflammation is a manifestation of a wide range of disorders which include; arthritis, atherosclerosis, Alzheimer’s disease, inflammatory bowel syndrome, physical injury and infection amongst many others. Common treatment modalities are usually non-steroidal anti-inflammatory drugs (NSAIDs) such as aspirin, paracetamol, indomethacin and ibuprofen as well as corticosteroids such as prednisone. These however, may be associated with a host of side effects due to non-selectivity for cyclooxygenase (COX) enzymes involved in inflammation and those with selectivity may be highly priced. Thus, there is a continuing search for safe and effective anti-inflammatory molecules from natural sources. Research has confirmed that iridoids exhibit promising anti-inflammatory activity which may be beneficial in the treatment of inflammation. Iridoids are secondary metabolites present in various plants, especially in species belonging to the Apocynaceae, Lamiaceae, Loganiaceae, Rubiaceae, Scrophulariaceae and Verbenaceae families. Many of these ethnobotanicals have an illustrious history of traditional use alluding to their use to treat inflammation. Although iridoids exhibit a wide range of pharmacological activities such as cardiovascular, hepatoprotection, hypoglycaemic, antimutagenic, antispasmodic, anti-tumour, antiviral, immunomodulation and purgative effects this review will acutely focus on their anti-inflammatory properties. The paper aims to present a summary for the most prominent iridoid-containing plants for which anti-inflammatory activity has been demonstrated in vitro and / or in vivo. PMID:22414102

  10. Eucommia ulmoides Oliver Extract, Aucubin, and Geniposide Enhance Lysosomal Activity to Regulate ER Stress and Hepatic Lipid Accumulation

    PubMed Central

    Lee, Hwa-Young; Lee, Geum-Hwa; Lee, Mi-Rin; Kim, Hye-Kyung; Kim, Nan-young; Kim, Seung-Hyun; Lee, Yong-Chul; Kim, Hyung-Ryong; Chae, Han-Jung

    2013-01-01

    Eucommia ulmoides Oliver is a natural product widely used as a dietary supplement and medicinal plant. Here, we examined the potential regulatory effects of Eucommia ulmoides Oliver extracts (EUE) on hepatic dyslipidemia and its related mechanisms by in vitro and in vivo studies. EUE and its two active constituents, aucubin and geniposide, inhibited palmitate-induced endoplasmic reticulum (ER) stress, reducing hepatic lipid accumulation through secretion of apolipoprotein B and associated triglycerides and cholesterol in human HepG2 hepatocytes. To determine how EUE diminishes the ER stress response, lysosomal and proteasomal protein degradation activities were analyzed. Although proteasomal activity was not affected, lysosomal enzyme activities including V-ATPase were significantly increased by EUE as well as aucubin and geniposide in HepG2 cells. Treatment with the V-ATPase inhibitor, bafilomycin, reversed the inhibition of ER stress, secretion of apolipoprotein B, and hepatic lipid accumulation induced by EUE or its component, aucubin or geniposide. In addition, EUE was determined to regulate hepatic dyslipidemia by enhancing lysosomal activity and to regulate ER stress in rats fed a high-fat diet. Together, these results suggest that EUE and its active components enhance lysosomal activity, resulting in decreased ER stress and hepatic dyslipidemia. PMID:24349058

  11. Structural determinants of reductive terpene cyclization in iridoid biosynthesis.

    PubMed

    Kries, Hajo; Caputi, Lorenzo; Stevenson, Clare E M; Kamileen, Mohammed O; Sherden, Nathaniel H; Geu-Flores, Fernando; Lawson, David M; O'Connor, Sarah E

    2016-01-01

    The carbon skeleton of ecologically and pharmacologically important iridoid monoterpenes is formed in a reductive cyclization reaction unrelated to canonical terpene cyclization. Here we report the crystal structure of the recently discovered iridoid cyclase (from Catharanthus roseus) bound to a mechanism-inspired inhibitor that illuminates substrate binding and catalytic function of the enzyme. Key features that distinguish iridoid synthase from its close homolog progesterone 5β-reductase are highlighted. PMID:26551396

  12. Structural determinants of reductive terpene cyclization in iridoid biosynthesis

    PubMed Central

    Stevenson, Clare E. M.; Kamileen, Mohammed O.; Sherden, Nathaniel H.; Geu-Flores, Fernando; Lawson, David M.; O’Connor, Sarah E.

    2015-01-01

    The carbon skeleton of ecologically and pharmacologically important iridoid monoterpenes is formed in a reductive cyclization reaction unrelated to canonical terpene cyclization. Here we report the crystal structure of the recently discovered iridoid cyclase (Catharanthus roseus) bound to a mechanism-inspired inhibitor that illuminates substrate binding and catalytic function of the enzyme. Key features that distinguish iridoid synthase from its close homologue, progesterone 5β-reductase, are highlighted. PMID:26551396

  13. Iridoid glycosides and cucurbitacin glycoside from Neopicrorhiza scrophulariiflora.

    PubMed

    Kim, Ik Hwi; Uchiyama, Nahoko; Kawahara, Nobuo; Goda, Yukihiro

    2006-12-01

    Three iridoid glycosides, picrorosides A (1), B (2) and C (3), and a cucurbitacin glycoside, scrophoside A (4), were isolated from the rhizomes of Neopicrorhiza scrophulariiflora (Scrophulariaceae), along with two known iridoid glycosides, picrosides I (5) and II (6), and three known cucurbitacin glycosides (7-9). Their structures were elucidated on the basis of both chemical and spectroscopic data. PMID:17070880

  14. A rapid and sensitive determination of aucubin in rat plasma by liquid chromatography-tandem mass spectrometry and its pharmacokinetic application.

    PubMed

    Xu, Wei; Deng, Zhipeng; Guo, Hong; Ling, Peixue

    2012-09-01

    A sensitive, accurate, rapid and robust LC-MS-MS method for the quantification of aucubin, a major bioactive constituent of Aucuba japonica, Eucommia ulmoides and Plantago asiatica, was established and validated in rat plasma. Plasma samples were simply precipitated by adding methanol and the supernatant was chromatographed by a Diamonsil® C(18)(2) column with the mobile phase comprising a mixture of 10 mm ammonium acetate in methanol and that in water with the ratio of 50:50 (v/v). Quantification of aucubin was performed by mass spectrometry in the multiple-reaction monitoring mode with positive atmospheric ionization at m/z 364 → 149 for aucubin, and m/z 380 → 165 for catalpol (IS), respectively. The retention time was 2.47 and 2.44 min for aucubin and the IS, respectively. The calibration curve (10.0-30,000 ng/mL) was linear (r²  > 0.99) and the lower limit of quantification was 10.0 ng/mL in the rat plasma sample. The method showed satisfactory results such as sensitivity, specificity, precision, accuracy, recovery, freeze-thaw and long-term stability. This simple LC-MS method was successfully applied in a pharmacokinetic study carried out in Sprague-Dawley rats after oral administration of aucubin at a single dose of 50 mg/kg. Herein the pharmacokinetic study of aucubin is reported for the first time. PMID:22113886

  15. Phenolic glucosides from Hasseltia floribunda.

    PubMed

    Dagvadorj, Enkhmaa; Shaker, Kamel H; Windsor, Donald; Schneider, Bernd; Boland, Wilhelm

    2010-11-01

    The leaves of Hasseltia floribunda were examined for their chemical constituents. Twelve phenolic glucosides, namely three hydroxycyclohexenyl acyl glucosides, four acylated salicortin derivatives, and five coumaroyl salicin derivatives, were isolated along with eight known phenolic glycosides, six known flavones, and two known sesquiterpenoid cyclohexenone derivatives. The structures of the isolated compounds were elucidated by NMR spectroscopic and HRMS spectrometric methods and by comparing analytical data with those of related structures. PMID:20822782

  16. Conduritol F glucosides and terpenoid glucosides from Cynanchum liukiuense and distribution of conduritol F glucosides in several Asclepiadaceous plants.

    PubMed

    Abe, F; Yamauchi, T; Honda, K; Hayashl, N

    2000-07-01

    Conduritol F 3-0- and 4-O-glucosides were obtained from Cynanchum liukiuense, along with conduritol F which was identified in all Asclepiadaceous plants examined, Tylophora tanakae, Asclepias curassavica and A. fruticosa, as well as in Marsdenia tomentosa. The pattern of the glucosidic linkage to conduritol F differed between individual species, 2-O-glucoside from T tanakae and M. tomentosa, 3-O-glucoside from A. curassavica, but none from A. fruticosa. Along with conduritol F glucosides, an 11-glucosyloxy-megastigmane and a monoterpenoid glucoside were isolated from C. liukiuense. PMID:10923848

  17. New iridoids from the fruits of Crescentia cujete.

    PubMed

    Wang, Gang; Yin, Wei; Zhou, Zhong-Yu; Hsieh, Kun-Lung; Liu, Ji-Kai

    2010-09-01

    Four new 11-nor-iridoids, 6-O-p-hydroxybenzoyl-10-deoxyeucommiol (1), 6-O-benzoyl-10-deoxyeucommiol (2), 6-O-benzoyl-dihydrocatalpolgenin (a mixture of 3 and 4), as well as two known iridoids, ningpogenin (5) and 6-O-p-hydroxybenzoylaucubin (6), were isolated from the fruits of Crescentia cujete Linn. The structures of these compounds were established on the basis of spectroscopic analysis. PMID:20839124

  18. Antiglycation Activity of Iridoids and Their Food Sources

    PubMed Central

    West, Brett J.; Uwaya, Akemi; Isami, Fumiyuki; Deng, Shixin; Nakajima, Sanae; Jensen, C. Jarakae

    2014-01-01

    Iridoids are dietary phytochemicals that may have the ability to inhibit the formation of advanced glycation end products (AGEs). Three studies were conducted to investigate this anti-AGE potential. First, the inhibition of fluorescence intensity by food-derived iridoids, after 4 days of incubation with bovine serum albumin, glucose, and fructose, was used to evaluate in vitro antiglycation activity. Next, an 8-week open-label pilot study used the AGE Reader to measure changes in the skin autofluorescence of 34 overweight adults who consumed daily a beverage containing food sources of iridoids. Finally, a cross-sectional population study with 3913 people analyzed the relationship between daily iridoid intake and AGE accumulation, as measured by skin autofluorescence with the TruAge scanner. In the in vitro test, deacetylasperulosidic acid and loganic acid both inhibited glycation in a concentration-dependent manner, with respective IC50 values of 3.55 and 2.69 mM. In the pilot study, average skin autofluorescence measurements decreased by 0.12 units (P < 0.05). The cross-sectional population survey revealed that, for every mg of iridoids consumed, there is a corresponding decline in AGE associated age of 0.017 years (P < 0.0001). These results suggest that consumption of dietary sources of iridoids may be a useful antiaging strategy. PMID:26904624

  19. Conversion of Substrate Analogs Suggests a Michael Cyclization in Iridoid Biosynthesis

    PubMed Central

    Lindner, Stephanie; Geu-Flores, Fernando; Bräse, Stefan; Sherden, Nathaniel H.; O’Connor, Sarah E.

    2014-01-01

    Summary The core structure of the iridoid monoterpenes is formed by a unique cyclization reaction. The enzyme that catalyzes this reaction, iridoid synthase, is mechanistically distinct from other terpene cyclases. Here we describe the synthesis of two substrate analogs to probe the mechanism of iridoid synthase. Enzymatic assay of these substrate analogs along with clues from the product profile of the native substrate strongly suggest that iridoid synthase utilizes a Michael reaction to achieve cyclization. This improved mechanistic understanding will facilitate the exploitation of the potential of iridoid synthase to synthesize new cyclic compounds from nonnatural substrates. PMID:25444551

  20. The seco-iridoid pathway from Catharanthus roseus.

    PubMed

    Miettinen, Karel; Dong, Lemeng; Navrot, Nicolas; Schneider, Thomas; Burlat, Vincent; Pollier, Jacob; Woittiez, Lotte; van der Krol, Sander; Lugan, Raphaël; Ilc, Tina; Verpoorte, Robert; Oksman-Caldentey, Kirsi-Marja; Martinoia, Enrico; Bouwmeester, Harro; Goossens, Alain; Memelink, Johan; Werck-Reichhart, Danièle

    2014-01-01

    The (seco)iridoids and their derivatives, the monoterpenoid indole alkaloids (MIAs), form two large families of plant-derived bioactive compounds with a wide spectrum of high-value pharmacological and insect-repellent activities. Vinblastine and vincristine, MIAs used as anticancer drugs, are produced by Catharanthus roseus in extremely low levels, leading to high market prices and poor availability. Their biotechnological production is hampered by the fragmentary knowledge of their biosynthesis. Here we report the discovery of the last four missing steps of the (seco)iridoid biosynthesis pathway. Expression of the eight genes encoding this pathway, together with two genes boosting precursor formation and two downstream alkaloid biosynthesis genes, in an alternative plant host, allows the heterologous production of the complex MIA strictosidine. This confirms the functionality of all enzymes of the pathway and highlights their utility for synthetic biology programmes towards a sustainable biotechnological production of valuable (seco)iridoids and alkaloids with pharmaceutical and agricultural applications. PMID:24710322

  1. The seco-iridoid pathway from Catharanthus roseus

    PubMed Central

    Miettinen, Karel; Dong, Lemeng; Navrot, Nicolas; Schneider, Thomas; Burlat, Vincent; Pollier, Jacob; Woittiez, Lotte; van der Krol, Sander; Lugan, Raphaël; Ilc, Tina; Verpoorte, Robert; Oksman-Caldentey, Kirsi-Marja; Martinoia, Enrico; Bouwmeester, Harro; Goossens, Alain; Memelink, Johan; Werck-Reichhart, Danièle

    2014-01-01

    The (seco)iridoids and their derivatives, the monoterpenoid indole alkaloids (MIAs), form two large families of plant-derived bioactive compounds with a wide spectrum of high-value pharmacological and insect-repellent activities. Vinblastine and vincristine, MIAs used as anticancer drugs, are produced by Catharanthus roseus in extremely low levels, leading to high market prices and poor availability. Their biotechnological production is hampered by the fragmentary knowledge of their biosynthesis. Here we report the discovery of the last four missing steps of the (seco)iridoid biosynthesis pathway. Expression of the eight genes encoding this pathway, together with two genes boosting precursor formation and two downstream alkaloid biosynthesis genes, in an alternative plant host, allows the heterologous production of the complex MIA strictosidine. This confirms the functionality of all enzymes of the pathway and highlights their utility for synthetic biology programmes towards a sustainable biotechnological production of valuable (seco)iridoids and alkaloids with pharmaceutical and agricultural applications. PMID:24710322

  2. A New Iridoid from the Aerial Parts of Hedyotis pilulifera.

    PubMed

    Hoai, Nguyen Thi; Duc, Ho Viet; Phu, Nguyen Dinh Quynh; Kodama, Takeshi; Itob, Takuya; Morita, Hiroyuki

    2016-03-01

    A new iridoid, 10-acetylborreriagenin (1), and five known iridoid glycosides (2-6), were isolated from the aerial parts of Hedyotis pilulifera. Their structures were elucidated by spectral analyses, including 1D- and 2D-NMR, and HR-ESI-MS, and comparisons with the NMR data reported in the literature. The isolated compounds 1-6 were tested against six bacterial species. Among them, 10-acetylborreriagenin (1) showed antibacterial activity against Staphylococcus aureus, with an MIC value of 100 µg/mL. PMID:27169182

  3. Iridoids and sesquiterpenoids from the roots of Valeriana jatamansi Jones.

    PubMed

    Dong, Fa-Wu; Liu Yang; Wu, Zhi-Kun; Wei-Gao; Zi, Chen-Ting; Dan Yang; Luo, Huai-Rong; Jun Zhou; Hu, Jiang-Miao

    2015-04-01

    Three new iridoids, jatamanvaltrates R-S (1-2) and jatamanin Q (3), as well as three new sesquiterpenoids, valeriananoids D-E (4, 5) and clovane-2β-isovaleroxy-9α-ol (6), together with nine known compounds were isolated from the roots of Valeriana jatamansi Jones. Compound 2 was the first reported iridoid with fatty acid esters in the Valerianaceae family. The structures of new compounds were established on the basis of extensive spectroscopic analysis. Moreover, all the isolates were evaluated for inhibitory activity on acetylcholinesterase (AChE). PMID:25665939

  4. Cucurbitacin glucosides from Citrullus colocynthis.

    PubMed

    Nayab, Durey; Ali, Dildar; Arshad, Nuzhat; Malik, Abdul; Choudhary, M Iqbal; Ahmed, Zaheer

    2006-05-10

    A new cucurbitacin glucoside 2-O-beta-D-glucopyranosyl-16alpha-20R-dihydroxy-cucurbita-1,5,23E,25(26)-tetraen-3,11,22-trione (1) has been isolated from the methanolic extract of the fruits of Citrulluscolocynthis. The structure has been assigned on the basis of spectral analysis including 1D and 2D NMR techniques. In addition 2-O-beta-D-glucopyranosyl-cucurbitacin B (arvenin I) (2) and 2,25-di-O-beta-D-glucopyranosyl-cucurbitacin L (3) are reported for the first time from this species. PMID:16644537

  5. A new isoflavone glucoside from Pterocarpus santalinus.

    PubMed

    Krishnaveni, K S; Srinivasa Rao, J V

    2000-01-01

    A new isoflavone glucoside (1) together with the known santal has been isolated from the heartwood of Pterocarpus santalinus. Based on spectral methods, the structure of the new compound was elucidated as 4',5-dihydroxy 7-O-methyl isoflavone 3'-O-beta-D-glucoside. PMID:11256696

  6. New Lignans and Iridoid Glycosides from Dipsacus asper Wall.

    PubMed

    Sun, Xinguang; Ma, Guoxu; Zhang, Dawei; Huang, Wenhua; Ding, Gang; Hu, Huagang; Tu, Guangzhong; Guo, Baolin

    2015-01-01

    Six new compounds, including four new lignans, dipsalignan A (1), B-D (3-5), and two new bis-iridoid glycoside dimmers, dipsanosides M (7) and N (8), together with two known compounds (2) and (6), have been isolated from the roots of Dipsacus asper Wall. Their structures were established on the basis of spectroscopic data (MS, 1D, 2D NMR, and CD) and chemical methods. All the isolated compounds were tested against human immunodeficiency virus-1 (HIV-1) integrase inhibition activities, and only compounds 1, 2, 7, and 8 displayed weak activities. PMID:25635380

  7. Bioactive Iridoid Glycosides from the Whole Plants of Rehmannia chingii.

    PubMed

    Liu, Yan-Fei; Shi, Guo-Ru; Wang, Xin; Zhang, Chun-Lei; Wang, Yan; Chen, Ruo-Yun; Yu, De-Quan

    2016-02-26

    Nine new iridoid glycosides, rehmachingiiosides A-I (1-9), together with 16 known analogues, were isolated from the whole plants of Rehmannia chingii. The structures of compounds 1-9 were elucidated on the basis of spectroscopic data analysis and from chemical evidence. Furthermore, in two vitro assays, compounds 5 and 10 showed an inhibitory effect on LPS-induced NO production with IC50 values of 2.5 and 7.3 μM, and compounds 4, 6, and 10-12 (when evaluated at 10 μM) exhibited evidence of hepatoprotective effects against APAP-induced HepG2 cell damage. PMID:26859776

  8. Secondary metabolites from Scrophularia canina L.

    PubMed

    Venditti, A; Frezza, C; Riccardelli, M; Foddai, S; Nicoletti, M; Serafini, M; Bianco, A

    2016-07-01

    A re-examination of Scrophularia canina L. confirmed the presence of iridoid glucosides considered as chemotaxonomic markers for the Scrophulariaceae family, like aucubin, harpagide and 8-O-acetylharpagide, besides the further presence of 8-epiloganic acid, which is, indeed, considered the biogenetic precursor of iridoids normally found in Scrophulariaceae, and was recognised here for the first time in the studied species. Also verbascoside and (E)-phytol were evidenced for the first time in S. canina. The former compound is an almost ubiquitous glycosidic phenyl-ethanoid, which attains systematic importance when in co-occurrence with iridoids, and its taxonomical implications were discussed. The latter compound, even though it is omnipresent, is interestingly endowed with several biological activities, which may give an additional reason for the traditional uses of this plant. PMID:26675659

  9. Three new monoterpene glucosides from Senecio solidagineus.

    PubMed

    Li, Dingxiang; Chou, Guixin; Wang, Zhengtao

    2014-07-01

    Three new monoterpene glucosides, solidagin A, B, and C (1-3), together with two known alkaloids, senecionine (4) and senkirkine (5), were isolated from Senecio solidagineus, and their structures were elucidated on the basis of 1D and 2D NMR spectral analysis. PMID:25230485

  10. Stability of Limonin Glucoside in Beverage Matrices

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Limonin glucoside, a highly oxygenated triterpenoid secondary metabolite found in significant quantities in Citrus and reported to possess multiple health-promoting properties, is being considered for incorporation into beverages as a functional component. In preparation of a multi-week human study...

  11. Cytogenetic activity of the coumarin glucoside seseloside

    SciTech Connect

    Arshava, E.A.

    1986-05-01

    The cytogenetic effect of the coumarin glucoside seseloside on plant objects was studied. It was established that low concentrations of the preparation (from 1 x 10/sup -5/ to 1 x 10/sup -3/ ..mu..g/ml) inhibit both spontaneous and radiation-induced mutagenesis. The effect of high concentrations (10 and 100 ..mu..g/ml) causes a mutagenic effect.

  12. UPLC-TOF-MS Characterization and Identification of Bioactive Iridoids in Cornus mas Fruit

    PubMed Central

    West, Brett J.; Jensen, C. Jarakae

    2013-01-01

    Cornus mas L. is indigenous to Europe and parts of Asia. Although Cornus is widely considered to be an iridoid rich genera, only two iridoids have been previously found in this plant. The lack of information on taxonomically and biologically active iridoids prompted us to develop and optimize an analytical method for characterization of additional phytochemicals in C. mas fruit. An ultra performance liquid chromatography (UPLC) coupled with photodiode array spectrophotometry (PDA) and electrospray time-of-flight mass spectrometry (ESI-TOF-MS) was employed and mass parameters were optimized. Identification was made by elucidating the mass spectral data and further confirmed by comparing retention times and UV spectra of target peaks with those of reference compounds. Primary DNA damage and antigenotoxicity tests in E. coli PQ37 were used to screen the iridoids for biological activity. As a result, ten phytochemicals were identified, including iridoids loganic acid, loganin, sweroside, and cornuside. Nine of these were reported for the first time from C. mas fruit. The iridoids did not induce SOS repair of DNA, indicating a lack of genotoxic activity in E. coli PQ37. However, loganin, sweroside, and cornuside did reduce the amount of DNA damage caused by 4-nitroquinoline 1-oxide, suggesting potential antigenotoxic activity. PMID:24228188

  13. Coumaroyl Iridoids and a Depside from Cranberry (Vaccinium macrocarpon)

    PubMed Central

    Turner, Allison; Chen, Shao-Nong; Nikolic, Dejan; van Breemen, Richard; Farnsworth, Norman R.; Pauli, Guido F.

    2006-01-01

    Cranberry (Vaccinium macrocarpon Ait., Ericaceae) juice has been used for urinary tract infections for approximately 50 years. Recent research suggests that this botanical blocks adherence of pathogenic E. coli to urinary tract cells, thus preventing infection. While current evidence indicates that proanthocyanidins are responsible for this activity, these compounds may not reach the urinary tract, thus further investigation is warranted. Fractionation of cranberry juice concentrate was guided by a recently published antiadherence assay, and the resulting fractions were phytochemically characterized. Two new coumaroyl iridoid glycosides, 10-p-trans- (1) and 10-p-cis-coumaroyl-1S-dihydromonotropein (2), and a depside, 2-O-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxyphenylmethylacetate (3) were isolated, and although these compounds did not have antiadherent activity in isolation, they might constitute a new group of marker compounds for this active fraction of cranberry. PMID:17269823

  14. [Development and research advances of iridoids from Valeriana jatamansi and their bioactivity].

    PubMed

    Zhang, Ning-ning; Ding, Guang-zhi

    2015-05-01

    Valeriana jatamansi (syn. V. wallichii), a traditional Chinese medicine recorded in Chinese Pharmacopeia (1977 and 2010 edition), has been used for treatment of a variety of conditions including sleep problems, obesity, nervous disorders, epilepsy, insanity, snake poisoning, eye trouble, and skin diseases. Also, it was used as an important substitute for the European V. officinalis, whose root preparation, popularly known as valerian, has been employed as a mild sedative for a long time. In recent years, much attention has been draw to the iridoids, one of the major bioactive constituents of V. jatamansi, leading to the discovery of a series of new iridoids with anti-tumor and neuroprotective activities. Their action machnism also has been discussed. This paper summerized the iridoids and their bioactivities from V. jatamansi in recent years, which could provide basic foundation for development and research of V. jatamansi. PMID:26390643

  15. A new acylated isoflavone glucoside from Pterocarpus santalinus.

    PubMed

    Krishnaveni, K S; Srinivasa Rao, J V

    2000-09-01

    Phytochemical investigation on the constituents of heartwood of Pterocarpus santalinus resulted in the isolation of a new acylated isoflavone glucoside. The structure of the new compound was elucidated on the basis of spectral studies as 4',5-dihydroxy-7-O-methyl isoflavone 3'-O-D-(3''-E-cinnamoyl)glucoside. PMID:10993243

  16. Characterization of 10-hydroxygeraniol dehydrogenase from Catharanthus roseus reveals cascaded enzymatic activity in iridoid biosynthesis.

    PubMed

    Krithika, Ramakrishnan; Srivastava, Prabhakar Lal; Rani, Bajaj; Kolet, Swati P; Chopade, Manojkumar; Soniya, Mantri; Thulasiram, Hirekodathakallu V

    2015-01-01

    Catharanthus roseus [L.] is a major source of the monoterpene indole alkaloids (MIAs), which are of significant interest due to their therapeutic value. These molecules are formed through an intermediate, cis-trans-nepetalactol, a cyclized product of 10-oxogeranial. One of the key enzymes involved in the biosynthesis of MIAs is an NAD(P)(+) dependent oxidoreductase system, 10-hydroxygeraniol dehydrogenase (Cr10HGO), which catalyses the formation of 10-oxogeranial from 10-hydroxygeraniol via 10-oxogeraniol or 10-hydroxygeranial. This work describes the cloning and functional characterization of Cr10HGO from C. roseus and its role in the iridoid biosynthesis. Substrate specificity studies indicated that, Cr10HGO has good activity on substrates such as 10-hydroxygeraniol, 10-oxogeraniol or 10-hydroxygeranial over monohydroxy linear terpene derivatives. Further it was observed that incubation of 10-hydroxygeraniol with Cr10HGO and iridoid synthase (CrIDS) in the presence of NADP(+) yielded a major metabolite, which was characterized as (1R, 4aS, 7S, 7aR)-nepetalactol by comparing its retention time, mass fragmentation pattern, and co-injection studies with that of the synthesized compound. These results indicate that there is concerted activity of Cr10HGO with iridoid synthase in the formation of (1R, 4aS, 7S, 7aR)-nepetalactol, an important intermediate in iridoid biosynthesis. PMID:25651761

  17. Characterization of 10-Hydroxygeraniol Dehydrogenase from Catharanthus roseus Reveals Cascaded Enzymatic Activity in Iridoid Biosynthesis

    PubMed Central

    Krithika, Ramakrishnan; Srivastava, Prabhakar Lal; Rani, Bajaj; Kolet, Swati P.; Chopade, Manojkumar; Soniya, Mantri; Thulasiram, Hirekodathakallu V.

    2015-01-01

    Catharanthus roseus [L.] is a major source of the monoterpene indole alkaloids (MIAs), which are of significant interest due to their therapeutic value. These molecules are formed through an intermediate, cis-trans-nepetalactol, a cyclized product of 10-oxogeranial. One of the key enzymes involved in the biosynthesis of MIAs is an NAD(P)+ dependent oxidoreductase system, 10-hydroxygeraniol dehydrogenase (Cr10HGO), which catalyses the formation of 10-oxogeranial from 10-hydroxygeraniol via 10-oxogeraniol or 10-hydroxygeranial. This work describes the cloning and functional characterization of Cr10HGO from C. roseus and its role in the iridoid biosynthesis. Substrate specificity studies indicated that, Cr10HGO has good activity on substrates such as 10-hydroxygeraniol, 10-oxogeraniol or 10-hydroxygeranial over monohydroxy linear terpene derivatives. Further it was observed that incubation of 10-hydroxygeraniol with Cr10HGO and iridoid synthase (CrIDS) in the presence of NADP+ yielded a major metabolite, which was characterized as (1R, 4aS, 7S, 7aR)-nepetalactol by comparing its retention time, mass fragmentation pattern, and co-injection studies with that of the synthesized compound. These results indicate that there is concerted activity of Cr10HGO with iridoid synthase in the formation of (1R, 4aS, 7S, 7aR)-nepetalactol, an important intermediate in iridoid biosynthesis. PMID:25651761

  18. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Methyl glucoside-coconut oil ester. 172.816... § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is the methyl glucoside-coconut oil...

  19. Dhurrin-6'-glucoside, a cyanogenic diglucoside from Sorghum bicolor.

    PubMed

    Selmar, D; Irandoost, Z; Wray, V

    1996-10-01

    A novel cyanogenic diglucoside has been isolated from methanolic extracts of young seedlings of Sorghum bicolor. Its structure was established as dhurrin-6-glucoside from NMR, mass spectrometry and enzymatic hydrolysis data. Compared with dhurrin, which is the major cyanogenic glucoside in sorghum leaves, dhurrin-6-glucoside occurs only in low concentrations. In contrast, however, the diglucoside is present in significant amounts in guttation droplets of young Sorghum seedlings. The presence of the diglucoside and its occurrence in apoplasmic exudates supports the hypothesis that diglucosides represent metabolites of cyanogenic monoglucosides which can be translocated within the plant. PMID:8987580

  20. Divergent synthetic route to new cyclopenta[c]pyran iridoids: syntheses of jatamanin A, F, G and J, gastrolactone and nepetalactone.

    PubMed

    Sim, Jaehoon; Yoon, Inah; Yun, Hwayoung; An, Hongchan; Suh, Young-Ger

    2016-01-28

    Six natural iridoids including jatamanin A, F, G and J, gastrolactone and nepetalactone have been synthesized via the efficient transformation of a core cyclopenta[c]pyran intermediate. Key features of the syntheses include the stereoselective construction of the core cyclopenta[c]pyran skeleton of the iridoid lactones via a Pd(0)-catalyzed intramolecular allylic alkylation, and the facile transformation of the common intermediate into natural iridoids. PMID:26647357

  1. Malonyl isoflavone glucosides are chiefly hydrolyzed and absorbed in the colon.

    PubMed

    Yonemoto-Yano, Hiroko; Maebuchi, Motohiro; Fukui, Kensuke; Tsuzaki, Shinichi; Takamatsu, Kiyoharu; Uehara, Mariko

    2014-03-12

    Malonyl isoflavone glucosides are water-soluble derivatives of soybean hypocotyls. This study compared the hydrolysis and absorption of malonyl isoflavone glucosides and nonmalonyl isoflavone glucosides in rats. Plasma concentrations of isoflavones were measured after oral administration of malonyl isoflavone glucosides or isoflavone glucosides. After fasting, the duodenum, jejunum, ileum, and colon were excised, and homogenates were prepared. The extent of hydrolysis of each glucoside by each intestinal homogenate was measured. Plasma levels of isoflavone aglycones, such as daidzein and glycitein, were higher in rats administered malonyl isoflavone glucosides than in those administered isoflavone glucosides. The area under the curve of daidzein in plasma of rats administered malonyl isoflavone glucosides was also significantly greater than that in those administered isoflavone glucosides. A transport experiment using Caco-2 cells suggested that degradation of malonyl glucosides to aglycones is necessary for intestinal absorption. Malonyl isoflavone glucosides were hydrolyzed only in the colon, whereas hydrolysis of isoflavone glucosides occurred in the jejunum, ileum, and colon. These results indicated more effective absorption of malonyl isoflavone glucosides than of nonmalonyl isoflavone glucosides. Moreover, effective absorption of malonyl isoflavone aglycones in the colon contributed to the significant increase in plasma isoflavone levels. PMID:24524651

  2. Anticomplement monoterpenoid glucosides from the root bark of Paeonia suffruticosa.

    PubMed

    Song, Wei-Hua; Cheng, Zhi-Hong; Chen, Dao-Feng

    2014-01-24

    Six new (1-6) and 19 known monoterpenoid glucosides were isolated from the root bark of Paeonia suffruticosa. The monoterpenoid glucosides 1, 2, 7, 10-19, and 22 exhibited anticomplement effects with CH50 and AP50 values ranging from 0.14 to 2.67 mM and 0.25 to 3.67 mM, respectively. In a mechanistic study, suffrupaeoniflorin A (1) interacted with C1q, C3, C5, and C9, while galloylpaeoniflorin (12) and galloyloxypaeoniflorin (19) acted on C1q, C3, and C5 components in the complement activation cascade. PMID:24377852

  3. Effect of qualitative and quantitative variation in allelochemicals on a generalist insect: Iridoid glycosides and the southern armyworm.

    PubMed

    Puttick, G M; Bowers, M D

    1988-01-01

    The behavioral and physiological effects of plant allelochemicals have been difficult to demonstrate; it is not often clear whether the compounds are deterrent, toxic, or both. In this study, we compared the qualitative and quantitative effects of several iridoid glycosides on a generalist lepidopteran herbivore,Spodoptera eridania (Noctuidae). Larval growth and survivorship and larval preference or avoidance were measured on artificial diets containing different iridoid glycosides at different concentrations. We also tested the toxicity/deterrence of these compounds. We found that iridoid glycosides retarded larval growth significantly at relatively low concentrations and that they were usually avoided in preference tests. The toxicity/ deterrence test did not always reflect the results of these other tests. The merits of using a variety of methods for determining deterrence and/or toxicity of plant allelochemicals are discussed. PMID:24277013

  4. 7-deoxyloganetic acid synthase catalyzes a key 3 step oxidation to form 7-deoxyloganetic acid in Catharanthus roseus iridoid biosynthesis.

    PubMed

    Salim, Vonny; Wiens, Brent; Masada-Atsumi, Sayaka; Yu, Fang; De Luca, Vincenzo

    2014-05-01

    Iridoids are key intermediates required for the biosynthesis of monoterpenoid indole alkaloids (MIAs), as well as quinoline alkaloids. Although most iridoid biosynthetic genes have been identified, one remaining three step oxidation required to form the carboxyl group of 7-deoxyloganetic acid has yet to be characterized. Here, it is reported that virus-induced gene silencing of 7-deoxyloganetic acid synthase (7DLS, CYP76A26) in Catharanthus roseus greatly decreased levels of secologanin and the major MIAs, catharanthine and vindoline in silenced leaves. Functional expression of this gene in Saccharomyces cerevisiae confirmed its function as an authentic 7DLS that catalyzes the 3 step oxidation of iridodial-nepetalactol to form 7-deoxyloganetic acid. The identification of CYP76A26 removes a key bottleneck for expression of iridoid and related MIA pathways in various biological backgrounds. PMID:24594312

  5. Absorption and excretion of conjugated flavonols, including quercetin-4'-O-beta-glucoside and isorhamnetin-4'-O-beta-glucoside by human volunteers after the consumption of onions.

    PubMed

    Aziz, A A; Edwards, C A; Lean, M E; Crozier, A

    1998-09-01

    Flavonols are polyphenols found ubiquitously in plants and plant-products. Flavonols, particularly quercetin, are potent antioxidants in vitro and their intake has been associated inversely with the incidence of coronary heart disease. The aim of this study was to investigate the accumulation in plasma and excretion in urine of flavonol glucosides following ingestion of lightly fried onions. Five healthy volunteers followed a low-flavonoid diet for 3 days. On day 4, after an overnight fast, subjects were given 300 g of lightly fried yellow onions which contain conjugates of quercetin and isorhamnetin, including quercetin-3,4 '-diO-beta-glucoside, isorhamnetin-4'-O-beta-glucoside and quercetin-4'-O-beta-glucoside. Blood collection was carried out at 0 min, 0.5, 1.0, 1.5, 2, 3, 4, 5 and 24h after the supplement. In addition, subjects collected all their urine for 24h following the onion supplement. Isorhamnetin-4'-O-beta-glucoside and quercetin-4 '-O-beta-glucoside accumulated in plasma with maximum levels, defined as proportion of intake, of 10.7+/-2.6% and 0.13+/-0.03% respectively. The time of the quercetin-4'glucoside peak plasma concentration was 1.3+/-0.2 h after the ingestion of onions while a value of 1.8+/-0.7 h was obtained for isorhamnetin-4'-glucoside. Excretion in urine, as a proportion of intake, was 17.4+/-8.3% for isorhamnetin-4'-O-beta-glucoside and 0.2+/-0.1% for quercetin-4'-O-beta-glucoside. Possible reasons for the accumulation and excretion of isorhamnetin-4'-glucoside in proportionally much higher amounts than quercetin-4'-glucoside are discussed. It is concluded that flavonols are absorbed into the bloodstream as glucosides and minor structural differences affect markedly both the level of accumulation and the extent to which the conjugates are excreted. PMID:9802557

  6. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Methyl glucoside-coconut oil ester. 178.3600... SANITIZERS Certain Adjuvants and Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of this chapter may be safely used as a...

  7. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut...

  8. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Methyl glucoside-coconut oil ester. 172.816 Section... HUMAN CONSUMPTION Multipurpose Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is...

  9. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Methyl glucoside-coconut oil ester. 178.3600... SANITIZERS Certain Adjuvants and Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of this chapter may be safely used as a...

  10. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Methyl glucoside-coconut oil ester. 178.3600 Section 178.3600 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester...

  11. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Methyl glucoside-coconut oil ester. 172.816... HUMAN CONSUMPTION Multipurpose Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is...

  12. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 6 2014-04-01 2014-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut...

  13. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 6 2012-04-01 2012-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut...

  14. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Methyl glucoside-coconut oil ester. 172.816... HUMAN CONSUMPTION Multipurpose Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is...

  15. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 6 2013-04-01 2013-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut...

  16. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Methyl glucoside-coconut oil ester. 178.3600... SANITIZERS Certain Adjuvants and Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of this chapter may be safely used as a...

  17. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 6 2011-04-01 2011-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut...

  18. Iridoids and sesquiterpenoids of Valeriana stenoptera and their effects on NGF-induced neurite outgrowth in PC12 cells.

    PubMed

    Dong, Fa-Wu; Wu, Zhi-Kun; Yang, Liu; Zi, Chen-Ting; Yang, Dan; Ma, Rui-Jing; Liu, Zhen-Hua; Luo, Huai-Rong; Zhou, Jun; Hu, Jiang-Miao

    2015-10-01

    Twenty-one compounds (nine iridoids and twelve sesquiterpenoids), including ten previously unknown (five iridoids and five sesquiterpenoids) were isolated from whole dried material of Valeriana stenoptera. Structures were established on the basis of extensive spectroscopic analysis and the relative stereochemistry of 13-hydroxypatchoulol A was further confirmed by X-ray crystallographic data. All isolates were evaluated for their effects on nerve growth factor (NGF)-mediated neurite outgrowth in pheochromocytoma (PC12) cells and seven compounds showed potent promoting effects. PMID:26343415

  19. Enzymatic Synthesis of Acylphloroglucinol 3-C-Glucosides from 2-O-Glucosides using a C-Glycosyltransferase from Mangifera indica.

    PubMed

    Chen, Dawei; Sun, Lili; Chen, Ridao; Xie, Kebo; Yang, Lin; Dai, Jungui

    2016-04-18

    A green and cost-effective process for the convenient synthesis of acylphloroglucinol 3-C-glucosides from 2-O-glucosides was exploited using a novel C-glycosyltransferase (MiCGTb) from Mangifera indica. Compared with previously characterized CGTs, MiCGTb exhibited unique de-O-glucosylation promiscuity and high regioselectivity toward structurally diverse 2-O-glucosides of acylphloroglucinol and achieved high yields of C-glucosides even with a catalytic amount of uridine 5'-diphosphate (UDP). These findings demonstrate for the first time the significant potential of a single-enzyme approach to the synthesis of bioactive C-glucosides from both natural and unnatural acylphloroglucinol 2-O-glucosides. PMID:26918309

  20. Analysis of several iridoid and indole precursors of terpenoid indole alkaloids with a single HPLC run.

    PubMed

    Dagnino, D; Schripsema, J; Verpoorte, R

    1996-06-01

    An isocratic HPLC system is described which allows the separation of the iridoid and indole precursors of terpenoid indole alkaloids, which are present in a single crude extract. The system consists of a column of LiChrospher 60 RP select B 5 microm, 250 x 4 mm (Merck) with an eluent of 1% formic acid-acetonitrile-trichloroacetic acid (100:10:0.25, v:v:w) at a flow of 1.2 ml/min. In the suspension cultures of Catharanthus roseus secologanin and tryptophan were detected. in the cultures of Tabernaemontana divaricata loganin, tryptophan, and tryptamine accumulated. PMID:17252445

  1. Effect of Morinda citrifolia fruit extract and its iridoid glycosides on blood fluidity.

    PubMed

    Murata, Kazuya; Abe, Yumi; Futamura-Masuda, Megumi; Uwaya, Akemi; Isami, Fumiyuki; Deng, Shixin; Matsuda, Hideaki

    2014-07-01

    The aim of this study was to investigate the effect of Morinda citrifolia fruit on blood fluidity. M. citrifolia fruit extract (MCF-ext) was investigated for its influence on blood aggregation and fibrinolysis. MCF-ext inhibited polybrene-induced erythrocyte aggregation and thrombin activity. The fibrinolytic activity of MCF-ext, in the euglobulin lysis time test and fibrin plate assay, is reported here for the first time. One of the active compounds was an iridoid glycoside, asperulosidic acid. The results indicated that MCF-ext is a potentially useful health food which is capable of improving blood flow and preventing lifestyle-related diseases. PMID:24604344

  2. Recent Developments of C-Aryl Glucoside SGLT2 Inhibitors.

    PubMed

    Zhang, Yang; Liu, Zhao-Peng

    2016-01-01

    Sodium-glucose cotransporter 2 (SGLT2) is almost exclusively expressed in the proximal renal tubules. It is responsible for about 90% of the glucose reabsorption from tubular fluid. Selective inhibition of SGLT2 is expected to favor in the normalization of plasma glucose levels in T2DM patients through the prevention of renal glucose reabsorption and the promotion of glucose excretion from urine. Selective SGLT2 inhibitors have the merits to minimize the gastrointestinal side effects associated with SGLT1 inhibition, and selective SGLT2 inhibition may have a low risk of hypoglycemia. Since the C-aryl glucosides are metabolically more stable than the O-glucosides, numerous efforts have been made in the development of potent and selective C-aryl glucoside SGLT2 inhibitors, and a number of them are now used as anti-diabetes drugs in clinic or at various stages of clinical developments. Based on their structural features, in this review, these SGLT2 inhibitors are classified as three types: the phenyl/arylmethylphenyl C-glucosides, with an emphasis on the modifications on the proximal and/or the distal phenyl ring, and the spacer; the heteroarylmethylphenyl Cglucosides, with a replacement of the distal phenyl ring by a heterocycle like pyridazine, pyrimidine, thiophene and benzothiophene, thiazole, 1,3,4-thiadiazole, and triazolopyridinone; and the glucose-modified Caryl glucosides, including the glucose C-1 derived O-spiroketals, C-4 gem-difluoro analogues, C-5 and C-6 modified derivatives, dioxa-bicyclo[3.2.1]octane bridged ketals, the thioglucosides, and carbasugars. The structure-activity relationships (SARs) of each type along with their inhibitory potency against human SGLT2 and selectivity over human SGLT1 are discussed. PMID:26861002

  3. One New Conjugate of a Secoiridoid Glucoside with a Sesquiterpene Glucoside from the Flower Buds of Lonicera japonica.

    PubMed

    Yang, Biao; Meng, Zhaoqing; Ma, Yimin; Wang, Zhenzhong; Ding, Gang; Huang, Wenzhe; Sun, Lin; Hu, Yumei; Liu, Wenjun; Zhang, Chunxiao; Cao, Zeyu; Li, Jiachun; Zhong, Yan; Xiao, Wei

    2015-09-01

    Secosesquside (1), a new secoiridoid glucoside-sesquiterpene conjugate, together with three known secoiridoid derivatives, were isolated from flower buds of Lonicerajaponica. The isolated compounds were elucidated by extensive spectroscopic analyses, especially 2D NMR experiments. The anti-inflammatory activities of the new compound were also evaluated by enzyme-linked immunosorbent assay. PMID:26594743

  4. RP-HPLC analysis of seco-iridoid glycoside swertiamarin from different Swertia species.

    PubMed

    Kshirsagar, Parthraj R; Pai, Sandeep R; Nimbalkar, Mansingraj S; Gaikwad, Nikhil B

    2016-01-01

    Genus Swertia is valued for its great medicinal potential; mainly Swertia chirayita (Roxb. ex Fleming) H. Karst. is used in traditional medicine for a wide range of diseases. Seco-iridoid glycosides like swertiamarin is referred with enormous pharmacological potentials. The aim of the study was to identify a suitable substitute to S. chirayita by quantifying seco-iridoid swertiamarin from five different Swertia species endemic to the Western Ghats. The reverse-phase high-performance liquid chromatography diode array detector analyses were performed and chromatographic separation was achieved on a Lichrospher 100, C18e (5 µm) column (250-4.6 mm). A mobile phase consisting of acetonitrile and water (25:75) was used for separation. Results indicated that the concentration of the marker compound has been found to vary largely between and within the species from different localities. The content of swertiamarin was the highest in S. chirayita compared to the other species studied herein, advocating the use of Swertia minor as an alternate source to S. chirayita. PMID:26299409

  5. Application of Cornelian Cherry Iridoid-Polyphenolic Fraction and Loganic Acid to Reduce Intraocular Pressure

    PubMed Central

    Szumny, Dorota; Sozański, Tomasz; Kucharska, Alicja Z.; Dziewiszek, Wojciech; Piórecki, Narcyz; Magdalan, Jan; Chlebda-Sieragowska, Ewa; Kupczynski, Robert; Szeląg, Adam; Szumny, Antoni

    2015-01-01

    One of the most common diseases of old age in modern societies is glaucoma. It is strongly connected with increased intraocular pressure (IOP) and could permanently damage vision in the affected eye. As there are only a limited number of chemical compounds that can decrease IOP as well as blood flow in eye vessels, the up-to-date investigation of new molecules is important. The chemical composition of the dried Cornelian cherry (Cornus mas L.) polar, iridoid-polyphenol-rich fraction was investigated. Loganic acid (50%) and pelargonidin-3-galactoside (7%) were found as the main components. Among the other constituents, iridoid compound cornuside and the anthocyans cyanidin 3-O-galactoside, cyanidin 3-O-robinobioside, and pelargonidin 3-O-robinobioside were quantified in the fraction. In an animal model (New Zealand rabbits), the influence of loganic acid and the polyphenolic fraction isolated from Cornelian cherry fruit was investigated. We found a strong IOP-hypotensive effect for a 0.7% solution of loganic acid, which could be compared with the widely ophthalmologically used timolol. About a 25% decrease in IOP was observed within the first 3 hours of use. PMID:26124854

  6. Antitrypanosomal Activities and Mechanisms of Action of Novel Tetracyclic Iridoids from Morinda lucida Benth.

    PubMed Central

    Kwofie, Kofi D.; Tung, Nguyen Huu; Amoa-Bosompem, Michael; Adegle, Richard; Sakyiamah, Maxwell M.; Ayertey, Frederick; Owusu, Kofi Baffour-Awuah; Tuffour, Isaac; Atchoglo, Philip; Frempong, Kwadwo K.; Anyan, William K.; Uto, Takuhiro; Morinaga, Osamu; Yamashita, Taizo; Aboagye, Frederic; Appiah, Alfred A.; Appiah-Opong, Regina; Nyarko, Alexander K.; Yamaguchi, Yasuchika; Edoh, Dominic; Koram, Kwadwo A.; Yamaoka, Shoji; Boakye, Daniel A.; Ohta, Nobuo; Shoyama, Yukihiro; Ayi, Irene

    2016-01-01

    Trypanosoma brucei parasites are kinetoplastid protozoa that devastate the health and economic well-being of millions of people in Africa through the disease human African trypanosomiasis (HAT). New chemotherapy has been eagerly awaited due to severe side effects and the drug resistance issues plaguing current drugs. Recently, there has been an emphasis on the use of medicinal plants worldwide. Morinda lucida Benth. is a popular medicinal plant widely distributed in Africa, and several research groups have reported on the antiprotozoal activities of this plant. In this study, we identified three novel tetracyclic iridoids, molucidin, ML-2-3, and ML-F52, from the CHCl3 fraction of M. lucida leaves, which possess activity against the GUTat 3.1 strain of T. brucei brucei. The 50% inhibitory concentrations (IC50) of molucidin, ML-2-3, and ML-F52 were 1.27 μM, 3.75 μM, and 0.43 μM, respectively. ML-2-3 and ML-F52 suppressed the expression of paraflagellum rod protein subunit 2, PFR-2, and caused cell cycle alteration, which preceded apoptosis induction in the bloodstream form of Trypanosoma parasites. Novel tetracyclic iridoids may be promising lead compounds for the development of new chemotherapies for African trypanosomal infections in humans and animals. PMID:26953191

  7. Antitrypanosomal Activities and Mechanisms of Action of Novel Tetracyclic Iridoids from Morinda lucida Benth.

    PubMed

    Kwofie, Kofi D; Tung, Nguyen Huu; Suzuki-Ohashi, Mitsuko; Amoa-Bosompem, Michael; Adegle, Richard; Sakyiamah, Maxwell M; Ayertey, Frederick; Owusu, Kofi Baffour-Awuah; Tuffour, Isaac; Atchoglo, Philip; Frempong, Kwadwo K; Anyan, William K; Uto, Takuhiro; Morinaga, Osamu; Yamashita, Taizo; Aboagye, Frederic; Appiah, Alfred A; Appiah-Opong, Regina; Nyarko, Alexander K; Yamaguchi, Yasuchika; Edoh, Dominic; Koram, Kwadwo A; Yamaoka, Shoji; Boakye, Daniel A; Ohta, Nobuo; Shoyama, Yukihiro; Ayi, Irene

    2016-06-01

    Trypanosoma brucei parasites are kinetoplastid protozoa that devastate the health and economic well-being of millions of people in Africa through the disease human African trypanosomiasis (HAT). New chemotherapy has been eagerly awaited due to severe side effects and the drug resistance issues plaguing current drugs. Recently, there has been an emphasis on the use of medicinal plants worldwide. Morinda lucida Benth. is a popular medicinal plant widely distributed in Africa, and several research groups have reported on the antiprotozoal activities of this plant. In this study, we identified three novel tetracyclic iridoids, molucidin, ML-2-3, and ML-F52, from the CHCl3 fraction of M. lucida leaves, which possess activity against the GUTat 3.1 strain of T. brucei brucei The 50% inhibitory concentrations (IC50) of molucidin, ML-2-3, and ML-F52 were 1.27 μM, 3.75 μM, and 0.43 μM, respectively. ML-2-3 and ML-F52 suppressed the expression of paraflagellum rod protein subunit 2, PFR-2, and caused cell cycle alteration, which preceded apoptosis induction in the bloodstream form of Trypanosoma parasites. Novel tetracyclic iridoids may be promising lead compounds for the development of new chemotherapies for African trypanosomal infections in humans and animals. PMID:26953191

  8. Enzymatic Biosynthesis of Novel Resveratrol Glucoside and Glycoside Derivatives.

    PubMed

    Pandey, Ramesh Prasad; Parajuli, Prakash; Shin, Ju Yong; Lee, Jisun; Lee, Seul; Hong, Young-Soo; Park, Yong Il; Kim, Joong Su; Sohng, Jae Kyung

    2014-12-01

    A UDP glucosyltransferase from Bacillus licheniformis was overexpressed, purified, and incubated with nucleotide diphosphate (NDP) d- and l-sugars to produce glucose, galactose, 2-deoxyglucose, viosamine, rhamnose, and fucose sugar-conjugated resveratrol glycosides. Significantly higher (90%) bioconversion of resveratrol was achieved with α-d-glucose as the sugar donor to produce four different glucosides of resveratrol: resveratrol 3-O-β-d-glucoside, resveratrol 4'-O-β-d-glucoside, resveratrol 3,5-O-β-d-diglucoside, and resveratrol 3,5,4'-O-β-d-triglucoside. The conversion rates and numbers of products formed were found to vary with the other NDP sugar donors. Resveratrol 3-O-β-d-2-deoxyglucoside and resveratrol 3,5-O-β-d-di-2-deoxyglucoside were found to be produced using TDP-2-deoxyglucose as a donor; however, the monoglycosides resveratrol 4'-O-β-d-galactoside, resveratrol 4'-O-β-d-viosaminoside, resveratrol 3-O-β-l-rhamnoside, and resveratrol 3-O-β-l-fucoside were produced from the respective sugar donors. Altogether, 10 diverse glycoside derivatives of the medically important resveratrol were generated, demonstrating the capacity of YjiC to produce structurally diverse resveratrol glycosides. PMID:25239890

  9. The bifurcation of the cyanogenic glucoside and glucosinolate biosynthetic pathways.

    PubMed

    Clausen, Mette; Kannangara, Rubini M; Olsen, Carl E; Blomstedt, Cecilia K; Gleadow, Roslyn M; Jørgensen, Kirsten; Bak, Søren; Motawie, Mohammed S; Møller, Birger Lindberg

    2015-11-01

    The biosynthetic pathway for the cyanogenic glucoside dhurrin in sorghum has previously been shown to involve the sequential production of (E)- and (Z)-p-hydroxyphenylacetaldoxime. In this study we used microsomes prepared from wild-type and mutant sorghum or transiently transformed Nicotiana benthamiana to demonstrate that CYP79A1 catalyzes conversion of tyrosine to (E)-p-hydroxyphenylacetaldoxime whereas CYP71E1 catalyzes conversion of (E)-p-hydroxyphenylacetaldoxime into the corresponding geometrical Z-isomer as required for its dehydration into a nitrile, the next intermediate in cyanogenic glucoside synthesis. Glucosinolate biosynthesis is also initiated by the action of a CYP79 family enzyme, but the next enzyme involved belongs to the CYP83 family. We demonstrate that CYP83B1 from Arabidopsis thaliana cannot convert the (E)-p-hydroxyphenylacetaldoxime to the (Z)-isomer, which blocks the route towards cyanogenic glucoside synthesis. Instead CYP83B1 catalyzes the conversion of the (E)-p-hydroxyphenylacetaldoxime into an S-alkyl-thiohydroximate with retention of the configuration of the E-oxime intermediate in the final glucosinolate core structure. Numerous microbial plant pathogens are able to detoxify Z-oximes but not E-oximes. The CYP79-derived E-oximes may play an important role in plant defense. PMID:26361733

  10. The glucosidic pathways and glucose production by frog muscle.

    PubMed

    Fournier, P A; Petrof, E O; Guderley, H

    1992-04-25

    Resting muscle is generally perceived as a glucose-utilizing organ; however, we show that resting well-oxygenated frog muscle recovering from strenuous exercise can release significant amounts of glucose. The metabolic pathway responsible for this process does not involve glucose-6-phosphatase because this enzyme is undetectable in frog muscle. The participation of amylo-1,6-glucosidase in the production of glucose is also ruled out since neither marked net phosphorolytic breakdown of glycogen nor considerable cycling between glycogen and glucose 6-phosphate occur. The glucosidic pathways of glycogen breakdown are the likely source of glucose as they are the only metabolic avenues with sufficient capacity to account for the rate at which glucose is released from post-exercised muscle. This rate of glucose production is high enough to be of physiological importance. Our results clearly indicate that to measure lactate glycogenesis in muscle, the simultaneous hydrolysis of muscle glycogen by the glucosidic pathways must be taken into account to prevent marked underestimation of the rate of glycogen synthesis. The glucosidic pathways seem the predominant avenues of glycogen breakdown in post-exercised resting frog muscle and are active enough to account for the rate of glycogen breakdown in resting muscle, suggesting that these rather than the phosphorolytic pathways are the chief routes of glycogen breakdown in resting muscle. PMID:1569076

  11. Identification of Iridoids in Edible Honeysuckle Berries (Lonicera caerulea L. var. kamtschatica Sevast.) by UPLC-ESI-qTOF-MS/MS.

    PubMed

    Kucharska, Alicja Z; Fecka, Izabela

    2016-01-01

    Iridoid profiles of honeysuckle berry were studied. Compounds were identified by ultra-performance liquid chromatography coupled with electrospray ionization mass spectrometry UPLC-ESI-qTOF-MS/MS in positive and negative ions mode. The MS fragmentation pathways of detected iridoid glycosides were also studied in both modes. In the negative ESI mass spectra, iridoids with a methyl ester or lactone structure have preferentially produced adduct [M + HCOOH - H](-) ions. However, protonated ions of molecular fragments, which were released by glycosidic bond cleavage and following fragmentation of aglycone rings, were more usable for iridoid structure analysis. In addition, the neutral losses of H₂O, CO, CO₂, CH₃OH, acetylene, ethenone and cyclopropynone have provided data confirming the presence of functional substituents in the aglycone. Among the 13 iridoids, 11 were identified in honeysuckle berries for the first time: pentosides of loganic acid (two isomers), pentosides of loganin (three isomers), pentosyl sweroside, and additionally 7-epi-loganic acid, 7-epi-loganin, sweroside, secologanin, and secoxyloganin. The five pentoside derivatives of loganic acid and loganin have not been previously detected in the analyzed species. Honeysuckle berries are a source of iridoids with different structures, compounds that are rarely present in fruits. PMID:27598106

  12. Evaluation of human neutrophil elastase inhibitory effect of iridoid glycosides from Hedyotis diffusa.

    PubMed

    Xu, Guang-Hua; Kim, Young-Hee; Chi, Seung-Wook; Choo, Soo-Jin; Ryoo, In-Ja; Ahn, Jong-Seog; Yoo, Ick-Dong

    2010-01-15

    Five iridoid glycosides were isolated from the MeOH extract of Hedyotis diffusa, and their structures were elucidated as E-6-O-p-methoxycinnamoyl scandoside methyl ester (1), Z-6-O-p-methoxycinnamoyl scandoside methyl ester (2), E-6-O-p-feruloyl scandoside methyl ester (3), E-6-O-p-coumaroyl scandoside methyl ester (4), and Z-6-O-p-coumaroyl scandoside methyl ester (5) by interpretation of their spectroscopic data. All the isolated compounds were evaluated for human neutrophil elastase inhibitory effect, and compound 1 showed potent activity with an IC(50) value of 18.0muM. The molecular docking simulation suggested a structural model for the inhibition of human neutrophil elastase by compound 1. PMID:20004577

  13. Antibacterial and Antiproliferative Activities of Plumericin, an Iridoid Isolated from Momordica charantia Vine.

    PubMed

    Saengsai, Jutamas; Kongtunjanphuk, Sumonthip; Yoswatthana, Nuttawan; Kummalue, Tanawan; Jiratchariyakul, Weena

    2015-01-01

    Plumericin, an iridoid lactone, was isolated with relatively high yield from Momordica charantia vine using the supercritical fluid extraction (SFE) and the separation box (Sepbox) comprising dual combination of high-performance liquid chromatography and solid phase extraction. This compound showed antibacterial activity against Enterococcus faecalis and Bacillus subtilis with minimum inhibitory concentration (MIC) values better than cloxacillin. Plumericin potently inhibited proliferation of two leukemic cancer cell lines: they were acute and chronic leukemic cancer cell lines, NB4 and K562, with the effective doses (ED50) of 4.35 ± 0.21 and 5.58 ± 0.35 μg/mL, respectively. In addition, the mechanism of growth inhibition in both cell lines was induced by apoptosis, together with G2/M arrest in K562 cells. PMID:25945113

  14. Antibacterial and Antiproliferative Activities of Plumericin, an Iridoid Isolated from Momordica charantia Vine

    PubMed Central

    Saengsai, Jutamas; Kongtunjanphuk, Sumonthip; Yoswatthana, Nuttawan; Kummalue, Tanawan

    2015-01-01

    Plumericin, an iridoid lactone, was isolated with relatively high yield from Momordica charantia vine using the supercritical fluid extraction (SFE) and the separation box (Sepbox) comprising dual combination of high-performance liquid chromatography and solid phase extraction. This compound showed antibacterial activity against Enterococcus faecalis and Bacillus subtilis with minimum inhibitory concentration (MIC) values better than cloxacillin. Plumericin potently inhibited proliferation of two leukemic cancer cell lines: they were acute and chronic leukemic cancer cell lines, NB4 and K562, with the effective doses (ED50) of 4.35 ± 0.21 and 5.58 ± 0.35 μg/mL, respectively. In addition, the mechanism of growth inhibition in both cell lines was induced by apoptosis, together with G2/M arrest in K562 cells. PMID:25945113

  15. Iridoid Synthase Activity Is Common among the Plant Progesterone 5β-Reductase Family.

    PubMed

    Munkert, Jennifer; Pollier, Jacob; Miettinen, Karel; Van Moerkercke, Alex; Payne, Richard; Müller-Uri, Frieder; Burlat, Vincent; O'Connor, Sarah E; Memelink, Johan; Kreis, Wolfgang; Goossens, Alain

    2014-09-19

    Catharanthus roseus, the Madagascar periwinkle, synthesizes bioactive monoterpenoid indole alkaloids, among which the anti-cancer drugs vinblastine and vincristine. The monoterpenoid branch of the alkaloid pathway leads to the secoiridoid secologanin and involves the enzyme iridoid synthase (IS), a member of the progesterone 5β-reductase (P5βR) family. IS reduces 8-oxogeranial to iridodial. Through transcriptome mining, we show that IS belongs to a family of six C. roseus P5βR genes. Characterisation of recombinant CrP5βR proteins demonstrates that all but CrP5βR3 can reduce progesterone, and thus can be classified as P5βRs. Three of them, namely CrP5βR1, CrP5βR2 and CrP5βR4, could also reduce 8-oxogeranial, pointing to a possible redundancy with IS (corresponding to CrP5βR5) in secoiridoid synthesis. In depth functional analysis by subcellular protein localisation, gene expression analysis, in situ hybridisation and virus-induced gene silencing, indicates that besides IS, CrP5βR4 may also participate in secoiridoid biosynthesis. Finally, we cloned a set of P5βR genes from angiosperm plant species not known to produce iridoids and demonstrate that the corresponding recombinant proteins are also capable of using 8-oxogeranial as a substrate. This suggests that 'IS activity' is intrinsic to angiosperm P5βR proteins and has evolved early during evolution. PMID:25239067

  16. Iridoid synthase activity is common among the plant progesterone 5β-reductase family.

    PubMed

    Munkert, Jennifer; Pollier, Jacob; Miettinen, Karel; Van Moerkercke, Alex; Payne, Richard; Müller-Uri, Frieder; Burlat, Vincent; O'Connor, Sarah E; Memelink, Johan; Kreis, Wolfgang; Goossens, Alain

    2015-01-01

    Catharanthus roseus, the Madagascar periwinkle, synthesizes bioactive monoterpenoid indole alkaloids, including the anti-cancer drugs vinblastine and vincristine. The monoterpenoid branch of the alkaloid pathway leads to the secoiridoid secologanin and involves the enzyme iridoid synthase (IS), a member of the progesterone 5β-reductase (P5βR) family. IS reduces 8-oxogeranial to iridodial. Through transcriptome mining, we show that IS belongs to a family of six C. roseus P5βR genes. Characterization of recombinant CrP5βR proteins demonstrates that all but CrP5βR3 can reduce progesterone and thus can be classified as P5βRs. Three of them, namely CrP5βR1, CrP5βR2, and CrP5βR4, can also reduce 8-oxogeranial, pointing to a possible redundancy with IS (corresponding to CrP5βR5) in secoiridoid synthesis. In-depth functional analysis by subcellular protein localization, gene expression analysis, in situ hybridization, and virus-induced gene silencing indicate that besides IS, CrP5βR4 may also participate in secoiridoid biosynthesis. We cloned a set of P5βR genes from angiosperm plant species not known to produce iridoids and demonstrate that the corresponding recombinant proteins are also capable of using 8-oxogeranial as a substrate. This suggests that IS activity is intrinsic to angiosperm P5βR proteins and has evolved early during evolution. PMID:25578278

  17. New anti-trypanosomal active tetracyclic iridoid isolated from Morinda lucida Benth.

    PubMed

    Suzuki, Mitsuko; Tung, Nguyen Huu; Kwofie, Kofi D; Adegle, Richard; Amoa-Bosompem, Michael; Sakyiamah, Maxwell; Ayertey, Frederick; Owusu, Kofi Baffour-Awuah; Tuffour, Isaac; Atchoglo, Philip; Frempong, Kwadwo Kyereme; Anyan, William K; Uto, Takuhiro; Morinaga, Osamu; Yamashita, Taizo; Aboagye, Frederic; Appiah, Alfred Ampomah; Appiah-Opong, Regina; Nyarko, Alexander K; Yamaoka, Shoji; Yamaguchi, Yasuchika; Edoh, Dominic; Koram, Kwadwo; Ohta, Nobuo; Boakye, Daniel A; Ayi, Irene; Shoyama, Yukihiro

    2015-08-01

    Human African trypanosomiasis (HAT), commonly known as sleeping sickness has remained a serious health problem in many African countries with thousands of new infected cases annually. Chemotherapy, which is the main form of control against HAT has been characterized lately by the viewpoints of toxicity and drug resistance issues. Recently, there have been a lot of emphases on the use of medicinal plants world-wide. Morinda lucida Benth. is one of the most popular medicinal plants widely distributed in Africa and several groups have reported on its anti-protozoa activities. In this study, we have isolated one novel tetracyclic iridoid, named as molucidin, from the CHCl3 fraction of the M. lucida leaves by bioassay-guided fractionation and purification. Molucidin was structurally elucidated by (1)H and (13)C NMR including HMQC, HMBC, H-H COSY and NOESY resulting in tetracyclic iridoid skeleton, and its absolute configuration was determined. We have further demonstrated that molucidin presented a strong anti-trypanosomal activity, indicating an IC50 value of 1.27 μM. The cytotoxicity study using human normal and cancer cell lines indicated that molucidin exhibited selectivity index (SI) against two normal fibroblasts greater than 4.73. Furthermore, structure-activity relationship (SAR) study was undertaken with molucidin and oregonin, which is identical to anti-trypanosomal active components of Alnus japonica. Overlapping analysis of the lowest energy conformation of molucidin with oregonin suggested a certain similarities of aromatic rings of both oregonin and molucidin. These results contribute to the future drug design studies for HAT. PMID:26048790

  18. A new 5-alkylresorcinol glucoside derivative from Cybianthus magnus.

    PubMed

    Cabanillas, B; Vásquez-Ocmín, P; Zebiri, I; Rengifo, E; Sauvain, M; Le, H L; Vaisberg, A; Voutquenne-Nazabadioko, L; Haddad, M

    2016-01-01

    One new 5-alkylresorcinol glucoside (1) was isolated from leaves of Cybianthus magnus, along with 12 known compounds (2-13), isolated from four plants belonging to Myrsinaceae family. Their structures were determined on the basis of spectroscopic analysis and by comparison of their spectral data with those reported in the literature. Among the tested molecules, only compound 2 displayed a strong cytotoxic activity with IC50 values ranging between 22 and 100 μM for all cell lines tested. One new 5-alkylresorcinol glucoside (1) was isolated from leaves of Cybianthus magnus, along with 12 known compounds, isolated from four plants belonging to Myrsinaceae family (2, 3 isolated from C. magnus; 4-7, 10 and 11 isolated from Myrsine latifolia; 4, 8 and 9 isolated from Myrsine sessiflora; 6, 7, 10, 12 and 13 isolated from Myrsine congesta). Their structures were determined on the basis of spectroscopic analysis and by comparison of their spectral data with those reported in the literature. So far, only nine 5-alkylresorcinol glucosides were isolated from leaves of Grevillea robusta. Since resorcinols are known to exhibit strong cytotoxic activity, compounds 1 and 2 were tested against cell lines 3T3, H460, DU145 and MCF-7 for cytotoxicity in vitro and compounds 3-13 were tested for their antileishmanial activity. Compound 2 displayed a strong cytotoxic activity with IC50 values ranging between 22 and 100 μM for all tested cell lines. Compounds 3-13 were not active against Leishmania amazonensis amastigotes. PMID:26181307

  19. Evaluation of anti-HIV-1 activity of a new iridoid glycoside isolated from Avicenna marina, in vitro.

    PubMed

    Behbahani, Mandana

    2014-11-01

    This study was carried out to check the efficacy of methanol seed extract of Avicenna marina and its column chromatographic fractions on Peripheral Blood Mono nuclear Cells (PBMCs) toxicity and HIV-1 replication. The anti-HIV-1 activities of crude methanol extract and its fractions were performed by use of real-time polymerase chain reaction (PCR) assay and HIV-1 p24 antigen kit. A time of drug addiction approach was also done to identify target of anti-HIV compound. The activity of the extracts on CD4, CD3, CD19 and CD45 expression in lymphocytes population was performed by use of flow cytometry. The most active anti-HIV agent was detected by spectroscopic analysis as 2'-O-(4-methoxycinnamoyl) mussaenosidic acid. The apparent effective concentrations for 50% virus replication (EC50) of methanol extract and iridoid glycoside were 45 and 0.1 μg/ml respectively. The iridoid glycoside also did not have any observable effect on the proportion of CD4, CD3, CD19 and CD45 cells or on the intensity of their expressions on PBMCs. In addition, the expression level of C-C chemokine receptor type 5 (CCR5) and chemokine receptor type 4 (CXCR4) on CD4(+) T cells were decreased in cells treated with this iridoid glycoside. The reduction of these two HIV coreceptors and the result of time of addition study demonstrated that this iridoid glycoside restricts HIV-1 replication on the early stage of HIV infection. PMID:25239814

  20. Guaiane-type sesquiterpenoid glucosides from Gardenia jasminoides Ellis.

    PubMed

    Yu, Yang; Gao, Hao; Dai, Yi; Xiao, Gao-Keng; Zhu, Hua-Jie; Yao, Xin-Sheng

    2011-05-01

    Two new guaiane-type sesquiterpenoid glucosides (1 and 2) were isolated from the fruit of Gardenia jasminoides Ellis. Their structures were elucidated to be (1R,7R,10S)-11-O-β-D-glucopyranosyl-4-guaien-3-one (1) and (1R,7R,10S)-7-hydroxy-11-O-β-D-glucopyranosyl-4-guaien-3-one (2) by one- and two-dimensional NMR techniques ((1)H NMR, (13)C NMR, HSQC, HMBC and NOESY), MS, CD spectrometry and chemical methods. PMID:21491483

  1. Two new cyanogenic glucosides from the leaves of Hydrangea macrophylla.

    PubMed

    Yang, Chun-Juan; Wang, Zhi-Bin; Zhu, Da-Ling; Yu, Ying; Lei, Yin-Ting; Liu, Yan

    2012-01-01

    Chemical investigation of the ethanol extract of the aerial parts of Hydrangea macrophylla collected in the Sichuan Province of China resulted in the isolation of two new cyanogenic glucosides. Their structures were elucidated as [(2R)-2-β-D-glucopyranosyloxy)-2-(3,4-dimethoxy-phenyl)] acetonitrile (1) and {(2R)-2-[α-D-glucopyranosyl(1-->6)β-D-glucopyranosyloxy]-2-(3-hydroxy-4-methoxy-phenyl)}acetonitrile (2) on the basis of extensive spectroscopic analysis (1D, 2D NMR and HRESIMS) and chemical studies. PMID:22569418

  2. The protein encoded by the rolB plant oncogene hydrolyses indole glucosides.

    PubMed Central

    Estruch, J J; Schell, J; Spena, A

    1991-01-01

    The rolB gene of Agrobacterium rhizogenes, whose expression stimulates the formation of roots by transformed plant tissues and other growth alterations in transgenic plants, codes for a beta-glucosidase able to hydrolyse indole-beta-glucosides. Indeed, we show that extracts of bacteria and/or plant tissue expressing the rolB protein hydrolyse indoxyl-beta-glucoside (plant indican). Because of the structural similarity between indoxyl-beta-glucoside and indole-3-acetyl-beta-glucoside (IAA-beta-glucoside), we propose that the physiological and developmental alterations in transgenic plants expressing the rolB gene could be the result of an increased intracellular auxin activity caused by the release of active auxins from inactive beta-glucosides. Thus two of the oncogenes carried by the T-DNA of the plant pathogen Agrobacterium rhizogenes (rolB and rolC) perturb plant growth and development by coding for beta-glucosidases with distinct specificities. Whereas the rolC beta-glucosidase releases cytokinins from their glucoside conjugates, the rolB encoded protein hydrolyses indole-beta-glucosides. The combined action of these two genes therefore is expected to modulate the intracellular concentration of two of the main growth factors active in plants. Images PMID:1915286

  3. Colorimetric Method for the Estimation of Total Limonoid Aglycones and Glucoside Contents in Citrus Juices

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A method for estimating the total limonoid aglycone and glucoside concentrations in Citrus samples in terms of limonin and limonin glucoside equivalents is presented. The method consists of extraction followed by colorimetric quantification. The colorimetric quantification was based on the formatio...

  4. Citrus limonin glucoside supplementation decreased biomarkers of liver disease in overweight human subjects

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Orange juice and mixtures of citrus limonoid glucosides isolated from orange juice or its byproducts demonstrated health benefits in human and animal studies. However, the risks and benefits of purified limonin glucoside (LG) in humans are unknown. Aim of this study was to determine the safety and m...

  5. Anomericity of T-2 Toxin-glucoside: Masked Mycotoxin in Cereal Crops

    PubMed Central

    2015-01-01

    T-2 toxin is a trichothecene mycotoxin produced when Fusarium fungi infect grains, especially oats and wheat. Ingestion of T-2 toxin contaminated grain can cause diarrhea, hemorrhaging, and feed refusal in livestock. Cereal crops infected with mycotoxin-producing fungi form toxin glycosides, sometimes called masked mycotoxins, which are a potential food safety concern because they are not detectable by standard approaches and may be converted back to the parent toxin during digestion or food processing. The work reported here addresses four aspects of T-2 toxin-glucosides: phytotoxicity, stability after ingestion, antibody detection, and the anomericity of the naturally occurring T-2 toxin-glucoside found in cereal plants. T-2 toxin-β-glucoside was chemically synthesized and compared to T-2 toxin-α-glucoside prepared with Blastobotrys muscicola cultures and the T-2 toxin-glucoside found in naturally contaminated oats and wheat. The anomeric forms were separated chromatographically and differ in both NMR and mass spectrometry. Both anomers were significantly degraded to T-2 toxin and HT-2 toxin under conditions that mimic human digestion, but with different kinetics and metabolic end products. The naturally occurring T-2 toxin-glucoside from plants was found to be identical to T-2 toxin-α-glucoside prepared with B. muscicola. An antibody test for the detection of T-2 toxin was not effective for the detection of T-2 toxin-α-glucoside. This anomer was produced in sufficient quantity to assess its animal toxicity. PMID:25520274

  6. Enzymatic Synthesis of Apigenin Glucosides by Glucosyltransferase (YjiC) from Bacillus licheniformis DSM 13

    PubMed Central

    Gurung, Rit Bahadur; Kim, Eun-Hee; Oh, Tae-Jin; Sohng, Jae Kyung

    2013-01-01

    Apigenin, a member of the flavone subclass of flavonoids, has long been considered to have various biological activities. Its glucosides, in particular, have been reported to have higher water solubility, increased chemical stability, and enhanced biological activities. Here, the synthesis of apigenin glucosides by the in vitro glucosylation reaction was successfully performed using a UDP-glucosyltransferase YjiC, from Bacillus licheniformis DSM 13. The glucosylation has been confirmed at the phenolic groups of C-4′ and C-7 positions ensuing apigenin 4′-O-glucoside, apigenin 7-O-glucoside and apigenin 4′,7-O-diglucoside as the products leaving the C-5 position unglucosylated. The position of glucosylation and the chemical structures of glucosides were elucidated by liquid chromatography/mass spectroscopy and nuclear magnetic resonance spectroscopy. The parameters such as pH, UDP glucose concentration and time of incubation were also analyzed during this study. PMID:24170092

  7. Amaranthin in feather cockscombs is synthesized via glucuronylation at the cyclo-DOPA glucoside step in the betacyanin biosynthetic pathway.

    PubMed

    Sasaki, Nobuhiro; Abe, Yutaka; Wada, Katsuhiro; Koda, Takatoshi; Goda, Yukihiro; Adachi, Taiji; Ozeki, Yoshihiro

    2005-12-01

    Uridine 5'-diphosphate (UDP)-glucuronic acid: cyclo-DOPA 5-glucoside glucuronosyltransferase activity was detected in a crude extract prepared from the purple flowers of feather cockscombs. This suggests that the glucuronic acid moiety of amaranthin and its derivatives may be introduced at the cyclo-DOPA glucoside step, but not at the betanidin glucoside step. PMID:16247652

  8. Fragmentation study of iridoid glycosides including epimers by liquid chromatography-diode array detection/electrospray ionization mass spectrometry and its application in metabolic fingerprint analysis of Gardenia jasminoides Ellis.

    PubMed

    Zhou, Tingting; Liu, Hua; Wen, Jun; Fan, Guorong; Chai, Yifeng; Wu, Yutian

    2010-09-15

    A high-performance liquid chromatography-diode array detection/electrospray ionization mass spectrometry (HPLC-DAD/ESI-MS) method was applied to the characterization of ten iridoid glycosides in Gardenia jasminoides Ellis, a traditional Chinese medicine. During the process of structural elucidation, two groups of isomers including two epimers were structurally characterized and differentiated according to their distinctive fragmentation patterns which were closely related to their isomeric differentiations. Subsequently, the major compounds were purified by multi-dimensional chromatography and semi-preparative HPLC and the structure identification was confirmed with NMR techniques. The major fragmentation pathways of iridoid glycosides in Gardenia jasminoides Ellis obtained through the MS data were schemed systematically, which provided the best sensitivity and specificity for characterization of the iridoid glycosides especially the isomers so far. Based on the fragmentation patterns of iridoid glycosides concluded, seven major iridoid glycosides were characterized in rat plasma after intravenous administration of Gardenia jasminoides Ellis. PMID:20740525

  9. Identification and Characterization of the Iridoid Synthase Involved in Oleuropein Biosynthesis in Olive (Olea europaea) Fruits.

    PubMed

    Alagna, Fiammetta; Geu-Flores, Fernando; Kries, Hajo; Panara, Francesco; Baldoni, Luciana; O'Connor, Sarah E; Osbourn, Anne

    2016-03-11

    The secoiridoids are the main class of specialized metabolites present in olive (Olea europaea L.) fruit. In particular, the secoiridoid oleuropein strongly influences olive oil quality because of its bitterness, which is a desirable trait. In addition, oleuropein possesses a wide range of pharmacological properties, including antioxidant, anti-inflammatory, and anti-cancer activities. In accordance, obtaining high oleuropein varieties is a main goal of molecular breeding programs. Here we use a transcriptomic approach to identify candidate genes belonging to the secoiridoid pathway in olive. From these candidates, we have functionally characterized the olive homologue of iridoid synthase (OeISY), an unusual terpene cyclase that couples an NAD (P)H-dependent 1,4-reduction step with a subsequent cyclization, and we provide evidence that OeISY likely generates the monoterpene scaffold of oleuropein in olive fruits. OeISY, the first pathway gene characterized for this type of secoiridoid, is a potential target for breeding programs in a high value secoiridoid-accumulating species. PMID:26709230

  10. In vitro anti-Leishmania activity of tetracyclic iridoids from Morinda lucida, benth.

    PubMed

    Amoa-Bosompem, Michael; Ohashi, Mitsuko; Mosore, Mba-Tihssommah; Agyapong, Jeffrey; Tung, Nguyen Huu; Kwofie, Kofi D; Ayertey, Frederick; Owusu, Kofi Baffuor-Awuah; Tuffour, Isaac; Atchoglo, Philip; Djameh, Georgina I; Azerigyik, Faustus A; Botchie, Senyo K; Anyan, William K; Appiah-Opong, Regina; Uto, Takuhiro; Morinaga, Osamu; Appiah, Alfred A; Ayi, Irene; Shoyama, Yukihiro; Boakye, Daniel A; Ohta, Nobuo

    2016-01-01

    Leishmaniasis is an infectious disease transmitted by the sand fly. It is caused by over 20 different species of Leishmania and has affected over 14 million people worldwide. One of the main forms of control of leishmaniasis is chemotherapy, but this is limited by the high cost and/or toxicity of available drugs. We previously found three novel compounds with an iridoid tetracyclic skeleton to have activity against trypanosome parasites. In this study, we determined the activity of the three anti-trypanosome compounds against Leishmania using field strain, 010, and the lab strain Leishmania hertigi. The minimum inhibitory concentration (MIC) of the compounds against 010 was determined by microscopy while the IC50 of compounds against L. hertigi was determined by fluorescence-activated cell sorting with Guava viacount analysis. We found two of the three compounds, molucidin and ML-F52, to have anti-Leishmania activity against both strains. The fluor-microscope observation with DAPI stain revealed that both Molucidin and ML-F52 induced abnormal parasites with two sets of nucleus and kinetoplast in a cell, suggesting that compounds might inhibit cytokinesis in Leishmania parasites. Molucidin and ML-F52 might be good lead compounds for the development of new anti-Leishmania chemotherapy. PMID:27536194

  11. Beetles do it differently: two stereodivergent cyclisation modes in iridoid-producing leaf-beetle larvae.

    PubMed

    Kunert, Maritta; Rahfeld, Peter; Shaker, Kamel H; Schneider, Bernd; David, Anja; Dettner, Konrad; Pasteels, Jacques M; Boland, Wilhelm

    2013-02-11

    Larvae of the Chrysomelina species Phaedon cochleariae, Hydrothassa marginella, Phratora vulgatissima, Gastrophysa viridula, Gastrophysa atrocyanea, Gastrophysa cyanea and Gastrophysa polygoni produce the iridoid chrysomelidial (1) to defend themselves against predators. Feeding experiments with a deuterated precursor ([(2)H(5)]8-hydroxygeraniol 9) and in vitro isotope exchange experiments with defensive secretion in (2)H(2)O revealed differences in the cyclisation of the ultimate precursor 8-oxogeranial (8) to 1, between members of the genus Gastrophysa and all other species. In P. cochleariae, H. marginella and P. vulgatissima 1 is most likely produced by a Rauhut-Currier-type cyclisation via a "transoid dienamine", with loss of a single deuterium atom from C(4) of the precursor. In contrast, members of the genus Gastrophysa cyclise 8 via a "cisoid dienamine" intermediate, with exchange of all three deuterium atoms from the methyl group at C(3). To study whether the different cyclisation modes influence the stereochemistry of 1, the absolute configuration of 1 of the larvae was determined by GC-MS on a chiral column. In accordance with literature (J. Meinwald, T. H. Jones, J. Am. Chem. Soc. 1978, 100, 1883 and N. Shimizu, R. Yakumaru, T. Sakata, S. Shimano, Y. Kuwahara, J. Chem. Ecol. 2012, 38, 29), we found (5S,8S)-chrysomelidial (1) in H. marginella and P. vulgatissima, but P. cochleariae and all investigated members of the genus Gastrophysa synthesise (5R,8R)-chrysomelidial (1). PMID:23341265

  12. Male-to-female transfer of 5-hydroxytryptophan glucoside during mating in Zygaena filipendulae (Lepidoptera).

    PubMed

    Zagrobelny, Mika; Motawia, Mohammed Saddik; Olsen, Carl Erik; Bak, Søren; Møller, Birger Lindberg

    2013-11-01

    Zygaena filipendulae accumulates the cyanogenic glucosides linamarin and lotaustralin by larval sequestration from the food plant or de novo biosynthesis. We have previously demonstrated that the Z. filipendulae male transfers linamarin and lotaustralin to the female in the course of mating. In this study we report the additional transfer of 5-hydroxytryptophan glucoside (5-(β-d-glucopyranosyloxy)-L-Tryptophan) from the Z. filipendulae male internal genitalia to the female spermatophore around 5 h into the mating process. 5-Hydroxytryptophan glucoside is present in the virgin male internal genitalia, and production continues during the early phase of mating. Following initiation of 5-hydroxytryptophan glucoside transfer to the female, the amount in male internal genitalia is drastically reduced until after mating where it is slowly replenished. For unambiguous structural identification, 5-hydroxytryptophan glucoside was chemically synthesized and used as an authentic standard. The biological function of 5-hydroxytryptophan glucoside remains to be established, although we have indications that it may be involved in inducing the female to stay in copula and delay egg-laying to prevent re-mating of the female. To our knowledge 5-hydroxytryptophan glucoside has not previously been reported present in animal tissues. PMID:24012995

  13. Officinalioside, a new lignan glucoside from Borago officinalis L.

    PubMed

    Samy, Mamdouh Nabil; Hamed, Ashraf Nageeb El-Sayed; Sugimoto, Sachiko; Otsuka, Hideaki; Kamel, Mohamed Salah; Matsunami, Katsuyoshi

    2016-01-01

    A new lignan glucoside, officinalioside (1), was isolated from n-BuOH fraction of the aerial parts of Borago officinalis L., together with four known compounds: actinidioionoside (2), roseoside (3), crotalionoside C (4) and kaempferol 3-O-β-D-galactopyranoside (5). The structure of the new compound was established by means of spectroscopic and chemical analyses. Compounds 1 and 2 showed a moderate DPPH radical scavenging activity (IC50: 52.6 ± 1.70 and 41.3 ± 0.25 μM, respectively) comparable with that of the standard trolox (16.6 ± 2.2 μM) without any significant cytotoxicity towards human cell line A549 (IC50 > 100 μM). PMID:26382913

  14. New triterpene glucosides from the roots of Rosa laevigata Michx.

    PubMed

    Yuan, Jing-Quan; Yang, Xin-Zhou; Miao, Jian-Hua; Tang, Chun-Ping; Ke, Chang-Qiang; Zhang, Ji-Bao; Ma, Xiao-Jun; Ye, Yang

    2008-01-01

    Two new ursane-type triterpene glucosides, 2alpha,3alpha,24-trihydroxyurs-12,18-dien-28-oic acid beta-D-glucopyranosyl ester (1) and 2alpha,3alpha,23-trihydroxyurs-12,19(29)-dien-28-oic acid beta-D-glucopyranosyl ester (2), were isolated from the roots of Rosa laevigata, together with three known compounds: 2alpha,3beta,19alpha-trihydroxyurs-12-en-28-oic acid beta-Dglucopyranosyl ester (3), 2alpha,3alpha,19alpha-trihydroxyurs-12-en-28-oic acid beta-D-glucopyranosyl ester (4) and 2alpha,3beta,19alpha,23-tetrahydroxyurs-12-en-28-oic acid beta-D-glucopyranosyl ester (5). The structures of new compounds were established on the basis of detailed 1D and 2D NMR spectroscopic analyses. Compounds 2 and 5 exhibited modest in vitro antifungal activities against Candida albicans and C. krusei. PMID:18830152

  15. Four new neolignan glucosides from the fruits of Arctium lappa.

    PubMed

    Huang, Xiao-Ying; Feng, Zi-Ming; Yang, Ya-Nan; Jiang, Jian-Shuang; Zhang, Pei-Cheng

    2015-05-01

    Four new neolignan glucosides named (7S, 8R)-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan-9'-O-β-d-apiofuranosyl-(1 → 6)-O-β-d-glucopyranoside (1), (8R)-4,9,9'-trihydroxy-3,3'-dimethoxy-7-oxo-8-O-4'-neolignan-4-O-β-d-glucopyranoside (2), (7R, 8S)-dihydrodehydrodiconiferyl alcohol-7'-oxo-4-O-β-d-glucopyranoside (3), and (7'S, 8'R, 8S)-4,4',9'-trihydroxy-3,3'-dimethoxy-7',9-epoxylignan-7-oxo-4-O-β-d-glucopyranoside (4) were isolated from the fruits of Arctium lappa L. Their structures and absolute configurations were elucidated on the basis of comprehensive spectroscopic analyses (UV, IR, HR-ESI-MS, 1D and 2D NMR, CD), as well as by comparison with known analogues in the literature. PMID:25978776

  16. Chemotaxonomic value of magastigmane glucosides of Cichorium calvum.

    PubMed

    Michalska, Klaudia; Beharav, Alex; Kisiel, Wanda

    2014-03-01

    Morphological characters and molecular analyses of Cichorium calvum and C. pumilum do not allow clear discrimination between these closely related wild species. Therefore, the aim of this study was to characterize the secondary metabolites of C. calvum and to select chemical markers which are unique to this species. From roots of C. calvum, ten sesquiterpene lactones were isolated, including seven lactucin-type guaianolides reported earlier from C. pumilum. Aerial parts also afforded secondary metabolites common to both species, along with the megastigmane glucosides staphylionoside D, saussureoside B and komaroveside A. This is the first report of the occurrence of these norisoprenoids in Cichorium species and the second record of their isolation from plants. Therefore, chemical discrimination of C. calvum is possible on the basis of its norisoprenoid composition. PMID:24689202

  17. Three new lignan glucosides from the roots of Scutellaria baicalensis.

    PubMed

    Long, Hailin; Zhang, Haijing; Deng, Anjun; Ma, Lin; Wu, Lianqiu; Li, Zhihong; Zhang, Zhihui; Wang, Wenjie; Jiang, Jiandong; Qin, Hailin

    2016-05-01

    Three new lignan glucosides, baicalensinosides A-C (1-3), were isolated from the roots of Scutellaria baicalensis. The structural elucidation was achieved by in-depth spectroscopic examinations and qualitative chemical test. Structurally, these compounds belong to the 3,4-dibenzyltetrahydrofuran-type lignan glycoside with a mono-hydroxyl substitution at the 7'-position of benzylidene group on the numbering system of lignans being one of their shared critical features. The anti-osteoporotic activity of the isolated compounds was assessed in an in vitro osteoprotegerin (OPG) transcriptional activity assay using dual luciferase reporter detection. At 10 μmol/L, compounds 1-3 increased the relative activating ratio of OPG transcription to 1.83, 0.84 and 0.98 times that of the control group, respectively. PMID:27175334

  18. Indole alkaloid glucosides from the roots of Isatis indigotica.

    PubMed

    Liu, Yu-Feng; Chen, Ming-Hua; Lin, Sheng; Li, Yu-Huan; Zhang, Dan; Jiang, Jian-Dong; Shi, Jian-Gong

    2016-01-01

    Five new indole alkaloid glucosides named isatindigotindolosides A-E (1-5), along with three known analogs (6-8), were isolated from an aqueous extract of the Isatis indigotica roots. Their structures including the absolute configurations were determined based on comprehensive spectroscopic data analysis, combined with chemical methods and electronic circular dichroism spectra calculations. In the preliminary assays, compounds 1, 6 and 7 showed antiviral activity against influenza virus A/Hanfang/359/95 (H3N2) with IC50 values of 14.6-33.3 μM. Compound 1 also exhibited inhibitory effect against nitric oxide (NO) production in microglial cell BV2 with an inhibition ratio of 93.0% at 10 μM. PMID:26651370

  19. Sesamolinol glucoside, disaminyl ether, and other lignans from sesame seeds.

    PubMed

    Grougnet, Raphael; Magiatis, Prokopios; Laborie, Helene; Lazarou, Despina; Papadopoulos, Athanasios; Skaltsounis, Alexios-Leandros

    2012-01-11

    The application of a procedure based on XAD-4 adsorption resin permitted the obtainment of an enriched polyphenolic extract from Sesamum indicum seeds. Chemical analysis of the obtained extract led to the identification of 12 lignans. Among them, 2 lignans, (+)-sesamolinol-4'-O-β-D-glucoside and disaminyl ether, are reported for the first time as natural compounds. Their structure has been determined by spectroscopic methods, mainly by the application of one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) techniques [heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC), and nuclear Overhauser effect spectrometry (NOESY)] and mass spectroscopy. The isolated compounds were evaluated for their antimutagenic activity. Among the tested lignans, the most active lignan was found to be sesamolin, followed by sesamolinol and samin, against H(2)O(2). Additionally, some of the tested lignans showed desmutagenic activity against benzo[a]pyrene (BaP). PMID:22148167

  20. Three new lignan glucosides from the roots of Scutellaria baicalensis

    PubMed Central

    Long, Hailin; Zhang, Haijing; Deng, Anjun; Ma, Lin; Wu, Lianqiu; Li, Zhihong; Zhang, Zhihui; Wang, Wenjie; Jiang, Jiandong; Qin, Hailin

    2016-01-01

    Three new lignan glucosides, baicalensinosides A–C (1–3), were isolated from the roots of Scutellaria baicalensis. The structural elucidation was achieved by in-depth spectroscopic examinations and qualitative chemical test. Structurally, these compounds belong to the 3,4-dibenzyltetrahydrofuran-type lignan glycoside with a mono-hydroxyl substitution at the 7′-position of benzylidene group on the numbering system of lignans being one of their shared critical features. The anti-osteoporotic activity of the isolated compounds was assessed in an in vitro osteoprotegerin (OPG) transcriptional activity assay using dual luciferase reporter detection. At 10 μmol/L, compounds 1–3 increased the relative activating ratio of OPG transcription to 1.83, 0.84 and 0.98 times that of the control group, respectively. PMID:27175334

  1. Olive leaf components apigenin 7-glucoside and luteolin 7-glucoside direct human hematopoietic stem cell differentiation towards erythroid lineage.

    PubMed

    Samet, Imen; Villareal, Myra O; Motojima, Hideko; Han, Junkyu; Sayadi, Sami; Isoda, Hiroko

    2015-06-01

    The generation of blood cellular components from hematopoietic stem cells is important for the therapy of a broad spectrum of hematological disorders. In recent years, several lines of evidence suggested that certain nutrients, vitamins and flavonoids may have important roles in controlling the stem cell fate decision by maintaining their self-renewal or stimulating the lineage-specific differentiation. In this study, main olive leaf phytochemicals oleuropein (Olp), apigenin 7-glucoside (Api7G) and luteolin 7-glucoside (Lut7G) were investigated for their potential effects on hematopoietic stem cell differentiation using both phenotypic and molecular analysis. Oleuropein and the combination of the three compounds enhanced the differentiation of CD34+ cells into myelomonocytic cells and lymphocytes progenitors and inhibited the commitment to megakaryocytic and erythroid lineages. Treatment with Lut7G stimulated both the erythroid and the myeloid differentiation, while treatment with Api7G specifically induced the differentiation of CD34+ cells towards the erythroid lineage and inhibited the myeloid differentiation. Erythroid differentiation induced by Api7G and Lut7G treatments was confirmed by the increase in hemoglobin genes expressions (α-hemoglobin, β-hemoglobin and γ-hemoglobin) and erythroid transcription factor GATA1 expression. As revealed by microarray analysis, the mechanisms underlying the erythroid differentiation-inducing effect of Api7G on hematopoietic stem cells involves the activation of JAK/STAT signaling pathway. These findings prove the differentiation-inducing effects of olive leaf compounds on hematopoietic stem cells and highlight their potential use in the ex vivo generation of blood cells. PMID:26299581

  2. Involvement of JAK/STAT signaling in the effect of cornel iridoid glycoside on experimental autoimmune encephalomyelitis amelioration in rats.

    PubMed

    Yin, Linlin; Chen, Yongyan; Qu, Zhao; Zhang, Li; Wang, Qi; Zhang, Qi; Li, Lin

    2014-09-15

    In the present study, we investigated the therapeutic benefit of cornel iridoid glycoside (CIG), the main component extracted from Cornus officinalis, in experimental autoimmune encephalomyelitis (EAE) rats. CIG was intragastrically administered daily after EAE initiation for 20days and reduced disease severity, incidence, disease onset and ongoing paralysis. Histopathological staining showed that CIG could reduce T cell entry to the central nervous system and microglia activation, increased brain-derived neurotrophic factor (BDNF) expression and mature oligodendrocytes, and decreased oligodendrocyte progenitor cells (OPCs). Also, CIG treatment inhibited brain JAK/STAT1/3 and reduced proinflammatory cytokines. CIG might be a novel potential therapeutic agent for multiple sclerosis (MS). PMID:25012120

  3. Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.

    PubMed

    Herrmann, Martina; Joppe, Holger; Schmaus, Gerhard

    2002-06-01

    The glycosylated pyrrolizidine alkaloid, thesinine-4'-O-beta-D-glucoside, has been isolated from the aqueous methanol extract of dried, defatted seeds of Borago officinalis (Boraginaceae). The structure was established by means of spectroscopic and chemical analysis. PMID:12031432

  4. Two new cucurbitacin glucosides, opercurins A and B, from the Brazilian folk medicine "Buchinha" (Luffa operculata).

    PubMed

    Kawahara, Nobuo; Kurata, Atsuyo; Hakamatsuka, Takashi; Sekita, Setsuko; Satake, Motoyoshi

    2004-08-01

    The structures of two new cucurbitacin glucosides designated opercurins A (1) and B (2), isolated from the fruit of Luffa operculata, have been confirmed by extensive spectroscopic investigation. PMID:15305007

  5. Small intestinal hydrolysis of plant glucosides: higher glucohydrolase activities in rodents than passerine birds.

    PubMed

    Lessner, Krista M; Dearing, M Denise; Izhaki, Ido; Samuni-Blank, Michal; Arad, Zeev; Karasov, William H

    2015-09-01

    Glycosides are a major group of plant secondary compounds characterized by one or more sugars conjugated to a lipophilic, possibly toxic aglycone, which is released upon hydrolysis. We compared small intestinal homogenate hydrolysis activity of three rodent and two avian species against four substrates: amygdalin and sinigrin, two plant-derived glucosides, the sugar lactose, whose hydrolysis models some activity against flavonoid and isoflavonoid glucosides, and the disaccharide sugar maltose (from starch), used as a comparator. Three new findings extend our understanding of physiological processing of plant glucosides: (1) the capacity of passerine birds to hydrolyze plant glucosides seems relatively low, compared with rodents; (2) in this first test of vertebrates' enzymic capacity to hydrolyze glucosinolates, sinigrin hydrolytic capacity seems low; (3) in laboratory mice, hydrolytic activity against lactose resides on the enterocytes' apical membrane facing the intestinal lumen, but activity against amygdalin seems to reside inside enterocytes. PMID:26113142

  6. Virus-induced gene silencing identifies Catharanthus roseus 7-deoxyloganic acid-7-hydroxylase, a step in iridoid and monoterpene indole alkaloid biosynthesis.

    PubMed

    Salim, Vonny; Yu, Fang; Altarejos, Joaquín; De Luca, Vincenzo

    2013-12-01

    Iridoids are a major group of biologically active molecules that are present in thousands of plant species, and one versatile iridoid, secologanin, is a precursor for the assembly of thousands of monoterpenoid indole alkaloids (MIAs) as well as a number of quinoline alkaloids. This study uses bioinformatics to screen large databases of annotated transcripts from various MIA-producing plant species to select candidate genes that may be involved in iridoid biosynthesis. Virus-induced gene silencing of the selected genes combined with metabolite analyses of silenced plants was then used to identify the 7-deoxyloganic acid 7-hydroxylase (CrDL7H) that is involved in the 3rd to last step in secologanin biosynthesis. Silencing of CrDL7H reduced secologanin levels by at least 70%, and increased the levels of 7-deoxyloganic acid to over 4 mg g(-1) fresh leaf weight compared to control plants in which this iridoid is not detected. Functional expression of this CrDL7H in yeast confirmed its biochemical activity, and substrate specificity studies showed its preference for 7-deoxyloganic acid over other closely related substrates. Together, these results suggest that hydroxylation precedes carboxy-O-methylation in the secologanin pathway in Catharanthus roseus. PMID:24103035

  7. A study of the substance dependence effect of the ethanolic extract and iridoid-rich fraction from Valeriana jatamansi Jones in mice

    PubMed Central

    Yu, Lin; Ke-ke, Xu; Chao-yong, Chen; Rui-tong, Zhang; Ming, Lan; Shao-hua, Li; Ling-zhen, Pan; Tian-e, Zhang; Zhi-yong, Yan

    2015-01-01

    Background: Recently we found the ethanolic extract and iridoid-rich fraction from Valeriana jatamansi Jones, which is a traditional Chinese medicine exhibited anxiolytic properties. Objective: This study aims to the substance dependence effect of the ethanolic extract and iridoid-rich fraction. Materials and Methods: The study included two experiments: Mice were given orally with ethanolic extract for 12 weeks or iridoid-rich fraction for 16 weeks in experiment I and experiment II, respectively. Diazepam was used as a control drug and the normal mice groups were administered with 0.5% carboxymethyl cellulose Na in both experiments. All groups were administered twice daily. Natural withdrawal symptoms, withdrawal-induced body weight change, audiogenic tail-erection test (in experiment I), and pentylenetetrazol (PTZ)-induced convulsion test (in experiment II) were measured. Results: (1) Compared to normal group in both experiments, the diazepam-treated group exhibited obvious withdrawal symptoms of tail-erection, irritability, teeth chattering, etc; the body weight of them after withdrawal had a period of significant loss (P < 0.05 or P < 0.01); and the ratios of tail-erection and seizure in two experiments were improved significantly when mice were induced by mixer noise ringtone (experiment I) or PTZ (experiment II) (P < 0.05 or P < 0.01).(2) In experiment I and II, there were no significant differences between mice that received ethanolic extract or iridoid-rich fraction and normal group in terms of natural withdrawal symptoms and withdrawal-induced body weight change (P > 0.05); in audiogenic tail-erection test, it found that the significant difference compared with normal group was just in ethanolic extract 900 mg/kg dose group on week 8 (P < 0.05); in PTZ-induced convulsion test, mice in iridoid-rich fraction groups had a slightly tail-erection and seizure, all results of them were with no significant difference compare to normal mice (P > 0.05), while

  8. Interaction of cyanidin-3-O-glucoside with three proteins.

    PubMed

    Tang, Lin; Li, Shu; Bi, Hongna; Gao, Xin

    2016-04-01

    We studied the binding of cyanidin-3-O-glucoside (C3G) with bovine serum albumin (BSA), hemoglobin (Hb) and myoglobin (Mb), using multi-spectral techniques and molecular modeling. Fluorescence and time-resolved fluorescence studies suggested that C3G quenched BSA, Hb or Mb fluorescence in a static mode with binding constants of 4.159, 0.695 and 1.545 × 10(4) L mol(-1) at 308K, respectively. The thermodynamic parameters represented hydrogen bonds and van der Waals forces dominated the binding. Furthermore, CD, UV-vis, and three-dimensional fluorescence spectra results indicated the secondary structures of BSA, Hb and Mb were partially destroyed by C3G with the α-helix percentage of C3G-Hb and C3G-Mb decreased while that of C3G-BSA was increased. UV-vis spectral results showed these binding interactions partially affected the heme bands of Hb and Mb. In addition, molecular modeling analysis supported the experimental results well. The calculated results of equilibrium fraction showed that the concentration of free C3G in plasma was high enough to be stored and transported from the circulatory system to reach their target sites to provide their therapeutic effects. PMID:26593527

  9. Cucurbitane glucosides from the root of Machilus yaoshansis.

    PubMed

    Gan, Maoluo; Liu, Mingtao; Liu, Bo; Lin, Sheng; Zhang, Yanling; Zi, Jiachen; Song, Weixia; Ye, Fei; Chen, Xiaoguang; Shi, Jiangong

    2011-11-28

    Seven new cucurbitane triterpene glucosides (1-5, 8, and 9) and five known analogues (6, 7, 10, cucurbitacin I 2-O-β-d-glucopyranoside, and khekadaengoside K) have been isolated from an ethanol extract of roots of Machilus yaoshansis. Compounds 1 and 2 have an unusual 16,23:22,25-diepoxy unit, 4 is an uncommon cucurbitane 25-carbamate with the carbamoyl amino group attached at C-24 to form an oxazolidinone ring in the side chain, and 8 is the first example of a trinorcucurbitane derivative. The configurations in several pairs of C-24 epimeric cucurbitacins with 24,25-dihydroxy-22-one side chains were assigned, and the validity of J(23a,24) and J(23b,24) values to differentiate the configuration at C-24 in these cucurbitane derivatives is discussed. Compounds 2-4 showed in vitro activity against protein tyrosine phosphatase 1B with IC50 values of 8.63, 2.81, and 4.26 μM, respectively. Cucurbitacin E 2-O-β-d-glucopyranoside (10) showed selective cytotoxicity against BGC-823 and A549 cancer cells with IC50 values of 4.98 and 3.20 μM, respectively. PMID:22044245

  10. Tetrahydroxystilbene Glucoside Improves Neurotrophic Factors Release in Cultured Astroglia.

    PubMed

    Lin, FengQin; Zhou, YanZhen; Shi, WanLan; Wan, YanYing; Zhang, ZeGang; Zhang, Feng

    2016-01-01

    Tetrahydroxystilbene glucoside (TSG), one of the main ingredients of Polygonum multiflorum, has a great number of beneficial effects for health including anti-oxidant, free radicalscavenging and anti-inflammatory properties. However, the potential effects of TSG on neurotrophic factors release remain unclear. In this study, rat primary astroglia cultures were applied to investigate TSG-mediated neurotrophic effects. The protein levels and production of glial cell-line derived neurotrophic factor (GDNF), brain-derived neurotrophic factor (BDNF) and nerve growth factor (NGF) in astroglia and the culture medium were determined by western blotting assay and ELISA, respectively. Results indicated that TSG increased the production of neurotrophic factors in a concentration-dependent manner. At different time points of TSG treatment, the BDNF and NGF production in the culture medium was increased 48 h after treatment, while GDNF secretion was initially induced 24 h after TSG treatment. Consistent with the neurotrophic factors release, TSG significantly increased the BDNF, GDNF and NGF protein expressions in astroglia. Furthermore, TSG significantly induced the phosphorylation of extracellular signal-regulated kinase (ERK) 1/2 and a specific ERK inhibitor-U0126 inhibited TSG-mediated secretion of BDNF, GDNF and NGF. Overall, this study demonstrated that TSG induces astroglia-derived neurotrophic factors release, suggesting TSG might hold a therapeutic potential for neurological disorders. PMID:26295829

  11. In vitro effects of cholesterol β-D-glucoside, cholesterol and cycad phytosterol glucosides on respiration and reactive oxygen species generation in brain mitochondria.

    PubMed

    Panov, Alexander; Kubalik, Nataliya; Brooks, Benjamin R; Shaw, Christopher A

    2010-10-01

    The cluster of neurodegenerative disorders in the western Pacific termed amyotrophic lateral sclerosis-parkinsonism dementia complex (ALS-PDC) has been repeatedly linked to the use of seeds of various species of cycad. Identification and chemical synthesis of the most toxic compounds in the washed cycad seeds, a variant phytosteryl glucosides, and even more toxic cholesterol β-D-glucoside (CG), which is produced by the human parasite Helicobacter pylori, provide a possibility to study in vitro the mechanisms of toxicity of these compounds. We studied in detail the effects of CG on the respiratory activities and generation of reactive oxygen species (ROS) by nonsynaptic brain and heart mitochondria oxidizing various substrates. The stimulatory effects of CG on respiration and ROS generation showed strong substrate dependence, suggesting involvement of succinate dehydrogenase (complex II). Maximal effects on ROS production were observed with 1 μmol CG/1 mg mitochondria. At this concentration the cycad toxins β-sitosterol-β-D-glucoside and stigmasterol-β-D-glucoside had effects on respiration and ROS production similar to CG. However, poor solubility precluded full concentration analysis of these toxins. Cholesterol, stigmasterol and β-sitosterol had no effect on mitochondrial functions studied at concentrations up to 100 μmol/mg protein. Our results suggest that CG may influence mitochondrial functions through changes in the packing of the bulk membrane lipids, as was shown earlier by Deliconstantinos et al. (Biochem Cell Biol 67:16-24, 1989). The neurotoxic effects of phytosteryl glucosides and CG may be associated with increased oxidative damage of neurons. Unlike heart mitochondria, in activated neurons mitochondria specifically increase ROS production associated with succinate oxidation (Panov et al., J Biol Chem 284:14448-14456, 2009). PMID:20938651

  12. The synthesis and antitumor activity of twelve galloyl glucosides.

    PubMed

    Li, Chang-Wei; Dong, Hua-Jin; Cui, Cheng-Bin

    2015-01-01

    Twelve galloyl glucosides 1-12, showing diverse substitution patterns with two or three galloyl groups, were synthesized using commercially available, low-cost D-glucose and gallic acid as starting materials. Among them, three compounds, methyl 3,6-di-O-galloyl-α-D-glucopyranoside (9), ethyl 2,3-di-O-galloyl-α-D-glucopyranoside (11) and ethyl 2,3-di-O-galloyl-β-D-glucopyranoside (12), are new compounds and other six, 1,6-di-O-galloyl-β-D-glucopyranose (1), 1,4,6-tri-O-galloyl-β-D-glucopyranose (2), 1,2-di-O-galloyl-β-D-glucopyranose (3), 1,3-di-O-galloyl-β-D-glucopyranose (4), 1,2,3-tri-O-galloyl-α-D-glucopyranose (6) and methyl 3,4,6-tri-O-galloyl-α-D-glucopyranoside (10), were synthesized for the first time in the present study. In in vitro MTT assay, 1-12 inhibited human cancer K562, HL-60 and HeLa cells with inhibition rates ranging from 64.2% to 92.9% at 100 μg/mL, and their IC50 values were determined to be varied in 17.2-124.7 μM on the tested three human cancer cell lines. In addition, compounds 1-12 inhibited murine sarcoma S180 cells with inhibition rates ranging from 38.7% to 52.8% at 100 μg/mL in the in vitro MTT assay, and in vivo antitumor activity of 1 and 2 was also detected in murine sarcoma S180 tumor-bearing Kunming mice using taxol as positive control. PMID:25633333

  13. Structure-activity relationships of oligo-beta-glucoside elicitors of phytoalexin accumulation in soybean.

    PubMed Central

    Cheong, J J; Birberg, W; Fügedi, P; Pilotti, A; Garegg, P J; Hong, N; Ogawa, T; Hahn, M G

    1991-01-01

    The abilities of a family of chemically synthesized oligo-beta-glucosides, ranging in size from hexamer to decamer, to induce phytoalexin accumulation in soybean cotyledons were investigated to determine which structural elements of the oligoglucosides are important for their biological activity. The results of the biological assays established that the following structural motif is necessary for the oligo-beta-glucosides to have high elicitor activity: [formula; see text] The branched trisaccharide at the nonreducing end of the oligoglucosides was found to be essential for maximum elicitor activity. Substitution of either the nonreducing terminal backbone glucosyl residue or the side-chain glucosyl residue closest to the nonreducing end with glucosaminyl or N-acetylglucosaminyl residues reduced the elicitor activity of the oligoglucosides between 10-fold and 10,000-fold. Elicitor activity was also reduced 1000-fold if the two side-chain glucosyl residues were attached to adjacent backbone glucosyl residues rather than to glucosyl residues separated by an unbranched residue. In contrast, modifications of the reducing terminal glucosyl residue of an elicitor-active hepta-beta-glucoside by conjugation with tyramine and subsequent iodination had no significant effect on the elicitor activity of the hepta-beta-glucoside. These results demonstrate that oligo-beta-glucosides must have a specific structure to trigger the signal transduction pathway, which ultimately leads to the de novo synthesis of phytoalexins in soybean. PMID:1840904

  14. Enzyme bread improvers affect the stability of deoxynivalenol and deoxynivalenol-3-glucoside during breadmaking.

    PubMed

    Vidal, Arnau; Ambrosio, Asier; Sanchis, Vicente; Ramos, Antonio J; Marín, Sonia

    2016-10-01

    The stability of deoxynivalenol (DON) and deoxynivalenol-3-glucoside (DON-3-glucoside) during the breadmaking process was studied. Some enzymes used in the bakery industry were examined to evaluate their effects on DON and DON-3-glucoside. The level of DON in breads without added enzymes was reduced (17-21%). Similarly, the addition of cellulase, protease, lipase and glucose-oxidase did not modify this decreasing trend. The effect of xylanase and α-amylase on DON content depended on the fermentation temperature. These enzymes reduced the DON content by 10-14% at 45°C. In contrast, at 30°C, these enzymes increased the DON content by 13-23%. DON-3-glucoside levels decreased at the end of fermentation, with a final reduction of 19-48% when no enzymes were used. However, the presence of xylanase, α-amylase, cellulase and lipase resulted in bread with greater quantities of DON-3-glucoside when fermentation occurred at 30°C. The results showed that wheat bran and flour may contain hidden DON that may be enzymatically released during the breadmaking process when the fermentation temperature is close to 30°C. PMID:27132852

  15. Sequestration, tissue distribution and developmental transmission of cyanogenic glucosides in a specialist insect herbivore.

    PubMed

    Zagrobelny, Mika; Olsen, Carl Erik; Pentzold, Stefan; Fürstenberg-Hägg, Joel; Jørgensen, Kirsten; Bak, Søren; Møller, Birger Lindberg; Motawia, Mohammed Saddik

    2014-01-01

    Considering the staggering diversity of bioactive natural products present in plants, insects are only able to sequester a small number of phytochemicals from their food plants. The mechanisms of how only some phytochemicals are sequestered and how the sequestration process takes place remains largely unknown. In this study the model system of Zygaena filipendulae (Lepidoptera) and their food plant Lotus corniculatus is used to advance the knowledge of insect sequestration. Z. filipendulae larvae are dependent on sequestration of the cyanogenic glucosides linamarin and lotaustralin from their food plant, and have a much lower fitness if reared on plants without these compounds. This study investigates the fate of the cyanogenic glucosides during ingestion, sequestration in the larvae, and in the course of insect ontogeny. To this purpose, double-labeled linamarin and lotaustralin were chemically synthesized carrying two stable isotopes, a (2)H labeled aglucone and a (13)C labeled glucose moiety. In addition, a small amount of (14)C was incorporated into the glucose residue. The isotope-labeled compounds were applied onto cyanogenic L. corniculatus leaves that were subsequently presented to the Z. filipendulae larvae. Following ingestion by the larvae, the destiny of the isotope labeled cyanogenic glucosides was monitored in different tissues of larvae and adults at selected time points, using radio-TLC and LC-MS analyses. It was shown that sequestered compounds are taken up intact, contrary to earlier hypotheses where it was suggested that the compounds would have to be hydrolyzed before transport across the gut. The uptake from the larval gut was highly stereo selective as the β-glucosides were retained while the α-glucosides were excreted and recovered in the frass. Sequestered compounds were rapidly distributed into all analyzed tissues of the larval body, partly retained throughout metamorphosis and transferred into the adult insect where they were

  16. Quercetin 3-O-glucoside suppresses epidermal growth factor-induced migration by inhibiting EGFR signaling in pancreatic cancer cells.

    PubMed

    Lee, Jungwhoi; Han, Song-I; Yun, Jeong-Hun; Kim, Jae Hoon

    2015-12-01

    Pancreatic cancer is one of the most dangerous cancers and is associated with a grave prognosis. Despite increased knowledge of the complex signaling networks responsible for progression of pancreatic cancer, many challenging therapies have fallen short of expectations. In this study, we examined the anti-migratory effect of quercetin 3-O-glucoside in epidermal growth factor-induced cell migration by inhibiting EGF receptor (EGFR) signaling in several human pancreatic cancer cell lines. Treatment with quercetin, quercetin 3-O-glucoside, and quercetin 7-O-glucoside differentially suppressed epidermal growth factor-induced migration activity of human pancreatic cancer cells. In particular, quercetin 3-O-glucoside strongly inhibited the infiltration activity of pancreatic cancer cells in a dose-dependent manner. Furthermore, quercetin 3-O-glucoside exerted the anti-migratory effect even at a relatively low dose compared with other forms of quercetin. The anti-tumor effects of quercetin 3-O-glucoside were mediated by selectively inhibiting the EGFR-mediated FAK, AKT, MEK1/2, and ERK1/2 signaling pathway. Combinatorial treatment with quercetin 3-O-glucoside plus gemcitabine showed the synergistic anti-migratory effect on epidermal growth factor-induced cell migration in human pancreatic cancer cell lines. These results suggest that quercetin 3-O-glucoside has potential for anti-metastatic therapy in human pancreatic cancer. PMID:26109002

  17. Metabolic utilization of pyridoxine-beta-glucoside in rats: influence of vitamin B-6 status and route of administration

    SciTech Connect

    Trumbo, P.R.; Gregory, J.F. 3d.

    1988-11-01

    (3H)5'-O-(beta-D-glucopyranosyl) pyridoxine (PN-glucoside) and (14C)pyridoxine (PN) were administered orally or intraperitoneally to vitamin B-6-adequate or -deficient rats. Analysis of intestinal contents and feces indicated effective intestinal absorption of PN-glucoside relative to PN. There was greater retention of 14C than 3H in the liver and carcass regardless of the route of administration of the radiolabeled vitamins. There was no major difference in the relative distribution of 3H and 14C among the vitamin B-6 metabolites in the liver between the treatment groups, and no (3H)PN-glucoside was detected in any of the livers. For all groups, the majority of the 3H administered was detected in the urine within 24 h. Less excretion of both 3H and 14C in the urine was observed for the deficient rats. There was no major difference in the relative proportion of urinary (3H)PN-glucoside or (3H)4-PA between rats fed or injected with the radiolabeled vitamins. These results indicate that vitamin B-6 status influences the clearance of metabolites derived from PN and PN-glucoside, as well as the clearance of intact PN-glucoside. Vitamin B-6 status, however, has little or no effect on the utilization of PN-glucoside. This study also suggests that the intestine is the primary site of the limited conversion of PN-glucoside to biologically active PN in the rat.

  18. Further characterization and regulation of malonyl-coenzyme A: flavonoid glucoside malonyltransferases from parsley cell suspension cultures

    SciTech Connect

    Matern, U.; Feser, C.; Hammer, D.

    1983-10-01

    Two malonyltransferases, malonyl-CoA:flavone/flavonol 7-O-glucoside malonyltransferase and malonyl-CoA:flavonol 3-O-glucoside malonyltransferase, were purified to apparent homogeneity from uv-irradiated parsley cell cultures. Both purified enzymes appear to be specific for flavonoid glycosides. Additional malonyltransferases, active toward several phenol glucosides other than flavonoids, were present in partially purified 7-O-glucoside malonyltransferase preparations. Antibodies raised against the purified 3-O-glucoside malonyltransferase did not inhibit the activity of the 7-O-glucoside malonyltransferase over a wide antibody concentration range. Determination of the rate of synthesis in vivo of the 3-O-glucoside malonyltransferase after ultraviolet light-pulse induction of parsley cells revealed two maxima at 6 and 30 h, respectively. These results indicate that the induced changes in 3-O-glucoside malonyltransferase activity were the consequence of either a repeated change in the rate of synthesis of one enzyme species or changes in the synthesis rates of more than one enzyme species.

  19. A specific, high-affinity binding site for the hepta-beta-glucoside elicitor exists in soybean membranes.

    PubMed Central

    Cheong, J J; Hahn, M G

    1991-01-01

    The presence of a specific binding site for a hepta-beta-glucoside elicitor of phytoalexin accumulation has been demonstrated in soybean microsomal membranes. A tyramine conjugate of the elicitor-active hepta-beta-glucoside was prepared and radiolabeled with 125I. The labeled hepta-beta-glucoside-tyramine conjugate was used as a ligand in binding assays with a total membrane fraction prepared from soybean roots. Binding of the radiolabeled hepta-beta-glucoside elicitor was saturable, reversible, and with an affinity (apparent Kd = 7.5 x 10(-10) M) comparable with the concentration of hepta-beta-glucoside required for biological activity. A single class of hepta-beta-glucoside binding sites was found. The binding site was inactivated by proteolysis and by heat treatment, suggesting that the binding site is a protein or glycoprotein. Competitive inhibition of binding of the radiolabeled hepta-beta-glucoside elicitor by a number of structurally related oligoglucosides demonstrated a direct correlation between the binding affinities and the elicitor activities of these oligoglucosides. Thus, the hepta-beta-glucoside-binding protein fulfills criteria expected of a bona fide receptor for the elicitor-active oligosaccharin. PMID:1840905

  20. Identification of delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside, a postulated intermediate in the biosynthesis of ternatin C5 in the blue petals of Clitoria ternatea (butterfly pea).

    PubMed

    Kazuma, Kohei; Kogawa, Koichiro; Noda, Naonobu; Kato, Naoki; Suzuki, Masahiko

    2004-11-01

    Ternatins are blue anthocyanins found in the petals of Clitoria ternata (butterfly pea). Among them, ternatin C5 (delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3',5'-di-O-beta-glucoside; 2) has the structure common to all the ternatins, which is characterized by its glucosylation pattern: a 3,3',5'-triglucosylated anthocyanidin. In the course of studying biosynthetic pathways of ternatins, the key enzymatic activities to produce ternatin C5 were discovered in a crude enzyme preparation from the petals of a blue petal line of C. ternatea. When this preparation was tested for activity against several delphinidin glycosides, delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside (6), a postulated intermediate, was found in the reaction mixture, together with three known anthocyanins, which were spectroscopically structurally identified. As a result of structural identification, the following enzymatic activities were identified: UDP-glucose :delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside 5'-O-glucosyltransferase (5'GT), UDP-glucose :delphinidin 3-O-(6''-O-malonyl)-beta-glucoside 3'-O-glucosyltransferase (3'GT), UDP-glucose :delphinidin 3-O-glucosyltransferase, and malonyl-CoA :delphinidin 3-O-beta-glucoside 6''-malonyltransferase. In a mauve petal line, which did not accumulate ternatins but delphinidin 3-O-(6''-O-malonyl)-beta-glucoside in its petal, there were neither 5'GT nor 3'GT activities. Thus, the early biosynthetic pathway of ternatins may be characterized by the stepwise transfer of two glucose residues to 3'- and 5'-position of delphinidin 3-O-(6''-O-malonyl)-beta-glucoside (1; Scheme) from UDP-glucose. PMID:17191814

  1. Purification and functional characterization of the first stilbene glucoside-specific β-glucosidase isolated from Lactobacillus kimchi.

    PubMed

    Ko, Jin-A; Park, J Y; Kwon, H J; Ryu, Y B; Jeong, H J; Park, S J; Kim, C Y; Oh, H M; Park, C S; Lim, Y H; Kim, D; Rho, M C; Lee, W S; Kim, Y M

    2014-12-01

    This study aimed to develop viable enzymes for bioconversion of resveratrol-glucoside into resveratrol. Out of 13 bacterial strains tested, Lactobacillus kimchi JB301 could completely convert polydatin into resveratrol. The purified enzyme had an optimum temperature of 30-40°C and optimum pH of pH 5.0 against polydatin. This enzyme showed high substrate specificities towards different substrates in the following order: isorhaponticin>polydatin>mulberroside A>oxyresveratrol-3-O-glucoside. Additionally, it rarely hydrolyzed astringin and desoxyrhaponticin. Based on these catalytic specificities, we suggest this enzyme be named stilbene glucoside-specific β-glucosidase. Furthermore, polydatin extracts from Polygonum cuspidatum were successfully converted to resveratrol with a high yield (of over 99%). Stilbene glucoside-specific β-glucosidase is the first enzyme isolated from lactic acid bacteria capable of bio-converting various stilbene glucosides into stilbene. PMID:25442950

  2. Cyclitol glucosides and their role in the synthesis of a glucan from uridine diphosphate glucose in Phaseolus aureus. Characterization of some cyclitol glucoside and their synthesis

    PubMed Central

    Kemp, Jennifer; Loughman, Brian C.

    1974-01-01

    Short-chained sugar compounds, thought to be involved in the synthesis of callose, were formed in small amounts from UDP-glucose by soluble extracts from hypocotyls of seedlings of Phaseolus aureus. The properties of the glycosides were investigated by treatment with various chemicals and analysis by paper chromatography, g.l.c. and mass spectrometry. The data obtained support the characterization of these compounds as myoinositol-β-glucoside and diglucosylmyoinositol. The cyclitol moiety was provided by the enzyme extract. Free myoinositol was not the immediate substrate but a compound containing myoinositol, isolated from the enzyme extract, may be involved. The method of synthesis of these glucosides is compared with that of other cyclitol glycosides. PMID:4441368

  3. Profiling of components and validated determination of iridoids in Gardenia Jasminoides Ellis fruit by a high-performance-thin-layer- chromatography/mass spectrometry approach.

    PubMed

    Coran, Silvia A; Mulas, Stefano; Vasconi, Alessio

    2014-01-17

    A novel method was set up with the aim to obtain a simultaneous cross comparative evaluation of different Gardenia Jasminoides Ellis fruits by the HPTLC fingerprint approach. The main components among the iridoid, hydroxycinnamic derivative and crocin classes were identified by TLC-MS ancillary techniques. The iridoids geniposide, gardenoside and genepin-1-β-d-gentiobioside were also quantitated by densitometric scanning at 240nm. LiChrospher HPTLC Silica gel 60 RP-18 W F254, 20cm×10cm plates with acetonitrile: formic acid 0.1% (40:60 v/v) as the mobile phase was used. The method was validated giving rise to a dependable and high throughput procedure well suited to routine applications. Iridoids were quantified in the range of 240-1140ng with RSD of repeatability and intermediate precision between 0.9-2.5% and accuracy with bias 1.6-2.6%. The method was tested on six commercial Gardenia Jasminoides fruit samples. PMID:24365117

  4. The bHLH transcription factor BIS1 controls the iridoid branch of the monoterpenoid indole alkaloid pathway in Catharanthus roseus.

    PubMed

    Van Moerkercke, Alex; Steensma, Priscille; Schweizer, Fabian; Pollier, Jacob; Gariboldi, Ivo; Payne, Richard; Vanden Bossche, Robin; Miettinen, Karel; Espoz, Javiera; Purnama, Purin Candra; Kellner, Franziska; Seppänen-Laakso, Tuulikki; O'Connor, Sarah E; Rischer, Heiko; Memelink, Johan; Goossens, Alain

    2015-06-30

    Plants make specialized bioactive metabolites to defend themselves against attackers. The conserved control mechanisms are based on transcriptional activation of the respective plant species-specific biosynthetic pathways by the phytohormone jasmonate. Knowledge of the transcription factors involved, particularly in terpenoid biosynthesis, remains fragmentary. By transcriptome analysis and functional screens in the medicinal plant Catharanthus roseus (Madagascar periwinkle), the unique source of the monoterpenoid indole alkaloid (MIA)-type anticancer drugs vincristine and vinblastine, we identified a jasmonate-regulated basic helix-loop-helix (bHLH) transcription factor from clade IVa inducing the monoterpenoid branch of the MIA pathway. The bHLH iridoid synthesis 1 (BIS1) transcription factor transactivated the expression of all of the genes encoding the enzymes that catalyze the sequential conversion of the ubiquitous terpenoid precursor geranyl diphosphate to the iridoid loganic acid. BIS1 acted in a complementary manner to the previously characterized ethylene response factor Octadecanoid derivative-Responsive Catharanthus APETALA2-domain 3 (ORCA3) that transactivates the expression of several genes encoding the enzymes catalyzing the conversion of loganic acid to the downstream MIAs. In contrast to ORCA3, overexpression of BIS1 was sufficient to boost production of high-value iridoids and MIAs in C. roseus suspension cell cultures. Hence, BIS1 might be a metabolic engineering tool to produce sustainably high-value MIAs in C. roseus plants or cultures. PMID:26080427

  5. The bHLH transcription factor BIS1 controls the iridoid branch of the monoterpenoid indole alkaloid pathway in Catharanthus roseus

    PubMed Central

    Van Moerkercke, Alex; Steensma, Priscille; Schweizer, Fabian; Pollier, Jacob; Gariboldi, Ivo; Payne, Richard; Vanden Bossche, Robin; Miettinen, Karel; Espoz, Javiera; Purnama, Purin Candra; Kellner, Franziska; Seppänen-Laakso, Tuulikki; O’Connor, Sarah E.; Rischer, Heiko; Memelink, Johan; Goossens, Alain

    2015-01-01

    Plants make specialized bioactive metabolites to defend themselves against attackers. The conserved control mechanisms are based on transcriptional activation of the respective plant species-specific biosynthetic pathways by the phytohormone jasmonate. Knowledge of the transcription factors involved, particularly in terpenoid biosynthesis, remains fragmentary. By transcriptome analysis and functional screens in the medicinal plant Catharanthus roseus (Madagascar periwinkle), the unique source of the monoterpenoid indole alkaloid (MIA)-type anticancer drugs vincristine and vinblastine, we identified a jasmonate-regulated basic helix–loop–helix (bHLH) transcription factor from clade IVa inducing the monoterpenoid branch of the MIA pathway. The bHLH iridoid synthesis 1 (BIS1) transcription factor transactivated the expression of all of the genes encoding the enzymes that catalyze the sequential conversion of the ubiquitous terpenoid precursor geranyl diphosphate to the iridoid loganic acid. BIS1 acted in a complementary manner to the previously characterized ethylene response factor Octadecanoid derivative-Responsive Catharanthus APETALA2-domain 3 (ORCA3) that transactivates the expression of several genes encoding the enzymes catalyzing the conversion of loganic acid to the downstream MIAs. In contrast to ORCA3, overexpression of BIS1 was sufficient to boost production of high-value iridoids and MIAs in C. roseus suspension cell cultures. Hence, BIS1 might be a metabolic engineering tool to produce sustainably high-value MIAs in C. roseus plants or cultures. PMID:26080427

  6. Hybrid reuteransucrase enzymes reveal regions important for glucosidic linkage specificity and the transglucosylation/hydrolysis ratio.

    PubMed

    Kralj, Slavko; van Leeuwen, Sander S; Valk, Vincent; Eeuwema, Wieger; Kamerling, Johannis P; Dijkhuizen, Lubbert

    2008-12-01

    The reuteransucrase enzymes of Lactobacillus reuteri strain 121 (GTFA) and L. reuteri strain ATCC 55730 (GTFO) convert sucrose into alpha-d-glucans (labelled reuterans) with mainly alpha-(1-->4) glucosidic linkages (50% and 70%, respectively), plus alpha-(1-->6) linkages. In the present study, we report a detailed analysis of various hybrid GTFA/O enzymes, resulting in the identification of specific regions in the N-termini of the catalytic domains of these proteins as the main determinants of glucosidic linkage specificity. These regions were divided into three equal parts (A1-3; O1-3), and used to construct six additional GTFA/O hybrids. All hybrid enzymes were able to synthesize alpha-glucans from sucrose, and oligosaccharides from sucrose plus maltose or isomaltose as acceptor substrates. Interestingly, not only the A2/O2 regions, with the three catalytic residues, affect glucosidic linkage specificity, but also the upstream A1/O1 regions make a strong contribution. Some GTFO derived hybrid/mutant enzymes displayed strongly increased transglucosylation/hydrolysis activity ratios. The reduced sucrose hydrolysis allowed the much improved conversion of sucrose into oligo- and polysaccharide products. Thus, the glucosidic linkage specificity and transglucosylation/hydrolysis ratios of reuteransucrase enzymes can be manipulated in a relatively simple manner. This engineering approach has yielded clear changes in oligosaccharide product profiles, as well as a range of novel reuteran products differing in alpha-(1-->4) and alpha-(1-->6) linkage ratios. PMID:19016850

  7. Effect of different exposed lights on quercetin and quercetin glucoside content in onion (Allium cepa L.)

    PubMed Central

    Ko, Eun Young; Nile, Shivraj Hariram; Sharma, Kavita; Li, Guan Hao; Park, Se Won

    2014-01-01

    Quercetin and quercetin glucosides are the major flavonols present in onion (Allium cepa L.) and are predominantly present as quercetin, quercetin-3,4′-diglucoside and quercetin-4′-glucoside. Effect of different light wavelengths on onion after harvest and storage, with fluorescent, blue, red and ultra violet light influenced the quercetin and quercetin glucosides profile. In a peeled onion, all the light treatments elevated quercetin content in bulb. Among them, particularly fluorescent light effect was more eminent which stimulates the maximum synthesis of quercetin in onion. In case of whole onion bulb, skin and pulp showed different responses to light treatment, respectively. The pulp had the highest quercetin glucosides under blue light, whereas the lowest under fluorescent light. Onion skin showed nearly opposite pattern as compared to the pulp. In particular, light treatment proved to be a better way to increase the level of quercetin content in onions which might be utilized for industrial production of bioactive compounds from onion and onion waste products. PMID:26150744

  8. Occurrence of deoxynivalenol and deoxynivalenol-3-glucoside in hard red spring wheat grown in the USA

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Deoxynivalenol (DON) is a mycotoxin found in wheat that is infected with Fusarium fungus. DON may also be converted to a type of "masked mycotoxin," named deoxynivalenol-3-glucoside (D3G), as a result of detoxification process of the plant. Both DON and D3G are known to be toxic. Due to the lack o...

  9. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Methyl glucoside-coconut oil ester. 178.3600 Section 178.3600 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: ADJUVANTS, PRODUCTION AIDS, AND SANITIZERS Certain Adjuvants and...

  10. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Methyl glucoside-coconut oil ester. 172.816 Section 172.816 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Multipurpose Additives...

  11. Serotonin 5-O-β-Glucoside and Its N-Methylated Forms in Citrus Genus Plants.

    PubMed

    Servillo, Luigi; Giovane, Alfonso; Casale, Rosario; D'Onofrio, Nunzia; Ferrari, Giovanna; Cautela, Domenico; Balestrieri, Maria Luisa; Castaldo, Domenico

    2015-04-29

    Citrus genus is characterized by a specific presence of indole metabolites deriving from the N-methylation of tryptamine and its hydroxylated form, 5-hydroxytryptamine (serotonin), which are likely involved in plant defense mechanisms. In this study, we identified for the first time the occurrence in Citrus plants of serotonin 5-O-β-glucoside and all its N-methylated derivatives, that is, N-methylserotonin 5-O-β-glucoside, N,N-dimethylserotonin (bufotenine) 5-O-β-glucoside, and N,N,N-trimethylserotonin (bufotenidine) 5-O-β-glucoside. The identification of the glucosylated compounds was based on mass spectrometric studies, hydrolysis by glucosidase, and in some cases, comparison to authentic compounds. Beside leaves, the distribution of the glucosylated forms and their aglycones in some Citrus species was evaluated in flavedo, albedo, juice, and seeds. The simultaneous presence of serotonin and its N-methylated derivatives, together with the corresponding glucosylated forms, is consistent with the occurrence of a metabolic pathway, specific for Citrus, aimed at potentiating the defensive response to biotic stress through the optimization of the production and use of the most toxic of such metabolites. PMID:25893818

  12. Effect of different exposed lights on quercetin and quercetin glucoside content in onion (Allium cepa L.).

    PubMed

    Ko, Eun Young; Nile, Shivraj Hariram; Sharma, Kavita; Li, Guan Hao; Park, Se Won

    2015-07-01

    Quercetin and quercetin glucosides are the major flavonols present in onion (Allium cepa L.) and are predominantly present as quercetin, quercetin-3,4'-diglucoside and quercetin-4'-glucoside. Effect of different light wavelengths on onion after harvest and storage, with fluorescent, blue, red and ultra violet light influenced the quercetin and quercetin glucosides profile. In a peeled onion, all the light treatments elevated quercetin content in bulb. Among them, particularly fluorescent light effect was more eminent which stimulates the maximum synthesis of quercetin in onion. In case of whole onion bulb, skin and pulp showed different responses to light treatment, respectively. The pulp had the highest quercetin glucosides under blue light, whereas the lowest under fluorescent light. Onion skin showed nearly opposite pattern as compared to the pulp. In particular, light treatment proved to be a better way to increase the level of quercetin content in onions which might be utilized for industrial production of bioactive compounds from onion and onion waste products. PMID:26150744

  13. Fate of dietary pyridoxine-beta-glucoside in the lactating rat

    SciTech Connect

    Trumbo, P.R.; Gregory, J.F. III

    1989-01-01

    (/sup 3/H)5'-O-(beta-D-glucopyranosyl) pyridoxine (PN-glucoside) and (/sup 14/C)pyridoxine (PN) were orally administered to lactating rats. Milk was collected from the dam, and the stomach contents and liver were collected from the suckling pups 24 and 48 h after administration. Analysis of the isotopic ratio (/sup 3/H//sup 14/C) in the milk and stomach contents indicated that the secretion of /sup 3/H in the milk was 20-25% as great as the secretion of /sup 14/C. The only labeled form of /sup 3/H and /sup 14/C in the stomach contents was pyridoxal phosphate (PLP), indicating that PN-glucoside was hydrolyzed to PN and subsequently metabolized prior to secretion by the mammary gland. The isotopic ratio in the livers of the pups was similar to that of the stomach contents. Furthermore, the relative distribution of the two isotopes among the hepatic metabolites of the pups was similar. The results of this study indicate that intact PN-glucoside is not secreted in milk, although vitamin B-6 derived from the limited hydrolysis and metabolism of PN-glucoside is delivered to the mammary gland for secretion.

  14. Quercetin from shallots (Allium cepa L. var. aggregatum) is more bioavailable than its glucosides.

    PubMed

    Wiczkowski, Wieslaw; Romaszko, Jerzy; Bucinski, Adam; Szawara-Nowak, Dorota; Honke, Joanna; Zielinski, Henryk; Piskula, Mariusz K

    2008-05-01

    The lipophilic character of quercetin suggests that it can cross enterocyte membranes via simple diffusion. Therefore, it should be more bioavailable than its glucosides, which require preliminary hydrolysis or active transport for absorption. However, the published human studies show that quercetin is less bioavailable than its glucosides. Assuming that low bioavailability of quercetin aglycone provided to humans as a pure substance is the result of its low solubility in the digestive tract, we studied its bioavailability from dietary sources in which quercetin was dispersed in the food matrix. In a randomized crossover study, 9 volunteers took a single dose of either shallot flesh (99.2% quercetin glucosides and 0.8% quercetin aglycone) or dry shallot skin (83.3% quercetin aglycone and 16.7% quercetin glucosides), providing 1.4 mg quercetin per kg of body weight. Blood samples were collected before and after consumption of shallot preparations. Plasma quercetin was measured on HPLC with electrochemical detection after plasma enzymatic treatment. The maximum plasma quercetin concentration of 1.02 +/- 0.13 micromol/L was reached at 2.33 +/- 0.50 h after shallot flesh consumption compared with 3.95 +/- 0.62 micromol/L at 2.78 +/- 0.15 h after dry skin consumption. The area under the concentration-time curve after dry skin consumption was 47.23 +/- 7.53 micromol x h(-1) x L(-1) and was significantly higher than that after shallot flesh intake (22.23 +/- 2.32 micromol x h(-1) x L(-1)). When provided along with dietary sources, quercetin aglycone is more bioavailable than its glucosides in humans. Results point to the food matrix as a key factor. PMID:18424596

  15. Beneficial effects of cornel iridoid glycoside on behavioral impairment and senescence status in SAMP8 mice at different ages.

    PubMed

    Ma, Denglei; Zhu, Yanqiu; Li, Yanzheng; Yang, Cuicui; Zhang, Li; Li, Yali; Li, Lin; Zhang, Lan

    2016-10-01

    The aim of the present study was to investigate the effects of cornel iridoid glycoside (CIG) on behavioral changes and senescent status in senescence-accelerated mouse-prone 8 (SAMP8) mice at different ages (6, 10, and 14 months old). The learning and memory ability, the motor function and the aging conditions of SAMP8 mice were evaluated after CIG treatment in this study. Results showed that intragastrical administration of CIG (100 and 200mg/kg) for two months obviously improved the impaired cognitive ability of SAMP8 mice at the age of 6 months and 10 months, respectively. The treatment with CIG significantly increased the motor function of SAMP8 mice at 10 months and 14 months of age, respectively. CIG also evidently decreased the high grading score of senescence and increased the low surviving rate of SAMP8 mice at the age of 14 months. In addition, CIG treatment inhibited tau hyperphosphorylation in the hippocampus and striatum of SAMP8 mice at different ages. Together, these results indicate that CIG represent a potentially useful treatment for ameliorating the impaired cognitive ability, the motor dysfunction, aging conditions and hyperphosphorylation of tau in aging and age-related neurodegenerative diseases, such as Alzheimer's disease. PMID:27283974

  16. The cytotoxic and tyrosine kinase inhibitory properties of C21 steroids and iridoids from the tubers of Alocasia cucullata.

    PubMed

    Peng, Wei; Liang, Shuang; Hu, JiaLiang; Chen, ZhiYu; Zheng, Xiangwei

    2016-07-01

    Ten steroids and iridoids were isolated from the tubers of Alocasia cucullata (Lour.) G. Don. Among them, alocasgenin A (1) and alocasgenoside B-C (2-3) were new compounds and the aglycone of compound 1, obtained from the acid hydrolysis of 1, was named alocasgenol (1a). Also, for the first time, tenacigenin B (4), 17β-tenacigenin-B (5), 3-O-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-β-D-oleandropyranosyl-tenacigenin C (6), marsdenoside A-B (7-8) and tenacigenoside A-B (9-10) were isolated from the genus Alocasia. The chemical structures were elucidated by the extensive analysis of spectral data and compared with the literature. By evaluation of the cytotoxic and tyrosine kinase inhibition, compounds 1-10, 1a and compound 2 showed significant growth inhibition against two tumour cell lines, MGC-803 and HT-29, while compounds 1, 1a, 3, 6 and 8 presented moderate inhibition. Furthermore, compound 2 had the inhibitory property against the enzyme activity biochemically. PMID:27120176

  17. Inhibition of the pro-inflammatory mediators' production and anti-inflammatory effect of the iridoid scrovalentinoside.

    PubMed

    Bas, Esperanza; Recio, M Carmen; Abdallah, Mohamed; Máñez, Salvador; Giner, Rosa M; Cerdá-Nicolás, Miguel; Ríos, José-Luis

    2007-04-01

    We have studied scrovalentinoside, an iridoid with anti-inflammatory properties isolated from Scrophularia auriculata ssp. pseudoauriculata, as an anti-inflammatory agent in different experimental models of delayed-type hypersensitivity. We found that scrovalentinoside reduced the edema induced by oxazolone at 0.5 mg/ear and sheep red blood cells at 10 mg/kg. The observed effect occurred during the last phase or inflammatory response; during the earlier phase or induction of the delayed-type hypersensitivity reaction, no significant activity was noted. Thus, scrovalentinoside reduced both the edema and cell infiltration in vivo and reduced lymphocyte proliferation in vitro, affecting the cycle principally during the first 48 h. Whereas cells stimulated with phytohemagglutinin changed from the G(0)/G(1) phase to the S and G(2)/M phases, when these same cells were treated with scrovalentinoside (100 microM), they remained in the G(0)/G(1) phase. Finally, scrovalentinoside inhibited the production of the pro-inflammatory mediators' TNF-alpha, IFN-gamma, IL-1beta, IL-2, IL-4, LTB(4), and NO, but had no effect on the production of the anti-inflammatory cytokine IL-10. PMID:17112695

  18. Engineering of a Nepetalactol-Producing Platform Strain of Saccharomyces cerevisiae for the Production of Plant Seco-Iridoids.

    PubMed

    Campbell, Alex; Bauchart, Philippe; Gold, Nicholas D; Zhu, Yun; De Luca, Vincenzo; Martin, Vincent J J

    2016-05-20

    The monoterpene indole alkaloids (MIAs) are a valuable family of chemicals that include the anticancer drugs vinblastine and vincristine. These compounds are of global significance-appearing on the World Health Organization's list of model essential medicines-but remain exorbitantly priced due to low in planta levels. Chemical synthesis and genetic manipulation of MIA producing plants such as Catharanthus roseus have so far failed to find a solution to this problem. Synthetic biology holds a potential answer, by building the pathway into more tractable organisms such as Saccharomyces cerevisiae. Recent work has taken the first steps in this direction by producing small amounts of the intermediate strictosidine in yeast. In order to help improve on these titers, we aimed to optimize the early biosynthetic steps of the MIA pathway to the metabolite nepetalactol. We combined a number of strategies to create a base strain producing 11.4 mg/L of the precursor geraniol. We also show production of the critical intermediate 10-hydroxygeraniol and demonstrate nepetalactol production in vitro. Lastly we demonstrate that activity of the iridoid synthase toward the intermediates geraniol and 10-hydroxygeraniol results in the synthesis of the nonproductive intermediates citronellol and 10-hydroxycitronellol. This discovery has serious implications for the reconstruction of the MIA in heterologous organisms. PMID:26981892

  19. Structures of Iridoid Synthase from Cantharanthus roseus with Bound NAD(+) , NADPH, or NAD(+) /10-Oxogeranial: Reaction Mechanisms.

    PubMed

    Hu, Yumei; Liu, Weidong; Malwal, Satish R; Zheng, Yingying; Feng, Xinxin; Ko, Tzu-Ping; Chen, Chun-Chi; Xu, Zhongxia; Liu, Meixia; Han, Xu; Gao, Jian; Oldfield, Eric; Guo, Rey-Ting

    2015-12-14

    Structures of the iridoid synthase nepetalactol synthase in the presence of NAD(+) , NADPH or NAD(+) /10-oxogeranial were solved. The 10-oxogeranial substrate binds in a transoid-O1-C3 conformation and can be reduced by hydride addition to form the byproduct S-10-oxo-citronellal. Tyr178 Oζ is positioned 2.5 Å from the substrate O1 and provides the second proton required for reaction. Nepetalactol product formation requires rotation about C1-C2 to form the cisoid isomer, leading to formation of the cis-enolate, together with rotation about C4-C5, which enables cyclization and lactol production. The structure is similar to that of progesterone-5β-reductase, with almost identical positioning of NADP, Lys146(147), Tyr178(179), and F342(343), but only Tyr178 and Phe342 appear to be essential for activity. The transoid 10-oxogeranial structure also serves as a model for β-face hydride attack in progesterone 5β-reductases and is of general interest in the context of asymmetric synthesis. PMID:26768532

  20. 4-Pentafluoroethylumbelliferyl-beta-D-glucoside as a new fluorogenic substrate for acid beta-D-glucosidase.

    PubMed

    Tsvetkova, I V; Karpova, E A; Dudukina, T V; Voznyi, Y V

    1996-04-30

    4-Pentafluoroethylumbelliferyl-beta-D-glucoside is proposed as an efficient substrate for human leukocyte acid beta-glucosidase. Its synthesis is described. This substrate was compared directly with 4-trifluoromethylumbelliferyl-beta-D-glucoside synthesized by us earlier and with 4-methylumbelliferyl-beta-D-glucoside which is commonly used for acid beta-glucosidase activity assay. The specific activity of acid beta-glucosidase with 4-pentafluoroethylumbelliferyl-beta-D-glucoside was 3- and 8-fold higher than it was with the substrates mentioned above. The kinetic parameters KM and VMAX for human leukocyte acid beta-glucosidase with the three substrates was determined. One possible application of the newly synthesized substrate is its use in the diagnosis of acid beta-glucosidase hereditary deficiency (Gaucher's disease). PMID:8740577

  1. Enzymatic synthesis, structural characterization and antioxidant capacity assessment of a new lipophilic malvidin-3-glucoside-oleic acid conjugate.

    PubMed

    Cruz, Luis; Fernandes, Iva; Guimarães, Marta; de Freitas, Victor; Mateus, Nuno

    2016-06-15

    The chemical modification of anthocyanins (water-soluble pigments) into more lipophilic compounds is very important to expand their application in the food, medical and cosmetic industries. In this work, the synthesis of a pure malvidin-3-glucoside-oleic acid ester derivative was achieved by enzymatic catalysis. This approach allowed us to synthesize a novel compound, malvidin-3-O-(6''-oleoyl)glucoside (Mv3glc-OA), which was structurally characterized by mass spectrometry and for the first time by NMR spectroscopy. The enzymatic reaction revealed to be regioselective giving only one ester product. Antioxidant features of the malvidin-3-glucoside lipophilic derivative by means of DPPH, FRAP and lipid peroxidation assays were assessed, which confirmed that the structural modification of the genuine malvidin-3-glucoside into a more lipophilic compound did not compromise its antioxidant potential and protected more effectively a lipidic substrate from oxidation, which is an important insight for future technological applications. PMID:27220831

  2. Biosynthesis of isoxazolin-5-one and 3-nitropropanoic acid containing glucosides in juvenile Chrysomelina.

    PubMed

    Becker, Tobias; Ploss, Kerstin; Boland, Wilhelm

    2016-07-14

    Stable-isotope-labeled precursors were used to establish the biosynthetic pathway leading from β-alanine towards isoxazolin-5-one glucoside 1 and its 3-nitropropanoate (3-NPA) ester 2 in Chrysomelina larvae. Both structural elements originate from sequestered plant-derived β-alanine or from propanoyl-CoA that is derived from the degradation of some essential amino acids, e.g. valine. β-Alanine is converted into 3-NPA and isoxazolinone 5 by consecutive oxidations of the amino group of β-Ala. Substituting the diphospho group of α-UDP-glucose with 5 generates the isoxazolin-5-one glucoside 1, which serves in the circulating hemolymph of the larva as a platform for esterification with 3-nitropropanoyl-CoA. The pathway was validated with larvae of Phaedon cochleariae, Chrysomela populi as well as Gastrophysa viridula. PMID:27272952

  3. Biosynthesis of Dehydrodiconiferyl Alcohol Glucosides: Implications for the Control of Tobacco Cell Growth 1

    PubMed Central

    Orr, John D.; Lynn, David G.

    1992-01-01

    The dehydrodiconiferyl alcohol glucosides A and B are factors isolated from transformed Vinca rosea tumor cells that can replace the cytokinin requirement for growth of tobacco (Nicotiana tabacum) pith and callus cells in culture. These factors, present in tobacco pith cells, have their concentrations elevated approximately 2 orders of magnitude after cytokinin exposure. Biosynthesis experiments showed that these compounds are not cell wall fragments, as previously suggested, but are produced directly from coniferyl alcohol. Their synthesis is probably associated with the existing pathway for cell wall biosynthesis in both Vinca tumors and tobacco pith explants. The pathway requires only two steps, the dimerization of coniferyl alcohol by a soluble intracellular peroxidase and subsequent glycosylation. Biosynthetic experiments suggested that dehydrodiconiferyl alcohol glucoside breakdown was very slow and control of its concentration was exerted through restricted availability of coniferyl alcohol. PMID:16668635

  4. Hepatoprotective activity of twelve novel 7'-hydroxy lignan glucosides from Arctii Fructus.

    PubMed

    Yang, Ya-Nan; Huang, Xiao-Ying; Feng, Zi-Ming; Jiang, Jian-Shuang; Zhang, Pei-Cheng

    2014-09-17

    Twelve novel 7'-hydroxy lignan glucosides (1-12), including two benzofuran-type neolignans, two 8-O-4' neolignans, two dibenzylbutyrolactone lignans, and six tetrahydrofuranoid lignans, together with six known lignan glucosides (13-18), were isolated from the fruit of Arctium lappa L. (Asteraceae), commonly known as Arctii Fructus. Their structures were elucidated using spectroscopy (1D and 2D NMR, MS, IR, ORD, and UV) and on the basis of chemical evidence. The absolute configurations of compounds 1-12 were confirmed using rotating frame nuclear overhauser effect spectroscopy (ROESY), the circular dichroic (CD) exciton chirality method, and Rh2(OCOCF3)4-induced CD spectrum analysis. All of the isolated compounds were tested for hepatoprotective effects against D-galactosamine-induced cytotoxicity in HL-7702 hepatic cells. Compounds 1, 2, 7-12, and 17 showed significantly stronger hepatoprotective activity than the positive control bicyclol at a concentration of 1 × 10(-5) M. PMID:25180661

  5. Effective catalytic conversion of cellulose into high yields of methyl glucosides over sulfonated carbon based catalyst.

    PubMed

    Dora, Sambha; Bhaskar, Thallada; Singh, Rawel; Naik, Desavath Viswanatha; Adhikari, Dilip Kumar

    2012-09-01

    An amorphous carbon based catalyst was prepared by sulfonation of the bio-char obtained from fast pyrolysis (N(2) atm; ≈ 550°C) of biomass. The sulfonated carbon catalyst contained high acidity of 6.28 mmol/g as determined by temperature programmed desorption of ammonia of sulfonated carbon catalyst and exhibited high catalytic performance for the hydrolysis of cellulose. Amorphous carbon based catalyst containing -SO(3)H groups was successfully tested and the complete conversion of cellulose in methanol at moderate temperatures with high yields ca. ≥ 90% of α, β-methyl glucosides in short reaction times was achieved. The methyl glucosides formed in methanol are more stable for further conversion than the products formed in water. The carbon catalyst was demonstrated to be stable for five cycles with slight loss in catalytic activity. The utilization of bio-char as a sulfonated carbon catalyst provides a green and efficient process for cellulose conversion. PMID:22776237

  6. Exclusive accumulation of Z-isomers of monolignols and their glucosides in bark of Fagus grandifolia

    NASA Technical Reports Server (NTRS)

    Lewis, N. G.; Inciong, E. J.; Ohashi, H.; Towers, G. H.; Yamamoto, E.

    1988-01-01

    In addition to Z-coniferyl and Z-sinapyl alcohols, bark extracts of Fagus grandifolia also contain significant amounts of the glucosides, Z-coniferin, Z-isoconiferin (previously called faguside) and Z-syringin. The corresponding E-isomers of these glucosides do not accumulate to a detectable level. The accumulation of the Z-isomers suggests that either they are not lignin precursors or that they are reservoirs of monolignols for subsequent lignin biosynthesis; it is not possible to distinguish between these alternatives. The co-occurrence of Z-coniferin and Z-isoconiferin demonstrate that glucosylation of monolignols can occur at either the phenolic or the allylic hydroxyl groups.

  7. A new hydroxyjasmone glucoside and its related compounds from the leaf of thyme.

    PubMed

    Kitajima, Junichi; Ishikawa, Toru; Urabe, Atushi

    2004-08-01

    From the polar portion of the methanol extract of thyme (leaf of Thymus vulgaris; Labiatae), which has been used as a stomachic, carminative, a component of prepared cough tea, and as a spice, a new hydroxyjasmone glucoside, (Z)-5'-hydroxyjasmone 5'-O-beta-D-glucopyranoside was isolated together with five related compounds and four aromatic compounds. The structures of the new compound was clarified by spectral investigation. PMID:15305005

  8. Modulation of protein tyrosine nitration and inflammatory mediators by isoprenylhydroquinone glucoside.

    PubMed

    Olmos, Ana; Giner, Rosa-María; Recio, María-Carmen; Ríos, José-Luis; Máñez, Salvador

    2007-03-01

    The nitration of tyrosine caused by peroxynitrite and other reactive nitrogen species is clearly detrimental for some physiological processes; however, its signalling role is still open to controversy. Among the natural phenolics known for their ability to oppose free tyrosine nitration, isoprenylhydroquinone glucoside is investigated due to its unusual structure, which contains a simple hydroxybenzene alkylated by a hemiterpenoid moiety. This hydroquinone was shown to be an effective inhibitor of peroxynitrite-induced protein tyrosine nitration in 3T3 fibroblasts. When tested on bovine seroalbumin nitration, however, the potency was reduced by half and the effect was almost abolished in the presence of bicarbonate. In contrast, addition of this anion had no effect on the nitrite/hydrogen peroxide/hemin system. Isoprenylhydroquinone glucoside was also active in the microM range on intra- and extracellular protein-bound tyrosine nitration by phorbol 12-myristate 13-acetate-stimulated neutrophils. The effects on nitric oxide synthase expression, interleukin-1beta and tumor necrosis factor-alpha production by lipopolysaccharide-stimulated macrophages were quite moderate. Thus, isoprenylhydroquinone glucoside is an inhibitor of protein nitration in situ, but lacks effect on the generation of either nitric oxide or inflammatory cytokines. PMID:17161592

  9. Occurrence of sarmentosin and other hydroxynitrile glucosides in Parnassius (papilionidae) butterflies and their food plants.

    PubMed

    Bjarnholt, Nanna; Nakonieczny, Mirosław; Kędziorski, Andrzej; Debinski, Diane M; Matter, Stephen F; Olsen, Carl Erik; Zagrobelny, Mika

    2012-05-01

    Sequestration of plant secondary metabolites is a widespread phenomenon among aposematic insects. Sarmentosin is an unsaturated γ-hydroxynitrile glucoside known from plants and some Lepidoptera. It is structurally and biosynthetically closely related to cyanogenic glucosides, which are commonly sequestered from food plants and/or de novo synthesized by lepidopteran species. Sarmentosin was found previously in Parnassius (Papilionidae) butterflies, but it was not known how the occurrence was related to food plants or whether Parnassius species could biosynthesize the compound. Here, we report on the occurrence of sarmentosin and related compounds in four different Parnassius species belonging to two different clades, as well as their known and suspected food plants. There were dramatic differences between the two clades, with P. apollo and P. smintheus from the Apollo group containing high amounts of sarmentosin, and P. clodius and P. mnemosyne from the Mnemosyne group containing low or no detectable amounts. This was reflected in the larval food plants; P. apollo and P. smintheus larvae feed on Sedum species (Crassulaceae), which all contained considerable amounts of sarmentosin, while the known food plants of the two other species, Dicentra and Corydalis (Fumariaceae), had no detectable levels of sarmentosin. All insects and plants containing sarmentosin also contained other biosynthetically related hydroxynitrile glucosides in patterns previously reported for plants, but not for insects. Not all findings could be explained by sequestration alone and we therefore hypothesize that Parnassius species are able to de novo synthesize sarmentosin. PMID:22527055

  10. Regulation of gene expression: cryptic β-glucoside (bgl) operon of Escherichia coli as a paradigm.

    PubMed

    Harwani, Dharmesh

    2014-01-01

    Bacteria have evolved various mechanisms to extract utilizable substrates from available resources and consequently acquire fitness advantage over competitors. One of the strategies is the exploitation of cryptic cellular functions encoded by genetic systems that are silent under laboratory conditions, such as the bgl (β-glucoside) operon of E. coli. The bgl operon of Escherichia coli, involved in the uptake and utilization of aromatic β-glucosides salicin and arbutin, is maintained in a silent state in the wild type organism by the presence of structural elements in the regulatory region. This operon can be activated by mutations that disrupt these negative elements. The fact that the silent bgl operon is retained without accumulating deleterious mutations seems paradoxical from an evolutionary view point. Although this operon appears to be silent, specific physiological conditions might be able to regulate its expression and/or the operon might be carrying out function(s) apart from the utilization of aromatic β-glucosides. This is consistent with the observations that the activated operon confers a Growth Advantage in Stationary Phase (GASP) phenotype to Bgl(+) cells and exerts its regulation on at least twelve downstream target genes. PMID:25763016

  11. Diversity of sugar acceptor of glycosyltransferase 1 from Bacillus cereus and its application for glucoside synthesis.

    PubMed

    Chiu, Hsi-Ho; Shen, Mo-Yuan; Liu, Yuan-Ting; Fu, Yu-Lieh; Chiu, Yu-An; Chen, Ya-Huei; Huang, Chin-Ping; Li, Yaw-Kuen

    2016-05-01

    Glycosyltransferase 1 from Bacillus cereus (BcGT1) catalyzes the transfer of a glucosyl moiety from uridine diphosphate glucose (UDP-glucose) to various acceptors; it was expressed and characterized. The specificity of acceptors was found to be broad: more than 20 compounds classified into O-, S-, and N-linkage glucosides can be prepared with BcGT1 catalysis. Based on this work, we conclude that the corresponding acceptors of these compounds must possess the following features: (1) the acceptors must contain at least one aromatic or fused-aromatic or heteroaromatic ring; (2) the reactive hydroxyl or sulfhydryl or amino group can attach either on the aromatic ring or on its aliphatic side chain; and (3) the acceptors can be a primary, secondary, or even a tertiary amine. Four representative acceptors-fluorescein methyl ester, 17-β-estradiol, 7-mercapto-4-methylcoumarin, and 6-benzylaminopurine-were chosen as a candidate acceptor for O-, S-, and N-glucosidation, respectively. These enzymatic products were purified and the structures were confirmed with mass and NMR spectra. As all isolated glucosides are β-anomers, BcGT1 is confirmed to be an inverting enzyme. This study not only demonstrates the substrate promiscuity of BcGT1 but also showed the great application prospect of this enzyme in bioconversion of valuable bioactive molecules. PMID:26795959

  12. Quantitative Analysis of Phenylpropanoid Glycerol Glucosides in Different Organs of Easter Lily (Lilium longiflorum Thunb.).

    PubMed

    Munafo, John P; Gianfagna, Thomas J

    2015-05-20

    The Easter lily (Lilium longiflorum Thunb.) is esteemed worldwide as an attractive ornamental plant, and the flower buds and bulbs are used for both culinary and medicinal purposes in many parts of the world. L. longiflorum contains significant amounts of phenylpropanoid glycerol glucosides, a group of compounds that may contribute to plant pathogen defense, ultraviolet/high-intensity visible light (UV/high light) protection, and the purported medicinal uses of lilies. To define the natural distribution of these compounds within the plant, a liquid chromatography-mass spectrometry (LC-MS) method performed in selected ion monitoring (SIM) mode was employed for the quantitative analysis of five phenylpropanoid glycerol glucosides, namely, (2S)-1-O-caffeoyl-2-O-β-D-glucopyranosylglycerol, 1; (2R)-1-O-β-D-glucopyranosyl-2-O-p-coumaroylglycerol, 2; (2S)-1-O-p-coumaroyl-2-O-β-D-glucopyranosylglycerol, 3; (2S)-1-O-caffeoyl-2-O-β-D-glucopyranosyl-3-O-acetylglycerol, 4; and (2S)-1-O-p-coumaroyl-2-O-β-D-glucopyranosyl-3-O-acetylglycerol, 5, in the different organs of L. longiflorum. The p-coumaroyl-based 3 and its acetylated derivative 5 were determined to be the most abundant of the phenylpropanoid glycerol glucosides found in Easter lily bulbs, at 776.3 ± 8.4 and 650.7 ± 32.6 μg/g dry weight, respectively. The acetylated p-coumaroyl- and caffeoyl-based derivatives, 5 and 4, accumulated to the highest concentration in the closed flower buds, at 4925.2 ± 512.8 and 3216.8 ± 406.4 μg/g dry weight, respectively. Compound 4, followed by 5 and 1, proved to be the most abundant in the mature flowers, occurring at 6006.2 ± 625.8, 2160.3 ± 556.5, and 1535.8 ± 174.1 μg/g dry weight, respectively. Total concentrations of the phenylpropanoid glycerol glucosides were 10-100-fold higher in the above-ground plant organs as compared to the bulbs and fleshy roots. Two of the five compounds, 1 and 2, were identified in L. longiflorum for the first time. The quantitative

  13. LC/MS/MS determination and pharmacokinetic study of iridoid glycosides monotropein and deacetylasperulosidic acid isomers in rat plasma after oral administration of Morinda officinalis extract.

    PubMed

    Li, Chunmin; Dong, Jian; Tian, Jingchang; Deng, Zhipeng; Song, Xiujing

    2016-02-01

    Morinda officinalis is a famous traditional Chinese medicine containing iridoid glycoside compounds, such as monotropein and deacetylasperulosidic acid. The aim of the study was to develop a novel and sensitive liquid chromatography-tandem mass spectrometry (LC/MS/MS) method for the simultaneous determination of the two isomeric iridoid glycosides and then evaluate their pharmacokinetic properties in rats. Selected-reaction monitoring mode was employed for quantification of two analytes in rat plasma. The calibration curves were linear over their respective concentration range with correlation coefficient >0.995 for both analytes. Precision for monotropein and deacetylasperulosidic acid ranged from 2.5 to 11.9% relative standard deviation, and the accuracy of two analytes was -2.0-3.7 and -6.4-10.7% relative error, respectively. This method was successfully applied in pharmacokinetic study after oral administration of M. officinalis extract in rats. The results provided a basis for further research on the bioactivity of M. officinalis. PMID:26053360

  14. Isolation and purification of six iridoid glycosides from gardenia jasminoides fruit by medium-pressure liquid chromatography combined with macroporous resin chromatography.

    PubMed

    Wang, Yun; Liu, Hui; Shen, Lifeng; Yao, Lan; Ma, Yinlian; Yu, Dingrong; Chen, Jianhong; Li, Puling; Chen, Ying; Zhang, Cun

    2015-12-01

    Gardeniae fructus is one of the most frequently used herbs in traditional Chinese medicine. In the present study, a process for the enrichment of six iridoid glycosides from Gardeniae fructus was developed using medium-pressure liquid chromatography combined with macroporous resin and reversed-phase chromatography. The purities of different fractions from Gardeniae fructus were assessed using quantitative high-performance liquid chromatography. After fractionation using HPD-100 column chromatography, a 30% ethanol fraction was selected based on high-performance liquid chromatography and liquid chromatography with mass spectrometry qualitative analysis to separate and purify. Based on the orientation analysis results, six compounds-deacetyl asperulosidic acid methyl ester, gardenoside, ixoroside, scandoside methyl ester, genipin-1-O-β-d-gentiobioside, and geniposide-were successfully isolated and purified in three to four combined steps from Gardeniae fructus. The purities of these compounds were found by high-performance liquid chromatography analysis to be 97.9, 98.1, 95.5, 96.3, 97.1, and 98.7%, respectively. Moreover, their structures were elucidated by NMR spectroscopy and liquid chromatography with tandem mass spectrometry. The separation process was highly efficient, rapid, and accurate, making it a potential approach for the large-scale production of iridoids in the laboratory and providing several marker compounds for quality control. This procedure may be meaningful for the purification of other natural products used in traditional Chinese medicine. PMID:26768549

  15. Comprehensive two-dimensional liquid chromatography tandem diode array detector (DAD) and accurate mass QTOF-MS for the analysis of flavonoids and iridoid glycosides in Hedyotis diffusa.

    PubMed

    Li, Duxin; Schmitz, Oliver J

    2015-01-01

    The analysis of chemical constituents in Chinese herbal medicines (CHMs) is a challenge because of numerous compounds with various polarities and functional groups. Liquid chromatography coupled with quadrupole time-of-flight (QTOF) mass spectrometry (LC/MS) is of particular interest in the analysis of herbal components. One of the main attributes of QTOF that makes it an attractive analytical technique is its accurate mass measurement for both precursor and product ions. For the separation of CHMs, comprehensive two-dimensional chromatography (LCxLC) provides much higher resolving power than traditional one-dimensional separation. Therefore, a LCxLC-QTOF-MS system was developed and applied to the analysis of flavonoids and iridoid glycosides in aqueous extracts of Hedyotis diffusa (Rubiaceae). Shift gradient was applied in the two-dimensional separation in the LCxLC system to increase the orthogonality and effective peak distribution area of the analysis. Tentative identification of compounds was done by accurate mass interpretation and validation by UV spectrum. A clear classification of flavonol glycosides (FGs), acylated FGs, and iridoid glycosides (IGs) was shown in different regions of the LCxLC contour plot. In total, five FGs, four acylated FGs, and three IGs were tentatively identified. In addition, several novel flavonoids were found, which demonstrates that LCxLC-QTOF-MS detection also has great potential in herbal medicine analysis. PMID:25171829

  16. Chemical Synthesis of Deoxynivalenol-3-β-d-[(13)C₆]-glucoside and Application in Stable Isotope Dilution Assays.

    PubMed

    Habler, Katharina; Frank, Oliver; Rychlik, Michael

    2016-01-01

    Modified mycotoxins have been gaining importance in recent years and present a certain challenge in LC-MS/MS analysis. Due to the previous lack of a labeled isotopologue of the modified mycotoxin deoxynivalenol-3-glucoside, in our study we synthesized the first (13)C-labeled internal standard. Therefore, we used the Königs-Knorr method to synthesize deoxynivalenol-3-β-d-[(13)C₆]-glucoside originated from unlabeled deoxynivalenol and [(13)C₆]-labeled glucose. Using the synthesized isotopically-labeled standard deoxynivalenol-3-β-d-[(13)C₆]-glucoside and the purchased labeled standard [(13)C15]-deoxynivalenol, a stable isotope dilution LC-MS/MS method was firstly developed for deoxynivalenol-3-glucoside and deoxynivalenol in beer. The preparation and purification of beer samples was based on a solid phase extraction. The validation data of the newly developed method gave satisfying results. Intra- and interday precision studies revealed relative standard deviations below 0.5% and 7%, respectively. The recoveries ranged for both analytes between 97% and 112%. The stable isotope dilution assay was applied to various beer samples from four different countries. In summary, deoxynivalenol-3-glucoside and deoxynivalenol mostly appeared together in varying molar ratios but were quantified in rather low contents in the investigated beers. PMID:27355938

  17. Enzymatic synthesis of stable, odorless, and powdered furanone glucosides by sucrose phosphorylase.

    PubMed

    Kitao, S; Matsudo, T; Sasaki, T; Koga, T; Kawamura, M

    2000-01-01

    Sucrose phosphorylase from Leuconostoc mesenteroides catalyzed transglucosylation from sucrose to 4-hydroxy-3(2H)-furanone derivatives. When 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) and 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone or 5-ethyl-4-hydroxy-2-methyl-3(2H)-furanone (EHMF) were used as acceptors, their transfer ratios were more than 45%. In the case of glucosylation of HDMF, the major transfer product was identified as 2,5-dimethyl-3(2H)-furanone 4-O-alpha-D-glucopyranoside (DMF-G). In the case of glucosylation of EHMF, two major transfer products were obtained, and their structures were identified as 2-ethyl-5-methyl-3(2H)-furanone 4-O-alpha-D-glucopyranoside (2E5MF-G) and 5-ethyl-2-methyl-3(2H)-furanone 4-O-alpha-D-glucopyranoside (5E2MF-G) on the bases of spectrometric investigations. These glucosides were more stable than each aglycone. The glucosylated HDMF, DMF-G, was an odorless chemical, on the other hand, HDMF had a pineapple flavor. The glucosylated EHMF (EMF-G) were white odorless powders, though aglycone EHMF was a pale yellow syrup like a caramel with an intense sweet odor. Although DMF-G and EMF-G showed little radical-scavenging activity, hydrolyzates of these glucosides by an intestinal acetone powder from pigs had antioxidative activity as well as their aglycones. It was suggested that these glucosides improved some physical properties and may become prodrugs by glucosylation. PMID:10705458

  18. Antioxidant neolignan and phenolic glucosides from the fruit of Euterpe oleracea.

    PubMed

    Hu, Jian; Zhao, Jianping; Khan, Shabana I; Liu, Qiang; Liu, Yang; Ali, Zulfiqar; Li, Xing-Cong; Zhang, Shui-han; Cai, Xiong; Huang, Hui-yong; Wang, Wei; Khan, Ikhlas A

    2014-12-01

    Three new glucosides, namely, (-)-7R8S-7',8'-dihydroxy-dihydrodehydroconiferyl alcohol-9-O-β-D-glucopyranoside (1), (+)-7S8R-7',8'-dihydroxy-dihydrodehydroconiferyl alcohol-9-O-β-D-glucopyranoside (2) and 4-hydroxy-2-methoxyphenyl 1-O-[6-(hydrogen 3-hydroxy-3-methylpentanedioate)]-β-D-glucopyranoside (3), along with 6 known compounds were isolated from the fruit of Euterpe oleracea Mart. Their structures were elucidated based on spectroscopic analyses including NMR, HR-ESI-MS and CD. All the isolated compounds demonstrated significant antioxidant activity and 2 displayed moderate cytotoxicity against HL-60 cells. PMID:25284430

  19. A new indole alkaloidal glucoside from the aerial parts of Clematis terniflora DC.

    PubMed

    Li, Wen-Ting; Yang, Bing-Xian; Zhu, Wei; Gong, Ming-Hua; Xu, Xiang-Dong; Lu, Xiang-Hong; Sun, Lian-Li; Tian, Jing-Kui; Zhang, Lin

    2013-01-01

    A new indole alkaloidal glucoside together with three known compounds aurantiamide acetate (2), eleutheroside E (3) and 1-O-caffeoyl-β-D-glucopyranoside (4) has been isolated from ethanol extract of the aerial parts of Clematis terniflora DC. On the basis of their spectroscopic and chemical evidence, the new compound was elucidated as (6-O-β-D-glucopyranosyl-1H-indol-3-yl) carboxylic acid methyl ester (1). Compounds 1 and 3 showed significant cytotoxicity against human ECA-109. PMID:24050211

  20. On the masked mycotoxin zearalenone-14-glucoside. Does the mask truly hide?

    PubMed

    Dellafiora, Luca; Perotti, Alessio; Galaverna, Gianni; Buschini, Annamaria; Dall'Asta, Chiara

    2016-03-01

    In the matter of foodborne mycotoxins, beside a number of regulated compounds, regulations are totally missing for phase-II plant metabolites--the toxicological knowledge of which is still in its infancy. Currently, zearalenone-14-glucoside is in the pipeline and its toxicological role is under a glowing scientific debate. In our work it clearly showed high toxicological concerns as it is prone to conversion to well-known toxic compounds (i.e. zearalenone and both zearalenol isomers) when exposed to breast cancer cells culture. The need of future risk assessment studies has been pointed out accordingly. PMID:26792714

  1. Synthesis of 1,2-cis-2-C-branched aryl-C-glucosides via desulfurization of carbohydrate based hemithioacetals

    PubMed Central

    Mebrahtu, Fanuel M; Manana, Mandlenkosi M; Madumo, Kagiso; Sokamisa, Mokela S

    2015-01-01

    Summary 1-C and 2-C-branched carbohydrates are present as substructures in a number of biologically important compounds. Although the synthesis of such carbohydrate derivatives is extensively studied, the synthesis of 1,2-cis-2-C-branched C-, S-, and N-glycosides is less explored. In this article a synthetic strategy for the synthesis of 1,2-cis-2-C-branched-aryl-C-glucosides is reported via a hydrogenolytic desulfurization of suitably orientated carbohydrate based hemithioacetals. 1,2-cis-2-Hydroxymethyl and 2-carbaldehyde of aryl-C-glucosides have been synthesized using the current strategy in very good yields. The 2-carbaldehyde-aryl-C-glucosides have been identified as suitable substrates for the stereospecific preparation of 2,3-unsaturated-aryl-C-glycosides (Ferrier products). PMID:26124859

  2. Novel Indole-N-glucoside, TA-1887 As a Sodium Glucose Cotransporter 2 Inhibitor for Treatment of Type 2 Diabetes.

    PubMed

    Nomura, Sumihiro; Yamamoto, Yasuo; Matsumura, Yosuke; Ohba, Kiyomi; Sakamaki, Shigeki; Kimata, Hirotaka; Nakayama, Keiko; Kuriyama, Chiaki; Matsushita, Yasuaki; Ueta, Kiichiro; Tsuda-Tsukimoto, Minoru

    2014-01-01

    Inhibition of the renal sodium glucose cotransporter (SGLT) increases urinary glucose excretion (UGE) and thus reduces blood glucose levels during hyperglycemia. To explore the potential of new antihyperglycemic agents, we synthesized and determined the human SGLT2 (hSGLT2) inhibitory potential of novel substituted 3-benzylindole-N-glucosides 6. Optimization of 6 resulted in the discovery of 3-(4-cyclopropylbenzyl)-4-fluoroindole-N-glucoside 6a-4 (TA-1887), a highly potent and selective hSGLT2 inhibitor, with pronounced antihyperglycemic effects in high-fat diet-fed KK (HF-KK) mice. Our results suggest the potential of indole-N-glucosides as novel antihyperglycemic agents through inhibition of renal SGLT2. PMID:24900773

  3. In vitro digestion and lactase treatment influence uptake of quercetin and quercetin glucoside by the Caco-2 cell monolayer

    PubMed Central

    Boyer, Jeanelle; Brown, Dan; Liu, Rui Hai

    2005-01-01

    Background Quercetin and quercetin glycosides are widely consumed flavonoids found in many fruits and vegetables. These compounds have a wide range of potential health benefits, and understanding the bioavailability of flavonoids from foods is becoming increasingly important. Methods This study combined an in vitro digestion, a lactase treatment and the Caco-2 cell model to examine quercetin and quercetin glucoside uptake from shallot and apple homogenates. Results The in vitro digestion alone significantly decreased quercetin aglycone recovery from the shallot digestate (p < 0.05), but had no significant effect on quercetin-3-glucoside recovery (p > 0.05). Digestion increased the Caco-2 cell uptake of shallot quercetin-4'-glucoside by 2-fold when compared to the non-digested shallot. Despite the loss of quercetin from the digested shallot, the bioavailability of quercetin aglycone to the Caco-2 cells was the same in both the digested and non-digested shallot. Treatment with lactase increased quercetin recovery from the shallot digestate nearly 10-fold and decreased quercetin-4'-glucoside recovery by more than 100-fold (p < 0.05), but had no effect on quercetin recovery from apple digestates. Lactase treatment also increased shallot quercetin bioavailability to the Caco-2 cells approximately 14-fold, and decreased shallot quercetin-4'-glucoside bioavailability 23-fold (p < 0.05). These Caco-2 cells had lactase activity similar to that expressed by a lactose intolerant human. Conclusions The increase in quercetin uptake following treatment with lactase suggests that dietary supplementation with lactase may increase quercetin bioavailability in lactose intolerant humans. Combining the digestion, the lactase treatment and the Caco-2 cell culture model may provide a reliable in vitro model for examining flavonoid glucoside bioavailability from foods. PMID:15644141

  4. Effects on Liver Lipid Metabolism of the Naturally Occurring Dietary Flavone Luteolin-7-glucoside.

    PubMed

    Sá, Carla; Oliveira, Ana Rita; Machado, Cátia; Azevedo, Marisa; Pereira-Wilson, Cristina

    2015-01-01

    Disruptions in whole-body lipid metabolism can lead to the onset of several pathologies such as nonalcoholic fatty liver disease (NAFLD) and cardiovascular diseases (CVDs). The present study aimed at elucidating the molecular mechanisms behind the lipid-lowering effects of the flavone luteolin-7-glucoside (L7G) which we previously showed to improve plasma lipid profile in rats. L7G is abundant in plant foods of Mediterranean diet such as aromatic plants used as herbs. Results show that dietary supplementation with L7G for one week induced the expression of peroxisome proliferator-activated receptor-alpha (PPAR-α) and of its target gene carnitine palmitoyl transferase 1 (CPT-1) in rat liver. L7G showed a tendency to decrease the hepatic expression of sterol regulatory element-binding protein-1 (SREBP-1), without affecting fatty acid synthase (FAS) protein levels. Although SREBP-2 and LDLr mRNA levels did not change, the expression of HMG CoA reductase (HMGCR) was significantly repressed by L7G. L7G also inhibited this enzyme's in vitro activity in a dose dependent manner, but only at high and not physiologically relevant concentrations. These results add new evidence that the flavone luteolin-7-glucoside may help in preventing metabolic diseases and clarify the mechanisms underlying the beneficial health effects of diets rich in fruits and vegetables. PMID:26113868

  5. Development and Evaluation of Monoclonal Antibodies for the Glucoside of T-2 Toxin (T2-Glc)

    PubMed Central

    Maragos, Chris M.; Kurtzman, Cletus; Busman, Mark; Price, Neil; McCormick, Susan

    2013-01-01

    The interactions between fungi and plants can yield metabolites that are toxic in animal systems. Certain fungi are known to produce sesquiterpenoid trichothecenes, such as T-2 toxin, that are biotransformed by several mechanisms including glucosylation. The glucosylated forms have been found in grain and are of interest as potential reservoirs of T-2 toxin that are not detected by many analytical methods. Hence the glucosides of trichothecenes are often termed “masked” mycotoxins. The glucoside of T-2 toxin (T2-Glc) was linked to keyhole limpet hemocyanin and used to produce antibodies in mice. Ten monoclonal antibody (Mab)-producing hybridoma cell lines were developed. The Mabs were used in immunoassays to detect T2-Glc and T-2 toxin, with midpoints of inhibition curves (IC50s) in the low ng/mL range. Most of the Mabs demonstrated good cross-reactivity to T-2 toxin, with lower recognition of HT-2 toxin. One of the clones (2-13) was further characterized with in-depth cross-reactivity and solvent tolerance studies. Results suggest Mab 2-13 will be useful for the simultaneous detection of T-2 toxin and T2-Glc. PMID:23877196

  6. Unambiguous Determination of the Absolute Configuration of Dimeric Stilbene Glucosides from the Rhizomes of Gnetum africanum.

    PubMed

    Buffeteau, Thierry; Cavagnat, Dominique; Bisson, Jonathan; Marchal, Axel; Kapche, Gilbert D; Battistini, Ilaria; Da Costa, Gregory; Badoc, Alain; Monti, Jean-Pierre; Mérillon, Jean-Michel; Waffo-Téguo, Pierre

    2014-08-22

    Dimeric stilbene glucosides 1-3 [two diastereomers of (-)-gnemonoside A (1a and 1b), (-)-gnemonoside C (2), and (-)-gnemonoside D (3)] as well as a mixture of the two enantiomers of gnetin C (4) were isolated from the rhizomes of Gnetum africanum. The two enantiomers of gnetin C, (+)-4 and (-)-4, were obtained from the aglycones of 1a and 1b, respectively. The configurations of these stilbenoids were investigated by NMR and vibrational circular dichroism (VCD) experiments. The absolute configurations of (-)-1a, (-)-2, (-)-3, and (-)-4 were established as 7aS,8aS by VCD spectroscopy in combination with density functional theory calculations. The antiamyloidogenic activity of the isolated stilbenes was also evaluated versus beta-amyloid fibrils. The four glucosides of gnetin C (1a, 1b, 2, and 3) were found to be the most active compounds, with inhibition percentages of 56, 56, 58, and 54 at 10 μM, respectively. PMID:25093453

  7. Enhanced production of β-glucosides by in-situ UDP-glucose regeneration.

    PubMed

    Huang, Fong-Chin; Hinkelmann, Jens; Hermenau, Alexandra; Schwab, Wilfried

    2016-04-20

    Glycosyltransferase (GT)-mediated methodology is recognized as one of the most practical approaches for large-scale production of glycosides. However, GT enzymes require a sugar nucleotide as donor substrate that must be generated in situ for preparative applications by recycling of the nucleotide moiety, e.g. by sucrose synthase (SUS). Three plant GT genes CaUGT2, VvGT14a, and VvGT15c and the fungal SbUGTA1 were successfully co-expressed with GmSUS from soybean in Escherichia coli BL21 and W cells. In vitro, the crude protein extracts prepared from four GT genes and GmSUS co-expressing cells were able to convert several small molecules to the corresponding glucosides, when sucrose and UDP were supplied. In addition, GmSUS was able to enhance the glucosylation efficiency and reduced the amount of supplying UDP-glucose. In the biotransformation system, co-expression of VvGT15c with GmSUS also improved the glucosylation of geraniol and enhanced the resistance of the cells against the toxic terpenol. GT-EcW and GTSUS-EcW cells tolerated up to 2mM geraniol and converted more than 99% of the substrate into the glucoside at production rates exceeding 40μgml(-1)h(-1). The results confirm that co-expression of SUS allows in situ regeneration of UDP-sugars and avoids product inhibition by UDP. PMID:26912290

  8. Ultraperformance liquid chromatography tandem mass spectrometry determination of cyanogenic glucosides in Trifolium species.

    PubMed

    Muzashvili, Tamar; Moniuszko-Szajwaj, Barbara; Pecio, Lukasz; Oleszek, Wieslaw; Stochmal, Anna

    2014-02-26

    Cyanogenic glucosides were analyzed by ultra-high-performance liquid chromatography combined with mass spectrometry in 88 Trifolium species grown at the same site. On the basis of the occurrence of cyanogenic glucosides and the linamarin/lotaustralin ratio species could be grouped into five clusters. Cluster C1 included 37 species, which did not contain cyanogens. Cluster C2 (22 species) included plants containing only lotaustralin. In clusters C3 (14 species), C4 (13 species), and C5 (2 species) both linamarin and lotaustralin were present but at different ratios. In C3 and C4 the linamarin/lotaustralin ratio was below 1, whereas in cluster C5 the ratio was much higher. Generally, the total content of cyanogens was below 500 μg/g dry matter. Only in Trifolium repens var. biasoletti and Trifolium montanum extremely high cyanogen concentrations were observed. There was no general rule of occurrence of cyanogens. Samples of the same species from different countries accumulated cyanogens or could be free of these compounds. PMID:24476020

  9. Indoline Amide Glucosides from Portulaca oleracea: Isolation, Structure, and DPPH Radical Scavenging Activity.

    PubMed

    Jiao, Ze-Zhao; Yue, Su; Sun, Hong-Xiang; Jin, Tian-Yun; Wang, Hai-Na; Zhu, Rong-Xiu; Xiang, Lan

    2015-11-25

    A polyamide column chromatography method using an aqueous ammonia mobile phase was developed for large-scale accumulation of water-soluble indoline amide glucosides from a medicinal plant, Portulaca oleracea. Ten new [oleraceins H, I, K, L, N, O, P, Q, R, S (1-10)] and four known [oleraceins A-D (11-14)] indoline amide glucosides were further purified and structurally characterized by various chromatographic and spectroscopic methods. The DPPH radical scavenging activities of oleraceins K (5) and L (6), with EC50 values of 15.30 and 16.13 μM, respectively, were twice that of a natural antioxidant, vitamin C; the EC50 values of the 12 other indoline amides, which ranged from 29.05 to 43.52 μM, were similar to that of vitamin C. Structure-activity relationships indicated that the DPPH radical scavenging activities of these indoline amides correlate with the numbers and positions of the phenolic hydroxy groups. PMID:26562741

  10. Novel quercetin-3-O-glucoside eicosapentaenoic acid ester ameliorates inflammation and hyperlipidemia.

    PubMed

    Sekhon-Loodu, Satvir; Ziaullah, Ziaullah; Rupasinghe, H P Vasantha; Wang, Yanwen; Kulka, Marianna; Shahidi, Fereidoon

    2015-08-01

    Quercetin, a major flavonol, present abundantly in apples and onions, is widely studied for ameliorating metabolic syndrome abnormalities. However, quercetin is mainly present in plant food in the form of quercetin glycosides and has been reported for poor gastrointestinal absorption. The present study was designed with the purpose of imparting a lipophilic property to quercetin-3-O-glucoside (QG) by its acylation with eicosapentaenoic acid (EPA) and to study the influence of eicosapentaenoic acid ester of quercetin-3-O-glucoside (QE) on hyperlipidemia and inflammation in vivo and in vitro. QE was more effective in reducing the production of tumor necrosis factor-alpha (TNF-α), prostaglandin 2 (PGE2), cyclo-oxygenase (COX)-2 levels and nuclear expression of nuclear factor-kappa B (NF-кB) compared to the parent compounds (QG and EPA) and commercial drugs, after lipopolysaccharides (LPS) induced inflammation in THP-1 derived macrophages. Serum high-density lipoprotein (HDL)-cholesterol was significantly higher and hepatic total cholesterol concentration was lower in the rats fed high-fat diet supplemented with QE, compared to the high-fat diet with inflammation (HFL). The serum concentrations of C-reactive protein (CRP), interleukin (IL)-6, and interferon-gamma (IFN-γ) were significantly lower in QE treatment group than HFL group. EPA conjugated flavonol, QE, had significant anti-inflammatory and hypolipidemic properties and may be effective for the treatment of obesity-related disorders. PMID:26165697

  11. Isoarnottinin 4'-glucoside, a glycosylated coumarin from Prangos uloptera, with biological activity.

    PubMed

    Razavi, Seyed Mehdi; Zarrini, Gholamreza; Rad, Farah Gholami

    2011-01-01

    Coumarins are a well-known group of natural products distributed in the plant kingdom especially in the family Apiaceae with various biological activities. Isoarnottinin 4'-glucoside is a simple glycosylated coumarin found previously in a few genera of Apiaceae, and its biological activities have not been previously described in details. In the present paper, the compound was isolated from Prangos uloptera (Apiaceae) leaves using HPLC techniques. Antimicrobial, phytotoxic and cytotoxic activities of the compound were evaluated by disk diffusion, lettuce assay and MTT method. Our results indicated that the compound has high antibacterial effect against Erwinia carotovora, a common plant pathogen with MIC value of 100 microg/mL. The compound also exhibited significant phytotoxic activity against lettuce and modest cytotoxic activity against HeLa cell line with IC50 of 0 .84 mg/mL. It could be concluded that isoamottinin 4'-glucoside may play phytoalexin or allelopathic role for plant and may be a candidate for an antibacterial agent or a bioherbicide. PMID:21717896

  12. Engineering of glucoside acceptors for the regioselective synthesis of beta-(1-->3)-disaccharides with glycosynthases.

    PubMed

    Marton, Zsuzanna; Tran, Vinh; Tellier, Charles; Dion, Michel; Drone, Jullien; Rabiller, Claude

    2008-11-24

    Glycosynthase mutants obtained from Thermotogamaritima were able to catalyze the regioselective synthesis of aryl beta-D-Galp-(1-->3)-beta-D-Glcp and aryl beta-D-Glcp-(1-->3)-beta-D-Glcp in high yields (up to 90 %) using aryl beta-D-glucosides as acceptors. The need for an aglyconic aryl group was rationalized by molecular modeling calculations, which have emphasized a high stabilizing interaction of this group by stacking with W312 of the enzyme. Unfortunately, the deprotection of the aromatic group of the disaccharides was not possible without partial hydrolysis of the glycosidic bond. The replacement of aryl groups by benzyl ones could offer the opportunity to deprotect the anomeric position under very mild conditions. Assuming that benzyl acceptors could preserve the stabilizing stacking, benzyl beta-d-glucoside firstly assayed as acceptor resulted in both poor yields and poor regioselectivity. Thus, we decided to undertake molecular modeling calculations in order to design which suitable substituted benzyl acceptors could be used. This study resulted in the choice of 2-biphenylmethyl beta-D-glucopyranoside. This choice was validated experimentally, since the corresponding beta-(1-->3) disaccharide was obtained in good yields and with a high regioselectivity. At the same time, we have shown that phenyl 1-thio-beta-D-glucopyranoside was also an excellent substrate leading to similar results as those obtained with the O-phenyl analogue. The NBS deprotection of the S-phenyl group afforded the corresponding disaccharide quantitatively. PMID:18828996

  13. Evolution of aromatic β-glucoside utilization by successive mutational steps in Escherichia coli.

    PubMed

    Zangoui, Parisa; Vashishtha, Kartika; Mahadevan, Subramony

    2015-02-15

    The bglA gene of Escherichia coli encodes phospho-β-glucosidase A capable of hydrolyzing the plant-derived aromatic β-glucoside arbutin. We report that the sequential accumulation of mutations in bglA can confer the ability to hydrolyze the related aromatic β-glucosides esculin and salicin in two steps. In the first step, esculin hydrolysis is achieved through the acquisition of a four-nucleotide insertion within the promoter of the bglA gene, resulting in enhanced steady-state levels of the bglA transcript. In the second step, hydrolysis of salicin is achieved through the acquisition of a point mutation within the bglA structural gene close to the active site without the loss of the original catabolic activity against arbutin. These studies underscore the ability of microorganisms to evolve additional metabolic capabilities by mutational modification of preexisting genetic systems under selection pressure, thereby expanding their repertoire of utilizable substrates. PMID:25448815

  14. Effects on Liver Lipid Metabolism of the Naturally Occurring Dietary Flavone Luteolin-7-glucoside

    PubMed Central

    Sá, Carla; Oliveira, Ana Rita; Machado, Cátia; Azevedo, Marisa; Pereira-Wilson, Cristina

    2015-01-01

    Disruptions in whole-body lipid metabolism can lead to the onset of several pathologies such as nonalcoholic fatty liver disease (NAFLD) and cardiovascular diseases (CVDs). The present study aimed at elucidating the molecular mechanisms behind the lipid-lowering effects of the flavone luteolin-7-glucoside (L7G) which we previously showed to improve plasma lipid profile in rats. L7G is abundant in plant foods of Mediterranean diet such as aromatic plants used as herbs. Results show that dietary supplementation with L7G for one week induced the expression of peroxisome proliferator-activated receptor-alpha (PPAR-α) and of its target gene carnitine palmitoyl transferase 1 (CPT-1) in rat liver. L7G showed a tendency to decrease the hepatic expression of sterol regulatory element-binding protein-1 (SREBP-1), without affecting fatty acid synthase (FAS) protein levels. Although SREBP-2 and LDLr mRNA levels did not change, the expression of HMG CoA reductase (HMGCR) was significantly repressed by L7G. L7G also inhibited this enzyme's in vitro activity in a dose dependent manner, but only at high and not physiologically relevant concentrations. These results add new evidence that the flavone luteolin-7-glucoside may help in preventing metabolic diseases and clarify the mechanisms underlying the beneficial health effects of diets rich in fruits and vegetables. PMID:26113868

  15. Phytochemistry, micromorphology and bioactivities of Ajuga chamaepitys (L.) Schreb. (Lamiaceae, Ajugoideae): Two new harpagide derivatives and an unusual iridoid glycosides pattern.

    PubMed

    Venditti, A; Frezza, C; Maggi, F; Lupidi, G; Bramucci, M; Quassinti, L; Giuliani, C; Cianfaglione, K; Papa, F; Serafini, M; Bianco, A

    2016-09-01

    Ajuga chamaepitys (L.) Schreb, well-known as Camaepitium or Ground Pine, is an annual herb typical of the Mediterranean area accounting several uses in the traditional medicine. In this work we have, analyzed the plant iridoid fraction together with the essential oil composition and study of the plant indumentum. Finally, we assayed the polar extracts and essential oil obtained from the aerial parts for antioxidant activity and cytotoxicity on tumor cells. The analysis of the monoterpene glycosides allowed us to isolate from roots and aerial parts and to structurally elucidate by NMR and MS the following compounds: ajugoside (1), reptoside (2), 8-O-acetylharpagide (3), harpagide (4), 5-O-β-d-glucopyranosyl-harpagide (5), asperulosidic acid (6), deacetyl asperulosidic acid (7) and 5-O-β-d-glucopyranosyl-8-O-acetylharpagide (8), among which 5 and 8 were two new natural products. Chemotaxomic relevance of these constituents was discussed. The chemical analysis of A. chamaepitys essential oil by GC-FID and GC-MS showed ethyl linoleate (13.7%), germacrene D (13.4%), kaurene (8.4%), β-pinene (6.8%), and (E)-phytol (5.3%) as the major volatile components. The micromorphological and histochemical study showed that iridoids and essential oil are mainly produced in the type III capitates and peltate trichomes of leaves and flowers. Biological evaluations of A. chamaepitys polar extracts and essential oil showed that the former were more potent as radical scavengers than the latter. MTT assay revealed that essential oil and ethanolic extracts were moderately cytotoxic on tumor cells with IC50 of 36.88 and 59.24μg/mL on MDA-MB 231 cell line, respectively, and IC50 of 60.48 and 64.12μg/mL on HCT116, respectively. PMID:27373875

  16. Flavonoid C-glucosides Derived from Flax Straw Extracts Reduce Human Breast Cancer Cell Growth In vitro and Induce Apoptosis

    PubMed Central

    Czemplik, Magdalena; Mierziak, Justyna; Szopa, Jan; Kulma, Anna

    2016-01-01

    Flax straw of flax varieties that are grown for oil production is a by product which represents a considerable biomass source. Therefore, its potential application for human use is of high interest. Our research has revealed that flax straw is rich in flavonoid C-glucosides, including vitexin, orientin, and isoorientin. The objective of this study was to evaluate the cytotoxicity and possible proapoptotic effect of flax straw derived C-glucosides of flavonoids in the human breast adenocarcinoma cell line (MCF-7). The effects of flax straw derived flavonoid C-glucosides on cell proliferation of MCF-7 cells were evaluated by 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl-tetrazolium bromide (MTT) and sulforhodamine B assays. The expression of apoptosis-related genes was assessed by real-time PCR. Our data revealed that flax C-glucosides as well as pure compounds are cytotoxic toward MCF-7 cells and inhibit their proliferation. Moreover, the induction of apoptosis was correlated with the changes in the mRNA level of pro-apoptotic genes. Increased expression of bax and caspase-7, -8, and -9 and decreased mRNA expression of bcl-2 was observed, whereas the mRNA levels of p53 and mdm2 were not altered. These results clearly demonstrated that flax straw metabolites effectively induced growth inhibition and apoptosis in human breast adenocarcinoma cells.

  17. A family 3 glycosyl hydrolase of Dickeya dadantii 3937 is involved in the cleavage of aromatic glucosides.

    PubMed

    Charaoui-Boukerzaza, Sana; Hugouvieux-Cotte-Pattat, Nicole

    2013-11-01

    Dickeya dadantii is a phytopathogenic bacterium secreting a large array of plant-cell-wall-degrading enzymes that participate in the infection and maceration of the host plant tissue. Sequencing of the D. dadantii 3937 genome predicted several genes encoding potential glycosidases. One of these genes, bgxA, encodes a protein classified in family 3 of glycosyl hydrolases. Inactivation of bgxA and the use of a gene fusion revealed that this gene is not essential for D. dadantii pathogenicity but that it is expressed during plant infection. The bgxA expression is induced in the presence of glycosidic or non-glycosidic aromatic compounds, notably ferulic acid, cinnamic acid, vanillic acid and salicin. The BgxA enzyme has a principal β-d-glucopyranosidase activity and a secondary β-d-xylopyranosidase activity (ratio 70 : 1). This enzyme activity is inhibited by different aromatic glycosides or phenolic compounds, in particular salicin, arbutin, ferulic acid and vanillic acid. Together, the induction effects and the enzyme inhibition suggest that BgxA is mostly involved in the cleavage of aromatic β-glucosides. There is evidence of functional redundancy in the D. dadantii β-glucoside assimilation pathway. In contrast to other β-glucoside assimilation systems, involving cytoplasmic phospho-β-glucosidases, the cleavage of aromatic glucosides in the periplasmic space by BgxA may avoid the release of a toxic phenolic aglycone into the cytoplasm while still allowing for catabolism of the glucose moiety. PMID:24002750

  18. Synthesis and biological evaluation of novel dioxa-bicycle C-aryl glucosides as SGLT2 inhibitors.

    PubMed

    Yan, Qi; Ding, Ning; Li, Yingxia

    2016-02-01

    A series of novel C-aryl glucosides containing dioxa-bicycle were synthesized and evaluated for inhibition activity against hSGLT2. Among the compounds tested, compound 6a showed moderate SGLT2 inhibition activities at 700 nM. The results could benefit the discovery of new SGLT2 inhibitors. PMID:26735747

  19. A UDP-glucosyltransferase functions in both acylphloroglucinol glucoside and anthocyanin biosynthesis in strawberry (Fragaria × ananassa).

    PubMed

    Song, Chuankui; Zhao, Shuai; Hong, Xiaotong; Liu, Jingyi; Schulenburg, Katja; Schwab, Wilfried

    2016-03-01

    Physiologically active acylphloroglucinol (APG) glucosides were recently found in strawberry (Fragaria sp.) fruit. Although the formation of the APG aglycones has been clarified, little is known about APG glycosylation in plants. In this study we functionally characterized ripening-related glucosyltransferase genes in Fragaria by comprehensive biochemical analyses of the encoded proteins and by a RNA interference (RNAi) approach in vivo. The allelic proteins UGT71K3a/b catalyzed the glucosylation of diverse hydroxycoumarins, naphthols and flavonoids as well as phloroglucinols, enzymatically synthesized APG aglycones and pelargonidin. Total enzymatic synthesis of APG glucosides was achieved by co-incubation of recombinant dual functional chalcone/valerophenone synthase and UGT71K3 proteins with essential coenzyme A esters and UDP-glucose. An APG glucoside was identified in strawberry fruit which has not yet been reported in other plants. Suppression of UGT71K3 activity in transient RNAi-silenced fruits led to a loss of pigmentation and a substantial decrease of the levels of various APG glucosides and an anthocyanin. Metabolite analyses of transgenic fruits confirmed UGT71K3 as a UDP-glucose:APG glucosyltransferase in planta. These results provide the foundation for the breeding of fruits with improved health benefits and for the biotechnological production of bioactive natural products. PMID:26859691

  20. In vitro anti-HIV-1 activities of kaempferol and kaempferol-7-O-glucoside isolated from Securigera securidaca

    PubMed Central

    Behbahani, M.; Sayedipour, S.; Pourazar, A.; Shanehsazzadeh, M.

    2014-01-01

    Previously, we reported that the kaempferol and kaempferol-7-O-glucoside isolated from Securigera securidaca showed potent anti-HSV activity. In the present study the anti-HIV-1 activities of kaempferol and kaempferol-7-O-glucoside are investigated at different concentrations (100, 50, 25 and 10 μg/ml) using HIV-1 p24 Antigen kit. Real-time Polymerase chain reaction (RT-PCR) assay was also used for quantification of full range of virus load observed in treated and untreated cells. According to the results of RT- PCR, tested compounds at a concentration of 100 μg/ml exerted potent inhibitory effect. Time of drug addition experiments demonstrated that these compounds exerted their inhibitory effects on the early stage of HIV infection. The results also showed potent anti-HIV-1 reverse transcriptase activity. Antiviral activity of kaempferol-7-O-glucoside was more pronounced than that of kaempferol. These findings demonstrate that kaempferol-7-O-glucoside could be considered as a new potential drug candidate for the treatment of HIV infection which requires further assessments. PMID:26339261

  1. In vitro anti-HIV-1 activities of kaempferol and kaempferol-7-O-glucoside isolated from Securigera securidaca.

    PubMed

    Behbahani, M; Sayedipour, S; Pourazar, A; Shanehsazzadeh, M

    2014-01-01

    Previously, we reported that the kaempferol and kaempferol-7-O-glucoside isolated from Securigera securidaca showed potent anti-HSV activity. In the present study the anti-HIV-1 activities of kaempferol and kaempferol-7-O-glucoside are investigated at different concentrations (100, 50, 25 and 10 μg/ml) using HIV-1 p24 Antigen kit. Real-time Polymerase chain reaction (RT-PCR) assay was also used for quantification of full range of virus load observed in treated and untreated cells. According to the results of RT- PCR, tested compounds at a concentration of 100 μg/ml exerted potent inhibitory effect. Time of drug addition experiments demonstrated that these compounds exerted their inhibitory effects on the early stage of HIV infection. The results also showed potent anti-HIV-1 reverse transcriptase activity. Antiviral activity of kaempferol-7-O-glucoside was more pronounced than that of kaempferol. These findings demonstrate that kaempferol-7-O-glucoside could be considered as a new potential drug candidate for the treatment of HIV infection which requires further assessments. PMID:26339261

  2. Clarification of Reconstituted Frozen Orange Juice Concentrate by Continuous Flow Centrifugation for Limonin Glucoside Solid Phase Extraction

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The clarification of reconstituted frozen orange juice concentrate by continuous-flow centrifugation in preparation to being applied to a solid phase extraction column for the isolation of limonin glucoside has been evaluated. Clarification experiments spanning over three different flow rates (325,...

  3. Chemical constituents of Chinese natural medicine, morindae radix, the dried roots of morinda officinalis how.: structures of morindolide and morofficinaloside.

    PubMed

    Yoshikawa, M; Yamaguchi, S; Nishisaka, H; Yamahara, J; Murakami, N

    1995-09-01

    A new iridoid lactone, morindolide, and a new iridoid glucoside, morofficinaloside, have been isolated from a Chinese natural medicine, Morindae Radix, the dried root of Morinda officinalis How. together with a number of known compounds: five anthraquinones, four iridoid glucosides, a monoterpene glycoside, two sterols, an ursane-type triterpene, and a lactone compound. The chemical structures of the new compounds were determined on the basis of chemical and physicochemical evidence. PMID:7586069

  4. Protective effects of cyanidin-3-O-glucoside from blackberry extract against peroxynitrite-induced endothelial dysfunction and vascular failure.

    PubMed

    Serraino, Ivana; Dugo, Laura; Dugo, Paola; Mondello, Luigi; Mazzon, Emanuela; Dugo, Giovanni; Caputi, Achille Patrizio; Cuzzocrea, Salvatore

    2003-07-18

    Anthocyanins are a group of naturally occurring phenolic compounds as colorants in several plants, flowers and fruits. These pigments have a great importance as quality indicators, as chemotaxonomic markers and antioxidants. The content of blackberry (Rubus species) juice was investigated by HPLC/ESI/MS using narrow bore HPLC columns. Using this method we demonstrated that cyanidin-3-O-glucoside represents about 80% of the total anthocyanin contents in blackberry extract. Here we investigated antioxidant activity of the blackberry juice and cyanidin-3-O-glucoside on the endothelial dysfunction in cells and in vascular rings exposed to peroxynitrite. In human umbilical vein endothelial cells (HUVEC) in vitro, peroxynitrite caused a significant suppression of mitochondrial respiration (38 +/- 2.1% of control cells), as measured by the mitochondrial-dependent conversion of the dye MTT to formazan. Peroxynitrite caused DNA strand breakage (63 +/- 1.9% single strand vs 3 +/- 0.9% single strand in control cells), as measured by the alkaline unwinding assay, and caused an activation of PARS, as measured by the incorporation of radiolabeled NAD(+) to nuclear proteins. Blackberry juice (different dilutions that contained 80 ppm;40 ppm;14.5 ppm of cyanidin-3-O-glucoside) and cyanidin-3-O-glucoside (as chloride) (0.085 microM; 0.028 microM; 0.0085 microM) reduced the peroxynitrite-induced suppression of mitochondrial respiration, DNA damage and PARS activation in HUVECs. Vascular rings exposed to peroxynitrite exhibited reduced endothelium-dependent relaxant responses in response to acetylcholine as well as a vascular contractility dysfunction in response to norepinephrine. The development of this peroxynitrite-induced vascular dysfunction was ameliorated by the blackberry juice (different dilutions that contained 80 ppm;40 ppm;14.5 ppm of cyanidin-3-O-glucoside) and cyanidin-3-O-glucoside (as chloride) (0.085 microM;0.028 microM;0.0085 microM). In conclusion our findings

  5. Helicobacter pylori Cholesteryl α-Glucosides Contribute to Its Pathogenicity and Immune Response by Natural Killer T Cells

    PubMed Central

    Ito, Yuki; Vela, Jose Luis; Matsumura, Fumiko; Hoshino, Hitomi; Tyznik, Aaron; Lee, Heeseob; Girardi, Enrico; Zajonc, Dirk M.; Liddington, Robert; Kobayashi, Motohiro; Bao, Xingfeng; Bugaytsova, Jeanna; Borén, Thomas; Jin, Rongsheng; Zong, Yinong; Seeberger, Peter H.; Nakayama, Jun; Kronenberg, Mitchell; Fukuda, Minoru

    2013-01-01

    Approximately 10–15% of individuals infected with Helicobacter pylori will develop ulcer disease (gastric or duodenal ulcer), while most people infected with H. pylori will be asymptomatic. The majority of infected individuals remain asymptomatic partly due to the inhibition of synthesis of cholesteryl α-glucosides in H. pylori cell wall by α1,4-GlcNAc-capped mucin O-glycans, which are expressed in the deeper portion of gastric mucosa. However, it has not been determined how cholesteryl α-glucosyltransferase (αCgT), which forms cholesteryl α-glucosides, functions in the pathogenesis of H. pylori infection. Here, we show that the activity of αCgT from H. pylori clinical isolates is highly correlated with the degree of gastric atrophy. We investigated the role of cholesteryl α-glucosides in various aspects of the immune response. Phagocytosis and activation of dendritic cells were observed at similar degrees in the presence of wild-type H. pylori or variants harboring mutant forms of αCgT showing a range of enzymatic activity. However, cholesteryl α-glucosides were recognized by invariant natural killer T (iNKT) cells, eliciting an immune response in vitro and in vivo. Following inoculation of H. pylori harboring highly active αCgT into iNKT cell-deficient (Jα18−/−) or wild-type mice, bacterial recovery significantly increased in Jα18−/− compared to wild-type mice. Moreover, cytokine production characteristic of Th1 and Th2 cells dramatically decreased in Jα18−/− compared to wild-type mice. These findings demonstrate that cholesteryl α-glucosides play critical roles in H. pylori-mediated gastric inflammation and precancerous atrophic gastritis. PMID:24312443

  6. Potential applications of glucosyltransferases in terpene glucoside production: impacts on the use of aroma and fragrance.

    PubMed

    Schwab, Wilfried; Fischer, Thilo C; Giri, Ashok; Wüst, Matthias

    2015-01-01

    The detection of glucoconjugated forms of monoterpene alcohols in rose petals in the late 1960s opened the new field of nonvolatile aroma precursors in flavor research. It is now well established that odorless glycosides represent a significant pool of aroma precursors in plants where they act as preformed but inactivated defense or attractive chemicals. Technical improvements in the separation and identification of plant secondary metabolites have provided a multitude of chemical structures, but functional characterization of glycosyltransferases that catalyze their formation lags behind. As technical efforts and costs for DNA sequencing dramatically dropped during the last decade, the number of plant genome sequences increased significantly, thus providing opportunities to functionally characterize the glycosyltransferase gene families in plants. These studies yielded the first glycosyltransferase genes that encode efficient biocatalysts for the production of monoterpene glucosides. They have applications in the food, feed, chemical, cosmetic, and pharmaceutical industries as slow release aroma chemicals. PMID:25431013

  7. Mozambioside Is an Arabica-Specific Bitter-Tasting Furokaurane Glucoside in Coffee Beans.

    PubMed

    Lang, Roman; Klade, Stefan; Beusch, Anja; Dunkel, Andreas; Hofmann, Thomas

    2015-12-01

    Sensory-guided fractionation of a roasted coffee beverage revealed a highly polar, bitter-tasting subfraction, from which the furokaurane glucoside mozambioside was isolated and identified in its chemical structure by means of HDMS and NMR spectra. Sensory evaluation revealed a bitter taste recognition threshold of 60 (± 10) μmol/L. UPLC-HDMS quantitation of raw coffee beans showed that Arabica coffees contained 396-1188 nmol/g mozambioside, whereas only traces (<5 nmol/g) were detected in Robusta coffees, thus suggesting that mozambioside can be used as an analytical marker for Arabica coffee. Roasted Arabica contained a substantially reduced concentration (232 ± 37 nmol/g), indicating partial degradation of mozambioside during coffee roasting. Mozambioside was nearly quantitatively extracted into the aqueous brew during coffee-making (86-98%). PMID:26585544

  8. Decyl glucoside as a corrosion inhibitor for magnesium-air battery

    NASA Astrophysics Data System (ADS)

    Deyab, M. A.

    2016-09-01

    In this research, the effects of decyl glucoside (DG) on the corrosion inhibition and battery performance of Mg-air battery have been investigated. Chemical and electrochemical techniques have been used to evaluate the corrosion rate and inhibitor efficiency. Mg surface has been characterized with scanning electron microscopy (SEM) and infrared spectroscopy (FTIR). A significant reduction in the corrosion rate of Mg in battery electrolyte (3.5% NaCl solution) has been observed in the presence of DG surfactant. Maximum inhibition efficiency (>94%) is achieved at critical micelle concentration of DG surfactant (CMC = 2.5 mM). The presence of DG surfactant increases the activation energy of the corrosion reaction. Physisorption mechanism has been suggested for the inhibition action of DG surfactant. The Mg-air battery containing DG surfactant offers higher operating voltage, discharge capacity and anodic utilization than in its absence.

  9. Occurrence of Deoxynivalenol and Deoxynivalenol-3-glucoside in Hard Red Spring Wheat Grown in the USA

    PubMed Central

    Simsek, Senay; Ovando-Martínez, Maribel; Ozsisli, Bahri; Whitney, Kristin; Ohm, Jae-Bom

    2013-01-01

    Deoxynivalenol (DON) is a mycotoxin found in wheat that is infected with Fusarium fungus. DON may also be converted to a type of “masked mycotoxin”, named deoxynivalenol-3-glucoside (D3G), as a result of detoxification of the plant. In this study, DON and D3G were measured using gas chromatographic (GC) and liquid chromatography-mass spectrometry (LC-MS) in wheat samples collected during 2011 and 2012 in the USA. Results indicate that the growing region had a significant effect on the DON and D3G (p < 0.0001). There was a positive correlation between both methods (GC and LC-MS) used for determination of DON content. DON showed a significant and positive correlation with D3G during 2011. Overall, DON production had an effect on D3G content and kernel damage, and was dependent on environmental conditions during Fusarium infection. PMID:24351720

  10. Polycyclic polyprenylated acylphloroglucinols and chromone O-glucosides from Hypericum henryi subsp. uraloides.

    PubMed

    Chen, Xuan-Qin; Li, Yan; Cheng, Xiao; Wang, Kou; He, Juan; Pan, Zheng-Hong; Li, Ming-Ming; Peng, Li-Yan; Xu, Gang; Zhao, Qin-Shi

    2010-01-01

    Two new C(30)-epimeric polycyclic polyprenylated acylphloroglucinols (PPAPs), named uralodins B and C (1 and 2, resp.), were isolated from the aerial parts of Hypericum henryi subsp. uraloides together with two new chromone glucosides, urachromones A and B (3 and 4, resp.), as well as 16 known compounds. Their structures were established by extensive NMR techniques and MS analysis. The epimers 1 and 2 always behaved like a single compound when examined by TLC, and were separated by HPLC. Their configuration was distinguished by comparative analysis of the NMR data with known analogues together with the ROESY experiment. All the isolated PPAPs were evaluated for their cytotoxic activities against HepG2, SGC7901, HL-60, and K562 cell lines. Compound 1 showed modest cytotoxic activities against SGC7901 and HL-60 cell lines, and 2 showed modest cytotoxic activities against HepG2, SGC7901, HL-60, and K562 cell lines. PMID:20087990

  11. Three spirostanol saponins and a flavane-O-glucoside from the fresh rhizomes of Tupistra chinensis.

    PubMed

    Xiao, Yan-Hua; Yin, Hai-Long; Chen, Li; Tian, Yin; Liu, Shi-Jun; Zhang, Guang-Jie; Chen, Heng-Wen; Jin, Hong; Li, Bin; Dong, Jun-Xing

    2015-04-01

    Four new compounds, including three new spirostanol saponins [tupistroside G-I (1-3)] and a new flavane-O-glucoside [tupichiside A (4)], together with ten known compounds, were isolated from the fresh rhizomes of Tupistra chinensis. The structures of the new compounds were elucidated by spectroscopic analysis and chemical evidence. All compounds were tested in vitro for their cytotoxic activities against the Human LoVo and BGC-823 cell lines, and six of them were found to possess potent cytotoxicity. Compounds 2, 8 and 9 showed significant cytotoxicity against the tested tumor cell lines with IC50 values ranging from 0.2 to 0.9μM. PMID:25707589

  12. Stability studies of ascorbic acid 2-glucoside in cosmetic lotion using surface response methodology.

    PubMed

    Huang, Wen-Ying; Lee, Pei-Chi; Huang, Ling-Kuei; Lu, Li-Ping; Liao, Wayne C

    2013-03-15

    Ascorbic acid 2-glucoside (AA-2G) has been widely used in cream and lotion types of cosmetic products. Thus, the degradation of AA-2G caused by the temperature change and pH variation was very critical for determining the bio-functionality of cosmetics. Response surface methodology (RSM) was introduced to study the influence of temperature and pH on the stability of AA-2G. The optimal condition of retaining AA-2G with the highest stability was determined to be 55.3°C and pH 6.4. The antioxidative activities of AA-2G including DPPH and ABTS free radical scavenging activities, metal chelating activity, and reducing ability were also determined. AA-2G was a good ascorbic acid derivative which could be used in cosmetic products as an active ingredient. PMID:23416010

  13. Molecular cloning and characterization of genistein 4'-O-glucoside specific glycosyltransferase from Bacopa monniera.

    PubMed

    Ruby; Santosh Kumar, R J; Vishwakarma, Rishi K; Singh, Somesh; Khan, Bashir M

    2014-07-01

    Health related benefits of isoflavones such as genistein are well known. Glycosylation of genistein yields different glycosides like genistein 7-O-glycoside (genistin) and genistein 4'-O-glycoside (sophoricoside). This is the first report on isolation, cloning and functional characterization of a glycosyltransferase specific for genistein 4'-O-glucoside from Bacopa monniera, an important Indian medicinal herb. The glycosyltransferase from B. monniera (UGT74W1) showed 49% identity at amino acid level with the glycosyltransferases from Lycium barbarum. The UGT74W1 sequence contained all the conserved motifs present in plant glycosyltransferases. UGT74W1 was cloned in pET-30b (+) expression vector and transformed into E. coli. The molecular mass of over expressed protein was found to be around 52 kDa. Functional characterization of the enzyme was performed using different substrates. Product analysis was done using LC-MS and HPLC, which confirmed its specificity for genistein 4'-O-glucoside. Immuno-localization studies of the UGT74W1 showed its localization in the vascular bundle. Spatio-temporal expression studies under normal and stressed conditions were also performed. The control B. monniera plant showed maximum expression of UGT74W1 in leaves followed by roots and stem. Salicylic acid treatment causes almost tenfold increase in UGT74W1 expression in roots, while leaves and stem showed decrease in expression. Since salicylic acid is generated at the time of injury or wound caused by pathogens, this increase in UGT74W1 expression under salicylic acid stress might point towards its role in defense mechanism. PMID:24664316

  14. Metabolism of Monoterpenes : Early Steps in the Metabolism of d-Neomenthyl-beta-d-Glucoside in Peppermint (Mentha piperita) Rhizomes.

    PubMed

    Croteau, R; Sood, V K; Renstrøm, B; Bhushan, R

    1984-11-01

    Previous studies have shown that the monoterpene ketone l-[G-(3)H] menthone is reduced to the epimeric alcohols l-menthol and d-neomenthol in leaves of flowering peppermint (Mentha piperita L.), and that a portion of the menthol is converted to menthyl acetate while the bulk of the neomenthol is transformed to neomenthyl-beta-d-glucoside which is then transported to the rhizome (Croteau, Martinkus 1979 Plant Physiol 64: 169-175). Analysis of the disposition of l-[G-(3)H]menthone applied to midstem leaves of intact flowering plants allowed the kinetics of synthesis and transport of the monoterpenyl glucoside to be determined, and gave strong indication that the glucoside was subsequently metabolized in the rhizome. Studies with d-[G-(3)H]neomenthyl-beta-d-glucoside as substrate, using excised rhizomes or rhizome segments, confirmed the hydrolysis of the glucoside as an early step in metabolism at this site, and revealed that the terpenoid moiety was further converted to a series of ether-soluble, methanol-soluble, and water-soluble products. Studies with d-[G-(3)H]neomenthol as the substrate, using excised rhizomes, showed the subsequent metabolic steps to involve oxidation of the alcohol back to menthone, followed by an unusual lactonization reaction in which oxygen is inserted between the carbonyl carbon and the carbon bearing the isopropyl group, to afford 3,4-menthone lactone. The conversion of menthone to the lactone, and of the lactone to more polar products, were confirmed in vivo using l-[G-(3)H]menthone and l-[G-(3)H]-3,4-menthone lactone as substrates. Additional oxidation products were formed in vivo via the desaturation of labeled neomenthol and/or menthone, but none of these transformations appeared to lead to ring opening of the p-menthane skeleton. Each step in the main reaction sequence, from hydrolysis of neomenthyl glucoside to lactonization of menthone, was demonstrated in cell-free extracts from the rhizomes of flowering mint plants. The

  15. The Metabolic Fate of Deoxynivalenol and Its Acetylated Derivatives in a Wheat Suspension Culture: Identification and Detection of DON-15-O-Glucoside, 15-Acetyl-DON-3-O-Glucoside and 15-Acetyl-DON-3-Sulfate.

    PubMed

    Schmeitzl, Clemens; Warth, Benedikt; Fruhmann, Philipp; Michlmayr, Herbert; Malachová, Alexandra; Berthiller, Franz; Schuhmacher, Rainer; Krska, Rudolf; Adam, Gerhard

    2015-08-01

    Deoxynivalenol (DON) is a protein synthesis inhibitor produced by the Fusarium species, which frequently contaminates grains used for human or animal consumption. We treated a wheat suspension culture with DON or one of its acetylated derivatives, 3-acetyl-DON (3-ADON), 15-acetyl-DON (15-ADON) and 3,15-diacetyl-DON (3,15-diADON), and monitored the metabolization over a course of 96 h. Supernatant and cell extract samples were analyzed using a tailored LC-MS/MS method for the quantification of DON metabolites. We report the formation of tentatively identified DON-15-O-β-D-glucoside (D15G) and of 15-acetyl-DON-3-sulfate (15-ADON3S) as novel deoxynivalenol metabolites in wheat. Furthermore, we found that the recently identified 15-acetyl-DON-3-O-β-D-glucoside (15-ADON3G) is the major metabolite produced after 15-ADON challenge. 3-ADON treatment led to a higher intracellular content of toxic metabolites after six hours compared to all other treatments. 3-ADON was exclusively metabolized into DON before phase II reactions occurred. In contrast, we found that 15-ADON was directly converted into 15-ADON3G and 15-ADON3S in addition to metabolization into deoxynivalenol-3-O-β-D-glucoside (D3G). This study highlights significant differences in the metabolization of DON and its acetylated derivatives. PMID:26274975

  16. The Metabolic Fate of Deoxynivalenol and Its Acetylated Derivatives in a Wheat Suspension Culture: Identification and Detection of DON-15-O-Glucoside, 15-Acetyl-DON-3-O-Glucoside and 15-Acetyl-DON-3-Sulfate

    PubMed Central

    Schmeitzl, Clemens; Warth, Benedikt; Fruhmann, Philipp; Michlmayr, Herbert; Malachová, Alexandra; Berthiller, Franz; Schuhmacher, Rainer; Krska, Rudolf; Adam, Gerhard

    2015-01-01

    Deoxynivalenol (DON) is a protein synthesis inhibitor produced by the Fusarium species, which frequently contaminates grains used for human or animal consumption. We treated a wheat suspension culture with DON or one of its acetylated derivatives, 3-acetyl-DON (3-ADON), 15-acetyl-DON (15-ADON) and 3,15-diacetyl-DON (3,15-diADON), and monitored the metabolization over a course of 96 h. Supernatant and cell extract samples were analyzed using a tailored LC-MS/MS method for the quantification of DON metabolites. We report the formation of tentatively identified DON-15-O-β-D-glucoside (D15G) and of 15-acetyl-DON-3-sulfate (15-ADON3S) as novel deoxynivalenol metabolites in wheat. Furthermore, we found that the recently identified 15-acetyl-DON-3-O-β-D-glucoside (15-ADON3G) is the major metabolite produced after 15-ADON challenge. 3-ADON treatment led to a higher intracellular content of toxic metabolites after six hours compared to all other treatments. 3-ADON was exclusively metabolized into DON before phase II reactions occurred. In contrast, we found that 15-ADON was directly converted into 15-ADON3G and 15-ADON3S in addition to metabolization into deoxynivalenol-3-O-β-D-glucoside (D3G). This study highlights significant differences in the metabolization of DON and its acetylated derivatives. PMID:26274975

  17. Colony stimulating factor-inducing activity of isoflavone C-glucosides from the bark of Dalbergia monetaria.

    PubMed

    Kawaguchi, K; Alves, S de M; Watanabe, T; Kikuchi, S; Satake, M; Kumazawa, Y

    1998-10-01

    To obtain immunomodulating substances from Amazonian medicinal plants, hot water extracts from 21 samples available commercially were tested in terms of mitogenic and colony-stimulating factor (CSF)-inducing activities. Among them, Dalbergia monetaria exhibited the highest CSF-inducing activity. Orobol 8-C-glucoside (OCG-8) and orobol 6-C-glucoside (OCG-6) were isolated from the bark of D. monetaria as major constituents. The CSF-inducing activity of OCG-8 was higher than that of OCG-6 and a dose-dependent manner at a range of 0.1-10 mg/mouse. Serum CSF production induced by an intraperitoneal (i.p.) injection with 1 mg OCG-8 reached a peak at 4-6 h later, suggesting that OCG-8 would act on hematopoietic system. PMID:9810271

  18. Diversified glucosinolate metabolism: biosynthesis of hydrogen cyanide and of the hydroxynitrile glucoside alliarinoside in relation to sinigrin metabolism in Alliaria petiolata

    PubMed Central

    Frisch, Tina; Motawia, Mohammed S.; Olsen, Carl E.; Agerbirk, Niels; Møller, Birger L.; Bjarnholt, Nanna

    2015-01-01

    Alliaria petiolata (garlic mustard, Brassicaceae) contains the glucosinolate sinigrin as well as alliarinoside, a γ-hydroxynitrile glucoside structurally related to cyanogenic glucosides. Sinigrin may defend this plant against a broad range of enemies, while alliarinoside confers resistance to specialized (glucosinolate-adapted) herbivores. Hydroxynitrile glucosides and glucosinolates are two classes of specialized metabolites, which generally do not occur in the same plant species. Administration of [UL-14C]-methionine to excised leaves of A. petiolata showed that both alliarinoside and sinigrin were biosynthesized from methionine. The biosynthesis of alliarinoside was shown not to bifurcate from sinigrin biosynthesis at the oxime level in contrast to the general scheme for hydroxynitrile glucoside biosynthesis. Instead, the aglucon of alliarinoside was formed from metabolism of sinigrin in experiments with crude extracts, suggesting a possible biosynthetic pathway in intact cells. Hence, the alliarinoside pathway may represent a route to hydroxynitrile glucoside biosynthesis resulting from convergent evolution. Metabolite profiling by LC-MS showed no evidence of the presence of cyanogenic glucosides in A. petiolata. However, we detected hydrogen cyanide (HCN) release from sinigrin and added thiocyanate ion and benzyl thiocyanate in A. petiolata indicating an enzymatic pathway from glucosinolates via allyl thiocyanate and indole glucosinolate derived thiocyanate ion to HCN. Alliarinoside biosynthesis and HCN release from glucosinolate-derived metabolites expand the range of glucosinolate-related defenses and can be viewed as a third line of defense, with glucosinolates and thiocyanate forming protein being the first and second lines, respectively. PMID:26583022

  19. Overexpression of the UGT73C6 alters brassinosteroid glucoside formation in Arabidopsis thaliana

    PubMed Central

    2011-01-01

    Background Brassinosteroids (BRs) are signaling molecules that play essential roles in the spatial regulation of plant growth and development. In contrast to other plant hormones BRs act locally, close to the sites of their synthesis, and thus homeostatic mechanisms must operate at the cellular level to equilibrate BR concentrations. Whilst it is recognized that levels of bioactive BRs are likely adjusted by controlling the relative rates of biosynthesis and by catabolism, few factors, which participate in these regulatory events, have as yet been identified. Previously we have shown that the UDP-glycosyltransferase UGT73C5 of Arabidopsis thaliana catalyzes 23-O-glucosylation of BRs and that glucosylation renders BRs inactive. This study identifies the closest homologue of UGT73C5, UGT73C6, as an enzyme that is also able to glucosylate BRs in planta. Results In a candidate gene approach, in which homologues of UGT73C5 were screened for their potential to induce BR deficiency when over-expressed in plants, UGT73C6 was identified as an enzyme that can glucosylate the BRs CS and BL at their 23-O-positions in planta. GUS reporter analysis indicates that UGT73C6 shows over-lapping, but also distinct expression patterns with UGT73C5 and YFP reporter data suggests that at the cellular level, both UGTs localize to the cytoplasm and to the nucleus. A liquid chromatography high-resolution mass spectrometry method for BR metabolite analysis was developed and applied to determine the kinetics of formation and the catabolic fate of BR-23-O-glucosides in wild type and UGT73C5 and UGT73C6 over-expression lines. This approach identified novel BR catabolites, which are considered to be BR-malonylglucosides, and provided first evidence indicating that glucosylation protects BRs from cellular removal. The physiological significance of BR glucosylation, and the possible role of UGT73C6 as a regulatory factor in this process are discussed in light of the results presented. Conclusion

  20. Continuous spectrophotometric assays for beta-glucosidases acting on the plant glucosides L-picein and prunasin.

    PubMed

    Lai, L B; Gopalan, V; Glew, R H

    1992-02-01

    The neutral pH optimum beta-glucosidases of mammalian liver and almonds are each capable of hydrolyzing a number of plant glucosides, including L-picein (p-hydroxyacetophenone-beta-D-glucoside) and prunasin (D-mandelonitrile-beta-D-glucoside). Taking advantage of the marked differences in the spectra of the substrate/product pairs of L-picein/p-hydroxyacetophenone and prunasin/mandelonitrile, we have devised spectrophotometric assays that permit the continuous monitoring at pH 7.0 of p-hydroxyacetophenone (piceol) release from L-picein by guinea pig hepatic cytosolic beta-glucosidase and mandelonitrile from prunasin by almond beta-glucosidase. When L-picein hydrolysis was monitored at 320 nm and prunasin at 282 nm, the molar absorption coefficients determined for their products, namely piceol and mandelonitrile, were 3200 and 1360 M-1 cm-1, respectively. The kinetic parameter Km and Vmax values obtained using these spectrophotometric procedures for the guinea pig liver cytosolic beta-glucosidase acting on L-picein were 0.88 mM and 5.29 x 10(5) units/mg protein and for the almond beta-glucosidase acting on prunasin, Km 1.1 mM and Vmax 5.24 x 10(6) units/mg protein. These values agreed well with previously reported values obtained using less convenient, discontinuous assay procedures. PMID:1632501

  1. Cyanidin-3-glucoside, a natural product derived from blackberry, exhibits chemopreventive and chemotherapeutic activity.

    PubMed

    Ding, Min; Feng, Rentian; Wang, Shiow Y; Bowman, Linda; Lu, Yongju; Qian, Yong; Castranova, Vincent; Jiang, Bing-Hua; Shi, Xianglin

    2006-06-23

    Epidemiological data suggest that consumption of fruits and vegetables has been associated with a lower incidence of cancer. Cyanidin-3-glucoside (C3G), a compound found in blackberry and other food products, was shown to possess chemopreventive and chemotherapeutic activity in the present study. In cultured JB6 cells, C3G was able to scavenge ultraviolet B-induced *OH and O2-* radicals. In vivo studies indicated that C3G treatment decreased the number of non-malignant and malignant skin tumors per mouse induced by 12-O-tetradecanolyphorbol-13-acetate (TPA) in 7,12-dimethylbenz[a]anthracene-initiated mouse skin. Pretreatment of JB6 cells with C3G inhibited UVB- and TPA-induced transactivation of NF-kappaB and AP-1 and expression of cyclooxygenase-2 and tumor necrosis factor-alpha. These inhibitory effects appear to be mediated through the inhibition of MAPK activity. C3G also blocked TPA-induced neoplastic transformation in JB6 cells. In addition, C3G inhibited proliferation of a human lung carcinoma cell line, A549. Animal studies showed that C3G reduced the size of A549 tumor xenograft growth and significantly inhibited metastasis in nude mice. Mechanistic studies indicated that C3G inhibited migration and invasion of A549 tumor cells. These finding demonstrate for the first time that a purified compound of anthocyanin inhibits tumor promoter-induced carcinogenesis and tumor metastasis in vivo. PMID:16618699

  2. Synthesis of α - mangostin-D-glucoside in supercritical carbon dioxide media.

    PubMed

    Zarena, A S; Sankar, Kadimi Udaya

    2015-10-01

    α-Mangostin, the major xanthone constituent of mangoteen fruit pericarp, has several important pharmaceutical application but its bioavailability is restricted due to its insolubility in water. Herein, we synthesized water soluble α-mangostin-D-glucoside by glycosylation of α-mangostin at hydroxyl group; using amyloglucosidase (3.2.1.3) catalyzed reaction in supercritical carbon dioxide (SC-CO2) media. Response surface methodology (RSM) based on a five-variable central composite rotatable design involving 32 experiments was used to determine the effect of pressure (80-160 bar), temperature (35-75 °C), enzyme concentration (15-45 mg), buffer pH (4.0-8.0) and buffer volume (1.0-5.0 mL). Experimental data fitted the second-order polynomial equation as indicated by R(2) value of 0.94. The optimal enzymatic conversion within the experimental range of the variables reached 20.3 % at a pressure of 120 bar, temperature of 55 °C, enzyme concentration of 30 mg, buffer volume of 3 mL and pH 6.0 which is well matched with the predictive yield. PMID:26396400

  3. Expression of a zeatin-O-glucoside-degrading beta-glucosidase in Brassica napus.

    PubMed Central

    Falk, A; Rask, L

    1995-01-01

    A beta-glucosidase was purified from seeds of Brassica napus L. (oilseed rape). The 130-kD native enzyme consisted of a disulfide-linked dimer of 64-kD monomers. Internal amino acid sequences were used to construct degenerate primers for polymerase chain reaction-mediated cloning of cDNA for the enzyme. One nearly full-length and one partial beta-glucosidase-encoding cDNA clone were isolated and sequenced. Southern hybridization showed that beta-glucosidase is encoded by a small gene family in B. napus. Northern hybridization showed that the genes are expressed in the seed, with a low degree of expression in other tissues. In the seed, the expression started at 30 days after pollination (DAP), with the highest expression at 40 DAP. The size of the transcript was approximately 1900 nucleotides. In situ hybridization to developing seeds of B. napus showed that the beta-glucosidase expression started at 30 DAP around the provascular tissue in the embryo axis. In the cotyledons, mRNA initially accumulated around the provascular tissues but was detected first at 35 DAP. At 40 DAP, expression occurred in most parts of the seed. In situ hybridization also detected beta-glucosidase mRNA in shoots, young roots, and the basal part of the hypocotyls. Zeatin-O-glucoside was identified as a natural substrate for B. napus beta-glucosidase. PMID:7659745

  4. Furofuran Lignan Glucosides with Estrogen-Inhibitory Properties from the Bangladeshi Medicinal Plant Terminalia citrina.

    PubMed

    Muhit, Md Abdul; Umehara, Kaoru; Mori-Yasumoto, Kanami; Noguchi, Hiroshi

    2016-05-27

    Extracts from the leaves of the Bangladeshi medicinal plant Terminalia citrina were prepared, and 13 new furofuran lignan glucosides, terminalosides A-K (1-4, 6-12), 2-epiterminaloside D (5), and 6-epiterminaloside K (13), were characterized using various spectroscopic techniques. Twelve of the isolates were found to contain rare tetraoxygenated aryl groups in their structures. Analysis of the NMR chemical shifts for the oxymethine signals in the furofuran ring suggested a pragmatic approach to determining the relative configuration of these compounds. The ECD and NOESY spectroscopic data obtained allowed for the deduction of the absolute configurations and conformations of the compounds. The isolates were tested for their estrogenic/antiestrogenic activity using the MCF-7 and T47D estrogen-responsive human breast cancer cell lines. Terminalosides B (2) and G (8) exhibited inhibitory effects for both cell lines, and estradiol-enhanced cell proliferation was suppressed by 90% at concentrations lower than 10 μM. Terminaloside E (6) showed inhibitory activity against the T47D cell line, whereas terminalosides C (3), F (7), and I (10) and 6-epiterminaloside K (13) displayed antiestrogenic activity against MCF-7 cells. PMID:27110635

  5. Enzymatic hydrolysis of steryl glucosides, major contaminants of vegetable oil-derived biodiesel.

    PubMed

    Aguirre, Andres; Peiru, Salvador; Eberhardt, Florencia; Vetcher, Leandro; Cabrera, Rodolfo; Menzella, Hugo G

    2014-05-01

    Biodiesels are mostly produced from lipid transesterification of vegetable oils, including those from soybean, jatropha, palm, rapeseed, sunflower, and others. Unfortunately, transesterification of oil produces various unwanted side products, including steryl glucosides (SG), which precipitate and need to be removed to avoid clogging of filters and engine failures. So far, efficient and cost-effective methods to remove SGs from biodiesel are not available. Here we describe for the first time the identification, characterization and heterologous production of an enzyme capable of hydrolyzing SGs. A synthetic codon-optimized version of the lacS gene from Sulfolobus solfataricus was efficiently expressed and purified from Escherichia coli, and used to treat soybean derived biodiesel containing 100 ppm of SGs. After optimizing different variables, we found that at pH 5.5 and 87 °C, and in the presence of 0.9 % of the emulsifier polyglycerol polyricinoleate, 81 % of the total amount of SGs present in biodiesel were hydrolyzed by the enzyme. This remarkable reduction in SGs suggests a path for the removal of these contaminants from biodiesel on industrial scale using an environmentally friendly enzymatic process. PMID:24265025

  6. The multiple strategies of an insect herbivore to overcome plant cyanogenic glucoside defence.

    PubMed

    Pentzold, Stefan; Zagrobelny, Mika; Roelsgaard, Pernille Sølvhøj; Møller, Birger Lindberg; Bak, Søren

    2014-01-01

    Cyanogenic glucosides (CNglcs) are widespread plant defence compounds that release toxic hydrogen cyanide by plant β-glucosidase activity after tissue damage. Specialised insect herbivores have evolved counter strategies and some sequester CNglcs, but the underlying mechanisms to keep CNglcs intact during feeding and digestion are unknown. We show that CNglc-sequestering Zygaena filipendulae larvae combine behavioural, morphological, physiological and biochemical strategies at different time points during feeding and digestion to avoid toxic hydrolysis of the CNglcs present in their Lotus food plant, i.e. cyanogenesis. We found that a high feeding rate limits the time for plant β-glucosidases to hydrolyse CNglcs. Larvae performed leaf-snipping, a minimal disruptive feeding mode that prevents mixing of plant β-glucosidases and CNglcs. Saliva extracts did not inhibit plant cyanogenesis. However, a highly alkaline midgut lumen inhibited the activity of ingested plant β-glucosidases significantly. Moreover, insect β-glucosidases from the saliva and gut tissue did not hydrolyse the CNglcs present in Lotus. The strategies disclosed may also be used by other insect species to overcome CNglc-based plant defence and to sequester these compounds intact. PMID:24625698

  7. Metabolism, excretion and avoidance of cyanogenic glucosides in insects with different feeding specialisations.

    PubMed

    Pentzold, Stefan; Zagrobelny, Mika; Bjarnholt, Nanna; Kroymann, Juergen; Vogel, Heiko; Olsen, Carl Erik; Møller, Birger Lindberg; Bak, Søren

    2015-11-01

    Cyanogenic glucosides (CNglcs) are widespread plant defence compounds releasing toxic hydrogen cyanide when hydrolysed by specific β-glucosidases after plant tissue damage. In contrast to specialist herbivores that have mechanisms to avoid toxicity from CNglcs, it is generally assumed that non-adapted herbivores are negatively affected by CNglcs. Recent evidence, however, implies that the defence potential of CNglcs towards herbivores may not be as effective as previously anticipated. Here, performance, metabolism and excretion products of insects not adapted to CNglcs were analysed, including species with different degrees of dietary specialisation (generalists, specialists) and different feeding modes (leaf-snipping lepidopterans, piercing-sucking aphids). Insects were reared either on cyanogenic or acyanogenic plants or on an artificial cyanogenic diet. Lepidopteran generalists (Spodoptera littoralis, Spodoptera exigua, Mamestra brassicae) were compared to lepidopteran glucosinolate-specialists (Pieris rapae, Pieris brassicae, Plutella xylostella), and a generalist aphid (Myzus persicae) was compared to an aphid glucosinolate-specialist (Lipaphis erysimi). All insects were tolerant to cyanogenic plants; in lepidopterans tolerance was mainly due to excretion of intact CNglcs. The two Pieris species furthermore metabolized aromatic CNglcs to amino acid conjugates (Cys, Gly, Ser) and derivatives of these, which is similar to the metabolism of benzylglucosinolates in these species. Aphid species avoided uptake of CNglcs during feeding. Our results imply that non-adapted insects tolerate plant CNglcs either by keeping them intact for excretion, metabolizing them, or avoiding uptake. PMID:26483288

  8. PLS-Prediction and Confirmation of Hydrojuglone Glucoside as the Antitrypanosomal Constituent of Juglans Spp.

    PubMed

    Ellendorff, Therese; Brun, Reto; Kaiser, Marcel; Sendker, Jandirk; Schmidt, Thomas J

    2015-01-01

    Naphthoquinones (NQs) occur naturally in a large variety of plants. Several NQs are highly active against protozoans, amongst them the causative pathogens of neglected tropical diseases such as human African trypanosomiasis (sleeping sickness), Chagas disease and leishmaniasis. Prominent NQ-producing plants can be found among Juglans spp. (Juglandaceae) with juglone derivatives as known constituents. In this study, 36 highly variable extracts were prepared from different plant parts of J. regia, J. cinerea and J. nigra. For all extracts, antiprotozoal activity was determined against the protozoans Trypanosoma cruzi, T. brucei rhodesiense and Leishmania donovani. In addition, an LC-MS fingerprint was recorded for each extract. With each extract's fingerprint and the data on in vitro growth inhibitory activity against T. brucei rhodesiense a Partial Least Squares (PLS) regression model was calculated in order to obtain an indication of compounds responsible for the differences in bioactivity between the 36 extracts. By means of PLS, hydrojuglone glucoside was predicted as an active compound against T. brucei and consequently isolated and tested in vitro. In fact, the pure compound showed activity against T. brucei at a significantly lower cytotoxicity towards mammalian cells than established antiprotozoal NQs such as lapachol. PMID:26035104

  9. Cyanidin 3-glucoside improves diet-induced metabolic syndrome in rats.

    PubMed

    Bhaswant, Maharshi; Fanning, Kent; Netzel, Michael; Mathai, Michael L; Panchal, Sunil K; Brown, Lindsay

    2015-12-01

    Increased consumption of dark-coloured fruits and vegetables may mitigate metabolic syndrome. This study has determined the changes in metabolic parameters, and in cardiovascular and liver structure and function, following chronic administration of either cyanidin 3-glucoside (CG) or Queen Garnet plum juice (QG) containing cyanidin glycosides to rats fed either a corn starch (C) or a high-carbohydrate, high-fat (H) diet. Eight to nine-week-old male Wistar rats were randomly divided into six groups for 16-week feeding with C, C with CG or QG, H or H with CG or QG. C or H were supplemented with CG or QG at a dose of ∼ 8 mg/kg/day cyanidin glycosides from week 8 to 16. H rats developed signs of metabolic syndrome including visceral adiposity, impaired glucose tolerance, hypertension, cardiovascular remodelling, increased collagen deposition in left ventricle, non-alcoholic fatty liver disease, increased plasma liver enzymes and increased inflammatory cell infiltration in the heart and liver. Both CG and QG reversed these cardiovascular, liver and metabolic signs. However, no intact anthocyanins or common methylated/conjugated metabolites could be detected in the plasma samples and plasma hippuric acid concentrations were unchanged. Our results suggest CG is the most likely mediator of the responses to QG but that further investigation of the pharmacokinetics of oral CG in rats is required. PMID:26477387

  10. Effects of iriflophenone 3-C-β-glucoside on fasting blood glucose level and glucose uptake

    PubMed Central

    Pranakhon, Ratree; Aromdee, Chantana; Pannangpetch, Patchareewan

    2015-01-01

    Background: One of the biological activities of agar wood (Aquilaria sinensis Lour., Thymelaeaceae), is anti-hyperglycemic activity. The methanolic extract (ME) was proven to possess the fasting blood glucose activity in rat and glucose uptake transportation by rat adipocytes. Objective: To determine the decreasing fasting blood glucose level of constituents affordable for in vivo test. If the test was positive, the mechanism which is positive to the ME, glucose transportation, will be performed. Materials and Methods: The ME was separated by column chromatography and identified by spectroscopic methods. Mice was used as an animal model (in vivo), and rat adipocytes were used for the glucose transportation activity (in vitro). Result: Iriflophenone 3-C-β-glucoside (IPG) was the main constituent, 3.17%, and tested for the activities. Insulin and the ME were used as positive controls. The ME, IPG and insulin lowered blood glucose levels by 40.3, 46.4 and 41.5%, respectively, and enhanced glucose uptake by 152, 153, and 183%, respectively. Conclusion: These findings suggest that IPG is active in lowering fasting blood glucose with potency comparable to that of insulin. PMID:25709215

  11. The plant oncogene rolC is responsible for the release of cytokinins from glucoside conjugates.

    PubMed Central

    Estruch, J J; Chriqui, D; Grossmann, K; Schell, J; Spena, A

    1991-01-01

    The rolC gene of Agrobacterium rhizogenes, which drastically affects growth and development of transgenic plants, codes for a cytokinin-beta-glucosidase. Indeed, rolC protein expressed in Escherichia coli as a fusion protein hydrolyses cytokinin glucosides, thus liberating free cytokinins. Furthermore, beta-glucosidase activity present in E. coli extracts expressing the rolC protein was inhibited by affinity-purified antibodies specific for the rolC protein. Finally, rolC proteins expressed in transgenic plants were shown to be responsible for cytokinin-beta-glucosidase activity. Morphological and phytohormonal analysis, performed on transgenic plants that are somatic mosaics for the expression of the rolC gene, extend and confirm our interpretation that the developmental, physiological and morphological alterations caused by rolC expression in transgenic plants are primarily due to a modification of the cytokinin balance. These observations shed new light on the control of growth and differentiation in plants by growth factors. Images PMID:1915268

  12. Isolation of Photosystem I Complexes from Octyl Glucoside/Sodium Dodecyl Sulfate Solubilized Spinach Thylakoids 1

    PubMed Central

    Dunahay, Terri G.; Staehelin, L. Andrew

    1985-01-01

    We have used the nonionic detergent octyl-β-d-glucopyranoside in combination with sodium dodecyl sulfate to isolate two novel Photosystem I (PSI) complexes from spinach (Spinacea oleracea L.) thylakoid membranes. These complexes have been characterized as to their spectral properties, content of PSI reaction center chlorophyll P700, and protein composition. PSI-B, purified from solubilized membranes by sucrose density gradient centrifugation, is a putative native PSI complex. PSI-B contains four polypeptides between 21 and 25 kilodaltons in addition to the components of the PSI antenna complex (LHCI); three of these polypeptides have not previously been associated with PSI. A second complex, CPI*, is purified from octyl glucoside/sodium dodecyl sulfate solubilized thylakoids by two cycles of preparative gel electrophoresis under mildly denaturing conditions. Electrophoresis under these conditions releases a discrete set of polypeptides from PSI producing a complex composed only of the PSI reaction center and the LHCI antenna. In addition, the PSI reaction center complex CPI isolated from preparative gels and PSI-B were reconstituted into lecithin liposomes for structural analysis using freeze-fracture electron microscopy. The results suggest that the native PSI complex produces 12- to 13-nanometer particles, while the PSI reaction center, depleted of LHCI and peripheral proteins, produces particles with an average diameter of 10 nanometers. Images Fig. 1 Fig. 2 Fig. 5 Fig. 6 Fig. 7 PMID:16664291

  13. Direct detection, cloning and characterization of a glucoside hydrolase from forest soil.

    PubMed

    Hua, Mei; Zhao, Shubo; Zhang, Lili; Liu, Dongbo; Xia, Hongmei; Li, Fan; Chen, Shan

    2015-06-01

    A glucoside hydrolase gene, egl01, was cloned from the soil DNA of Changbai Mountain forest by homologous PCR amplification. The deduced sequence of 517 amino acids included a catalytic domain of glycoside hydrolase family 5 and was homologous to a putative cellulase from Bacillus licheniformis. The recombinant enzyme, Egl01, was maximally active at pH 5 and 50 °C and it was stable at pH 3-9, 4-50 °C, and also stable in the presence of metal ions, organic solvents, surfactants and salt. Its activity was above 120 % in 2-3 M NaCl/KCl and over 70 % was retained in 1-4 M NaCl/KCl for 6d. Egl01 hydrolyzed carboxymethyl cellulose, beechwood xylan, crop stalk, laminarin, filter paper, and avicel but not pNPG, indicating its broad substrate specificity. These properties make this recombinant enzyme a promising candidate for industrial applications. PMID:25700816

  14. Prophylactic Efficacy of Quercetin 3-β-O-d-Glucoside against Ebola Virus Infection.

    PubMed

    Qiu, Xiangguo; Kroeker, Andrea; He, Shihua; Kozak, Robert; Audet, Jonathan; Mbikay, Majambu; Chrétien, Michel

    2016-09-01

    Ebola outbreaks occur on a frequent basis, with the 2014-2015 outbreak in West Africa being the largest one ever recorded. This outbreak has resulted in over 11,000 deaths in four African countries and has received international attention and intervention. Although there are currently no approved therapies or vaccines, many promising candidates are undergoing clinical trials, and several have had success in promoting recovery from Ebola. However, these prophylactics and therapeutics have been designed and tested only against the same species of Ebola virus as the one causing the current outbreak. Future outbreaks involving other species would require reformulation and possibly redevelopment. Therefore, a broad-spectrum alternative is highly desirable. We have found that a flavonoid derivative called quercetin 3-β-O-d-glucoside (Q3G) has the ability to protect mice from Ebola even when given as little as 30 min prior to infection. Furthermore, we have demonstrated that this compound targets the early steps of viral entry. Most promisingly, antiviral activity against two distinct species of Ebola virus was seen. This study serves as a proof of principle that Q3G has potential as a prophylactic against Ebola virus infection. PMID:27297486

  15. Phenylpropenoic Acid Glucoside from Rooibos Protects Pancreatic Beta Cells against Cell Death Induced by Acute Injury

    PubMed Central

    Himpe, Eddy; Cunha, Daniel A.; Song, Imane; Bugliani, Marco; Marchetti, Piero; Cnop, Miriam; Bouwens, Luc

    2016-01-01

    Objective Previous studies demonstrated that a phenylpropenoic acid glucoside (PPAG) from rooibos (Aspalathus linearis) extract had anti-hyperglycemic activity and significant protective effects on the pancreatic beta cell mass in a chronic diet-induced diabetes model. The present study evaluated the cytoprotective effect of the phytochemical on beta cells exposed to acute cell stress. Methods Synthetically prepared PPAG was administered orally in mice treated with a single dose of streptozotocin to acutely induce beta cell death and hyperglycemia. Its effect was assessed on beta cell mass, proliferation and apoptotic cell death. Its cytoprotective effect was also studied in vitro on INS-1E beta cells and on human pancreatic islet cells. Results Treatment with the phytochemical PPAG protected beta cells during the first days after the insult against apoptotic cell death, as evidenced by TUNEL staining, and prevented loss of expression of anti-apoptotic protein BCL2 in vivo. In vitro, PPAG protected INS-1E beta cells from streptozotocin-induced apoptosis and necrosis in a BCL2-dependent and independent way, respectively, depending on glucose concentration. PPAG also protected human pancreatic islet cells against the cytotoxic action of the fatty acid palmitate. Conclusions These findings show the potential use of PPAG as phytomedicine which protects the beta cell mass exposed to acute diabetogenic stress. PMID:27299564

  16. Glucosidic pathways of glycogen breakdown and glucose production by muscle from postexercised frogs.

    PubMed

    Fournier, P A; Guderley, H

    1993-11-01

    Muscle and body glucose in frogs increases markedly during the initial hour of recovery after strenuous exercise. The liver is not the major source responsible for this accumulation. This is indicated by the stability of liver glycogen levels after exercise and by the observation that hepatectomized and normal frogs accumulate similar amounts of glucose in their muscles and body during recovery. The renal contribution cannot account for this increase in body glucose. Most of the glucose that accumulates in the body after exercise has a muscular origin, as indicated by the facts that two-thirds of the body glucose is found in muscle and that the intracellular levels of muscle glucose are much higher than those of the plasma. The glucose that accumulates outside muscle may also have a muscular origin. The glucosidic pathways of glycogen breakdown are the only metabolic avenue with sufficient capacity to account for the amount of glucose accumulated in muscle during the first hour of recovery. These results indicate that the ability of an isolated preparation of frog muscle to liberate glucose during recovery from exercise (Fournier et al. J. Biol. Chem. 267: 8234-8238, 1992) is not an artifactual metabolic curiosity but rather a metabolic reality that takes place in vivo. Glucose accumulation during recovery is thought to facilitate the metabolic transition of frog carbohydrate metabolism from a catabolic state, characteristic of exercise, to an anabolic one. PMID:8238616

  17. Simultaneous determination of four secoiridoid and iridoid glycosides in rat plasma by ultra performance liquid chromatography-tandem mass spectrometry and its application to a comparative pharmacokinetic study.

    PubMed

    Wu, Yun; Ai, Yu; Wang, Fenrong; Ma, Wen; Bian, Qiaoxia; Lee, David Y-W; Dai, Ronghua

    2016-02-01

    A simple, reliable and rapid ultra-performance liquid chromatography-tandem mass spectrometry method was developed and validated for the simultaneous quantification of four secoiridoid (gentiopicroside, swertiamarin, sweroside) and iridoid glycosides (loganic acid), the bio-active ingredients in rat plasma. After liquid-liquid extraction, chromatographic separation was accomplished on a Shim-pack XR-ODS column with a mobile phase consisting of methanol and 0.1% formic acid in water. A triple quadrupole tandem mass spectrometry equipped with an electrospray ionization source was used as detector operating both in positive and negative ionization mode and operated by multiple-reaction monitoring scanning. The lower limits of quantitation were 0.25-30 ng/mL for all the analytes. Both intra-day and inter-day precision and accuracy of analytes were well within acceptance criteria (±15%). The mean extraction recoveries of analytes and internal standard (amygdalin) from rat plasma were all >71.4%. The validated method was successfully applied to a comparative pharmacokinetic study of four analytes in rat plasma between normal and arthritic rats after oral administration of Huo Luo Xiao Ling Dan and Gentiana macrophylla extract, respectively. Results showed significant differences in pharmacokinetic properties of the analytes among the different groups. PMID:26014753

  18. Novel glyceryl glucoside is a low toxic alternative for cryopreservation agent.

    PubMed

    Su, Cathy; Allum, Allison J; Aizawa, Yasushi; Kato, Takamitsu A

    2016-08-01

    Glyceryl glucoside (GG, α-d-glucosyglycerol) is a natural glycerol derivative found in alcoholic drinks. Recently GG has been used as an alternative for glycerol in cosmetic products. However, the safety of using GG is still unclear. Currently, dimethyl sulfoxide (DMSO) and glycerol are wildly used in cryopreservation. Despite GG being a derivative of glycerol, the ability of GG in cryopreservation is still unknown. By using a system of Chinese Hamster Ovary cells (CHO), A549 cells and AG1522 cells, the study examined the cryoprotective effects of DMSO, glycerol and GG. Cytotoxic and genotoxic responses induced by the three chemicals were also investigated with CHO to determine the safety of GG for cosmetic products. Our data suggests that GG has great cryopresearvation ability in the concentration of 30%-40% (v/v). For cytotoxic studies, DMSO showed the highest cytotoxicity above 3% (v/v) in cell doubling time delay among three chemicals. For the acute cytotoxicity with trypan blue dye exclusion assay, GG showed stronger cell killing effect within 24 h above 4% (v/v). For the continuous cytotoxicity with colony formation assay for 7 days, DMSO showed significantly reduced clonogenic ability above 2%. In genotoxicity studies, CHO treated with glycerol at 2% concentration induced three times higher frequencies of sister chromatid exchange (SCE) than background levels. GG did not induce significant amounts of SCE compared to background. Micronuclei formation was equally observed in the 2% and above concentrations of glycerol and GG. Our data showed that GG has significant effects on cryopreservation compared to DMSO. Glycerol and GG have similar cytotoxicity effects to CHO, but glycerol induced genotoxic responses in the same concentration. Therefore, we conclude that GG may be a safer alternative compound to glycerol in cosmetic products and safer alternative to DMSO in cryopreservation. PMID:27235553

  19. Dispersion of Vesicles Composed of Industrially Produced Alkyl (Oligo) Glucoside Using Diol-Boron Complexation.

    PubMed

    Aikawa, Tatsuo; Asano, Yuuka; Kondo, Takeshi; Yuasa, Makoto

    2016-07-01

    Alkyl (oligo)glucosides (AOG) are known to be environmentally compatible amphiphiles whose commercial applicability should be broadened. The present paper describes the preparation of molecular assemblies of industrially produced AOG, which is a mixture composed of different length of alkyl chains (C9-C12) with oligoglucoside moiety with a few (1-3) of glucose units. It was also described that regulation of the dispersibility of the molecular assemblies prepared by diol-boron complexation between the sugar moiety on AOG and boric acid in a dispersion medium. The molecular assembly of AOG was successfully formed by mixing AOG and cholesterols (CH). When using a suitable amount of CH (20-40 mol% with respect to AOG), the molecular assembly formed a vesicle structure. The dispersion ability of the resulting vesicle was dependent on both the boric acid concentration and pH of the dispersion medium. The light-scattering and ζ-potential measurements revealed that high concentrations (≥10 mM) of boric acid improved dispersibility the vesicles. In contrast, the vesicle agglomerated at low concentrations of boric acid (1-7.5 mM). In the absence of boric acid in dispersion medium, the vesicles were completely agglomerated. The optimum pH range for vesicle dispersion was found to be from neutral to basic (7.4-10.1). The (11)B NMR study revealed that borate ester formation occurred between boric acid and the diol of the sugar moiety on AOG vesicle. The present data suggest that borate ester formation that occurred on the surface of the vesicle provided negative charge to the vesicles, contributing to their dispersion via repulsive forces. PMID:27321117

  20. Intestinal toxicity of the masked mycotoxin deoxynivalenol-3-β-D-glucoside.

    PubMed

    Pierron, Alix; Mimoun, Sabria; Murate, Leticia S; Loiseau, Nicolas; Lippi, Yannick; Bracarense, Ana-Paula F L; Liaubet, Laurence; Schatzmayr, Gerd; Berthiller, Franz; Moll, Wulf-Dieter; Oswald, Isabelle P

    2016-08-01

    Natural food contaminants such as mycotoxins are an important problem for human health. Deoxynivalenol (DON) is one of the most common mycotoxins detected in cereals and grains. Its toxicological effects mainly concern the immune system and the gastrointestinal tract. This toxin is a potent ribotoxic stressor leading to MAP kinase activation and inflammatory response. DON frequently co-occurs with its glucosylated form, the masked mycotoxin deoxynivalenol-3-β-D-glucoside (D3G). The toxicity of this later compound remains unknown in mammals. This study aimed to assess the ability of D3G to elicit a ribotoxic stress and to induce intestinal toxicity. The toxicity of D3G and DON (0-10 µM) was studied in vitro, on the human intestinal Caco-2 cell line, and ex vivo, on porcine jejunal explants. First, an in silico analysis revealed that D3G, contrary to DON, was unable to bind to the A-site of the ribosome peptidyl transferase center, the main targets for DON toxicity. Accordingly, D3G did not activate JNK and P38 MAPKs in treated Caco-2 cells and did not alter viability and barrier function on cells, as measured by the trans-epithelial electrical resistance. Treatment of intestinal explants for 4 h with 10 µM DON induced morphological lesions and up-regulated the expression of pro-inflammatory cytokines as measured by qPCR and pan-genomic microarray analysis. By contrast, expression profile of D3G-treated explants was similar to that of controls, and these explants did not show histomorphology alteration. In conclusion, our data demonstrated that glucosylation of DON suppresses its ability to bind to the ribosome and decreases its intestinal toxicity. PMID:26404761

  1. Leaching of cyanogenic glucosides and cyanide from white clover green manure.

    PubMed

    Bjarnholt, Nanna; Laegdsmand, Mette; Hansen, Hans C B; Jacobsen, Ole H; Møller, Birger Lindberg

    2008-06-01

    Use of crops for green manure as a substitute for chemical fertilizers and pesticides is an important approach towards more sustainable agricultural practices. Green manure from white clover is rich in nitrogen but white clover also produces the cyanogenic glucosides (CGs) linamarin and lotaustralin; CGs release toxic hydrogen cyanide (HCN) upon hydrolysis which may be utilized for pest control. We demonstrate that applying CGs in the form of a liquid extract of white clover to large columns of intact agricultural soils can result in leaching of toxic cyanide species to a depth of at least 1m. Although degradation of the CGs during leaching proceeded with half lives in the interval 1.5-35 h depending on soil characteristics, a fraction of the applied CGs (0.9-3.2%) was recovered in the leachate as either CGs or toxic cyanide species. Detoxification of the HCN formed was rapid in soil and leachate from both sandy and loamy soil. However, 30% of the leachate samples exceeded the EU threshold value of 50 micrgl(-1) total cyanide for drinking water and 85% exceeded the US threshold of 5 micrgl(-1) for cyanide chronic ecotoxicity in fresh water. This study demonstrates that even easily degradable natural products present in crop plants as defense compounds pose a threat to the quality of groundwater and surface waters. This aspect needs consideration in assessment of the risk associated with use of crops as green manure to replace chemical fertilizers and pesticides as well as in genetic engineering approaches to design crops with improved pest resistance. PMID:18472138

  2. Orcinol glucoside produces antidepressant effects by blocking the behavioural and neuronal deficits caused by chronic stress.

    PubMed

    Ge, Jin-Fang; Gao, Wen-Chao; Cheng, Wen-Ming; Lu, Wei-Li; Tang, Jie; Peng, Lei; Li, Ning; Chen, Fei-Hu

    2014-01-01

    This study focused on the antidepressant potential of orcinol glucoside (OG) and its possible mechanisms of action. We established a depressed rat model using 3 consecutive weeks of chronic unpredictable mild stress (CUMS). The antidepressant-like effect of OG was revealed using the sucrose preference test, the open field test, the forced swimming test (FST), and the tail suspension test (TST). The activity of the hypothalamic-pituitary-adrenal (HPA) axis was evaluated by detecting the serum corticosterone (CORT) concentrations and mRNA expression of corticotrophin-releasing hormone (CRH) in the hypothalamus. The protein expression levels of brain-derived neurotrophic factor (BDNF) and total phosphorylated-ERK1/2 were detected by western blot. The results showed that OG treatment (1.5, 3, or 6mg/kg) alleviated the depression-like behaviour of rats under CUMS, as indicated by the increased sucrose preference and the decreased immobility in both the FST and TST, although the rearing frequency in the open field test increased only in the group that received the lowest dose (1.5mg/kg OG). Rats that received OG treatment exhibited reduced serum CORT levels and CRH mRNA expression in the hypothalamus, suggesting that the hyperactivity of the HPA axis in CUMS rats was reversed by OG treatment. Moreover, OG treatment upregulated the protein levels of BDNF and phosphorylated-ERK1/2 in the hippocampus, even above control levels. Our findings suggest that OG improved depressive behaviour in CUMS rats by downregulating HPA axis hyperactivity and increasing BDNF expression and ERK1/2 phosphorylation in the hippocampus. PMID:23838013

  3. Functional diversification of two UGT80 enzymes required for steryl glucoside synthesis in Arabidopsis

    PubMed Central

    Stucky, Daniel F.; Arpin, James C.

    2015-01-01

    Steryl glucosides (SG) are abundant steroid conjugates in plant membranes. Beyond structural roles in lipid bilayers, functions in sugar transport, storage, and/or signalling are predicted. UDP-glucose:sterol glucosyltransferase 80A2 (UGT80A2) and UGT80B1, which share similarity to fungal counterparts, are implicated in SG synthesis in Arabidopsis thaliana. A third related enzyme, which seems specific to the plant lineage, is encoded by UGT713B1/At5g24750. Genetic and biochemical approaches were employed to determine the role of each UGT gene in the production of specific SGs and acyl SGs (ASGs). Using direct infusion electrospray ionization tandem mass spectrometry (ESI-MS/MS), SG and acyl SG (ASG) contents of ugt80 and ugt713 mutants, and triple and double mutants were profiled in seeds. In vitro enzyme assays were performed to assay substrate preferences. Both UGT80A2 and UGT80B1, but not UGT713B1 were shown to be coordinately down-regulated during seed imbibition when SG levels decline, consistent with similar functions as UGT80 enzymes. UGT80A2 was found to be required for normal levels of major SGs in seeds, whereas UGT80B1 is involved in accumulation of minor SG and ASG compounds. Although the results demonstrate specific activities for UGT80A2 and UGT80B1, a role for UGT713B1 in SG synthesis was not supported. The data show that UGT80A2, the more highly conserved enzyme, is responsible for the bulk production of SGs in seeds, whereas UGT80B1 plays a critical accessory role. This study extends our knowledge of UGT80 enzymes and provides evidence for specialized functions for distinct classes of SG and ASG molecules in plants. PMID:25316063

  4. Plant growth inhibition by cis-cinnamoyl glucosides and cis-cinnamic acid.

    PubMed

    Hiradate, Syuntaro; Morita, Sayaka; Furubayashi, Akihiro; Fujii, Yoshiharu; Harada, Jiro

    2005-03-01

    Spiraea thunbergii Sieb. contains 1-O-cis-cinnamoyl-beta-D-glucopyranose (CG) and 6-O-(4'-hydroxy-2'-methylene-butyroyl)-1-O-cis-cinnamoyl-beta-D-glucopyranose (BCG) as major plant growth inhibiting constituents. In the present study, we determined the inhibitory activity of CG and BCG on root elongation of germinated seedlings of lettuce (Lactuca sativa), pigweed (Amaranthus retroflexus), red clover (Trifolium pratense), timothy (Phleum pratense), and bok choy (Brassica rapa var chinensis) in comparison with that of two well-known growth inhibitors, 2,4-dichlorophenoxyacetic acid (2,4-D) and (+)-2-cis-4-trans-abscisic acid (cis-ABA), as well as two related chemicals of CG and BCG, cis-cinnamic acid (cis-CA) and trans-cinnamic acid (trans-CA). The EC50 values for CG and BCG on lettuce were roughly one-half to one-quarter of the value for cis-ABA. cis-Cinnamic acid, which is a component of CG and BCG, possessed almost the same inhibitory activity of CG and BCG, suggesting that the essential chemical structure responsible for the inhibitory activity of CG and BCG is cis-CA. The cis-stereochemistry of the methylene moiety is apparently needed for high inhibitory activity, as trans-CA had an EC50 value roughly 100 times that of CG, BCG, and cis-CA. Growth inhibition by CG, BCG, and cis-CA was influenced by the nature of the soil in the growing medium: alluvial soil preserved the bioactivity, whereas volcanic ash and calcareous soils inhibited bioactivity. These findings indicate a potential role of cis-CA and its glucosides as allelochemicals for use as plant growth regulators in agricultural fields. PMID:15898503

  5. Trihydroxybenzoic acid glucoside as a global skin color modulator and photo-protectant

    PubMed Central

    Chajra, Hanane; Redziniak, Gérard; Auriol, Daniel; Schweikert, Kuno; Lefevre, Fabrice

    2015-01-01

    Background 3,4,5-Trihydroxybenzoic acid glucoside (THBG), a molecule produced by an original biocatalysis-based technology, was assessed in this study with respect to its skin photoprotective capacity and its skin color control property on Asian-type skin at a clinical level and on skin explant culture models. Methods The double-blinded clinical study was done in comparison to a vehicle by the determination of objective color parameters thanks to recognized quantitative and qualitative analysis tools, including Chroma-Meter, VISIA-CR™, and SIAscope™. Determination of L* (brightness), a* and b* (green–red and blue–yellow chromaticity coordinates), individual typology angle, and C* (chroma) and h* (hue angle) parameters using a Chroma-Meter demonstrated that THBG is able to modify skin color while quantification of ultraviolet (UV) spots by VISIA-CR™ confirmed its photoprotective effect. The mechanism of action of THBG molecule was determined using explant skin culture model coupled to histological analysis (epidermis melanin content staining). Results We have demonstrated that THBG was able to modulate significantly several critical parameters involved in skin color control such as L* (brightness), a* (redness), individual typology angle (pigmentation), and hue angle (yellowness in this study), whereas no modification occurs on b* and C* parameters. We have demonstrated using histological staining that THBG decrease epidermis melanin content under unirradiated and irradiated condition. We also confirmed that THBG molecule is not a sunscreen agent. Conclusion This study demonstrated that THBG controls skin tone via the inhibition of melanin synthesis as well as the modulation of skin brightness, yellowness, and redness. PMID:26648748

  6. The flavonoid luteolin, but not luteolin-7-O-glucoside, prevents a transthyretin mediated toxic response.

    PubMed

    Iakovleva, Irina; Begum, Afshan; Pokrzywa, Malgorzata; Walfridsson, Malin; Sauer-Eriksson, A Elisabeth; Olofsson, Anders

    2015-01-01

    Transthyretin (TTR) is a homotetrameric plasma protein with amyloidogenic properties that has been linked to the development of familial amyloidotic polyneuropathy (FAP), familial amyloidotic cardiomyopathy, and senile systemic amyloidosis. The in vivo role of TTR is associated with transport of thyroxine hormone T4 and retinol-binding protein. Loss of the tetrameric integrity of TTR is a rate-limiting step in the process of TTR amyloid formation, and ligands with the ability to bind within the thyroxin binding site (TBS) can stabilize the tetramer, a feature that is currently used as a therapeutic approach for FAP. Several different flavonoids have recently been identified that impair amyloid formation. The flavonoid luteolin shows therapeutic potential with low incidence of unwanted side effects. In this work, we show that luteolin effectively attenuates the cytotoxic response to TTR in cultured neuronal cells and rescues the phenotype of a Drosophila melanogaster model of FAP. The plant-derived luteolin analogue cynaroside has a glucoside group in position 7 of the flavone A-ring and as opposed to luteolin is unable to stabilize TTR tetramers and thus prevents a cytotoxic effect. We generated high-resolution crystal-structures of both TTR wild type and the amyloidogenic mutant V30M in complex with luteolin. The results show that the A-ring of luteolin, in contrast to what was previously suggested, is buried within the TBS, consequently explaining the lack of activity from cynaroside. The flavonoids represent an interesting group of drug candidates for TTR amyloidosis. The present investigation shows the potential of luteolin as a stabilizer of TTR in vivo. We also show an alternative orientation of luteolin within the TBS which could represent a general mode of binding of flavonoids to TTR and is of importance concerning the future design of tetramer stabilizing drugs. PMID:26020516

  7. Eriodictyol-7-O-glucoside activates Nrf2 and protects against cerebral ischemic injury

    SciTech Connect

    Jing, Xu; Ren, Dongmei; Wei, Xinbing; Shi, Huanying; Zhang, Xiumei; Perez, Ruth G.; Lou, Haiyan; Lou, Hongxiang

    2013-12-15

    Stroke is a complex disease that may involve oxidative stress-related pathways in its pathogenesis. The nuclear factor erythroid-2-related factor 2/antioxidant response element (Nrf2/ARE) pathway plays an important role in inducing phase II detoxifying enzymes and antioxidant proteins and thus has been considered a potential target for neuroprotection in stroke. The aim of the present study was to determine whether eriodictyol-7-O-glucoside (E7G), a novel Nrf2 activator, can protect against cerebral ischemic injury and to understand the role of the Nrf2/ARE pathway in neuroprotection. In primary cultured astrocytes, E7G increased the nuclear localization of Nrf2 and induced the expression of the Nrf2/ARE-dependent genes. Exposure of astrocytes to E7G provided protection against oxygen and glucose deprivation (OGD)-induced oxidative insult. The protective effect of E7G was abolished by RNA interference-mediated knockdown of Nrf2 expression. In vivo administration of E7G in a rat model of focal cerebral ischemia significantly reduced the amount of brain damage and ameliorated neurological deficits. These data demonstrate that activation of Nrf2/ARE signaling by E7G is directly associated with its neuroprotection against oxidative stress-induced ischemic injury and suggest that targeting the Nrf2/ARE pathway may be a promising approach for therapeutic intervention in stroke. - Highlights: • E7G activates Nrf2 in astrocytes. • E7G stimulates expression of Nrf2-mediated cytoprotective proteins in astrocytes. • E7G protects astrocytes against OGD-induced cell death and apoptosis. • The neuroprotective effect of E7G involves the Nrf2/ARE pathway. • E7G protects rats against cerebral ischemic injury.

  8. The Flavonoid Luteolin, but Not Luteolin-7-O-Glucoside, Prevents a Transthyretin Mediated Toxic Response

    PubMed Central

    Pokrzywa, Malgorzata; Walfridsson, Malin; Sauer-Eriksson, A. Elisabeth; Olofsson, Anders

    2015-01-01

    Transthyretin (TTR) is a homotetrameric plasma protein with amyloidogenic properties that has been linked to the development of familial amyloidotic polyneuropathy (FAP), familial amyloidotic cardiomyopathy, and senile systemic amyloidosis. The in vivo role of TTR is associated with transport of thyroxine hormone T4 and retinol-binding protein. Loss of the tetrameric integrity of TTR is a rate-limiting step in the process of TTR amyloid formation, and ligands with the ability to bind within the thyroxin binding site (TBS) can stabilize the tetramer, a feature that is currently used as a therapeutic approach for FAP. Several different flavonoids have recently been identified that impair amyloid formation. The flavonoid luteolin shows therapeutic potential with low incidence of unwanted side effects. In this work, we show that luteolin effectively attenuates the cytotoxic response to TTR in cultured neuronal cells and rescues the phenotype of a Drosophila melanogaster model of FAP. The plant-derived luteolin analogue cynaroside has a glucoside group in position 7 of the flavone A-ring and as opposed to luteolin is unable to stabilize TTR tetramers and thus prevents a cytotoxic effect. We generated high-resolution crystal-structures of both TTR wild type and the amyloidogenic mutant V30M in complex with luteolin. The results show that the A-ring of luteolin, in contrast to what was previously suggested, is buried within the TBS, consequently explaining the lack of activity from cynaroside. The flavonoids represent an interesting group of drug candidates for TTR amyloidosis. The present investigation shows the potential of luteolin as a stabilizer of TTR in vivo. We also show an alternative orientation of luteolin within the TBS which could represent a general mode of binding of flavonoids to TTR and is of importance concerning the future design of tetramer stabilizing drugs. PMID:26020516

  9. Consequences of transferring three sorghum genes for secondary metabolite (cyanogenic glucoside) biosynthesis to grapevine hairy roots.

    PubMed

    Franks, T K; Powell, K S; Choimes, S; Marsh, E; Iocco, P; Sinclair, B J; Ford, C M; van Heeswijck, R

    2006-04-01

    A multigenic trait (biosynthesis of the secondary metabolite, dhurrin cyanogenic glucoside) was engineered de novo in grapevine (Vitis vinifera L.). This follows a recent report of transfer of the same trait to Arabidopsis (Arabidopsis thaliana) using three genetic sequences from sorghum (Sorghum bicolor): two cytochrome P450-encoding cDNAs (CYP79A1 and CYP71E1) and a UDPG-glucosyltransferase-encoding cDNA (sbHMNGT). Here we describe the two-step process involving whole plant transformation followed by hairy root transformation, which was used to transfer the same three sorghum sequences to grapevine. Transgenic grapevine hairy root lines that accumulated transcript from none, one (sbHMNGT), two (CYP79A1 and CYP71E1) or all three transgenes were recovered and characterisation of these lines provided information about the requirements for dhurrin biosynthesis in grapevine. Only lines that accumulated transcripts from all three transgenes had significantly elevated cyanide potential (up to the equivalent of about 100 mg HCN kg(-1) fresh weight), and levels were highly variable. One dhurrin-positive line was tested and found to release cyanide upon maceration and can therefore be considered 'cyanogenic'. In in vitro dual co-culture of this cyanogenic hairy root line or an acyanogenic line with the specialist root-sucking, gall-forming, aphid-like insect, grapevine phylloxera (Daktulosphaira vitifoliae, Fitch), there was no evidence for protection of the cyanogenic plant tissue from infestation by the insect. Consistently high levels of dhurrin accumulation may be required for this to occur. The possibility that endogenous grapevine gene expression is modulated in response to engineered dhurrin biosynthesis was investigated using microarray analysis of 1225 grapevine ESTs, but differences in patterns of gene expression associated with dhurrin-positive and dhurrin-negative phenotypes were not identified. PMID:16604459

  10. Antioxidative and radioprotective activities of semiquinone glucoside derivative (SQGD) isolated from Bacillus sp. INM-1.

    PubMed

    Kumar, Raj; Bansal, Deen Dayal; Patel, Dev Dutt; Mishra, Saurabh; Karamalakova, Yana; Zheleva, A; Gadjeva, Vessilina; Sharma, Rakesh Kumar

    2011-03-01

    A semiquinone glucoside derivative (SQGD) was isolated from a radioresistant bacterium Bacillus sp. INM-1 and its antioxidant and radioprotective activities were evaluated using in vitro assays. Natural stable free radical properties of SQGD in solid as well as in solution form were estimated using Electron Paramagnetic Resonance (EPR) spectrometry. Results of the study were demonstrated high reducing power (1.267 ± 0.03356 U(abs)) and nitric oxide radicals scavenging activity (34.684 ± 2.132%) of SQGD. Maximum lipid peroxidation inhibitory activity of SQGD was found to be 74.09 ± 0.08% at 500 μg/ml concentration. Similarly, significant (39.54%; P < 0.05) protection to the liposomal artificial membrane against gamma radiation was observed by SQGD in terms of neutralization of gamma radiation-induced TBARS radicals in vitro. OH(-) radicals scavenging efficacy of SQGD was estimated in terms of % inhibition in deoxy D: -ribose degradation by non-site-specific and site-specific assay. The maximum (54.01 ± 1.01%) inhibition of deoxy D: -ribose degradation was observed in non-site-specific manner, whereas, site-specific inhibition was observed to be 46.36 ± 0.5% at the same concentration (250 μg/ml) of SQGD. EPR spectroscopic analysis of the SQGD indicated ~80% reduction of DPPH radicals at 6.4% concentration. EPR spectral analysis of SQGD was revealed an appearance of very strong EPR signal of 2.00485 (crystalline form) and 2.00520 (solution form) g(y) tensor value, which were an established characteristic of o-semiquinone radicals. Therefore, it can be concluded that SQGD is a natural stable o-semiquinone-type radical, possessing strong antioxidant activities and can effectively neutralize radiation induced free radicals in biological system. PMID:21116688

  11. Total glucosides of paeony for rheumatoid arthritis: a protocol for a systematic review

    PubMed Central

    Luo, Jing; Jin, Di-Er; Yang, Guo-Yan; Zhang, Ying-Ze; Wang, Jian-Ming; Kong, Wei-Ping; Tao, Qing-Wen

    2016-01-01

    Introduction Total glucosides of paeony (TGP) is a natural plant extract, which is widely used in China for treating rheumatoid arthritis (RA). Many relevant randomised controlled trials (RCTs) of TGP for RA are available, but they have not been systematically reviewed. This systematic review aims to examine the effectiveness and safety of TGP in patients with RA. Methods and analyses We will search for RCTs of TGP in the treatment of RA, performed up until February 2016, in PubMed, Embase, Cochrane Central Register of Controlled Trials, and four Chinese databases (Chinese Biomedical Database, China National Knowledge Infrastructure, Wanfang Database and Chinese Scientific Journal Database). Trial registers and reference lists of retrieved articles will also be searched to identify potential articles. RCTs comparing TGP with placebo, no treatment, or disease-modifying antirheumatic drugs for patients with RA will be retrieved. The primary outcomes will be disease improvement and disease remission. The secondary outcomes will be surrogate outcomes, symptoms, adverse effects, and quality of life. Two reviewers will independently extract data on participants, interventions, comparisons, outcomes, etc. The methodological quality of each included study will be evaluated using the Cochrane risk of bias tool, and the strength of evidence on prespecified outcomes will be assessed in accordance with the GRADE (Grading of Recommendations Assessment, Development and Evaluation) approach. Review Manager 5.3 software will be used for data analyses. Meta-analyses will be performed if the data are sufficiently homogeneous, both statistically and clinically. Possible publication bias will also be checked using funnel plots once the number of included studies is sufficient. Ethics and dissemination Ethics approval is not required, as this study will not involve patients. The results of this study will be submitted to a peer-reviewed journal for publication, to inform both clinical

  12. Application of amylomaltase for the synthesis of salicin-α-glucosides as efficient anticoagulant and anti-inflammatory agents.

    PubMed

    Rudeekulthamrong, Prakarn; Kaulpiboon, Jarunee

    2016-09-01

    The focus of this study was the synthesis of α-glucosyl derivatives of salicin by a transglucosylation reaction. The reaction was catalyzed by recombinant amylomaltase using tapioca starch as a glucosyl donor. Several reaction parameters, such as the enzyme-substrate concentrations, pH, temperature and incubation time, were optimized. Using the optimum conditions, at least three products with retention times (Rt) of 6.2, 9.2 and 14.1 were observed. The maximum yield of glucosylated salicin derivatives was 63% (w/w) of the total products. The structures of the glucosylated salicin derivatives were confirmed to be salicin-α-D-glucopyranoside, salicin-α-D-maltopyranoside and salicin-α-D-maltotriopyranoside through a combination of enzyme treatments, mass spectrometry and NMR analyses. The glycosidic bond between glucose units consisted of an α-1,4-configuration. The water solubility of salicin-α-D-glucopyranoside, salicin-α-D-maltopyranoside and salicin-α-D-maltotriopyranoside was 3-, 5- and 8-fold higher, respectively, than that of salicin, whereas their relative sweetness values were lower than that of sucrose. Interestingly, the long-chain salicin-α-D-glucosides showed greater anticoagulant and anti-inflammatory activities than salicin. In addition, the synthesized salicin-α-D-glucosides were able to tolerate acidic and high temperature conditions, but not α-glucosidase or human digestive enzymes. Therefore, these salicin-α-D-glucosides should be applied by the injection route to achieve greater bioavailability than is possible by the oral route. PMID:27394039

  13. Use of countercurrent chromatography during isolation of 6-hydroxyluteolin-7-O-β-glucoside, a major antioxidant of Athrixia phylicoides.

    PubMed

    de Beer, Dalene; Joubert, Elizabeth; Malherbe, Christiaan J; Jacobus Brand, D

    2011-09-01

    Athrixia phylicoides, an indigenous South African herbal tea, has potential as a source of nutraceutical antioxidant extracts. Countercurrent chromatography (CCC) was employed as part of a multi-step process to isolate one of the major antioxidant compounds in A. phylicoides extracts. Antioxidant activity of the extracts was comparable to commercial nutraceutical extracts from Aspalathus linearis and Cyclopia spp. in a range of assays. The extracts were tested for radical scavenging (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) di-ammonium radical cation (ABTS·⁺) scavenging, 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) scavenging and oxygen radical absorbance capacity (ORAC)), ferric reducing antioxidant potential (FRAP) and iron chelating activity, as well as inhibition of microsomal lipid and linoleic acid emulsion oxidation. After extraction optimisation, the antioxidant activity of the major phenolic compounds in an A. phylicoides extract was determined using the on-line HPLC-diode-array-DPPH and -ABTS·⁺ radical scavenging assays. Major compounds reported for the first time included chlorogenic acid, 1,3-dicaffeoylquinic acid, several hydroxycinnamic acid derivatives, including dicaffeoyl quinic acids, and an unidentified flavone-hexose. Finally, CCC was used in conjunction with liquid-liquid partitioning and semi-preparative reversed-phase HPLC to isolate 6-hydroxyluteolin-7-O-β-glucoside (a major antioxidant) and quercetagetin-7-O-β-glucoside (a minor compound present in CCC fraction containing 6-hydroxyluteolin-7-O-β-glucoside) from an A. phylicoides extract. The chemical structures of the isolated compounds were confirmed by LC high-resolution electrospray ionisation MS, as well as ¹H, ¹³C and 2D NMR spectroscopy. This is the first report of the isolation of these compounds from A. phylicoides. PMID:21236437

  14. Chronic Exposure to Dietary Sterol Glucosides is Neurotoxic to Motor Neurons and Induces an ALS-PDC Phenotype

    PubMed Central

    Tabata, R. C.; Wilson, J. M. B.; Ly, P.; Zwiegers, P.; Kwok, D.; Van Kampen, J. M.; Cashman, N.; Shaw, C. A.

    2008-01-01

    Epidemiological studies of the Guamanian variants of amyotrophic lateral sclerosis (ALS) and parkinsonism, amyotrophic lateral sclerosis-parkinsonism dementia complex (ALS-PDC), have shown a positive correlation between consumption of washed cycad seed flour and disease occurrence. Previous in vivo studies by our group have shown that the same seed flour induces ALS and PDC phenotypes in out bred adult male mice. In vitro studies using isolated cycad compounds have also demonstrated that several of these are neurotoxic, specifically, a number of water insoluble phytosterol glucosides of which β-sitosterol β-d-glucoside (BSSG) forms the largest fraction. BSSG is neurotoxic to motor neurons and other neuronal populations in culture. The present study shows that an in vitro hybrid motor neuron (NSC-34) culture treated with BSSG undergoes a dose-dependent cell loss. Surviving cells show increased expression of HSP70, decreased cytosolic heavy neurofilament expression, and have various morphological abnormalities. CD-1 mice fed mouse chow pellets containing BSSG for 15 weeks showed motor deficits and motor neuron loss in the lumbar and thoracic spinal cord, along with decreased glutamate transporter labelling, and increased glial fibrillary acid protein reactivity. Other pathological outcomes included increased caspase-3 labelling in the striatum and decreased tyrosine-hydroxylase labelling in the striatum and substantia nigra. C57BL/6 mice fed BSSG-treated pellets for 10 weeks exhibited progressive loss of motor neurons in the lumbar spinal cord that continued to worsen even after the BSSG exposure ended. These results provide further support implicating sterol glucosides as one potential causal factor in the motor neuron pathology previously associated with cycad consumption and ALS-PDC. PMID:18196479

  15. Effect of Multiple Dietary Supplement Containing Lutein, 
Astaxanthin, Cyanidin-3-Glucoside, and DHA on Accommodative Ability

    PubMed Central

    Kono, Keiko; Shimizu, Yoshiki; Takahashi, Satomi; Matsuoka, Sayuri; Yui, Kei

    2014-01-01

    Objective The study aimed to verify that ingestion of multiple dietary supplement containing lutein, astaxanthin, cyanidin-3-glucoside and docosahexaenoic acid (DHA) would improve accommodative ability of aged and older subjects who were aware of eye strain on a daily basis. Methods A randomized double-blind placebo-controlled parallel group comparison study was conducted for 48 participants aged 45 to 64 years who complained of eye strain. The subjects took multiple dietary supplement containing 10 mg of lutein, 20 mg of bilberry extract and 26.5 mg of black soybean hull extract (a total of 2.3 mg of cyanidin-3-glucoside in both extracts), 4 mg of astaxanthin, and 50 mg of DHA (test supplement) or placebo for four consecutive weeks. Near-point accommodation (NPA) and subjective symptoms were evaluated both before and after four weeks’ intake. Results The variation of the NPA of both eyes from baseline to 4 weeks’ post-intake in the test supplement group was significantly higher than in the placebo group (1.321±0.394 diopter (D) in the test supplement group and 0.108±0.336 D in the placebo group, p=0.023). The multiple dietary supplement group showed improvement in the NPA. Regarding subjective symptoms, significant improvement of “stiff shoulders or neck” and “blurred vision” was also found in the test supplement group compared to the placebo group (p<0.05). There were no safety concerns in this study. Conclusion This study shows that multiple dietary supplement containing lutein, astaxanthin, cyanidin-3-glucoside, and DHA has effect to improve accommodative ability and subjective symptoms related to eye fatigue.

  16. Comparison of nano and conventional liquid chromatographic methods for the separation of (+)-catechin-ethyl-malvidin-3-glucoside diastereoisomers.

    PubMed

    Kučera, Lukáš; Fanali, Salvatore; Aturki, Zeineb; Pospíšil, Tomáš; Bednář, Petr

    2016-01-01

    Nano-liquid chromatography and conventional HPLC were used for the separation of diastereomers of (+)-catechin-ethyl-malvidin-3-glucoside. Those bridged anthocyanin dyes were obtained by reaction of (+)-catechin with malvidin-3-glucoside in the presence of acetaldehyde. Both diastereomers were isolated with semipreparative chromatography and their structures were confirmed by nuclear magnetic resonance and mass spectrometry. In-laboratory prepared capillary columns packed with fully porous particles Chromosphere C18, dp=3μm, core-shell particles Kinetex C18, dp=2.6μm (100μm i.d.) and monolithic column Chromolith CapRod (100μm i.d.) were used for the separation of (+)-catechin, malvidin-3-glucoside and both diastereomers. Chromosphere C18 stationary phase provided the best chromatographic performance. Mobile phase containing water:acetonitrile (80:20) acidified with trifluoroacetic acid (0.1%, v/v/v) was used in an isocratic elution mode with a flow rate of 360nLmin(-1). Separation of studied compounds was achieved in less than 7min under optimized conditions. The nano-liquid chromatographic method and a conventional HPLC one using the same fully porous particles (Chromosphere C18, 3μm, 100mm×4.6mm) were compared providing higher separation efficiency with the first analytical method and similar selectivity. A better peak symmetry and higher resolution of the studied diastereomers was achieved by conventional chromatography. Nevertheless, nano-liquid chromatography appeared to be useful for the separation of complex anthocyanin dyes and can be utilized for their analysis in plant and food micro-samples. The developed method was used for analysis of red wine grape pomace. PMID:26433264

  17. Periplanosides A-C: new insect-derived dihydroisocoumarin glucosides from Periplaneta americana stimulating collagen production in human dermal fibroblasts.

    PubMed

    Yang, Yong-Xun; Luo, Qi; Hou, Bo; Yan, Yong-Ming; Wang, Yue-Hu; Tang, Jian-Jun; Dong, Xiao-Ping; Ma, Xiu-Ying; Yang, Tong-Hua; Zuo, Zhi-Li; Cheng, Yong-Xian

    2015-01-01

    Three new dihydroisocoumarin glucosides, termed periplanosides A-C (1-3), a known analog, pericanaside (4), and the other twenty known compounds were isolated from the insect Periplaneta americana. Their structures including absolute configurations were determined by comprehensive spectroscopic analyses and computational methods. Biological evaluation showed that compound 2 could stimulate collagen production by 31.2% in human dermal fibroblasts-adult (HDFa) at the concentration of 30 μM, indicating its significance in skin repair and ulcer. PMID:26499169

  18. A study of transglucosylation kinetic in an enzymatic synthesis of benzyl alcohol glucoside by α-glucosidase from S. cerevisiae

    NASA Astrophysics Data System (ADS)

    Pavlović, M.; Dimitrijević, A.; Trbojević, J.; Milosavić, N.; Gavrović-Jankulović, M.; Bezbradica, D.; Veličković, D.

    2013-12-01

    α-1,4-Glucosidase from Saccharomyces cerevisiae is an enzyme which is widely used in synthesis of different drugs. Glucosidase inhibitors are studied as potential drugs for prevention of HIV and diabetes. For understanding of these processes it is very important to have insights in the transglucosylation activity of this enzyme. In this paper the kinetics of transglucosylation reaction catalyzed by this enzyme in the synthesis of benzyl alcohol glucoside was studied and all relevant kinetic constants for this system are found. It was shown one additional property of transglycosylation reactions catalyzed by glycosidases—inhibition by both, glucose acceptor and glucose donor, and mechanisms for these inhibitions were proposed.

  19. Syntheses of phosphatidyl-beta-D-glucoside analogues to probe antigen selectivity of monoclonal antibody 'DIM21'.

    PubMed

    Greimel, Peter; Lapeyre, Milaine; Nagatsuka, Yasuko; Hirabayashi, Yoshio; Ito, Yukishige

    2008-08-01

    Herein, we report the chemical syntheses of a series of phosphatidyl-beta-D-glucoside (PtdGlc) analogues, including 6-O-Ac, sn-2-O-Me, phosphorothioate as well as phosphatidylgalactoside and -mannoside derivatives. In the key step, beta-glycosyl H-phosphonate was condensed with enantiomerically pure diacylglycerol. Comparison of spectroscopic data with mono-acetylated PtdGlc from natural source confirmed the presence of an acetyl moiety at position 6. Furthermore, the reactivity of PtdGlc and its analogues toward monoclonal antibody 'DIM21' (MAb DIM21) was evaluated, revealing the crucial structural antigen features for successful MAb DIM21 binding. PMID:18625561

  20. Iridoid Glycosides Fraction of Folium syringae Leaves Modulates NF-κB Signal Pathway and Intestinal Epithelial Cells Apoptosis in Experimental Colitis

    PubMed Central

    Liu, Xin; Wang, Jian Ming

    2011-01-01

    Background and Aims Iridoid glycosides (IG), the major active fraction of F. syringae leaves has been demonstrated to have strong anti-inflammatory properties to ulcerative colitis (UC) in our previous study. The aim of this study was to investigate whether IG modulates the inflammatory response in experimental colitis at the level of NF-κB signal pathway and epithelial cell apoptosis. Methods UC in rats was induced by administration with dextran sulfate sodium (DSS) in drinking water. The inflammatory damage was assessed by disease activity index (DAI), macroscopic findings, histology and myeloperoxidase (MPO) activity. The effect of IG on pro-inflammatory cytokines TNF-α, IL-8, COX-2 and regulatory peptide TGF-β1 was measured. Epithelial cell apoptosis and the protein and mRNA expressions of Fas/FasL, Bcl-2/Bax, caspase-3, NF-κB p65, IκBα, p-IκBα and IKKβ were detected by TUNEL method, immunohistochemistry, Western blotting and real-time quantitative PCR, respectively. Results IG significantly ameliorated macroscopic damage and histological changes, reduced the activity of MPO, and strongly inhibited epithelial cell apoptosis. Moreover, IG markedly depressed TNF-α, IL-8, COX-2 and TGF-β1 levels in the colon tissues in a dose-dependent manner. Furthermore, IG significantly blocked of NF-κB signaling by inhibiting IκBα phosphorylation/degradation and IKKβ activity, down-regulated the protein and mRNA expressions of Fas/FasL, Bax and caspase-3, and activated Bcl-2 in intestinal epithelial cells. Conclusions These results demonstrated for the first time that IG possessed marked protective effects on experimental colitis through inhibition of epithelial cell apoptosis and blockade of NF-κB signal pathway. PMID:21931839

  1. Comparison of Sugars, Iridoid Glycosides and Amino Acids in Nectar and Phloem Sap of Maurandya barclayana, Lophospermum erubescens, and Brassica napus

    PubMed Central

    Lohaus, Gertrud; Schwerdtfeger, Michael

    2014-01-01

    Background Floral nectar contains sugars and amino acids to attract pollinators. In addition, nectar also contains different secondary compounds, but little is understood about their origin or function. Does nectar composition reflect phloem composition, or is nectar synthesized and/or modified in nectaries? Studies where both, the nectar as well as the phloem sap taken from the same plant species were analyzed in parallel are rare. Therefore, phloem sap and nectar from different plant species (Maurandya barclayana, Lophospermum erubescens, and Brassica napus) were compared. Methodology and Principal Findings Nectar was collected with microcapillary tubes and phloem sap with the laser-aphid-stylet technique. The nectar of all three plant species contained high amounts of sugars with different percentages of glucose, fructose, and sucrose, whereas phloem sap sugars consisted almost exclusively of sucrose. One possible reason for this could be the activity of invertases in the nectaries. The total concentration of amino acids was much lower in nectars than in phloem sap, indicating selective retention of nitrogenous solutes during nectar formation. Nectar amino acid concentrations were negatively correlated with the nectar volumes per flower of the different plant species. Both members of the tribe Antirrhineae (Plantaginaceae) M. barclayana and L. erubescens synthesized the iridoid glycoside antirrhinoside. High amounts of antirrhinoside were found in the phloem sap and lower amounts in the nectar of both plant species. Conclusions/Significance The parallel analyses of nectar and phloem sap have shown that all metabolites which were found in nectar were also detectable in phloem sap with the exception of hexoses. Otherwise, the composition of both aqueous solutions was not the same. The concentration of several metabolites was lower in nectar than in phloem sap indicating selective retention of some metabolites. Furthermore, the existence of antirrhinoside in nectar

  2. Metabolism of monoterpenes: early steps in the metabolism of d-neomenthyl-. beta. -D-glucoside in peppermint (Mentha piperita) rhizomes

    SciTech Connect

    Croteau, R.; Sood, V.K.; Renstroem, B.; Bhushan, R.

    1984-11-01

    Previous studies have shown that the monoterpene ketone l-(G-/sup 3/H) menthone is reduced to the epimeric alcohols l-menthol and d-neomenthol in leaves of flowering peppermint (Mentha piperita L.), and that a portion of the menthol is converted to methyl acetate while the bulk of the neomenthol is transformed to neomenthyl-..beta..-D-glucoside which is then transported to the rhizome. Analysis of the disposition of l-(G)/sup 3/H)menthone applied to midstem leaves of intact flowering plants allowed the kinetics of synthesis and transport of the monoterpenyl glucoside to be determined, and gave strong indication that the glucoside was subsequently metabolized in the rhizome. Studies with d-(G-/sup 3/H)neomenthyl-..beta..-D-glucoside as substrate, using excised rhizomes or rhizome segments, confirmed the hydrolysis of the glucoside as an early step in metabolism at this site, and revealed that the terpenoid moiety was further converted to a series of ether-soluble, methanol-soluble, and water-soluble products. The conversion of menthone to the lactone, and of the lactone to more polar products, were confirmed in vivo using l-(G-/sup 3/H)menthone and l-(G-/sup 3/H)-3,4-menthone lactone as substrates. Additional oxidation products were formed in vivo via the desaturation of labeled neomenthol and/or menthone, but none of these transformations appeared to lead to ring opening of the p-menthane skeleton. Each step in the main reaction sequence, from hydrolysis of neomenthyl glucoside to lactonization of menthone, was demonstrated in cell-free extracts from the rhizomes of flowering mint plants. The lactomization step is of particular significance in providing a means of cleaving the p-methane ring to afford an acyclic carbon skeleton that can be further degraded by modifications of the well-known ..beta..-oxidation sequence. 41 references, 3 figures, 1 table.

  3. Occurrence and fate of the norsesquiterpene glucoside ptaquiloside (PTA) in soils

    NASA Astrophysics Data System (ADS)

    Zaccone, Claudio; Cavoski, Ivana; Costi, Roberta; Sarais, Giorgia; Caboni, Pierluigi; Miano, Teodoro M.; Lattanzio, Vincenzo

    2014-05-01

    The bracken fern Pteridium aquilinum (L.) Kuhn, one of the most common plant species on Earth, produces a wide range of secondary metabolites including the norsesquiterpene glucoside ptaquiloside (PTA). This bracken constituent causes acute poisoning, blindness and cancer in animals, and can be transferred to man when bracken is utilized as food. Also milk from cows eating bracken is thought to be the vector for the transfer of PTA to humans, as well as PTA-contaminated drinking waters. Although some studies on the effect of growth conditions and soil properties on the production and mobility of PTA have been carried out (mainly in the North of Europe), results are sometimes conflicting and further investigations are needed. The aim of the present work is to study the occurrence and the fate of PTA in soils showing different physico-chemical features, collected in different pedoclimatic areas (from the South of Italy), but having the extensive ("wild") livestock farming as common denominator. The PTA content was determined in both soil and fern samples by GC-MS; both the extraction protocol and recovery were previously tested through incubation studies. Soils samples were also characterizes from the physical and chemical point of view (pH, EC, texture, total carbonates, cation exchange capacity, organic C, total N, available nutrients and heavy metal concentration) in order to correlate the possible influence of soil parameters on PTA production, occurrence and mobility. PTA concentration in soil samples was always

  4. Enzymatic Formation of Novel Ginsenoside Rg1-α-Glucosides by Rat Intestinal Homogenates.

    PubMed

    Mathiyalagan, Ramya; Kim, Young-Hoi; Kim, Yeon Ju; Kim, Myung-Kon; Kim, Min-Ji; Yang, Deok Chun

    2015-12-01

    The variation of linkage positions in ginsenosides leads to diverse pharmacological efficiencies. The hydrolysis and transglycosylation properties of glycosyl hydrolase family enzymes have a great impact on the synthesis of novel and structurally diversified compounds. In this study, six ginsenoside Rg1-α-glucosides were found to be synthesized from the reaction mixture of maltose as a donor and ginsenoside Rg1 as a sugar acceptor in the presence of rat small intestinal homogenates, which exhibit high α-glucosidase activities. The individual compounds were purified and were identified by spectroscopy (HPLC-MS, (1)H-NMR, and (13)C-NMR) as 6-O-[α-D-glcp-(1→4)-β-D-glcp]-20-O-(β-D-glcp)-20(S)-protopanaxatriol, 6-O-β-D-glcp-20-O-[α-D-glcp-(1→6)-(β-D-glcp)]-20(S)-protopanaxatriol, 6-O-β-D-glcp-20-O-[α-D-glcp-(1→4)-(β-D-glcp)]-20(S)-protopanaxatriol, 6-O-[α-D-glcp-(1→6)-β-D-glcp]-20-O-(β-glcp)-20(S)-protopanaxatriol, 6-O-[α-D-glcp-(1→3)-β-D-glcp]-20-O-(β-D-glcp)-20(S)-protopanaxatriol, and 6-O-β-D-glcp-20-O-[α-D-glcp-(1→3)-(β-D-glcp)]-20(S)-protopanaxatriol. Among these six, 6-O-β-D-glcp-20-O-α-D-glcp-(1→6)-(β-D-glcp)-20(S)-protopanaxatriol and 6-O-α-D-glcp-(1→6)-β-D-glcp-20-O-(β-D-glcp)-20(S)-protopanaxatriol are considered to be novel compounds of alpha-ginsenosidal saponins which pharmacological activities should be further characterized. This is the first report on the enzymatic elaboration of ginsenoside Rg1 derivatives using rat intestinal homogenates. To the best of our knowledge, it is also the first to reveal the sixth and 20th positions of an unusual α-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl sugar chain with 20(S)-protopanaxatriol saponins in Panax ginseng Mayer. PMID:26411353

  5. Non-water miscible ionic liquid improves biocatalytic production of geranyl glucoside with Escherichia coli overexpressing a glucosyltransferase.

    PubMed

    Schmideder, Andreas; Priebe, Xenia; Rubenbauer, Mark; Hoffmann, Thomas; Huang, Fong-Chin; Schwab, Wilfried; Weuster-Botz, Dirk

    2016-09-01

    Whole cells of Escherichia coli overexpressing a glucosyltransferase from Vitis vinifera were used for the glucosylation of geraniol to geranyl glucoside. A high cell density cultivation process for the production of whole-cell biocatalysts was developed, gaining a dry cell mass concentration of up to 67.6 ± 1.2 g L(-1) and a glucosyltransferase concentration of up to 2.7 ± 0.1 g protein L(-1) within a process time of 48 h. Whole-cell batch biotransformations in milliliter-scale stirred-tank bioreactors showed highest conversion of geraniol at pH 7.0 although the pH optimum of the purified glucosyltransferase was at pH 8.5. The biocatalytic batch process performance was improved significantly by the addition of a water-immiscible ionic liquid (N-hexylpyridinium bis(trifluoromethylsulfonyl)imid) for in situ substrate supply. The so far highest final geranyl glucoside concentration (291 ± 9 mg L(-1)) and conversion (71 ± 2 %) reported for whole-cell biotransformations of geraniol were achieved with 5 % (v/v) of the ionic liquid. PMID:27142377

  6. Long-term cultured hairy roots of chicory-a rich source of hydroxycinnamates and 8-deoxylactucin glucoside.

    PubMed

    Malarz, Janusz; Stojakowska, Anna; Kisiel, Wanda

    2013-12-01

    A 12-year-old hairy root culture of Cichorium intybus L., a callus culture of the plant as well as roots and leaves of a wild plant of chicory, and roots of two C. intybus L. var. sativum cultivars were examined in respect of their hydroxycinnamate and sesquiterpene lactone compositions and contents. Total phenolics and diphenylpicrylhydrazyl radical scavenging activity of the examined plant tissues were also analyzed. The most active in radical scavenging were extracts from the hairy roots and leaves of chicory. 3,5-Dicaffeoylquinic acid was the major antioxidant present in the hairy roots. Its content in the root biomass reached 5.5 %, calculated on a dry weight basis. 8-Deoxylactucin glucoside (crepidiaside A) was the major sesquiterpene lactone in the hairy roots. Its content reached 1.4 %, calculated on a dry weight basis, and was nearly two orders of magnitude higher than that in the roots of wild chicory plant. The glucosidic derivative of 8-deoxylactucin constituted over 85 % of the total sesquiterpene lactone content in the long-term cultured hairy roots of chicory. Aglycone of this compound was reported to possess anti-inflammatory activity. The qualitative and quantitative analyses of hydroxycinnamates in callus and hairy root cultures of C. intybus were undertaken for the first time. PMID:23975347

  7. Dirigent Protein-Mediated Lignan and Cyanogenic Glucoside Formation in Flax Seed: Integrated Omics and MALDI Mass Spectrometry Imaging.

    PubMed

    Dalisay, Doralyn S; Kim, Kye Won; Lee, Choonseok; Yang, Hong; Rübel, Oliver; Bowen, Benjamin P; Davin, Laurence B; Lewis, Norman G

    2015-06-26

    An integrated omics approach using genomics, transcriptomics, metabolomics (MALDI mass spectrometry imaging, MSI), and bioinformatics was employed to study spatiotemporal formation and deposition of health-protecting polymeric lignans and plant defense cyanogenic glucosides. Intact flax (Linum usitatissimum) capsules and seed tissues at different development stages were analyzed. Transcriptome analyses indicated distinct expression patterns of dirigent protein (DP) gene family members encoding (-)- and (+)-pinoresinol-forming DPs and their associated downstream metabolic processes, respectively, with the former expressed at early seed coat development stages. Genes encoding (+)-pinoresinol-forming DPs were, in contrast, expressed at later development stages. Recombinant DP expression and DP assays also unequivocally established their distinct stereoselective biochemical functions. Using MALDI MSI and ion mobility separation analyses, the pinoresinol downstream derivatives, secoisolariciresinol diglucoside (SDG) and SDG hydroxymethylglutaryl ester, were localized and detectable only in early seed coat development stages. SDG derivatives were then converted into higher molecular weight phenolics during seed coat maturation. By contrast, the plant defense cyanogenic glucosides, the monoglucosides linamarin/lotaustralin, were detected throughout the flax capsule, whereas diglucosides linustatin/neolinustatin only accumulated in endosperm and embryo tissues. A putative biosynthetic pathway to the cyanogens is proposed on the basis of transcriptome coexpression data. Localization of all metabolites was at ca. 20 μm resolution, with the web based tool OpenMSI enabling not only resolution enhancement but also an interactive system for real-time searching for any ion in the tissue under analysis. PMID:25981198

  8. In vitro evaluation of the effects of protein-polyphenol-polysaccharide interactions on (+)-catechin and cyanidin-3-glucoside bioaccessibility.

    PubMed

    Oliveira, Ana; Pintado, Manuela

    2015-11-01

    The bioaccessibility of cyanidin-3-glucoside and (+)-catechin in model solutions when β-lactoglobulin (β-LG) and pectin/chitosan are present was investigated using an in vitro model simulating gastrointestinal conditions. In the mouth, the free cyanidin content increased (+) 90 and 14% while the (+)-catechin content decreased (-) 23 and 13%, respectively for mixtures with -pectin and -β-LG-pectin. Under gastric conditions, the cyanidin content decreased 85 and 28% for mixtures with -pectin and -β-LG-pectin. On the contrary, after gastric digestion, (+)-catechin bioaccessibility increased and exhibited values similar to the original samples for all the systems tested. The transition to the intestinal environment induced a significant alteration on both polyphenols and this effect was more marked for cyanidin. Systems with pectin allowed obtaining a higher content of bioaccessible cyanidin. The gastric conditions promoted an increase in the antioxidant capacity, followed by a decrease of it in the intestine. The free (+)-catechin and cyanidin-3-glucoside contents decreased when exposed to the gastrointestinal tract conditions. However, when incorporated in food matrix components, the gastrointestinal tract may act positively on the extraction of polyphenols, since they are progressively released from protein and polysaccharide bonds, being available for the absorption and to exert their biological effects. PMID:26289110

  9. Phytochemical analysis of Plantago sempervirens from Majella National Park.

    PubMed

    Venditti, A; Serrilli, A M; Di Cecco, M; Ciaschetti, G; Andrisano, T; Bianco, A

    2012-11-01

    In this study, we report the isolation and identification of several compounds from Plantago sempervirens Crantz, collected in the protected area of Majella National Park. We examined the polar fraction, in particular the iridoidic one. Aucubin, caryoptoside, plantarenaloside and gardoside were isolated and identified. For the first time, in this species, 8-epiloganic acid was recognised. Also, verbascoside, a phenylethanoid glycoside, was recognised in this plant. PMID:22081901

  10. Nectar chemistry mediates the behavior of parasitized bees: consequences for plant fitness.

    PubMed

    Richardson, Leif L; Bowers, M Deane; Irwin, Rebecca E

    2016-02-01

    Plants produce an array of secondary metabolites that play important ecological roles as anti-herbivore and anti-pathogen defenses. Many herbivores experience physiological costs when they consume secondary metabolites, yet some also benefit, for example when these chemicals confer resistance to parasites and predators. Secondary metabolites are often present in nectar and pollen, which is paradoxical given that floral rewards are important in the attraction of mutualists rather than deterrence of antagonists. Motivated by studies of interactions among plants, herbivores, and parasites, as well as research showing that secondary metabolites can reduce bee disease, we characterized the occurrence of two iridoid glycosides, aucubin and catalpol, in floral rewards and other tissues of the bee pollinated plant, Chelone glabra. We then experimentally investigated effects of nectar iridoid glycoside concentrations on the foraging behavior of bumble bee pollinators naturally afflicted by a parasitoid fly and a protozoan intestinal parasite, and subsequent effects on an estimate of plant reproduction. We found that floral nectar had lower iridoid glycoside concentrations than leaves, pollen, and corollas, and that, compared to those plant parts, the relative ratio of the two primary iridoid glycosides, aucubin and catalpol, was reversed in nectar. Whether bees carried parasitoid fly larvae did not affect their response to nectar chemistry; however, there was a significant interaction between protozoan parasite infection and nectar treatment, with infected bees foraging longer at flowers with high compared to low nectar iridoid glycoside concentrations. Parasitized bees were also more likely to return to inflorescences with high iridoid glycoside nectar. Consequently, flowers in the high iridoid glycoside nectar treatment donated significantly more pollen to conspecific stigmas than did flowers in the low iridoid glycoside treatment, suggesting an increase in male plant

  11. Separation of vitexin-4″-O-glucoside and vitexin-2″-O-rhamnoside from hawthorn leaves extracts using macroporous resins.

    PubMed

    Li, Hongjuan; Liu, Ying; Jin, Haizhu; Liu, Sujing; Fang, Shengtao; Wang, Chunhua; Xia, Chuanhai

    2015-12-15

    Vitexin-4″-O-glucoside and vitexin-2″-O-rhamnoside are the major flavonoids of hawthorn leaves. In this work, the adsorption and desorption characteristics of vitexin-4″-O-glucoside and vitexin-2″-O-rhamnoside on seven macroporous resins were evaluated. Among the tested resins, the HPD-400 resin showed the best adsorption and desorption capacities. Adsorption isotherms were constructed for the HPD-400 resin and well fitted to Langmuir and Freundlich models. Dynamic adsorption and desorption tests were performed on column packed with the HPD-400 resin to optimize the chromatographic parameters. After one run treatment with the HPD-400 resin, the contents of vitexin-4″-O-glucoside and vitexin-2″-O-rhamnoside in the product were increased 8.44-fold and 8.43-fold from 0.720% and 2.63% to 6.08% and 22.2% with recovery yields of 79.1% and 81.2%, respectively. These results show that the developed method is a promising basis for the large-scale purification of vitexin-4″-O-glucoside and vitexin-2″-O-rhamnoside from hawthorn leaves and other plant materials. PMID:26562804

  12. Transepithelial permeability studies of flavan-3-ol-C-glucosides and procyanidin dimers and trimers across the Caco-2 cell monolayer.

    PubMed

    Hemmersbach, Sarah; Brauer, Susanne S; Hüwel, Sabine; Galla, Hans-Joachim; Humpf, Hans-Ulrich

    2013-08-21

    In this study the permeability of two flavanol-C-glucosides (FCglcs) and five dimeric and trimeric flavan-3-ols, namely, procyanidins (PCs), was investigated with the human colon carcinoma cell line (Caco-2) model. These compounds can be found especially in cocoa, and they are of great interest due to their assumed beneficial health effects. Transepithelial electrical resistance (TEER) and capacitance were measured online with a CellZscope device prior to and during the whole experiment to guarantee the maintenance of the barrier properties. The transport experiments with pure, single compounds (50-300 μM) from apical to basolateral side showed slight permeation of PCs A2, B2, and B5 and cinnamtannin B1 (CB1) as well as (-)-catechin-6-C-glucoside (C6Cglc) and (-)-catechin-8-C-glucoside (C8Cglc) of about 0.02-0.2% after 24 h. Transport of PC C1 could not be detected. Inhibition of P-glycoprotein (Pgp) increased the permeation of PC B2 and CB1 to the basolateral side, which indicates that Pgp counteracts the transport of these compounds. Metabolites (epicatechin, 3'- and 4'-O-epicatechin) in very small amounts were detectable only for PC B2. These are the first data concerning the permeability of flavan-3-ol-C-glucosides across the Caco-2 cell monolayer. PMID:23885956

  13. Liquid Chromatography-Electrospray Ionization Mass Spectrometry Method for the Rapid Identification of Citrus Limonoid Glucosides in Citrus Juices and Extracts

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A rapid and selective liquid chromatography-electrospray ionization mass spectrometry (LC-ESI-MS) method to screen citrus samples for limonoid glucosides and estimate their relative concentrations has been developed. This method utilizes a phenyl stationary phase, whereas previous methods have reli...

  14. SGLT-1 Transport and Deglycosylation inside Intestinal Cells Are Key Steps in the Absorption and Disposition of Calycosin-7-O-β-d-Glucoside in Rats.

    PubMed

    Shi, Jian; Zheng, Haihui; Yu, Jia; Zhu, Lijun; Yan, Tongmeng; Wu, Peng; Lu, Linlin; Wang, Ying; Hu, Ming; Liu, Zhongqiu

    2016-03-01

    Hydrolysis by lactase-phloridzin hydrolase (LPH) is the first and critical step in the absorption of isoflavonoid glucosides. However, the absorption characteristics of calycosin-7-O-β-d-glucoside (CG) slightly differ from other isoflavonoid glucosides. In this study, we used the rat intestinal perfusion model and performed pharmacokinetic studies and in vitro experiments to determine the factors influencing CG absorption and disposition. After oral administration of isoflavonoid glucosides, LPH was found to play minimal or no role on the hydrolysis of CG, in contrast to that of daidzin. CG was mainly transported into the small intestinal cells by sodium-dependent glucose transporter 1 (SGLT-1) as intact. This pathway could be the main mechanism underlying the high permeability of CG in the small intestine. CG was likely to be hydrolyzed in enterocytes to its aglycone calycosin by broad-specific β-glucuronides (BSβG) and glucocerebrosidase or rapidly metabolized. Calycosin was also rapidly and extensively metabolized to 3'-glucuronide in the enterocytes and liver, and the glucuronidation rates of calycosin and CG were much higher in the former. The metabolites were also transported into lumen by breast cancer resistance protein and multidrug resistance-associated protein 2. In conclusion, the enterocytes could be an important site for CG absorption, deglycosylation, and metabolism in rats. This study could contribute to the theoretical foundation and mechanism of absorption and disposition of flavonoid compounds. PMID:26658676

  15. Determination of citrus limonoid glucosides by high performance liquid chromatography coupled to post-column reaction with Ehrlich’s Reagent

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A method for the identification and quantification of citrus limonoid glucosides in juices based upon high performance liquid chromatography (HPLC) separation coupled to post-column reaction with Ehrlichs’s reagent has been developed. This method utilizes a phenyl stationary phase and an isocratic ...

  16. Cyanidin-3-O-beta-glucoside inhibits LPS-induced expression of inflammatory mediators through decreasing IkBa Phosphorylation in THP-1 Cells

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Objective and design: As a common phytochemical, cyanidin 3-O-beta-glucoside (C3G) has a role in inhibiting inflammatory mediators; however, its mechanism of action remains unclear. The purpose of this study was to explore the effect of C3G on lipopolysaccharide (LPS)-stimulated TNFa and IL-6 expres...

  17. Development and Validation of a Decigram-Scale Method for the Separation of Limonin from Limonin Glucoside by C-18 Flash Chromatography

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A preparative method for decigram-scale polishing of limonin glucoside with regard to removing traces of limonin, the main bitter principle in Citrus, is reported. During the method development and up-scaling stages, in which sample purity, sample size, solvent amounts, and drying conditions were v...

  18. A Versatile Family 3 Glycoside Hydrolase from Bifidobacterium adolescentis Hydrolyzes β-Glucosides of the Fusarium Mycotoxins Deoxynivalenol, Nivalenol, and HT-2 Toxin in Cereal Matrices

    PubMed Central

    Varga, Elisabeth; Malachova, Alexandra; Nguyen, Nhung Thi; Lorenz, Cindy; Haltrich, Dietmar; Berthiller, Franz; Adam, Gerhard

    2015-01-01

    Glycosylation plays a central role in plant defense against xenobiotics, including mycotoxins. Glucoconjugates of Fusarium toxins, such as deoxynivalenol-3-O-β-d-glucoside (DON-3G), often cooccur with their parental toxins in cereal-based food and feed. To date, only limited information exists on the occurrence of glucosylated mycotoxins and their toxicological relevance. Due to a lack of analytical standards and the requirement of high-end analytical instrumentation for their direct determination, hydrolytic cleavage of β-glucosides followed by analysis of the released parental toxins has been proposed as an indirect determination approach. This study compares the abilities of several fungal and recombinant bacterial β-glucosidases to hydrolyze the model analyte DON-3G. Furthermore, substrate specificities of two fungal and two bacterial (Lactobacillus brevis and Bifidobacterium adolescentis) glycoside hydrolase family 3 β-glucosidases were evaluated on a broader range of substrates. The purified recombinant enzyme from B. adolescentis (BaBgl) displayed high flexibility in substrate specificity and exerted the highest hydrolytic activity toward 3-O-β-d-glucosides of the trichothecenes deoxynivalenol (DON), nivalenol, and HT-2 toxin. A Km of 5.4 mM and a Vmax of 16 μmol min−1 mg−1 were determined with DON-3G. Due to low product inhibition (DON and glucose) and sufficient activity in several extracts of cereal matrices, this enzyme has the potential to be used for indirect analyses of trichothecene-β-glucosides in cereal samples. PMID:25979885

  19. Progesterone 5β-reductases/iridoid synthases (PRISE): gatekeeper role of highly conserved phenylalanines in substrate preference and trapping is supported by molecular dynamics simulations.

    PubMed

    Petersen, Jan; Lanig, Harald; Munkert, Jennifer; Bauer, Peter; Müller-Uri, Frieder; Kreis, Wolfgang

    2016-08-01

    Vein Patterning 1 (VEP1)-encoded progesterone 5β-reductases/iridoid synthases (PRISE) belong to the short-chain dehydrogenase/reductase superfamily of proteins. They are characterized by a set of highly conserved amino acids in the substrate-binding pocket. All PRISEs are capable of reducing the activated C=C double bond of various enones enantioselectively and therefore have a potential as biocatalysts in bioorganic synthesis. Here, recombinant forms of PRISEs of Arabidopsis thaliana and Digitalis lanata were modified using site-directed mutagenesis (SDM). In rDlP5βR, a set of highly conserved amino acids in the vicinity of the catalytic center was individually substituted for alanine resulting in considerable to complete loss of enone reductase activity. F153 and F343, which can be found in most PRISEs known, are located at the outer rim of the catalytic cavity and seem to be involved in substrate binding and their role was addressed in a series of SDM experiments. The wild-type PRISE accepted progesterone (large hydrophobic 1,4-enone) as well as 2-cyclohexen-1-one (small hydrophilic 1,4-enone), whereas the double mutant rAtP5βR_F153A_F343A converted progesterone much better than the wild-type enzyme but almost lost its capability of reducing 2-cyclohexen-1-one. Recombinant Draba aizoides P5βR (rDaP5βR) has a second pair of phenylalanines at position 156 and 345 at the rim of the binding site. These two phenylalanines were introduced into rAtP5βR_F153A_F343A and the resulting quadruple mutant rAtP5βR_F153A_F343A_V156F_V345F partly recovered the ability to reduce 2-cyclohexen-1-one. These results can best be explained by assuming a trapping mechanism in which phenylalanines at the rim of the substrate-binding pocket are involved. The dynamic behavior of individual P5βRs and mutants thereof was investigated by molecular dynamics simulations and all calculations supported the 'gatekeeper' role of phenylalanines at the periphery of the substrate

  20. Thermodynamic and kinetic properties of a red wine pigment: catechin-(4,8)-malvidin-3-O-glucoside.

    PubMed

    Nave, Frederico; Petrov, Vesselin; Pina, Fernando; Teixeira, Natércia; Mateus, Nuno; de Freitas, Victor

    2010-10-28

    Catechin-(4,8)-malvidin-3-glucoside, a red pigment adduct (at acid pH) found in red wine and resulting from the reaction between malvidin-3-glucoside and flavan-3-ols during wine aging, was synthesized. The thermodynamic and kinetic constants of the network of chemical reactions were fully determined by stopped flow: (i) Direct pH jumps, from thermal equilibrated solutions at pH = 1.0 (flavylium cation, AH(+)), show three kinetic processes. The first one occurs within the mixing time of the stopped flow and leads to the formation of quinoidal bases A and/or A(-) depending on the final pH; the second one takes place with a rate constant equal to 0.075 + 33[H(+)] and was attributed to the hydration reaction that forms the pseudobases (hemiketals), B/B(-). The third process is much slower, 2 × 10(-4) s(-1), and is due to the cis-trans isomerization giving rise to a small fraction of trans-chalcones, Ct/Ct(-). (ii) Reverse pH jumps from the thermally equilibrated solution at moderate to neutral pH values back to a sufficiently acidic medium clearly distinguish three kinetic processes: the first one takes place within the dead time and is due to the protonation of the bases; the second process occurs with the same rate constant of the hydration reaction monitored by direct pH jumps and is attributed to the formation of flavylium cation from the B; the last process occurs with a rate constant of 1.8 s(-1), and results from the formation of AH(+) from Ct through B, reflecting the rate of the ring closure (tautomerization). The separation of the hydration from the tautomerization upon a reverse pH jump is only possible because at pH < 1 the former reaction is faster than the last. An identical situation was observed for malvidin-3-glucoside (oenin) for pH < 2. PMID:20925351

  1. Theoretical study of 1,6-anhydrosugar formation from phenyl D-glucosides under basic condition: reasons for higher reactivity of β-anomer.

    PubMed

    Hosoya, Takashi; Nakao, Yoshihide; Sato, Hirofumi; Sakaki, Shigeyoshi

    2010-12-17

    Degradation of anomeric phenyl d-glucosides to levoglucosan under basic condition is theoretically studied. MP4(SDQ)//DFT(B3LYP)-computational results indicate that the degradation of phenyl α-glucoside (R(α)) occurs via the S(N)icB mechanism. In this mechanism, the oxyanion at the C6, which is formed through deprotonation of the OH group, directly attacks the anomeric carbon. On the other hand, the degradation of phenyl β-glucoside (R(β)) occurs via the S(N)icB(2) mechanism. In this mechanism, the oxyanion at the C2 attacks the anomeric carbon in a nucleophilic manner to afford 1,2-anhydride intermediate and then the oxyanion at the C6 attacks the anomeric carbon to afford levoglucosan. The activation barrier is much lower in the reaction of R(β) (ΔG(0++) = 25.6 kcal/mol and E(a) = 26.5 kcal/mol) than in the reaction of R(α) (ΔG(0++) = 38.1 kcal/mol and E(a) = 37.2 kcal/mol), which is consistent with the experimental observation that β-glucoside is generally much more reactive than the corresponding α-glucoside. The lower activation barrier of the reaction of R(β) arises from the stereoelectronic effect, which is induced by the charge transfer from the ring oxygen to the anomeric carbon, and the staggered conformation around the C1-C2 bond. When the stereoelectronic effect is absent, the degradation needs larger activation energy; for instance, the degradation of phenyl 5a-carba-β-d-glucoside (R(Cβ)) occurs with large ΔG(0++) and E(a) values like those of α-glucosides, because the methylene group of R(Cβ) does not contribute to the stereoelectronic effect. Also, the conformation around the C1-C2 bond is staggered in the transition state of the R(β) reaction but eclipsed in that of the R(α) reaction, which also leads to the larger reactivity of R(β). PMID:21082769

  2. Entropy-driven complex formation of malvidin-3- O-glucoside with common polyphenols in ethanol-water binary solutions

    NASA Astrophysics Data System (ADS)

    Kunsági-Máté, Sándor; Ortmann, Erika; Kollár, László; Nikfardjam, Martin Pour

    2008-09-01

    The complex formation of malvidin-3- O-glucoside with several polyphenols, the so-called "copigmentation" phenomenon, was studied in aqueous solutions. To simulate the copigmentation process during fermentation, the stability of the formed complexes was examined in dependence of the ethanol content of the aqueous solution. Results indicate that stronger and larger complexes are formed, when the ethanol content exceeds a critical margin of 8 vol.% However, the size of complexes of malvidin/procyanidin and malvidin/epicatechin is drastically reduced above this critical concentration. Fluorescence lifetime and solvent relaxation measurements give insight into the particular processes at molecular level and will help us comprehend the first important steps during winemaking in order to recommend an optimized winemaking technology to ensure extraordinary colour stability in red wines.

  3. High accumulation of dehydrodiconiferyl alcohol-4-beta-D: -glucoside in free and immobilized Linum usitatissimum cell cultures.

    PubMed

    Attoumbré, Jacques; Charlet, Stéphane; Baltora-Rosset, Sylvie; Hano, Christophe; Raynaud-Le Grandic, Sophie; Gillet, Françoise; Bensaddek, Lamine; Mesnard, François; Fliniaux, Marc-André

    2006-08-01

    As flaxseed mainly accumulates lignans (secoisolariciresinol diglucoside and matairesinol), these compounds were barely or not detected in plant cell suspensions initiated from Linum usitatissimum. In contrast, these cell suspensions were shown to accumulate substantial amounts of a neolignan identified as dehydrodiconiferyl alcohol-4-beta-D: -glucoside (DCG) (up to 47.7 mg g(-1) DW). The formation of this pharmacologically active compound was evaluated as a function of cell growth and in relation to phytohormone balance of the culture media. After establishment of efficient culture conditions, production of DCG was investigated in immobilized plant cell suspensions initiated from plantlet roots of L. usitatissimum. The results indicate that immobilization enhances the DCG production up to 60.0 mg g(-1) DW but depresses the cell growth resulting in no improvement of the total DCG yield. Nevertheless, with immobilized cell suspensions, a release of DCG into the medium is observed allowing an easier recovery. PMID:16523286

  4. Separation and identification of 1,2,4-trihydroxynaphthalene-1-O-glucoside in Impatiens glandulifera Royle.

    PubMed

    Tříska, Jan; Vrchotová, Naděžda; Sýkora, Jan; Moos, Martin

    2013-01-01

    Methanolic extract from lyophilized roots of Impatiens glandulifera Royle was analyzed by high performance liquid chromatography using DAD and FLD detection and this revealed one dominant highly fluorescent very unstable substance. The stability of this derivative is strongly dependent on the plant material drying procedure and extraction procedure used. The structure of the substance was established as 1,2,4-trihydroxynaphthalene-1-O-glucoside (THNG) according LC-MS and NMR measurements. When lyophilized plant material was extracted with methanol an almost four times higher amount of THNG was found in the extract, compared to the amount of 2-hydroxy-1,4-naphthoquinone obtained, while in the case of the same lyophilized plant material extracted with water there was no THNG in the extract. The main compounds in this case was 2-hydroxy-1,4-naphthoquinone. In the plant material dried at the laboratory temperature and extracted by methanol there are only traces of THNG. PMID:23867652

  5. Steroidal Glucosides from the Rhizomes of Tacca chantrieri and Their Inhibitory Activities of NO Production in BV2 Cells.

    PubMed

    Yen, Pham Hai; Chi, Vu Thi Quynh; Kim, Dong-Cheol; Ko, Wonmin; Oh, Hyuncheol; Kim, Youn-Chul; Dung, Duong Thi; Thanh, Nguyen Thi Viet; Quang, Tran Hong; Ngan, Nguyen Thi Thanh; Nhiema, Nguyen Xuan; Anh, Hoang Le Tuan; Minh, Chan Van; Kiem, Phan Van

    2016-01-01

    Two new steroidal glucosides, chantriolides D and E (1 and 2), along with four known compounds, chantriolide A (3), chantriolide B (4), chantriolide C (5), and (25S)-spirost-5-en-3-ol 3-O-α-L-rhamnopyranosyl-(1-->2)-O-[α-L-rhamnopyranosyl-(1-->3)]-β-D-glucopyranoside (6) were isolated from the rhizomes of Tacca chantrieri. Their structures were determined by 1D and 2D NMR spectroscopic and HR-ESI-MS data, as well as by comparison with reported data. Compounds 1 and 2 were found to show strong inhibitory NO effect in BV2 cells, with IC₅₀ values of 12.45 and 59.03 µM, respectively. PMID:26996017

  6. Isolation of cyanidin 3-glucoside from blue honeysuckle fruits by high-speed counter-current chromatography.

    PubMed

    Chen, Liang; Xin, Xiulan; Lan, Rong; Yuan, Qipeng; Wang, Xiaojie; Li, Ye

    2014-01-01

    Blue honeysuckle fruits are rich in anthocyanins with many beneficial effects such as reduction of the risk of cardiovascular diseases, diabetes and cancers. High-speed counter-current chromatography (HSCCC) was used for the separation of anthocyanin on a preparative scale from blue honeysuckle fruit crude extract with a biphasic solvent system composed of tert-butyl methyl ether/n-butanol/acetonitrile/water/trifluoroacetic acid (2:2:1:5:0.01, v/v) for the first time in this paper. Each injection of 100 mg crude extract yielded 22.8 mg of cyanidin 3-glucoside (C3G) at 98.1% purity. The compound was identified by means of electro-spray ionisation mass (ESI/MS) and (1)H and (13)C nuclear magnetic resonance (NMR) spectra. PMID:24444952

  7. Anti-inflammatory effect of the blueberry anthocyanins malvidin-3-glucoside and malvidin-3-galactoside in endothelial cells.

    PubMed

    Huang, Wu-Yang; Liu, Ya-Mei; Wang, Jian; Wang, Xing-Na; Li, Chun-Yang

    2014-01-01

    Blueberry fruits have a wide range of health benefits because of their abundant anthocyanins, which are natural antioxidants. The purpose of this study was to investigate the inhibitory effect of blueberry's two main anthocyanins (malvidin-3-glucoside and malvidin-3-galactoside) on inflammatory response in endothelial cells. These two malvidin glycosides could inhibit tumor necrosis factor-alpha (TNF-α) induced increases of monocyte chemotactic protein-1 (MCP-1), intercellular adhesion molecule-1 (ICAM-1), and vascular cell adhesion molecule-1 (VCAM-1) production both in the protein and mRNA levels in a concentration-dependent manner. Mv-3-glc at the concentration of 1 μM could inhibit 35.9% increased MCP-1, 54.4% ICAM-1, and 44.7% VCAM-1 protein in supernatant, as well as 9.88% MCP-1 and 48.6% ICAM-1 mRNA expression (p<0.05). In addition, they could decrease IκBα degradation (Mv-3-glc, Mv-3-gal, and their mixture at the concentration of 50 μM had the inhibition rate of 84.8%, 75.3%, and 43.2%, respectively, p<0.01) and block the nuclear translocation of p65, which suggested their anti-inflammation mechanism was mediated by the nuclear factor-kappa B (NF-κB) pathway. In general malvidin-3-glucoside had better anti-inflammatory effect than malvidin-3-galactoside. These results indicated that blueberry is good resource of anti-inflammatory anthocyanins, which can be promising molecules for the development of nutraceuticals to prevent chronic inflammation in many diseases. PMID:25153881

  8. CTG-loaded liposomes as an approach for improving the intestinal absorption of asiaticoside in Centella Total Glucosides.

    PubMed

    Wang, Jiayu; Ma, Changhua; Guo, Chengjie; Yuan, Ruijuan; Zhan, Xueyan

    2016-07-25

    Centella Total Glucosides (CTG),obtained from Centella asiatica (L.), have been shown to possess a multitude of pharmacological activities, however, oral administeration of CTG failed to fulfill their therapeutic potentials due to the low bioavailability. In this study, the author prepared the liposomes encapsulated CTG using the ethanol injection method in order to enhance their intestinal absorption. The average particle size and the polydispersityindex(PDI) of CTG-loaded liposome in a batch are 137.0nm and 0.283, and the CTG-loaded amounts in CTG-loaded liposomes were 0.177mgmL(-1) and the zeta potential of CTG-loaded lipsomes is -21.2mV. The TEM images of CTG-loaded lipsomes showed that CTG-loaded liposomes are round and maintain high structural integrity, and their DSC thermograms indicated that CTG might be incorporated into the aqueous phase of DPPC to become more stable. The everted rat gut sac model was used to study the absorption characteristic of CTG-loaded solution in rat intestines. The cumulative absorption amount (Q) and the cumulative absorption percentage (P%) of asiaticoside in the CTG-loaded liposome was significantly higher than that in CTG (P<0.05), both the steady-state infiltration rate (Jss, μgcm(-2)s(-1)) and the permeability coefficient (Papp, cms(-1)) of asiaticoside in CTG-loaded liposomes were significantly higher than those in CTG (P<0.05), which revealed that the liposomes encapsulated CTG can promote the absorption of asiaticoside in the ileum of the rats by enhancing its transmembrane permeability. The above study will provide the experimental evidence and a reference for the development of the oral dosage forms of Centella total glucosides. PMID:27251012

  9. A comparative chemotaxonomic study on Vinca sardoa steam and Vinca difformis pourret.

    PubMed

    Bianco, Armandodoriano; Guiso, Marcella; Nicoletti, Marcello; Foddai, Sebastiano; Piccin, Antonella; Serafini, Mauro; Ballero, Mauro; Poli, Ferruccio

    2005-09-01

    The phytochemical analysis of iridoidic fraction of the aerial parts of Vinca sardoa and Vinca difformis, gave the identification of loganic acid in V. difformis as unique iridoid glucoside, while loganin is also present in V. sardoa. The two taxa highly differ in alkaloids, so the chemotaxonomic classification in two different species is supported. PMID:16010829

  10. cDNA Cloning, Heterologous Expressions, and Functional Characterization of Malonyl-Coenzyme A:Anthocyanidin 3-O-Glucoside-6"-O-Malonyltransferase from Dahlia Flowers1

    PubMed Central

    Suzuki, Hirokazu; Nakayama, Toru; Yonekura-Sakakibara, Keiko; Fukui, Yuko; Nakamura, Noriko; Yamaguchi, Masa-atsu; Tanaka, Yoshikazu; Kusumi, Takaaki; Nishino, Tokuzo

    2002-01-01

    In the flowers of important ornamental Compositae plants, anthocyanins generally carry malonyl group(s) at their 3-glucosyl moiety. In this study, for the first time to our knowledge, we have identified a cDNA coding for this 3-glucoside-specific malonyltransferase for anthocyanins, i.e. malonyl-coenzyme A:anthocyanidin 3-O-glucoside-6"-O-malonyltransferase, from dahlia (Dahlia variabilis) flowers. We isolated a full-length cDNA (Dv3MaT) on the basis of amino acid sequences specifically conserved among anthocyanin acyltransferases of the versatile plant acyltransferase family. Dv3MaT coded for a protein of 460 amino acids. Quantitative real-time PCR analyses of Dv3MaT showed that the transcript was present in accordance with the distribution of 3MaT activities and the anthocyanin accumulation pattern in the dahlia plant. The Dv3MaT cDNA was expressed in Escherichia coli, and the recombinant enzyme was purified to homogeneity and characterized. The recombinant Dv3MaT catalyzed the regiospecific transfer of the malonyl group from malonyl-coenzyme A (Km, 18.8 μm) to pelargonidin 3-O-glucoside (Km, 46.7 μm) to produce pelargonidin 3-O-6"-O-malonylglucoside with a kcat value of 7.3 s−1. The other enzymatic profiles of the recombinant Dv3MaT were closely related to those of native anthocyanin malonyltransferase activity in the extracts of dahlia flowers. Dv3MaT cDNA was introduced into petunia (Petunia hybrida) plants whose red floral color is exclusively provided by cyanidin 3-O-glucoside and 3,5-O-diglucoside. Thirteen transgenic lines of petunia were found to produce malonylated products of these anthocyanins (11–63 mol % of total anthocyanins in the flower). The spectral stability of cyanidin 3-O-6"-O-malonylglucoside at the pHs of intracellular milieus of flowers was significantly higher than that of cyanidin 3-O-glucoside. Moreover, 6"-O-malonylation of cyanidin 3-O-glucoside effectively prevented the anthocyanin from attack of β-glucosidase. These results

  11. Identification of rice Os4BGlu13 as a β-glucosidase which hydrolyzes gibberellin A4 1-O-β-d-glucosyl ester, in addition to tuberonic acid glucoside and salicylic acid derivative glucosides.

    PubMed

    Hua, Yanling; Ekkhara, Watsamon; Sansenya, Sompong; Srisomsap, Chantragan; Roytrakul, Sittiruk; Saburi, Wataru; Takeda, Ryosuke; Matsuura, Hideyuki; Mori, Haruhide; Ketudat Cairns, James R

    2015-10-01

    Gibberellin 1-O-β-d-glucose ester hydrolysis activity has been detected in rice seedling extracts, but no enzyme responsible for this activity has ever been purified and identified. Therefore, gibberellin A4 glucosyl ester (GA4-GE) β-d-glucosidase activity was purified from ten-day rice seedling stems and leaves. The family 1 glycoside hydrolase Os4BGlu13 was identified in the final purification fraction. The Os4BGlu13 cDNA was amplified from rice seedlings and expressed as an N-terminal thioredoxin-tagged fusion protein in Escherichia coli. The purified recombinant Os4BGlu13 protein (rOs4BGlu13) had an optimum pH of 4.5, for hydrolysis of p-nitrophenyl β-d-glucopyranoside (pNPGlc), which was the best substrate identified, with a kcat/Km of 637 mM(-1) s(-1). rOs4BGlu13 hydrolyzed helicin best among natural glycosides tested (kcat/Km of 74.4 mM(-1) s(-1)). Os4BGlu13 was previously designated tuberonic acid glucoside (TAG) β-glucosidase (TAGG), and here the kcat/Km of rOsBGlu13 for TAG was 6.68 mM(-1) s(-1), while that for GA4-GE was 3.63 mM(-1) s(-1) and for salicylic acid glucoside (SAG) is 0.88 mM(-1) s(-1). rOs4BGlu13 also hydrolyzed oligosaccharides, with preference for short β-(1 → 3)-linked over β-(1 → 4)-linked glucooligosaccharides. The enzymatic data suggests that Os4BGlu13 may contribute to TAG, SAG, oligosaccharide and GA4-GE hydrolysis in the rice plant, although helicin or a similar compound may be its primary target. PMID:26241499

  12. In vitro and in vivo study of cucurbitacins-type triterpene glucoside from Citrullus colocynthis growing in Saudi Arabia against hepatocellular carcinoma.

    PubMed

    Ayyad, Seif-Eldin N; Abdel-Lateff, Ahmed; Alarif, Walied M; Patacchioli, Francesca R; Badria, Farid A; Ezmirly, Saleh T

    2012-03-01

    Chromatographic investigation of fruits obtained from Citrullus colocynthis, growing in Saudi Arabia, led to isolation of two compounds; Cucurbitacin E glucoside (Cu E, 1), and Cucurbitacin I glucoside (Cu I, 2). The chemical structures of 1 and 2, were elucidated by spectroscopic analyses include; 1D ((1)H and (13)C) and 2D (COSY, HMQC and HMBC) NMR and ESI-MS spectroscopy. The in vitro cytotoxic activity against hepatoma cell line (HepG2) and mice-bearing tumor of Ehrlich's ascites carcinoma (EAC) of the compounds were estimated. Both compounds had potent inhibitory activity on HepG2 with IC(50) 3.5 and 2.8 nmol/mL, respectively. In addition to these activities, the in vivo study employing EAC, showed the capability of both compounds to prolong the survival time, life span and normalize the biochemical parameters of the infected mice with EAC. PMID:22245841

  13. Assessment of extraction parameters on antioxidant capacity, polyphenol content, epigallocatechin gallate (EGCG), epicatechin gallate (ECG) and iriflophenone 3-C-β-glucoside of agarwood (Aquilaria crassna) young leaves.

    PubMed

    Tay, Pei Yin; Tan, Chin Ping; Abas, Faridah; Yim, Hip Seng; Ho, Chun Wai

    2014-01-01

    The effects of ethanol concentration (0%-100%, v/v), solid-to-solvent ratio (1:10-1:60, w/v) and extraction time (30-180 min) on the extraction of polyphenols from agarwood (Aquilaria crassna) were examined. Total phenolic content (TPC), total flavonoid content (TFC) and total flavanol (TF) assays and HPLC-DAD were used for the determination and quantification of polyphenols, flavanol gallates (epigallocatechin gallate--EGCG and epicatechin gallate--ECG) and a benzophenone (iriflophenone 3-C-β-glucoside) from the crude polyphenol extract (CPE) of A. crassna. 2,2'-Diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity was used to evaluate the antioxidant capacity of the CPE. Experimental results concluded that ethanol concentration and solid-to-solvent ratio had significant effects (p<0.05) on the yields of polyphenol and antioxidant capacity. Extraction time had an insignificant influence on the recovery of EGCG, ECG and iriflophenone 3-C-β-glucoside, as well as radical scavenging capacity from the CPE. The extraction parameters that exhibited maximum yields were 40% (v/v) ethanol, 1:60 (w/v) for 30 min where the TPC, TFC, TF, DPPH, EGCG, ECG and iriflophenone 3-C-β-glucoside levels achieved were 183.5 mg GAE/g DW, 249.0 mg QE/g DW, 4.9 mg CE/g DW, 93.7%, 29.1 mg EGCG/g DW, 44.3 mg ECG/g DW and 39.9 mg iriflophenone 3-C-β-glucoside/g DW respectively. The IC50 of the CPE was 24.6 mg/L. PMID:25153858

  14. Dianthosaponins G-I, triterpene saponins, an anthranilic acid amide glucoside and a flavonoid glycoside from the aerial parts of Dianthus japonicus and their cytotoxicity.

    PubMed

    Kanehira, Yuka; Kawakami, Susumu; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki

    2016-10-01

    Extensive isolation work on the 1-BuOH-soluble fraction of a MeOH extract of the aerial parts of Dianthus japonicus afforded three further triterpene glycosyl estsers, termed dianthosaponins G-I, an anthranilic acid amide glucoside and a C-glycosyl flavonoid along with one known triterpene saponin. Their structures were elucidated from spectroscopic evidence. The cytotoxicity of the isolated compounds toward A549 cells was evaluated. PMID:27351981

  15. A flavonoid 3-O-glucoside:2″-O-glucosyltransferase responsible for terminal modification of pollen-specific flavonols in Arabidopsis thaliana

    PubMed Central

    Yonekura-Sakakibara, Keiko; Nakabayashi, Ryo; Sugawara, Satoko; Tohge, Takayuki; Ito, Takuya; Koyanagi, Misuzu; Kitajima, Mariko; Takayama, Hiromitsu; Saito, Kazuki

    2014-01-01

    Flavonol 3-O-diglucosides with a 1→2 inter-glycosidic linkage are representative pollen-specific flavonols that are widely distributed in plants, but their biosynthetic genes and physiological roles are not well understood. Flavonoid analysis of four Arabidopsis floral organs (pistils, stamens, petals and calyxes) and flowers of wild-type and male sterility 1 (ms1) mutants, which are defective in normal development of pollen and tapetum, showed that kaempferol/quercetin 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosides accumulated in Arabidopsis pollen. Microarray data using wild-type and ms1 mutants, gene expression patterns in various organs, and phylogenetic analysis of UDP-glycosyltransferases (UGTs) suggest that UGT79B6 (At5g54010) is a key modification enzyme for determining pollen-specific flavonol structure. Kaempferol and quercetin 3-O-glucosyl-(1→2)-glucosides were absent from two independent ugt79b6 knockout mutants. Transgenic ugt79b6 mutant lines transformed with the genomic UGT79B6 gene had the same flavonoid profile as wild-type plants. Recombinant UGT79B6 protein converted kaempferol 3-O-glucoside to kaempferol 3-O-glucosyl-(1→2)-glucoside. UGT79B6 recognized 3-O-glucosylated/galactosylated anthocyanins/flavonols but not 3,5- or 3,7-diglycosylated flavonoids, and prefers UDP-glucose, indicating that UGT79B6 encodes flavonoid 3-O-glucoside:2″-O-glucosyltransferase. A UGT79B6-GUS fusion showed that UGT79B6 was localized in tapetum cells and microspores of developing anthers. PMID:24916675

  16. Resistance of glucose-6-phosphate dehydrogenase deficiency to malaria: effects of fava bean hydroxypyrimidine glucosides on Plasmodium falciparum growth in culture and on the phagocytosis of infected cells.

    PubMed

    Ginsburg, H; Atamna, H; Shalmiev, G; Kanaani, J; Krugliak, M

    1996-07-01

    The balanced polymorphism of glucose-6-phosphate dehydrogenase deficiency (G6PD-) is believed to have evolved through the selective pressure of malarial combined with consumption of fava beans. The implicated fava bean constituents are the hydroxypyrimidine glucosides vicine and convicine, which upon hydrolysis of their beta-O-glucosidic bond, became protein pro-oxidants. In this work we show that the glucosides inhibit the growth of Plasmodium falciparum, increase the hexose-monophosphate shunt activity and the phagocytosis of malaria-infected erythrocytes. These activities are exacerbated in the presence of beta-glucosidase, implicating their pro-oxidant aglycones in the toxic effect, and are more pronounced in infected G6PD- erythrocytes. These results suggest that G6PD- infected erythrocytes are more susceptible to phagocytic cells, and that fava bean pro-oxidants are more efficiently suppressing parasite propagation in G6PD- erythrocytes, either by directly affecting parasite growth, or by means of enhanced phagocytic elimination of infected cells. The present findings could account for the relative resistance of G6PD- bearers to falciparum malaria, and establish a link between dietary habits and malaria in the selection of the G6PD- genotype. PMID:8710417

  17. HPLC determination of malondialdehyde in ECV304 cell culture medium for measuring the antioxidant effect of vitexin-4''-O-glucoside.

    PubMed

    Ying, Xi-xiang; Li, Hai-bo; Chu, Zheng-yun; Zhai, Yan-jun; Leng, Ai-jing; Liu, Xun; Xin, Chun; Zhang, Wen-jie; Kang, Ting-guo

    2008-07-01

    To investigate the antioxidant effect of vitexin-4''-O-glucoside, a flavone glycoside, isolated from the leaves of Crataegus pinnatifida Bge. var. major, we developed a simple and sensitive high-performance liquid chromatography (HPLC) method to determine levels of malondialdehyde (MDA) in ECV304 cell culture medium after induction by tert-butyl-hydroperoxide (TBHP). The preparation of analyzed samples involved a one-step derivatization with thiobarbituric acid (TBA). HPLC analysis was performed on a Synergi Hydro-RP, a polar end-capped C18 column (250 x 4.6 mm, 4 mum), using an acetonitrile-ammonium acetate aqueous solution (10 mM, pH 6.8) as the mobile phase under linear gradient conditions with UV detection at 532 nm. The calibration curve was linear over 0.0125-1.25 microM MDA (r = 0.9951). Relative standard deviations (RSDs) of intra-day and inter-day precision were less than 6.1% and 5.0%, respectively. The mean recovery was 96.9 +/- 1.6%. The lower limit of quantification (LLOQ) of MDA was 0.0125 microM. This chromatographic method was successfully applied to investigating the in vitro antioxidant effect of vitexin-4''-O-glucoside. Vitexin-4''-O-glucoside (120 M) protected ECV304 cells from peroxidation induced by TBHP. PMID:18704330

  18. Comparative abilities and optimal conditions for beta-glycosidase enzymes to hydrolyse the glucuronide, glucoside, and N-acetylglucosaminide conjugates of bile acids.

    PubMed

    Momose, T; Maruyama, J; Iida, T; Goto, J; Nambara, T

    1997-08-01

    Enzymatic hydrolyses were described for three variants of glycosidic conjugated bile acids with one beta-glucuronidase (Helix pomatia), three beta-glucosidase (almonds, sweet almonds, and Escherichia coli), and four beta-N-acetylglucosaminidase (jack beans, bovine kidney, human placenta, and Diplococcus pneumoniae) preparations. The substrates include the beta-glucuronide, beta-glucoside, and beta-N-acetylglucosaminide conjugates of bile acids related to hyodeoxycholic, murideoxycholic, chenodeoxycholic, and ursodeoxycholic acids possessing a sugar moiety at position C-3, C-6 or C-7. The comparative abilities and optimal conditions for the beta-glycosidases to catalyze the hydrolyses of the substrates were clarified by changing pHs and incubation times. Hydrolysis rates of the bile acid glycosides with beta-glycosidase treatments were influenced by both the source of the enzyme preparations and the conjugated position of a sugar moiety in the substrates, and the 3-glucoside and 3-N-acetylglucosaminide conjugates were usually hydrolyzed more efficiently than their corresponding 6- and 7-analogs. Escherichia coli and jack bean enzymes were chosen to hydrolyse the glucosidic and N-acetylglucosaminidic conjugated bile acids, respectively. PMID:9300125

  19. Cytotoxicity of obacunone and obacunone glucoside in human prostate cancer cells involves Akt-mediated programmed cell death.

    PubMed

    Murthy, Kotamballi N Chidambara; Jayaprakasha, Guddadarangavvanahally K; Patil, Bhimanagouda S

    2015-03-01

    Obacunone and obacunone glucoside (OG) are naturally occurring triterpenoids commonly found in citrus and other plants of the Rutaceae family. The current study reports the mechanism of cytotoxicity of citrus-derived obacunone and OG on human androgen-dependent prostate cancer LNCaP cells. Both limonoids exhibited time- and dose-dependent inhibition of cell proliferation, with more than 60% inhibition of cell viability at 100 μM, after 24 and 48 h. Analysis of fragmentation of DNA, activity of caspase-3, and cytosolic cytochrome-c in the cells treated with limonoids provided evidence for activation of programmed cell death by limonoids. Treatment of LNCaP cells with obacunone and OG resulted in dose-dependent changes in expression of proteins responsible for the induction of programmed cell death through the intrinsic pathway and down-regulation of Akt, a key molecule in cell signaling pathways. In addition, obacunone and OG also negatively regulated an inflammation-associated transcription factor, androgen receptor, and prostate-specific antigen, and activated proteins related to the cell cycle, confirming the ability of limonoids to induce cytotoxicity through multiple pathways. The results of this study provided, for the first time, an evidence of the cytotoxicity of obacunone and OG in androgen-dependent human prostate cancer cells. PMID:25592883

  20. Anti-diabetic effects of luteolin and luteolin-7-O-glucoside on KK-A(y) mice.

    PubMed

    Zang, Yanqing; Igarashi, Kiharu; Li, Yu

    2016-08-01

    Anti-diabetic potential of luteolin (LU) and luteolin-7-O-glucoside (LUG) were investigated in the amount of equimolar on KK-A(y) mice. The results showed that both of LU and LUG significantly improved blood glucose, HbA1c, insulin, and HOMR-IR levels. Anti-inflammatory and anti-oxidative effects of the LU and LUG were also proved. Furthermore, TGs in serum and liver were significantly decreased in the LU and LUG groups, as well as the mRNA expression of fat acid expression-related genes (SREBP-1c), compared to the basal diet group (CON). When compared the effects between the LU and LUG groups, TGs of the LU group were lower than those of the LUG group, accompanied with significantly decreased FAS activity and SREBP-1c expression in liver. These results suggested that both LU and LUG had positive effects of anti-diabetes on KK-A(y) mice, but LU more potently ameliorated diabetes than LUG, which might be attributed to the inhibitory of lipid synthesis. PMID:27170065

  1. ABCC1, an ATP Binding Cassette Protein from Grape Berry, Transports Anthocyanidin 3-O-Glucosides[W][OA

    PubMed Central

    Francisco, Rita Maria; Regalado, Ana; Ageorges, Agnès; Burla, Bo J.; Bassin, Barbara; Eisenach, Cornelia; Zarrouk, Olfa; Vialet, Sandrine; Marlin, Thérèse; Chaves, Maria Manuela; Martinoia, Enrico; Nagy, Réka

    2013-01-01

    Accumulation of anthocyanins in the exocarp of red grapevine (Vitis vinifera) cultivars is one of several events that characterize the onset of grape berry ripening (véraison). Despite our thorough understanding of anthocyanin biosynthesis and regulation, little is known about the molecular aspects of their transport. The participation of ATP binding cassette (ABC) proteins in vacuolar anthocyanin transport has long been a matter of debate. Here, we present biochemical evidence that an ABC protein, ABCC1, localizes to the tonoplast and is involved in the transport of glucosylated anthocyanidins. ABCC1 is expressed in the exocarp throughout berry development and ripening, with a significant increase at véraison (i.e., the onset of ripening). Transport experiments using microsomes isolated from ABCC1-expressing yeast cells showed that ABCC1 transports malvidin 3-O-glucoside. The transport strictly depends on the presence of GSH, which is cotransported with the anthocyanins and is sensitive to inhibitors of ABC proteins. By exposing anthocyanin-producing grapevine root cultures to buthionine sulphoximine, which reduced GSH levels, a decrease in anthocyanin concentration is observed. In conclusion, we provide evidence that ABCC1 acts as an anthocyanin transporter that depends on GSH without the formation of an anthocyanin-GSH conjugate. PMID:23723325

  2. Deoxynivalenol & Deoxynivalenol-3-Glucoside Mitigation through Bakery Production Strategies: Effective Experimental Design within Industrial Rusk-Making Technology

    PubMed Central

    Generotti, Silvia; Cirlini, Martina; Malachova, Alexandra; Sulyok, Michael; Berthiller, Franz; Dall’Asta, Chiara; Suman, Michele

    2015-01-01

    In the scientific field, there is a progressive awareness about the potential implications of food processing on mycotoxins especially concerning thermal treatments. High temperatures may cause, in fact, transformation or degradation of these compounds. This work is aimed to study the fate of mycotoxins during bakery processing, focusing on deoxynivalenol (DON) and deoxynivalenol-3-glucoside (DON3Glc), along the chain of industrial rusk production. Starting from naturally contaminated bran, we studied how concentrations of DON and DON3Glc are influenced by modifying ingredients and operative conditions. The experiments were performed using statistical Design of Experiment (DoE) schemes to synergistically explore the relationship between mycotoxin reduction and the indicated processing transformation parameters. All samples collected during pilot plant experiments were analyzed with an LC-MS/MS multimycotoxin method. The obtained model shows a good fitting, giving back relevant information in terms of optimization of the industrial production process, in particular suggesting that time and temperature in baking and toasting steps are highly relevant for minimizing mycotoxin level in rusks. A reduction up to 30% for DON and DON3Glc content in the finished product was observed within an acceptable technological range. PMID:26213969

  3. In-vivo absorption of pinocembrin-7-O-β-D-glucoside in rats and its in-vitro biotransformation

    PubMed Central

    Guo, Wei-Wei; Qiu, Feng; Chen, Xiao-Qing; Ba, Yin-Ying; Wang, Xing; Wu, Xia

    2016-01-01

    Pinocembrin-7-O-β-D-glucoside (PCBG), a flavonoid isolated from Penthorum chinense Pursh., has significant liver-protecting effects. The pharmacokinetics of PCBG and its major metabolite pinocembrin (PCB) in rats were investigated in this study. A sensitive and accurate UPLC-MS/MS method was developed and validated for the simultaneous quantitative determination of PCBG and PCB in rat plasma after oral and intravenous administration of PCBG. After intravenous administration, PCBG was the main form in plasma. In contrast, after oral administration, the concentration of PCB was about 4-fold higher than that of PCBG, indicating that PCBG was metabolized to PCB. We also investigated the biotransformation of PCBG in vitro in order to understand whether the pH and the intestinal flora of gastrointestinal tract could affect the metabolism of PCBG. PCBG was incubated in rat plasma, liver homogenization, gastrointestial contents, liver microsomes (RLM) and hepatocytes in vitro. The data showed that PCB was quickly formed in the gastrointestinal incubation but PCBG was converted to PCB gradually in other incubations. The results indicated that the majority of PCBG was converted to its aglycone PCB in digestive system after oral administration, and PCB could be the active ingredient in the body. PMID:27378517

  4. Facile preparation of water soluble curcuminoids extracted from turmeric (Curcuma longa L.) powder by using steviol glucosides.

    PubMed

    Nguyen, Thi Thanh Hanh; Si, Jinbeom; Kang, Choongil; Chung, Byoungsang; Chung, Donghwa; Kim, Doman

    2017-01-01

    Curcuminoids from rhizomes of Curcuma longa possess various biological activities. However, low aqueous solubility and consequent poor bioavailability of curcuminoids are major limitations to their use. In this study, curcuminoids extracted from turmeric powder using stevioside (Ste), rebaudioside A (RebA), or steviol glucosides (SG) were solubilized in water. The optimum extraction condition by Ste, RebA, or SG resulted in 11.3, 9.7, or 6.7mg/ml water soluble curcuminoids. Curcuminoids solubilized in water showed 80% stability at pH from 6.0 to 10.0 after 1week of storage at 25°C. The particle sizes of curcuminoids prepared with Ste, RebA, and SG were 110.8, 95.7, and 32.7nm, respectively. The water soluble turmeric extracts prepared with Ste, RebA, and SG showed the 2,2-diphenyl-1-picrylhydrazyl radical scavenging (SC50) activities of 127.6, 105.4, and 109.8μg/ml, and the inhibition activities (IC50) against NS2B-NS3(pro) from dengue virus type IV of 14.1, 24.0 and 15.3μg/ml, respectively. PMID:27507487

  5. Five furofuranone lignan glucosides from Terminalia citrina inhibit in vitro E2-enhanced breast cancer cell proliferation.

    PubMed

    Muhit, Md Abdul; Umehara, Kaoru; Noguchi, Hiroshi

    2016-09-01

    Five new polyalkoxylated furofuranone lignan glucosides, terminalosides L-P (1-5), were isolated from EtOAc extracts of the leaves of Terminalia citrina, a Bangladeshi medicinal plant. The structures of the isolates were deduced primarily by NMR spectroscopy, and four of the isolates were found to contain rare tetraoxygenated aryl groups in their structures. The absolute configurations and conformations of the furofuranone ring were confirmed by ECD spectroscopy. All of the isolates were evaluated for their estrogenic and/or antiestrogenic properties using two estrogen responsive breast cancer cell lines, T47D and MCF-7. At a concentration of 10nM, terminaloside L (1) suppressed E2-enhanced T47D cell proliferation by 90%, while terminaloside M (2) showed 90% antiestrogenic activity against MCF-7 cells. Compared to 2, the antiestrogenic activity of terminaloside O (4) and P (5) was weak, possibly due to the different attachment positions of the sugar moiety that they share in common. This is the first report of furofuranone lignans from any Terminalia species, and also of their antiestrogenic activity. PMID:27425446

  6. Long Chain Fatty Acid Acylated Derivatives of Quercetin-3-O-Glucoside as Antioxidants to Prevent Lipid Oxidation

    PubMed Central

    Warnakulasuriya, Sumudu N.; Ziaullah; Rupasinghe, H.P. Vasantha

    2014-01-01

    Flavonoids have shown promise as natural plant-based antioxidants for protecting lipids from oxidation. It was hypothesized that their applications in lipophilic food systems can be further enhanced by esterification of flavonoids with fatty acids. Quercetin-3-O-glucoside (Q3G) was esterified individually with six selected long chain fatty acids: stearic acid (STA), oleic acid (OLA), linoleic acid (LNA), α-linolenic acid (ALA), eicosapentaenoic acid (EPA) and decosahexaenoic acid (DHA), using Candida antarctica B lipase as the biocatalyst. The antioxidant activity of esterified flavonoids was evaluated using lipid oxidation model systems of poly-unsaturated fatty acids-rich fish oil and human low density lipoprotein (LDL), in vitro. In the oil-in-water emulsion, Q3G esters exhibited 50% to 100% inhibition in primary oxidation and 30% to 75% inhibition in secondary oxidation. In bulk oil, Q3G esters did not provide considerable protection from lipid oxidation; however, Q3G demonstrated more than 50% inhibition in primary oxidation. EPA, DHA and ALA esters of Q3G showed significantly higher inhibition in Cu2+- and peroxyl radical-induced LDL oxidation in comparison to Q3G. PMID:25384198

  7. Stability, Antioxidant Capacity and Degradation Kinetics of Pelargonidin-3-glucoside Exposed to Ultrasound Power at Low Temperature.

    PubMed

    Sun, Jianxia; Mei, Zhouxiong; Tang, Yajuan; Ding, Lijun; Jiang, Guichuan; Zhang, Chi; Sun, Aidong; Bai, Weibin

    2016-01-01

    As an alternative preservation method to thermal treatment, ultrasound is a novel non-thermal processing technology that can significantly avoid undesirable nutritional changes. However, recently literature indicated that anthocyanin degradation occurred when high amplitude ultrasound was applied to juice. This work mainly studied the effect of ultrasound on the stability and antioxidant capacity of pelargonidin-3-glucoside (Pg-3-glu) and the correlation between anthocyanin degradation and •OH generation in a simulated system. Results indicated that the spectral intensities of Pg-3-glu decreased with increasing ultrasound power (200-500 W) and treatment time (0-60 min). The degradation trend was consistent with first-order reaction kinetics (R² > 0.9100). Further study showed that there was a good linear correlation between Pg-3-glu degradation and •OH production (R² = 0.8790), which indicated the important role of •OH in the degradation of anthocyanin during ultrasound exposure. Moreover, a decrease in the antioxidant activity of solution(s) containing Pg-3-glu as evaluated by the DPPH and FRAP methods was observed after ultrasound treatment. PMID:27563863

  8. Isolation of a flavonoid, apigenin 7-O-glucoside, from Mentha longifolia (L.) Hudson subspecies longifolia and its genotoxic potency.

    PubMed

    Gulluce, Medine; Orhan, Furkan; Yanmis, Derya; Arasoglu, Tulin; Guvenalp, Zuhal; Demirezer, Lutfiye Omur

    2015-09-01

    Mentha is a medicinal and aromatic plant belonging to the Lamiaceae family, which is widely used in food, flavor, cosmetic and pharmaceutical industries. Recently, it has been found that the use of Mentha as a pharmaceutical source is based on its phytochemical constituents that have far been identified as tannins, saponins, phenolic acids and flavonoids. This study was designed to evaluate the mutagenic and antimutagenic activities of apigenin 7-O-glucoside (A7G), a flavonoid isolated from Mentha longifolia (L.) Hudson subspecies longifolia (ML). The possible antimutagenic potential of A7G was examined against mutagens ethyl methanesulfonate and acridine in an eukaryotic cell system Saccharomyces cerevisiae and sodium azide in Salmonella typhimurium TA1535 and 9-aminoacridine in S. typhimurium TA1537. According to our findings, any concentrations of the A7G used did not show mutagenic activity but exerted strong antimutagenic activities at tested concentrations. The inhibition rates for the Ames test ranged from 27.2% (S. typhimurium TA1535: 0.4 μM/plate) to 91.1% (S. typhimurium TA1537: 0.2 μM/plate) and for the yeast deletion assay from 4% to 57.7%. This genotoxicological study suggests that a flavonoid from ML owing to antimutagenic properties is of great pharmacological importance and might be beneficial to industries producing food additives, cosmetics and pharmaceuticals products. PMID:23377117

  9. Combined multispectroscopic and molecular docking investigation on the interaction between delphinidin-3-O-glucoside and bovine serum albumin.

    PubMed

    Zuo, Huijun; Tang, Lin; Li, Shu; Huang, Junwei

    2015-02-01

    Anthocyanin is one of the flavonoid phytopigments with specific health benefits. The interaction between delphinidin-3-O-glucoside (D3G) and bovine serum albumin (BSA) was investigated by fluorescence spectroscopy, synchronous fluorescence spectroscopy, three-dimensional fluorescence spectroscopy, ultraviolet-visible absorption spectroscopy, circular dichroism spectroscopy and molecular modeling. D3G effectively quenched the intrinsic fluorescence of BSA via static quenching. The number of binding sites and binding constant Ka were determined, and the hydrogen bonds and van der Waals forces played major roles in stabilizing the D3G-BSA complex. The distance r between donor and acceptor was obtained as 2.81 nm according to Förster's theory. In addition, the effects of pH and metal ions on the binding constants were discussed. The results studied by synchronous fluorescence, three-dimensional fluorescence and circular dichroism experiments indicated that the secondary structures of the protein has been changed by the addition of D3G and the α-helix content of BSA decreased (from 56.1% to 52.4%). Furthermore, the study of site marker competitive experiments and molecular modeling indicated that D3G could bind to site I of BSA, which was in the large hydrophobic cavity of subdomain IIA. PMID:24891226

  10. Deoxynivalenol & Deoxynivalenol-3-Glucoside Mitigation through Bakery Production Strategies: Effective Experimental Design within Industrial Rusk-Making Technology.

    PubMed

    Generotti, Silvia; Cirlini, Martina; Malachova, Alexandra; Sulyok, Michael; Berthiller, Franz; Dall'Asta, Chiara; Suman, Michele

    2015-08-01

    In the scientific field, there is a progressive awareness about the potential implications of food processing on mycotoxins especially concerning thermal treatments. High temperatures may cause, in fact, transformation or degradation of these compounds. This work is aimed to study the fate of mycotoxins during bakery processing, focusing on deoxynivalenol (DON) and deoxynivalenol-3-glucoside (DON3Glc), along the chain of industrial rusk production. Starting from naturally contaminated bran, we studied how concentrations of DON and DON3Glc are influenced by modifying ingredients and operative conditions. The experiments were performed using statistical Design of Experiment (DoE) schemes to synergistically explore the relationship between mycotoxin reduction and the indicated processing transformation parameters. All samples collected during pilot plant experiments were analyzed with an LC-MS/MS multimycotoxin method. The obtained model shows a good fitting, giving back relevant information in terms of optimization of the industrial production process, in particular suggesting that time and temperature in baking and toasting steps are highly relevant for minimizing mycotoxin level in rusks. A reduction up to 30% for DON and DON3Glc content in the finished product was observed within an acceptable technological range. PMID:26213969

  11. A natural flavonoid glucoside icariin inhibits Th1 and Th17 cell differentiation and ameliorates experimental autoimmune encephalomyelitis.

    PubMed

    Shen, Ruile; Deng, Wenjing; Li, Chun; Zeng, Guangwei

    2015-02-01

    Multiple sclerosis (MS) is an autoimmune disease that is characterized by recurrent episodes of T cell-mediated immune attack on central nervous system (CNS) myelin, leading to axon damage and progressive disability. Icariin, a natural flavonoid glucoside isolated from plants in the Epimedium family, has been proved to have various pharmacological activities. However, the effect of icariin on experimental autoimmune encephalomyelitis (EAE) has never been investigated. In our current study, we found that icariin treatment leads to alleviated inflammatory infiltration and reduced blood-brain barrier leakage (BBB) of the paracellular tracer (FITC-dextran) in EAE. Mice that received icariin-treated T cells also displayed lower EAE scores and better clinical recovery from EAE. Icariin administration suppresses the frequencies of Th1 and Th17 cells in the splenocytes and lymph node cells. Icariin-treated mice also show lower frequency of Th17 cells in CNS mononuclear cells. The effect of icariin on Th1 and Th17 cell differentiation may be mediated via modulation of dendritic cells (DCs). Furthermore, icariin suppresses the proliferation of T cells and the differentiation of Th1 and Th17 cells in vitro. In conclusion, icariin ameliorates EAE and this was associated with suppressed Th1 and Th17 cell differentiation. PMID:25528476

  12. Tetrahydroxystilbene glucoside improves TNF-α-induced endothelial dysfunction: involvement of TGFβ/Smad pathway and inhibition of vimentin expression.

    PubMed

    Yao, Wenjuan; Gu, Chengjing; Shao, Haoran; Meng, Guoliang; Wang, Huiming; Jing, Xiang; Zhang, Wei

    2015-01-01

    Endothelial dysfunction plays an important role in the pathogenesis of atherogenesis. 2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucoside (TSG), an active component of the rhizome extract from Polygonum multiflorum (PM), exhibits significant anti-atherosclerotic activity. Here, we used human umbilical vein endothelial cells (HUVECs) induced by tumor necrosis factor-α (TNF-α) in vitro to investigate the cytoprotective effects of TSG on TNF-α-induced endothelial injury and the related mechanisms. Pretreatment with 50 and 100 μM TSG markedly attenuated TNF-α-induced loss of cell viability and release of lactate dehydrogenase (LDH) and inhibited TNF-α-induced cell apoptosis. The inhibition of vimentin expression was involved in the cytoprotection afforded by TSG. Using inhibitors for PI3K and TGFβ or siRNA for Akt and Smad2, we found that vimentin production in HUVECs is regulated by TGFβ/Smad signaling, but not by PI3K-Akt-mTOR signaling. Meanwhile, TSG inhibited both the expression of TGFβ1 and the phosphorylation of Smad2 and Smad3, and TSG suppressed the nuclear translocation of Smad4 induced by TNF-α. These results suggest that TSG protects HUVECs against TNF-α-induced cell damage by inhibiting vimentin expression via the interruption of the TGFβ/Smad signaling pathway. PMID:25571766

  13. Behaviour of cyanidin-3-glucoside, β-lactoglobulin and polysaccharides nanoparticles in bulk and oil-in-water interfaces.

    PubMed

    Oliveira, Ana; Ruiz-Henestrosa, Víctor M Pizones; von Staszewski, Mariana; Pilosof, Ana M R; Pintado, Manuela

    2015-11-01

    Particle size distributions as well the interfacial and rheological properties of the films at the oil/water interface were used to study the effect of the interacting system between β-lactoglobulin, cyanidin-3-glucoside and pectin or chitosan in buffer solutions. The particles obtained were smaller with cy-3-gluc-β-lg-pectin and had reduced polydispersity with cy-3-gluc-β-lg-chitosan. Based on time dependent surface pressure results, β-lg-pectin mixtures showed a slower increase at the beginning of the measurement, while β-lg-chitosan mixtures showed no differences with β-lg alone. Contrarily, dilatational properties increased for ternary chitosan mixtures, but they remained similar to the pure protein in ternary pectin mixtures. Cy-3-gluc interfacial properties were reduced by the presence of pectin and chitosan. The interactions between cy-3-gluc and the biopolymers that have been selected in the present work resulted in a lower content of free polyphenol, reduced antioxidant properties as well as free β-lg. The impact of this effect was more relevant when pectin was used. PMID:26256371

  14. Copigmentation of malvidin-3-O-glucoside with five hydroxybenzoic acids in red wine model solutions: experimental and theoretical investigations.

    PubMed

    Zhang, Bo; Liu, Rui; He, Fei; Zhou, Pan-Pan; Duan, Chang-Qing

    2015-03-01

    In the present research, the copigmentations of malvidin-3-O-glucoside with five hydroxybenzoic cofactors (p-hydroxybenzoic acid, protocatechuic acid, gallic acid, vanillic acid, and syringic acid) were investigated. The influence of the concentration of these cofactors and the reaction temperature was examined. The equilibrium constant (K), stoichiometric ratio (n) and the thermodynamic parameters (ΔG°, ΔH°, ΔS°) related to the copigmentation were also reported here. Theoretical calculations were performed to identify the relative arrangement between the pigment and cofactors in the copigmentation complexes. Besides, the comparison of the relative binding free energies (ΔΔGbinding) derived from the theoretical calculations and experimental data were made, and the binding strength of these copigmentation complexes was discussed with the interaction energies (ΔE). AIM analysis was also used to explore the main driving forces contributing to the copigmentation. In the comparison of the five studied cofactors, syringic acid had a stronger copigmentation effect than the other four phenolic acids investigated. PMID:25306339

  15. Flavonol Glucoside and Antioxidant Enzyme Biosynthesis Affected by Mycorrhizal Fungi in Various Cultivars of Onion (Allium cepa L.).

    PubMed

    Mollavali, Mohanna; Bolandnazar, Saheb Ali; Schwarz, Dietmar; Rohn, Sascha; Riehle, Peer; Zaare Nahandi, Fariborz

    2016-01-13

    The objective of this study was to investigate the impact of mycorrhizal symbiosis on qualitative characteristics of onion (Allium cepa L.). For this reason, five onion cultivars with different scale color and three different strains of arbuscular mycorrhizal fungi (Diversispora versiformis, Rhizophagus intraradices, Funneliformis mosseae) were used. Red cultivars, mainly 'Red Azar-shahr', showed the highest content in vitamin C, flavonols, and antioxidant enzymes. Mycorrhizal inoculation increased total phenolic, pyruvic acid, and vitamin C of onion plants. Considerable increase was observed in quercetin-4'-O-monoglucoside and isorhamnetin-4'-O-monoglucoside content in plants inoculated with Diversispora versiformis, but quercetin-3,4'-O-diglucoside was not significantly influenced. Analyses for phenylalanine ammonia-lyase (PAL) and antioxiodant enzyme activities such as polyphenol oxidase (PPO), catalase (CAT), and peroxidase (POD) revealed that all except PPO were enhanced by mycorrhizal inoculation. Overall, these findings suggested that mycorrhizal inoculation influenced biosynthesis of flavonol glucosides and antioxidant enzymes by increasing nutrient uptake or by induction of the plant defense system. PMID:26694086

  16. Binding of the alkaloid aristololactam-β-D-glucoside and daunomycin to human hemoglobin: spectroscopy and calorimetry studies.

    PubMed

    Das, Abhi; Suresh Kumar, Gopinatha

    2016-04-01

    The interaction of the plant alkaloid aristololactam-β-D-glucoside (ADG) and the anticancer agent daunomycin (DAN) with human hemoglobin was studied by different spectroscopic and calorimetric methods. The binding affinity values of ADG and DAN, estimated from spectroscopic experiments, were 3.79 × 10(4) and 6.68 × 10(4) M(-1), respectively. From circular dichroism, 3D fluorescence, and FTIR studies it was observed that, DAN induced stronger conformational changes than ADG in the protein. From synchronous fluorescence spectroscopy results, a pronounced shift in the maximum emission wavelength of tyrosine residues was observed in both cases suggesting that the drugs changed the polarity around tyrosine residues with marginal change around the tryptophan residues. The thermodynamics of the binding interaction analyzed using microcalorimetry presented single binding events that were exothermic in nature in both cases. The binding was driven by large positive standard molar entropy changes with small favorable enthalpy contributions. Negative heat capacity changes in both cases are correlated to the involvement of significant hydrophobic forces in the complexation process. The affinity of DAN to Hb was higher than that of ADG. PMID:26065442

  17. Analysis of deoxynivalenol and deoxynivalenol-3-glucosides content in Canadian spring wheat cultivars inoculated with Fusarium graminearum.

    PubMed

    Amarasinghe, Chami C; Simsek, Senay; Brûlé-Babel, Anita; Fernando, W G Dilantha

    2016-07-01

    Contamination of wheat grains with Fusarium mycotoxins and their modified forms is an important issue in wheat industry. The objective of this study was to analyse the deoxynivalenol (DON) and deoxynivalenol-3-glucosides (D3G) content in Canadian spring wheat cultivars grown in two locations, inoculated with a mixture of 3-acetyldeoxynivalenol (3-ADON)-producing Fusarium graminearum strains and a mixture of 15-acetlyldeoxynivalenol (15-ADON)-producing F. graminearum strains. According to the analysis of variance, significant differences were observed among the cultivars for Fusarium head blight (FHB) disease index, Fusarium-damaged kernel percentage (%FDK), DON content and D3G content. When the effect of chemotype was considered, significant differences were observed for FHB disease index, FDK percentage and DON content. The D3G content and D3G/DON ratio were not significantly different between the chemotypes, except for D3G content at the Winnipeg location. The Pearson correlation coefficient between DON and D3G was 0.84 and 0.77 at Winnipeg and Carman respectively. The highest D3G/DON ratio was observed in cultivars Carberry (44%) in Carman and CDC Kernen (63.8%) in Winnipeg. The susceptible cultivars showed lower D3G/DON ratio compared with the cultivars rated as moderately resistant and intermediate. The current study indicated that Canadian spring cultivars produce D3G upon Fusarium infection. PMID:27264644

  18. A new monoterpene glucoside and complete assignments of dihydroflavonols of Pulicaria jaubertii: potential cytotoxic and blood pressure lowering activity.

    PubMed

    Ragab, Ehab A; Raafat, Mohamed

    2016-06-01

    One new monoterpene glucoside and five dihydroflavonols were isolated for the first time from the aerial parts of Pulicaria jaubertii and identified as p-menthane-2-O-β-D-glucopyranoside [1], dihydroquercetin (taxifolin) [2], 7,3'-di-O-methyltaxifolin [3], 3'-O-methyltaxifolin [4], 7-O-methyltaxifolin (padmatin) [5] and 7-O-methyl-dihydrokampferol (7-O-methylaromadenderin) [6]. The structures of these compounds were unambiguously assigned on the basis of NMR spectroscopic data ((1)H, (13)C, DEPT, HSQC, HMBC) and MS analysis. 2D-NMR methods required revision of assignments of H-6 and H-8 for dihydroflavonol compounds. Possible cytotoxic activity as well as blood pressure (BP) lowering activity were tested. The alcoholic extract showed cytotoxic activity against prostate carcinoma (PC-3), breast carcinoma (MCF-7) and hepatocellular carcinoma (HepG-2) human cell lines with IC50 19.1, 20.0 and 24.1 μg, respectively. The higher dose levels of the alcoholic extract significantly reduced normal BP of rats in a dose-dependent manner. PMID:26247309

  19. In-vivo absorption of pinocembrin-7-O-β-D-glucoside in rats and its in-vitro biotransformation.

    PubMed

    Guo, Wei-Wei; Qiu, Feng; Chen, Xiao-Qing; Ba, Yin-Ying; Wang, Xing; Wu, Xia

    2016-01-01

    Pinocembrin-7-O-β-D-glucoside (PCBG), a flavonoid isolated from Penthorum chinense Pursh., has significant liver-protecting effects. The pharmacokinetics of PCBG and its major metabolite pinocembrin (PCB) in rats were investigated in this study. A sensitive and accurate UPLC-MS/MS method was developed and validated for the simultaneous quantitative determination of PCBG and PCB in rat plasma after oral and intravenous administration of PCBG. After intravenous administration, PCBG was the main form in plasma. In contrast, after oral administration, the concentration of PCB was about 4-fold higher than that of PCBG, indicating that PCBG was metabolized to PCB. We also investigated the biotransformation of PCBG in vitro in order to understand whether the pH and the intestinal flora of gastrointestinal tract could affect the metabolism of PCBG. PCBG was incubated in rat plasma, liver homogenization, gastrointestial contents, liver microsomes (RLM) and hepatocytes in vitro. The data showed that PCB was quickly formed in the gastrointestinal incubation but PCBG was converted to PCB gradually in other incubations. The results indicated that the majority of PCBG was converted to its aglycone PCB in digestive system after oral administration, and PCB could be the active ingredient in the body. PMID:27378517

  20. Differentiation of flavonol glucoside and galactoside isomers combining chemical isopropylidenation with liquid chromatography-mass spectrometry analysis.

    PubMed

    de Souza, Lauro M; Dartora, Nessana; Scoparo, Camila T; Gorin, Philip A J; Iacomini, Marcello; Sassaki, Guilherme L

    2016-05-20

    Flavonol glycosides are important components of leaves from vascular plants. A lot of isomers of these compounds are produced by plants, making their analysis very difficult and causing many structural misinterpretations. Galactosides and glucosides as mono- or oligosaccharides yield many diastereoisomers, hindering the analysis by mass spectrometry. In order to enable the mass spectrometric distinctions of these isomers, in this work we combine an isopropylidene based chemical derivatization with liquid chromatography with multiple-stage mass spectrometry (LC-MS(n)) analysis. The isomers of flavonol triglycosides, after the reaction, yielded products with different molecular weight, therefore, they were no longer isomers, allowing their identification by MS(1) analysis. However, to the 4 isomers of flavonol diglycosides, only one yielded, after isopropylidenation, a product with different molecular weight. To the other 3 species, the incorporation of 2 isopropylidene groups retained them in the isomeric form. For such species, chromatographic separation and MS(n) detection targeting the lithium adducts of 3,4-O-isopropylidene-galactosyl or 4,6-O-isopropylidene-glucosyl residues (m/z 209.099) provided specific MS profile. PMID:27109198

  1. Determination of the relative contribution of quercetin and its glucosides to the antioxidant capacity of onion by cyclic voltammetry and spectrophotometric methods.

    PubMed

    Zielinska, Danuta; Wiczkowski, Wieslaw; Piskula, Mariusz Konrad

    2008-05-28

    This paper describes the use of cyclic voltammetry (CV), spectrophotometric methods [Trolox equivalent antioxidant capacity (TEAC), peroxyl radical trapping capacity (PRTC), DPPH radical scavenging activity (RSA), and Folin-Ciocalteu reagent (FCR) reducing capacity], and photochemiluminescence (PCL) for the measurement of the antioxidant capacity of onion var. Sochaczewska and var. Szalotka. The antioxidant and reducing activity of the dominant onion flavonoids quercetin (Q), quercetin-3- O-beta-glucoside (Q3G), quercetin-4'- O-beta-glucoside (Q4'G), and quercetin-3,4'-di- O-beta-glucoside (Q3,4'G) were determined by spectrophotometric (TEAC and PRTC) and CV methods, respectively. The contribution of quercetin and its glucosides to the antioxidant capacity of onion was calculated in consequence of the qualitative and quantitative analysis of onion flavonoids by high-performance liquid chromatography-ultraviolet-mass spectrometry. The dominant forms of quercetin in the onion var. Sochaczewska and Szalotka included Q4'G (61 and 54%), Q3,4'G (37 and 44%), Q3G (1.4 and 1.1%), and free quercetin (1.1 and 0.7%), respectively. The CV experiment showed the highest reducing activity of Q while Q3G, Q4'G, and Q3,4'G exhibited about 68, 51, and 30% of the reducing power noted for Q. The order of the reducing activity of onion flavonoids was confirmed by their free radical scavenging activity and evaluated by TEAC and PRTC assays as follows: Q > Q3G > Q4'G > Q3,4'G. The Q4'G and Q3,4'G showed poor antioxidant activity under both applied spectrophotometric assays but still exhibited reducing activity based on CV experiments. The reducing capacity of onions determined by CV method was twice higher than the antioxidant capacity formed by water-soluble compounds (ACW) evaluated by PCL, and it was about 50% higher than PRTC and DPPH RSA results and the converted FCR reducing capacity. In contrast, the reducing capacity of onions determined by the CV method was 3-fold and about four

  2. Repellent activity of catmint, Nepeta cataria, and iridoid nepetalactone isomers against Afro-tropical mosquitoes, ixodid ticks and red poultry mites.

    PubMed

    Birkett, Michael A; Hassanali, Ahmed; Hoglund, Solveig; Pettersson, Jan; Pickett, John A

    2011-01-01

    The repellent activity of the essential oil of the catmint plant, Nepeta cataria (Lamiaceae), and the main iridoid compounds (4aS,7S,7aR) and (4aS,7S,7aS)-nepetalactone, was assessed against (i) major Afro-tropical pathogen vector mosquitoes, i.e. the malaria mosquito, Anopheles gambiae s.s. and the Southern house mosquito, Culex quinquefasciatus, using a World Health Organisation (WHO)-approved topical application bioassay (ii) the brown ear tick, Rhipicephalus appendiculatus, using a climbing repellency assay, and (iii) the red poultry mite, Dermanyssus gallinae, using field trapping experiments. Gas chromatography (GC) and coupled GC-mass spectrometry (GC-MS) analysis of two N. cataria chemotypes (A and B) used in the repellency assays showed that (4aS,7S,7aR) and (4aS,7S,7aS)-nepetalactone were present in different proportions, with one of the oils (from chemotype A) being dominated by the (4aS,7S,7aR) isomer (91.95% by GC), and the other oil (from chemotype B) containing the two (4aS,7S,7aR) and (4aS,7S,7aS) isomers in 16.98% and 69.83% (by GC), respectively. The sesquiterpene hydrocarbon (E)-(1R,9S)-caryophyllene was identified as the only other major component in the oils (8.05% and 13.19% by GC, respectively). Using the topical application bioassay, the oils showed high repellent activity (chemotype A RD(50)=0.081 mg cm(-2) and chemotype B RD(50)=0.091 mg cm(-2)) for An. gambiae comparable with the synthetic repellent DEET (RD(50)=0.12 mg cm(-2)), whilst for Cx. quinquefasciatus, lower repellent activity was recorded (chemotype A RD(50)=0.34 mg cm(-2) and chemotype B RD(50)=0.074 mg cm(-2)). Further repellency testing against An. gambiae using the purified (4aS,7S,7aR) and (4aS,7S,7aS)-nepetalactone isomers revealed overall lower repellent activity, compared to the chemotype A and B oils. Testing of binary mixtures of the (4aS,7S,7aR) and (4aS,7S,7aS) isomers across a range of ratios, but all at the same overall dose (0.1 mg), revealed not only a

  3. A pre-clinical pharmacokinetic study in rats of three naturally occurring iridoid glycosides, Picroside-I, II and III, using a validated simultaneous HPLC-MS/MS assay.

    PubMed

    Zhu, Jianwei; Xue, Bingyang; Ma, Bo; Zhang, Qi; Liu, Ming; Liu, Lei; Yao, Di; Qi, Huanhuan; Wang, Yonglu; Ying, Hanjie; Wu, Zimei

    2015-07-01

    A selective and sensitive high-performance liquid chromatography-electro-spray ionization tandem mass spectrometry (LC-ESI-MS/MS) method was developed for the simultaneous quantitative determination of Picroside-I, II, and III in rat plasma and tissue homogenate to aid the pre-clinical studies. The chromatographic separation was performed on a Hypersil GOLD AQ C18 column using a gradient elution program with a mobile phase consisting of 2mM ammonium acetate and acetonitrile. The detection was achieved using a triple quadrupole tandem MS in negative ionization multiple reaction monitoring (MRM) mode. One-step protein precipitation was selected for plasma and tissue sample preparation while liquid-liquid extraction failed to achieve satisfactory recoveries. The calibration curves of all three analytes in either plasma or tissue homogenate showed good linearity over the concentration range of 0.5-500ng/mL with a limit of quantitation at 0.5ng/mL. Both the intra- and inter-day accuracy and precision were within ±10%. The extraction recoveries were >70%, and the relative matrix effect ranged from 80.4% to 107.4% in all the biological samples. All the analytes were stable in matrices for at least 24h at room temperature, or 21 days in frozen. Three freeze/thaw cycles did not cause degradation. The method was successfully applied for quantification of the three iridoid glycosides in the collected plasma and various tissues following intravenous administration in rats. Picroside-I, II, and III were all eliminated rapidly with large volume of distribution. Among the three glycosides, Picroside-II showed the highest liver uptake, and only Picroside-I and II were found to get across the blood brain barrier (BBB). These results were consistent with their hepatoprotective or neuroprotective effects reported clinically. With the aid of the efficient and reliable simultaneous LC-ESI-MS/MS assay this pharmacokinetic study provided insights into their therapeutic targets of these

  4. The Human Fecal Microbiota Metabolizes Deoxynivalenol and Deoxynivalenol-3-Glucoside and May Be Responsible for Urinary Deepoxy-Deoxynivalenol

    PubMed Central

    Duncan, Gary; Richardson, Anthony J.

    2013-01-01

    Deoxynivalenol (DON) is a potent mycotoxin produced by Fusarium molds and affects intestinal nutrient absorption and barrier function in experimental and farm animals. Free DON and the plant metabolite DON-3-β-d-glucoside (D3G) are frequently found in wheat and maize. D3G is stable in the upper human gut, but some human intestinal bacteria release DON from D3G in vitro. Furthermore, some bacteria derived from animal digestive systems degrade DON to a less toxic metabolite, deepoxy-deoxynivalenol (DOM-1). The metabolism of D3G and DON by the human microbiota has not been fully assessed. We therefore conducted in vitro batch culture experiments assessing the activity of the human fecal microbiota to release DON from D3G. We also studied detoxification of DON to DOM-1 by the microbiota and its potential effect on urinary DON excretion in humans. Fecal slurry from five volunteers was spiked with DON or D3G and incubated anaerobically (from 1 h to 7 days), and mycotoxins were extracted into acetonitrile. Mycotoxins were detected in fecal extracts and urine by liquid chromatography-tandem mass spectrometry (LC-MS/MS). The fecal microbiota released DON from D3G very efficiently, with hydrolysis peaking after 4 to 6 h. The fecal microbiota from one volunteer transformed DON to DOM-1. Urine from the same volunteer also contained DOM-1 (4.7% of DON), whereas DOM-1 was not detectable in urine from other volunteers. Our results confirm that the fecal microbiota releases DON from its glycosylated form, hence increasing the toxic burden in exposed individuals. Furthermore, this is first evidence that the human fecal microbiota of one volunteer detoxifies DON, resulting in the appearance of DOM-1 in urine. PMID:23315729

  5. A Validated HPLC Method for Simultaneous Determination of Caffeoyl Phenylethanoid Glucosides and Flavone 8-C-glycosides in Haberlea rhodopensis.

    PubMed

    Zheleva-Dimitrova, Dimitrina; Nedialkov, Paraskev; Giresser, Ulrich

    2016-06-01

    A HPLC-UV method for analysis of the main compounds: caffeoyl phenylethanoid glucosides myconoside (1) and paucifloside (2) and flavone 8-C-glycosides: hispidulin 8-C-β-galactopyranoside (3), hispidulin 8-C-(2"-O-syringoyl-β-glucopyranoside) (4), hispidulin 8-C-(6-O-acetyl-β-glucopyranoside) (5) and hispidulin 8-C-(6-O-acetyl-2"-O-syringoyl--glucopyranoside) (6) in Haberlea rhodopensis leaves was developed and validated. Compound 3 was isolated for the first time from the title species. Ultrasound extraction with 80% methanol at room temperature allowed a good recovery of analytes (from 87.2 % for 1 to 109.8 % for 3) and the precision of the entire procedure was between 1.6% and 6.9%. The subsequent HPLC separation and quantification was achieved using a Hypersil ODS C18 column and UV detection at 280 nm. The mobile phase comprised methanol and 0.1 % o-phosphoric acid, and gradient elution mode was applied. The detection limits ranged from 0.042 μg/mL (6) to 0.18 μg/mL (5). The total amount in leaves of the assayed phenolic compounds was 374.2 mg/g. Myconoside was found to be the dominant compound in H. rhodopensis extract (332.2 ± 0.7 mg/g dw) and reached up to 88.8% of the analyzed mixture in leaves, while the total content of flavone C-glycosides was 17.1 mg/g dw. PMID:27534117

  6. Maltotriose Utilization by Industrial Saccharomyces Strains: Characterization of a New Member of the α-Glucoside Transporter Family

    PubMed Central

    Salema-Oom, Madalena; Valadão Pinto, Vera; Gonçalves, Paula; Spencer-Martins, Isabel

    2005-01-01

    Maltotriose utilization by Saccharomyces cerevisiae and closely related yeasts is important to industrial processes based on starch hydrolysates, where the trisaccharide is present in significant concentrations and often is not completely consumed. We undertook an integrated study to better understand maltotriose metabolism in a mixture with glucose and maltose. Physiological data obtained for a particularly fast-growing distiller's strain (PYCC 5297) showed that, in contrast to what has been previously reported for other strains, maltotriose is essentially fermented. The respiratory quotient was, however, considerably higher for maltotriose (0.36) than for maltose (0.16) or glucose (0.11). To assess the role of transport in the sequential utilization of maltose and maltotriose, we investigated the presence of genes involved in maltotriose uptake in the type strain of Saccharomyces carlsbergensis (PYCC 4457). To this end, a previously constructed genomic library was used to identify maltotriose transporter genes by functional complementation of a strain devoid of known maltose transporters. One gene, clearly belonging to the MAL transporter family, was repeatedly isolated from the library. Sequence comparison showed that the novel gene (designated MTY1) shares 90% and 54% identity with MAL31 and AGT1, respectively. However, expression of Mty1p restores growth of the S. cerevisiae receptor strain on both maltose and maltotriose, whereas the closely related Mal31p supports growth on maltose only and Agt1p supports growth on a wider range of substrates, including maltose and maltotriose. Interestingly, Mty1p displays higher affinity for maltotriose than for maltose, a new feature among all the α-glucoside transporters described so far. PMID:16151085

  7. Deoxynivalenol, deoxynivalenol-3-glucoside, and enniatins: the major mycotoxins found in cereal-based products on the Czech market.

    PubMed

    Malachova, Alexandra; Dzuman, Zbynek; Veprikova, Zdenka; Vaclavikova, Marta; Zachariasova, Milena; Hajslova, Jana

    2011-12-28

    Fusarium toxins, Alternaria toxins, and ergot alkaloids represent common groups of mycotoxins that can be found in cereals grown under temperate climatic conditions. Because most of them are chemically and thermally stable, these toxic fungal secondary metabolites might be transferred from grains into the final products. To get information on the commensurate contamination of various cereal-based products collected from the Czech retail market in 2010, the occurrence of "traditional" mycotoxins such as groups of A and B trichothecenes and zearalenone, less routinely determined Alternaria toxins (alternariol, alternariol monomethyl ether and altenuene), ergot alkaloids (ergosine, ergocryptine, ergocristine, and ergocornine) and "emerging" mycotoxins (enniatins A, A1, B, and B1 and beauvericin) were monitored. In a total 116 samples derived from white flour and mixed flour, breakfast cereals, snacks, and flour, only trichothecenes A and B and enniatins were found. Deoxynivalenol was detected in 75% of samples with concentrations ranging from 13 to 594 μg/kg, but its masked form, deoxynivalenol-3-β-d-glucoside, has an even higher incidence of 80% of samples, and concentrations ranging between 5 and 72 μg/kg were detected. Nivalenol was found only in three samples at levels of 30 μg/kg. For enniatins, all of the samples investigated were contaminated with at least one of four target enniatins. Enniatin A was detected in 97% of samples (concentration range of 20-2532 μg/kg) followed by enniatin B with an incidence in 91% of the samples (concentration range of 13-941 μg/kg) and enniatin B1 with an incidence of 80% in the samples tested (concentration range of 8-785 μg/kg). Enniatin A1 was found only in 44% of samples at levels ranging between 8 and 851 μg/kg. PMID:22070284

  8. Total Glucosides of Paeony Promote Intestinal Motility in Slow Transit Constipation Rats through Amelioration of Interstitial Cells of Cajal

    PubMed Central

    Zhu, Feiye; Xu, Shan; Zhang, Yongsheng; Chen, Fangming; Ji, Jinjun; Xie, Guanqun

    2016-01-01

    Objectives Using an atropine-diphenoxylate-induced slow transit constipation (STC) model, this study explored the effects of the total glucosides of paeony (TGP) in the treatment of STC and the possible mechanisms. Study Design A prospective experimental animal study. Methods The constipation model was set up in rats with an oral gavage of atropine-diphenoxylate and then treated with the TGP. The volume and moisture content of the faeces were observed and the intestinal kinetic power was evaluated. Meanwhile, the colorimetric method and enzyme linked immunosorbent assay (ELISA) were employed to determine the changes of nitric oxide (NO), nitric oxide synthase (NOS), vasoative intestinal peptide (VIP) and the P substance (SP) in the serum, respectively. The protein expressions of c-kit and stem cell factor (SCF) were assessed by immunohistochemical analysis and western blot, respectively, and the mRNA level of c-kit was measured by a reverse transcription polymerase chain reaction (RT-PCR). Results The TGP attenuated STC responses in terms of an increase in the fecal volume and moisture content, an enhancement of intestinal transit rate and the reduction of NO, NOS and VIP in the serum. In addition, the c-kit, a labeling of interstitial cells of Cajal (ICC) increased at both protein and mRNA levels. SCF, which serves as a ligand of c-kit also increased at protein level. Conclusion The analysis of our data indicated that the TGP could obviously attenuate STC through improving the function of ICC and blocking the inhibitory neurotransmitters such as NO, NOS and VIP. PMID:27478893

  9. Molecular dynamics simulations of the lyotropic reverse hexagonal (HII) of Guerbet branched-chain β-D-glucoside.

    PubMed

    Nguan, Hockseng; Ahmadi, Sara; Hashim, Rauzah

    2014-01-01

    Through atomistic molecular dynamic simulations using a GROMOS53a6 force field for the carbohydrate, we studied the lyotropic reverse hexagonal phase HII from a glycolipid, namely the Guerbet branched-chain β-d-glucoside, at 14% and 22% water concentrations. Our simulations showed that at low water concentration (14%) the sugar head group overlapped extensively and protruded into the water channel. In contrast, in the 22% concentration system a water column free from the sugar headgroup ('free' water) was formed as expected for the system close to the limit of maximum hydration. In both concentrations, we found anomalous water diffusion in the xy-plane, i.e. the two-dimensional space confined by the surface of the cylinder. On the other hand, along the z-axis, the water diffusion obeyed the Einstein relation for the 22% system, while for the 14% system it was slightly anomalous. For the 22% system, the diffusion along the z-axis of the 'free' water obeyed the Einstein relation, while that of the 'bound' water is slightly anomalous. The xy-plane displacement of the 'bound' water was higher than that for the 'free' water at times longer than 200 ps, as a consequence of the exchange of water molecules between the two regions. Based on our findings, we proposed an alternative explanation to the observed spatial heterogeneity in the HII phase from probe diffusion by Penaloza et al. (Phys. Chem. Chem. Phys., 2012, 14(15), 5247-5250). We found the extent of contact with water was different at different oxygen atoms within the sugar ring. Generally, a higher probability of hydrogen bonding but a shorter lifetime was found in 22% water compared to the case of 14% water. Finally, we examined the extension and compression of the alkyl chain of a columnar. PMID:24257208

  10. Metabolic profile of FYX-051 (4-(5-pyridin-4-yl-1h-[1,2,4]triazol-3-yl)pyridine-2-carbonitrile) in the rat, dog, monkey, and human: identification of N-glucuronides and N-glucosides.

    PubMed

    Nakazawa, Takashi; Miyata, Kengo; Omura, Koichi; Iwanaga, Takashi; Nagata, Osamu

    2006-11-01

    FYX-051, 4-(5-pyridin-4-yl-1H-[1,2,4]triazol-3-yl)pyridine-2-carbonitrile, is a novel xanthine oxidoreductase inhibitor that can be used for the treatment of gout and hyperuricemia. We examined the metabolism of FYX-051 in rats, dogs, monkeys, and human volunteers after the p.o. administration of this inhibitor. The main metabolites in urine were pyridine N-oxide in rats, triazole N-glucoside in dogs, and triazole N-glucuronide in monkeys and humans, respectively. Furthermore, N-glucuronidation and N-glucosidation were characterized by two types of conjugation: triazole N(1)- and N(2)-glucuronidation and N(1)- and N(2)-glucosidation, respectively. N(1)- and N(2)-glucuronidation was observed in each species, whereas N(1)- and N(2)-glucosidation was mainly observed in dogs. With regard to the position of conjugation, N(1)-conjugation was predominant; this resulted in a considerably higher amount of N(1)-conjugate in each species than N(2)-conjugate. The present results indicate that the conjugation reaction observed in FYX-051 metabolism is unique, i.e., N-glucuronidation and N-glucosidation occur at the same position of the triazole ring, resulting in the generation of four different conjugates in mammals. In addition, a urinary profile of FYX-051 metabolites in monkeys and humans was relatively similar; triazole N-glucuronides were mainly excreted in urine. PMID:16914512

  11. The crystal structure of rice (Oryza sativa L.) Os4BGlu12, an oligosaccharide and tuberonic acid glucoside-hydrolyzing β-glucosidase with significant thioglucohydrolase activity.

    PubMed

    Sansenya, Sompong; Opassiri, Rodjana; Kuaprasert, Buabarn; Chen, Chun-Jung; Cairns, James R Ketudat

    2011-06-01

    Rice Os4BGlu12, a glycoside hydrolase family 1 (GH1) β-glucosidase, hydrolyzes β-(1,4)-linked oligosaccharides of 3-6 glucosyl residues and the β-(1,3)-linked disaccharide laminaribiose, as well as certain glycosides. The crystal structures of apo Os4BGlu12, and its complexes with 2,4-dinitrophenyl-2-deoxyl-2-fluoroglucoside (DNP2FG) and 2-deoxy-2-fluoroglucose (G2F) were solved at 2.50, 2.45 and 2.40Å resolution, respectively. The overall structure of rice Os4BGlu12 is typical of GH1 enzymes, but it contains an extra disulfide bridge in the loop B region. The glucose ring of the G2F in the covalent intermediate was found in a (4)C(1) chair conformation, while that of the noncovalently bound DNP2FG had a (1)S(3) skew boat, consistent with hydrolysis via a (4)H(3) half-chair transition state. The position of the catalytic nucleophile (Glu393) in the G2F structure was more similar to that of the Sinapsis alba myrosinase G2F complex than to that in covalent intermediates of other O-glucosidases, such as rice Os3BGlu6 and Os3BGlu7 β-glucosidases. This correlated with a significant thioglucosidase activity for Os4BGlu12, although with 200- to 1200-fold lower k(cat)/K(m) values for S-glucosides than the comparable O-glucosides, while hydrolysis of S-glucosides was undetectable for Os3BGlu6 and Os3BGlu7. PMID:21521631

  12. Functional characterization, homology modeling and docking studies of β-glucosidase responsible for bioactivation of cyanogenic hydroxynitrile glucosides from Leucaena leucocephala (subabul).

    PubMed

    Shaik, Noor M; Misra, Anurag; Singh, Somesh; Fatangare, Amol B; Ramakumar, Suryanarayanarao; Rawal, Shuban K; Khan, Bashir M

    2013-02-01

    Glycosyl hydrolase family 1 β-glucosidases are important enzymes that serve many diverse functions in plants including defense, whereby hydrolyzing the defensive compounds such as hydroxynitrile glucosides. A hydroxynitrile glucoside cleaving β-glucosidase gene (Llbglu1) was isolated from Leucaena leucocephala, cloned into pET-28a (+) and expressed in E. coli BL21 (DE3) cells. The recombinant enzyme was purified by Ni-NTA affinity chromatography. The optimal temperature and pH for this β-glucosidase were found to be 45 °C and 4.8, respectively. The purified Llbglu1 enzyme hydrolyzed the synthetic glycosides, pNPGlucoside (pNPGlc) and pNPGalactoside (pNPGal). Also, the enzyme hydrolyzed amygdalin, a hydroxynitrile glycoside and a few of the tested flavonoid and isoflavonoid glucosides. The kinetic parameters K (m) and V (max) were found to be 38.59 μM and 0.8237 μM/mg/min for pNPGlc, whereas for pNPGal the values were observed as 1845 μM and 0.1037 μM/mg/min. In the present study, a three dimensional (3D) model of the Llbglu1 was built by MODELLER software to find out the substrate binding sites and the quality of the model was examined using the program PROCHEK. Docking studies indicated that conserved active site residues are Glu 199, Glu 413, His 153, Asn 198, Val 270, Asn 340, and Trp 462. Docking of rhodiocyanoside A with the modeled Llbglu1 resulted in a binding with free energy change (ΔG) of -5.52 kcal/mol on which basis rhodiocyanoside A could be considered as a potential substrate. PMID:23079707

  13. Plant Community Diversity Influences Allocation to Direct Chemical Defence in Plantago lanceolata

    PubMed Central

    Mraja, Anne; Unsicker, Sybille B.; Reichelt, Michael; Gershenzon, Jonathan; Roscher, Christiane

    2011-01-01

    Background Forecasting the consequences of accelerating rates of changes in biodiversity for ecosystem functioning requires a mechanistic understanding of the relationships between the structure of biological communities and variation in plant functional characteristics. So far, experimental data of how plant species diversity influences the investment of individual plants in direct chemical defences against herbivores and pathogens is lacking. Methodology/Principal Findings We used Plantago lanceolata as a model species in experimental grasslands differing in species richness and composition (Jena Experiment) to investigate foliar concentrations of the iridoid glycosides (IG), catalpol and its biosynthetic precursor aucubin. Total IG and aucubin concentrations decreased, while catalpol concentrations increased with increasing plant diversity in terms of species or functional group richness. Negative plant diversity effects on total IG and aucubin concentrations correlated with increasing specific leaf area of P. lanceolata, suggesting that greater allocation to light acquisition reduced the investment into these carbon-based defence components. In contrast, increasing leaf nitrogen concentrations best explained increasing concentrations of the biosynthetically more advanced IG, catalpol. Observed levels of leaf damage explained a significant proportion of variation in total IG and aucubin concentrations, but did not account for variance in catalpol concentrations. Conclusions/Significance Our results clearly show that plants growing in communities of varying species richness and composition differ in their defensive chemistry, which may modulate plant susceptibility to enemy attack and consequently their interactions with higher trophic level organisms. PMID:22174766

  14. Human lens coloration and aging. Evidence for crystallin modification by the major ultraviolet filter, 3-hydroxy-kynurenine O-beta-D-glucoside.

    PubMed

    Hood, B D; Garner, B; Truscott, R J

    1999-11-12

    The human lens becomes increasingly yellow with age and thereby reduces our perception of blue light. This coloration is associated with lens proteins (crystallins), but its molecular basis was unknown. Here we show that the coloration occurs because of the interaction of crystallins with a UV filter compound, 3-hydroxykynurenine glucoside (3-OHKG). Crystallin modification results from deamination of the 3-OHKG amino acid side chain, yielding an unsaturated ketone that is susceptible to nucleophilic attack by cysteine, histidine, and lysine residues. This novel protein modification contributes to age-related lens coloration and may play a role in human nuclear cataractogenesis. PMID:10551806

  15. Biological Activities of 2,3,5,4′-Tetrahydroxystilbene-2-O-β-D-Glucoside in Antiaging and Antiaging-Related Disease Treatments

    PubMed Central

    2016-01-01

    2,3,5,4′-Tetrahydroxystilbene-2-O-β-D-glucoside (THSG) is active component of the Chinese medicinal plant Polygonum multiflorum Thunb. (THSG). Pharmacological studies have demonstrated that THSG exhibits numerous biological functions in treating atherosclerosis, lipid metabolism, vascular and cardiac remodeling, vascular fibrosis, cardiac-cerebral ischemia, learning and memory disorders, neuroinflammation, Alzheimer and Parkinson diseases, diabetic complications, hair growth problems, and numerous other conditions. This review focuses on the biological effects of THSG in antiaging and antiaging-related disease treatments and discusses its molecular mechanisms. PMID:27413420

  16. Biological Activities of 2,3,5,4'-Tetrahydroxystilbene-2-O-β-D-Glucoside in Antiaging and Antiaging-Related Disease Treatments.

    PubMed

    Ling, Shuang; Xu, Jin-Wen

    2016-01-01

    2,3,5,4'-Tetrahydroxystilbene-2-O-β-D-glucoside (THSG) is active component of the Chinese medicinal plant Polygonum multiflorum Thunb. (THSG). Pharmacological studies have demonstrated that THSG exhibits numerous biological functions in treating atherosclerosis, lipid metabolism, vascular and cardiac remodeling, vascular fibrosis, cardiac-cerebral ischemia, learning and memory disorders, neuroinflammation, Alzheimer and Parkinson diseases, diabetic complications, hair growth problems, and numerous other conditions. This review focuses on the biological effects of THSG in antiaging and antiaging-related disease treatments and discusses its molecular mechanisms. PMID:27413420

  17. Production of rosmarinic acid and a new rosmarinic acid 3'-O-beta-D-glucoside in suspension cultures of the hornwort Anthoceros agrestis Paton.

    PubMed

    Vogelsang, Katharina; Schneider, Bernd; Petersen, Maike

    2006-01-01

    Cell suspension cultures of the hornwort Anthoceros agrestis Paton (Anthocerotaceae) were cultivated and characterized in CB-media containing 2 and 4% sucrose. The suspension cells accumulated rosmarinic acid up to 5.1% of the cell dry weight as well as caffeoyl-4'-hydroxyphenyllactate. Moreover, a more hydrophilic compound was detected which was isolated and identified as rosmarinic acid 3'-O-beta-D-glucoside, a new rosmarinic acid derivative. This new rosmarinic acid derivative was found up to 1.0% of the cell dry weight in suspension cells of A. agrestis. PMID:16133208

  18. Impact of the dual defence system of Plantago lanceolata (Plantaginaceae) on performance, nutrient utilisation and feeding choice behaviour of Amata mogadorensis larvae (Lepidoptera, Erebidae).

    PubMed

    Pankoke, Helga; Gehring, René; Müller, Caroline

    2015-11-01

    Iridoid glycosides are plant defence compounds with potentially detrimental effects on non-adapted herbivores. Some plant species possess β-glucosidases that hydrolyse iridoid glycosides and thereby release protein-denaturing aglycones. To test the hypothesis that iridoid glycosides and plant β-glucosidases form a dual defence system, we used Plantago lanceolata and a polyphagous caterpillar species. To analyse the impact of leaf-age dependent differences in iridoid glycoside concentrations and β-glucosidase activities on insect performance, old or young leaves were freeze-dried and incorporated into artificial diets or were provided freshly to the larvae. We determined larval consumption rates and the amounts of assimilated nitrogen. Furthermore, we quantified β-glucosidase activities in artificial diets and fresh leaves and the amount of iridoid glycosides that larvae feeding on fresh leaves ingested and excreted. Compared to fresh leaves, caterpillars grew faster on artificial diets, on which larval weight gain correlated positively to the absorbed amount of nitrogen. When feeding fresh young leaves, larvae even lost weight and excreted only minute proportions of the ingested iridoid glycosides intact with the faeces, indicating that the hydrolysis of these compounds might have interfered with nitrogen assimilation and impaired larval growth. To disentangle physiological effects from deterrent effects of iridoid glycosides, we performed dual choice feeding assays. Young leaves, their methanolic extracts and pure catalpol reduced larval feeding in comparison to the respective controls, while aucubin had no effect on larval consumption. We conclude that the dual defence system of P. lanceolata consisting of iridoid glycosides and β-glucosidases interferes with the nutrient utilisation via the hydrolysis of iridoid glycosides and also mediates larval feeding behaviour in a concentration- and substance-specific manner. PMID:26306994

  19. Genetic transformation of Gentiana macrophylla with Agrobacterium rhizogenes: growth and production of secoiridoid glucoside gentiopicroside in transformed hairy root cultures.

    PubMed

    Tiwari, Rajesh Kumar; Trivedi, Mala; Guang, Zhang Chun; Guo, Guang-Qin; Zheng, Guo-Chang

    2007-02-01

    Hairy root cultures of Gentiana macrophylla were established by infecting the different explants four Agrobacterium rhizogenes strains namely A(4)GUS, R1000, LBA 9402 and ATCC11325, and hairy root lines were established with A. rhizogenes strain R1000 in 1/2 MS + B(5) medium. Initially, 42 independent hairy root clones were maintained and seven clones belongs to different category were evaluated for growth, morphology, integration and expression of Ri T-DNA genes, and alkaloid contents in dry root samples. On the basis of total root elongation, lateral root density and biomass accumulation on solid media, hairy root clones were separated into three categories. PCR and Southern hybridization analysis revealed both left and right T-DNA integration in the root clones and RT-PCR analysis confirmed the expression of hairy root inducible gene. GUS assay was also performed to confirm the integration of left T-DNA. The accumulation of considerable amounts of the root-specific secoiridoid glucosides gentiopicroside was observed in GM1 (T +/L and T +/R) and the GM2 (T +/L and T -/R DNA) type clones in considerably higher amount whether as two T -/L but T +/R callus-type clones (GM3) accumulated much less or only very negligible amounts of gentiopicroside. Out of four media composition the 1/2 MS + B(5) vitamin media was found most suitable. We found that initial establishment of root cultures largely depends on root:media ratio. Maximum growth rate was recorded in 1:50 root:media ratio. The maximum biomass in terms of fresh weight (33-fold) was achieved in 1/2 MS + B(5) media composition after 35 days in comparison to sixfold increase in control. The biomass increase was most abundant maximum from 15 to 30 days. Influence of A. rhizogenes strains and Ri plasmid of hairy root induction, the possible role of the T(L)-DNA and T(R)-DNA genes on growth pattern of hairy root, initial root inoculum:media ratio and effect of media composition is discussed. PMID:16972092

  20. Kinetics of the hydrolysis of cellobiose and p-nitrophenyl-beta-D-glucoside by cellobiase of Trichoderma viride.

    PubMed

    Maguire, R J

    1977-01-01

    Cellobiase has been isolated from the crude cellulase mixture of enzymes of Trichoderma viride using column chromatographic and ion-exchange methods. The steady-state kinetics of the hydrolysis of cellobiose have been investigated as a function of cellobiose and glucose concentrations, pH of the solution, temperature, and dielectric constant, using isopropanol-buffer mixtures. The results show that (i) there is a marked activation of the reaction by initial glucose concentrations of 4 X 10(-3) M to 9 X 10(-2) M and strong inhibition of the reaction at higher initial concentrations, (ii) the log rate -pH curve has a maximum at pH 5.2 and enzyme pK values of 3.5 and 6.8, (iii) the energy of activation at pH 5.1 is 10.2 kcal mol-1 over the temperature range 5-56 degrees C, and (iv) the rate decreases from 0 to 20% (v/v) isopropanol. The hydrolysis by cellobiase (EC 3.2.1.21) of p-nitrophenyl-beta-D-glucoside was examined by pre-steady-state methods in which [enzyme]0 greater than [substrate]0, and by steady-state methods as a function of pH and temperature. The results show (i) a value for k2 of 21 S-1 at pH 7.0 (where k2 is the rate constant for the second step in the assumed two-intermediate mechanism (formula: see text), (ii) a log rate -pH curve, significantly different from that for hydrolysis of cellobiose, in which the rate increases with decreasing pH below pH 4.5, is constant in the region pH 4.5-6, and decreases above pH 6 (exhibiting an enzyme pK value of 7.3), and (iii) an activation energy of 12.5 kcal mol-1 at pH 5.7 over the temperature range 10-60 degrees C. PMID:13917

  1. Evaluation of ozonation technique for pesticide residue removal and its effect on ascorbic acid, cyanidin-3-glucoside, and polyphenols in apple (Malus domesticus) fruits.

    PubMed

    Swami, Saurabh; Muzammil, Raunaq; Saha, Supradip; Shabeer, Ahammed; Oulkar, Dasharath; Banerjee, Kaushik; Singh, Shashi Bala

    2016-05-01

    Ozonated water dip technique was evaluated for the detoxification of six pesticides, i.e., chlorpyrifos, cypermethrin, azoxystrobin, hexaconazole, methyl parathion, and chlorothalonil from apple fruits. Results revealed that ozonation was better than washing alone. Ozonation for 15 min decreased residues of the test pesticides in the range of from 26.91 to 73.58%, while ozonation for 30 min could remove the pesticide residues by 39.39-95.14 % compared to 19.05-72.80 % by washing. Cypermethrin was the least removed pesticide by washing as well as by ozonation. Chlorothalonil, chlorpyrifos, and azoxystrobin were removed up to 71.45-95.14 % in a 30-min ozonation period. In case of methyl parathion removal, no extra advantage could be obtained by ozonation. The HPLC analysis indicated that ozonation also affected adversely the ascorbic acid and cyanidin-3-glucoside content of apples. However, 11 polyphenols studied showed a mixed trend. Gallic acid, 3,4-dihydroxybenzoic acid, catechin, epicatechin, p-coumaric acid, quercetin-3-O-glucoside, quercetin, and kaempferol were found to decrease while syringic acid, rutin, and resveratrol were found to increase in 30-min ozonation. PMID:27098519

  2. Molecular cloning and biochemical characterization of a recombinant sterol 3-O-glucosyltransferase from Gymnema sylvestre R.Br. catalyzing biosynthesis of steryl glucosides.

    PubMed

    Tiwari, Pragya; Sangwan, Rajender Singh; Asha; Mishra, B N; Sabir, Farzana; Sangwan, Neelam S

    2014-01-01

    Gymnema sylvestre R.Br., a pharmacologically important herb vernacularly called Gur-Mar (sugar eliminator), is widely known for its antidiabetic action. This property of the herb has been attributed to the presence of bioactive triterpene glycosides. Although some information regarding pharmacology and phytochemical profiles of the plant are available, no attempts have been made so far to decipher the biosynthetic pathway and key enzymes involved in biosynthesis of steryl glucosides. The present report deals with the identification and catalytic characterization of a glucosyltransferase, catalyzing biosynthesis of steryl glycosides. The full length cDNA (2572 bp) contained an open reading frame of 2106 nucleotides that encoded a 701 amino acid protein, falling into GT-B subfamily of glycosyltransferases. The GsSGT was expressed in Escherichia coli and biochemical characterization of the recombinant enzyme suggested its key role in the biosynthesis of steryl glucosides with catalytic preference for C-3 hydroxyl group of sterols. To our knowledge, this pertains to be the first report on cloning and biochemical characterization of a sterol metabolism gene from G. sylvestre R.Br. catalyzing glucosylation of a variety of sterols of biological origin from diverse organisms such as bacteria, fungi, and plants. PMID:25250339

  3. Biochemical Characterization of a Recombinant UDP-glucosyltransferase from Rice and Enzymatic Production of Deoxynivalenol-3-O-β-d-glucoside

    PubMed Central

    Michlmayr, Herbert; Malachová, Alexandra; Varga, Elisabeth; Kleinová, Jana; Lemmens, Marc; Newmister, Sean; Rayment, Ivan; Berthiller, Franz; Adam, Gerhard

    2015-01-01

    Glycosylation is an important plant defense mechanism and conjugates of Fusarium mycotoxins often co-occur with their parent compounds in cereal-based food and feed. In case of deoxynivalenol (DON), deoxynivalenol-3-O-β-d-glucoside (D3G) is the most important masked mycotoxin. The toxicological significance of D3G is not yet fully understood so that it is crucial to obtain this compound in pure and sufficient quantities for toxicological risk assessment and for use as an analytical standard. The aim of this study was the biochemical characterization of a DON-inactivating UDP-glucosyltransferase from rice (OsUGT79) and to investigate its suitability for preparative D3G synthesis. Apparent Michaelis constants (Km) of recombinant OsUGT79 were 0.23 mM DON and 2.2 mM UDP-glucose. Substrate inhibition occurred at DON concentrations above 2 mM (Ki = 24 mM DON), and UDP strongly inhibited the enzyme. Cu2+ and Zn2+ (1 mM) inhibited the enzyme completely. Sucrose synthase AtSUS1 was employed to regenerate UDP-glucose during the glucosylation reaction. With this approach, optimal conversion rates can be obtained at limited concentrations of the costly co-factor UDP-glucose. D3G can now be synthesized in sufficient quantity and purity. Similar strategies may be of interest to produce β-glucosides of other toxins. PMID:26197338

  4. Molecular Cloning and Biochemical Characterization of a Recombinant Sterol 3-O-Glucosyltransferase from Gymnema sylvestre R.Br. Catalyzing Biosynthesis of Steryl Glucosides

    PubMed Central

    Sangwan, Rajender Singh; Asha; Mishra, B. N.; Sangwan, Neelam S.

    2014-01-01

    Gymnema sylvestre R.Br., a pharmacologically important herb vernacularly called Gur-Mar (sugar eliminator), is widely known for its antidiabetic action. This property of the herb has been attributed to the presence of bioactive triterpene glycosides. Although some information regarding pharmacology and phytochemical profiles of the plant are available, no attempts have been made so far to decipher the biosynthetic pathway and key enzymes involved in biosynthesis of steryl glucosides. The present report deals with the identification and catalytic characterization of a glucosyltransferase, catalyzing biosynthesis of steryl glycosides. The full length cDNA (2572 bp) contained an open reading frame of 2106 nucleotides that encoded a 701 amino acid protein, falling into GT-B subfamily of glycosyltransferases. The GsSGT was expressed in Escherichia coli and biochemical characterization of the recombinant enzyme suggested its key role in the biosynthesis of steryl glucosides with catalytic preference for C-3 hydroxyl group of sterols. To our knowledge, this pertains to be the first report on cloning and biochemical characterization of a sterol metabolism gene from G. sylvestre R.Br. catalyzing glucosylation of a variety of sterols of biological origin from diverse organisms such as bacteria, fungi, and plants. PMID:25250339

  5. β-D-Glucoside utilization by Mycoplasma mycoides subsp. mycoides SC: possible involvement in the control of cytotoxicity towards bovine lung cells

    PubMed Central

    Vilei, Edy M; Correia, Ivone; Ferronha, M Helena; Bischof, Daniela F; Frey, Joachim

    2007-01-01

    Background Contagious bovine pleuropneumonia (CBPP) caused by Mycoplasma mycoides subsp. mycoides small-colony type (SC) is among the most serious threats for livestock producers in Africa. Glycerol metabolism-associated H2O2 production seems to play a crucial role in virulence of this mycoplasma. A wide number of attenuated strains of M. mycoides subsp. mycoides SC are currently used in Africa as live vaccines. Glycerol metabolism is not affected in these vaccine strains and therefore it does not seem to be the determinant of their attenuation. A non-synonymous single nucleotide polymorphism (SNP) in the bgl gene coding for the 6-phospho-β-glucosidase (Bgl) has been described recently. The SNP differentiates virulent African strains isolated from outbreaks with severe CBPP, which express the Bgl isoform Val204, from strains to be considered less virulent isolated from CBPP outbreaks with low mortality and vaccine strains, which express the Bgl isoform Ala204. Results Strains of M. mycoides subsp. mycoides SC considered virulent and possessing the Bgl isoform Val204, but not strains with the Bgl isoform Ala204, do trigger elevated levels of damage to embryonic bovine lung (EBL) cells upon incubation with the disaccharides (i.e., β-D-glucosides) sucrose and lactose. However, strains expressing the Bgl isoform Val204 show a lower hydrolysing activity on the chromogenic substrate p-nitrophenyl-β-D-glucopyranoside (pNPbG) when compared to strains that possess the Bgl isoform Ala204. Defective activity of Bgl in M. mycoides subsp. mycoides SC does not lead to H2O2 production. Rather, the viability during addition of β-D-glucosides in medium-free buffers is higher for strains harbouring the Bgl isoform Val204 than for those with the isoform Ala204. Conclusion Our results indicate that the studied SNP in the bgl gene is one possible cause of the difference in bacterial virulence among strains of M. mycoides subsp. mycoides SC. Bgl does not act as a direct virulence

  6. Higenamine 4'-O-β-d-glucoside in the lotus plumule induces glucose uptake of L6 cells through β2-adrenergic receptor.

    PubMed

    Kato, Eisuke; Inagaki, Yosuke; Kawabata, Jun

    2015-07-01

    Hypoglycemic effect is an efficient means to modulate elevated blood glucose levels in patients with diabetes. We found that the extract of lotus plumule (the germ of Nelumbo nucifera Gaertn. seed) showed potent glucose uptake enhancement activity against L6 myotubes, which results in a hypoglycemic effect. This activity was further investigated, and an active constituent was identified as a single bioactive compound, higenamine 4'-O-β-d-glucoside. Mechanistic studies employing phosphatidylinositol 3-kinase (PI3K) inhibitor, AMP-activated protein kinase (AMPK) inhibitor, or adrenergic receptor antagonist showed that the compound induced its activity through β2-adrenergic receptor. Patients with type II diabetes mellitus frequently develop insulin resistance. Owing to the differences between the mechanism of action of insulin and of the isolated compound, the compound or lotus plumule itself may have the possibility of modulating blood glucose levels in insulin-resistant patients effectively. PMID:25943853

  7. Phenanthrenes, 9,10-dihydrophenanthrenes, bibenzyls with their derivatives, and malate or tartrate benzyl ester glucosides from tubers of Cremastra appendiculata.

    PubMed

    Wang, Yang; Guan, Shu-Hong; Meng, Yu-Hui; Zhang, Yi-Bei; Cheng, Chun-Ru; Shi, Yang-Yang; Feng, Rui-Hong; Zeng, Feng; Wu, Zhi-Yuan; Zhang, Jing-Xian; Yang, Min; Liu, Xuan; Li, Qing; Chen, Xiao-Hui; Bi, Kai-Shun; Guo, De-An

    2013-10-01

    Eleven previously unknown compounds and 23 known compounds, including 20 phenanthrene or 9,10-dihydrophenanthrene derivatives, five bibenzyls, seven malate or tartrate benzyl ester glucosides, adenosine and gastrodin were isolated from tubers of Cremastra appendiculata. Among the obtained compounds, two are the first isolated dimers with one phenanthrene or bibenzyl unit connected to C-3 of 2,3,4,5-tetrahydro-phenanthro[2,1-b]furan moiety. In addition, 33 of these compounds were evaluated in vitro for their cytotoxic activity against two cancer cell lines. Among the compounds examined, one compound showed moderate cytotoxic activity, while five showed weak cytotoxic activity against the A549 cell line. PMID:23820314

  8. High-performance liquid chromatographic determination and pharmacokinetic study of apigenin-7-O-β-D-glucoside in rat plasma after intravenous administration.

    PubMed

    Chen, Zaixing; Ying, Xixiang; Meng, Shu; Zhu, Xu; Jiang, Hong; Cao, Qishen; Li, Xuying; Meng, Fanhao

    2011-05-01

    The present study was designed to validate an analytical method based on HPLC for the quantitative measurement of the Apigenin-7-O-β-D-glucoside (AGL) in rat plasma after intravenous administration. HPLC analysis was done using a C18 column, UV detection at 335 nm, and a mobile phase of methanol:0.2% phosphoric acid (1:1, v/v). Good linearity was observed over the range of 0.06-7.20 μg/mL with a lower limit of quantication of 0.06 μg/mL. The intra-and inter-day precision values were below 9.97%. No interference peaks or matrix effects were observed. The method was fully validated and successfully applied to a pharmacokinetic study of AGL. PMID:21656359

  9. The color expression of copigmentation between malvidin-3-O-glucoside and three phenolic aldehydes in model solutions: The effects of pH and molar ratio.

    PubMed

    Zhang, Bo; He, Fei; Zhou, Pan-Pan; Liu, Yue; Duan, Chang-Qing

    2016-05-15

    Copigmentation was investigated in model solutions between the anthocyanin malvidin-3-O-glucoside and three phenolic aldehydes (vanillic, syringic and coniferyl aldehydes) as a function of the pH and the pigment/copigment molar ratio. Tristimulus colorimetry was applied to evaluate the chromatic variations induced by copigmentation process. The results indicated that the greatest magnitude of copigmentation was obtained at pH 3.0 and molar ratio of 1:100, being significantly higher with coniferyl aldehyde, followed by syringic and vanillic aldehydes. The equilibrium constant (K) and Gibbs free energies (ΔG°) determined here show a spontaneous exothermic reaction. Theoretical calculations (ΔGbinding, ΔE) specified the relative arrangement of the pigment and copigment molecules within the complexes. In addition, an atoms in molecules (AIM) analysis was used to explore the main driving forces contributing to the formation of copigmentation complexes. PMID:26775964

  10. Hypoglycaemic effect of mollic acid glucoside, a 1alpha-hydroxycycloartenoid saponin extractive from Combretum molle R. Br. ex G. Don (Combretaceae) leaf, in rodents.

    PubMed

    Ojewole, John A O; Adewole, Stephen O

    2009-04-01

    In this study, we investigated the hypoglycaemic and antidiabetic properties of mollic acid glucoside (MAG), a 1alpha-hydroxycycloartenoid extractive from Combretum molle leaf, in rodents. Stepwise, escalated doses of MAG (5-80 mg/kg p.o.) produced dose-dependent and significant (P < 0.05-0.01) hypoglycaemic and antidiabetic effects in normal (normoglycaemic) and streptozotocin-treated diabetic rats. Experimental evidence obtained from this laboratory animal study indicates that MAG, an extractive from C. molle leaf, possesses hypoglycaemic and antidiabetic properties. These findings lend pharmacological credence to the folkloric, ethnomedical uses of the plant's leaf in the management and/or control of diabetes mellitus in some rural communities of southern Africa. PMID:19050993

  11. Fluorescence Up-Conversion Studies of [2,2'-Bipyridyl]-3,3'-diol in Octyl-β-d-glucoside and Other Micellar Aggregates.

    PubMed

    Satpathi, Sagar; Gavvala, Krishna; Hazra, Partha

    2015-12-24

    In this present work, excited state double proton transfer dynamics (ESIDPT) of 2,2'-bipyridyl-3,3'-diol (BP(OH)2) molecules has been probed in a nontoxic, biocompatible sugar surfactant assembly, namely, octyl-β-d-glucoside (OBG) micelle with the help of steady state and fluorescence up-conversion techniques. Moreover, the ultrafast double proton transfer dynamics in conventional micelles (SDS, CTAB) and bile salts aggregates have been probed and compared. Interestingly, in all these supramolecular aggregates, the ESIDPT dynamics is found to follow sequential pathway; however, the time-scale of proton transfer dynamics varies from 11 to 30 ps. This difference in proton transfer time scale in different supramolecular aggregates has been explained in terms of accessibility of water molecules in the vicinity of probe. PMID:26613290

  12. Quercetin 7-O-glucoside suppresses nitrite-induced formation of dinitrosocatechins and their quinones in catechin/nitrite systems under stomach simulating conditions.

    PubMed

    Morina, Filis; Takahama, Umeo; Yamauchi, Ryo; Hirota, Sachiko; Veljovic-Jovanovic, Sonja

    2015-01-01

    Foods of plant origin contain flavonoids. In the adzuki bean, (+)-catechin, quercetin 3-O-rutinoside (rutin), and quercetin 7-O-β-D-glucopyranoside (Q7G) are the major flavonoids. During mastication of foods prepared from the adzuki bean, the flavonoids are mixed with saliva and swallowed into the stomach. Here we investigated the interactions between Q7G and (+)-catechin at pH 2, which may proceed in the stomach after the ingestion of foods prepared from the adzuki bean. Q7G reacted with nitrous acid producing nitric oxide (˙NO) and a glucoside of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone. (+)-Catechin reacted with nitrous acid producing ˙NO and 6,8-dinitrosocatechin. The production of the dinitrosocatechin was partly suppressed by Q7G, and the suppression resulted in the enhancement of Q7G oxidation. 6,8-Dinitrosocatechin reacted further with nitrous acid generating the o-quinone, and the quinone formation was effectively suppressed by Q7G. In the flavonoids investigated, the suppressive effect decreased in the order Q7G≈quercetin>kaempferol>quercetin 4'-O-glucoside>rutin. Essentially the same results were obtained when (-)-epicatechin was used instead of (+)-catechin. The results indicate that nitrous acid-induced formation of 6,8-dinitrosocatechins and the o-quinones can be suppressed by flavonols in the stomach, and that both a hydroxyl group at C3 and ortho-hydroxyl groups in the B-ring are required for efficient suppression. PMID:25375233

  13. Simultaneous determination of major type B trichothecenes and deoxynivalenol-3-glucoside in animal feed and raw materials using improved DSPE combined with LC-MS/MS.

    PubMed

    Zhao, Zhiyong; Rao, Qinxiong; Song, Suquan; Liu, Na; Han, Zheng; Hou, Jiafa; Wu, Aibo

    2014-07-15

    A simple and reliable method for simultaneous determination of deoxynivalenol-3-glucoside and major type B trichothecenes (deoxynivalenol, nivalenol, fusarenon X, 3-acetyldeoxynivalenol, 15-acetyldeoxynivalenol and deepoxy-deoxynivalenol) in animal feed and raw materials has been developed and validated in this study. The method was based on an improved dispersive solid-phase extraction (DSPE) followed by analysis using high performance liquid chromatography coupled to tandem mass spectrometry (HPLC-MS/MS). Also, matrix-matched calibration curve (R(2)>0.99) was employed to minimize matrix effects and ensure accurate quantification. The recoveries during sample preparation process (including extraction and clean-up) ranged from 79.03% to 118.39%, with intra-day and inter-day relative standard deviation lower than 20% for all the analytes. The limit of quantification ranged from 5.0 μg/kg for deoxynivalenol to 13.6 μg/kg for fusarenon X. The validated method was successfully applied to the analysis of animal feed and corn. The pilot study showed that 37 out of 41 samples were contaminated with deoxynivalenol-3-glucoside at the levels of 6.0-121.0 μg/kg. Most of the type B trichothecenes were also found with the exception of fusarenon X, at the contaminated levels of 10.0-1,382 μg/kg. To the best of our knowledge, this was the first scientific report on the co-occurrence of masked deoxynivalenol and type B trichothecenes in animal feed and raw materials. PMID:24935763

  14. Discovery of the glycogen phosphorylase-modulating activity of a resveratrol glucoside by using a virtual screening protocol optimized for solvation effects.

    PubMed

    Mavrokefalos, Nikolaos; Myrianthopoulos, Vassilios; Chajistamatiou, Aikaterini S; Chrysina, Evangelia D; Mikros, Emmanuel

    2015-04-01

    The identification of natural products that can modulate blood glucose levels is of great interest as it can possibly facilitate the utilization of mild interventions such as herbal medicine or functional foods in the treatment of chronic diseases like diabetes. One of the established drug targets for antihyperglycemic therapy is glycogen phosphorylase. To evaluate the glycogen phosphorylase inhibitory properties of an in-house compound collection consisting to a large extent of natural products, a stepwise virtual and experimental screening protocol was devised and implemented. The fact that the active site of glycogen phosphorylase is highly hydrated emphasized that a methodological aspect needed to be efficiently addressed prior to an in silico evaluation of the compound collection. The effect of water molecules on docking calculations was regarded as a key parameter in terms of virtual screening protocol optimization. Statistical analysis of 125 structures of glycogen phosphorylase and solvent mapping focusing on the active site hydration motif in combination with a retrospective screening revealed the importance of a set of 29 crystallographic water molecules for achieving high enrichment as to the discrimination between active compounds and inactive decoys. The scaling of Van der Waals radii of system atoms had an additional effect on screening performance. Having optimized the in silico protocol, a prospective evaluation of the in-house compound collection derived a set of 18 top-ranked natural products that were subsequently evaluated in vitro for their activity as glycogen phosphorylase inhibitors. Two phenolic glucosides with glycogen phosphorylase-modulating activity were identified, whereas the most potent compound affording mid-micromolar inhibition was a glucosidic derivative of resveratrol, a stilbene well-known for its wide range of biological activities. Results show the possible phytotherapeutic and nutraceutical potential of products common in

  15. Analgesic and antiinflammatory effects of mollic acid glucoside, a 1 alpha-hydroxycycloartenoid saponin extractive from Combretum molle R. Br. ex G. Don (Combretaceae) leaf.

    PubMed

    Ojewole, John A O

    2008-01-01

    The analgesic and antiinflammatory properties of mollic acid glucoside (MAG), a 1 alpha-hydroxycycloartenoid extract from Combretum molle leaf, have been investigated in mice and rats. The effects of graded doses of mollic acid glucoside (MAG, 5-80 mg/kg i.p.) were examined against thermally- and chemically-induced nociceptive pain in mice. Furthermore, the effects of graded doses of the plant extract (MAG, 5-80 mg/kg p.o.) were also investigated on rat paw oedema induced by subplantar injections of fresh egg albumin (0.5 mg/kg). Morphine (MPN, 10 mg/kg i.p.) and diclofenac (DIC, 100 mg/kg i.p.) were used as reference analgesic and antiinflammatory agents for comparison, respectively. Like DIC (100 mg/kg i.p.) and MPN (10 mg/kg i.p.), MAG (5-80 mg/kg i.p.) produced dose-dependent, significant (p < 0.05-0.001) analgesic effects against thermally and chemically induced nociceptive pain in mice. The extractive (MAG, 5-80 mg/kg i.p.) also significantly reduced (p < 0.05-0.001) rat paw oedema induced by subplantar injections of fresh egg albumin in a dose-related fashion. However, the extract (MAG, 5-80 mg/kg i.p.) was found to be less potent than diclofenac (DIC) as an analgesic or antiinflammatory agent. Experimental evidence obtained from this laboratory animal study indicates that the Combretum molle leaf extractive (MAG) possesses analgesic and antiinflammatory properties, and thus lend pharmacological credence to the folkloric, ethnomedical uses of the plant's leaf in the management, control and/or treatment of painful, arthritic and other inflammatory conditions in some rural communities of southern Africa. PMID:17685389

  16. Expression pattern of NMDA receptors reveals antiepileptic potential of apigenin 8-C-glucoside and chlorogenic acid in pilocarpine induced epileptic mice.

    PubMed

    Aseervatham, G Smilin Bell; Suryakala, U; Doulethunisha; Sundaram, S; Bose, P Chandra; Sivasudha, T

    2016-08-01

    The present study was aimed to evaluate the effect of apigenin 8-C-glucoside (Vitexin) and chlorogenic acid on epileptic mice induced by pilocarpine and explored its possible mechanisms. Intraperitonial administration of pilocarpine (85mg/kg) induced seizure in mice was assessed by behavior observations, which is significantly (p>0.05) reduced by apigenin 8-C-glucoside (AP8CG) (10mg/kg) and chlorogenic acid (CA) (5mg/kg), similar to diazepam. Seizure was accompanied by an imbalance in the levels of Gamma-aminobutyric acid (GABA) and glutamate in the pilocarpine administered group. Moreover, convulsion along with reduced acetylcholinesterase, increased monoamine oxidase and oxidative stress was observed in epileptic mice brain. AP8CG and CA significantly restored back to normal levels even at lower doses. Further, increased lipid peroxidation and nitrite content was also significantly attenuated by AP8CG and CA. However, CA was found to be more effective when compared to AP8CG. In addition, the mRNA expression of N-methyl-d-aspartate receptor (NMDAR), mGluR1 and mGlu5 was significantly (P≤0.05) inhibited by AP8CG and CA in a lower dose. The mRNA expression of GRIK1 did not differ significantly in any of the group and showed a similar pattern of expression. Our result shows that AP8CG and CA selectively inhibit NMDAR, mGluR1 and mGlu5 expression. Modification in the provoked NMDAR calcium response coupled with neuronal death. Hence, these findings underline that the polyphenolics, AP8CG and CA have exerted antiepileptic and neuroprotective activity by suppressing glutamate receptors. PMID:27470339

  17. Halohydrins and polyols derived from antirrhinoside: structural revisions of muralioside and epimuralioside

    PubMed

    Franzyk; Jensen; Thale; Olsen

    1999-02-01

    Treatment of the iridoid glucoside antirrhinoside (1) with pyridinium chloride in dimethylformamide gave rise to the two possible trans-halohydrins, linarioside (4) and isolinarioside (5). Pyridinium bromide gave the two analogous bromohydrins. It is shown that the iridoid glucosides 8-epi-muralioside from Linaria arcusangeli and 7,8-epi-antirrhinoside from Linaria dalmatica are both identical with isolinarioside, and therefore, these names are redundant. The structure of muralioside isolated from Cymbalaria muralis is revised to that of its 8-epimer (8), while the structure of an isomeric, new iridoid glucoside from Paulownia tomentosa has been elucidated to be 7beta-hydroxyharpagide (3), the structure originally assigned to 8. In addition, 7alpha-hydroxyharpagide (2), the known product from the base-catalyzed hydrolytic opening of 1, has been isolated from Antirrhinum majus and thus shown to be a natural product. PMID:10075758

  18. Malonyl-CoA:anthocyanin 5-O-glucoside-6"'-O-malonyltransferase from scarlet sage (Salvia splendens) flowers. Enzyme purification, gene cloning, expression, and characterization.

    PubMed

    Suzuki, H; Nakayama, T; Yonekura-Sakakibara, K; Fukui, Y; Nakamura, N; Nakao, M; Tanaka, Y; Yamaguchi, M A; Kusumi, T; Nishino, T

    2001-12-28

    The orange to blue coloration of flowers in nature is, in most cases, provided by anthocyanins, a class of plant flavonoids, many of which are modified by malonyl group(s). However, the identity of the enzyme catalyzing the malonylation reaction remains to be established. Here, we describe for the first time the purification, characterization, and cDNA cloning of an anthocyanin malonyltransferase from scarlet sage (Salvia splendens) flowers. The purified enzyme (termed Ss5MaT1) was a monomeric 50-kDa protein catalyzing the regiospecific transfer of the malonyl group from malonyl-CoA to the 6"'-hydroxyl group of the 5-glucosyl moiety of anthocyanins. Ss5MaT1 showed a k(cat) value of 7.8 s(-1) at 30 degrees C and pH 7.0 for the malonylation of bisdemalonylsalvianin (pelargonidin 3-(6"-O-caffeyl-beta-glucopyranoside)-5-beta-glucopyranoside) and K(m) values of 101 microm and 57 microm for bisdemalonylsalvianin and malonyl-CoA, respectively. p-Coumaric acid, which mimics an aromatic acyl group linked to the 3-glucosidic moiety of an anthocyanin substrate, was a competitive inhibitor with respect to the substrate. This strongly suggests that the presence of an aromatic acyl group at the 3-glucosidic moiety of anthocyanin is important for substrate recognition by the enzyme. On the basis of the partial amino acid sequences of the purified enzyme, we isolated a cDNA encoding Ss5MaT1. Ss5MaT1 consisted of 462 amino acids and shared motifs that are commonly found among members of a versatile plant acyltransferase family, which was recently shown to include numerous homologs of unknown biochemical functions. Northern blot analysis revealed that the transcripts of Ss5MaT1 were detected in petals, sepals, bracts, and red stems, in accordance with the pigment accumulation patterns. Phylogenetic analysis suggests that the aliphatic and aromatic acylations of anthocyanins are generally catalyzed by subfamily members of the plant acyltransferase family. PMID:11598135

  19. The evolutionary appearance of non-cyanogenic hydroxynitrile glucosides in the Lotus genus is accompanied by the substrate specialization of paralogous β-glucosidases resulting from a crucial amino acid substitution.

    PubMed

    Lai, Daniela; Abou Hachem, Maher; Robson, Fran; Olsen, Carl Erik; Wang, Trevor L; Møller, Birger L; Takos, Adam M; Rook, Fred

    2014-07-01

    Lotus japonicus, like several other legumes, biosynthesizes the cyanogenic α-hydroxynitrile glucosides lotaustralin and linamarin. Upon tissue disruption these compounds are hydrolysed by a specific β-glucosidase, resulting in the release of hydrogen cyanide. Lotus japonicus also produces the non-cyanogenic γ- and β-hydroxynitrile glucosides rhodiocyanoside A and D using a biosynthetic pathway that branches off from lotaustralin biosynthesis. We previously established that BGD2 is the only β-glucosidase responsible for cyanogenesis in leaves. Here we show that the paralogous BGD4 has the dominant physiological role in rhodiocyanoside degradation. Structural modelling, site-directed mutagenesis and activity assays establish that a glycine residue (G211) in the aglycone binding site of BGD2 is essential for its ability to hydrolyse the endogenous cyanogenic glucosides. The corresponding valine (V211) in BGD4 narrows the active site pocket, resulting in the exclusion of non-flat substrates such as lotaustralin and linamarin, but not of the more planar rhodiocyanosides. Rhodiocyanosides and the BGD4 gene only occur in L. japonicus and a few closely related species associated with the Lotus corniculatus clade within the Lotus genus. This suggests the evolutionary scenario that substrate specialization for rhodiocyanosides evolved from a promiscuous activity of a progenitor cyanogenic β-glucosidase, resembling BGD2, and required no more than a single amino acid substitution. PMID:24861854

  20. Preparative isolation of pseudolaric acids A and B, and their glucosides from the root bark of Pseudolarix kaempferi using high-speed counter-current chromatography.

    PubMed

    Han, Quan-Bin; Wong, Lina; Lai, Fanny; Yang, Nian-Yun; Song, Jing-Zheng; Qiao, Chun-Feng; Xu, Hong-Xi

    2009-01-01

    In order to provide the chemical markers for the quality control of herbal medicines, four diterpenoids, pseudolaric acids A and B (PAA and PAB), and their glucosides were isolated from the methanol extract of the Chinese herb Pseudolarix kaempferi using high-speed counter-current chromatography (HSCCC). The diphase solvent system was n-hexane/EtOAc/MeOH/H(2)O which was used at two ratios (5:5:5:5 and 1:9:4:6 by volume) in the separation of pseudolaric acids and their glycosides, respectively. As a result, PAA (14 mg), PAB (129 mg), PAA-O-beta-D-glucopyranoside (8 mg, PAAG), and PAB-O-beta-D-glucopyranoside (42 mg, PABG) were obtained from 0.5 g of the crude extract. Their purities were determined to be above 97% by HPLC analysis. Their chemical structures were confirmed by( 1)H and( 13)C NMR analysis or HPLC comparison with the reference compounds. PMID:19072902

  1. Luteolin-7-glucoside inhibits IL-22/STAT3 pathway, reducing proliferation, acanthosis, and inflammation in keratinocytes and in mouse psoriatic model.

    PubMed

    Palombo, R; Savini, I; Avigliano, L; Madonna, S; Cavani, A; Albanesi, C; Mauriello, A; Melino, G; Terrinoni, A

    2016-01-01

    The epidermis is a dynamic tissue in which keratinocytes proliferate in the basal layer and undergo a tightly controlled differentiation while moving into the suprabasal layers. The balance between keratinocyte proliferation, differentiation, and death is essential, and its perturbation can result in pathological changes. Some common skin diseases, such as psoriasis, are characterized by hyperproliferation accompanied by inflammatory reactions, suggesting that molecules with topical anti-inflammatory and ROS scavenging abilities may be useful for their treatment. Here we investigate the potential of the flavone Luteolin-7-glucoside (LUT-7G) as a treatment for psoriasis. We show that LUT-7G leads to a modification of the cell cycle and the induction of keratinocyte differentiation, with modification of energy, fatty acid, and redox metabolism. LUT-7G treatment also neutralizes the proliferative stimulus induced by the proinflammatory cytokines IL-22 and IL-6 in HEKn. Moreover, in the Imiquimod (IMQ) mouse model of psoriasis, topical administration of LUT-7G leads to a marked reduction of acanthosis and re-expression of epidermal differentiation markers. Dissection of the IL-22 signalling pathway, activated by IMQ treatment, demonstrates that LUT-7G impairs the nuclear translocation of phosphorylated (activated) STAT3, blocking the IL-22 signalling cascade. Thus LUT-7G appears to be a promising compound for the treatment of hyperproliferative and inflammatory skin diseases, such as psoriasis. PMID:27537526

  2. Stimulation of callose synthesis in vivio correlates with changes in intracellular distribution of the callose synthase activator [beta]-Furfuryl-[beta]-Glucoside

    SciTech Connect

    Ohana, P.; Benziman, M.; Delmer, D.P. )

    1993-01-01

    [beta]-Furfuryl-[beta]-glucoside (FG) has been shown to be a specific endogenous activator of higher plant callose synthase. Because glycosides such as FG are usually sequestered in vacuoles, we have proposed that activation of callose synthesis in vivo may involve a change in the compartmentation on FG and Ca[sup 2+], resulting in a synergistic activation of callose synthase. The use of suspension-cultured barley (Hordeum bulbosum L.) cells provides evidence that FG is largely sequestered in the vacuole. Furthermore, conditions that lead to induction of callose synthesis in vivo correspondingly lead to elevation of the cytoplasmic concentration of FG. These conditions include the lowering of cytoplasmic pH or elevation of cytoplasmic Ca[sup 2+]. Oligogalacturonide elicitors have also been reported to cause similar changes in cytoplasmic pH and Ca[sup 2+] concentration, and such an elicitor also causes and elevation in cytoplasmic FG coupled with stimulation of callose synthesis. These results support the concept that a relative redistribution of FG between cytoplasm and vacuole may be one of the components of the signal transduction pathway for elicitation of callose synthase in vivo. 18 refs., 1 fig., 2 tabs.

  3. Seasonal alteration in amounts of lignans and their glucosides and gene expression of the relevant biosynthetic enzymes in the Forsythia suspense leaf.

    PubMed

    Morimoto, Kinuyo; Satake, Honoo

    2013-01-01

    Lignans of Forsythia spp. are essential components of various Chinese medicines and health diets. However, the seasonal alteration in lignan amounts and the gene expression profile of lignan-biosynthetic enzymes has yet to be investigated. In this study, we have assessed seasonal alteration in amounts of major lignans, such as pinoresinol, matairesinol, and arctigenin, and examined the gene expression profile of pinoresinol/lariciresinol reductase (PLR), pinoresinol-glucosylating enzyme (UGT71A18), and secoisolariciresinol dehydrogenase (SIRD) in the leaf of Forsythia suspense from April to November. All of the lignans in the leaf continuously increased from April to June, reached the maximal level in June, and then decreased. Ninety percent of pinoresinol and matairesinol was converted into glucosides, while approximately 50% of arctigenin was aglycone. PLR was stably expressed from April to August, whereas the PLR expression was not detected from September to November. In contrast, the UGT71A18 expression was found from August to November, but not from April to July. The SIRD expression was prominent from April to May, not detected in June to July, and then increased again from September to November. These expression profiles of the lignan-synthetic enzymes are largely compatible with the alteration in lignan contents. Furthermore, such seasonal lignan profiles are in good agreement with the fact that the Forsythia leaves for Chinese medicinal tea are harvested in June. This is the first report on seasonal alteration in lignans and the relevant biosynthetic enzyme genes in the leaf of Forsythia species. PMID:23832493

  4. Aortic Remodelling Is Improved by 2,3,5,4′-Tetrahydroxystilbene-2-O-β-D-glucoside Involving the Smad3 Pathway in Spontaneously Hypertensive Rats

    PubMed Central

    Duan, Ju; Han, Xin; Ling, Shuang; Gan, Woting; Sun, Li; Ni, Rong-Zhen; Xu, Jin-Wen

    2015-01-01

    Hypertension is a common health problem that substantially increases the risk of cardiovascular disease. The condition increases blood pressure, which causes alterations in vascular structure and leads to the development of vascular pathologies. 2,3,5,4′-Tetrahydroxystilbene-2-O-β-D-glucoside (THSG), a resveratrol analogue extracted from a Chinese medicinal plant, has been proven to have numerous vascular protection functions. This study investigated whether THSG can improve vascular remodeling, which has thus far remained unclear. Orally administering THSG to spontaneously hypertensive rats (SHRs) aged 12 weeks for 14 weeks significantly inhibited intima-media thickness in the lower parts of the aortic arch, increased the vascular diastolic rate in response to acetylcholine, and reduced remodelling-related mRNA expression, such as that of ACTA2, CCL3, COL1A2, COL3A1, TIMP1 WISP2, IGFBP1, ECE1, KLF5, MYL1 BMP4, FN1, and PAI-1. Immunofluorescence staining also showed an inhibitory effect similar to that of THSG on PAI-1 protein expression in rat aortas. Results from immunoprecipitation and a Western blot assay showed that THSG inhibited the acetylation of Smad3. A chromatin immunoprecipitation assay showed that THSG prevented Smad3 binding to the PAI-1 proximal promoter in SHR aortas. In conclusion, our results demonstrated that the inhibitory effect of THSG on aortic remodelling involved the deacetylating role of Smad3 with increasing blood flow and with constant blood pressure. PMID:26693246

  5. Complexation of bovine β-lactoglobulin with malvidin-3-O-glucoside and its effect on the stability of grape skin anthocyanin extracts.

    PubMed

    He, Zhiyong; Zhu, Haidong; Xu, Mingzhu; Zeng, Maomao; Qin, Fang; Chen, Jie

    2016-10-15

    The binding interaction between bovine β-lactoglobulin and malvidin-3-O-glucoside (MG), the major anthocyanin in grape skin anthocyanin extracts (GSAE), was studied at pH 6.3 using fluorescence, Fourier transform infrared and circular dichroism spectroscopy. The binding constant (KS), binding force and effect of the interaction on the β-lactoglobulin conformation and GSAE stability were investigated. The results indicated that β-lactoglobulin complexed with MG mainly via hydrophobic interaction with KS of 0.67×10(3)M(-)(1) at 297K. The secondary structure of β-lactoglobulin was changed by MG binding, with a decrease in α-helix, turn and random coil and an increase in β-sheet. Bovine whey protein effectively prevented the color fading and degradation of anthocyanin in the GSAE solution during the thermal treatment (80°C/2h), H2O2 oxidation (0.005% H2O2/1h) and photo illumination (5000lx/5d). The whey protein-anthocyanin complexation appeared to have a positive effect on the thermal, oxidation and photo stability of GSAE. PMID:27173557

  6. Involvement of the GABAergic system in the neuroprotective and sedative effects of acacetin 7-O-glucoside in rodents

    PubMed Central

    Gálvez, Javier; Estrada-Reyes, Rosa; Benítez-King, Gloria; Araujo, Gabriela; Orozco, Sandra; Fernández-Mas, Rodrigo; Almazán, Salvador; Calixto, Eduardo

    2015-01-01

    Abstract Purpose: Characterization of sedative, possible anticonvulsant, and protective effects of Acacetin-7-O-glucoside (7-ACAG). Methods: 7-ACAG was separated and its purity was analyzed. Its sedative and anti-seizure effects (1, 10, 20, and 40 mg/kg) were evaluated in male mice. Synaptic responses were acquired from area CA1 of hippocampal slices obtained from male Wistar rats. Rats were subjected to stereotaxic surgeries to allow Electroencephalographic (EEG) recordings. Functional recovery was evaluated by measuring the time rats spent in completing the motor task. Then the rats were subjected to right hemiplegia and administered 7-ACAG (40 mg/kg) 1 h or 24 h after surgery. Brains of each group of rats were prepared for histological analysis. Results: Effective sedative doses of 7-ACAG comprised those between 20 and 40 mg/kg. Latency and duration of the epileptiform crisis were delayed by this flavonoid. 7-ACAG decreased the synaptic response in vitro, similar to Gamma-aminobutyric acid (GABA) effects. The flavonoid facilitated functional recovery. This data was associated with preserved cytoarchitecture in brain cortex and hippocampus. Conclusions: 7-ACAG possesses anticonvulsive and sedative effects. Results suggest that GABAergic activity and neuroprotection are involved in the mechanism of action of 7-ACAG and support this compound’s being a potential drug for treatment of anxiety or post-operative conditions caused by neurosurgeries. PMID:26410208

  7. Phosphorylation of Akt Mediates Anti-Inflammatory Activity of 1-p-Coumaroyl β-D-Glucoside Against Lipopolysaccharide-Induced Inflammation in RAW264.7 Cells

    PubMed Central

    Vo, Van Anh; Lee, Jae-Won; Kim, Ji-Young; Park, Jun-Ho; Lee, Hee Jae; Kim, Sung-Soo; Kwon, Yong-Soo

    2014-01-01

    Hydroxycinnamic acids have been reported to possess numerous pharmacological activities such as antioxidant, anti-inflammatory, and anti-tumor properties. However, the biological activity of 1-p-coumaroyl β-D-glucoside (CG), a glucose ester derivative of p-coumaric acid, has not been clearly examined. The objective of this study is to elucidate the anti-inflammatory action of CG in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. In the present study, CG significantly suppressed LPS-induced excessive production of pro-inflammatory mediators such as nitric oxide (NO) and PGE2 and the protein expression of iNOS and COX-2. CG also inhibited LPS-induced secretion of pro-inflammatory cytokines, IL-1β and TNF-α. In addition, CG significantly suppressed LPS-induced degradation of IκB. To elucidate the underlying mechanism by which CG exerts its anti-inflammatory action, involvement of various signaling pathways were examined. CG exhibited significantly increased Akt phosphorylation in a concentration-dependent manner, although MAPKs such as Erk, JNK, and p38 appeared not to be involved. Furthermore, inhibition of Akt/PI3K signaling pathway with wortmannin significantly, albeit not completely, abolished CG-induced Akt phosphorylation and anti-inflammatory actions. Taken together, the present study demonstrates that Akt signaling pathway might play a major role in CG-mediated anti-inflammatory activity in LPS-stimulated RAW264.7 macrophage cells. PMID:24634601

  8. Sensitive analysis and pharmacokinetic study of the isomers paeoniflorin and albiflorin after oral administration of Total Glucosides Of White Paeony Capsule in rats.

    PubMed

    Fei, Fei; Yang, Hailing; Peng, Ying; Wang, Pei; Wang, Shuyao; Zhao, Yuqing; Huang, Jingqiu; Yu, Xiaoyi; Feng, Siqi; Sun, Runbin; Yang, Na; Wang, Hongbo; Aa, Jiye; Wang, Guangji

    2016-06-01

    A sensitive and reliable method using liquid chromatography tandem mass spectrometry (LC-MS/MS) was established for the simultaneous assay of paeoniflorin and albiflorin in bio-samples of rats after liquid-liquid extraction with ethylacetate. For the first time, the developed method was validated and successfully applied to the pharmacokinetics study of paeoniflorin and albiflorin after oral administration of Total Glucosides Of White Paeony Capsule (TGP). Relative to the intravenous injection, the absolute bio-availabilities of paeoniflorin and albiflorin were 2.8 and 1.7%, while their excretion in feces was 43.06 and 40.87%, respectively. Both paeoniflorin and albiflorin showed dose-dependent exposure in plasma, with a half-life of approximately 1.8h. No significant differences were observed between a single equal dose of paeoniflorin or albiflorin and that of TGP for the pharmacokinetic parameters, including AUC, T1/2 and Cmax. Paeoniflorin and albiflorin were exposed at high levels in immune relevant organ/tissues, such as the spleen, thymus and bone, which could facilitate immuno-regulatory activities. PMID:27070118

  9. 2,3,5,4′-Tetrahydroxystilbene-2-O-β-glucoside Isolated from Polygoni Multiflori Ameliorates the Development of Periodontitis

    PubMed Central

    Chin, Yu-Tang; Hsieh, Meng-Ti; Lin, Chi-Yu; Kuo, Po-Jan; Yang, Yu-Chen S. H.; Shih, Ya-Jung; Lai, Hsuan-Yu; Cheng, Guei-Yun; Tang, Heng-Yuan; Lee, Chen-Chen; Lee, Sheng-Yang; Wang, Ching-Chiung; Whang-Peng, Jacqueline; Liu, Leroy F.

    2016-01-01

    Periodontitis, a chronic infection by periodontopathic bacteria, induces uncontrolled inflammation, which leads to periodontal tissue destruction. 2,3,5,4′-Tetrahydroxystilbene-2-O-beta-glucoside (THSG), a polyphenol extracted from Polygoni Multiflori, reportedly has anti-inflammatory properties. In this study, we investigated the mechanisms of THSG on the Porphyromonas gingivalis-induced inflammatory responses in human gingival fibroblasts and animal modeling of ligature-induced periodontitis. Human gingival fibroblast cells were treated with lipopolysaccharide (LPS) extracted from P. gingivalis in the presence of resveratrol or THSG to analyze the expression of TNF-α, IL-1β, and IL-6 genes. Increased AMP-activated protein kinase (AMPK) activation and SirT1 expression were induced by THSG. Treatment of THSG decreased the expression of LPS-induced inflammatory cytokines, enhanced AMPK activation, and increased the expression of SirT1. In addition, it suppressed the activation of NF-κB when cells were stimulated with P. gingivalis LPS. The anti-inflammatory effect of THSG and P. Multiflori crude extracts was reproduced in ligature-induced periodontitis animal modeling. In conclusion, THSG inhibited the inflammatory responses of P. gingivalis-stimulated human gingival fibroblasts and ameliorated ligature-induced periodontitis in animal model. PMID:27504055

  10. Elucidation of the Final Reactions of DIMBOA-Glucoside Biosynthesis in Maize: Characterization of Bx6 and Bx71[W][OA

    PubMed Central

    Jonczyk, Rafal; Schmidt, Holger; Osterrieder, Anne; Fiesselmann, Andreas; Schullehner, Katrin; Haslbeck, Martin; Sicker, Dieter; Hofmann, Diana; Yalpani, Nasser; Simmons, Carl; Frey, Monika; Gierl, Alfons

    2008-01-01

    Benzoxazinoids were identified in the early 1960s as secondary metabolites of the grasses that function as natural pesticides and exhibit allelopathic properties. Benzoxazinoids are synthesized in seedlings and stored as glucosides (glcs); the main aglucone moieties are 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one (DIBOA) and 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA). The genes of DIBOA-glc biosynthesis have previously been isolated and the enzymatic functions characterized. Here, the enzymes for conversion of DIBOA-glc to DIMBOA-glc are identified. DIBOA-glc is the substrate of the dioxygenase BENZOXAZINLESS6 (BX6) and the produced 2,4,7-trihydroxy-2H-1,4-benzoxazin-3-(4H)-one-glc is metabolized by the methyltransferase BX7 to yield DIMBOA-glc. Both enzymes exhibit moderate Km values (below 0.4 mm) and kcat values of 2.10 s−1 and 0.25 s−1, respectively. Although BX6 uses a glucosylated substrate, our localization studies indicate a cytoplasmic localization of the dioxygenase. Bx6 and Bx7 are highest expressed in seedling tissue, a feature shared with the other Bx genes. At present, Bx6 and Bx7 have no close relatives among the members of their respective gene families. Bx6 and Bx7 map to the cluster of Bx genes on the short arm of chromosome 4. PMID:18192444

  11. Aortic Remodelling Is Improved by 2,3,5,4'-Tetrahydroxystilbene-2-O-β-D-glucoside Involving the Smad3 Pathway in Spontaneously Hypertensive Rats.

    PubMed

    Duan, Ju; Han, Xin; Ling, Shuang; Gan, Woting; Sun, Li; Ni, Rong-Zhen; Xu, Jin-Wen

    2015-01-01

    Hypertension is a common health problem that substantially increases the risk of cardiovascular disease. The condition increases blood pressure, which causes alterations in vascular structure and leads to the development of vascular pathologies. 2,3,5,4'-Tetrahydroxystilbene-2-O-β-D-glucoside (THSG), a resveratrol analogue extracted from a Chinese medicinal plant, has been proven to have numerous vascular protection functions. This study investigated whether THSG can improve vascular remodeling, which has thus far remained unclear. Orally administering THSG to spontaneously hypertensive rats (SHRs) aged 12 weeks for 14 weeks significantly inhibited intima-media thickness in the lower parts of the aortic arch, increased the vascular diastolic rate in response to acetylcholine, and reduced remodelling-related mRNA expression, such as that of ACTA2, CCL3, COL1A2, COL3A1, TIMP1 WISP2, IGFBP1, ECE1, KLF5, MYL1 BMP4, FN1, and PAI-1. Immunofluorescence staining also showed an inhibitory effect similar to that of THSG on PAI-1 protein expression in rat aortas. Results from immunoprecipitation and a Western blot assay showed that THSG inhibited the acetylation of Smad3. A chromatin immunoprecipitation assay showed that THSG prevented Smad3 binding to the PAI-1 proximal promoter in SHR aortas. In conclusion, our results demonstrated that the inhibitory effect of THSG on aortic remodelling involved the deacetylating role of Smad3 with increasing blood flow and with constant blood pressure. PMID:26693246

  12. Antiproliferative activity of long chain acylated esters of quercetin-3-O-glucoside in hepatocellular carcinoma HepG2 cells.

    PubMed

    Sudan, Sudhanshu; Rupasinghe, Hp Vasantha

    2015-11-01

    Despite their strong role in human health, poor bioavailability of flavonoids limits their biological effects in vivo. Enzymatically catalyzed acylation of fatty acids to flavonoids is one of the approaches of increasing cellular permeability and hence, biological activities. In this study, six long chain fatty acid esters of quercetin-3-O-glucoside (Q3G) acylated enzymatically and were used for determining their antiproliferative action in hepatocellular carcinoma cells (HepG2) in comparison to precursor compounds and two chemotherapy drugs (Sorafenib and Cisplatin). Fatty acid esters of Q3G showed significant inhibition of HepG2 cell proliferation by 85 to 90% after 6 h and 24 h of treatment, respectively. The cell death due to these novel compounds was associated with cell-cycle arrest in S-phase and apoptosis observed by DNA fragmentation, fluorescent microscopy and elevated caspase-3 activity and strong DNA topoisomerase II inhibition. Interestingly, Q3G esters showed significantly low toxicity to normal liver cells than Sorafenib (P < 0.05), a chemotherapy drug for hepatocellular carcinoma. Among all, oleic acid ester of Q3G displayed the greatest antiproliferation action and a high potential as an anti-cancer therapeutic. Overall, the results of the study suggest strong antiproliferative action of these novel food-derived compounds in treatment of cancer. PMID:25681471

  13. Assessment of the Therapeutic Effect of Total Glucosides of Peony for Juvenile Idiopathic Arthritis: A Systematic Review and Meta-Analysis.

    PubMed

    Cai, Yongsong; Yuan, Qiling; Xu, Ke; Zhu, Jialin; Li, Yuanbo; Wu, Xiaoqing; Yang, Le; Qiu, Yusheng; Xu, Peng

    2016-01-01

    Juvenile idiopathic arthritis (JIA) is the most common rheumatic disease in children; some clinical trials have reported the effects of total glucosides of peony (TGP) in the treatment of JIA. However, no systematic review has yet been conducted. In this study, we assessed the efficacy and safety in patients with JIA enrolled in randomized controlled trials (RCTs) of TGP. We extracted data for studies searched from 8 electronic databases that were searched and also evaluated the methodological quality of the included studies. We assessed the following outcome measures: overall response rate, pain, tender joint count (TJC), swollen joint count (SJC), duration of morning stiffness (DMS), grip strength (GS), rheumatoid factor (RF), erythrocyte sedimentation rate (ESR), C-reactive protein (CRP), and adverse effects (AEs) in short term (4-8 weeks), intermediate term (9-26 weeks), and long term (>26 weeks). The final analysis showed that TGP acted as a unique nonbiologic disease-modifying antirheumatic drug (nonbiologic DMARD), and its therapeutic effects were safe and efficacious for the treatment of JIA with few AEs. However, more high-quality RCTs are needed to confirm these therapeutic effects. PMID:27525026

  14. Assessment of the Therapeutic Effect of Total Glucosides of Peony for Juvenile Idiopathic Arthritis: A Systematic Review and Meta-Analysis

    PubMed Central

    Cai, Yongsong; Yuan, Qiling; Xu, Ke; Zhu, Jialin; Li, Yuanbo; Wu, Xiaoqing; Yang, Le

    2016-01-01

    Juvenile idiopathic arthritis (JIA) is the most common rheumatic disease in children; some clinical trials have reported the effects of total glucosides of peony (TGP) in the treatment of JIA. However, no systematic review has yet been conducted. In this study, we assessed the efficacy and safety in patients with JIA enrolled in randomized controlled trials (RCTs) of TGP. We extracted data for studies searched from 8 electronic databases that were searched and also evaluated the methodological quality of the included studies. We assessed the following outcome measures: overall response rate, pain, tender joint count (TJC), swollen joint count (SJC), duration of morning stiffness (DMS), grip strength (GS), rheumatoid factor (RF), erythrocyte sedimentation rate (ESR), C-reactive protein (CRP), and adverse effects (AEs) in short term (4–8 weeks), intermediate term (9–26 weeks), and long term (>26 weeks). The final analysis showed that TGP acted as a unique nonbiologic disease-modifying antirheumatic drug (nonbiologic DMARD), and its therapeutic effects were safe and efficacious for the treatment of JIA with few AEs. However, more high-quality RCTs are needed to confirm these therapeutic effects. PMID:27525026

  15. Synthesis, colon-targeted studies and pharmacological evaluation of an anti-ulcerative colitis drug 4-Aminosalicylic acid-β-O-glucoside.

    PubMed

    Li, Feifei; Wu, Guoli; Zheng, Huixia; Wang, Li; Zhao, Zhengbao

    2016-01-27

    A glycoside prodrug of 4-aminosalicylic acid (4-ASA) with d-glucose was synthesized for targeted drug delivery to inflammatory bowel. The in vitro assessment of 4-aminosalicylic acid-β-O-glucoside (4-ASA-Glu) as a colon-specific prodrug was studied using colitis rat with the healthy one as control. The stability studies in aqueous buffers (pH 1.2, 6.8 and 7.4) indicated that 4-ASA-Glu was stable over a period of 12 h. The incubation of 4-ASA-Glu with cecal or colonic contents of healthy rats at 37 °C released 4-ASA in 77 or 80% of the dose in 12 h, respectively. The amount of 4-ASA liberated from the incubation of 4-ASA-Glu in cecal or colonic contents of colitis rats at 37 °C was 69 or 79% in 12 h respectively, while less than 9% 4-ASA was detected from the incubation of 4-ASA-Glu with the homogenates of stomach or small intestine. The curative effect of 4-ASA-Glu was evaluated in 2, 4, 6-trinitrobenzenesulfonic acid (TNBS) induced experimental colitis model in male Sprague-Dawley (SD) rats. It was found that 4-ASA-Glu possess significantly ameliorate effect than sulfasalazine, oral 4- and 5-aminosalicylic acid. PMID:26717200

  16. Modulation of the CD4+ T-cell response by Helicobacter pylori depends on known virulence factors and bacterial cholesterol and cholesterol α-glucoside content.

    PubMed

    Beigier-Bompadre, Macarena; Moos, Verena; Belogolova, Elena; Allers, Kristina; Schneider, Thomas; Churin, Yuri; Ignatius, Ralf; Meyer, Thomas F; Aebischer, Toni

    2011-11-01

    Helicobacter pylori blocks the proliferation of human CD4(+) T cells, facilitated by vacuolating exotoxin (VacA) and γ-glutamyl transpeptidase (GGT). H. pylori-triggered T-cell reactions in mice correlate with bacterial cholesterol and cholesterol α-glucoside content but their role in human cells is unclear. We characterized the effect of VacA, GGT, and cholesterol on T-helper 1, T-helper 2, T-regulatory and T-helper 17 associated cytokines and T-cell proliferation. VacA, GGT, and bacterial cholesterol content exhibited differential and synergistic inhibitory effects on the expression of activation markers CD25 and CD69 and on interleukin 2, interleukin 4, interleukin 10, and interferon γ production. These factors did not affect the H. pylori-mediated abrogation of transforming growth factor β secretion or increased interleukin 6 production. Cholesterol α-glucosyltransferase-deficient bacteria exerted strongly reduced antiproliferative effects on primary human CD4(+) T cells. In conclusion, H. pylori shapes rather than suppresses human CD4(+) T-cell responses, and glucosylated cholesterol is a relevant bacterial component involved in this modulation. PMID:21921201

  17. A fragmentation study of an isoflavone glycoside, genistein-7-O-glucoside, using electrospray quadrupole time-of-flight mass spectrometry at high mass resolution

    NASA Astrophysics Data System (ADS)

    March, Raymond E.; Miao, Xiu-Sheng; Metcalfe, Chris D.; Stobiecki, Maciej; Marczak, Lukasz

    2004-03-01

    A mass spectrometric method based on the combined use of electrospray ionization, collision-induced dissociation and tandem mass spectrometry at high mass resolution has been applied to an investigation of the structural characterization of genistein-7-O-[beta]--glucoside (5,7,4'-trihydroxyisoflavone). The product ion mass spectrum of [M-H]- ions shows neutral losses of the glycan residue (162 Da) and of the glycan residue + H[radical sign] (163 Da) by rearrangement and scission, respectively, where the latter loss dominates at higher collision energies. The genistein moiety remained intact and only minor fragmentation of the glucose moiety was observed. The low-energy product ion mass spectrum of [M+H]+ ions shows extensive fragmentation of the glucose moiety, though at low ion signal intensity, loss of the glycan residue, and simple fragmentation of the genistein moiety that permits characterization of the substituents in the A and B rings. The use of elevated cone voltages permitted observation of product ion mass spectra of selected primary fragment ions. Product ion mass spectra examined at high mass resolution allowed unambiguous determination of the elemental composition of fragment ions. Fragmentation mechanisms and ion structures have been proposed.

  18. Beta-D-glucoside protects against advanced glycation end products (AGEs)-mediated diabetic responses by suppressing ERK and inducing PPAR gamma DNA binding.

    PubMed

    Mahali, Sidhartha K; Manna, Sunil K

    2012-12-15

    Accumulation of advanced glycation end products (AGEs), due to excessive amounts of 3- or 4-carbon sugars derived from glucose; cause multiple consequences in diabetic patients and older persons. The transcription factor, peroxisome proliferator-activated receptor gamma (PPARγ), is down regulated in the diabetic condition. Drugs targeting PPARγ were developed for diabetes therapy. We found that AGE inhibited PPARγ activity in different cell types induced by PPARγ activators, like troglitazone, rosiglitazone, oleamide, and anandamide. AGE induced translocation of PPARγ from nucleus to cytoplasm, increased on activation of ERK in cells. Antioxidants that inhibit AGE-induced NF-κB activation by preventing ROI generation were unable to protect AGE-mediated decrease in PPARγ activity. Only mangiferin, a β-D-glucoside, prevented AGE-mediated decrease in PPARγ activity and inhibited phosphorylation of ERK and cytoplasmic translocation of PPARγ. Mangiferin interacts with PPARγ and enhanced its DNA binding activity as predicted by in silico and shown by in vitro DNA-binding activity. Overall, the data suggest that (i) mangiferin inhibited AGE-induced ERK activation thereby inhibited PPARγ phosphorylation and cytoplasmic translocation; (ii) mangiferin interacts with PPARγ and enhances its DNA-binding ability. With these dual effects, mangiferin can be a likely candidate for developing therapeutic drug against diabetes. PMID:23058985

  19. Interactions of milk α- and β-casein with malvidin-3-O-glucoside and their effects on the stability of grape skin anthocyanin extracts.

    PubMed

    He, Zhiyong; Xu, Mingzhu; Zeng, Maomao; Qin, Fang; Chen, Jie

    2016-05-15

    The interactions of α- and β-casein with malvidin-3-O-glucoside (MG), the major anthocyanin in grape skin anthocyanin extracts (GSAE), were examined at pH 6.3 by fluorescence, fourier transform infrared (FTIR) and circular dichroism (CD) spectroscopy. The binding constant (KS), binding force and effects of the interactions on the caseins conformation and GSAE stability were investigated. The results showed that α- and β-casein bound with MG via hydrophilic (van der Waals forces or hydrogen bonding) and hydrophobic interactions, respectively. α-Casein had a slightly stronger binding affinity toward MG than β-casein, with respective KS values of 0.51×10(3)M(-1) and 0.46×10(3)M(-1) at 297K. The secondary structures of α- and β-casein were changed by MG binding, with a decrease in α-helix and an increase in turn for α-casein and no change in α-helix and a decrease in turn for β-casein. The casein-anthocyanin interaction appeared to have a positive effect on the thermal, oxidation and photo stability of GSAE. PMID:26775977

  20. Validation of a RP-HPLC-DAD Method for Chamomile (Matricaria recutita) Preparations and Assessment of the Marker, Apigenin-7-glucoside, Safety and Anti-Inflammatory Effect

    PubMed Central

    Miguel, Felipe Galeti; Cavalheiro, Amanda Henriques; Spinola, Nathália Favaretto; Ribeiro, Diego Luis; Barcelos, Gustavo Rafael Mazzaron; Antunes, Lusânia Maria Greggi; Hori, Juliana Issa; Marquele-Oliveira, Franciane; Rocha, Bruno Alves; Berretta, Andresa Aparecida

    2015-01-01

    Chamomile is a medicinal plant, which presents several biological effects, especially the anti-inflammatory effect. One of the compounds related to this effect is apigenin, a flavonoid that is mostly found in its glycosylated form, apigenin-7-glucoside (APG), in natural sources. However, the affectivity and safety of this glycoside have not been well explored for topical application. In this context, the aim of this work was to develop and validate a reversed-phase high-performance liquid chromatography (RP-HPLC-DAD) method to quantify APG in chamomile preparations. Additionally, the safety and the anti-inflammatory potential of this flavonoid were verified. The RP-HPLC-DAD method was developed and validated with linearity at 24.0–36.0 μg/mL range (r = 0.9994). Intra- and interday precision (RSD) were 0.27–2.66% and accuracy was 98.27–101.21%. The validated method was applied in the analysis of chamomile flower heads, glycolic extract, and Kamillen cream, supporting the method application in the quality control of chamomile preparations. Furthermore, the APG safety was assessed by MTT cytotoxicity assay and mutagenic protocols and the anti-inflammatory activity was confirmed by a diminished TNF-α production showed by mice macrophages treated with APG following LPS treatment. PMID:26421053

  1. Development and validation of an HPTLC method for apigenin 7-O-glucoside in chamomile flowers and its application for fingerprint discrimination of chamomile-like materials.

    PubMed

    Guzelmeric, Etil; Vovk, Irena; Yesilada, Erdem

    2015-03-25

    Brewed tea of chamomile flowers (Matricaria recutita L.) (Asteraceae) has been extensively consumed for centuries due to either its pleasant taste or medicinal purposes. On the other hand, the major problem is difficulty in distinguishing the genuine specimen when supplying chamomile through nature-picking. Consequently flowers of other Asteraceae members resembling to chamomile in appearance may frequently be practiced by lay people or marketed in spice shops or bazaars. Evidently detection of such adulterations plays a vital role in terms of public health to avoid risk of toxicity (i.e. pyrazolidin alkaloids) and ineffective treatments (lack or insufficient concentration of the active constituents). This work presents either development and validation of a high performance thin-layer chromatographic (HPTLC) method for apigenin 7-O-glucoside which is one of the active markers in chamomile flowers or its application for the fingerprint discrimination of chamomile-like materials i.e. Anthemis spp., Bellis spp., Chrysanthemum sp. and Tanacetum sp. gathered by local people assuming as chamomile. Separation was performed on the silica gel 60 NH2 F254s HPTLC plates using the developing solvent system of ethyl acetate-formic acid-acetic acid-water (30:1.5:1.5:3, v/v/v/v). The proposed HPTLC method may also be a leading guide for the quality assessment of chamomile tea products on the market. PMID:25575175

  2. Validation of a RP-HPLC-DAD Method for Chamomile (Matricaria recutita) Preparations and Assessment of the Marker, Apigenin-7-glucoside, Safety and Anti-Inflammatory Effect.

    PubMed

    Miguel, Felipe Galeti; Cavalheiro, Amanda Henriques; Spinola, Nathália Favaretto; Ribeiro, Diego Luis; Barcelos, Gustavo Rafael Mazzaron; Antunes, Lusânia Maria Greggi; Hori, Juliana Issa; Marquele-Oliveira, Franciane; Rocha, Bruno Alves; Berretta, Andresa Aparecida

    2015-01-01

    Chamomile is a medicinal plant, which presents several biological effects, especially the anti-inflammatory effect. One of the compounds related to this effect is apigenin, a flavonoid that is mostly found in its glycosylated form, apigenin-7-glucoside (APG), in natural sources. However, the affectivity and safety of this glycoside have not been well explored for topical application. In this context, the aim of this work was to develop and validate a reversed-phase high-performance liquid chromatography (RP-HPLC-DAD) method to quantify APG in chamomile preparations. Additionally, the safety and the anti-inflammatory potential of this flavonoid were verified. The RP-HPLC-DAD method was developed and validated with linearity at 24.0-36.0 μg/mL range (r = 0.9994). Intra- and interday precision (RSD) were 0.27-2.66% and accuracy was 98.27-101.21%. The validated method was applied in the analysis of chamomile flower heads, glycolic extract, and Kamillen cream, supporting the method application in the quality control of chamomile preparations. Furthermore, the APG safety was assessed by MTT cytotoxicity assay and mutagenic protocols and the anti-inflammatory activity was confirmed by a diminished TNF-α production showed by mice macrophages treated with APG following LPS treatment. PMID:26421053

  3. Determination of cyanidin 3-glucoside in rat brain, liver and kidneys by UPLC/MS-MS and its application to a short-term pharmacokinetic study.

    PubMed

    Fornasaro, Stefano; Ziberna, Lovro; Gasperotti, Mattia; Tramer, Federica; Vrhovšek, Urška; Mattivi, Fulvio; Passamonti, Sabina

    2016-01-01

    Anthocyanins exert neuroprotection in various in vitro and in vivo experimental models. However, no details regarding their brain-related pharmacokinetics are so far available to support claims about their direct neuronal bioactivity as well as to design proper formulations of anthocyanin-based products. To gather this missing piece of knowledge, we intravenously administered a bolus of 668 nmol cyanidin 3-glucoside (C3G) in anaesthetized Wistar rats and shortly after (15 s to 20 min) we collected blood, brain, liver, kidneys and urine samples. Extracts thereof were analysed for C3G and its expected metabolites using UPLC/MS-MS. The data enabled to calculate a set of pharmacokinetics parameters. The main finding was the distinctive, rapid distribution of C3G in the brain, with an apparently constant plasma/brain ratio in the physiologically relevant plasma concentration range (19-355 nM). This is the first report that accurately determines the distribution pattern of C3G in the brain, paving the way to the rational design of future tests of neuroprotection by C3G in animal models and humans. PMID:26965389

  4. Evaluation of the new anti-inflammatory compound ethyl salicylate 2-O-β-D-glucoside and its possible mechanism of action.

    PubMed

    Xin, Wenyu; Huang, Chao; Zhang, Xue; Zhang, Guidong; Ma, Xiaowei; Sun, Lan; Wang, Chao; Zhang, Dongming; Zhang, Tiantai; Du, Guanhua

    2013-02-01

    Ethyl salicylate 2-O-β-d-glucoside (ESG) is a derivative of natural salicylate isolated from Gaultheria yunnanensis (Franch.) Rehder, it has been used for the treatments of rheumatoid arthritis, swelling and pain. The aim of this study was to evaluate the anti-inflammatory effects of ESG and explore the anti-inflammatory mechanisms. We found that ESG had potent anti-inflammatory effects on the lipopolysaccharide (LPS)-activated murine macrophages RAW264.7. ESG exerted a dose-dependent inhibition of the LPS-stimulated release of the pro-inflammatory cytokines TNF-α and IL-1β. Moreover, it significantly inhibited LPS-stimulated the production of NO and PGE2 by repressing the expression of iNOS and COX protein respectively. Western blot analysis showed that ESG prominently inhibited LPS-induced activation of NF-κB in RAW264.7 cells by blocking phosphorylation of inhibitor IκBα and p65. Consistent with these results, we found that ESG prevented the nuclear translocation of NF-κB induced by LPS. Our study suggests that ESG may be effective in the treatment of inflammatory diseases by inhibiting the pro-inflammatory cytokine production and regulating the NF-κB signal pathway. PMID:23219581

  5. Delphinidin-3-Glucoside Protects against Oxidized Low-Density Lipoprotein-Induced Mitochondrial Dysfunction in Vascular Endothelial Cells via the Sodium-Dependent Glucose Transporter SGLT1

    PubMed Central

    Chen, Ming-liang; Chen, Chun-ye; Chang, Hui; Zhang, Ting; Wang, Li; Zhu, Jun-dong; Zhang, Qian-yong; Mi, Man-tian

    2013-01-01

    Delphinidin-3-glucoside (Dp) is a member of a family of bioactive compounds known as anthocyanins that occur naturally in pigmented plants and are known to ameliorate oxidative stress. Previous studies have showed that Dp decreased oxidative stress in vascular endothelial cells, however, the underlying mechanisms remain largely unknown. In the present study, we showed that pretreatment with Dp significantly suppressed oxidized low-density lipoprotein (oxLDL)-induced cell proliferation inhibition and apoptosis in primary human umbilical vein endothelial cells (HUVECs). Also, Dp pretreatment attenuated oxLDL-induced mitochondrial dysfunction via decreased reactive oxygen species (ROS) and superoxide anion generation, thereby repressing mitochondrial membrane potential and closing mitochondrial permeability transition pore. Furthermore, in vitro and in vivo data showed that Dp was transported into endothelial cells in a temperature, concentration, and time-dependent manner via the sodium-dependent glucose transporter (SGLT1). Suppression of SGLT1 by its substrate glucose, its inhibitor phlorizin or SGLT1 siRNA blocked Dp transportation. Repression of SGLT1 significantly inhibited Dp function of ameliorating mitochondrial dysfunction induced by pro-apoptotic factors (Apoptosis-inducing factor, Cytochrome c, Caspase-3 and Bax/Bcl-2 ratio). Taken together, our data indicate that Dp protects VECs via the SGLT1-ROS-mitochodria pathway. This new insight may help to elucidate the molecular mechanisms underlying the vascular protection afforded by Dp, and anthocyanins in general, in the context of prevention of endothelial dysfunction and atherosclerosis. PMID:23874689

  6. A novel soybean (Glycine max) gene encoding a family 3 β-glucosidase has high isoflavone 7-O-glucoside-hydrolyzing activity in transgenic rice.

    PubMed

    Hsu, Chia-Chen; Wu, Tsung-Meng; Hsu, Yi-Ting; Wu, Chih-Wen; Hong, Chwan-Yang; Su, Nan-Wei

    2015-01-28

    A previous study demonstrated that purified Glycine max β-glucosidase (GmBGL) could hydrolyze glucosyl isoflavone to the aglyconic form. This study reports the cloning and functional characterization of a soybean cDNA encoding the β-glucosidase. GmBGL was isolated by use of a purified soybean N-terminal amino acid sequence and conserved sequences of β-glucosidase genes from other plants. Sequence analysis of GmBGL revealed an open reading frame of 1884 bp encoding a polypeptide of 627 amino acids with a calculated molecular mass of 69 kDa. Phylogenetic analysis classified the GmBGL into the glycosyl hydrolase 3 family. In soybean, the GmBGL transcript was predominantly accumulated in roots and leaves. To examine the enzymatic activity and substrate specificity, GmBGL was ectopically expressed in transgenic rice. Purified GmBGL protein from transgenic rice could catalyze the hydrolysis of genistin and daidzin to produce genistein and daidzein, respectively, which confirmed GmBGL as a functional β-glucosidase with isoflavone glucoside-hydrolyzing activity. This paper reveals that GmBGL is a key enzyme in transforming glucosyl isoflavones to aglycones in soybean, which may help in genetic manipulation of aglycone-rich soybean seeds. PMID:25569564

  7. Novel long chain fatty acid derivatives of quercetin-3-O-glucoside reduce cytotoxicity induced by cigarette smoke toxicants in human fetal lung fibroblasts.

    PubMed

    Warnakulasuriya, Sumudu N; Ziaullah; Rupasinghe, H P Vasantha

    2016-06-15

    Smoking has become a global health concern due to its association with many disease conditions, such as chronic obstructive pulmonary disease (COPD), cardiovascular diseases (CVD) and cancer. Flavonoids are plant polyphenolic compounds, studied extensively for their antioxidant, anti-inflammatory, and anti-carcinogenic properties. Quercetin-3-O-glucoside (Q3G) is a flavonoid which is widely found in plants. Six novel long chain fatty acid [stearic acid, oleic acid, linoleic acid, α-linolenic acid (ALA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)] derivatives of Q3G were evaluated for their potential in protecting human lung fibroblasts against cytotoxicity induced by selected cigarette smoke toxicants: 4-(methylnitrosoamino)-1-(3-pyridinyl)-1-butanone (NNK), benzo-α-pyrene (BaP), nicotine and chromium (Cr[VI]). Nicotine and Cr[VI] induced toxicity in fibroblasts and reduced the percentage of viable cells, while BaP and NNK did not affect cell viability. The fatty acid derivatives of Q3G provided protection against nicotine- and Cr[VI]-induced cell death and membrane lipid peroxidation. Based on the evaluation of inflammatory markers of cyclooxygenase-2 (COX-2) and prostaglandin E2 (PGE2), the fatty acid derivatives of Q3G were found to be effective in lowering the inflammatory response. Overall, these novel fatty acid esters of Q3G warrant further investigation as potential cytoprotective agents. PMID:27071958

  8. Efficient one-pot enzymatic synthesis of alpha-(1-->4)-glucosidic disaccharides through a coupled reaction catalysed by Lactobacillus acidophilus NCFM maltose phosphorylase.

    PubMed

    Nakai, Hiroyuki; Dilokpimol, Adiphol; Abou Hachem, Maher; Svensson, Birte

    2010-05-27

    Lactobacillus acidophilus NCFM maltose phosphorylase (LaMalP) of glycoside hydrolase family 65 catalysed enzymatic synthesis of alpha-(1-->4)-glucosidic disaccharides from maltose and five monosaccharides in a coupled phosphorolysis/reverse phosphorolysis one-pot reaction. Thus phosphorolysis of maltose to beta-glucose 1-phosphate circumvented addition of costly beta-glucose 1-phosphate for reverse phosphorolysis with different monosaccharide acceptors, resulting in 91%, 89%, 88%, 86% and 84% yield of alpha-d-glucopyranosyl-(1-->4)-N-acetyl-D-glucosaminopyranose [N-acetyl-maltosamine], alpha-D-glucopyranosyl-(1-->4)-D-glucosaminopyranose [maltosamine], alpha-D-glucopyranosyl-(1-->4)-D-mannopyranose, alpha-D-glucopyranosyl-(1-->4)-L-fucopyranose and alpha-D-glucopyranosyl-(1-->4)-D-xylopyranose, respectively, from 0.1M maltose, 0.5M N-acetyl glucosamine, 0.1M glucosamine, 0.1M mannose, 1M L-fucose and 0.5M xylose in 0.2M phosphate-citrate pH 6.2. These current yields of 0.27-0.34 g of disaccharide products from 10 mL reaction mixtures are easy to scale up and moreover the strategy can be applied to large-scale production of other oligosaccharides from low-cost disaccharides as catalysed by phosphorylases with different substrate specificities. PMID:20392438

  9. Total glucosides of paeony (TGP) inhibits the production of inflammatory cytokines in oral lichen planus by suppressing the NF-κB signaling pathway.

    PubMed

    Wang, Yanni; Zhang, Han; Du, Guanhuan; Wang, Yufeng; Cao, Tianyi; Luo, Qingqiong; Chen, Junjun; Chen, Fuxiang; Tang, Guoyao

    2016-07-01

    Total glucosides of paeony (TGP) is a bioactive compound extracted from paeony roots and has been widely used to ameliorate inflammation in several autoimmune and inflammatory diseases. However, the anti-inflammatory effect of TGP on oral lichen planus (OLP), a chronic inflammatory oral condition characterized by T-cell infiltration and abnormal epithelial keratinization cycle remains unclear. In this study, we found that TLR4 was highly expressed and activation of the NF-κB signaling pathway was obviously observed in the OLP tissues. Moreover, there was significant higher mRNA expression of inflammatory cytokines interleukin-6 (IL-6) and tumor necrosis factor-α (TNF-α) in OLP keratinocytes than normal oral epithelial keratinocytes. With the help of the cell culture model by stimulating the keratinocyte HaCaT cells with lipopolysaccharides (LPS), we mimicked the local inflammatory environment of OLP. And we further confirmed that TGP could inhibit LPS-induced production of IL-6 and TNF-α in HaCaT cells via a dose-dependent manner. TGP treatment decreased the phosphorylation of IκBα and NF-κB p65 proteins, thus leading to less nuclear translocation of NF-κB p65 in HaCaT cells. Therefore, our data suggested that TGP may be a new potential candidate for the therapy of OLP. PMID:27107800

  10. The Efficacy and Safety of the Combination of Total Glucosides of Peony and Leflunomide for the Treatment of Rheumatoid Arthritis: A Systemic Review and Meta-Analysis

    PubMed Central

    Feng, Zhitao; Xu, Juan; He, Guochao; Cao, Meiqun; Duan, Lihong; Chen, Liguo; Wu, Zhengzhi

    2016-01-01

    Objective. To evaluate the efficacy and safety of the total glucosides of peony (TGP) and leflunomide (LEF) for the treatment of rheumatoid arthritis (RA). Methods. Randomized controlled trials (RCTs) on the efficacy and safety of the combination of TGP and LEF versus LEF alone for the treatment of RA were retrieved by searching PubMed, EMBASE, Cochrane Library, the China National Knowledge Infrastructure database, and Wanfang database. Results. Eight RCTs including 643 RA patients were included in the present meta-analysis. The quality of included studies was poor. The levels of ESR (P < 0.0001), CRP (P < 0.0001), and RF (P < 0.0001) in RA patients who received the combination of TGP and LEF were significantly lower than RA patients who received LEF therapy alone. The pooled results suggest that the combination of TGP and LEF caused less abnormal liver function than LEF alone (P = 0.02). No significant difference in the gastrointestinal discomfort was identified between the combination of TGP and LEF and LEF alone groups (P = 0.18). Conclusion. The combination of TGP and LEF in treatment of RA presented the characteristics of notably decreasing the levels of laboratory indexes and higher safety in terms of liver function. However, this conclusion should be further investigated based on a larger sample size. PMID:27143990

  11. The Role of Sodium-Dependent Glucose Transporter 1 and Glucose Transporter 2 in the Absorption of Cyanidin-3-O-β-Glucoside in Caco-2 Cells

    PubMed Central

    Zou, Tang-Bin; Feng, Dan; Song, Gang; Li, Hua-Wen; Tang, Huan-Wen; Ling, Wen-Hua

    2014-01-01

    Anthocyanins have multiple biological activities of benefit to human health. While a few studies have been conducted to evaluate the bioavailability of anthocyanins, the mechanisms of their absorption mechanism remain ill-defined. In the present study, we investigated the absorption mechanism of cyanidin-3-O-β-glucoside (Cy-3-G) in human intestinal epithelial (Caco-2) cells. Cy-3-G transport was assessed by measuring the absorptive and efflux direction. Inhibition studies were conducted using the pharmacological agents, phloridzin, an inhibitor of sodium-dependent glucose transporter 1 (SGLT1), or phloretin, an inhibitor of glucose transporter 2 (GLUT2). The results showed that phloridzin and phloretin significantly inhibited the absorption of Cy-3-G. In addition, Caco-2 cells transfected with small interfering RNA (siRNA) specific for SGLT1 or GLUT2 showed significantly decreased Cy-3-G absorption. These siRNA transfected cells also showed a significantly decreased rate of transport of Cy-3-G compared with the control group. These findings suggest that Cy-3-G absorption is dependent on the activities of SGLT1 and GLUT2 in the small intestine and that SGLT1 and GLUT2 could be a limiting step for the bioavailability of Cy-3-G. PMID:25314643

  12. Gas chromatographic separation of bile acid 3-glucosides and 3-glucuronides without prior deconjugation on a stainless-steel capillary column.

    PubMed

    Iida, T; Tazawa, S; Tamaru, T; Goto, J; Nambara, T

    1995-01-01

    A method for the gas chromatographic (GC) separation of the 3-glucoside and 3-glucuronide conjugates of bile acids without the necessity for a hydrolytic step is described. The bile acid glycosides were derivatized to their complete methyl ester trimethylsilyl (Me-TMS) or methyl ester dimethylethylsilyl (Me-DMES) ether derivatives, which in turn were chromatographed on an inert and thermostable stainless-steel capillary column, Ultra ALLOY-1 (HT), coated with a thin film (0.15 micron) of chemically bonded and cross-linked dimethylsiloxane. They exhibited a single peak of the theoretical shape without any accompanying peaks due to thermal decomposition, even at oven temperatures of 320-330 degrees C. Excellent GC separation of isomeric bile acid glycosides was achieved by the combined use of suitable derivatives and column. This method, which does not need the prior deconjugation of the glycosidic moiety, could be usefully applied to biosynthetic and metabolic studies of bile acids in biological materials. PMID:7881536

  13. Biosynthesis of the Cyanogenic Glucoside Dhurrin in Seedlings of Sorghum bicolor (L.) Moench and Partial Purification of the Enzyme System Involved 1

    PubMed Central

    Halkier, Barbara Ann; Møller, Birger Lindberg

    1989-01-01

    The cyanogenic glucoside dhurrin is rapidly synthesized in etiolated seedlings of Sorghum bicolor (L.) Moench. The dhurrin content of the seedlings increases sigmoidally with the germination time. Shoots of 10 centimeters height contain 850 nanomoles of dhurrin per shoot corresponding to 6% of the dry weight. The biosynthetic activity sharply rises upon germination and reaches a maximum level of 10 nanomoles dhurrin/(hour × shoot) after 48 hours when the shoots are 3 centimeters high. This maximum level is followed by a sharp decline in activity when germination time exceeds 65 hours. Dhurrin and the dhurrin-synthesizing enzyme system are primarily located in the upper part of the etiolated shoot where both are evenly distributed between the coleoptile, the primary leaves and the upper 0.5 centimeter of the first internode including the shoot apex. Dhurrin constitutes 30% of the dry weight of the upper 1.2 centimeter of 10 centimeter high shoots. The seed and root contain neither dhurrin nor the dhurrin-synthesizing enzyme system. The codistribution of dhurrin and the enzyme system throughout the seedling indicates that production and storage sites are located within the same cell. Purification of the dhurrin-synthesizing enzyme by gel filtration or by sucrose gradient centrifugations results in a tenfold increase in specific activity. Further purification is accompained by a decline in specific activity due to loss of essential components as demonstrated by reconstitution experiments. Images Figure 7 Figure 8 PMID:16666964

  14. TSG (2,3,5,4'-Tetrahydroxystilbene-2-O- β -D-glucoside) from the Chinese Herb Polygonum multiflorum Increases Life Span and Stress Resistance of Caenorhabditis elegans.

    PubMed

    Büchter, Christian; Zhao, Liang; Havermann, Susannah; Honnen, Sebastian; Fritz, Gerhard; Proksch, Peter; Wätjen, Wim

    2015-01-01

    2,3,5,4'-Tetrahydroxystilbene-2-O-β-D-glucoside (TSG) was isolated from Polygonum multiflorum, a plant which is traditionally used as an anti-ageing drug. We have analysed ageing-related effects of TSG in the model organism C. elegans in comparison to resveratrol. TSG exerted a high antioxidative capacity both in a cell-free assay and in the nematode. The antioxidative capacity was even higher compared to resveratrol. Presumably due to its antioxidative effects, treatment with TSG decreased the juglone-mediated induction of the antioxidative enzyme SOD-3; the induction of the GST-4 by juglone was diminished slightly. TSG increased the resistance of C. elegans against lethal thermal stress more prominently than resveratrol (50 μM TSG increased mean survival by 22.2%). The level of the ageing pigment lipofuscin was decreased after incubation with the compound. TSG prolongs the mean, median, and maximum adult life span of C. elegans by 23.5%, 29.4%, and 7.2%, respectively, comparable to the effects of resveratrol. TSG-mediated extension of life span was not abolished in a DAF-16 loss-of-function mutant strain showing that this ageing-related transcription factor is not involved in the effects of TSG. Our data show that TSG possesses a potent antioxidative capacity, enhances the stress resistance, and increases the life span of the nematode C. elegans. PMID:26075030

  15. Malvidin-3-O-β glucoside, major grape anthocyanin, inhibits human macrophage-derived inflammatory mediators and decreases clinical scores in arthritic rats.

    PubMed

    Decendit, Alain; Mamani-Matsuda, Maria; Aumont, Virginie; Waffo-Teguo, Pierre; Moynet, Daniel; Boniface, Katia; Richard, Emmanuel; Krisa, Stéphanie; Rambert, Jérôme; Mérillon, Jean-Michel; Mossalayi, M D

    2013-11-15

    Polyphenolic anthocyanins are major colorful compounds in red fruits, known to prevent cardiovascular and other diseases. Grape polyphenols are a mixture of various molecules and their exact contribution to above bioactivities remains to be clarified. In the present study, we first analyzed the effect of purified grape-derived compounds on human peripheral blood mononuclear cell (PBMC) survival, proliferation, as well as for their ability to inhibit the activation of human normal macrophages. Data indicated that malvidin-3-O-β glucoside (Malβg), the major grape anthocyanin, is bioactive with no toxicity on human PBMC. Malβg decreased the transcription of genes encoding inflammatory mediators, confirmed by the inhibition of TNFα, IL1, IL-6 and iNOS-derived nitric oxide (NO) secretion from activated macrophages. As Malβg also inhibited inflammatory response of rat macrophages, we investigated the anti-inflammatory potential of Malβg in chronic rat adjuvant-induced arthritis (AIA). Malβg significantly diminished inflammatory cachexia and arthritic paw scores in AIA rats at both therapeutic and preventive levels. In vivo effects of Malβg correlated with down-regulation of NO generation from AIA rats' peritoneal macrophages ex vivo. These data indicate that Malβg, major grape anthocyanin, is a potent anti-inflammatory agent in vitro and in vivo, without detectable toxic effect. PMID:23796750

  16. The role of sodium-dependent glucose transporter 1 and glucose transporter 2 in the absorption of cyanidin-3-o-β-glucoside in Caco-2 cells.

    PubMed

    Zou, Tang-Bin; Feng, Dan; Song, Gang; Li, Hua-Wen; Tang, Huan-Wen; Ling, Wen-Hua

    2014-10-01

    Anthocyanins have multiple biological activities of benefit to human health. While a few studies have been conducted to evaluate the bioavailability of anthocyanins, the mechanisms of their absorption mechanism remain ill-defined. In the present study, we investigated the absorption mechanism of cyanidin-3-O-β-glucoside (Cy-3-G) in human intestinal epithelial (Caco-2) cells. Cy-3-G transport was assessed by measuring the absorptive and efflux direction. Inhibition studies were conducted using the pharmacological agents, phloridzin, an inhibitor of sodium-dependent glucose transporter 1 (SGLT1), or phloretin, an inhibitor of glucose transporter 2 (GLUT2). The results showed that phloridzin and phloretin significantly inhibited the absorption of Cy-3-G. In addition, Caco-2 cells transfected with small interfering RNA (siRNA) specific for SGLT1 or GLUT2 showed significantly decreased Cy-3-G absorption. These siRNA transfected cells also showed a significantly decreased rate of transport of Cy-3-G compared with the control group. These findings suggest that Cy-3-G absorption is dependent on the activities of SGLT1 and GLUT2 in the small intestine and that SGLT1 and GLUT2 could be a limiting step for the bioavailability of Cy-3-G. PMID:25314643

  17. Inhibition of Carrageenan-Induced Acute Inflammation in Mice by Oral Administration of Anthocyanin Mixture from Wild Mulberry and Cyanidin-3-Glucoside

    PubMed Central

    Hassimotto, Neuza Mariko Aymoto; Moreira, Vanessa; do Nascimento, Neide Galvão; Souto, Pollyana Cristina Maggio de Castro; Teixeira, Catarina; Lajolo, Franco Maria

    2013-01-01

    Anthocyanins are flavonoids which demonstrated biological activities in in vivo and in vitro models. Here in the anti-inflammatory properties of an anthocyanin-enriched fraction (AF) extracted from wild mulberry and the cyanidin-3-glucoside (C3G), the most abundant anthocyanin in diet, were studied in two acute inflammation experimental models, in the peritonitis and in the paw oedema assays, both of which were induced by carrageenan (cg) in mice. In each trial, AF and C3G (4 mg/100 g/animal) were orally administered in two distinct protocols: 30 min before and 1 h after cg stimulus. The administration of both AF and C3G suppresses the paw oedema in both administration times (P < 0.05). In the peritonitis, AF and C3G reduced the polymorphonuclear leukocytes (PMN) influx in the peritoneal exudates when administered 1 h after cg injection. AF was more efficient reducing the PMN when administered 30 min before cg. Both AF and C3G were found to suppress mRNA as well as protein levels of COX-2 upregulated by cg in both protocols, but the inhibitory effect on PGE2 production in the peritoneal exudates was observed when administered 30 min before cg (P < 0.05). Our findings suggest that AF and C3G minimize acute inflammation and they present positive contributions as dietary supplements. PMID:23484081

  18. Determination of cyanidin 3-glucoside in rat brain, liver and kidneys by UPLC/MS-MS and its application to a short-term pharmacokinetic study

    PubMed Central

    Fornasaro, Stefano; Ziberna, Lovro; Gasperotti, Mattia; Tramer, Federica; Vrhovšek, Urška; Mattivi, Fulvio; Passamonti, Sabina

    2016-01-01

    Anthocyanins exert neuroprotection in various in vitro and in vivo experimental models. However, no details regarding their brain-related pharmacokinetics are so far available to support claims about their direct neuronal bioactivity as well as to design proper formulations of anthocyanin-based products. To gather this missing piece of knowledge, we intravenously administered a bolus of 668 nmol cyanidin 3-glucoside (C3G) in anaesthetized Wistar rats and shortly after (15 s to 20 min) we collected blood, brain, liver, kidneys and urine samples. Extracts thereof were analysed for C3G and its expected metabolites using UPLC/MS-MS. The data enabled to calculate a set of pharmacokinetics parameters. The main finding was the distinctive, rapid distribution of C3G in the brain, with an apparently constant plasma/brain ratio in the physiologically relevant plasma concentration range (19–355 nM). This is the first report that accurately determines the distribution pattern of C3G in the brain, paving the way to the rational design of future tests of neuroprotection by C3G in animal models and humans. PMID:26965389

  19. Bioconversion of Cyanidin-3-Rutinoside to Cyanidin-3-Glucoside in Black Raspberry by Crude α-L-Rhamnosidase from Aspergillus Species.

    PubMed

    Lim, Taehwan; Jung, Hana; Hwang, Keum Taek

    2015-11-28

    Cyanidin-3-glucoside (C3G) has been known to be more bioavailable than cyanidin-3- rutinoside (C3R), the most abundant anthocyanin in black raspberry (Rubus occidentalis). The aim of this study was to enhance the bioavailability of anthocyanins in black raspberry by cleaving L-rhamnose in C3R using crude enzyme extracts (CEEs) from Aspergillus usamii KCTC 6956, A. awamori KCTC 60380, A. niger KCCM 11724, A. oryzae KCCM 12698, and A. kawachii KCCM 32819. The enzyme activities of the CEEs were determined by a spectrophotometric method using rho-nitrophenyl-rhamnopyranoside and rho-nitrophenyl-glucopyranoside. The CEE from A. usamii had the highest α-L-rhamnosidase activity with 2.73 U/ml at 60°C, followed by those from A. awamori and A. niger. When bioconversion of C3R to C3G in black raspberry was analyzed by HPLC-DAD, the CEEs from A. usamii and A. awamori hydrolyzed 95.7% and 95.6% of C3R to C3G, respectively, after 2 h incubation. The CEEs from A. kawachii and A. oryzae did not convert C3R to C3G in black raspberry. PMID:26165319

  20. Cucurbitacin L 2-O-β-Glucoside Demonstrates Apoptogenesis in Colon Adenocarcinoma Cells (HT-29): Involvement of Reactive Oxygen and Nitrogen Species Regulation.

    PubMed

    Abdelwahab, Siddig Ibrahim; Hassan, Loiy Elsir Ahmed; Abdul Majid, Amin M S; Yagi, Sakina M Ahmed; Mohan, Syam; Elhassan Taha, Manal Mohamed; Ahmad, Syahida; Chuen, Cheah Shiau; Narrima, Putri; Rais, Mohd Mustafa; Syam, Suvitha; Moharam, Bushra Abdulkarim; Hadi, A Hamid A

    2012-01-01

    Emerging evidence suggests that reactive oxygen (ROS) and nitrogen (RNS) species can contribute to diverse signalling pathways of inflammatory and tumour cells. Cucurbitacins are a group of highly oxygenated triterpenes. Many plants used in folk medicine to treat cancer have been found to contain cucurbitacins displaying potentially important anti-inflammatory actions. The current study was designed to investigate the anti-ROS and -RNS effects of cucurbitacin L 2-O-β-glucoside (CLG) and the role of these signaling factors in the apoptogenic effects of CLG on human colon cancer cells (HT-29). This natural cucurbitacin was isolated purely from Citrullus lanatus var. citroides (Cucurbitaceae). The results revealed that CLG was cytotoxic to HT-29. CLG increased significantly (P < 0.05) RNA and protein levels of caspase-3 in HT-29 cells when verified using a colorimetric assay and realtime qPCR, respectively. The results showed that lipopolysaccharide/interferon-gamma (LPS/INF-γ) increased nitrous oxide (NO) production inR AW264.7macrophages, whereas N(G)-nitro-L-argininemethyl ester (L-NAME) and CLG curtailed it. This compound did not reveal any cytotoxicity on RAW264.7 macrophages and human normal liver cells (WRL-68) when tested using the MTT assay. Findings of ferric reducing antioxidant power (FRAP) and oxygen radical absorption capacity (ORAC) assays demonstrate the antioxidant properties of CLG. The apoptogenic property of CLG on HT-29 cells is thus related to inhibition of reactive nitrogen and oxygen reactive species and the triggering of caspase-3-regulated apoptosis. PMID:22685485

  1. Cucurbitacin L 2-O-β-Glucoside Demonstrates Apoptogenesis in Colon Adenocarcinoma Cells (HT-29): Involvement of Reactive Oxygen and Nitrogen Species Regulation

    PubMed Central

    Abdelwahab, Siddig Ibrahim; Hassan, Loiy Elsir Ahmed; Abdul Majid, Amin M. S.; Yagi, Sakina M. Ahmed; Mohan, Syam; Elhassan Taha, Manal Mohamed; Ahmad, Syahida; Chuen, Cheah Shiau; Narrima, Putri; Rais, Mohd Mustafa; Syam, Suvitha; Moharam, Bushra Abdulkarim; Hadi, A. Hamid A.

    2012-01-01

    Emerging evidence suggests that reactive oxygen (ROS) and nitrogen (RNS) species can contribute to diverse signalling pathways of inflammatory and tumour cells. Cucurbitacins are a group of highly oxygenated triterpenes. Many plants used in folk medicine to treat cancer have been found to contain cucurbitacins displaying potentially important anti-inflammatory actions. The current study was designed to investigate the anti-ROS and -RNS effects of cucurbitacin L 2-O-β-glucoside (CLG) and the role of these signaling factors in the apoptogenic effects of CLG on human colon cancer cells (HT-29). This natural cucurbitacin was isolated purely from Citrullus lanatus var. citroides (Cucurbitaceae). The results revealed that CLG was cytotoxic to HT-29. CLG increased significantly (P < 0.05) RNA and protein levels of caspase-3 in HT-29 cells when verified using a colorimetric assay and realtime qPCR, respectively. The results showed that lipopolysaccharide/interferon-gamma (LPS/INF-γ) increased nitrous oxide (NO) production inR AW264.7macrophages, whereas N(G)-nitro-L-argininemethyl ester (L-NAME) and CLG curtailed it. This compound did not reveal any cytotoxicity on RAW264.7 macrophages and human normal liver cells (WRL-68) when tested using the MTT assay. Findings of ferric reducing antioxidant power (FRAP) and oxygen radical absorption capacity (ORAC) assays demonstrate the antioxidant properties of CLG. The apoptogenic property of CLG on HT-29 cells is thus related to inhibition of reactive nitrogen and oxygen reactive species and the triggering of caspase-3-regulated apoptosis. PMID:22685485

  2. Cytotoxicity, Antioxidant and Apoptosis Studies of Quercetin-3-O Glucoside and 4-(β-D-Glucopyranosyl-1→4-α-L-Rhamnopyranosyloxy)-Benzyl Isothiocyanate from Moringa oleifera.

    PubMed

    Maiyo, Fiona C; Moodley, Roshila; Singh, Moganavelli

    2016-01-01

    Moringa oleifera, from the family Moringaceae, is used as a source of vegetable and herbal medicine and in the treatment of various cancers in many African countries, including Kenya. The present study involved the phytochemical analyses of the crude extracts of M.oleifera and biological activities (antioxidant, cytotoxicity and induction of apoptosis in-vitro) of selected isolated compounds. The compounds isolated from the leaves and seeds of the plant were quercetin-3-O-glucoside (1), 4-(β-D-glucopyranosyl-1→4-α-L-rhamnopyranosyloxy)-benzyl isothiocyanate (2), lutein (3), and sitosterol (4). Antioxidant activity of compound 1 was significant when compared to that of the control, while compound 2 showed moderate activity. The cytotoxicity of compounds 1 and 2 were tested in three cell lines, viz. liver hepatocellular carcinoma (HepG2), colon carcinoma (Caco-2) and a non-cancer cell line Human Embryonic Kidney (HEK293), using the MTT cell viability assay and compared against a standard anticancer drug, 5-fluorouracil. Apoptosis studies were carried out using the acridine orange/ethidium bromide dual staining method. The isolated compounds showed selective in vitro cytotoxic and apoptotic activity against human cancer and non-cancer cell lines, respectively. Compound 1 showed significant cytotoxicity against the Caco-2 cell line with an IC50 of 79 μg mL(-1) and moderate cytotoxicity against the HepG2 cell line with an IC50 of 150 μg mL(-1), while compound 2 showed significant cytotoxicity against the Caco- 2 and HepG2 cell lines with an IC50 of 45 μg mL(-1) and 60 μg mL(-1), respectively. Comparatively both compounds showed much lower cytotoxicity against the HEK293 cell line with IC50 values of 186 μg mL(-1) and 224 μg mL(-1), respectively. PMID:26428271

  3. Impact of Cyanidin-3-Glucoside on Glycated LDL-Induced NADPH Oxidase Activation, Mitochondrial Dysfunction and Cell Viability in Cultured Vascular Endothelial Cells

    PubMed Central

    Xie, Xueping; Zhao, Ruozhi; Shen, Garry X.

    2012-01-01

    Elevated levels of glycated low density lipoprotein (glyLDL) are frequently detected in diabetic patients. Previous studies demonstrated that glyLDL increased the production of reactive oxygen species (ROS), activated NADPH oxidase (NOX) and suppressed mitochondrial electron transport chain (mETC) enzyme activities in vascular endothelial cells (EC). The present study examined the effects of cyanidin-3-glucoside (C3G), a type of anthocyanin abundant in dark-skinned berries, on glyLDL-induced ROS production, NOX activation and mETC enzyme activity in porcine aortic EC (PAEC). Co-treatment of C3G prevented glyLDL-induced upregulation of NOX4 and intracellular superoxide production in EC. C3G normalized glyLDL-induced inhibition on the enzyme activities of mETC Complex I and III, as well as the abundances of NADH dehydrogenase 1 in Complex I and cytochrome b in Complex III in EC. Blocking antibody for the receptor of advanced glycation end products (RAGE) prevented glyLDL-induced changes in NOX and mETC enzymes. Combination of C3G and RAGE antibody did not significantly enhance glyLDL-induced inhibition of NOX or mETC enzymes. C3G reduced glyLDL-induced RAGE expression with the presence of RAGE antibody. C3G prevented prolonged incubation with the glyLDL-induced decrease in cell viability and the imbalance between key regulators for cell viability (cleaved caspase 3 and B cell Lyphoma-2) in EC. The findings suggest that RAGE plays an important role in glyLDL-induced oxidative stress in vascular EC. C3G may prevent glyLDL-induced NOX activation, the impairment of mETC enzymes and cell viability in cultured vascular EC. PMID:23443099

  4. Reversal of multidrug resistance by 5,5’-dimethoxylariciresinol-4-O-β-D-glucoside in doxorubicin-resistant human leukemia K562/DOX

    PubMed Central

    Wang, Tian-Xiao; Shi, Xiao-Yan; Cong, Yue; Wang, Shi-Guang; Wang, Ying-Ying; Zhang, Zhong-Qin

    2013-01-01

    Objective: The objective of this study was to investigate the reversal effects of 5,5’-dimethoxylariciresinol-4’-O-β-D-glucoside (DMAG) extracted from traditional Chinese medicines Mahonia on multidrug resistance (MDR) of human leukemia cells to chemotherapeutic agents. Materials and Methods: MTT(3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay was performed to determine the effect of DMAG on doxorubicin sensitivity to K562/DOX cells. Propidium iodide /Hoechst 33342 double staining assay was used to investigate the effect of DMAG on doxorubicin-induced cellular apoptosis. Intracellular accumulation of doxorubicin and rhodamine 123 assay were performed to evaluate the effect of DMAG on drugs efflux activity of P-glycoprotein. Results: DMAG significantly enhanced the doxorubicin cytotoxicity to K562/DOX cells. In the presence of 1.0 μM of DMAG, the IC50 of doxorubicin decreased from 34.93 ± 1.37 μM to 12.51 ± 1.28 μM. DMAG of 1.0 μM significantly enhanced doxorubicin-induced cell apoptosis in K562/DOX cells and the enhancement was time-dependent. A significant increase in accumulation of doxorubicin in the presence of DMAG was observed. After treatment of the K562/DOX cells for 1 h with 15.0 μM doxorubicin alone, the fluorescence intensity was 33093.12. With the addition of 1.0 μM of DMAG, the fluorescence intensity of doxorubicin was 2.3-fold higher. A significant increase of accumulation of rhodamine 123 in the presence of DMAG was also observed. With the addition of 1.0 μM of DMAG, the fluorescence intensity was increased by 49.11% compared with rhodamine 123 alone. Conclusion: DMAG was shown to effectively enhance chemosensitivity of resistant cells, which makes it might be a suitable candidate for potential MDR-reversing agents. PMID:24347768

  5. Isolation, Purification and Characterization of a Novel Steroidal Saponin Cholestanol Glucoside from Lasiodiplodia theobromae that Induces Apoptosis in A549 Cells.

    PubMed

    Valayil, Jinu Mathew; Kuriakose, Gini C; Jayabaskaran, C

    2016-01-01

    Search for novel anticancer lead molecules continues to be a major focus of cancer research due to the limitations of existing drugs such as lack of tumor selectivity, narrow therapeutic index and multidrug resistance of cancer types. Natural molecules often possess better pharmacokinetic traits compared to synthetic molecules as they continually evolve by natural selection process to interact with biological macromolecules. Microbial metabolites constitute nearly half of the pharmaceuticals in market today. Endophytic fungi, owing to its rich chemical diversity, are viewed as attractive sources of novel bioactive compounds. In the present study, we report the purification and characterization of a novel steroidal saponin, cholestanol glucoside (CG) from Saraca asoca endophytic fungus Lasiodiplodia theobromae. The compound was assessed for its cytotoxic potentialities in six human cancer cell lines, A549, PC3, HepG2, U251, MCF7 and OVCAR3. CG exhibited significant cytotoxicities towards A549, PC3 and HepG2 among which A549 cells were most vulnerable to CG treatment. However, CG treatment exhibited negligible cytotoxicity in non malignant human lung fibroblast cell line (WI-38). Induction of cell death by CG treatment in A549 cells was further investigated. CG induced the generation of reactive oxygen species (ROS) and mitochondrial membrane permeability loss followed by apoptotic cell death. Mitochondrial membrane depolarization and apoptotic cell death in CG treated A549 cells were completely blocked in presence of an antioxidant, N-acetyl cysteine (NAC). Hence it could be concluded that CG initiates apoptosis in cancer cells by augmenting the basal oxidative stress and that the generation of intracellular ROS is crucial for the induction of apoptosis. PMID:26338072

  6. Study on the interaction between pelargonidin-3-O-glucoside and bovine serum albumin using spectroscopic, transmission electron microscopy and molecular modeling techniques.

    PubMed

    Li, Shu; Tang, Lin; Bi, Hongna

    2016-03-01

    The aim of this study is to evaluate the binding behavior between pelargonidin-3-O-glucoside (P3G) and bovine serum albumin (BSA) using multi-spectroscopic, transmission electron microscopy (TEM) and molecular docking methods under physiological conditions. Fluorescence spectroscopy and time-resolved fluorescence showed that the fluorescence of BSA could be quenched remarkably by P3G via a static quenching mechanism, and there is a single class of binding site on BSA. In addition, the thermodynamic functions ΔH and ΔS were -21.69 kJ/mol and 24.46 J/mol/K, indicating that an electrostatic interaction was a main acting force. The distance between BSA and P3G was 2.74 nm according to Förster's theory, illustrating that energy transfer occurred. In addition, the secondary structure of BSA changed with a decrease in the α-helix content from 66.2% to 64.0% as seen using synchronous fluorescence, UV/vis, circular dichroism and Fourier transform infrared spectroscopies, whereas TEM images showed that P3G led to BSA aggregation and fibrillation. Furthermore, site marker competitive experiments and molecular docking indicated that P3G could bind with subdomain IIA of BSA. The calculated results of the equilibrium fraction showed that the concentration of free P3G in plasma was high enough to be stored and transported from the circulatory system to its target sites to provide therapeutic effects. PMID:26249529

  7. 2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucoside suppresses human colorectal cancer cell metastasis through inhibiting NF-κB activation.

    PubMed

    Lin, Chien-Liang; Hsieh, Shu-Ling; Leung, Wan; Jeng, Jiiang-Huei; Huang, Guan-Cheng; Lee, Chining-Ting; Wu, Chih-Chung

    2016-08-01

    2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucoside (THSG), a major component of Polygonum multiflorum Thunb (He-Shou-Wu), has been reported to exhibit antioxidant and anti-inflammatory effects. However, its anti-metastatic effect against colorectal cancer is still unclear. In this study, cell migration, invasion and adhesion abilities as well as metastasis-associated protein and NF-κB pathway signaling factor expression were analyzed after treating HT-29 cells with THSG. According to the results, the migration and invasiveness of HT-29 cells were reduced after treatment with 5 or 10 mM THSG (p<0.05). Additionally, the levels of matrix metalloproteinase-2 (MMP-2) and phosphorylated VE-cadherin in HT-29 cells were reduced and the transepithelial electrical resistance (TEER) of EA.hy926 endothelial cell monolayers was increased after incubation in THSG for 24 h (p<0.05). Cell adhesion ability and the E-selectin and intercellular adhesion molecule-1 (ICAM-1) protein levels were reduced when EA.hy926 endothelial cells were treated with THSG (p<0.05). In addition, the cytoplasmic phosphorylation of IκB, the nuclear p65 level and the DNA-binding activity of NF-κB were reduced after treating HT-29 or EA.hy926 cells with 5 or 10 mM THSG (p<0.05). These results suggest that THSG inhibits HT-29 cell metastasis by suppressing cell migration, invasion and adhesion. Furthermore, THSG inhibits metastasis-associated protein expression by suppressing NF-κB pathway activation. PMID:27278328

  8. Reduction in the amplitude of shortening and Ca(2+) transient by phlorizin and quercetin-3-O-glucoside in ventricular myocytes from streptozotocin-induced diabetic rats.

    PubMed

    Hamouda, N N; Qureshi, M A; Alkaabi, J M; Oz, M; Howarth, F C

    2016-06-20

    Diabetes mellitus is the leading cause of cardiovascular morbidity and mortality. Phlorizin (PHLOR) and quercetin-3-O-glucoside (QUER-3-G) are two natural compounds reported to have antidiabetic properties by inhibiting sodium/glucose transporters. Their effects on ventricular myocyte shortening and intracellular Ca(2+) in streptozotocin (STZ)-induced diabetic rats were investigated. Video edge detection and fluorescence photometry were used to measure ventricular myocyte shortening and intracellular Ca(2+), respectively. Blood glucose in STZ rats was 4-fold higher (469.64+/-22.23 mg/dl, n=14) than in Controls (104.06+/-3.36 mg/dl, n=16). The amplitude of shortening was reduced by PHLOR in STZ (84.76+/-2.91 %, n=20) and Control (83.72+/-2.65 %, n=23) myocytes, and by QUER-3-G in STZ (79.12+/-2.28 %, n=20) and Control (76.69+/-1.92 %, n=30) myocytes. The amplitude of intracellular Ca(2+) was also reduced by PHLOR in STZ (82.37+/-3.16 %, n=16) and Control (73.94+/-5.22 %, n=21) myocytes, and by QUER-3-G in STZ (73.62+/-5.83 %, n=18) and Control (78.32+/-3.54 %, n=41) myocytes. Myofilament sensitivity to Ca(2+) was not significantly altered by PHLOR; however, it was reduced by QUER-3-G modestly in STZ myocytes and significantly in Controls. PHLOR and QUER-3-G did not significantly alter sarcoplasmic reticulum Ca(2+) in STZ or Control myocytes. Altered mechanisms of Ca(2+) transport partly underlie PHLOR and QUER-3-G negative inotropic effects in ventricular myocytes from STZ and Control rats. PMID:26447513

  9. Cyanidin-3-O-glucoside Induces Apoptosis and Inhibits Migration of Tumor Necrosis Factor-α-Treated Rat Aortic Smooth Muscle Cells.

    PubMed

    Yan, Xuerui; Wu, Lin; Li, Bin; Meng, Xianjun; Dai, Hanping; Zheng, Yanan; Fu, Junfan

    2016-07-01

    Blueberries are rich in anthocyanins (ACNs), which have recently been noted to protect against atherosclerosis development in mice. Cyanidin-3-O-glucoside (C3G), a member of blueberry ACN family, can inhibit the tumor necrosis factor-α (TNF-α)-induced proliferation of vascular smooth muscle cells (VSMCs). However, the effects of C3G on VSMC apoptosis and migration remain unclear. This study was thus conducted to examine whether and how C3G affected the apoptosis and migration of rat aortic smooth muscle cells (RASMCs) challenged by TNF-α. Primary cultured RASMCs were pretreated with C3G (25, 50 or 100 μM) for 2 h and then stimulated with TNF-α (10 ng/ml) for additional 24 h. Our results illustrated that C3G pretreatment induced significant apoptosis in TNF-α-stimulated RASMCs in a dose-dependent way, which was accompanied with increased cleaved caspase-3, caspase-9 and Bax and decreased Bcl-2. Moreover, RASMC migration was enhanced by TNF-α, but markedly suppressed by C3G pretreatment. The expressions and activities of matrix metalloproteinase-2 (MMP-2) and MMP-9 were inhibited by C3G. In addition, TNF-α-enhanced nuclear translocation of nuclear factor kappa B (NF-κB) subunit p65 and phosphorylation of NF-κB inhibitor α (IκBα) in RASMCs were attenuated by C3G. In summary, our study reveals that C3G can induce significant apoptosis in TNF-α-treated RASMCs and markedly inhibit their migration. PMID:26138096

  10. Transcriptional regulation of de novo biosynthesis of cyanogenic glucosides throughout the life-cycle of the burnet moth Zygaena filipendulae (Lepidoptera).

    PubMed

    Fürstenberg-Hägg, Joel; Zagrobelny, Mika; Olsen, Carl Erik; Jørgensen, Kirsten; Møller, Birger Lindberg; Bak, Søren

    2014-06-01

    The six-spotted burnet moth Zygaena filipendulae (Lepidoptera) utilize the two cyanogenic glucosides (CNglcs) linamarin and lotaustralin as deterrents against predators throughout the entire life cycle. CNglcs can be hydrolyzed and bioactivated by β-glucosidases, resulting in the release of toxic hydrogen cyanide. CNglcs are retained through metamorphosis, probably involved in mating communication, and transferred during mating from the male to the female as a nuptial gift. CNglcs can be biosynthesized de novo by Z. filipendulae larvae, but may also be sequestered from their food plant Lotus corniculatus (Fabaceae). These two strategies are tightly linked and adjusted according to the CNglc content and composition of the food plant in order to balance CNglc homeostasis in the larva. In this study, the amounts of CNglcs and transcript levels of the biosynthetic genes were monitored in all life-stages and tissues of Z. filipendulae. During pupation, transcription of the biosynthetic genes is turned off and the CNglc content slowly declines. In females but not males, transcription of the biosynthetic genes is re-activated at the end of pupation. Eggs and embryos do not biosynthesize CNglcs de novo, but are endowed with CNglcs following eclosion of the female. Similarly to larvae, de novo biosynthesis in female adults takes place in the integument from which CNglcs are then transported to other organs. This study demonstrates that Z. filipendulae has evolved the ability to adjust the production of CNglcs throughout its life-cycle for optimal utilization in defense and possibly other metabolic functions, while at the same time avoiding intoxication. PMID:24727026

  11. Cyanidin-3-O-β-glucoside ameliorates lipopolysaccharide-induced acute lung injury by reducing TLR4 recruitment into lipid rafts.

    PubMed

    Fu, Yunhe; Zhou, Ershun; Wei, Zhengkai; Wang, Wei; Wang, Tiancheng; Yang, Zhengtao; Zhang, Naisheng

    2014-07-15

    Cyanidin-3-O-β-glucoside (C3G), a typical anthocyanin pigment that exists in the human diet, has been reported to have anti-inflammatory properties. The aim of this study was to detect the effect of C3G on LPS-induced acute lung injury and to investigate the molecular mechanisms. Acute lung injury was induced by intratracheal administration of LPS in mice. Alveolar macrophages from mice were stimulated with LPS and were treated with C3G. Our results showed that C3G attenuated lung histopathologic changes, myeloperoxidase (MPO) activity, TNF-α, IL-1β and IL-6 production in LPS-induced acute lung injury model. In vitro, C3G dose-dependently inhibited TNF-α, IL-1β, IL-6, IL-10 and IFN-β production, as well as NF-κB and IRF3 activation in LPS-stimulated alveolar macrophages. Furthermore, C3G disrupted the formation of lipid rafts by depleting cholesterol and inhibited TLR4 translocation into lipid rafts. Moreover, C3G activated LXRα-ABCG1-dependent cholesterol efflux. Knockout of LXRα abrogated the anti-inflammatory effects of C3G. In conclusion, C3G has a protective effect on LPS-induced acute lung injury. The promising anti-inflammatory mechanisms of C3G is associated with up-regulation of the LXRα-ABCG1 pathway which result in disrupting lipid rafts by depleting cholesterol and reducing translocation of TLR4 to lipid rafts, thereby suppressing TLR4 mediated inflammatory response. PMID:24841888

  12. Cardiovascular effects of mollic acid glucoside, a 1α-hydroxycycloartenoid saponin extractive from Combretum molle R Br ex G Don (Combretaceae) leaf

    PubMed Central

    Ojewole, John AO

    2008-01-01

    Summary Summary The cardiovascular effects of mollic acid glucoside (MAG), a 1α-hydroxycycloartenoid saponin extractive from Combretum molle R Br ex G Don (Combretaceae) leaf, have been investigated in some experimental animal paradigms. The plant extract (MAG, 5–80 μg/ml) produced concentration-dependent, significant (p < 0.05–0.001) negative inotropic and negative chronotropic effects on guinea pig isolated electrically driven left, and spontaneously beating right atrial muscle preparations, respectively. MAG also significantly reduced (p < 0.05–0.001) or abolished, in a concentration-dependent manner, the rhythmic, spontaneous contractions of portal veins isolated from healthy, normal Wistar rats. Like acetylcholine (ACh, 10-8–10-5 M), the plant extract (5–80 μg/ml) produced concentration-related relaxations of rat isolated endothelium-containing thoracic aortic rings pre-contracted with noradrenaline (NA, 10-10–10-5 M). The vasorelaxant effects of MAG in the aortic rings were markedly inhibited or annulled by NG-nitro-L-arginine methyl ester (L-NAME, 10-5 M), a nitric oxide synthase inhibitor. Furthermore, MAG (2.5–40 mg/kg iv) caused dose-related, transient but significant reductions (p < 0.05–0.001) in the systemic arterial blood pressures and heart rates of anaesthetised normotensive and hypertensive rats. The results of this laboratory animal study indicate that MAG caused bradycardia, vasorelaxation and hypotension in the mammalian experimental models used. The vasorelaxant action of MAG was endothelium dependent, and was therefore possibly dependent on the synthesis and release of nitric oxide (NO). The findings of this study suggest that Combretum molle leaf may be used as a natural supplementary remedy in essential hypertension and in certain cases of cardiac dysfunctions in rural African communities. PMID:18568171

  13. Cyanidin-3-O-β-Glucoside and Protocatechuic Acid Exert Insulin-Like Effects by Upregulating PPARγ Activity in Human Omental Adipocytes

    PubMed Central

    Scazzocchio, Beatrice; Varì, Rosaria; Filesi, Carmelina; D’Archivio, Massimo; Santangelo, Carmela; Giovannini, Claudio; Iacovelli, Annunziata; Silecchia, Gianfranco; Volti, Giovanni Li; Galvano, Fabio; Masella, Roberta

    2011-01-01

    OBJECTIVE Insulin resistance (IR) represents an independent risk factor for metabolic, cardiovascular, and neoplastic disorders. Preventing/attenuating IR is a major objective to be reached to preserve population health. Because many insulin-sensitizing drugs have shown unwanted side effects, active harmless compounds are sought after. Dietary anthocyanins have been demonstrated to ameliorate hyperglycemia and insulin sensitivity. This study aimed at investigating whether cyanidin-3-O-β-glucoside (C3G) and its metabolite protocatechuic acid (PCA) might have a role in glucose transport activation in human omental adipocytes and 3T3-L1 cells. RESEARCH DESIGN AND METHODS In cells treated with 50 µmol/L C3G and 100 µmol/L PCA, [3H]-2-deoxyglucose uptake, GLUT4 translocation by immunoblotting, adiponectin secretion, and peroxisome proliferator–activated receptor-γ (PPARγ) activation by enzyme-linked immunosorbent assay kits were evaluated. Parallel experiments were carried out in murine adipocyte 3T3-L1. To define the role of PPARγ in modulating polyphenol effects, small interfering RNA technique and PPARγ antagonist were used to inhibit transcription factor activity. RESULTS C3G and PCA increased adipocyte glucose uptake (P < 0.05) and GLUT4 membrane translocation (P < 0.01). Significant increases (P < 0.05) in nuclear PPARγ activity, as well as in adiponectin and GLUT4 expressions (P < 0.01), were also shown. It is interesting that PPARγ inhibition counteracted the polyphenol-induced adiponectin and GLUT4 upregulations, suggesting a direct involvement of PPARγ in this process. CONCLUSIONS Our study provides evidence that C3G and PCA might exert insulin-like activities by PPARγ activation, evidencing a causal relationship between this transcription factor and adiponectin and GLUT4 upregulation. Dietary polyphenols could be included in the preventive/therapeutic armory against pathological conditions associated with IR. PMID:21788573

  14. Comparison of Anorectic and Emetic Potencies of Deoxynivalenol (Vomitoxin) to the Plant Metabolite Deoxynivalenol-3-Glucoside and Synthetic Deoxynivalenol Derivatives EN139528 and EN139544

    PubMed Central

    Wu, Wenda; Zhou, Hui-Ren; Bursian, Steven J.; Pan, Xiao; Link, Jane E.; Berthiller, Franz; Adam, Gerhard; Krantis, Anthony; Durst, Tony; Pestka, James J.

    2014-01-01

    The mycotoxin deoxynivalenol (DON) elicits robust anorectic and emetic effects in several animal species. However, less is known about the potential for naturally occurring and synthetic congeners of this trichothecene to cause analogous responses. Here we tested the hypothesis that alterations in DON structure found in the plant metabolite deoxynivalenol-3-glucoside (D3G) and two pharmacologically active synthetic DON derivatives, EN139528 and EN139544, differentially impact their potential to evoke food refusal and emesis. In a nocturnal mouse food consumption model, oral administration with DON, D3G, EN139528, or EN139544 at doses from 2.5 to 10 mg/kg BW induced anorectic responses that lasted up to 16, 6, 6, and 3 h, respectively. Anorectic potency rank orders were EN139544>DON>EN139528>D3G from 0 to 0.5 h but DON>D3G>EN139528>EN139544 from 0 to 3 h. Oral exposure to each of the four compounds at a common dose (2.5 mg/kg BW) stimulated plasma elevations of the gut satiety peptides cholecystokinin and to a lesser extent, peptide YY3–36 that corresponded to reduced food consumption. In a mink emesis model, oral administration of increasing doses of the congeners differentially induced emesis, causing marked decreases in latency to emesis with corresponding increases in both the duration and number of emetic events. The minimum emetic doses for DON, EN139528, D3G, and EN139544 were 0.05, 0.5, 2, and 5 mg/kg BW, respectively. Taken together, the results suggest that although all three DON congeners elicited anorectic responses that mimicked DON over a narrow dose range, they were markedly less potent than the parent mycotoxin at inducing emesis. PMID:25173790

  15. Determination of free and glucosidically-bound volatiles in plants. Two case studies: L-menthol in peppermint (Mentha x piperita L.) and eugenol in clove (Syzygium aromaticum (L.) Merr. & L.M.Perry).

    PubMed

    Sgorbini, Barbara; Cagliero, Cecilia; Pagani, Alberto; Sganzerla, Marla; Boggia, Lorenzo; Bicchi, Carlo; Rubiolo, Patrizia

    2015-09-01

    This study arises from both the today's trend towards exploiting plant resources exhaustively, and the wide quantitative discrepancy between the amounts of commercially-valuable markers in aromatic plants and those recovered from the related essential oil. The study addresses the determination of both the qualitative composition and the exhaustive distribution of free and glucosidically-bound L-menthol in peppermint aerial parts (Mentha x piperita L., Lamiaceae) and of eugenol in dried cloves (Syzygium aromaticum (L.) Merr. & L.M.Perry, Myrtaceae), two plants known to provide widely ranging essential oil yields. The two markers were investigated in essential oils and residual hydrodistillation waters, before and after enzymatic hydrolysis. Their amounts were related to those in the headspace taken as reference. The results showed that the difference between marker compound in headspace and in essential oil amounted to 22.8% for L-menthol in peppermint, and 16.5% for eugenol in cloves. The aglycones solubilised in the residual hydrodistillation waters were 7.2% of the headspace reference amount for L-menthol, and 13.3% for eugenol, respectively representing 9.3% and 15.9% of their amounts in the essential oil. The amount of L-menthol from its glucoside in residual hydrodistillation waters was 20.6% of that in the related essential oil, while eugenol from its glucoside accounted for 7.7% of the amount in clove essential oil. The yield of L-menthol, after submitting the plant material to enzymatic hydrolysis before hydrodistillation, increased by 23.1%, and for eugenol the increase was 8.1%, compared to the amount in the respective conventional essential oils. This study also aimed to evaluate the reliability of recently-introduced techniques that are little applied, if at all, in this field. The simultaneous use of high-concentration-capacity sample preparation techniques (SBSE, and HS-SPME and in-solution SPME) to run quali-quantitative analysis without sample

  16. [Influence of metal ions on stability of 2,3,5,4'-tetrahydroxy stilbene-2-O-β-D-glucoside contained in Polygoni Multiflori Radix].

    PubMed

    Li, Rui-yu; Feng, Wu-wen; Li, Xiao-fei; Zhang, Ding-kun; Li, Chun-yu; Meng, Ya-kun; Bai, Zhao-fang; Song, Hai-bo; Du, Xiao-xi; Xia, Hou-lin; Wang, Jia-bo; Xiao, Xiao-he

    2016-01-01

    Decoction is one of the most commonly used dosage forms of traditional Chinese medicine. The stability of chemical constituents in decoction is closely related to the clinical efficacy and safety. There were few reports about the influence of metal ions in the stability of chemical constituents in traditional Chinese medicine. However, there is no evidence that metal ions in decoction water need to be controlled. In this study, 2,3,5,4'-tetrahydroxy stilbene-2-O-β-D-glucoside (THSG), one of the main constituents in Polygoni Multiflori Radix was studied. Ordinary tap water, deionized water, and water containing different metal ions were used to investigate and compare the influence on THSG. The results showed that after storage in a dark place at the room temperature for 10 days, the degradation of THSG was 7% in deionized water, while undetectable in tap water. The content of THSG could be decreased by different kinds of metal ions, and the effect was concentration-dependent. Moreover, Fe3+ and Fe2+ showed the greatest influence at the same concentration; and our study has shown that THSG decreased more than 98% in Fe and Fe2+ solutions at 500 ppm concentration. In the same time we found out p-hydroxybenzaldehyde (molecular weight: 122.036 7) and 2,3,5-trihydroxybenzaldehyde-2-O-glycoside (molecular weight: 316.079 4) were the main degradation products of THSG in tap water and water containing Cu2+, Ca2+, Zn2+, Mg2+ and Al3+. The product of THSG dimer with a water molecule was found in water containing Fe3+ and Fe2+. The above results showed that the metal ions in water could significantly influence the stability of THSG in water, indicating that the clinical efficacy and safety of decoction would be affected if the metal ions in water were not under control. It's suggested that deionized water should be used in the preparation of decoction containing Polygoni Multiflori Radix in the clinic to avoid degradation of THSG. Meanwhile, decoction prepared by tap water

  17. Protodioscin-glycosidase-1 hydrolyzing 26-O-β-D-glucoside and 3-O-(1 → 4)-α-L-rhamnoside of steroidal saponins from Aspergillus oryzae.

    PubMed

    Liu, Tingqiang; Yu, Hongshan; Liu, Chunying; Wang, Yuanhao; Tang, Minqian; Yuan, Xiaodong; Luo, Ning; Wang, Qingyu; Xu, Xiaodong; Jin, Fengxie

    2013-12-01

    A novel protodioscin-(steroidal saponin)-glycoside hydrolase, named protodioscin-glycosidase-1 (PGase-1), was purified and characterized from the Aspergillus oryzae strain. The molecular mass of this enzyme was determined to be about 55 kDa based on SDS-polyacrylamide gel electrophoresis. PGase-1 was able to hydrolyze the terminal 26-O-β-D-glucopyranoside of protodioscin (furostanoside) to produce dioscin (spirostanoside), and then further hydrolyze the terminal 3-O-(1 → 4)-α-L-rhamnopyranoside of dioscin to form progenin III. However, PGase-1 could hardly hydrolyze the 3-O-(1 → 2)-α-L-rhamnopyranoside of progenin III, 3-O-β-D-glucoside of trillin, and the 1-O-glycosides of ophiopogonin D (steroidal saponin). In addition, PGase-1 also could hydrolyze the α-D-galactopyranoside, β-D-glucopyranoside, and β-D-galactopyranoside of p-nitrophenyl-glycosides, but the enzyme could not hydrolyze the α-D-mannopyranoside, α-L-arabinopyranoside, α-D-glucopyranoside, β-D-xylopyranoside, and α-L-rhamnopyranoside of p-nitrophenyl-glycosides. These new properties of PGase-1 were significantly different from those of previously described steroidal saponin-glycosidases and the glycosidases currently described in Enzyme Nomenclature by the NC-IUBMB. The gene (termed as pgase-1) encoding PGase-1 was cloned, sequenced, and expressed in Pichia pastoris GS115. The complete nucleotide sequence of pgase-1 consists of 1,725 bp. The recombinant PGase-1 from recombinant P. pastoris GS115 strain also showed the activity hydrolyzing glycosides of steroidal saponins which was similar to that of the wild-type PGase-1 from A. oryzae. The PGase-1 gene is highly similar to Aspergilli α-amylase (EC 3.2.1.1), and PGase-1 should be classified as glycoside hydrolase family 13 by the method of gene sequence-based classification. But the enzyme properties of PGase-1 are different from those of α-amylase in this family. PMID:23467827

  18. Cyanidin-3-glucoside inhibits UVB-induced oxidative damage and inflammation by regulating MAP kinase and NF-κB signaling pathways in SKH-1 hairless mice skin

    SciTech Connect

    Pratheeshkumar, Poyil; Son, Young-Ok; Wang, Xin; Divya, Sasidharan Padmaja; Joseph, Binoy; Hitron, John Andrew; Wang, Lei; Kim, Donghern; Yin, Yuanqin; Roy, Ram Vinod; Lu, Jian; Zhang, Zhuo; Wang, Yitao; and others

    2014-10-01

    Skin cancer is one of the most commonly diagnosed cancers in the United States. Exposure to ultraviolet-B (UVB) radiation induces inflammation and photocarcinogenesis in mammalian skin. Cyanidin-3-glucoside (C3G), a member of the anthocyanin family, is present in various vegetables and fruits especially in edible berries, and displays potent antioxidant and anticarcinogenic properties. In this study, we have assessed the in vivo effects of C3G on UVB irradiation induced chronic inflammatory responses in SKH-1 hairless mice, a well-established model for UVB-induced skin carcinogenesis. Here, we show that C3G inhibited UVB-induced skin damage and inflammation in SKH-1 hairless mice. Our results indicate that C3G inhibited glutathione depletion, lipid peroxidation and myeloperoxidation in mouse skin by chronic UVB exposure. C3G significantly decreased the production of UVB-induced pro-inflammatory cytokines, such as IL-6 and TNF-α, associated with cutaneous inflammation. Likewise, UVB-induced inflammatory responses were diminished by C3G as observed by a remarkable reduction in the levels of phosphorylated MAP kinases, Erk1/2, p38, JNK1/2 and MKK4. Furthermore, C3G also decreased UVB-induced cyclooxygenase-2 (COX-2), PGE{sub 2} and iNOS levels, which are well-known key mediators of inflammation and cancer. Treatment with C3G inhibited UVB-induced nuclear translocation of NF-κB and degradation of IκBα in mice skin. Immunofluorescence assay revealed that topical application of C3G inhibited the expression of 8-hydroxy-2′-deoxyguanosine, proliferating cell nuclear antigen, and cyclin D1 in chronic UVB exposed mouse skin. Collectively, these data indicates that C3G can provide substantial protection against the adverse effects of UVB radiation by modulating UVB-induced MAP kinase and NF-κB signaling pathways. - Highlights: • C3G inhibited UVB-induced oxidative damage and inflammation. • C3G inhibited UVB-induced COX-2, iNOS and PGE{sub 2} production. • C3G

  19. On the chemical constituents of Dipsacus asper.

    PubMed

    Tian, Xiao-Yan; Wang, Ying-Hong; Liu, Hong-Yue; Yu, Shi-Shan; Fang, Wei-Shuo

    2007-12-01

    Bioassay-guided fractionation of 95% EtOH extract from the roots of Dipsacus asper lead to the isolation of some phenolic acids (caffeic acid, 2,6-dihydroxycinnamic acid, vanillic acid, 2'-O-caffeoyl-D-glucopyranoside ester, and caffeoylquinic acid) as the major active components, and five new iridoid glucoside dimers (1-5) and one new iridoid glucoside monomer (6), other known iridoid glycosides loganin, cantleyoside, triplostoside A, lisianthioside, 6'-O-beta-D-apiofuranosyl sweroside, as well as triterpenoids oleanic acid and akebiasaponin D. The structures of new compounds 1-6 were determined as dipsanosides C (1), D (2), E (3), F (4), G (5), and 3'-O-beta-D-glucopyranosyl sweroside (6) by spectroscopic, including 1D and 2D NMR techniques, and chemical methods. PMID:18057739

  20. Nucleotide sequences of the arb genes, which control beta-glucoside utilization in Erwinia chrysanthemi: comparison with the Escherichia coli bgl operon and evidence for a new beta-glycohydrolase family including enzymes from eubacteria, archeabacteria, and humans.

    PubMed Central

    el Hassouni, M; Henrissat, B; Chippaux, M; Barras, F

    1992-01-01

    The phytopathogenic bacterium Erwinia chrysanthemi, unlike other members of the family Enterobacteriaceae, is able to metabolize the beta-glucosides, arbutin, and salicin. A previous genetic analysis of the E. chrysanthemi arb genes, which mediate beta-glucoside metabolism, suggested that they were homologous to the Escherichia coli K-12 bgl genes. We have now determined the nucleotide sequence of a 5,065-bp DNA fragment containing three genes, arbG, arbF, and arbB. Deletion analysis, expression in minicell systems, and comparison with sequences of other proteins suggest that arbF and arbB encode a beta-glucoside-specific phosphotransferase system-dependent permease and a phospho-beta-glucosidase, respectively. The ArbF amino acid sequence shares 55% identity with that of the E. coli BglF permease and contains most residues thought to be important for a phosphotransferase. One change, however, was noted, since BglF Arg-625, presumably involved in phosphoryl transfer, was replaced by a Cys residue in ArbF. An analysis of the ArbB sequence led to the definition of a protein family which contained enzymes classified as phospho-beta-glucosidases, phospho-beta-galactosidases, beta-glucosidases, and beta-galactosidases and originating from gram-positive and gram-negative bacteria, archebacteria, and mammals, including humans. An analysis of this family allowed us (i) to speculate on the ways that these enzymes evolved, (ii) to identify a glutamate residue likely to be a key amino acid in the catalytic activity of each protein, and (iii) to predict that domain II of the human lactate-phlorizin hydrolase, which is involved in lactose intolerance, is catalytically nonactive. A comparison between the untranslated regions of the E. chrysanthemi arb cluster and the E. coli bgl operon revealed the conservation of two regions which, in the latter, are known to terminate transcription under noninducing conditions and be the target of the BglG transcriptional antiterminator under

  1. Ionic liquids-lithium salts pretreatment followed by ultrasound-assisted extraction of vitexin-4″-O-glucoside, vitexin-2″-O-rhamnoside and vitexin from Phyllostachys edulis leaves.

    PubMed

    Hou, Kexin; Chen, Fengli; Zu, Yuangang; Yang, Lei

    2016-01-29

    An efficient method for the extraction of vitexin, vitexin-4″-O-glucoside, and vitexin-2″-O-rhamnoside from Phyllostachys edulis leaves comprises heat treatment using an ionic liquid-lithium salt mixture (using 1-butyl-3-methylimidazolium bromide as the solvent and lithium chloride as the additive), followed by ultrasound-assisted extraction. To obtain higher extraction yields, the effects of the relevant experimental parameters (including heat treatment temperature and time, relative amounts of 1-butyl-3-methylimidazolium bromide and lithium chloride, power and time of the ultrasound irradiation, and the liquid-solid ratio) are evaluated and response surface methodology is used to optimize the significant factors. The morphologies of the treated and untreated P. edulis leaves are studied by scanning electron microscopy. The improved extraction method proposed provides high extraction yield, good repeatability and precision, and has wide potential applications in the analysis of plant samples. PMID:26763300

  2. Cytochromes P-450 from cassava (Manihot esculenta Crantz) catalyzing the first steps in the biosynthesis of the cyanogenic glucosides linamarin and lotaustralin. Cloning, functional expression in Pichia pastoris, and substrate specificity of the isolated recombinant enzymes.

    PubMed

    Andersen, M D; Busk, P K; Svendsen, I; Møller, B L

    2000-01-21

    The first committed steps in the biosynthesis of the two cyanogenic glucosides linamarin and lotaustralin in cassava are the conversion of L-valine and L-isoleucine, respectively, to the corresponding oximes. Two full-length cDNA clones that encode cytochromes P-450 catalyzing these reactions have been isolated. The two cassava cytochromes P-450 are 85% identical, share 54% sequence identity to CYP79A1 from sorghum, and have been assigned CYP79D1 and CYP79D2. Functional expression has been achieved using the methylotrophic yeast, Pichia pastoris. The amount of CYP79D1 isolated from 1 liter of P. pastoris culture exceeds the amounts that putatively could be isolated from 22,000 grown-up cassava plants. Each cytochrome P-450 metabolizes L-valine as well as L-isoleucine consistent with the co-occurrence of linamarin and lotaustralin in cassava. CYP79D1 was isolated from P. pastoris. Reconstitution in lipid micelles showed that CYP79D1 has a higher k(c) value with L-valine as substrate than with L-isoleucine, which is consistent with linamarin being the major cyanogenic glucoside in cassava. Both CYP79D1 and CYP79D2 are present in the genome of cassava cultivar MCol22 in agreement with cassava being allotetraploid. CYP79D1 and CYP79D2 are actively transcribed, and production of acyanogenic cassava plants would therefore require down-regulation of both genes. PMID:10636899

  3. Hydrolytic activity toward pyridoxine-5'-beta-D-glucoside in rat intestinal mucosa is not increased by vitamin B-6 deficiency: effect of basal diet composition and pyridoxine intake.

    PubMed

    Mackey, Amy D; Lieu, Siam O; Carman, Catherine; Gregory, Jesse F

    2003-05-01

    Pyridoxine-5'-beta-D-glucoside (PNG), a glycosylated form of dietary vitamin B-6, is partially hydrolyzed in the small intestine by the cytosolic enzyme pyridoxine-5'-beta-D-glucoside hydrolase (PNG hydrolase) and by the brush border enzyme lactase phlorizin hydrolase (LPH) to release free pyridoxine (PN). This laboratory has previously shown that PNG hydrolase activity is inversely related to dietary vitamin B-6 in rats and guinea pigs. The current investigation was done to examine the effect of dietary PN on PNG hydrolytic activity and its distribution. Nutrient compositional differences between the AIN-76A and AIN-93G purified diets that were unrelated to vitamin B-6 were also examined in relation to PNG hydrolysis in rat small intestinal mucosa. Study one included rats (n = 29) that were fed the AIN-93G diet providing a range of PN concentrations for 5 wk. Rats (n = 49) in study two were fed either AIN-76A or AIN-93G each with graded concentrations of PN. In both studies, rat growth and plasma and liver pyridoxal 5'-phosphate (PLP) concentrations increased (P < 0.05) with increasing concentrations of dietary PN. PNG hydrolytic activity localized to the brush border membrane was five times that measured in the cytosol. Cytosolic PNG hydrolytic activity increased significantly with increasing dietary PN concentration in rats fed the AIN-76A, but not AIN-93G diet. Activity in the mucosal total membrane fraction did not increase in proportion to dietary PN concentration for either diet. Regardless of dietary PN concentration, the basal nutrient composition of the diets affected growth and PNG hydrolytic activity in intestinal mucosa. In contrast to previous results from this laboratory, intestinal hydrolytic activity toward PNG did not increase in vitamin B-6-deficient rats. PMID:12730423

  4. Identification and Quantification of Oxidoselina-1,3,7(11)-Trien-8-One and Cyanidin-3-Glucoside as One of the Major Volatile and Non-Volatile Low-Molecular-Weight Constituents in Pitanga Pulp.

    PubMed

    Josino Soares, Denise; Pignitter, Marc; Ehrnhöfer-Ressler, Miriam Margit; Walker, Jessica; Montenegro Brasil, Isabella; Somoza, Veronika

    2015-01-01

    The pulp of pitanga (Eugenia uniflora L.) is used to prepare pitanga juice. However, there are no reports on the identification and quantification of the main constituents in pitanga pulp. The aim of this study was to identify and quantify the major volatile and non-volatile low-molecular-weight constituents of the pulp. Isolation of volatile compounds was performed by solvent-assisted flavor evaporation technique. Characterization of the main volatile and non-volatile constituents was performed by GC-MS, LC-MS and NMR spectroscopy. For quantitative measurements, the main volatile compound needed to be isolated from pitanga pulp to obtain a commercially not available reference standard. Cyanidin-3-glucoside was determined as one of the most abundant non-volatile pulp compound yielding 53.8% of the sum of the intensities of all ions detected by LC-MS. Quantification of cyanidin-3-glucoside in pitanga pulp resulted in a concentration of 344 ± 66.4 μg/mL corresponding to 688 ± 133 μg/g dried pulp and 530 ± 102 μg/g fruit. For the volatile fraction, oxidoselina-1,3,7(11)-trien-8-one was identified as the main volatile pulp constituent (27.7% of the sum of the intensities of all ions detected by GC-MS), reaching a concentration of 89.0 ± 16.9 μg/mL corresponding to 1.34 ± 0.25 μg/g fresh pulp and 1.03 ± 0.19 μg/g fruit. The results provide quantitative evidence for the occurrence of an anthocyanin and an oxygenated sesquiterpene as one of the major volatile and non-volatile low-molecular-weight compounds in pitanga pulp. PMID:26394146

  5. Identification and Quantification of Oxidoselina-1,3,7(11)-Trien-8-One and Cyanidin-3-Glucoside as One of the Major Volatile and Non-Volatile Low-Molecular-Weight Constituents in Pitanga Pulp

    PubMed Central

    Ehrnhöfer-Ressler, Miriam Margit; Walker, Jessica; Montenegro Brasil, Isabella; Somoza, Veronika

    2015-01-01

    The pulp of pitanga (Eugenia uniflora L.) is used to prepare pitanga juice. However, there are no reports on the identification and quantification of the main constituents in pitanga pulp. The aim of this study was to identify and quantify the major volatile and non-volatile low-molecular-weight constituents of the pulp. Isolation of volatile compounds was performed by solvent-assisted flavor evaporation technique. Characterization of the main volatile and non-volatile constituents was performed by GC-MS, LC-MS and NMR spectroscopy. For quantitative measurements, the main volatile compound needed to be isolated from pitanga pulp to obtain a commercially not available reference standard. Cyanidin-3-glucoside was determined as one of the most abundant non-volatile pulp compound yielding 53.8% of the sum of the intensities of all ions detected by LC-MS. Quantification of cyanidin-3-glucoside in pitanga pulp resulted in a concentration of 344 ± 66.4 μg/mL corresponding to 688 ± 133 μg/g dried pulp and 530 ± 102 μg/g fruit. For the volatile fraction, oxidoselina-1,3,7(11)-trien-8-one was identified as the main volatile pulp constituent (27.7% of the sum of the intensities of all ions detected by GC-MS), reaching a concentration of 89.0 ± 16.9 μg/mL corresponding to 1.34 ± 0.25 μg/g fresh pulp and 1.03 ± 0.19 μg/g fruit. The results provide quantitative evidence for the occurrence of an anthocyanin and an oxygenated sesquiterpene as one of the major volatile and non-volatile low-molecular-weight compounds in pitanga pulp. PMID:26394146

  6. A Double-Blind, 12-Week Study to Evaluate the Antiaging Efficacy of a Cream Containing the NFκB Inhibitor 4-Hexyl-1, 3-Phenylenediol and Ascorbic Acid-2 Glucoside in Adult Females.

    PubMed

    Roure, Romain; Nollent, Virginie; Dayan, Liliane; Camel, Etienne; Bertin, Christiane

    2016-06-01

    The 5 main physical manifestations of aged skin are wrinkles, uneven tone, brown spots, loss of elasticity, and dryness. One mechanism resulting in these physical manifestations is increased activity of the nuclear factor kappa B (NFκB) protein. This 12-week, double-blind, placebo-controlled, randomized split-face study compared the antiaging effect and safety of a face cream containing 4-Hexyl-1, 3-phenylenediol, an NFκB inhibitor, and ascorbic acid-2 glucoside versus placebo in adult females aged 45-70 years old. Subjects (n=42) applied active treatment or placebo to the same half face twice daily at home for 12 weeks. Clinical evaluation was carried out by a dermatologist. Subjects carried out similar self-grading assessments. Colorimetric measurements analyzed skin color, and biomechanical skin properties were evaluated. Clinical grading showed that most wrinkle parameters were significantly improved after 8 weeks of active treatment compared with baseline and placebo (P≤.05), with improvements maintained after 12 weeks. Only Marionette wrinkles did not show a significant improvement. Brown spots (color intensity/number), overall photodamage, and most complexion parameters improved significantly after 8 and 12 weeks compared with baseline and placebo (P≤.05). Self-grading yielded similar results compared with baseline. Self-grading did not demonstrate improvements with active treatment versus placebo, except for skin firmness at 8 and 12 weeks (P≤.05). A significant difference was seen with active treatment compared with placebo in all colorimetric parameters (L*, b*, and ITA°) after 8 weeks, and in spot coloration (b*) after 12 weeks (P<.05). Improvements in skin elasticity were not significantly different between treatments. Overall tolerability of active treatment was judged as good. In conclusion, a cream containing 4-Hexyl-1, 3-phenylenediol and ascorbic acid-2 glucoside improves the clinical appearance of aged

  7. The biosynthesis of cyanogenic glucosides in higher plants. The (E)- and (Z)-isomers of p-hydroxyphenylacetaldehyde oxime as intermediates in the biosynthesis of dhurrin in Sorghum bicolor (L. ) Moench

    SciTech Connect

    Halkier, B.A.; Olsen, C.E.; Moller, B.L. )

    1989-11-25

    The biosynthesis of the tyrosine-derived cyanogenic glucoside dhurrin has been studied with a microsomal preparation obtained from etiolated seedlings of sorghum. The biosynthetic pathway involves tyrosine, N-hydroxytyrosine, and p-hydroxyphenylacetaldehyde oxime as early intermediates. The use of deuterium-labeled tyrosine and mass spectrometric analyses demonstrate that the alpha-hydrogen atom of tyrosine is retained in the conversion of tyrosine to p-hydroxyphenylacetaldehyde oxime. This excludes p-hydroxyphenylpyruvic acid oxime as intermediate in the pathway. A high pressure liquid chromatography method was developed to separate the (E)- and (Z)-isomers of p-hydroxyphenylacetaldehyde oxime. The microsomal enzyme system was found to produce initially the (E)-isomer of p-hydroxyphenylacetaldehyde oxime. An isomerase then converts the (E)-isomer to the (Z)-isomer, which is the isomer preferentially utilized by the microsomal enzyme system in the subsequent biosynthetic reactions. The (E)-isomer produced in situ is more efficiently converted to the (Z)-isomer than exogenously added (E)-isomer and may thus be metabolically channeled.

  8. Transcriptome profiling and digital gene expression analysis of Fallopia multiflora to discover putative genes involved in the biosynthesis of 2,3,5,4'-tetrahydroxy stilbene-2-O-β-D-glucoside.

    PubMed

    Zhao, Wei; Xia, Wanxia; Li, Jiewen; Sheng, Shujing; Lei, Lei; Zhao, Shujing

    2014-08-15

    The compound 2,3,5,4'-tetrahydroxy stilbene-2-O-ß-d-glucoside (THSG) synthesized by Fallopia multiflora (F. multiflora) exhibits pharmacological potency. However, the mechanistic details of its biosynthesis pathway are still vague. To clear this ambiguity, we performed de novo transcriptome assembly and digital gene expression (DGE) profiling analyses of F. multiflora using the Illumina RNA-seq system. RNA-seq generated approximately 70 million high-quality reads that were assembled into 65,653 unigenes (mean length=750 bp), including 26,670 clusters and 38,983 singletons. A total of 48,173 (73.4%) unigenes were annotated using public protein databases with a cut-off e-value above 10(-5). Furthermore, we investigated the transcriptome difference of four different F. multiflora tissues using DGE profiling. Variations in gene expression were identified based on comparisons of transcriptomes from various parts of a high-level THSG- and a low-level THSG-producing F. multiflora plant. Clusters with similar differential expression patterns and enriched metabolic pathways with regard to the differentially expressed genes putatively involved in THSG biosynthesis were revealed for the first time. Our data provides the most comprehensive sequence resource regarding F. multiflora so far. Taken together, the results of this study considerably extend the knowledge on THSG production. PMID:24967942

  9. TSG (2,3,5,4′-Tetrahydroxystilbene-2-O-β-D-glucoside) from the Chinese Herb Polygonum multiflorum Increases Life Span and Stress Resistance of Caenorhabditis elegans

    PubMed Central

    Büchter, Christian; Zhao, Liang; Fritz, Gerhard; Proksch, Peter

    2015-01-01

    2,3,5,4′-Tetrahydroxystilbene-2-O-β-D-glucoside (TSG) was isolated from Polygonum multiflorum, a plant which is traditionally used as an anti-ageing drug. We have analysed ageing-related effects of TSG in the model organism C. elegans in comparison to resveratrol. TSG exerted a high antioxidative capacity both in a cell-free assay and in the nematode. The antioxidative capacity was even higher compared to resveratrol. Presumably due to its antioxidative effects, treatment with TSG decreased the juglone-mediated induction of the antioxidative enzyme SOD-3; the induction of the GST-4 by juglone was diminished slightly. TSG increased the resistance of C. elegans against lethal thermal stress more prominently than resveratrol (50 μM TSG increased mean survival by 22.2%). The level of the ageing pigment lipofuscin was decreased after incubation with the compound. TSG prolongs the mean, median, and maximum adult life span of C. elegans by 23.5%, 29.4%, and 7.2%, respectively, comparable to the effects of resveratrol. TSG-mediated extension of life span was not abolished in a DAF-16 loss-of-function mutant strain showing that this ageing-related transcription factor is not involved in the effects of TSG. Our data show that TSG possesses a potent antioxidative capacity, enhances the stress resistance, and increases the life span of the nematode C. elegans. PMID:26075030

  10. Chemical defense, mycorrhizal colonization and growth responses in Plantago lanceolata L.

    PubMed

    De Deyn, Gerlinde Barbra; Biere, A; van der Putten, W H; Wagenaar, R; Klironomos, J N

    2009-06-01

    Allelochemicals defend plants against herbivore and pathogen attack aboveground and belowground. Whether such plant defenses incur ecological costs by reducing benefits from plant mutualistic symbionts is largely unknown. We explored a potential trade-off between inherent plant chemical defense and belowground mutualism with arbuscular mycorrhizal fungi (AMF) in Plantago lanceolata L., using plant genotypes from lines selected for low and high constitutive levels of the iridoid glycosides (IG) aucubin and catalpol. As selection was based on IG concentrations in leaves, we first examined whether IG concentrations covaried in roots. Root and leaf IG concentrations were strongly positively correlated among genotypes, indicating genetic interdependence of leaf and root defense. We then found that root AMF arbuscule colonization was negatively correlated with root aucubin concentration. This negative correlation was observed both in plants grown with monocultures of Glomus intraradices and in plants colonized from whole-field soil inoculum. Overall, AMF did not affect total biomass of plants; an enhancement of initial shoot biomass was offset by a lower root biomass and reduced regrowth after defoliation. Although the precise effects of AMF on plant biomass varied among genotypes, plants with high IG levels and low AMF arbuscule colonization in roots did not produce less biomass than plants with low IG and high AMF arbuscule colonization. Therefore, although an apparent trade-off was observed between high root chemical defense and AMF arbuscule colonization, this did not negatively affect the growth responses of the plants to AMF. Interestingly, AMF induced an increase in root aucubin concentration in the high root IG genotype of P. lanceolata. We conclude that AMF does not necessarily stimulate plant growth, that direct plant defense by secondary metabolites does not necessarily reduce potential benefits from AMF, and that AMF can enhance concentrations of root

  11. Hydrophilic interaction liquid chromatography coupled with tandem mass spectrometry for the quantification of uridine diphosphate-glucose, uridine diphosphate-glucuronic acid, deoxynivalenol and its glucoside: In-house validation and application to wheat.

    PubMed

    Warth, Benedikt; Siegwart, Gerald; Lemmens, Marc; Krska, Rudolf; Adam, Gerhard; Schuhmacher, Rainer

    2015-12-01

    Nucleotide sugars, the activated forms of monosaccharides, are important metabolites involved in a multitude of cellular processes including glycosylation of xenobiotics. Especially in plants, UDP-glucose is one of the most prominent members among these nucleotide-sugars, as it is involved in the formation of glucose conjugates of xenobiotics, including mycotoxins, but also holds a central role in the interconversion of energized sugars such as the formation of UDP-glucuronic acid required for cell wall biosynthesis. Here, we present the first HILIC-LC-ESI-TQ-MS/MS method for the quantification of UDP-glucose and UDP-glucuronic acid together with the Fusarium toxin deoxynivalenol (DON) and its major plant detoxification product DON-3-O-glucoside (DON-3-Glc) utilizing a polymer-based column. For sample preparation a time-effective and straightforward 'dilute and shoot' protocol was applied. The chromatographic run time was minimized to 9min including proper column re-equilibration. In-house validation of the method verified its linear range, intra- (1-7%) and interday (8-20%) precision, instrumental LODs between 0.6 and 10ngmL(-1), selectivity and moderate matrix effects with mean recoveries of 85-103%. To prove the methods applicability, we analyzed two sets of wheat extracts obtained from different cultivars grown under standardized greenhouse conditions. The results clearly demonstrated the suitability of the developed method to quantify UDP-glucose, DON and its masked form D3G in diluted wheat extracts. We observed differing concentration levels of UDP-glucose in the two wheat cultivars showing different resistance to the severe plant disease Fusarium head blight. We propose that the higher ability to detoxify DON into DON-3-Glc might be a consequence of the higher cellular UDP-glucose pool in the resistant cultivar. PMID:26554298

  12. Mechanisms of membrane protein insertion into liposomes during reconstitution procedures involving the use of detergents. 1. Solubilization of large unilamellar liposomes (Prepared by reverse-phase evaporation) by Triton X-100 octyl glucoside, and sodium cholate

    SciTech Connect

    Paternostre, M.T.; Roux, M.; Rigaud, J.L.

    1988-04-19

    The mechanisms governing the solubilization by Triton X-100, octyl glucoside, and sodium cholate of large unilamellar liposomes prepared by reverse-phase evaporation were investigated. The solubilization process is described by the three-stage model previously proposed for the detergents. In stage I, detergent monomers are incorporated into the phospholipid bilayers until they saturate the liposomes. At this point, i.e., stage II, mixed phospholipid-detergent micelles begin to form. By stage III, the lamellar to micellar transition is complete and all the phospholipids are present as mixed micelles. The turbidity of liposome preparations was systematically measured as a function of the amount of detergent added for a wide range of phospholipid concentrations. The results allowed a quantitative determination of the effective detergent to lipid molar ratios in the saturated liposomes. The monomer concentrations of the three detergents in the aqueous phase were also determined at the lamellar to micellar transitions. These transitions were also investigated by /sup 31/P NMR spectroscopy, and complete agreement was found with turbidity measurements. Freeze-fracture electron microscopy and permeability studies in the sublytic range of detergent concentrations indicated that during stage I of solubilization detergent partitioning between the aqueous phase and the lipid bilayer greatly affects the basic permeability of the liposomes without significantly changing the morphology of the preparations. A rough approximation of the partition coefficients was derived from the turbidity and permeability data. It is concluded that when performed systematically, turbidity measurements constitute a very convenient and powerful technique for the quantitative study of the liposome solubilization process by detergents.

  13. Protective effects of 2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucoside in the MPTP-induced mouse model of Parkinson's disease: Involvement of reactive oxygen species-mediated JNK, P38 and mitochondrial pathways.

    PubMed

    He, Hong; Wang, Songhai; Tian, Jiyu; Chen, Lei; Zhang, Wei; Zhao, Junjie; Tang, Haifeng; Zhang, Xiaojun; Chen, Jianzong

    2015-11-15

    Parkinson's disease (PD) is characterized by the selective death of dopaminergic neurons in the substantia nigra pars compacta. Oxidative stress-induced neuron loss is thought to play a crucial role in the pathogenesis of PD. Previous work from our group suggests that 2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucoside (TSG), an active component extracted from a traditional Chinese herb, Polygonum multiflorum thunb, can attenuate 1-methyl-4-phenyl pyridium-induced apoptosis in the neuronal cell line PC12, by inhibiting reactive oxygen species generation and modulating c-Jun N-terminal kinases (JNK) activation. Here, we investigated the protective effects of TSG against 1-methyl-4-phenyl-1,2,3,6-tetrahydropypridine (MPTP)-induced loss of tyrosine hydroxylase positive cells in mice and the underlying mechanisms. The results showed that MPTP-induced loss of tyrosine hydroxylase positive cells and reactive oxygen species generation were prevented by TSG in a dose-dependent manner. The reactive oxygen species scavenger N-acetylcysteine could also mitigate reactive oxygen species generation. Moreover, JNK and P38 were activated by MPTP, but extracellular signal-regulated protein kinases phosphorylation did not change after MPTP treatment. TSG at different doses blocked the activation of JNK and P38. The protective effect of TSG was also associated with downregulation of the bax/bcl-2 ratio, reversed the release of cytochrome c and smac, and inhibited the activation of caspase-3, -6, and -9 induced by MPTP. In conclusion, our studies demonstrated that the protective effects of TSG in the MPTP-induced mouse model of PD are involved, at least in part, in controlling reactive oxygen species-mediated JNK, P38, and mitochondrial pathways. PMID:26477638

  14. Direct comparison between genomic constitution and flavonoid contents in Allium multiple alien addition lines reveals chromosomal locations of genes related to biosynthesis from dihydrokaempferol to quercetin glucosides in scaly leaf of shallot (Allium cepa L.).

    PubMed

    Masuzaki, S; Shigyo, M; Yamauchi, N

    2006-02-01

    The extrachromosome 5A of shallot (Allium cepa L., genomes AA) has an important role in flavonoid biosynthesis in the scaly leaf of Allium fistulosum-shallot monosomic addition lines (FF+nA). This study deals with the production and biochemical characterisation of A. fistulosum-shallot multiple alien addition lines carrying at least 5A to determine the chromosomal locations of genes for quercetin formation. The multiple alien additions were selected from the crossing between allotriploid FFA (female symbol) and A. fistulosum (male symbol). The 113 plants obtained from this cross were analysed by a chromosome 5A-specific PGI isozyme marker of shallot. Thirty plants were preliminarily selected for an alien addition carrying 5A. The chromosome numbers of the 30 plants varied from 18 to 23. The other extrachromosomes in 19 plants were completely identified by using seven other chromosome markers of shallot. High-performance liquid chromatography analyses of the 19 multiple additions were conducted to identify the flavonoid compounds produced in the scaly leaves. Direct comparisons between the chromosomal constitution and the flavonoid contents of the multiple alien additions revealed that a flavonoid 3'-hydroxylase (F3'H) gene for the synthesis of quercetin from kaempferol was located on 7A and that an anonymous gene involved in the glucosidation of quercetin was on 3A or 4A. As a result of supplemental SCAR analyses by using genomic DNAs from two complete sets of A. fistulosum-shallot monosomic additions, we have assigned F3'H to 7A and flavonol synthase to 4A. PMID:16411131

  15. 2-Nitro-3-(p-hydroxyphenyl)propionate and aci-1-nitro-2-(p-hydroxyphenyl)ethane, two intermediates in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L. ) Moench

    SciTech Connect

    Halkier, B.A.; Lykkesfeldt, J.; Moller, B.L. )

    1991-01-15

    The biosynthetic pathway for the cyanogenic glucoside dhurrin derived from tyrosine has been studied in vitro by using ({sup 18}O)oxygen and a microsomal enzyme system obtained from etiolated sorghum seedlings. The products formed were purified by HPLC and TLC, and the incorporation of ({sup 18}O)oxygen was monitored by mass spectrometry. In the presence of NADPH and ({sup 18}O)dioxygen, L-tyrosine is converted to (E)- and (Z)-p-hydroxyphenylacetaldhyde oxime with quantitative incorporation of an ({sup 18}O)oxygen atom into the oxime function. These data demonstrate that the conversion of N-hydroxytyrosine to p-hydroxyphenylacetaldehyde oxime involves additional N-hydroxylation and N-oxidation reactions giving rise to the formation of 2-nitro-3-(p-hydroxyphenyl)propionate, which by decarboxylation produces aci-1-nitro-2-(p-hydroxyphenyl)ethane. Both compounds are additional intermediates in the pathway. The two ({sup 18}O)oxygen atoms introduced by the N-hydroxylations are enzymatically distinguishable as demonstrated by the specific loss of the oxygen atom introduced by the first N-hydroxylation reaction in the subsequent conversion of aci-1-nitro-2-(p-hydroxyphenyl)ethane to (E)-p-hydroxyphenylacetaldehyde oxime. A high flux of intermediates through the microsomal enzyme system is obtained with N-hydroxytyrosine as a substrate. This renders the conversion of the aci-nitro compound rate limiting and results in its release from the active site of the enzyme system and accumulation of the tautomeric nitro compound.

  16. The biosynthesis of cyanogenic glucosides in higher plants. Identification of three hydroxylation steps in the biosynthesis of dhurrin in Sorghum bicolor (L. ) Moench and the involvement of 1-ACI-nitro-2-(p-hydroxyphenyl)ethane as an intermediate

    SciTech Connect

    Halkier, B.A.; Moller, B.L. )

    1990-12-05

    N-Hydroxytyrosine, (E)- and (Z)-p-hydroxyphenyl-acetaldehyde oxime, p-hydroxyphenylacetonitrile, and p-hydroxymandelonitrile are established intermediates in the biosynthesis of the tyrosine-derived cyanogenic glucoside dhurrin. Simultaneous measurements of oxygen consumption and biosynthetic activity using a microsomal enzyme system isolated from etiolated sorghum seedlings demonstrate a requirement for three oxygen molecules in the conversion of tyrosine to p-hydroxymandelonitrile. Two oxygen molecules are consumed in the conversion of tyrosine to (E)-p-hydroxyphenylacetaldehyde oxime, indicating the existence of a previously undetected hydroxylation step in addition to that resulting in the formation of N-hydroxytyrosine. Radioactively labeled 1-nitro-2-(p-hydroxyphenyl)ethane was chemically synthesized and tested as a possible intermediate. Biosynthetic experiments demonstrate that the microsomal enzyme system metabolizes the nitro compound to the subsequent intermediates in dhurrin synthesis (Km = 0.05 mM; Vmax = 14 nmol/mg of protein/h). Low amounts of 1-nitro-2-(p-hydroxyphenyl)ethane are produced in the microsomal reaction mixtures when tyrosine is used as substrate. These data support the involvement of 1-nitro-2-(p-hydroxyphenyl)ethane or more likely its aci-nitro tautomer as an intermediate between N-hydroxytyrosine and p-hydroxyphenylacetaldehyde oxime. The conversion of (E)-p-hydroxyphenylacetaldehydeoxime to p-hydroxymandelonitrile requires a single oxygen molecule. The oxygen molecule is utilized for hydroxylation of p-hydroxyphenylacetonitrile into p-hydroxymandelonitrile. This indicates that the conversion of p-hydroxyphenylacetaldehyde oxime into p-hydroxyphenylacetonitrile proceeds by a simple dehydration reaction.

  17. Inhibitory effects of an ellagic acid glucoside, okicamelliaside, on antigen-mediated degranulation in rat basophilic leukemia RBL-2H3 cells and passive cutaneous anaphylaxis reaction in mice.

    PubMed

    Kuba-Miyara, Megumi; Agarie, Kengo; Sakima, Rina; Imamura, Shihoko; Tsuha, Kazuyo; Yasumoto, Takeshi; Gima, Shinichi; Matsuzaki, Goro; Ikehara, Tsuyoshi

    2012-04-01

    Degranulation inhibitors in plants are widely used for prevention and treatment of immediate-type allergy. We previously isolated a new ellagic acid glucoside, okicamelliaside (OCS), from Camellia japonica leaves for use as a potent degranulation inhibitor. Crude extracts from leaves also suppressed allergic conjunctivitis in rats. In this study, we evaluated the in vivo effect of OCS using a pure sample and performed in vitro experiments to elucidate the mechanism underlying the extraordinary high potency of OCS and its aglycon. The IC(50) values for degranulation of rat basophilic leukemia cells (RBL-2H3) were 14 nM for OCS and 3 μM for aglycon, indicating that the two compounds were approximately 2 to 3 orders of magnitude more potent than the anti-allergic drugs ketotifen fumarate, DSCG, and tranilast (0.17, 3, and >0.3 mM, respectively). Antigen-induced calcium ion (Ca(2+)) elevation was significantly inhibited by OCS and aglycon at all concentrations tested (p<0.05). Upstream of the Ca(2+) elevation in the principle signaling pathway, phosphorylation of Syk (Tyr525/526) and PLCγ-1 (Tyr783 and Ser1248) were inhibited by OCS and aglycon. In DNA microarray-screening test, OCS inhibited expression of proinflammatory cytokines [interleukin (IL)-4 and IL-13], cytokine-producing signaling factors, and prostaglandin-endoperoxidase 2, indicating that OCS broadly inhibits allergic inflammation. During passive cutaneous anaphylaxis in mice, OCS significantly inhibited vascular hyperpermeability by two administration routes: a single intraperitoneal injection at 10 mg/kg and per os at 5 mg/kg for 7 days (p<0.05). These results suggest the potential for OCS to alleviate symptoms of immediate-type allergy. PMID:22330086

  18. Molecular Characterization of a Novel Glucosyltransferase from Lactobacillus reuteri Strain 121 Synthesizing a Unique, Highly Branched Glucan with α-(1→4) and α-(1→6) Glucosidic Bonds

    PubMed Central

    Kralj, S.; van Geel-Schutten, G. H.; Rahaoui, H.; Leer, R. J.; Faber, E. J.; van der Maarel, M. J. E. C.; Dijkhuizen, L.

    2002-01-01

    Lactobacillus reuteri strain 121 produces a unique, highly branched, soluble glucan in which the majority of the linkages are of the α-(1→4) glucosidic type. The glucan also contains α-(1→6)-linked glucosyl units and 4,6-disubstituted α-glucosyl units at the branching points. Using degenerate primers, based on the amino acid sequences of conserved regions from known glucosyltransferase (gtf) genes from lactic acid bacteria, the L. reuteri strain 121 glucosyltransferase gene (gtfA) was isolated. The gtfA open reading frame (ORF) was 5,343 bp, and it encodes a protein of 1,781 amino acids with a deduced Mr of 198,637. The deduced amino acid sequence of GTFA revealed clear similarities with other glucosyltransferases. GTFA has a relatively large variable N-terminal domain (702 amino acids) with five unique repeats and a relatively short C-terminal domain (267 amino acids). The gtfA gene was expressed in Escherichia coli, yielding an active GTFA enzyme. With respect to binding type and size distribution, the recombinant GTFA enzyme and the L. reuteri strain 121 culture supernatants synthesized identical glucan polymers. Furthermore, the deduced amino acid sequence of the gtfA ORF and the N-terminal amino acid sequence of the glucosyltransferase isolated from culture supernatants of L. reuteri strain 121 were the same. GTFA is thus responsible for the synthesis of the unique glucan polymer in L. reuteri strain 121. This is the first report on the molecular characterization of a glucosyltransferase from a Lactobacillus strain. PMID:12200277

  19. Chemical constituents from the fruits of Gardenia jasminoides Ellis.

    PubMed

    Yu, Yang; Feng, Xiao-Lin; Gao, Hao; Xie, Zuo-Lei; Dai, Yi; Huang, Xiao-Jun; Kurihara, Hiroshi; Ye, Wen-Cai; Zhong, Yi; Yao, Xin-Sheng

    2012-04-01

    A new lignan glucoside, (+)-(7S,8R,8'R)-lyoniresinol 9-O-β-D-(6″-O-trans-sinapoyl)glucopyranoside (1), and a new iridoid glucoside, 10-O-trans-sinapoylgeniposide (2), together with eight known compounds, were isolated from the fruits of Gardenia jasminoides Ellis. The structures of the isolates were elucidated by extensive spectroscopic studies, including UV, IR, 1D and 2D NMR, ESI-MS, HR-ESI-MS, and CD experiments. The short-term-memory-enhancement activities of some compounds were evaluated on an Aβ transgenic drosophila model. PMID:22245087

  20. [Chemical and biological evaluation of the effect of plant extracts against Plasmodium berghei].

    PubMed

    Castro, O; Barrios, M; Chinchilla, M; Guerrero, O

    1996-08-01

    Extracts from thirteen species of plants were evaluated by "in vivo" antimalarial test against plasmodium berghei effects. Significant activities were observed in the ethyl acetate and aqueous extracts, elaborated of Cedrela tonduzii leaves, Trichilia havanensis and Trichilia americana barks, Neurolaena lobata and Gliricidia sepium leaves and Duranta repens fruits. Compounds identified include flavanoids, coumarins, mellilotic acid and iridoids which some kind of biodynamic activity has previously been reported. The flavone quercetin 1 purified from C. tonduzii gave strong antimalarial activity, however, its respective glucosides (quercetin 3-glucoside 2 y robinine 7) showed little significant activity. PMID:9246360

  1. A New Lignan Glucoside from Lagochilus ilicifolius

    PubMed Central

    Jing-Shi, Qian; Cheng-Gang, Zhang; Wei, Wang; Ting, Zhang; Hong, Xu; Gui-Xin, Chou

    2015-01-01

    Background: The whole herb of Lagochilus ilicifolius has been used as a folk medicine for treating hemostatic, inflammation and ulcer in China. There were only limited reports on its chemical constituents, and no reports on its pharmacology study. Objective: To isolate compounds from the whole herb of L. ilicifolius and evaluate their cytotoxic activity. Materials and Methods: The column chromatographic techniques were used for separating the constituents of the n-butanol-soluble fraction of the 95% ethanol extract from the whole plant of L. ilicifolius. The structures of one new lignan and two known lignans were elucidated on the basis of spectroscopic analyses and comparison with literature data. The cytotoxic activities of these three lignans were evaluated using the MTT-assay against PC12 cell line derived from rat adrenal pheochromocytoma. Results: The new lignan was identified as erythro-1-[(4-O-β-D-glucopyranosyl-3-methoxyl)-phenyl]-2-[(5’-methoxyl)-pinoresinol]-propane-1,3-diol (1), and two known lignans were identified as tortoside C (2) and sisymbrifolin (3). The new lignan exhibited significant cytotoxic activity against PC12 cell line with IC50 value of 1.22 ± 0.03 μmol/L. Conclusions: A new lignan, erythro-1-[(4-O-β-D-glucopyranosyl-3-methoxyl)-phenyl]-2-[(5’-methoxyl)-pinoresinol]-propane-1,3-diol and two known lignans were isolated from the whole herbs of L. ilicifolius. The two known lignans were reported for the first time in the genus Lagochilus. Three lignans were evaluated for in vitro cytotoxic activity. The new lignan showed relatively strong cytotoxicity against PC12 cell line, while sisymbrifolin and tortoside C exibited no cytotoxicity. PMID:25709232

  2. Light and Nutrient Dependent Responses in Secondary Metabolites of Plantago lanceolata Offspring Are Due to Phenotypic Plasticity in Experimental Grasslands

    PubMed Central

    Miehe-Steier, Annegret; Roscher, Christiane; Reichelt, Michael; Gershenzon, Jonathan; Unsicker, Sybille B.

    2015-01-01

    A few studies in the past have shown that plant diversity in terms of species richness and functional composition can modify plant defense chemistry. However, it is not yet clear to what extent genetic differentiation of plant chemotypes or phenotypic plasticity in response to diversity-induced variation in growth conditions or a combination of both is responsible for this pattern. We collected seed families of ribwort plantain (Plantago lanceolata) from six-year old experimental grasslands of varying plant diversity (Jena Experiment). The offspring of these seed families was grown under standardized conditions with two levels of light and nutrients. The iridoid glycosides, catalpol and aucubin, and verbascoside, a caffeoyl phenylethanoid glycoside, were measured in roots and shoots. Although offspring of different seed families differed in the tissue concentrations of defensive metabolites, plant diversity in the mothers' environment did not explain the variation in the measured defensive metabolites of P. lanceolata offspring. However secondary metabolite levels in roots and shoots were strongly affected by light and nutrient availability. Highest concentrations of iridoid glycosides and verbascoside were found under high light conditions, and nutrient availability had positive effects on iridoid glycoside concentrations in plants grown under high light conditions. However, verbascoside concentrations decreased under high levels of nutrients irrespective of light. The data from our greenhouse study show that phenotypic plasticity in response to environmental variation rather than genetic differentiation in response to plant community diversity is responsible for variation in secondary metabolite concentrations of P. lanceolata in the six-year old communities of the grassland biodiversity experiment. Due to its large phenotypic plasticity P. lanceolata has the potential for a fast and efficient adjustment to varying environmental conditions in plant communities of

  3. Chemical Constituents and LC-profile of Fresh Formosan Lonicera japonica Flower Buds.

    PubMed

    Lo, I-Wen; Cheng, Yuan-Bin; Hsieh, Yi-Jin; Hwang, Tsong-Long; Shieh, Deng-En; Chang, Fang-Rong; Wu, Yang-Chang

    2016-01-01

    One new secoiridoid glucoside, ethylsecologanin dimethyl acetal (1), along with 15 known compounds, comprising six iridoid glucosides (2-7), six flavonoids (8-13), two sterol glucosides (14 and 15), and chlorogenic acid (16) were isolated from the flower buds of Formosan Lonicera japonica. The structures of these isolates were determined on the basis of mass and spectroscopic analyzes. In addition, the chemical profiles of fresh Formosan honeysuckle buds and the dried Chinese one were compared by HPLC with a PDA detector. The calibration curve of the active component, chlorogenic acid, was also provided. As a result of the constituent similarity, Formosan L.japonica can be an alternative to the Chinese honeysuckles. PMID:26996003

  4. New Glycosides and Trypanocidal Metabolites from Vangueria edulis

    PubMed Central

    Mohamed, Shaymaa M. M.; Elokely, Khaled M.; Bachkeet, Enaam Y.; Bayoumi, Soad A. L.; Carnevale, Vincenzo; Klein, Michael L.; Cutler, Stephen J.

    2016-01-01

    A new iridoid glucoside, 10-methoxy apodanthoside (1), and a new monoterpene glycoside, (3S,6S)-cis linalool-3,7-oxide O-β-D-glucopyranosyl-(1″→5′)-β-D-xylofuranoside (2), were isolated from V. edulis (Rubiaceae), along with eighteen known compounds (3–20), including monoterpenes, iridoid glycosides, and a lignin, which were encountered for the first time in the genus Vangueria,. The structural elucidation of the isolates was based on the analysis of spectroscopic (1D and 2D NMR) and HR-ESI-MS data. Detailed stereochemical studies of 1 and related iridoid glucosides (compounds 3, 4 and 8) were made by matching the calculated ECD peaks with the experimental ones. All isolates were tested for their antiprotozoal, antifungal, and antiplasmodial activities. Compounds 9, 15 and 16 showed good trypanocidal activities against Trypanosoma brucei brucei with IC50 values of 8.18, 9.02 and 7.80 μg/mL, respectively and IC90 values of >10, >10 and 9.76 μg/mL, respectively. Compound 16 showed a moderate activity against Candida glabrata with an IC50 value of 8.66 μg/mL. Compound 20 showed a weak antiplasmodial activity against chloroquine-sensitive (D6) and resistant (W2) Plasmodium falciparum with IC50 values of 3.29 (SI, >1.4) and 4.53 (SI, >1) μg/mL, respectively. PMID:26749819

  5. [Chemical constituents from Callicarpa nudiflora and their cytotoxic activities].

    PubMed

    Ma, Yan-Chun; Zhang, Min; Xu, Wen-Tong; Feng, Shi-Xiu; Lei, Ming; Yi, Bo

    2014-08-01

    The chemical consitituents from cytotoxic fraction of the Callicarpa nudiflora extract were isolated and purified by a combination of HP-20 macroporous resin, silica gel and Sephadex LH-20 column chromatographies. The structures were elucidated on the basis of the spectroscopic data and comparison of their spectroscopic data with reported data. The cytotoxicity was evaluated by the MTT assay. The 50% and 70% EtOH elutions of EtOH-extract showed significant cytotoxic activities, leading to the isolation of twelve compounds, which were identified as luteoloside(1), lutedin-4'-O-β-D-glucoside(2), 6-hydroxyluteolin-7-O-β-glucoside(3), lutedin-7-O-neohesperidoside(4), rhoifolin (5), luteolin-7, 4'-di-O-glucoside (6), forsythoside B (7), acteoside (8), alyssonoside (9), catalpol(10), nudifloside(11), and leonuride(12). Compounds 3-6, 10 and 12 were isolated from this genus for the first time, and compound 9 was isolated from this plant for the first time. The cytotoxicity assay demonstrated that flavonoids 1-6, in various concentrations, showed monolithic proliferation inhibitory activities against Hela, A549 and MCF-7 cell lines. Compounds 3, 5 and iridoid glycoside 11 possessed higher cytotoxicacivities. In short, flavonoids are the main components of cytotoxic extract from C. nudiflora, while phenylethanoid glycosides are the predominant ingredient but inactive to cancer cell lines. In addition, the minor iridoid glycoside expressed weak cytotoxic activity. PMID:25509294

  6. Phytochemistry and Ethnopharmacology of Some Medicinal Plants Used in the Kurdistan Region of Iraq.

    PubMed

    Amin, Hawraz Ibrahim M; Ibrahim, Mohammed F; Hussain, Faiq H S; Sardar, Abdullah Sh; Vidari, Giovanni

    2016-03-01

    The majority of Kurds inhabit a region that includes adjacent parts of Iran, Iraq, Syria and Turkey. This review shows that the traditional medicine is still used by Kurdish peoples and underlines the medicinal value of a great number of plants used locally. The medicinal uses include the treatment of a variety of diseases, ranging from simple stomach-ache to highly complicate male and female disorders; even sexual weakness and kidney stones are treated by plants. The majority of the plants that are used are for curing gastro-intestinal disorders and inflammation, followed by urinary tract disorders, skin burns, irritations and liver problems. In the last part of this paper, we also report the first results of our ongoing research project on the constituents of some uninvestigated Kurdish medicinal plants. The C-glycosylflavone embinin, the α-methylene acyl derivative 6-tuliposide A, and the iridoids aucubin and ajugol were isolated for the first time from Iris persica, Tulipa systole and Verbascum calvum, respectively. These plants are traditionally used against inflammation, pain, and skin burns. PMID:27169177

  7. Does vegetation complexity affect host plant chemistry, and thus multitrophic interactions, in a human-altered landscape?

    PubMed

    Wäschke, Nicole; Hancock, Christine; Hilker, Monika; Obermaier, Elisabeth; Meiners, Torsten

    2015-09-01

    Anthropogenic land use may shape vegetation composition and affect trophic interactions by altering concentrations of host plant metabolites. Here, we investigated the hypotheses that: (1) plant N and defensive secondary metabolite contents of the herb Plantago lanceolata are affected by land use intensity (LUI) and the surrounding vegetation composition (=plant species richness and P. lanceolata density), and that (2) changes in plant chemistry affect abundances of the herbivorous weevils Mecinus pascuorum and Mecinus labilis, as well as their larval parasitoid Mesopolobus incultus, in the field. We determined plant species richness, P. lanceolata density, and abundances of the herbivores and the parasitoid in 77 grassland plots differing in LUI index in three regions across Germany. We also measured the N and secondary metabolite [the iridoid glycosides (IGs) aucubin and catalpol] contents of P. lanceolata leaves. Mixed-model analysis revealed that: (1) concentrations of leaf IGs were positively correlated with plant species richness; leaf N content was positively correlated with the LUI index. Furthermore: (2) herbivore abundance was not related to IG concentrations, but correlated negatively with leaf N content. Parasitoid abundance correlated positively only with host abundance over the three regions. Structural equation models revealed a positive impact of IG concentrations on parasitoid abundance in one region. We conclude that changes in plant chemistry due to land use and/or vegetation composition may affect higher trophic levels and that the manifestation of these effects may depend on local biotic or abiotic features of the landscape. PMID:25986560

  8. A new furofuran lignan diglycoside and other secondary metabolites from the antidepressant extract of Castilleja tenuiflora Benth.

    PubMed

    Herrera-Ruiz, Maribel; López-Rodríguez, Ricardo; Trejo-Tapia, Gabriela; Domínguez-Mendoza, Blanca Eda; González-Cortazar, Manases; Tortoriello, Jaime; Zamilpa, Alejandro

    2015-01-01

    Castilleja tenuiflora has been used for the treatment of several Central Nervous System (CNS) diseases. Herein we report the antidepressant activity of the methanol extract from the leaves of this medicinal plant. The oral administration of MeOH extract (500 mg/kg) induced a significant (p < 0.05) decrement of the immobility parameter on Forced Swimming Test (FST) and an increment in the latency and duration of the hypnosis, induced by administration of sodium pentobarbital (Pbi, 40 mg/kg, i.p.). Chemical analysis of this antidepressant extract allowed the isolation of (+)-piperitol-4-O-xylopyranosyl-(1→6)-O-glucopyranoside. This new furofuran lignan diglycoside was named tenuifloroside (1) and its complete chemical structure elucidation on the basis of 1D and 2D NMR spectra analysis of the natural compound 1 and its peracetylated derivative 1a is described. This compound was found together with two flavones-apigenin and luteolin 5-methyl ether-a phenylethanoid-verbascoside-and three iridoids-geniposide, caryoptoside and aucubin. All these compounds were purified by successive normal and reverse phase column chromatography. Tenuifloroside, caryoptoside and luteolin 5-methyl ether were isolated from Castilleja genus for the first time. These findings demonstrate that C. tenuiflora methanol extract has beneficial effect on depressive behaviors, and the knowledge of its chemical constitution allows us to propose a new standardized treatment for future investigations of this species in depressive illness. PMID:26197306

  9. Sonication-assisted Agrobacterium rhizogenes-mediated transformation of Verbascum xanthophoeniceum Griseb. for bioactive metabolite accumulation.

    PubMed

    Georgiev, Milen I; Ludwig-Müller, Jutta; Alipieva, Kalina; Lippert, Annemarie

    2011-05-01

    An efficient protocol for the establishment of transformed root culture of Verbascum xanthophoeniceum using sonication-assisted Agrobacterium rhizogenes-mediated transformation is reported. Only 10 days after the inoculation with A. rhizogenes ATCC 15834 and 45 s ultrasound exposure, hairy roots appeared on 75% of the Verbascum leaves. Ten hairy root lines were isolated, although only half of them were free of bacterial contamination and started growing when excised from mother explants. The transgenic nature of the most vigorously growing hairy root clones (VX1 and VX6) was confirmed by polymerase chain reaction. Under submerged cultivation both hairy root clones accumulated high biomass amounts (12.8 and 14.3 g L(-1), respectively) and significant amounts of bioactive phenylethanoid glycoside verbascoside (over 6-times more than in mother plant leaves). LC-APCI-MS analyses confirmed verbascoside accumulation in hairy root clones along with three other phenylethanoid glycosides (forsythoside B, leucosceptoside B and martynoside) and an iridoid glycoside aucubin. This is the first report on the induction of hairy roots of Verbascum plants. PMID:21184229

  10. New flavanol and cycloartane glucosides from Landoltia punctata.

    PubMed

    Wang, Nini; Xu, Guobo; Fang, Yang; Yang, Tao; Zhao, Hai; Li, Guoyou

    2014-01-01

    Chemical investigation on the constituents of Landoltia punctata led to the isolation and identification of 17 compounds, four of which were new and identified as (3b,24S)-9,19-cycloartane-3,22,24,25-tetraol 3-O-[b-D-glucopyranosyl-(1→2)]-[b-D-glucopyranosyl-(1→6)]-b-D-glucopyranoside (1), (3b,24S)-9,19-cycloartane-3,24,25-triol 3-O-[b-d-glucopyranosyl-(1→2)]-[b-D-glucopyranosyl-(1→6)]-b-D-glucopyranoside (2), 3,4'-dihydroxy-7,3'-dimethoxyflavan-5-O-b-D-glucopyranoside (3) and 3,4'-dihydroxy-4,7,3'-trimethoxyflavan-5-O-b-D-glucopyranoside (4). Their structures were elucidated by spectroscopic, chemical, and biochemical methods. Thus, cycloartane triterpenoids were discovered in the Lemnaceae family for the first time. Compound 3 showed antioxidant capacity in the positively charged 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid radical (ABTS+•) and superoxide anion radical scavenging assays. PMID:24858096

  11. Spirostanol glucosides from the leaves of Cestrum laevigatum L.

    PubMed

    Ribeiro, Paulo Riceli Vasconcelos; Araújo, Ana Jérsia; Costa-Lotufo, Letícia Veras; Braz-Filho, Raimundo; Nobre Junior, Hélio Vitoriano; da Silva, Cecília Rocha; de Andrade Neto, João Batista; Silveira, Edilberto Rocha; Lima, Mary Anne Sousa

    2016-02-01

    Two new steroidal saponins, (25R)-spirost-5-ene-3β,26β-diol 3-O-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 4)-[(1 → 2)-α-L-rhamnopyranosyl]-β-D-glucopyranoside (1) and (25R)-spirost-6-ene-3β,5β-diol 3-O-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 4)-[(1 → 2)-α-L-rhamnopyranosyl]-β-D-glucopyranoside (2), along with the known diosgenin 3-O-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranoside (3), chonglouoside SL-5 (4) and Paris saponin Pb (5) were isolated from the leaves of Cestrum laevigatum. The structures of the compounds were determined using spectroscopic analyses including HRESI-MS, 1D and 2D NMR data, followed by comparison with data from the literature. Among them, two are particularly unique, compound 1 is the first (6)Δ-spirostanol saponin and compound 2 has an unusual C-26 hydroxyl in the (5)Δ-spirostanol skeleton. Antifungal testing showed a potent activity to formosanin C against Candida albicans and Candida parapsilosis. Evaluation of the cytotoxic activity indicated that compound 1 has a moderate activity against HL-60 and SF-295 cell lines, while compound 2 were active only against HL-60. PMID:26705702

  12. Host Shifts from Lamiales to Brassicaceae in the Sawfly Genus Athalia

    PubMed Central

    Opitz, Sebastian E. W.; Boevé, Jean-Luc; Nagy, Zoltán Tamás; Sonet, Gontran; Koch, Frank; Müller, Caroline

    2012-01-01

    Plant chemistry can be a key driver of host shifts in herbivores. Several species in the sawfly genus Athalia are important economic pests on Brassicaceae, whereas other Athalia species are specialized on Lamiales. These host plants have glucosides in common, which are sequestered by larvae. To disentangle the possible direction of host shifts in this genus, we examined the sequestration specificity and feeding deterrence of iridoid glucosides (IGs) and glucosinolates (GSs) in larvae of five species which either naturally sequester IGs from their hosts within the Plantaginaceae (Lamiales) or GSs from Brassicaceae, respectively. Furthermore, adults were tested for feeding stimulation by a neo-clerodane diterpenoid which occurs in Lamiales. Larvae of the Plantaginaceae-feeders did not sequester artificially administered p-hydroxybenzylGS and were more deterred by GSs than Brassicaceae-feeders were by IGs. In contrast, larvae of Brassicaceae-feeders were able to sequester artificially administered catalpol (IG), which points to an ancestral association with Lamiales. In line with this finding, adults of all tested species were stimulated by the neo-clerodane diterpenoid. Finally, in a phylogenetic tree inferred from genetic marker sequences of 21 Athalia species, the sister species of all remaining 20 Athalia species also turned out to be a Lamiales-feeder. Fundamental physiological pre-adaptations, such as the establishment of a glucoside transporter, and mechanisms to circumvent activation of glucosides by glucosidases are therefore necessary prerequisites for successful host shifts between Lamiales and Brassicaceae. PMID:22485146

  13. Host shifts from Lamiales to Brassicaceae in the sawfly genus Athalia.

    PubMed

    Opitz, Sebastian E W; Boevé, Jean-Luc; Nagy, Zoltán Tamás; Sonet, Gontran; Koch, Frank; Müller, Caroline

    2012-01-01

    Plant chemistry can be a key driver of host shifts in herbivores. Several species in the sawfly genus Athalia are important economic pests on Brassicaceae, whereas other Athalia species are specialized on Lamiales. These host plants have glucosides in common, which are sequestered by larvae. To disentangle the possible direction of host shifts in this genus, we examined the sequestration specificity and feeding deterrence of iridoid glucosides (IGs) and glucosinolates (GSs) in larvae of five species which either naturally sequester IGs from their hosts within the Plantaginaceae (Lamiales) or GSs from Brassicaceae, respectively. Furthermore, adults were tested for feeding stimulation by a neo-clerodane diterpenoid which occurs in Lamiales. Larvae of the Plantaginaceae-feeders did not sequester artificially administered p-hydroxybenzylGS and were more deterred by GSs than Brassicaceae-feeders were by IGs. In contrast, larvae of Brassicaceae-feeders were able to sequester artificially administered catalpol (IG), which points to an ancestral association with Lamiales. In line with this finding, adults of all tested species were stimulated by the neo-clerodane diterpenoid. Finally, in a phylogenetic tree inferred from genetic marker sequences of 21 Athalia species, the sister species of all remaining 20 Athalia species also turned out to be a Lamiales-feeder. Fundamental physiological pre-adaptations, such as the establishment of a glucoside transporter, and mechanisms to circumvent activation of glucosides by glucosidases are therefore necessary prerequisites for successful host shifts between Lamiales and Brassicaceae. PMID:22485146

  14. Oleuropein, a non-toxic olive iridoid, is an anti-tumor agent and cytoskeleton disruptor

    SciTech Connect

    Hamdi, Hamdi K. . E-mail: hkhamdi@gmail.com; Castellon, Raquel

    2005-09-02

    Oleuropein, a non-toxic secoiridoid derived from the olive tree, is a powerful antioxidant and anti-angiogenic agent. Here, we show it to be a potent anti-cancer compound, directly disrupting actin filaments in cells and in a cell-free assay. Oleuropein inhibited the proliferation and migration of advanced-grade tumor cell lines in a dose-responsive manner. In a novel tube-disruption assay, Oleuropein irreversibly rounded cancer cells, preventing their replication, motility, and invasiveness; these effects were reversible in normal cells. When administered orally to mice that developed spontaneous tumors, Oleuropein completely regressed tumors in 9-12 days. When tumors were resected prior to complete regression, they lacked cohesiveness and had a crumbly consistency. No viable cells could be recovered from these tumors. These observations elevate Oleuropein from a non-toxic antioxidant into a potent anti-tumor agent with direct effects against tumor cells. Our data may also explain the cancer-protective effects of the olive-rich Mediterranean diet.

  15. Bioactive iridoids and a new lignan from Allamanda cathartica and Himatanthus fallax from the Suriname rainforest.

    PubMed

    Abdel-Kader, M S; Wisse, J; Evans, R; van der Werff, H; Kingston, D G

    1997-12-01

    Bioassay-guided fractionation of the EtOAc extract of both Allamanda cathartica and Himatanthus fallax (Apocynaceae) using the Sc-7 yeast strain resulted in the isolation of the weakly cytotoxic isoplumericin and plumericin. In addition, the new lignan 7(R)-methoxy-8-epi-matairesional and three known compounds, plumieride, matairesinol, and pinoresinol, were isolated from H. fallax. PMID:9428163

  16. Antioxidant and neurosedative properties of polyphenols and iridoids from Lippia alba.

    PubMed

    Hennebelle, Thierry; Sahpaz, Sevser; Gressier, Bernard; Joseph, Henry; Bailleul, François

    2008-02-01

    The neurosedative and antioxidative properties of some major compounds isolated from a citral chemotype of Lippia alba were investigated. Binding assays were performed on two CNS inhibitory targets: benzodiazepine and GABA(A) receptors. The most active compound was luteolin-7-diglucuronide, with half maximal inhibitory concentrations (IC(50)) of 101 and 40 microm, respectively. Fifteen compounds isolated from Lippia alba were tested for their radical scavenging capacities against DPPH. Four of the major compounds (verbascoside, calceolarioside E, luteolin-7-diglucuronide and theveside) were also tested for their antioxidant activity against superoxide radical-anion in cell-free (hypoxanthine-xanthine oxidase) and cellular (PMA-stimulated neutrophil granulocytes) systems. PMID:17705148

  17. Compounds from the Fruits of the Popular European Medicinal Plant Vitex agnus-castus in Chemoprevention via NADP(H):Quinone Oxidoreductase Type 1 Induction

    PubMed Central

    Li, Shenghong; Qiu, Shengxiang; Yao, Ping; Sun, Handong; Fong, Harry H. S.; Zhang, Hongjie

    2013-01-01

    As part of our continuing efforts in the search for potential biologically active compounds from medicinal plants, we have isolated 18 compounds including two novel nitrogen containing diterpenes from extracts of the fruits of Vitex agnus-castus. These isolates, along with our previously obtained novel compound vitexlactam A (1), were evaluated for potential biological effects, including cancer chemoprevention. Chemically, the nitrogenous isolates were found to be two labdane diterpene alkaloids, each containing an α, β-unsaturated γ-lactam moiety. Structurally, they were elucidated to be 9α-hydroxy-13(14)-labden-16,15-amide (2) and 6β-acetoxy-9α-hydroxy-13(14)-labden-15,16-amide (3), which were named vitexlactams B and C, respectively. The 15 known isolates were identified as vitexilactone (4), rotundifuran (5), 8-epi-manoyl oxide (6), vitetrifolin D (7), spathulenol (8), cis-dihydro-dehydro-diconiferylalcohol-9-O-β-D-glucoside (9), luteolin-7-O-glucoside (10), 5-hydroxy-3,6,7,4′-tetramethoxyflavone (11), casticin (12), artemetin (13), aucubin (14), agnuside (15), β-sitosterol (16), p-hydroxybenzoic acid (17), and p-hydroxybenzoic acid glucose ester (18). All compound structures were determined/identified on the basis of 1D and/or 2D NMR and mass spectrometry techniques. Compounds 6, 8, 9, and 18 were reported from a Vitex spieces for the first time. The cancer chemopreventive potentials of these isolates were evaluated for NADP(H):quinone oxidoreductase type 1 (QR1) induction activity. Compound 7 demonstrated promising QR1 induction effect, while the new compound vitexlactam (3) was only slightly active. PMID:23662135

  18. Hedyotis diffusa water extract diminished the cytotoxic effects of chemotherapy drugs against human breast cancer MCF7 cells.

    PubMed

    Dong, Qiulin; Ling, Binbing; Gao, Bosong; Maley, Jason; Sammynaiken, Ramaswami; Yang, Jian

    2014-05-01

    Hedyotis diffusa is a Chinese herbal medicine widely used in combination with other herbal medicines such as Scutellaria barbata to treat various types of cancer. Late-stage and recurrent cancer patients usually use H. diffusa during chemotherapy in expecting to achieve additive or synergistic therapeutic effects. Several classes of active ingredients, including anthraquinones, iridoid glucosides and stigmasterols. have been isolated and characterized from H. diffusa. In the current study, we isolated alkaloid/flavonoid from H diffusa and showed that the crude alkaloid/flavonoid extract rather than its three major components possessed antitumor activity against human breast cancer cell line MCF7. Co-administration of H. diffusa water extract diminished the cytotoxicities of chemotherapy drugs doxorubicin, cyclophosphamide and docetaxel towards the MCF7 cells, implicating that H. diffusa should not be used during breast cancer chemotherapy. PMID:25026725

  19. Multi-Target Strategy and Experimental Studies of Traditional Chinese Medicine for Alzheimer's Disease Therapy.

    PubMed

    Li, Lin; Zhang, Lan; Yang, Cui-cui

    2016-01-01

    Alzheimer's disease (AD) is a multifactorial complex disease. The pathogenesis of AD is very complicated, and involves the β-amyloid (Aβ) cascade, tau hyperphosphorylation, neuroinflammation, oxidative stress, mitochondrial dysfunction, reduced levels of neurotrophic factors, and damage and loss of synapses as well as cholinergic neurons. The multi-target characteristics of traditional Chinese medicine (TCM) may be advantageous over single-target drugs in the treatment of complex diseases. These drugs have therefore attracted more attention in the research and development of AD therapies. This review describes advances made in experimental studies of TCM for AD treatment. It discusses research, from our group and other laboratories, on TCM compound drugs (Shenwu capsule) and approximately 10 Chinese medicinal herb extracts (tetrahydroxystilbene glucoside, epimedium flavonoid, icariin, cornel iridoid glycoside, ginsenoside, puerarin, clausenamide, huperzine A, and timosaponins). PMID:26268330

  20. Comprehensive Chemical Profiling of Picrorhiza kurroa Royle ex Benth Using NMR, HPTLC and LC-MS/MS Techniques.

    PubMed

    Kumar, Dinesh; Kumar, Rakesh; Singh, Bikram; Ahuja, Paramvir Singh

    2016-01-01

    Picrorhiza kurroa is an important herb in Indian medicine and contains cucurbitacins, flavonoids, phenolics, iridoid-glucoside and their derivatives as active constituents for the treatment of indigestion, fever, hepatitis, cancer, liver and respiratory diseases. Extensive use of P. kurroa needs detailed analysis and recognition of chemical diversity, is of great importance to evaluate their role as quality control markers. In the present study, comprehensive metabolic profiling of crude extracts of leaves and rhizomes of P. kurroa was carried out using NMR, HPTLC and LC-MS/MS. Primary and secondary metabolites were unambiguously identified along with a new report of monoterpenic glycoside (1-β-D-glucopyranosyl)-8-hydroxy-3,7-dimethyl-oct-2(E),6(E)-dienoate) in P. Kurroa. Significant qualitative differences with respect to the secondary metabolites were noticed between the leaves and rhizomes tissues. Leaves contained more cucurbitacins and flavonoids while iridoids were present more in rhizomes. The comprehensive chemical profiling is expected to give an idea of chemical diversity and quality of P. kurroa, for their ultimate utilisation in various applications. PMID:26777484

  1. Phytochemical analysis, biological evaluation and micromorphological study of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande endemic to central Apennines, Italy.

    PubMed

    Venditti, Alessandro; Bianco, Armandodoriano; Nicoletti, Marcello; Quassinti, Luana; Bramucci, Massimo; Lupidi, Giulio; Vitali, Luca Agostino; Petrelli, Dezemona; Papa, Fabrizio; Vittori, Sauro; Lucarini, Domenico; Maleci Bini, Laura; Giuliani, Claudia; Maggi, Filippo

    2013-10-01

    Stachys alopecuros subsp. divulsa (Lamiaceae), a perennial herb endemic to central Italy growing on mountain pastures, was investigated for the first time for the content of secondary metabolites, for the micromorphology and histochemistry of glandular trichomes, and for the biological activity of the volatile oil, namely cytotoxic, antioxidant and antimicrobial. The plant showed the molecular pattern of iridoids, among which a new iridoid diglycoside (4'-O-β-D-galactopyranosyl-teuhircoside) was detected, together with a sterol glucoside and a phenylethanoid glycoside. The essential oil from the flowering aerial parts was characterized by a high proportion of sesquiterpene hydrocarbons (65.1%), with (E)-caryophyllene (33.2%) as the most abundant, while other main components were germacrene D (7.6%), α-humulene (6.4%) and the oxygenated cis-sesquisabinene hydrate (10.2%). Taken together, polar and apolar chemical profiles support the classification of the species within the section Betonica of the genus Stachys. Micromorphological study revealed three types of glandular hairs secreting different classes of compounds, with type A peltate hairs producing the bulk of the essential oil. MTT assay revealed the potential of the volatile oil in inhibiting A375, HCT116 and MDA-MB 231 tumor cells (IC₅₀ values below 20 μg/ml). PMID:23827382

  2. Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones

    PubMed Central

    Zimmermann, Nicole; Hilgraf, Robert; Lehmann, Lutz; Ibarra, Daniel

    2012-01-01

    Summary Starting from the enantiomers of limonene, all eight stereoisomers of trans-fused dihydronepetalactones were synthesized. Key compounds were pure stereoisomers of 1-acetoxymethyl-2-methyl-5-(2-hydroxy-1-methylethyl)-1-cyclopentene. The stereogenic center of limonene was retained at position 4a of the target compounds and used to stereoselectively control the introduction of the other chiral centers during the synthesis. Basically, this approach could also be used for the synthesis of enantiomerically pure trans-fused iridomyrmecins. Using synthetic reference samples, the combination of enantioselective gas chromatography and mass spectrometry revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain the enantiomerically pure trans-fused (4R,4aR,7R,7aS)-dihydronepetalactone as a minor component, showing an unusual (R)-configured stereogenic center at position 7. PMID:23019455

  3. Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins

    PubMed Central

    Hilgraf, Robert; Zimmermann, Nicole; Lehmann, Lutz; Tröger, Armin

    2012-01-01

    Summary Following our earlier approach to the synthesis of dihydronepetalactones, all eight stereoisomers of trans-fused iridomyrmecins were synthesized starting from the enantiomers of limonene. Combined gas chromatography and mass spectrometry including enantioselective gas chromatography revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain (4S,4aR,7S,7aR)-iridomyrmecin of 95–97% ee and stereochemically pure (4S,4aS,7R,7aS)-iridomyrmecin as a minor component. PMID:23019456

  4. Bitter Gentian Teas: Nutritional and Phytochemical Profiles, Polysaccharide Characterisation and Bioactivity.

    PubMed

    Olennikov, Daniil N; Kashchenko, Nina I; Chirikova, Nadezhda K; Koryakina, Lena P; Vladimirov, Leonid N

    2015-01-01

    As a result of the wide distribution of herbal teas the data on nutritional characterisation, chemical profile and biological activity of these products are required. The decoctions of Gentiana algida, G. decumbens, G. macrophylla and G. triflora herb teas were nutritionally characterized with respect to their macronutrients, demonstrating the predominance of polysaccharides and low lipid content. Gentian decoctions were also submitted to a microcolumn RP-HPLC-UV analysis of phytochemicals demonstrating a high content of iridoids (177.18-641.04 μg/mL) and flavonoids (89.15-405.71 μg/mL). Additionally, mangiferin was detected in samples of G. triflora tea (19.89 μg/mL). Five free sugars (fructose, glucose, sucrose, gentiobiose, gentianose) were identified in all gentian teas studied, as well as six organic acids (malic, citric, tartaric, oxalic, succinic, quinic). Pectic polysaccharides with a high content of rhamnogalacturonans and arabinogalactans were also identified and characterized in gentian decoctions for the first time. Gentian tea decoctions and their specific compounds (gentiopicroside, loganic acid-6'-O-β-d-glucoside, isoorientin, isoorientin-4'-O-β-d-glucoside, mangiferin, water-soluble polysaccharides) showed a promising antimicrobial, anti-inflammatory and antioxidant potentials. Evidences obtained indicate the prospective use of gentian herb teas as food products and medicines. PMID:26556333

  5. Two new naphthalene glucosides and other bioactive compounds from the carnivorous plant Nepenthes mirabilis.

    PubMed

    Thanh, Nguyen Van; Thao, Nguyen Phuong; Dat, Le Duc; Huong, Phan Thi Thanh; Lee, Sang Hyun; Jang, Hae Dong; Cuong, Nguyen Xuan; Nam, Nguyen Hoai; Kiem, Phan Van; Minh, Chau Van; Kim, Young Ho

    2015-10-01

    Two new naphthalene diglucosides named nepenthosides A (1) and B (2), together with eleven known compounds (3-13), were isolated from the carnivorous plant Nepenthes mirabilis. The structures of these compounds were elucidated based on extensive spectroscopic analysis, including 1D- and 2D-NMR, and MS. The antioxidant activities of compounds 1-13 were evaluated in terms of their peroxyl radical-scavenging (trolox equivalent, TE) and reducing capacities. All isolates showed peroxyl radical-scavenging and reducing activities at concentrations of 1.0 and 10.0 μM. Anti-osteoporotic activities were investigated using murine osteoclastic RAW 264.7 cells. Compounds 1-7 and 9-12 significantly suppressed tartrate-resistant acid phosphatase activity down to 91.13 ± 1.18 to 42.39 ± 1.11%, relative to the control (100%) in nuclear factor-κB ligand (RANκL)-induced osteoclastic RAW 264.7 macrophage cells. PMID:25724283

  6. ABC transporter functions as a pacemaker for sequestration of plant glucosides in leaf beetles

    PubMed Central

    Strauss, Anja S; Peters, Sven; Boland, Wilhelm; Burse, Antje

    2013-01-01

    Plant-herbivore interactions dominate the planet’s terrestrial ecology. When it comes to host–plant specialization, insects are among the most versatile evolutionary innovators, able to disarm multiple chemical plant defenses. Sequestration is a widespread strategy to detoxify noxious metabolites, frequently for the insect’s own benefit against predation. In this study, we describe the broad-spectrum ATP-binding cassette transporter CpMRP of the poplar leaf beetle, Chrysomela populi as the first candidate involved in the sequestration of phytochemicals in insects. CpMRP acts in the defensive glands of the larvae as a pacemaker for the irreversible shuttling of pre-selected metabolites from the hemolymph into defensive secretions. Silencing CpMRP in vivo creates a defenseless phenotype, indicating its role in the secretion process is crucial. In the defensive glands of related leaf beetle species, we identified sequences similar to CpMRP and assume therefore that exocrine gland-based defensive strategies, evolved by these insects to repel their enemies, rely on ABC transporters as a key element. DOI: http://dx.doi.org/10.7554/eLife.01096.001 PMID:24302568

  7. ABC transporter functions as a pacemaker for sequestration of plant glucosides in leaf beetles.

    PubMed

    Strauss, Anja S; Peters, Sven; Boland, Wilhelm; Burse, Antje

    2013-01-01

    Plant-herbivore interactions dominate the planet's terrestrial ecology. When it comes to host-plant specialization, insects are among the most versatile evolutionary innovators, able to disarm multiple chemical plant defenses. Sequestration is a widespread strategy to detoxify noxious metabolites, frequently for the insect's own benefit against predation. In this study, we describe the broad-spectrum ATP-binding cassette transporter CpMRP of the poplar leaf beetle, Chrysomela populi as the first candidate involved in the sequestration of phytochemicals in insects. CpMRP acts in the defensive glands of the larvae as a pacemaker for the irreversible shuttling of pre-selected metabolites from the hemolymph into defensive secretions. Silencing CpMRP in vivo creates a defenseless phenotype, indicating its role in the secretion process is crucial. In the defensive glands of related leaf beetle species, we identified sequences similar to CpMRP and assume therefore that exocrine gland-based defensive strategies, evolved by these insects to repel their enemies, rely on ABC transporters as a key element. DOI: http://dx.doi.org/10.7554/eLife.01096.001. PMID:24302568

  8. A Class of Rigid Linker-bearing Glucosides for Membrane Protein Structural Study

    PubMed Central

    Sadaf, Aiman; Mortensen, Jonas S.; Capaldi, Stefano; Tikhonova, Elena; Hariharan, Parameswaran; de Castro Ribeiro, Orquidea; Loland, Claus J; Guan, Lan; Byrne, Bernadette

    2015-01-01

    Membrane proteins are amphipathic bio-macromolecules incompatible with the polar environments of aqueous media. Conventional detergents encapsulate the hydrophobic surfaces of membrane proteins allowing them to exist in aqueous solution. Membrane proteins stabilized by detergent micelles are used for structural and functional analysis. Despite the availability of a large number of detergents, only a few agents are sufficiently effective at maintaining the integrity of membrane proteins to allow successful crystallization. In the present study, we describe a novel class of synthetic amphiphiles with a branched tail group and a triglucoside head group. These head and tail groups were connected via an amide or ether linkage by using a tris(hydroxylmethyl)aminomethane (TRIS) or neopentyl glycol (NPG) linker to produce TRIS-derived triglucosides (TDTs) and NPG-derived triglucosides (NDTs), respectively. Members of this class conferred enhanced stability on target membrane proteins compared to conventional detergents. Because of straightforward synthesis of the novel agents and their favourable effects on a range of membrane proteins, these agents should be of wide applicability to membrane protein science. PMID:27110345

  9. Linking Microbial Community Structure to β-Glucosidic Function in Soil Aggregates

    SciTech Connect

    Bailey, Vanessa L.; Fansler, Sarah J.; Stegen, James C.; McCue, Lee Ann

    2013-10-01

    To link microbial community 16S structure to a measured function in a natural soil we have scaled both DNA and β-glucosidase assays down to a volume of soil that may approach a unique microbial community. β-glucosidase activity was assayed in 450 individual aggregates which were then sorted into classes of high or low activities, from which groups of 10 or 11 aggregates were identified and grouped for DNA extraction and pyrosequencing. Tandem assays of ATP were conducted for each aggregate in order to normalize these small groups of aggregates for biomass size. In spite of there being no significant differences in the richness or diversity of the microbial communities associated with high β-glucosidase activities compared with the communities associated with low β-glucosidase communities, several analyses of variance clearly show that the communities of these two groups differ. The separation of these groups is partially driven by the differential abundances of members of the Chitinophagaceae family. It may be that observed functional differences in otherwise similar soil aggregates can be largely attributed to differences in resource availability, rather than to presence or absence of particular taxonomic groups.

  10. SANS with contrast variation study of the bacteriorhodopsin-octyl glucoside complex

    NASA Astrophysics Data System (ADS)

    Mo, Yiming; Heller, William T.

    2010-11-01

    Membrane proteins (MPs), which play vital roles in trans-membrane trafficking and signalling between cells and their external environment, comprise a major fraction of the expressed proteomes of many organisms. MP production for biophysical characterization requires detergents for extracting MPs from their native membrane and to solubilize the MP in solution for purification and study. In a proper detergent solution, the detergent-associated MPs retain their native fold and oligomerization state, key requirements for biophysical characterization and crystallization. SANS with contrast variation was performed to characterize BR in complex with OG to better understand the MP-detergent complex. Contrast variation makes it possible to not only probe the conformation of the entire structure but also investigate the conformation of the polypeptide chain within the BR-OG complex. The BR-OG SANS contrast variation series is not consistent with a compact structure, such as a trimeric BR complex surrounded by a belt of detergent. The data strongly suggest that the protein is partially unfolded through its association with the detergent micelles.

  11. SANS with Contrast Variation Study of the Bacteriorhodopsin-octyl Glucoside Complex

    SciTech Connect

    Heller, William T; Mo, Yiming

    2010-01-01

    Membrane proteins (MPs), which play vital roles in trans-membrane trafficking and signaling between cells and their external environment, comprise a major fraction of the expressed proteomes of many organisms. MP production for biophysical characterization requires detergents for extracting MPs from their native membrane and to solubilize the MP in solution for purification and study. In a proper detergent solution, the detergent-associated MPs retain their native fold and oligomerization state, key requirements for biophysical characterization and crystallization. SANS with contrast variation was performed to characterize BR in complex with OG to better understand the MP-detergent complex. Contrast variation makes it possible to not only probe the conformation of the entire structure but also investigate the conformation of the polypeptide chain within the BR-OG complex. The BR-OG SANS contrast variation series is not consistent with a compact structure, such as a trimeric BR complex surrounded by a belt of detergent. The data strongly suggest that the protein is partially unfolded through its association with the detergent micelles.

  12. Treatment of Xerosis with a Topical Formulation Containing Glyceryl Glucoside, Natural Moisturizing Factors, and Ceramide

    PubMed Central

    Kausch, Martina; Rippke, Frank; Schoelermann, Andrea M.; Filbry, Alexander W.

    2012-01-01

    Objective: To assess the effects of Light Formulation, an oil-in-water emulsion, and Rich Formulation, a water-in-oil emulsion, for the treatment of xerosis. Design: Two double-blind, vehicle-controlled trials (both formulations); a double-blind, randomized regression study (Rich Formulation); and a single-blind tolerability study (Light Formulation). The two formulations were applied twice daily for two weeks, for five days in the regression study, and twice daily for two weeks in the tolerability study. Setting: Studies were conducted during winter in Hamburg, Germany. Participants: A total of 169 subjects were enrolled and 154 completed the studies. The majority were between 50 and 80 years of age, women, all with very dry skin. One withdrew because of an incompatibility reaction that reoccurred with the subject's own body lotion after sun exposure. Measurements: Skin hydration and skin barrier function with both formulations over two weeks, long-term moisturization effect after discontinuation of Rich Formulation, and symptom improvement and skin tolerability with Light Formulation. Results: Vehicle-controlled studies of Light and Rich Formulations demonstrated significantly improved hydration at Weeks 1 and 2 versus the untreated site and vehicles, and significantly reduced transepidermal water loss versus untreated site and basic vehicle. Both products significantly decreased visible dryness and tactile roughness. In the regression study, Rich Formulation maintained significant moisturization six days after treatment discontinuation. Light Formulation reduced symptoms of itching, burning, tightness, tingling, and feeling of dryness. Conclusion: These formulations represent a new approach for the treatment of xerosis by addressing multiple key deficiencies in skin hydration. PMID:22916312

  13. Synthesis and structural characterization of three unique Helicobacter pylori α-cholesteryl phosphatidyl glucosides.

    PubMed

    Nguyen, Huy Q; Davis, Ryan A; Gervay-Hague, Jacquelyn

    2014-12-01

    Steryl glycosides produced by bacteria play important biological roles in the evasion and modulation of host immunity. Step-economical syntheses of three cholesteryl-6-O-phosphatidyl-α-D-glucopyranosides (αCPG) unique to Helicobacter pylori have been achieved. The approach relies upon regioselective deprotection of per-O-trimethylsilyl-α-D-cholesterylglucoside at C6 followed by phosphoramidite coupling. Global TMS ether deprotection in the presence of oxygen and subsequent deprotection of the cyano ethyl phosphoester afforded the target compounds in 16-21 % overall yield starting from D-glucose. The structures of these natural products were determined using a combination of 2D NMR methods and mass spectrometry. These robust synthesis and characterization protocols provide analogues to facilitate glycolipidomic profiling and biological studies. PMID:25195783

  14. Reactivity of cellulose reducing end in pyrolysis as studied by methyl glucoside-impregnation.

    PubMed

    Matsuoka, Seiji; Kawamoto, Haruo; Saka, Shiro

    2016-02-01

    For better understanding of the roles of cellulose reducing ends during thermal degradation of cellulose and wood, cellulose samples impregnated with methyl-β-D-glucopyranoside (GlcβOMe), a simple non-reducing sugar model, were pyrolyzed under N2 at relatively low temperatures of 200-280 °C. By the impregnation, cellulose was rather stabilized against discoloration and weight-loss through converting the reducing ends into the glycosides with GlcβOMe. Alternatively, polymerization and discoloration of GlcβOMe were accelerated in the presence of cellulose. A mechanism via reducing sugars as reactive intermediates formed through hydrolysis is proposed to explain these phenomena. These information would be useful to understand the interactions between cellulose and hemicellulose in wood cell wall as well as the role of the reducing ends in cellulose thermal degradation. PMID:26717548

  15. Isolation of two new ionone glucosides from quince (Cydonia oblonga Mill.) leaves.

    PubMed

    Lutz-Röder, Andrea; Schneider, Marc; Winterhalter, Peter

    2002-04-01

    The 9-O-beta-D-glucopyranosides of (6R)-3-oxo-4-hydroxy-7,8-dihydro-alpha-ionol 1 and 3-oxo-5,6-epoxy-beta-ionol 2 were isolated from quince leaves. The glycosidic extract was obtained by XAD-2 adsorption and MeOH elution. After DCCC separation and flash chromatography, purification by high performance liquid chromatography was carried out. The novel quince leaf constituents were characterized as peracetates 1a and 2a. PMID:11990428

  16. The identification and quantification of steryl glucosides in precipitates from commercial biodiesel

    Technology Transfer Automated Retrieval System (TEKTRAN)

    There have been several experiences of the occurrence of precipitates in manufacturing facilities, transport vessels, and storage tanks containing biodiesel. In some cases these have been formed during storage at temperatures above the cloud point of the fuel. High performance liquid chromatograph...

  17. Anomericity of T-2 toxin-glucosides; masked mycotoxins in cereal crops

    Technology Transfer Automated Retrieval System (TEKTRAN)

    T-2 toxin is a trichothecene mycotoxin produced when the fungus Fusarium infects small grains, especially oats. Ingestion of T-2 toxin contaminated grain can cause diarrhea, hemorrhaging, and feed refusal. Cereal crops infected with mycotoxin-producing fungi form toxin glycosides, sometimes called m...

  18. Development and evaluation of monoclonal antibodies for the glucoside of T-2 toxin (T2-Glc)

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The interactions between fungi and plants can yield metabolites that are toxic in animal systems. Certain fungi are known to produce sesquiterpenoid trichothecenes, such as T-2 toxin, that are biotransformed by several mechanisms including glucosylation. The glucosylated forms have been found in gra...

  19. Benzylbenzoate and norlignan glucosides from Curculigo pilosa: structural analysis and in vitro vascular activity.

    PubMed

    Palazzino, G; Galeffi, C; Federici, E; Delle Monache, F; Cometa, M F; Palmery, M

    2000-11-01

    From the rhizomes of Curculigo pilosa, two benzylbenzoate diglucosides, piloside A and piloside B, and a glucosyl-fused norlignan, pilosidine, previously obtained only as the tetra-O-methyl derivative, were isolated. Pilosidine showed facilitating effect on adrenaline evoked contractions in rabbit aorta isolated preparations. PMID:11140602

  20. Antimicrobial activity of phenolics and glucosinolate hydrolysis products and their synergy with streptomycin against pathogenic bacteria.

    PubMed

    Saavedra, Maria J; Borges, Anabela; Dias, Carla; Aires, Alfredo; Bennett, Richard N; Rosa, Eduardo S; Simões, Manuel

    2010-05-01

    The purpose of the present study was to evaluate the in vitro antibacterial effects of different classes of important and common dietary phytochemicals (5 simple phenolics - tyrosol, gallic acid, caffeic acid, ferulic acid, and chlorogenic acid; chalcone - phloridzin; flavan-3-ol - (-) epicatechin; seco-iridoid - oleuropein glucoside; 3 glucosinolate hydrolysis products - allylisothiocyanate, benzylisothiocyanate and 2-phenylethylisothiocyanate) against Escherichia coli, Pseudomonas aeruginosa, Listeria monocytogenes and Staphylococcus aureus. Another objective of this study was to evaluate the effects of dual combinations of streptomycin with the different phytochemicals on antibacterial activity. A disc diffusion assay was used to evaluate the antibacterial activity of the phytochemicals and 3 standard antibiotics (ciprofloxacin, gentamicin and streptomycin) against the four bacteria. The antimicrobial activity of single compounds and dual combinations (streptomycin-phytochemicals) were quantitatively assessed by measuring the inhibitory halos. The results showed that all of the isothiocyanates had significant antimicrobial activities, while the phenolics were much less efficient. No antimicrobial activity was observed with phloridzin. In general P. aeruginosa was the most sensitive microorganism and L. monocytogenes the most resistant. The application of dual combinations demonstrated synergy between streptomycin and gallic acid, ferulic acid, chlorogenic acid, allylisothiocyanate and 2-phenylethylisothiocyanate against the Gram-negative bacteria. In conclusion, phytochemical products and more specifically the isothiocyanates were effective inhibitors of the in vitro growth of the Gram-negative and Gram-positive pathogenic bacteria. Moreover, they can act synergistically with less efficient antibiotics to control bacterial growth. PMID:20632977

  1. Hydrolysis of Oleuropein by Lactobacillus plantarum Strains Associated with Olive Fermentation

    PubMed Central

    Ciafardini, G.; Marsilio, V.; Lanza, B.; Pozzi, N.

    1994-01-01

    Oleuropein (Chemical Abstracts Service registry number 32619-42-4), a bitter-tasting secoiridoid glucoside commonly found in leaves of the olive tree as well as in olives (Olea europaea L.), was found to be hydrolyzed by the β-glucosidase (EC 3.2.1.2.1) produced by oleuropeinolytic Lactobacillus plantarum-type strains. Three strains, designated B17, B20, and B21, were isolated from the brine of naturally ripe olives not treated with alkali. These strains were rod-shaped forms, grown at a pH 3.5 limit, and tolerated 1% oleuropein and 8% NaCl in the growth medium. The β-glucosidase produced hydrolyzed 5-bromo-4-chloro-3-indolyl-β-d-glucopy-ranoside as well as oleuropein. The presence of 2% glucose in the medium inhibited activity by 40 to 50%, depending on the bacterial strain. Chromatographic analysis of the trimethylsilyl derivatives of the products obtained after 7 days of incubation at 30°C of strain B21 showed all the hydrolysis products of oleuropein, i.e., aglycone, iridoid monoterpen, and 3,4-dihydroxyphenylethanol (hydroxytyrosol). Oleuropein and its aglycone after 21 days of incubation decreased to trace levels with the simultaneous increase in concentration of β-3,4-dihydroxyphenylethanol. Images PMID:16349442

  2. How insects overcome two-component plant chemical defence: plant β-glucosidases as the main target for herbivore adaptation.

    PubMed

    Pentzold, Stefan; Zagrobelny, Mika; Rook, Fred; Bak, Søren

    2014-08-01

    Insect herbivory is often restricted by glucosylated plant chemical defence compounds that are activated by plant β-glucosidases to release toxic aglucones upon plant tissue damage. Such two-component plant defences are widespread in the plant kingdom and examples of these classes of compounds are alkaloid, benzoxazinoid, cyanogenic and iridoid glucosides as well as glucosinolates and salicinoids. Conversely, many insects have evolved a diversity of counteradaptations to overcome this type of constitutive chemical defence. Here we discuss that such counter-adaptations occur at different time points, before and during feeding as well as during digestion, and at several levels such as the insects’ feeding behaviour, physiology and metabolism. Insect adaptations frequently circumvent or counteract the activity of the plant β-glucosidases, bioactivating enzymes that are a key element in the plant’s two-component chemical defence. These adaptations include host plant choice, non-disruptive feeding guilds and various physiological adaptations as well as metabolic enzymatic strategies of the insect’s digestive system. Furthermore, insect adaptations often act in combination, may exist in both generalists and specialists, and can act on different classes of defence compounds. We discuss how generalist and specialist insects appear to differ in their ability to use these different types of adaptations: in generalists, adaptations are often inducible, whereas in specialists they are often constitutive. Future studies are suggested to investigate in detail how insect adaptations act in combination to overcome plant chemical defences and to allow ecologically relevant conclusions. PMID:25165798

  3. Antidiabetic compounds from Sarracenia purpurea used traditionally by the Eeyou Istchee Cree First Nation.

    PubMed

    Muhammad, Asim; Guerrero-Analco, Jose A; Martineau, Louis C; Musallam, Lina; Madiraju, Padma; Nachar, Abir; Saleem, Ammar; Haddad, Pierre S; Arnason, John T

    2012-07-27

    Through ethnobotanical surveys, the CIHR Team in Aboriginal Antidiabetic Medicines identified 17 boreal forest plants stemming from the pharmacopeia of the Cree First Nations of Eeyou Istchee (James Bay region of Northern Quebec) that were used traditionally against diabetes symptoms. The leaves of Sarracenia purpurea (pitcher plant), one of the identified Cree plants, exhibited marked antidiabetic activity in vitro by stimulating glucose uptake in C2C12 mouse muscle cells and by reducing glucose production in H4IIE rat liver cells. Fractionation guided by glucose uptake in C2C12 cells resulted in the isolation of 11 compounds from this plant extract, including a new phenolic glycoside, flavonoid glycosides, and iridoids. Compounds 6 (isorhamnetin-3-O-glucoside), 8 [kaempferol-3-O-(6″-caffeoylglucoside], and 11 (quercetin-3-O-galactoside) potentiated glucose uptake in vitro, which suggests they represent active principles of S. purpurea (EC(50) values of 18.5, 13.8, and 60.5 μM, respectively). This is the first report of potentiation of glucose uptake by compounds 6 and 8, while compound 11 (isolated from Vaccinium vitis) was previously shown to enhance glucose uptake. Treatment of H4IIE liver cells with the new compound 1, 6'-O-caffeoylgoodyeroside, decreased hepatic glucose production by reducing glucose-6-phosphatase enzymatic activity (IC(50) = 13.6 μM), which would contribute to lowering glycemia and to the antidiabetic potential of S. purpurea. PMID:22738356

  4. Biotransformation and metabolic profile of catalpol with human intestinal microflora by ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry.

    PubMed

    Tao, Jin-hua; Zhao, Min; Wang, Dong-geng; Yang, Chi; Du, Le-Yue; Qiu, Wen-qian; Jiang, Shu

    2016-01-15

    Traditional Chinese medicine (TCM) has been used in clinical practice for thousands of years. Catalpol, an iridoid glucoside, abundantly found in the root of the common used herb medicine Rehmannia glutinosa Libosch, has been reported to show various biological effects and pharmacological activities. After oral administration, the active ingredient might have interactions with the intestinal bacteria, which could help unravel how the medicine was processed in vivo. In this work, different pure bacteria from healthy human feces were isolated and used to bioconvert catalpol. Ultra performance liquid chromatography/quadrupole-time-of-flight mass spectrometry (UPLC-Q-TOF/MS) technique combined with Metabolynx(™) software was applied to analyze catalpol metabolites. Compared with blank samples, parent compound (M0) and four metabolites (M1-M4) were detected and tentatively identified based on the characteristics of their protonated ions. The metabolites were likely to be: catalpol aglycone (M1), acetylated catalpol (M2), dimethylated and hydroxylated catalpol aglycone (M3), nitrogen-containing catalpol aglycone (M4). M1 and M4 were generated in the majority of the samples like Bacteroides sp. 45. M3 was obtained in several bacterial samples like Enterococcus sp. 8-2 and M2 was detected only in the sample of Enterococcus sp. 43-1. To our knowledge, the metabolic routes and metabolites of catalpol produced by human intestinal bacteria were all firstly reported. PMID:26741989

  5. Specioside ameliorates oxidative stress and promotes longevity in Caenorhabditis elegans.

    PubMed

    Asthana, Jyotsna; Yadav, A K; Pant, Aakanksha; Pandey, Swapnil; Gupta, M M; Pandey, Rakesh

    2015-03-01

    Specioside (6-O-coumaroylcatalpol) is an iridoid glucoside which possesses multifunctional activities viz. analgesic, antidyspeptic, astringent, liver stimulating and wound healing properties. The present study for the first time delineates stress alleviating and lifespan prolonging action of specioside (SPC), isolated from Stereospermum suaveolens in the free living, multicellular nematode model Caenorhabditis elegans. A strong correlation between lifespan extension and stress modulation in adult worms was established in a dose dependent manner. The dietary intake of this phytomolecule elevated juglone induced oxidative and heat induced thermal stress tolerance in C. elegans. On evaluation, it was found that 25 μM dose of SPC significantly extended lifespan by 15.47% (P≤0.0001) with reduction in stress level. Furthermore, SPC enhanced mean survival in mev-1 mutant suggesting its oxidative stress reducing potential. Furthermore, SPC augmented stress modulatory enzymes superoxide dismutase (SOD) and catalase (CAT) level in C. elegans. Altogether, these findings broaden current perspectives concerning stress alleviating potentials of SPC and have implications in development of therapeutics for curing age related disorders. PMID:25619942

  6. Nano-liquid chromatography coupled to time-of-flight mass spectrometry for phenolic profiling: a case study in cranberry syrups.

    PubMed

    Contreras, María del Mar; Arráez-Román, David; Fernández-Gutiérrez, Alberto; Segura-Carretero, Antonio

    2015-01-01

    A new method based on nano-liquid chromatography coupled to time-of-flight mass spectrometry (nano-LC-TOF-MS) using lock-mass calibration was developed to facilitate the accurate and routine characterization and quantification of phenolic compounds. Thus, it was applied to study cranberry syrups, in which, using negative ionization mode, a total of nine phenolic compounds were unequivocally identified using standards and 38 tentatively taking into account their retention time, accurate mass (errors<5 ppm) data and isotope pattern, as well as literature. Among them, 13 compounds, belonging to flavonols and iridoids conjugated with phenolic acids, were reported for first time in cranberry or cranberry based-products. The analytical method was also validated using chlorogenic acid, p-coumaric acid, (+)-catechin, (-)-epicatechin, procyanidin A2, quercetin 3-O-glucoside, quercetin 3-O-rhamnoside, quercetin, and myricetin standards. In this way, the analytical method showed adequate linearity, with R(2) above 0.99, and acceptable values of intra- and inter-day repeatability of the retention time and peak area. The detection limits and quantification were between 1.0-15.6 ng mL(-1) and 2.0-62.5 ng mL(-1), respectively. The method can be extended to characterize phenolic compounds in other food and plant matrices, and as well biological samples. PMID:25476399

  7. Rapid quantitative analysis of adulterant Lonicera species in preparations of Lonicerae Japonicae Flos.

    PubMed

    Zhang, Xiao; Guo, Qing; Yu, Boyang

    2015-12-01

    Lonicerae Japonicae Flos is often adulterated with Lonicerae Flos, which is derived from the other four Lonicera species, in both the crude drug and Lonicerae Japonicae Flos preparations. We proposed a methodology for the quantitative analysis of adulterant Lonicerae Flos in Lonicerae Japonicae Flos preparations. Taking macranthoidins A, B, dipsacoside B (saponins), sweroside (iridoids), and luteolin-7-O-d-glucoside (flavonoids) as markers, a method of ultra high performance liquid chromatography with triple quadrupole mass spectrometry was employed to determine their amounts in Lonicerae Flos, Lonicerae Japonicae Flos, and Lonicerae Japonicae Flos preparations. The proportion of adulterant Lonicerae Flos in Lonicerae Japonicae Flos preparations was estimated based on the saponin contents of Lonicerae Japonicae Flos and Lonicerae Flos. All analytes separated under isocratic elution in 12 min with acceptable linearity, precision, repeatability, and accuracy. Lonicerae Japonicae Flos was easily distinguished from Lonicerae Flos by the total amount of saponins (0.067 and > 45.8 mg/g for Lonicerae Japonicae Flos and Lonicerae Flos, respectively). Eighteen of twenty one Lonicerae Japonicae Flos preparation samples were adulterated with Lonicerae Flos in proportions of 11.3-100%. The developed ultra high performance liquid chromatography with triple quadrupole mass spectrometry method could be used for the identification of Lonicerae Japonicae Flos and the four species of Lonicerae Flos and for the analysis of Lonicerae Japonicae Flos preparations adulterated with Lonicerae Flos. PMID:26420337

  8. Characterization of Microemulsion Systems Formed by a Mixed 1,3-Dioxolane Ethoxylate / Octyl Glucoside Surfactant System

    SciTech Connect

    Alkhatib, Mayson H; Hayes, Douglas G; Urban, Volker S

    2009-01-01

    The phase behavior of microemulsion systems containing water (or 1.0 wt% NaCl{sub aq}), isooctane, and the binary surfactant system consisting of n-octyl-{beta}-D-glucopyranoside, C{sub 8}{beta}G{sub 1}, and the acid-cleavable alkyl ethoxylate, 4-CH{sub 3}O (CH{sub 2}CH{sub 2}O){sub 7.2}, 2-(CH{sub 2}){sub 12}CH{sub 3}, 2-(CH{sub 2})CH{sub 3}, 1,3-dioxolane, or 'cyclic ketal' ('CK-2,13'), was determined. Large temperature-insensitive one, two, and three-phase microemulsion-phase regions were obtained when equal masses of the two surfactants were employed, suggesting that C{sub 8}{beta}G{sub 1} reduces the temperature sensitivity of CK-2,13's ethoxylate group. Addition of C{sub 8}{beta}G{sub 1} to CK-2,13 greatly improves the latter's low efficiency, evidenced by the formation of a three-phase microemulsion system for surfactant concentrations at low fractions of total surfactants for systems with equal mass ratios of water to oil and CK-2,13 to C{sub 8}{beta}G{sub 1}. Analysis of the phase diagrams also suggests that CK-2,13 and C{sub 8}{beta}G{sub 1} impart hydrophobic and hydrophilic character, respectively, to the surfactant mixture, and that addition of salt further increases the hydrophilicity of C{sub 8}{beta}G{sub 1}, presumably because of the salting-in of the latter. Analysis of small-angle neutron scattering data revealed that the mixed surfactant system formed spherical oil-in-water microemulsions, and that increasing the CK-2,13 fraction among the surfactants reduced the critical microemulsion concentration but slightly increased the nanodroplet size.

  9. Neutral Loss Ion Mapping Experiment Combined with Precursor Mass List and Dynamic Exclusion for Screening Unstable Malonyl Glucoside Conjugates

    NASA Astrophysics Data System (ADS)

    Yang, Min; Zhou, Zhe; Yao, Shuai; Li, Shangrong; Yang, Wenzhi; Jiang, Baohong; Liu, Xuan; Wu, Wanying; Qv, Hua; Guo, De-an

    2016-01-01

    Malonates are one type of the acylation conjugates and found abundantly in ginseng and soybean. Malonyl conjugates of ginsenosides and isoflavone glycosides were often considered as the characteristic components to evaluate various species and different forms of ginseng and soybean products because of their thermal instability. Another famous isoflavonoid-rich leguminous traditional Chinese medicine (TCM), named Puerarin lobata (Gegen), has also been reported to contain malonyl daidzin and malonyl genistin. However, the conjugates were found to present in very low amount and particularly unstable in the negative ion mode scan using LTQ Orbitrap mass spectrometry with electrospray ionization (ESI). In order to screen and characterize the malonyl conjugates in Gegen, a specific method was designed and developed combining neutral loss ion mapping (NLIM) experiment and precursor mass list (PL) triggered data dependent acquisition (DDA). Along with the activation of dynamic exclusion (DE), the method was proven to be specific and efficient for searching the malonate derivatives from Gegen. Two samples were examined by the established method. A total of 66 compounds were found, and 43 of them were malonates of isoflavone glycoside. Very few compounds were reported previously in Gegen. The results are helpful to understand the constituents of Gegen with more insight. The study not only provided a method for analyzing the malonyl conjugates from complex matrices but also explored a way to trace other low amount components in TCMs.

  10. Neutral Loss Ion Mapping Experiment Combined with Precursor Mass List and Dynamic Exclusion for Screening Unstable Malonyl Glucoside Conjugates.

    PubMed

    Yang, Min; Zhou, Zhe; Yao, Shuai; Li, Shangrong; Yang, Wenzhi; Jiang, Baohong; Liu, Xuan; Wu, Wanying; Qv, Hua; Guo, De-an

    2016-01-01

    Malonates are one type of the acylation conjugates and found abundantly in ginseng and soybean. Malonyl conjugates of ginsenosides and isoflavone glycosides were often considered as the characteristic components to evaluate various species and different forms of ginseng and soybean products because of their thermal instability. Another famous isoflavonoid-rich leguminous traditional Chinese medicine (TCM), named Puerarin lobata (Gegen), has also been reported to contain malonyl daidzin and malonyl genistin. However, the conjugates were found to present in very low amount and particularly unstable in the negative ion mode scan using LTQ Orbitrap mass spectrometry with electrospray ionization (ESI). In order to screen and characterize the malonyl conjugates in Gegen, a specific method was designed and developed combining neutral loss ion mapping (NLIM) experiment and precursor mass list (PL) triggered data dependent acquisition (DDA). Along with the activation of dynamic exclusion (DE), the method was proven to be specific and efficient for searching the malonate derivatives from Gegen. Two samples were examined by the established method. A total of 66 compounds were found, and 43 of them were malonates of isoflavone glycoside. Very few compounds were reported previously in Gegen. The results are helpful to understand the constituents of Gegen with more insight. The study not only provided a method for analyzing the malonyl conjugates from complex matrices but also explored a way to trace other low amount components in TCMs. PMID:26334988

  11. Prenylfuranocoumarin-HMGA-flavonol glucoside conjugates and other constituents of the fruit peels of Citrus hystrix and their anticholinesterase activity.

    PubMed

    Seeka, Chonticha; Sutthivaiyakit, Pakawadee; Youkwan, Juthamanee; Hertkorn, Norbert; Harir, Mourad; Schmitt-Kopplin, Philippe; Sutthivaiyakit, Somyote

    2016-07-01

    Sixteen compounds including dihydroxy prenylfuranocoumarins/3-hydroxy-3-methylglutaric acid conjugates and dihydroxy prenylfuranocoumarins/3-hydroxy-3-methylglutaric acid/1-O-flavonyl-β-d-glucopyranoside conjugates, together with other dihydroxyprenylfuranocoumarins conjugates, were isolated from the ethyl acetate extract of the fruit peels of Citrus hystrix. Some of the isolates were evaluated for their cholinesterase inhibitory activity, but only one compound possessing a 3-O-β-d-glucopyranosyl-3,5,7,4'-tetrahydroxy-6,8,3'-trimethoxyflavonol nucleus in the prenylfuranocoumarin-HMGA conjugate showed strong activity. PMID:26995149

  12. Developing transgenic wheat and barley that exhibit resistance to Fusarium graminearum via glucoside conjugation of trichothecene mycotoxins

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Fusarium graminearum infection of wheat and barley results in production of trichothecene mycotoxins including deoxynivalenol (DON) and nivalenol (NIV). These mycotoxins result in increased fungal virulence and reduce grain quality. Numerous transcriptomic studies have been conducted by our lab on t...

  13. An on-line method for pressurized hot water extraction and enzymatic hydrolysis of quercetin glucosides from onions.

    PubMed

    Lindahl, Sofia; Liu, Jiayin; Khan, Samiullah; Karlsson, Eva Nordberg; Turner, Charlotta

    2013-06-27

    A novel environmentally sound continuous-flow hot water extraction and enzymatic hydrolysis method for determination of quercetin in onion raw materials was successfully constructed using a stepwise optimization approach. In the first step, enzymatic hydrolysis of quercetin-3,4'-diglucoside to quercetin was optimized using a three level central composite design considering temperature (75-95°C), pH (3-6) and volume concentration of ethanol (5-15%). The enzyme used was a thermostable β-glucosidase variant (termed TnBgl1A_N221S/P342L) covalently immobilized on either of two acrylic support-materials (Eupergit(®) C 250L or monolithic cryogel). Optimal reaction conditions were irrespective of support 84°C, 5% ethanol and pH 5.5, and at these conditions, no significant loss of enzyme activity was observed during 72 h of use. In a second step, hot water extractions from chopped yellow onions, run at the optimal temperature for hydrolysis, were optimized in a two level design with respect to pH (2.6 and 5.5), ethanol concentration (0 and 5%) and flow rate (1 and 3 mL min(-1)) Obtained results showed that the total quercetin extraction yield was 1.7 times higher using a flow rate of 3 mL min(-1) (extraction time 90 min), compared to a flow rate of 1 mL min(-1) (extraction time 240 min). Presence of 5% ethanol was favorable for the extraction yield, while a further decrease in pH was not, not even for the extraction step alone. Finally, the complete continuous flow method (84°C, 5% ethanol, pH 5.5, 3 mL min(-1)) was used to extract quercetin from yellow, red and shallot onions and resulted in higher or similar yield (e.g. 8.4±0.7 μmol g(-1) fresh weight yellow onion) compared to a conventional batch extraction method using methanol as extraction solvent. PMID:23764443

  14. Efficacy of topical treatment of pigmentation skin disorders with plant hydroquinone glucosides as assessed by quantitative color analysis.

    PubMed

    Clarys, P; Barel, A

    1998-06-01

    Hydroquinone is a well known reagent used in the treatment of pigmentation disorders. The instability of the quinones and the required active concentration make topical treatment rather difficult. We tested the efficacy of an ascorbate-phytohydroquinone complex that inhibits the synthesis of melanin and promotes the degradation of the existing melanin. Lentigo senile lesions were evaluated before and after 1 month of treatment. Objective skin color evaluation was performed instrumentally. After one month of treatment, a clear depigmentation of the macules was measured. None of the volunteers reported any side effects from the prolonged treatment with the hydroquinone containing product. PMID:9675352

  15. Search for constituents with neurotrophic factor-potentiating activity from the medicinal plants of paraguay and Thailand.

    PubMed

    Li, Yushan; Ohizumi, Yasushi

    2004-07-01

    20 medicinal plants of Paraguay and 3 medicinal plants of Thailand were examined on nerve growth factor (NGF)-potentiating activities in PC12D cells. The trail results demonstrated that the methanol extracts of four plants, Verbena littoralis, Scoparia dulcis, Artemisia absinthium and Garcinia xanthochymus, markedly enhanced the neurite outgrowth induced by NGF from PC12D cells. Furthermore, utilizing the bioactivity-guided separation we successfully isolated 32, 4 and 5 constituents from V. littoralis, S. dulcis and G. xanthochymus, respectively, including nine iridoid and iridoid glucosides (1-9), two dihydrochalcone dimers (10 and 11), two flavonoids and three flavonoid glycosides (12-16), two sterols (17 and 18), ten triterpenoids (19-28), five xanthones (29-33), one naphthoquinone (34), one benzenepropanamide (35), four phenylethanoid glycosides (36-39) and two other compounds (40 and 41). Among which, 15 compounds (1-4, 10-11, 14-18, 29-31 and 34) were new natural products. The results of pharmacological trails verified that littoralisone (1), gelsemiol (5), 7a-hydroxysemperoside aglucone (6), verbenachalcone (10), littorachalcone (11), stigmast-5-ene 3beta,7alpha,22alpha-triol (18), ursolic acid (19), 3beta-hydroxyurs-11-en-28,13beta-olide (24), oleanolic acid (25), 2alpha,3beta-dihydroxyolean-12-en-28-oic acid (26), 1,4,5,6-tetrahydroxy-7,8-di(3-methylbut-2-enyl)xanthone (29), 1,2,6-trihydroxy-5-methoxy-7-(3-methylbut-2-enyl)xanthone (30), 1,3,5,6-tetrahydroxy-4,7,8-tri(3-methyl-2-butenyl)xanthone (31), 12b-hydroxy-des-D-garcigerrin A (32), garciniaxanthone E (33) and (4R)-4,9-dihydroxy-8-methoxy-alpha-lapachone (34) elicited marked enhancement of NGF-mediated neurite outgrowth in PC12D cells. These substances may contribute to the basic study and the medicinal development for the neurodegenerative disorder. PMID:15235225

  16. Geniposide, from Gardenia jasminoides Ellis, inhibits the inflammatory response in the primary mouse macrophages and mouse models.

    PubMed

    Fu, Yunhe; Liu, Bo; Liu, Jinhua; Liu, Zhicheng; Liang, Dejie; Li, Fengyang; Li, Depeng; Cao, Yongguo; Zhang, Xichen; Zhang, Naisheng; Yang, Zhengtao

    2012-12-01

    Geniposide, a main iridoid glucoside component of gardenia fruit, has been known to exhibit antibacterial, anti-inflammatory and other important therapeutic activities. The objective of this study was to investigate the protective effects of geniposide on inflammation in lipopolysaccharide (LPS) stimulated primary mouse macrophages in vitro and LPS induced lung injury model in vivo. The expression of pro-inflammatory cytokines was determined by enzyme-linked immunosorbent assay (ELISA). Nuclear factor-kappa B (NF-κB), inhibitory kappa B (IκBα) protein, p38, extracellular signal-regulated kinase (ERK), c-Jun N-terminal kinase (JNK) and Toll-like receptor 4 (TLR4) were determined by Western blot. Further analysis was carried out in mTLR4 and mMD-2 co-transfected HEK293 cells. The results showed that geniposide markedly inhibited the LPS-induced TNF-α, IL-6 and IL-1β production both in vitro and in vivo. Geniposide blocked the phosphorylation of IκBα, p65, p38, ERK and JNK in LPS stimulated primary mouse macrophages. Furthermore, geniposide inhibited the expression of TLR4 in LPS stimulated primary mouse macrophages and inhibited the LPS-induced IL-8 production in HEK293-mTLR4/MD-2 cells. In vivo study, it was also observed that geniposide attenuated lung histopathologic changes in the mouse models. These results suggest that geniposide exerts an anti-inflammatory property by down-regulating the expression of TLR4 up-regulated by LPS. Geniposide is highly effective in inhibiting acute lung injury and may be a promising potential therapeutic reagent for acute lung injury treatment. PMID:22878137

  17. Geniposide alleviates inflammation by suppressing MeCP2 in mice with carbon tetrachloride-induced acute liver injury and LPS-treated THP-1 cells.

    PubMed

    Ma, Tao-tao; Li, Xiao-feng; Li, Wan-xia; Yang, Yang; Huang, Cheng; Meng, Xiao-ming; Zhang, Lei; Li, Jun

    2015-12-01

    Geniposide (GP), an iridoid glucoside extracted from Gardenia jasminoides Ellis fruits, has been used as a herbal medicine to treat liver and gall bladder disorders for many years. However the mechanism of anti-inflammatory is largely unknown. In this study, GP significantly attenuated inflammation in acute liver injury (ALI) mice model and in lipopolysaccharide (LPS)-induced THP-1 cells. It was demonstrated that GP obviously decreased the expression of Methyl-CpG binding protein 2 (MeCP2) in vivo and in vitro. Knockdown of MeCP2 with siRNA suppressed the expressions of IL-6 and TNF-α, while over-expression of MeCP2 had a proinflammatory effect on the expression of IL-6 and TNF-α in LPS-induced THP-1 cells. Mechanistically, it was indicated that GP had anti-inflammatory effects at least in part, through suppressing MeCP2. Interestingly, GP could attenuate expressions of Sonic hedgehog (Shh) and GLIS family zinc finger 1 (GLIS1) but increase Ptched1 (PTCH1) expression. Similar findings were also demonstrated at the protein level by siRNA MeCP2. Furthermore, over-expression of MeCP2 obviously increased Shh and GLIS1 expressions but reduced PTCH1 expression. Taken together, GP may serve as an effective modulator of MeCP2-hedgehog pathway (Hh)-axis during the pathogenesis of inflammation. Our findings shed light on the potential therapeutic feature of GP in recovering inflammatory diseases. PMID:26371859

  18. Effective 2D-RPLC/RPLC enrichment and separation of micro-components from Hedyotis diffusa Willd. and characterization by using ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry.

    PubMed

    Li, Cunman; Zhao, Yanyan; Guo, Zhimou; Zhang, Xiuli; Xue, Xingya; Liang, Xinmiao

    2014-10-01

    An effective method aiming at enrichment and analysis of micro-components in traditional Chinese medicine (TCM) was developed. One fraction (fraction E) from the extract of Hedyotis diffusa Willd. was selected as test sample, which was isolated by using the XAD-4 macroporous resin. To study the micro-components, a two-dimensional reverse-phase liquid chromatography (2D-RPLC/RPLC) method was developed, comprising Click OEG and C18 stationary phases as the first and second dimensions, respectively. Of the eight sub-fractions isolated from the first dimension, three sub-fractions (fractions II-IV) containing micro-components were further separated with the second dimension. The 2D-RPLC/RPLC system was proved to possess high orthogonality. Furthermore, the micro-components were characterized by using ultra-performance liquid chromatography-diode array detector/quadrupole time-of-flight mass spectrometry (UPLC-DAD/Q-TOF MS) with electrospray ionization (ESI) source. With the optimized separation and characterization method, a large number (>400) of micro-components were enriched and detected from the extracts of H. diffusa Willd., the majority of which has not been isolated from the herb before. Among these isolated micro-components, 38 compounds involving 24 phenylpropanoids, 7 flavonoids and 7 iridoid glucosides (IGs), were identified or tentatively identified from the H. diffusa extracts on the basis of spectral data of the authentic standards and the fragmentation characteristics information available in literatures. The proposed method made it possible to effectively screen and analyze the micro-components in TCMs or other complex natural medicines. PMID:25061712

  19. A review of phytotherapy of gout: perspective of new pharmacological treatments.

    PubMed

    Ling, X; Bochu, W

    2014-04-01

    The purpose of this review article is to outline plants currently used and those with high promise for the development of anti-gout products. All relevant literature databases were searched up to 25 March 2013. The search terms were 'gout', 'gouty arthritis', 'hyperuricemia', 'uric acid', 'xanthine oxidase (XO) inhibitor', 'uricosuric', 'urate transporter 1(URAT1)' and 'glucose transporter 9 (GLUT9)'. Herbal keywords included 'herbal medicine', 'medicinal plant', 'natural products', 'phytomedicine' and 'phytotherapy'. 'antiinflammatory effect' combined with the words 'interleukin-6 (IL-6)', 'interleukin-8 (IL-8)', 'interleukin-1beta (IL-1beta)', and 'tumor necrosis factor alpha (TNF-alpha)'. XO inhibitory effect, uricosuric action, and anti-inflammatory effects were the key outcomes. Numerous agents derived from plants have anti-gout potential. In in vitro studies, flavonoids, alkaloids, essential oils, phenolic compounds, tannins, iridoid glucosides, and coumarins show the potential of anti-gout effects by their XO inhibitory action, while lignans, triterpenoids and xanthophyll are acting through their anti-inflammatory effects. In animal studies, essential oils, lignans, and tannins show dual effects including reduction of uric acid generation and uricosuric action. Alkaloids reveal inhibit uric acid generation, show anti-inflammatory effects, or a combination of the two. Phenolic compounds and flavonoids inhibit uric acid production, show uricosuric anti-inflammatory effects. In the rare human studies, colchicine from Colchicum autumnale showed anti-inflammatory effects while for other plant extracts, although revealing anti-gout potential, further phytochemical investigations are needed to identify their active constituents. Besides, the plants which give antioxidant activities are much potent in the management of gout and need to be further investigated. The current review is a detailed discussion of the potential of medicinal plants for treatment of gout

  20. Phytochemical composition of polar fraction of Stachys germanica L. subsp. salviifolia (Ten.) Gams, a typical plant of Majella National Park.

    PubMed

    Venditti, A; Serrilli, A M; Di Cecco, M; Ciaschetti, G; Andrisano, T; Bianco, A

    2013-01-01

    In this study, we report the isolation and identification of several compounds present in the polar fraction of Stachys germanica L. subsp. salviifolia (Ten.) Gams, collected in the protected area of Majella National Park. In particular, we have isolated and identified harpagide, 7-β-hydroxy-harpagide, ajugol, 5-allosyloxy-aucubin, verbascoside and, for the first time in this genus, arbutin. PMID:22372659