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Iridoid glucosides from Veronica pectinata var. glandulosa.  


A new highly oxygenated iridoid glucoside, urphoside B (1) was isolated from the Veronica pectinata var. glandulosa together with seven known iridoid glucosides, aucubin, catalpol, veronicoside, catalposide, verproside, amphicoside and 6-O-veratroyl catalpol. The planar as well as the stereo structures of the isolated compounds were determined by means of extensive 1D- and 2D-NMR spectroscopy and confirmed by HR-Mass. PMID:12939031

Harput, U Sebnem; Nagatsu, Akito; Ogihara, Yukio; Saracoglu, Iclal


Iridoid glucosides from Plantago cornuti, Plantago major and Veronica cymbalaria  

Microsoft Academic Search

The new iridoid glucoside from the rare ?8,9 type, 10-acetoxymajoroside, was isolated from Plantago cornuti and P. major along with known iridoids. The main constituents in V. cymbalaria were the known catalpol, amphicoside and verproside together with alpinoside, aucubin, 6-O-veratroylcatalpol and verminoside. The iridoid alpinoside with a 8,9-double bond was found for the first time in genus Veronica.

Rilka Taskova; Nedjalka Handjieva; Ljubka Evstatieva; Simeon Popov



Iridoid glucosides of Paederota lutea and the relationships between Paederota and Veronica.  


In a chemical investigation of the water soluble compounds in Paederota lutea eight known iridoids were isolated together with a new one with a 8,9-double bond, namely paederotoside (10-O-benzoyl-6'-O-alpha-arabino(1-->6)-beta-glucopyranosyl arborescosidic acid) and the 6-hydroxy-flavone glucoside 4'-O-methylscutellarein 7-O-beta-glucopyranoside. The known iridoid glucosides were 8-epiloganic acid, gardoside, aucubin, catalpol and the 6-O-esters of catalpol: veronicoside, catalposide, amphicoside and verproside. The compounds isolated show that Paederota has a glycoside content almost identical to that of a general Veronica species, and this is in good agreement with the results from recent investigations of the phylogeny of Veronica and its closest relatives, where Paederota is placed as a sister-group next to Veronica. In an analysis of the iridoid glucosides from some of these relatives, it is shown that Veronica, Paederota, Picrorhiza and Veronicastrum are all characterized by containing 6-O-esters of catalpol. Some less closely related taxa namely: Lagotis, Wulfenia, Plantago, Aragoa and Globularia instead contain 10-O-esters of catalpol or aucubin. PMID:15279984

Albach, Dirk C; Gotfredsen, Charlotte Held; Jensen, Søren Rosendal



In vitro cytotoxic activity and structure activity relationships of iridoid glucosides derived from Veronica species.  


This study was an investigation of the cytotoxic activity of iridoid glucosides, including aucubin, catalpol, 6-O-acetylcatalpol, veronicoside, catalposide, verproside, amphicoside, veratroylcatalposide, verminoside, aquaticosides B and C isolated from different Veronica species. The cytotoxic activity was determined against Hep-2 (human epidermoid carcinoma), RD (human rhabdomyosarcoma), L-20B (transgenic murine L-cells) cancer cell lines and Vero (African green monkey kidney cells) non-cancerous cell line using the MTT method. While verminoside, amphicoside and veronicoside were found to exhibit cytotoxic activity in the concentration range of 70-355?µM, acetylcatalpol, aquaticosides B and C, catalposide, veratroylcatalposide and verproside showed cytostatic activity. Apoptotic cell death was observed as the effect of verminoside in the histological analysis of the tested cell lines. In conclusion, iridoid glucosides are considered to show a biphasic effect on cancer cells that is both cytostatic and cytotoxic, depending on the chemical structure and the type of cancer cell. PMID:21678519

Saracoglu, Iclal; Harput, U Sebnem



Iridoid glucosides with insecticidal activity from Galium melanantherum.  


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

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


Acylated iridoid glucosides from Veronica anagallis-aquatica.  


Three new (1-3) and four known iridoid glucosides (4-7) as well as a known phenylethanoid glycoside (8) were isolated from the aerial parts of Veronica anagallis-aquatica and their structures were determined as 6'-O-benzoyl-8-epiloganic acid named aquaticoside A (1), 6'-O-p-hydroxybenzoyl-8-epiloganic acid named aquaticoside B (2), 6'-O-benzoyl-gardoside named aquaticoside C (3), veronicoside (4), catalposide (5), verproside (6), verminoside (7) and martynoside (8) on the basis of 1D and 2D NMR spectral analysis. PMID:15279985

Harput, U Sebnem; Varel, Mehtap; Nagatsu, Akito; Saracoglu, Iclal



Chlorinated iridoid glucosides from Veronica longifolia and their antioxidant activity.  


From Veronica longifolia were isolated three chlorinated iridoid glucosides, namely, asystasioside E (6) and its 6-O-esters 6a and 6b, named longifoliosides A and B, respectively. The structures of 6a and 6b were proved by analysis of their spectroscopic data and by conversion to the catalpol ester verproside (5a) or to catalpol (5), respectively. The configuration of the previously known vanilloyl analogue, urphoside B, was shown to be the 6?-epimer (6c) of the structure originally reported. Longifoliosides A (6a) and B (6b) were found to exhibit radical-scavenging activity against nitric oxide, superoxide, and 2,2-diphenyl-1-picrylhydrazyl radicals. PMID:20806928

Jensen, Søren R; Gotfredsen, Charlotte H; Harput, U Sebnem; Saracoglu, Iclal



Sequestration of glucosinolates and iridoid glucosides in sawfly species of the genus Athalia and their role in defense against ants.  


In this study, the larval sequestration abilities and defense effectiveness of four sawfly species of the genus Athalia (Hymenoptera: Tenthredinidae) that feed as larvae either on members of the Brassicaceae or Plantaginaceae were investigated. Brassicaceae are characterized by glucosinolates (GLSs), whereas Plantaginaceae contain iridoid glucosides (IGs) as characteristic secondary compounds. Athalia rosae and A. liberta feed on members of the Brassicaceae. Larvae of A. rosae sequester aromatic and aliphatic GLSs of Sinapis alba in their hemolymph, as shown previously, but no indolic GLSs; A. liberta larvae with a narrower host range sequester aliphatic as well as indolic GLSs from their host plant Alliaria petiolata. Larvae of A. circularis and A. cordata are specialized on members of the Plantaginaceae. Athalia circularis utilizes mainly Veronica beccabunga as host plant, whereas A. cordata feeds additionally on Plantago lanceolata. Both sawfly species sequester the IGs aucubin and catalpol. In V. beccabunga, catalpol esters and carboxylated IGs also occur. The high catalpol concentrations in hemolymph of A. circularis can only be explained by a metabolization of catalpol esters and subsequent uptake of the resulting catalpol. The carboxylated IGs of the plant are excreted. The IG-sequestering sawfly species are able to accumulate much higher glucoside concentrations in their hemolymph than the GLS-sequestering species, and the concentration of IGs in hemolymph increases constantly during larval development. The defensive effectiveness of hemolymph that contains GLSs or IGs and of the respective glucosides was tested in feeding-bioassays against a potential predator, the ant Myrmica rubra (Hymenoptera: Formicidae). Hemolymph of IG-sequestering cryptic A. cordata larvae has a higher deterrence potential than hemolymph of the GLS-sequestering conspicuous A. rosae larvae. The results show that glucoside sequestration is widespread in the genus Athalia, but that the specific glucoside uptake can result in different defense effectiveness against a predator species. PMID:20127151

Opitz, Sebastian E W; Jensen, Søren R; Müller, Caroline



Iridoid glucosides from Galium album and G. lovcense  

Microsoft Academic Search

The iridoid composition of Galium album ssp. album, G. album ssp. pychnotrichum and G. lovcense was studied. Eleven known iridoids were isolated and identified. Two new iridoids, 7-O-acetyl-10-acetoxyloganin and 7?-hydroxy-11-methyl forsythide, were isolated from G. lovcense, and their structure elucidated.

Nedjalka Handjieva; Maya Mitova; Mincho Ancev; Simeon Popov



Triterpene saponins and iridoid glucosides from galium rivale.  


Three new glycosides of the oleanene-type triterpenes, rivalosides C-E (1-3), along with three known triterpene saponins, momordin IIb (4) and rivalosides A-B (5-6), and five known iridoid glucosides: monotropein, scandoside, deacetylasperulosidic acid, geniposidic acid and asperulosidic acid, were isolated from aerial parts of Galium rivale. The structures of the new compounds were elucidated by spectral methods and chemical means as 2alpha-acetoxy-3alpha, 19alpha-dihydroxy-olean-12-en-28-oic acid 28-O-beta-D-glucopyranosyl-(1--> 6)-beta-D-glucopyranoside, 2alpha,3alpha, 19alpha-trihydroxy-olean- 12-en-28-oic acid 28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranoside and 3-O-beta-D-glucuronopyranosyl-24-hydroxy-olean-12-en-28-oic acid 28-O-beta-D-glucopyranoside, for rivalosides C-E, respectively. The taxonomic significance of the rivalosides in G. rivale was discussed. PMID:11014260

de Rosa, S; Iodice, C; Mitova, M; Handjieva, N; Popov, S; Anchev, M



The iridoid glucoside, antirrhinoside, from Antirrhinum majus L. has differential effects on two generalist insect herbivores.  


The iridoid glucoside, antirrhinoside, is constitutively distributed throughout Antirrhinum majus L. in a manner consistent with its possible role as an allelochemical, but there is no evidence that it has a defensive function with respect to insect herbivory. To address this question, two generalist herbivores, Lymantria dispar L. (gypsy moth) and Trichoplusia ni Hübner (cabbage looper) were chosen for feeding trials on excised whole leaves of A. majus and in artificial diet assays. In leaf excision feeding trials, fourth instar gypsy moth rejected, without sampling, the leaves of A. majus regardless of what node the leaf was excised from. In contrast, fourth instar cabbage looper readily fed on the excised leaves, and antirrhinoside was not found in their bodies or feces (frass) as determined by thin layer and high-pressure liquid chromatography. In the leaf and diet assays, a second major leaf iridoid in A. majus, antirrhide, was found in both cabbage looper and gypsy moth frass. In diet feeding assays, the growth of gypsy moth and cabbage looper were not inhibited by methanol extracts, iridoid fractions, or pure antirrhinoside at concentrations of 0.6% in diet, but cabbage looper growth was enhanced. At an antirrhinoside concentration of 3.3% in diet, gypsy moth growth was reduced, whereas cabbage looper growth again increased significantly relative to the control. It is likely that antirrhinoside functions as defense against herbivory for one generalist insect herbivore but also, at low concentrations, enhances the growth of another. PMID:18414950

Beninger, Clifford W; Cloutier, Renée R; Grodzinski, Bernard



Glucosides from Vitex agnus-castus.  


The methanolic extract of the flowering stems of Vitex agnus-castus yielded three new iridoids: 6'-O-foliamenthoylmussaenosidic acid (agnucastoside A), 6'-O-(6,7-dihydrofoliamenthoyl)mussaenosidic acid (agnucastoside B) and 7-O-trans-p-coumaroyl-6'-O-trans-caffeoyl-8-epiloganic acid (agnucastoside C) in addition to four known iridoids (aucubin, agnuside, mussaenosidic acid and 6'-O-p-hydroxybenzoylmussaenosidic acid) and one known phenylbutanone glucoside (myzodendrone). The structure elucidations were mainly done by spectroscopic methods (1D and 2D NMR spectra) and MS data interpretation. The purified compounds were tested for biological activities against various microorganisms and cancer cell lines. PMID:12895546

Kuruüzüm-Uz, Ay?e; Ströch, Karsten; Demirezer, L Omür; Zeeck, Axel



Effect of iridoid glucoside on plasma lipid profile, tissue fatty acid changes, inflammatory cytokines, and GLUT4 expression in skeletal muscle of streptozotocin-induced diabetic rats.  


The present study was designed to examine the antihyperlipidaemic potential of iridoid glucoside isolated from Vitex negundo leaves in STZ-induced diabetic rats. The levels of cholesterol (TC), triglycerides, lipoproteins, free fatty acids, phospholipids, fatty acid composition, proinflammatory cytokines, muscle glycogen content, and glucose transporter 4 (GLUT4) expression were estimated in control and diabetic rats. Oral administration of iridoid glucoside at a dose of 50 mg/kg body weight per day to STZ-induced diabetic rats for a period of 30 days resulted in a significant reduction in plasma and tissue (liver and kidney) cholesterol, triglycerides, free fatty acids, and phospholipids. In addition, the decreased plasma levels of high-density lipoprotein-cholesterol and increased plasma levels of low density lipoprotein- and very low density lipoprotein-cholesterol in diabetic rats were restored to near normal levels following treatment with iridoid glucoside. The fatty acid composition of the liver and kidney was analyzed by gas chromatography. The altered fatty acid composition in the liver and kidney of diabetic rats was also restored upon treatment with iridoid glucoside. Moreover, the elevated plasma levels of proinflammatory cytokines and decreased levels of muscle glycogen and GLUT4 expression in the skeletal muscle of diabetic rats were reinstated to their normal levels via enhanced secretion of insulin from the remnant ? cells of pancreas by the administration of iridoid glucoside. The effect produced by iridoid glucoside on various parameters was comparable with that of glibenclamide, a well-known antihyperglycemic drug. PMID:23625195

Sundaram, Ramalingam; Shanthi, Palanivelu; Sachdanandam, Panchanatham



Asymmetric Total Synthesis of the Iridoid ?-Glucoside (+)-Geniposide via Phosphine Organocatalysis  

PubMed Central

Phosphine catalyzed [3+2] cycloaddition of ethyl-2,3-butadienoate with enone (S)-3b occurs with high levels of regio- and stereocontrol to deliver the cis-fused cyclopenta[c]pyran 4 characteristic of the iridoid family of natural products. Cycloadduct 4 was converted to the iridoid glycoside (+)-geniposide in 10 steps.

Jones, Regan A.; Krische, Michael J.



Aquaticol, a bis-sesquiterpene and iridoid glucosides from Veronica anagallis-aquatica.  


Aquaticol, an unusual bis-sesquiterpene was isolated from the medicinal plant Veronica anagallis-aquatica, in addition to 11 known compounds, aucubin, geniposidic acid, mussaenoside, catalposide, verproside, amphicoside, catalpol, boschnaloside, shanzhiside methyl ester, sitosterol and beta-stigmast-4-en-6 beta-ol-3-one. The structure of aquaticol was determined by spectroscopic means and by X-ray crystallographic analysis. PMID:10821060

Su, B N; Yang, L; Gao, K; Jia, Z J



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


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

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



Bioassay-guided isolation of iridoid glucosides with antinociceptive and anti-inflammatory activities from Veronica anagallis-aquatica L.  


Extracts obtained from the herbs of various Veronica species are used as folk remedy worldwide for the treatment of various inflammatory ailments including rheumatism. In vivo anti-inflammatory and antinociceptive activities of Veronica anagallis-aquatica L. aerial parts were investigated. Methanolic extract of the plant was shown to possess significant inhibitory activity against carrageenan-induced hind paw edema model and of p-benzoquinone-induced writhings in mice. Through bioassay-guided fractionation and isolation procedures eight compounds, aquaticoside A (1), aquaticoside B (2), aquaticoside C (3), veronicoside (4), catalposide (5), verproside (6), verminoside (7) and martynoside (8) were isolated and their structures were elucidated by spectral techniques. Catapol derivative iridoid glucosides, verproside (6) and catalposide (5), were found to possess potent antinociceptive and anti-inflammatory activities, per os without inducing any apparent acute toxicity as well as gastric damage. Results of the present study supported the utilization of the plant in Turkish folk medicine. PMID:16019176

Küpeli, Esra; Harput, U Sebnem; Varel, Mehtap; Yesilada, Erdem; Saracoglu, Iclal



Separation and purification of water-soluble iridoid glucosides by high speed counter-current chromatography combined with macroporous resin column separation.  


Four iridoid glucosides, shanzhiside methyl ester, phloyoside II, chlorotuberside, and penstemonoside, were isolated and purified from an herbal medicinal plant for the first time by high-speed counter-current chromatography (HSCCC) using a two-phase solvent system composed of ethyl acetate-n-butanol-water (5:14:12, v/v/v). A total of 37mg of shanzhiside methyl ester, 29mg of phloyoside II, 27mg of chlorotuberside, and 21mg of penstemonoside with the purity of 99.2%, 98.5%, 97.3%, and 99.3%, respectively, were obtained in one-step separation within 4h from 150mg of crude extract. To the best of our knowledge, this is the first report of separation and purification of iridoid glucosides from natural sources by HSCCC. The chemical structures of all the four compounds were identified by ESI-MS, (1)H NMR, and (13)C NMR. PMID:23981483

Yue, Hui-Lan; Zhao, Xiao-Hui; Wang, Qi-Lan; Tao, Yan-Duo



Phenylethanoid and iridoid glycosides from Veronica persica.  


A new phenylethanoid glycoside, persicoside (1) and three known phenylethanoid glycosides, acteoside (2), isoacteoside (3) and lavandulifolioside (4) were isolated from the aerial parts of Veronica persica. On the basis of spectral analyses, the structure of the new compound was elucidated to be 3,4-dihydroxy-beta-phenylethoxy-O-[beta-D-glucopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-4-O-caffeoyl-beta-D-glucopyranoside. Persicoside (1) and acteoside (2) exhibited radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Beside phenylethanoid glycosides, a hexitol, dulcitol (5) and seven known iridoid glucosides, aucubin (6), veronicoside (7), amphicoside (8), 6-O-veratroyl-catalpol (9), catalposide (10), verproside (11) and verminoside (12) were isolated. PMID:12045353

Harput, U Sebnem; Saracoglu, Iclal; Inoue, Makoto; Ogihara, Yukio



Iridoids from Lippia graveolens  

Microsoft Academic Search

An investigation of the leaves of Lippia graveolens from Guatemala provided 10 iridoid and secoiridoid glucosides as well as their ester derivatives. Minor constituents were loganin, secologanin, secoxyloganin, dimethylsecologanoside, loganic acid, 8-epi-loganic acid and caryoptoside. Major constituents were the novel iridoids caryoptosidic acid and lippioside I and II consisting of caryoptosidic acid esterified at the C-6 position of glucose with

L Rastrelli; A Caceres; C Morales; F De Simone; R Aquino



Iridoids from Lippia graveolens.  


An investigation of the leaves of Lippia graveolens from Guatemala provided 10 iridoid and secoiridoid glucosides as well as their ester derivatives. Minor constituents were loganin, secologanin, secoxyloganin, dimethylsecologanoside, loganic acid, 8-epi-loganic acid and caryoptoside. Major constituents were the novel iridoids caryoptosidic acid and lippioside I and II consisting of caryoptosidic acid esterified at the C-6 position of glucose with p-coumaroyl or caffeoyl residues, respectively. Their structures were mainly elucidated by NMR spectroscopy. PMID:11711112

Rastrelli, L; Caceres, A; Morales, C; De Simone, F; Aquino, R



Liquid chromatography-mass spectrometry for the simultaneous determination of the catalpol-related iridoid glucosides, verproside, isovanilloylcatalpol, catalposide and 6-O-veratroyl catalpol in rat plasma.  


Verproside, isovanilloylcatalpol, catalposide and 6-O-veratroyl catalpol are bioactive iridoid glucosides isolated from in a number of folk medicinal plants. A rapid, sensitive and selective liquid chromatography/mass spectrometric (LC/MS) method for the simultaneous determination of verproside, isovanilloylcatalpol, catalposide and 6-O-veratroyl catalpol in rat plasma was developed. The analytes were extracted from 50 microL of rat plasma with ethyl acetate using 7-carboxymethyloxy-3',4',5-trimethoxyflavone as internal standard and analyzed on an X-Bridge C(18) column within 6.5 min with 40% methanol in 10 mm ammonium formate (pH 3.0). The analytes were quantified using an electrospray ionization mass spectrometry in the selected ion monitoring mode. The standard curves were linear over the concentration ranges of 10-2000 ng/mL for verproside, isovanilloylcatalpol and catalposide and 20-2000 ng/mL for 6-O-veratroyl catalpol. The coefficients of variation and relative errors of verproside, isovanilloylcatalpol, catalposide and 6-O-veratroyl catalpol for intra- and inter-assay at four quality control levels were 2.5-8.0 and-4.0-6.6%, respectively. This method was successfully applied to the pharmacokinetic study of verproside and its possible metabolite isovanilloylcatalpol after intravenous administration of verproside, a candidate anti-asthma drug, in male Sprague-Dawley rats. PMID:19353737

Park, Eun Jeong; Oh, Sei-Ryang; Lee, Hyeong-Kyu; Lee, Hye Suk



Iridoid patterns in Galium L. and some phylogenetic considerations.  


From 19 species of Galium, members of 6 European sections of the genus, 24 compounds were isolated, namely 16 iridoid glucosides, 2 secoiridoid glucosides and 6 triterpene saponins (the later found only in G. rivale (Sibth. & Sm. Griseb.) The iridoid content was analyzed by thin layer chromatography - densitometry. An effort was made to clarify interspecies relationships, based on the obtained results and previous data. Generally, a nearly uniform iridoid pattern in the studied species was observed. Nevertheless, some distinctions gave reason the following chemical characters to be treated as taxonomic markers: iridoids, secogalioside (characteristic of G. mollugo group), iridoids V1 and V2 (G. humifusum Bieb. and G. verum L.), 6-acetylscandoside (G. incurvum group and G. verum) and the triterpene saponins, rivalioside A and rivalioside C (characteristic of G. rivale). The studied species regarding to the iridoids could be attributed to three lines of evolutionary differentiation. One line is leading to the differentiation of G. rivale. It contains specific triterpenoids as well as iridoid acids, which show parallel development of both glyceraldehyde 3-phosphate/pyruvate and mevalonate biosynthetic routes in this species. A second line includes G. mollugo and G. incurvum species groups and the species G. humifusum and G. verum. Variety of iridoid esters, hydroxy and carboxy derivatives of iridoids and secoiridoids characterised this line. Third line comprises the remaining studied species, members of different sections and species groups. They posses a nearly identical iridoid pattern, which suggests a convergent evolution regarding to the iridoids. PMID:12064718

Mitova, Maya Iv; Anchev, Mincho E; Handjieva, Nedjalka V; Popov, Simeon S


Extraction of iridoid glycosides and their determination by micellar electrokinetic capillary chromatography  

Microsoft Academic Search

Several methods for the extraction of two iridoid glycosides, catalpol and aucubin, from the plant matrix (Veronica longifolia leaves) were compared. Pressurized hot water extraction and hot water extraction were the most efficient isolation techniques for both. Pressurized liquid extraction and maceration with various organic solvents were also tested. Relative to the amounts extracted with hot water, ethanol extracted only

Johanna Suomi; Heli Sirén; Kari Hartonen; Marja-Liisa Riekkola



Iridoid-specific glucosyltransferase from Gardenia jasminoides.  


Iridoids are one of the most widely distributed secondary metabolites in higher plants. They are pharmacologically active principles in various medicinal plants and key intermediates in the biosynthesis of monoterpenoid indole alkaloids as well as quinoline alkaloids. Although most iridoids are present as 1-O-glucosides, the glucosylation step in the biosynthetic pathway has remained obscure. We isolated a cDNA coding for UDP-glucose:iridoid glucosyltransferase (UGT85A24) from Gardenia jasminoides. UGT85A24 preferentially glucosylated the 1-O-hydroxyl group of 7-deoxyloganetin and genipin but exhibited only weak activity toward loganetin and no activity toward 7-deoxyloganetic acid. This suggests that, in the biosynthetic pathway of geniposide, a major iridoid compound in G. jasminoides, glucosylation occurs after methylation of 7-deoxyloganetic acid. UGT85A24 showed negligible activity toward any acceptor substrates other than iridoid aglycones. Thus, UGT85A24 has a remarkable specificity for iridoid aglycones. The mRNA level of UGT85A24 overlaps with the marked increase in genipin glucosylation activity in the methyl jasmonate-treated cell cultures of G. jasminoides and is related to iridoid accumulation in G. jasminoides fruits. PMID:21799001

Nagatoshi, Mai; Terasaka, Kazuyoshi; Nagatsu, Akito; Mizukami, Hajime



Effect of hostplant genotype and predators on iridoid glycoside content of pupae of a specialist insect herbivore, Junonia coenia (Nymphalidae)  

Microsoft Academic Search

Two field experiments assessed the effects of hostplant genotype, presence or absence of predators, and type of predator on chemical content of pupae of the Buckeye butterfly, Junonia coenia (Nymphalidae). When fed Plantago lanceolata (Plantaginaceae), J. coenia larvae sequester two iridoid glycosides, aucubin and catalpol, which are retained into the pupal stage. In the first experiment, it is found that

M. Deane Bowers; Nancy E. Stamp



Shoot regeneration and determination of iridoid levels in the medicinal plant Castilleja tenuiflora Benth  

Microsoft Academic Search

Castilleja tenuiflora is a medicinal plant that grows in pine–oak woods primarily in southern and central Mexico. It is highly valued for its medicinal\\u000a properties, which have been attributed to aucubin-like iridoids. In the present study, we developed an efficient protocol\\u000a for in vitro shoot proliferation and ex vitro rooting of C. tenuiflora. Using a colorimetric method, we determined total

Blanca P. Martínez-Bonfil; Guadalupe Salcedo-Morales; Alma R. López-Laredo; Elsa Ventura-Zapata; Silvia Evangelista-Lozano; Gabriela Trejo-Tapia


Antiinflammatory activities of Hungarian Stachys species and their iridoids.  


The antiinflammatory activities of aqueous extracts prepared from the aerial parts of ten Hungarian Stachys species were investigated in vivo in the carrageenan-induced paw oedema test after intraperitoneal and oral administration to rats. Some of the extracts were found to display significant antiphlogistic effects when administered intraperitoneally and orally; in particular, the extracts of S. alpina, S. germanica, S. officinalis and S. recta demonstrated high activity following intraperitoneal administration. At the same dose of 5.0 mg/kg, these extracts exhibited similar or greater potency than that of the positive control diclofenac-Na. The main iridoids present in the investigated extracts, ajugoside, aucubin, acetylharpagide, harpagide and harpagoside, were also assayed in the same test, and high dose-dependent antiphlogistic effects were recorded for aucubin and harpagoside. These results led to the conclusion that most probably iridoids are responsible for the antiinflammatory effect of Stachys species, but other active constituents or their synergism must also be implicated in the antiinflammatory effect. PMID:21887806

Háznagy-Radnai, Erzsébet; Balogh, Ágnes; Czigle, Szilvia; Máthé, Imre; Hohmann, Judit; Blazsó, Gábor



Influence of iridoid glycoside containing host plants on midgut ?-glucosidase activity in a polyphagous caterpillar, Spilosoma virginica Fabricius (Arctiidae).  


Iridoid glycosides are secondary plant compounds that have deterrent, growth reducing or even toxic effects on non-adapted herbivorous insects. To investigate the effects of iridoid glycoside containing plants on the digestive metabolism of a generalist herbivore, larvae of Spilosoma virginica (Lepidoptera: Arctiidae) were reared on three plant species that differ in their secondary plant chemistry: Taraxacum officinale (no iridoid glycosides), Plantago major (low iridoid glycoside content), and P. lanceolata (high iridoid glycoside content). Midguts of fifth instar larvae were assayed for the activity and kinetic properties of ?-glucosidase using different substrates. Compared to the larvae on T. officinale, the ?-glucosidase activity of larvae feeding on P. lanceolata was significantly lower measured with 4-nitrophenyl-?-d-glucopyranoside. Using the iridoid glycoside aucubin as a substrate, we did not find differences in the ?-glucosidase activity of the larvae reared on the three plants. Heat inactivation experiments revealed the existence of a heat-labile and a more heat-stable ?-glucosidase with similar Michaelis constants for 4-nitrophenyl-?-d-glucopyranoside. We discuss possible mechanisms leading to the observed decrease of ?-glucosidase activity for larvae reared on P. lanceolata and its relevance for generalist herbivores in adapting to iridoid glycoside containing plant species and their use as potential host plants. PMID:20727899

Pankoke, Helga; Bowers, M Deane; Dobler, Susanne



Loasafolioside, a minor iridoid dimer from the leaves of Loasa acerifolia 1 The investigation here presented is part of a joint venture between the Institute of Systematic Botany and the Institute of Pharmaceutical Biology, Munich, for the investigation of the biology and systematics of Loasaceae and a screening program for antiinflammatory plant drugs from ethnopharmacology. 1  

Microsoft Academic Search

In continuation of our phytochemical studies on Loasa acerifolia Dombey, Loasaceae, a further novel dimeric iridoid glucoside named loasafolioside, 1, was isolated from the leaves. The structure of 1 is similar to the recently isolated iridoid dimer, asaolaside, but owns an hemiacetalic group at position 3 of unit b. Compound 1 exists as an isomeric mixture like the iridoid dimer,

Andreas A Müller; Maximilian Weigend



Two herbivore-deterrent iridoid glycosides reduce the in-vitro growth of a specialist but not of a generalist pathogenic fungus of Plantago lanceolata L  

Microsoft Academic Search

Summary.   Many secondary plant compounds are involved in defense against both insect herbivores and pathogens. Two secondary plant\\u000a compounds of Plantago lanceolata, the iridoid glycosides catalpol and its precursor aucubin, are well known for their deterrent effects on generalist and\\u000a non-adapted specialist insect herbivores. We tested the effects of these compounds on the in-vitro growth of a specialist\\u000a and generalist

Hamida B. Marak; Arjen Biere; Jos M. M. van Damme



Implication of HMGR in homeostasis of sequestered and de novo produced precursors of the iridoid biosynthesis in leaf beetle larvae.  


Insects employ iridoids to deter predatory attacks. Larvae of some Chrysomelina species are capable to produce those cyclopentanoid monoterpenes de novo. The iridoid biosynthesis proceeds via the mevalonate pathway to geranyl diphospate (GDP) subsequently converted into 8-hydroxygeraniol-8-O-beta-D-glucoside followed by the transformation into the defensive compounds. We tested whether the glucoside, its aglycon or geraniol has an impact on the activity of 3-hydroxy-3-methylglutaryl-CoA reductase (HMGR), the key regulatory enzyme of the mevalonate pathway and also the iridoid biosynthesis. To address the inhibition site of the enzyme, initially a complete cDNA encoding full length HMGR was cloned from Phaedon cochleariae. Its catalytic portion was then heterologously expressed in Escherichia coli. Purification and characterization of the recombinant protein revealed attenuated activity in enzyme assays by 8-hydroxygeraniol whereas no effect has been observed by addition of the glucoside or geraniol. Thus, the catalytic domain is the target for the inhibitor. Homology modeling of the catalytic domain and docking experiments demonstrated binding of 8-hydroxygeraniol to the active site and indicated a competitive inhibition mechanism. Iridoid producing larvae are potentially able to sequester glucosidically bound 8-hydroxygeraniol whose cleavage of the sugar moiety results in 8-hydroxygeraniol. Therefore, HMGR may represent a regulator in maintenance of homeostasis between de novo produced and sequestered intermediates of iridoid metabolism. Furthermore, we demonstrated that HMGR activity is not only diminished in iridoid producers but most likely prevalent within the Chrysomelina subtribe and also within the insecta. PMID:18070667

Burse, Antje; Frick, Sindy; Schmidt, Axel; Buechler, Rita; Kunert, Maritta; Gershenzon, Jonathan; Brandt, Wolfgang; Boland, Wilhelm



Protective effects of aucubin isolated from Eucommia ulmoides against UVB-induced oxidative stress in human skin fibroblasts.  


Ultraviolet-B (UVB) irradiation has been demonstrated to produce reactive oxygen species (ROS) in the cells and skin, which induces the synthesis of matrix metalloproteinases (MMPs), causing skin photoaging. Using the human skin fibroblast HS68 cell line in the present study, we investigated the photoprotective effects of aucubin from Eucommia ulmoides. Pretreatment with aucubin significantly inhibited the production of MMP-1 by 57% when compared to the UVB-irradiated cells. Additionally, the senescence-associated beta-galactosidase (SA beta-gal) activity was markedly decreased in the presence of aucubin, which indicates it as an antiphoto-induced aging compound. As the effect of aucubin was determined against ROS, the inhibited ROS formation and malondialdehyde (MDA) levels, and the increased cell viability and glutathione (GSH) level were observed with aucubin under UVB irradiation. Based upon these results, it was suggested that aucubin might play an important role in the cellular defense mechanism against UV radiation-induced photoaging. An understanding of the antioxidant properties of aucubin could, in part, act to elucidate its protective mechanism on the human skin photoaging. PMID:15997107

Ho, Jin Nyoung; Lee, Yoo Hyun; Park, Jong Seok; Jun, Woo Jin; Kim, Hye Kyung; Hong, Bum Shik; Shin, Dong Hoon; Cho, Hong Yon



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


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 ?-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 ?-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 ?-glucosidase activity, should be highest in younger leaves and decrease with increasing leaf age. Both species possessed ?-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 ?-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 ?-glucosidase interact in a dual defense system. PMID:23773298

Pankoke, Helga; Buschmann, Torsten; Müller, Caroline



The interplay between toxin-releasing ?-glucosidase and plant iridoid glycosides impairs larval development in a generalist caterpillar, Grammia incorrupta (Arctiidae).  


Herbivores with polyphagous feeding habits must cope with a diet that varies in quality. One of the most important sources of this variation in host plant suitability is plant secondary chemistry. We examined how feeding on plants containing one such group of compounds, the iridoid glycosides, might affect the growth and enzymatic activity in a polyphagous caterpillar that feeds on over 80 plant species in 50 different families. Larvae of the polyphagous arctiid, Grammia incorrupta, were reared exclusively on one of two plant species, one of which contains iridoid glycosides (Plantago lanceolata, Plantaginaceae) while the other does not (Taraxacum officinale, Asteraceae). Larval weight was measured on the two host plants, and midgut homogenates of last instar larvae were then assayed for activity and kinetic properties of ?-glucosidases, using both a standard substrate, 4-nitrophenyl-?-D-glucose (NP?Glc), and the iridoid glycoside aucubin, one of the two main iridoid glycosides in P. lanceolata. Larvae feeding on P. lanceolata weighed significantly less and developed more slowly compared to larvae on T. officinale. While the larval midgut ?-glucosidase activity determined with NP?Glc was significantly decreased when fed on P. lanceolata, aucubin was substantially hydrolyzed and the larval ?-glucosidase activity towards both substrates correlated negatively with larval weight. Our results demonstrate that host plants containing high concentrations of iridoid glycosides have a negative impact on larval development of this generalist insect herbivore. This is most likely due to the hydrolysis of plant glycosides in the larval midgut which results in the release of toxic aglycones. Linking the reduced larval weight to the toxin-releasing action of an iridoid glycoside cleaving ?-glucosidase, our results thus support the detoxification limitation hypothesis, suggesting fitness costs for the larvae feeding solely on P. lanceolata. Thus, in addition to the adaptive regulation of midgut ?-glucosidase activity, host plant switching as a behavioral adaptation might be a prerequisite for generalist herbivores that allows them to circumvent the negative effects of plant secondary compounds. PMID:22446106

Pankoke, Helga; Bowers, M Deane; Dobler, Susanne



Anti-Inflammatory Activity of Iridoids and Verbascoside Isolated from Castilleja tenuiflora.  


Castilleja tenuiflora (Orobanchaceae) has been used in Mexican traditional medicine as a treatment for cough, dysentery, anxiety, nausea and vomiting as well as hepatic and gastrointestinal diseases. The ethanolic extract of the aerial parts of Castilleja tenuiflora was separated by silica gel column chromatography. The fractions were evaluated using the induced edema acetate 12-O-tetradecanoylphorbol (TPA) anti-inflammatory activity model. The most active fraction was subjected to medium-pressure liquid chromatography (MPLC) with UV detection at 206 and 240 nm. The following iridoids were isolated: geniposidic acid, aucubin, bartioside, 8-epi-loganin, mussaenoside, and the phenylpropanoid verbascoside. The most active iridoid was geniposidic acid, which was more active than the control (indomethacin), and the least active iridoid was mussaenoside. 8-epi-Loganin, and mussaenoside have not been previously reported to be anti-inflammatory compounds. The results of these investigations confirm the potential of Mexican plants for the production of bioactive compounds and validate the ethnomedical use of Castilleja tenuiflora-like anti-inflammatory plants. PMID:24084016

Carrillo-Ocampo, Danae; Bazaldúa-Gómez, Sugeyla; Bonilla-Barbosa, Jaime R; Aburto-Amar, Rola; Rodríguez-López, Verónica



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


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

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



Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana.  


From the aerial parts of Veronica turrilliana two phenylethanoid glycosides, turrilliosides A and B and a steroidal saponin, turrillianoside were isolated and their structures elucidated as beta-(3,4-dihydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[beta-glucopyranosyl-(1-->4)-alpha-rhamnopyranosyl-(1-->6)]-beta-glucopyranoside, beta-(3,4-dihydroxyphenyl)ethyl-4-O-E-caffeoyl-[6-O-E-feruloyl-beta-glucopyranosyl-(1-->4)-alpha-rhamnopyranosyl-(1-->6)]-beta-glucopyranoside and (23S,25S)-12beta,23-dihydroxyspirost-5-en-3beta-yl O-alpha-rhamnopyranosyl-(1-->4)-beta-glucopyranoside, respectively. Furthermore, eight known glucosides are reported namely, catalpol, catalposide, verproside, amphicoside, isovanilloylcatalpol, aucubin, arbutin, and 6-O-E-caffeoylarbutin, the latter two for the first time in the genus Veronica. The two phenylethanoid glycosides were found to be potent DPPH radical scavengers. All of the tested compounds were inactive against the representative species of fungi and bacteria. PMID:17399747

Kostadinova, Emanuela P; Alipieva, Kalina I; Kokubun, Tetsuo; Taskova, Rilka M; Handjieva, Nedjalka V



Biological and pharmacological activity of naturally occurring iridoids and secoiridoids.  


The biological and pharmacological activities reported for naturally occurring iridoids and secoiridoids are reviewed. The hypothesis that iridoid glycoside and acetal esters can best be considered as pro-drugs and that corresponding hemiacetals and compounds derived from them carry the pharmacophores is discussed. The possibility that the activity of some iridoids is determined by their conversion to pyridine monoterpene alkaloids (PMTA) is also considered. The evidence available suggests that iridoids show activities consistent with those presented by immunomodulators and adaptogens. PMID:23195768

Ghisalberti, E L



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


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

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



Anti-inflammatory iridoids of botanical origin.  


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

Viljoen, A; Mncwangi, N; Vermaak, I



Glucosides from Curculigo orchioides.  


From the rhizomes of Curculigo orchioides two phenolic glucosides named orchiosides A and B were isolated besides four known compounds and their structures were elucidated by the combination of 2D-NMR analysis, mass spectrometry and chemical evidences. PMID:15771886

Gupta, Moumita; Achari, Basudeb; Pal, Bikas C



Biological and pharmacological activities of iridoids: recent developments.  


Iridoids represent a large group of cyclopenta[c]pyran monoterpenoids that occur wide-spread in nature, mainly in dicotyledonous plant families like Apocynaceae, Scrophulariaceae, Diervillaceae, Lamiaceae, Loganiaceae and Rubiaceae. Recently, more extensive studies revealed that iridoids exhibit a wide range of bioactivity, such as neuroprotective, antinflammatory and immunomodulator, hepatoprotective and cardioprotective effects. Anticancer, antioxidant, antimicrobic, hypoglycaemic, hypolipidemic, choleretic, antispasmodic and purgative properties were also reported. The aim of the present review is to discuss the recent developments on biological and pharmacological activities of iridoids, supporting the new therapeutic possibilities for the use of these compounds. PMID:18473930

Tundis, Rosa; Loizzo, Monica R; Menichini, Federica; Statti, Giancarlo A; Menichini, Francesco



Macedonine, a non-glycosidic iridoid from Galium macedonicum  

Microsoft Academic Search

A new non-glycosidic iridoid, macedonine, was isolated from Galium macedonicum. The structure, stereochemistry and conformation were determined by spectral methods and molecular mechanics calculations. Macedonine lacks the 3,4-double bond and the C-1 substituent.

Maya Mitova; Nedjalka Handjieva; Stefan Spassov; Simeon Popov



The iridoid pathway in Catharanthus roseus alkaloid biosynthesis  

Microsoft Academic Search

The Apocynaceae Catharanthus roseus accumulates a number of monoterpene indole alkaloids (MIAs) that originate from the coupling of the indole and the iridoid\\u000a pathways. The latter pathway is usually considered as limiting for MIA biosynthesis, but evidence is now strong that the precursors\\u000a tryptamine (from the indole pathway) and secologanin (from the iridoid pathway) have to be provided within the

Audrey Oudin; Martine Courtois; Marc Rideau; Marc Clastre



Host plant influences on iridoid glycoside sequestration of generalist and specialist caterpillars.  


The effect of diet on sequestration of iridoid glycosides was examined in larvae of three lepidopteran species. Larvae were reared upon Plantago major, or P. lanceolata, or switched from one to the other in the penultimate instar. Junonia coenia is a specialist on iridoid glycoside-producing plants, whereas the arctiids, Spilosoma congrua and Estigmene acrea, are both polyphagous and eat iridoid-producing plants. All species sequestered iridoids. The specialist J. coenia sequestered from three to seven times the amounts sequestered by the two generalist species. Junonia coenia iridoid glycoside content depended on diet, and they sequestered from 5 to 15% dry weight iridoid glycosides. Estigmene acrea iridoid glycoside sequestration was relatively low, around 2% dry weight and did not vary with diet. Spilosoma congrua sequestration varied with diet and ranged from approximately 3 to 6% dry weight. PMID:20809144

Lampert, Evan C; Bowers, M Deane



Stilbene C-glucosides from Cissus repens.  


Four new stilbene C-glucosides, namely trans-3-O-methyl-resveratrol-2-C-beta-glucoside (1), cis-3-O-methyl-resveratrol-2-C-beta-glucoside (2), trans-3-O-methyl-resveratrol-2-(2-p-coumaric)-C-beta-glucoside (cissuside A) (3), and trans-3-O-methyl-resveratrol-2-(3-p-coumaric)-C-beta-glucoside (cissuside B) (4), were isolated from the aerial parts of Cissus repens, along with known trans-resveratrol (5), trans-resveratrol-2-C-beta-glucoside (6) and cis-resveratrol-2-C-beta-glucoside (7). Their structures were established by spectroscopic methods. Stilbene C-glucosides were found in the genus Cissus for the first time. PMID:17943557

Wang, Y-H; Zhang, Z-K; He, H-P; Wang, J-S; Zhou, H; Ding, M; Hao, X-J


Monoterpene glucosides from Origanum syriacum.  


From the aerial parts of Origanum syriacum, three new monoterpene glucosides thymoquinol 2,5-O-beta-diglucopyranoside (3), carvacrol 2-O-beta-glucopyranosyl-(1-->2)-beta-glucopyranoside (4) and p-menth-1-ene-3,4-diol 4-O-beta-glucopyranoside (5) together with two known monoterpene glucosides thymoquinol 2-O-beta-glucopyranoside (1), thymoquinol 5-O-beta-glucopyranoside (2) have been isolated. The structures of the isolated compounds were verified by means of MS and NMR spectral analyses. PMID:11738398

Kamel, M S; Assaf, M H; Hasanean, H A; Ohtani, K; Kasai, R; Yamasaki, K



Glucosides from the roots of Capparis tenera.  


Two new lignan glucosides, compounds 2 and 3, two new 1H-indole-alkaloid glucosides, 5 and 6, as well as two new phenolic glucosides, 7 and 10, were isolated from the roots of Capparis tenera, together with five known compounds. Their structures were characterized by chemical and spectroscopic methods. Most of these isolates were obtained for the first time from Capparidaceae. The antioxidant and anti-inflammatory activities of the new compounds were investigated. PMID:18081096

Su, Dong-Min; Wang, Ying-Hong; Yu, Shi-Shan; Yu, De-Quan; Hu, You-Cai; Tang, Wen-Zhao; Liu, Geng-Tao; Wang, Wen-Jie



Enzymatic synthesis of novel phloretin glucosides.  


A UDP-glycosyltransferase from Bacillus licheniformis was exploited for the glycosylation of phloretin. The in vitro glycosylation reaction confirmed the production of five phloretin glucosides, including three novel glucosides. Consequently, we demonstrated the application of the same glycosyltransferase for the efficient whole-cell biocatalysis of phloretin in engineered Escherichia coli. PMID:23542617

Pandey, Ramesh Prasad; Li, Tai Feng; Kim, Eun-Hee; Yamaguchi, Tokutaro; Park, Yong Il; Kim, Joong Su; Sohng, Jae Kyung



Downstream processing of enzymatically produced geranyl glucoside.  


Geraniol plays an important role in the fragrance and flavor industry. The corresponding glucoside has interesting properties as a "slow release" aroma compound. Therefore, the enzymatic production and downstream processing of geranyl glucoside were investigated. Geranyl glucoside was produced in a spray column reactor with an initial production rate of 0.58 mg x U(-1) x h(-1). A pretreated hydrophobic microfiltration membrane was used to prevent migration of the aqueous, enzyme-containing phase to the downstream process. No retention of the glucoside, which accumulated in the geraniol phase, was found. On the basis of examples from the literature, four downstream processes were tested on their viability for this system. Extraction with water and foaming were not suitable to recover geranyl glucoside from geraniol. In the first case, the glucoside selectivity for the geraniol phase was found to be high, which made extraction with water unsuccessful. In the second case it was possible to obtain a stable foam, but significant enrichment of the foam with glucoside did not occur. Adsorption on alumina and distillation under reduced pressure were applied successfully and tested in-line with the bioreactor. A maximum glucoside adsorption of 7.86 mg x g(-1) was achieved on alumina. After desorption and evaporation of the extractant the pure glucoside was obtained quantitatively. A pure product could not be obtained after distillation because a small amount of glucose was present in the permeate as well, which accumulated in the bottom fraction. It was shown that with this reactor system a production of 1 kg of geranyl glucoside in 2 days is possible using an initial amount of 50,000 units of enzyme. PMID:11587579

de Roode, B M; Oliehoek, L; van der Padt, A; Franssen, M C; Boom, R M


New humantenine-type indole alkaloids with iridoid unit from Gelsemium species  

Microsoft Academic Search

Two new oxindole alkaloids, rankiniridine (1) and humanteniridine (2), having a nitrogen–carbon linkage between a humantenine-type monoterpenoid indole alkaloid and a monoterpene unit with an iridoid skeleton, were isolated from Gelsemium rankinii and Gelsemium elegans, respectively.

Noriyuki Kogure; Hiromi Kobayashi; Naoko Ishii; Mariko Kitajima; Sumphan Wongseripipatana; Hiromitsu Takayama



Minor iridoids from Scutellaria albida ssp. albida. Inhibitory potencies on lipoxygenase, linoleic acid lipid peroxidation and antioxidant activity of iridoids from Scutellaria sp.  


A new iridoid glycoside, 6'-O-E-caffeoyl-mussaenosidic acid , in addition to one known aglycon, four known triterpenes and one known flavonoid, were isolated from the aerial parts of Scutellaria albida subsp. albida. Furthermore, 12 iridoids with similar structures isolated from Scutellaria sp., were examined for their inhibitory potency on lipoxygenase and lipid peroxidation, as well as their antioxidant activity, in comparison to known antioxidants e.g. caffeic acid, nordihydroguaretic acid (NDGA) and trolox. AAPH, DPPH and soybean lipoxygenase (LOX) assays were used for the tests. This investigation led to interesting observations considering the Structure-Activity Relationship. According to our results, the presence of a p-coumaroyl group optimized and even dramatically changed the biological responses of the investigated iridoids. PMID:22630074

Gousiadou, Chrysoula; Gotfredsen, Charlotte H; Matsa, Marina; Hadjipavlou-Litina, Dimitra; Skaltsa, Helen



An orsellinic acid glucoside from syzygium aromatica  

Microsoft Academic Search

The buds of Syzygium aromatica yielded two triterpenoid acids, oleanolic acid and crategolic acid, and a new phenolic glucoside, orsellinic-2-O-?-d-glucopyranoside, from its methanolic extract. The structure was elucidated by spectroscopic methods and acid hydrolysis.

Reena Charles; Shri Niwas Garg; Sushil Kumar



Inducible System for the Utilization of ?-Glucosides in Escherichia coli I. Active Transport and Utilization of ?-Glucosides1  

PubMed Central

Wild-type Escherichia coli strains (?-gl?) do not split ?-glucosides, but inducible mutants (?-gl+) can be isolated which do so. This inducible system consists of a ?-glucoside permease and an aryl ?-glucoside splitting enzyme. Both can be induced by aryl and alkyl ?-glucosides. In ?-gl? and noninduced ?-gl+ cells, C14-labeled thioethyl ?-glucoside (TEG) is taken up by a constitutive permease, apparently identical with a glucose permease (GP). This permease has a high affinity for ?-methyl glucoside and a low affinity for aryl ?-glucosides. No accumulation of TEG occurs in a ?-gl? strain lacking glucose permease (GP?). In induced ?-gl+ strains, there appears a second ?-glucoside permease with low affinity for ?-methyl glucoside and high affinity for aryl ?-glucosides. Autoradiography shows that TEG is accumulated by the ?-glucoside permease and glucose permease in two different forms (one being identical with TEG, the other probably phosphorylated TEG). In GP+ ?-gl+ strains with high GP activity, alkyl ?-glucosides induce the enzyme and the ?-glucoside permease after a prolonged induction lag, and they competitively inhibit the induction by aryl ?-glucosides. The induction lag and competition do not exist in GP? ?-gl+ strains. It is assumed that phosphorylated alkyl and thioalkyl ?-glucosides inhibit the induction, and that this inhibition is responsible for the induction lag.

Schaefler, S.



Acylated iridoids from the roots of Valeriana officinalis var. latifolia.  


Phytochemical investigation of the roots of Valeriana officinalis var. latifolia resulted in the isolation and characterization of six new acylated iridoids, (5S,7S,8S,9S)-7-hydroxy-8-isovaleroyloxy-??,¹¹-dihyronepetalactone (1), (5S,7S,8S,9S)-7-hydroxy-10-isovaleroyloxy-??,¹¹-dihyronepetalactone (2), (5S,8S,9S)-10-isovaleroyloxy-??,¹¹-dihyronepetalactone (3), (5S,6S,8S,9R)-6-isovaleroyloxy-??,¹¹-1,3-diol (4), (5S,6S,8S,9R)-1,3-isovaleroxy-?4,11-1,3-diol (5), and (5S,6S,8S,9R)-3-isovaleroxy-6-isovaleroyloxy-??,¹¹-1,3-diol (6). Their structures were determined mainly by 1D and 2D?NMR spectroscopic techniques. We also report herein for the first time the single crystal X-ray structure of compound 1. In addition, the cytotoxic activities of compounds 1-6 were evaluated against A549 (human lung adenocarcinoma), HCT116 (human colon carcinoma), SK-BR-3 (human breast carcinoma), and HepG2 (human hepatoma) cell lines. Compound 6 showed weak cell growth inhibition of A549, HCT116, SK-BR-3, and HepG2 cells. PMID:22872588

Han, Zhu-zhen; Yan, Zhao-hui; Liu, Qing-xin; Hu, Xian-qing; Ye, Ji; Li, Hui-liang; Zhang, Wei-dong



Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina.  


Eight iridoid glycosides and four phenolic compounds were isolated from the EtOAc soluble fraction of Veronica peregrina MeOH extract as the radical scavengers for antioxidant activity. The compounds were identified as protocatechuic acid (1), luteolin (2), veronicoside (3), minecoside (4), specioside (5), amphicoside (6), catalposide (7), 6-O-cis-p-coumaroyl catalpol (8), p-hydroxy benzoic acid methyl ester (9), verproside (10), verminoside (11), and chrysoeriol 7-glucuronide (12) by spectroscopic analysis. All compounds except for 1 and 2 were isolated for the first time from this plant. The antioxidant activity was evaluated by the ORAC(Oxygen Radical Absorbance Capacity) assay, which measures scavenging activity against peroxy radicals induced by 2,2'-azobis (2-methoxypropion-amidine) dihydrochloride, and the ORAC value is expressed as relative trolox equivalent. Compounds 2, 4, 5, 6, 8, and 12 exhibited potent antioxidant activity, and compounds 1, 11 had similar activity with trolox, whereas the other compounds showed weaker activity than trolox. PMID:19280150

Kwak, Jong Hwan; Kim, Hyun Jung; Lee, Kwang Ho; Kang, Se Chan; Zee, Ok Pyo



Lignan bis-glucosides from Galium sinaicum  

Microsoft Academic Search

The new lariciresinol-based lignan bis-glucosides, 7S,8R,8?R-(?)-lariciresinol-4,4?-bis-O-?-d-glucopyranoside and 7S,8R,8?R-(?)-5-methoxylariciresinol-4,4?-bis-O-?-d-glucopyranoside, together with (?)-syringaresinol-4,4?-bis-O-?-d-glucopyranoside were isolated from the n-butanol extract of Galium sinaicum roots and their structures were established by various spectroscopic techniques. The isolated compounds represent the first report of lignan glycosides from the Rubiaceae. The two lariciresinol-type glucosides exhibited weak cytotoxic activity against the P388 cell line.

A. A. El Gamal; K. Takeya; H. Itokawa; A. F. Halim; M. M. Amer; H.-E. A. Saad



Investigation of iridoid substances in Arctostaphylos uva-ursi.  


Active principles of bearberry have been studied for several decades. The drug Folium uvae-ursi is useful to the pharmaceutical industry (in production of medicinal teas) for its disinfective effect on the urinary tract which is derived from the content of phenolic glucosides. This work is a part of the total evaluation of the drug from the point of view of contents of active principles, biogenesis, isolation, qualitative and quantitative differences during the vegetative period, and the changes during technological treatment and pharmacological activity of its active principles. PMID:569336

Jahodár, L; Leifertová, I; Lisá, M



Iridoidic pattern in endemic Sardinian plants: the case of Galium species.  


The monoterpenoid fractions of three endemic Galium ssp. (Rubiaceae) from Sardinia Island were examined and compared with the iridoidic pattern yet known in Galium species. This comparison evidenced theirs endemic characters. In particular, in G.corsicum and in G. glaucophyllum loganic acid was isolated and identified for the first time in Galium genus. In G. schmidii a rare iridoid is present, 10-hydroxy-loganin, whose presence in this genus was evidenced only in G. mollugo and loganin isolated for the first time. PMID:18569700

Serrilli, Anna Maria; Ramunno, Alessia; Amicucci, Francesca; Chicarella, Valentina; Santoni, Sabrina; Ballero, Mauro; Serafini, Mauro; Bianco, Armandodoriano



A divergent approach to the diastereoselective synthesis of several ant-associated iridoids.  


The ant-associated iridoids nepetalactol, actinidine, dolichodial, isoiridomyrmecin, and dihydronepetalactone were prepared from citronellal using a divergent approach. Key features include a three-step synthesis of the individual antipodes of actinidine by a novel tandem cycloaddition/pyridine formation and a facile diastereoselective synthesis of both enantiomers of dolichodial. PMID:20222691

Beckett, Joel S; Beckett, James D; Hofferberth, John E



Biosynthesis of Cholesteryl Glucoside by Mycoplasma gallinarum  

PubMed Central

The biosynthesis of cholesteryl glucoside by Mycoplasma gallinarum strain J proceeds by the transfer of glucose from uridine-5?-diphosphoglucose to membrane-bound sterol. Galactose also can be coupled to cholesterol via uridine-5?-diphosphogalactose. The reaction is specific for the uridine-5?-diphospho sugars. Enzymatic activity is associated with the membrane. Treatment of the membrane to remove endogenous sterol inactivates the enzyme. Only sterol which has been bound to the membrane participates in the reaction. The optimum pH is about 8.0, and Mg2+ is required. The reaction is unaffected by nucleotide triphosphate, uridine-5?-monophosphate, and uridine-5?-diphosphate. Reduction of pH to the optimum for ?-glucosidase in the membrane results in loss of synthesized glucoside. The enzyme is saturated at 0.5 mm uridine-5?-diphosphoglucose. The apparent Km of 2.05 × 10?7 indicates a high affinity of the enzyme for the nucleotide sugar.

Smith, Paul F.



Lignan Glucosides from Sinomenium acutum Rhizomes.  


The new lignan glucoside, acutumoside (1), was isolated from Sinomenium acutum rhizomes together with nine known compounds (2-10). The structure of 1 was elucidated on the basis of extensive spectroscopic analyses, including two-dimensional nuclear magnetic resonance and chemical reactions. Compounds 2, 7, 8, and 10 displayed potential antiproliferative activity against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines, while compound 1 showed weak activity against these human tumor cells. PMID:24096673

Kim, Ki Hyun; Moon, Sae Rom; Kim, Chung Sub; Woo, Kyeong Wan; Choi, Sang Un; Lee, Kang Ro



Two new benzylbenzoate glucosides from Curculigo orchioides.  


An extract from in vitro cultures of Curculigo orchioides grown as bulbils in shake flasks, afforded two new glucosides of substituted benzylbenzoate - curculigoside C (3) and curculigoside D (4) - together with two known compounds - curculigoside A (1) and curculigoside B (2). Their structures were elucidated on the basis of spectral evidence, in particular by using 2D NMR methods. Their vasoactive properties were assessed in isolated rat aortic rings. PMID:16814485

Valls, Josep; Richard, Tristan; Larronde, Fabienne; Leblais, Véronique; Muller, Bernard; Delaunay, Jean-Claude; Monti, Jean-Pierre; Ramawat, K G; Mérillon, Jean-Michel



New unusual iridoids from the leaves of noni ( Morinda citrifolia L.) show inhibitory effect on ultraviolet B-induced transcriptional activator protein-1 (AP1) activity  

Microsoft Academic Search

A novel iridoid dimer in whose structure the two iridoid units are connected by a rare ether group, together with two new unusual iridoids showing significant inhibition of UVB-induced Activator Protein-1 (AP-1) activity in cell cultures, have been isolated from the leaves of noni (Morinda citrifolia L.). Their structures were determined on the basis of detailed high-field 1D and 2D

Shengmin Sang; Guangming Liu; Kan He; Nanqun Zhu; Zigang Dong; Qunyi Zheng; Robert T Rosen; Chi-Tang Ho



Naphthoquinone glucosides of Drosera gigantea from in vitro cultures.  


From the shoots of Drosera gigantea propagated under in vitro culture, the rare naphthoquinone glucosides droserone (3,5-dihydroxy-2-methyl-1,4-naphthoquinone) and hydroxydroserone (3,5,8-trihydroxy-2-methyl-1,4-napthoquinone) 5-O-beta-glucosides, together with the free naphthoquinones droserone, hydroxydroserone and plumbagin were isolated. The structures of the glucosides and hydroxydroserone were studied by 2D NMR techniques. The glucosides appear to be responsible for the brown-red (maroon) colour of this plant. Of the other naphthoquinones typical for the family Droseraceae only hydroplumbagin glucoside could be detected, whereas the presence of 7-methyljuglone and rossoliside (= 7-methylhydrojuglone glucoside) was excluded. PMID:11105579

Budzianowski, J



Enzymatic synthesis of alkyl glucosides using Leuconostoc   mesenteroides dextransucrase  

Microsoft Academic Search

Alkyl glucosides were synthesized by the reaction of Leuconostoc mesenteroides dextransucrase with sucrose and various alcohols. Alkyl ?-d-glucosides were obtained with a yield of 30% (mol\\/mol) with primary alcohols, but secondary alcohols or tertiary alcohols\\u000a gave yields below 5%. The optimal yield was 50% using 1-butyl ?-d-glucoside with 0.9 M 1-butanol. The acceptor products of methanol or ethanol were confirmed as methyl

Young-Min Kim; Byung-Hoon Kim; Joon-Seob Ahn; Go-Eun Kim; Sheng-De Jin; Thanh-Hanh Nguyen; Doman Kim



Cucurbitacin glucosides: Antioxidant and free-radical scavenging activities  

Microsoft Academic Search

The cucurbitacins are of great interest because of the wide range of biological activities they exhibit in plants and animals. We studied the antioxidant properties of cucurbitacin B + E glucosides (cucurbitacin glucoside combination, CGC) and their direct free-radical scavenging properties, using ESR spectroscopy. Antioxidant activity was measured by the ability of the CGC to reduce preformed ABTS•+ into its

Tehila Tannin-Spitz; Margalit Bergman; Shlomo Grossman



Hirtionosides A-C, gallates of megastigmane glucosides, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside from the whole plants of Euphorbia hirta.  


From the 1-BuOH-soluble fraction of a MeOH extract of Euphorbia hirta, collected in the Okinawa islands, three new megastigmane glucoside gallates, named hirtionosides A-C, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside were isolated along with 15 known compounds. The structures of the new compounds were elucidated by detailed analysis of physical data, including one- and two-dimensional NMR spectra, and those of known compounds were determined by comparison of physico-chemical data with those reported in the literature. The absolute structures of the megastigmanes were determined by comparison of NMR data and Cotton effects in the CD spectra. The modified Mosher's method was applied to determine the absolute structure of the chiral center in 3-hydroxyoctanoic acid. The DPPH radical-scavenging properties of megastigmane glucoside gallates were assayed and, as expected, they showed moderate activity. PMID:22836810

Nomoto, Yuya; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki



Analysis of eleven iridoid glycosides by micellar electrokinetic capillary chromatography (MECC) and screening of plant samples by partial filling (MECC)–electrospray ionisation mass spectrometry  

Microsoft Academic Search

Of ammonium, lithium and sodium salts of dodecyl sulfate studied as surfactants in the separation of iridoid glycosides by micellar electrokinetic capillary chromatography (MECC), the last one gave the best results. Eleven neutral iridoid glycosides were separated by MECC with sodium dodecyl sulfate as surfactant, and the water–micelle partition coefficients of the compounds were calculated. The separation system was coupled

Johanna Suomi; Susanne K Wiedmer; Matti Jussila; Marja-Liisa Riekkola



Leucine-Derived Cyano Glucosides in Barley1  

PubMed Central

Barley (Hordeum vulgare) seedlings contain five cyano glucosides derived from the amino acid l-leucine (Leu). The chemical structure and the relative abundance of the cyano glucosides were investigated by liquid chromatography-mass spectrometry and nuclear magnetic resonance analyses using spring barley cultivars with high, medium, and low cyanide potential. The barley cultivars showed a 10-fold difference in their cyano glucoside content, but the relative content of the individual cyano glucosides remained constant. Epiheterodendrin, the only cyanogenic glucoside present, comprised 12% to 18% of the total content of cyano glucosides. It is proposed that the aglycones of all five cyano glucosides are formed by the initial action of a cytochrome P450 enzyme of the CYP79 family converting l-Leu into Z-3-methylbutanal oxime and subsequent action of a less specific CYP71E enzyme converting the oxime into 3-methylbutyro nitrile and mediating subsequent hydroxylations at the ?-, as well as ?- and ?-, carbon atoms. Presence of cyano glucosides in the barley seedlings was restricted to leaf tissue, with 99% confined to the epidermis cell layers of the leaf blade. Microsomal preparations from epidermal cells were not able to convert l-[14C]Leu into the biosynthetic intermediate, Z-3-methylbutanal-oxime. This was only achieved using microsomal preparations from other cell types in the basal leaf segment, demonstrating translocation of the cyano glucosides to the epidermal cell layers after biosynthesis. A ?-glucosidase able to degrade epiheterodendrin was detected exclusively in yet a third compartment, the endosperm of the germinating seed. Therefore, in barley, a putative function of cyano glucosides in plant defense is not linked to cyanide release.

Nielsen, Kirsten Annette; Olsen, Carl Erik; Pontoppidan, Katrine; M?ller, Birger Lindberg



Monoterpenoid indole alkaloids bearing an N4-Iridoid from Gelsemium elegans.  


Five new alkaloids, gelseganines A-D (1-4) and humantenine N(4)-oxide (5), were isolated from the stems and leaves of Gelsemium elegans. Compounds 1-4 represent a rare class of monoterpenoid indole alkaloids that bear an N(4)-iridoid unit. The structures of 1-5 were determined by spectroscopic analysis, single-crystal X-ray diffraction, and chemical correlation, and their absolute configurations were elucidated by CD analysis. A plausible biogenetic pathway for alkaloids 1-5 was also postulated. PMID:18604820

Yin, Sheng; He, Xiu-Feng; Wu, Yan; Yue, Jian-Min



Rigenolide A, a new secoiridoid glucoside with a cyclobutane skeleton, and three new acylated secoiridoid glucosides from Gentiana rigescens Franch.  


Rigenolide A (1), a new secoiridoid glucoside with a cyclobutane skeleton and three new acylated secoiridoid glucosides, 2'-(2,3-dihydroxybenzoyl)-gentiopicroside (2), 2'-(2,3-dihydroxybenzoyl)-swertiamarin (3), 3'-(2,3-dihydroxybenzoyl)-sweroside (4), along with two noriridoids (7 and 8) and two known secoiridoid glucosides (5 and 6), were isolated from Gentiana rigescens Franch. The structures of new compounds were elucidated by extensive spectroscopic analyses. The isolated compounds were evaluated for DPPH free-radical scavenging activity. PMID:23994629

Suyama, Yoshihiro; Kurimoto, Shin-Ichiro; Kawazoe, Kazuyoshi; Murakami, Kotaro; Sun, Han-Dong; Li, Shun-Lin; Takaishi, Yoshihisa; Kashiwada, Yoshiki



A New Phenolic Glucoside, Curculigoside from Rhizomes of Curculigo orchioides.  


A new phenolic glucoside, named curculigoside (I), was isolated from the rhizomes of CURCULIGO ORCHIOIDES G AERTN. and its structure was elucidated as 5-hydroxy-2-O-beta-D-glucopyranosylbenzyl 2,6-dimetoxybenzoate. PMID:17405094

Kubo, M; Namba, K; Nagamoto, N; Nagao, T; Nakanishi, J; Uno, H; Nishimura, H



Identification of a Saccharomyces cerevisiae Glucosidase That Hydrolyzes Flavonoid Glucosides? †  

PubMed Central

Baker's yeast (Saccharomyces cerevisiae) whole-cell bioconversions of naringenin 7-O-?-glucoside revealed considerable ?-glucosidase activity, which impairs any strategy to generate or modify flavonoid glucosides in yeast transformants. Up to 10 putative glycoside hydrolases annotated in the S. cerevisiae genome database were overexpressed with His tags in yeast cells. Examination of these recombinant, partially purified polypeptides for hydrolytic activity with synthetic chromogenic ?- or ?-glucosides identified three efficient ?-glucosidases (EXG1, SPR1, and YIR007W), which were further assayed with natural flavonoid ?-glucoside substrates and product verification by thin-layer chromatography (TLC) or high-performance liquid chromatography (HPLC). Preferential hydrolysis of 7- or 4?-O-glucosides of isoflavones, flavonols, flavones, and flavanones was observed in vitro with all three glucosidases, while anthocyanins were also accepted as substrates. The glucosidase activities of EXG1 and SPR1 were completely abolished by Val168Tyr mutation, which confirmed the relevance of this residue, as reported for other glucosidases. Most importantly, biotransformation experiments with knockout yeast strains revealed that only EXG1 knockout strains lost the capability to hydrolyze flavonoid glucosides.

Schmidt, Sabine; Rainieri, Sandra; Witte, Simone; Matern, Ulrich; Martens, Stefan



Complete NMR spectral assignments of two new iridoid diastereoisomers from the flowers of Plumeria rubra L. cv. acutifolia.  


Two new iridoid diastereoisomers (1, 2), together with five known compounds, were isolated from the flowers of Plumerian rubra L. cv. acutifolia. Their structures were elucidated by the means of in-depth spectroscopic and mass-spectrometric analyses, particularly 1D and 2D NMR spectroscopy. PMID:18802971

Ye, Guan; Yang, Yan-ling; Xia, Guang-xin; Fan, Ming-song; Huang, Cheng-gang



Circular dichroism of anthocyanidin 3-glucoside self-aggregates.  


Self-association constants for the flavylium cations of the six most common anthocyanidin 3-glucosides were determined by circular dichroism (CD) and UV-Vis spectroscopy. Along with previous (1)H NMR results, all measurements were consistent with a monomer-dimer model. The CD spectra of the anthocyanidin 3-glucosides were similar to the analogues 3,5-diglucosides. All dimers of the anthocyanidin 3-glucosides exhibited left-handed CD signals, with petunidin-3-glucoside and myrtillin having the most intense signals. In addition, the magnitude of the molar ellipticity, [?], was generally higher for the 3-glucosides than for the 3,5-diglucosides. For all six anthocyanins studied, the CD absorption spectra of their dimers showed evidence of the splitting of the monomer absorption into lower (J aggregates) and higher (H aggregates) energy bands. The angle and the distance between the dipolar moments of the two monomers comprising the dimer were obtained from the lower energy absorption band. While the angle was more or less similar in all six dimers, the separation distance between the monomer dipole moments differed dramatically. The intensity of the CD signal displayed a linear dependence with the inverse square of the dipole moment distances. PMID:23337569

Gavara, Raquel; Petrov, Vesselin; Quintas, Alexandre; Pina, Fernando



Unique cholesteryl glucosides in Helicobacter pylori: composition and structural analysis.  

PubMed Central

A chloroform-methanol-extracted lipid of Helicobacter pylori was studied. Three kinds of glycolipids, accounting for about 25% (wt/wt) of the total lipid, were detected and identified to be cholesteryl glucosides. The structures of two of them were determined to be cholesteryl-alpha-D-glucopyranoside and cholesteryl-6-O-tetrade-canoyl-alpha-D-glucopyranoside, and the plausible structure of the third one was identified as cholesteryl-6-O-phosphatidyl-alpha-D-glucopyranoside. Cholesteryl glucosides are very rare in animals and bacteria. Furthermore, those in H. pylori had an alpha-glycosidic linkage, which is rather unusual for natural glycosides, and a phosphate-linked cholesteryl glycoside like the cholesteryl-6-O-phosphatidyl-alpha-D-glucopyranoside has not been reported previously. As the cholesterol glucosides were detected in strains obtained from diverse geographical locations, the presence of cholesteryl glucosides in H. pylori is a very unique and a characteristic feature of the species. These findings add a new facet to the physiology and biochemistry, especially the cholesterol and glucose metabolism, of H. pylori. Furthermore, the cholesteryl glucosides of H. pylori showed hemolytic activities.

Hirai, Y; Haque, M; Yoshida, T; Yokota, K; Yasuda, T; Oguma, K



Strategies for engineering plant natural products: the iridoid-derived monoterpene indole alkaloids of Catharanthus roseus.  


The manipulation of pathways to make unnatural variants of natural compounds, a process often termed combinatorial biosynthesis, has been robustly successful in prokaryotic systems. The development of approaches to generate new-to-nature compounds from plant-based pathways is, in comparison, much less advanced. Success will depend on the specific chemistry of the pathway, as well as on the suitability of the plant system for transformation and genetic manipulation. As plant pathways are elucidated, and can be heterologously expressed in hosts that are more amenable to genetic manipulation, biosynthetic production of new-to-nature compounds from plant pathways will become more widespread. In this chapter, some of the key strategies that have been developed for metabolic engineering of plant pathways, namely directed biosynthesis, mutasynthesis, and pathway incorporation of engineered enzymes are highlighted. The iridoid-derived monoterpene indole alkaloids from C. roseus, which are the focus of this chapter, provide an excellent system for developing these strategies. PMID:22999175

O'Connor, Sarah E



Phenolic acid glucosides from the seeds of Entada phaseoloides Merill.  


Phytochemical investigation of the defatted seeds of Entada phaseoloides Merill. (Mimosaceae) led to the isolation of three new phenolic acid glucosides, which were characterized as 2-hydroxy-5-methylbenzoyl-?-L-glucopyranoside (p-cresotyl glucoside, 1), 2-hydroxy-5-methylbenzoyl-?-L-glucopyranosyl (2 ? 1)-?-L-glucopyranosyl (2 ? 1)-?-L-glucopyranoside (p-cresotyl triglucoside, 2), and 2-hydroxybenzoyl-?-L-glucopyranosyl (2 ? 1)-?-L-glucopyranosyl (2 ? 1)-?-L-glucopyranosyl (2 ? 1)-?-L-glucopyranoside (salicylic acid tetraglucoside, 5), along with sucrose and triglucoside. The structures of these phytoconstituents have been established on the basis of spectral data analysis and chemical reactions. PMID:21751835

Singh, Onkar; Ali, Mohd; Akhtar, Nida



Interaction of quercetin glucosides with the intestinal sodium\\/glucose co-transporter (SGLT-1)  

Microsoft Academic Search

Recently it has been postulated that flavonoid glucosides may be absorbed by the small intestine via the SGLT-1. Therefore, we applied an in vitro mucosal uptake method to investigate mucosal uptake of the non-metabolisable glucose analogue methyl-?-d-glucopyranoside (MDG) as influenced by quercetin-3-glucoside (isoquercitrin) and quercetin-4? -glucoside (spiraeosid). We found that both glucosides significantly inhibited SGLT-1-mediated MDG uptake whereas the aglycon

Peter Ader; Markus Blöck; Silke Pietzsch; Siegfried Wolffram



21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2010 CFR

...2009-04-01 true Methyl glucoside-coconut oil ester. 172.816 Section 172.816 ...Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in...



21 CFR 178.3600 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2010 CFR

...2009-04-01 true Methyl glucoside-coconut oil ester. 178.3600 Section 178.3600...Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of...



21 CFR 178.3600 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2010 CFR

...2009-04-01 false Methyl glucoside-coconut oil ester. 178.3600 Section 178.3600...Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of...



21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2010 CFR

...2009-04-01 false Methyl glucoside-coconut oil ester. 172.816 Section 172.816 ...Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in...



21 CFR 573.660 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2010 CFR

...2009-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660 ...Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in accordance...



Hybridaphniphyllines A and B, Daphniphyllum alkaloid and iridoid hybrids suggestive of Diels-Alder cycloaddition in Daphniphyllum longeracemosum.  


Two Daphniphyllum alkaloid and iridoid hybrids with the hitherto unknown decacyclic fused skeletons, hybridaphniphyllines A and B, along with one diamino Daphniphyllum alkaloid, daphnicyclidin I, were isolated from dried stems and leaves of Daphniphyllum longeracemosum. Their structures were elucidated on the basis of extensive spectroscopic analysis, and the absolute configuration of daphnicyclidin I was deduced by the CD exciton chirality method. A biogenetic pathway for 1 and 2 involving natural Diels-Alder cycloaddition is proposed. PMID:23906551

Wang, Fei; Mao, Mei-Fen; Wei, Guo-Zhu; Gao, Yuan; Ren, Fu-Cai; Liu, Ji-Kai



Micellar electrokinetic capillary chromatography of limonoid glucosides from citrus seeds  

Microsoft Academic Search

This report presents the results of an investigation into the application of micellar electrokinetic capillary chromatography (MECC) for the analysis of limonoid glucosides in a citrus seed extract. MECC based on sodium dodecyl sulphate (SDS) was used to provide highly efficient separations of the closely related structures. A phosphate-borate buffer containing SDS was used to optimize the separation conditions for

Vinayagum E. Moodley; Dulcie A. Mulholland; Mark W. Raynor



A new phenylethanoid glucoside from Plantago depressa Willd  

Microsoft Academic Search

Chemical research of Plantago depressa Willd. led to one new phenylethanoid glucoside with ?-L-rhamnosyl (1???2)-?-D-glucose structure, together with four known compounds. These five compounds (1–5) were isolated from the family Plantaginaceae for the first time; the chemotaxonomic significance of cerebrosides was also discussed.

Chang-Yuan Yu; Yi-Chao Sun; Guang Chen



Stigmasteryl-?-D-glucoside as an auxin synergist  

Microsoft Academic Search

The presence of an auxin synergist was confirmed in the neutral fraction of extracts from peanut plants (Arachis hypogaea L.). The main component resposible for the activity was established as stigmasteryl-ß-D-glucoside. It promoted markedly the elongation of Avena coleoptile segments induced by indoleacetic acid (IAA), but was only weakly active in the absence of IAA.

Yasuo Kimura; Arno Tietz; Saburo Tamura



Taxonomical markers in two endemic plants of Sardinia: Verbascum conocarpum and Scrophularia trifoliata.  


The monoterpenoid composition of Verbascum conocarpum and Scrophularia trifoliata, both endemic plants of Sardinia, was examined. The main chemotaxonomic markers of Scrophulariaceae, the iridoids aucubin, verbascoside and catalpol, were isolated. PMID:16644551

Ramunno, Alessia; Serrilli, Anna Maria; Piccioni, Francesco; Serafini, Mauro; Ballero, Mauro



Antioxidant constituents from rhubarb: structural requirements of stilbenes for the activity and structures of two new anthraquinone glucosides  

Microsoft Academic Search

The methanolic extracts from five kinds of rhubarb were found to show scavenging activity for DPPH radical and O2?. Two new anthraquinone glucosides were isolated from the rhizome of Rheum undulatum L. together with two anthraquinone glucosides, a naphthalene glucoside, and 10 stilbenes. In the screening test for radical scavenging activity of rhubarb constituents, stilbenes and a naphthalene glucoside showed

Hisashi Matsuda; Toshio Morikawa; Iwao Toguchida; Ji-Young Park; Shoichi Harima; Masayuki Yoshikawa



Phenolic glucosides from Dendrobium aurantiacum var. denneanum and their bioactivities.  


A new 8,4'-oxyneolignane glucoside 1 has been isolated from the stems of Dendrobium aurantiacum var. denneanum together with six known phenolic glucosides 2?7. The structure of the new compound, including its absolute configuration, was determined by spectroscopic and chemical methods as (?)-(7S,8R,7'E)-4-hydroxy-3,3',5,5'-tetramethoxy-8,4'-oxyneolign-7'-ene-7,9,9'-triol 7,9'-bis-O-?-D-glucopyranoside (1). In the in vitro assays, compound 1 and (?)-syringaresinol-4,4'-bis-O-?-D-glucopyranoside (2) showed evident activity against glutamate-induced neurotoxicity in PC12 cells. Shashenoside I (4) showed a selective cytotoxic activity with the IC?? value of 4.17 ?M against the acute myeloid leukemia cell line MV4-11, while it was inactive against 10 other human tumor cell lines. PMID:23702921

Xiong, Liang; Cao, Zhi-Xing; Peng, Cheng; Li, Xiao-Hong; Xie, Xiao-Fang; Zhang, Ting-Mo; Zhou, Qin-Mei; Yang, Lian; Guo, Li



Carboxymethyl flavonoids and a monoterpene glucoside from Selaginella moellendorffii.  


A new dihydroflavone, 5-carboxymethyl-7,4'-dihydroxyflavonone (1), and its glucoside 5-carboxymethyl-7,4'-dihydroxyflavonone-7-O-?-D: -glucopyranoside (2), and one new monoterpene glucoside, (4Z,6E)-2,7-dimethyl-8-hydroxyocta-4,6-dienoic acid 8-O-?-D: -glucopyranoside (3), were isolated from the whole plants of Selaginella moellendorffii. Their structures were determined by spectroscopic methods and chemical transformation. Compound 2 was evaluated for the ability to enhance glucose consumption in normal and insulin-resistant L6 muscle cells induced by high concentrations of insulin and glucose. Glucose consumption in insulin-resistant cells (but not in normal cells) was increased 15.2 ± 3.3% (p < 0.01) by compound 2 at a concentration of 0.1 ?M in the presence of insulin (1 nM). PMID:21910049

Wang, Hong-Sheng; Sun, Ling; Wang, Yue-Hu; Shi, Ya-Na; Tang, Gui-Hua; Zhao, Fu-Wei; Niu, Hong-Mei; Long, Chun-Lin; Li, Ling



[Effects of cornel iridoid glycoside on activity of cholinesterases in vitro].  


The purpose of the present study was to investigate the effects of cornel iridoid glycoside (CIG) on the activity of cholinesterases in vitro, and to investigate the mechanism of CIG's treating Alzheimer's disease (AD). The sources of cholinesterases were prepared from human blood cells, rat brain homogenate and human blood plasma, respectively. The biochemical methods were used to detect the activity of acetylcholine esterase (AChE) and butyryl cholinesterase (BuChE) to investigate the influence of CIG on cholinesterases. The results showed that CIG inhibited the activity of AChE of human blood cells and rat brain homogenate, with the 50% inhibition rate (IC50) of 1.6 g . L-1 and 3.3 g . L-1, respectively; and the inhibition of AChE of CIG is reversible. CIG also inhibited the activity of BuChE of human blood plasma, with the IC50 of 2.9 g . L-1. In conclusion, CIG can inhibit the activity of AChE and BuChE in vitro, which may be one of the mechanisms of CIG to treat AD. PMID:23944063

Chu, Si-Juan; Zhang, Lan; Liu, Gang; Zhou, Wen-Xia; Li, Lin



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


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

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



Inhibition of phenobarbitone N-glucosidation by valproate.  

PubMed Central

Plasma phenobarbitone concentrations and daily urinary excretion of phenobarbitone and its metabolites p-hydroxyphenobarbitone (conjugated and unconjugated), and [S]-phenobarbitone-N-glucoside were measured under steady-state conditions in two groups of epileptic patients, (i) taking phenobarbitone with or without other drugs, but not valproate (n = 12), and (ii) taking phenobarbitone with other drugs including valproate (n = 8). Mean steady-state plasma phenobarbitone concentrations were 5.9 mg l-1 higher, relative to drug dose, in the patients taking valproate than in those not taking valproate. Urinary excretion of [S]-phenobarbitone-N-glucoside was significantly lower in the group taking valproate (1.9 +/- s.d. 2.0% of phenobarbitone dose vs 16.2 +/- s.d. 9.9%). Urinary excretion of phenobarbitone (23.7 +/- s.d. 9.8% vs 48.2 +/- s.d. 13.6%) and unconjugated p-hydroxyphenobarbitone (5.7 +/- s.d. 3.9% vs 16.0 +/- s.d. 9.1%) was higher in those taking valproate, while conjugated p-hydroxyphenobarbitone excretion was similar in both groups (8.3 +/- s.d. 4.9% vs 6.5 +/- s.d. 2.9%). Valproate appeared to inhibit both the direct N-glucosidation of phenobarbitone and the O-glucuronidation of p-hydroxyphenobarbitone.

Bernus, I; Dickinson, R G; Hooper, W D; Eadie, M J



Phytotoxic cis-cinnamoyl glucosides from Spiraea thunbergii.  


Spiraea thunbergii Sieb. was found to contain 1-O-cis-cinnamoyl-beta-D-glucopyranose and 6-O-(4'-hydroxy-2'-methylene-butyroyl)-1-O-cis-cinnamoyl-beta-D-glucopyranose as major plant growth inhibitory constituents along with related compounds of lower phytotoxicity including 6-O-(trans-cinnamoyl)-1-O-(4"-hydroxy-3"-methyl-furan-2"-one)-beta-D-glucopyranose, 6-O-(4'-hydroxy-2'-methylene-butyroyl)-1-O-trans-cinnamoyl-beta-D-glucopyranose, and 1-O-trans-cinnamoyl-beta-D-glucopyranose. The former three compounds were cinnamoyl glucosides. PMID:15016569

Hiradate, Syuntaro; Morita, Sayaka; Sugie, Hajime; Fujii, Yoshiharu; Harada, Jiro



Two diterpenes and three diterpene glucosides from Phlogacanthus curviflorus.  


Two new diterpene lactones, phlogacantholides B (1) and C (2), and three new diterpene lactone glucosides, phlogacanthosides A (3), B (4), and C (5), together with lupeol, beta-sitosterol, betulin, beta-daucosterol, (+)-syringaresinol, and (+)-syringaresinol-4-O-beta-D-glucopyranoside, were isolated from the roots of Phlogacanthus curviflorus. Their structures were elucidated by chemical and spectroscopic evidence. The structure, including the relative configuration of phlogacantholide B (1), was confirmed by X-ray crystallographic analysis of its diacetate (6). PMID:15679324

Yuan, Xiao-Hong; Li, Bo-Gang; Zhang, Xiu-Yun; Qi, Hua-Yi; Zhou, Min; Zhang, Guo-Lin



Antibacterial sesquiterpene lactone glucoside from seed pods of Bauhinia retusa.  


From the seed pods of Bauhinia retusa, a new eudesmane sesquiterpene glucoside, 1-O-?-D-glucopyranosyl-9?,15-dihydroxy-5?,6?H-eudesma-3-ene-6?,12-olide (1), has been isolated together with three known compounds, 4'-hydroxy-7-methoxy flavane (2), ?-sitosterol (3), and stigmasterol (4). The structures of isolated compounds were verified with the help of 1D, 2D NMR, and HR-ESI-MS spectroscopies. Compound 1 showed moderate antibacterial activity against Pseudomonas aeruginosa and Escherichia coli when a disc diffusion method is used. PMID:21253953

Semwal, Sushma; Sharma, Rajni Kant



Simultaneous determination of iridoid glycosides and flavanoids in Lamionphlomis rotate and its herbal preparation by a simple and rapid capillary zone electrophoresis method.  


Iridoid glycosides and flavanoids are two main effective components of Lamiophlomis rotata (Benth.) kudo. However, there is no method for simultaneous analysis of iridoid glycosides and flavanoids in L. rotata and its pharmaceutical preparations. A simple and rapid capillary zone electrophoresis (CZE) method was developed and validated for simultaneous determination of two iridoid glycosides (8-O-acetylshanzhiside methylester and 8-deoxyshanzhiside) and three flavanoids (apigenin, quercetin and luteolin) in L. rotata. Operational variables, such as the voltage, buffer concentration and pH were optimized, the final optimum separation condition was 10 mM sodium tetraborate-20 mM NaH(2) PO(4) (pH 8.5)-15% (v/v) methanol, 238 nm UV detection, 18 kV applied voltage. The linearity and the recovery of the proposed method were very satisfactory (correlation coefficients were 0.9994-0.9998 and the recoveries were 94.5-108.8% for the analytes) and the method allowed analytes in real samples to be determined within 9 min. The proposed CZE method can be used for quality control of iridoid glycosides and flavanoids in L. rotata and its herbal preparation. PMID:21548111

Lü, Wenjuan; Li, Maoxing; Chen, Yonglei; Chen, Hongli; Chen, Xingguo



Citrifolinin A , a new unusual iridoid with inhibition of Activator Protein1 (AP1) from the leaves of noni ( Morinda citrifolia L.)  

Microsoft Academic Search

A new unusual iridoid, named citrifolinin A, showing significant inhibition of UVB-induced Activator Protein-1 (AP-1) activity in cell cultures, has been isolated from the leaves of Morinda citrifolia. Its structure was elucidated based on a detailed high-field 1D and 2D spectral analysis.

Shengmin Sang; Kan He; Guangming Liu; Nanqun Zhu; Mingfu Wang; Jin-woo Jhoo; Qunyi Zheng; Zigang Dong; Geetha Ghai; Robert T. Rosen; Chi-Tang Ho



Melanogenesis inhibitory activities of iridoid-, hemiterpene-, and fatty acid-glycosides from the fruits of Morinda citrifolia (Noni).  


A new iridoid glycoside, 9-epi-6alpha-methoxy geniposidic acid (4), three new hemiterpene glycosides, 3-methylbut-3-enyl 2'-O-(beta-D-glucopyranosyl)-beta-D-glucopyranoside (nonioside K) (6), 3-methylbut-3-enyl 6'-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside (nonioside L) (8), and 3-methylbut-3-enyl 6'-O-(beta-D-xylofuranosyl)-beta-D-glucopyranoside (nonioside M) (9), and two new saccharide fatty acid esters, 6'-O-(beta-D-glucopyranosyl)-1'-O-[(2xi)-2-methylbutanoyl]-beta-D-glucopyranose (nonioside N) (16) and 6'-O-(beta-D-xylopyranosyl)-1'-O-[(2xi)-2-methylbutanoyl]-beta-D-glucopyranose (nonioside O) (17), were isolated from a methanol extract of the fruits of Morinda citrifolia (noni), along with 11 known compounds, namely, three iridoid glycosides (1-3), two hemiterpene glycosides (5 and 7), and five saccharide fatty acid esters (10-15). Upon evaluation of compounds 1-17 on the melanogenesis in the B16 melanoma cells induced with alpha-melanocyte-stimulating hormone (alpha-MSH), 13 compounds (1, 3, 4, 6-14, and 17) exhibited marked inhibitory effects with 34-49% reduction of melanin content at 100 muM with no or almost no toxicity to the cells (91-116% of cell viability at 100 microM). PMID:20032599

Akihisa, Toshihiro; Seino, Ken-ichi; Kaneko, Etsuyo; Watanabe, Kensuke; Tochizawa, Shun; Fukatsu, Makoto; Banno, Norihiro; Metori, Koichi; Kimura, Yumiko



New ?-glucosides of caffeoyl quinic acid from the leaves of Moringa oleifera Lam.  


Two new caffeoyl quinic acid ?-glucosides, together with three known caffeoyl quinic acids and five known flavonoid glucosides, were isolated from the leaves of Moringa oleifera Lam. The structures of the new compounds were elucidated as 4-O-(4'-O-?-D-glucopyranosyl)-caffeoyl quinic acid (1) and 4-O-(3'-O-?-D-glucopyranosyl)-caffeoyl quinic acid (2) by spectroscopic analyses. PMID:21748486

Kashiwada, Yoshiki; Ahmed, Fakhruddin Ali; Kurimoto, Shin-ichiro; Kim, Sang-Yong; Shibata, Hirofumi; Fujioka, Toshihiro; Takaishi, Yoshihisa



Trans-resveratrol-3- O- ?-glucoside (piceid) in cell suspension cultures of vitis vinifera  

Microsoft Academic Search

Suspension cultures of Vitis vinifera were found to produce catechins and stilbenes. When the cells were grown in a polyphenol-inducing medium, a stilbene glucoside (piceid) was isolated. By using spectroscopic methods, the structure was determined as trans-resveratrol-3-O-?-glucoside.

Pierre Waffo Teguo; Alain Decendit; Joseph Vercauteren; Gérard Deffieux; Jean-Michel Mérillon



Pyrazole O-glucosides as novel Na +-glucose cotransporter (SGLT) inhibitors  

Microsoft Academic Search

O-glucuronides and O-glucosides of a series of pyrazoles analogues were synthesized and evaluated for their SGLT inhibitory activity in brush border membrane vehicles (BBMVs) of rat kidney. O-glucosides of certain pyrazole analogues inhibited the transport of [14C]-glucose in BBMVs, and induced glucosuria in Wistar rats by intravenous injection.

Koji Ohsumi; Hiroyuki Matsueda; Toshihiro Hatanaka; Ryusuke Hirama; Takashi Umemura; Akiko Oonuki; Nozomu Ishida; Yoko Kageyama; Katsumi Maezono; Nobuo Kondo



Cytotoxic furostanol saponins and a megastigmane glucoside from tribulus parvispinus.  


Two new furostanol saponins, (25R)-26-O-beta-D-glucopyranosyl-5alpha-furostan-2alpha,3beta,22alpha,26-tetraol 3-O-{beta-D-galactopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside} (1) and (25R)-26-O-beta-D-glucopyranosyl-5alpha-furostan-3beta,22alpha,26-triol 3-O-{beta-D-galactopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside} (2), and their O-methyl derivatives (3 and 4), and a new megastigmane glucoside, (6S,7E,9xi)-6,9,10-trihydroxy-4,7-megastigmadien-3-one 10-O-beta-D-glucopyranoside (6), along with one known spirostanol saponin, gitonin (5), and four known megastigmane glucosides were isolated from the aerial parts of Tribulus parvispinus. Their structures were established by detailed spectroscopic analysis. The cytotoxic activities of 1-6 against U937, MCF7, and HepG2 cells were evaluated. Compounds 2 (IC(50) 0.5 microM) and 5 (IC(50) 0.1 microM) showed the highest activity against U937 cells. PMID:16252924

Perrone, Angela; Plaza, Alberto; Bloise, Elena; Nigro, Patrizia; Hamed, Arafa I; Belisario, Maria Antonietta; Pizza, Cosimo; Piacente, Sonia



Cyanogenic allosides and glucosides from Passiflora edulis and Carica papaya.  


Leaf and stem material of Passiflora edulis (Passifloraceae) contains the new cyanogenic glycosides (2R)-beta-D-allopyranosyloxy-2-phenylacetonitrile (1a) and (2S)-beta-D-allopyranosyloxy-2-phenylacetonitrile (1b), along with smaller amounts of (2R)-prunasin (2a), sambunigrin (2b), and the alloside of benzyl alcohol (4); the major cyanogens of the fruits are (2R)-prunasin (2a) and (2S)-sambunigrin (2b). The major cyanogenic glycoside of Carica papaya (Caricaceae) is 2a; only small amounts of 2b also are present. We were not able to confirm the presence of a cyclopentenoid cyanogenic glycoside, tetraphyllin B, in Carica papaya leaf and stem materials. In detailed 1H NMR studies of 1a/b and 2a/b, differences in higher order effects in glucosides and allosides proved to be valuable for assignment of structures in this series. The diagnostic chemical shifts of cyanogenic methine and anomeric protons in 1a/b are sensitive to anisotropic environmental effects. The assignment of C-2 stereochemistry of 1a/b was made in analogy to previous assignments in the glucoside series and was supported by GLC analysis of the TMS ethers. PMID:12150815

Seigler, David S; Pauli, Guido F; Nahrstedt, Adolf; Leen, Rosemary



A new abietic acid-type diterpene glucoside from the needles of Pinus densiflora.  


From the ethyl acetate fraction of the methanol extract of the needles of Pinus densiflora (Pinaceae), a new diterpenoid glucoside [9alpha,13alpha-epoxy-8beta,14beta-dihydroxy-abietic acid-18-O-beta-D: -glucopyranoside] (1), two flavonoid glucosides [kaempferol 3-O-beta-D: -glucoside (2) and 6-C-methyl kaempferol 3-O-beta-D: -glucoside (3)], and two monoterpenoid glucosides [bornyl 6-O-alpha-Larabinofuranosyl (1-->6)-beta-D: -glucopyranoside (4) and bornyl 6-O-beta-D: -apiofuranosyl (1-->6)-beta-D: -glucopyranoside (5)] were isolated and characterized on the basis of spectral analysis. Of all the compounds, 2 and 3 showed peroxynitrite scavenging activity. PMID:20162397

Jung, Mee Jung; Jung, Hyun Ah; Kang, Sam Sik; Hwang, Geum-Sook; Choi, Jae Sue



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

Microsoft Academic Search

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.

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



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


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

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



Regulation of the ?-Glucoside System in Escherchia coli K-12  

PubMed Central

In Escherichia coli wild-type cells, a mutation at the ?-glucoside regulatory gene (bglR+ to bglR?) leads to simultaneous expression of inducible phospho-?-glucosidase B (bglB+) and a ?-glucoside-specific species of enzyme II (?-glucoside transport I [bglC+]); an additional mutation (bglS+ to bglS4) allows these enzymes to be formed constitutively. The bgl alleles have been mapped in the following order: pyrE, bglA, bglB, bglS, bglR, bglC, ilvD. The back mutation in the regulatory allele (bglR? to bglR+) caused the cessation of the expression of the bglB+, bglS+ or bglS4, bglC+ alleles. However, a mutation in a strain with bglB+, bglS4, bglR8, bglC+ alleles, at the ini site that lies between the bglS4 and the bglR8 allele, allowed the expression of the bglS4 and bglB+ alleles, but showed no affect on the expression of the bglC+ allele. It is suggested that the ini mutation possesses a promotor-type function that in the absence of regulatory allele function (bglR8) renews the functioning of only the bglS4 and bglB+ alleles. The complementation studies have shown that the bglB+, bglS+ or bglS4, bglC+ alleles are expressed only in cis to the bglR? allele. In the constitutive strain (bglB+, bglS4, bglR?, bglC+), the expressed bglS4 allele formed a soluble product that acts in trans over the bglB+ and bglC+ alleles and that appears effective only when the bglB+ and the bglC+ alleles are expressed in cis to the bglR? allele. It thus showed that the constitutive biosynthesis of phospho-?-glucosidase B and ?-glucoside transport I is under positive control. Since the regulatory allele bglR? lies between the bglS4 and the blgC+ alleles, and acts in cis, it appears that the mutation (bglR+ to bglR?) allows the initiation of transcription in one direction to express the bglS4, bglB+ alleles and in the other to express the bglC+ allele. The structural genes bglB and bglC lie adjacent to the regulatory genes bglR and bglS, and the structural genes are coordinately controlled by the regulatory genes. It is, therefore, proposed that the bglB, bglS, bglR, bglC genes form a bgl operon.

Prasad, Ishwari; Schaefler, Sam



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


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-?-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

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



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


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-(?-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

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



Lipase-catalyzed regioselective synthesis of steryl (6'-O-acyl)glucosides.  


The regioselective acylation of cholesteryl beta-D-glucoside, at the C-6 of the glucose moiety, was achieved using microbial lipases in organic solvents. With palmitic acid as an acyl donor 81 or 63% conversions of cholesteryl glucoside to its 6'-O-palmitoyl derivative were obtained using Candida antarctica or Rhizomucor miehei enzymes, respectively. High yields (64-92%) were also obtained with fatty acids 6:0-22:0 and 16:1 (n-7). The synthesis of cholesteryl (6'-O-palmitoyl)glucoside was also achieved via transesterification, using mono-, di- and tri-palmitoylglycerols or methyl and ethyl palmitate as acyl sources. With R. miehei lipase transesterification between methyl palmitate (80 mM) and cholesteryl glucoside (1 mM) proceeded after 24 h with a nearly quantitative yield (97%). PMID:17549435

Paczkowski, Cezary; Musial, Arkadiusz; Wlodkowski, Leszek; Kalinowska, Malgorzata; Wojciechowski, Zdzislaw A



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


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

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



A condensed phenylpropanoid glucoside and pregnane saponins from the roots of Hemidesmus indicus.  


From the roots of Hemidesmus indicus, one new condensed phenylpropanoid glucoside and three new pregnenolone glycosides, named hemidesmosides A-C, were isolated along with one known related compound, plocoside A. PMID:22456894

Zhao, Zhimin; Matsunami, Katsuyoshi; Otsuka, Hideaki; Negi, Nisha; Kumar, Ashok; Negi, Devendra Singh



Chromone and chromanone glucosides from Hypericum sikokumontanum and their anti-Helicobacter pylori activities.  


Chromone glucosides, takanechromones A-C (1, 2 and 5) and chromanone glucosides, named takanechromanones A and B (3 and 4), were isolated from the methanolic extracts of Hypericumsikokumontanum together with 27 known compounds. Their structures were established based on spectroscopic evidence. The isolated compounds and some chromone derivatives were assayed for antimicrobial activity against Helicobacter pylori and cytotoxicity against human cancer cell lines. PMID:19121528

Tanaka, Naonobu; Kashiwada, Yoshiki; Nakano, Tatsuro; Shibata, Hirofumi; Higuchi, Tomihiko; Sekiya, Michiko; Ikeshiro, Yasumasa; Takaishi, Yoshihisa



Identification of glucosides in green beans of Vanilla planifolia Andrews and kinetics of vanilla ?-glucosidase  

Microsoft Academic Search

Natural vanilla is extracted from the fruits of Vanilla planifolia. In the overall vanilla aroma, minor compounds p-cresol, creosol, guaiacol and 2-phenylethanol have a high impact. This is shown by GC-Olfactometry analysis of cured vanilla beans. The presence of ?-D-glucosides of these compounds was investigated, in order to determine if these compounds are derived from glucosides or if they are

Mark J. W. Dignum; Rob van der Heijden; Josef Kerler; Chris Winkel; Rob Verpoorte



Daidzein and genistein but not their glucosides are absorbed from the rat stomach  

Microsoft Academic Search

Absorption of isoflavone aglycones and glucosides was compared in rats. Daidzein, genistein, daidzin and genistin were orally administered at a dose of 7.9 ?mol\\/kg in 25 mM Na2CO3 and next their metabolite concentration in blood plasma was monitored for 30 min. After isoflavone glucosides administration, their metabolites appeared in plasma with a few minutes delay as compared to aglycones, which

Mariusz K Piskula; Jun Yamakoshi; Yukihiko Iwai



(6 S)Hydroxy3-oxo-?-ionol glucosides from Capparis spinosa fruits  

Microsoft Academic Search

Two new (6S)-hydroxy-3-oxo-?-ionol glucosides, together with corchoionoside C ((6S,9S)-roseoside) and a prenyl glucoside, were isolated from mature fruits of Capparis spinosa. The structures were established on the basis of spectroscopic, chiroptic and chemical evidence. In addition, the 13C-resonance of C-9 was found to be of particular diagnostic value in assigning the absolute configuration at that center in ionol glycosides. The

?hsan Çal??; Ay?e Kuruüzüm-Uz; Piergiorgio A. Lorenzetto; Peter Rüedi



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


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 ?-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 ?mol CG/1 mg mitochondria. At this concentration the cycad toxins ?-sitosterol-?-D-glucoside and stigmasterol-?-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 ?-sitosterol had no effect on mitochondrial functions studied at concentrations up to 100 ?mol/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

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



Antinociceptive and anti-inflammatory effects of saponin and iridoid glycosides from Verbascum pterocalycinum var. mutense Hub.-Mor.  


The anti-inflammatory and antinociceptive properties of four major compounds from the flowers of Verbascum pterocalycinum var. mutense were investigated. Saponin glycosides called ilwensisaponin A and C and iridoid glycosides known as ajugol and picroside IV were isolated from the methanolic extract. A dose-related anti-inflammatory and antinociceptive response were obtained in this study at doses of 100 and 200 mg/kg. The results of the evaluation of the anti-inflammatory activity induced by carrageenan and PGE1 showed that this species possesses active constituents that could diminish the cyclooxygenase activitiy. No effects were observed in the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear edema model. Our results support the anti-inflammatory and analgesic effects of Verbascum pterocalycinum var. mutense. Ilwensisaponins A and C could explain in part the anti-inflammatory and analgesic activities of this species. Although antinociceptive and anti-inflammatory activities of ajugol and picroside IV were found insignificant in the statistical analysis, ilwensisaponin A and C showed notable activity without inducing any apparent acute toxicity as well as gastric damage. PMID:18274283

Akkol, Esra Küpeli; Tatli, I Irem; Akdemir, Zeliha S


Synthesis of hexyl ?-glucoside and ?-polyglucosides by a novel Microbacterium isolate.  


Alkyl-glucosides and alkyl-polyglucosides are the new-generation biodegradable surfactants with good emulsifying and wetting properties. The ?-forms of these glucosides occur in antibiotics and also stimulate nasal absorption of many drugs. In this paper, we report the synthesis of hexyl ?-glucoside and ?-polyglucosides using cell-bound ?-glucosidase activity of a novel strain of Microbacterium paraoxydans. A number of cell-bound glycosyl hydrolase activities were detected in the isolate with the maximum hydrolytic activity of 180 IU g(-1) dry wt cells on p-nitrophenyl-?-D-glucopyranoside. In a micro-aqueous system, at a water activity of 0.69, 1.8 g l(-1) of hexyl ?-glucoside (corresponding to about 25 % yield) was synthesized by whole cells with maltose and hexanol as substrates. The concentration was enhanced to 11 g l(-1) (~60 % yield) in a biphasic system at a water content of 60 %. (1)H and (13)C NMR spectra of the purified compound confirmed the synthesized product to be hexyl-?-D-glucopyranoside, while the presence of hexyl di- and tri-glucosides was confirmed by electrospray ionization mass spectrometry. The cell-driven synthesis makes this an extremely attractive alternative for synthesis of such compounds. PMID:23579729

Ojha, Swati; Mishra, Saroj; Kapoor, Sumeet; Chand, Subhash



Biosynthesis of cyanohydrin glucosides from unnatural nitriles in intact tissue of Passiflora morifolia and Turnera angustifolia.  


Passiflora morifolia, which under natural conditions contains cyanohydrin glucosides linamarin, lotaustralin and epilotaustralin, converted cyclopentanecarbonitrile, 2-cyclopentenecarbonitrile and 3-methylbutanenitrile into the corresponding cyanohydrin glucosides. Turnera angustifolia, which normally produces glucosides of cyclopentenone cyanohydrin, converted cyclopentanecarbonitrile, 2-methylpropanenitrile and 2-methylbutanenitrile, but not 3-methylbutanenitrile, into the corresponding cyanohydrin glucosides. Mixtures of epimers were produced when these glucosides contained chiral cyanohydrin carbon atoms. Feeding with cyclopentanecarbonitrile resulted in formation of 1-(beta-D-glucopyranosyloxy)cyclopentanecarbonitrile, a saturated analogue of deidaclin and tetraphyllin A. Neither plant utilized cyclopropanecarbonitrile as substrate. The experiments demonstrate broad substrate specificity of nitrile hydroxylases present in these plants. A novel glycoside, 2-[6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranosyloxy]propane (isopropyl primeveroside), was isolated from P. morifolia. The compound represents a rare example of natural isopropyl glycoside; its characterization included assignment of all 1H and 13C NMR signals of the primeverosyl group using two-dimensional NMR methods. Biosynthesis of the isopropyl moiety of the primeveroside is unclear, but the formation of alcohols corresponding to natural cyanohydrins may be a previously unrecognized extension of the cyanohydrin biosynthesis pathway in higher plants. PMID:8768320

Jaroszewski, J W; Rasmussen, A B; Rasmussen, H B; Olsen, C E; Jørgensen, L B



Liquid chromatography coupled to nuclear magnetic resonance spectroscopy for the identification of isoflavone glucoside malonates in T. pratense L. leaves.  


Previous studies revealed that the main isoflavones in extracts of leaves of T. pratense L. are biochanin A and formononetin, their 7-O-glucosides, and two glucoside malonate isomers of each of them. Since LC-MS(/MS) did not provide sufficient information to distinguish the glucoside malonate isomers, in the present paper LC-NMR as well as off-line two-dimensional NMR were used to obtain further structural information. Matrix solid-phase dispersion (MSPD) was applied to obtain sufficiently high analyte concentrations to perform LC-NMR. Stop-flow reversed-phase LC-NMR was performed using a gradient of deuterated water and deuterated acetonitrile. Offline COSY and NOESY experiments were carried out to determine the positions of the glucose moiety on the flavonoid aglycone, and of the malonate moiety on the glucose. Based on the fragmentation patterns in MS/MS and the NMR spectra, the two formononetin glucoside malonate isomers were identified as 7-O-beta-D-glucoside 6"-O-malonate and 7-O-beta-D-glucoside 4"-O-malonate; i.e. they only differ in the substitution position of the malonate group on the glucoside ring. The biochanin A glucoside malonate isomers, however, have quite different structures. The main and later eluting isomer is biochanin A 7-O-beta-D-glucoside 6"-O-malonate, and the minor and earlier eluting isomer is 5-hydroxy-7-methoxyisoflavone 4'-O-beta-D-glucoside 4"-O-malonate: the positions of the methoxy group and the glucoside 6"-O-malonate group on the flavonoid skeleton are interchanged. PMID:15495407

de Rijke, Eva; de Kanter, Frans; Ariese, Freek; Brinkman, Udo A Th; Gooijer, Cees



Simultaneous determination of citrus limonoid aglycones and glucosides by high performance liquid chromatography.  


High performance liquid chromatography (HPLC) method has been developed for simultaneous quantification of limonoid aglycones and glucosides on a reversed phase C18 column using a binary solvent system, coupled with diode array detector. Seven limonoids such as limonin, nomilin, isolimonic acid, ichangin, isoobacunoic acid, limonin 17-beta-D glucopyranoside and deacetyl nomilinic acid 17-beta-D glucopyranoside were separated and detected at 210 nm. Furthermore, limonoids were separated, identified and quantified in four varieties of citrus fruits and seeds using developed method. Limonin and limonin glucoside were found to be the predominant limonoid aglycone and glucoside, respectively, in all tested samples. The sensitivity of the method was found to be 0.25-0.50 microg for tested limonoids. PMID:17448343

Vikram, Amit; Jayaprakasha, G K; Patil, Bhimanagouda S



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

PubMed Central

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.

Cheong, J J; Hahn, M G



N-glucosides as human sodium-dependent glucose cotransporter 2 (hSGLT2) inhibitors.  


Inhibition of renal sodium-dependent glucose cotransporter 2 (SGLT2) increases urinary glucose excretion (UGE), and thus reduces blood glucose levels in hyperglycemia. A series of N-glucosides was synthesized for biological evaluation as human SGLT2 (hSGLT2) inhibitors. Among these compounds, N-glucoside 9d possessing an indole core structure showed good in vitro activity (IC50=7.1nM against hSGLT2). Furthermore, 9d exhibited favorable in vivo potency with regard to UGE in rats based on good pharmacokinetic profiles. PMID:23999047

Yamamoto, Yasuo; Kawanishi, Eiji; Koga, Yuichi; Sakamaki, Shigeki; Sakamoto, Toshiaki; Ueta, Kiichiro; Matsushita, Yasuaki; Kuriyama, Chiaki; Tsuda-Tsukimoto, Minoru; Nomura, Sumihiro



Purification and characterization of a hydroxamic acid glucoside ?-glucosidase from wheat ( Triticum aestivum L.) seedlings  

Microsoft Academic Search

.  ?A ?-glucosidase (EC with a high affinity for cyclic hydroxamic acid ?-d-glucosides was purified from 48-h-old wheat (Triticum aestivum L.) seedlings. The activity occurred transiently at a high level during the non-autotrophic stage of growth, and the nature\\u000a of the transient occurrence was correlated with that of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside (DIMBOA-Glc).\\u000a The glucosidase had maximum activity at an acidic pH

Masayuki Sue; Atsushi Ishihara; Hajime Iwamura



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


The galloylated cyanogenic glucosides based on prunasin (1-7), gallotannins (8-14), ellagitannins (15-17), ellagic acid derivatives (18, 19) and gallic acid (20) isolated from the leaves of Phyllagathis rotundifolia (Melastomataceae) were investigated for their neuroprotective activity against hydrogen peroxide (H(2)O(2))-induced oxidative damage in NG108-15 hybridoma cell line. Among these compounds, the gallotannins and ellagitannins exhibited remarkable neuroprotective activities against oxidative damage in vitro as compared to galloylated cyanogenic glucosides and ellagic acid derivatives in a dose-dependent manner. They could be explored further as potential natural neuroprotectors in various remedies of neurodegenerative diseases. PMID:22093753

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



Acylated anthocyanidin 3-sophoroside-5-glucosides from Ajuga reptans flowers and the corresponding cell cultures  

Microsoft Academic Search

Four anthocyanins from Ajuga reptans flowers and its cell cultures were isolated, and a fifth was also characterized by HPLC-mass spectrometry. By means of chemical and spectroscopic analyses, their structures were identified as delphinidin 3-(p-coumaroyl-feruloyl)sophoroside-5-malonylglucoside, delphinidin 3-(diferuloyl)sophoroside-5-malonylglucoside, and cyanidin 3-(di-p-coumaroyl)sophoroside-5-glucoside, respectively. The other two were tentatively identified as delphinidin 3-(diferuloyl)sophoroside-5-glucoside and cyanidin 3-(feruloyl-p-coumaroyl)sophoroside-5-malonylglucoside. In neutral aqueous solution, the crude extract

Norihiko Terahara; Alfons Callebaut; Riichiro Ohba; Tadahiro Nagata; Mayumi Ohnishi-Kameyama; Masahiro Suzuki



Demonstration of long-chain n-alkyl caffeates and delta7-steryl glucosides in the bark of Acacia species by gas chromatography-mass spectrometry.  


The GC-MS identification of several abundant long-chain aliphatic n-alkyl caffeates, together with other phydroxycinnamic acid esters, in the dichloromethane extracts of the bark of Acacia dealbata and A. melanoxylon, is reported. In addition, the unambiguous differentiation between two delta7-steryl glucosides (namely, spinasteryl glucoside and dihydrospinasteryl glucosides) and the homologous delta5-steryl glucosides was achieved based on the EI-MS fragmentation features of their trimethylsilyl derivatives. PMID:17439016

Freire, Carmen S R; Silvestre, Armando J D; Neto, Carlos Pascoal


Iridoid compound 10-O-trans-p-Coumaroylcatalpol extends longevity and reduces alpha synuclein aggregation in Caenorhabditis elegans.  


Aging, the major cause of several ailments has led to intense exploration of potential drugs that delay aging and its associated effects. We mined the information on traditional Indian medicines and identified an iridoid, 10-O-trans-p-Coumaroylcatalpol (OCC), a major ingredient of Premna integrifolia Linn. (syn: Premna serratifolia). OCC forms an important constituent of famous herbal formulation 'Dashmula', a ten herb formulation, commonly used for its various medicinal properties. Employing model system C. elegans, the effect of OCC on life span, stress resistance, chemotaxis, the content of reactive oxygen species (ROS) and on the aggregation of alpha synuclein was studied. OCC extended the mean life span of nematodes, increased their tolerance against chemical induced stress, improved the chemotaxis index and reduced the ROS content. Further, the aggregation of Parkinson's disease (PD) associated protein, alpha synuclein (asyn), was decreased when transgenic a-syn expressing worms were raised on OCC mixed diet. We extended the studies further to explore the possible genetic mechanism that mediates the observed effects of OCC. Employing the genetic knockout mutants TK22 [mev-1(kn1)III]; GR1307 [daf-16(mgDf50)I]; VC199 [sir-2.1(ok434)IV] and transgenic GFP expressing strain TJ356 [zls356; DAF-16::GFP], our studies revealed that the effects were mediated by daf-16 and not by sir-2.1 or mev-1. Our results indicate that OCC has the ability to ameliorate a-syn aggregation, reduce oxidative stress and promote longevity in C. elegans via activation of longevity promoting transcription factor DAF-16. Thus, OCC may serve as a lead compound of plant origin for important nutraceutical intervention against aging and age associated PD. PMID:23244417

Shukla, Virendra; Phulara, Suresh C; Yadav, Deepti; Tiwari, Sudeep; Kaur, Supinder; Gupta, M M; Nazir, Aamir; Pandey, Rakesh



GABA, ?-alanine and glycine in the digestive juice of privet-specialist insects: convergent adaptive traits against plant iridoids.  


The privet tree, Ligustrum obtusifolium (Oleaceae), defends its leaves against insects with a strong lysine-decreasing activity that make proteins non-nutritive. This is caused by oleuropein, an iridoid glycoside. We previously found that some privet-specialist caterpillars adapt by secreting glycine in the digestive juice as a neutralizer that prevents the loss of lysine. Here, we extended the survey into 42 lepidopteran and hymenopteran species. The average concentration of glycine in digestive juice for 11 privet-feeding species (40.396 mM) was higher than that for 32 non-privet-feeding species (2.198 mM). The glycine concentrations exceeded 10 mM in 7 out of 11 privet-feeding species. In Macrophya timida (Hymenoptera), it reached 164.8 mM. Three out of the four remaining privet-feeding species had other amino acids instead. Larvae of a privet-specialist butterfly, Artopoetes pryeri (Lycaenidae), had a high concentration (60.812 mM) of GABA. In two other specialists, ?-alanine was found. GABA, ?-alanine, and glycine as well as alanine, amines, and ammonium ion inhibited the lysine decrease, indicating that amino residues are responsible for the inhibition. However, the three amino acids found in the specialists were far more effective (20 mM showed 80% inhibition) than the rest (>140 mM was required for 80% inhibition). Our results show a clear and rare case of the apparent convergent evolution of herbivores' molecular adaptations of feeding on a plant with a chemical defense in a manner that minimizes the cost of adaptation. The novel role of GABA in plant-herbivore interactions shown here is probably the first reported non-neuronal role of animal-derived GABA. PMID:20809148

Konno, Kotaro; Hirayama, Chikara; Yasui, Hiroe; Okada, Sachiko; Sugimura, Masahiro; Yukuhiro, Fumiko; Tamura, Yasumori; Hattori, Makoto; Shinbo, Hiroshi; Nakamura, Masatoshi



Analgesic effect of iridoid glycosides from Paederia scandens (LOUR.) MERRILL (Rubiaceae) on spared nerve injury rat model of neuropathic pain.  


Iridoid glycosides of Paederia scandens (IGPS) is a major active component isolated from traditional Chinese herb P. scandens (LOUR.) MERRILL (Rubiaceae). The aim of the present study was to investigate the analgesic effect of IGPS on spared nerve injury (SNI) model of neuropathic pain. The SNI model in rats was established by complete transection of the common peroneal and tibial distal branches of the sciatic nerve, leaving the sural branch intact. The mechanical withdrawal threshold (MWT) in response to mechanical stimulation was measured by electronic von Frey filaments on day 1 before operation and on days 1, 3, 5, 7, 10, and 14 after operation, respectively. Nitric oxide synthase (NOS) activity and nitric oxide (NO) production of spinal cord were measured by spectrophotometry and its cyclic guanosine monophosphate (cGMP) content by radioimmunoassay, mRNA expression of inducible NOS (iNOS) and protein kinase G type I (PKG-I, including PKG ?? and PKG I?) of spinal cord were analyzed by RT-PCR. There was a marked mechanical hypersensitivity response observed on day 1 after operation in SNI model, which accompanied with decreased MWT. Treatment with IGPS (70, 140, 280 mg/kg) significantly alleviated SNI-induced mechanical hypersensitivity response evidenced by increased MWT; as well as markedly decreased NOS activity, NO and cGMP levels. At the same time, IGPS (70, 140, 280 mg/kg) could also inhibit mRNA expression of iNOS, PKG ?? and PKG I? in the spinal cord. The results suggested that IGPS possesses antinociceptive effect, which may be partly related to the inhibition of NO/cGMP/PKG signaling pathway in the rat SNI model of neuropathic pain. PMID:22698486

Liu, Mei; Zhou, Lanlan; Chen, Zhiwu; Hu, Caibiao



Occurrence of Deoxynivalenol and Its Major Conjugate, Deoxynivalenol3Glucoside, in Beer and Some Brewing Intermediates  

Microsoft Academic Search

Since deoxynivalenol (DON), the main representative of Fusarium toxic secondary metabolites, is a relatively common natural contaminant in barley, its traces can be detected in many commercial beers. Our previous study reporting for the first time the occurrence of relatively high levels of DON- 3-glucoside (DON-3-Glc) in malt and beer prepared from relatively \\

Marta Kostelanska; Jana Hajslova; Milena Zachariasova; Alexandra Malachova; Kamila Kalachova; Jan Poustka; Jaromir Fiala; Peter M. Scott; Franz Berthiller; Rudolf Krska



A new stilbene glucoside from the roots of Polygonum multiflorum Thunb  

Microsoft Academic Search

One new stillbene glucoside (6), along with five known compounds (1–5), were isolated from the roots ofPolygonum multiflorum Thumb., and their chemical structures established based on physicochemical and spectroscopic data. Of the compounds, compound3 showed DNA topoisomerase I and II inhibitory activities.

Ming-Lu Xu; Ming Shan Zheng; Yeon-Kyong Lee; Dong-Cheol Moon; Chong-Soon Lee; Mi-Hee Woo; Byeong-Seon Jeong; Eung Seok Lee; Yurngdong Jahng; Hyeun-Wook Chang; Seung-Ho Lee; Jong-Keun Son



Vitamin B6 Status Indicators Decrease in Women Consuming a Diet High in Pyridoxine Glucoside1\\  

Microsoft Academic Search

Previous research has shown that the pyridoxine glucoside (PNG) form of vitamin B-6 has a reduced bioavailability compared with pyridoxine, but its effect on vitamin B-6 status has not been assessed. Following an 8-d adjustment period, nine women con sumed diets containing a high or low amount of PNG for 18 d each, in a crossover design. The high and



Attachment of rhamnosyl glucoside on quercetin confers potent iron-chelating ability on its antioxidant properties  

Microsoft Academic Search

The pharmacological essence of the natural addition of rhamnosyl glucoside on quercetin that is commonly found in nature in medicinal plants is rather obscure. The present study therefore sought to compare the antioxidant activities of both compounds by comparing their ability to decolourise DPPH radicals, reduce Fe3+, chelate Fe2+, prevent deoxyribose degradation and inhibit hepatic thiobarbituric acid reactive substances induced

P. A. Omololu; J. B. T. Rocha; I. J. Kade



Construction of cellobiose phosphorylase variants with broadened acceptor specificity towards anomerically substituted glucosides.  


The general application of glycoside phosphorylases such as cellobiose phosphorylase (CP) for glycoside synthesis is hindered by their relatively narrow substrate specificity. We have previously reported on the creation of Cellulomonas uda CP enzyme variants with either modified donor or acceptor specificity. Remarkably, in this study it was found that the donor mutant also displays broadened acceptor specificity towards several beta-glucosides. Triple mutants containing donor (T508I/N667A) as well as acceptor mutations (E649C or E649G) also display a broader acceptor specificity than any of the parent enzymes. Moreover, further broadening of the acceptor specificity has been achieved by site-saturation mutagenesis of residues near the active site entrance. The best enzyme variant contains the additional N156D and N163D mutations and is active towards various alkyl beta-glucosides, methyl alpha-glucoside and cellobiose. In comparison with the wild-type C. uda CP enzyme, which cannot accept anomerically substituted glucosides at all, the obtained increase in substrate specificity is significant. The described CP enzyme variants should be useful for the synthesis of cellobiosides and other glycosides with prebiotic and pharmaceutical properties. PMID:20517986

De Groeve, Manu R M; Remmery, Laurens; Van Hoorebeke, Annelies; Stout, Jan; Desmet, Tom; Savvides, Savvas N; Soetaert, Wim



Involvement of Streptococcus gordonii Beta-Glucoside Metabolism Systems in Adhesion, Biofilm Formation, and In Vivo Gene Expression  

PubMed Central

Streptococcus gordonii genes involved in beta-glucoside metabolism are induced in vivo on infected heart valves during experimental endocarditis and in vitro during biofilm formation on saliva-coated hydroxyapatite (sHA). To determine the roles of beta-glucoside metabolism systems in biofilm formation, the loci of these induced genes were analyzed. To confirm the function of genes in each locus, strains were constructed with gene inactivation, deletion, and/or reporter gene fusions. Four novel systems responsible for beta-glucoside metabolism were identified, including three phosphoenolpyruvate-dependent phosphotransferase systems (PTS) and a binding protein-dependent sugar uptake system for metabolizing multiple sugars, including beta-glucosides. Utilization of arbutin and esculin, aryl-beta-glucosides, was defective in some mutants. Esculin and oligochitosaccharides induced genes in one of the three beta-glucoside metabolism PTS and in four other genetic loci. Mutation of genes in any of the four systems affected in vitro adhesion to sHA, biofilm formation on plastic surfaces, and/or growth rate in liquid medium. Therefore, genes associated with beta-glucoside metabolism may regulate S. gordonii in vitro adhesion, biofilm formation, growth, and in vivo colonization.

Kilic, Ali O.; Tao, Lin; Zhang, Yongshu; Lei, Yu; Khammanivong, Ali; Herzberg, Mark C.



Acylated Cyanidin 3-sophoroside-5-glucosides from the Purple Roots of Red Radish (Raphanus sativus L.) ‘Benikanmi’  

Microsoft Academic Search

Four new acylated cyanidin glycosides were isolated from the purple root peers of Raphanus sativus L. 'Benikanmi', along with five known anthocyanins. These pigments were based on cyanidin 3-sophoroside-5- glucoside, and acylated diversely with malonic, p-coumaric, caffeic, and ferulic acids. Two pigments of these four new anthocyanins were determined to be cyanidin 3-O-(2-O-(?-glucopyranosyl)-6-O-(trans-feruloyl)-?- glucopyranoside)-5-O-(6-O-(malonyl)-?-glucopyranoside) and cyanidin 3-(2-(glucosyl)-6-(cis-p-coumaroyl)- glucoside)-5-(6-(malonyl)-glucoside) by chemical

Fumi Tatsuzawa; Norio Saito; Kenjiro Toki; Koichi Shinoda; Atsushi Shigihara; Toshio Honda



Identification of rice ?-glucosidase with high hydrolytic activity towards salicylic acid ?-D-glucoside.  


?-Glucosidases (EC split ?-glucosidic linkages at the non-reducing end of glucosides and oligosaccharides to release ?-D-glucose. One of the important functions of plant ?-glucosidase is deglucosylation of inactive glucosides of phytohormones to regulate levels of active hormones. Tuberonic acid is a jasmonate-related compound that shows tuber-inducing activity in the potato. We have identified two enzymes, OsTAGG1 and OsTAGG2, that have hydrolytic activity towards tuberonic acid ?-D-glucoside in rice (Oryza sativa L.). The expression of OsTAGG2 is upregulated by wounding and by methyl jasmonate, suggesting that this isozyme is involved in responses to biotic stresses and wounding, but the physiological substrate of OsTAGG2 remains ambiguous. In this study, we produced recombinant OsTAGG2 in Pichia pastoris (rOsTAGG2P), and investigated its substrate specificity in detail. From 1 L of culture medium, 2.1 mg of purified recombinant enzyme was obtained by ammonium sulfate precipitation and Ni-chelating column chromatography. The specific activity of rOsTAGG2P (182 U/mg) was close to that of the native enzyme (171 U/mg), unlike recombinant OsTAGG2 produced in Escherichia coli, which had approximately 3-fold lower specific activity than the native enzyme. The optimum pH and temperature for rOsTAGG2P were pH 3.4 and 60 °C. After pH and heat treatments, the enzyme retained its original activity in a pH range of 3.4-9.8 and below 55 °C. Native OsTAGG2 and rOsTAGG2P showed 4.5-4.7-fold higher activities towards salicylic acid ?-D-glucoside, an inactive storage-form of salicylic acid, than towards tuberonic acid ?-D-glucoside (TAG), although OsTAGG2 was originally isolated from rice based on TAG-hydrolytic activity. PMID:23649259

Himeno, Nami; Saburi, Wataru; Wakuta, Shinji; Takeda, Ryosuke; Matsuura, Hideyuki; Nabeta, Kensuke; Sansenya, Sompong; Ketudat Cairns, James R; Mori, Haruhide; Imai, Ryozo; Matsui, Hirokazu



Preparation of quinoline hexose analogs as novel chloroquine-resistant malaria treatments (1). Synthesis of 4-hydroxyquinoline-beta-glucosides.  


Quinoline hexose analogs are expected to be useful as novel agents for treatment of chloroquine-resistant malaria. Here, we report preparation of 4-hydroxy quinoline-beta-glucosides from anilines in 4 steps. PMID:17473479

Suzuki, Hiroshi; Aly, Nagwa S M; Wataya, Yusuke; Kim, Hye-Sook; Tamai, Ikumi; Kita, Masaki; Uemura, Daisuke



Effects and mechanisms of total glucosides of paeony on joint damage in rat collagen-induced arthritis  

Microsoft Academic Search

Objective and design: To investigate the therapeutic effects and mechanisms of total glucosides of paeony (TGP), an effective compound of Chinese traditional herbal medicine (CTM), on collagen -induced arthritis (CIA) in rats.

L. Zhu; W. Wei; Y.-Q. Zheng; X.-Y. Jia



Factors affecting the specificity of ?-glucosidase from Fusarium oxysporum in enzymatic synthesis of alkyl- ?- d-glucosides  

Microsoft Academic Search

Fusarium oxysporum?-glucosidase has been used to catalyze the production of alkyl-?-d-glucosides from various disaccharides, based on the transglucosylation reaction, in the presence of primary, secondary and tertiary alcohols as glucosyl acceptors. Primary alcohols were found to be the best acceptors. The influence of the glucosyl donor concentration, as well as the enzyme specificity towards the cleaved glucosidic bond and the

M Makropoulou; P Christakopoulos; C Tsitsimpikou; D Kekos; F. N Kolisis; B. J Macris



Protective effects of naringenin-7- O-glucoside on doxorubicin-induced apoptosis in H9C2 cells  

Microsoft Academic Search

Doxorubicin, a widely used chemotherapeutic agent, can give rise to severe cardiotoxicity by inducing cardiomyocyte apoptosis. Dracocephalum rupestre Hance, a Chinese traditional herb, has therapeutic potential for cardiovascular diseases. Naringenin-7-O-glucoside is the main active constituent of D. rupestre and there is increasing interest in its therapeutic applications. The aim of this study was to evaluate the effects of naringenin-7-O-glucoside on

Xiuzhen Han; Dongmei Ren; Peihong Fan; Tao Shen; Hongxiang Lou



?-glucosidase from Penicillium aculeatum hydrolyzes exo-, 3-O-, and 6-O-?-glucosides but not 20-O-?-glucoside and other glycosides of ginsenosides.  


A novel ?-glucosidase from Penicillium aculeatum was purified as a single 110.5-kDa band on SDS-PAGE with a specific activity of 75.4 U?mg?¹ by salt precipitation and Hi-Trap Q HP and Resource Q ion exchange chromatographies. The purified enzyme was identified as a member of the glycoside hydrolase 3 family based on its amino acid sequence. The hydrolysis activity for p-nitrophenyl-?-D-glucopyranoside was optimal at pH 4.5 and 70 °C with a half-life of 55 h. The enzyme hydrolyzed exo-, 3-O-, and 6-O-?-glucosides but not 20-O-?-glucoside and other glycosides of ginsenosides. Because of the novel specificity, this enzyme had the transformation pathways for ginsenosides: Rb????Rd???F????compound K, Rb????compound O???compound Y, Rc???compound Mc????compound Mc, Rg????Rh????aglycone protopanaxadiol (APPD), Rg????F?, and Rf???Rh????aglycone protopanaxatriol (APPT). Under the optimum conditions, the enzyme converted 0.5 mM Rb?, Rc, Rd, Rg?, Rg?, and Rf to 0.49 mM compound Y, 0.49 mM compound Mc, 0.47 mM compound K, 0.23 mM APPD, 0.49 mM?F?, and 0.44 mM APPT after 6 h, respectively. PMID:23504080

Lee, Gi-Woong; Yoo, Mi-Hyun; Shin, Kyung-Chul; Shin, Kyung-Cheol; Kim, Kyoung-Rok; Kim, Yeong-Su; Lee, Ki-Won; Oh, Deok-Kun



Production of ascorbic acid glucoside by alginate-entrapped mycelia of Aspergillus niger  

Microsoft Academic Search

The mycelia of Aspergillus niger, cultivated in a medium containing 45 g l?1 maltose, 66 g l?1 yeast extract, and 5 g l?1 K2HPO4 at 30°C and 200 rpm, were used as a biocatalyst in the glucosylation of ascorbic acid. Free mycelia from 3-day-old culture,\\u000a when used in a 6-h reaction with maltose as the acyl donor, gave 16.07 g l?1 ascorbic acid glucoside corresponding

Hsin-Ju Hsieh; Kai-Yu Tung; Giridhar R. Nair; I-Ming Chu; Wen-Teng Wu



Conformational change of giant DNA induced by ascorbic acid 2-glucoside in relation to radiosensitivity  

Microsoft Academic Search

We performed single-molecule observation of DNA double-strand breaks caused by Co60 ?-ray irradiation and quantitatively evaluated the protective effect of ascorbic acid 2-glucoside (AA-2G). AA-2G is a stable derivative of ascorbic acid. We found that AA-2G induces a significant conformational change on DNA. We also evaluated the protective effect of AA-2G against radiation-induced DNA double-strand breaks in a quantitative manner.

M. Suzuki; Y. Yoshikawa; Ning Chen; A. Zinchenko; T. Mori; T. Kanbe; S. Murata; T. Imanaka; K. Yoshikawa



Resveratrol glucoside (Piceid) synthesis in seeds of transgenic oilseed rape ( Brassica napus L .)  

Microsoft Academic Search

Resveratrol is a phytoalexin produced in various plants like wine, peanut or pine in response to fungal infection or UV irradiation,\\u000a but it is absent in members of the Brassicaceae. Moreover, resveratrol and its glucoside (piceid) are considered to have beneficial effects on human health, known to reduce\\u000a heart disease, arteriosclerosis and cancer mortality. Therefore, the introduction of the gene

Alexandra Hüsken; Alfred Baumert; Carsten Milkowski; Heiko C. Becker; Dieter Strack; Christian Möllers



Kiwifruits ( Actinidia deliciosa ) transformed with a Vitis stilbene synthase gene produce piceid (resveratrol-glucoside)  

Microsoft Academic Search

A stilbene synthase gene was isolated from three Vitis spp. (V. vinifera, V. labrusca and V. riparia). These genes were placed under the control of the cauliflower mosaic virus 35S promoter and introduced into kiwifruit (Actinidia deliciosa) plants by Agrobacterium-mediated gene transfer. The introduced gene(s) were expressed and piceid (resveratrol-glucoside) rather than resveratrol\\u000a was produced in the leaves of the

S. Kobayashi; C. K. Ding; Y. Nakamura; I. Nakajima; R. Matsumoto



Tetra-acylated cyanidin 3-sophoroside-5-glucosides from the flowers of Iberis umbellata L. (Cruciferae)  

Microsoft Academic Search

The structures of 11 acylated cyanidin 3-sophoroside-5-glucosides (pigments 1–11), isolated from the flowers of Iberis umbellata cultivars (Cruciferae), were elucidated by chemical and spectroscopic methods. Pigments 1–11 were acylated with malonic acid, p-coumaric acid, ferulic acid, sinapic acid and\\/or glucosylhydroxycinnamic acids.Pigments 1–11 were classified into four groups by the substitution patterns of the linear acylated residues at the 3-position of

Norio Saito; Fumi Tatsuzawa; Eri Suenaga; Kenjiro Toki; Koichi Shinoda; Atsushi Shigihara; Toshio Honda



Biological activity of quercetin-3- O -glucoside, a known plant flavonoid  

Microsoft Academic Search

Cytotoxic, phytotoxic, antimicrobial and antioxidant effects of quercetin 3-O-glucoside (Q3G) isolated by HPLC from aerial parts of Prangos ferulaceae was studied by MTT assay, lettuce germination assay, disk diffusion and DPPH method. Our results showed that Q3G exhibits\\u000a high antioxidant effect with RC50 of 22 ?g\\/mL, it has low cytotoxicity and no antibacterial effects. Q3G exhibits high phytotoxic effect with

Seyed Mehdi Razavi; Saber Zahri; Gholamreza Zarrini; Hossein Nazemiyeh; Sariyeh Mohammadi



Developmental fate of the cyanogenic glucoside linamarin in Costa Rican wild lima bean seeds  

Microsoft Academic Search

WHEN a seed germinates, we expect the defensive secondary compounds it contains to be transferred intact to the growing seedling, or variously decomposed to produce resources for the growing seedling. The seeds of wild indigenous Costa Rican lima beans (Phaseolus lunatus L.) contain about 3.45% fresh weight of linamarin1, a cyanogenic glucoside that can enzymatically decompose to produce 0.37% fresh

D. O. Clegg; E. E. Conn; D. H. JANZEN



Consequences of Transferring Three Sorghum Genes for Secondary Metabolite (Cyanogenic Glucoside) Biosynthesis to Grapevine Hairy Roots  

Microsoft Academic Search

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

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



New isopimarane diterpene and new cineole type glucoside from Nepeta prattii.  


Together with sixteen known compounds, a new isopimarane diterpene (prattol) and a new cineole type glucoside were isolated from Nepeta prattii. Their structures were elucidated on the basis of spectral methods as isopimar-15-en-3 beta,8 beta,20-triol, and (1R, 2R, 4S)-1,8-epoxy-p-methan-2-O-beta-D-glucopyranosyl(1-->6)-beta- D-glucopyranoside. PMID:11998451

Hou, Zhen-Fu; Tu, Yong-Qiang; Li, Yu



Obtaining Vitis Vinifera cell cultures producing higher amounts of malvidin-3- O -?-glucoside  

Microsoft Academic Search

To obtain a cell line of Vitis vinifera producing mainly malvidin-3-O-ß-glucoside, three methods were studied: the initiation of new cell cultures from different varieties, the modification of phytohormones in the culture media of a high anthocyanin-producing cell line, and the selection by small-aggregate cloning of new cell lines from this high producing strain. The latter technique gave a cell line

Stéphanie Krisa; Xavier Vitrac; Alain Decendit; Fabienne Larronde; Gérard Deffieux; Jean-Michel Mérillon



Novel macrocyclic C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents  

Microsoft Academic Search

Novel macrocyclic C-aryl glucoside SGLT2 inhibitors were designed and synthesized. Two different synthetic routes of macrocyclization were adopted to prepare novel ansa SGLT2 inhibitors. Among the compounds tested, [1,7]dioxacyclopentadecine macrocycles possessing methylthiophenyl at the distal ring 40 or ethoxyphenyl at the distal ring 23 showed the best in vitro inhibitory activity in this series to date (40, IC50=0.778nM and 23,

Min Ju Kim; Suk Ho Lee; So Ok Park; Hyunku Kang; Jun Sung Lee; Ki Nam Lee; Myung Eun Jung; Jeongmin Kim; Jinhwa Lee



Cyanidin-3-glucoside suppresses cytokine-induced inflammatory response in human intestinal cells: comparison with 5-aminosalicylic Acid.  


The potential use of polyphenols in the prevention and treatment of chronic inflammatory diseases has been extensively investigated although the mechanisms involved in cellular signaling need to be further elucidated. Cyanidin-3-glucoside is a typical anthocyanin of many pigmented fruits and vegetables widespread in the human diet. In the present study, the protection afforded by cyanidin-3-glucoside against cytokine-triggered inflammatory response was evaluated in the human intestinal HT-29 cell line, in comparison with 5-aminosalicylic acid, a well-established anti-inflammatory drug, used in inflammatory bowel disease. For this purpose, some key inflammatory mediators and inflammatory enzymes were examined. Our data showed that cyanidin-3-glucoside reduced cytokine-induced inflammation in intestinal cells, in terms of NO, PGE2 and IL-8 production and of iNOS and COX-2 expressions, at a much lower concentration than 5-aminosalicylic acid, suggesting a higher anti-inflammatory efficiency. Interestingly, cyanidin-3-glucoside and 5-aminosalicylic acid neither prevented IkB-? degradation nor the activation of NF-kB, but significantly reduced cytokine-induced levels of activated STAT1 accumulated in the cell nucleus. In addition, we established that phosphorylated p38 MAPK was not involved in the protective effect of cyanidin-3-glucoside or 5-aminosalicylic acid. Taking into account the high concentrations of dietary anthocyanins potentially reached in the gastrointestinal tract, cyanidin-3-glucoside may be envisaged as a promising nutraceutical giving complementary benefits in the context of inflammatory bowel disease. PMID:24039842

Serra, Diana; Paixão, Joana; Nunes, Carla; Dinis, Teresa C P; Almeida, Leonor M



Cyanidin-3-Glucoside Suppresses Cytokine-Induced Inflammatory Response in Human Intestinal Cells: Comparison with 5-Aminosalicylic Acid  

PubMed Central

The potential use of polyphenols in the prevention and treatment of chronic inflammatory diseases has been extensively investigated although the mechanisms involved in cellular signaling need to be further elucidated. Cyanidin-3-glucoside is a typical anthocyanin of many pigmented fruits and vegetables widespread in the human diet. In the present study, the protection afforded by cyanidin-3-glucoside against cytokine-triggered inflammatory response was evaluated in the human intestinal HT-29 cell line, in comparison with 5-aminosalicylic acid, a well-established anti-inflammatory drug, used in inflammatory bowel disease. For this purpose, some key inflammatory mediators and inflammatory enzymes were examined. Our data showed that cyanidin-3-glucoside reduced cytokine-induced inflammation in intestinal cells, in terms of NO, PGE2 and IL-8 production and of iNOS and COX-2 expressions, at a much lower concentration than 5-aminosalicylic acid, suggesting a higher anti-inflammatory efficiency. Interestingly, cyanidin-3-glucoside and 5-aminosalicylic acid neither prevented IkB-? degradation nor the activation of NF-kB, but significantly reduced cytokine-induced levels of activated STAT1 accumulated in the cell nucleus. In addition, we established that phosphorylated p38 MAPK was not involved in the protective effect of cyanidin-3-glucoside or 5-aminosalicylic acid. Taking into account the high concentrations of dietary anthocyanins potentially reached in the gastrointestinal tract, cyanidin-3-glucoside may be envisaged as a promising nutraceutical giving complementary benefits in the context of inflammatory bowel disease.

Serra, Diana; Paixao, Joana; Nunes, Carla; Dinis, Teresa C. P.; Almeida, Leonor M.



Isolation of novel glucosides related to gingerdiol from ginger and their antioxidative activities.  


Two novel glucosides of 6-gingerdiol were isolated from fresh ginger (Zingiber officinale Roscoe). Their structures were determined as 1-(4-O-beta-D-glucopyranosyl-3-methoxyphenyl)-3,5-dihydroxydecane (1) and 5-O-beta-D-glucopyranosyl-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)deca ne (2) by HRFAB-MS and NMR analyses, and the absolute configurations of both aglycons were identified as (3S,5S) by a comparison with synthetic compounds. After incubating these glucosides with acetone powder prepared from fresh ginger, they were confirmed to have been hydrolyzed to 6-gingerdiol by HPLC. This result suggests that these glucosides are the precursors or intermediates of 6-gingerdiol. To recognize their function, their antioxidative activities were investigated and compared to that of their aglycon, 6-gingerdiol, by a linoleic acid model system and by their DPPH radical-scavenging ability. Although 1 did not indicate any activity, 2 had as strong activity as the aglycon in both measurements. PMID:10691642

Sekiwa, Y; Kubota, K; Kobayashi, A



Hydrolysis of aromatic ?-glucosides by non-pathogenic bacteria confers a chemical weapon against predators.  


Bacteria present in natural environments such as soil have evolved multiple strategies to escape predation. We report that natural isolates of Enterobacteriaceae that actively hydrolyze plant-derived aromatic ?-glucosides such as salicin, arbutin and esculin, are able to avoid predation by the bacteriovorous amoeba Dictyostelium discoideum and nematodes of multiple genera belonging to the family Rhabditidae. This advantage can be observed under laboratory culture conditions as well as in the soil environment. The aglycone moiety released by the hydrolysis of ?-glucosides is toxic to predators and acts via the dopaminergic receptor Dop-1 in the case of Caenorhabditis elegans. While soil isolates of nematodes belonging to the family Rhabditidae are repelled by the aglycone, laboratory strains and natural isolates of Caenorhabditis sp. are attracted to the compound, mediated by receptors that are independent of Dop-1, leading to their death. The ?-glucosides-positive (Bgl(+)) bacteria that are otherwise non-pathogenic can obtain additional nutrients from the dead predators, thereby switching their role from prey to predator. This study also offers an evolutionary explanation for the retention by bacteria of 'cryptic' or 'silent' genetic systems such as the bgl operon. PMID:23677347

Sonowal, Robert; Nandimath, Krithi; Kulkarni, Sucheta S; Koushika, Sandhya P; Nanjundiah, Vidyanand; Mahadevan, S



Cassava Plants with a Depleted Cyanogenic Glucoside Content in Leaves and Tubers. Distribution of Cyanogenic Glucosides, Their Site of Synthesis and Transport, and Blockage of the Biosynthesis by RNA Interference Technology1  

PubMed Central

Transgenic cassava (Manihot esculenta Crantz, cv MCol22) plants with a 92% reduction in cyanogenic glucoside content in tubers and acyanogenic (<1% of wild type) leaves were obtained by RNA interference to block expression of CYP79D1 and CYP79D2, the two paralogous genes encoding the first committed enzymes in linamarin and lotaustralin synthesis. About 180 independent lines with acyanogenic (<1% of wild type) leaves were obtained. Only a few of these were depleted with respect to cyanogenic glucoside content in tubers. In agreement with this observation, girdling experiments demonstrated that cyanogenic glucosides are synthesized in the shoot apex and transported to the root, resulting in a negative concentration gradient basipetal in the plant with the concentration of cyanogenic glucosides being highest in the shoot apex and the petiole of the first unfolded leaf. Supply of nitrogen increased the cyanogenic glucoside concentration in the shoot apex. In situ polymerase chain reaction studies demonstrated that CYP79D1 and CYP79D2 were preferentially expressed in leaf mesophyll cells positioned adjacent to the epidermis. In young petioles, preferential expression was observed in the epidermis, in the two first cortex cell layers, and in the endodermis together with pericycle cells and specific parenchymatic cells around the laticifers. These data demonstrate that it is possible to drastically reduce the linamarin and lotaustralin content in cassava tubers by blockage of cyanogenic glucoside synthesis in leaves and petioles. The reduced flux to the roots of reduced nitrogen in the form of cyanogenic glucosides did not prevent tuber formation.

J?rgensen, Kirsten; Bak, S?ren; Busk, Peter Kamp; S?rensen, Charlotte; Olsen, Carl Erik; Puonti-Kaerlas, Johanna; M?ller, Birger Lindberg



Characterization and activities of S-adenosyl- l-methionine:cyanidin 3-glucoside 3?- O-methyltransferase in relation to anthocyanin accumulation in Vitis vinifera cell suspension cultures  

Microsoft Academic Search

A cell suspension of Vitis vinifera cv Gamay Fréaux was grown in a maintenance and an anthocyanin-promoting medium (APM). Time-course changes in anthocyanin accumulation and S-adenosyl-l-methionine:cyanidin 3-glucoside 3?-O-methyltransferase (CGMT) activity were examined throughout the growth cycle. An increase in anthocyanin accumulation mainly due to peonidin 3-glucoside and peonidin 3- p-coumaroylglucoside i.e. 3?-methylated derivatives of cyanidin 3-glucoside (Cy3G), of cells grown

Christophe Bailly; François Cormier; Chi Bao Do



Plant chemical defense against herbivores and pathogens: generalized defense or trade-offs?  

Microsoft Academic Search

Plants are often attacked by multiple enemies, including pathogens and herbivores. While many plant secondary metabolites show specific effects toward either pathogens or herbivores, some can affect the performance of both these groups of natural enemies and are considered to be “generalized defense compounds”. We tested whether aucubin and catalpol, two iridoid glycosides present in ribwort plantain ( Plantago lanceolata),

Arjen Biere; Hamida B. Marak; Jos M. M. van Damme



Octyl glucoside inhibits [{sup 14}C]DHP mineralization whereas peroxidase activity is stimulated in Phanerochaete chrysosporium  

SciTech Connect

Octyl glucoside stimulated peroxidase formation in Phanerochaete chrysosporium ME-446 cultivated in cellulose-based media. Addition of 0.1% of the nonionic surfactant resulted in a ninefold (143 U/L) and sixfold (119 U/L) increase in UP formation under conditions of N limitation and N excess, respectively. Octyl glucoside also stimulated MnP formation, but to a lesser extent than observed with LiP. The cellobiose-oxidizing enzymes (cellobiose dehydrogenase and cellobiose:quinone oxidoreductase) were stimulated by octyl glucoside when used at a concentration of up to 0.05%, but higher concentrations gave values similar to those for the controls. Little proteolytic activity was detected in the presence of the surfactant. In general, activities of the enzymes studied were of the same order as those seen using Tween-80. In contrast with Tween-80, octyl glucoside markedly inhibited [{sup 14}C]DHP mineralization. Attempts to account for the observed inhibition of synthetic lignin degradation by P. chrysosporium in the presence of octyl glucoside are discussed. 29 refs., 3 figs., 5 tabs.

Silva, A. [National Institute for Industrial Engineering and Technology (INETI), Lisbon (Portugal)]|[Univ of Lisboa (Portugal)



A new oviposition deterrent to the leafminer, Liriomyza trifolii: cucurbitane glucoside from Momordica charantia.  


A new cucurbitane glucoside, 23-O-beta-D-glucopyranosyl-7-hydroxy-3-O-malonylcucurbita-5,24-dien-19-al, named momordicine V, has been isolated from Momordica charantia leaves, along with the previously reported compounds, momordicines I, II, IV and 3-O-malonylmomordicine I. The structure of the new compound was established on the basis of spectral analysis, as well as by its conversion to momordicine II by alkaline catalyzed hydrolysis. Momordicine V deterred significantly the oviposition by L. trifolii on host plant leaves treated at 26.16 microg/cm2 leaf surface. PMID:17913080

Kashiwagi, Takehiro; Mekuria, Daniel Bisrat; Dekebo, Aman; Sato, Keiko; Tebayashi, Shin-ichi; Kim, Chul-Sa


A lupane-triterpene and a 3(2?1)abeolupane glucoside from Hovenia trichocarea  

Microsoft Academic Search

A new lupane-triterpene, hovenic acid and 3(2?1)abeolupane glucoside, hovetrichoside H were isolated from the fresh bark of Hovenia trichocarea, together with ceanothetric acid, (+)-lyoniresinol-3a-O-?-d-glucopyranoside, (?)-lyoniresinol-3a-O-?-d-glucopyranoside, and citrusin B. The structures of the new compounds were established by extensive NMR experiments and chemical methods. Hovenic acid was established to be 2?,3?,23-trihydroxylup-20(29)-en-28-oic acid (2?,23-dihydroxybetulinic acid). Hovetrichoside H was identified as 2?-carboxy-3?-hydroxy-3(2?1)abeolup-20(29)-en-27,28-dioic acid

Kazuko Yoshikawa; Yuko Kondo; Eiko Kimura; Shigenobu Arihara



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

Microsoft Academic Search

The reuteransucrase enzymes of Lactobacillus reuteri strain 121 (GTFA)\\u000aand L. reuteri strain ATCC 55730 (GTFO) convert sucrose into a-d-glucans\\u000a(labelled reuterans) with mainly a-(1fi4) glucosidic linkages (50% and\\u000a70%, respectively), plus a-(1fi6) linkages. In the present study, we report a\\u000adetailed analysis of various hybrid GTFA?O enzymes, resulting in the identification\\u000aof specific regions in the N-termini of the

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



A new diterpenoid glucoside and two new diterpenoids from the fruit of Vitex agnus-castus.  


A new labdane-type diterpenoid glucoside and two new labdane-type diterpenoids were isolated from the fruit (chasteberry) of Vitex agnus-castus L. (Verbenaceae) along with 14 known compounds comprising seven labdane-type diterpenoids, one halimane-type diterpenoid, two oleanane-type triterpenoids, two ursane-type triterpenoids, one aromadendrane-type sesquiterpenoid, and one flavonoid. Their structures were characterized on the basis of spectroscopic data as well as chemical evidence. Furthermore, the antioxidative activities of the flavonoid were evaluated using five different analyses. PMID:21372425

Ono, Masateru; Eguchi, Keisuke; Konoshita, Masatarou; Furusawa, Chisato; Sakamoto, Junich; Yasuda, Shin; Ikeda, Tsuyoshi; Okawa, Masafumi; Kinjo, Junei; Yoshimitsu, Hitoshi; Nohara, Toshihiro



Lipid profile of Helicobacter spp.: presence of cholesteryl glucoside as a characteristic feature.  

PubMed Central

The lipid and fatty acid profiles of eight Helicobacter spp. (H. nemestrinae, H. acinonyx, H. canis, Helicobacter sp. strain CLO-3, "H. rappini" [Flexispira rappini], H. pametensis, Helicobacter sp. strain Bird-B, and Helicobacter sp. strain Bird-C) and the fatty acid profiles of five additional species (H. pylori, H. felis, H. muridarum, H. mustelae, and H. fennelliae) were analyzed and compared. A heterologous fatty acid profile was observed among the Helicobacter spp., and on that basis the species could be divided into two groups. Group A had 19-carbon cyclopropane fatty acid (19:0cyc) and tetradecanoic acid (14:0) as the major fatty acids, and group B characteristically lacked the 19:0cyc and had hexadecanoic acid (16:0) and octadecenoic (18:1) acids as the major fatty acids. The species of group A are primarily gastric colonizers, and those of group B are primarily intestinal colonizers. Seven of the eight species studied showed the unusual and characteristic presence of cholesteryl glucosides (CGs), and most of these seven showed a very large amount (9.7 to 27.4% of the weight of total extractable lipid). The types of CGs and their distribution in different species were as follows: cholesteryl-6-O-acyl-alpha-D-glucopyranoside (cholesteryl-6-O-tetradecanoyl-alpha-D-glucopyranoside in H. nemestrinae and mainly cholesteryl-6-O-dodecanoyl-alpha-D-glucopyranoside in "H. rappini"), cholesteryl-alpha-D-glucopyranoside (H. nemestrinae, H. acinonyx, H. canis, Helicobacter sp. strain CLO-3, and "H. rappini"), and cholesteryl-6-O-phosphatidyl-alpha-D-glucopyranoside (H. nemestrinae, H. acinonyx, H. canis, and Helicobacter sp. strain CLO-3). Besides this, we could also detect cholesteryl acyl glucoside in H. acinonyx, cholesteryl glucoside in Helicobacter sp. strains Bird-B and -C, and cholesteryl phosphatidyl glucoside in "H. rappini" and Helicobacter sp. strain Bird-C. A selective accumulation of free cholesterol was observed in the neutral lipid fractions. On the basis of the detection of CGs in 11 of the 13 species studied so far, the presence of CGs appears to be a characteristic feature of the genus Helicobacter. In view of this and also because of a simple and rapid detection method described herein, the CGs can be used as a valuable chemotaxonomic marker.

Haque, M; Hirai, Y; Yokota, K; Mori, N; Jahan, I; Ito, H; Hotta, H; Yano, I; Kanemasa, Y; Oguma, K



Phytochemical and Antimicrobial Studies of Methyl Angolensate and Luteolin-7-O-glucoside Isolated from Callus Cultures of Soymida febrifuga  

PubMed Central

Soymida febrifuga (Roxb.) A. Juss. is an indigenous lofty deciduous medicinal tree, monotypic genus endemic to India. Hexane, ethyl acetate and methanol extracts of Soymida febrifuga root callus were tested for their phytochemical constituents and antimicrobial activity. Among them, ethyl acetate extract was found to be most effective, which on subjection to silica gel column chromatography led to the separation and isolation of methyl angolensate and luteolin-7-O-glucoside. Structures were determined by Nuclear Magnetic Resonance and Liquid Chromatographic Mass Spectroscopic methods. Further studies indicated that methyl angolensate and luteolin-7-O-glucoside had an anti-bacterial effect against Bacillus subtilis and Salmonella typhimurium, respectively. In addition to that methyl angolensate had an anti-fungal activity against Aspergillus niger while luteolin-7-O-glucoside inhibited Alternaria alternata.

Chiruvella, Kishore K.; Mohammed, Arifullah; Dampuri, Gayathri; Ghanta, Rama Gopal; Raghavan, Sathees C.



Genetic Screening Identifies Cyanogenesis-Deficient Mutants of Lotus japonicus and Reveals Enzymatic Specificity in Hydroxynitrile Glucoside Metabolism[W][OA  

PubMed Central

Cyanogenesis, the release of hydrogen cyanide from damaged plant tissues, involves the enzymatic degradation of amino acid–derived cyanogenic glucosides (?-hydroxynitrile glucosides) by specific ?-glucosidases. Release of cyanide functions as a defense mechanism against generalist herbivores. We developed a high-throughput screening method and used it to identify cyanogenesis deficient (cyd) mutants in the model legume Lotus japonicus. Mutants in both biosynthesis and catabolism of cyanogenic glucosides were isolated and classified following metabolic profiling of cyanogenic glucoside content. L. japonicus produces two cyanogenic glucosides: linamarin (derived from Val) and lotaustralin (derived from Ile). Their biosynthesis may involve the same set of enzymes for both amino acid precursors. However, in one class of mutants, accumulation of lotaustralin and linamarin was uncoupled. Catabolic mutants could be placed in two complementation groups, one of which, cyd2, encoded the ?-glucosidase BGD2. Despite the identification of nine independent cyd2 alleles, no mutants involving the gene encoding a closely related ?-glucosidase, BGD4, were identified. This indicated that BGD4 plays no role in cyanogenesis in L. japonicus in vivo. Biochemical analysis confirmed that BGD4 cannot hydrolyze linamarin or lotaustralin and in L. japonicus is specific for breakdown of related hydroxynitrile glucosides, such as rhodiocyanoside A. By contrast, BGD2 can hydrolyze both cyanogenic glucosides and rhodiocyanosides. Our genetic analysis demonstrated specificity in the catabolic pathways for hydroxynitrile glucosides and implied specificity in their biosynthetic pathways as well. In addition, it has provided important tools for elucidating and potentially modifying cyanogenesis pathways in plants.

Takos, Adam; Lai, Daniela; Mikkelsen, Lisbeth; Abou Hachem, Maher; Shelton, Dale; Motawia, Mohammed Saddik; Olsen, Carl Erik; Wang, Trevor L.; Martin, Cathie; Rook, Fred



Isolation, identification and stability of acylated derivatives of apigenin 7- O-glucoside from chamomile ( Chamomilla recutita [L.] Rauschert)  

Microsoft Academic Search

The major flavonoids in the white florets of chamomile (Chamomilla recutita [L.] Rauschert) were rapidly purified using a combination of polyamide solid-phase extraction and preparative HPLC. From the combined LC\\/MS, LC\\/MS\\/MS, and NMR data the apigenin glucosides were identified as apigenin 7-O-glucoside (Ap-7-Glc), Ap-7-(6?-malonyl-Glc), Ap-7-(6?-acetyl-Glc), Ap-7-(6?-caffeoyl-Glc), Ap-7-(4?-acetyl-Glc), Ap-7-(4?-acetyl,6?-malonyl-Glc), and a partially characterised apigenin-7-(mono-acetyl\\/mono-malonylglucoside) isomer. Malonyl and caffeoyl derivatives of Ap-7-Glc

Vanda Švehl??ková; Richard N. Bennett; Fred A. Mellon; Paul W. Needs; Sonia Piacente; Paul A. Kroon; Yongping Bao



Anticancer effect of ursolic acid stearoyl glucoside in chemically induced hepatocellular carcinoma.  


Hepatocellular carcinoma is one of the leading causes of death in cancer and yet no drug has proven to be a successful candidate for its treatment in advanced stages. Ursolic acid stearoyl glucoside (UASG) is a newly discovered triterpene in Lantana camara and there lies a possibility that it possess anti-hepatocellular carcinoma property. In the present study, we induced hepatocellular carcinoma in Wistar rats by diethylnitrosamine (DENA) and treated it with ursolic acid stearoyl glucoside. The ability to treat hepatocellular carcinoma was measured by comparing biochemical serum markers such as serum alanine aminotransferase, serum aspartate aminotransferase, serum alkaline phosphatase, and the specific marker for hepatocellular carcinoma, alpha fetoprotein. The histological studies of the livers were also performed. The results have shown significant elevated levels of these parameters as compared to normal control and the drug receiving groups have shown significant reduction in these marker levels. Histopathological studies also indicated the reduced liver damage in drug-treated groups. It was noted that a significant and dose-dependent reversal of DENA-diminished activity of antioxidant enzymes like superoxide dismutase, catalase, glutathione peroxidase, glutathione transferase, and the reduced DENA-elevated level of lipid peroxidation (LPO) with a marked change. UASG significantly suppressed free radical formation by scavenging the hydroxyl radicals. It also modulates the levels of LPO and markedly increases the endogenous antioxidant enzymes level in DENA-induced hepatocellular carcinogenesis. PMID:23512248

Kazmi, Imran; Narooka, Anil Raj; Afzal, Muhammad; Singh, Rajbala; Al-Abbasi, Fahad A; Ahmad, Aftab; Anwar, Firoz



Therapeutic potential of cholesteryl O-acyl ?-glucoside found in Helicobacter pylori.  


Steryl glycosides are derivatives of sterols where the 3?-hydroxy group is glycosylated. Some of them are further converted to steryl O-acyl glycosides. Steryl glycosides and their derivatives are widely distributed in plants, algae, and fungi, but are relatively rarely distributed in bacteria and animals. Accumulating evidence suggests that glycosylation of sterols not only modifies physicochemical properties of cell membranes but also alters immunogenicity of the cells. Helicobacter pylori, that colonizes the stomach and causes gastric diseases, is auxotrophic for cholesterol, so that it extracts this lipid from plasma membranes of epithelial cells of the host stomach. Since incorporation of cholesterol promotes immune responses of the host, Helicobacter pylori converts cholesterol to cholesteryl glucoside (ChG) and then to cholesteryl 6'-O-acyl glucoside (ChAcG) to evade the immune surveillance. We have found that ChAcG thus produced is specifically recognized by invariant V?14-J?18 TCR(+) (V?14) NKT cells in a CD1-dependent manner. We have also found that activation of V?14 NKT cells by administration of ChAcG retains homeostasis of immunity upon exposure to allergens and reduces the incidence of allergy. In this article, overview of immunological functions of steryl glycosides with an emphasis on the immunoregulatory functions of ChAcG, is demonstrated. PMID:22934809

Shimamura, M; Hidaka, H



New steroidal lactones and homomonoterpenic glucoside from fruits of Malva sylvestris L.  


Phytochemical investigation of the ethanolic extract of defatted fruits of Malva sylvestris Linn. (Malvaceae) led to the isolation of six new steroidal lactones and a homomonoterpenic glucoside along with beta-sitosterol-3-beta-D-glucopyranoside. The structures of new phytoconstituents have been elucidated as cholest-5-en-3a-ol-18(21)-olide (sylvestrosterol A), cholest-9(11)-en-3alpha-ol-18(21)-olide (sylvestrosterol B), cholest-4,6,22-trien-3alpha-ol-18(21)-olide (sylvestrosterol C), 2-methyl-6-methylene-n-decan-2-olyl- 3beta-D-glucopyranoside (malvanoyl glucoside), cholest-7-en-18(21)-olide-3alpha-olyl-3beta-D-glucopyranoside (sylvestrogenin A), cholest-9(11)-en-18(21)-olide-3alpha-olyl-3beta-D-glucopyranoside (sylvestrogenin B) and cholest-5-en-8(21)-olide-3alpha-olyl-3beta-D-glucopyranoside (sylvestrogenin C).The structures of all these phytoconstituents have been established on the basis of spectral data analysis and chemical reactions. PMID:21648194

Mustafa, Akhlaq; Ali, Mohammed


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


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 ?-d-glucopyranosidase activity and a secondary ?-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 ?-glucosides. There is evidence of functional redundancy in the D. dadantii ?-glucoside assimilation pathway. In contrast to other ?-glucoside assimilation systems, involving cytoplasmic phospho-?-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

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



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,...


Cholinesterase inhibitory and antioxidant properties of Verbascum mucronatum Lam. and its secondary metabolites.  


The aqueous extract of Verbascum mucronatum Lam. along with its fractions and secondary metabolites were assessed for their antioxidant, acetylcholinesterase (AChE), and butyrylcholinesterase (BChE) inhibitory activities. The antioxidant activity was evaluated by three methods: as 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, ferrous ion-chelating effect, and ferric-reducing antioxidant power (FRAP) tests. The AChE activity was determined by the Ellman method using an ELISA microplate reader. Phytochemical investigations revealed the presence of four iridoid glucosides, ajugol (1), aucubin (2), lasianthoside I (3) and catalpol (4), two saponins, ilwensisaponin A (5) and C (6), and a phenylethanoid glycoside, verbascoside (7), in Verbascum mucronatum. Their structures were elucidated by spectral techniques. The aqueous extract and fractions including the phenylethanoid glycoside 7 showed DPPH scavenger effect and had the best FRAP. Besides these results, one of the phenylethanoid fractions displayed the highest ferrous ion-chelating effect. While only 7 was found to possess moderate AChE inhibition, the extract, fractions, and all other tested compounds did not inhibit AChE and BChE. PMID:21319708

Kahraman, Cigdem; Tatli, I Irem; Orhan, Ilkay Erdogan; Akdemir, Zeliha S


Cloning and biochemical analysis of ?-glucoside utilization (bgl) operon without phosphotransferase system in Pectobacterium carotovorum subsp. carotovorum LY34.  


?-Glucosidases are widespread in bacteria and involved in the metabolism of various carbohydrate substrates. Studying of ?-glucoside utilization (bgl) operons on operon of Pectobacterium carotovorum subsp. carotovorum LY34 (Pcc LY34) will help us understanding how ?-glucoside utilization (bgl) operon can cooperate with other systems in bacterium caused soft-rot disease. Pcc LY34 causes soft-rot disease in plants and expresses multiple enzymatic forms of ?-glucosidases. To fully explore the ?-glucoside utilization system in Pcc LY34, we have isolated a bgl operon from a genomic library for screening of ?-glucosidase activities. Sequence analysis of a 3050bp cloned DNA fragment (accession number AY870655) shows two open reading frames (bglY and bglK) that are predicted to encode proteins of 474 and 278 amino acid residues, respectively. Pair wise similarity analysis suggests BglY is a beta-glucosidase (a member of glycosyl hydrolase family 1) and BglK is a transcriptional antiterminator protein. bglY promoter region contains an inverted repeat sequence similar to transcriptional terminator. Different from other four ?-glucoside utilization operons of Pcc LY34 strain, BglY contains signal peptide sequences as extracellular ?-glucosidase. Comparisons of five ?-glucoside utilization operons of Pcc LY34 strain showed that bglYK operon does not have phosphotransferase system domain which are responsible for sugar transportation. BglY shares 33-44% identity with other four ?-glucosidases of Pcc LY34 strain. Enzyme assay showed that purified BglY enzyme hydrolyzed salicin, arbutin, pNPG, and MUG, and exhibited maximal activity at pH 7.0 and 40°C. This activity was enhanced Mg(2+). Site-directed mutagenesis revealed E166 and E371 are critical of BglY's ?-glucosidase activity. PMID:22502871

An, Chang Long; Kim, Min Keun; Kang, Tae Ho; Kim, Jungho; Kim, Hoon; Yun, Han Dae



Pharmacokinetics of vitexin-4?-O-glucoside in rats after intravenous application.  


Vitexin-4?-O-glucoside (VOG), being a main component in the leaves of Crataegus pinnatifida Bge. var. major, was isolated and then three different doses (20, 40, and 60 mg/kg) of VOG were administered intravenously to rats. To study its pharmacokinetics, a simple and rapid HPLC method was developed using hesperidin as internal standard and the relative parameters were calculated by both compartmental and non-compartmental approach. The results showed that VOG fitted a two-compartment open model. The values of AUC increased proportionally within the range of 20-60 mg/kg. Additionally, ? half-life, ? half-life, (a)CL, MRT(0?t ), MRT(0?? ), and terminal half-life of VOG in rats showed significant differences between 20 mg/kg and other doses. Thereby, VOG presented a dose-dependent pharmacokinetics in the range of 20-60 mg/kg and non-linear pharmacokinetics at lower dose. PMID:22058050

Ying, Xi Xiang; Wang, Fei; Cheng, Zhong Zhe; Zhang, Wen Jie; Li, Hai Bo; Du, Yang; Liu, Xun; Wang, Si Yuan; Kang, Ting Guo



Some aspects of the inhibitory activity of hypolaetin-8-glucoside in acute inflammation.  


Hypolaetin-8-glucoside (H-8-G) has been examined for its mode of action in several models of acute inflammation. Its anti-inflammatory activity in carrageenan-induced inflammation of the rat hind-paw is not affected either by adrenalectomy or by phentolamine given with propranolol. H-8-G and its aglycone, hypolaetin, did not antagonize the actions of histamine, 5-hydroxytryptamine (5-HT), bradykinin or prostaglandin E2 (PGE2) on various smooth muscle preparations in-vitro, but protected erythrocytes from heat-induced lysis. The glycoside was more potent than troxerutin on capillary permeability increased by histamine and exerted inhibitory effects on protein exudation, leucocyte migration and beta-glucuronidase activity in the carrageenan air pouch, thereby showing some difference from indomethacin. These results are discussed in relation to the features of non-steroidal anti-inflammatory drugs (NSAID) and flavonoid anti-inflammatory actions. PMID:2886616

Villar, A; Gascó, M A; Alcaraz, M J



Secoiridoid glucosides and related compounds from Syringa reticulata and their antioxidant activities.  


A 70% EtOH extract from the bark of Syringareticulata has shown significant antioxidant activity. Chemical study on the extract resulted in the isolation of seventeen compounds (1-17), including a novel oleoside-type secoiridoid glucoside, reticuloside (1), and the structures were elucidated on the basis of extensive spectroscopic analyses. Among the isolated compounds, jaspolyoside (2), oleuropein (4) and 2-(3,4-dihydroxy)-phenylethyl-?-d-glucopyranoside (17), showed the most potent superoxide anion scavenging activity with the EC(50) values of 4.97, 2.57 and 4.97?M, respectively. The structure-activity relationship indicated that the presence of 2-(3,4-dihydroxyphenyl)-ethoxy group is important for exhibiting the activity. PMID:21955940

Bi, Xueyan; Li, Wei; Sasaki, Tatsunori; Li, Qin; Mitsuhata, Naoko; Asada, Yoshihisa; Zhang, Qingbo; Koike, Kazuo



The crystal structure and physicochemical properties of L-ascorbic acid 2-glucoside.  


The stable L-ascorbic acid glucoside produced by the action of the cyclomaltodextrin glucanotransferase (CGTase, EC from Bacillus stearothermophilus was crystallized from an aqueous solution. Determination of the molecular structure by single crystal X-ray analysis showed the compound to be 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G). The crystals are orthorhombic, space group P2(1)2(1)2(1), with unit-cell dimensions a = 11.929 A, b = 24.351 A, and c = 4.864 A. The D-glucopyranose residue has the 4C1 conformation. These conclusions are in good agreement with those based on the 13C-NMR spectrum. The general physicochemical properties of crystalline AA-2G are reported. PMID:1423355

Mandai, T; Yoneyama, M; Sakai, S; Muto, N; Yamamoto, I



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


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

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



Emodin-6-O-?-D-glucoside down-regulates endothelial protein C receptor shedding.  


Endothelial protein C receptor (EPCR) plays an important role in the protein C anticoagulation pathway and in the cytoprotective pathway. Previously, EPCR can be shed from the cell surface, which is mediated by tumor necrosis factor-? converting enzyme (TACE). Soluble EPCR levels are increased in patients with systemic inflammatory diseases. Recently, we reported that a new active compound, emodin-6-O-?-D-glucoside (EG) from Reynoutria japonica, has anti-inflammatory activities. However, little is known of the effects of EG on EPCR shedding. Here, we investigated this issue by monitoring the effects of EG on the phorbol-12-myristate 13-acetate (PMA) or the cecal ligation and puncture (CLP)-mediated EPCR shedding and its underlying mechanisms. Data showed that EG potently inhibited the PMA and CLP-induced EPCR shedding by suppressing TACE expression. Given these results, EG could be used as a candidate therapeutic for the treatment of vascular inflammatory diseases. PMID:23588681

Lee, Wonhwa; Ku, Sae-Kwang; Bae, Jong-Sup



Protocatechuic acid is the major human metabolite of cyanidin-glucosides.  


The metabolic fate of dietary anthocyanins (ACN) has not been fully clarified in humans. In all previous studies, the proportion of total ACN absorbed and excreted in urine was <1% intake. This study aimed to elucidate the human metabolism of cyanidin-glucosides (CyG) contained in blood orange juice (BOJ). One liter of BOJ, containing 71 mg CyG, was consumed by 6 healthy, fasting volunteers. Blood, urine, and fecal samples were collected at baseline and at different times up to 24 h after juice consumption. The content of native CyG, glucuronidated/methylated derivatives, and various phenolic acids was determined by HPLC/MS/MS. The serum maximal concentration of cyanidin-3-glucoside (Cy-3-glc) was 1.9 +/- 0.6 nmol/L and that of protocatechuic acid (PCA) was 492 +/- 62 nmol/L at 0.5 h and 2 h after juice consumption, respectively. The calculated total amounts in plasma corresponded for Cy-3-glc to 0.02% and for PCA to 44% of CyG ingested. CyG and glucuronidated/methylated metabolites, but not PCA, were detected in urine. ACN recovered in 24-h urine collections represented approximately 1.2% of the ingested dose. Both CyG (1.90 +/- 0.04 nmol/g) and PCA (277 +/- 0.2 nmol/g) were recovered in 24-h fecal samples. Data explained the metabolic fate of 74% of BOJ ACN. PCA was for the first time, to our knowledge, identified in humans as a CyG metabolite, accounting for almost 73% of ingested CyG. A high concentration of PCA may explain the short-term increased plasma antioxidant activity observed after intake of cyanidin-rich food and it can also contribute to the numerous health benefits attributed to dietary ACN consumption. PMID:17709440

Vitaglione, Paola; Donnarumma, Giovanna; Napolitano, Aurora; Galvano, Fabio; Gallo, Assunta; Scalfi, Luca; Fogliano, Vincenzo



Biosynthesis of geraniol and nerol and their ?-d-glucosides in Perlargonium graveolens and Rosa dilecta  

PubMed Central

1. 3R-[2-14C]Mevalonate was incorporated into geranyl and neryl ?-d-glucosides in petals of Rosa dilecta in up to 10.6% yield, and the terpenoid part was specifically and equivalently labelled in the moieties derived from isopentenyl pyrophosphate and 3,3-dimethylallyl pyrophosphate. A similar labelling pattern, with incorporations of 0.06–0.1% was found for geraniol or nerol formed in leaves of Pelargonium graveolens The former results provide the best available evidence for the mevalonoid route to regular monoterpenes in higher plants. 2. Incorporation studies with 3RS-[2-14C,(4R)-4-3H1]-mevalonate and its (4S)-isomer showed that the pro-4R hydrogen atom of the precursor was retained and the pro-4S hydrogen atom was eliminated in both alcohols and both glucosides. These results suggest that the correlation of retention of the pro-4S hydrogen atom of mevalonate with formation of a cis-substituted double bond, such as has been found in certain higher terpenoids, does not apply to the biosynthesis of monoterpenes. It is proposed that either nerol is derived from isomerization of geraniol or the two alcohols are directly formed by different prenyltransferases. Possible mechanisms for these processes are discussed. 3. The experiments with [14C,3H]mevalonate also show that in these higher plants, as has been previously found in animal tissue and yeast, the pro-4S hydrogen atom of mevalonate was lost in the conversion of isopentenyl pyrophosphate into 3,3-dimethylallyl pyrophosphate.

Banthorpe, Derek V.; Le Patourel, Geoffrey N. J.; Francis, Martin J. O.



Homonojirimycin analogues and their glucosides from Lobelia sessilifolia and Adenophora spp. (Campanulaceae).  


2,6-Dideoxy-7-O-(beta-D-glucopyranosyl) 2,6-imino-D-glycero-L-gulo- heptitol (7-O-beta-D-glucopyranosyl-alpha-homonojirimycin, 1) was isolated from the 50% methanol extract of the whole plant of Lobelia sessilifolia (Campanulaceae), which was found to potently inhibit rice alpha-glucosidase. Adenophorae radix, roots of Adenophora spp. (Campanulaceae), yielded new homonojirimycin derivatives, adenophorine (2), 1-deoxyadenophorine (3), 5-deoxyadenophorine (4), 1-C-(5-amino-5-deoxy-beta-D-galactopyranosyl)butane (beta-1-C-butyl-deoxygalactonojirimycin, 5), and the 1-O-beta-D-glucosides of 2 (6) and 4 (7), in addition to the recently discovered alpha-1-C-ethylfagomine (8) and the known 1-deoxymannojirimycin (9) and 2R,5R-bis(hydroxymethyl)-3R,4R- dihydroxypyrrolidine (DMDP, 10). Compound 4 is a potent inhibitor of coffee bean alpha-galactosidase (IC50 = 6.4 microM) and a reasonably good inhibitor of bovine liver beta-galactosidase (IC50 = 34 microM). Compound 5 is a very specific and potent inhibitor of coffee bean alpha-galactosidase (IC50 = 0.71 microM). The glucosides 1 and 7 were potent inhibitors of various alpha-glucosidases, with IC50 values ranging from 1 to 0.1 microM. Furthermore, 1 potently inhibited porcine kidney trehalase (IC50 = 0.013 microM) but failed to inhibit alpha-galactosidase, whereas 7 was a potent inhibitor of alpha-galactosidase (IC50 = 1.7 microM) without trehalase inhibitory activity. PMID:10782288

Ikeda, K; Takahashi, M; Nishida, M; Miyauchi, M; Kizu, H; Kameda, Y; Arisawa, M; Watson, A A; Nash, R J; Fleet, G W; Asano, N



Anti-allergic effects of enzymatically modified isoquercitrin (?-oligoglucosyl quercetin 3-O-glucoside), quercetin 3-O-glucoside, ?-oligoglucosyl rutin, and quercetin, when administered orally to mice.  


Quercetin, a flavonol distributed widely in edible and medicinal plants, has beneficial biological activities in vitro. However, the low water solubility of quercetin limits its bioavailability to exhibit activity in vivo. We evaluated the anti-allergic effects of quercetin, quercetin 3-O-glucoside (isoquercitrin, IQC), ?-oligoglucosyl rutin (?OR), and enzymatically modified isoquercitrin (?-oligoglucosyl isoquercitrin; EMIQ) in the murine ear passive cutaneous anaphylaxis (PCA) reaction using ovalbumin as an antigen. The substances to be tested were dissolved or suspended in water, and administered orally to mice (4 mmol 10 ml(-1) kg(-1)). EMIQ exhibited a significant inhibitory effect on the PCA reaction. We detected 600 ?M IQC and 95.1 ?M Q3Glcn in the plasma of mice 30 min after EMIQ treatment, suggesting that IQC and Q3Glcn might be the genuine active compounds mediating the anti-allergic effects of EMIQ. Oral treatments of quercetin and ?OR at this dosage exhibited no anti-allergic effect, and IQC showed less effect than EMIQ. Since IQC and quercetin cannot completely dissolve in water at this concentration, the water solubilities of these substances might affect their biological activities. ?OR dissolved well in water at the concentration used but plasma concentrations of quercetin metabolites in mice orally treated with ?OR were low, suggesting that ?OR might not be converted to IQC or quercetin by the enzymes in small intestine and thus not exhibit any activity. Glycosyl conjugation of quercetin with specific sugar motifs is an effective strategy to improve the biological activity of quercetin in vivo. PMID:23494818

Makino, Toshiaki; Kanemaru, Misaki; Okuyama, Shuji; Shimizu, Ryosuke; Tanaka, Hisashi; Mizukami, Hajime



Iridoid and secoiridoid glycosides in a hybrid complex of bush honeysuckles (Lonicera spp., Caprifolicaceae): implications for evolutionary ecology and invasion biology.  


Interspecific hybridization among non-native plant species can generate genotypes that are more reproductively successful in the introduced habitat than either parent. One important mechanism that may serve as a stimulus for the evolution of invasiveness in hybrids is increased variation in secondary metabolite chemistry, but still very little is known about patterns of chemical trait introgression in plant hybrid zones. This study examined the occurrence of iridoid and secoiridoid glycosides (IGs), an important group of plant defense compounds, in three species of honeysuckle, Lonicera morrowii A. Gray, Lonicera tatarica L., and their hybrid Lonicera×bella Zabel. (Caprifoliaceae), all of which are considered invasive in various parts of North America. Hybrid genotypes had a diversity of IGs inherited from both parent species, as well as one component not detected in either parent. All three species were similar in that overall concentrations of IGs were significantly higher in fruits than in leaves, and several compounds that were major components of fruits were never found in leaves. However, specific patterns of quantitative distribution among leaves, unripe fruits, and ripe fruits differed among the three species, with a relatively higher allocation to fruits in the hybrid species than for either parent. These patterns likely have important consequences for plant interactions with antagonistic herbivores and pathogens as well as mutualistic seed dispersers, and thus the potential invasiveness of hybrid and parental species in their introduced range. Methods established here for quantitative analysis of IGs will allow for the exploration of many compelling research questions related to the evolutionary ecology and invasion biology of these and other related species in the genus Lonicera. PMID:23228598

Whitehead, Susan R; Bowers, M Deane



Interactions between n-octyl and n-nonyl ?- d-glucosides and ?- and ?-cyclodextrins as seen by self-diffusion NMR  

Microsoft Academic Search

In this work 1H NMR self-diffusion experiments have been performed to determine the self-diffusion coefficients of n-octyl ?-d-glucoside and n-nonyl ?-d-glucoside in ?-cyclodextrin and ?-cyclodextrin solutions at 25?°C. Two questions are addressed. The first concerns the general influence on nonionic surfactant transport properties when cyclodextrins are present in solution. The second question concerns the influence of surfactant-chain length and cyclodextrin

Artur J. M. Valente; Markus Nilsson; Olle Söderman



Overexpression of the UGT73C6 alters brassinosteroid glucoside formation in Arabidopsis thaliana  

PubMed Central

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 The present study generates essential knowledge and molecular and biochemical tools, that will allow for the verification of a potential physiological role of UGT73C6 in BR glucosylation and will facilitate the investigation of the functional significance of BR glucoside formation in plants.



Protective Effects of Dietary Cyanidin 3- O-?- d-Glucoside on Liver Ischemia–Reperfusion Injury in Rats  

Microsoft Academic Search

We recently reported that feeding cyanidin 3-O-?-d-glucoside (C3G), a typical anthocyanin pigment, lowered the serum thiobarbituric acid-reactive substance (TBARS) concentration and increased the oxidation resistance of the serum to lipid peroxidation in rats. These results suggest that C3G acts as a potent antioxidant in vivo when acute oxidative stress is encountered. In the present study, we evaluated whether feeding C3G

Takanori Tsuda; Fumihiko Horio; Junzoh Kitoh; Toshihiko Osawa



Chemical studies on an endemic Philippine plant: sulfated glucoside and seco-A-ring triterpenoids from Dillenia philippinensis.  


The leaves of the endemic Philippine plant, Dillenia philippinensis yielded 11 compounds including one new sulfated glucoside and a new seco-A-ring oleanane-type triterpenoid. The molecular structures of these compounds were elucidated by means of NMR, MS and other spectroscopic techniques, as well as by comparison with literature data. Anti-Leishmania activity and cytotoxic activity against A549 human lung adenocarcinoma cells were also examined. PMID:21372426

Macahig, Rene Angelo Sarmiento; Matsunami, Katsuyoshi; Otsuka, Hideaki



Protective Effects of Amburoside A, a Phenol Glucoside from Amburana cearensis, against CCl4-lnduced Hepatotoxicity in Rats  

Microsoft Academic Search

The aim of this study was to investigate the pos- sible beneficial effects of amburoside A.AMB(4- (O-\\/3-D-glycopyranosyl )benzyl protocatechoate J. against carbon tetrachloride (CCI4)toxicity in rats. AMBis a phenol glucoside from the Brazilian medicinal plant Amburana cearensis. popularly used for the treatment of respiratory tract affec- tions. Acute AMB(25 and 50 mg\\/kg. i.p. or p.o.) treatments of CCl4-intoxicated rats significantiy

Francisco Noé Fonseca; Fábio Azevedo Pereira; Kirley M. Canut; Cícero F. B. Felipe; Márcia V. Pitombelra; Glauce S. B. Viana; Brasil Fortaleza


High-performance liquid chromatographic analysis of secoisolariciresinol diglucoside and hydroxycinnamic acid glucosides in flaxseed by alkaline extraction  

Microsoft Academic Search

A HPLC method was developed for the analysis of secoisolariciresinol diglucoside (SDG) and hydroxycinnamic acid glucosides in milled defatted flaxseed flour. Direct extraction by 1 M NaOH for 1 h at 20°C resulted in a higher yield than that obtained by hydrolysis of alcoholic extracts. An internal standard, o-coumaric acid, was used and the method was found to be easy,

Christina Eliasson; Afaf Kamal-Eldin; Roger Andersson; Per Åman



Quercetin3Glucoside Is Transported by the Glucose Carrier SGLT1 across the Brush Border Membrane of Rat Small Intestine  

Microsoft Academic Search

In the present study we investigated a possible involvement of the intestinal sodium-dependent glucose transporter (SGLT)1 in the absorption of quercetin-3-glucoside (Q3G). Pieces of rat jejunum or proximal colon were mounted in Ussing-type chambers and incubated under short-circuited conditions. Test flavonols were added to the mucosal or serosal bathing solution (initial concentration, 100 mol\\/L) and disappearance from the donor compartment

S. Wolffram; M. Block; P. Ader


Ontogenetic and regional changes in alpha-methyl-D-glucoside and L-proline intestinal transport in guinea pig.  


Regional brush-border uptakes of alpha-methyl-D-glucose and L-proline as well as morphometric parameters were studied from birth until adulthood in guinea pig small intestine. Intestinal weight, length, and area were fitted to two-segmented straight lines: from birth until the 2nd wk there was a sharp rise, whereas from day 14 to the adult stage the increase was slower. In everted sleeves, total uptakes of alpha-methyl-D-glucoside were higher on day 1 in duodenum, jejunum, and ileum, diminishing with increasing age. The initial fluxes of L-proline were higher during the 1st wk, diminishing to values that kept constant thereafter. Total uptakes of L-proline relative to alpha-methyl-D-glucoside showed a peak in the 1st wk in the three segments studied, reflecting the high demand for protein during the postnatal period. Regional ratios of L-proline to alpha-methyl-D-glucoside indicated that the ileum is the segment best suited to transporting this amino acid during the first 3 wk. Changes observed in the present study indicated a different pattern between hexose and amino acid transport during development and along the small intestine of guinea pig. PMID:9728089

Juan, M E; Turmo, M C; Planas, J M



Anthocyanin-rich black currant extract and cyanidin-3-O-glucoside have cytoprotective and anti-inflammatory properties.  


Periodontal diseases are a group of multifactorial polymicrobial infections characterized by a progressive inflammatory destruction of the periodontium. Flavonoids, including anthocyanins, are receiving increasing attention because of their promising human health benefits. The aim of our study was to investigate the effect of anthocyanins, pure or as part of a standardized black currant extract, on nicotine-induced cytotoxicity and lipopolysaccharide (LPS)-induced inflammatory responses in human cells. Using a colorimetric assay that measures cell viability, it was found that a pretreatment with an anthocyanin-rich black currant extract or cyanidin-3-O-glucoside neutralized the cytotoxic effect of nicotine on epithelial cells and fibroblasts in a dose-dependent manner. The black currant extract and cyanidin-3-O-glucoside also inhibited the LPS-induced secretion of interleukin-6 by human macrophages. The results of the present study suggest that black currant extract and cyanidin-3-O-glucoside may be promising candidates for the development of novel therapies to prevent and/or to treat smoking-related periodontal diseases. PMID:22738124

Desjardins, Jacynthe; Tanabe, Shinichi; Bergeron, Chantal; Gafner, Stefan; Grenier, Daniel



Cool-cultivated red leaf lettuce accumulates cyanidin-3-O-(6?-O-malonyl)-glucoside and caffeoylmalic acid.  


Cultivating lettuce in greenhouses at low temperatures improves its CO2-balance and may increase its content of flavonoid glycosides and phenolic acids. We cultivated 5weeks old red leaf lettuce seedlings at 20/15°C (day/night) or 12/7°C until plants reached comparable growth stages: small heads were harvested after 13 (warm) and 26 (cool)days, while mature heads were harvested after 26 (warm) or 52 (cool)days. Additionally, some plants were cultivated first cool then warm and vice versa (39days). Cool-cultivated small heads had higher concentrations of cyanidin-3-O-(6?-O-malonyl)-glucoside and caffeoylmalic acid than warm-cultivated ones but we detected no differences concerning quercetin and luteolin glycosides or di-O-caffeoyltartaric and 5-O-caffeoylquinic acid. Regarding mature heads, there were only differences concerning cyanidin-3-O-(6?-O-malonyl)-glucoside. We therefore suggest that only cyanidin-3-O-(6?-O-malonyl)-glucoside was truly responsive to temperatures alone. Previously reported contrasting effects may rather be due to comparison of different growth stages or interactive effects with radiation. PMID:24176360

Becker, Christine; Klaering, Hans-Peter; Kroh, Lothar W; Krumbein, Angelika



Pathobiochemical effect of acylated steryl-?-glucoside on aggregation and cytotoxicity of ?-synuclein.  


Cycad seed consumption by the native islanders of Guam is frequently associated with high rates of amyotrophic lateral sclerosis-parkinsonism dementia complex (ALS/PDC); furthermore, accompanying pathological examination often exhibits ?-synuclein inclusions in the neurons of the affected brain. Acylated steryl-?-glucoside (ASG) contained in cycad seeds is considered as causative environmental risk factor. We aimed to investigate whether ASG influences aggregation and cell toxicity of ?-synuclein. To understand whether ASG is a causative factor in the development of ALS/PDC, soybean-derived ASG was tested for its effect on in vitro aggregation of ?-synuclein using Thioflavin-T. ASG was also tested to determine whether it modulates ?-synuclein cytotoxicity in yeast cells. In addition, we determined whether an interaction between ASG and ?-synuclein occurs in the plasma membrane or cytoplasm using three factors: GM1 ganglioside, small unilamellar vesicles, and ATP. In the present study, we found that ASG-mediated acceleration of ?-synuclein aggregation is influenced by the presence of ATP, but not by the presence of GM1. ASG accelerated the ?-synuclein aggregation in the cytoplasm. ASG also enhanced ?-synuclein-induced cytotoxicity in yeast cells. This study demonstrated that ASG directly enhances aggregation and cytotoxicity of ?-synuclein, which are often observed in patients with ALS/PDC. These results, using assays that replicate cytoplasmic conditions, are consistent with the molecular mechanism that cytotoxicity is caused by intracellular ?-synuclein fibril formation in neuronal cells. PMID:22124781

Usuki, Seigo; Kamitani, Tetsu; Matsuo, Yasuhiro; Yu, Robert K



Salicylic acid and salicylic acid glucoside in xylem sap of Brassica napus infected with Verticillium longisporum  

PubMed Central

Salicylic acid (SA) and its glucoside (SAG) were detected in xylem sap of Brassica napus by HPLC–MS. Concentrations of SA and SAG in xylem sap from the root and hypocotyl of the plant, and in extracts of shoots above the hypocotyl, increased after infection with the vascular pathogen Verticillium longisporum. Both concentrations were correlated with disease severity assessed as the reduction in shoot length. Furthermore, SAG levels in shoot extracts were correlated with the amount of V. longisporum DNA in the hypocotyls. Although the concentration of SAG (but not SA) in xylem sap of infected plants gradually declined from 14 to 35 days post infection, SAG levels remained significantly higher than in uninfected plants during the whole experiment. Jasmonic acid (JA) and abscisic acid (ABA) levels in xylem sap were not affected by infection with V. longisporum. SA and SAG extend the list of phytohormones potentially transported from root to shoot with the transpiration stream. The physiological relevance of this transport and its contribution to the distribution of SA in plants remain to be elucidated.

Ratzinger, Astrid; Riediger, Nadine; von Tiedemann, Andreas



Chrysophanol-8-O-glucoside, an anthraquinone derivative in rhubarb, has antiplatelet and anticoagulant activities.  


Rhubarb is a widely used traditional medicine and has been reported to elicit a number of biological effects including anti-inflammatory and antiplatelet effects. In the present study, we investigated the effects of anthraquinone derivatives isolated from rhubarb on platelet activity. Of four anthraquinone derivatives isolated from rhubarb examined, chrysophanol-8-O-glucoside (CP-8-O-glc) was found to have the most potent inhibitory effect on collagen- and thrombin-induced platelet aggregation. CP-8-O-glc-treated mice showed significantly prolonged bleeding times. Furthermore, CP-8-O-glc was found to have a significant inhibitory effect on rat platelet aggregation ex vivo and on thromboxane A(2) formation in vitro. In coagulation tests, CP-8-O-glc did not alter prothrombin time, and it prolonged the activated partial thromboplastin time. However, CP-8-O-glc only inhibited platelet phosphatidylserine exposure, but not exert direct inhibition on intrinsic factors. This study demonstrates the antiplatelet and anticoagulant effects of CP-8-O-glc and suggests that this compound might be of therapeutic benefit for the prevention of platelet-related cardiovascular diseases. PMID:22302018

Seo, Eun Ji; Ngoc, Tran Minh; Lee, Sun-Mee; Kim, Yeong Shik; Jung, Yi-Sook



Cucurbitane glucosides from Momordica charantia leaves as oviposition deterrents to the leafminer, Liriomyza trifolii.  


The American serpentine leaf mining fly, Liriomyza trifolii, whose larva feeds on more than 120 plant species is well characterized by its high degree of polyphagy. Observations on the oviposition behavior by L. trifolii demonstrated that among cucurbitaceous plants, Momordica charantia is rarely attacked by L. trifolii. The methanol extract of M. charantia leaves strongly deterred the females from ovipositing on kidney bean leaves treated at a concentration of 1 g leaf equivalent extract/ml. Analysis of the polar fraction of the methanol extract of M. charantia leaves resulted in the isolation of a novel cucurbitane glucoside, 7-O-beta-D-glucopyranosyl-3,23-dihydroxycucurbita-5,24-dien-19-al, named momordicine IV, along with another known compound, momordicine II. Momordicine II and IV deterred oviposition by L. trifolii significantly when bioassays were carried out on kidney bean leaves treated at 75.6 and 20.3 microg/cm2 leaf surface, respectively. There was no synergistic effect on oviposition deterrent when the two compounds were combined in their natural abundance. PMID:16610222

Mekuria, Daniel Bisrat; Kashiwagi, Takehiro; Tebayashi, Shin-ichi; Kim, Chul-Sa


Spectral alteration and degradation of cyanidin-3-glucoside exposed to pulsed electric field.  


Anthocyanins are polyphenol antioxidants that have been shown to prevent many chronic diseases. The compounds are not stable, so they tend to be decolorized or degraded during processing and storage. In this study, the spectral characteristics alteration and degradation products of cyanidin-3-glucoside (Cyd-3-glc) exposed to pulsed electric field (PEF) were investigated, and the reaction kinetics was discussed. The intensity of the UV-vis spectra decreased noticeably upon PEF treatment without modification of the spectral pattern. Protocatechuic acid and 2,4,6-trihydroxybenzoic acid were identified as degradation products of both PEF and thermally treated Cyd-3-glc, but cyanidin present in thermally treated Cyd-3-glc was absent in PEF-treated Cyd-3-glc, indicating that the first step of Cyd-3-glc degradation induced by PEF was not the hydrolysis of glycosidic bonds, which was different from that of thermal degradation. With increased electric field intensity or treatment time, the degradation of Cyd-3-glc and the formation of protocatechuic acid were enhanced; their kinetics (except 7 kV/cm for protocatechuic acid formation) were well fitted to a first-order reaction. Meanwhile, a good correlation was present between Cyd-3-glc degradation and protocatechuic acid formation. PMID:20163112

Zhang, Yan; Sun, Jianxia; Hu, Xiaosong; Liao, Xiaojun



Enzymatic synthesis of piceid glucosides using maltosyltransferase from Caldicellulosiruptor bescii DSM 6725.  


Piceid is widely used in food, cosmetics, and pharmaceuticals because of its therapeutic benefits. However, the use of piceid as a drug is limited because of its low solubility. To increase solubility, we synthesized piceid glucosides using maltosyltransferase from Caldicellulosiruptor bescii. The MTase gene was cloned and expressed in Escherichia coli. The enzyme had a unique transfer specificity to the transfer of maltosyl units. Four piceid transglycosylation products were present and identified by thin-layer chromatography and recycling preparative high-performance liquid chromatography. The major product was purified by C(18) and gel filtration chromatography, and its molecular structure was determined using nuclear magnetic resonance spectroscopy to be ?-D-maltosyl-(1?4)-piceid. The solubility of maltosyl piceid was 8.54 × 10(3) and 1.86 × 10(3) times those of natural resveratrol and piceid, respectively, suggesting that the transglycosylation greatly increased the water solubility. This suggests that dietary intake of this compound can enhance the bioavailability of resveratrol in the human body. PMID:22823185

Park, Hyunsu; Kim, Jieun; Choi, Kyoung-Hwa; Hwang, Sungmin; Yang, Sung-Jae; Baek, Nam-In; Cha, Jaeho



Neuroprotection by tetrahydroxystilbene glucoside in the MPTP mouse model of Parkinson's disease.  


Our in vitro experiments suggested that tetrahydroxystilbene glucoside (TSG) affords a significant neuroprotective effect against MPP(+)-induced damage and apoptosis in PC12 cells though activation of the PI3K/Akt pathway. This study was aimed to investigate the potential neuroprotective effect of TSG in 1-methyl-4-phenyl-1,2,3,6-tetrahydropypridine (MPTP)-treated mouse model of Parkinson's disease (PD). We found that treatment of TSG protected dopaminergic neurons by preventing MPTP-induced decreases in substantia nigra tyrosine hydroxylase (TH)-positive cells and striatal dopaminergic transporter (DAT) protein levels. Furthermore, it was also associated with increasing striatal Akt and GSK3? phosphorylation, up-regulation of the Bcl-2/BAD ratio, and inhibition of the activation of caspase-9 and caspase-3. These results showed that TSG promoted dopamine neuron survival in vivo, the PI3K/Akt signaling pathway may have mediated the protection of TSG against MPTP, suggesting that TSG treatment might represent a neuroprotective treatment for PD. PMID:23911879

Zhang, Lingling; Huang, Linhong; Chen, Liangwei; Hao, Dingjun; Chen, Jianzong



Salicylic acid and salicylic acid glucoside in xylem sap of Brassica napus infected with Verticillium longisporum.  


Salicylic acid (SA) and its glucoside (SAG) were detected in xylem sap of Brassica napus by HPLC-MS. Concentrations of SA and SAG in xylem sap from the root and hypocotyl of the plant, and in extracts of shoots above the hypocotyl, increased after infection with the vascular pathogen Verticillium longisporum. Both concentrations were correlated with disease severity assessed as the reduction in shoot length. Furthermore, SAG levels in shoot extracts were correlated with the amount of V. longisporum DNA in the hypocotyls. Although the concentration of SAG (but not SA) in xylem sap of infected plants gradually declined from 14 to 35 days post infection, SAG levels remained significantly higher than in uninfected plants during the whole experiment. Jasmonic acid (JA) and abscisic acid (ABA) levels in xylem sap were not affected by infection with V. longisporum. SA and SAG extend the list of phytohormones potentially transported from root to shoot with the transpiration stream. The physiological relevance of this transport and its contribution to the distribution of SA in plants remain to be elucidated. PMID:19449088

Ratzinger, Astrid; Riediger, Nadine; von Tiedemann, Andreas; Karlovsky, Petr



pH-dependent interaction of rhodopsin with cyanidin-3-glucoside. 2. Functional aspects.  


Anthocyanins are a class of phytochemicals that confer color to flowers, fruits, vegetables and leaves. They are part of our regular diet and serve as dietary supplements because of numerous health benefits, including improved vision. Recent studies have shown that the anthocyanin cyanidin-3-O-glucoside (C3G) increased regeneration of the dim-light photoreceptor rhodopsin (Matsumoto et al. [2003] J. Agric. Food Chem., 51, 3560-3563). In an accompanying study (Yanamala et al. [2009] Photochem. Photobiol.), we show that C3G directly binds to rhodopsin in a pH-dependent manner. In this study, we investigated the functional consequences of C3G binding to rhodopsin. As observed previously in rod outer segments, regeneration of purified rhodopsin in detergent micelles is also accelerated in the presence of C3G. Thermal denaturation and stability studies using circular dichroism, fluorescence and UV/visible absorbance spectroscopy show that C3G exerts a destabilizing effect on rhodopsin structure while it only modestly alters G-protein activation and the rates at which the light-activated Metarhodopsin II state decays to opsin and free retinal. These results indicate that the mechanism of C3G-enhanced regeneration may be based on changes in opsin structure promoting access to the retinal binding pocket. PMID:19267871

Tirupula, Kalyan C; Balem, Fernanda; Yanamala, Naveena; Klein-Seetharaman, Judith


Proanthocyanidin profile of cowpea (Vigna unguiculata) reveals catechin-O-glucoside as the dominant compound.  


Proanthocyanidin (PA) profile and content can have important nutritional and health implications on plant foods. Six diverse cowpea phenotypes (black, red, green, white, light-brown and golden-brown) were investigated for PA composition using normal-phase HPLC and reversed-phase UPLC-TQD-MS. Catechin and (epi)afzelechin were the major flavan-3-ol units. Unusual composition was observed in all cowpea phenotypes with significant degrees of glycosylation in the monomers and dimers. The PA content of cowpea (dry basis) ranged between 2.2 and 6.3 mg/g. Monomeric flavan-3-ols were the largest group of PA (36-69%) in cowpea, with catechin-7-O-glucoside accounting for most (about 88%) of the monomers. The oligomers with degree of polymerization (DP) 2-4 ranged from 0.41 to 1.3 mg/g (15-20%), whereas DP>10 polymers accounted for only 13.5% of PA. Future studies that highlight the impact of the unusual cowpea PA profile on nutritional and bioactive properties of this important legume are warranted. PMID:23561075

Ojwang, Leonnard O; Yang, Liyi; Dykes, Linda; Awika, Joseph



Proteomic analysis for anti-atherosclerotic effect of tetrahydroxystilbene glucoside in rats.  


2,3,5,4'-tetrahydroxystilbene-2-O-?-D-glucoside (TSG) extracted from Polygonum multiflorum (a traditional Chinese medicinal herb) has been proved to exhibit significant anti-atherosclerotic activity. In this study, we firstly used proteomic analyses to investigate the molecular events occurring in the atherosclerotic rats after TSG treatment. Aortic samples were collected from the atherosclerotic rat group and the TSG-treated group, and its proteome was analyzed by two-dimensional gel electrophoresis (2-DE). Proteins showing significant changes in expression were identified and analyzed by matrix-assisted desorption/ionization time of flight mass spectrometry (MALDI-TOF-MS). As a result, 21 protein spots were found with significant differential expression after the treatment with TSG. A total of 18 spots were identified by database searching, and 17 spots matched with known proteins. Among these proteins (11 proteins up-regulated and six proteins down-regulated), five proteins were mainly involved in inflammation, cholesterol transport, cell apoptosis and adhesion. TSG treatment enhanced the expression of HSP 70, lipocortin 1 and Apo A-I, and inhibited the expression of calreticulin, vimentin. Furthermore, we randomly selected four proteins and confirmed the results of proteomic analysis by RT-PCR and western blotting. In conclusion, TSG treatment suppresses atherosclerosis by altering the expression of different proteins. Calreticulin, vimentin, HSP 70, lipocortin 1, and Apo A-I, are key proteins that may be novel molecular targets responsible for atherogenesis suppression induced by TSG treatment. PMID:23206751

Yao, Wenjuan; Fan, Wenjun; Huang, Chao; Zhong, Hui; Chen, Xiangfan; Zhang, Wei



Effect of heat/pressure on cyanidin-3-glucoside ethanol model solutions  

NASA Astrophysics Data System (ADS)

The stability of cyanidin-3-glucoside (Cy3gl) in 50% ethanol model solutions under heat/pressure treatments was investigated. Cy3gl was rapidly degraded when solutions were subjected to a heat/pressure treatment. The higher the pressure and the temperature used, the higher the degradation. Moreover, the degradation was increased according to increasing holding times. Parallel to the degradation of Cy3gl several hydrolytic products were formed and identified by LC-DAD/ESI-MS. The degradation of Cy3gl was well fitted to a first order reaction (R=0.99). This study pointed out the rate of susceptibility of Cy3gl in model solutions to degrade when exposed to a heat/pressure treatment and the trigger effect of high hydrostatic pressure to hydrolyse Cy3gl. By contrast, the degradation of anthocyanins in a food matrix (red grape extract solutions) was negligible after a heat/pressure process at 600MPa, 70°C during 1h (P >0.05).

Corrales, M.; Lindauer, R.; Butz, P.; Tauscher, B.



454 pyrosequencing based transcriptome analysis of Zygaena filipendulae with focus on genes involved in biosynthesis of cyanogenic glucosides  

PubMed Central

Background An essential driving component in the co-evolution of plants and insects is the ability to produce and handle bioactive compounds. Plants produce bioactive natural products for defense, but some insects detoxify and/or sequester the compounds, opening up for new niches with fewer competitors. To study the molecular mechanism behind the co-adaption in plant-insect interactions, we have investigated the interactions between Lotus corniculatus and Zygaena filipendulae. They both contain cyanogenic glucosides which liberate toxic hydrogen cyanide upon breakdown. Moths belonging to the Zygaena family are the only insects known, able to carry out both de novo biosynthesis and sequestration of the same cyanogenic glucosides as those from their feed plants. The biosynthetic pathway for cyanogenic glucoside biosynthesis in Z. filipendulae proceeds using the same intermediates as in the well known pathway from plants, but none of the enzymes responsible have been identified. A genomics strategy founded on 454 pyrosequencing of the Z. filipendulae transcriptome was undertaken to identify some of these enzymes in Z. filipendulae. Results Comparisons of the Z. filipendulae transcriptome with the sequenced genomes of Bombyx mori, Drosophila melanogaster, Tribolium castaneum, Apis mellifera and Anopheles gambiae indicate a high coverage of the Z. filipendulae transcriptome. 11% of the Z. filipendulae transcriptome sequences were assigned to Gene Ontology categories. Candidate genes for enzymes functioning in the biosynthesis of cyanogenic glucosides (cytochrome P450 and family 1 glycosyltransferases) were identified based on sequence length, number of copies and presence/absence of close homologs in D. melanogaster, B. mori and the cyanogenic butterfly Heliconius. Examination of biased codon usage, GC content and selection on gene candidates support the notion of cyanogenesis as an "old" trait within Ditrysia, as well as its origins being convergent between plants and insects. Conclusion Pyrosequencing is an attractive approach to gain access to genes in the biosynthesis of bio-active natural products from insects and other organisms, for which the genome sequence is not known. Based on analysis of the Z. filipendulae transcriptome, promising gene candidates for biosynthesis of cyanogenic glucosides was identified, and the suitability of Z. filipendulae as a model system for cyanogenesis in insects is evident.



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


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 ?-glucoside (R(?)) 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 ?-glucoside (R(?)) 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(?) (?G(0++) = 25.6 kcal/mol and E(a) = 26.5 kcal/mol) than in the reaction of R(?) (?G(0++) = 38.1 kcal/mol and E(a) = 37.2 kcal/mol), which is consistent with the experimental observation that ?-glucoside is generally much more reactive than the corresponding ?-glucoside. The lower activation barrier of the reaction of R(?) 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-?-d-glucoside (R(C?)) occurs with large ?G(0++) and E(a) values like those of ?-glucosides, because the methylene group of R(C?) does not contribute to the stereoelectronic effect. Also, the conformation around the C1-C2 bond is staggered in the transition state of the R(?) reaction but eclipsed in that of the R(?) reaction, which also leads to the larger reactivity of R(?). PMID:21082769

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



Synthesis of a series of phenylacetic acid 1-?-O-acyl glucosides and comparison of their acyl migration and hydrolysis kinetics with the corresponding acyl glucuronides.  


We report the synthesis of the 1-?-O-acyl glucoside conjugates of phenylacetic acid (PAA), R- and S-?-methyl-PAA and ?,?'-dimethyl-PAA, and measurement of their transacylation and hydrolysis reactivity by NMR methods. These are analogues of acyl glucuronides, the transacylation kinetics of which could be important in adverse drug effects. One aim of this work was to investigate whether, as previously postulated, the free carboxylate group of the acyl glucuronides plays a part in the mechanism of the internal acyl migration. In addition, such acyl glucosides are known to be endogenous biochemicals in their own right and investigation of their acyl migration propensities is novel. Our previously described selective acylation procedure has proved highly successful for 1-?-O-acyl glucuronide synthesis and when subsequently applied to 6-O-trityl glucose, it gave good yields and excellent anomeric selectivity. Mild acidolysis of the O-trityl intermediates gave the desired acyl glucosides in excellent yield with essentially complete ?-selectivity. Measurement of the acyl glucoside transacylation kinetics by (1)H NMR spectroscopy, based simply on the disappearance of the 1-?-isomer in aqueous buffer at pH 7.4, showed marked differences depending on the degree of methyl substitution. Further kinetic modelling of the isomerisation and hydrolysis reactions of the acyl glucosides showed considerable differences in kinetics for the various isomeric reactions. Reactions involving the -CH(2)OH group, presumably via a 6-membered ring ortho-ester intermediate, are facile and the ?-glucoside anomers are significantly more reactive than their ?-counterparts. By comparison with degradation rates for the corresponding acyl glucuronides, it can be inferred that substitution of the carboxylate by -CH(2)OH in the acyl glucosides has a significant effect on acyl migration for those compounds, especially for rapidly transacylating molecules, and that thus the charged glucuronide carboxylate is a factor in the kinetics. PMID:21152488

Iddon, Lisa; Richards, Selena E; Johnson, Caroline H; Harding, John R; Wilson, Ian D; Nicholson, Jeremy K; Lindon, John C; Stachulski, Andrew V



Phenylethanoid glucosides from in vitro propagated plants and callus cultures of Plantago lanceolata.  


The well-known medicinal plant Plantago lanceolata L. (ribwort plantain) was effectively propagated by direct organogenesis from segments of leaves and roots using MS medium supplemented with IAA (11.42 microM), kinetin (9.29 microM) for multiplication and IAA (5.71 microM) for rooting. The plantlets were successfully hardened (80 %) and transferred to field cultivation (100 %). Two lines of callus tissue, derived from leaves and roots, were obtained on MS medium without NH (4)NO (3) and supplemented with 2,4-D (4.52 microM) and kinetin ( 0.46 microM). From plant materials--leaf rosettes from in vitro, leaves from plants in field cultivation obtained by micropropagation, root-derived callus and leaf-derived callus--sixteen phenylethanoid glucosides representing nine different structures were isolated and identified by spectral methods (1D and 2D NMR) as known for the species: lavandulifolioside ( 1), plantamajoside ( 2,) acteoside ( 3); new for the species: leucosceptoside A ( 4), martynoside ( 5), desrhamnosylisoacteoside ( 6), plantainoside D ( 7), desrhamnosylacteoside ( 8) and - 2-(4-hydroxyphenyl)ethyl beta- D-glucopyranosyl-(1-->3)-4- O- trans- and cis- p-coumaroyl-beta- D-glucopyranoside ( 9)--the latter also being found for the first time in nature and named lancetoside. Only plantamajoside ( 2) and acteoside ( 3) were common to all plant materials, the former was the main constituent of calli (1.19 - 2.84 % of dry weight), while the latter was the main constituent of the leaves (1.78 - 10.43 % of dry weight). Flavonoids were present only in plants of field cultivation. PMID:15386192

Budzianowska, Anna; Skrzypczak, Lutos?awa; Budzianowski, Jaromir



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


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

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



Application of ascorbic acid 2-glucoside as a solubilizing agent for clarithromycin: solubilization and nanoparticle formation.  


Clarithromycin (CAM) was co-ground with l-ascorbic acid 2-glucoside (AA-2G), a newly developed food additive, to improve the solubility characteristics. The complete solubilizing effect of AA-2G was observed for the ground mixture with 1:1 molar ratio. When ground mixtures of CAM and AA-2G (2:1) were dispersed into water, not only the solubilization of CAM was observed but also nanoparticle formation with a mean particle diameter of 280 nm. The CAM particles obtained in this manner were stable in suspension for at least 7 days. Zeta potential analysis showed that positive charges on the particle surface may be contributing to the stability of the suspension. 1H NMR spectrum of CAM dissolved in a phosphate buffer (pH 5.5) showed a signal derived from the N,N-dimethylamino group at 2.73 ppm, while that of an equimolar ground mixture of CAM with AA-2G in D2O (pH 5.5) showed clearly two signals at 2.65 and 2.77 ppm derived from the splitting of the two methyl groups. The 13C NMR spectrum of the equimolar ground mixture dissolved in D2O exhibited two signals derived from N,N-dimethyl carbons of desosamine group at 37.2 and 42.3 ppm, whereas unprocessed CAM showed no resonance signal arising from those carbons. Moreover, the carbon resonance at 163 and 173 ppm arising from the ketone group in the CAM lactone ring shifted downfield to 177 and 180 ppm after the co-grinding with AA-2G. The formation of nanoparticles was only observed when CAM was co-ground with AA-2G in the molar ratio of 2:1, which might be attributable to a grinding-induced interaction in the solid-state via the ketone group in lactone ring of CAM. PMID:17055675

Inoue, Yutaka; Yoshimura, Sachie; Tozuka, Yuichi; Moribe, Kunikazu; Kumamoto, Takuya; Ishikawa, Tsutomu; Yamamoto, Keiji



Maintenance of cold-preserved porcine hepatocyte function with UW solution and ascorbic acid-2 glucoside.  


Normal human hepatocytes are an ideal source of liver-targeted cell therapies, such as hepatocyte transplantation and bioartificial livers, but availability of human donor livers for liver cell isolation is severely limited. To effectively utilize scarce donor organs for cell therapies, it is of extreme importance to establish an efficient isolation technique and an effective cold preservation solution for transportation of isolated cells. A lateral segment of the liver was surgically resected from pigs weighing 10 kg and a four-step collagenase and dispase digestion was conducted. Isolated hepatocytes were subjected to 8-h cold storage on ice. The following preservation solutions were tested: 1) University of Wisconsin (UW) solution, 2) UW with 100 microg/ml of ascorbic acid-2 glucoside (AA2G), 3) 100% fetal bovine serum (FBS), and 4) Dulbecco's modified Eagle's medium (DMEM) supplemented with 100% FBS. The mean viability of porcine hepatocytes was 95.5 +/- 2.5% when isolated in three independent experiments. Viability, plating efficiency, membrane stability, and ammonia metabolic capacity of cold-preserved hepatocytes were significantly better maintained by the use of UW solution. When AA2G (100 microg/ml) was combined with UW solution, such parameters were further improved. It was explained by inhibition of caspase-3 activation and retention of ATP at high levels of hepatocytes preserved with UW solution containing AA2G. The present work demonstrates that a combination of UW solution with AA2G (100 microg/ml) would be a useful cold preservation means for the development of cell therapies. PMID:14579928

Takesue, Michihiko; Maruyama, Masanobu; Shibata, Norikuni; Kunieda, Takemi; Okitsu, Teru; Sakaguchi, Masakiyo; Totsugawa, Toshinori; Kosaka, Yoshikazu; Arata, Akira; Ikeda, Hideaki; Matsuoka, Junji; Oyama, Toshie; Kodama, Makoto; Ohmoto, Kenji; Yamamoto, Shinichiro; Kurabayashi, Yuzuru; Yamamoto, Itaru; Tanaka, Noriaki; Kobayashi, Naoya



Interconverting flavanone glucosides and other phenolic compounds in Lippia salviaefolia Cham. ethanol extracts.  


Four interconverting flavanone glycosides [(2R)- and (2S)-3',4',5,6-tetrahydroxyflavanone 7-O-?-D-glucopyranoside, and (2R)- and (2S)-3',4',5,8-tetrahydroxyflavanone 7-O-?-D-glucopyranoside], in addition to eight known flavonoids [naringenin, asebogenin, sakuranetin, 6-hydroxyluteolin 7-O-?-D-glucoside, (2R)- and (2S)-eriodictyol 7-O-?-D-glucopyranoside, aromadendrin and phloretin], three phenylpropanoid glycosides [forsythoside B, alyssonoside and verbascoside] and the epoxylignan lariciresinol 4'-O-?-D-glucopyranoside were isolated and identified in the EtOH extract of the aerial parts of Lippia salviaefolia Cham. The phytochemical study herein was guided by preliminary antioxidant tests, namely, ?-carotene protection and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging activity. The crude extracts, their active fractions and the isolated compounds were assayed against intracellular reactive oxygen species (ROS) and human embryonic kidney HEK-293 and human melanoma M14 cancer cell growth. Aromadendrin and phloretin were able to counteract elevation of ROS induced by the oxidant t-butylhydroperoxide (t-BOOH) in HEK-293 cells, whereas phloretin strongly protected HEK-293 cells from ROS damage at 1 ?M. Additionally, phloretin exhibited a significant growth inhibitory effect at 20-40 ?M in both HEK-293 and M14 cells and induced a concentration dependent apoptosis at 20 ?M in M14 cells, suggesting a selective action towards malignant cells. Due to their equilibria, the four interconverting flavanone glycosides were studied using 1D and 2D NMR, HPLC-CD-PDA and HRMS analyses. PMID:21871644

Funari, Cristiano Soleo; Passalacqua, Thais Gaban; Rinaldo, Daniel; Napolitano, Assunta; Festa, Michela; Capasso, Anna; Piacente, Sonia; Pizza, Cosimo; Young, Maria Claudia Marx; Durigan, Giselda; Silva, Dulce Helena Siqueira



Knockout of the Erythromycin Biosynthetic Cluster Gene, eryBI, Blocks Isoflavone Glucoside Bioconversion during Erythromycin Fermentations in Aeromicrobium erythreum but Not in Saccharopolyspora erythraea?  

PubMed Central

Isoflavone glucosides are valuable nutraceutical compounds and are present in commercial fermentations, such as the erythromycin fermentation, as constituents of the soy flour in the growth medium. The purpose of this study was to develop a method for recovery of the isoflavone glucosides as value-added coproducts at the end of either Saccharopolyspora erythraea or Aeromicrobium erythreum fermentation. Because the first step in isoflavone metabolism was known to be the conversion of isoflavone glucosides to aglycones by a ?-glucosidase, we chose to knock out the only ?-glucosidase gene known at the start of the study, eryBI, to see what effect this had on metabolism of isoflavone glucosides in each organism. In the unicellular erythromycin producer A. erythreum, knockout of eryBI was sufficient to block the conversion of isoflavone glucosides to aglycones. In S. erythraea, knockout of eryBI had no effect on this reaction, suggesting that other ?-glucosidases are present. Erythromycin production was not significantly affected in either strain as a result of the eryBI knockout. This study showed that isoflavone metabolism could be blocked in A. erythreum by eryBI knockout but that eryBI knockout was not sufficient to block isoflavone metabolism in S. erythraea.

Reeves, Andrew R.; Seshadri, Ramya; Brikun, Igor A.; Cernota, William H.; Gonzalez, Melissa C.; Weber, J. Mark



Knockout of the erythromycin biosynthetic cluster gene, eryBI, blocks isoflavone glucoside bioconversion during erythromycin fermentations in Aeromicrobium erythreum but not in Saccharopolyspora erythraea.  


Isoflavone glucosides are valuable nutraceutical compounds and are present in commercial fermentations, such as the erythromycin fermentation, as constituents of the soy flour in the growth medium. The purpose of this study was to develop a method for recovery of the isoflavone glucosides as value-added coproducts at the end of either Saccharopolyspora erythraea or Aeromicrobium erythreum fermentation. Because the first step in isoflavone metabolism was known to be the conversion of isoflavone glucosides to aglycones by a beta-glucosidase, we chose to knock out the only beta-glucosidase gene known at the start of the study, eryBI, to see what effect this had on metabolism of isoflavone glucosides in each organism. In the unicellular erythromycin producer A. erythreum, knockout of eryBI was sufficient to block the conversion of isoflavone glucosides to aglycones. In S. erythraea, knockout of eryBI had no effect on this reaction, suggesting that other beta-glucosidases are present. Erythromycin production was not significantly affected in either strain as a result of the eryBI knockout. This study showed that isoflavone metabolism could be blocked in A. erythreum by eryBI knockout but that eryBI knockout was not sufficient to block isoflavone metabolism in S. erythraea. PMID:18836015

Reeves, Andrew R; Seshadri, Ramya; Brikun, Igor A; Cernota, William H; Gonzalez, Melissa C; Weber, J Mark



Tannins and related polyphenols of euphorbiaceous plants. XI. Three new hydrolyzable tannins and a polyphenol glucoside from Euphorbia humifusa.  


Three new hydrolyzable tannins, euphormisins M1, M2, and M3, were isolated from Euphorbia humifusa WILLD., and respectively characterized as 1,3,6-tri-O-galloyl-4-O- brevifolincarboxyl-beta-D-glucose (19), an oxidative metabolite (23) of geraniin, and 1,3,6-tri-O-galloyl-alpha-D-glucose (18), by spectroscopic and chemical methods. A new ellagic acid glucoside (16) and fifteen known tannins, including geraniin (8) and four dimers [euphorbins A (13), B (14), excoecarianin (15) and eumaculin A (12)], were also isolated. PMID:7954930

Yoshida, T; Amakura, Y; Liu, Y Z; Okuda, T



The water\\/ n-octane\\/octyl- ?- d-glucoside\\/1-octanol system: Phase diagrams and phase properties  

Microsoft Academic Search

The partial phase diagram of D2O\\/n-octyl-?-d-alkyl-glucoside(C8G1)\\/n-octane has been determined at T=25°C. The diagram contains a funnel-shaped micellar phase originating from the water corner of the phase diagram D2O\\/C8G1 with the stem forming a narrow three-phase region, in which the three phases in equilibrium are two microemulsions of similar composition and an excess oil phase. The microemulsions have been characterized with

Johan Reimer; Markus Nilsson; Marta Álvarez Chamorro; Olle Söderman



Glucose and glucose esters in the larval secretion of Chrysomela lapponica; selectivity of the glucoside import system from host plant leaves.  


Larvae of Chrysomela lapponica (Coleoptera: Chrysomelidae) sequester characteristic O-glucosides from the leaves of their food plants, namely Betula and/or Salix The present study focuses on birch-feeding larvae of C. lapponica from the Altai region in East Kazakhstan. As in other sequestering leaf beetle larvae, the compounds are transported intact via different membrane barriers into the defensive system, followed by glucoside cleavage and subsequent transformations of the plant-derived aglycones. Unlike previous studies with model compounds, we studied the sequestration of phytogenic precursors by analyzing the complex pattern of glucosides present in food plant Betula rotundifolia (39 compounds) and compared this composition with the aglycones present as butyrate esters in the defensive secretion. In addition to the analytic approach, the insect's ability, to transport individual glucosides was tested by using hydrolysis-resistant thioglucoside analogs, applied onto the leaf surface. The test compounds reach the defensive system intact and without intermediate transformation. No significant difference of the transport capacity and selectivity was observed between larvae of birch-feeding population from Kazakhstan, and previous results for larvae of birch-feeding population from the Czech Republic or willow-feeding populations. Overall, the transport of the phytogenic glucosides is highly selective and highly efficient, since only minor compounds of the spectrum of phytogenic glucoside precursors contribute to the limited number of aglycones utilized in the defensive secretion. Interestingly, salicortin 44 and tremulacin 60 were found in the leaves, but no aldehyde or esters of salicylalcohol. Surprisingly, we observed large amounts of free glucose, together with small amounts of 6-O-butyrate esters of glucose (27a/b and 28a/b). PMID:21301937

Tolzin-Banasch, Karla; Dagvadorj, Enkhmaa; Sammer, Ulrike; Kunert, Maritta; Kirsch, Roy; Ploss, Kerstin; Pasteels, Jacques M; Boland, Wilhelm



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

SciTech Connect

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.

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



Lavandulifolioside B: a new phenylethanoid glycoside from the aerial parts of Stachys lavandulifolia Vahl.  


Reversed-phase preparative HPLC analyses of the methanol extract of the aerial parts of Stachys lavandulifolia afforded a new phenylethanoid glycoside, 4,3',4'-trimethoxy-lavandulifolioside A, named lavandulifolioside B, together with three other known phenylethanoid glycosides, lavandulifolioside A, verbascoside and leucosceptoside A, and an iridoid glycoside 5-O-?-allopyranosyloxy-aucubin (5-O-?-allopyranosyl-monomelittoside). While the structures of the known compounds, except the iridoid glycoside, were established by direct comparison of their spectroscopic data with respective literature data, lavandulifolioside B and 5-O-?-allopyranosyloxy-aucubin were identified comprehensively by extensive 1D and 2D NMR analyses. The distribution of the isolated compounds within the genus Stachys has been discussed. PMID:21240755

Delazar, Abbas; Delnavazi, Mohammad R; Nahar, Lutfun; Moghadam, Sadeigh B; Mojarab, Mahdi; Gupta, Abhishek; Williams, Angela S; Mukhlesur Rahman, M; Sarker, Satyajit D



Direct intestinal absorption of red fruit anthocyanins, cyanidin-3-glucoside and cyanidin-3,5-diglucoside, into rats and humans.  


We determined red fruit anthocyanins, cyanidin-3-glucoside (Cy-g) and cyanidin-3,5-diglucoside (Cy-dg), incorporated into plasma and liver of rats and human plasma by UV-HPLC. Fifteen minutes after an oral supplementation of a mixture of 320 mg of Cy-g and 40 mg of Cy-dg/kg of body weight, rats showed an increase to a maximum of 1563 microg (3490 nmol) of Cy-g/L and 195 microg (320 nmol) of Cy-dg/L in plasma and 0.067 microg (0.15 nmol) of Cy-g/g and a trace of Cy-dg together with methylated metabolites such as peonidin-3-glucoside in liver. In human plasma, 30 min after intake (2.7 mg of Cy-g and 0.25 mg of Cy-dg/kg of body weight), an average of 11 microg (24 nmol) of Cy-g/L and a trace of Cy-dg were found. Cyanidin as aglycone of Cy-g and Cy-dg was not found in such plasma samples, neither were conjugated and methylated anthocyanins. The results indicated that anthocyanins are incorporated keeping structurally intact glycoside forms, from the digestive tract into the blood circulation system in mammals. PMID:10552420

Miyazawa, T; Nakagawa, K; Kudo, M; Muraishi, K; Someya, K



Hexaconazole induces antioxidant protection and apigenin-7-glucoside accumulation in Matricaria chamomilla plants subjected to drought stress.  


In this experiment, the possibility of enhancing the water deficit stress tolerance of chamomile (Matricaria chamomilla L.) during two growth stages by the exogenous application of hexaconazole (HEX) was investigated. To improve water deficit tolerance, HEX was applied in three concentrations during two different stages (50 and 80 days after sowing). After HEX applications, the plants were subjected to water deficit stress. Although all HEX concentrations improved the water deficit stress tolerance in chamomile plants, the application of 15 mg L(-1) provided better protection when compared to the other concentration. The exogenous application of HEX provided significant protection against water deficit stress compared to non-HEX-treated plants, significantly affecting the morphological characteristics and aspects of productivity, the relative water, protein and proline contents; non-enzymatic and enzymatic antioxidants; and the flower's apigenin-7-glucoside content. These results suggest that the HEX-induced tolerance to water deficit stress in chamomile was related to the changes in growth variables, antioxidants and the apigenin-7-glucoside content. PMID:21208683

Hojati, Mostafa; Modarres-Sanavy, Seyed Ali Mohammad; Ghanati, Faezeh; Panahi, Mehdi



Phytochemical analysis of Plantago sempervirens from Majella National Park.  


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

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



Detection of type A trichothecene di-glucosides produced in corn by high-resolution liquid chromatography-Orbitrap mass spectrometry.  


The existence of di-glucosylated derivative of T-2 toxin in plant (corn powder) was confirmed for the first time in addition to that of HT-2 toxin. These masked mycotoxins (mycotoxin glucosides) were identified as T-2 toxin-di-glucoside (T2GlcGlc) and HT-2 toxin-di-glucoside (HT2GlcGlc) based on accurate mass measurements of characteristic ions and fragmentation patterns using high-resolution liquid chromatography-Orbitrap mass spectrometric (LC-Orbitrap MS) analysis. Although the absolute structure of T2GlcGlc was not clarified, two glucose molecules were suggested to be conjugated at 3-OH position in tandem when considering the structure of T-2 toxin. On the other hand, the specification of the structure seems to be more complicated in the case of HT2GlcGlc, since HT-2 toxin has two possible positions (at 3-OH and 4-OH) to be glusocylated. In addition, 15-monoacetoxyscirpenol-glucoside (MASGlc) was also detected in the identical sample. PMID:23524332

Nakagawa, Hiroyuki; Sakamoto, Shigeru; Sago, Yuki; Nagashima, Hitoshi



Protective Role of Malvidin-3-Glucoside on Peroxynitrite-Induced Damage in Endothelial Cells by Counteracting Reactive Species Formation and Apoptotic Mitochondrial Pathway  

PubMed Central

The health-promoted benefits of anthocyanins, including vascular protective effects and antiatherogenic properties, have now been recognized, but the involved molecular mechanisms have not been well elucidated. Following our previous work on cytoprotective mechanisms of some anthocyanins against apoptosis triggered by peroxynitrite in endothelial cells, here we investigated the protective role of malvidin-3-glucoside, a major dietary anthocyanin, on such deleterious process, by exploring the interference on cellular reactive species formation and on apoptotic mitochondrial pathway. Preincubation of cells with 25??M malvidin-3-glucoside protected efficiently endothelial cells from peroxynitrite-promoted apoptotic death, an effect which may be partially mediated by its ability to decrease the formation of reactive species after cell aggression, as assessed by the dichlorodihydrofluorescein diacetate assay and by carbonyl groups formation. Moreover, malvidin-3-glucoside inhibited mitochondrial apoptotic signaling pathways induced by peroxynitrite, by counteracting mitochondrial membrane depolarization, the activation of caspase-3 and -9, and the increase in the expression of the proapoptotic Bax protein. Altogether, our data expands our knowledge about the molecular mechanisms underlying the vascular protection afforded by malvidin-3-glucoside, and anthocyanins in general, in the context of prevention of endothelial dysfunction and atherosclerosis.

Paixao, Joana; Dinis, Teresa C. P.; Almeida, Leonor M.



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

NASA Astrophysics Data System (ADS)

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.

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



beta-Glucoside Permease Represses the bgl Operon of Escherichia Coli by Phosphorylation of the Antiterminator Protein and also Interacts with Glucose-Specific Enzyme III, the Key Element in Catabolite Control  

Microsoft Academic Search

The beta-glucoside (bgl) operon of Escherichia coli is subject to both positive control by transcriptional termination\\/antitermination and negative control by the beta-glucoside-specific transport protein, an integral membrane protein known as enzyme IIBgl. Previous results led us to speculate that enzyme IIBgl exerts its negative control by phosphorylating and thereby inactivating the antiterminator protein, BglG. Specifically, our model postulated that the

Karin Schnetz; Bodo Rak



Biologically relevant lyotropic liquid crystalline phases in mixtures of n-octyl-?-D-glucoside and water. Determination of the phase diagram by fluorescence spectroscopy  

PubMed Central

When mixed with water, n-octyl-?-D-glucoside forms self-assembled nanostructures, several of which are liquid crystalline and all of which depend on the water/glucoside ratio and temperature. For practical use of these phases, a detailed understanding of the conditions under which they exist (i.e., the isobaric phase diagram) is required. We use the fluorescence of the dye molecule prodan as a new approach to probe the phases formed in these mixtures. The prodan fluorescence signal depends on the polarity of its environment and thus the phase(s) in which the dye exists. Visual inspection of the total fluorescence signal can qualitatively determine the phases present, including co-existing phases. Temperature-induced phase changes are also detected from variations observed in the prodan fluorescence spectrum. The sensitivity of this new technique allows the single and multiple phase regions to be mapped carefully for the first time.

Karukstis, Kerry K.; Duim, Whitney C.; Van Hecke, Gerald R.; Hara, Nagiko



Isolation of bile acid glucosides and N-acetylglucosaminides from human urine by ion-exchange chromatography and reversed-phase high-performance liquid chromatography.  


A method for the isolation, separation and analysis of glucosides and N-acetylglucosaminides of non-amidated bile acids and of glycine- and taurine-conjugated bile acid glucosides from normal human urine is described. Total bile acids were extracted from 24-h collections of urine by repetitive use of Sep-Pak C18 cartridges. After elution with 80% aqueous methanol, a group separation into non-amidated, glycine- and taurine-conjugated bile acids was performed by ion-exchange chromatography on Lipidex-DEAP. The glycosylated compounds were then separated from the corresponding non-glycosylated ones by high-performance liquid chromatography (HPLC) using a reversed-phase system with a linear methanol gradient. The glycosylated compounds isolated by HPLC were analysed by fast atom bombardment mass spectrometry and, after derivatization, by gas chromatography-mass spectrometry. Information about the sugar moieties of the bile acid glycosides was also obtained by treatment with different glycosidases. PMID:3243856

Marschall, H U; Green, G; Egestad, B; Sjövall, J



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


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

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



Isolation, structural elucidation, MS profiling, and evaluation of triglyceride accumulation inhibitory effects of benzophenone C-glucosides from leaves of Mangifera indica L.  


Seventy percent ethanol-water extract from the leaves of Mangifera indica L. (Anacardiaceae) was found to show an inhibitory effect on triglyceride (TG) accumulation in 3T3-L1 cells. From the active fraction, six new benzophenone C-glucosides, foliamangiferosides A(3) (1), A(4) (2), C(4) (3), C(5) (4), C(6) (5), and C(7) (6) together with 11 known benzophenone C-glucosides (7-17) were obtained. In this paper, isolation, structure elucidation (1-6), and MS fragment cleavage pathways of all 17 isolates were studied. 1-6 showed inhibitory effects on TG and free fatty acid accumulation in 3T3-L1 cells at 10 ?M. PMID:23368644

Zhang, Yi; Han, Lifeng; Ge, Dandan; Liu, Xuefeng; Liu, Erwei; Wu, Chunhua; Gao, Xiumei; Wang, Tao



Differential cell-protective function of two resveratrol (trans-3,5,4'-trihydroxystilbene) glucosides against oxidative stress.  


Resveratrol (trans-3,5,4'-trihydroxystilbene; RSV), a natural polyphenol, exerts a beneficial effect on health and diseases. RSV targets and activates the NAD(+)-dependent protein deacetylase SIRT1; in turn, SIRT1 induces an intracellular antioxidative mechanism by inducing mitochondrial superoxide dismutase (SOD2). Most RSV found in plants is glycosylated, and the effect of these glycosylated forms on SIRT1 has not been studied. In this study, we compared the effects of RSV and two glycosyl RSVs, resveratrol-3-O-?-d-glucoside (3G-RSV; polydatin/piceid) and resveratrol-4'-O-?-d-glucoside (4'G-RSV), at the cellular level. In oxygen radical absorbance capacity and 2,2-diphenyl-1-picrylhydrazyl radical scavenging assays, the antioxidant activity of 3G-RSV was comparable to that of RSV, whereas the radical-scavenging efficiency of 4'G-RSV was less than 50% of that of RSV. However, 4'G-RSV, but not 3G-RSV, induced SIRT1-dependent histone H3 deacetylation and SOD2 expression in mouse C2C12 skeletal myoblasts; as with RSV, SIRT1 knockdown blunted these effects. RSV and 4'G-RSV, but not 3G-RSV, mitigated oxidative stress-induced cell death in C2C12 cells and primary neonatal rat cardiomyocytes. RSV and 4'G-RSV inhibited C2C12 cell proliferation, but 3G-RSV did not. RSV was found in both the intracellular and extracellular fractions of C2C12 cells that had been incubated with 4'G-RSV, indicating that 4'G-RSV was extracellularly deglycosylated to RSV, which was then taken up by the cells. C2C12 cells did not deglycosylate 3G-RSV. Our results point to 4'G-RSV as a useful RSV prodrug with high water solubility. These data also show that the in vitro antioxidative activity of these molecules did not correlate with their ability to protect cells from oxidative stress-induced apoptosis. PMID:23042952

Hosoda, Ryusuke; Kuno, Atsushi; Hori, Yusuke S; Ohtani, Katsuki; Wakamiya, Nobutaka; Oohiro, Azusa; Hamada, Hiroki; Horio, Yoshiyuki



Improvement of the post-thaw qualities of Okinawan native pig spermatozoa frozen in an extender supplemented with ascorbic acid 2- O-?-glucoside  

Microsoft Academic Search

The technical establishment of boar sperm cryopreservation is indispensable for effective breeding of the scarce Okinawan native pig Agu. The objective of the present study was to determine whether ascorbic acid 2-O-?-glucoside (AA-2G), a stable ascorbate derivative, is capable of improving the quality of cryopreserved Agu spermatozoa. Ejaculated Agu sperm frozen in an extender supplemented with 0, 100, 200, 400

Teppei Yoshimoto; Satoshi Nakamura; Shogo Yamauchi; Norio Muto; Tadashi Nakada; Koji Ashizawa; Hideki Tatemoto



Determination of the thermodynamic parameters of the complex formation between malvidin-3-O-glucoside and polyphenols. Copigmentation effect in red wines  

Microsoft Academic Search

The thermodynamics of the molecular association process between the malvidin-3-O-glucoside and a series of polyphenol derivatives (called ‘copigmentation’ in food chemistry) were studied in aqueous media. The Gibbs free energy, enthalpy and entropy values were determined by the fluorometric method. A combination of the Job's method with the van't Hoff theory was applied for data evaluation. The results show the

Sándor Kunsági-Máté; Kornélia Szabó; Martin P. Nikfardjam; László Kollár



Concise synthesis of flavocommelin, 7-O-methylapigenin 6-C-, 4'-O-bis-?-D-glucoside, a component of the blue supramolecular pigment from Commelina communis.  


Flavocommelin, 7-O-methylapigenin 6-C-, 4'-O-bis-?-D-glucoside, was synthesized in 9 steps from the C-glycosylation of 6-O-benzy-4-O-methylphloroacetophenone via the introduction of a cinnamoyl residue by aldol condensation and the formation of a C-ring by regioselective and oxidative ring-closure to regio- and stereoselective O-glycosylation for an overall yield of 31%. PMID:23603241

Misawa, Kazufumi; Gunji, Yoshiki; Sato, Shingo



Assessment for the light-induced cis– trans isomerization of rhapontigenin and its glucoside rhaponticin by capillary electrophoresis and spectrometric methods  

Microsoft Academic Search

The light-induced cis–trans isomerization of rhapontigenin (RHA) and its glucoside rhaponticin (RHA-Glc) were evaluated under ultraviolet (UV) light irradiation. A simple and rapid capillary electrophoresis method was developed for the kinetic study of four stilbenes (both cis and trans form of RHA and RHA-Glc). These analyses were achieved by using ?-cyclodextrin (?-CD) modified capillary zone electrophoresis with diode array detector

Yang Hui; Xi Li; Xingguo Chen



Cyanidin3- O-?-glucoside inhibits iNOS and COX2 expression by inducing liver X receptor alpha activation in THP1 macrophages  

Microsoft Academic Search

Anthocyanins belong to a large and widespread group of water-soluble phytochemicals and exhibit potent antioxidative and anti-inflammatory properties; however, the molecular mechanisms of these biochemical actions mediated by anthocyanins remain unclear. In this study, our data show that pretreatment of THP-1 macrophages with Cyanidin-3-O-?-glucoside (C3G) for 12 h can enhance the expression and transcriptional activities of the nuclear receptor peroxisome proliferator-activated

Qing Wang; Min Xia; Chi Liu; Honghui Guo; Qingyuan Ye; Yan Hu; Yinghui Zhang; Mengjun Hou; Huilian Zhu; Jing Ma; Wenhua Ling



IGF-1 Induction by Acylated Steryl ?-Glucosides Found in a Pre-Germinated Brown Rice Diet Reduces Oxidative Stress in Streptozotocin-Induced Diabetes  

Microsoft Academic Search

BackgroundThe pathology of diabetic neuropathy involves oxidative stress on pancreatic ?-cells, and is related to decreased levels of Insulin-like growth factor 1 (IGF-1). Acylated steryl ?-glucoside (PR-ASG) found in pre-germiated brown rice is a bioactive substance exhibiting properties that enhance activity of homocysteine-thiolactonase (HTase), reducing oxidative stress in diabetic neuropathy. The biological importance of PR-ASG in pancreatic ?-cells remains unknown.Here

Seigo Usuki; Ying-Ying Tsai; Keiko Morikawa; Shota Nonaka; Yasuhide Okuhara; Mitsuo Kise; Robert K. Yu



C-Glycosyl flavonoids and coloratane-type sesquiterpene glucosides from the water-soluble fraction of a leaf extract of a Malagasy endemic plant, Cinnamosma fragrans (Canellaceae).  


Leaves of Cinnamosma fragrans were extracted with MeOH, and the concentrated MeOH extract was partitioned with EtOAc and H2O. From the H2O-soluble fraction, three new flavonol C-glycosides and two coloratane glucosides were isolated, along with nine known compounds. On extensive spectroscopic analysis, C-glycosylation was found to have occurred on the B-ring. PMID:23274915

Nomoto, Yuya; Harinantenaina, Liva; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki



Protective effect of cyanidin 3-O-glucoside on beta-amyloid peptide-induced cognitive impairment in rats.  


Alzheimer's disease (AD) is a neurodegenerative disorder that results in cognitive impairment. It has been proposed that deposits of beta-amyloid (A?) form the cores of the plaque and, subsequently, induce the activation of GSK-3? and the hyperphosphorylation of tau, resulting in cognitive impairment. Oxidative stress has been proposed to be an important factor in the pathogenesis of AD. Cyanidin 3-O-glucoside (Cy3G) is a neuroprotective antioxidant. However, the effects of Cy3G on cognition are unclear. In this paper, we show that Cy3G is protective against the A?-induced impairment of learning and memory, but has no effect on normal learning and memory. Moreover, we found that Gy3G attenuated the A?-induced tau hyperphosphorylation and GSK-3? hyperactivation observed in AD. Taken together, these results demonstrated that Cy3G can rescue the cognitive impairments that are induced by A? via the modulation of GSK-3?/tau, suggesting a potential therapeutic role of Cy3G in AD. PMID:23274703

Qin, Lina; Zhang, Jianlong; Qin, Mali



Quantitative determination of secoiridoid glucosides in in vitro propagated plants of Gentiana davidii var. formosana by high performance liquid chromatography.  


A simple protocol for in vitro mass propagation of Gentiana davidii var. formosana (Gentianaceae) has been developed. Multiple shoot development was achieved by culturing the stem node explants on Murashige and Skoog (MS) medium supplemented with 4.44 microM N6-benzyladenine (BA). The shoots were multiplied by subculturing on MS medium supplemented with 1.07-10.74 microM alpha-naphthaleneacetic acid (NAA) and 8.88 microM BA. Shoots were rooted on MS basal medium supplemented with various auxins. Shoots rooted on growth regulator-free medium were transferred to peat moss:vermiculite mixture and acclimatized in the growth chamber. The contents of gentiopicroside and swertiamarin, the two important secoiridoid glucosides, in different plant material were determined by high performance liquid chromatography (HPLC). The analysis revealed that the content of gentiopicroside and swertiamarin in the aerial and underground parts of G. davidii var. formosana was higher than the marketed crude drug (underground parts of G. scabra) and varied with the age of the plant. PMID:11270726

Chueh, F S; Chen, C C; Sagare, A P; Tsay, H S



Cholesteryl Glucoside Stimulates Activation of Protein Kinase B/Akt in the Motor Neuron-Derived NSC34 Cell Line  

PubMed Central

Steryl glycosides and related compounds are commonly found in the environment and have been associated with neurodegenerative changes in vulnerable individuals. However, their mechanisms of action in mammalian cells have not been well investigated. In the present study the effects of cholesterol glucoside (CG), a variant form of steryl glycoside, was investigated in the motor neuron-derived NSC34 cell line. Prolonged treatment with CG was found to induce cell death in a dose- and time-dependent manner. However, transient exposure of CG preconditioned NSC34 cells for stress from serum deprivation. To study the signaling pathways activated by CG, we employed the Kinetworks™ KPSS 1.3 Phospho-site Screen to track the phosphorylation level of at least 35 diverse signaling proteins. The survival protein kinase B (PKB/Akt) displayed a 2-fold increase in phosphorylation at its Ser-473 activation site following CG stimulation. Akt signaling was important for conferring cytoprotection against serum deprivation-induced stress. Inhibition of phosphatidylinositol 3-kinase (PI3K), which indirectly triggers Akt stimulation, completely abolished CG preconditioning against serum deprivation. Our findings revealed that there may be a PI3K-independent pathway which also mediated Akt Ser-473 phosphorylation. Improved understanding of the mechanisms of action of CG should provide insights to the how other members of the steryl glycoside family induce toxicity in the mouse model of ALS-PDC, and how cells respond to these toxins.

Ly, Philip T.T.; Pelech, Steven; Shaw, Christopher A.



Effects of baking on cyanidin-3-glucoside content and antioxidant properties of black and yellow soybean crackers.  


Black soybean is a potential functional food ingredient with high anthocyanin content, but the ability to maintain anthocyanin content under dry heat processing has not been reported. This study investigated the effects of soybean seed coat colour and baking time-temperature combinations on the extractable antioxidant properties of a soy cracker food model. Crackers prepared with black soybeans had significantly higher TPC, total isoflavones, and peroxyl, hydroxyl, and ABTS(+) radical scavenging abilities than their yellow counterparts, at all time-temperature combinations. Cyanidin-3-glucoside (C3G) was detected only in black soybean crackers, and all baking treatments significantly decreased C3G. The greatest losses occurred at the low temperature×long time and high temperature×short time, the smallest loss with moderate temperature×short/medium time. The high temperature treatment altered phenolic acid and isoflavone profiles; however, total isoflavones were unaffected. Overall results suggest that moderate baking temperature at minimal time may best preserve anthocyanin and other phenolics in baked black soybean crackers. PMID:23790899

Slavin, Margaret; Lu, Yingjian; Kaplan, Nicholas; Yu, Liangli Lucy



Isolation of a flavonoid, apigenin 7-O-glucoside, from Mentha longifolia (L.) Hudson subspecies longifolia and its genotoxic potency.  


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 ?M/plate) to 91.1% (S. typhimurium TA1537: 0.2 ?M/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

Gulluce, Medine; Orhan, Furkan; Yanmis, Derya; Arasoglu, Tulin; Guvenalp, Zuhal; Demirezer, Lutfiye Omur



Stilbene glucoside from Polygonum multiflorum Thunb.: a novel natural inhibitor of advanced glycation end product formation by trapping of methylglyoxal.  


Methylglyoxal (MGO), the reactive dicarbonyl intermediate generated during the nonenzymatic glycation between reducing sugars and amino groups of proteins, lipids, and DNA, is the precursor of advanced glycation end products (AGEs). Many studies have shown that AGEs play a major pathogenic role in diabetes and its complications. This study found that 2,3,5,4'-tetrahydroxystilbene 2-O-beta-D-glucoside (THSG), the major bioactive compound from Polygonum multiflorum Thunb., can efficiently inhibit the formation of AGEs in a dose-dependent manner by trapping reactive MGO under physiological conditions (pH 7.4, 37 degrees C). More than 60% MGO was trapped by THSG within 24 h, which was much more effective than resveratrol and its methylated derivative, pterostilbene, the two major bioactive dietary stilbenes. The major mono- and di-MGO adducts of THSG were successfully purified and found to be mixtures of tautomers. LC-MS and NMR data showed that positions 4 and 6 of the A ring were the major active sites for trapping MGO. It was also found that THSG could significantly inhibit the formation of AGEs in the human serum albumin (HSA)-MGO assay and both mono- and di-MGO adducts of THSG were detected in this assay using LC-MS. The results suggest that the ability of THSG to trap reactive dicarbonyl species makes it a potential natural inhibitor of AGEs. PMID:20104848

Lv, Lishuang; Shao, Xi; Wang, Liyan; Huang, Derong; Ho, Chi-Tang; Sang, Shengmin



Deoxynivalenol, deoxynivalenol-3-glucoside, and enniatins: the major mycotoxins found in cereal-based products on the Czech market.  


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 ?g/kg, but its masked form, deoxynivalenol-3-?-d-glucoside, has an even higher incidence of 80% of samples, and concentrations ranging between 5 and 72 ?g/kg were detected. Nivalenol was found only in three samples at levels of 30 ?g/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 ?g/kg) followed by enniatin B with an incidence in 91% of the samples (concentration range of 13-941 ?g/kg) and enniatin B1 with an incidence of 80% in the samples tested (concentration range of 8-785 ?g/kg). Enniatin A1 was found only in 44% of samples at levels ranging between 8 and 851 ?g/kg. PMID:22070284

Malachova, Alexandra; Dzuman, Zbynek; Veprikova, Zdenka; Vaclavikova, Marta; Zachariasova, Milena; Hajslova, Jana



Deglycosylation is a key step in biotransformation and lifespan effects of quercetin-3-O-glucoside in Caenorhabditis elegans.  


Due to their purported healthful activities, quercetin and other flavonoids are being increasingly proposed as nutraceuticals. Quercetin occurs in food as glycosides; however, most assays on its activity have been performed with the aglycone, despite glycosylation deeply affects compound bioavailability. In this work, the uptake and lifespan effects of quercetin-3-O-glucoside (Q3Glc) and quercetin have been assessed in Caenorhabditis elegans. Q3Glc was taken up by this nematode in a concentration-dependent manner and rapidly deglycosylated to quercetin, which was accumulated in the worm and partially biotransformed to conjugated metabolites. Significant mean lifespan extension up to 23% compared to controls was observed in wild type worms cultivated in the presence of low concentrations of Q3Glc (10?M and 25?M), whereas exposure to greater concentrations of Q3Glc (50-200?M) caused a reduction in mean and maximum lifespan compared with the control. By contrast, treatment of klo-1 and klo-2 mutant worms lacking ?-glucosidase activity with 200?M of Q3Glc led to extended mean lifespan (up to 39%), similar to quercetin aglycone at the same concentration levels. In those mutants, Q3Glc was accumulated without important deglycosylation to quercetin was produced. Taken together, these findings indicated that Q3Glc was taken up by the nematode in greater extent than quercetin, and that deglycosylation and subsequent aglycone accumulation in the worm appeared as key points to explain the observed lifespan effects. The obtained results also suggested that facilitated absorption should be more important for the uptake of quercetin derivatives than passive diffusion. PMID:23856528

Dueñas, Montserrat; Surco-Laos, Felipe; González-Manzano, Susana; González-Paramás, Ana M; Gómez-Orte, Eva; Cabello, Juan; Santos-Buelga, Celestino



The Human Fecal Microbiota Metabolizes Deoxynivalenol and Deoxynivalenol-3-Glucoside and May Be Responsible for Urinary Deepoxy-Deoxynivalenol  

PubMed Central

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-?-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.

Duncan, Gary; Richardson, Anthony J.



Reduced hepatotoxicity by total glucosides of paeony in combination treatment with leflunomide and methotrexate for patients with active rheumatoid arthritis.  


Combination use of methotrexate (MTX) and leflunomide (LEF) has been proved effective in the treatment of active rheumatoid arthritis (RA). However, previous trials have documented that both are associated with increased incidence of liver toxicity. As active compounds extracted from the roots of the traditional Chinese herb Paeonia lactiflora Pall, total glucosides of paeony (TGP) have been shown to have anti-inflammatory, hepatoprotective and immuno-regulatory activities, without evident toxicity or side effects. In this 24-week, open label, randomized multicenter clinical trial, we investigated the efficacy of TGP and the protective effect on hepatotoxicity in the combination treatment with LEF and MTX for patients with active RA. A total of 204 patients with active RA (DAS28>3.2) recruited from 3 regional referral centers were enrolled and received MTX and LEF combination therapy (MTX 10 mg/week plus LEF 20 mg/day) with or without TGP for up to 24 weeks by randomization. Hepatotoxicity was defined as an increase of at least 1.5-fold the upper limits of normal (ULN) of alanine aminotransferase (ALT) or aspartate aminotransferase (AST). Significantly less frequent hepatotoxicity was observed in patients with TGP than those without (9.5% vs 34.8%, p < 0.001) at 12 weeks. The proportion of patients whose ALT or AST levels were > 1.5 to ?2 times and >2 to ?3 times the ULN were lower in TGP group than the control (1.9% vs 10.1%, 2.9% vs 12.4%, p < 0.05 respectively). More patients in the TGP group achieved a European League Against Rheumatism (EULAR) good response or moderate response at 12 weeks, although there is no statistical significance. Similar results were observed at 24 weeks. Our preliminary study demonstrates the hepatoprotective and additive role of TGP in combination with MTX and LEF in the treatment of active RA. PMID:23415907

Chen, Zhu; Li, Xiang-Pei; Li, Zhi-Jun; Xu, Liang; Li, Xiao-Mei



Effects of milling and baking technologies on levels of deoxynivalenol and its masked form deoxynivalenol-3-glucoside.  


The co-occurrence of the major Fusarium mycotoxin deoxynivalenol (DON) and its conjugate deoxynivalenol-3-glucoside (DON-3-Glc) has been documented in infected wheat. This study reports on the fate of this masked DON within milling and baking technologies for the first time and compares its levels with those of the free parent toxin. The fractionation of DON-3-Glc and DON in milling fractions was similar, tested white flours contained only approximately 60% of their content in unprocessed wheat grains. No substantial changes of both target analytes occurred during the dough preparation process, i.e. kneading, fermentation, and proofing. However, when bakery improvers enzymes mixtures were employed as a dough ingredient, a distinct increase up to 145% of conjugated DON-3-Glc occurred in fermented dough. Some decrease of both DON-3-Glc and DON (10 and 13%, respectively, compared to fermented dough) took place during baking. Thermal degradation products of DON, namely norDON A, B, C, D, and DON-lactone were detected in roasted wheat samples and baked bread samples by means of UPLC-Orbitrap MS. Moreover, thermal degradation products derived from DON-3-Glc were detected and tentatively identified in heat-treated contaminated wheat and bread based on accurate mass measurement performed under the ultrahigh mass resolving power. These products, originating from DON-3-Glc through de-epoxidation and other structural changes in the seskviterpene cycle, were named norDON-3-Glc A, B, C, D, and DON-3-Glc-lactone analogically to DON degradation products. Most of these compounds were located in the crust of experimental breads. PMID:21797213

Kostelanska, Marta; Dzuman, Zbynek; Malachova, Alexandra; Capouchova, Ivana; Prokinova, Evzenie; Skerikova, Alena; Hajslova, Jana



The human fecal microbiota metabolizes deoxynivalenol and deoxynivalenol-3-glucoside and may be responsible for urinary deepoxy-deoxynivalenol.  


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-?-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

Gratz, Silvia W; Duncan, Gary; Richardson, Anthony J



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.  


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

Nakazawa, Takashi; Miyata, Kengo; Omura, Koichi; Iwanaga, Takashi; Nagata, Osamu



Glucosylceramidase from calf spleen. Characterization of its active site with 4-n-alkylumbelliferyl beta-glucosides and N-alkyl derivatives of 1-deoxynojirimycin.  


The beta-glucosides of 4-heptyl-, -nonyl-, and -undecylumbelliferone were synthesized and their substrate properties studied with calf spleen glucosylceramidase. Self-association of the free long chain alkylumbelliferones in aqueous buffer was inferred from their low fluorescence in the absence and strongly enhanced fluorescence in the presence of detergents. Association of the higher alkylumbelliferyl glucosides with detergent micelles was indicated by the influence of detergent on solubility and on enzyme activity which differed markedly between the methyl and the higher alkyl substrates. Compared to 4-methylumbelliferyl beta-glucoside their Km was 14 to 23 times smaller and Vmax/Km 20 to 30 times larger with no significant difference between the nonyl and undecyl derivatives. The enzyme was inhibited by 1-deoxynojirimycin (1,5-dideoxy-1,5-imino-D-glucitol, dNM) and a series of its N-alkyl derivatives with Ki-values that ranged from 390 microM for the parent compound to 330 microM for the butyl derivative and 0.08 microM for the tetradecyl derivative. The biphasic linear plot of - RT X 1n [Ki/Ki (dNM)] vs. chain length is interpreted in terms of an aglycon binding site that has an extended hydrophobic region starting at about 5 carbon atoms from the catalytic site. dNM inhibited greater than or equal to 10(3) times better than D-glucose, and N-decanoyl-dNM was a very weak inhibitor compared to N-decyl-dNM. It is concluded that the formation of an ion pair consisting of the protonated dNM derivative and an essential carboxylate at the catalytic site makes a large contribution to the binding energy. Strong shielding of this site from the aqueous environment is indicated by identical effects of ionic strength on Km and Ki. PMID:2936366

Legler, G; Liedtke, H



Isolation and absolute structures of enantiomeric 1,2-bis(4-hydroxy-3-methoxyphenyl)-1,3-propanediol 1-O-glucosides from the bark of Hovenia trichocarpa.  


Two 1,2-bis(4-hydroxy-3-methoxyphenyl)-1,3-propanediol 1-O-glucosides, hovetrichosides A (1) and B (2), were isolated from the bark of Hovenia trichocarpa. Their structures were established by extensive NMR experiments and chemical methods. Compounds 1 and 2 were (1R), (2S)-1-(4-hydroxy-3-methoxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)-1, 3-propanediol 1-O-beta-D-glucopyranoside and (1S), (2R)-1-(4-hydroxy-3-methoxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)-1, 3-propanediol 1-O-beta-D-glucopyranoside, respectively. PMID:9748383

Yoshikawa, K; Mimura, N; Arihara, S



Isolation of Liquiritigenin-4'-Apiosyl-Glucoside and Liquiritin from the Root of Glycyrrhiza uralensis by High-Performance Centrifugal Partition Chromatography.  


High-performance centrifugal partition chromatography (HPCPC) combined with ultraviolet detection was employed for the separation and purification of flavonoids from Glycyrrhiza. At the detection wavelength of 276 nm, two flavonoids, liquiritigenin-4'-apiosyl-glucoside and liquiritin, were successfully separated by HPCPC with an optimized two-phase solvent system composed of ethyl acetate-ethanol-water (1:0.1:1, v/v/v). The purity of these compounds was 95.0 and 97.1%, respectively, as determined by high-performance liquid chromatography. Their structures were identified by electrospray ion source mass spectroscopy (ESI-MS(n)) in the negative ion mode. PMID:23552847

Wang, Jing; Wang, Duo; Yu, Jing; Liu, Chunming; Li, Li; Zhang, Yuchi



Genetic engineering of plant secondary metabolism. Accumulation of 4-hydroxybenzoate glucosides as a result of the expression of the bacterial ubiC gene in tobacco.  

PubMed Central

The ubiC gene of Escherichia coli encodes chorismate pyruvatelyase, an enzyme that converts chorismate into 4-hydroxybenzoate (4HB) and is not normally present in plants. The ubiC gene was expressed in Nicotiana tabacum L. plants under control of a constitutive plant promoter. The gene product was targeted into the plastid by fusing it to the sequence for the chloroplast transit peptide of the small subunit of ribulose-1,5-bisphosphate carboxylase/oxygenase. Transgenic plants showed high chorismate pyruvate-lyase activity and accumulated 4HB as beta-glucosides, with the glucose attached to either the hydroxy or the carboxyl function of 4HB. The total content of 4HB glucosides was approximately 0.52% of dry weight, which exceeded the content of untransformed plants by at least a factor of 1000. Feeding experiments with [1,7-13C2]shikimic acid unequivocally proved that the 4HB that was formed in the transgenic plants was not derived from the conventional phenylpropanoid pathway but from the newly introduced chorismate pyruvate-lyase reaction.

Siebert, M; Sommer, S; Li, S M; Wang, Z X; Severin, K; Heide, L



Efficient synthesis and antimicrobial activity of some novel S-?-d-glucosides of 5-aryl-1,2,4-triazole-3-thiones derivatives.  


A series of 3-S-?-d-glucosides-4-arylideneamino-5-aryl-1,2,4-triazoles were rationally designed and synthesized according to the principle of superposition of bioactive substructures by the combination of 1,2,4-triazole, Schiff base and glucosides. The structures of the target compounds have been characterized by (1)H NMR, (13)C NMR, IR, MS and HRMS. All the newly synthesized compounds have been evaluated for their antimicrobial activities in vitro against Staphylococcus aureus (ATCC 6538), Escherichia coli (ATCC 8099) as well as Monilia albican (ATCC 10231). The bioactive assay showed that most of the tested compounds displayed variable inhibitory effects on the growth of the Gram-positive bacterial strain (Staphylococcus aureus), Gram-negative bacterial strains (Escherichia coli) and fungal strains (Monilia albican). All the target compounds exhibited better antifungal activity than antibacterial activity. Especially, compounds 6b, 6c, 6f, 6j, 6k and 6l showed excellent activity against fungus Monilia albican with MIC values of 16 ?g/mL. PMID:23466234

Ji, Dan; Lu, JunRui; Lu, BoWei; Xin, ChunWei; Mu, JiangBei; Li, JianFa; Peng, ChunYong; Bao, XiuRong



?-D-Glucoside utilization by Mycoplasma mycoides subsp. mycoides SC: possible involvement in the control of cytotoxicity towards bovine lung cells  

PubMed Central

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-?-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., ?-D-glucosides) sucrose and lactose. However, strains expressing the Bgl isoform Val204 show a lower hydrolysing activity on the chromogenic substrate p-nitrophenyl-?-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 ?-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 factor, but strains possessing the Bgl isoform Val204 with low hydrolysing activity are more prone to survive in environments that contain high levels of ?-D-glucosides, thus contributing in some extent to mycoplasmaemia.

Vilei, Edy M; Correia, Ivone; Ferronha, M Helena; Bischof, Daniela F; Frey, Joachim



Separation of patuletin-3-O-glucoside, astragalin, quercetin, kaempferol and isorhamnetin from Flaveria bidentis (L.) Kuntze by elution-pump-out high-performance counter-current chromatography.  


Flaveria bidentis (L.) Kuntze is an annual alien weed of Flaveria Juss. (Asteraceae) in China. Bioactive compounds, mainly flavonol glycosides and flavones from F. bidentis (L.) Kuntze, have been studied in order to utilize this invasive weed, Analytical high-performance counter-current chromatography (HPCCC) was successfully used to separate patuletin-3-O-glucoside, a mixture of hyperoside (quercetin-3-O-galactoside) and 6-methoxykaempferol-3-O-galactoside, astragalin, quercetin, kaempferol and isorhamnetin using two runs with different solvent system. Ethyl acetate-methanol-water (10:1:10, v/v) was selected by analytical HPCCC as the optimum phase system for the separation of patuletin-3-O-glucoside, a mixture of hyperoside and 6-methoxykaempferol-3-O-galactoside, and astragalin. A Dichloromethane-methanol-water (5:3:2, v/v) was used for the separation of quercetin, kaempferol and isorhamnetin. The separation was then scaled up: the crude extract (ca 1.5 g) was separated by preparative HPCCC, yielding 12 mg of patuletin-3-O-glucoside at a purity of 98.3%, yielding 9 mg of a mixture of hyperoside and 6-methoxykaempferol-3-O-galactoside constituting over 98% of the fraction, and 16 mg of astragalin (kaempferol-3-O-glucoside) at a purity of over 99%. The pump-out peaks are isorhanetin (98% purity), kaemferol (93% purity) and quercitin (99% purity). The chemical structure of patuletin-3-O-glucoside and astragalin were confirmed by MS and ¹H, ¹³C NMR. PMID:21329934

Wei, Yun; Xie, Qianqian; Fisher, Derek; Sutherland, Ian A



Phenanthrenes, 9,10-dihydrophenanthrenes, bibenzyls with their derivatives, and malate or tartrate benzyl ester glucosides from tubers of Cremastra appendiculata.  


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

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



Radiation protection by 6-palmitoyl ascorbic acid-2-glucoside: studies on DNA damage in vitro, ex vivo, in vivo and oxidative stress in vivo.  


A palmitoyl derivative of ascorbic acid 2-glucoside, 6-palmitoyl ascorbic acid-2-glucoside (PAsAG), which possess good antioxidant properties, is examined for radioprotection in vitro, ex vivo and in vivo models. PAsAG protected plasmid DNA from gamma-radiation induced damages under in vitro conditions. Presence of 1.6 mM PAsAG inhibited the disappearance of ccc (covalently closed circular) form of plasmid pBR322 with a dose modifying factor of 1.5. Comet assay studies on mouse spleen cells exposed to 6 Gy gamma-radiation (ex vivo) in presence and absence of PAsAG revealed that cellular DNA was effectively protected by this compound from radiation induced damages. Oral administration of 80 mg/kg body weight of PAsAG to mice 1 hour prior to 6 Gy whole body gamma-radiation exposure, efficiently protected cellular DNA in tissues such as spleen, bone marrow and blood, from radiation induced damages as indicated by alkaline comet assay. Oxidative stress in tissues such as liver and brain of mice, following whole body exposure to various doses of gamma-radiation (2-8 Gy), monitored as levels of GSH and peroxidation of lipids, were found considerably reduced when PAsAG was orally administered (80 mg/kg body weight) to the mice one hour prior to the radiation exposure. PAsAG administration improved the per cent survival of mice following exposure to 10 Gy whole body gamma-radiation. Thus PAsAG could act as a radioprotector under in vitro, ex vivo and in vivo conditions of ionizing-radiation exposure. PMID:19384055

Chandrasekharan, Dhanya K; Kagiya, Tsutomu V; Nair, Cherupally Krishnan Krishnan



Analgesic and antiinflammatory effects of mollic acid glucoside, a 1 alpha-hydroxycycloartenoid saponin extractive from Combretum molle R. Br. ex G. Don (Combretaceae) leaf.  


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

Ojewole, John A O



Separation of patuletin-3-O-glucoside, astragalin, quercetin, kaempferol and isorhamnetin from Flaveria bidentis (L.) Kuntze by elution-pump-out high-performance counter-current chromatography  

Microsoft Academic Search

Flaveria bidentis (L.) Kuntze is an annual alien weed of Flaveria Juss. (Asteraceae) in China. Bioactive compounds, mainly flavonol glycosides and flavones from F. bidentis (L.) Kuntze, have been studied in order to utilize this invasive weed, Analytical high-performance counter-current chromatography (HPCCC) was successfully used to separate patuletin-3-O-glucoside, a mixture of hyperoside (quercetin-3-O-galactoside) and 6-methoxykaempferol-3-O-galactoside, astragalin, quercetin, kaempferol and isorhamnetin

Yun Wei; Qianqian Xie; Derek Fisher; Ian A. Sutherland



The presence of CYP79 homologues in glucosinolate-producing plants shows evolutionary conservation of the enzymes in the conversion of amino acid to aldoxime in the biosynthesis of cyanogenic glucosides and glucosinolates  

Microsoft Academic Search

A cDNA encoding CYP79B1 has been isolated from Sinapis alba. CYP79B1 from S. alba shows 54% sequence identity and 73% similarity to sorghum CYP79A1 and 95% sequence identity to the Arabidopsis T42902, assigned CYP79B2. The high identity and similarity to sorghum CYP79A1, which catalyses the conversion of tyrosine to p-hydroxyphenylacetaldoxime in the biosynthesis of the cyanogenic glucoside dhurrin, suggests that

Søren Bak; Hanne Linde Nielsen; Barbara Ann Halkier



Signal transduction pathway for L-ascorbic acid- and L-ascorbic acid 2-glucoside-induced DNA synthesis and cell proliferation in primary cultures of adult rat hepatocytes.  


We examined the effects of L-ascorbic acid and its analogues on DNA synthesis and cell proliferation. We also investigated the signal transduction pathways involved in the induction of mitogenesis by L-ascorbic acid and its analogues using primary cultures of adult rat hepatocytes. Following a 4-h serum-free cultivation, both L-ascorbic acid and its stable analogue, L-ascorbic acid 2-glucoside, time- and dose-dependently stimulated hepatocyte DNA synthesis and cell proliferation, with EC?? values of 6.46×10?? M and 3.34×10?? M, respectively. Dehydroascorbic acid (10?? M-10?? M) weakly stimulated hepatocyte mitogenesis, whereas isoascorbic acid (10?? M-10?? M) had no effect. Hepatocyte mitogenesis induced by L-ascorbic acid or L-ascorbic acid 2-glucoside was dose-dependently abolished by treatment with monoclonal antibodies against insulin-like growth factor (IGF)-I receptor, but not by treatment with monoclonal antibodies against insulin receptor or IGF-II receptor. Western blot analysis showed that both L-ascorbic acid and L-ascorbic acid 2-glucoside significantly stimulated IFG-I receptor tyrosine kinase activity within 3 min, and mitogen-activated protein (MAP) kinase activity within 5 min. These results demonstrate that both L-ascorbic acid and L-ascorbic acid 2-glucoside induce DNA synthesis and cell proliferation in primary cultures of adult rat hepatocytes by interacting with the IGF-I receptor site and by activating the receptor tyrosine kinase/MAP kinase pathway. PMID:22429571

Moteki, Hajime; Shimamura, Yuya; Kimura, Mitsutoshi; Ogihara, Masahiko



The chemical synthesis of 1-O-(indol-3'-ylacetyl)-beta-D-glucopyranose. The higher activity of the glucoside in comparison with exogenous indol-3-ylacetic acid in plant-section elongation tests.  


1. The synthesis of 1-O-(indol-3'-ylacetyl)-beta-d-glucopyranose via the fully benzylated 1-O-(indol-3'-ylacetyl)-d-glucopyranose is described. The configuration of the free ester glucoside was confirmed by complete hydrolysis with beta-glucosidase and by the n.m.r. spectrum of the tetra-acetyl derivative. 2. The growth-promoting effect of the glucoside in Avena coleoptile- and pea stem-section tests distinctly exceeds the responses stimulated by equimolar amounts of indol-3-ylacetic acid or equimolar mixtures of indol-3-ylacetic acid and glucose at all concentrations investigated. Time-sequence experiments revealed that the sections stimulated by the glucoside exhibit a markedly greater rate of elongation than those promoted by indol-3-ylacetic acid. 3. 1-O-(Indol-3'-ylacetyl)-beta-d-glucopyranose was isolated from intact Avena coleoptiles. 4. According to the results, the conjugation of indol-3-ylacetic acid with glucose could not be considered merely as a detoxication mechanism for indol-3-ylacetic acid in plant tissues. PMID:5343792

Keglevi?, D; Pokorny, M



Stimulation of callose synthesis in vivio correlates with changes in intracellular distribution of the callose synthase activator [beta]-Furfuryl-[beta]-Glucoside  

SciTech Connect

[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.

Ohana, P.; Benziman, M.; Delmer, D.P. (Hebrew Univ., Jerusalem (Israel))



Cyanidin-3-Glucoside-Rich Extract from Chinese Bayberry Fruit Protects Pancreatic ? Cells and Ameliorates Hyperglycemia in Streptozotocin-Induced Diabetic Mice  

PubMed Central

Abstract Chinese bayberry fruit is a rich source of anthocyanins, especially cyanidin-3-glucoside (C3G). The present study investigated the protective effects of C3G-rich bayberry fruit extract (CRBFE) against pancreatic ? cells against oxidative stress–induced injury as well as its hypoglycemic effect in diabetic mice. Bayberry extract from “Biqi” was used for both in vitro and in vivo testing because of its high C3G content and high antioxidant capacity. Pretreatment of ? cells with CRBFE (containing 0.5??mol/L C3G) prevented cell death, increased cellular viability, and decreased mitochondrial reactive oxygen species production and cell necrosis induced by 800 or 1,200??mol/L H2O2. CRBFE dose-dependently up-regulated pancreatic duodenal homeobox 1 gene expression, contributing to increased insulin-like growth factor II gene transcript levels and insulin protein in INS-1 cells. In addition, administration of CRBFE (150??g of C3G/10?g of body weight twice per day) significantly reduced blood glucose in streptozotocin-induced diabetic ICR mice and increased the glucose tolerance in an oral glucose tolerance test (P<.05). Such results indicated that CRBFE might be useful in prevention and control of diabetes mellitus and diabetes-associated complications.

Sun, Chong-De; Zhang, Bo; Zhang, Jiu-Kai; Xu, Chang-Jie; Wu, Yu-Lian; Chen, Kun-Song



Tetrahydroxystilbene glucoside improves the learning and memory of amyloid-?(????)-injected rats and may be connected to synaptic changes in the hippocampus.  


The aim of this study was to evaluate the protective effects of 2,3,5,4'-tetrahydroxystilbene-2-O-?-D-glucoside (TSG), an active component extracted from Polygonum multiflorum, on learning/memory deficits in Alzheimer's disease (AD). We randomly divided 24 male Sprague-Dawley rats among 4 groups: (i) the sham-operated group (control); (ii) sham-operated group also treated with TSG (sham+TSG); (iii) beta amyloid treated group (A?); and (iv) A? treatment group also treated with TSG (A?+TSG). Rats in the A? and A?+TSG groups were treated with A????? intracerebroventricularly, whereas the control and sham+TSG groups were given phosphate-buffered saline. Rats in the sham+TSG and A?+TSG groups were then treated intragastrically with TSG (50 mg·(kg body mass)?¹·day?¹) for 4 weeks, and rats in the A? and control groups were treated with saline. The results from Morris water maze tests, electron microscopy, real-time polymerase chain reaction, and Western blotting demonstrated that A????? induced impairment in learning and memory, degeneration in synaptic structures, and downregulation of Src and NR2B at the gene and protein level, respectively. These alterations were reversed by the administration of TSG, suggesting that TSG exerts anti-AD properties by protecting synaptic structure and function. TSG-induced upregulation of Src and NR2B may be responsible for this process. PMID:23181273

Zhou, Lin; Hou, Ying; Yang, Qidong; Du, Xiaoping; Li, Min; Yuan, Mei; Zhou, Zhiwen



Evaluation of the new anti-inflammatory compound ethyl salicylate 2-O-?-D-glucoside and its possible mechanism of action.  


Ethyl salicylate 2-O-?-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-? and IL-1?. 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-?B in RAW264.7 cells by blocking phosphorylation of inhibitor I?B? and p65. Consistent with these results, we found that ESG prevented the nuclear translocation of NF-?B 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-?B signal pathway. PMID:23219581

Xin, Wenyu; Huang, Chao; Zhang, Xue; Zhang, Guidong; Ma, Xiaowei; Sun, Lan; Wang, Chao; Zhang, Dongming; Zhang, Tiantai; Du, Guanhua



CoMFA and CoMSIA studies on C-aryl glucoside SGLT2 inhibitors as potential anti-diabetic agents.  


SGLT2 has become a target of therapeutic interest in diabetes research. CoMFA and CoMSIA studies were performed on C-aryl glucoside SGLT2 inhibitors (180 analogues) as potential anti-diabetic agents. Three different alignment strategies were used for the compounds. The best CoMFA and CoMSIA models were obtained by means of Distill rigid body alignment of training and test sets, and found statistically significant with cross-validated coefficients (q²) of 0.602 and 0.618, respectively, and conventional coefficients (r²) of 0.905 and 0.902, respectively. Both models were validated by a test set of 36 compounds giving satisfactory predicted correlation coefficients (r² pred) of 0.622 and 0.584 for CoMFA and CoMSIA models, respectively. A comparison was made with earlier 3D QSAR study on SGLT2 inhibitors, which shows that our 3D QSAR models are better than earlier models to predict good inhibitory activity. CoMFA and CoMSIA models generated in this work can provide useful information to design new compounds and helped in prediction of activity prior to synthesis. PMID:23305412

Vyas, V K; Bhatt, H G; Patel, P K; Jalu, J; Chintha, C; Gupta, N; Ghate, M



Pharmacokinetics of 2,3,5,4'-tetrahydroxystilbene-2-O-?-D-glucoside in rat using ultra-performance LC-quadrupole TOF-MS.  


2,3,5,4'-Tetrahydroxystilbene-2-O-?-D-glucoside (THSG) from Polygoni multiflori has been demonstrated to possess a variety of pharmacological activities, including antioxidant, anti-inflammatory and hepatoprotective activities. Ultra-performance LC-quadrupole TOF-MS with MS Elevated Energy data collection technique and rapid resolution LC with diode array detection and ESI multistage MS(n) methods were developed for the pharmacokinetics, tissue distribution, metabolism, and excretion studies of THSG in rats following a single intravenous or oral dose. The three metabolites were identified by rapid resolution LC-MS(n). The concentrations of the THSG in rat plasma, bile, urine, feces, or tissue samples were determined by ultra-performance LC-MS. The results showed that THSG was rapidly distributed and eliminated from rat plasma. After the intravenous administration, THSG was mainly distributing in the liver, heart, and lung. For the rat, the major distribution tissues after oral administration were heart, kidney, liver, and lung. There was no long-term storage of THSG in rat tissues. Total recoveries of THSG within 24 h were low (0.1% in bile, 0.007% in urine, and 0.063% in feces) and THSG was excreted mainly in the forms of metabolites, which may resulted from biotransformation in the liver. PMID:23371758

Zhao, Ying-Yong; Zhang, Li; Feng, Ya-Long; Chen, Dan-Qian; Xi, Zhi-Hui; Du, Xiao; Bai, Xu; Lin, Rui-Chao



Intestinal SGLT1-mediated absorption and metabolism of benzyl beta-glucoside contained in Prunus mume: carrier-mediated transport increases intestinal availability.  


The intestinal absorption of benzyl beta-glucoside (BNZ beta glc) contained in the fruit of Prunus mume SIEB. et ZUCC. (Rosaceae), which is traditionally used as a medicinal food in Japan, was studied in rat intestines. BNZ beta glc was absorbed from the mucosal to serosal sides. Its metabolite, benzyl alcohol (BAL), was also detected on both the mucosal and serosal sides. In the presence of phloridzin (Na(+)/glucose cotransporter (SGLT1) inhibitor) or in the absence of Na+ (driving force), BNZ beta glc absorption was significantly decreased. Transport clearance of BNZ beta glc across the brush border membrane decreased as its concentration increased. These results indicate that BNZ beta glc is transported by SGLT1. Metabolic clearance of BNZ beta glc also decreased as its concentration increased. The amount ratio of BNZ beta glc to BAL on the serosal side increased with the increase of BNZ beta glc concentration. The intestinal availability of BNZ beta glc was lower in the absence of Na+ than in the presence of Na+, indicating that the SGLT1-mediated transport of BNZ beta glc increases intestinal availability by decreasing the intestinal extraction ratio. This neutraceutical study concluded that intestinal carrier-mediated transport across the brush border membrane improves the intestinal availability of nutritionally, pharmacologically or physiologically active compounds that undergo intestinal metabolism (first-pass effect). PMID:15716003

Mizuma, Takashi; Nakamura, Maya; Ina, Hiroji; Miyazaki, Toshio; Hayashi, Masahiro



Seasonal alteration in amounts of lignans and their glucosides and gene expression of the relevant biosynthetic enzymes in the Forsythia suspense leaf.  


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

Morimoto, Kinuyo; Satake, Honoo



Determination of Iriflophenone 3-C-?-d-Glucoside From Aquilaria spp. by an Indirect Competitive Enzyme-linked Immunosorbent Assay Using a Specific Polyclonal Antibody.  


Polyclonal antibody against iriflophenone 3-C-?-d-glucoside (IP3G), a major compound from the leaves of Aquilaria spp., was produced for the development of an enzyme-linked immunosorbent assay (ELISA). The results showed that the antibodies were specific for IP3G. The produced antibody has low cross reactivity with iriflophenone 3,5-C-?-d-diglucopyranoside (13%), genkwanin 5-O-?-primeveroside (3.55%) and no cross reactivity found in other compounds. The range of ELISA assay extends from 100 to 1560 ng/mL with coefficient of variation (CV) 1.19% to 2.07% for intra-assay and 3.76% to 7.15% for inter-assay precision levels. The recovery rates of IP3G in the leaves of Aquilaria spp. were in the range of 96.0% to 99.0% with CV 4.50% to 5.32%. A correlation between ELISA and high-performance liquid chromatography methods was obtained when analysis of IP3G in the plant samples (R(2) = 0.9321). These results suggest that the developed ELISA method can be applied to determine IP3G content with high specificity, rapidity, and simplicity. The developed immunosorbent assay in this study provides a useful tool for the analysis of IP3G in plant samples and products. PMID:23924405

Putalun, Waraporn; Yusakul, Gorawit; Saensom, Paritad; Sritularak, Boonchoo; Tanaka, Hiroyuki



Nondigestible saccharides suppress the bacterial degradation of quercetin aglycone in the large intestine and enhance the bioavailability of quercetin glucoside in rats.  


Contribution of intestinal bacterial degradation of quercetin aglycone to the promotive effects of fructooligosaccharides and di-D-fructose anhydride III (DFAIII) on quercetin-3-O-beta-glucoside (Q3G) bioavailability was examined. Male Sprague-Dawley rats were fed 0.68% Q3G diets with or without 1.5% or 3% oligosaccharides for 2 weeks. Blood levels and urinary excretion of quercetin and methylquercetin conjugates, measured by methanol extraction and LC-MS analyses, were dose-dependently and adaptively increased by the oligosaccharide supplementation with increasing cecal fermentation (Experiment 1). Degradation of Q3G and quercetin aglycone by cecal bacteria in oligosaccharide-fed rats was much lower than that in the control rats using an anaerobic culture system (Experiment 2). Using the ligated intestinal sacs of anesthetized rats, we found that the cecum possessed high absorptive capacity for quercetin derivatives (Experiment 3). These results demonstrate that feeding of the oligosaccharides strongly suppresses the bacterial degradation of quercetin aglycone in the cecum, thus largely contributing to the increased bioavailability of Q3G. PMID:19807098

Matsukawa, Noriko; Matsumoto, Megumi; Shinoki, Aki; Hagio, Masahito; Inoue, Ryo; Hara, Hiroshi



Malvidin-3-O-? glucoside, major grape anthocyanin, inhibits human macrophage-derived inflammatory mediators and decreases clinical scores in arthritic rats.  


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-? glucoside (Mal?g), the major grape anthocyanin, is bioactive with no toxicity on human PBMC. Mal?g decreased the transcription of genes encoding inflammatory mediators, confirmed by the inhibition of TNF?, IL1, IL-6 and iNOS-derived nitric oxide (NO) secretion from activated macrophages. As Mal?g also inhibited inflammatory response of rat macrophages, we investigated the anti-inflammatory potential of Mal?g in chronic rat adjuvant-induced arthritis (AIA). Mal?g significantly diminished inflammatory cachexia and arthritic paw scores in AIA rats at both therapeutic and preventive levels. In vivo effects of Mal?g correlated with down-regulation of NO generation from AIA rats' peritoneal macrophages ex vivo. These data indicate that Mal?g, major grape anthocyanin, is a potent anti-inflammatory agent in vitro and in vivo, without detectable toxic effect. PMID:23796750

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



Radioprotection to small intestine of the mice against ionizing radiation by semiquinone glucoside derivative (SQGD) isolated from Bacillus sp. INM-1.  


Ionizing irradiation induces severe damage to the intestinal crypt cells which are responsible for renovation and maintenance of the intestinal cellular architecture. Therefore, protection of intestinal cells and tissue against lethal irradiation using a semiquinone glucoside derivative (SQGD) isolated from radioresistant bacterium Bacillus sp. INM-1 is the prime focus of the present investigation. BALB/c mice were administered by SQGD (50 mg/kg.b.wt. i.p.) 2 h before whole body irradiation (10 Gy), and histological analysis of the jejunum section was carried out and compared to the irradiated mice. Significant (p < 0.0001) increase in villus length, number of cells per villus, crypts numbers per villus section, total cells counts and mitotic cell counts per crypt and low goblet cells per villus section, and low apoptotic index per crypt section were observed in the irradiated mice pre-treated by SQGD at 48-168 h. Significant induction in NF-k? at 24 h and Bcl-2/Bax ratio was observed in irradiated mice pre-treated by SQGD compared to only irradiated animals. SQGD pre-treatment before irradiation was found instrumental to reverse the radiation-induced degenerative changes by replenishment of the damaged cells by enhancing mitotic, proliferating, pro-survival, and apoptosis inhibitory activities probably through modulation of cell cycle arrest in G(1)/S phase in the intestinal cellular milieu. PMID:22875666

Patel, Dev Dutt; Bansal, Deen Dayal; Mishra, Saurabh; Arora, Rajesh; Sharma, Ashok; Jain, Swatantra Kumar; Kumar, Raj



Elucidation of the Final Reactions of DIMBOA-Glucoside Biosynthesis in Maize: Characterization of Bx6 and Bx71[W][OA  

PubMed Central

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.

Jonczyk, Rafal; Schmidt, Holger; Osterrieder, Anne; Fiesselmann, Andreas; Schullehner, Katrin; Haslbeck, Martin; Sicker, Dieter; Hofmann, Diana; Yalpani, Nasser; Simmons, Carl; Frey, Monika; Gierl, Alfons



2, 3, 5, 4?-Tetrahydroxystilbene-2-O-Beta-D-Glucoside Improves Gastrointestinal Motility Disorders in STZ-Induced Diabetic Mice  

PubMed Central

Oxidative stress has recently been considered as a pivotal player in the pathogenesis of diabetic gastrointestinal dysfunction. We therefore investigated the role of 2, 3, 5, 4?-tetrahydroxystilbene-2-O-beta-D-glucoside (THSG) that has a strong anti-oxidant property, in diabetic gastrointestinal dysmotility as well as the underlying protective mechanisms. THSG restored the delayed gastric emptying and the increased intestinal transit in streptozotocin (STZ)-induced diabetic mice. Loss of neuronal nitric oxide synthase (nNOS) expression and impaired nonadrenergic, noncholinergic (NANC) relaxations in diabetic mice were relieved by long-term preventive treatment with THSG. Meanwhile, THSG (10?7?10?4 mol/L) enhanced concentration-dependently NANC relaxations of isolated colons in diabetic mice. Diabetic mice displayed a significant increase in Malondialdehyde (MDA) level and decrease in the activity of glutathione peroxidase (GSH-Px), which were ameliorated by THSG. Inhibition of caspase-3 and activation of ERK phosphorylation related MAPK pathway were involved in prevention of enhanced apoptosis in diabetes afforded by THSG. Moreover, THSG prevented the significant decrease in PPAR-? and SIRT1 expression in diabetic ileum. Our study indicates that THSG improves diabetic gastrointestinal disorders through activation of MAPK pathway and upregulation of PPAR-? and SIRT1.

Chang, Mu-Jun; Xiao, Jun-Hua; Wang, Yong; Yan, Yong-Li; Yang, Jun; Wang, Jia-Ling



Further study of the Hansenula polymorpha MAL locus: characterization of the alpha-glucoside permease encoded by the HpMAL2 gene.  


The HpMAL2 gene of the MAL gene cluster of Hansenula polymorpha codes for a permease similar to yeast maltose and alpha-glucoside transporters. Genomic disruption of HpMAL2 resulted in an inability of cells to grow on maltose, sucrose, trehalose, maltotriose and turanose, as well as a lack of p-nitrophenyl-alpha-D-glucopyranoside (PNPG) transport. PNPG uptake was competitively inhibited by all these substrates, with Ki values between 0.23 and 1.47 mM. Transport by HpMal2p was sensitive to pH and a protonophore carbonyl cyanide-m-chlorophenylhydrazone (CCCP), revealing its energization by the proton gradient over the cell membrane. Although HpMAL2 was responsible for trehalose uptake, its expression was not induced during trehalose growth. A maltase disruption mutant did not grow on maltotriose and turanose, whereas it showed normal growth on trehalose, demonstrating the dispensability of maltase for intracellular hydrolysis of trehalose. In a Genolevures clone pBB0AA011B12, the promoter region and the N-terminal fragment of the putative transactivator of MAL genes is located adjacent to HpMAL2. A reporter gene assay showed that expression from that promoter was induced by maltose and sucrose, repressed by glucose, and derepressed during glycerol and trehalose growth. Therefore, we presume that the gene encodes a functional regulator. PMID:17559409

Viigand, Katrin; Alamäe, Tiina



Inhibitory effects of isorhamnetin-3-O-beta-D-glucoside from Salicornia herbacea on rat lens aldose reductase and sorbitol accumulation in streptozotocin-induced diabetic rat tissues.  


The inhibitory effects of compounds from Salicornia herbacea (Chenopodiaceae) on rat lens aldose reductase (RLAR) and sorbitol accumulation in streptozotocin-induced diabetic rat tissues were investigated. The various fractions from the MeOH extract of S. herbacea were tested for their effects on RLAR in vitro. Among them, the EtOAc fraction was found to exhibit a potent RLAR inhibition (IC(50)=0.75 microg/ml), from which an active principle as a potent AR inhibitor was isolated and its chemical structure was elucidated as isorhamnetin-3-O-beta-D-glucoside (1) by spectral analysis. Compound 1 exhibited a potent RLAR inhibition in vitro, its IC(50) being 1.4 microM. Compound 1, when administered orally at 25 mg/kg in streptozotocin (STZ)-induced diabetic rats, caused not only a significant inhibition of serum glucose concentration but also sorbitol accumulation in the lenses, red blood cells (RBC), and sciatic nerves. These results indicate that compound 1 from S. herbacea is a leading compound for further study as a new drug for the prevention and/or treatment of diabetes and its complications. PMID:15863906

Lee, Yeon Sil; Lee, Sanghyun; Lee, Hye Seung; Kim, Bak-Kwang; Ohuchi, Kazuo; Shin, Kuk Hyun



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)

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.

March, Raymond E.; Miao, Xiu-Sheng; Metcalfe, Chris D.; Stobiecki, Maciej; Marczak, Lukasz



Combining high-performance liquid chromatography with on-line microdialysis sampling for the simultaneous determination of ascorbyl glucoside, kojic acid, and niacinamide in bleaching cosmetics.  


We have used on-line microdialysis sampling coupled with high-performance liquid chromatography and UV-vis detection to simultaneously determine the contents of ascorbyl glucoside (AA-2G), kojic acid (KA), and niacinamide (VitB(3)) in commercial bleaching cosmetics. Our results indicate that AA-2G, KA, and VitB(3) separated well within 4.5 min on a reverse-phase Hypersil Fluophase PFP column when eluting with 0.020 M phosphate buffer solution in 40% (v/v) methanol at pH 5.5. The calibration curves were linear over the ranges 0.068-304, 0.071-284, and 0.024-488 microg mL(-1) for AA-2G, KA, and VitB(3), respectively, with correlation coefficients for the linear regression analyses falling within the range 0.9982-0.9999. The detection limits for AA-2G, KA, and VitB(3) were 0.01, 0.01, and 0.007 microg mL(-1), respectively. The detection wavelength was robust when the levels of the analytes in the samples were high (0.1-2%). The analytes were all detected using ultraviolet light (254 nm). The compounds diffuse through the membrane more readily when KA and VitB(3) are in their molecular forms and AA-2G is ionized. The recoveries were in the range 92-106% with good reproducibility (R.S.D.=3.9-8.7%). We used this procedure to assay six commercially available bleaching cosmetics; our results confirmed not only the precision of the method but also the claims made on the labels of the cosmetics. This approach provides a very simple means to determine the contents of AA-2G, KA, and VitB(3) in various dosages in bleaching cosmetics. PMID:17386432

Lin, Cheng-Hui; Wu, Hsin-Lung; Huang, Yeou-Lih



Cyanidin-3-O-?-glucoside with the aid of its metabolite protocatechuic acid, reduces monocyte infiltration in apolipoprotein E-deficient mice.  


Polyphenols, including anthocyanins, from various plant foods are effective in reducing the severity of atherosclerosis in animal and human studies. Due to the poor understanding of the bioavailability of anthocyanins, the potential antiatherogenic mechanisms underlying the action remain largely unknown. Herein, we found that oral gavage of cyanidin-3-O-?-glucoside (Cy-3-G) could be transformed into protocatechuic acid (PCA), and the plasma maximal levels of Cy-3-G were 3.7-fold lower than that of PCA in the apolipoprotein E (ApoE)-deficient mice. Subsequently, we observed that PCA treatment has a higher capacity than Cy-3-G treatment in decreasing CC chemokine receptor 2 (CCR2) expression in the mouse peripheral blood monocytes (PBMs), along with reducing the mouse PBMs chemokine toward CC ligand-2 (CCL2) in a Boyden chamber. Interesting, in the ApoE-deficient mouse model, orally gavaged with Cy-3-G has a higher ability than gavaged with PCA to reduce CCR2 expression in PBMs. PBMs deprived from the Cy-3-G-treated ApoE-deficient mice have a lower ability than those from PCA-treated animals to migrate toward CCL2. Furthermore, as compared with the PCA group, Cy-3-G treatment more efficiently reduced thioglycollate-induced macrophage infiltration into the abdominal cavity. Thus, we suggest that Cy-3-G may reduce the monocyte infiltration in mice via down-regulation of CCR2 expression in monocytes, at least in part, with the aid of its metabolite PCA. These above data imply that the anti-monocyte/macrophage infiltration property of Cy-3-G and its metabolite PCA may be an important antiatherogenic mechanism for anthocyanins. PMID:21569764

Wang, Dongliang; Zou, Tangbin; Yang, Yan; Yan, Xiao; Ling, Wenhua



Purification and characterization of guinea-pig liver microsomal deacetylase involved in the deacetylation of the O-glucoside of N-hydroxyacetanilide.  

PubMed Central

A microsomal deacetylase that catalyses the deacetylation of the O-glucoside of N-hydroxyacetanilide (GHA) was purified from guinea-pig liver. The activity was located exclusively in the microsomes and not detected in the cytosol. The purified GHA deacetylase was a trimeric protein with a molecular mass of 160+/-10 (S.D.) kDa composed of subunits of 53+/-2 kDa; its pI was 4.7. The N-terminal amino acid sequence of GHA deacetylase was similar to those reported for guinea-pig and rat liver microsomal carboxylesterases. The GHA deacetylase showed a comparable hydrolytic activity towards p-nitrophenyl acetate (PNPA), although the activities towards N-hydroxyacetanilide, acetanilide and some endogenous acylated compounds were very low or not detectable. The deacetylase activity towards GHA was inhibited by organophosphates but not by p-chloromercuribenzoate, suggesting that GHA deacetylase can be classified as a B-esterase. The enzyme exhibited a positive homotropic co-operativity towards GHA. The values of the Hill coefficient, the half-saturating concentration ([S]0.5) for GHA, and Vmax were 1.59+/-0.03, 5.51+/-0.07 mM and 32.5+/-1.4 micromol/min per mg respectively, at the optimum pH of 8.5. The bell-shaped pH dependence of the Vmax/[S]0.5 profile indicated pKa values attributed to histidine and lysine residues. The study of stoichiometric inhibition by di-isopropyl fluorophosphate and kinetic analysis with the Monod-Wyman-Changeux model suggests that GHA deacetylase has six substrate binding sites and three catalytically essential serine residues per enzyme molecule.

Suzuki-Kurasaki, M; Yoshioka, T; Uematsu, T



Cucurbitacin L 2-O-?-Glucoside Demonstrates Apoptogenesis in Colon Adenocarcinoma Cells (HT-29): Involvement of Reactive Oxygen and Nitrogen Species Regulation  

PubMed Central

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-?-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-?) 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.

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.



Comparative study on the excretion of vitexin-4''-O-glucoside in mice after oral and intravenous administration by using HPLC.  


The aim of the present study was to characterize the excretion of pure vitexin-4"-O-glucoside (VOG) in mice following oral and intravenous administration at a dose of 30 mg/kg. A sensitive and specific HPLC method with hespridin as internal standard, a Diamonsil C18 column protected with a KR C18 guard column and a mixture consisting of methanol-acetonitrile-tetrahydrofuran-0.1% glacial acetic acid (6:2:18:74, v/v/v/v) as mobile phase was developed and validated for quantitative analysis in biological samples. VOG could be excreted as prototype in excreta including urine and feces after both routes of administration, and the cumulative excretion of VOG was 24.31?±?11.10% (17.97?±?5.59% in urinary excretion; 6.34?±?5.51% in fecal excretion) following oral dosing and 5.66?±?3.94% (4.78?±?3.13% in urinary excretion; 0.88?±?0.81% in fecal excretion) following intravenous dosing. The results showed that the elimination of VOG after the two routes was fairly low, which meant that VOG was metabolized as other forms and the elimination after oral dosing was almost 4.3-fold that after intravenous dosing. For both routes of administration, VOG excreted as prototype in urine was much more than that in feces, nearly 2.83-fold for oral administration and 5.43-fold for intravenous administration, which should be attributed to enterohepatic circulation. Taken together, renal excretion was the dominant path of elimination of VOG for oral and intravenous administration in mice and biliary excretion contributed less. Copyright © 2013 John Wiley & Sons, Ltd. PMID:23760836

Cai, Shuang; Chen, Yinghui; Zhang, Wenjie; Ying, Xixiang



Metabolism of cyanidin-3-O-beta-D-glucoside isolated from black colored rice and its antiscratching behavioral effect in mice.  


Black-colored rice (BCR), the main constituent of which is cyanidin-3-O-beta-D-glucoside (C3G), exhibits an anti-allergic effect, and orally administered C3G is mainly metabolized to protocatechuic acid in rats. Therefore, to understand the relationship between the metabolism of C3G and its pharmacological effect, we isolated C3G from BCR, anaerobically incubated it with fecal microflora, investigated its metabolite(s) by LC-MS/MS, and measured the antiscratching behavioral effects of C3G and its metabolites. C3G was metabolized to protocatechuic acid via cyanidin. Protocatechuic acid and cyanidin were identified as the metabolites. The activities transforming C3G to protocatechuic acid and cyanidin were 28.2 +/- 11.7 and 21.8 +/- 5.2 nmol/h/mg fecal microflora, respectively. C3G and its metabolites showed inhibitory effects against histamine- or compound 48/80-induced scratching behaviors in mice. C3G more potently inhibited scratching behaviors following oral administration than following intraperitoneal administration. However, protocatechuic acid and cyanidin showed more potent inhibition when administered intraperitoneally than when administered orally. These metabolites also inhibited the expression of allergic cytokines, IL-4 and TNF-alpha, and the activation of their transcription factor, NF-kappaB, in RBL-2H3 cells stimulated with IgE-antigen. These findings suggest that C3G-rich BCR may be a beneficial food for diseases involving scratching behaviors, such as chronic dermatitis, rhinitis, and psoriasis. PMID:19799667

Han, S-J; Ryu, S-N; Trinh, H-T; Joh, E-H; Jang, S-Y; Han, M J; Kim, D-H



Antifungal property of dihydrodehydrodiconiferyl alcohol 9'-O-beta-D-glucoside and its pore-forming action in plasma membrane of Candida albicans.  


The aims of this study wereto investigate the antifungal activity as a bioactive property of dihydrodehydro-diconiferyl alcohol 9'-O-3-D-glucoside (DDDC9G) and the mode of action(s) involved in its effect. Antifungal susceptibility testing showed that DDDC9G possessed potent antifungal activities toward various fungal strains with almost no hemolytic effect. To understand the antifungal mechanism(s) of DDDC9G, we conducted the following experiments in this study using Candida albicans. Fluorescence experiments using the probe 1,6-eiphenyl-1, 3, 5-hexatriene (DPH) and propidium iodide suggested that DDDC9G perturbed the fungal plasma membrane. Consecutively, the analysis of the transmembrane electrical potential (DeltaPsi) with 3, 3'-dipropylthiadicarbocyanine iodide [DiSC3(5)] and bis-(1,3-dibutylbarbituric acid) trimethine oxonol [DiBAC4(3)] indicated that DDDC9G induced membrane-depolarization. Furthermore, model membrane studies were performed wiith rhodamine-labeled giant unilamellar vesicles (GUVs), calcein encapsulating large unilamellar vesicles (ILUVs), and FITC-dextran (FD) loaded LUVs. These results demonstrated that the antifungal effects of DDDC9G upon the fungal plasma membrane were through the formation of pores with the radii between 0.74 nm and 1.4 nm. Finally, in three dimensional (3D) flow cytometric contour plots, a reduced cell size was observed as a result of osmolarity changes from DDDC9G-induced structural and functional membrane damages.Therefore, the present study suggests that DDDC9G exerts its antifungal effect by damaging the membrane through pore formation in the fungal plasma membrane. PMID:22406553

Choi, Hyemin; Cho, Jaeyong; Jin, Qinglong; Woo, Eun-Rhan; Lee, Dong Gun



Enhancement by ascorbic acid 2-glucoside or repeated additions of ascorbate of mitogen-induced IgM and IgG productions by human peripheral blood lymphocytes.  


In this study, the effect of ascorbic acid 2-glucoside (AA-2G), a stable derivative of ascorbic acid (AsA), or repeated additions of ascorbate on antibody productions by human peripheral blood lymphocytes (PBLs) was examined, and the physiological function of AsA was evaluated. When human PBLs were stimulated with Staphylococcus aureus Cowan I or pokeweed mitogen, AA-2G remarkably increased the numbers of IgM- and IgG-secreting cells which were detected by enzyme-linked immunospot assay. Although a single addition of ascorbate was without effect, the effect of AA-2G was remarkably inhibited by the addition of castanospermine, an alpha-glucosidase inhibitor; and moreover, repeated additions of AsA to the culture medium during the culture period enhanced the response to the same level as did a single addition of AA-2G. These results indicate that AsA has the ability to stimulate the immunoglobulin productions by AA-2G. The phytohemagglutinin-induced proliferative response of PBLs was also stimulated by AA-2G. The intracellular AsA content in PBLs cultured with AA-2G was maintained at relatively high levels during the culture period, whereas the content with a single dose of AsA reached nearly zero by the end of the experiment. These in vitro findings suggest that AA-2G and AsA function as potent immunostimulators of antibody production in humans and that the intracellular AsA content is a key parameter for establishing the immune response of PBLs. PMID:7723222

Tanaka, M; Muto, N; Gohda, E; Yamamoto, I



Isolation and reconstitution of cytochrome P450ox and in vitro reconstitution of the entire biosynthetic pathway of the cyanogenic glucoside dhurrin from sorghum.  

PubMed Central

A cytochrome P450, designated P450ox, that catalyzes the conversion of (Z)-p-hydroxyphenylacetaldoxime (oxime) to p-hydroxymandelonitrile in the biosynthesis of the cyanogenic glucoside beta-D-glucopyranosyloxy-(S)-p-hydroxymandelonitrile (dhurrin), has been isolated from microsomes prepared from etiolated seedlings of sorghum (Sorghum bicolor L. Moench). P450ox was solubilized using nonionic detergents, and isolated by ion-exchange chromatography, Triton X-114 phase partitioning, and dye-column chromatography. P450ox has an apparent molecular mass of 55 kD, its N-terminal amino acid sequence is -ATTATPQLLGGSVP, and it contains the internal sequence MDRLVADLDRAAA. Reconstitution of P450ox with NADPH-P450 oxidoreductase in micelles of L-alpha-dilauroyl phosphatidylcholine identified P450ox as a multifunctional P450 catalyzing dehydration of (Z)-oxime to p-hydroxyphenylaceto-nitrile (nitrile) and C-hydroxylation of p-hydroxyphenylacetonitrile to nitrile. P450ox is extremely labile compared with the P450s previously isolated from sorghum. When P450ox is reconstituted in the presence of a soluble uridine diphosphate glucose glucosyltransferase, oxime is converted to dhurrin. In vitro reconstitution of the entire dhurrin biosynthetic pathway from tyrosine was accomplished by the insertion of CYP79 (tyrosine N-hydroxylase), P450ox, and NADPH-P450 oxidoreductase in lipid micelles in the presence of uridine diphosphate glucose glucosyltransferase. The catalysis of the conversion of Tyr into nitrile by two multifunctional P450s explains why all intermediates in this pathway except (Z)-oxime are channeled.

Kahn, R A; Bak, S; Svendsen, I; Halkier, B A; M?ller, B L



Development and validation of a liquid chromatography/linear ion trap mass spectrometry method for the quantitative determination of deoxynivalenol-3-glucoside in processed cereal-derived products.  


Cereal-based food can be frequently contaminated by the presence of mycotoxins derived from Fusarium fungus, and, in particular, by deoxynivalenol (DON). Nowadays, analytical strategies for the detection of DON are well developed, but there are gaps for what concerns a correct identification, quantification and toxicological evaluation of the respective metabolites, mainly related to detoxifying actions via plant metabolism or to processing technologies and also referred to as "masked" mycotoxins. Here, we report the development of a liquid chromatography/linear ion trap mass spectrometry method capable of determining deoxynivalenol-3-glucoside (DON-3G), which is the main known DON metabolite, in different processed cereal-derived products. Samples were extracted with a mixture of methanol/water (80:20; v/v) and cleaned up using immunoaffinity columns. Chromatographic separation was performed using a core-shell C(18) column with an aqueous acetic acid/methanol mixture as the mobile phase under gradient conditions. The method was in-house validated on a bread matrix as follows: matrix-matched linearity (r(2)>0.99) was established in the range of 10-200 ?g kg(-1); trueness expressed as recovery was close to 90%; good intermediate precision (overall RSD<9%) and adequate detection quantitation limits (4 and 11 ?g kg(-1), respectively) were achieved. Furthermore, applying a metrology approach based on intralaboratory data, the estimated measurement expanded uncertainty was determined to be equal to 29%. The reliability of the method was finally demonstrated in bread, cracker, biscuit and minicake commodities, resulting in relatively low levels of DON-3G, which were not higher than 30 ?g kg(-1). PMID:23194564

Suman, M; Bergamini, E; Catellani, D; Manzitti, A



Further isolation of antioxidative (+)-1-hydroxypinoresinol-1- O -?- d -glucoside from the rhizome of Salvia miltiorrhiza that acts on peroxynitrite, total ROS and 1,1-diphenyl-2-picrylhydrazyl radical  

Microsoft Academic Search

A furanofuranoid lignan glycoside, with radical scavenging on peroxynitrite, total reactive oxygen species (ROS) and 1,1-diphenyl-2-picrylhydrazyl\\u000a (DPPH) radical, was isolated from the rhizome ofSalvia miltiorrhiza and characterized as (+)-1-hydroxypinoresinol-1-O-?-d-glucoside based on spectroscopic evidence. The compound exhibited peroxynitrite, total ROS and DPPH radical scavenging activities\\u000a with IC50 values of 3.23 ± 0.04, 2.26 ± 0.07 and 32.3 ± 0.13 ?M, respectively.

Hye Sook Kang; Hae Young Chung; Dae Seok Byun; Jae Sue Choi



Supplementation of cyanidin-3-O-?-glucoside promotes endothelial repair and prevents enhanced atherogenesis in diabetic apolipoprotein E-deficient mice.  


Atherosclerosis is accelerated in diabetes mellitus mainly due to the reduced availability and function of endothelial progenitor cells (EPCs). The purpose of this study was to determine the protective effects of the anthocyanin cyanidin-3-O-?-glucoside (C3G) on EPC function and endothelial repair in diabetic apolipoprotein E-deficient (apoE(-/-)) mice. Diabetes mellitus was induced in 8-wk-old male apoE(-/-) mice with streptozotocin. Diabetic apoE(-/-) mice were fed the AIN-93 diet or an AIN-93 diet supplemented with C3G (0.2% wt:wt) for 6 wk. Sham-injected apoE(-/-) mice fed the AIN-93 diet served as nondiabetic controls. The endothelium-dependent relaxation response to acetylcholine in the aortas of C3G-fed mice was greater by 51% compared with diabetic mice fed the AIN-93 diet (P < 0.05) and was similar to that in nondiabetic apoE(-/-) mice. The capacity of in vitro adhesion to fibronectin, migration, and tube formation was significantly impaired in diabetic EPCs (decreased by 83, 61.9, and 74.5%, respectively, compared with nondiabetic controls; all P < 0.01), which was significantly rescued in response to C3G (increased by 3.9-, 2-, and 1.8-fold compared with diabetic EPCs, respectively; all P < 0.05). At the molecular level, the phosphorylation levels of AMP-activated protein kinase (AMPK) Thr 172 and endothelial nitric oxide synthase (eNOS) Ser1177 were higher in EPCs derived from the C3G-treated diabetic mice compared with those in nondiabetic mice. Furthermore, compared with nondiabetic controls, diabetic apoE(-/-) mice had a 3.5-fold increase in the aortic lesion area, which was lowered by 45% in C3G-fed diabetic mice. This study extends our current knowledge that C3G improves the impairment of EPC function, enhances endothelial repair, and thus limits accelerated atherogenesis caused by diabetes. Our findings emphasize the potential utility of anthocyanin in the prevention and treatment of diabetic vascular complications. PMID:23761653

Zhang, Yuhua; Wang, Xiaoming; Wang, Yun; Liu, Yan; Xia, Min



Plasma pharmacokinetics and urinary excretion of isoflavones after ingestion of soy products with different aglycone/glucoside ratios in South Korean women.  


Asian populations are thought to receive significant health benefits from traditional diets rich in soybeans due to high isoflavone contents. However, available epidemiologic data only weakly support this hypothesis. The present study was carried out to assess the pharmacokinetics of isoflavones in South Korean women after ingestion of soy-based foods. Twenty-six healthy female volunteers (20-30 y old) consumed three different soy products (i.e., isogen, soymilk, and fermented soybeans) with different aglycone/glucoside ratios. Plasma and urine isoflavone concentrations were measured by high-performance liquid chromatography (HPLC) after ingestion of one of the soy products. Pharmacokinetic parameters were determined using the WinNonlin program. The area under the curve (AUC) for plasma daidzein levels of the soymilk group (2,101 ± 352 ng · h/mL) was significantly smaller than those of the isogen (2,628 ± 573 ng · h/mL) and fermented soybean (2,593 ± 465 ng · h/mL) groups. The maximum plasma concentration (Cmax ) of daidzein for the soymilk group (231 ± 44 ng/mL) was significantly higher than those of the isogen (160 ± 32 ng/mL) and fermented soybean (195 ± 35 ng/mL) groups. The half-lives of daidzein and genistein in the soymilk group (5.9 and 5.6 h, respectively) were significantly shorter than those in the individuals given isogen (9.6 and 8.5 h, respectively) or fermented soybean (9.5 and 8.2 h, respectively). The urinary recovery rates of daidzein and genistein were 42% and 17% for the isogen group, 46% and 23% for the fermented soybean group, and 33% and 22% for the soymilk group. In conclusion, our data indicated that soy products containing high levels of isoflavone aglycone are more effective for maintaining plasma isoflavone concentrations. Additional dose-response, durational, and interventional studies are required to evaluate the ability of soy-based foods to increase the bioavailability of isoflavones that positively affect human health. PMID:24133619

Chang, Youngeun; Choue, Ryowon



Plasma pharmacokinetics and urinary excretion of isoflavones after ingestion of soy products with different aglycone/glucoside ratios in South Korean women  

PubMed Central

Asian populations are thought to receive significant health benefits from traditional diets rich in soybeans due to high isoflavone contents. However, available epidemiologic data only weakly support this hypothesis. The present study was carried out to assess the pharmacokinetics of isoflavones in South Korean women after ingestion of soy-based foods. Twenty-six healthy female volunteers (20-30 y old) consumed three different soy products (i.e., isogen, soymilk, and fermented soybeans) with different aglycone/glucoside ratios. Plasma and urine isoflavone concentrations were measured by high-performance liquid chromatography (HPLC) after ingestion of one of the soy products. Pharmacokinetic parameters were determined using the WinNonlin program. The area under the curve (AUC) for plasma daidzein levels of the soymilk group (2,101 ± 352 ng · h/mL) was significantly smaller than those of the isogen (2,628 ± 573 ng · h/mL) and fermented soybean (2,593 ± 465 ng · h/mL) groups. The maximum plasma concentration (Cmax) of daidzein for the soymilk group (231 ± 44 ng/mL) was significantly higher than those of the isogen (160 ± 32 ng/mL) and fermented soybean (195 ± 35 ng/mL) groups. The half-lives of daidzein and genistein in the soymilk group (5.9 and 5.6 h, respectively) were significantly shorter than those in the individuals given isogen (9.6 and 8.5 h, respectively) or fermented soybean (9.5 and 8.2 h, respectively). The urinary recovery rates of daidzein and genistein were 42% and 17% for the isogen group, 46% and 23% for the fermented soybean group, and 33% and 22% for the soymilk group. In conclusion, our data indicated that soy products containing high levels of isoflavone aglycone are more effective for maintaining plasma isoflavone concentrations. Additional dose-response, durational, and interventional studies are required to evaluate the ability of soy-based foods to increase the bioavailability of isoflavones that positively affect human health.

Chang, Youngeun



Annexin V assay-proven anti-apoptotic effect of ascorbic acid 2-glucoside after cold ischemia/reperfusion injury in rat liver transplantation.  


Controversy exists over whether the predominant cell death of hepatocytes is due to apoptosis or necrosis after ischemia/reperfusion injury. In this study we investigated the predominant cell death of hepatocytes after cold ischemia/reperfusion injury using the Annexin V-based assay, and evaluated the anti-apoptotic effect of ascorbic acid 2-glucoside (AA-2G) added to the University of Wisconsin solution (UW solution) in rat liver transplantation. The retrieved liver was preserved in 4 UW solution for 24 h, and then transplanted orthotopically to the syngeneic Wistar recipient. The animals were divided into 2 groups, a control group (n=10), in which liver grafts were preserved in UW solution (4), and an AA-2G group (n=10), in which liver grafts were preserved in UW solution (4) with AA-2G (100 ug/ml). The serum AST level 4 h after reperfusion in the control group was significantly suppressed in the AA-2G group, and the bile production of the liver graft in the AA-2G group was well recovered. The mean survival time in the AA-2G group was significantly improved compared with that in the control group. Annexin-V and Propidium iodide staining 4 h after reperfusion showed a significantly higher percentage of viable hepatocytes in the AA-2G group compared with the control group (93.4 +/- 2.0 vs. 80.3 +- 2.1%, P<0.05). In the control group, the main cell death of hepatocytes was apoptosis (early apoptosis: 10.0 +- 4.7%, late apoptosis: 6.4 +/- 1.7%). The addition of AA-2G to the UW solution significantly inhibited both early and late apoptotic cell death 4 h after reperfusion (early apoptosis: 0.98 +/- 0.88%, late apoptosis: 2.2 +/- 1.1%). The expression of caspase 9 in the immunostaining of the liver graft was suppressed in the AA-2G group compared with in the control group. Our study using the Annexin V-based assay provided evidence that the predominant cell death of hepatocytes was apoptosis after 24 h cold ischemia/reperfusion injury in rat liver transplantation. The addition of AA-2G to the UW solution attenuated 24 h cold ischemia/reperfusion injury by inhibiting the apoptosis of hepatocytes. PMID:14679398

Liu, Jie; Yagi, Takahito; Sadamori, Hiroshi; Matsukawa, Hiroyoshi; Sun, Dong-Sheng; Mitsuoka, Naoshi; Yamamura, Masao; Matsuoka, Junji; Jin, Zaishun; Yamamoto, Itaru; Tanaka, Noriaki



Maintenance of glucose-sensitive insulin secretion of cryopreserved human islets with University of Wisconsin solution and ascorbic acid-2 glucoside.  


Normal human islet cells are an ideal source for pancreas-targeted cell therapies, but the availability of human donor pancreata for islet isolation is severely limited. To effectively utilize such scarce donor organs for cell therapies, it is crucial to develop an excellent isolation, effective cryopreservation, and efficient gene transfer techniques for the transportation of isolated cells. In the present study, we investigate the effect of University of Wisconsin (UW) solution and ascorbic acid-2 glucoside (AA2G) on the cryopreservation of human islets. We also evaluate the gene transfer efficiency of a lentiviral vector expressing the E. coli LacZ gene, Lt-NLS/LacZ, in human islets. Human islets were isolated with a standard digestion method at the University of Alberta. Isolated islets were transported to Japan for 40 h and then subjected to cryopreservation experiments. The following preservation solutions were tested: UW solution with 100 micro g/mL of AA2G, UW solution, 100% fetal bovine serum (FBS), and CMRL supplemented with 10% FBS. Following three months of cryopreservation, the islets were thawed and analyzed for viability, glucose-sensitive insulin secretion, proinsulin gene expression profile, and in vivo engraftment. The islets were also subjected to monolayer formation with 804G-cell-line-derived extracellular matrix (ECM), followed by Lt-NLS/LacZ transduction. The viability, morphology, glucose-sensitive insulin secretion, proinsulin gene expression, and monolayer formation efficiency of the thawed cryopreserved islets are significantly better maintained by the use of UW solution. When AA2G (100 microg/mL) is combined with UW, such parameters are further improved. The adequate engraftment of UW + AA2G-cryopreserved human islets is achieved in the liver of nude mice. Efficient Lt-NLS/LacZ transduction is identified in monolayered islets cryopreserved with UW solution with AA2G. The present work demonstrates that the combination of UW solution with AA2G (100 microg/mL) would be a useful cryopreservation means for human islets. Human islets monolayer-cultured with 804G-derived ECM are efficiently transduced with a lentiviral vector Lt-NLS/LacZ. PMID:15153144

Arata, Takashi; Okitsu, Teru; Fukazawa, Takuya; Ikeda, Hideaki; Kobayashi, Kazuya; Yong, Chen; Kosaka, Yoshikazu; Narushima, Michiki; Matsuoka, Junji; Yamamoto, Itaru; Tanaka, Noriaki; Lakey, Jonathan R T; Kobayashi, Naoya



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

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 inducing conditions. ArbG was found to share a high level of similarity with the BglG antiterminator as well as with Bacillus subtilis SacT and SacY antiterminators, suggesting that ArbG functions as an antiterminator in regulating the expression of the E. chrysanthemi arb genes. Images

el Hassouni, M; Henrissat, B; Chippaux, M; Barras, F



Incorporation of an introduced weed into the diet of a native butterfly: consequences for preference, performance and chemical defense.  


The introduction of exotic plants, animals, and pathogens into non-native ecosystems can have profound effects on native organisms. Plantago lanceolata, narrow-leaf or ribwort plantain (Plantaginaceae), is a weed that was introduced to North America from Eurasia approximately 200 years ago and that has been incorporated into the diet of a variety of native North American herbivores. Plantain contains two iridoid glycosides, aucubin and catalpol, that can be toxic or deterrent to non-specialized herbivores or herbivores that have recently incorporated this species into their diet. Anartia jatrophae (Nymphalidae), the white peacock, feeds on plants in five families including the Plantaginaceae, and was recently observed feeding on plantain; however, the effects of feeding on this novel host plant are unknown. In this study, we performed a series of experiments to assess larval preference and performance on the introduced P. lanceolata and on a native host plant that does not contain iridoid glycosides, water hyssop, Bacopa monnieri (Plantaginaceae). We also tested whether or not white peacocks were able to sequester iridoid glycosides and compared this ability with an iridoid specialist, the buckeye, Junonia coenia (Nymphalidae). White peacocks successfully developed to the adult stage on plantain; larvae grew more slowly but pupae were heavier when compared with larvae and pupae reared on the native host plant. Larvae showed induced feeding preferences for the host plant on which they were reared. Furthermore, larvae sequestered small amounts of iridoids that were also retained in pupae and adults. These results suggest that incorporation of the introduced weed, plantain, into the diet of the white peacock may have important consequences for larval performance and preference, as well as for interactions with natural enemies. PMID:24142264

Knerl, Angela; Bowers, M Deane



The presence of CYP79 homologues in glucosinolate-producing plants shows evolutionary conservation of the enzymes in the conversion of amino acid to aldoxime in the biosynthesis of cyanogenic glucosides and glucosinolates.  


A cDNA encoding CYP79B1 has been isolated from Sinapis alba. CYP79B1 from S. alba shows 54% sequence identity and 73% similarity to sorghum CYP79A1 and 95% sequence identity to the Arabidopsis T42902, assigned CYP79B2. The high identity and similarity to sorghum CYP79A1, which catalyses the conversion of tyrosine to p-hydroxyphenylacetaldoxime in the biosynthesis of the cyanogenic glucoside dhurrin, suggests that CYP79B1 similarly catalyses the conversion of amino acid(s) to aldoxime(s) in the biosynthesis of glucosinolates. Within the highly conserved 'PERF' and the heme-binding region of A-type cytochromes, the CYP79 family has unique substitutions that define the family-specific consensus sequences of FXP(E/D)RH and SFSTG(K/R)RGC(A/I)A, respectively. Sequence analysis of PCR products generated with CYP79B subfamily-specific primers identified CYP79B homologues in Tropaeolum majus, Carica papaya, Arabidopsis, Brassica napus and S. alba. The five glucosinolate-producing plants identified a CYP79B amino acid consensus sequence KPERHLNECSEVTLTENDLRFISFSTGKRGC. The unique substitutions in the 'PERF' and the heme-binding domain and the high sequence identity and similarity of CYP79B1, CYP79B2 and CYP79A1, together with the isolation of CYP79B homologues in the distantly related Tropaeolaceae, Caricaceae and Brassicaceae within the Capparales order, show that the initial part of the biosynthetic pathway of glucosinolates and cyanogenic glucosides is catalysed by evolutionarily conserved cytochromes P450. This confirms that the appearance of glucosinolates in Capparales is based on a cyanogen 'predisposition'. Identification of CYP79 homologues in glucosinolate-producing plants provides an important tool for tissue-specific regulation of the level of glucosinolates to improve nutritional value and pest resistance. PMID:9862490

Bak, S; Nielsen, H L; Halkier, B A



A new flavonoid and other polar compounds from Galeopsis angustifolia Ehrh. ex Hoffm.  


The analysis of the polar fraction of Galeopsis angustifolia Ehrh. ex Hoffm. indicates that the main components are iridoids and flavonoids. Six compounds were identified: a new flavonoid, 3'-hydroxy-isoscutellarein 7-O-[6'?acetyl-?-D-glucopyranosyl-(1???2)-?-D-glucopyranoside]; three iridoid glucosides: harpagide, acetyl harpagide and for the first time in this species, 8-epi-loganin; two known acetylated flavonoid glycosides: 3'-hydroxy-4'-O-methylisoscutellarein 7-O-[6'?acetyl-?-D-allopyranosyl-(1???2)-6?-acetyl-?-D-glucopyranoside], 3'-hydroxy-4'-O-methylisoscutellarein 7-O-[6'?acetyl-?-D-allopyranosyl-(1???2)-?-D-glucopyranoside]. Both flavonoids and iridoids are present in high amount; respectively, 16.7% and 4.5% of the crude extract. PMID:22963374

Venditti, Alessandro; Serrilli, Anna Maria; Bianco, Armandodoriano



Enzymatic bioconversion of citrus hesperidin by Aspergillus sojae naringinase: enhanced solubility of hesperetin-7-O-glucoside with in vitro inhibition of human intestinal maltase, HMG-CoA reductase, and growth of Helicobacter pylori.  


Hesperetin-7-O-glucoside (Hes-7-G) was produced by the enzymatic conversion of hesperidin by Aspergillus sojae naringinase due to the removal of the terminal rhamnose. Extracts from orange juice and peel containing the hesperidin were so treated by this enzyme that the hesperidin could also be converted to Hes-7-G. The solubility of Hes-7-G in 10% ethanol was enhanced 55- and 88-fold over those of hesperidin and hesperetin, respectively, which may make Hes-7-G more bioavailable. Hes-7-G was 1.7- and 2.4-fold better than hesperidin and hesperetin, respectively, in the inhibition of human intestinal maltase. Hes-7-G was more potent by 2- and 4-fold than hesperidin in the inhibition of human HMG-CoA reductase. Additionally, Hes-7-G exhibited more effective inhibition of the growth of Helicobacter pylori than hesperetin, while its effectiveness was similar to that of hesperidin. Therefore, the results suggest that bioconverted Hes-7-G is more effective and bioavailable than hesperidin, as it has enhanced inhibitory and solubility properties. PMID:22980799

Lee, Young-Su; Huh, Ji-Young; Nam, So-Hyun; Moon, Sung-Kwon; Lee, Soo-Bok



Kaempferol-7-O-beta-D-glucoside (KG) isolated from Smilax china L. rhizome induces G2/M phase arrest and apoptosis on HeLa cells in a p53-independent manner.  


Kaempferol-7-O-beta-D-glucoside (KG), a flavonoid glycoside, isolated from Smilax china L. rhizome, displayed marked anticancer activity on a panel of established cancer cells, of which, HeLa human cervix carcinoma cells were the most sensitive. Meanwhile, the cytotoxic effects of KG on normal human cells (HEK293 embryonic kidney cells and L-02 embryonic liver cells) were much smaller than on cancer cells. This work studied the molecular mechanisms underlying KG induced growth inhibition in HeLa cells. The results showed that KG induced G2/M phase growth arrest correlated with Cyclin B1 and Cdk1 decrease in a p53-independent manner, and also caused an increase in apoptosis, which was confirmed by characteristic morphological changes, evident DNA fragmentation, increased apoptotic sub-G1 population. Furthermore, inhibition of NF-kappaB nuclear translocation, up-regulation of Bax and down-regulation of Bcl-2, were observed in HeLa cells treated with KG, which indicated that the mitochondrial pathway was involved in the apoptosis signal pathway. In summary, KG displayed a significant anti-tumor effect through cell cycle arrest and apoptotic induction in HeLa cells, which suggested that KG might have therapeutic potential against cervix carcinoma. PMID:18343026

Xu, Wen; Liu, Jianwen; Li, Changlong; Wu, He-Zhen; Liu, Yan-Wen



A new isoflavone glycitein 7-O-beta-D-glucoside 4''-O-methylate, isolated from Cordyceps militaris grown on germinated soybeans extract, inhibits EGF-induced mucus hypersecretion in the human lung mucoepidermoid cells.  


A new isoflavone glycitein 7-O-beta-d-glucoside 4''-O-methylate (CGLM) has been isolated recently from Cordyceps militaris grown on germinated soybean extract and has antioxidant activity. In the present study, CGLM was investigated for its suppression of airway mucous hyper-secretion in epidermal growth factor (EGF)-treated human lung mucoepidermoid cells. NCI-H292 cells were treated with CGLM for 1?h, followed by EGF treatment for 24?h. The decrease in cyclooxygenase-2 (COX-2) production was correlated with reduced levels of protein and mRNA of inducible matrix metalloproteinase 9 (MMP-9) and also MUC5AC gene expression. CGLM directly inhibited down-regulated NF-?B activity, and significantly inhibited the phosphorylation of p38 and ERK1/2 (p42/p44) in NCI-H292 cells. These results suggest that CGLM protects NCI-H292 cells from EGF-induced damage by down-regulation of COX-2, MMP-9 and MUC5AC gene expression, mediated via blocking the NF-kappa-B and p38/ERK MAPK pathways. PMID:22407817

Kim, Jung-Hee; Park, Dong Ki; Lee, Choong Hwan; Yoon, Do-Young



Gynecological efficacy and chemical investigation of Vitex agnus-castus L. fruits growing in Egypt.  


Flavonoid glycosides, orientin and apigenin 3, 8-di-C-glycosides in addition to, iridoid compound, aucubin were isolated from the ethanolic extract of Vitex agnus-castus fruits. Their structures were identified on the basis of the spectroscopic data. The estrogenic activity of the ethanolic extract in two dose levels 0.6 and 1.2 g kg(-1) per body weight (b.w.) was studied by the vaginal smear, and uterine weight methods for normal and ovariectomized female rats. The extract induced significant increase in the uterine weight of ovariectomized rats at two dose levels comparable to that of control group. The percentages of the total average number of scores were increased significantly too. Significant increases in plasma progesterone and total estrogens levels were shown at the two dose levels when compared to that of control group. On the other side, the extract induced significant reduction in luteinizing and plasma prolactin hormones. PMID:18415863

Ibrahim, N A; Shalaby, A S; Farag, R S; Elbaroty, G S; Nofal, S M; Hassan, E M



Catalpol inhibits apoptosis in hydrogen peroxide-induced endothelium by activating the PI3K\\/Akt signaling pathway and modulating expression of Bcl2 and Bax  

Microsoft Academic Search

Catalpol, an iridoid glucoside found in the root of Rehmannia glutinosa Libosch, has been demonstrated to reduce apoptosis in neuronal cell lines. Recent data suggests that catalpol also exerts anti-apoptotic effects on other cell types. The aim of the present study was to investigate whether catalpol protects against hydrogen peroxide (H2O2) induced apoptosis in human umbilical vein endothelial cells (HUVECs).

Lingai Hu; Yukun Sun; Jian Hu



Chemical defense, mycorrhizal colonization and growth responses in Plantago lanceolata L.  


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 chemical defenses, but that these responses are plant genotype-dependent. PMID:19271240

De Deyn, Gerlinde Barbra; Biere, A; van der Putten, W H; Wagenaar, R; Klironomos, J N



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

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.

Paternostre, M.T.; Roux, M.; Rigaud, J.L.



Screening of common Plantago species in Hungary for bioactive molecules and antioxidant activity.  


Five species of Plantago genus, namely P. lanceolata, P. major, P. media, P. altissima and P. maritima were screened for iridoid content (CE-MEKC), total caffeoyl phenylethanoid glycoside (CPG) content and antioxidant activity (CUPRAC assay). The five species could be distinguished by TLC pattern analysis in a single run in a system commonly used for quality management of P. lanceolata leaves, as shown by cluster analysis of major bands; with the exception, that P. altissima and P. lanceolata did not show enough pattern difference to be fully separated. P. maritima was shown to have the highest antioxidant capacity (0.42 ?mol ascorbic acid equivalent (AAE)/g DW), and the highest level of CPGs (4.29%). P. altissima was shown to be chemically indistinguishable from P. lanceolata with repsect to iridoid content (aucubin 0.55 ± 0.04%, 0.68 ± 0.23%, catalpol 0.66 ± 0.13% and 0.89 ± 0.22%, respectively), CPG content (2.40 ± 0.38% and 2.54 ± 0.56%, respectively) and antioxidant capacity (0.2206 ± 0.0290 and 0.2428 ± 0.0191 ?mol AAEAC/g DW). The presented data show the potency of medicinal use of Hungarian wild populations of the studied five species, especially in the case of P. maritima, and that P. altissima can be a potential replacement of P. lanceolata in herbal mixtures. PMID:21565762

Gonda, S; Tóth, L; Parizsa, P; Nyitrai, M; Vasas, G



Insect Inhibitory Lactone Glucosides of Physalis peruviana  

Microsoft Academic Search

The ergostanoid lactones, perulactone 3-O-?-D-glucopyranoside (1) and isoperulactone 3-O-?-D-glucopyranoside (2) were isolated from leaves of Physalis peruviana. Compound 1 reduces the growth of Helicoverpa zea larvae to 50% of control size at a dietary concentration of 150 mg kg

Anthony C. Waiss Jr; Carl A. Elliger; Mabry Benson



Bioactive iridoids and a new lignan from Allamanda cathartica and Himatanthus fallax from the Suriname rainforest.  


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

Abdel-Kader, M S; Wisse, J; Evans, R; van der Werff, H; Kingston, D G



Sonication-assisted Agrobacterium rhizogenes-mediated transformation of Verbascum xanthophoeniceum Griseb. for bioactive metabolite accumulation.  


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

Georgiev, Milen I; Ludwig-Müller, Jutta; Alipieva, Kalina; Lippert, Annemarie



Host shifts from Lamiales to Brassicaceae in the sawfly genus Athalia.  


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

Opitz, Sebastian E W; Boevé, Jean-Luc; Nagy, Zoltán Tamás; Sonet, Gontran; Koch, Frank; Müller, Caroline



A new eudesmane sesquiterpene glucoside from Liriope muscari fibrous roots.  


The screening of several Chinese medicinal herbs for nematocidal properties showed that the ethanol extract of Liriope muscari fibrous roots possessed significant nematocidal activity against the pine wood nematode (Bursaphelenchus xylophilus). From the ethanol extract, a new constituent (1,4-epoxy-cis-eudesm-6-O-?-D-glucopyranoside) and three known glycosides [1?,6?-dihydroxy-cis-eudesm-3-ene-6-O-?-D-glucopyranoside (liriopeoside A), 1?,6?-dihydroxy-cis-eudesm-3-ene-6-O-?-D-glucopyranoside, and 1?,6?-dihydroxy-5,10-bis-epi-eudesm-4(15)-ene-6-O-? D-glucopyranoside] were isolated by bioassay-guided fractionation. The structures were elucidated by 1D and 2D NMR and MS techniques. 1,4-Epoxy-cis-eudesm-6-O-?-D-glucopyranoside possessed moderate nemato-cidal activity against B. xylophilus with a LC(50 )value of 339.76 ?g/mL, while liriopeoside A (LC(50) = 82.84 ?g/mL) and 1?,6?-dihydroxy-cis-eudesm-3-ene-6-O-?-D-glucopyranoside (LC(50) = 153.39 ?g/mL) also exhibited nematocidal activity against B. xylophilus. The crude extract of L. muscari fibrous roots exhibited nematocidal activity against the pine wood nematode with a LC(50) value of 182.56 ?g/mL. PMID:22031065

Zhang, Hai Ming; Wang, Gang Li; Bai, Chun Qi; Liu, Peng; Liu, Zi Mu; Liu, Qi Zhi; Wang, Yong Yan; Liu, Zhi Long; Du, Shu Shan; Deng, Zhi Wei



Linking microbial community structure to ?-glucosidic function in soil aggregates.  


To link microbial community 16S structure to a measured function in a natural soil, we have scaled both DNA and ?-glucosidase assays down to a volume of soil that may approach a unique microbial community. ?-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 ?-glucosidase activities compared with the communities associated with low ?-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 observed that functional differences in otherwise similar soil aggregates can be largely attributed to differences in resource availability, rather than to the presence or absence of particular taxonomic groups. PMID:23719152

Bailey, Vanessa L; Fansler, Sarah J; Stegen, James C; McCue, Lee Ann



Two new steroidal glucosides from Tribulus terrestris L.  


Two new furostanol saponins, tribufurosides D (1) and E (2), were isolated from the fruits of Tribulus terrestris L. With the help of chemical and spectral analyses (IR, MS, 1D, and 2D NMR), the structures of the two new furostanol saponins were established as 26-O-beta-d-glucopyranosyl-(25S)-5alpha-furost-12-one-2alpha,3beta,22alpha,26-tetraol-3-O-beta-d-glucopyranosyl-(1 --> 4)-beta-d-galactopyranoside (1) and 26-O-beta-d-glucopyranosyl-(25R)-5alpha-furost-12-one-2alpha,3beta,22alpha,26-tetraol-3-O-beta-d-glucopyranosyl-(1 --> 4)-beta-d-galactopyranoside (2). PMID:20183289

Xu, Ya-Juan; Xu, Tun-Hai; Liu, Yue; Xie, Sheng-Xu; Si, Yun-Shan; Xu, Dong-Ming



Psychollatine, a glucosidic monoterpene indole alkaloid from Psychotria umbellata.  


A monoterpene indole alkaloid, psychollatine ( 1), was isolated from Psychotria umbellata leaves. Its structure was characterized by interpretation of spectroscopic data and by comparison of its NMR data with those of croceaine A ( 2) from Palicourea crocea. The configuration of psychollatine ( 1) was established by NOE difference and circular dichroism (CD) techniques, while its conformation was evaluated through molecular modeling studies and NMR coupling constants. PMID:18288808

Kerber, V A; Passos, C S; Verli, H; Fett-Neto, A G; Quirion, J P; Henriques, A T



Lessons learned from metabolic engineering of cyanogenic glucosides  

Microsoft Academic Search

Plants produce a plethora of secondary metabolites which constitute a wealth of potential pharmaceuticals, pro-vitamins, flavours,\\u000a fragrances, colorants and toxins as well as a source of natural pesticides. Many of these valuable compounds are only synthesized\\u000a in exotic plant species or in concentrations too low to facilitate commercialization. In some cases their presence constitutes\\u000a a health hazard and renders the

Anne Vinther Morant; Kirsten Jørgensen; Bodil Jørgensen; Winnie Dam; Carl Erik Olsen; Birger Lindberg Møller; Søren Bak



Partitioning of octyl glucoside between octyl glucoside/phosphatidylcholine mixed aggregates and aqueous media as studied by isothermal titration calorimetry.  

PubMed Central

Stepwise dilution of lipid-surfactant mixed micelles first results in extraction of surfactant from the mixed micelles into the aqueous medium. Subsequently mixed micelles transform into vesicles, within a range of compositions that corresponds to equilibrium coexistence between these two types of aggregates. Further dilution results in extraction of surfactant from the resultant mixed vesicles. In the present study, we have investigated the heat evolution of these processes, as they occur in mixed systems composed of egg phosphatidylcholine (PC) and the nonionic surfactant octylglucoside (OG). A combined use of isothermal titration calorimetry (ITC) and photon correlation spectroscopy (PCS), capable of monitoring phase transformations, revealed that 1) The sum of all of the studied processes (i.e., extraction of OG from mixed micelles and vesicles and the phase transformation) is isocaloric at approximately 40 degrees C throughout the whole dilution. At lower temperatures, all of the dilution steps are exothermic, whereas at higher temperatures all of them are endothermic. 2) At all temperatures, the absolute value of the heat associated with each dilution step within the range of coexistence of micelles and vesicles is almost constant and larger than in either the micellar or the vesicular range. We give an interpretation of these calorimetric data in terms of the relationship between the composition of the mixed aggregates Re and the aqueous concentration of surfactant monomers Dw. Assuming that the main contribution to the heat evolution is due to extraction of surfactant from mixed aggregates to the aqueous solution, we deduce the relationship Dw(Re) characterizing the system over the whole range of compositions. We find that, in accord with thermodynamic expectations, Dw is almost constant throughout the range of coexistence of mixed micelles and vesicles.

Opatowski, E; Kozlov, M M; Lichtenberg, D



Phytochemical analysis, biological evaluation and micromorphological study of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande endemic to central Apennines, Italy.  


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-?-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%), ?-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?g/ml). PMID:23827382

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



Rapid measurement and evaluation of the effect of drying conditions on harpagoside content in Harpagophytum procumbens (devil's claw) root.  


The effect of drying conditions on harpagoside (HS) retention, as well as the use of near-infrared spectroscopy (NIRS) for rapid quantification of the iridoids, HS, and 8-rho-coumaroyl harpagide (8rhoCHG) and moisture, in dried Harpagophytum procumbens (devil's claw) root was investigated. HS retention was significantly (P < 0.05) lower in sun-dried samples as compared to tunnel-dried (60 degrees C, 30% relative humidity) and freeze-dried samples. The best retention of HS was obtained at 50 degrees C when evaluating tunnel drying at dry bulb temperatures of 40, 50, and 60 degrees C and 30% relative humidity. NIRS can effectively predict moisture content with a standard error of prediction (SEP) and correlation coefficient (r) of 0.24% and 0.99, respectively. The HS and 8rhoCHG NIRS calibration models established for both iridoid glucosides can be used for screening purposes to get a semiquantitative classification of devil's claw roots (for HS: SEP = 0.236%, r = 0.64; for 8rhoCHG: SEP = 0.048%, r = 0.73). PMID:15853393

Joubert, Elizabeth; Manley, Marena; Gray, Brian R; Schulz, Hartwig



Minor secondary metabolic products from the stem bark of Plumeria rubra Linn. displaying antimicrobial activities.  


Four new iridoids viz., plumeridoids A, B, and C and epiplumeridoid C were isolated from the stem bark of Plumeria rubra Linn. together with twenty-four known compounds viz., 1-( P-hydroxyphenyl)propan-1-one, isoplumericin, plumericin, dihydroplumericin, allamcin, fulvoplumerin, allamandin, plumieride, P- E-coumaric acid, 2,6-dimethoxy- P-benzoquinone, scopoletin, cycloart-25-en-3 beta,24-diol, 2,4,6-trimethoxyaniline, ajunolic acid, ursolic acid, oleanolic acid, beta-amyrin acetate, betulinic acid, lupeol and its acetate, 2,3-dihydroxypropyl octacosanoate, glucoside of beta-sitosterol, and a mixture of common sterols (stigmasterol and beta-sitosterol). Their structures were determined by means of spectroscopic data including HREIMS, 1H NMR, 13C NMR, 2D NMR (HMQC, HMBC, NOESY) and by comparison with published data. All but one of thirteen tested compounds exhibited antifungal, antialgal, and/or antibacterial activities. PMID:19937550

Kuigoua, Guy Merlin; Kouam, Simeon F; Ngadjui, Bonaventure T; Schulz, Barbara; Green, Ivan R; Choudhary, M Iqbal; Krohn, Karsten



Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones  

PubMed Central

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.

Zimmermann, Nicole; Hilgraf, Robert; Lehmann, Lutz; Ibarra, Daniel



Genetic transformation of Harpagophytum procumbens by Agrobacterium rhizogenes : iridoid and phenylethanoid glycoside accumulation in hairy root cultures  

Microsoft Academic Search

A genetic transformation method using Agrobacterium rhizogenes was developed for Harpagophytum procumbens. The influence of three factors on hairy root formation was tested: bacterial strains (A4 and ATCC 15834), various types\\u000a of explants and acetosyringone (AS) (200 ?M). The highest frequency of transformation (over 50% of explants forming roots\\u000a at the infected sites after 6 weeks of culture on Lloyd and McCown

Renata Gr?bkowska; Aleksandra Królicka; Wojciech Mielicki; Marzena Wielanek; Halina Wysoki?ska



Potential hepatotoxicity of geniposide, the major iridoid glycoside in dried ripe fruits of Gardenia jasminoides (Zhi-zi)  

Microsoft Academic Search

The safety of geniposide, mainly focusing on its hepatotoxicity in rats, was determined by liver enzymes in serum and histopathology ultrastructural preparation. The lethal dose, 50% (LD50) of per oral geniposide was 1431.1?mg?kg. The acute toxicity study indicated geniposide at dose of 574?mg?kg or more could cause hepatic toxicity in rats and the hepatotoxicity often appeared at 24–48?h after the

Yue Ding; Tong Zhang; Jian-sheng Tao; Li-ying Zhang; Jian-rong Shi; Guang Ji



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

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 ?, ?-unsaturated ?-lactam moiety. Structurally, they were elucidated to be 9?-hydroxy-13(14)-labden-16,15-amide (2) and 6?-acetoxy-9?-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-?-D-glucoside (9), luteolin-7-O-glucoside (10), 5-hydroxy-3,6,7,4?-tetramethoxyflavone (11), casticin (12), artemetin (13), aucubin (14), agnuside (15), ?-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.

Li, Shenghong; Qiu, Shengxiang; Yao, Ping; Sun, Handong; Fong, Harry H. S.; Zhang, Hongjie



Compounds from the Fruits of the Popular European Medicinal Plant Vitex agnus-castus in Chemoprevention via NADP(H):Quinone Oxidoreductase Type 1 Induction.  


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 ? , ? -unsaturated ? -lactam moiety. Structurally, they were elucidated to be 9 ? -hydroxy-13(14)-labden-16,15-amide (2) and 6 ? -acetoxy-9 ? -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- ? -D-glucoside (9), luteolin-7-O-glucoside (10), 5-hydroxy-3,6,7,4'-tetramethoxyflavone (11), casticin (12), artemetin (13), aucubin (14), agnuside (15), ? -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

Li, Shenghong; Qiu, Shengxiang; Yao, Ping; Sun, Handong; Fong, Harry H S; Zhang, Hongjie



Theoretical studies of structure, energetics and properties of Ca(2+) complexes with alizarin glucoside.  


The effective dissolution of calcium oxalate, the main component of kidney stones, is important in the treatment of nephrolithisis. Polyphenol glycosides constitute compounds supporting dissolution and inhibition of formation of stones. These moieties possess oxygen atoms which can interact with calcium cations. Density functional theory studies of interactions of polyphenol glycosides and Ca(2+) were performed to determine preferred structures and the role of polyphenol and carbohydrate parts in the formation of complexes. The determination of these properties may be useful in designing new complexes, effectively interacting with calcium compounds. In the present study we try to define factors influencing interaction energies and stabilization. The determined structures were divided according to coordination numbers. Obtained data indicate that for stronger interactions complexes maximize the number of O-Ca(2+) contacts. PMID:23605140

Toczek, Dariusz; Kubas, Karolina; Turek, Micha?; Roszak, Szczepan; Gancarz, Roman



Anti-diabetic properties of chrysophanol and its glucoside from rhubarb rhizome.  


An ethanol extract of rhubarb rhizome exhibited marked glucose transport activity in differentiated L6 rat myotubes. Activity-guided fractionation resulted in the isolation of two anthraquinones, chrysophanol-8-O-beta-D-glucopyranoside (1) and chrysophanol (2). The anti-diabetic effect was examined by glucose transport activity, glucose transporter 4 (Glut4) expression in myotubes, and the level of insulin receptor (IR) tyrosine phosphorylation as influenced by tyrosine phosphatase 1B, each of which is a major target of diabetes treatment. Chrysophanol-8-O-beta-D-glucopyranoside up to 25 microM dose-dependently activated glucose transport in insulin-stimulated myotubes. Increased tyrosine phosphorylation of IR due to tyrosine phosphatase 1B inhibitory activity with an IC50 value of 18.34+/-0.29 microM and unchanged Glut4 mRNA levels was observed following chrysophanol-8-O-beta-D-glucopyranoside treatment. Chrysophanol up to 100 microM exerted mild glucose transport activity and elevated the tyrosine phosphorylation of IR via tyrosine phosphatase 1B inhibition (IC50=79.86+/-0.12 microM); Glut4 mRNA expression was also significantly increased by 100 microM. The ED50 values of the two compounds were 59.38+/-0.66 and 79.69+/-0.03 microM, respectively. Therefore, these two anthraquinones from rhubarb rhizome, chrysophanol-8-O-beta-D-glucopyranoside and chrysophanol, have mild cytotoxicity and anti-diabetic properties and could play metabolic roles in the insulin-stimulated glucose transport pathway. PMID:18981591

Lee, Myung Sun; Sohn, Cheon Bae



Maltotriose Utilization by Industrial Saccharomyces Strains: Characterization of a New Member of the  Glucoside Transporter Family  

Microsoft Academic Search

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 metab- olism in a mixture with glucose and maltose. Physiological data obtained for a particularly fast-growing distiller's strain (PYCC

Madalena Salema-Oom; Vera Valadao Pinto; Paula Goncalves; Isabel Spencer-Martins




Technology Transfer Automated Retrieval System (TEKTRAN)

Even though the bioavailability of isoflavones from aglycone forms is believed to be higher than glycosides, human studies testing the bioavailability of isoflavones in Eastern and Western human subjects have been contradictory. To investigate the postprandial absorption and bioavailability of soy ...


Bone mineralization enhancing activity of a methoxyellagic acid glucoside from a Feijoa sellowiana leaf extract.  


The capability of an aqueous methanol extract obtained from the leaves of Feijoa sellowiana Berg. on possible prevention and treatment of osteoporosis has been examined by evaluating its stimulating effect on the two human osteoblastic cell lines HOS58 and SaOS-2. The extract was found to increase significantly the mineralization of cultivated human bone cell, whereby a clear increment (15.3 +/- 2.7%) in von Kossa positive area was determined when administering 25 microg/ml leaf extract. A phytochemical investigation of the extract has demonstrated the high phenolic content and led to the isolation and identification of twenty three of them, among which the new 3-methoxyellagic acid 4-O-beta-glucopyranoside was fully identified. All structures were elucidated on the basis of conventional analytical methods and confirmed by FTMS, 1D- and 2D-NMR data. The new compound was found to cause a significant increase of mineralized area at 20 microg/mL, while at lower concentrations the effect was not significant. However, an increase of the number of mineralized spots (nodules) at all tested concentrations of the compound was observed. PMID:19320288

Ayoub, N A; Hussein, S A; Hashim, A N; Hegazi, N M; Linscheid, M; Harms, M; Wende, K; Lindequist, U; Nawwar, M A M



Bioactivity of aviprin and aviprin-3''-O-glucoside, two linear furanocoumarins from Apiaceae.  


Furanocoumarins are well-known natural products that occur in the most evolved genera of Apiaceae family. This compounds were found to have cytotoxic, phytotoxic, photosensitizing, insecticidal, antibacterial and high anti-fungal effects. Aviprin is considered as a linear furanocoumarin substituted at C8 with an oxygenated prenyl residue. In this study we found that aviprin is a bioactive compound that exhibits high antibacterial, antifungal and phytotoxic activity. The compound stunted the germination of lettuce seeds with IC50 value of 0.270 mg/mL. The compound also inhibited the mycelia growth of Sclerotinia sclerotiorum. Aviprin indicated antibacterial activity against tested gram negative and positive bacteria with inhibition zone of 19-23.5 mm. Our results shown that aviprin can play an allelopatic role for plant. PMID:20644594

Razavi, Seyed Mehdi; Zarrini, Gholamreza


A flavonol glycoside-lignan ester and accompanying acylated glucosides from Monochaetum multiflorum.  


Four acylated glycosides along with six known glycosides were isolated from the leaves of Monochaetum multiflorum. The new compounds were characterized as 4-O-(6'-O-galloyl-beta-glucopyranosyl)-cis-p-coumaric acid, 6'-O-galloylprunasin, benzyl 6'-O-galloyl-beta-glucopyranoside, and a novel diester of tetrahydroxy-mu-truxinic acid with 2 mol of hyperin (monochaetin), based on NMR and MS spectral data and chemical evidence. PMID:11551558

Isaza, J H; Ito, H; Yoshida, T



A flavonol glycoside-lignan ester and accompanying acylated glucosides from Monochaetum multiflorum  

Microsoft Academic Search

Four acylated glycosides along with six known glycosides were isolated from the leaves of Monochaetum multiflorum. The new compounds were characterized as 4-O-(6?-O-galloyl-?-glucopyranosyl)-cis-p-coumaric acid, 6?-O-galloylprunasin, benzyl 6?-O-galloyl-?-glucopyranoside, and a novel diester of tetrahydroxy-?-truxinic acid with 2 mol of hyperin (monochaetin), based on NMR and MS spectral data and chemical evidence.

Jose H Isaza; Hideyuki Ito; Takashi Yoshida



New lignan glucosides with tyrosinase inhibitory activities from exocarp of Castanea henryi.  


Three novel lignan glycosides, 1-[4-(?-glucopyranosyl (1?2)-[?-glucopyranosyl (1?6)]-?-glucopyranosyloxy)-3-methoxyphenyl]-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-1,3-propanediol (1), 2,3-dihydro-2-[4-(?-glucopyranosyl (1?2)-[?-glucopyranosyl (1?6)]-?-glucopyranosyloxy)-3-methoxyphenyl]-3-(hydroxymethyl)-7-methoxy-5-benzofuranpropanol (2), 7-hydroxy-9'-?-glucopyranosyloxyl secoisolariciresinol (3) and two known lignans were isolated from exocarp of Castanea henryi. Their structures were established by spectroscopic means, and their tyrosinase inhibitory potentials were evaluated in vitro using mushroom tyrosinase. PMID:22575748

Wu, Bin; Zhang, Xingde; Wu, Xiaodan



Stereoselective Glycosylations of 2-Azido-2-Deoxy-Glucosides using Intermediate Sulfonium Ions  

PubMed Central

TMSOTf promoted glycosylations of 2-azido-2-deoxy-glucosyl trichloroacetimidates provide excellent ?-anomeric selectivities when performed at a relatively high reaction temperature in the presence of PhSEt or thiophene. NMR and computation studies have shown that these glycosylations proceed through an equatorial anomeric sulfonium-ion, which upon displacement by a sugar alcohol provides an axial glycoside. Computational studies have indicated that steric factors determine the selective formation of the ?-anomeric sulfonium ion.

Park, Jin; Kawatkar, Sameer; Kim, Jin-Hwan; Boons, Geert-Jan



21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2013 CFR

...crystallization of sucrose and dextrose at a level not to exceed the minimum quantity required to produce its intended effect. (2) As a surfactant in molasses at a level not to exceed 320 parts per million in the...



SANS with Contrast Variation Study of the Bacteriorhodopsin-octyl Glucoside Complex  

SciTech Connect

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.

Heller, William T [ORNL; Mo, Yiming [ORNL



21 CFR 178.3600 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2013 CFR

...172.816(a) of this chapter may be safely used as a processing aid (filter aid) in the manufacture of starch, including industrial starch-modified complying with § 178.3520, intended for use as a component of articles that contact...



Treatment of Xerosis with a Topical Formulation Containing Glyceryl Glucoside, Natural Moisturizing Factors, and Ceramide  

PubMed Central

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.

Kausch, Martina; Rippke, Frank; Schoelermann, Andrea M.; Filbry, Alexander W.



Stereochemical aspects of the biosynthesis of the epimeric cyanogenic glucosides dhurrin and taxiphyllin.  


Dhurrin, I ((S)-p-hydroxymandelonitrile-beta-D-glucopyranoside), and taxiphyllin, II (the (R) epimer), occur in the genera Sorghum and Taxus, respectively. Both derive biosynthetically from L-tyrosine via the hydroxylation of p-hydroxyphenylacetonitrile, III. (3R)- and (3S)-L-[3-3H1]tyrosine, prepared by enzymic hydroxylation of the corresponding phenylalanines, were fed separately to shoots from sorghum seedlings (Sorghum bicolor (Linn) Moench) and cuttings from Japanese Yew (Taxus cuspidata Sieb. and Zucc.) and the appropriate cyanogenic glycoside was isolated (I or II). The fraction of the 3H conserved in I and II was calculated from both parallel feeding and 3H:14C double labeling experiments. The results for II were the reverse of I. Both hydroxylations of III, which give rise to the enantiomeric products (S)- and (R)-p-hydroxymandelonitrile, occurred with retention of configuration. The retention mode is characteristic of hydroxylations at aliphatic carbons catalyzed by mixed function oxidases. PMID:1194256

Rosen, M A; Farnden, K J; Conn, E E



A new lignan glucoside from the whole plants of salvia scapiformis.  


Phytochemical investigation of the whole plants of Salvia scapiformis Hance afforded eight compounds, including one new lignan, (+)-8?-hydroxypinoresinol-8-O-[6''-O-(4'''-hydroxybenzoyl)]-?-d-glucopyranoside (1), four known lignans, (+)-8?-hydroxy-pinoresinol-8-O-?-d-glucopyranoside (2), (+)-8?-hydroxypinoresinol (3), (+)-pinoresinol (4), and (+)-medioresinol (5), and three known triterpenoids, ursolic acid (6), 4-epi-niga-ichigoside F1 (7), and niga-ichigoside F1 (8). Their structures were determined on the basis of extensive spectroscopic analyses and comparison with spectroscopic data in the literature. The absolute configuration of the new compound 1 was determined by chemical transformation and GC analysis. PMID:24064455

Lai, Yongji; Ding, Shuiping; Qian, Huiqin; Zhang, Jinwen; Xue, Yongbo; Luo, Zengwei; Yao, Guangmin; Zhang, Yonghui



Isolation and identification of phenolic glucosides from thermally treated olive oil byproducts.  


A liquid phase rich in bioactive compounds, such as phenols and sugars, is obtained from olive oil waste by novel thermal treatment. Two groups of fractions with common characteristics were obtained and studied after thermal treatment, acid hydrolysis, and separation by ultrafiltration, chromatography, and finally Superdex Peptide HR. In the first group, which eluted at the same time as oligosaccharides with a low DP (4-2), an oleosidic secoiridoid structure conjugated to a phenolic compound (hydroxytyrosol) was identified as oleuropeinic acid, and three possible structures were detected. In the second group, glucosyl structures formed by hydroxytyrosol and one, two, or three units of glucose or by tyrosol and glucose have been proposed. Verbascoside, a heterosidic ester of caffeic acid, in which hydroxytyrosol is linked to rhamnose-glucose or one of its isomers was also identified. Neutral oligosaccharides bound to a phenol-containing compound could be antioxidant-soluble fibers with bioactive properties. PMID:23323788

Rubio-Senent, Fátima; Lama-Muñoz, Antonio; Rodríguez-Gutiérrez, Guillermo; Fernández-Bolaños, Juan



Effect of atrial natriuretic peptide on ?-methyl- d-glucoside intestinal active uptake in rats  

Microsoft Academic Search

In vivo, atrial natriuretic peptide (ANP) inhibits water and sodium absorption by the intestine. In addition, ANP inhibits glucose (re)absorption at the level of both the intestine and kidney. ANP also decreases sodium absorption in the rat small intestine in vitro, but only if glucose is present on the luminal side of the tissue. These findings suggest that ANP inhibits

L. V González Bosc; N. A Vidal; R Prieto; J. A Tur



SANS with contrast variation study of the bacteriorhodopsin-octyl glucoside complex  

Microsoft Academic Search

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

Yiming Mo; William T. Heller



Catalpol protects primary cultured cortical neurons induced by Abeta(1-42) through a mitochondrial-dependent caspase pathway.  


It has been reported that catalpol, an iridoid glucoside, isolated from the root of Rehmannia glutinosa, protected cells from damage induced by a variety of toxic stimulus such as LPS, MPP(+) and rotenone. Here, we further evaluated the effect of catalpol against Abeta(1-42)-induced apoptosis in primary cortical neuron cultures. In the present study, the primary cortical neuron culture treated with Abeta(1-42) was severed as cell model of Alzheimer's disease (AD) in vitro. By exposure to Abeta(1-42) (5 microM) for 72 h in cultures, neuronal apoptosis occurred characterized by enhancement of activities of caspases and reactive oxygen species (ROS) as well as Bax increase, loss of mitochondrial membrane potential and cytochrome c release. Pretreatment with catalpol (0.5mM) for 30 min prior to Abeta(1-42) treatment attenuated neuronal apoptosis not only by reversing intracellular ROS accumulation, Bax level, mitochondrial membrane potential and, cytochrome c release to some extent, but also through regulating the activity and cleavage of caspase-3 and caspase-9. Thus, catalpol protects primary cultured cortical neurons induced by Abeta(1-42) through a mitochondrial-dependent caspase pathway. PMID:19631247

Liang, Jian Hua; Du, Jing; Xu, Lian Deng; Jiang, Tao; Hao, Shuang; Bi, Jing; Jiang, Bo



Pharmacokinetics of verproside after intravenous and oral administration in rats.  


Verproside, a catalpol derivative iridoid glucoside isolated from Pseudolysimachion longifolium, is a candidate for anti-asthmatic drug. The dose-dependency of the pharmacokinetics of verproside was evaluated in rats after intravenous and oral administration. After intravenous administration of verproside (2, 5 and 10 mg/kg doses), the systemic clearance (Cl) was significantly reduced and AUC was significantly increased at 10 mg/kg dose compared to 2 and 5 mg/kg doses. The volume of distribution at steady state (V (ss)) remained unchanged as the dose was increased. The extent of urinary excretion was low for both intravenous (3.3-6.2%) and oral (0.01-0.04%) doses. Isovanilloylcatalpol was identified as a metabolite after intravenous administration of verproside and showed the significant decreases in AUC and C (max) at 10 mg/kg verproside dose. The reduced systemic clearance of verproside at high doses appears to be due to the saturable metabolism. Upon oral administration of verproside (20, 50 and 100 mg/kg doses), C (max) was nonlinearly increased. The extent of verproside recovered from the gastrointestinal tract at 24 h after oral administration was 0.01-0.72% for all three doses studied. The absolute oral bioavailability (F) was 0.3 and 0.5% for 50 and 100 mg/kg doses, respectively. Low F appears to be due to first-pass metabolism. PMID:19407974

Park, Eun Jeong; Lee, Hyun Sook; Oh, Sei-Ryang; Lee, Hyeong-Kyu; Lee, Hye Suk



Mining for treatment-specific and general changes in target compounds and metabolic fingerprints in response to herbivory and phytohormones in Plantago lanceolata.  


Induction studies focusing on target metabolites may not reveal metabolic changes occurring in plants after various challenges. By contrast, metabolic fingerprinting can be a powerful tool to find patterns that are either treatment-specific or general and was therefore used to depict plant responses after various challenges. Plants of Plantago lanceolata were challenged by mechanical damage, specialist herbivores (aphids or sawfly larvae), generalist herbivores (Lepidopteran caterpillars) or phytohormones (jasmonic or salicylic acid). After 3 d of treatment, local and systemic leaves were analyzed for characteristic target metabolites (iridoid glucosides and verbascoside) by gas chromatography coupled with mass spectrometry (GC-MS) and for metabolic fingerprints by liquid chromatography coupled with time of flight mass spectrometry (LC-TOF-MS). Whereas only marginal changes in target metabolite concentrations were found, metabolic fingerprints were substantially affected especially by generalist and phytohormone treatments. By contrast, mechanical damage and specialist herbivory caused fewer changes. Responses to generalists partly overlapped with the changes caused by jasmonic acid, but many additional peaks were up-regulated. Furthermore, many peaks were co-induced by jasmonic and salicylic acid. The surprisingly high co-induction of peaks by both phytohormones suggests that the signaling pathways regulate a set of common targets. Furthermore, only metabolic fingerprinting could reveal that herbivores induce additional species-specific pathways beyond these phytohormone responses. PMID:21592133

Sutter, Rabea; Müller, Caroline



A comparison of flavonoid glycosides by electrospray tandem mass spectrometry  

Microsoft Academic Search

A comparison is presented of product ion mass spectra of protonated and deprotonated molecules of kaempferol-3-O-glucoside, quercitin-3-O-glucoside (isoquercitrin), quercitin-3-O-galactoside (hyperoin), apigenin-7-O-glucoside, luteolin-7-O-glucoside, genistein-7-O-glucoside, naringenin-7-O-glucoside (prunin), luteolin-4'-O-glucoside, luteolin-6-C-glucoside (homoorientin, known also as isoorientin), apigenin-8-C-glucoside (vitexin), and luteolin-8-C-glucoside (orientin) together with the product ion mass spectrum of deprotonated kaempferol-7-O-glucoside. All isomeric ions were distinguishable on the basis of their product ion mass

Raymond E. March; Errol G. Lewars; Christopher J. Stadey; Xiu-Sheng Miao; Xiaoming Zhao; Chris D. Metcalfe



Transglucosylation of ascorbic acid to ascorbic acid 2-glucoside by a recombinant sucrose phosphorylase from Bifidobacterium longum  

Microsoft Academic Search

A novel transglycosylation reaction from sucrose to l-ascorbic acid by a recombinant sucrose phosphorylase from Bifidobacterium longum was used to produce a stable l-ascorbic acid derivative. The major product was detected by HPLC, and confirmed to be 2-O-?-d-glucopyranosyl-l-ascorbic acid by LC-MS\\/MS analysis.

Taeyeon Kwon; Cheong Tae Kim; Jong-Hoon Lee



Promotion of IL4- and IL5-dependent differentiation of anti-?-primed B cells by ascorbic acid 2-glucoside  

Microsoft Academic Search

The stable ascorbic acid derivative 2-O-?-d-glucopyranosyl-l-ascorbic acid (AA-2G) was used to investigate the role of ascorbic acid (AA) in B cell differentiation in vitro. AA-2G is stable in a solution unlike AA but is hydrolyzed by cellular ?-glucosidase to release AA. Mouse spleen B cells were primed for 2 days with an anti-? antibody in the presence of interleukin (IL)-4

Kenji Ichiyama; Hitoshi Mitsuzumi; Ming Zhong; Akihiro Tai; Akihiro Tsuchioka; Saeko Kawai; Itaru Yamamoto; Eiichi Gohda



Participation of regulator AscG of the beta-glucoside utilization operon in regulation of the propionate catabolism operon.  


The asc operon of Escherichia coli is one of the cryptic genetic systems for beta-D-galactoside utilization as a carbon source. The ascFB genes for beta-D-galactoside transport and catabolism are repressed by the AscG regulator. After genomic SELEX screening, AscG was found to recognize and bind the consensus palindromic sequence TGAAACC-GGTTTCA. AscG binding was detected at two sites upstream of the ascFB promoter and at three sites upstream of the prpBC operon for propionate catabolism. In an ascG-disrupted mutant, transcription of ascFB was enhanced, in agreement with the repressor model of AscG. This repression was indicated to be due to interference of binding of cyclic AMP-CRP to the CRP box, which overlaps with the AscG-binding site 1, as well as binding of RNA polymerase to the promoter. Under conditions of steady-state E. coli growth in a rich medium, the intracellular level of AscG stayed constant at a level supposedly leading to tight repression of the ascFB operon. The level of prpR, encoding the activator of prpBCDE, was also increased in the absence of AscG, indicating the involvement of AscG in repression of prpR. Taken together, these data suggest a metabolic link through interplay between the asc and prp operons. PMID:19633077

Ishida, Yuji; Kori, Ayako; Ishihama, Akira



454 pyrosequencing based transcriptome analysis of Zygaena filipendulae with focus on genes involved in biosynthesis of cyanogenic glucosides  

Microsoft Academic Search

BACKGROUND: An essential driving component in the co-evolution of plants and insects is the ability to produce and handle bioactive compounds. Plants produce bioactive natural products for defense, but some insects detoxify and\\/or sequester the compounds, opening up for new niches with fewer competitors. To study the molecular mechanism behind the co-adaption in plant-insect interactions, we have investigated the interactions

Mika Zagrobelny; Karsten Scheibye-Alsing; Niels Bjerg Jensen; Birger Møller; Jan Gorodkin; Søren Bak



An on-line method for pressurized hot water extraction and enzymatic hydrolysis of quercetin glucosides from onions.  


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 ?-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 ?mol g(-1) fresh weight yellow onion) compared to a conventional batch extraction method using methanol as extraction solvent. PMID:23764443

Lindahl, Sofia; Liu, Jiayin; Khan, Samiullah; Karlsson, Eva Nordberg; Turner, Charlotta



Cyanidin3Glucoside inhibits ethanol-induced invasion of breast cancer cells overexpressing ErbB2  

Microsoft Academic Search

BACKGROUND: Ethanol is a tumor promoter. Both epidemiological and experimental studies suggest that ethanol may enhance the metastasis of breast cancer cells. We have previously demonstrated that ethanol increased the migration\\/invasion of breast cancer cells expressing high levels of ErbB2. Amplification of ErbB2 is found in 20-30% of breast cancer patients and is associated with poor prognosis. We sought to

Mei Xu; Kimberly A Bower; Siying Wang; Jacqueline A Frank; Gang Chen; Min Ding; Shiow Wang; Xianglin Shi; Zunji Ke; Jia Luo



Genetic transformation of Gentiana macrophylla with Agrobacterium rhizogenes : growth and production of secoiridoid glucoside gentiopicroside in transformed hairy root cultures  

Microsoft Academic Search

Hairy root cultures of Gentiana macrophylla were established by infecting the different explants four Agrobacterium rhizogenes strains namely A4GUS, R1000, LBA 9402 and ATCC11325, and hairy root lines were established with A. rhizogenes strain R1000 in 1\\/2 MS + B5 medium. Initially, 42 independent hairy root clones were maintained and seven clones belongs to different category were evaluated\\u000a for growth,

Rajesh Kumar Tiwari; Mala Trivedi; Zhang Chun Guang; Guang-Qin Guo; Guo-Chang Zheng



Method 1600: 'Enterococci' in Water by Membrane Filtration Using membrane-Enterococcus Indoxyl-D-Glucoside Agar (mEI).  

National Technical Information Service (NTIS)

This method describes a membrane filter (MF) procedure for the detection and enumeration of the enterococci bacteria in water. Enterococci are commonly found in the feces of humans and other warm-blooded animals. Although some strains are ubiquitous and n...



Novel phosphotransferase system genes revealed by bacterial genome analysis: unique, putative fructose- and glucoside-specific systems.  


Analyses of sequences made available through the Escherichia coli genome project in the 87.2-89.2-min and 81.5-84.5-min regions have revealed 2 putative operons encoding proteins of the phosphoenolpyruvate:sugar phosphotransferase system (PTS). The first putative operon, designated frv, includes 4 open reading frames (ORFs), ORFf147, ORFf485, ORFf356, and ORFf582, ORFf147 and ORFf485 comprise an Enzyme IIA-Enzyme IIBC pair of the PTS. The sequence similarity of ORFf485 to previously characterized fructose-specific Enzymes IIBC suggests that ORFf485 may be specific for fructose. ORFf147 encodes a protein with comparable degrees of sequence similarity to fructose and mannitol-specific Enzymes IIA as well as homologous proteins implicated in sigma 54-dependent transcriptional regulation. Unique features of this system include a detached IIA protein and the absence of a IIB domain duplication. ORFf356 and ORFf582 are functionally unidentified and nonhomologous to other ORFs in the current protein databases, but ORFf582 contains 2 N-terminal helix-turn-helix motifs, suggestive of a role in frv operon transcriptional regulation. The second putative operon, designated glv, includes 3 ORFs, ORFf455, ORFf161, and ORFf212. We suggest that ORFf455 was incorrectly assigned and should be designated ORFf368. ORFf368 and ORFf161 encode an Enzyme IIC and IIB pair of the PTS showing greatest sequence similarity to Enzymes II specific for sugars of the gluco configuration. ORFf212 encodes a protein with sequence similarity to a phospho-beta-glucosidase and an alpha-galactosidase. No putative transcriptional regulator of the glv operon was found. This operon is the first one encoding a putative PTS permease with detached Enzymes IIB and IIC and lacking an Enzyme IIA. It is suggested that both the frv and glv operons are cryptic in E. coli and that additional genes encoding novel PTS-related proteins will be revealed by bacterial genome sequence analyses. PMID:8019415

Reizer, J; Michotey, V; Reizer, A; Saier, M H



Transglucosylation of ascorbic acid to ascorbic acid 2-glucoside by a recombinant sucrose phosphorylase from Bifidobacterium longum.  


A novel transglycosylation reaction from sucrose to L-ascorbic acid by a recombinant sucrose phosphorylase from Bifidobacterium longum was used to produce a stable L-ascorbic acid derivative. The major product was detected by HPLC, and confirmed to be 2-O-alpha-D-glucopyranosyl-L-ascorbic acid by LC-MS/MS analysis. PMID:17216298

Kwon, Taeyeon; Kim, Cheong Tae; Lee, Jong-Hoon



12-hydroxyjasmonic acid glucoside is a COI1-JAZ-independent activator of leaf-closing movement in Samanea saman.  


Jasmonates are ubiquitously occurring plant growth regulators with high structural diversity that mediate numerous developmental processes and stress responses. We have recently identified 12-O-?-D-glucopyranosyljasmonic acid as the bioactive metabolite, leaf-closing factor (LCF), which induced nyctinastic leaf closure of Samanea saman. We demonstrate that leaf closure of isolated Samanea pinnae is induced upon stereospecific recognition of (-)-LCF, but not by its enantiomer, (+)-ent-LCF, and that the nonglucosylated derivative, (-)-12-hydroxyjasmonic acid also displays weak activity. Similarly, rapid and cell type-specific shrinkage of extensor motor cell protoplasts was selectively initiated upon treatment with (-)-LCF, whereas flexor motor cell protoplasts did not respond. In these bioassays related to leaf movement, all other jasmonates tested were inactive, including jasmonic acid (JA) and the potent derivates JA-isoleucine and coronatine. By contrast, (-)-LCF and (-)-12-hydroxyjasmonic acid were completely inactive with respect to activation of typical JA responses, such as induction of JA-responsive genes LOX2 and OPCL1 in Arabidopsis (Arabidopsis thaliana) or accumulation of plant volatile organic compounds in S. saman and lima bean (Phaseolus lunatus), generally considered to be mediated by JA-isoleucine in a COI1-dependent fashion. Furthermore, application of selective inhibitors indicated that leaf movement in S. saman is mediated by rapid potassium fluxes initiated by opening of potassium-permeable channels. Collectively, our data point to the existence of at least two separate JA signaling pathways in S. saman and that 12-O-?-D-glucopyranosyljasmonic acid exerts its leaf-closing activity through a mechanism independent of the COI1-JAZ module. PMID:21228101

Nakamura, Yoko; Mithöfer, Axel; Kombrink, Erich; Boland, Wilhelm; Hamamoto, Shin; Uozumi, Nobuyuki; Tohma, Kentaro; Ueda, Minoru



Characterization of sterol glucosyltransferase from Salinispora tropica CNB-440: potential enzyme for the biosynthesis of sitosteryl glucoside.  


A sterol glucosyltransferase-encoded gene was isolated from Salinispora tropica CNB-440, a marine, sediment-dwelling, Gram positive bacterium that produces the potent anticancer compound, salinosporamide A. The full-length gene consists of 1284 nucleotides and encodes 427 amino acids with a calculated mass of 45.65kDa. The gene was then cloned and heterologously expressed in Escherichia coli BL21(DE3). The amino acid sequence shares 39% similarity with the glycosyltransferase from Withania somnifera, which belongs to glycosyltransferase family 1. Enzyme reactions were carried out with the various free sterols (acceptor) and NDP-sugars (donor). The purified protein only showed activity for glucosylation of ?-sitosterol with UDP-D-glucose and TDP-D-glucose donors, and optimal activity at pH 7.5 and 37°C. Among these two donors, UDP-D-glucose was preferred. PMID:23540924

Thuan, Nguyen Huy; Yamaguchi, Tokutaro; Lee, Joo Ho; Sohng, Jae Kyung



Search for constituents with neurotrophic factor-potentiating activity from the medicinal plants of paraguay and Thailand.  


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

Li, Yushan; Ohizumi, Yasushi



Catalpol inhibits apoptosis in hydrogen peroxide-induced endothelium by activating the PI3K/Akt signaling pathway and modulating expression of Bcl-2 and Bax.  


Catalpol, an iridoid glucoside found in the root of Rehmannia glutinosa Libosch, has been demonstrated to reduce apoptosis in neuronal cell lines. Recent data suggests that catalpol also exerts anti-apoptotic effects on other cell types. The aim of the present study was to investigate whether catalpol protects against hydrogen peroxide (H(2)O(2)) induced apoptosis in human umbilical vein endothelial cells (HUVECs). Apoptotic cells were detected by terminal deoxyribonucleotidyl transferase-mediated deoxyuridine triphosphate-biotin nick end labeling, Annexin V-fluorescein isothiocyanate binding assay and by assessment of caspase-3 activity. The level of intracellular reactive oxygen species was quantified by 2', 7'-dichlorofluorescein diacetate assay. Expression of Akt, Bad, Bcl-2 and Bax mRNA and protein was determined by real-time semiquantitative reverse transcription-polymerase chain reaction and Western blotting. Apoptosis in HUVECs was associated with increased Bax, decreased Bcl-2 activity and inactivated phosphorylation of Akt and Bad after 24h of H(2)O(2) exposure. Pre-treatment of HUVECs with catalpol significantly reduced H(2)O(2)-induced intracellular reactive oxygen species release. Catalpol not only increased the expression of Bcl-2, while decreasing Bax expression, but also induced Akt activation and Bad phosphorylation, and ultimately reduced H(2)O(2)-induced apoptosis. The protective effects of catalpol were partially inhibited by the phosphatidylinositol 3-kinase (PI3K) antagonist wortmannin or 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one (LY294002). Taken together, these results suggest that pre-treatment of HUVECs with catalpol can block H(2)O(2)-induced apoptosis, and that the underlying mechanism involves reactive oxygen species scavenging, activation of the PI3K/Akt-Bad signaling pathway and increased Bcl-2 and decreased Bax expression. PMID:19962976

Hu, Lingai; Sun, Yukun; Hu, Jian



Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver ?-glucosidase activity  

Microsoft Academic Search

Flavonoid and isoflavonoid glycosides are common dietary phenolics which may be absorbed from the small intestine of humans. The ability of cell-free extracts from human small intestine and liver to deglycosylate various (iso)flavonoid glycosides was investigated. Quercetin 4?-glucoside, naringenin 7-glucoside, apigenin 7-glucoside, genistein 7-glucoside and daidzein 7-glucoside were rapidly deglycosylated by both tissue extracts, whereas quercetin 3,4?-diglucoside, quercetin 3-glucoside, kaempferol

Andrea J Day; M. Susan DuPont; Saxon Ridley; Mike Rhodes; Michael J. C Rhodes; Michael R. A Morgan; Gary Williamson



The Safety and Pharmacokinetics of Cyanidin-3-Glucoside after 2-Week Administration of Black Bean Seed Coat Extract in Healthy Subjects  

PubMed Central

We analyzed the pharmacokinetics of C3G on data from twelve subjects, after 2-week multiple dosing of black bean (Phaseolus vulgaris, Cheongjakong-3-ho) seed coat extract, using the mixed effect analysis method (NONMEM, Ver. 6.2), as well as the conventional non-compartmental method. We also examined the safety and tolerability. The PK analysis used plasma concentrations of the C3G on day 1 and 14. There was no observed accumulation of C3G after 2-week multiple dosing of black bean seed coat extract. The typical point estimates of PK were CL (clearance)=3,420 l/h, V (volume)=7,280 L, Ka (absorption constant)=9.94 h-1, ALAG (lag time)=0.217 h. The black bean seed coat extract was well tolerated and there were no serious adverse events. In this study, we confirmed that a significant amount of C3G was absorbed in human after given the black bean seed coat extract.

Jeon, Sangil; Han, Seunghoon; Lee, Jongtae; Hong, Taegon



Cloning and comparison of third beta-glucoside utilization (bglEFIA) operon with two operons of Pectobacterium carotovorum subsp. carotovorum LY34.  


A third bgl operon containing bglE, bglF, bglI, and bglA was isolated from Pectobacterium carotovorum subsp. carotovorum LY34 (Pcc LY34). The sequences of BglE, BglF, and Bgll were similar to those of the phosphotransferase system (PTS) components IIB, IIC, and IIA respectively. BglF contains important residues for the phosphotransferase system. The amino acid sequence of BglA showed high similarity to various 6-phospho-beta-glucosidases and to a member of glycosyl hydrolase family 1. Sequence and structural analysis also revealed that these four genes were organized in a putative operon that differed from two operons previously isolated from Pcc LY34, bglTPB (accession no. AY542524) and ascGFB (accession no. AY622309). The transcription regulator for this operon was not found, and the EII complexes for PTS were encoded separately by three genes (bglE, bglF, and bglI). The BglA enzyme had a molecular weight estimated to be 57,350 Da by SDS-PAGE. The purified beta-glucosidase hydrolyzed salicin, arbutin, rhoNPG, rhoNPbetaG6P, and MUG, exhibited maximal activity at pH 7.0 and 40 degrees C, and displayed enhanced activity in the presence of Mg2+ and Ca2+. Two glutamate residues (Glu178 and Glu378) were found to be essential for enzyme activity. PMID:16636444

Hong, Su Young; An, Chang Long; Cho, Kye Man; Lee, Sun Mi; Kim, Yong Hee; Kim, Min Keun; Cho, Soo Jeong; Lim, Yong Pyo; Kim, Hoon; Yun, Han Dae



Sustrate-specificity of glucomylase (E.C. exemplified by p-nitroaniline n-glucosides.  


The present paper supplements the previous investigations on the mechanism of reactions catalyzed by amylolytic enzymes. The performed experiments corroborated the data on transglucosylative properties of animal glucoamylases which were found to depend on the structure and concentration of substrate. The p-nitroanilines were first introduced in this type of research enabling to find the differences of activity mechanism of animal glucoamylases and Aspergillus niger glucoamylase. In complement to the data reported by Japanese students the transglucosylative properties of glucoamylases were shown to depend not only on the enzyme origin and substrate concentration but also on the chemical composition of applied substrate and concentration of hydrogen ions in the reaction medium. PMID:13765

Kossobudzki, L



Fusicoccin a, a phytotoxic carbotricyclic diterpene glucoside of fungal origin, reduces proliferation and invasion of glioblastoma cells by targeting multiple tyrosine kinases.  


Glioblastoma multiforme (GBM) is a deadly cancer that possesses an intrinsic resistance to pro-apoptotic insults, such as conventional chemotherapy and radiotherapy, and diffusely invades the brain parenchyma, which renders it elusive to total surgical resection. We found that fusicoccin A, a fungal metabolite from Fusicoccum amygdali, decreased the proliferation and migration of human GBM cell lines in vitro, including several cell lines that exhibit varying degrees of resistance to pro-apoptotic stimuli. The data demonstrate that fusicoccin A inhibits GBM cell proliferation by decreasing growth rates and increasing the duration of cell division and also decreases two-dimensional (measured by quantitative video microscopy) and three-dimensional (measured by Boyden chamber assays) migration. These effects of fusicoccin A treatment translated into structural changes in actin cytoskeletal organization and a loss of GBM cell adhesion. Therefore, fusicoccin A exerts cytostatic effects but low cytotoxic effects (as demonstrated by flow cytometry). These cytostatic effects can partly be explained by the fact that fusicoccin inhibits the activities of a dozen kinases, including focal adhesion kinase (FAK), that have been implicated in cell proliferation and migration. Overexpression of FAK, a nonreceptor protein tyrosine kinase, directly correlates with the invasive phenotype of aggressive human gliomas because FAK promotes cell proliferation and migration. Fusicoccin A led to the down-regulation of FAK tyrosine phosphorylation, which occurred in both normoxic and hypoxic GBM cell culture conditions. In conclusion, the current study identifies a novel compound that could be used as a chemical template for generating cytostatic compounds designed to combat GBM. PMID:23544164

Bury, Marina; Andolfi, Anna; Rogister, Bernard; Cimmino, Alessio; Mégalizzi, Véronique; Mathieu, Véronique; Feron, Olivier; Evidente, Antonio; Kiss, Robert



An enzyme catalyzing O-prenylation of the glucose moiety of fusicoccin A, a diterpene glucoside produced by the fungus Phomopsis amygdali.  


Isoprenoids form the largest family of compounds found in nature. Isoprenoids are often attached to other moieties such as aromatic compounds, indoles/tryptophan, and flavonoids. These reactions are catalyzed by three phylogenetically distinct prenyltransferases: soluble aromatic prenyltransferases identified mainly in actinobacteria, soluble indole prenyltransferases mostly in fungi, and membrane-bound prenyltransferases in various organisms. Fusicoccin A (FC A) is a diterpene glycoside produced by the plant-pathogenic fungus Phomopsis amygdali and has a unique O-prenylated glucose moiety. In this study, we identified for the first time, from a genome database of P. amygdali, a gene (papt) encoding a prenyltransferase that reversibly transfers dimethylallyl diphosphate (DMAPP) to the 6'-hydroxy group of the glucose moiety of FC A to yield an O-prenylated sugar. An in vitro assay with a recombinant enzyme was also developed. Detailed analyses with recombinant PAPT showed that the enzyme is likely to be a monomer and requires no divalent cations. The optimum pH and temperature were 8.0 and 50?°C, respectively. K(m) values were calculated as 0.49±0.037 ?M for FC P (a plausible intermediate of FC A biosynthesis) and 8.3±0.63 ?M for DMAPP, with a k(cat) of 55.3±3.3×10?³ s. The enzyme did not act on representative substrates of the above-mentioned three types of prenyltransferase, but showed a weak transfer activity of geranyl diphosphate to FC P. PMID:22287087

Noike, Motoyoshi; Liu, Chengwei; Ono, Yusuke; Hamano, Yoshimitsu; Toyomasu, Tomonobu; Sassa, Takeshi; Kato, Nobuo; Dairi, Tohru



Studies on the anti-diabetic and hypolipidemic potentials of mangiferin (Xanthone Glucoside) in streptozotocin-induced Type 1 and Type 2 diabetic model rats  

Microsoft Academic Search

Context: Mangifera indica (Anacardiaceae) stem bark contains a rich content of mangiferin and is used traditionally in Indian Ayurvedic system to treat diabetes. Purpose of the study: To investigate anti-diabetic and hypolipidemic effects of mangiferin in type 1 and type 2 diabetic rats models. Streptozotocin was used to induce type 1 and type 2 diabetic rats. Mangiferin (at a dose

Dineshkumar B; Analava Mitra; M Manjunatha



Enhanced accumulation of caffeic acid, rosmarinic acid and luteolin-glucoside in red perilla cultivated under red diode laser and blue LED illumination followed by UVA irradiation  

Microsoft Academic Search

Red perilla (Perilla frutescens var. purpurea cv. Akajiso) is a plant rich in polyphenols such as rosmarinic acid and luteolin with great potential as a functional food material. The present study examines whether growth under controlled artificial illumination could be used for cultivation of red perilla to enhance rosmarinic acid and luteolin content. Red perilla plants were cultivated for 7weeks

Mayuko Iwai; Mari Ohta; Hiroshi Tsuchiya; Tetsuya Suzuki



Implications of low-power He-Ne laser and monochromatic red light biostimulation in the metabolism of proteins and glucosides  

NASA Astrophysics Data System (ADS)

We checked the changes occurring in the metabolism of proteins (seric cholinesterase, total proteins) and in the metabolism of glycosides (seric glucose) in Cavia cobaia. A simple blind study was carried out and the results were checked on the first, tenth and twentieth days of treatment. The data thus obtained were graphically represented and statistically processed according to the Duncan test. The technique and treatment doses were similar and they were compared with the data obtained from controls and environment controls. In the groups biostimulated with He-Ne laser, seric cholinesterase levels increased proportionally with the dose reaching a peak on day 10, which was not the case with the controls. Monochromatic red light caused a similar but quantitatively lower effect. The same results were obtained in the case of seric proteins as well, however, the effect did not depend on the dose and it was less significant statistically than in the case of seric cholinesterase both in laser treated and in monochromatic red light treated groups.

Onac, I.; Pop, L.; Ungur, Rodica; Giurgiu, Ioana



Quercetin Glucosides Interact With the Intestinal Glucose Transport Pathway 1 1 This work was supported by a UK Biotechnology and Biological Sciences Research Council Competitive Strategic Grant  

Microsoft Academic Search

Flavonols are efficient antioxidants with the potential to protect biological macromolecules from oxidative damage in vivo, and if absorbed into the circulation they may protect against cardiovascular disease. Although flavonol aglycones are present in foods at low concentrations, their glycosides are abundant in onions, apples, beans and tea, and are thought to be stable under the conditions of the human

Jennifer M Gee; M. Susan DuPont; Michael J. C Rhodes; Ian T Johnson



Method 1600: Enterococci in Water by Membrane Filtration Using membrane-Enterococcus Indoxyl-Beta-D-Glucoside Agar (mEI), April 2005.  

National Technical Information Service (NTIS)

Method 1600 describes a membrane filter (MF) procedure for the detection and enumeration of the enterococci bacteria in water. This is a single-step method that is a modification of EPA Method 1106.1 (mE-EIA). Unlike the mE-EIA method, it does not require...



Method 1600: Enterococci in Water by Membrane Filtration Using Membrane-Enterococcus Indoxyl-Beta-D-Glucoside Agar (mEI), July 2006.  

National Technical Information Service (NTIS)

The MF method provides a direct count of bacteria in water based on the development of colonies on the surface of the membrane filter (Reference 18.5). A water sample is filtered through the membrane which retains the bacteria. Following filtration, the m...



Enzymatic Synthesis of the Flavone Glucosides, Prunin and Isoquercetin, and the Aglycones, Naringenin and Quercetin, with Selective ?-L-Rhamnosidase and ?-D-Glucosidase Activities of Naringinase  

PubMed Central

The production of flavonoid glycosides by removing rhamnose from rutinosides can be accomplished through enzymatic catalysis. Naringinase is an enzyme complex, expressing both ?-L-rhamnosidase and ?-D-glucosidase activities, with application in glycosides hydrolysis. To produce monoglycosylated flavonoids with naringinase, the expression of ?-D-glucosidase activity is not desirable leading to the need of expensive methods for ?-L-rhamnosidase purification. Therefore, the main purpose of this study was the inactivation of ?-D-glucosidase activity expressed by naringinase keeping ?-L-rhamnosidase with a high retention activity. Response surface methodology (RSM) was used to evaluate the effects of temperature and pH on ?-D-glucosidase inactivation. A selective inactivation of ?-D-glucosidase activity of naringinase was achieved at 81.5°C and pH 3.9, keeping a very high residual activity of ?-L-rhamnosidase (78%). This was a crucial achievement towards an easy and cheap production method of very expensive flavonoids, like prunin and isoquercetin starting from naringin and rutin, respectively.

Vila-Real, Helder; Alfaia, Antonio J.; Bronze, M. Rosario; Calado, Antonio R. T.; Ribeiro, Maria H. L.



Effects of benzyl glucoside and chlorogenic acid from Prunus mume on adrenocorticotropic hormone (ACTH) and catecholamine levels in plasma of experimental menopausal model rats.  


To investigate the effectiveness of benzyl beta-D-glucopyranoside (BG) and chlorogenic acid (CA), the constituents of the fruit of Prunus mume, for relieving tension in experimental menopausal model rats (M-rats) caused by ether stress, the effects of BG and CA on adrenocorticotropic hormone (ACTH) and catecholamine (adrenaline, noradrenaline, and dopamine) levels were examined in the plasma of M-rats. Caffeic acid, quinic acid, and rosmarinic acid, which are compounds structurally related to CA, were also examined. BG obviously recovered catecholamine levels decreased by ether stress and increased dopamine to high levels. On the other hand, CA significantly decreased the ACTH level increased by ether stress and showed the greatest effect of all compounds. These results suggest that BG and CA may contribute to relieving the tension in M-rats caused by ether stress. PMID:14709918

Ina, Hiroji; Yamada, Kenji; Matsumoto, Kosai; Miyazaki, Toshio



Fusicoccin A, a Phytotoxic Carbotricyclic Diterpene Glucoside of Fungal Origin, Reduces Proliferation and Invasion of Glioblastoma Cells by Targeting Multiple Tyrosine Kinases1  

PubMed Central

Glioblastoma multiforme (GBM) is a deadly cancer that possesses an intrinsic resistance to pro-apoptotic insults, such as conventional chemotherapy and radiotherapy, and diffusely invades the brain parenchyma, which renders it elusive to total surgical resection. We found that fusicoccin A, a fungal metabolite from Fusicoccum amygdali, decreased the proliferation and migration of human GBM cell lines in vitro, including several cell lines that exhibit varying degrees of resistance to pro-apoptotic stimuli. The data demonstrate that fusicoccin A inhibits GBM cell proliferation by decreasing growth rates and increasing the duration of cell division and also decreases two-dimensional (measured by quantitative video microscopy) and three-dimensional (measured by Boyden chamber assays) migration. These effects of fusicoccin A treatment translated into structural changes in actin cytoskeletal organization and a loss of GBM cell adhesion. Therefore, fusicoccin A exerts cytostatic effects but low cytotoxic effects (as demonstrated by flow cytometry). These cytostatic effects can partly be explained by the fact that fusicoccin inhibits the activities of a dozen kinases, including focal adhesion kinase (FAK), that have been implicated in cell proliferation and migration. Overexpression of FAK, a nonreceptor protein tyrosine kinase, directly correlates with the invasive phenotype of aggressive human gliomas because FAK promotes cell proliferation and migration. Fusicoccin A led to the down-regulation of FAK tyrosine phosphorylation, which occurred in both normoxic and hypoxic GBM cell culture conditions. In conclusion, the current study identifies a novel compound that could be used as a chemical template for generating cytostatic compounds designed to combat GBM.

Bury, Marina; Andolfi, Anna; Rogister, Bernard; Cimmino, Alessio; Megalizzi, Veronique; Mathieu, Veronique; Feron, Olivier; Evidente, Antonio; Kiss, Robert



Radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl of ascorbic acid 2-glucoside (AA-2G) and 6-acyl-AA-2G.  


The radical scavenging activity of the stable derivatives, which are O-substituted at the C-2 position of ascorbic acid (AA), against 1,1-diphenyl-2-picrylhydrazyl (DPPH) was evaluated in buffer under different pH conditions, and compared with those of AA and alpha-tocopherol. AA was shown to have 50% radical scavenging ability (EC50) at a concentration of 2.2 x 10(-5) M against 0.1 mM DPPH in 60% ethanol. Ascorbyl 6-palmitate, a lipophilic AA derivative which has a free endiol group and is therefore unstable, also showed potent radical scavenging activity with EC50 of 2.9 x 10(-5) M. A typical lipophilic antioxidant, alpha-tocopherol gave a similar EC50 value as that of AA. In contrast, ascorbyl 2,6-dipalmitate, AA 2-phosphate and AA 2-sulfate exhibited negligible scavenging activity. On the other hand, 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G) and a series of 6-O-acyl-2-O-alpha-D-glucopyranosyl-L-ascorbic acids (6-Acyl-AA-2G) themselves exhibited the radical scavenging activity of EC50: 6.1 x 10(-5) M and 4.4 x 10(-5)-5.9 x 10(-5) M, respectively, although their activities were lower than that of AA. Among 6-Acyl-AA-2G derivatives, the EC50 values tended to decrease with increasing length of their acyl carbon group. Increasing pH of the buffer resulted in decrease in the scavenging activity of all compounds tested as expected. We speculate that the difference in the radical scavenging activity of derivatives O-substituted at the C-2 position of AA may be ascribed to the linkage type of the substituent group to the endiol-lactone resonance system and the degree of dissociation of the C-3 proton. PMID:11383624

Fujinami, Y; Tai, A; Yamamoto, I



Antiscorbutic activity of L-ascorbic acid 2-glucoside and its availability as a vitamin C supplement in normal rats and guinea pigs.  


Bioavailability of a newly-synthesized and chemically-stable 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G) as a vitamin C supplement was investigated in rats and guinea pigs. Oral administration of AA-2G to the animals resulted in an increase of serum ascorbic acid (AA) levels. However, in these sera the intact form was not detectable by the high performance liquid chromatography (HPLC) method, indicating its hydrolysis through the process of absorption. After an intravenous injection of AA-2G, the intact form diminished rapidly from the serum, followed by prolonged and marked elevation of serum AA levels. Various tissue homogenates from rats and guinea pigs were examined for their releasing activity of AA from AA-2G. High activity was observed in kidney, small intestine and serum of rats and in small intestine and kidney of guinea pigs. These hydrolytic activities were completely inhibited by castanospermine, a specific alpha-glucosidase inhibitor, suggesting the participation of alpha-glucosidase in the in vivo hydrolysis of AA-2G. AA-2G was found to exhibit obvious therapeutic effect in scorbutic guinea pigs by its repeated oral administrations. These results indicate that AA-2G is a readily available source of vitamin C activity in vivo. PMID:2093127

Yamamoto, I; Suga, S; Mitoh, Y; Tanaka, M; Muto, N



Promotion of IL-4- and IL-5-dependent differentiation of anti-mu-primed B cells by ascorbic acid 2-glucoside.  


The stable ascorbic acid derivative 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G) was used to investigate the role of ascorbic acid (AA) in B cell differentiation in vitro. AA-2G is stable in a solution unlike AA but is hydrolyzed by cellular alpha-glucosidase to release AA. Mouse spleen B cells were primed for 2 days with an anti-mu antibody in the presence of interleukin (IL)-4 and IL-5 and then washed and recultured with AA-2G in the presence of IL-4 and IL-5. AA-2G, but not AA, dose-dependently increased IgM production, the greatest enhancement being 150% at concentrations of more than 0.5mM. In the absence of IL-4 and IL-5, primed B cells produced a negligible amount of IgM, and AA-2G had no effect. AA-2G-induced IgM production in the presence of IL-4 and IL-5 was inhibited by the alpha-glucosidase inhibitor castanospermine. Intracellular AA content, depleted during the priming period, increased by adding AA-2G at the start of reculture. Treatment of B cells with AA-2G resulted in an increase in the number of IgM-secreting cells, CD138-positive cells and CD45R/B220-negative cells. The number of viable cells in untreated cultures decreased gradually, but the decrease was significantly attenuated by AA-2G, resulting in about 70% more viable cells in AA-2G-treated cultures. AA-2G caused a slight but reproducible enhancement of DNA synthesis and a slight decrease in the number of cells with a sub-G1 DNA content. These results demonstrated that AA released from AA-2G enhanced cytokine-dependent IgM production in anti-mu-primed B cells and suggest that its effect is caused through promoting the differentiation of B cells to plasma cells and attenuating the gradual decrease in the number of viable cells. PMID:19201381

Ichiyama, Kenji; Mitsuzumi, Hitoshi; Zhong, Ming; Tai, Akihiro; Tsuchioka, Akihiro; Kawai, Saeko; Yamamoto, Itaru; Gohda, Eiichi



12-Hydroxyjasmonic Acid Glucoside Is a COI1-JAZ-Independent Activator of Leaf-Closing Movement in Samanea saman1[OA  

PubMed Central

Jasmonates are ubiquitously occurring plant growth regulators with high structural diversity that mediate numerous developmental processes and stress responses. We have recently identified 12-O-?-d-glucopyranosyljasmonic acid as the bioactive metabolite, leaf-closing factor (LCF), which induced nyctinastic leaf closure of Samanea saman. We demonstrate that leaf closure of isolated Samanea pinnae is induced upon stereospecific recognition of (?)-LCF, but not by its enantiomer, (+)-ent-LCF, and that the nonglucosylated derivative, (?)-12-hydroxyjasmonic acid also displays weak activity. Similarly, rapid and cell type-specific shrinkage of extensor motor cell protoplasts was selectively initiated upon treatment with (?)-LCF, whereas flexor motor cell protoplasts did not respond. In these bioassays related to leaf movement, all other jasmonates tested were inactive, including jasmonic acid (JA) and the potent derivates JA-isoleucine and coronatine. By contrast, (?)-LCF and (?)-12-hydroxyjasmonic acid were completely inactive with respect to activation of typical JA responses, such as induction of JA-responsive genes LOX2 and OPCL1 in Arabidopsis (Arabidopsis thaliana) or accumulation of plant volatile organic compounds in S. saman and lima bean (Phaseolus lunatus), generally considered to be mediated by JA-isoleucine in a COI1-dependent fashion. Furthermore, application of selective inhibitors indicated that leaf movement in S. saman is mediated by rapid potassium fluxes initiated by opening of potassium-permeable channels. Collectively, our data point to the existence of at least two separate JA signaling pathways in S. saman and that 12-O-?-d-glucopyranosyljasmonic acid exerts its leaf-closing activity through a mechanism independent of the COI1-JAZ module.

Nakamura, Yoko; Mithofer, Axel; Kombrink, Erich; Boland, Wilhelm; Hamamoto, Shin; Uozumi, Nobuyuki; Tohma, Kentaro; Ueda, Minoru



Production, stability, and antioxidative and antimicrobial activities of two L-ascorbate analogues from phycomyces blakesleeanus: D-erythroascorbate and D-erythroascorbate glucoside.  


D-erythroascorbate (D-EAA), a five-carbon analogue of L-ascorbate (L-AA), and D-erythroascorbate monoglucoside (D-EAAG) are accumulated in Phycomyces blakesleeanus grown on glucose (99.5 and 1084 ?g/g mycelial dry weight, respectively) and also excreted into the culture medium. Both compounds showed UV spectral properties and ionization constants similar to those of L-AA. D-EAAG was much more stable to aerobic oxidation than D-EAA and L-AA at acidic pH. D-EAAG is synthesized from D-erythroascorbate by a mycelial glucosyltransferase activity that uses UDP-glucose as glucose substrate donor with K(m) = 2.5 mM and 41.3 ?M for D-EAA. This glucosyltransferase activity was maximal in the stationary growth phase in parallel with maximal production of D-EAAG. The presence of D-arabinose or D-arabinono-1,4-lactone in the culture medium produces the maximal accumulation of D-EAA and D-EAAG (about 30- and 4-fold with respect to that obtained in glucose culture). Both compounds showed greater antioxidant activity than L-AA and other standard antioxidants, with a capacity similar to that of L-AA to inhibit the growth of Escherichia coli. PMID:20815349

Gutierrez-Larrainzar, Marta; de Castro, Cristina; del Valle, Pilar; Rúa, Javier; García-Armesto, María Rosario; Busto, Félix; de Arriaga, Dolores



Chemical nature of the weak linkages Communication 1. Effect of carboxy groups in the cellulose molecule on the stability of the glucosidic link  

Microsoft Academic Search

In recent years much attention has been devoted to the study of details of the chemical structure of the cellulose molecule [1], for the known chemical structure of the cellulose molecule [2, 3] cannot explain some of the properties of cellulose, for example the change in the values of hydrolysis constants with time in an acid medium. These investigations were

V. I. Ivanov; Z. I. Kuznetsova



Identification of benzophenone C-glucosides from mango tree leaves and their inhibitory effect on triglyceride accumulation in 3T3-L1 adipocytes.  


A 70% ethanol-water extract from the leaves of Mangifera indica L. (Anacardiaceae) inhibited triglyceride (TG) accumulation in 3T3-L1 cells. From the active fraction, seven new benzophenone C-glycosides, foliamangiferosides A (1), A(1) (2), A(2) (3), B (4), C(1) (5), C(2) (6), and C(3) (7), together with five known compounds were isolated and the structures were elucidated on the basis of chemical and physicochemical evidence. The effects of these compounds on TG and the free fatty acid level in 3T3-L1 cells were determined, and the structure-activity relationship was discussed. On the basis of the AMPK signaling pathway, several compounds were found to increase the AMPK enzyme expression and down-regulate lipogenic enzyme gene expression such as SREBP1c, FAS, and HSL. PMID:21923172

Zhang, Yi; Qian, Qian; Ge, Dandan; Li, Yuhong; Wang, Xinrui; Chen, Qiu; Gao, Xiumei; Wang, Tao



Determination of CD59 protein in normal human serum by enzyme immunoassay, using octyl-glucoside detergent to release glycosyl-phosphatidylinositol-CD59 from lipid complex  

Microsoft Academic Search

In this study we have optimised the enzyme immunoassay (ELISA) to quantify CD59 antigen in human serum or plasma. The glycosyl-phosphatidylinositol (GPI)-linked form of CD59 is known to complex with serum high-density lipoprotein. For ELISA optimisation, therefore, we investigated the effect of detergents, added to the sample diluent, on the determined values of CD59. Values obtained in the presence of

A. P. G Landi; A. B Wilson; A Davies; P. J Lachmann; V. P. L Ferriani; D. J Seilly; A. I Assis-Pandochi



Phytochemical composition of polar fraction of Stachys germanica L. subsp. salviifolia (Ten.) Gams, a typical plant of Majella National Park.  


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-?-hydroxy-harpagide, ajugol, 5-allosyloxy-aucubin, verbascoside and, for the first time in this genus, arbutin. PMID:22372659

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



Constituents of Cissus quadrangularis.  


Two new iridoids 6-O-[2,3-dimethoxy]-trans-cinnamoyl catalpol (1) and 6-O-meta-methoxy-benzoyl catalpol (2) along with a known iridoid picroside 1 (3), two stilbenes quadrangularin A (4) and pallidol (5), quercitin (6), quercitrin (7), beta-sitosterol (8) and beta-sitosterol glycoside (9) were isolated from Cissus quadrangularis Linn. The compounds 3 and 7 are first reported from this plant. The structures were elucidated by analysis of their spectroscopic data and by direct comparison with literature. This is the first reported occurrence of iridoids in C. quadrangularis. PMID:17497424

Singh, Geetu; Rawat, Preeti; Maurya, Rakesh



Anthocyanins and flavonoids from shredded red onion and changes during storage in perforated films  

Microsoft Academic Search

From the edible parts of the Spanish red onion (cultivar ‘Morada de Amposta’), the anthocyanins cyanidin 3-glucoside, cyanidin 3-arabinoside, cyanidin 3-malonyl-glucoside and cyanidin 3-malonylarabinoside and the flavonoids quercetin 3,4?-diglucoside, quercetin 7,4?-diglucoside, quercetin 3-glucoside, dihydro-quercetin 3-glucoside and isorhamnetin 4?-glucoside were identified. The amount of anthocyanins reached 233 mg kg?1 and that of the flavonoids 943 mg kg?1 fresh weight of onions.

Federico Ferreres; María I. Gil; Francisco A. Tomás-Barberán



Constituents of Cissus quadrangularis  

Microsoft Academic Search

Two new iridoids 6-O-[2,3-dimethoxy]-trans-cinnamoyl catalpol (1) and 6-O-meta-methoxy-benzoyl catalpol (2) along with a known iridoid picroside 1 (3), two stilbenes quadrangularin A (4) and pallidol (5), quercitin (6), quercitrin (7), ?-sitosterol (8) and ?-sitosterol glycoside (9) were isolated from Cissus quadrangularis Linn. The compounds 3 and 7 are first reported from this plant. The structures were elucidated by analysis of

Geetu Singh; Preeti Rawat; Rakesh Maurya



Effects of stilbene constituents from rhubarb on nitric oxide production in lipopolysaccharide-activated macrophages  

Microsoft Academic Search

Two new anthraquinone glucosides [chrysophanol 8-O-?-d-(6?-galloyl)-glucopyranoside, aloe-emodin 1-O-?-d-glucopyranoside] together with various known stilbenes and their glucosides, anthraquinone glucosides, and a naphthalene glucoside were isolated from the rhizome of Rheum undulatum L. Three stilbenes (rhapontigenin, piceatannol, resveratrol), a naphthalene glucoside (torachrysone 8-O-?-d-glucopyranoside), and two stilbene glucoside gallates (rhaponticin 2??-O-gallate, rhaponticin 6??-O-gallate) showed inhibitory activity of NO production in lipopolysaccharide-activated macrophages. (IC50=11–69

Hisashi Matsuda; Tadashi Kageura; Toshio Morikawa; Iwao Toguchida; Shoichi Harima; Masayuki Yoshikawa



Method for Synthesis of BETA Glucans.  

National Technical Information Service (NTIS)

The invention provides a method for forming P-glucoside linkages in carbohydrate polymers, particularly synthetic glucan molecules, by attaching a protecting group to the C2 position of a glucoside donor. The protecting group of the invention stabilizes t...

D. L. Williams H. Yu H. E. Ensley



Inhibition of Th1/Th17 responses via suppression of STAT1 and STAT3 activation contributes to the amelioration of murine experimental colitis by a natural flavonoid glucoside icariin.  


Inflammatory bowel disease (IBD) is a chronic inflammatory disorder in the intestine which involves overproduction of pro-inflammatory cytokines and excessive functions of inflammatory cells. However, current treatments for IBD may have potential adverse effects including steroid dependence, infections and lymphoma. Therefore new therapies or drug candidates for the treatment of IBD are desperately needed. In the present study we found that icariin, a major bioactive compound from plants in Epimedium family, exerted protective effect on intestinal inflammation in mice induced by dextran sulfate sodium. Oral administration of icariin significantly attenuated the disease progression and alleviated the pathological changes of colitis. It also inhibited the production of pro-inflammatory cytokines and expression of p-p65, p-STAT1 and p-STAT3 in colon tissues. Further study showed that icariin dose-dependently inhibited the proliferation and activation of T lymphocytes, and suppressed pro-inflammatory cytokine levels of activated T cells. Moreover, icariin treatment inhibited the phosphorylations of STAT1 and STAT3 in CD4(+) T cells, which were the crucial transcription factors for Th1 and Th17 respectively. Taken together, these results indicate that icariin is a potential therapeutic agent for IBD. PMID:23261528

Tao, Feifei; Qian, Cheng; Guo, Wenjie; Luo, Qiong; Xu, Qiang; Sun, Yang



Modifications in Lignin and Accumulation of Phenolic Glucosides in Poplar Xylem upon Down-regulation of Caffeoyl-Coenzyme A O-Methyltransferase, an Enzyme Involved in Lignin Biosynthesis  

Microsoft Academic Search

Caffeoyl-coenzyme A O-methyltransferase (CCoAOMT) methylates, in vitro, caffeoyl-CoA and 5-hydroxyferuloyl- CoA, two possible precursors in monolignol biosynthesis in vivo. To clarify the in vivo role of CCoAOMT in lignin bio- synthesis, transgenic poplars with 10% residual CCoAOMT protein levels in the stem xylem were generated. Upon anal- ysis of the xylem, the affected transgenic lines had a 12% reduced Klason

Hugo Meyermans; Kris Morreel; Catherine Lapierre; Brigitte Pollet; AndreDe Bruyn; Roger Busson; Piet Herdewijn; Bart Devreese; Jozef Van Beeumen; Jane M. Marita; John Ralph; Cuiying Chen; Bart Burggraeve; Marc Van Montagu; Eric Messens; Wout Boerjana



Modifications in lignin and accumulation of phenolic glucosides in poplar xylem upon down-regulation of caffeoyl-coenzyme A O-methyltransferase, an enzyme involved in lignin biosynthesis.  


Caffeoyl-coenzyme A O-methyltransferase (CCoAOMT) methylates, in vitro, caffeoyl-CoA and 5-hydroxyferuloyl-CoA, two possible precursors in monolignol biosynthesis in vivo. To clarify the in vivo role of CCoAOMT in lignin biosynthesis, transgenic poplars with 10% residual CCoAOMT protein levels in the stem xylem were generated. Upon analysis of the xylem, the affected transgenic lines had a 12% reduced Klason lignin content, an 11% increased syringyl/guaiacyl ratio in the noncondensed lignin fraction, and an increase in lignin-attached p-hydroxybenzoate but otherwise a lignin composition similar to that of wild type. Stem xylem of the CCoAOMT-down-regulated lines had a pink-red coloration, which coincided with an enhanced fluorescence of mature vessel cell walls. The reduced production of CCoAOMT caused an accumulation of O(3)-beta-d-glucopyranosyl-caffeic acid, O(4)-beta-d-glucopyranosyl-vanillic acid, and O(4)-beta-d-glucopyranosyl-sinapic acid (GSA), as authenticated by (1)H NMR. Feeding experiments showed that O(3)-beta-d-glucopyranosyl-caffeic acid and GSA are storage or detoxification products of caffeic and sinapic acid, respectively. The observation that down-regulation of CCoAOMT decreases lignin amount whereas GSA accumulates to 10% of soluble phenolics indicates that endogenously produced sinapic acid is not a major precursor in syringyl lignin biosynthesis. Our in vivo results support the recently obtained in vitro enzymatic data that suggest that the route from caffeic acid to sinapic acid is not used for lignin biosynthesis. PMID:10934215

Meyermans, H; Morreel, K; Lapierre, C; Pollet, B; De Bruyn, A; Busson, R; Herdewijn, P; Devreese, B; Van Beeumen, J; Marita, J M; Ralph, J; Chen, C; Burggraeve, B; Van Montagu, M; Messens, E; Boerjan, W



Flavonoids of four Cleome and three Capparis species  

Microsoft Academic Search

The aerial parts of four Cleome and three Capparis species were investigated for their flavonoid constituents. Thirteen flavonoid glycosides were isolated and identified as kaempferol 7-rhamnoside, kaempferol 3-rutinoside, kaempferol 3,7-dirhamnoside, kaempferol 3-glucoside-7-rhamnoside, kaempferol 3-rhamnoside-7-glucoside, quercetin 7-rhamnoside, quercetin 3-rutinoside, quercetin 7-rutinoside, quercetin 3,7-dirhamnoside, quercetin 3-glucoside-7-rhamnoside, isorhamnetin 3-rutinoside, isorhamnetin 3,7-dirhamnoside, and apigenin 6,8-di-C-glucoside.

Mohamed Sharaf; Mohamed A. El-Ansari; Nabiel A. M. Saleh



Polar lipids of defatted chickpea ( Cicer arietinum L.) flour and protein isolates  

Microsoft Academic Search

Polar lipid composition of defatted chickpea flour and protein isolates was studied. The main compounds were phosphatidylcholine, phosphatidylinositol and phosphatidylethanolamine. Other compounds, in lower amounts, were sterol glucosides, esterified sterol glucosides and digalactosyldiglycerides. Palmitic, oleic and linoleic acid were the main fatty acids in polar lipids. A reduction in the content of phosphatidylinositol and sterol glucosides in the protein isolates

R. Sánchez-Vioque; A. Clemente; J. Vioque; J. Bautista; F. Millán



Quercetin triglycoside from Capparis spinosa  

Microsoft Academic Search

In addition to rutin, quercetin 3-O-glucoside and quercetin 3-O-glucoside-7-O-rhamnoside, the methanolic extract of the aerial parts of Capparis spinosa yielded the new flavonoid quercetin 3-O-[6??-?-l-rhamnosyl-6?-?-d-glucosyl]-?-d-glucoside (1).

M. Sharaf; M. A. El-Ansari; N. A. M. Saleh



Neighbor species differentially alter resistance phenotypes in Plantago.  


In this study, we investigated how neighbors (i.e., competitors) altered resistance phenotypes, namely plant size and levels of secondary compounds (iridoid glycosides), of individual plants and specifically tested whether neighbor identity mattered. We conducted a greenhouse experiment with Plantago lanceolata and Plantago major (Plantaginaceae) in which each species served as focal plants as well as neighbors in a factorial design. In addition, we harvested plants six and nine weeks after transplantation to test whether effects changed as plants grew. In both species, competition reduced plant size, and this effect increased over time. Plantago lanceolata neighbors suppressed growth of both focal plant species more than P. major neighbors. Effects of competition on levels of secondary compounds were more complex. Concentrations of iridoid glycosides were increased by competition in both species at harvest one. By the second harvest, an effect of competition on iridoid glycosides was found only in P. major. Neighbor identity influenced levels of iridoid glycosides in P. lanceolata at harvest one; concentrations were higher in plants grown with P. lanceolata neighbors than in plants grown with P. major neighbors. We also tested whether there was a trade-off between growth (biomass) and defense (levels of iridoid glycosides). Biomass and iridoid glycoside content were significantly correlated only in plants grown with competition and harvested at nine weeks, and this relationship was positive in both species, indicating that there was no trade-off between growth and defense. This study suggests that neighbor identity could play an important role in interspecific interactions, including the interactions of plants with other trophic levels. PMID:16944243

Barton, Kasey E; Bowers, M Deane



Glycosides from the Aerial Parts of Patrinia villosa.  


An investigation of the Korean medicinal plant Patrinia villosa (THUNB.) JUSS. (Valerianaceae) led to the isolation of two new flavonoid glycosides, patrivilosides 1 (1) and 2 (2), a new iridoid glycoside, patrinovalerosidate (3), and two new saponins, patrinovilosides A (4) and B (5), along with six known compounds including three flavonoid glycosides and three iridoid glycosides. The structures of the new compounds were elucidated based on analysis of their one dimensional (1D)- and 2D-NMR spectra along with their mass spectrometric data and the results of acid hydrolysis. PMID:23800854

Lee, Joo Young; Kim, Ju Sun; Kim, Yeong Shik; Kang, Sam Sik



Rehmannia glutinosa: Review of botany, chemistry and pharmacology  

Microsoft Academic Search

Rehmannia glutinosa, a widely used traditional Chinese herb, belongs to the family of Scrophulariaceae, and is taken to nourish Yin and invigorate the kidney in traditional Chinese medicine (TCM) and has a very high medicinal value. In recent decades, a great number of chemical and pharmacological studies have been done on Rehmannia glutinosa. More than 70 compounds including iridoids, saccharides,

Ru-Xue Zhang; Mao-Xing Li; Zheng-Ping Jia



Early ontogenetic patterns in chemical defense in Plantago (Plantaginaceae): genetic variation and trade-offs.  


Predictions based on the plant age and growth-differentiation balance hypotheses of defense were tested in two congeneric species, Plantago lanceolata and P. major, by quantifying iridoid glycosides, defensive chemicals, in seeds and leaves during the first 6 wk of growth. Concentrations decreased from the seed to 2-wk-old seedling stage in P. lanceolata, but increased during this period in P. major. In both species, levels were similar for 2- and 4-wk-old plants, then significantly increased from 4 to 6 wk. Genetic variation in the ontogeny of iridoid glycoside production was significant in both species at the maternal family level and at the population level. To examine whether allocation costs could explain the low production of iridoid glycosides in seedlings, relationships between growth and defense (iridoid glycosides) were characterized. Growth and defense had a positive or null relationship in all age groups, indicating that there was no trade-off in these plants at any age. This study provides some support for the growth-differentiation balance hypothesis, but offers no support for the plant age hypothesis. Measuring how herbivory affects plant fitness at different ontogenetic stages may shed light on these patterns in Plantago and on the evolution of the ontogeny of defense. PMID:21642208

Barton, Kasey E



Divergent diastereoselective synthesis of iridomyrmecin, isoiridomyrmecin, teucrimulactone, and dolicholactone from citronellol.  


The iridoid natural products iridomyrmecin, isoiridomyrmecin, teucriumlactone, and dolicholactone were prepared from citronellol using a divergent diastereoselective approach. Key steps include a highly diastereoselective enamine/enal cycloaddition and the selective reduction of masked aldehyde functionalities by ionic hydrogenation. PMID:23790053

Fischman, Clara J; Adler, Snow; Hofferberth, John E



Constituents of the Stems of Arbutus unedo.  


The dried stems of ARBUTUS UNEDO have been investigated for secondary metabolites. In addition to the previously reported lupeol, ursolic acid, monotropein, unedoside, and stilbericoside, the iridoids geniposide ( 2) and monotropein methyl ester ( 1) have been isolated for the first time from this source. Betulinic acid ( 4) has also been isolated for the first time from this plant. PMID:17269002

Karikas, G A; Euerby, M R; Waigh, R D



Antioxidant properties of different fractions of Vitex negundo Linn  

Microsoft Academic Search

Vitex negundo Linn. (VN), belonging to family Verbenaceae, is an aromatic shrub distributed throughout India. In the ayurvedic system of medicine it is used as a drug of choice to manage pain, inflammation and other related diseases. It contains many polyphenolic compounds, terpenoids, glycosidic iridoids and alkaloids. Since polyphenolic compounds have high antioxidant potential, the antioxidant potency of V. negundo

Om Prakash Tiwari; Yamini B. Tripathi




Technology Transfer Automated Retrieval System (TEKTRAN)

Genipin, a derivative of the iridoid glycoside geniposide in the fruit of Gardenia jasmindides Ellis, is a naturally occurring protein crosslinking agent, which is beginning to replace glutaraldehyde as a fixative for biological tissues. This study was undertaken to evaluate the potential of iridoi...


Potential application for genipin-modified gelatin in leather processing  

Technology Transfer Automated Retrieval System (TEKTRAN)

Genipin is an iridoid compound extracted from gardenia fruits. Because of its low cytotoxicity, genipin can be used to replace both glutaraldehyde and formaldehyde as a crosslinking reagent. In recent years, research into the utilization of genipin for the modification of gelatin, particularly in ...


Identification of a beta-D-glucopyranoside precursor to guaiacol in grape juice following grapevine exposure to smoke.  


The presence of the beta-D-glucopyranoside of guaiacol (glucoside) in juice of grapes following grapevine exposure to smoke was investigated. The glucoside was synthesized as a reference compound and an HPLC-MS/MS method was developed for its detection in juice. The glucoside was found in the juice extracts of grapes exposed to bushfire smoke, as well as grapes experimentally exposed to smoke. Compared to the control (unsmoked) juice sample, the experimentally smoked juice contained a significant amount of the glucoside, indicating glucosylation of guaiacol occurred following grapevine smoke exposure. The reference compound, and the glucoside found in the smoked juice samples were less susceptible to acid treatment but virtually disappeared after enzyme treatment with beta-glucosidase. The susceptibility of the glucoside to enzyme hydrolysis could be one reason for the release of guaiacol from smoke affected grapes during fermentation. PMID:20103155

Hayasaka, Y; Dungey, K A; Baldock, G A; Kennison, K R; Wilkinson, K L



Production of Hesperetin Glycosides by Xanthomonas campestris and Cyclodextrin Glucanotransferase and Their Anti-allergic Activities  

PubMed Central

The production of hesperetin glycosides was investigated using glycosylation with Xanthomonas campestris and cyclodextrin glucanotransferase (CGTase). X. campestris glucosylated hesperetin to its 3'-, 5-, and 7-O-glucosides, and CGTase converted hesperetin glucosides into the corresponding maltosides. The resulting 7-O-glucoside and 7-O-maltoside of hesperetin showed inhibitory effects on IgE antibody production and on O2- generation from rat neutrophils.

Shimoda, Kei; Hamada, Hiroki



Inhibitors from Rhubarb on Lipopolysaccharide-Induced Nitric Oxide Production in Macrophages: Structural Requirements of Stilbenes for the Activity  

Microsoft Academic Search

By bioassay-guided separation, three stilbenes (rhapontigenin, piceatannol, and resveratrol), two stilbene glucoside gallates (rhaponticin 2?-O-gallate and rhaponticin 6?-O-gallate), and a naphthalene glucoside (torachrysone 8-O-?-d-glucopyranoside) with inhibitory activity against nitric oxide (NO) production in lipopolysaccharide-activated macrophages were isolated (IC50=11–69?M). The oxygen functions (–OH, –OCH3) of stilbenes at the benzene ring were essential for the activity. The glucoside moiety reduced the activity,

Tadashi Kageura; Hisashi Matsuda; Toshio Morikawa; Iwao Toguchida; Shoichi Harima; Mamiko Oda; Masayuki Yoshikawa



Insertion and excision of a transposable element governs the red floral phenotype in commercial petunias  

Microsoft Academic Search

Commercial cultivars of Petunia hybrida with red flowers (red petunias) accumulate cyanidin 3-glucoside as a main floral anthocyanin pigment. The conversion of anthocyanidin 3-glucosides to anthocyanidin 3-rutinosides is catalyzed by a UDP-rhamnose: anthocyanidin 3-glucoside-rhamnosyltransferase (RT). In red petunias, the RT gene is known to be disrupted by the insertion of a transposable element (dTph3). We have clo