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1

Iridoid and phenylethanoid glucosides from Veronica lavaudiana.  

PubMed

From an extract of Veronica (sect. Hebe) lavaudiana we have identified mannitol and isolated 11 iridoid glucosides, the carbohydrate ester hebitol II, and four phenylethanoid glycoside esters. Five of the iridoid glycosides are new; of these, lavaudiosides A, B, and C (2a, 3a, and 4) are 1-mannityl esters of 8-epiloganic acid, while 7e and 7f are 6'-O-caffeoyl derivatives of catalpol. The new phenylethanoid glycoside esters, heliosides A, B, and C (8b-d), are 6'-xylosyl derivatives of aragoside. The structures of the new compounds were elucidated mainly by spectroscopic analysis, but also by chemical degradation. We also demonstrated that the structures of the known glycosides globularitol and hebitols I and II should be revised. These compounds are derivatives of mannitol and not glucitol as previously believed. PMID:21568305

Taskova, Rilka M; Kokubun, Tetsuo; Ryan, Ken G; Garnock-Jones, Phil J; Jensen, Søren R

2011-06-24

2

A tetrahydroisoquinoline-monoterpene glucoside and an iridoid glucoside from Alangium kurzii.  

PubMed

From the leaves of Alangium kurzii, a new tetrahydroisoquinoline-monoterpene glucoside, 6-O-methyl-N-deacetylipecosidic acid and a new iridoid glucoside, 10-O-benzoyladoxosidic acid, were isolated along with alangiside, demethylalangiside, 6''-O-beta-D-glucosylhenryoside, uridine and four known flavonoid glycosides. The structures of new glucosides were determined on the basis of spectroscopic and chemical methods. PMID:10726868

Tanahashi, T; Kobayashi, C; Itoh, A; Nagakura, N; Inoue, K; Kuwajima, H; Wu, H X

2000-03-01

3

Benzoxazinoids and iridoid glucosides from four Lamium species.  

PubMed

A new class of compounds for the plant family Lamiaceae, benzoxazinoids, was found in Lamium galeobdolon. From the aerial parts of the species were isolated the new 2-O-beta-D-glucopyranosyl-6-hydroxy-2H-1,4-benzoxazin-3(4H)-one (6-hydroxy blepharin) together with four known benzoxazinoids, DHBOA-Glc, blepharin, DIBOA, DIBOA-Glc, as well as harpagide, 8-O-acetyl-harpagide and salidroside. Eight known iridoid glucosides, 24-epi-pterosterone and verbascoside were isolated from Lamium amplexicaule, L. purpureum and L. garganicum. The iridoids, 5-deoxylamiol and sesamoside, as well as the phytoecdysone, 24-epi-pterosterone, were found for the first time for the genus Lamium. The phytochemical data are discussed from a systematic and evolutionary point of view. PMID:14630008

Alipieva, Kalina I; Taskova, Rilka M; Evstatieva, Ljubka N; Handjieva, Nedjalka V; Popov, Simeon S

2003-12-01

4

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

PubMed

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

2010-02-01

5

Megastigmane and Iridoid glucosides from Avicennia Germinans: Two Isomeric Forms of an Iridoid  

Microsoft Academic Search

The iridoid 2?-coumaroyl mussaenosidic acid, isolated from Avicennia germinans (Avicenniaceae), was analysed by NMR and molecular modeling: two isomeric forms were confirmed. In addition, the known compound 1 (6S, 9R) roseoside was isolated for the first time from this species of Avicennia.

Marie-ThÉRÈSe Fauvel; Maryse Bon; François Crasnier; Claude Moulis; Isabelle Fouraste

1999-01-01

6

[Studies on the constituents of Ligustrum species. XIX. Structures of iridoid glucosides from the leaves of Ligustrum lucidum AIT].  

PubMed

Two new iridoid glucosides, named iso-8-epikingiside and 8-demethyl-7-ketologanin, were isolated together with 8-epikingiside, kingiside, ligustroside, 10-hydroxyligustroside, ligustaloside A and ligustaloside B from the leaves of Ligustrum lucidum AIT. (Oleaceae). The stereochemical structures of these new compounds were elucidated on the basis of spectroscopic evidence. PMID:10376004

Kikuchi, M; Kakuda, R

1999-06-01

7

Coumarin glycosides and iridoid glucosides with neuroprotective effects from Hydrangea paniculata.  

PubMed

Five new coumarin glycosides, umbelliferone 7-O-sophoroside (1), umbelliferone 7-O-?-D-glucopyranosyl(1???3)-?-D-glucopyranoside (2), umbelliferone 7-O-?-D-glucopyranosyl(1???3)-[?-D-apiofuranosyl(1???6)]-?-D-glucopyranoside (3), umbelliferone 7-O-?-D-glucopyranosyl(1???2)-?-D-apiofuranosyl(1???6)-?-D-glucopyranoside (4), and umbelliferone 7-O-?-D-glucopyranosyl(1???5)-?-D-apiofuranosyl(1???6)-?-D-glucopyranoside (5), and two new iridoid glucosides, 7-O-E-isoferuloyl loganic acid (6) and 7-O-?-D-glucopyranosyl loganin (7), together with eight known compounds (8-15) were isolated from the stems of Hydrangea paniculata. Their structures were established by spectroscopic analysis and chemical methods. At 10?µM, compounds 1, 3, 5, 6, 8, 9, and 13 showed neuroprotective effects against serum deprivation-induced PC12 cell damage. PMID:23047248

Shi, Jing; Li, Chuang-Jun; Yang, Jing-Zhi; Yuan, Yu-He; Chen, Nai-Hong; Zhang, Dong-Ming

2012-11-01

8

Protective effect of iridoid glucosides from Boschniakia rossica on acute liver injury induced by carbon tetrachloride in rats.  

PubMed

The protective effect of iridoid glucosides from Boschniakia rossica (BRI) against carbon tetrachloride (CCl4)-induced liver injury was examined. CCl4 at a dose of 0.5 ml/kg of body weight was given intraperitoneally to rats to induce liver damage. The rats were sacrificed 16 h after the CCl4 injection. The CCl4 challenge caused a marked increase in the levels of serum animotransferases, tumor necrosis factor-alpha (TNF-alpha) and of hepatic inducible nitric oxide synthase (iNOS) protein, depleted reduced glutathione (GSH), and propagated lipid peroxidation. The liver antioxidative defense system, including superoxide dismutase (SOD), glutathione peroxidase (GPx) and glutathione reductase (GR), as well as the cytochrome P450 2E1 (CYP2E1) expression were suppressed, however. Preadministration of BRI reversed the significant changes of all liver function parameters induced by CCl4 and restored the liver CYP2E1 content and function. These results demonstrate that BRI produced a protective action on CCl4-induced acute hepatic injury via reduced oxidative stress, suppressed inflammatory response and improved CYP2E1 function in the liver. PMID:19352025

Quan, Jishu; Piao, Long; Xu, Huixian; Li, Tian; Yin, Xuezhe

2009-04-23

9

Iridoids from Lippia graveolens.  

PubMed

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

1998-11-20

10

The inhibitory effect of phenylpropanoid glycosides and iridoid glucosides on free radical production and beta2 integrin expression in human leucocytes.  

PubMed

Rapid production of reactive oxygen species (ROS) and upregulation of beta2 integrin by leucocytes are two important inflammatory responses in human leucocytes. To evaluate whether three phenylpropanoid glycosides (acteoside, crenatoside, and rossicaside B) and two iridoid glucosides (boschnaloside and 8-epideoxyloganic acid) identified from two medicinal plants with similar indications (Orobanche caerulescens and Boschniakia rossica) exhibited anti-inflammatory activity, their effects on N-formyl-methionyl-leucyl-phenylalanine (fMLP) and phorbol-12-myristate-13-acetate (PMA)-activated peripheral human neutrophils (PMNs) and mononuclear cells were examined. Pretreatment with 1-50 microM phenylpropanoid glycoside concentration-dependently diminished PMA- and fMLP-induced ROS production with IC50 values of approximately 6.8-23.9 and 3.0-8.8 muM, respectively. Iridoid glucoside was less effective than phenylpropanoid glycoside with an IC50 value of approximately 8.9-28.4 microM in PMA-activated PMNs and 19.1-21.1 microM in fMLP-activated mononuclear cells. Phenylpropanoid glycosides also effectively inhibited NADPH oxidase (NOX) and displayed potent free radical-scavenging activity, but did not interfere with pan-protein kinase C (PKC) activity. Furthermore, all compounds, except rossicaside B, significantly inhibited PMA- and fMLP-induced Mac-1 (a beta2 integrin) upregulation at 50 microM but not that of fMLP-induced intracellular calcium mobilization. These drugs had no significant cytotoxicity as compared with the vehicle control. Our data suggested that inhibition of ROS production, possibly through modulation of NOX activity and/or the radical scavenging effect, and beta2 integrin expression in leucocytes indicated that these compounds had the potential to serve as anti-inflammatory agents during oxidative stress. PMID:16393473

Lin, Lie-Chwen; Wang, Yea-Hwey; Hou, Yu-Chang; Chang, Shiou; Liou, Kuo-Tong; Chou, Yueh-Ching; Wang, Wen-Yen; Shen, Yuh-Chiang

2006-01-01

11

A new iridoid glycoside and NO production inhibitory activity of compounds isolated from Russelia equisetiformis.  

PubMed

From the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Russelia equisetiformis, one new iridoid glucoside was isolated along with 24 known compounds, comprising iridoids and iridoid glucosides, phenyl propane glucosides, phenyl ethanoids, lignan glucosides, and flavonoid glucosides. The structure of the new compound was elucidated to be 10-O-cinnamoyl sinuatol. Of the 25 compounds isolated, rehmaglutin B exhibited moderate inhibitory activity toward NO production, which was not associated with cytotoxicity. PMID:21822607

Ochi, Madoka; Matsunami, Katsuyoshi; Otsuka, Hideaki; Takeda, Yoshio

2012-01-01

12

Iridoid glycosides from Alonsoa meridionalis.  

PubMed

A new iridoid glucoside has been isolated from the Chilean native Alonsoa meridionalis (L.f.) Kuntze. Its structure has been assigned as 6'-O-?-d-glucopyranosyl-8-O-acetylharpagide (1) by using spectroscopic methods. Harpagoside (2), laterioside (3) and verbascoside (4) were also identified. PMID:24735384

Tomassini, Lamberto; Serafini, Mauro; Foddai, Sebastiano; Ventrone, Antonio; Nicoletti, Marcello

2014-08-01

13

8-Epi-iridodial glucoside from Boschniakia rossica.  

PubMed

Boschnaside, 8-epi-iridodial glucoside a new iridoid glucoside was isolated from Boschniakia rossica Hult., and its absolute structure was determined by chemical correlation of boschnaloside tetraacetate with boschnaside tetraacetate. PMID:17396939

Murai, F; Tagawa, M

1982-09-01

14

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

PubMed

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

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

2007-03-01

15

Anti-inflammatory activity of iridoids and verbascoside isolated from Castilleja tenuiflora.  

PubMed

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

2013-01-01

16

Iridoid compounds from Boschniakia rossica.  

PubMed

Four iridoid compounds were isolated from methanol extract of Boschniakia rossica by repeated column chromatography. Their structures were determined as boschnaloside (1), boschnarol (2), bosnarol methylether (3), and 7-deoxy 8-epiloganic acid (4), respectively. Compound 2, 3, and 4 were isolated for the first time from this plant. PMID:10071965

Yin, Z Z; Kim, H S; Kim, Y H; Lee, J J

1999-02-01

17

Tetrahydroisoquinoline-monoterpene and iridoid glycosides from Alangium lamarckii.  

PubMed

From the water soluble fraction of the dried fruits of Alangium lamrckii, four tetrahydroisoquinoline-monoterpene glycosides, 6-O-methyl-N-deacetylisoipecosidic acid, 7-O-methyl-N-deacetylisoipecosidic acid, 6,7-di-O-methyl-N-deacetylisoipecosidic acid and 6"-O-alpha-D-glucopyranosyl-6-O-methyl-N-deacetylisoipecosidic acid, and an iridoid glycoside, 6'-O-alpha-D-glucopyranosylloganic acid, were isolated, together with six known compounds. The structures of the previously unknown compounds were determined by spectroscopic and chemical means. The significance of these glucosides in the biogenesis of Alangium alkaloids is discussed; 6-O-methyl-N-deacetylisoipecosidic acid was also chemically converted into 10-O-demethylprotoemetine and dihydroisoalangine. PMID:11281140

Itoh, A; Tanahashi, T; Tabata, M; Shikata, M; Kakite, M; Nagai, M; Nagakura, N

2001-03-01

18

Morinda citrifolia and iridoid based formulations  

US Patent & Trademark Office Database

Embodiments of the invention relate to fortified food and dietary supplement products which may be administered to produce desirable physiological improvement. In particular, embodiments of the invention relates to the administration of products enhanced with Morinda citrifolia and iridoids.

2014-07-29

19

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

PubMed Central

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

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

2013-01-01

20

Anti-Inflammatory Iridoids of Botanical Origin  

PubMed Central

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

Viljoen, A; Mncwangi, N; Vermaak, I

2012-01-01

21

Anti-inflammatory iridoids of botanical origin.  

PubMed

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

2012-01-01

22

A novel iridoid from Boschniakia rossica.  

PubMed

A novel iridoid, (4R)-4-hydroxymethylboschnialactone (1), has been isolated from Boschniakia rossica, together with three previously known compounds, (24S)-3beta-hydroxy-24-ethylcholest-5-en-7-one (2), (24R)-3beta-hydroxy-24-ethylcholest-5-en-7-one (3) and methyl p-coumarate, using column chromatography. The structures of compounds were elucidated by spectroscopic methods. PMID:14758022

Yim, Soon-Ho; Kim, Hyun Jung; Liu, Yong Zhen; Lee, Ik-Soo

2004-02-01

23

Morinda citrifolia juice formulations comprising iridoids  

US Patent & Trademark Office Database

Fortified food and dietary supplement products may be administered to produce desirable physiological improvement. In particular, embodiments of the invention relates to the administration of products enhanced with plant products and iridoids. A study was performed to evaluate the iridoid content, as well as the in vitro and in vivo bioactivities, of a beverage containing noni fruit, Cornelian cherries, and olive leaf extract. The major iridoids present were identified as asperulosidic acid, deacetylasperulosidic acid, oleuropein, morroniside, loganic acid, and loganin In the 2,2-Diphenylpicrylhydrazyl (DPPH) radical scavenging assay, remarkably high in vitro antioxidant activity was observed, with an IC.sub.50 of 3.8 .mu.L/mL. In vivo bioactivities were evaluated in type 2 diabetic Sprague Dawley rats. In a dose-dependent manner, the composition reduced abnormal weight gain, blood glucose levels, and serum advanced glycation end products (AGEs), as well as improved immunity via increased T cell counts and CD4+/CD8.sup.+ ratios.

2014-03-25

24

Andrographidine G, a new flavone glucoside from Andrographis paniculata.  

PubMed

A new flavone glucoside, andrographidine G (1), was isolated from Andrographis paniculata together with 13 known compounds, including flavonoids, diterpenoids, and iridoids. The structure of 1 was established by spectroscopic and spectrometric techniques, including HR-ESI-TOF-MS, 1D and 2D NMR, and chemical methods. The known compounds were identified as andrographidine A (2), (2R)-5-hydroxy-7,8-dimethoxyflavanone-5-O-beta-D-glucopyranoside (3), acanthoside B (4), neoandrographiside (5), andropanoside (6), andrographiside (7), andrographolide (8), 14-deoxy-11,12-didehydroandrographiside (9), 14-deoxy-11,12-didehydroandrographolide (10), procumbide (11), procumboside (12), 6-epi-8-O-acetylharpagide (13), and curvifloruside F (14). PMID:23678804

Hapuarachchi, Swarna D; Ali, Zulfiqar; Abe, Naohito; Sugandhika, Suresh T; Sandun, Senerath T P; Khan, Ikhlas A

2013-03-01

25

Chemotaxonomic aspects of iridoids occurring in Plantago subg. Psyllium ( Plantaginaceae )  

Microsoft Academic Search

Within the genusPlantago, subg.Psyllium is characterized by the accumulation of the iridoids plantarenaloside and bartsioside. The latter compound was identified as constituent ofP. sempervirens for the first time. The structures of iridoids were determined by UV, IR,13C-NMR and1H-NMR. Both compounds are of chemotaxonomic value, as they are typical only of subg.Psyllium withinPlantago. The distribution of plantarenaloside within subg.Psyllium suggests the

Emilia Andrzejewska-Golec; Silke Ofterdinger-Daegel; Ihsan Calis; Lucjan ?wiatek

1993-01-01

26

New iridoid glycoside from Gratiola officinalis.  

PubMed

A new iridoid glycoside, 1?,6?-di-O-trans-cinnamoyl-9-O-?-D-glucopyranosyl-3-iridene-5?-ol (1), along with four known compounds loliolide (2), ?-sitosterol-3-O-?-D-glucopyranoside (3), betulinic acid (4), and ?-amyrin (5), was isolated from the aerial parts of Gratiola officinalis L. The structure of the new compound was deduced on the basis of 1D ¹H and ¹³C NMR and 2D HMQC, HMBC, and COSY experiments, and mass spectrometric techniques (EI-MS and HR-EI-MS). The relative configuration of 1 was assigned by comparative analysis of the NMR spectral data with known analogs, together with NOESY experiments. PMID:23134347

Ali, Liaqat; Rizvi, Tania Shamim; Ahmad, Manzoor; Shaheen, Farzana

2012-01-01

27

The seco-iridoid pathway from Catharanthus roseus.  

PubMed

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

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

2014-01-01

28

The seco-iridoid pathway from Catharanthus roseus  

PubMed Central

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

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

2014-01-01

29

Development and validation of high liquid performance chromatography-tandem mass spectrometry method for simultaneous determination of geniposidic acid and aucubin in rat plasma for pharmacokinetic study after oral administration of Du-zhong tea extract.  

PubMed

A specific and sensitive high performance liquid chromatography coupled with tandem mass spectrometric (HPLC-MS/MS) method was developed and validated for the simultaneous determination of geniposidic acid and aucubin in rat plasma after oral administration of Du-zhong tea extract. The plasma samples were pretreated by protein precipitation with methanol and the chromatographic separation was performed on a Hypersil C18 column (4.6mm×250mm, 5?m), using a gradient mobile phase system of water-methanol (0.05% formic acid). The detection was accomplished by multiple-reaction monitoring (MRM) scanning via electrospray ionization source operating in the negative ionization mode. The linear range was 1-1000ng/mL for geniposidic acid and 0.2-200ng/mL for aucubin, respectively. The accuracy (relative error, R.E.%) were between -5.40 and 5.00%, while the intra-day and inter-day precisions were less than 7.95 and 7.87% for the two analytes, respectively. The method was fully validated for the sensitivity, selectivity, recovery, matrix effect and stability. Then this method was successfully applied to the pharmacokinetic study of geniposidic acid and aucubin after oral administration of Du-zhong tea extract to rats and the results indicated that this HPLC-MS/MS assay is a valuable method for the pharmacokinetic study of geniposidic acid and aucubin in rat plasma. PMID:24929551

Zhang, Lin; Ma, Yu-Liang; Liu, Yang; Zu, Yuan-Gang

2014-07-15

30

Phenolic glucosides from Alangium plantanifolium.  

PubMed

A novel phenolic glucoside alangitanifoliside A (1) together with two known phenolic glucosides 4',6'-O-(S)-hexahydroxydiphenylsalicin (2) and salicin (3), and gallic acid were isolated from stem barks of Alangium plantanifolium. Their structures were determined by spectroscopic and chemical methods. The structure of 1 was elucidated to be 1-O-[2-(1-hydroxy-6-oxocyclohex-2-ene-1-carboxymethyl)-phenyl]-4,6-O-[(S)-,4,4',5,5' 6,6'-hexahydroxydiphenoyl]-beta-D-glucopyranose. PMID:11991192

Shi, Jian-Gong; Hu, Wen-Yan; Yang, Yong-Chun; Zhou, Guang-Xiong

2002-03-01

31

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

Microsoft Academic Search

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,

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

2008-01-01

32

Lignan, phenolic and iridoid glycosides from Stereospermum cylindricum.  

PubMed

A lignan glycoside [(+)-cycloolivil 4'-O-beta-d-glucopyranoside], a phenolic glycoside [3,4-dimethoxyphenyl 1-O-beta-d-xylopyranosyl-(1-->6)-beta-d-glucopyranoside] and a iridoid glycoside (stereospermoside) were isolated from the leaves and branches of Stereospermum cylindricum, together with (+)-cycloolivil, (+)-cycloolivil 6-O-beta-d-glucopyranoside, (-)-olivil, (-)-olivil 4-O-beta-d-glucopyranoside, (-)-olivil 4'-O-beta-d-glucopyranoside, vanilloloside, decaffeoyl-verbascoside, isoverbascoside, 3,4,5-trimethoxyphenyl 1-O-beta-d-xylopyranosyl-(1-->6)-beta-d-glucopyranoside, ajugol, verminoside, and specioside. The structure elucidations were based on spectroscopic evidence. PMID:16310232

Kanchanapoom, Tripetch; Noiarsa, Pawadee; Otsuka, Hideaki; Ruchirawat, Somsak

2006-03-01

33

An alternative route to cyclic terpenes by reductive cyclization in iridoid biosynthesis.  

PubMed

The iridoids comprise a large family of distinctive bicyclic monoterpenes that possess a wide range of pharmacological activities, including anticancer, anti-inflammatory, antifungal and antibacterial activities. Additionally, certain iridoids are used as sex pheromones in agriculturally important species of aphids, a fact that has underpinned innovative and integrated pest management strategies. To harness the biotechnological potential of this natural product class, the enzymes involved in the biosynthetic pathway must be elucidated. Here we report the discovery of iridoid synthase, a plant-derived enzyme that generates the iridoid ring scaffold, as evidenced by biochemical assays, gene silencing, co-expression analysis and localization studies. In contrast to all known monoterpene cyclases, which use geranyl diphosphate as substrate and invoke a cationic intermediate, iridoid synthase uses the linear monoterpene 10-oxogeranial as substrate and probably couples an initial NAD(P)H-dependent reduction step with a subsequent cyclization step via a Diels-Alder cycloaddition or a Michael addition. Our results illustrate how a short-chain reductase was recruited as cyclase for the production of iridoids in medicinal plants. Furthermore, we highlight the prospects of using unrelated reductases to generate artificial cyclic scaffolds. Beyond the recognition of an alternative biochemical mechanism for the biosynthesis of cyclic terpenes, we anticipate that our work will enable the large-scale heterologous production of iridoids in plants and microorganisms for agricultural and pharmaceutical applications. PMID:23172143

Geu-Flores, Fernando; Sherden, Nathaniel H; Courdavault, Vincent; Burlat, Vincent; Glenn, Weslee S; Wu, Cen; Nims, Ezekiel; Cui, Yuehua; O'Connor, Sarah E

2012-12-01

34

Cyclohexylethanoids and related glucosides from Millingtonia hortensis  

Microsoft Academic Search

From the dried flowers of Millingtonia hortensis, nine cyclohexylethanoids, including four glucosides were isolated along with 12 related known compounds. Biogenetic relationships between these compounds are discussed.

Takeshi Hase; Yuka Kawamoto; Kazuhiro Ohtani; Ryoji Kasai; Kazuo Yamasaki; Chayan Picheansoonthon

1995-01-01

35

?-Radiolysis of aqueous solution of glucosides  

NASA Astrophysics Data System (ADS)

In this paper, three types of aqueous solution of glucoside, baicalin (I), 1, 8-dihydroxyanthraquinone-?-D-glucoside (II) and glycyrrhizin (III), have been investigated. The yields of decomposition of glucosides are determined. Their G values decrease as doses increase. Some radiolysis products are identified. The influences of different radical scavengers such as, O 2, N 2O, KCNS and isopropanol, are observed. Radiolysis is mainly caused by OH radical. Radiation induced hydrolysis of glucosidic linkage is not the main process, the proportions of dissociated aglycon to total radiolysis products are less than 10%.

Rongyao, Yuan; Jilan, Wu

36

HCV-NS3/4A protease inhibitory iridoid glucosides and dimeric foliamenthoic acid derivatives from Anarrhinum orientale.  

PubMed

Four new compounds were isolated from the methanol extract of the aerial parts of Anarrhinum orientale: 6'-O-cinnamoylmussaenosidic acid (1), 6'-O-cinnamoyl-8-O-(6'''-O-cinnamoylglucopyranosyl)mussaenosidic acid (2), (2E,6E)-8-{[(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoyl]oxy}-2,6-dimethylocta-2,6-dienoic acid (3), and (2E,6E)-8-{[(2E,6E)-8-acetoxy-2,6-dimethylocta-2,6-dienoyl]oxy}-2,6-dimethylocta-2,6-dienoic acid (4). The known 8-O-cinnamoylmussaenosidic acid (5) was also identified. All five compounds were tested for inhibition of the hepatitis C virus (HCV) protease. Compounds 1 and 5 exhibited moderate activity, while 2 and 3 showed weak effects. No inhibitory activity on the human serine protease was observed for any of these compounds, which may infer the selectivity toward the viral protease. A computational docking study of the isolated compounds against HCV protease was used to formulate a hypothetical mechanism for the inhibitory activity of the active compounds on the enzymes tested. PMID:21506603

Salah El Dine, Riham; Abdel Monem, Azza R; El-Halawany, Ali M; Hattori, Masao; Abdel-Sattar, Essam

2011-05-27

37

Immunochemical approach for zearalenone-4-glucoside determination.  

PubMed

Zearalenone-4-?-D-glucopyranoside (zearalenone-4-glucoside) detection techniques, based on a combination of acidic or enzymatic hydrolysis of the masked mycotoxin to the parent form (i.e. zearalenone), and immunochemical determination of zearalenone-4-glucoside as a difference between the zearalenone concentration after and before cleavage of the glycosidic bond were developed. The limit of detection for zearalenone-4-glucoside, achieved for the enzyme linked immunosorbent assay, was 3 ?g kg(-1); the cut-off level for the sum of zearalenone and zearalenone-4-glucoside determination by a qualitative gel-based immunoassay was 50 ?g kg(-1). Trifluoromethanesulfonic acid was checked for acidic hydrolysis and resulted in approximately 70% of glycosidic bond cleavage in optimal conditions. Seven different glycoside hydrolases were tested during the design of the enzymatic hydrolysis technique. Enzymatic hydrolysis combined with enzyme linked immunosorbent assay and gel-based immunoassay determinations was applied for the determination of zearalenone-4-glucoside or the sum of zearalenone and zearalenone-4-glucoside in cereal samples. The chosen enzyme (glucosidase from Aspergillus niger) allowed to cleave 102% of zearalenone-4-glucoside in standard solutions and 85% in cereal samples. Liquid chromatography coupled to tandem mass spectrometry was used as confirmatory method. As a result, good correlations between immunochemical techniques and the chromatographic data were obtained. The developed technique is suitable for simultaneous immunochemical determination of zearalenone and its masked form, zearalenone-4-glucoside. PMID:23598147

Beloglazova, N V; De Boevre, M; Goryacheva, I Yu; Werbrouck, S; Guo, Y; De Saeger, S

2013-03-15

38

Enzymatic synthesis of novel phloretin glucosides.  

PubMed

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

2013-06-01

39

Coumaroyl iridoids and a depside from cranberry (Vaccinium macrocarpon).  

PubMed

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

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

2007-02-01

40

Two flavone 2?-glucosides from Scutellaria baicalensis  

Microsoft Academic Search

Two new flavone glucosides, 5,2?,6?-trihydroxy-6,7,8-trimethoxyflavone 2?-O-glucoside and 5,2?,6?-trihydroxy-6,7-dimethoxyflavone 2?-O-glucoside were isolated from the aqueous methanol extract of the roots of Scutellaria baicalensis. From the extract, seven phenolics, 5,7,2?,6?-terahydroxyflavone, 5,7,2?,5?-tetrahydroxy-8,6?-dimethoxyflavone, skullcapflavone II, baicalin, baicalin methyl ester, wogonin 7-glucuronide and 3,5,7,2?,6?-pentahydroxyflavanone were also isolated.

Kanji Ishimaru; Kazutaka Nishikawa; Toshio Omoto; Iwao Asai; Kunitoshi Yoshihira; Koichiro Shimomura

1995-01-01

41

Comparison of pharmacokinetic behavior of two iridoid glycosides in rat plasma after oral administration of crude Cornus officinals and its jiuzhipin by high performance liquid chromatography triple quadrupole mass spectrometry combined with multiple reactions monitoring mode  

PubMed Central

Objective: The present study examined the pharmacokinetic profiles of two iridoid glycosides named morroniside and loganin in rat plasma after oral administration of crude and processed Cornus officinals. Materials and Methods: A rapid, selective and specific high-performance liquid chromatography/electrospray ionization tandem mass spectrometry with multiple reactions monitoring mode was developed to simultaneously investigate the pharmacokinetic profiles of morroniside and loganin in rat plasma after oral administration of crude C. officinals and its jiuzhipin. Results: The morroniside and loganin in crude and processed C. officinals could be simultaneously determined within 7.4 min. Linear calibration curves were obtained over the concentration ranges of 45.45-4800 ng/mL for all the analytes. The intra-and inter-day precisions relative standard deviation was lesser than 2.84% and 4.12%, respectively. Conclusion: The pharmacokinetic parameters of two iridoid glucosides were also compared systematically between crude and processed C. officinals. This paper provides the theoretical proofs for further explaining the processing mechanism of Traditional Chinese Medicines.

Chen, Xiaocheng; Cao, Gang; Jiang, Jianping

2014-01-01

42

A new chromene glucoside from Ageratum conyzoides.  

PubMed

The aerial parts of AGERATUM CONYZOIDES afforded a new chromene glucoside, 2,2-dimethylchromene 7- O-beta-glucopyranoside, together with a known benzofuran derivative. The structures were elucidated by high-field NMR spectroscopy. PMID:17260251

Ahmed, A A; Abou-Douh, A M; Mohamed, A el-H; Hassan, M E; Karchesy, J

1999-03-01

43

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

PubMed

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

2012-10-01

44

Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina.  

PubMed

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

2009-02-01

45

Iridoid and phenylpropanoid glycosides from Scrophularia ningpoensis Hemsl. and their ?-Glucosidase inhibitory activities.  

PubMed

A new phenylpropanoid glycoside, designated Scrophuside (1) and two new iridoid glycosides, respectively named Ningposide I (2) and Ningposide II (3), along with twelve known (4-15) iridoid and phenylpropanoid glycosides were obtained from the roots of Scrophularia ningpoensis Hemsl. by various chromatographic techniques and their structures were established through chemical methods and spectroscopic analyses. Most of the obtained compounds have been screened for ?-Glucosidase inhibitory activity, in which compounds 4, 5, 7, 11, 12, 13, and 14 show significant activity. PMID:24321577

Hua, Jing; Qi, Jin; Yu, Bo-Yang

2014-03-01

46

Phenylethanoid and iridoid glycosides in the New Zealand snow hebes (Veronica, Plantaginaceae).  

PubMed

Snow hebes are the alpine cushion-forming plants of New Zealand Veronica, formerly classified as Chionohebe. The chemical compositions of Veronica pulvinaris and Veronica thomsonii were studied and 33 water-soluble compounds were isolated. The structures of 14 previously unknown esters of phenylethanoid glycosides were elucidated by spectroscopic analyses. Further, eight known phenylethanoids, nine iridoids, 6'-feruloyl-sucrose and mannitol are also reported. It was found that the iridoid profile of the snow hebes was different from the other species of Veronica in New Zealand but similar to the alpine Northern Hemisphere representatives of the genus. PMID:20460800

Taskova, Rilka M; Kokubun, Tetsuo; Ryan, Ken G; Garnock-Jones, Phil John; Jensen, Soren Rosendal

2010-05-01

47

Protection against Amanita phalloides by the iridoid glycoside mixture of Picrorhiza kurroa (kutkin)  

Microsoft Academic Search

Survival of mice after lethal doses of a lyophilizate fromAmanita phalloides (‘death cap’) was markedly increased by pretreatment with single doses of kutkin, a mixture of iridoid glycosides picroside I and kutkoside isolated from the roots ofPicrorhiza kurroa. The protective effect of kutkin was comparable to that of silibinin. The curative efficacy of kutkin appeared to be slightly superior.

G. L. Floersheim; A. Bieri; R. Koenig; A. Pletscher

1990-01-01

48

Protection against Amanita phalloides by the iridoid glycoside mixture of Picrorhiza kurroa (kutkin).  

PubMed

Survival of mice after lethal doses of lyophilizate from Amanita phalloides ('death cap') was markedly increased by pretreatment with single doses of kutkin, a mixture of iridoid glycosides picroside I and kutkoside isolated from the roots of Picrorhiza kurroa. The protective effect of kutkin was comparable to that of silibinin. The curative efficacy of kutkin appeared to be slightly superior. PMID:2339676

Floersheim, G L; Bieri, A; Koenig, R; Pletscher, A

1990-03-01

49

Making iridoids/secoiridoids and monoterpenoid indole alkaloids: progress on pathway elucidation.  

PubMed

Members of the Acanthaceae, Apocynaceae, Bignoniaceae, Caprifoliaceae, Gentianaceae, Labiatae, Lamiaceae, Loasaceae, Loganiaceae, Oleaceae, Plantaginaceae, Rubiaceae, Saxifragaceae, Scrophulariaceae, Valerianaceae, and Verbenaceae plant families are well known to accumulate thousands of bioactive iridoids/secoiridoids while the Apocynaceae, Loganiaceae and Rubiaceae families also accumulate thousands of bioactive monoterpenoid indole alkaloids (MIAs), mostly derived from the secologanin and tryptamine precursors. Several large-scale RNA-sequencing projects have greatly advanced the tools available for identifying candidate genes whose gene products are involved in the biosynthesis of iridoids/MIAs. This has led to the rapid comparative bioinformatics guided elucidation of several key remaining steps in secologanin biosynthesis as well as other steps in MIA biosynthesis. The availability of these tools will permit broad scale biochemical and molecular description of the reactions required for making thousands of iridoid/MIAs. This information will advance our understanding of the evolutionary and ecological roles played by these metabolites in Nature and the genes will be used for biotechnological production of useful iridoids/MIAs. PMID:24709280

De Luca, Vincenzo; Salim, Vonny; Thamm, Antje; Masada, Sayaka Atsumi; Yu, Fang

2014-06-01

50

Regioselective enzymatic acetylation of the aglycone moiety of a secoiridoid glucoside. Two new secoiridoid glucoside acetates.  

PubMed

Candida antarctica lipase (CAL) catalyses the regioselective acetylation of the 10-hydroxyl group of 10-hydroxyoleoside dimethyl ester, a secoiridoid glucoside, using THF as a solvent and ethyl acetate or vinyl acetate as acetyl group suppliers. Two acetyl derivatives at 3'- and 6'-sites of the glucosidic ring of 10-acetoxyoleoside dimethylester, not previously described, were obtained by acetylation in the same conditions. PMID:15340202

Pérez, José Andrés; Boluda, Carlos; López, Hermelo; Trujillo, Juan Manvel; Hernández, José Manuel

2004-09-01

51

Cycloartane triterpene glucosides from Corchorus depressus  

Microsoft Academic Search

Depressoside A and B, two new cycloartane triterpene glucosides were isolated from Corchorus depressus. The structures of depressoside A and B were elucidated as 9,19-cyclolanosta-22(R),25-epoxy-3?,16?,24(S)-triol-3-O-?-d-glucopyranoside and 9,19-cyclolanosta-22(R),25-epoxy-24(S)-acetoxy-3?,16?-diol-3-O-?-d-glucopyranoside respectively on the basis of 1D and 2D spectroscopic studies and chemical analysis.

Viqar Uddin Ahmad; Akbar Ali; Zulfiqar Ali; Fehmida T. Baqai; Farah Naz Zafar

1998-01-01

52

Metabolically Active Glucosides in Oleaceae Seeds  

PubMed Central

The seeds of six woody species of Oleaceae representing three genera, contain high concentrations of water-soluble glucosides, with major absorption maxima below 240 nanometers. In Fraxinus americana seeds three of these compounds, designated GL-3, GL-5, and GL-6, account for almost 10% of the dry weight. They are found in the endosperm and embryo but not in the pericarp. While the level of GL-5 is not particularly influenced by the physiological state of the embryo, that of GL-3 and GL-6 decreases as a result of germination and growth during a 10-day period. As the concentrations of GL-3 and GL-6 decrease, new ultraviolet-absorbing compounds are formed. The changes in the concentration of the ultraviolet-absorbing glucosides during cold temperature after-ripening, prior to germination, are small. When germination of dormant embryos is induced with gibberellic acid, the concentrations of GL-3 and GL-6 decrease in a manner similar to that observed with nondormant embryos. In the presence of abscisic acid no losses of GL-3 and GL-6 were observed. It is suggested that GL-3 and GL-6 fulfill some definite functions in the germination and growth of F. americana embryos, and that gibberellic acid and abscisic acid can exert a regulatory effect on the metabolism of these glucosides. Images

Sondheimer, E.; Blank, G. E.; Galson, Eva C.; Sheets, F. M.

1970-01-01

53

Cornel Iridoid Glycoside Inhibits Inflammation and Apoptosis in Brains of Rats with Focal Cerebral Ischemia  

Microsoft Academic Search

The capacity of cornel iridoid glycoside (CIG) to suppress the manifestations of ischemic stroke was investigated. CIG was\\u000a administered to rats by the intragastric route once daily for 7 days. Focal cerebral ischemia was induced by 2 h of middle\\u000a cerebral artery occlusion followed by 24 h of reperfusion. In non-treated rats large infarct areas were observed within 24 h\\u000a of reperfusion. Examination of

Bai-liu YaChun-yang; Chun-yang Li; Lan Zhang; Wen Wang; Lin Li

2010-01-01

54

Monoterpene glucosides from Ziziphora clinopodioides (Labiatae).  

PubMed

Three new monoterpene glucosides, ziziphoroside A (1), B (2), and C (3), together with fifteen known compounds were isolated from the whole herb of Z. clinopodioides. The structures of new compounds were determined primarily from 1D-, 2D-NMR and circular dichroism (CD) spectroscopic analyses. The isolated compounds were evaluated for their inhibitory activity against nitric oxide (NO) production by lipopolysaccharide (LPS) and interferon (IFN)-? activated macrophages, RAW 264.7. Shizonepetoside A (8) and flavones (11, 12, 13) showed potent inhibitory activity against NO production. PMID:22382423

Furukawa, Megumi; Oikawa, Naoki; Imohata, Toru; Makino, Mitsuko; Ogawa, Shoujiro; Iida, Takashi; Fujimoto, Yasuo; Kitanaka, Susumu

2012-01-01

55

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

PubMed

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

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

2014-05-01

56

Geniposide and its iridoid analogs exhibit antinociception by acting at the spinal GLP-1 receptors.  

PubMed

We recently discovered that the activation of the spinal glucagon-like peptide-1 receptors (GLP-1Rs) by the peptidic agonist exenatide produced antinociception in chronic pain. We suggested that the spinal GLP-1Rs are a potential target molecule for the management of chronic pain. This study evaluated the antinociceptive activities of geniposide, a presumed small molecule GLP-1R agonist. Geniposide produced concentration-dependent, complete protection against hydrogen peroxide-induced oxidative damage in PC12 and HEK293 cells expressing rat and human GLP-1Rs, but not in HEK293T cells that do not express GLP-1Rs. The orthosteric GLP-1R antagonist exendin(9-39) right-shifted the concentration-response curve of geniposide without changing the maximal protection, with identical pA2 values in both cell lines. Subcutaneous and oral geniposide dose-dependently blocked the formalin-induced tonic response but not the acute flinching response. Subcutaneous and oral geniposide had maximum inhibition of 72% and 68%, and ED50s of 13.1 and 52.7 mg/kg, respectively. Seven days of multidaily subcutaneous geniposide and exenatide injections did not induce antinociceptive tolerance. Intrathecal geniposide induced dose-dependent antinociception, which was completely prevented by spinal exendin(9-39), siRNA/GLP-1R and cyclic AMP/PKA pathway inhibitors. The geniposide iridoid analogs geniposidic acid, genipin methyl ether, 1,10-anhydrogenipin, loganin and catalpol effectively inhibited hydrogen peroxide-induced oxidative damage and formalin pain in an exendin(9-39)-reversible manner. Our results suggest that geniposide and its iridoid analogs produce antinociception during persistent pain by activating the spinal GLP-1Rs and that the iridoids represented by geniposide are orthosteric agonists of GLP-1Rs that function similarly in humans and rats and presumably act at the same binding site as exendin(9-39). PMID:24747181

Gong, Nian; Fan, Hui; Ma, Ai-Niu; Xiao, Qi; Wang, Yong-Xiang

2014-09-01

57

Zearalenone-16-O-glucoside: a new masked mycotoxin.  

PubMed

This paper reports the identification of a barley UDP-glucosyltransferase, HvUGT14077, which is able to convert the estrogenic Fusarium mycotoxin zearalenone into a near-equimolar mixture of the known masked mycotoxin zearalenone-14-O-?-glucoside and a new glucose conjugate, zearalenone-16-O-?-glucoside. Biocatalytical production using engineered yeast expressing the HvUGT14077 gene allowed structural elucidation of this compound. The purified zearalenone-16-O-?-glucoside was used as an analytical calibrant in zearalenone metabolization experiments. This study confirmed the formation of this new masked mycotoxin in barley seedlings as well as in wheat and Brachypodium distachyon cell suspension cultures. In barley roots, up to 18-fold higher levels of zearalenone-16-O-?-glucoside compared to the known zearalenone-14-O-?-glucoside were found. Incubation of zearalenone-16-O-?-glucoside with human fecal slurry showed that this conjugate can also be hydrolyzed rapidly by intestinal bacteria, converting the glucoside back to the parental mycotoxin. Consequently, it should be considered as an additional masked form of zearalenone with potential relevance for food safety. PMID:24386883

Kovalsky Paris, Maria Paula; Schweiger, Wolfgang; Hametner, Christian; Stückler, Romana; Muehlbauer, Gary J; Varga, Elisabeth; Krska, Rudolf; Berthiller, Franz; Adam, Gerhard

2014-02-01

58

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

PubMed

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

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

2014-07-01

59

Synthesis and SAR of Thiazolylmethylphenyl Glucoside as Novel C-Aryl Glucoside SGLT2 Inhibitors  

PubMed Central

Novel C-aryl glucoside SGLT2 inhibitors containing the thiazole motif were designed and synthesized for biological evaluation. Among the compounds assayed, thiazole containing furanyl moiety 14v and thiophenyl moiety 14y demonstrated the best in vitro inhibitory activity against SGLT2 in this series to date (IC50 = 0.720 nM for 14v and IC50 = 0.772 nM for 14y). Both of these compounds have been further evaluated on a urinary glucose excretion test and the urine volumes excreted.

2010-01-01

60

Preparative isolation and purification of iridoid glycosides from Fructus Corni by high-speed countercurrent chromatography  

PubMed Central

Using a two-phase solvent system composed of dichloromethane–methanol–n-butanol–water–acetic acid (5:5:3:4:0.1, v/v/v/v/v), high-speed countercurrent chromatography was successfully performed for isolation and purification of three iridoid glycosides from Fructus Corni for the first time. From 100 mg of a crude extract of Fructus Corni 7.9 mg of sweroside, 13.1 mg of morroniside, and 10.2 mg of loganin were obtained in less than 3 h with purities of 92.3, 96.3 and 94.2%, respectively. These target compounds were identified by ESI-MS, 1H NMR and 13C NMR.

Liang, Jinru; He, Jiao; Zhu, Sha; Zhao, Wenna; Zhang, Yongmin; Ito, Yoichiro; Sun, Wenji

2012-01-01

61

Nicotinamide metabolism in ferns: formation of nicotinic acid glucoside.  

PubMed

The metabolic fate of [carbonyl-(14)C]nicotinamide was investigated in 9 fern species, Psilotum nudum, Angiopteris evecta, Lygodium japonicum, Acrostichum aureum, Asplenium antiquum, Diplazium subsinuatum, Thelypteris acuminate, Blechnum orientale and Crytomium fortune. All fern species produce a large quantity of nicotinic acid glucoside from [(14)C]nicotinamide, but trigonelline formation is very low. Increases in the release of (14)CO(2) with incubation time was accompanied by decreases in [carboxyl-(14)C]nicotinic acid glucoside. There was slight stimulation of nicotinic acid glucoside formation by 250 mM NaCl in mature leaves of the mangrove fern, Acrostichum aureum, but it is unlikely that this compound acts as a compatible solute. Nicotinamide and nicotinic acid salvage for pyridine nucleotide synthesis was detected in all fern species, although this activity was always less than nicotinic acid glucoside synthesis. Predominant formation of nicotinic acid glucoside is characteristic of nicotinic acid metabolism in ferns. This reaction appears to act as a detoxication mechanism, removing excess nicotinic acid. PMID:21251843

Ashihara, Hiroshi; Yin, Yuling; Watanabe, Shin

2011-03-01

62

Access to intrinsically glucoside-based microspheres with boron affinity.  

PubMed

Intrinsically glucoside-based microspheres are prepared in olive oil via a water in oil inverse suspension polymerization. The microspheres are characterized by scanning electron microscopy (SEM), Fourier transform infrared (FTIR) microscopy, and X-ray photoelectron spectroscopy (XPS), evidencing the intrinsic glucose character of the spheres. A novel boronic acid fluorescent molecule was subsequently conjugated to the microspheres in an aqueous environment, exhibiting the spatial and uniform distribution of glucoside as well as the affinity of the microspheres to bind with boron, evidenced via fluorescence spectroscopy measurements. PMID:23533161

Vogt, Andrew P; Tischer, Thomas; Geckle, Udo; Greiner, Alexandra M; Trouillet, Vanessa; Kaupp, Michael; Barner, Leonie; Hofe, Thorsten; Barner-Kowollik, Christopher

2013-06-13

63

Humoral and cellular immune responses induced in mice by purified iridoid mixture that inhibits penetration of Schistosoma mansoni cercariae upon topical treatment of mice tails.  

PubMed

When tested for possible blocking effect on the cercarial, serine proteinase, elastase (CE) activity, an iridoid mixture extracted from leaves of Citharexylum quadrangular abolished 31% of the enzyme activity at final concentration 15 microg. When formulated in jojoba oil and applied to mice tails followed by infection with Schistosoma mansoni cercariae, the iridoid mixture blocked cercarial penetration and caused significant reducetion (94%; P < 0.05) in worm burden in treated mice in comparison to controls. Also, immunomodulatory effects of iridoid mixture, iridoid-treated S. mansoni worm homogenate on mice were studied by measuring IgG and IgM levels against E. coli lysates (ECL), solube S. mansoni worm antigenic preparation (SWAP) and cancer bladder homogenates (CBH) as antigens by ELISA. Cellular immune responses were studied by calculating mean percent of CD4+, CD8(+)-T, B-mesenteric lymph node cells (MLNC) and CD4+, CD8(+)-T thymocytes by direct immunofluorescence staining in treated mice as compared to untreated homogenate given mice or untreated mice. Injecting mice with serial dilutions of iridoid mixture resulted in fluctuation, peaks and troughs, in both IgG and IgM responses against the above mentioned antigens. 1st and 2nd immunizations with iridoid mixture treated homogenate resulted in significantly elevated (P < 0.05). IgM and IgG levels against the 3 used antigens in comparison with sera from control mice. Immunized mice with homogenate treated with iridoid mixture showed a significant increase (P < 0.05) in CD4+T thymocytes, a non significant increase in CD8+T thymocytes, a significant increase (P < 0.05) in CD4+T lymphocytes (MLNC) and a non significant increase in CD8+ T- and B-lymphocytes (MLNC) compared with mice immunized with untreated homogenate or non-injected normal mice. PMID:16083070

Bahgat, Mahmoud; Shalaby, Nagwa M M; Ruppel, Andreas; Maghraby, Amany S

2005-08-01

64

Soy Isoflavone Aglycones Are Absorbed Faster and in Higher Amounts than Their Glucosides in Humans  

Microsoft Academic Search

Isoflavones are contained in soybean or soy foods in two chemical forms, i.e., aglycones and glucosides. We investigated the difference in the absorption of soy isoflavone aglycones and glucosides in humans. After a single, low dose intake (0.11 mmol), the highest isoflavone concentrations in plasma were reached 2 and 4 h after ingestion of aglycones and glucosides, respectively; subjects were

Toru Izumi; Mariusz K. Piskula; Sachiko Osawa; Akio Obata; Koichiro Tobe; Makoto Saito; Shigehiro Kataoka; Yoshiro Kubota; Mamoru Kikuchi

65

Butanoic acid glucoside composition of whole body and in vitro plantlets of Anoectochilus formosanus  

Microsoft Academic Search

A butanoic acid glucoside, 3-O-?-D-glucopyranosyl-(3R)-4-dihydroxy butanoic acid, with known aliphatic glucosides were isolated from the methanol extract of dried whole plants of Anoectochilus formosanus Hay. Butanoic acid glucosides were formed in 3 types of regenerated plantlets in vitro.

Xiao-Ming Du; Toyokichi Yoshizawa; Yukihiro Shoyama

1998-01-01

66

Metabolism of conjugated sterols in eggplant. Part 2. Phospholipid : steryl glucoside acyltransferase  

Microsoft Academic Search

A membrane-bound phospholipid : steryl glucoside acyltransferase from Solanum melongena leaves was partially purified and its specificity and molecular as well as kinetic properties were defined. Among the steryl glycosides tested (e.g. typical plant steryl glucosides, steryl galacto - sides and cholesteryl xyloside) the highest activity was found with cholesteryl glucoside, but some structurally related compounds such as sito- and

Anna Potocka; Jan Zimowski

67

Conjugates of an abscisic acid derivative and phenolic glucosides, and a new sesquiterpene glucoside from Lindera strychnifolia.  

PubMed

Three conjugates of the abscisic acid derivative (2Z,4E)-5-[(1S,3S,5R,8S)-3,8-dihydroxy-1,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid and phenolic glucosides (1-3), and an eremophilane-type sesquiterpene glucoside (4), along with ten known compounds, were isolated from the roots of Lindera strychnifolia. The structures of all compounds were elucidated by means of spectroscopic analysis, and by application of the modified Mosher's method for the methyl ester of the abscisic acid derivative and the octant rule for 4. PMID:20119718

Mimura, Akinori; Sumioka, Hitomi; Matsunami, Katsuyoshi; Otsuka, Hideaki

2010-04-01

68

A new sesquiterpene glucoside from Nicotiana rustica L.  

PubMed

A new compound, rel-2R,5S,9S,10R,11R,12-trihydroxy-6(7)-spirovetiven-8-one-9- O-?-D-glucopyranoside (1), along with a known spirovetiven glucoside (2), was isolated from the leaves of Nicotiana rustica L. The structure of compound (1) was elucidated on the basis of spectroscopic data. PMID:22974363

Zhou, Rong; Li, Dong-Liang; Feng, Guang-Lin; Li, Guo-You

2013-01-01

69

Ring B aromatic norpimarane glucoside from a Xylaria sp.  

PubMed

A novel 20-norpimarane glucoside, xylopimarane (1), together with the known sphaeropsidin C (2) and clonostachydiol (3), was isolated from the fungus Xylaria sp. BCC 4297. Compound 1 exhibited cytotoxicity to cancer cell lines KB, MCF-7, and NCI-H187 with respective IC(50) values of 1.0, 13, and 65 ?M. PMID:21226484

Isaka, Masahiko; Yangchum, Arunrat; Auncharoen, Patchanee; Srichomthong, Kitlada; Srikitikulchai, Prasert

2011-02-25

70

The absorption of protons with alpha-methyl glucoside and alpha-thioethyl glucoside by the yeast N.C.Y.C. 240. Evidence against the phosphorylation hypothesis.  

PubMed Central

1. When yeast N.C.Y.C. 240 was grown with maltose in a complex medium based on yeast extract and peptone, washed cell preparations fermented alpha-methyl glucoside much more slowly than maltose. 2. The yeast absorbed alpha-methyl[14C]glucoside from a 10mM solution in the presence of antimycin and iodoacetamide, producing [14C]glucose, which accumulated outside the cells. The yeast itself contained hexose phosphates, trehalose, alpha-methyl glucoside and other products labelled with 14C, but no alpha-methyl glucoside phosphate. 3. About 1 equiv. of protons was absorbed with each equivalent of alpha-methylglucoside, and 1 equiv. of K+ ions left the yeast. 4. alpha-Thioethyl glucoside was also absorbed along with protons. Studies by g.l.c. showed that the yeast concentrated the compound without metabolizing it. 5. The presence of trehalose, sucrose, maltose, L-sorbose, glucose or alpha-phenyl glucoside in each case immediately stimulated proton uptake, whereas fructose, 3-O-methylglucose and 2-deoxyglucose failed to do so. 6. The observations support the conclusion that alpha-thioethyl glucoside, alpha-methyl glucoside and maltose are substrates of one or more proton symports, whereas they seem inconsistent with the notion that the absorption of alpha-methyl glucoside involves the phosphorylation of the carbohydrate [Van Stevenick (1970) Biochim. Biophys. Acta 203, 376-384].

Brocklehurst, R; Gardner, D; Eddy, A A

1977-01-01

71

Conjugates of a secoiridoid glucoside with a phenolic glucoside from the flower buds of Lonicera japonica Thunb.  

PubMed

Secoiridoid glucosides, including two conjugates with a phenolic and two conjugates with a nicotinic acid derivative (3 and 4), together with seven known secoiridoid derivatives, were isolated from flower buds of Lonicera japonica. The structures were elucidated by spectroscopic analyses. Anti-influenza activities of six isolated compounds were also evaluated by plaque assay and neuraminidase inhibitory assay. PMID:24120297

Kashiwada, Yoshiki; Omichi, Yuka; Kurimoto, Shin-ichiro; Shibata, Hirofumi; Miyake, Yoshiyuki; Kirimoto, Tsukasa; Takaishi, Yoshihisa

2013-12-01

72

Cornel Iridoid Glycoside Attenuates Tau Hyperphosphorylation by Inhibition of PP2A Demethylation.  

PubMed

Aim. The aim of the present study was to investigate the effect of cornel iridoid glycoside (CIG) on tau hyperphosphorylation induced by wortmannin (WT) and GF-109203X (GFX) and the underlying mechanisms. Methods. Human neuroblastoma SK-N-SH cells were preincubated with CIG (50, 100, and 200?µg/ml, resp.) for 24 h and then exposed to 10?µM WT and 10?µM GFX for 3 h after washing out CIG. Immunohistochemistry was used to observe the microtubular cytoskeleton of the cultured cells. Western blotting was used to measure the phosphorylation level of tau protein, glycogen synthase kinase 3 ? (GSK-3 ? ), and protein phosphatase 2A (PP2A). The activity of PP2A was detected by a biochemical assay. Results. Preincubation of CIG significantly attenuated the WT/GFX-induced tau hyperphosphorylation at the sites of Thr205, Thr212, Ser214, Thr217, Ser396, and PHF-1 and improved the damage of morphology and microtubular cytoskeleton of the cells. CIG did not prevent the decrease in p-AKT-ser473 and p-GSK-3 ? -ser9 induced by WT/GFX. However, CIG significantly elevated the activity of PP2A by reducing the demethylation of PP2A catalytic subunit (PP2Ac) at Leu309 and the ratio of PME-1/LCMT in the WT/GFX-treated cells. The results suggest that CIG may be beneficial to the treatment of AD. PMID:24454482

Yang, Cui-Cui; Kuai, Xue-Xian; Li, Ya-Li; Zhang, Li; Yu, Jian-Chun; Li, Lin; Zhang, Lan

2013-01-01

73

Cornel Iridoid Glycoside Attenuates Tau Hyperphosphorylation by Inhibition of PP2A Demethylation  

PubMed Central

Aim. The aim of the present study was to investigate the effect of cornel iridoid glycoside (CIG) on tau hyperphosphorylation induced by wortmannin (WT) and GF-109203X (GFX) and the underlying mechanisms. Methods. Human neuroblastoma SK-N-SH cells were preincubated with CIG (50, 100, and 200?µg/ml, resp.) for 24 h and then exposed to 10?µM WT and 10?µM GFX for 3 h after washing out CIG. Immunohistochemistry was used to observe the microtubular cytoskeleton of the cultured cells. Western blotting was used to measure the phosphorylation level of tau protein, glycogen synthase kinase 3? (GSK-3?), and protein phosphatase 2A (PP2A). The activity of PP2A was detected by a biochemical assay. Results. Preincubation of CIG significantly attenuated the WT/GFX-induced tau hyperphosphorylation at the sites of Thr205, Thr212, Ser214, Thr217, Ser396, and PHF-1 and improved the damage of morphology and microtubular cytoskeleton of the cells. CIG did not prevent the decrease in p-AKT-ser473 and p-GSK-3?-ser9 induced by WT/GFX. However, CIG significantly elevated the activity of PP2A by reducing the demethylation of PP2A catalytic subunit (PP2Ac) at Leu309 and the ratio of PME-1/LCMT in the WT/GFX-treated cells. The results suggest that CIG may be beneficial to the treatment of AD.

Yang, Cui-cui; Kuai, Xue-xian; Li, Ya-li; Zhang, Li; Yu, Jian-chun; Li, Lin; Zhang, Lan

2013-01-01

74

Stereochemistry of megastigmane glucosides from Glochidion zeylanicum and Alangium premnifolium.  

PubMed

From Glochidion zeylanicum, two megastigmane glucosides, 3- and 9-O-beta-D-glucopyranosides of (3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol (1 and 2, respectively), were isolated. Their structures were different from those of kiwiionoside (3) and actinidioionoside (4), isolated from Actinidia chinensis and Actinidia polygama, respectively, in the stereochemistry at the 9-positions. Alangionosides E (5) and O (6), isolated from the leaves of Alangium premnifolium, are also megastigmane glucosides, and the latter is closely related to 1 and actinidioionoside (4). However, the absolute configurations of the 9-position remained to be determined. They were analyzed to be R by means of a modified Mosher's method. Alangionoside E (5) is identical with corchoionoside A in all aspects. The name of corchoionoside A must be retained thereafter. PMID:12620329

Otsuka, Hideaki; Hirata, Eiji; Shinzato, Takakazu; Takeda, Yoshio

2003-03-01

75

Dihydroisocoumarin glucosides from stem bark of Caryocar glabrum.  

PubMed

Two dihydroisocoumarin glucosides have been isolated from the stem bark of Caryocar glabrum (Aubl.) Pers. Their structures and absolute stereochemistry were established on the basis of extensive 1D and 2D NMR, UV, IR, HRESIMS, and CD studies. These compounds represent the first members of a new biogenetic pathway for the isocoumarins nucleus involving shikimate derived A-ring coupling with a phenyl propanoid derivative. PMID:17618658

Magid, Abdulmagid Alabdul; Voutquenne-Nazabadioko, Laurence; Moroy, Gautier; Moretti, Christian; Lavaud, Catherine

2007-10-01

76

A phloracetophenone glucoside with choleretic activity from Curcuma comosa  

Microsoft Academic Search

Three known diarylheptanoids, 1,7-diphenyl-5-hydroxy-(1E)-1-heptene, 5-hydroxy-7-(4-hydroxyphenyl)-1-phenyl-(1E)-1-heptene and 7-(3,4-dihydroxyphenyl)-5-hydroxy-1-phenyl-(1E)-1-heptene, were isolated from the ethyl acetate extract of Curcuma comosa rhizomes. A phloracetophenone glucoside, 4,6-dihydroxy-2-O-(?-d-glucopyranosyl)acetophenone, was isolated from the ethyl acetate and n-butanol extracts. This compound exhibited choleretic activity in rats.

Apichart Suksamrarn; Salinee Eiamong; Pawinee Piyachaturawat; Lindsay T. Byrne

1997-01-01

77

Structural revisions of blumenol C glucoside and byzantionoside B.  

PubMed

The absolute stereochemistry of blumenol C glucoside and byzantionoside B was revised here as (6R,9S)- and (6R,9R)-9-hydroxymegastigman-4-en-3-one 9-O-beta-D-glucopyranosides, respectively, by modified Mosher's method. The empirical rules of (13)C-NMR chemical shift to determine the absolute stereochemistry of C-9 of 9-hydroxymegastigmane 9-O-beta-D-glucopyranoside were also discussed. PMID:20190461

Matsunami, Katsuyoshi; Otsuka, Hideaki; Takeda, Yoshio

2010-03-01

78

Nicotinamide metabolism in ferns: Formation of nicotinic acid glucoside  

Microsoft Academic Search

The metabolic fate of [carbonyl-14C]nicotinamide was investigated in 9 fern species, Psilotum nudum, Angiopteris evecta, Lygodium japonicum, Acrostichum aureum, Asplenium antiquum, Diplazium subsinuatum, Thelypteris acuminate, Blechnum orientale and Crytomium fortune. All fern species produce a large quantity of nicotinic acid glucoside from [14C]nicotinamide, but trigonelline formation is very low. Increases in the release of 14CO2 with incubation time was accompanied by

Hiroshi Ashihara; Yuling Yin; Shin Watanabe

2011-01-01

79

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

PubMed

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

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

2013-12-01

80

New dimeric and trimeric coumarin glucosides from Daphne retusa Hemsl.  

PubMed

New dimeric and a trimeric coumarin glucosides namely Daphneretusin A (1) Daphneretusin B (2) along with three known oligomers (3-5) were obtained as a result of bioassay guided fractionation of Daphne retusa Hemsl. Fractions (n-hexane, CHCl3, AcOEt, CH3OH and water) exhibited potent radical scavenging activity in relevant non-physiological bioassays. The structures of isolated compounds were elucidated by UV, IR, EIMS, FAB-MS, 1D, and 2D NMR spectroscopic analysis. PMID:23570839

Mansoor, Farrukh; Anis, Itrat; Ali, Sajjad; Choudhary, Muhammad Iqbal; Shah, Muhammad Raza

2013-07-01

81

Two new cyanogenic glucosides from the leaves of Hydrangea macrophylla.  

PubMed

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

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

2012-01-01

82

Antioxidative glucosides from the fruits of Ligustrum lucidum.  

PubMed

The ethanol extract of the fruits of Ligustrum lucidum was shown to have inhibitory effects on the hemolysis of red blood cells induced by 2,2'-azo-bis-(2-amidinopropane) dihydrochloride. Bioassay-guided analysis led to the isolation of ten secoiridoid glucosides. Two of them were new, lucidumosides C and D. Their structures were elucidated by spectroscopic methods. The other eight compounds were identified as oleoside dimethyl ester, ligustroside, oleuropein, nuezhenide, isonuezhenide, neonuezhenide, lucidumoside A and lucidumoside B. Five compounds, oleoside dimethyl ester, oleuropein, neonuezhenide, lucidumoside B and lucidumoside C, exhibited strong antioxidant effect against hemolysis of red blood cells induced by free radicals. PMID:11411539

He, Z D; But PPH; Chan, T W; Dong, H; Xu, H X; Lau, C P; Sun, H D

2001-06-01

83

Glucosides from MBOA and BOA detoxification by Zea mays and Portulaca oleracea.  

PubMed

Incubation of Zea mays cv. Nicco seedlings with 6-methoxybenzoxazolin-2(3H)-one (MBOA) led to a minor detoxification product hitherto only found in Poaceae. This new compound was identified as 1-(2-hydroxy-4-methoxyphenylamino)-1-deoxy-beta-glucoside 1,2-carbamate (1) (methoxy glucoside carbamate) and represents an analogue to the previously described 1-(2-hydroxyphenylamino)-1-deoxy-beta-glucoside 1,2-carbamate (glucoside carbamate) from benzoxazolin-2(3H)-one (BOA). In Portulaca oleracea var. sativa cv. Gelber treatment with BOA resulted in further unknown detoxification products, which were not synthesized in detectable amounts after BOA absorption in all other species tested. Compound 1 easily undergoes decay into BOA-5-O-glucoside (2). Z. mays seedlings, known to produce BOA-6-O-Glc on incubation with BOA, are able to transform BOA-5-OH into BOA-5-O-glucoside (2). Besides the known compounds, maize contained a formerly unseen product that accumulated during late stages of the detoxification process. It was isolated and identified as 1-(2-hydroxyphenylamino)-6-O-malonyl-1-deoxy-beta-glucoside 1,2-carbamate (3) (malonyl glucoside carbamate). PMID:16441064

Hofmann, Diana; Knop, Mona; Hao, Huang; Hennig, Lothar; Sicker, Dieter; Schulz, Margot

2006-01-01

84

In Vitro Effects of Cholesterol ?- d Glucoside, Cholesterol and Cycad Phytosterol Glucosides on Respiration and Reactive Oxygen Species Generation in Brain Mitochondria  

Microsoft Academic Search

The cluster of neurodegenerative disorders in the western Pacific termed amyotrophic lateral sclerosis–parkinsonism dementia\\u000a complex (ALS-PDC) has been repeatedly linked to the use of seeds of various species of cycad. Identification and chemical\\u000a synthesis of the most toxic compounds in the washed cycad seeds, a variant phytosteryl glucosides, and even more toxic cholesterol\\u000a ?-d-glucoside (CG), which is produced by the

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

2010-01-01

85

Enzymatic synthesis of apigenin glucosides by glucosyltransferase (YjiC) from Bacillus licheniformis DSM 13.  

PubMed

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

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

2013-10-01

86

Iridoids from Fraxinus excelsior with adipocyte differentiation-inhibitory and PPARalpha activation activity.  

PubMed

Two new secoiridoid glucosides, excelsides A (1) and B (2), were isolated from the seeds of Fraxinus excelsior. Their structures were elucidated as (2S,4S,3E)-methyl 3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-[(6-O-beta-D-glucopyranosyl-beta-d-glucopyranosyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylate and (2S,4S,3E)-methyl 3-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethyl]oxy-2-oxoethyl}-2-[(6-O-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylate, respectively, on the basis of NMR and MS data. Eight known compounds were identified as nuzhenide (3), GI3 (4), GI5 (5), ligstroside (6), oleoside 11-methyl ester (7), oleoside dimethyl ester (8), 1'''-O-beta-D-glucosylformoside (9), and salidroside (10). Compounds 1-9 inhibited adipocyte differentiation in 3T3-L1 cells. Dilutions of the aqueous extract of F. excelsior (1:10,000) as well as compounds 2, 3, 4, 5, and 8 activated the peroxisome proliferator-mediated receptor-alpha (PPARalpha) reporter cell system in the range of 10(-4) M, compared to 10(-7)-10(-8) M for the synthetic PPARalpha activator, WY14,643. Both biological activity profiles support the hypothesis that inhibition of adipocyte differentiation and PPARalpha-mediated mechanisms might be relevant pathways for the antidiabetic activity of F. excelsior extract. PMID:20000781

Bai, Naisheng; He, Kan; Ibarra, Alvin; Bily, Antoine; Roller, Marc; Chen, Xiaozhuo; Rühl, Ralph

2010-01-01

87

Two Unusual Methylidenecyclopropane Glucosides from Metaxya rostrata C.Presl  

PubMed Central

Two new natural compounds, (1R,2E)-2-(6-hydroxyhexylidene)cyclopropyl-?-D-glucopyranoside (1) and (6E)-6-[(2R)-2-(?-D-glucopyranosyloxy)cyclopropylidene]hexanoic acid (2), glucosides of a very rare methylidenecyclopropane alcohol, as well as two known glycosides of phenolic acids, namely 4-O-?-D-glucopyranosylcaffeic acid (3) and (E)-4-O-?-D-glucopyranosylcoumaric acid (4), and methyl ?-fructofuranoside (5) were isolated for the first time from the rhizomes of the tree fern Metaxya rostrata C.Presl. The structures were elucidated on the basis of detailed spectroscopic data analysis, and the structure of 1 was additionally confirmed by X-ray crystal-structure analysis.

Kainz, Kerstin P; Virtbauer, Judith; Kahlig, Hanspeter; Arion, Vladimir; Donath, Oliver; Reznicek, Gottfried; Huber, Werner; Marian, Brigitte; Krenn, Liselotte

2012-01-01

88

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

PubMed

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

2013-11-01

89

Analysis of interaction property of calycosin-7-O-?-d-glucoside with human gut microbiota.  

PubMed

Calycosin-7-O-?-d-glucoside as the major isoflavonoids in Astragali Radix has been investigated intensively and has been reported to possess a wide range of pharmacological properties. However, the route and metabolites of calycosin-7-O-?-d-glucoside by human intestinal bacteria are not well understood and its metabolites may accumulate to exert physiological effects. Therefore, the objective of this study was to screen the ability of the bacteria to metabolize calycosin-7-O-?-d-glucoside and assess the effect of this compound on the intestinal bacteria. Finally, five strains including Bacteroides sp.13, and sp.58, Clostridium sp.21-2, Veillonella sp.43-1, and Bacillus sp.46 were isolated from human intestinal bacteria and were studied their abilities to convert calycosin-7-O-?-d-glucoside. A total of six metabolites were identified in human incubated solution by ultra performance liquid chromatography/quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS). The results indicated that hydrolysis, demethylation, dehydroxylation and acetylation were the major metabolism of calycosin-7-O-?-d-glucoside. On the other hand, different strains of intestinal bacteria have varying degrees of growth sensitivity to calycosin-7-O-?-d-glucoside. Growth of certain pathogenic bacteria such as Enterobacter, Enterococcus, Clostridium and Bacteroides was significantly repressed by calycosin-7-O-?-d-glucoside, while commensal probiotics such as Lactobacillus, Bifidobacterium were less severely affected. This indicates that calycosin-7-O-?-d-glucoside exert significant effects on the intestinal environment by modulation of the intestinal bacterial population. Our observation provided further evidence for the importance of intestinal bacteria in the metabolism, absorption and potential activity of calycosin-7-O-?-d-glucoside in human health and diseases. PMID:24922599

Zhang, Wei; Jiang, Shu; Qian, Dawei; Shang, Er-Xin; Duan, Jin-Ao

2014-07-15

90

Regioselective glucosidation of trans-resveratrol in Escherichia coli expressing glucosyltransferase from Phytolacca americana.  

PubMed

A glucosyltransferase (GT) of Phytolacca americana (PaGT3) was expressed in Escherichia coli and purified for the synthesis of two O-?-glucoside products of trans-resveratrol. The reaction was moderately regioselective with a ratio of 4'-O-?-glucoside: 3-O-?-glucoside at 10:3. We used not only the purified enzyme but also the E. coli cells containing the PaGT3 gene for the synthesis of glycoconjugates. E. coli cell cultures also have other advantages, such as a shorter incubation time compared with cultured plant cells, no need for the addition of exogenous glucosyl donor compounds such as UDP-glucose, and almost complete conversion of the aglycone to the glucoside products. Furthermore, a homology model of PaGT3 and mutagenesis studies suggested that His-20 would be a catalytically important residue. PMID:22048846

Ozaki, Shin-ichi; Imai, Hiroya; Iwakiri, Tomoya; Sato, Takehiro; Shimoda, Kei; Nakayama, Toru; Hamada, Hiroki

2012-03-01

91

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

PubMed

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

Herrmann, Martina; Joppe, Holger; Schmaus, Gerhard

2002-06-01

92

Thesinine-4?- O-?- d-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis  

Microsoft Academic Search

The glycosylated pyrrolizidine alkaloid, thesinine-4?-O-?-d-glucoside, has been isolated from the aqueous methanolic extract of dried seeds of Borago officinalis (Boraginaceae). The structure was established by means of spectroscopic and chemical analyses.

Martina Herrmann; Holger Joppe; Gerhard Schmaus

2002-01-01

93

Inhibition of platelet aggregation by colchicine, thiocolchicine, and their phenolic and glucosidic congeners  

Microsoft Academic Search

Inhibition of platelet aggregation by colchicine, thiocolchicine, O-demethylated and 3-glucosidic congeners was measured in\\u000a vitro. 2- And 3-demethylated analogs of colchicine and thiocolchicine were found to be as potent as colchicine and thiocolchicine,\\u000a respectively, whereas 1-demethylated compounds were found to be considerably less active. Both glucosides, colchicoside and\\u000a thiocolchicoside, were not very active in this assay. 2,3-Didemethylcolchicine, which is much

Arnold Brossi; Raymond Dumont; Hye Sook Yun-Choi; Jong Ran Lee

1987-01-01

94

Transport of Quercetin and Its Glucosides across Human Intestinal Epithelial Caco-2 Cells  

Microsoft Academic Search

There is mounting evidence from human epidemiological, animal in vivo, and in vitro studies to suggest beneficial effects related to the consumption of quercetin and its glucosides. However, there is limited knowledge on the oral bioavailability of these natural products. This study examined the intestinal epithelial membrane transport of quercetin, quercetin 4?-glucoside, and quercetin 3,4?-diglucoside, using the Caco-2 human colonic

Richard A Walgren; U. Kristina Walle; Thomas Walle

1998-01-01

95

Succinyl-coenzyme A: Anthocyanidin 3-glucoside succinyltransferase in flowers of Centaurea cyanus  

Microsoft Academic Search

The acyltransferase from blue flowers of Centaurea cyanus containing succinylated cyanidin 3,5-diglucosides catalysed the transfer of the succinyl moiety from succinyl-CoA to 3-glucosides of cyanidin and pelargonidin, but not to 3,5-diglucosides. Similar results were obtained using the enzyme from pink flowers containing succinylated pelargonidin 3,5-diglucosides. The enzyme also catalysed these anthocyanidin 3-glucosides to malonylate at nearly the same rate as

Masa-atu Yamaguchi; Tatsunori Maki; Takako Ohishi; Ikuo Ino

1995-01-01

96

New Facile Syntheses of Monolignols Glucosides; p- Glucocoumaryl Alcohol, Coniferin and Syringin  

Microsoft Academic Search

The monolignols glucosides p-glucocoumaryl alcohol, coniferin and syringin, have been found in cambial sap of gymnospermous trees (Freudenberg and Harkin 1963) and some species of angiospermous trees (Terazawa et al. 1984). Coniferin has been shown to bean effective precursor of lignin biosynthesis in pine (Freudenberg et al. 1955). When three kinds of monolignols glucosides labeled with,C or,H were administered to

Noritsugu Terashima; Sally A. Ralph; Lawrence L. Landucci

1996-01-01

97

Cyanidin-3-Glucoside Ameliorates Ethanol Neurotoxicity in the Developing Brain  

PubMed Central

Ethanol exposure induces neurodegeneration in the developing central nervous system (CNS). Fetal Alcohol Spectrum Disorders (FASD) are caused by ethanol exposure during pregnancy and are the most common nonhereditary cause of mental retardation. It is important to identify agents that provide neuroprotection against ethanol neurotoxicity. Multiple mechanisms have been proposed for ethanol-induced neurodegeneration, and oxidative stress is one of the most important mechanisms. Recent evidence indicates that glycogen synthase kinase 3? (GSK3?) is a potential mediator of ethanol-mediated neuronal death (Luo, 2009). Cyanidin-3-glucoside (C3G), a member of the anthocyanin family, is a potent natural antioxidant. Our previous study suggested that C3G inhibited GSK3? activity in neurons (Chen et al., 2009). Using a third trimester equivalent mouse model of ethanol exposure, we tested the hypothesis that C3G can ameliorate ethanol-induced neuronal death in the developing brain. Intraperitoneal injection of C3G reduced ethanol-meditated caspase-3 activation, neurodegeneration and microglial activation in the cerebral cortex of seven-day-old mice. C3G blocked ethanol-mediated GSK3? activation by inducing the phosphorylation at serine 9 while reducing the phosphorylation at tyrosine 216. C3G also inhibited ethanol-stimulated expression of malondialdehyde (MDA) and p47phox, indicating that C3G alleviated ethanol-induced oxidative stress. These results provide important insight into the therapeutic potential of C3G.

Ke, Zunji; Liu, Ying; Wang, Xin; Fan, Zhiqin; Chen, Gang; Xu, Mei; Bower, Kimberley A.; Frank, Jacqueline A.; Ou, Xiaoming; Shi, Xianglin; Luo, Jia

2011-01-01

98

Hydrolytic fate of deoxynivalenol-3-glucoside during digestion.  

PubMed

Deoxynivalenol-3-?-D-glucoside (D3G), a plant phase II metabolite of the Fusarium mycotoxin deoxynivalenol (DON), occurs in naturally contaminated wheat, maize, oat, barley and products thereof. Although considered as a detoxification product in plants, the toxicity of this substance in mammals is currently unknown. A major concern is the possible hydrolysis of the D3G conjugate back to its toxic precursor mycotoxin DON during mammalian digestion. We used in vitro model systems to investigate the stability of D3G to acidic conditions, hydrolytic enzymes and intestinal bacteria, mimicking different stages of digestion. D3G was found resistant to 0.2 M hydrochloric acid for at least 24 h at 37 °C, suggesting that it will not be hydrolyzed in the stomach of mammals. While human cytosolic ?-glucosidase also had no effect, fungal cellulase and cellobiase preparations could cleave a significant portion of D3G. Most importantly, several lactic acid bacteria such as Enterococcus durans, Enterococcus mundtii or Lactobacillus plantarum showed a high capability to hydrolyze D3G. Taken together these data indicate that D3G is of toxicological relevance and should be regarded as a masked mycotoxin. PMID:21878373

Berthiller, Franz; Krska, Rudolf; Domig, Konrad J; Kneifel, Wolfgang; Juge, Nathalie; Schuhmacher, Rainer; Adam, Gerhard

2011-10-30

99

Hydrolytic fate of deoxynivalenol-3-glucoside during digestion  

PubMed Central

Deoxynivalenol-3-?-d-glucoside (D3G), a plant phase II metabolite of the Fusarium mycotoxin deoxynivalenol (DON), occurs in naturally contaminated wheat, maize, oat, barley and products thereof. Although considered as a detoxification product in plants, the toxicity of this substance in mammals is currently unknown. A major concern is the possible hydrolysis of the D3G conjugate back to its toxic precursor mycotoxin DON during mammalian digestion. We used in vitro model systems to investigate the stability of D3G to acidic conditions, hydrolytic enzymes and intestinal bacteria, mimicking different stages of digestion. D3G was found resistant to 0.2 M hydrochloric acid for at least 24 h at 37 °C, suggesting that it will not be hydrolyzed in the stomach of mammals. While human cytosolic ?-glucosidase also had no effect, fungal cellulase and cellobiase preparations could cleave a significant portion of D3G. Most importantly, several lactic acid bacteria such as Enterococcus durans, Enterococcus mundtii or Lactobacillus plantarum showed a high capability to hydrolyze D3G. Taken together these data indicate that D3G is of toxicological relevance and should be regarded as a masked mycotoxin.

Berthiller, Franz; Krska, Rudolf; Domig, Konrad J.; Kneifel, Wolfgang; Juge, Nathalie; Schuhmacher, Rainer; Adam, Gerhard

2011-01-01

100

Tetrahydroxystilbene glucoside attenuates neuroinflammation through the inhibition of microglia activation.  

PubMed

Neuroinflammation is closely implicated in the pathogenesis of neurological diseases. The hallmark of neuroinflammation is the microglia activation. Upon activation, microglia are capable of producing various proinflammatory factors and the accumulation of these factors contribute to the neuronal damage. Therefore, inhibition of microglia-mediated neuroinflammation might hold potential therapy for neurological disorders. 2,3,5,4'-Tetrahydroxystilbene-2-O-?-D-glucoside (TSG), an active component extracted from Polygonum multiflorum, is reported to be beneficial for human health with a great number of pharmacological properties including antioxidant, free radical-scavenging, anti-inflammation, antilipemia, and cardioprotective effects. Recently, TSG-mediated neuroprotective effects have been well demonstrated. However, the neuroprotective actions of TSG on microglia-induced neuroinflammation are not known. In the present study, microglia BV2 cell lines were applied to investigate the anti-neuroinflammatory effects of TSG. Results showed that TSG reduced LPS-induced microglia-derived release of proinflammatory factors such as TNF?, IL-1?, and NO. Moreover, TSG attenuated LPS-induced NADPH oxidase activation and subsequent reactive oxygen species (ROS) production. Further studies indicated that TSG inhibited LPS-induced NF-?B signaling pathway activation. Together, TSG exerted neuroprotection against microglia-mediated neuroinflammation, suggesting that TSG might present a promising benefit for neurological disorders treatment. PMID:24349614

Zhang, Feng; Wang, Yan-Ying; Yang, Jun; Lu, Yuan-Fu; Liu, Jie; Shi, Jing-Shan

2013-01-01

101

Screening for limonoid glucosides in Citrus tangerina (Tanaka) Tseng by high-performance liquid chromatography-electrospray ionization mass spectrometry.  

PubMed

A screening method for limonoid glucosides in the peel of Citrus tangerina (Tanaka) Tseng, which utilizes high-performance liquid chromatography (HPLC) with diode-array detection and interfaced to electrospray ionization mass spectrometry, has been developed. In this way, the UV-Vis spectra and the mass spectra indicate the presence of limonoid glucosides without the necessity of isolating the individual compounds. Two major limonoid glucosides--obacunone glucoside (OG) and nomilin glucoside (NG)--were identified in the methanol extract of the peel. The two limonoid glucosides were taken as the target and isolated by means of preparative HPLC on a C18 reversed-phase column with an acidic acetonitrile-water mobile phase. The structures of OG and NG were further confirmed by nuclear magnetic resonance spectrometry. PMID:10768495

Tian, Q; Ding, X

2000-03-31

102

On the glucoside analysis: simultaneous determination of free and esterified steryl glucosides in olive oil. Detailed analysis of standards as compulsory first step.  

PubMed

This work covers two important gaps in the field of micronutrient databases: herein we describe a short and easy protocol that allows the analysis of both free and esterified steryl gulcosides in olive oil. By utilising accurate quantitative methods we achieve a better understanding of olive oil composition and health promoting properties. The procedure consists of isolating the fraction of interest through solid phase extraction, and using gas chromatography-flame ionisation detection for both identification and quantification of the derivatised species. Additionally, mass-spectrometry detection has been utilised for confirming the identity of the individual esterified steryl glucosides in some cases. The method's limit of detection has been set at 0.37mg/kg for each free steryl glucoside and 0.20mg/kg for each esterified steryl glucoside, whereas the recoveries are around 96% and 77%, respectively. Finally, we provide a complete analysis of the commercial standard for esterified steryl glucosides, since such information was not yet available. PMID:23790913

Gómez-Coca, Raquel B; Pérez-Camino, María Del Carmen; Moreda, Wenceslao

2013-11-15

103

Malonylglucoside Conjugates of Isoflavones Are Much Less Bioavailable Compared with Unconjugated ?-Glucosidic Forms in Rats.  

PubMed

Despite considerable interest in the physiologic effects of isoflavones, the in vivo bioavailability of the most common isoflavone forms, malonylglucoside conjugates, has not been determined. Differences in the bioavailability of malonylglucosides compared with the nonconjugated ?-glucoside forms may explain the inconsistent findings regarding the physiologic effects of isoflavones. Therefore, our objective was to determine the effect of malonyl- conjugation on isoflavone bioavailability in an animal model. Malonylgenistin and malonyldaidzin, and their corresponding nonconjugated glucosides, were extracted from soy grits and purified using liquid chromatography. Purity of the isolated forms was confirmed by nuclear magnetic resonance analysis. Male rats were gavaged with malonylgenistin, genistin, malonyldaidzin, or daidzin at a dose of 100 ?mol/kg body weight. Blood and urine samples were collected at time intervals ranging from 0 to 48 h. Isoflavone metabolites in plasma and urine were determined using stable isotope dilution-liquid chromatography/mass spectrometry. Comparisons of pharmacokinetic variables were made between nonconjugated and conjugated glucosides and over time of plasma collection. The areas under the time-concentration curve of the metabolites in the plasma obtained after the administration of nonconjugated ?-glucosides were 1 to 6 times higher than those of their respective malonylglucosides (P ? 0.05). Additionally, maximum plasma concentration and urinary excretion of isoflavone metabolites were significantly higher (1-9 times; P ? 0.05) after the administration of nonconjugated ?-glucosides. To our knowledge, these results demonstrated, for the first time, that nonconjugated ?-glucosides are relatively more bioavailable than their respective malonylglucosides. These differences in the bioavailability of conjugated and nonconjugated ?-glucosides should be considered in future studies focused on the bioactivity of isoflavones. PMID:24647389

Yerramsetty, Vamsidhar; Gallaher, Daniel D; Ismail, Baraem

2014-05-01

104

Metabolism of the masked mycotoxin deoxynivalenol-3-glucoside in rats  

PubMed Central

Deoxynivalenol-3-?-d-glucoside (D3G), a plant metabolite of the Fusarium mycotoxin deoxynivalenol (DON), might be hydrolyzed in the digestive tract of mammals, thus contributing to the total dietary DON exposure of individuals. Yet, D3G has not been considered in regulatory limits set for DON for foodstuffs due to the lack of in vivo data. The aim of our study was to evaluate whether D3G is reactivated in vivo by investigation of its metabolism in rats. Six Sprague-Dawley rats received water, DON (2.0 mg/kg body weight (b.w.)) and the equimolar amount of D3G (3.1 mg/kg b.w.) by gavage on day 1, 8 and 15, respectively. Urine and feces were collected for 48 h and analyzed for D3G, DON, deoxynivalenol-glucuronide (DON-GlcA) and de-epoxy deoxynivalenol (DOM-1) by a validated LC–tandem mass spectrometry (MS/MS) based biomarker method. After administration of D3G, only 3.7 ± 0.7% of the given dose were found in urine in the form of analyzed analytes, compared to 14.9 ± 5.0% after administration of DON, and only 0.3 ± 0.1% were detected in the form of urinary D3G. The majority of administered D3G was recovered as DON and DOM-1 in feces. These results suggest that D3G is little bioavailable, hydrolyzed to DON during digestion, and partially converted to DOM-1 and DON-GlcA prior to excretion. Our data indicate that D3G is of considerably lower toxicological relevance than DON, at least in rats.

Nagl, Veronika; Schwartz, Heidi; Krska, Rudolf; Moll, Wulf-Dieter; Knasmuller, Siegfried; Ritzmann, Mathias; Adam, Gerhard; Berthiller, Franz

2012-01-01

105

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

PubMed Central

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

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

1991-01-01

106

Evidence for bile acid glucosides as normal constituents in human urine.  

PubMed

A glucosyltransferase catalysing formation of bile acid glucosides was recently isolated from human liver microsomes. In order to investigate the potential occurrence of such bile acid derivatives in vivo, a method was devised for their isolation and purification from urine. Conditions were established with the aid of glucosides of radiolabelled, unconjugated glycine and taurine conjugated bile acids prepared enzymatically using human liver microsomes. Analysis by gas chromatography and mass spectrometry of methyl ester trimethylsilyl ether derivatives indicated the excretion of glucosides of nonamidated hyodeoxycholic, chenodeoxycholic, deoxycholic, ursodeoxycholic and cholic acids and of glycine and taurine conjugated chenodeoxycholic and cholic acids. Additional compounds were present giving mass spectral fragmentation patterns typical of di- and trihydroxy bile acid glycosides. Semiquantitative estimates indicated a total daily excretion of about 1 mumol. PMID:2951276

Marschall, H U; Egestad, B; Matern, H; Matern, S; Sjövall, J

1987-03-23

107

Cell division promoting activity of naturally occurring dehydrodiconiferyl glucosides: do cell wall components control cell division?  

PubMed Central

Naturally occurring isomers of the dehydrodiconiferyl glucosides have been isolated from Vinca rosea crown gall tumors and have been tested for cell division promoting activities in the tobacco pith and leaf assay systems. The enantiomeric isomers A and B are active, although they are required at concentrations up to 2 orders of magnitude higher than zeatin riboside to promote comparable growth. We estimate that the active dehydrodiconiferyl glucosides are present in rapidly growing tissues (tumor tissue, habituated tissue, cultured nontransformed tissue) in micromolar concentrations. In quiescent tobacco pith tissue, the levels of these compounds are reduced by a factor of 100. These results suggest that cytokinin may exert control of cell division through the accumulation of molecules (the dehydrodiconiferyl glucosides) that are apparent cell wall components. Images

Binns, A N; Chen, R H; Wood, H N; Lynn, D G

1987-01-01

108

Purification and structure determination of glucosides of capsaicin and dihydrocapsaicin from various Capsicum fruits.  

PubMed

Two new glucosides, capsaicin-beta-D-glucopyranoside (1) and dihydrocapsaicin-beta-D-glucopyranoside (2), were discovered in the fruit of the Capsicum annuum cultivar 'High Heat'. They were sequentially purified by acetone extraction, n-hexane extraction, and acetonitrile extraction, followed by medium-pressure liquid chromatography and high-performance liquid chromatography performed on an octadecylsilane column. Their chemical structures were elucidated by proton nuclear magnetic resonance, carbon nuclear magnetic resonance, and hydrolysis with alpha- and beta-glucosidases. The glucosides were also detected in various pungent cultivars of C. annuum, Capsicum frutescens, and Capsicum chinense by liquid chromatography-mass spectrometry. However, they were not detected in nonpungent cultivars of C. annuum. Furthermore, a positive correlation was observed between the quantity of the capsaicinoids, capsaicin, and dihydrocapsaicin and their glucosides. PMID:16881699

Higashiguchi, Fumiharu; Nakamura, Hiroyasu; Hayashi, Hideo; Kometani, Takashi

2006-08-01

109

Metabolism of the masked mycotoxin deoxynivalenol-3-glucoside in pigs.  

PubMed

Plants can metabolize the Fusarium mycotoxin deoxynivalenol (DON) by forming the masked mycotoxin deoxynivalenol-3-?-d-glucoside (D3G). D3G might be cleaved during digestion, thus increasing the total DON burden of an individual. Due to a lack of invivo data, D3G has not been included in the various regulatory limits established for DON so far. The aim of our study was to contribute to the risk assessment of D3G by determination of its metabolism in pigs. Four piglets received water, D3G (116?g/kg b.w.) and the equimolar amount of DON (75?g/kg b.w.) by gavage on day 1, 5 and 9 of the experiment, respectively. Additionally, 15.5?g D3G/kg b.w. were administered intravenously on day 13. Urine and feces were collected for 24h and analyzed for DON, D3G, deoxynivalenol-3-glucuronide (DON-3-GlcA), deoxynivalenol-15-GlcA (DON-15-GlcA) and deepoxy-deoxynivalenol (DOM-1) by UHPLC-MS/MS. After oral application of DON and D3G, in total 84.8±9.7% and 40.3±8.5% of the given dose were detected in urine, respectively. The majority of orally administered D3G was excreted in form of DON, DON-15-GlcA, DOM-1 and DON-3-GlcA, while urinary D3G accounted for only 2.6±1.4%. In feces, just trace amounts of metabolites were found. Intravenously administered D3G was almost exclusively excreted in unmetabolized form via urine. Data indicate that D3G is nearly completely hydrolyzed in the intestinal tract of pigs, while the toxin seems to be rather stable after systemic absorption. Compared to DON, the oral bioavailability of D3G and its metabolites seems to be reduced by a factor of up to 2, approximately. PMID:24968060

Nagl, Veronika; Woechtl, Bettina; Schwartz-Zimmermann, Heidi Elisabeth; Hennig-Pauka, Isabel; Moll, Wulf-Dieter; Adam, Gerhard; Berthiller, Franz

2014-08-17

110

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

PubMed

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

2012-12-01

111

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

PubMed

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

2012-09-01

112

Comparison of Stevia plants grown from seeds, cuttings and stem-tip cultures for growth and sweet diterpene glucosides  

Microsoft Academic Search

The growth and sweet diterpene glucosides of Stevia plants propagated by stem-tip cultures were compared with those of the control plants propagated by seeds. There was no significant difference between the two groups both in growth and in chemical composition. As for the contents of sweet diterpene glucosides, however, the clonal plants showed significantly smaller variations than the sexually propagated

Yukiyoshi Tamura; Shigeharu Nakamura; Hiroshi Fukui; Mamoru Tabata

1984-01-01

113

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

SciTech Connect

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

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

1988-11-01

114

(6S)-Hydroxy-3-oxo-alpha-ionol glucosides from Capparis spinosa fruits.  

PubMed

Two new (6S)-hydroxy-3-oxo-alpha-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 alpha-ionol derivatives are metabolites of (+)-(S)-abscisic acid. PMID:11830166

Cali?, Ihsan; Kuruüzüm-Uz, Ay?e; Lorenzetto, Piergiorgio A; Rüedi, Peter

2002-02-01

115

[Study on antioxidant activity of two major secoiridoid glucosides in the fruits of Ligustrum lucidum Ait].  

PubMed

The antioxidant effects of two major secoiridoid glucosides (nuezhenoside and G13, separated in our laboratory) from Fructus Ligustri Lucidi had already been assayed though DPPH radicals, respectively. The results revealed that these ingredients showed significant antioxidant activities. A positive correlation existed between total content and antioxidant activity. G13 had shown higher antioxidant activity than nuezhenoside. It implied that the structure of secoiridoid glucoside was postitive to antioxidant activity. Otherwise, the results could promote the deep research of Furctus Ligustri Lucidi on antioxidant mechanism. PMID:17727057

Li, Yang; Zuo, Yan; Sun, Wen-Ji

2007-05-01

116

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

PubMed

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

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

2004-11-01

117

Iridoid glycoside-based quantitative chromatographic fingerprint analysis: a rational approach for quality assessment of Indian medicinal plant Gambhari (Gmelina arborea).  

PubMed

A sensitive, selective and robust qualitative and quantitative densitometric high-performance thin layer chromatographic method was developed and validated for the determination of iridoid glycoside in the aerial part of Gambhari (Gmelina arborea). Iridoid gycoside 6-O-(2'',3''-dibenzoyl)-alpha-l-rhamnopyranosylcatalpol (IG) was used as a chemical marker for the standardization of G. arborea plant extracts. The separation was performed on aluminum Kieselgel 60F254 TLC plates using chloroform-methanol as mobile phase. The quantitation of IG was carried out using the densitometric reflection/absorption mode at 240 and 430 nm after post-chromatographic derivatization with vanillin-sulphuric acid reagent. A precise and accurate quantification can be performed in the linear working concentration range of 1000-5000 ng/spot with good correlation (r2=0.994). The method was validated for peak purities, precision, robustness, limit of detection (LOD) and quantitation (LOQ), etc., as per ICH guidelines. Specificity of quantitation was confirmed using retention factor (R(f)), UV-vis spectral correlation and ESI-MS spectra of marker compound (IG) in sample track. PMID:18524530

Yadav, Akhilesh K; Tiwari, N; Srivastava, P; Singh, Subhash C; Shanker, K; Verma, Ram K; Gupta, Madan M

2008-08-01

118

Beta-glucoside kinase (BglK) from Klebsiella pneumoniae. Purification, properties, and preparative synthesis of 6-phospho-beta-D-glucosides.  

PubMed

ATP-dependent beta-glucoside kinase (BglK) has been purified from cellobiose-grown cells of Klebsiella pneumoniae. In solution, the enzyme (EC ) exists as a homotetramer composed of non-covalently linked subunits of M(r) approximately 33,000. Determination of the first 28 residues from the N terminus of the protein allowed the identification and cloning of bglK from genomic DNA of K. pneumoniae. The open reading frame (ORF) of bglK encodes a 297-residue polypeptide of calculated M(r) 32,697. A motif of 7 amino acids (AFD(7)IG(9)GT) near the N terminus may comprise the ATP-binding site, and residue changes D7G and G9A yielded catalytically inactive proteins. BglK was progressively inactivated (t(12) approximately 19 min) by N-ethylmaleimide, but ATP afforded considerable protection against the inhibitor. By the presence of a centrally located signature sequence, BglK can be assigned to the ROK (Repressor, ORF, Kinase) family of proteins. Preparation of (His6)BglK by nickel-nitrilotriacetic acid-agarose chromatography provided high purity enzyme in quantity sufficient for the preparative synthesis (200-500 mg) of ten 6-phospho-beta-d-glucosides, including cellobiose-6'-P, gentiobiose-6'-P, cellobiitol-6-P, salicin-6-P, and arbutin-6-P. These (and other) derivatives are substrates for phospho-beta-glucosidase(s) belonging to Families 1 and 4 of the glycosylhydrolase superfamily. The structures, physicochemical properties, and phosphorylation site(s) of the 6-phospho-beta-d-glucosides have been determined by fast atom bombardment-negative ion spectrometry, thin-layer chromatography, and (1)H and (13)C NMR spectroscopy. The recently sequenced genomes of two Listeria species, L. monocytogenes EGD-e and L. innocua CLIP 11262, contain homologous genes (lmo2764 and lin2907, respectively) that encode a 294-residue polypeptide (M(r) approximately 32,200) that exhibits approximately 58% amino acid identity with BglK. The protein encoded by the two genes exhibits beta-glucoside kinase activity and cross-reacts with polyclonal antibody to (His6)BglK from K. pneumoniae. The location of lmo2764 and lin2907 within a beta-glucoside (cellobiose):phosphotransferase system operon, may presage both enzymatic (kinase) and regulatory functions for the BglK homolog in Listeria species. PMID:12110692

Thompson, John; Lichtenthaler, Frieder W; Peters, Siegfried; Pikis, Andreas

2002-09-13

119

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

CHRISTINE M. HANSEN; JAMES E. LEKLEM; LORRAINE T. MILLER

120

Rapid Method for Determination of Anthocyanin Glucosides and Free Delphinidin in Grapes Using u-HPLC.  

PubMed

A rapid method for the determination of anthocyanin glucosides and free delphinidin in food using ultra-high-performance liquid chromatography (u-HPLC) was validated through tests of precision, accuracy and linearity. The u-HPLC separation was performed on a reversed-phase C18 column (particle size 2 µm, i.d. 2 mm, length 100 mm) with a photodiode array detector. The limits of detection and quantification of the u-HPLC analyses ranged from 0.07 to 0.65 mg/kg for nine types of anthocyanin glucosides and from 0.08 to 0.26 mg/kg for delphinidin aglycone. The intra-day and inter-day precision of individual anthocyanin glucosides and delphinidin aglycone were less than 9.42%. All calibration curves showed good linearity (coefficient of determination = 0.99) within the tested ranges. The rapid and simultaneous u-HPLC method presented in this study significantly improved the speed, sensitivity and resolution of the analyses of nine types of anthocyanin glucosides and free delphidinin aglycone in grapes. PMID:23839806

Shim, You-Shin; Kim, Seunghee; Seo, Dongwon; Park, Hyun-Jin; Ha, Jaeho

2014-08-01

121

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

2009-01-01

122

In vitro evaluation of secoiridoid glucosides from the fruits of Ligustrum lucidum as antiviral agents.  

PubMed

Six secoiridoid glucosides, lucidumoside C (1), oleoside dimethylester (2), neonuezhenide (3), oleuropein (4), ligustroside (5) and lucidumoside A (6), isolated from the fruits of Ligustrum lucidum (Oleaceae), were examined in vitro for their activities against four strains of pathogenic viruses, namely herpes simplex type I virus (HSV-1), influenza type A virus (Flu A), respiratory syncytial virus (RSV) and parainfluenza type 3 virus (Para 3). Antiviral activities were evaluated by the cytopathic effect (CPE) inhibitory assay. The purpose was to check if the antioxidative potency of these glucosides correlated with their antiviral potency. Results showed that none of the glucosides had any significant activity against HSV-1 and Flu A. Oleuropein, however, showed significant antiviral activities against RSV and Para 3 with IC50 value of 23.4 and 11.7 microg/ml, respectively. Lucidumoside C, oleoside dimethylester and ligustroside showed potent or moderate antiviral activities against Para 3 with IC50 values of 15.6-20.8 microg/ml. These results also documented that the anti-oxidative potency of these secoiriodoid glucosides was not directly related to their antiviral effects. PMID:11724241

Ma, S C; He, Z D; Deng, X L; But, P P; Ooi, V E; Xu, H X; Lee, S H; Lee, S F

2001-11-01

123

Simultaneous extraction of bioactive limonoid aglycones and glucoside from Citrus aurantium L. using hydrotropy.  

PubMed

Citrus limonoids were demonstrated to possess potential biological activities in reducing the risk of certain diseases. Limonoids are present in citrus fruits in the form of aglycones and glucosides. At present, limonoid aglycones and limonoid glucosides are extracted in multiple steps using different solvents. In order to understand their potential bioactivity, it may be beneficial to isolate and purify these compounds using environment friendly methods. A new method of extraction and purification of limonoids was established using a hydrotrope polystyrene adsorbent resin. Extraction of aglycones and glucosides was achieved in a single step, using an aqueous solution of sodium cumene sulphonate (Na-CuS). Sour orange (Citrus aurantium L.) seed powder was extracted with 2 M Na-CuS solution at 45 degrees C for 6 h. The filtered extract was diluted with water and loaded on an SP 700 adsorbent column. The column was washed with distilled water to remove the hydrotrope and then eluted using water and methanol in different compositions to obtain three compounds. The structures of the isolated compounds were confirmed by NMR spectroscopy as deacetyl nomilinic acid glucoside (DNAG), deacetyl nomilin (DAN) and limonin (LIM). PMID:18533458

Dandekar, Deepak V; Jayaprakasha, Guddadarangavvanahally K; Patil, Bhimanagouda S

2008-01-01

124

Thunberginols C, D, and E, new antiallergic and antimicrobial dihydroisocoumarins, and thunberginol G 3'-O-glucoside and (-)-hydrangenol 4'-O-glucoside, new dihydroisocoumarin glycosides, from Hydrangeae Dulcis Folium.  

PubMed

New antiallergic and antimicrobial dihydroisocoumarins, thunberginols C, D, and E, were isolated from Hydrangeae Dulcis Folium, the fermented and dried leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO, together with new dihydroisocoumarin glycosides, thunberginol G 3'-O-glucoside and (-)-hydrangenol 4'-O-glucoside. Their chemical structures have been determined on the basis of chemical and physicochemical evidence. Thunberginols C, D, E, G, and (-)-hydrangenol 4'-O-glucoside showed antiallergic activity in the in vitro bioassay using the Schults-Dale reaction in sensitized guinea pig bronchial muscle, and they also exhibited antimicrobial activity against oral bacteria. PMID:1363465

Yoshikawa, M; Uchida, E; Chatani, N; Kobayashi, H; Naitoh, Y; Okuno, Y; Matsuda, H; Yamahara, J; Murakami, N

1992-12-01

125

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.

2004-01-01

126

LC determination of luteolin-7-O-?-D-glucoside and apigenin-7-O-?-D-glucoside in rat plasma after administration of Humulus scandens extract and its application to pharmacokinetic studies  

Microsoft Academic Search

The present study was to investigate the pharmacokinetics of luteolin-7-O-?-D-glucoside (LGL) and apigenin-7-O-?-D-glucoside (AGL) in rat plasma after intravenous administration of the Humulus scandens extract (HSE). A simple and accurate high-performance liquid chromatographic (HPLC) method was successfully developed for simultaneous determination of LGL and AGL in rat plasma after the plasma protein was precipitated with methanol. HPLC analysis was performed

Zaixing Chen; Xixiang Ying; Shu Meng; Xu Zhu; Hong Jiang; Qishen Cao; Lin Wang; Fanhao Meng

2012-01-01

127

LC determination of luteolin-7-O-?-D-glucoside and apigenin-7-O-?-D-glucoside in rat plasma after administration of Humulus scandens extract and its application to pharmacokinetic studies  

Microsoft Academic Search

The present study was to investigate the pharmacokinetics of luteolin-7-O-?-D-glucoside (LGL) and apigenin-7-O-?-D-glucoside (AGL) in rat plasma after intravenous administration of the Humulus scandens extract (HSE). A simple and accurate high-performance liquid chromatographic (HPLC) method was successfully developed for simultaneous determination of LGL and AGL in rat plasma after the plasma protein was precipitated with methanol. HPLC analysis was performed

Zaixing Chen; Xixiang Ying; Shu Meng; Xu Zhu; Hong Jiang; Qishen Cao; Lin Wang; Fanhao Meng

2011-01-01

128

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

Microsoft Academic Search

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

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

2004-01-01

129

Isolation of N,N-dimethyl and N-methylserotonin 5-O-?-glucosides from immature Zanthoxylum piperitum seeds.  

PubMed

Two serotonin derivatives, N,N-dimethylserotonin 5-O-?-glucoside (1a) and N-methylserotonin 5-O-?-glucoside (1b) were isolated from immature seeds of Zanthoxylum piperitum. Their structures were determined by multi-step conversion reactions and spectroscopic analyses. Immature seeds of Z. piperitum contained extremely high levels of compounds 1a and 1b of approximately 0.29% and 0.15% (w/w), respectively. PMID:20834148

Yanase, Emiko; Ohno, Masaki; Harakawa, Hironari; Nakatsuka, Shin-ichi

2010-01-01

130

Biosynthesis of dehydrodiconiferyl alcohol glucosides: implications for the control of tobacco cell growth.  

PubMed

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

Orr, J D; Lynn, D G

1992-01-01

131

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

PubMed Central

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

Orr, John D.; Lynn, David G.

1992-01-01

132

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

PubMed

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

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

2012-09-01

133

Evidence of cytokinin bases, ribosides and glucosides in roots of Douglas-fir, Pseudotsuga menziesii.  

PubMed

Concentrations of cytokinin-like compounds were measured in root tips of Douglas-fir (Pseudotsuga menziesii (Mirb.) Franco) collected in spring. Cytokinin bases and ribosides were estimated by radioimmunoassay after purification by immunoaffinity (zeatin riboside and isopentenyladenosine antibodies coupled to cellulose gel) and high performance liquid chromatography. Cytokinin glucosides were similarly analyzed in root extracts treated with beta-glucosidase and octadecyl-silica column chromatography in conjunction with immunoaffinity purification. The identity of predominant cytokinins obtained after enzymatic degradation was confirmed by gas chromatography-mass spectrometry. Each of the observed cytokinin bases and ribosides seemed to have a corresponding hexose conjugate form. Total quantity of cytokinin glucosides was twice that of cytokinin bases and ribosides, and the major compound was isopentenyladenosine hexose conjugate. PMID:14972999

Doumas, P; Bonnet-Masimbert, M; Zaerr, J B

1989-03-01

134

Development of bioactive functions in hydrangeae dulcis folium. V. On the antiallergic and antimicrobial principles of hydrangeae dulcis folium. (2). Thunberginols C, D, and E, thunberginol G 3'-O-glucoside, (-)-hydrangenol 4'-o-glucoside, and (+)-hydrangenol 4'-O-glucoside.  

PubMed

Following the characterization of thunberginols A, B, and F, six bioactive principles, thunberginols C, D, and E, thunberginol G 3'-O-glucoside, (-)-hydrangenol 4'-O-glucoside, and (+)-hydrangenol 4'-O-glucoside, were isolated from Hydrangeae Dulcis Folium, the processed leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO, together with four kaempferol and quercetin oligoglycosides. Their chemical structures have been determined on the basis of chemical and physicochemical evidence. Thunberginols C, D, E, and G and (-)-hydrangenol 4'-O-glucoside showed antiallergic activity in the in vitro bioassay using the Schultz-Dale reaction. These components also exhibited inhibitory activities on the histamine release from rat mast cells and on the histamine-induced contraction in isolated guinea pig tracheal chain. In addition, thunberginols C, D, E, and G showed antimicrobial activities against oral bacteria. PMID:8795265

Yoshikawa, M; Matsuda, H; Shimoda, H; Shimada, H; Harada, E; Naitoh, Y; Miki, A; Yamahara, J; Murakami, N

1996-08-01

135

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.

2013-01-01

136

Identification of a Novel Fluorophore, Xanthurenic Acid 8- O -?- D -glucoside in Human Brunescent Cataract  

Microsoft Academic Search

We have identified the chemical structure of a novel protein-unbound fluorescent glucoside (Fl-Glc), found to be far more abundant in the human brunescent cataractous lens nuclei than in non-brunescent ones. Our earlier experiments showed that long-term incubation of the protein-free filtrate of non-brunescent cataractous nuclei generated increasing amounts of a particular yet to be characterized fluorophore (Fl-X). High performance liquid

Etsuko Shirao; Kanako Ando; Amane Inoue; Yutaka Shirao; Dorairajan Balasubramanian

2001-01-01

137

Amyloglucosidase-catalysed synthesis of curcumin-bis-?- d -glucoside—a response surface methodological study  

Microsoft Academic Search

Response surface methodology (RSM) was employed to optimize amyloglucosidase-catalyzed synthesis of curcumin-bis-?-d-glucoside. A central composite rotatable design (CCRD) was employed involving five variables (enzyme concentration, curcumin concentration, incubation period, buffer concentration and pH) at five levels. A second-order polynomial equation with a R\\u000a 2 value 0.9 showed good correspondence between experimental and predicted yields. Three-dimensional surface and contour plots generated

Giriyapura R. Vijayakumar; Balaraman Manohar; Soundar Divakar

2006-01-01

138

Anaerobic transformation of quercetin-3-glucoside by bacteria from the human intestinal tract  

Microsoft Academic Search

From human feces two phenotypically different types of bacteria were isolated on quercetin-3-glucoside as carbon and energy\\u000a source. Isolates of one type were identified as strains of Enterococcus casseliflavus. They utilized the sugar moiety of the glycoside, but did not degrade the aglycon further. The sugar moiety (4 mM) was fermented\\u000a to 5.5 ± 2.1 mM formate, 2.1 ± 0.7

Heiko Schneider; Andreas Schwiertz; Matthew David Collins; M. Blaut

1999-01-01

139

Cytopiloyne, a novel polyacetylenic glucoside from Bidens pilosa, functions as a T helper cell modulator  

Microsoft Academic Search

An extract of Bidens pilosa, an anti-diabetic Asteraceae plant, has recently been reported to modulate T cell differentiation and prevent the development of non-obese diabetes (NOD) in NOD mice. In this paper, a novel bioactive polyacetylenic glucoside, cytopiloyne (1), was identified from the Bidens pilosa extract using ex vivo T cell differentiation assays based on a bioactivity-guided fractionation and isolation

Yi-Ming Chiang; Cicero Lee-Tian Chang; Shu-Lin Chang; Wen-Chin Yang; Lie-Fen Shyur

2007-01-01

140

Preparation of novel reagents 4-alkoxytrityl chlorides and their reaction with methyl ? -d-glucoside  

Microsoft Academic Search

A series of novel 4- O-alkoxytrityl chlorides ( 1) with different chain lengths was synthesized as a novel reagent for obtaining 6- O-alkylated cellulose with high regioselectivity via trityl groups in one reaction step without the use of any protective groups. These chlorides were reacted with methyl ?-d-glucoside, which was used as a model compound, to examine the reactivities toward

Shinsuke Ifuku; Hiroshi Kamitakahara; Fumiaki Nakatsubo

2004-01-01

141

Dietary cyanidin 3- O -?- d -glucoside increases ex vivo oxidation resistance of serum in rats  

Microsoft Academic Search

The effect of dietary cyanidin 3-O-?-d-glucoside (C3G), a typical anthocyanin pigment, on the generation of thiobarbituric acid reactive substances (TBARS) during\\u000a serum formation ex vivo and susceptibility of serum to further lipid peroxidation was studied in rats. Rats were fed a diet containing C3G (2 g\\/kg)\\u000a for 14 d. Feeding C3G resulted in a significant decrease in generation of TBARS

Takanori Tsuda; Fumihiko Horio; Toshihiko Osawa

1998-01-01

142

3-Desoxycallunin and 2?-acetylcallunin, two minor 2,3-dihydroflavonoid glucosides from Calluna vulgaris  

Microsoft Academic Search

The ethyl acetate soluble fraction obtained from the acetone extract of fresh Calluna vulgaris heather flowers afforded a mixture of two minor 2,3-dihydroflavonoid glucosides. Separations were achieved by column chromatography on polyamide as well as by reversed phase MPLC and HPLC. Structural elucidations were performed by UV, 1H and 13C NMR. The two novel compounds which are related to the

Daovy P. Allais; Albert J. Chulia; Mourad Kaouadji; Alain Simon; Christiane Delage

1995-01-01

143

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

PubMed Central

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.

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

2013-01-01

144

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

PubMed

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

2000-02-01

145

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

2005-01-01

146

Antiprotozoal activity of Melampyrum arvense and its metabolites.  

PubMed

An activity guided isolation of the H(2)O subextract of the crude extract of Melampyrum arvense L. afforded iridoid glucosides: aucubin (1), melampyroside (2), mussaenoside (3), mussaenosidic acid (4), 8-epi-loganin (5); flavonoids: apigenin (6), luteolin (7), luteolin 7-O-?-glucopyranoside (8); a lignan glycoside dehydrodiconiferyl alcohol 9-O-?-glucopyranoside (9); and benzoic acid (10). ?-Sitosterol (11) and a fatty acid mixture (12) were identified as the active principles of the CHCl(3) subextract. The structures of the isolates were elucidated by spectroscopic methods, while the composition of 12 was identified by GC-MS after methylation. Luteolin (7) appeared as the most active compound against Trypanosoma brucei rhodesiense and Leishmania donovani (IC(50) values 3.8 and 3.0??g/mL). Luteolin 7-O-?-glucopyranoside (8) displayed the best antiplasmodial activity against Plasmodium falciparum (IC(50) value 2.9??g/mL). This is the first detailed phytochemical study on Turkish M. arvense and the first report of the antiprotozoal effect of Melampyrum species and its constituents. PMID:20623589

Kirmizibekmez, Hasan; Atay, Irem; Kaiser, Marcel; Brun, Reto; Cartagena, Michelle M; Carballeira, Néstor M; Yesilada, Erdem; Tasdemir, Deniz

2011-01-01

147

Ethyl glucoside in human urine following dietary exposure: detection by 1H NMR spectroscopy as a result of metabonomic screening of humans.  

PubMed

Metabonomic screening of human urine samples using 1H NMR spectroscopy has revealed the presence of signals resulting from the excretion of ethyl glucoside. Experiments in volunteers have demonstrated that this ethyl glucoside results from dietary exposure to the compound, which is present in beverages such as rice wine and sake, rather than representing a new route for the metabolism of ethanol by humans. The limited studies undertaken in volunteers indicate that ethyl glucoside has a longer biological half life than ethanol itself. The potential problems associated with using this glucoside metabolite as a marker of ethanol consumption are considered. PMID:14978530

Teague, Claire; Holmes, Elaine; Maibaum, Elaine; Nicholson, Jeremy; Tang, Huiru; Chan, Queenie; Elliott, Paul; Stamler, Jeremiah; Ueshima, Hirotsugu; Zhou, Beifan; Wilson, Ian

2004-03-01

148

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

PubMed

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

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

2000-01-01

149

Amyloglucosidase-catalyzed synthesis of n -octyl- d -glucoside—analysis using response surface methodology  

Microsoft Academic Search

Amyloglucosidase (3.2.1.3)-catalyzed synthesis of n-octyl-d-glucoside was optimized using response surface methodology. A central composite rotatable design involving 32 experiments of five variables at five levels was employed to study the glucosylation reaction. Among the variables studied, namely, n-octanol (15–75 MEq to d-glucose), enzyme (20–100 mg ), pH (4.0–8.0), buffer volume (0.2–1.0 ml) and temperature (30–70°C), amyloglucosidase concentration, pH and temperature were found to

Giriyapura R. Vijayakumar; Balaraman Manohar; Soundar Divakar

2005-01-01

150

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

PubMed

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

2007-01-01

151

Glochidionionosides A-D: megastigmane glucosides from leaves of Glochidion zeylanicum (Gaertn.) A. Juss.  

PubMed

Five megastigmane glucosides were isolated from the leaves of Glochidion zeylanicum. One of them was a known compound, blumenol C O-beta-D-glucopyranoside (1), and the structures of the four new compounds, glochidionionosides A-D (2-5), were mainly elucidated by spectroscopic methods, including a modified Mosher's method. The absolute configurations of the six-membered ring of glochidionionoside D (5) were deduced by beta-D-glucopyranosylation-induced shift trends in the (13)C-NMR spectra and confirmed by X-ray analysis as its p-bromobenzoate (5b), and the axis chirality of C-7 was determined to be R. PMID:12612412

Otsuka, Hideaki; Kijima, Hidehiko; Hirata, Eiji; Shinzato, Takakazu; Takushi, Anki; Bando, Masahiko; Takeda, Yoshio

2003-03-01

152

New CuCl2-induced glucoside esters and other constituents from Portucala oleracea.  

PubMed

Two new glucoside esters 1 and 2 were produced as stress metabolites in the fresh leaves of Portulaca oleracea, in response to abiotic stress elicitation by CuCl(2). A new sugar ester (3) and two known compounds (4 and 5) were also isolated. Their structures were established by spectroscopic means. The antioxidative activities of stress metabolites and the related isolates were evaluated by DPPH assay. The results showed that new stress-driven adducts of monolignans and monoterpenes with a glucose bridge exhibited much stronger antioxidative activities than other compounds. PMID:22361155

Wu, Bin; Yu, Liyan; Wu, Xiaodan; Chen, Jianbo

2012-04-01

153

Effects of hypolaetin-8-glucoside and related flavonoids on soybean lipoxygenase and snake venom phospholipase A2.  

PubMed

Hypolaetin-8-glucoside, a novel flavonoid isolated from Sideritis mugronensis and possessing anti-inflammatory and gastroprotective properties in the rat, was compared with the structurally related flavonoids hypolaetin, isoscutellarein, rutin, quercetin and kaempferol for inhibitory effects on the enzymes soybean 15-lipoxygenase and snake venom phospholipase A2. The aglycone flavonoids dose-dependently inhibited snake venom phospholipase A2 but the glycosides hypolaetin-8-glucoside and rutin were inactive. All 6 flavonoids inhibited soybean 15-lipoxygenase with no differences between glycosides and aglycones, although flavonols appeared more active than flavones. The inhibition of these enzyme activities cannot explain the anti-inflammatory action of hypolaetin-8-glucoside, unless a significant proportion of the drug reaches the target tissue as the aglycone, hypolaetin. PMID:3938206

Alcaraz, M J; Hoult, J R

1985-11-01

154

Responses of maxillary sensilla styloconica inBombyx mori to glucosides fromOsmunda japonica, a nonhost plant.  

PubMed

We isolated glucosides from the royal fern,Osmunda japonica, which elicit a deterrent response in larvae ofBombyx mori. These compounds were absent in taro (Colocasia antiquorum) and castor-oil plant (Ricinus communis) leaves and did not evoke responses of sensory cells in the lateral and medial sensilla styloconica ofSpodoptera litura. This glucoside extract of the royal fern leaves stimulates receptors generally associated with deterrent. It is also possible that this compound may act as a behavioral deterrent, and from actual feeding tests, it is suggested that this compound may prevent feeding in some monophagous insects, such asBombyx mori. The deterrent glucoside possesses a noncyclic aglycon. PMID:24248706

Shimizu, T; Yazawa, M; Hirao, T; Arai, N

1993-11-01

155

Oviposition Cues for a Specialist Butterfly-Plant Chemistry and Size  

PubMed Central

The oviposition choice of an insect herbivore is based on a complex set of stimuli and responses. In this study, we examined the effect of plant secondary chemistry (the iridoid glycosides aucubin and catalpol) and aspects of size of the plant Plantago lanceolata, on the oviposition behavior of the specialist butterfly Melitaea cinxia. Iridoid glycosides are known to deter feeding or decrease the growth rate of generalist insect herbivores, but can act as oviposition cues and feeding stimulants for specialized herbivores. In a previous observational study of M. cinxia in the field, oviposition was associated with high levels of aucubin. However, this association could have been the cause (butterfly choice) or consequence (plant induction) of oviposition. We conducted a set of dual- and multiple-choice experiments in cages and in the field. In the cages, we found a positive association between the pre-oviposition level of aucubin and the number of ovipositions. The association reflects the butterfly oviposition selection rather than plant induction that follows oviposition. Our results also suggest a threshold concentration below which females do not distinguish between levels of iridoid glycosides. In the field, the size of the plant appeared to be a more important stimulus than iridoid glycoside content, with bigger plants receiving more oviposition than smaller plants, regardless of their secondary chemistry. Our results illustrate that the rank of a cue used for oviposition may be dependent on environmental context.

Biere, A.; Harvey, J. A.; van Nouhuys, S.

2008-01-01

156

Protective effect of iridoid glycosides from Paederia scandens (LOUR.) MERRILL (Rubiaceae) on uric acid nephropathy rats induced by yeast and potassium oxonate.  

PubMed

Iridoid glycosides of Paederia scandens (IGPS) are an active component isolated from Chinese herb P. scandens (LOUR.) MERRILL (Rubiaceae). Uric acid nephropathy (UAN) is caused by excessive uric acid, which results in damage of kidney tissue via urate crystals deposition in the kidneys. This study aimed to investigate the protective effects of IGPS on UAN in rats induced by yeast and potassium oxonate. Treatment groups received different doses of IGPS and allopurinol (AP) daily for 35 days respectively. The results showed that treatment with IGPS significantly prevented the increases of uric acid in serum and the elevation of systolic blood pressure (SBP), attenuated renal tissue injury, improved renal function and reserved the biological activity of NOS-1. IGPS also inhibited the biological activity of TNF-? and TGF-?1, and suppressed the mRNA expressions of TNF-? and TGF-?1 in renal tissue. Taken together, the present and our previous findings suggest that IGPS exerts protective effects against kidney damage in UAN rats through its uric acid-lowering, anti-inflammatory and immunomodulatory properties. Furthermore, decreasing SBP by up regulation of NOS-1 expression and down regulation of TNF-? and TGF-?1 expression are involved in the effect of IGPS on high uric acid-induced nephropathy. PMID:24287205

Hou, Shi-xiang; Zhu, Wen-jing; Pang, Ming-qun; Jeffry, Joseph; Zhou, Lan-lan

2014-02-01

157

Extraction parameters and capillary electrophoresis analysis of limonin glucoside and phlorin in citrus byproducts.  

PubMed

Limonin glucoside (LG) and phlorin were extracted from citrus fruit tissues and assayed by capillary electrophoresis (CE). LG was determined in dried [1.20 +/- 0.10 mg of dry weight (dw)] and wet peel residues (1.16 +/- 0.04 mg of dw), orange juice finisher pulp (0.58 +/- 0.03 mg of dw), dried grapefruit seeds (2.70 +/- 0.15 mg of dw), and 50 degrees Brix molasses (2225 +/- 68 mg/L). Phlorin was purified from orange peel residue and grapefruit albedo, and concentrations were determined in some citrus products. Phlorin and LG were extracted from residues with water/pectinase or with water solutions of methanol and ethanol. Efficient LG extraction from grapefruit seeds (2.40 +/- 0.15 mg/g) was achieved with 50-65% methanol, solvent polarity P' approximately equal to 7-8. Extracts were purified and concentrated by adsorptive resins and HPLC to obtain 95% pure compounds of LG and phlorin. CE analysis did not require extract purification beyond filtration. LG and phlorin migrated as anions in electropherograms containing peaks representing other citrus flavonoids and limonoid glucosides. PMID:11743796

Braddock, R J; Bryan, C R

2001-12-01

158

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

PubMed

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

2013-12-01

159

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

PubMed Central

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

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

2013-01-01

160

Freezing and melting behavior of an octyl ?-D-glucoside-water binary system--inhibitory effect of octyl ?-D-glucoside on ice crystal formation.  

PubMed

Phase transition behavior of lyotropic liquid crystals of an octyl ?-D-glucoside (OG)-water binary system during ice freezing and melting was studied by differential scanning calorimetry (DSC) and polarizing optical microscopy (POM). Not the thermotropic, but the lyotropic phase transition due to the change of OG concentration during ice freezing and melting was observed. The concentration-temperature phase diagram of the binary system was constructed. Melting temperature of ice, T(m), lyotropic phase transition temperature, T(tr), and glass transition temperatures of unfrozen phases in the absence and presence of ice, T(g) and T(g)', were shown in the phase diagram. The phase diagram indicated that the OG aqueous system was concentrated to ca. 90-92 wt% by ice freezing and exhibited glass transition at T(g)'. An observation of the concentration-gradient specimen by the cryo-POM showed the evidence of the inhibitory effects of OG on nucleation and growth of ice crystals in the extremely high OG concentration system in which the lamellar liquid crystalline phase was formed. This study provided the importance of the influence of concentration change by ice freezing on the behaviour of the sugar-based surfactant-water system under low temperature conditions. PMID:23133837

Ogawa, Shigesaburo; Asakura, Kouichi; Osanai, Shuichi

2012-12-21

161

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

PubMed

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

2013-11-01

162

Eriodictyol-7-O-glucoside, a novel Nrf2 activator, confers protection against cisplatin-induced toxicity.  

PubMed

Eriodictyol-7-O-glucoside, a flavonoid isolated from Dracocephalum rupestre, is among the most potent free radical scavenger. In the present study, we identified eriodictyol-7-O-glucoside as a novel nuclear factor E2-related factor 2 (Nrf2) activator using a high-throughput cellular screening method. This compound activated Nrf2 signaling pathway and was able to stabilize Nrf2 by delaying Nrf2 degradation, resulting in accumulation of Nrf2 protein and activation of the Nrf2-dependent protective response. Recent studies have suggested that activation of Nrf2 pathway would confer protection against cisplatin-induced toxicity. The protective role of eriodictyol-7-O-glucoside in cisplatin-induced toxicity was investigated in a human renal mesangial cell line, HRMC. Cotreatment of HRMC cells with eriodictyol-7-O-glucoside significantly improved cell survival under cisplatin exposure. These findings demonstrated the feasibility of using natural compounds targeting Nrf2 as a therapeutic approach to subvert the side effects of cisplatin in normal cells. PMID:22465804

Hu, Qingwen; Zhang, Donna D; Wang, Limei; Lou, Hongxiang; Ren, Dongmei

2012-06-01

163

Anti-diabetic potential of ursolic acid stearoyl glucoside: a new triterpenic gycosidic ester from Lantana camara.  

PubMed

A new stearoyl glucoside of ursolic acid, urs-12-en-3?-ol-28-oic acid 3?-D-glucopyranosyl-4'-octadecanoate and other compounds were isolated from the leaves of Lantana camara L. The structure of this new glycoside was elucidated and established by standard spectroscopic methods. In streptozotocin-induced diabetic rats it showed significant reduction in blood glucose level. PMID:22051701

Kazmi, Imran; Rahman, Mahfoozur; Afzal, Muhammad; Gupta, Gaurav; Saleem, Shakir; Afzal, Obaid; Shaharyar, Md Adil; Nautiyal, Ujjwal; Ahmed, Sayeed; Anwar, Firoz

2012-01-01

164

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

Microsoft Academic Search

BACKGROUND: Quercetin and quercetin glycosides are widely consumed flavonoids found in many fruits and vegetables. These compounds have a wide range of potential health benefits, and understanding the bioavailability of flavonoids from foods is becoming increasingly important. METHODS: This study combined an in vitro digestion, a lactase treatment and the Caco-2 cell model to examine quercetin and quercetin glucoside uptake

Jeanelle Boyer; Dan Brown; Rui Hai Liu

2005-01-01

165

Two novel aromatic glucosides, marylaurencinosides D and E, from the fresh flowers of Cymbidium Great Flower 'Marylaurencin'.  

PubMed

Two novel aromatic glucosides, named marylaurencinosides D (1) and E (2), were isolated from the fresh flowers of Cymbidium Great Flower 'Marylaurencin'. In addition, eight known aromatic compounds (3-10) were isolated. These structures were determined on the basis of NMR experiments as well as chemical evidence. PMID:24448888

Yoshikawa, Kazuko; Okahuji, Mariko; Iseki, Kanako; Ito, Takuya; Asakawa, Yoshinori; Kawano, Sachiko; Hashimoto, Toshihiro

2014-04-01

166

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

PubMed

Anthocyanins are a group of naturally occurring phenolic compounds as colorants in several plants, flowers and fruits. These pigments have a great importance as quality indicators, as chemotaxonomic markers and antioxidants. The content of blackberry (Rubus species) juice was investigated by HPLC/ESI/MS using narrow bore HPLC columns. Using this method we demonstrated that cyanidin-3-O-glucoside represents about 80% of the total anthocyanin contents in blackberry extract. Here we investigated antioxidant activity of the blackberry juice and cyanidin-3-O-glucoside on the endothelial dysfunction in cells and in vascular rings exposed to peroxynitrite. In human umbilical vein endothelial cells (HUVEC) in vitro, peroxynitrite caused a significant suppression of mitochondrial respiration (38 +/- 2.1% of control cells), as measured by the mitochondrial-dependent conversion of the dye MTT to formazan. Peroxynitrite caused DNA strand breakage (63 +/- 1.9% single strand vs 3 +/- 0.9% single strand in control cells), as measured by the alkaline unwinding assay, and caused an activation of PARS, as measured by the incorporation of radiolabeled NAD(+) to nuclear proteins. Blackberry juice (different dilutions that contained 80 ppm;40 ppm;14.5 ppm of cyanidin-3-O-glucoside) and cyanidin-3-O-glucoside (as chloride) (0.085 microM; 0.028 microM; 0.0085 microM) reduced the peroxynitrite-induced suppression of mitochondrial respiration, DNA damage and PARS activation in HUVECs. Vascular rings exposed to peroxynitrite exhibited reduced endothelium-dependent relaxant responses in response to acetylcholine as well as a vascular contractility dysfunction in response to norepinephrine. The development of this peroxynitrite-induced vascular dysfunction was ameliorated by the blackberry juice (different dilutions that contained 80 ppm;40 ppm;14.5 ppm of cyanidin-3-O-glucoside) and cyanidin-3-O-glucoside (as chloride) (0.085 microM;0.028 microM;0.0085 microM). In conclusion our findings clearly demonstrate that blackberry juice containing cyanidin-3-O-glucoside is a scavenger of peroxynitrite and that exert a protective effect against endothelial dysfunction and vascular failure induced by peroxynitrite. PMID:12818719

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

2003-07-18

167

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

PubMed

The stable L-ascorbic acid glucoside produced by the action of the cyclomaltodextrin glucanotransferase (CGTase, EC 2.4.1.19) 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

1992-08-01

168

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

PubMed

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

2013-09-01

169

Oligo(phenylene ethynylene) Glucosides: Modulation of Cellular Uptake Capacity Preserving Light ON.  

PubMed

A new family of oligo(phenylene ethynylene) (OPE) glucosides has been prepared and characterized. Our results demonstrate that fine-tuning of their photophysical properties can be obtained by acting on the electronics of the core and molecular skeleton. Modulation of the hydrophobic chain length and substituents on the central moieties influences the bioaffinity too. In particular, introducing a NMe2 group on the aromatic central core affords a highly efficient biocompatible fluorescent probe that can be taken up in cytoplasmic vesicles of HEp-2 cells (cells from epidermoid carcinoma larynx tissue). The photophysical behavior, high quantum yield, and stability open the way to the use of the OPE family as stains for cellular imaging analysis by fluorescence microscopy. PMID:24815093

Barattucci, Anna; Deni, Elisa; Bonaccorsi, Paola; Ceraolo, Maria Grazia; Papalia, Teresa; Santoro, Antonio; Sciortino, Maria Teresa; Puntoriero, Fausto

2014-06-01

170

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

PubMed

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

2013-03-15

171

Structure and cytotoxic activity of enzymatic hydrolysis products of secoiridoid glucosides, isoligustroside and isooleuropein.  

PubMed

Hydrolysis of isoligustroside (1) and isooleuropein (2), secoiridoid glucosides, in the presence of ?-glucosidase provided 2-(4-hydroxyphenyl)methyl (2R,3S,4S)-3-formyl-3,4-dihydro-4-(2-methoxy-2-oxoethyl)-2-methyl-2H-pyran-5-carboxylate (3) and 2-(3,4-dihydroxyphenyl)methyl (2R,3S,4S)-3-formyl-3,4-dihydro-4-(2-methoxy-2-oxoethyl)-2-methyl-2H-pyran-5-carboxylate (4), respectively. The structures of 3 and 4 were elucidated on the basis of extensive spectral analyses, including 2D-NMR experiments. Compounds 3 and 4 were found to be new rearrangement products of the aglycones of 1 and 2. The cytotoxic activities of 3 and 4 were evaluated using a disease-oriented panel of 39 human cancer cell lines and showed moderate cytotoxic activity for 4, while 3 exhibited weaker activity compared to that of 4. PMID:21480510

Kikuchi, Masafumi; Yaoita, Yasunori; Mano, Nariyasu; Kikuchi, Masao

2011-04-01

172

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

PubMed

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

2011-11-01

173

The effect of octyl glucoside on rheological behavior of diluted and concentrated lamellar phases.  

PubMed

We have investigated the rheological properties of lamellar liquid crystal formed by nonionic surfactants at low and high surfactant concentrations with a small amount of octyl glucoside and their relationship with the topology of the bilayer. Rheology is a specific signature of each bilayer topology. The decrease in viscosity by increasing the shear rate according to a power law with exponent close to -0.8 was found for the concentrated system of LSB/1-butanol/water and 1% in weight of OG. On the contrary, the decrease in the viscosity by increasing the shear rate for the diluted system is less pronounced with lower exponent values. The rheological data agrees with the presence of vesicles. A special case is the system with benzyl alcohol. The apparent viscosity does not follow the same power law than for alkanols. PMID:16380125

Granizo, N; Alvarez, M; Valiente, M

2006-06-01

174

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

PubMed

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

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

2013-12-01

175

Daphnane-type diterpenoid glucosides and further constituents of Euphorbia pilosa.  

PubMed

Phytochemical investigation of whole plants of Euphorbia pilosa led to the isolation and identification of two new daphnane-diterpenoid glucosides, euphopilosides A and B (1 and 2, resp.), and a new ent-abietane, euphopilolide (3), together with eight known compounds. Compounds 1 and 2 are the first daphnane-type diterpenoid glycosides. Their structures were elucidated by a combination of 1D- and 2D-NMR, and MS analyses, and acid hydrolysis. Compounds 1-9 were evaluated for their in vitro cytotoxicities against five human tumor cell lines, HL-60, SMMC-7721, A-549, MCF-7, and SW-480. Compound 7 showed moderate inhibitory activity against all five cell lines. PMID:24827685

Zhang, Xu-Dong; Ni, Wei; Yan, Huan; Li, Gen-Tao; Zhong, Hui-Min; Li, Yan; Liu, Hai-Yang

2014-05-01

176

New secoiridoid glucosides from Ligustrum lucidum induce ERK and CREB phosphorylation in cultured cortical neurons.  

PubMed

Two new secoiridoid glucosides, namely iso-oleonuezhenide (1) and methyloleoside 7-ethyl ester (2), along with five known ones, oleonuezhenide (3), nuezhenide (4), oleuropein (5), G13 (6), and jaspolyside methyl ester (7), were isolated from the fruits of Ligustrum lucidum. Their structures were assigned based on 1H-NMR, 13C-NMR, and 2D-NMR analyses, in combination with HR-MS experiments and the comparison with literature data of related compounds, as well as on chemical experiments. We have examined the ability of these compounds to activate ERK and CREB in cultured cortical neurons. Our studies demonstrate that compound 1 induces ERK and CREB phosphorylation in primary cortical neurons in a dose- and temporal-dependent manner, suggesting its bioactivity on neurons. PMID:20143293

Fu, Guangmiao; Ip, Fanny C F; Pang, Haihong; Ip, Nancy Y

2010-07-01

177

Baimantuoluosides D-G, four new withanolide glucosides from the flower of Datura metel L.  

PubMed

In our search for bioactive anti-psoriasis compounds from the flower of Datura metel L, we isolated four new withanolide glucosides, baimantuoluosides D, E, F and G (1-4). The structures of the new compounds are (5alpha,6alpha,7beta,22R)-5,6,7,27-tetrahydroxy-1-oxowitha-2,24-dien-27-O-beta-D-glucopyranoside (1), (5alpha,6beta,7alpha,22R)-5,6,7,27-tetrahydroxy-1-oxowitha-2,24-dien-27-O-beta-D-glucopyranoside (2), (5alpha,6beta,7alpha,12beta,22R)-5,6,7,12,27-pentahydroxy-1-oxowitha-2,24-dien-27-O-beta-D-glucopyranoside (3), and (5alpha,6beta,22R)-5,6,27-trihydroxy-1-oxowitha-2,24-dien-27-O-beta-D-glucopyranoside (4) on the basis of chemical and physicochemical evidence. PMID:20803115

Yang, Bing-you; Xia, Yong-gang; Wang, Qiu-hong; Dou, De-qiang; Kuang, Hai-xue

2010-08-01

178

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

PubMed

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

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

2014-07-01

179

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

PubMed Central

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

Lohaus, Gertrud; Schwerdtfeger, Michael

2014-01-01

180

An LC-MS method for simultaneous determination of five iridoids from Zhi-zi-chi Decoction in rat brain microdialysates and tissue homogenates: Towards an in depth study for its antidepressive activity.  

PubMed

Zhi-zi-chi Decoction has been clinically utilized for the treatment of depression for more than thousand years. In order to investigate the possible bioactive components that could pass through the blood brain barrier (BBB) and the mechanism of antidepressant, a sensitive LC-MS method was developed to detect the ingredients (geniposide, scandoside methyl ester, gardenoside, deacetyl asperulosidic acid methyl ester and genipin-1-?-gentiobioside) in rat brain microdialysates and tissue homogenates samples (hippocampus, hypothalamus, premotor cortex, striatum, oblongata and cerebellum). Method development and validation are described in terms of calibration curves, extraction yield, lower limit of quantification (LLOQ), precision, accuracy, intra- and inter-day variability, which are in accordance with the requirements. Microdialysis in hippocampus demonstrated that the five iridoids possessed complete pharmacokinetic process while brain tissue homogenate method testified the distribution regularity in brain. The work clarified that the five iridoids, as antidepressant ingredients, could pass through the BBB, distribute targeted and possess complete pharmacokinetics in brain. These observations, along with the large database of rat brain microdialysates and tissue homogenates data, could enable future efforts aimed to improve our understanding of the relationship between bioactive ingredients and clinical therapy of depression. PMID:25049209

Qu, Kankan; Zhao, Longshan; Luo, Xinyi; Zhang, Chenning; Hou, Pengyi; Bi, Kaishun; Chen, Xiaohui

2014-08-15

181

PREPARATIVE SEPARATION OF AXIFOLIN-3-GLUCOSIDE, HYPEROSIDE AND AMYGDALIN FROM PLANT EXTRACTS BY HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY.  

PubMed

High-speed countercurrent chromatography (HSCCC) was successfully used to isolate three bioactive compounds, i.e., amygdalin from bitter almond and taxifolin-3-glucoside and quercetin-3-galactoside (hyperoside) from water extract of Agrimonia pilosa Ledeb, respectively. From 1 g of the crude extract 65 mg of amygdalin was isolated at 97% purity using a two-phase solvent system composed of ethyl acetate-n-butanol-water (5:2:5, v/v) by preparative HSCCC. From a 400 mg amount of crude extract of Agrimonia pilosa Ledeb, 11 mg of taxifolin-3-glucoside and 8 mg of hyperoside were isolated at 96% purity using a two-phase solvent system composed of ethyl acetate-methanol-water (25:1:25, v/v) similarly by preparative HSCCC. The final structural identification was performed by MS, (1)H-NMR and (13)C-NMR Spectra. PMID:20046896

Wei, Yun; Xie, Qianqian; Ito, Yoichiro

2009-01-01

182

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.

2011-01-01

183

Flavone Glucoside Uptake into Barley Mesophyll and Arabidopsis Cell Culture Vacuoles. Energization Occurs by H+-Antiport and ATP-Binding Cassette-Type Mechanisms1  

PubMed Central

In many cases, secondary plant products accumulate in the large central vacuole of plant cells. However, the mechanisms involved in the transport of secondary compounds are only poorly understood. Here, we demonstrate that the transport mechanisms for the major barley (Hordeum vulgare) flavonoid saponarin (apigenin 6-C-glucosyl-7-O-glucoside) are different in various plant species: Uptake into barley vacuoles occurs via a proton antiport and is competitively inhibited by isovitexin (apigenin 6-C-glucoside), suggesting that both flavone glucosides are recognized by the same transporter. In contrast, the transport into vacuoles from Arabidopsis, which does not synthesize flavone glucosides, displays typical characteristics of ATP-binding cassette transporters. Transport of saponarin into vacuoles of both the species is saturable with a Km of 50 to 100 ?m. Furthermore, the uptake of saponarin into vacuoles from a barley mutant exhibiting a strongly reduced flavone glucoside biosynthesis is drastically decreased when compared with the parent variety. Thus, the barley vacuolar flavone glucoside/H+ antiporter could be modulated by the availability of the substrate. We propose that different vacuolar transporters may be responsible for the sequestration of species-specific/endogenous and nonspecific/xenobiotic secondary compounds in planta.

Frangne, Nathalie; Eggmann, Thomas; Koblischke, Carsten; Weissenbock, Gottfried; Martinoia, Enrico; Klein, Markus

2002-01-01

184

Isolation of antioxidative phenolic glucosides from lemon juice and their suppressive effect on the expression of blood adhesion molecules.  

PubMed

Phenolic glucosides having radical scavenging activity were examined from the fraction eluted with 20% methanol on Amberlite XAD-2 resin applied to lemon (Citrus limon) juice by using reversed phase chromatography. Four phenolic glucosides were identified as 1-feruloyl-beta-D-glucopyranoside, 1-sinapoyl-beta-D-glucopyranoside, 6,8-di-C-glucosylapigenin and 6,8-di-C-glucosyldiosmetin by (1)H-NMR, (13)C-NMR, and MS analyses. They exhibited radical scavenging activity for 1,1-diphenyl-2-picrylhydrazyl (DPPH) and superoxide, although the activity was low in comparison with eriocitrin, a potent antioxidant in lemon fruit, and the eriodictyol of its aglycone. The phenolic compounds in lemon juice were examined for their suppressive effect on the expression of blood adhesion molecules by measuring the expression of intercellular adhesion molecule-1 (ICAM-1) in human umbilical vein endothelial cells (HUVECs) induced by necrosis factor-alpha (TNF-alpha). 6,8-Di-C-glucosylapigenin, apigenin, and diosmentin of the flavones were found to significantly suppress the expression of ICAM-1 at 10 muM (P<0.05). The phenolic glucosides isolated in this study were contained in comparative abundance in daidai (Citrus aurantium) and niihime (Citrus unshiu x Citrus tachibana) among the sour citrus juices. PMID:17690486

Miyake, Yoshiaki; Mochizuki, Mika; Okada, Miki; Hiramitsu, Masanori; Morimitsu, Yasujiro; Osawa, Toshihiko

2007-08-01

185

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

PubMed

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

2012-06-01

186

Vesicle-micelle transition of phosphatidylcholine and octyl glucoside elucidated by cryo-transmission electron microscopy.  

PubMed Central

Vesicle-micelle transition structures of egg phosphatidylcholine (PC) and octyl glucoside (OG) mixtures were observed in the vitrified hydrated state by cryo-transmission electron microscopy (cryo-TEM) and correlated with the macroscopic and molecular changes previously associated with micellization monitored by 90 degrees light scattering and resonance energy transfer between fluorescent lipid probes. Several distinct structural changes occurred as OG was added to the PC vesicles. First, the average vesicle size decreased from 160 nm to less than 66 nm with no apparent change or decrease in optical density (OD). Then, associated with a small rise in OD, samples with open vesicles were observed coexisting with pieces of lamellae and long cylindrical micelles; more micelles were seen at higher [OG]. This mixture of vesicles and cylindrical micelles occurred in the region of the phase diagram previously attributed to vesicle opening, and possibly vesicle size increase. At higher [OG], small spheroidal micelles coexisting with cylindrical micelles correlated with a decrease in OD and changes in the fluorescence signal. At high [OG] when the solution appeared clear, spheroidal micelles were the dominant structure. By using cryo-TEM, a technique which preserves the original microstructure of fluid systems and provides direct images at 1 nm resolution, we have elucidated the vesicle-micelle transition and identified intermediates not known previously in the PC/OG system. Images FIGURE 1 FIGURE 2 FIGURE 4 FIGURE 6 FIGURE 7 FIGURE 8

Vinson, P K; Talmon, Y; Walter, A

1989-01-01

187

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

PubMed

Stroke is a complex disease that may involve oxidative stress-related pathways in its pathogenesis. The nuclear factor erythroid-2-related factor 2/antioxidant response element (Nrf2/ARE) pathway plays an important role in inducing phase II detoxifying enzymes and antioxidant proteins and thus has been considered a potential target for neuroprotection in stroke. The aim of the present study was to determine whether eriodictyol-7-O-glucoside (E7G), a novel Nrf2 activator, can protect against cerebral ischemic injury and to understand the role of the Nrf2/ARE pathway in neuroprotection. In primary cultured astrocytes, E7G increased the nuclear localization of Nrf2 and induced the expression of the Nrf2/ARE-dependent genes. Exposure of astrocytes to E7G provided protection against oxygen and glucose deprivation (OGD)-induced oxidative insult. The protective effect of E7G was abolished by RNA interference-mediated knockdown of Nrf2 expression. In vivo administration of E7G in a rat model of focal cerebral ischemia significantly reduced the amount of brain damage and ameliorated neurological deficits. These data demonstrate that activation of Nrf2/ARE signaling by E7G is directly associated with its neuroprotection against oxidative stress-induced ischemic injury and suggest that targeting the Nrf2/ARE pathway may be a promising approach for therapeutic intervention in stroke. PMID:24466583

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

2013-12-15

188

Evaluation of an amylase method utilizing p-nitrophenyl glucosides as substrates.  

PubMed

An enzymatic method which uses p-nitrophenyl glucosides as substrates for the determination of amylase activity has been evaluated. The kit can be used in either a two point or multiple point mode but these give different results. In both modes the reagent gave a linear response to at least 800 U/I. No interference by endogenous compounds was observed as has been reported with some enzymatic procedures. Within-batch precision (coefficient of variation 1% at 340 U/I and 5% at 10 U/I) and inter-batch precision (coefficient of variation 3.4% at 170 U/I and 3.7% at 56 U/I) are comparable to other amylase methodologies. Correlation with both the manual dye-starch (Phadebas) (r2 = 0.994) and the Beckman Amylase-DS (r2 = 0.998) methods was good for the sera and urines examined. Normal range for serum was 17 to 84 U/I (mean +/- 2 SD). The method is rapid (assay time 10 min), requires very little specimen (20 microliters for the two point assay and 5 microliters for the multiple point assay) and is suitable for both routine and emergency use. PMID:6179424

Bais, R

1982-08-01

189

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

PubMed

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

2013-03-01

190

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

PubMed

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

2006-01-01

191

Triterpene glucosides from the leaves of Aralia elata and their cytotoxic activities.  

PubMed

Three new triterpene glucosides, named congmuyenosides C-E (1-3, resp.), along with four known ones, were isolated from an EtOH extract of Aralia elata (Miq.) Seem. leaves. The structures of the new compounds were identified as 3-O-{?-D-glucopyranosyl-(1?3)-?-D-glucopyranosyl-(1?3)-[?-D-glucopyranosyl-(1?2)]-?-D-glucopyranosyl}caulophyllogenin (1), 3-O-{?-D-glucopyranosyl-(1?3)-?-D-glucopyranosyl-(1?3)-[?-D-glucopyranosyl-(1?2)]-?-D-glucopyranosyl}hederagenin 28-O-?-D-glucopyranosyl ester (2), 3-O-{?-D-glucopyranosyl-(1?3)-?-D-glucopyranosyl-(1?3)-[?-D-glucopyranosyl-(1?2)]-?-D-glucopyranosyl}echinocystic acid 28-O-?-D-glucopyranosyl ester (3) on the basis of spectral analyses, including MS, (1) H-NMR, (13) C-NMR, DEPT, HSQC, HMBC, NOESY, and HSQC-TOCSY experiments. All isolates obtained were evaluated for their cytotoxic activities against three human tumor cell lines (HepG2, SKOV3, and A549). Compound 3 showed significant cytotoxicity against A549 cell line (IC50 9.9±1.5??M). PMID:23576356

Kuang, Hai-Xue; Wang, Zhi-Bin; Wang, Qiu-Hong; Yang, Bing-You; Xiao, Hong-Bin; Okada, Yoshihito; Okuyama, Tohru

2013-04-01

192

Tetrahydroxystilbene glucoside, a plant-derived cognitive enhancer, promotes hippocampal synaptic plasticity.  

PubMed

Plant or food derived polyphenols have received a great deal of attention due to their biological properties including anti-oxidative effects, neuroprotection and memory enhancement. Here, we investigated the roles of 2,3,5,4'-tetrahydroxystilbene-2-O-?-d-glucoside (TSG), an active component of the rhizome extracted from Polygonum multiflorum, in the regulation of hippocampal synaptic plasticity in normal mice as well as the underlying mechanisms. It was shown that TSG promoted the differentiation of PC12 cells and increased the intracellular calcium level in hippocampal neurons. TSG facilitated high-frequency stimulation (HFS)-induced hippocampal long-term potentiation (LTP) in a bell-shaped manner. The facilitation of LTP induction by TSG required calcium/calmodulin-dependent protein kinase II (CaMKII) and extracellular signal-regulated kinase (ERK) activation. Taken together, our data demonstrate that TSG promotes LTP induction and this effect may contribute to the enhancement of learning and memory seen in animal models. PMID:20951128

Wang, Ting; Yang, Yuan-Jian; Wu, Peng-Fei; Wang, Wei; Hu, Zhuang-Li; Long, Li-Hong; Xie, Na; Fu, Hui; Wang, Fang; Chen, Jian-Guo

2011-01-10

193

Tetrahydroxystilbene glucoside protects human neuroblastoma SH-SY5Y cells against MPP+-induced cytotoxicity.  

PubMed

1-methyl-4-phenylpyridinium (MPP+), an inhibitor of mitochondrial complex I, has been widely used as a neurotoxin for inducing a cell model of Parkinson's disease. This study aimed to evaluate the effects of 2,3,5,4'-tetrahydroxystilbene-2-O-?-D-glucoside (TSG), an active component extracted from Polygonum multiflorum, on MPP+-induced cytotoxicity in human dopaminergic neuroblastoma SH-SY5Y cells. The results from the MTT and lactate dehydrogenase (LDH) assays showed that incubating cells with 500 ?M MPP+ for 24 h decreased cell viability and increased LDH leakage, whereas preincubating cells with 3.125 to 50 ?M TSG for 24 h protected the cells against MPP+-induced cell damage. Using 2',7'-dichlorofluorescin diacetate (DCFH-DA) and rhodamine 123, respectively, we found that TSG inhibited both the elevation of intracellular reactive oxygen species and the disruption of mitochondrial membrane potential induced by MPP+. In addition, TSG suppressed both the upregulation of the ratio of Bax to Bcl-2 and the activation of caspase-3 induced by MPP+, and TSG inhibited apoptosis as detected by flow cytometric analysis using Annexin-V and propidium (PI) label. These results suggest that TSG may protect neurons against MPP+-induced cell death through improving mitochondrial function, decreasing oxidative stress and inhibiting apoptosis, and this may provide a potentially new strategy for preventing and treating neurodegenerative disorders such as Parkinson's disease. PMID:21497157

Sun, Fang-ling; Zhang, Lan; Zhang, Ru-yi; Li, Lin

2011-06-25

194

Cytopiloyne, a novel polyacetylenic glucoside from Bidens pilosa, functions as a T helper cell modulator.  

PubMed

An extract of Bidens pilosa, an anti-diabetic Asteraceae plant, has recently been reported to modulate T cell differentiation and prevent the development of non-obese diabetes (NOD) in NOD mice. In this paper, a novel bioactive polyacetylenic glucoside, cytopiloyne (1), was identified from the Bidens pilosa extract using ex vivo T cell differentiation assays based on a bioactivity-guided fractionation and isolation procedure. Its structure was elucidated as 2beta-D-glucopyranosyloxy-1-hydroxytrideca-5,7,9,11-tetrayne by various spectroscopic methods. Functional studies showed that cytopiloyne was able to inhibit the differentiation of naïve T helper (Th0) cells into type I T helper (Th1) cells but to promote the differentiation of Th0 cells into type II T helper (Th2) cell. Accordingly, cytopiloyne also suppressed IFN-gamma expression and promoted IL-4 expression in mouse splenocytes ex vivo. These results suggest that cytopiloyne functions as a T cell modulator that may directly contribute to the ethnopharmacological effect of Bidens pilosa extract on preventing diabetes. Moreover, cytopiloyne can serve as an index compound for quality control of lot-to-lot extract preparations of Bidens pilosa. PMID:17101254

Chiang, Yi-Ming; Chang, Cicero Lee-Tian; Chang, Shu-Lin; Yang, Wen-Chin; Shyur, Lie-Fen

2007-04-01

195

Analysis of deoxynivalenol and deoxynivalenol-3-glucoside in hard red spring wheat inoculated with Fusarium graminearum.  

PubMed

Deoxynivalenol (DON) is a mycotoxin affecting wheat quality. The formation of the "masked" mycotoxin deoxinyvalenol-3-glucoside (D3G) results from a defense mechanism the plant uses for detoxification. Both mycotoxins are important from a food safety point of view. The aim of this work was to analyze DON and D3G content in inoculated near-isogenic wheat lines grown at two locations in Minnesota, USA during three different years. Regression analysis showed positive correlation between DON content measured with LC and GC among wheat lines, locality and year. The relationship between DON and D3G showed a linear increase until a certain point, after which the DON content and the D3G increased. Wheat lines having higher susceptibility to Fusarium showed the opposite trend. ANOVA demonstrated that the line and location have a greater effect on variation of DON and D3G than do their interaction among years. The most important factor affecting DON and D3G was the growing location. In conclusion, the year, environmental conditions and location have an effect on the D3G/DON ratio in response to Fusarium infection. PMID:24351715

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

2013-12-01

196

The first total synthesis of cytopiloyne, an anti-diabetic, polyacetylenic glucoside.  

PubMed

The first total synthesis of cytopiloyne 1, a novel bioactive polyacetylenic glucoside isolated from the extract of Bidens pilosa, is described. The structure of cytopiloyne was determined to be 2-?-D-glucopyranosyloxy-1-hydroxytrideca-5,7,9,11-tetrayne by using various spectroscopic methods, but the chirality of the polyyne moiety was unknown. Herein, the convergent synthesis of two diastereomers of cytopiloyne by starting from commercially available 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-diozolane is described. The synthetic sequence involved two key steps: stereoselective glycosylation of the glucosyl trichloroacetimidate with 1-[(4-methoxybenzyl)oxy]hex-5-yn-2-ol to give the desired ?-glycoside and the construction of the glucosyl tetrayne skeleton by using a palladium/silver-catalyzed cross-coupling reaction to form the alkyne-alkyne bond, the first such use of this reaction. Comparison between the observed and published characterization data showed the 2R isomer to be the natural product cytopiloyne. PMID:21681841

Kumar, Chidambaram Ramesh; Tsai, Chi-Hui; Chao, Yu-Sheng; Lee, Jinq-Chyi

2011-07-25

197

Structural characterization of inclusion complexes between cyanidin-3-O-glucoside and ?-cyclodextrin.  

PubMed

Inclusion complex formation between the multiple equilibrium forms of cyanidin-3-O-glucoside (cy3glc) and ?-cyclodextrin (?-CD) was investigated using a combined approach of NMR spectroscopy and Molecular Dynamics simulation. Diffusion ordered NMR spectroscopy (DOSY) and study of nuclear Overhauser effects (NOE) were used to determine the selective intermolecular interactions and structure of these complexes in aqueous solution. The observed chemical shift displacements of resonance signals of protons from the interior of ?-CD cavity and protons belonging to the hemiketal (B) and cis-chalcone forms (Cc), the diffusion measurements using DOSY and the NOE studies have anticipated the formation of an inclusion complex between these two forms and ?-CD. The analysis of the NMR spectral data has shown no evidence of internal interaction between ?-CD and the flavylium cation (AH(+)) or trans-chalcone (Ct) forms of cy3glc. The hemiketal formed a 1:1 inclusion complex with ?-cyclodextrin in which the pyranic C ring is deeply included inside the ?-CD cavity while B ring lies on the plane of the wider rim of ?-CD. The structure of the complexes was also clarified through a theoretical approach by Molecular Dynamics simulation. PMID:24507282

Fernandes, Ana; Ivanova, Galya; Brás, Natércia F; Mateus, Nuno; Ramos, Maria J; Rangel, Maria; de Freitas, Victor

2014-02-15

198

Citrus limonin and its glucoside inhibit colon adenocarcinoma cell proliferation through apoptosis.  

PubMed

The current study was an attempt to elucidate the mechanism of human colon cancer cell proliferation inhibition by limonin and limonin glucoside (LG) isolated from seeds of Citrus reticulata. The structures of purified compounds were confirmed by NMR and quantified using HPLC. These compounds of more than 95% purity were subjected to proliferation inhibition assay using human colon adenocarcinoma (SW480) cells. The IC50 value of 54.74 and 37.39 ?M was observed for limonin and LG, respectively at 72 h. Following confirmation of proliferation inhibition, pattern of DNA fragmentation and activation of caspase-3 of the cells treated with limonoids suggest involvement of apoptosis. Furthermore, reduction in the transcription ratio of bcl2/bax and induction of cytochrome c release from mitochondria to cytosol with treatment of limonoids confirm the activation of intrinsic apoptosis pathway. The activity of Bax and Bcl2 was confirmed through analysis of mitochondrial membrane potential and intracellular calcium in the cells treated with limonin and LG; the net content of caspase-8 was not affected by limonoids. Results of the current study provide compelling evidence on the induction of mitochondria mediated intrinsic apoptosis by both limonin and LG in cultured SW480 cells for the first time. PMID:21338095

Chidambara Murthy, Kotamballi N; Jayaprakasha, G K; Kumar, Vinod; Rathore, Keerti S; Patil, Bhimanagouda S

2011-03-23

199

Effect of atrial natriuretic peptide on alpha-methyl-D-glucoside intestinal active uptake in rats.  

PubMed

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 the sodium-glucose cotransporter (SGLT) of enterocytes. In the present study the inhibitory effect of 1 microM ANP on SGLT1 in rat small intestine and colon was tested. For this purpose, the apparent kinetic constants of SGLT1 were determined using radioactive alpha-methyl-D-glucoside (alpha-MG), a non-metabolizable glucose analogue that selectively serves the luminal Na+-dependent intestinal uptake, but not the serosal-facilitated diffusion sugar carrier. In both tissues, incubation with ANP increased Km without modifying the Vmax. In addition, Vmax in the small intestine was found to be higher than in the colon. The evidence presented here suggests that ANP, through its second messenger, may be a competitive inhibitor of SGLT1. Since SGLT1 is also expressed in the brush-border membrane of the renal proximal tubule, we suggest that this peptide might regulate the hydro-saline balance at intestinal and proximal tubular nephron levels. PMID:9786175

González Bosc, L V; Vidal, N A; Prieto, R; Tur, J A

1998-01-01

200

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

PubMed

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

2010-12-17

201

Maltotriose Utilization by Industrial Saccharomyces Strains: Characterization of a New Member of the ?-Glucoside Transporter Family  

PubMed Central

Maltotriose utilization by Saccharomyces cerevisiae and closely related yeasts is important to industrial processes based on starch hydrolysates, where the trisaccharide is present in significant concentrations and often is not completely consumed. We undertook an integrated study to better understand maltotriose metabolism in a mixture with glucose and maltose. Physiological data obtained for a particularly fast-growing distiller's strain (PYCC 5297) showed that, in contrast to what has been previously reported for other strains, maltotriose is essentially fermented. The respiratory quotient was, however, considerably higher for maltotriose (0.36) than for maltose (0.16) or glucose (0.11). To assess the role of transport in the sequential utilization of maltose and maltotriose, we investigated the presence of genes involved in maltotriose uptake in the type strain of Saccharomyces carlsbergensis (PYCC 4457). To this end, a previously constructed genomic library was used to identify maltotriose transporter genes by functional complementation of a strain devoid of known maltose transporters. One gene, clearly belonging to the MAL transporter family, was repeatedly isolated from the library. Sequence comparison showed that the novel gene (designated MTY1) shares 90% and 54% identity with MAL31 and AGT1, respectively. However, expression of Mty1p restores growth of the S. cerevisiae receptor strain on both maltose and maltotriose, whereas the closely related Mal31p supports growth on maltose only and Agt1p supports growth on a wider range of substrates, including maltose and maltotriose. Interestingly, Mty1p displays higher affinity for maltotriose than for maltose, a new feature among all the ?-glucoside transporters described so far.

Salema-Oom, Madalena; Valadao Pinto, Vera; Goncalves, Paula; Spencer-Martins, Isabel

2005-01-01

202

Antiobesity potential of ursolic acid stearoyl glucoside by inhibiting pancreatic lipase.  

PubMed

The present study was designed to evaluate the hypolipidemic effect of ursolic acid stearoyl glucoside (UASG) in high-fat diet-induced obesity. Two in vivo experiments such as high-fat diet-induced obesity mice model and lipid emulsion tolerance test in normal rats were performed. In vitro inhibition of pancreatic lipase activity was further measured to substantiate the results. In high-fat diet-induced obesity mice model, female Swiss mice were fed a high fat diet (HFD; 40% fat) with or without 1 or 2% of UASG or 0.012% orlistat for nine weeks. In lipid emulsion tolerance test male Wister rats were orally administered, lipid emulsion with or without 500 or 1000 mg/kg of UASG and the plasma triglycerides were measured from 0.5 to 5 h. Consumption of HFD containing UASG to mice for nine weeks exhibited significant reduction in lipid parameters, body weight, parametrial adipose tissue weight, liver triglyceride (TG) and different organ weight compared to HFD fed control. Further it was noted the improvement in insulin resistance induced by the HFD alone group. Furthermore, consumption of an HFD containing 1 or 2% of UASG significantly increased the fecal content and fecal triglyceride compared with the HFD group. Pre-treatment with UASG inhibited the elevated plasma triglyceride level after the oral administration of the lipid emulsion to rats. Further, UASG significantly inhibits activity of pancreatic lipase at a concentration of 2.5 mg/ml. Data obtained from the results indicated that UASG prevent high-fat diet-induced obesity in mice possibly by inhibiting pancreatic lipase activity. PMID:23500199

Kazmi, Imran; Afzal, Muhammad; Rahman, Shakilur; Iqbal, Muzaffar; Imam, Faisal; Anwar, Firoz

2013-06-01

203

Total glucosides of paeony prevents juxta-articular bone loss in experimental arthritis  

PubMed Central

Background Total glucosides of paeony (TGP) is a biologically active compound extracted from Paeony root. TGP has been used in rheumatoid arthritis therapy for many years. However, the mechanism by which TGP prevents bone loss has been less explored. Methods TGP was orally administered for 3 months to New Zealand rabbits with antigen-induced arthritis (AIA). Digital x-ray knee images and bone mineral density (BMD) measurements of the subchondral knee bone were performed before sacrifice. Chondrocytes were observed using transmission electron microscopy (TEM). Histological analysis and mRNA expression of receptor activator of nuclear factor-B ligand (RANKL) and osteoprotegerin (OPG) were evaluated in joint tissues. Results The BMD value in TGP rabbits was significantly higher compared with that seen in the AIA model rabbits. In addition, the subchondral bone plate was almost completely preserved by TGP treatment, while there was a decrease in bone plate integrity in AIA rabbits. There was less damage to the chondrocytes of the TGP treated group. Immunohistochemical examination of the TGP group showed that a higher percentage of TGP treated chondrocytes expressed OPG as compared to the chondrocytes isolated from AIA treated animals. In contrast, RANKL expression was significantly decreased in the TGP treated group compared to the AIA group. In support of the immunohistochemistry data, the expression of RANKL mRNA was decreased and OPG mRNA expression was enhanced in the TGP group when compared to that of the AIA model group. Conclusion These results reveal that TGP suppresses juxta-articular osteoporosis and prevents subchondral bone loss. The decreased RANKL and increased OPG expression seen in TGP treated animals could explain how administration of TGP maintains higher BMD.

2013-01-01

204

The bioavailability of apigenin-7-glucoside is influenced by human intestinal microbiota in rats.  

PubMed

We investigated the impact of human intestinal microbiota on bioavailability of the flavone apigenin-7-glucoside (A7G) by comparing germ-free and human microbiota-associated (HMA) rats. First, the ability of the human intestinal microbiota to convert A7G was proven in vitro by incubating A7G with fecal suspensions. Apigenin, naringenin, and 3-(4-hydroxyphenyl)propionic acid were formed as main metabolites. After application of A7G to germ-free rats, apigenin, luteolin, and their conjugates were detected in urine and feces. In HMA rats, naringenin, eriodictyol, phloretin, 3-(3,4-dihydroxyphenyl)propionic acid, 3-(4-hydroxyphenyl)propionic acid, 3-(3-hydroxyphenyl)propionic acid, and 4-hydroxycinnamic acid in their free and conjugated forms were additionally formed. In whole-blood samples from germ-free and HMA rats, only apigenin conjugates and phloretin, respectively, were detected. The total excretion of A7G and its metabolites within 48 h was similarly low in both germ-free and HMA rats, with 11 and 13% of the A7G dose, respectively. In germ-free rats, A7G metabolites dominated by apigenin and its conjugates were mainly excreted with feces. In contrast, the compounds in HMA rats were predominantly recovered from urine, 3-(4-hydroxyphenyl)propionic acid being the main metabolite. The ability of selected gut bacteria and the host intestinal mucosa to deglycosylate A7G was tested using cell extracts. Apigenin was formed by cytosolic extracts of Eubacterium ramulus and Bacteroides distasonis and by the microsomal fraction of the small intestinal mucosa of rats. Overall, human intestinal microbiota largely contributed to A7G metabolism, indicating its influence on the bioactivity of flavones. PMID:19403720

Hanske, Laura; Loh, Gunnar; Sczesny, Silke; Blaut, Michael; Braune, Annett

2009-06-01

205

Targeting RNA by Small Molecules: Comparative Structural and Thermodynamic Aspects of Aristololactam-?-D-glucoside and Daunomycin Binding to tRNAphe  

PubMed Central

Background Interaction of aristololactam-?-D-glucoside and daunomycin with tRNAphe was investigated using various biophysical techniques. Methodology/Principal Findings Absorption and fluorescence studies revealed that both the compounds bind tRNAphe non-cooperatively. The binding of daunomycin was about one order of magnitude higher than that of aristololactam-?-D-glucoside. Stronger binding of the former was also inferred from fluorescence quenching data, quantum efficiency values and circular dichroic results. Results from isothermal titration calorimetry experiments suggested that the binding of both compounds was predominantly entropy driven with a smaller but favorable enthalpy term that increased with temperature. A large favorable electrostatic contribution to the binding of daunomycin to tRNAphe was revealed from salt dependence data and the dissection of the free energy values. The electrostatic component to the free energy change for aristololactam-?-D-glucoside-tRNAphe interaction was smaller than that of daunomycin. This was also inferred from the slope of log K versus [Na+] plots. Both compounds enhanced the thermal stability of tRNAphe. The small heat capacity changes of -47 and -99 cal/mol K, respectively, observed for aristololactam-?-D-glucoside and daunomycin, and the observed enthalpy-entropy compensation phenomenon confirmed the involvement of multiple weak noncovalent interactions. Molecular aspects of the interaction have been revealed. Conclusions/Significance This study presents the structural and eneregetic aspects of the binding of aristololactam-?-D-glucoside and daunomycin to tRNAphe.

Das, Abhi; Bhadra, Kakali; Suresh Kumar, Gopinatha

2011-01-01

206

Specificity of binding of beta-glucoside activators of ryegrass (1-->3)-beta-glucan synthase and the synthesis of some potential photoaffinity activators.  

PubMed Central

Structure-activity relationships among glycoside activators of ryegrass (Lolium multiflorum) (1-->3)-beta-glucan synthase were investigated using a number of natural and synthetic glycosides, including some carrying photoaffinity functions. There is an absolute requirement for a beta-D-glycosyl moiety in the activator, both S- and N-glucosides are active, and the position of the glucosidic linkage in beta-glucose disaccharides has a significant effect on the affinity of binding. However, the binding requirement does not extend beyond a single beta-D-glucosyl residue, and beta-D-oligoglucosides are less effective than disaccharides. The nature of the aglycon has a major influence on the binding affinity. Hydrophobic aglycons lower the concentration required for half-maximal stimulation of the enzyme obtained from an Eadie-Hofstee plot of kinetic data (Ka) for activation, but charge aglycons increase Ka. Relative to methyl-beta-D-glucoside and cellobiose (Ka 1.1 mM), the most potent compounds tested were N-[4-(benzoyl)benzoyl]-beta-D-glucosylamine and 2'-[4-azidosalicylamino]ethyl-1-thio-beta-D-glucoside with K(a)s of approximately 30 microM. The latter also was tested for its potential to specifically label the beta-glucoside-binding site on the synthase, but under the conditions used the binding was found to be nonspecific.

Ng, K; Johnson, E; Stone, B A

1996-01-01

207

Functional characterization, homology modeling and docking studies of ?-glucosidase responsible for bioactivation of cyanogenic hydroxynitrile glucosides from Leucaena leucocephala (subabul).  

PubMed

Glycosyl hydrolase family 1 ?-glucosidases are important enzymes that serve many diverse functions in plants including defense, whereby hydrolyzing the defensive compounds such as hydroxynitrile glucosides. A hydroxynitrile glucoside cleaving ?-glucosidase gene (Llbglu1) was isolated from Leucaena leucocephala, cloned into pET-28a (+) and expressed in E. coli BL21 (DE3) cells. The recombinant enzyme was purified by Ni-NTA affinity chromatography. The optimal temperature and pH for this ?-glucosidase were found to be 45 °C and 4.8, respectively. The purified Llbglu1 enzyme hydrolyzed the synthetic glycosides, pNPGlucoside (pNPGlc) and pNPGalactoside (pNPGal). Also, the enzyme hydrolyzed amygdalin, a hydroxynitrile glycoside and a few of the tested flavonoid and isoflavonoid glucosides. The kinetic parameters K (m) and V (max) were found to be 38.59 ?M and 0.8237 ?M/mg/min for pNPGlc, whereas for pNPGal the values were observed as 1845 ?M and 0.1037 ?M/mg/min. In the present study, a three dimensional (3D) model of the Llbglu1 was built by MODELLER software to find out the substrate binding sites and the quality of the model was examined using the program PROCHEK. Docking studies indicated that conserved active site residues are Glu 199, Glu 413, His 153, Asn 198, Val 270, Asn 340, and Trp 462. Docking of rhodiocyanoside A with the modeled Llbglu1 resulted in a binding with free energy change (?G) of -5.52 kcal/mol on which basis rhodiocyanoside A could be considered as a potential substrate. PMID:23079707

Shaik, Noor M; Misra, Anurag; Singh, Somesh; Fatangare, Amol B; Ramakumar, Suryanarayanarao; Rawal, Shuban K; Khan, Bashir M

2013-02-01

208

Kinetic analysis of the degradation and its color change of cyanidin-3-glucoside exposed to pulsed electric field  

Microsoft Academic Search

The degradation and its corresponding color change of cyaniding-3-glucoside (Cy-3-glu) exposed to pulsed electric field (PEF)\\u000a was investigated in the study. In an aqueous-methanol solution of H2O (0.5% TFA) and methanol (MeOH) (7:3, v\\/v), the degradation of Cy-3-glu, which was exposed to PEF at 1.2, 2.2 and 3.3 kV\\/cm,\\u000a was increased as the electric field intensity and the treatment time increased

Yan Zhang; Xiaojun Liao; Yuanying Ni; Jihong Wu; Xiaosong Hu; Zhengfu Wang; Fang Chen

2007-01-01

209

Synthesis of zearalenone-16-?,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation  

PubMed Central

Summary The development of a reliable procedure for the synthesis of the 16-glucoside and 16-sulfate of the resorcylic acid lactone (RAL) type compound zearalenone is presented. Different protective group strategies were considered and applied to enable the preparation of glucosides and sulfates that are difficult to access up to now. Acetyl and p-methoxybenzyl protection led to undesired results and were shown to be inappropriate. Finally, triisopropylsilyl-protected zearalenone was successfully used as intermediate for the first synthesis of the corresponding mycotoxin glucoside and sulfate that are highly valuable as reference materials for further studies in the emerging field of masked mycotoxins. Furthermore, high stability was observed for aryl sulfates prepared as tetrabutylammonium salts. Overall, these findings should be applicable for the synthesis of similar RAL type and natural product conjugates.

Weber, Julia; Svatunek, Dennis; Skrinjar, Philipp; Adam, Gerhard; Krska, Rudolf; Hametner, Christian; Frohlich, Johannes

2014-01-01

210

LC determination of luteolin-7-O-?-D-glucoside and apigenin-7-O-?-D-glucoside in rat plasma after administration of Humulus scandens extract and its application to pharmacokinetic studies.  

PubMed

The present study was to investigate the pharmacokinetics of luteolin-7-O-?-D-glucoside (LGL) and apigenin-7-O-?-D-glucoside (AGL) in rat plasma after intravenous administration of the Humulus scandens extract (HSE). A simple and accurate high-performance liquid chromatographic (HPLC) method was successfully developed for simultaneous determination of LGL and AGL in rat plasma after the plasma protein was precipitated with methanol. HPLC analysis was performed on a C?? column with UV detection at 350?nm and a mobile phase of methanol-0.2% phosphoric acid (1?:?1, v/v). Calibration curves of LGL and AGL were linear over the concentration range of 0.16-20.0 and 0.06-7.20?µg?mL?¹, respectively. The accuracy and precision of the two analytes at low, medium and high concentrations were within the range of -3.4% to 8.1%. The relative standard deviations (RSDs) of the intra- and inter-day precisions were less than 11.7% and 10.0%, respectively. The extraction recoveries (n?=?5) varied from 91.9% to 104.1% for LGL and from 92.6% to 109.3% for AGL. The method was fully validated and successfully applied to a pharmacokinetic study of LGL and AGL in rat plasma after the intravenous administration of HSE. PMID:21756194

Chen, Zaixing; Ying, Xixiang; Meng, Shu; Zhu, Xu; Jiang, Hong; Cao, Qishen; Wang, Lin; Meng, Fanhao

2012-01-01

211

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

NASA Astrophysics Data System (ADS)

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

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

2014-05-01

212

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.

1984-11-01

213

Analysis of the metabolites of isorhamnetin 3-O-glucoside produced by human intestinal flora in vitro by applying ultraperformance liquid chromatography/quadrupole time-of-flight mass spectrometry.  

PubMed

Isorhamnetin 3-O-glucoside, which is widely contained in many vegetables and rice, is expected to be metabolized by intestinal microbiota after digestion, which brings about the profile of its pharmacological effect. However, little is known about the interactions between this active ingredient and the intestinal flora. In this study, the preculture bacteria and GAM (general anaerobic medium) broth with isorhamnetin 3-O-glucoside were mixed for 48 h of incubation. Ultraperformance liquid chromatography/quadrupole time-of-flight mass spectrometry was used for analysis of the metabolites of isorhamnetin 3-O-glucoside in the corresponding supernatants of fermentation. The parent and five metabolites were found and preliminarily identified on the basis of the chromatograms and characteristics of their protonated ions. Four main metabolic pathways, including deglycosylation, demethoxylation, dehydroxylation, and acetylation, were summarized to explain how the metabolites were converted. Acetylated isorhamnetin 3-O-glucoside and kaempferol 3-O-glucoside were detected only in the sample of Escherichia sp. 12, and quercetin existed only in the sample of Escherichia sp. 4. However, the majority of bacteria could metabolize isorhamnetin 3-O-glucoside to its aglycon isorhamnetin, and then isorhamnetin was degraded to kaempferol. The metabolic pathway and the metabolites of isorhamnetin 3-O-glucoside yielded by different isolated human intestinal bacteria were investigated for the first time. The results probably provided useful information for further in vivo metabolism and active mechanism research on isorhamnetin 3-O-glucoside. PMID:24601527

Du, Le-yue; Zhao, Min; Xu, Jun; Qian, Da-wei; Jiang, Shu; Shang, Er-xin; Guo, Jian-ming; Duan, Jin-ao

2014-03-26

214

Occurrence of different trichothecenes and deoxynivalenol-3-?-D-glucoside in naturally and artificially contaminated Danish cereal grains and whole maize plants.  

PubMed

Fusarium mycotoxins such as deoxynivalenol (DON) can occur in cereals conjugated to glucose and probably also to other sugars. These conjugates, which are often referred to as "masked mycotoxins", will not be detected with routine analytical techniques. Furthermore, it is suspected that the parent toxin may again be released after hydrolysis in the digestive tracts of animals and humans. Today, our knowledge of the occurrence of these compounds in cereal grains is limited. In this paper, a LC-MS/MS method for the simultaneous determination of DON, deoxynivalenol-3-?-D-glucoside (DON-3-glucoside), 3 acetyl-DON, nivalenol, fusarenon-X, diacetoxyscirpenol, HT-2 toxin, and T-2 toxin in naturally (n?=?48) and artificially (n?=?30) contaminated cereal grains (wheat, barley, oat, rye triticale) is reported. The method has also been applied to whole fresh maize plant intended for production of maize silage (n?=?10). The samples were collected from the harvest years 2006-2010, The results show that DON-3-glucoside and DON co-occurred in cereal grains and, especially in several of the highly contaminated samples, the concentration of the glucoside can be relatively high, corresponding to over 37 % of the DON concentration. The DON-3-glucoside levels in both the naturally and in the artificially grain inoculated with Fusarium were second only to DON, and were generally higher than those of the other tested trichothecenes, which were found at low concentrations in most samples, in many cases even below the detection limit of the method. This argues for the importance of taking DON-3-glucoside into account in the ongoing discussion within the European Community concerning exposure re-evaluations for setting changed values for the tolerable intake for DON. Our results indicate that, in the naturally contaminated grains and in the Fusarium infested cereal grains (winter and spring wheat, oat, triticale), the concentration level of DON-3-glucoside is positively correlated to the DON content. When the DON concentration is high, then the content of DON-3-glucoside will most probably also be high and vice versa. PMID:23606126

Rasmussen, P H; Nielsen, K F; Ghorbani, F; Spliid, N H; Nielsen, G C; Jørgensen, L N

2012-08-01

215

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

PubMed

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

2011-05-15

216

Protective effects of amburoside A, a phenol glucoside from Amburana cearensis, against CCl4-induced hepatotoxicity in rats.  

PubMed

The aim of this study was to investigate the possible beneficial effects of amburoside A, AMB [4-(O-beta- D-glycopyranosyl)benzyl protocatechoate], against carbon tetrachloride (CCl (4)) toxicity in rats. AMB is a phenol glucoside from the Brazilian medicinal plant Amburana cearensis, popularly used for the treatment of respiratory tract affections. Acute AMB (25 and 50 mg/kg, I. P. or P. O.) treatments of CCl (4)-intoxicated rats significantly inhibited the increase in serum aspartate aminotransferase (AST) and alanine aminotransferase (ALT) levels, as compared to the group treated with CCl (4) only. Histological studies showed less centrolobular necrosis and inflammatory cell infiltrates in the liver of animals treated with AMB plus CCl (4), when compared to the group treated with CCl (4) alone. In hepatic tissues, AMB at both doses inhibited CCl (4)-induced thiobarbituric acid-reactive substances (TBARS) formation, indicating a blockade of CCl (4)-induced lipid peroxidation. AMB also reversed the decrement in glutathione contents of hepatic tissues in CCl (4)-intoxicated rats. Furthermore, it restored catalase activity to normal values, which was significantly increased after CCl (4) treatment. Our results indicate that CCl (4)-induced oxidative damage in hepatic tissues is reversed by AMB treatment. The protective effect of AMB is probably due to the phenolic nature of this glucoside. PMID:18404596

Leal, Luzia K; Fonseca, Francisco Noé; Pereira, Fábio Azevedo; Canuto, Kirley M; Felipe, Cícero F; Fontenele, Juvênia Bezerra; Pitombeira, Márcia V; Silveira, Edilberto R; Viana, Glauce S

2008-04-01

217

Repellent activity of catmint, Nepeta cataria, and iridoid nepetalactone isomers against Afro-tropical mosquitoes, ixodid ticks and red poultry mites.  

PubMed

The repellent activity of the essential oil of the catmint plant, Nepeta cataria (Lamiaceae), and the main iridoid compounds (4aS,7S,7aR) and (4aS,7S,7aS)-nepetalactone, was assessed against (i) major Afro-tropical pathogen vector mosquitoes, i.e. the malaria mosquito, Anopheles gambiae s.s. and the Southern house mosquito, Culex quinquefasciatus, using a World Health Organisation (WHO)-approved topical application bioassay (ii) the brown ear tick, Rhipicephalus appendiculatus, using a climbing repellency assay, and (iii) the red poultry mite, Dermanyssus gallinae, using field trapping experiments. Gas chromatography (GC) and coupled GC-mass spectrometry (GC-MS) analysis of two N. cataria chemotypes (A and B) used in the repellency assays showed that (4aS,7S,7aR) and (4aS,7S,7aS)-nepetalactone were present in different proportions, with one of the oils (from chemotype A) being dominated by the (4aS,7S,7aR) isomer (91.95% by GC), and the other oil (from chemotype B) containing the two (4aS,7S,7aR) and (4aS,7S,7aS) isomers in 16.98% and 69.83% (by GC), respectively. The sesquiterpene hydrocarbon (E)-(1R,9S)-caryophyllene was identified as the only other major component in the oils (8.05% and 13.19% by GC, respectively). Using the topical application bioassay, the oils showed high repellent activity (chemotype A RD(50)=0.081 mg cm(-2) and chemotype B RD(50)=0.091 mg cm(-2)) for An. gambiae comparable with the synthetic repellent DEET (RD(50)=0.12 mg cm(-2)), whilst for Cx. quinquefasciatus, lower repellent activity was recorded (chemotype A RD(50)=0.34 mg cm(-2) and chemotype B RD(50)=0.074 mg cm(-2)). Further repellency testing against An. gambiae using the purified (4aS,7S,7aR) and (4aS,7S,7aS)-nepetalactone isomers revealed overall lower repellent activity, compared to the chemotype A and B oils. Testing of binary mixtures of the (4aS,7S,7aR) and (4aS,7S,7aS) isomers across a range of ratios, but all at the same overall dose (0.1 mg), revealed not only a synergistic effect between the two, but also a surprising ratio-dependent effect, with lower activity for the pure isomers and equivalent or near-equivalent mixtures, but higher activity for non-equivalent ratios. Furthermore, a binary mixture of (4aS,7S,7aR) and (4aS,7S,7aS) isomers, in a ratio equivalent to that found in chemotype B oil, was less repellent than the oil itself, when tested at two doses equivalent to 0.1 and 0.01 mg chemotype B oil. The three-component blend including (E)-(1R,9S)-caryophyllene at the level found in chemotype B oil had the same activity as chemotype B oil. In a tick climbing repellency assay using R. appendiculatus, the oils showed high repellent activity comparable with data for other repellent essential oils (chemotype A RD(50)=0.005 mg and chemotype B RD(50)=0.0012 mg). In field trapping assays with D. gallinae, addition of the chemotype A and B oils, and a combination of the two, to traps pre-conditioned with D. gallinae, all resulted in a significant reduction of D. gallinae trap capture. In summary, these data suggest that although the nepetalactone isomers have the potential to be used in human and livestock protection against major pathogen vectors, intact, i.e. unfractionated, Nepeta spp. oils offer potentially greater protection, due to the presence of both nepetalactone isomers and other components such as (E)-(1R,9S)-caryophyllene. PMID:21056438

Birkett, Michael A; Hassanali, Ahmed; Hoglund, Solveig; Pettersson, Jan; Pickett, John A

2011-01-01

218

C-Glucoside xanthone from the stem bark extract of Bersama engleriana  

PubMed Central

Background: The genus Bersama belongs to the Melianthaceae family and comprises of four species (B. swinnyi, B. yangambiensis, B. abyssinica, and B. engleriana) all of which are very high trees; the latter two detected species are found in Cameroon. Previous phytochemical investigation on B. yangambiensis, B. swinnyi, and B. abyssinica led to the isolation of triterpenes, saponins, flavonoids, and xanthones. Method: The stem bark of B. engleriana were collected in the village, Baham near Bafoussam city, Cameroon in August 2003 and identifi ed by Dr. Onana National Herbaruim, Yaound?, Cameroon. The air dried and powdered stem bark of B. engleriana (1 kg) was extracted at room temperature with CH2Cl2-MeOH (1:1) 5 L for 48 hours. The mixture of the solvent was removed by evaporation to yield 200 g of crude extract. The latter was then dissolved in CH2Cl2 to give the CH2Cl2 soluble fraction of 5 g and a remaining gum of 195 g. Part of the remaining gum (22 g) was dissolved in water and extracted four times with butanol to give 12 g of red oil; which was then separated by paper chromatography, with butanol-acetic acid-water (4:1:5), to give 3 g of orange gum; purification was carried out on HPLC with MeOH (100%) to yield 2 g of mangiferin (1) as red oil. The CH2Cl2 soluble extract was eluted on silica gel n-hexane-CH2Cl2 gradient ratio and Sephadex LH-20 (n-hexane -CH2Cl2 -MeOH, (7:4:0.5) to afford compounds swinniol (2), ?4-stigmaster-3?-ol (3), 4-methylstigmaster-5,23-dien-3?-ol(4). Results: Herein, we carried out a phytochemical study of the stem bark of B. engleriana, and we report herein the isolation and structural elucidation of mangiferin, in addition to three triterpenes, previously reported from other species of the genus.[35] The assignment of the signals of mangiferin was determined using 1H, 13C-NMR, and 2D-NMR spectral data (HMQC, COSY, HMBC). The terpenoids were identifi ed by comparison of their 1H and 13C-NMR spectra with the literature data. Fractionation of the CH2Cl2-MeOH (1:1) extract of the stem bark of B. engleriana Guike gave mangiferin (1), in addition to three previously reported triterpenes, swinniol (2), ?4-stigmaster-3?-ol (3), and 4-methylstigmaster-5,23-dien-3-?-ol (4). Conclusions: A chemical investigation of the CH2Cl2-MeOH extract of the stem bark of Bersama engleriana afforded a xanthone C-glucoside (mangiferin) and fi rst isolation of three terpenoids from this species: swinniol (2), ?4-stigmaster-3?-ol (3), and 4-methylstigmaster-5,23-dien-3-?-ol (4). The complete 1H and 13C chemical shift assignments of mangiferin were determined using 1D and 2D NMR spectroscopic data (COSY, HMQC, HMBC, DEPT). The structures of the terpenoids were determined from their 1H and 13C NMR data and compared with the literature data.

Djemgou, Pierre C.; Hussien, Taha A.; Hegazy, Mohamed-Elamir F.; Ngandeu, Francois; Neguim, Gilles; Tane, Pierre; Mohamed, Abou-El-Hamd H.

2010-01-01

219

A putative ?-glucoside transporter gene BbAGT1 contributes to carbohydrate utilization, growth, conidiation and virulence of filamentous entomopathogenic fungus Beauveria bassiana.  

PubMed

Carbohydrate transporters are critical players mediating nutrient uptake during saprophytic and pathogenic growth for most filamentous fungi. For entomopathogenic fungi, such as Beauveria bassiana, assimilation of ?-glucosides, in particular, trehalose, the major carbohydrate constituent of the insect haemolymph, has been hypothesized to represent an important ability for infectious growth within the insect hemocoel. In this study, a B. bassiana ?-glucoside transporter homolog was identified and genetically characterized via generation of a targeted gene disruption mutant. Trehalose utilization was compromised in the mutant strain. In addition, inactivation of the ?-glucoside transporter resulted in decreased conidial germination, growth, and yield on various carbohydrates (?-glucosides, monosaccharides and polyols) as compared to the wild-type strain. Insect bioassays revealed decreased mean lethal mortality time using both topical and intrahemocoel injection assays, although final mortality levels were comparable in both the mutant and wild type. Gene expression profiles showed altered expression of other putative transporters in the knockout mutant as compared to the wild type. These results highlighted complex sugar utilization and responsiveness in B. bassiana and the potential role for trehalose assimilation during fungal pathogenesis of insects. PMID:23499939

Wang, Xiu-Xiu; Ji, Xiao-Ping; Li, Jing-Xin; Keyhani, Nemat O; Feng, Ming-Guang; Ying, Sheng-Hua

2013-06-01

220

The Apparent Absorptions of Isoflavone Glucosides and Aglucons Are Similar in Women and Are Increased by Rapid Gut Transit Time and Low Fecal Isoflavone Degradation1,2  

Microsoft Academic Search

We hypothesized that there would be no difference in apparent absorption, as assessed by urinary excretion, between isoflavone sources rich in glucosides or aglucons and that subjects with rapid gut transit time (GTT) and low fecal isoflavone degradation phenotype would absorb more isoflavones. Women (n 13) with a fecal daidzein degradation rate constant, Dk 0.30 h 1 (high degraders) and

Yan Zheng; Sun-Ok Lee; Marian A. Verbruggen; Patricia A. Murphy; Suzanne Hendrich

221

Structural determination of kochiosides A-C, new steroidal glucosides from Kochia prostrata, by 1D and 2D NMR spectroscopy.  

PubMed

Kochiosides A-C, three new steroidal glucosides, have been isolated from the ethyl acetate fraction of Kochia prostrata and their structures assigned from its (1)H and (13)C NMR spectra, DEPT and by 2D COSY, NOESY, HMQC and HMBC experiments. PMID:17640023

Imran, Muhammad; Ahmed, Ejaz; Malik, Abdul

2007-09-01

222

Detection of Type A Trichothecene Di-Glucosides Produced in Corn by High-Resolution Liquid Chromatography-Orbitrap Mass Spectrometry  

PubMed Central

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.

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

2013-01-01

223

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

PubMed

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

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

2013-08-21

224

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

Microsoft Academic Search

The intestinal absorption of benzyl ?-glucoside (BNZ?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?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

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

2005-01-01

225

Renal effects of a novel endogenous natriuretic agent xanthurenic acid 8-o-?-d-glucoside in rats.  

PubMed

Xanthurenic acid 8-o-?-d-glucoside is an endogenous derivative of tryptophan metabolism, isolated from urine of patients with chronic renal disease. This compound was suggested previously to act as a natriuretic hormone based on its ability to block short circuit currents in a frog skin assay and to induce a sustained natriuresis when injected into rats (C. D. Cain et al., Proc. Natl. Acad. Sci. USA 2007: 17873-17878). The present communication describes the effects of the compound on renal clearance and hemodynamic parameters in male Sprague-Dawley rats maintained on a normal salt (0.4-0.5%) diet. Intravenous administration of synthetic xanthurenic acid 8-o-?-d-glucoside in two consecutive incremental doses (6.3 and 31.5 nmol) resulted in a significant increase (P < 0.05), in urine flow (43.91 ± 6.31 ?L/min vs. 10.54 ± 2.21 ?L/min), absolute rate of sodium excretion (3.99 ± 0.95 ?Eq/min vs. 1.15 ± ?Eq/min), and percentage sodium excretion (1.63 ± 0.46% vs. 0.37 ± 0.12%, peak response vs. baseline, respectively). The natriuretic/diuretic effect was associated also with a significant increase in potassium excretion. These effects were not related to changes in renal hemodynamics or in arterial blood pressure. Pretreatment with the sodium channel blocker, amiloride, completely abolished the natriuretic and kaluretic actions of the compound. Administration of the xanthurenic acid derivative caused a dose-related increase in urinary nitrite/nitrate excretion. Moreover, under chronic nitric oxide blockade by l-NG-Nitro-Arginine-Methyl-Esther (l-NAME) sodium excretion was similar in rats treated or untreated with the compound. Our data demonstrate that xanthurenic acid 8-o-?-d-glucoside has significant diuretic/natriuretic and kaluretic properties. An intact amiloride-sensitive sodium channel is required for the renal effects of the compound. The data further suggest that the natriuretic effect is mediated in part by a nitric oxide-dependent mechanism. PMID:24400157

Hoffman, Aaron; Okun-Gurevich, Marina; Ovcharenko, Elena; Goltsman, Ilia; Karram, Tony; Cain, Cristopher; Abassi, Zaid; Winaver, Joseph

2013-11-01

226

Renal effects of a novel endogenous natriuretic agent xanthurenic acid 8-o-?-d-glucoside in rats  

PubMed Central

Xanthurenic acid 8-o-?-d-glucoside is an endogenous derivative of tryptophan metabolism, isolated from urine of patients with chronic renal disease. This compound was suggested previously to act as a natriuretic hormone based on its ability to block short circuit currents in a frog skin assay and to induce a sustained natriuresis when injected into rats (C. D. Cain et al., Proc. Natl. Acad. Sci. USA 2007: 17873–17878). The present communication describes the effects of the compound on renal clearance and hemodynamic parameters in male Sprague–Dawley rats maintained on a normal salt (0.4–0.5%) diet. Intravenous administration of synthetic xanthurenic acid 8-o-?-d-glucoside in two consecutive incremental doses (6.3 and 31.5 nmol) resulted in a significant increase (P < 0.05), in urine flow (43.91 ± 6.31 ?L/min vs. 10.54 ± 2.21 ?L/min), absolute rate of sodium excretion (3.99 ± 0.95 ?Eq/min vs. 1.15 ± ?Eq/min), and percentage sodium excretion (1.63 ± 0.46% vs. 0.37 ± 0.12%, peak response vs. baseline, respectively). The natriuretic/diuretic effect was associated also with a significant increase in potassium excretion. These effects were not related to changes in renal hemodynamics or in arterial blood pressure. Pretreatment with the sodium channel blocker, amiloride, completely abolished the natriuretic and kaluretic actions of the compound. Administration of the xanthurenic acid derivative caused a dose-related increase in urinary nitrite/nitrate excretion. Moreover, under chronic nitric oxide blockade by l-NG-Nitro-Arginine-Methyl-Esther (l-NAME) sodium excretion was similar in rats treated or untreated with the compound. Our data demonstrate that xanthurenic acid 8-o-?-d-glucoside has significant diuretic/natriuretic and kaluretic properties. An intact amiloride-sensitive sodium channel is required for the renal effects of the compound. The data further suggest that the natriuretic effect is mediated in part by a nitric oxide-dependent mechanism.

Hoffman, Aaron; Okun-Gurevich, Marina; Ovcharenko, Elena; Goltsman, Ilia; Karram, Tony; Cain, Cristopher; Abassi, Zaid; Winaver, Joseph

2013-01-01

227

Identification, amounts, and kinetics of extraction of C-glucosidic ellagitannins during wine aging in oak barrels or in stainless steel tanks with oak chips.  

PubMed

The C-glucosidic ellagitannins are found in wine as a result of its aging in oak barrels or in stainless steel tanks with oak chips. Once dissolved in this slightly acidic solution, the C-glucosidic ellagitannins vescalagin can react with nucleophilic entities present in red wine, such as ethanol, catechin, and epicatechin, to generate condensed hybrid products such as the ?-1-O-ethylvescalagin and the flavano-ellagitannins (acutissimin A/B and epiacutissimin A/B), respectively. During this study, we first monitored the extraction kinetic and the evolution of the eight major oak-derived C-glucosidic ellagitannins in red wines aged in oak barrels or in stainless steel tank with oak chips. Their extraction rates appeared to be faster during red wine aging in stainless steel tanks with oak chips. However, their overall concentrations in wines were found higher in the wine aged in barrels. The formation rates of the vescalagin-coupled derivatives were also estimated for the first time under both red wine aging conditions (i.e., oak barrels or stainless steel tanks with oak chips). As observed for the oak-native C-glucosidic ellagitannins, the concentrations of these vescalagin derivatives were higher in the red wine aged in oak barrels than in stainless steel tanks with oak chips. Despite these differences, their relative composition was similar under both red wine aging conditions. Finally, the impact of the oak chips size and toasting level on the C-glucosidic ellagitannins concentration in wine was also investigated. PMID:21479542

Jourdes, Michaël; Michel, Julien; Saucier, Cédric; Quideau, Stéphane; Teissedre, Pierre-Louis

2011-09-01

228

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

PubMed

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

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

2006-08-01

229

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

2008-09-01

230

cDNA cloning, heterologous expressions, and functional characterization of malonyl-coenzyme a:anthocyanidin 3-o-glucoside-6"-o-malonyltransferase from dahlia flowers.  

PubMed

In the flowers of important ornamental Compositae plants, anthocyanins generally carry malonyl group(s) at their 3-glucosyl moiety. In this study, for the first time to our knowledge, we have identified a cDNA coding for this 3-glucoside-specific malonyltransferase for anthocyanins, i.e. malonyl-coenzyme A:anthocyanidin 3-O-glucoside-6"-O-malonyltransferase, from dahlia (Dahlia variabilis) flowers. We isolated a full-length cDNA (Dv3MaT) on the basis of amino acid sequences specifically conserved among anthocyanin acyltransferases of the versatile plant acyltransferase family. Dv3MaT coded for a protein of 460 amino acids. Quantitative real-time PCR analyses of Dv3MaT showed that the transcript was present in accordance with the distribution of 3MaT activities and the anthocyanin accumulation pattern in the dahlia plant. The Dv3MaT cDNA was expressed in Escherichia coli, and the recombinant enzyme was purified to homogeneity and characterized. The recombinant Dv3MaT catalyzed the regiospecific transfer of the malonyl group from malonyl-coenzyme A (K(m), 18.8 microM) to pelargonidin 3-O-glucoside (K(m), 46.7 microM) to produce pelargonidin 3-O-6"-O-malonylglucoside with a k(cat) value of 7.3 s(-1). The other enzymatic profiles of the recombinant Dv3MaT were closely related to those of native anthocyanin malonyltransferase activity in the extracts of dahlia flowers. Dv3MaT cDNA was introduced into petunia (Petunia hybrida) plants whose red floral color is exclusively provided by cyanidin 3-O-glucoside and 3,5-O-diglucoside. Thirteen transgenic lines of petunia were found to produce malonylated products of these anthocyanins (11-63 mol % of total anthocyanins in the flower). The spectral stability of cyanidin 3-O-6"-O-malonylglucoside at the pHs of intracellular milieus of flowers was significantly higher than that of cyanidin 3-O-glucoside. Moreover, 6"-O-malonylation of cyanidin 3-O-glucoside effectively prevented the anthocyanin from attack of beta-glucosidase. These results suggest that malonylation should serve as a strategy for pigment stabilization in the flowers. PMID:12481098

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

2002-12-01

231

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

PubMed Central

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

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

2002-01-01

232

Profiling and identification of the metabolites of calycosin in rat hepatic 9000×g supernatant incubation system and the metabolites of calycosin-7-O-?-D-glucoside in rat urine by HPLC-DAD-ESI-IT-TOF-MS(n) technique.  

PubMed

Calycosin and calycosin-7-O-?-D-glucoside are two main bioactive isoflavonoids in Astragali Radix. To profile the metabolites of calycosin in rat hepatic 9000×g supernatant incubation system and the metabolites of calycosin-7-O-?-D-glucoside in rat urine, high performance liquid chromatography with diode array detector and combined with electrospray ionization ion trap time-of-flight multistage mass spectrometry (HPLC-DAD-ESI-IT-TOF-MS(n)) technique was used. Totally, 24 new in vitro metabolites of calycosin and 33 new in vivo metabolites of calycosin-7-O-?-D-glucoside were identified. Monoglucosylation, monopentosylation, demethylation, dehydroxylation, dimerization, and trimerization were found to be new in vitro metabolic reactions of calycosin; hydroxylation and hydrogenation were new metabolic reactions of calycosin-7-O-?-D-glucoside in vivo. The major metabolic reactions of calycosin in rat hepatic 9000×g supernatant incubation system were monohydroxylation on A-ring, dimerization (CO coupling), dimerization (CC coupling) and dehydroxylation; the major phase I metabolic reactions of calycosin-7-O-?-D-glucoside in rats were deglycosylation, hydroxylation, demethylation and dehydroxylation. Hydroxylation, dehydroxylation, and demethylation were common metabolic pathways to calycosin and calycosin-7-O-?-D-glucoside, and some of their metabolites formed through these reactions, such as 8-hydroxycalycosin (S10, M10), pratensein (5-hydroxycalycosin, S19, M27) and formononetin (S22, M28), daidzein (M22), 7,3',4'-trihydroxyisoflavone (S13, aglycon of M3 and M8), equol (aglycon of M19 and M20) had been reported to have many bioactivities related to the pharmacological effects of calycosin and calycosin-7-O-?-D-glucoside. These findings would enhance understanding of the metabolism and real active forms of calycosin and calycosin-7-O-?-D-glucoside. PMID:22766358

Zhang, Ya-Zhou; Xu, Feng; Dong, Jing; Liang, Jing; Hashi, Yuki; Shang, Ming-Ying; Yang, Dong-Hui; Wang, Xuan; Cai, Shao-Qing

2012-11-01

233

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

PubMed

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

2013-02-27

234

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

PubMed

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

2013-01-01

235

Enhanced Catalytic Efficiency in Quercetin-4'-glucoside Hydrolysis of Thermotoga maritima ?-Glucosidase A by Site-Directed Mutagenesis.  

PubMed

Te-BglA and Tm-BglA are glycoside hydrolase family 1 ?-glucosidases from Thermoanaerobacter ethanolicus JW200 and Thermotoga maritima, respectively, with 53% sequence identity. However, Te-BglA could more effectively hydrolyze isoflavone glucosides to their aglycones than could Tm-BglA, possibly due to the difference in amino acid residues around their glycone binding pockets. Site-directed mutagenesis was used to replace the amino acid residues of Tm-BglA with the corresponding residues of Te-BglA, generating three single mutants (F221L, N223L, and G224T), as well as the corresponding three double mutants (F221L/N223L, F221L/G224T, and N223L/G224T) and one triple mutant (F221L/N223L/G224T). The seven mutants have been purified, characterized, and compared to the wild-type Tm-BglA. The effects of the mutations on kinetics, enzyme activity, and substrate specificity were determined. All mutants showed pH-activity curves narrower on the basic side and wider on the acid side and had similar optimal pH and stability at pH 6.5-8.3. They were more stable up to 85 °C, but G224T displayed higher optimal temperature than Tm-BglA. Seven mutants indicated an obvious increase in catalytic efficiency toward p-nitrophenyl ?-d-glucopyranoside (pNPG) but an increase or not change in Km. All mutants showed a decrease in catalytic efficiency of isoflavonoid glycosides and were not changed for F221L and lost for N223L in enzymatic hydrolysis on quercetin glucosides. Contrarily, G224T resulted in a dramatic increase conversion of Q4' (35.5%) and Q3,4' (28.6%) in accord with an increased turnover number (kcat, 1.4×) and catalytic efficiency (kcat/Km, 2.2×) as well as a decrease in Km (0.24) for Q4'. Modeling showed that G224T mutation at position 224 may enhance the interaction between G224T and 5-OH and 3-OH on the quercetin backbone of Q4'. PMID:24933681

Sun, Huihui; Xue, Yemin; Lin, Yufei

2014-07-16

236

Vibrational spectra and stereochemistry of mono- and polysaccharides. IV. ?-methyl-d-glucoside, ?-methyl-d-galactopyranoside, and ?-methyl-d-mannopyranoside  

Microsoft Academic Search

The IR and Raman spectra of ?-methyl-D-glucoside (?MDG), ?-methyl-D-galactoside (?MDGal), and ?-methyl-D-mannoside (?MDM)\\u000a are compared. The main distinctions between these spectra have been interpreted using experimental and theoretical data on\\u000a the frequencies and modes of normal vibrations and on the potential energy distributions over particular bonds and atomic\\u000a groups of the substances under investigation. Spectral characteristics that are determined by

R. G. Zhbankov; V. M. Andrianov; H. Ratajczak; M. Marchewka

1995-01-01

237

Molecular Characterization of a Novel Glucosyltransferase from Lactobacillus reuteri Strain 121 Synthesizing a Unique, Highly Branched Glucan with ?-(1?4) and ?-(1?6) Glucosidic Bonds  

Microsoft Academic Search

Lactobacillus reuteri strain 121 produces a unique, highly branched, soluble glucan in which the majority of the linkages are of the ?-(1?4) glucosidic type. The glucan also contains ?-(1?6)-linked glucosyl units and 4,6-disubstituted ?-glucosyl units at the branching points. Using degenerate primers, based on the amino acid sequences of conserved regions from known glucosyltransferase (gtf) genes from lactic acid bacteria,

S. Kralj; G. H. van Geel-Schutten; H. Rahaoui; R. J. Leer; E. J. Faber; M. J. E. C. van der Maarel; L. Dijkhuizen

2002-01-01

238

Retargeting a maize ?-glucosidase to the vacuole--evidence from intact plants that zeatin-O-glucoside is stored in the vacuole.  

PubMed

Cytokinin (CK) activity is regulated by the complex interplay of their metabolism, transport, stability and cellular/tissue localization. O-glucosides of zeatin-type CKs are postulated to be storage and/or transport forms. Active CK levels are determined in part by their differential distribution of CK metabolites across different subcellular compartments. We have previously shown that overexpressing chloroplast-localized Zm-p60.1, a maize ?-glucosidase capable of releasing active cytokinins from their O- and N3-glucosides, perturbs CK homeostasis in transgenic tobacco. We obtained tobacco (Nicotiana tabacum L., cv Petit Havana SR1) plants overexpressing a recombinant Zm-p60.1 that is targeted to the vacuole. The protein is correctly processed and localized to the vacuole. When grown on medium containing exogenous zeatin, transgenic seedlings rapidly accumulate fresh weight due to ectopic growths at the base of the hypocotyl. The presence of the enzyme in these ectopic structures is shown by histochemical staining. CK quantification reveals that these transgenic seedlings are unable to accumulate zeatin-O-glucoside to levels similar to those observed in the wild type. When crossed with tobacco overexpressing the zeatin-O-glucosyltransferase gene from Phaseolus, the vacuolar variant shows an almost complete reversion in the root elongation assay. This is the first evidence from intact plants that the vacuole is the storage organelle for CK O-glucosides and that they are available to attack by Zm-p60.1. We propose the use of Zm-p60.1 as a robust molecular tool that exploits the reversibility of O-glucosylation and enables delicate manipulations of active CK content at the cellular level. PMID:22552277

Kiran, Nagavalli S; Benková, Eva; Reková, Alena; Dubová, Jaroslava; Malbeck, Ji?í; Palme, Klaus; Brzobohatý, B?etislav

2012-07-01

239

Protective Effect of Tetrahydroxystilbene Glucoside on 6-OHDA-Induced Apoptosis in PC12 Cells through the ROS-NO Pathway  

Microsoft Academic Search

Oxidative stress plays an important role in the pathogenesis of neurodegenerative diseases, such as Parkinson's disease. The molecule, 2,3,5,4?-tetrahydr- oxystilbene-2-O-?-D-glucoside (TSG), is a potent antioxidant derived from the Chinese herb, Polygonum multiflorum Thunb. In this study, we investigated the protective effect of TSG against 6-hydroxydopamine-induced apoptosis in rat adrenal pheochromocytoma PC12 cells and the possible mechanisms. Our data demonstrated that

Lizhen Tao; Xiaofeng Li; Lingling Zhang; Jiyu Tian; Xiaobing Li; Xin Sun; Xuefen Li; Lin Jiang; Xiaojun Zhang; Jianzong Chen; Mark R. Cookson

2011-01-01

240

Secondary metabolites in transgenic tobacco and potato: high accumulation of 4-hydroxybenzoic acid glucosides results from high expression of the bacterial gene ubiC  

Microsoft Academic Search

The bacterial gene ubiC encodes chorismate pyruvate-lyase (CPL), which converts chorismate to 4-hydroxybenzoate (4HB). The ubiC gene was expressed in tobacco (Nicotiana tabacum L., Solanaceae) and potato (Solanum tuberosum L., Solanaceae) under the control of the very strong constitutive plant promotor (ocs3) mas. High accumulation of 4HB glucosides as new, artificial secondary metabolites was observed in the transgenic plants. 4HB

Annegret Köhle; Susanne Sommer; Shu-Ming Li; Lieselotte Schilde-Rentschler; Helga Ninnemann; Lutz Heide

2003-01-01

241

Inhibitory effect of sesaminol glucosides on lipopolysaccharide-induced NF-?B activation and target gene expression in cultured rat astrocytes  

Microsoft Academic Search

The inflammatory reaction plays an important role in the pathogenesis of the neurodegenerative disorder including Alzheimer's disease (AD). Sesame lignan compounds such as sesaminol glucosides (SG) exhibit a range of pharmacological activities including anti-oxidative and anti-inflammatory action. In this study, we tried to elucidate possible effects of SG on lipopolysaccharide (LPS)-induced inflammatory reaction and its underlying mechanism in cultured astrocytes.

Sun Young Lee; Dong Ju Son; Yong Kyoung Lee; Jae Woong Lee; Hwa Jung Lee; Young Won Yun; Tae Youl Ha; Jin Tae Hong

2006-01-01

242

Gneyulins A and B, stilbene trimers, and noidesols A and B, dihydroflavonol-C-glucosides, from the bark of Gnetum gnemonoides.  

PubMed

Gneyulins A (1) and B (2), two new stilbene trimers consisting of oxyresveratrol constituent units, and noidesols A (3) and B (4), two new dihydroflavonol-C-glucosides, were isolated from the bark of Gnetum gnemonoides. The structures and configurations of 1-4 were elucidated on the basis of 2D NMR correlations and X-ray analysis. Gneyulins A (1) and B (2) showed inhibition of Na(+)-glucose transporters (SGLT-1 and SGLT-2). PMID:20192242

Shimokawa, Yoko; Akao, Yusuke; Hirasawa, Yusuke; Awang, Khalijah; Hadi, A Hamid A; Sato, Seizo; Aoyama, Chihiro; Takeo, Jiro; Shiro, Motoo; Morita, Hiroshi

2010-04-23

243

Simultaneous determination of two iridoid glycosides, two anthraquinones and four flavonoid glycosides of Zhi-Zi-Da-Huang decoction in rat plasma by UFLC-MS/MS: Application to a comparative pharmacokinetic study in normal and cholestatic liver injury rats.  

PubMed

A selective, sensitive and reliable ultra fast liquid chromatography-tandem mass spectrometry (UFLC-MS/MS) method has been developed for the simultaneous determination of two iridoid glycosides (geniposide and genipin gentiobioside), two anthraquinones (rhein and emodin) and four flavonoid glycosides (isonaringin, naringin, hesperidin and neohesperidin), the major active ingredients of Zhi-Zi-Da-Huang decoction (ZZDHD), in rat plasma using paeoniflorin as internal standard (IS). After liquid-liquid extraction with ethyl acetate-isopropanol (1:1, v/v), separation was achieved on a Shim-pack XR-ODS C18 column (75mm×3.0mm, 2.2?m) using gradient elution with a mobile phase consisting of water (containing 0.1% formic acid) and acetonitrile at a flow rate of 0.4mL/min. Detection was performed on 4000 QTRAP mass spectrometry equipped with turbo ion spray source in the negative ionization and multiple reaction monitoring (MRM) mode. The intra- and inter-day precisions (as relative standard deviation) were less than 11.4%, and accuracy (as relative error) was within ±10.0%. The lower limits of quantification (LLOQ) were 4.0, 0.5, 2.0, 0.1, 1.0, 2.0, 1.0, 2.0ng/mL for geniposide, genipin gentiobioside, rhein, emodin, isonaringin, naringin, hesperidin and neohesperidin, respectively. The extraction recoveries of the analytes and IS from rat plasma were all more than 86.0%. The method was fully validated and applied to compare the pharmacokinetic profiles of the analytes in normal and cholestatic liver injury (CLI) rats after oral administration of ZZDHD. Results showed that there were remarkable differences in pharmacokinetic properties of the analytes between normal and CLI group. PMID:24793084

Zhu, Heyun; Bi, Kaishun; Han, Fei; Guan, Jiao; Tang, Zheng; Chen, Kelin; Zhao, Longshan; Li, Qing; Yin, Ran; Hou, Xiaohong

2014-06-01

244

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

PubMed

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

2013-02-13

245

ABCC1, an ATP Binding Cassette Protein from Grape Berry, Transports Anthocyanidin 3-O-Glucosides[W][OA  

PubMed Central

Accumulation of anthocyanins in the exocarp of red grapevine (Vitis vinifera) cultivars is one of several events that characterize the onset of grape berry ripening (véraison). Despite our thorough understanding of anthocyanin biosynthesis and regulation, little is known about the molecular aspects of their transport. The participation of ATP binding cassette (ABC) proteins in vacuolar anthocyanin transport has long been a matter of debate. Here, we present biochemical evidence that an ABC protein, ABCC1, localizes to the tonoplast and is involved in the transport of glucosylated anthocyanidins. ABCC1 is expressed in the exocarp throughout berry development and ripening, with a significant increase at véraison (i.e., the onset of ripening). Transport experiments using microsomes isolated from ABCC1-expressing yeast cells showed that ABCC1 transports malvidin 3-O-glucoside. The transport strictly depends on the presence of GSH, which is cotransported with the anthocyanins and is sensitive to inhibitors of ABC proteins. By exposing anthocyanin-producing grapevine root cultures to buthionine sulphoximine, which reduced GSH levels, a decrease in anthocyanin concentration is observed. In conclusion, we provide evidence that ABCC1 acts as an anthocyanin transporter that depends on GSH without the formation of an anthocyanin-GSH conjugate.

Francisco, Rita Maria; Regalado, Ana; Ageorges, Agnes; Burla, Bo J.; Bassin, Barbara; Eisenach, Cornelia; Zarrouk, Olfa; Vialet, Sandrine; Marlin, Therese; Chaves, Maria Manuela; Martinoia, Enrico; Nagy, Reka

2013-01-01

246

Enzymatic and metabolic engineering for efficient production of syringin, sinapyl alcohol 4-O-glucoside, in Arabidopsis thaliana.  

PubMed

To promote efficient production of syringin, a plant-derived bioactive monolignol glucoside, synergistic effects of enzymatic and metabolic engineering were combined. Recombinant UGT72E3/E2 chimeras, generated by exchanging parts of the C-terminal domain including the Putative Secondary Plant Glycosyltransferase (PSPG) motif of UGT72E3 and UGT72E2, were expressed in leaves of transgenic Arabidopsis plants; syringin production was measured in vivo and by enzymatic assays in vitro. In both tests, UGT72E3/2 displayed substrate specificity for sinapyl alcohol like the parental enzyme UGT72E3, and the syringin production was significantly increased compared to UGT72E3. In particular, in the in vitro assay, which was performed in the presence of a high concentration of sinapyl alcohol, the production of syringin by UGT72E3/2 was 4-fold higher than by UGT72E3. Furthermore, to enhance metabolic flow through the phenylpropanoid pathway and maintain a high basal concentration of sinapyl alcohol in the leaves, UGT72E3/2 was combined with the sinapyl alcohol synthesis pathway gene F5H encoding ferulate 5-hydroxylase and the lignin biosynthesis transcriptional activator MYB58. The resulting UGT72E3/2+F5H+MYB58 OE plants, which simultaneously overexpress these three genes, accumulated a 56-fold higher level of syringin in their leaves than wild-type plants. PMID:24667164

Chu, Yang; Kwon, Tackmin; Nam, Jaesung

2014-06-01

247

Genotoxicity of nitrosated red wine and of the nitrosatable phenolic compounds present in wine: tyramine, quercetin and malvidine-3-glucoside.  

PubMed

Phenolic compounds and biogenic amines are known to be present in some foodstuffs which become directly genotoxic after nitrosation in vitro. Red wine has previously been shown to be genotoxic and this activity has been attributed mainly to flavonoids. Besides flavonoids, red wine contains a multiplicity of compounds, including biogenic amines. Using the Ames assay and the SOS chromotest, this study has shown that red wine and some of the nitrosatable molecules present in wine become directly genotoxic on nitrosation in vitro: these include the phenolic molecules tyramine, quercetin and malvidine-3-glucoside, whereas phenylethylamine and histamine were negative on nitrosation. Interestingly, quercetin had been predicted to be negative after nitrosation, using the CASE methodology. The concentrations of these three positive nitrosatable compounds in wine were determined by HPLC. Comparison of these concentrations and their respective levels of genotoxicity suggests that the genotoxicity after nitrosation is probably attributable to other molecules. It is also possible that synergistic effects may occur between various nitrosatable compounds in wine. PMID:8282283

Laires, A; Gaspar, J; Borba, H; Proença, M; Monteiro, M; Rueff, J

1993-12-01

248

Characterization of intermolecular interaction between cyanidin-3-glucoside and bovine serum albumin: Spectroscopic and molecular docking methods.  

PubMed

The intermolecular interaction between cyanidin-3-glucoside (Cy-3-G) and bovine serum albumin (BSA) was investigated using fluorescence, circular dichroism and molecular docking methods. The experimental results revealed that the fluorescence quenching of BSA at 338?nm by Cy-3-G resulted from the formation of Cy-3-G-BSA complex. The number of binding sites (n) for Cy-3-G binding on BSA was approximately equal to 1. The experimental and molecular docking results revealed that after binding Cy-3-G to BSA, Cy-3-G is closer to the Tyr residue than the Trp residue, the secondary structure of BSA almost not change, the binding process of Cy-3-G with BSA is spontaneous, and Cy-3-G can be inserted into the hydrophobic cavity of BSA (site II') in the binding process of Cy-3-G with BSA. Moreover, based on the sign and magnitude of the enthalpy and entropy changes (?H(0) ?=?- 29.64?kcal/mol and ?S(0) ?=?- 69.51?cal/mol?K) and the molecular docking results, it can be suggested that the main interaction forces of Cy-3-G with BSA are Van der Waals and hydrogen bonding interactions. Copyright © 2013 John Wiley & Sons, Ltd. PMID:24123897

Shi, Jie-Hua; Wang, Jing; Zhu, Ying-Yao; Chen, Jun

2014-08-01

249

A new thermostable ?-glucosidase mined from Dictyoglomus thermophilum: properties and performance in octyl glucoside synthesis at high temperatures.  

PubMed

A new ?-glucosidase (DtGH) representing 40% identity with an apple seed glycosidase (ASG) was cloned from Dictyoglomus thermophilum. DtGH showed extremely high thermostability in aqueous solution, with half-lives of 533, 44, and 5 h measured at 70, 80 and 90 °C, respectively. Therefore it was used for direct glycosylation of n-octanol at 70 °C instead of 50 °C as usually. As a result, the glucose based conversion was increased by 27%, but the time spent to reach equilibrium was decreased from 7 d to 3 d. This enzyme also exhibited excellent stability under the reaction environment, retaining 70-80% of its initial activity after 7 d of incubation at 70 °C in either 1.7 M glucose solution or octanol-aqueous (85:15, v/v) system. It could retain part of synthetic activity even in boiling water. Owing to the strong glucose-tolerance and extremely high thermostability, DtGH should be promising for various glucosides synthesis. PMID:22705966

Zou, Zheng-Zheng; Yu, Hui-Lei; Li, Chun-Xiu; Zhou, Xin-Wen; Hayashi, Chihiro; Sun, Jie; Liu, Bao-Hong; Imanaka, Tadeyuki; Xu, Jian-He

2012-08-01

250

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

PubMed

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

2010-02-24

251

Tetrahydroxystilbene glucoside attenuates MPP+-induced apoptosis in PC12 cells by inhibiting ROS generation and modulating JNK activation.  

PubMed

It is known that oxidative stress plays a major role in the progression of Parkinson's disease (PD). Previous studies have suggested that 2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside (TSG), an active component extracted from a traditional Chinese herb Polygonum multiflorum Thunb., has significant antioxidant and free radical-scavenging activities. This is the first study that investigated the protective effects of TSG against MPP(+)-induced apoptosis in PC12 cells and determined the underlying mechanism. The results showed that incubation of PC12 cells with TSG before exposing them to MPP(+) could significantly decrease cell viability loss and reverse cell apoptosis in a dose-dependent manner. The anti-apoptotic effects of TSG were probably mediated via the inhibition of ROS generation and modulation of JNK activation because TSG blocked ROS increase and JNK phosphorylation induced by MPP(+). Taken together, these results indicated that TSG may provide a useful therapeutic strategy for the treatment of neurodegenerative diseases such as PD. PMID:20643188

Li, Xiaobing; Li, Yan; Chen, Jianzong; Sun, Jing; Li, Xiaofeng; Sun, Xin; Kang, Xiaogang

2010-10-01

252

Protection by tetrahydroxystilbene glucoside against neurotoxicity induced by MPP+: the involvement of PI3K/Akt pathway activation.  

PubMed

Oxidative stress plays an important role in the pathogenesis of Parkinson's disease (PD). 2,3,5,4'-tetrahydroxystilbene-2-O-?-D-glucoside (TSG), which is an active component of the rhizome extract from polygonum multiflorum, shows potent antioxidant properties. In this paper, the neuroprotective effects of TSG on 1-methyl-4-phenylpyridinium (MPP+-induced apoptosis in PC12 cells were investigated. Pretreatment with TSG markedly attenuated MPP+-induced loss of cell viability and release of lactate dehydrogenase (LDH), and reduced MPP+-induced apoptotic cell death in a dose-dependent manner. The anti-apoptotic effects of TSG were probably mediated by the phosphatidylinositol 3-kinase (PI3K)/Akt signaling pathway since TSG failed to rescue cells from MPP+ injury in the presence of the PI3K inhibitor, LY294002. These results indicate that TSG affords a significant neuroprotective effect against MPP+-induced damage and apoptosis in PC12 cells. The PI3K/Akt signaling pathway might be involved in the TSG-mediated anti-apoptotic effects. PMID:21237255

Qin, Rong; Li, Xiaobing; Li, Gang; Tao, Lizhen; Li, Yan; Sun, Jing; Kang, Xiaogang; Chen, Jianzong

2011-04-10

253

Determination of the relative contribution of quercetin and its glucosides to the antioxidant capacity of onion by cyclic voltammetry and spectrophotometric methods.  

PubMed

This paper describes the use of cyclic voltammetry (CV), spectrophotometric methods [Trolox equivalent antioxidant capacity (TEAC), peroxyl radical trapping capacity (PRTC), DPPH radical scavenging activity (RSA), and Folin-Ciocalteu reagent (FCR) reducing capacity], and photochemiluminescence (PCL) for the measurement of the antioxidant capacity of onion var. Sochaczewska and var. Szalotka. The antioxidant and reducing activity of the dominant onion flavonoids quercetin (Q), quercetin-3- O-beta-glucoside (Q3G), quercetin-4'- O-beta-glucoside (Q4'G), and quercetin-3,4'-di- O-beta-glucoside (Q3,4'G) were determined by spectrophotometric (TEAC and PRTC) and CV methods, respectively. The contribution of quercetin and its glucosides to the antioxidant capacity of onion was calculated in consequence of the qualitative and quantitative analysis of onion flavonoids by high-performance liquid chromatography-ultraviolet-mass spectrometry. The dominant forms of quercetin in the onion var. Sochaczewska and Szalotka included Q4'G (61 and 54%), Q3,4'G (37 and 44%), Q3G (1.4 and 1.1%), and free quercetin (1.1 and 0.7%), respectively. The CV experiment showed the highest reducing activity of Q while Q3G, Q4'G, and Q3,4'G exhibited about 68, 51, and 30% of the reducing power noted for Q. The order of the reducing activity of onion flavonoids was confirmed by their free radical scavenging activity and evaluated by TEAC and PRTC assays as follows: Q > Q3G > Q4'G > Q3,4'G. The Q4'G and Q3,4'G showed poor antioxidant activity under both applied spectrophotometric assays but still exhibited reducing activity based on CV experiments. The reducing capacity of onions determined by CV method was twice higher than the antioxidant capacity formed by water-soluble compounds (ACW) evaluated by PCL, and it was about 50% higher than PRTC and DPPH RSA results and the converted FCR reducing capacity. In contrast, the reducing capacity of onions determined by the CV method was 3-fold and about four times lower when compared to the antioxidant capacity evaluated by the TEAC method and that formed by lipid-soluble compounds (ACL) provided by PCL, respectively. The highest antioxidant capacity of onion was found under cumulative consideration of PCL (ACW + ACL) and TEAC assays. The relative contribution of Q and its glucosides to the antioxidant capacity of onions showed a low contribution of Q, Q3G, and Q3,4'G derived from CV, TEAC, and PRTC assays while the highest contribution to the antioxidant capacity of onions was provided by Q4'G. PMID:18454541

Zielinska, Danuta; Wiczkowski, Wieslaw; Piskula, Mariusz Konrad

2008-05-28

254

The effect of 2,3,4',5-tetrahydroxystilbene-2-O-?-D-glucoside on pressure overload-induced cardiac remodeling in rats and its possible mechanism.  

PubMed

The aim of the present study was to investigate the effects of 2,3,4',5-tetrahydroxystilbene-2-O-beta-D-glucoside, an active component extracted from Polygonum multiflorum, on pressure overload-induced cardiac remodeling in rats. A rat model with cardiac remodeling was induced by abdominal aortic banding. 2,3,4',5-Tetrahydroxystilbene-2-O-beta-D-glucoside (30, 60, 120?mg/kg/day) was administered 3 days after abdominal aortic banding and continued for 30 days. The abdominal aortic banding-treated rats had significantly elevated blood pressure, left ventricular hypertrophy, and myocardial fibrosis. Left ventricular hypertrophy was characterized by an increase in the ratios of the heart and left ventricular weights to body weight, and increased myocyte cross-sectional areas, hypertrophic ventricular septum, and left ventricular posterior wall. The accumulation of myocardial interstitial perivascular collagen and elevated cardiac hydroxyproline content indicated myocardial fibrosis. The pathological changes above were attenuated by 2,3,4',5-tetrahydroxystilbene-2-O-beta-D-glucoside. Additionally, it markedly reduced collagen I and III expressions and regulated matrix metalloproteinase-2,9 and inhibitors of metalloproteinase expressions, as markers of myocardial fibrosis. Furthermore, we explored the underlying mechanisms for such effects of 2,3,4',5-tetrahydroxystilbene-2-O-beta-D-glucoside. The results showed that it significantly reduced myocardium angiotensin II, enhanced the activities of superoxide dismutase and glutathione peroxidase in serum and myocardial tissue, as well as inhibited protein expression of transforming growth factor-?1 and phosphorylation of extracellular signal-regulated kinase 1/2 and p38 mitogen-activated protein kinase in the myocardial tissue. Our results suggest that 2,3,4',5-tetrahydroxystilbene-2-O-beta-D-glucoside could prevent cardiac remodeling induced by pressure overload in rats. The underlying mechanisms may be related to a decreasing angiotensin II level, an antioxidant effect of the tested compound, suppression of transforming growth factor-?1 expression, and inhibition of extracellular signal-regulated kinase 1/2 and p38 mitogen-activated protein kinase activation. PMID:24431015

Xu, Xiao Le; Zhu, Qiu Yan; Zhao, Cheng; Wang, Fei; Zhou, Zhong Yin; Hu, Ya E; Zhang, Wei

2014-02-01

255

Plant Food Delphinidin-3-Glucoside Significantly Inhibits Platelet Activation and Thrombosis: Novel Protective Roles against Cardiovascular Diseases  

PubMed Central

Delphinidin-3-glucoside (Dp-3-g) is one of the predominant bioactive compounds of anthocyanins in many plant foods. Although several anthocyanin compounds have been reported to be protective against cardiovascular diseases (CVDs), the direct effect of anthocyanins on platelets, the key players in atherothrombosis, has not been studied. The roles of Dp-3-g in platelet function are completely unknown. The present study investigated the effects of Dp-3-g on platelet activation and several thrombosis models in vitro and in vivo. We found that Dp-3-g significantly inhibited human and murine platelet aggregation in both platelet-rich plasma and purified platelets. It also markedly reduced thrombus growth in human and murine blood in perfusion chambers at both low and high shear rates. Using intravital microscopy, we observed that Dp-3-g decreased platelet deposition, destabilized thrombi, and prolonged the time required for vessel occlusion. Dp-3-g also significantly inhibited thrombus growth in a carotid artery thrombosis model. To elucidate the mechanisms, we examined platelet activation markers via flow cytometry and found that Dp-3-g significantly inhibited the expression of P-selectin, CD63, CD40L, which reflect platelet ?- and ?-granule release, and cytosol protein secretion, respectively. We further demonstrated that Dp-3-g downregulated the expression of active integrin ?IIb?3 on platelets, and attenuated fibrinogen binding to platelets following agonist treatment, without interfering with the direct interaction between fibrinogen and integrin ?IIb?3. We found that Dp-3-g reduced phosphorylation of adenosine monophosphate-activated protein kinase, which may contribute to the observed inhibitory effects on platelet activation. Thus, Dp-3-g significantly inhibits platelet activation and attenuates thrombus growth at both arterial and venous shear stresses, which likely contributes to its protective roles against thrombosis and CVDs.

Yang, Yan; Shi, Zhenyin; Reheman, Adili; Jin, Joseph W.; Li, Conglei; Wang, Yiming; Andrews, Marc C.; Chen, Pingguo; Zhu, Guangheng; Ling, Wenhua; Ni, Heyu

2012-01-01

256

Cyanidin-3-Glucoside inhibits ethanol-induced invasion of breast cancer cells overexpressing ErbB2  

PubMed Central

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 identify agents that can prevent or ameliorate ethanol-induced invasion of breast cancer cells. Cyanidin-3-glucoside (C3G), an anthocyanin present in many vegetables and fruits, is a potent natural antioxidant. Ethanol exposure causes the accumulation of intracellular reactive oxygen species (ROS). This study evaluated the effect of C3G on ethanol-induced breast cancer cell migration/invasion. Results C3G attenuated ethanol-induced migration/invasion of breast cancer cells expressing high levels of ErbB2 (BT474, MDA-MB231 and MCF7ErbB2) in a concentration dependent manner. C3G decreased ethanol-mediated cell adhesion to the extracellular matrix (ECM) as well as the amount of focal adhesions and the formation of lamellipodial protrusion. It inhibited ethanol-stimulated phosphorylation of ErbB2, cSrc, FAK and p130Cas, as well as interactions among these proteins. C3G abolished ethanol-mediated p130Cas/JNK interaction. Conclusions C3G blocks ethanol-induced activation of the ErbB2/cSrc/FAK pathway which is necessary for cell migration/invasion. C3G may be beneficial in preventing/reducing ethanol-induced breast cancer metastasis.

2010-01-01

257

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

PubMed

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

2013-03-01

258

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

PubMed

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

2011-09-14

259

A semiquinone glucoside derivative provides protection to male reproductive system of the mice against gamma radiation toxicity.  

PubMed

Present investigation was carried out to evaluate the radioprotective efficacy of a novel Semiquinone glucoside derivative (SQGD), isolated from Bacillus sp. INM-1, in the male reproductive system of BALB/c mice. Animals were administered 50 mg/kg b.wt. (i.p.) SQGD 2 h before whole body ?-irradiation (10 Gy). Radiation-induced cellular toxicity and its modulation by SQGD pretreatment was evaluated in the mice testes by quantitative histological and protein expression analysis. SQGD pretreatment protects irradiated mice from radiation-induced testicular atrophy and germ cells degeneration, which may lead to emptiness of seminiferous tubules. Significant decrease in P53 and P21((Cip/WAF-1)) expression was observed in the irradiated mice pretreated (2 h) by SQGD at 6 h compared with only irradiated mice. However, contrary to P53, expressions of P21 at latter time, that is, 24-72 h was found to be increased significantly in the irradiated mice pretreated by SQGD. Significant increase in the intact PARP-1 protein expression were observed in the testes of the mice pretreated by SQGD 2 h before irradiation at 24-72 h compared with the only irradiated mice, whereas significant increase in PARP-1 cleaved fragment was noticed at 24 h. Similarly, significant increase in NF-kB and BCL-2/BAX expressions ratio was noticed in SQGD-treated mice (± irradiation) compared with irradiated mice, suggested a role of SQGD in the activation of prosurvival signaling in the testicular germinal cells population of the irradiated mice and thus contributed to protection against lethal ?-irradiation. PMID:22730153

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

2014-05-01

260

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.

2013-01-01

261

Cyanidin-3-O-?-glucoside ameliorates lipopolysaccharide-induced acute lung injury by reducing TLR4 recruitment into lipid rafts.  

PubMed

Cyanidin-3-O-?-glucoside (C3G), a typical anthocyanin pigment that exists in the human diet, has been reported to have anti-inflammatory properties. The aim of this study was to detect the effect of C3G on LPS-induced acute lung injury and to investigate the molecular mechanisms. Acute lung injury was induced by intratracheal administration of LPS in mice. Alveolar macrophages from mice were stimulated with LPS and were treated with C3G. Our results showed that C3G attenuated lung histopathologic changes, myeloperoxidase (MPO) activity, TNF-?, IL-1? and IL-6 production in LPS-induced acute lung injury model. In vitro, C3G dose-dependently inhibited TNF-?, IL-1?, IL-6, IL-10 and IFN-? production, as well as NF-?B and IRF3 activation in LPS-stimulated alveolar macrophages. Furthermore, C3G disrupted the formation of lipid rafts by depleting cholesterol and inhibited TLR4 translocation into lipid rafts. Moreover, C3G activated LXR?-ABCG1-dependent cholesterol efflux. Knockout of LXR? abrogated the anti-inflammatory effects of C3G. In conclusion, C3G has a protective effect on LPS-induced acute lung injury. The promising anti-inflammatory mechanisms of C3G is associated with up-regulation of the LXR?-ABCG1 pathway which result in disrupting lipid rafts by depleting cholesterol and reducing translocation of TLR4 to lipid rafts, thereby suppressing TLR4 mediated inflammatory response. PMID:24841888

Fu, Yunhe; Zhou, Ershun; Wei, Zhengkai; Wang, Wei; Wang, Tiancheng; Yang, Zhengtao; Zhang, Naisheng

2014-07-15

262

Contribution of gut bacteria to the metabolism of cyanidin 3-glucoside in human microbiota-associated rats.  

PubMed

Cyanidin 3-glucoside (C3G) is one of the major dietary anthocyanins implicated in the prevention of chronic diseases. To evaluate the impact of human intestinal bacteria on the fate of C3G in the host, we studied the metabolism of C3G in human microbiota-associated (HMA) rats in comparison with germ-free (GF) rats. Urine and faeces of the rats were analysed for C3G and its metabolites within 48 h after the application of 92 ?mol C3G/kg body weight. In addition, we tested the microbial C3G conversion in vitro by incubating C3G with human faecal slurries and selected human gut bacteria. The HMA rats excreted with faeces a three times higher percentage of unconjugated C3G products and a two times higher percentage of conjugated C3G products than the GF rats. These differences were mainly due to the increased excretion of 3,4-dihydroxybenzoic acid, 2,4,6-trihydroxybenzaldehyde and 2,4,6-trihydroxybenzoic acid. Only the urine of HMA rats contained peonidin and 3-hydroxycinnamic acid and the percentage of conjugated C3G products in the urine was decreased compared with the GF rats. Overall, the presence of intestinal microbiota resulted in a 3·7% recovery of the C3G dose in HMA rats compared with 1·7% in GF rats. Human intestinal bacteria rapidly degraded C3G in vitro. Most of the C3G products were also found in the absence of bacteria, but at considerably lower levels. The higher concentrations of phenolic acids observed in the presence of intestinal bacteria may contribute to the proposed beneficial health effects of C3G. PMID:22906731

Hanske, Laura; Engst, Wolfram; Loh, Gunnar; Sczesny, Silke; Blaut, Michael; Braune, Annett

2013-04-28

263

BglR protein, which belongs to the BglG family of transcriptional antiterminators, is involved in beta-glucoside utilization in Lactococcus lactis.  

PubMed Central

A fragment of the Lactococcus lactis chromosome containing an open reading frame of 265 codons, denoted bglR, has been characterized. The polypeptide encoded by bglR shares 36 to 30% sequence identity with a family of regulatory proteins including ArbG from Erwinia chrysanthemi, BglG from Escherichia coli, and SacT and SacY from Bacillus subtilis. These regulatory proteins are involved in positive control of the utilization of different sugars by transcription antitermination. For some of these regulatory proteins it has been demonstrated that antitermination is exerted by binding to a conserved RNA sequence, partially overlapping the transcription terminator and thus preventing transcription termination. Upstream of bglR, we identified a transcription terminator whose 5' end was overlapped by a 32-bp sequence, highly homologous to the RNA-binding site that is conserved in other regulatory systems. Constitutive expression of bglR in E. coli increased the expression of a bglG::lacZ transcriptional fusion. The fact that that the expression of BglG is autoregulated in E. coli suggests that BglG and BglR are functionally equivalent. In L. lactis, we observed that (i) the expression of a bglR::lacZ fusion is increased by beta-glucoside sugars, (ii) disruption of bglR impairs growth on some beta-glucosides, and (iii) the expression of bglR is positively autoregulated. Because of these structural and functional similarities between BglR and the transcription antiterminators of the BglG family, we propose that BglR may be the lactococcal counterpart of the E. coli BglG regulator of beta-glucoside utilization.

Bardowski, J; Ehrlich, S D; Chopin, A

1994-01-01

264

The crystal structure of rice (Oryza sativa L.) Os4BGlu12, an oligosaccharide and tuberonic acid glucoside-hydrolyzing ?-glucosidase with significant thioglucohydrolase activity.  

PubMed

Rice Os4BGlu12, a glycoside hydrolase family 1 (GH1) ?-glucosidase, hydrolyzes ?-(1,4)-linked oligosaccharides of 3-6 glucosyl residues and the ?-(1,3)-linked disaccharide laminaribiose, as well as certain glycosides. The crystal structures of apo Os4BGlu12, and its complexes with 2,4-dinitrophenyl-2-deoxyl-2-fluoroglucoside (DNP2FG) and 2-deoxy-2-fluoroglucose (G2F) were solved at 2.50, 2.45 and 2.40Å resolution, respectively. The overall structure of rice Os4BGlu12 is typical of GH1 enzymes, but it contains an extra disulfide bridge in the loop B region. The glucose ring of the G2F in the covalent intermediate was found in a (4)C(1) chair conformation, while that of the noncovalently bound DNP2FG had a (1)S(3) skew boat, consistent with hydrolysis via a (4)H(3) half-chair transition state. The position of the catalytic nucleophile (Glu393) in the G2F structure was more similar to that of the Sinapsis alba myrosinase G2F complex than to that in covalent intermediates of other O-glucosidases, such as rice Os3BGlu6 and Os3BGlu7 ?-glucosidases. This correlated with a significant thioglucosidase activity for Os4BGlu12, although with 200- to 1200-fold lower k(cat)/K(m) values for S-glucosides than the comparable O-glucosides, while hydrolysis of S-glucosides was undetectable for Os3BGlu6 and Os3BGlu7. PMID:21521631

Sansenya, Sompong; Opassiri, Rodjana; Kuaprasert, Buabarn; Chen, Chun-Jung; Cairns, James R Ketudat

2011-06-01

265

Isolation of liquiritigenin-4'-apiosyl-glucoside and liquiritin from the root of Glycyrrhiza uralensis by high-performance centrifugal partition chromatography.  

PubMed

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

2014-04-01

266

Formononetin 7-O-glucoside (ononin), an additional growth inhibitor in soils associated with the weed,Pluchea lanceolata (DC) C.B. Clarke (Asteraceae).  

PubMed

Formononetin 7-O-glucoside (ononin), an isoflavonoid, was isolated from the soils of cultivated areas associated with the perennial weed,Pluchea lanceolata. Aqueous solutions of this compound inhibited significantly root and shoot growth of mustard at 1×10(-4) M, 5×10(-4) M, and 1×10(-3)M. The level of inhibition was similar to that of hesperidin and taxifolin 3-arabinoside, as reported earlier. The potential allelopathic effect of this compound under field conditions is discussed. PMID:24253965

Inderjit; Dakshini, K M

1992-05-01

267

Chemical constituents from the leaves of Hydrangea macrophylla var. thunbergii (III): Absolute stereostructures of hydramacrosides A and B, secoiridoid glucoside complexes with inhibitory activity on histamine release.  

PubMed

Following the characterization of dihydroisocoumarin constituents, two secoiridoid glucoside complexes, called hydramacrosides A and B, were isolated from the leaves of Hydrangea macrophylla Seringe var. thunbergii Makino. The absolute stereostructures of hydramacrosides A and B were elucidated on the basis of chemical and physicochemical evidence, which included the application of the 13C-NMR glycosylation shift rule of 1,1'-disaccharides and the modified Mosher's method. Hydramacrosides A and B exhibited an inhibitory effect on histamine release from rat mast cells induced by an antigen-antibody reaction. PMID:10748718

Matsuda, H; Shimoda, H; Uemura, T; Ueda, T; Yamahara, J; Yoshikawa, M

1999-12-01

268

Absolute stereostructures of hydramacrosides A and B, new bioactive secoiridoid glucoside complexes from the leaves of Hydrangea macrophylla Seringe var. thunbergii Makino.  

PubMed

Two new bioactive secoiridoid glucoside complexes named hydramacrosides A and B were isolated from the leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO. The absolute stereostructures of hydramacrosides A and B were elucidated on the basis of chemical and physicochemical evidence which included the application of the 13C NMR glycosylation shift rule of 1, 1'-disaccharides and the modified Mosher's method. Hydramacrosides A and B exhibited inhibitory effect on the histamine release from rat mast cells induced by antigen-antibody reaction. PMID:7525087

Yoshikawa, M; Ueda, T; Matsuda, H; Yamahara, J; Murakami, N

1994-08-01

269

Natural Variation in Maize Aphid Resistance Is Associated with 2,4-Dihydroxy-7-Methoxy-1,4-Benzoxazin-3-One Glucoside Methyltransferase Activity[C][W  

PubMed Central

Plants differ greatly in their susceptibility to insect herbivory, suggesting both local adaptation and resistance tradeoffs. We used maize (Zea mays) recombinant inbred lines to map a quantitative trait locus (QTL) for the maize leaf aphid (Rhopalosiphum maidis) susceptibility to maize Chromosome 1. Phytochemical analysis revealed that the same locus was also associated with high levels of 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one glucoside (HDMBOA-Glc) and low levels of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside (DIMBOA-Glc). In vitro enzyme assays with candidate genes from the region of the QTL identified three O-methyltransferases (Bx10a-c) that convert DIMBOA-Glc to HDMBOA-Glc. Variation in HDMBOA-Glc production was attributed to a natural CACTA family transposon insertion that inactivates Bx10c in maize lines with low HDMBOA-Glc accumulation. When tested with a population of 26 diverse maize inbred lines, R. maidis produced more progeny on those with high HDMBOA-Glc and low DIMBOA-Glc. Although HDMBOA-Glc was more toxic to R. maidis than DIMBOA-Glc in vitro, BX10c activity and the resulting decline of DIMBOA-Glc upon methylation to HDMBOA-Glc were associated with reduced callose deposition as an aphid defense response in vivo. Thus, a natural transposon insertion appears to mediate an ecologically relevant trade-off between the direct toxicity and defense-inducing properties of maize benzoxazinoids.

Meihls, Lisa N.; Handrick, Vinzenz; Glauser, Gaetan; Barbier, Hugues; Kaur, Harleen; Haribal, Meena M.; Lipka, Alexander E.; Gershenzon, Jonathan; Buckler, Edward S.; Erb, Matthias; Kollner, Tobias G.; Jander, Georg

2013-01-01

270

Plantagiolides I and J, two new withanolide glucosides from Tacca plantaginea with nuclear factor-kappaB inhibitory and peroxisome proliferator-activated receptor transactivational activities.  

PubMed

A novel withanolide glucoside, plantagiolide I (1), a new withanolide glucoside, plantagiolide J (2), and six known compounds (3-8) were isolated from the whole plant of Tacca plantaginea. Their structures were determined by spectroscopic and chemical methods. Compound 3 significantly inhibited tumor necrosis factor alpha (TNF?)-induced nuclear factor-kappaB (NF-?B) transcriptional activity in HepG2 cells in a dose-dependent manner, with IC(50) values of 9.0?µM. Compounds 1-8 enhanced the transcriptional activity of peroxisome proliferator-activated receptors (PPARs) in a dose-dependent manner, with EC(50) values ranging from 1.6 to 49.7?µM. In addition, the transactivational effects of compounds 1-8 on three individual PPAR subtypes, including PPAR?, ?(?), and ? were evaluated. Compounds 1-8 significantly activated the transcriptional activity of PPAR?(?), with EC(50) values in a ranging from 4.1 to 29.6?µM. These results provide scientific support for the use of T. plantaginea and its components for the prevention and treatment of inflammatory and metabolic diseases. PMID:23207631

Quang, Tran Hong; Ngan, Nguyen Thi Thanh; Minh, Chau Van; Kiem, Phan Van; Yen, Pham Hai; Tai, Bui Huu; Nhiem, Nguyen Xuan; Thao, Nguyen Phuong; Anh, Hoang Le Tuan; Luyen, Bui Thi Thuy; Yang, Seo Young; Kim, Young Ho

2012-01-01

271

Halohydrins and polyols derived from antirrhinoside: structural revisions of muralioside and epimuralioside  

PubMed

Treatment of the iridoid glucoside antirrhinoside (1) with pyridinium chloride in dimethylformamide gave rise to the two possible trans-halohydrins, linarioside (4) and isolinarioside (5). Pyridinium bromide gave the two analogous bromohydrins. It is shown that the iridoid glucosides 8-epi-muralioside from Linaria arcusangeli and 7,8-epi-antirrhinoside from Linaria dalmatica are both identical with isolinarioside, and therefore, these names are redundant. The structure of muralioside isolated from Cymbalaria muralis is revised to that of its 8-epimer (8), while the structure of an isomeric, new iridoid glucoside from Paulownia tomentosa has been elucidated to be 7beta-hydroxyharpagide (3), the structure originally assigned to 8. In addition, 7alpha-hydroxyharpagide (2), the known product from the base-catalyzed hydrolytic opening of 1, has been isolated from Antirrhinum majus and thus shown to be a natural product. PMID:10075758

Franzyk; Jensen; Thale; Olsen

1999-02-01

272

High-performance liquid chromatographic determination and pharmacokinetic study of apigenin-7-O-?-D-glucoside in rat plasma after intravenous administration.  

PubMed

The present study was designed to validate an analytical method based on HPLC for the quantitative measurement of the Apigenin-7-O-?-D-glucoside (AGL) in rat plasma after intravenous administration. HPLC analysis was done using a C18 column, UV detection at 335 nm, and a mobile phase of methanol:0.2% phosphoric acid (1:1, v/v). Good linearity was observed over the range of 0.06-7.20 ?g/mL with a lower limit of quantication of 0.06 ?g/mL. The intra-and inter-day precision values were below 9.97%. No interference peaks or matrix effects were observed. The method was fully validated and successfully applied to a pharmacokinetic study of AGL. PMID:21656359

Chen, Zaixing; Ying, Xixiang; Meng, Shu; Zhu, Xu; Jiang, Hong; Cao, Qishen; Li, Xuying; Meng, Fanhao

2011-05-01

273

The extraction of imperialine and imperialine-3 beta-glucoside from Fritillaria pallidiflora Schrenk and quantitative determination by HPLC-evaporative light scattering detection.  

PubMed

The extraction procedure and quantitative determination by HPLC-evaporative light scattering detection (ELSD) of the main bioactive components, namely, imperialine (1) and imperialine-3 beta-glucoside (2), of bulbs of Fritillaria pallidiflora Schrenk have been investigated. The most efficient method for the simultaneous extraction of 1 and 2 involved pre-treatment of the bulb powder with ammonia, followed by reflux with dichloromethane:methanol at 90 degrees C for 4 h. Simultaneous determination of non-chromophoric 1 and 2 by HPLC-ELSD employed a Kromasil C18 column eluted with acetonitrile:water:diethylamine. The assay was accurate and reproducible with an overall variation lower than 4% and a sample recovery higher than 98%. The methods described have been successfully used to evaluate the quality of three batches of the crude traditional Chinese medicinal herb derived from the bulbs of F. pallidiflora. PMID:12099106

Li, Ping; Zeng, Ling-Jie; Li, Song-Lin; Lin, Ge

2002-01-01

274

Simultaneous determination of major type B trichothecenes and deoxynivalenol-3-glucoside in animal feed and raw materials using improved DSPE combined with LC-MS/MS.  

PubMed

A simple and reliable method for simultaneous determination of deoxynivalenol-3-glucoside and major type B trichothecenes (deoxynivalenol, nivalenol, fusarenon X, 3-acetyldeoxynivalenol, 15-acetyldeoxynivalenol and deepoxy-deoxynivalenol) in animal feed and raw materials has been developed and validated in this study. The method was based on an improved dispersive solid-phase extraction (DSPE) followed by analysis using high performance liquid chromatography coupled to tandem mass spectrometry (HPLC-MS/MS). Also, matrix-matched calibration curve (R(2)>0.99) was employed to minimize matrix effects and ensure accurate quantification. The recoveries during sample preparation process (including extraction and clean-up) ranged from 79.03% to 118.39%, with intra-day and inter-day relative standard deviation lower than 20% for all the analytes. The limit of quantification ranged from 5.0?g/kg for deoxynivalenol to 13.6?g/kg for fusarenon X. The validated method was successfully applied to the analysis of animal feed and corn. The pilot study showed that 37 out of 41 samples were contaminated with deoxynivalenol-3-glucoside at the levels of 6.0-121.0?g/kg. Most of the type B trichothecenes were also found with the exception of fusarenon X, at the contaminated levels of 10.0-1382?g/kg. To the best of our knowledge, this was the first scientific report on the co-occurrence of masked deoxynivalenol and type B trichothecenes in animal feed and raw materials. PMID:24935763

Zhao, Zhiyong; Rao, Qinxiong; Song, Suquan; Liu, Na; Han, Zheng; Hou, Jiafa; Wu, Aibo

2014-07-15

275

Screening of a glucoside 3-dehydrogenase-producing strain, Sphingobacterium faecium, based on a high-throughput screening method and optimization of the culture conditions for enzyme production.  

PubMed

The objective of this study was to screen glucoside 3-dehydrogenase (G3DH)-producing strain based on a high-throughput G3DH screening method. Optimization of culture conditions of the isolated strain was also applied in this study. This screening method employed electron transfer reaction in 96-well microtiter plates, ?-methyl-D-glucoside, galactose, 2-deoxy-D-glucose, and 3-O-methyl-D-glucose were used as substrates. Using this screening method, one out of 78 strains isolated from different soil samples was obtained with high G3DH activity. The accuracy of the screening method was proved by alkaline treatment analysis of 3-keto sugars. The isolated strain was identified as Sphingobacterium faecium ZJF-D6 by phenotypic characterization and 16S rDNA sequence analysis. The culture conditions of S. faecium for G3DH production were optimized. Sucrose was found as the most suitable carbon source for the G3DH production. The highest G3DH production and cell growth were achieved using the medium at the initial pH of 7.0 at 25 °C for 36 h with activity of 8.03?×?10(-2) U/mL culture. This strain appears promising for potential application in the industry to produce 3-keto sugars. To our knowledge, this is the first report on S. faecium for G3DH production. The method described herein represents a useful tool for the high-throughput isolation of G3DH. PMID:24532484

Zhang, Jianfen; Chen, Weiqing; Ke, Wei; Chen, Hong

2014-04-01

276

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  

Microsoft Academic Search

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

Marie Therese Paternostre; Michel Roux; Jean Louis Rigaud

1988-01-01

277

PHARMACOKINETICS, BIOAVAILABILITY, AND METABOLISM OF 2,3,5,4?-TETRAHYDROXYSTILBENE-2-O-?;-D-GLUCOSIDE IN RATS BY ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY–QUADRUPOLE TIME-OF-FLIGHT MASS SPECTROMETRY AND HIGH PERFORMANCE LIQUID CHROMATOGRAPHY-ULTRAVIOLET DETECTION  

Microsoft Academic Search

2,3,5,4?-tetrahydroxystilbene-2-O-?-D-glucoside (THSG), a natural product purified from the Chinese medical herb Polygoni multiflori Radix, has been demonstrated to possess many pharmacological activities, including antioxidant, anti-inflammatory, hepatoprotective and antitumor properties. Ultra performance liquid chromatography– time-of-flight mass spectrometry (UPLC-Q-TOF\\/MS) and high performance liquid chromatography-ultraviolet detection (HPLC-UV) methods were developed for the pharmacokinetics, bioavailability, absorption and metabolism studies of THSG in rats following

Ying-Yong Zhao; Xian-Long Cheng; Feng Wei; Xiao-Qiang Han; Xin-Yue Xiao; Rui-Chao Lin

2012-01-01

278

Identification of Candida dubliniensis Based on Temperature and Utilization of Xylose and a-Methyl-D-Glucoside as Determined with the API 20C AUX and Vitek YBC Systems  

Microsoft Academic Search

To have a better understanding of the role of Candida dubliniensis in clinical infections, it is essential that microbiology laboratories can identify this species rapidly and accurately in clinical specimens. C. dubliniensis has been reported to lack the ability to utilize xylose (XYL) and a-methyl-D-glucoside (MDG) and to grow poorly or not at all at 45°C, whereas Candida albicans isolates

A. C. GALES; M. A. PFALLER; A. K. HOUSTON; S. JOLY; D. J. SULLIVAN; D. C. COLEMAN; D. R. SOLL

1999-01-01

279

Kaempferol7- O-?- d-glucoside (KG) isolated from Smilax china L. rhizome induces G 2\\/M phase arrest and apoptosis on HeLa cells in a p53-independent manner  

Microsoft Academic Search

Kaempferol-7-O-?-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

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

2008-01-01

280

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))

1993-01-01

281

Identification of xanthurenic acid 8-O-beta-D-glucoside and xanthurenic acid 8-O-sulfate as human natriuretic hormones.  

PubMed

Hormonal regulation of salt excretion and water balance by the kidneys is well documented. Before 1961, it was widely believed that the glomerular filtration rate and the steroid hormone aldosterone controlled sodium balance in the body. In 1961, deWardener et al. [de Wardener HE, Mills IH, Clapham WF, Hayter CJ (1961) Clin Sci 21:249-258] showed that when these two variables were controlled, the kidney was still able to increase sodium excretion in response to a salt load. Several lines of evidence argued for a small-molecule signal as a definitive modulator of sodium excretion by the kidney. However, the chemical nature of the suspected natriuretic agent remained unknown. Here we report the identification and natriuretic activity of two closely related small molecules isolated from human urine, xanthurenic acid 8-O-beta-d-glucoside and xanthurenic acid 8-O-sulfate. The two compounds were partially purified by activity-guided fractionation and subsequently identified by using NMR spectroscopic analyses of enriched active fractions. Both compounds caused substantial and sustained (1- to 2-h) natriuresis in rats and no or minimal concomitant potassium excretion. We believe these compounds constitute a class of kidney hormones that also could influence sodium transport in nonkidney tissues given that these tryptophan metabolites presumably represent evolutionarily old structures. PMID:17978185

Cain, Christopher D; Schroeder, Frank C; Shankel, Stewart W; Mitchnick, Mark; Schmertzler, Michael; Bricker, Neal S

2007-11-01

282

Delphinidin-3-Glucoside Protects against Oxidized Low-Density Lipoprotein-Induced Mitochondrial Dysfunction in Vascular Endothelial Cells via the Sodium-Dependent Glucose Transporter SGLT1  

PubMed Central

Delphinidin-3-glucoside (Dp) is a member of a family of bioactive compounds known as anthocyanins that occur naturally in pigmented plants and are known to ameliorate oxidative stress. Previous studies have showed that Dp decreased oxidative stress in vascular endothelial cells, however, the underlying mechanisms remain largely unknown. In the present study, we showed that pretreatment with Dp significantly suppressed oxidized low-density lipoprotein (oxLDL)-induced cell proliferation inhibition and apoptosis in primary human umbilical vein endothelial cells (HUVECs). Also, Dp pretreatment attenuated oxLDL-induced mitochondrial dysfunction via decreased reactive oxygen species (ROS) and superoxide anion generation, thereby repressing mitochondrial membrane potential and closing mitochondrial permeability transition pore. Furthermore, in vitro and in vivo data showed that Dp was transported into endothelial cells in a temperature, concentration, and time-dependent manner via the sodium-dependent glucose transporter (SGLT1). Suppression of SGLT1 by its substrate glucose, its inhibitor phlorizin or SGLT1 siRNA blocked Dp transportation. Repression of SGLT1 significantly inhibited Dp function of ameliorating mitochondrial dysfunction induced by pro-apoptotic factors (Apoptosis-inducing factor, Cytochrome c, Caspase-3 and Bax/Bcl-2 ratio). Taken together, our data indicate that Dp protects VECs via the SGLT1-ROS-mitochodria pathway. This new insight may help to elucidate the molecular mechanisms underlying the vascular protection afforded by Dp, and anthocyanins in general, in the context of prevention of endothelial dysfunction and atherosclerosis.

Chen, Ming-liang; Chen, Chun-ye; Chang, Hui; Zhang, Ting; Wang, Li; Zhu, Jun-dong; Zhang, Qian-yong; Mi, Man-tian

2013-01-01

283

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

2008-01-01

284

Microarray Analysis of mRNA and MicroRNA Expression Profile Reveals the Role of ?-Sitosterol-D-glucoside in the Proliferation of Neural Stem Cell  

PubMed Central

Neural stem cells (NSCs) are self-regenerating cells, but their regenerative capacity is limited. The present study was conducted to investigate the effect of ?-sitosterol-D-glucoside (BSSG) on the proliferation of hippocampal NSCs and to determine the corresponding molecular mechanism. Results of CCK-8 assay showed that BSSG significantly increased NSC proliferation and the effectiveness of BSSG was similar to that of basic fibroblast growth factor and epidermal growth factor. mRNA expression profiling showed that 960 genes were differentially expressed after NSCs were treated with BSSG. Among the 960 genes, IGF1 is considered as a key regulatory gene that functionally promotes NSC proliferation. MicroRNA (miRNA) expression profiling indicated that 30 and 84 miRNAs were upregulated and downregulated, respectively. miRNA-mRNA relevance analysis revealed that numerous mRNAs including IGF1 mRNA were negatively regulated by miRNAs with decreased expression, thereby increasing the corresponding mRNA expression. The increased expression of IGF1 protein was validated by ELISA. Picropodophyllin (PPP, an inhibitor of IGF-1R) inhibition test confirmed that the proliferation-enhancing effect depended on IGF1. This study provided information about BSSG as an efficient and inexpensive growth factor alternative, of which the effect is closely involved in IGF1.

Jiang, Li-hua; Yang, Nian-yun; Yuan, Xiao-lin; Zou, Yi-jie; Jiang, Ze-qun; Zhao, Feng-ming; Chen, Jian-ping; Wang, Ming-yan; Lu, Da-xiang

2013-01-01

285

Degradation of cyanidin 3-glucoside by caffeic acid o-quinone. Determination of the stoichiometry and characterization of the degradation products.  

PubMed

Caffeic acid o-quinone (CQ) was prepared by oxidation of caffeic acid with o-chloranil in organic media. The reaction between the purified CQ and cyanidin 3-glucoside (Cy 3-glc, o-diphenolic anthocyanin) was monitored by HPLC, and quantitative analyses were performed to establish the stoichiometry of the reaction. The results indicate that Cy 3-glc is degraded by a coupled oxidation mechanism with integration of CQ into the degradation products. The ratio of degraded Cy 3-glc to CQ incorporated into the condensation products was approximately 2.0. No brown products could be detected, only a slight orange color. Moreover, the addition of purified polyphenol oxidase to the slightly colored media resulted in the disappearance of the caffeic acid formed from the reaction of coupled oxidation (Cy 3-glc/CQ) and the formation of brown polymers. The degradation products were isolated by gel filtration on Sephadex G-25. The UV-vis spectra and chemical analysis (acidic hydrolysis) of the degradation products suggest that they resulted from the condensation of caffeic acid and Cy 3-glc. HPLC analysis showed that the partial purified fraction contained a mixture of complex condensation products. PMID:10552861

Kader, F; Irmouli, M; Zitouni, N; Nicolas, J P; Metche, M

1999-11-01

286

Determination of iriflophenone 3-C-?-d-glucoside from Aquilaria spp. by an indirect competitive enzyme-linked immunosorbent assay using a specific polyclonal antibody.  

PubMed

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

2013-09-01

287

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

PubMed

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

2013-02-01

288

Cyanidin 3-O-glucoside reduces Helicobacter pylori VacA-induced cell death of gastric KATO III cells through inhibition of the SecA pathway.  

PubMed

Two key virulence factors of Helicobacter pylori are the secreted virulent proteins of vacuolating toxin A (VacA) and cytotoxin associated protein A (CagA) which lead to damages of gastric epithelial cells. We previously identified that the cyanidin 3-O-glucoside (C3G) inhibits the secretion of both VacA and CagA. In the current report, we show that C3G inhibits VacA secretion in a dose-dependent manner by inhibiting secretion system subunit protein A (SecA) synthesis. As SecA is involved in translocation of bacterial proteins, we predicted that inhibition of the SecA pathway by C3G should decrease H. pylori-induced cell death. To test this hypothesis, the human gastric cell line KATO III cells were co-cultured with H. pylori 60190 (VacA(+)/CagA(+)) and C3G. We found that C3G treatment caused a decrease in activation of the pro-apoptotic proteins caspase-3/-8 in H. pylori-infected cells leading to a decrease in cell death. Our data suggest that consumption of foods containing anthocyanin may be beneficial in reducing cell damage due to H. pylori infection. PMID:24904230

Kim, Sa-Hyun; Woo, Hyunjun; Park, Min; Rhee, Ki-Jong; Moon, Cheol; Lee, Dongsup; Seo, Woo Duck; Kim, Jong Bae

2014-01-01

289

Total glucosides of paeony induces regulatory CD4(+)CD25(+) T cells by increasing Foxp3 demethylation in lupus CD4(+) T cells.  

PubMed

Total glucosides of paeony (TGP), an active compound extracted from Paeony root, has been used in therapy for autoimmune diseases. However the molecular mechanism of TGP in the prevention of autoimmune response remains unclear. In this study, we found that TGP treatment significantly increased the percentage and number of Treg cells in lupus CD4(+) T cells. Further investigation revealed that treatment with TGP increased the expression of Foxp3 in lupus CD4(+) T cells by down-regulating Foxp3 promoter methylation levels. However, we couldn't observe similar results in healthy control CD4(+) T cells treated by TGP. Moreover, our results also showed that IFN-? and IL-2 expression was enhanced in TGP-treated lupus CD4(+) T cells. These findings indicate that TGP inhibits autoimmunity in SLE patients possibly by inducing Treg cell differentiation, which may in turn be due to its ability to regulate the methylation status of the Foxp3 promoter and activate IFN-? and IL-2 signaling. PMID:22406048

Zhao, Ming; Liang, Gong-ping; Tang, Mei-ni; Luo, Shuang-yan; Zhang, Jing; Cheng, Wen-jing; Chan, Tak-mao; Lu, Qian-jin

2012-05-01

290

Total Glucosides of Paeony Attenuate Renal Tubulointerstitial Injury in STZ-Induced Diabetic Rats: Role of Toll-Like Receptor 2.  

PubMed

Accumulating evidence suggested that macrophages induce tubulointerstitial injury. Total glucosides of paeony (TGP), extracted from Paeonia lactiflora, has presented anti-inflammatory activities in diabetic kidney disease. This research will investigate the protective effect of TGP on renal tubulointerstitium and its mechanism in streptozotocin-induced diabetic rats. TGP was administered orally at a dose of 50, 100, and 200 mg·kg(-1)·d(-1) for 8 weeks. Tubulointerstitial injury was quantified, followed by immunohistochemistry analysis of renal ?-smooth muscle actin (?-SMA), E-cadherin (E-cad) expression, nuclear factor kappa B (NF-?B)-p-p-65(+), Toll-like receptor (TLR)2(+), and ED-1(+) cell infiltration in renal tubulointerstitium. Renal TLR2(+) macrophages were detected by double immunohistochemical staining. Western blotting was used to detect the TLR2 expression. Histologically, there was marked accumulation of TLR2(+), NF-?B-p-p-65(+), ED-1(+) cells, and ED-1(+)TLR2(+) cells (macrophages) in the diabetic kidney and TGP treatment could alleviate it. Accompanying with that, the tubulointerstitial injury was ameliorated, ?-SMA expression was lower, and E-cad expression was higher compared with the diabetic rats. Western blot analysis showed that the expression of TLR2 protein was significantly increased in the kidney of the diabetic rats, whereas TGP treatment reduced it. Our study showed that TGP could prevent renal tubulointerstitium injury in diabetic rats through a mechanism that may be at least partly correlated with suppression of increased macrophage infiltration and the expression of TLR2. PMID:24739281

Zhang, Wei; Zhao, Li; Su, Shuang-Quan; Xu, Xing-Xin; Wu, Yong-Gui

2014-05-20

291

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

2004-03-01

292

Potential protection of 2,3,5,4'-tetrahydroxystilbene-2-O-?-d-glucoside against staurosporine-induced toxicity on cultured rat hippocampus neurons.  

PubMed

The present study explored the effect of 2,3,5,4'-tetrahydroxystilbene-2-O-?-d-glucoside (THSG) on the staurosporine (STS)-induced toxicity in cultured rat hippocampal neurons. The results showed that administration of 200?M of THSG significantly protected against 0.3?M of STS-induced apoptosis in cultured rat hippocampal neurons tested by methyl thiazolyl tetrazolium (MTT) and terminal deoxynucleotidyl transferase-mediated dUTP nick-end labeling (TUNEL) assays. Furthermore, when the Akt signaling pathway was blocked by LY294002, an inhibitor of Phosphatidyl Inositol 3-kinase (PI3K), the protective effects of THSG against STS-induced neurotoxicity were abrogated. We further examined the involvement of PI3K/Akt signaling pathway in THSG protection against STS-induced cytotoxicity on cultured neurons and found that administration of THSG significantly inhibited the STS-induced decreases in the content of phosphorylated AKt (p-Akt). Moreover, we found that THSG rescued the down-regulation of B cell lymphoma/lewkmia-2 (Bcl2) and pro-caspase-3 (pro-Csp3) caused by STS in the neurons. These results indicate that THSG protect the cultured rat hippocampal neurons against STS-induced cytotoxicity and the PI3K/Akt signaling and mitochondrial apoptotic pathways are involved in the THSG-induced protective effects. PMID:24887581

Yang, Xiao-Ping; Liu, Tao-Yan; Qin, Xiao-Yan; Yu, Long-Chuan

2014-07-25

293

Cyanidin-3-O-glucoside modulates intracellular redox status and prevents HIF-1 stabilization in endothelial cells in vitro exposed to chronic hypoxia.  

PubMed

The term hypoxia refers to conditions characterized by a relative restriction of oxygen supply. It is usually associated to a paradoxical overproduction of reactive oxygen species (ROS) and to the activation of several transcription factors, including HIF-1?, which in turn trigger angiogenic and apoptotic response. In this study we have investigated the mechanisms by which the anthocyanin cyanidin-3-O-glucoside (C3G) modulates hypoxia induced response in human endothelial cells (HUVECs). In fact, hypoxia induces an increase of ROS generation in HUVECs paralleled by a loss of antioxidant cellular capacity. According to the observed increase of HO-1 mRNA expression, pretreatment of C3G to HUVEC reduces the entity of oxidative stress thanks to the activation of cellular antioxidant response. C3G also attenuates HIF-1? protein accumulation conditions supporting the hypothesis of a major role of oxidative stress in the presence of low oxygen. Furthermore, the increased expression of angiogenesis and apoptosis markers (MMP-2 and caspase-3) due to HIF-1? activation by hypoxia is reduced in C3G pretreated cells. Overall, our data suggest that the modulation of intracellular redox status induced by C3G may be an important protective mechanism against endothelial damage in hypoxic conditions. PMID:24518827

Anwar, S; Speciale, A; Fratantonio, D; Cristani, M; Saija, A; Virgili, F; Cimino, F

2014-04-21

294

Effects of 2,3,4',5-tetrahydroxystilbene 2-O-beta-D-glucoside on vascular endothelial dysfunction in atherogenic-diet rats.  

PubMed

2,3,4',5-Tetrahydroxystilbene 2- O-beta- D-glucoside (TSG), an active component extracted from Polygonum multiflorum, has been found to have an anti-atherosclerotic effect. The aim of this study was to investigate whether the TSG could prevent the development of atherosclerosis through influencing endothelial function in atherogenic-diet rats and to explore the possible mechanisms. Vascular endothelial dysfunction was assessed using isolated aortic ring preparation, transmission electron microscopy of the aorta, and levels of nitrate/nitrite (NOx) in serum and aorta. Endothelial nitric oxide (NO) synthase (eNOS) and inducible NO synthase (iNOS) mRNA and protein expression were also measured. After 12 weeks treatment, TSG improved acetylcholine-induced endothelium-dependent relaxation, prevented intimal remodeling, inhibited the decreased NOx content in serum and aorta in atherogenic-diet rats. Furthermore, the observed decreased eNOS mRNA and protein expression and increased iNOS mRNA and protein expression in atherogenic-diet rats were attenuated by TSG treatment. These results suggest that TSG could restore vascular endothelial function, which may be related to its ability to prevent changes of eNOS and iNOS expression, leading to preservation of NO bioactivity. PMID:19350477

Zhang, Wei; Xu, Xiao-Le; Wang, Yu-Qin; Wang, Chun-Hua; Zhu, Wei-Zhong

2009-09-01

295

Protective Effect of Tetrahydroxystilbene Glucoside on 6-OHDA-Induced Apoptosis in PC12 Cells through the ROS-NO Pathway  

PubMed Central

Oxidative stress plays an important role in the pathogenesis of neurodegenerative diseases, such as Parkinson's disease. The molecule, 2,3,5,4?-tetrahydr- oxystilbene-2-O-?-D-glucoside (TSG), is a potent antioxidant derived from the Chinese herb, Polygonum multiflorum Thunb. In this study, we investigated the protective effect of TSG against 6-hydroxydopamine-induced apoptosis in rat adrenal pheochromocytoma PC12 cells and the possible mechanisms. Our data demonstrated that TSG significantly reversed the 6-hydroxydopamine-induced decrease in cell viability, prevented 6-hydroxydopamine-induced changes in condensed nuclei and decreased the percentage of apoptotic cells in a dose-dependent manner. In addition, TSG slowed the accumulation of intracellular reactive oxygen species and nitric oxide, counteracted the overexpression of inducible nitric oxide syntheses as well as neuronal nitric oxide syntheses, and also reduced the level of protein-bound 3-nitrotyrosine. These results demonstrate that the protective effects of TSG on rat adrenal pheochromocytoma PC12 cells are mediated, at least in part, by the ROS-NO pathway. Our results indicate that TSG may be effective in providing protection against neurodegenerative diseases associated with oxidative stress.

Tao, Lizhen; Li, Xiaofeng; Zhang, Lingling; Tian, Jiyu; Li, Xiaobing; Sun, Xin; Li, Xuefen; Jiang, Lin; Zhang, Xiaojun; Chen, Jianzong

2011-01-01

296

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

PubMed

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

2012-11-01

297

Protective effect of tetrahydroxystilbene glucoside on 6-OHDA-induced apoptosis in PC12 cells through the ROS-NO pathway.  

PubMed

Oxidative stress plays an important role in the pathogenesis of neurodegenerative diseases, such as Parkinson's disease. The molecule, 2,3,5,4'-tetrahydr- oxystilbene-2-O-?-D-glucoside (TSG), is a potent antioxidant derived from the Chinese herb, Polygonum multiflorum Thunb. In this study, we investigated the protective effect of TSG against 6-hydroxydopamine-induced apoptosis in rat adrenal pheochromocytoma PC12 cells and the possible mechanisms. Our data demonstrated that TSG significantly reversed the 6-hydroxydopamine-induced decrease in cell viability, prevented 6-hydroxydopamine-induced changes in condensed nuclei and decreased the percentage of apoptotic cells in a dose-dependent manner. In addition, TSG slowed the accumulation of intracellular reactive oxygen species and nitric oxide, counteracted the overexpression of inducible nitric oxide syntheses as well as neuronal nitric oxide syntheses, and also reduced the level of protein-bound 3-nitrotyrosine. These results demonstrate that the protective effects of TSG on rat adrenal pheochromocytoma PC12 cells are mediated, at least in part, by the ROS-NO pathway. Our results indicate that TSG may be effective in providing protection against neurodegenerative diseases associated with oxidative stress. PMID:21998750

Tao, Lizhen; Li, Xiaofeng; Zhang, Lingling; Tian, Jiyu; Li, Xiaobing; Sun, Xin; Li, Xuefen; Jiang, Lin; Zhang, Xiaojun; Chen, Jianzong

2011-01-01

298

Protection by tetrahydroxystilbene glucoside against cerebral ischemia: involvement of JNK, SIRT1, and NF-kappaB pathways and inhibition of intracellular ROS/RNS generation.  

PubMed

Many natural polyphenolic compounds have been shown to attenuate reactive oxygen/nitrogen species (ROS/RNS) formation and protect against ischemia/reperfusion injury both in vitro and in vivo. 2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside (TSG), an active component of the rhizome extract from Polygonum multiflorum, exhibits antioxidative and anti-inflammatory effects. Here, we used an in vitro ischemic model of oxygen-glucose deprivation followed by reperfusion (OGD-R) and an in vivo ischemic model of middle cerebral artery occlusion (MCAO) to investigate the neuroprotective effects of TSG on ischemia/reperfusion brain injury and the related mechanisms. We demonstrated that OGD-R-induced neuronal injury, intracellular ROS generation, and mitochondrial membrane potential dissipation were reversed by TSG. The elevation of H2O2-induced [Ca2+]i was also attenuated by TSG. Inhibition of the c-Jun N-terminal kinase (JNK) and Bcl-2 family-related apoptotic signaling pathway was involved in the neuroprotection afforded by TSG. Meanwhile, TSG inhibited iNOS mRNA expression induced by OGD-R, which may be mediated by the activation of SIRT1 and inhibition of NF-kappaB activation. In vivo studies further demonstrated that TSG significantly reduced the brain infarct volume and the number of positive cells by TUNEL staining in the cerebral cortex compared to the MCAO group. Our study indicates that TSG protects against cerebral ischemia/reperfusion injury through multifunctional cytoprotective pathways. PMID:19272442

Wang, Ting; Gu, Jun; Wu, Peng-Fei; Wang, Fang; Xiong, Zhe; Yang, Yuan-Jian; Wu, Wen-Ning; Dong, Ling-Dan; Chen, Jian-Guo

2009-08-01

299

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

2012-01-01

300

Protective effect of tetrahydroxystilbene glucoside against hydrogen peroxide-induced dysfunction and oxidative stress in osteoblastic MC3T3-E1 cells.  

PubMed

Oxidative stress can induce apoptosis and decrease activities of osteoblasts. 2,3,5,4'-tetrahydroxystilbene-2-O-?-D-glucoside (TSG), is a potent antioxidant derived from a Chinese herb Polygonum multiflorum Thunb. To evaluate the protective effect provided by TSG to osteoblastic MC3T3-E1 cells, the cells were pretreated with TSG for 24h before being treated with 0.3mM hydrogen peroxide (H(2)O(2)) for 24 h, then some markers of osteoblast function and oxidative damage of the cells were examined. Our data demonstrated that TSG significantly (P< 0.05) increased cell survival, alkaline phosphatase (ALP) activity, calcium deposition, and the mRNA expression of ALP, collagen I (COL-I) and osteocalcin (OCN) in the presence of H(2)O(2). In addition, TSG decreased the production of receptor activator of nuclear factor-?B ligand (RANKL), interleukin-6 (IL-6), intracellular reactive oxygen species and malondialdehyde (MDA) of osteoblastic MC3T3-E1 cells induced by H(2)O(2). Taken together, these results demonstrated that the protective effect provided by TSG to osteoblastic MC3T3-E1 cells was mediated, at least in part, via inhibition of the release of bone-resorbing mediators and oxidative damage of the cells. Our results indicated that TSG may be effective in providing protection against osteoporosis associated with oxidative stress. PMID:22683865

Zhang, Jin-Kang; Yang, Liu; Meng, Guo-Lin; Fan, Jing; Chen, Jian-Zong; He, Qi-Zhen; Chen, Shi; Fan, Jin-Zhu; Luo, Zhuo-Jing; Liu, Jian

2012-08-15

301

Purification and characterization of the glucoside 3-dehydrogenase produced by a newly isolated Sphingobacterium faecium ZJF-D6 CCTCC M 2013251.  

PubMed

A soluble glucoside 3-dehydrogenase (G3DH) was purified from a newly isolated Sphingobacterium faecium ZJF-D6 CCTCC M 2013251. The enzyme was purified to 35.71-fold with a yield of 41.91 % and was estimated by sodium dodecyl sulphate-polyacrylamide gel electrophoresis with a molecular mass of 62 kDa. The sequences of two peptides of the enzyme were all contained in a GMC family oxidoreductase (EFK55866) by mass spectrometry analysis. The optimal pH of the enzyme was around 6.2. The enzyme was stable within a pH range of 5.0-6.6 and was sensitive to heat. G3DH from S. faecium exhibited extremely broad substrate specificity and well regioselectivity to validoxylamine A. The enzyme was completely inhibited by Hg2Cl2 and partly inhibited by Cu(2+), Fe(2+), Ca(2+), and Cd(2+). The apparent K m values for D-glucose, sucrose, and validoxylamine were calculated to be 1.1, 1.7, and 2.1 mM, respectively. With this purified enzyme, 3-keto sucrose was prepared at pH 5.0, 30 °C for 10 h with a yield of 28.7 %. PMID:24585380

Zhang, Jian-Fen; Yang, Bo; Chen, Weiqing; Chen, Jing

2014-04-01

302

Microarray Analysis of mRNA and MicroRNA Expression Profile Reveals the Role of ? -Sitosterol-D-glucoside in the Proliferation of Neural Stem Cell.  

PubMed

Neural stem cells (NSCs) are self-regenerating cells, but their regenerative capacity is limited. The present study was conducted to investigate the effect of ? -sitosterol-D-glucoside (BSSG) on the proliferation of hippocampal NSCs and to determine the corresponding molecular mechanism. Results of CCK-8 assay showed that BSSG significantly increased NSC proliferation and the effectiveness of BSSG was similar to that of basic fibroblast growth factor and epidermal growth factor. mRNA expression profiling showed that 960 genes were differentially expressed after NSCs were treated with BSSG. Among the 960 genes, IGF1 is considered as a key regulatory gene that functionally promotes NSC proliferation. MicroRNA (miRNA) expression profiling indicated that 30 and 84 miRNAs were upregulated and downregulated, respectively. miRNA-mRNA relevance analysis revealed that numerous mRNAs including IGF1 mRNA were negatively regulated by miRNAs with decreased expression, thereby increasing the corresponding mRNA expression. The increased expression of IGF1 protein was validated by ELISA. Picropodophyllin (PPP, an inhibitor of IGF-1R) inhibition test confirmed that the proliferation-enhancing effect depended on IGF1. This study provided information about BSSG as an efficient and inexpensive growth factor alternative, of which the effect is closely involved in IGF1. PMID:24391673

Jiang, Li-Hua; Yang, Nian-Yun; Yuan, Xiao-Lin; Zou, Yi-Jie; Jiang, Ze-Qun; Zhao, Feng-Ming; Chen, Jian-Ping; Wang, Ming-Yan; Lu, Da-Xiang

2013-01-01

303

Cyanidin 3-O-Glucoside Reduces Helicobacter pylori VacA-Induced Cell Death of Gastric KATO III Cells through Inhibition of the SecA Pathway  

PubMed Central

Two key virulence factors of Helicobacter pylori are the secreted virulent proteins of vacuolating toxin A (VacA) and cytotoxin associated protein A (CagA) which lead to damages of gastric epithelial cells. We previously identified that the cyanidin 3-O-glucoside (C3G) inhibits the secretion of both VacA and CagA. In the current report, we show that C3G inhibits VacA secretion in a dose-dependent manner by inhibiting secretion system subunit protein A (SecA) synthesis. As SecA is involved in translocation of bacterial proteins, we predicted that inhibition of the SecA pathway by C3G should decrease H. pylori-induced cell death. To test this hypothesis, the human gastric cell line KATO III cells were co-cultured with H. pylori 60190 (VacA+/CagA+) and C3G. We found that C3G treatment caused a decrease in activation of the pro-apoptotic proteins caspase-3/-8 in H. pylori-infected cells leading to a decrease in cell death. Our data suggest that consumption of foods containing anthocyanin may be beneficial in reducing cell damage due to H. pylori infection.

Kim, Sa-Hyun; Woo, Hyunjun; Park, Min; Rhee, Ki-Jong; Moon, Cheol; Lee, Dongsup; Seo, Woo Duck; Kim, Jong Bae

2014-01-01

304

Impact of Cyanidin-3-Glucoside on Glycated LDL-Induced NADPH Oxidase Activation, Mitochondrial Dysfunction and Cell Viability in Cultured Vascular Endothelial Cells  

PubMed Central

Elevated levels of glycated low density lipoprotein (glyLDL) are frequently detected in diabetic patients. Previous studies demonstrated that glyLDL increased the production of reactive oxygen species (ROS), activated NADPH oxidase (NOX) and suppressed mitochondrial electron transport chain (mETC) enzyme activities in vascular endothelial cells (EC). The present study examined the effects of cyanidin-3-glucoside (C3G), a type of anthocyanin abundant in dark-skinned berries, on glyLDL-induced ROS production, NOX activation and mETC enzyme activity in porcine aortic EC (PAEC). Co-treatment of C3G prevented glyLDL-induced upregulation of NOX4 and intracellular superoxide production in EC. C3G normalized glyLDL-induced inhibition on the enzyme activities of mETC Complex I and III, as well as the abundances of NADH dehydrogenase 1 in Complex I and cytochrome b in Complex III in EC. Blocking antibody for the receptor of advanced glycation end products (RAGE) prevented glyLDL-induced changes in NOX and mETC enzymes. Combination of C3G and RAGE antibody did not significantly enhance glyLDL-induced inhibition of NOX or mETC enzymes. C3G reduced glyLDL-induced RAGE expression with the presence of RAGE antibody. C3G prevented prolonged incubation with the glyLDL-induced decrease in cell viability and the imbalance between key regulators for cell viability (cleaved caspase 3 and B cell Lyphoma-2) in EC. The findings suggest that RAGE plays an important role in glyLDL-induced oxidative stress in vascular EC. C3G may prevent glyLDL-induced NOX activation, the impairment of mETC enzymes and cell viability in cultured vascular EC.

Xie, Xueping; Zhao, Ruozhi; Shen, Garry X.

2012-01-01

305

Cardiovascular effects of mollic acid glucoside, a 1?-hydroxycycloartenoid saponin extractive from Combretum molle R Br ex G Don (Combretaceae) leaf  

PubMed Central

Summary Summary The cardiovascular effects of mollic acid glucoside (MAG), a 1?-hydroxycycloartenoid saponin extractive from Combretum molle R Br ex G Don (Combretaceae) leaf, have been investigated in some experimental animal paradigms. The plant extract (MAG, 5–80 ?g/ml) produced concentration-dependent, significant (p < 0.05–0.001) negative inotropic and negative chronotropic effects on guinea pig isolated electrically driven left, and spontaneously beating right atrial muscle preparations, respectively. MAG also significantly reduced (p < 0.05–0.001) or abolished, in a concentration-dependent manner, the rhythmic, spontaneous contractions of portal veins isolated from healthy, normal Wistar rats. Like acetylcholine (ACh, 10-8–10-5 M), the plant extract (5–80 ?g/ml) produced concentration-related relaxations of rat isolated endothelium-containing thoracic aortic rings pre-contracted with noradrenaline (NA, 10-10–10-5 M). The vasorelaxant effects of MAG in the aortic rings were markedly inhibited or annulled by NG-nitro-L-arginine methyl ester (L-NAME, 10-5 M), a nitric oxide synthase inhibitor. Furthermore, MAG (2.5–40 mg/kg iv) caused dose-related, transient but significant reductions (p < 0.05–0.001) in the systemic arterial blood pressures and heart rates of anaesthetised normotensive and hypertensive rats. The results of this laboratory animal study indicate that MAG caused bradycardia, vasorelaxation and hypotension in the mammalian experimental models used. The vasorelaxant action of MAG was endothelium dependent, and was therefore possibly dependent on the synthesis and release of nitric oxide (NO). The findings of this study suggest that Combretum molle leaf may be used as a natural supplementary remedy in essential hypertension and in certain cases of cardiac dysfunctions in rural African communities.

Ojewole, John AO

2008-01-01

306

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

1997-01-01

307

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

1997-01-01

308

Increased bioavailability of hesperetin-7-glucoside compared with hesperidin results in more efficient prevention of bone loss in adult ovariectomised rats.  

PubMed

Hesperidin (Hp), a citrus flavonoid predominantly found in oranges, shows bone-sparing effects in ovariectomised (OVX) animals. In human subjects, the bioavailability of Hp can be improved by the removal of the rhamnose group to yield hesperetin-7-glucoside (H-7-glc). The aim of the present work was to test whether H-7-glc was more bioavailable and therefore more effective than Hp in the prevention of bone loss in the OVX rat. Adult 6-month-old female Wistar rats were sham operated or OVX, then pair fed for 90 d a casein-based diet supplemented or not with freeze-dried orange juice enriched with Hp or H-7-glc at two dose equivalents of the hesperetin aglycone (0.25 and 0.5 %). In the rats fed 0.5 %, a reduction in OVX-induced bone loss was observed regarding total bone mineral density (BMD):+7.0 % in OVX rats treated with Hp (HpOVX) and +6.6 % in OVX rats treated with H-7-glc (H-7-glcOVX) v. OVX controls (P < 0.05). In the rats fed 0.25 % hesperetin equivalents, the H-7-glcOVX group showed a 6.6 % improvement in total femoral BMD v. the OVX controls (P < 0.05), whereas the Hp diet had no effect at this dose. The BMD of rats fed 0.25 % H-7-glc was equal to that of those given 0.5 % Hp, but was not further increased at 0.5 % H-7-glc. Plasma hesperetin levels and relative urinary excretion were significantly enhanced in the H-7-glc v. Hp groups, and the metabolite profile showed the absence of eriodictyol metabolites and increased levels of hesperetin sulphates. Taken together, improved bioavailability of H-7-glc may explain the more efficient bone protection of this compound. PMID:19393110

Habauzit, Véronique; Nielsen, Inge-Lise; Gil-Izquierdo, Angel; Trzeciakiewicz, Anna; Morand, Christine; Chee, Winnie; Barron, Denis; Lebecque, Patrice; Davicco, Marie-Jeanne; Williamson, Gary; Offord, Elizabeth; Coxam, Véronique; Horcajada, Marie-Noëlle

2009-10-01

309

Frequency dependence in the action of the class III antiarrhythmic drug dofetilide is modulated by altering L-type calcium current and digitalis glucoside.  

PubMed

We investigated how modulation of L-type calcium current affects the class II antiarrhythmic effect of dofetilide. Action-potential duration (APD) was determined in guinea pig papillary muscle by microelectrode techniques at different stimulation frequencies (0.5-3 Hz). The APD-prolonging effect (deltaAPD) of 10 nM dofetilide was reversed frequency dependent; it was 51 +/- 6 ms at 0.5 Hz and lower at 3 Hz, 21 +/- 3 ms. Either 10 microM diltiazem or 0.1 microM Bay K 8644 (BayK) was added to decrease or increase L-type calcium currents. In the presence of dofetilide + diltiazem, deltaAPD was reduced to 32 +/- 4 ms at 0.5 Hz but not affected at 3 Hz. Conversely, dofetilide + BayK further prolonged deltaAPD to 78 +/- 10 ms at 0.5 Hz but not at 3 Hz. When 10 microM dihydroouabain, a digitalis glucoside, was added to dofetilide, deltaAPD was more pronounced at 0.5 Hz and reduced at 3 Hz. We conclude that the reversed frequency-dependent effect of dofetilide on APD can be modulated by altering L-type calcium currents. With reduced calcium current, the frequency profile is less reversed and more favorable. The similarity of BayK and dihydroouabain in aggravating the reversed frequency-dependent effect of dofetilide is in line with a contribution of intracellular calcium to this reversed rate-dependent profile in the guinea pig ventricle. PMID:9456283

Gjini, V; Schreieck, J; Korth, M; Weyerbrock, S; Schömig, A; Schmitt, C

1998-01-01

310

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

PubMed

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. PMID:23760836

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

2013-11-01

311

Transcriptional regulation of de novo biosynthesis of cyanogenic glucosides throughout the life-cycle of the burnet moth Zygaena filipendulae (Lepidoptera).  

PubMed

The six-spotted burnet moth Zygaena filipendulae (Lepidoptera) utilize the two cyanogenic glucosides (CNglcs) linamarin and lotaustralin as deterrents against predators throughout the entire life cycle. CNglcs can be hydrolyzed and bioactivated by ?-glucosidases, resulting in the release of toxic hydrogen cyanide. CNglcs are retained through metamorphosis, probably involved in mating communication, and transferred during mating from the male to the female as a nuptial gift. CNglcs can be biosynthesized de novo by Z. filipendulae larvae, but may also be sequestered from their food plant Lotus corniculatus (Fabaceae). These two strategies are tightly linked and adjusted according to the CNglc content and composition of the food plant in order to balance CNglc homeostasis in the larva. In this study, the amounts of CNglcs and transcript levels of the biosynthetic genes were monitored in all life-stages and tissues of Z. filipendulae. During pupation, transcription of the biosynthetic genes is turned off and the CNglc content slowly declines. In females but not males, transcription of the biosynthetic genes is re-activated at the end of pupation. Eggs and embryos do not biosynthesize CNglcs de novo, but are endowed with CNglcs following eclosion of the female. Similarly to larvae, de novo biosynthesis in female adults takes place in the integument from which CNglcs are then transported to other organs. This study demonstrates that Z. filipendulae has evolved the ability to adjust the production of CNglcs throughout its life-cycle for optimal utilization in defense and possibly other metabolic functions, while at the same time avoiding intoxication. PMID:24727026

Fürstenberg-Hägg, Joel; Zagrobelny, Mika; Olsen, Carl Erik; Jørgensen, Kirsten; Møller, Birger Lindberg; Bak, Søren

2014-06-01

312

Cyanidin-3-O-?-glucoside protects primary mouse hepatocytes against high glucose-induced apoptosis by modulating mitochondrial dysfunction and the PI3K/Akt pathway.  

PubMed

Apoptosis is an early event of steatohepatitis in non-alcoholic fatty liver disease (NAFLD), and an increase in oxidative stress induced by hyperglycemia has been linked to an acceleration of apoptosis in hepatocytes. Cyanidin-3-O-?-glucoside (C3G), a classic anthocyanin, has been reported to reduce oxidative stress and attenuate non-alcoholic steatohepatitis in mice. In this study, we evaluated the toxicity of high glucose in primary hepatocytes of mice fed with a high fat diet and amelioration of this toxicity by C3G. Incubation of hepatocytes with 35mM glucose for 12h resulted in a significant decrease in cell viability and increase in apoptotic cell death. Furthermore, hyperglycemia-induced mitochondrial depolarization was accompanied by the release of cytochrome c and altered expression of Bax and Bcl-2, suggesting a mitochondria-mediated apoptotic mode of cell death. Pre-incubation with 50?M C3G induced changes associated with better cell survival and function, including a reduction in reactive species generation, improvement of mitochondrial membrane potential, inactivation of caspase-3 and -9, and down-regulation of the pro-apoptotic Bax protein. We further investigated the role of the phosphatidylinositol 3-kinase (PI3K)/Akt and mitogen-activated protein kinases (MAPKs) pathways with respect to the anti-apoptotic action of C3G, and our results showed that C3G could activate Akt. Additionally, C3G inactivated c-Jun N-terminal protein kinase (JNK), but not extracellular signal-regulated kinase or p38 MAPK, in glucose-stressed cells. Interestingly, JNK inhibitor enhanced the protective effect of C3G on cell survival. Our results suggest that anthocyanin C3G may exhibit hepatoprotective potential against NAFLD by promoting functional integrity and survival of hepatocytes. PMID:24821109

Jiang, Xinwei; Tang, Xilan; Zhang, Peiwen; Liu, Guoling; Guo, Honghui

2014-07-15

313

2,3,4',5-tetrahydroxystilbene-2-O-?-D-glucoside inhibits proliferation of vascular smooth muscle cells: involvement of NO/cGMP/PKG pathway.  

PubMed

The proliferation of vascular smooth muscle cells (VSMCs) induced by injury to the intima of arteries is an important etiologic factor in vascular proliferative disorders such as atherosclerosis and restenosis. 2,3,4',5-Tetrahydroxystilbene-2-O-?-D-glucoside (TSG), an active component extracted from Polygonum multiflorum, has been found to have an antiatherosclerotic effect. The aim of this study was to investigate the effects of TSG on platelet derived growth factor (PDGF)-BB induced VSMCs proliferation and to explore the possible mechanisms of such effects. Pretreatment of VSMCs with TSG significantly inhibited PDGF-BB-induced cell proliferation in a concentration-dependent but not time-dependent manner. In addition, flow cytometry analysis of the DNA content revealed blocking of the PDGF-BB-inducible cell cycle progression by TSG. On the contrary, an inhibitory effect of TSG on VSMCs proliferation and expression of cell cycle regulators were markedly attenuated by addition of an nitric oxide (NO) synthase inhibitor, a soluble guanylate cyclase inhibitor and a cyclic GMP (cGMP)-dependent protein kinase (PKG) inhibitor: N(G)-nitro-L-arginine methyl ester (L-NAME), 1H-[1,2,4] oxadiazolo [4,3-?] quinoxalin-1-one (ODQ) and KT5823, respectively. It was also demonstrated that TSG enhanced NO and cGMP formation through up-regulating endothelial NO synthase expression in VSMCs. The findings indicate that TSG inhibited VSMCs proliferation induced by PDGF-BB may involve the NO/cGMP/PKG signal pathway. PMID:22213189

Xu, Xiao-Le; Huang, Yan-Juan; Chen, Xiang-Fan; Lin, Dan-Yan; Zhang, Wei

2012-07-01

314

Protodioscin-glycosidase-1 hydrolyzing 26-O-?-D-glucoside and 3-O-(1 ? 4)-?-L-rhamnoside of steroidal saponins from Aspergillus oryzae.  

PubMed

A novel protodioscin-(steroidal saponin)-glycoside hydrolase, named protodioscin-glycosidase-1 (PGase-1), was purified and characterized from the Aspergillus oryzae strain. The molecular mass of this enzyme was determined to be about 55 kDa based on SDS-polyacrylamide gel electrophoresis. PGase-1 was able to hydrolyze the terminal 26-O-?-D-glucopyranoside of protodioscin (furostanoside) to produce dioscin (spirostanoside), and then further hydrolyze the terminal 3-O-(1 ? 4)-?-L-rhamnopyranoside of dioscin to form progenin III. However, PGase-1 could hardly hydrolyze the 3-O-(1 ? 2)-?-L-rhamnopyranoside of progenin III, 3-O-?-D-glucoside of trillin, and the 1-O-glycosides of ophiopogonin D (steroidal saponin). In addition, PGase-1 also could hydrolyze the ?-D-galactopyranoside, ?-D-glucopyranoside, and ?-D-galactopyranoside of p-nitrophenyl-glycosides, but the enzyme could not hydrolyze the ?-D-mannopyranoside, ?-L-arabinopyranoside, ?-D-glucopyranoside, ?-D-xylopyranoside, and ?-L-rhamnopyranoside of p-nitrophenyl-glycosides. These new properties of PGase-1 were significantly different from those of previously described steroidal saponin-glycosidases and the glycosidases currently described in Enzyme Nomenclature by the NC-IUBMB. The gene (termed as pgase-1) encoding PGase-1 was cloned, sequenced, and expressed in Pichia pastoris GS115. The complete nucleotide sequence of pgase-1 consists of 1,725 bp. The recombinant PGase-1 from recombinant P. pastoris GS115 strain also showed the activity hydrolyzing glycosides of steroidal saponins which was similar to that of the wild-type PGase-1 from A. oryzae. The PGase-1 gene is highly similar to Aspergilli ?-amylase (EC 3.2.1.1), and PGase-1 should be classified as glycoside hydrolase family 13 by the method of gene sequence-based classification. But the enzyme properties of PGase-1 are different from those of ?-amylase in this family. PMID:23467827

Liu, Tingqiang; Yu, Hongshan; Liu, Chunying; Wang, Yuanhao; Tang, Minqian; Yuan, Xiaodong; Luo, Ning; Wang, Qingyu; Xu, Xiaodong; Jin, Fengxie

2013-12-01

315

Enhancement of neurite outgrowth in PC12 cells stimulated with cyclic AMP and NGF by 6-acylated ascorbic acid 2-O-alpha-glucosides (6-Acyl-AA-2G), novel lipophilic ascorbate derivatives.  

PubMed

It has been shown that ascorbate (AsA) and its stable derivative, ascorbic acid 2-O-alpha-glucoside (AA-2G), do not elicit neurite outgrowth in PC12 cells. However, these ascorbates are synergistically enhanced by both dibutyryl cyclic AMP (Bt(2)cAMP)- and nerve growth factor (NGF)-induced neurite outgrowth in this model. In the present study, the effects of a series of novel lipophilic ascorbate derivatives, 6-acylated ascorbic acid 2-O-alpha-glucosides (6-Acyl-AA-2G), on neurite outgrowth induced by Bt(2)cAMP and NGF were examined in PC12 cells. We found that all the tested acylated ascorbate derivatives enhanced neurite formation induced by both agents in a dose-dependent manner. Of the 6-Acyl-AA-2G derivatives, 6-octanoyl ascorbic acid 2-O-alpha-glucoside (6-Octa-AA-2G) enhanced the Bt(2)cAMP-induced phosphorylated MAPK p44 and p42 expression. A alpha-glucosidase inhibitor, castanospermine, completely abrogated the promotion of neurite outgrowth and MAPK expression by 6-Octa-AA-2G. Addition of 6-Octa-AA-2G (0.5 mM) to PC12 cells caused a rapid and significant increase in intracellular AsA content, which reached a maximum and was maintained from 12 to 24 h after the culture. These findings suggest that 6-Acyl-AA-2G is rapidly hydrolyzed to AsA within the cell and enhances neurite differentiation through the interaction with the inducer-activated MAPK pathway. PMID:12612444

Zhou, Xiaohua; Tai, Akihiro; Yamamoto, Itaru

2003-03-01

316

Effects of phyllodulcin, hydrangenol, and their 8-O-glucosides, and thunberginols A and F from Hydrangea macrophylla SERINGE var. thunbergii MAKINO on passive cutaneous anaphylaxis reaction in rats.  

PubMed

We examined the antiallergic effects of phyllodulcin, hydrangenol, and their 8-O-glucosides, and thunberginols A and F isolated from the processed leaves (Hydrangeae Dulcis Folium) and dried leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO using the passive cutaneous anaphylaxis (PCA) reaction. With the exception of phyllodulcin, these constituents were found to significantly inhibit the PCA reaction. Although thunberginol A showed the most potent inhibitory effect, hydrangenol was considered to be the principal antiallergic component in the processed leaves, after taking into account their contents. PMID:10480329

Matsuda, H; Shimoda, H; Yamahara, J; Yoshikawa, M

1999-08-01

317

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

2013-01-01

318

Simultaneous determination of calycosin-7-O-?-d-glucoside, calycosin, formononetin, astragaloside IV and schisandrin in rat plasma by LC-MS/MS: application to a pharmacokinetic study after oral administration of Shenqi Wuwei chewable tablets.  

PubMed

A rapid, sensitive and reliable high-performance liquid chromatography-mass spectrometry (LC-MS/MS) method was developed and validated for simultaneous quantification of the five main bioactive components, calycosin, calycosin-7-O-?-d-glucoside, formononetin, astragaloside IV and schisandrin in rat plasma after oral administration of Shenqi Wuwei chewable tablets. Plasma samples were extracted using solid-phase extraction separated on a CEC18 column and detected by MS with an electrospray ionization interface in multiple-reaction monitoring mode. Calibration curves offered linear ranges of two orders of magnitude with r?>?0.995. The method had a lower limit of quantitation of 0.1, 0.02, 0.1, 1 and 0.1?ng/mL for calycosin, calycosin-7-O-?-d-glucoside, formononetin, astragaloside IV and schisandrin, respectively. Intra- and inter-day precisions (relative standard deviation) for all analytes ranged from 0.97 to 7.63% and from 3.45 to 10.89%, respectively. This method was successfully applied to the pharmacokinetic study of the five compounds in rats after oral administration of Shenqi Wuwei chewable tablets. Copyright © 2014 John Wiley & Sons, Ltd. PMID:24652759

Sun, Xuehui; Zhang, Pingping; Wu, Xiujun; Wu, Qiong; Zhang, Mengmeng; An, Ye; Shi, Guobing

2014-08-01

319

Aglycone specificity of Thermotoga neapolitana ?-glucosidase 1A modified by mutagenesis, leading to increased catalytic efficiency in quercetin-3-glucoside hydrolysis  

PubMed Central

Background The thermostable ?-glucosidase (TnBgl1A) from Thermotoga neapolitana is a promising biocatalyst for hydrolysis of glucosylated flavonoids and can be coupled to extraction methods using pressurized hot water. Hydrolysis has however been shown to be dependent on the position of the glucosylation on the flavonoid, and e.g. quercetin-3-glucoside (Q3) was hydrolysed slowly. A set of mutants of TnBgl1A were thus created to analyse the influence on the kinetic parameters using the model substrate para-nitrophenyl-?-D-glucopyranoside (pNPGlc), and screened for hydrolysis of Q3. Results Structural analysis pinpointed an area in the active site pocket with non-conserved residues between specificity groups in glycoside hydrolase family 1 (GH1). Three residues in this area located on ?-strand 5 (F219, N221, and G222) close to sugar binding sub-site +2 were selected for mutagenesis and amplified in a protocol that introduced a few spontaneous mutations. Eight mutants (four triple: F219L/P165L/M278I, N221S/P165L/M278I, G222Q/P165L/M278I, G222Q/V203M/K214R, two double: F219L/K214R, N221S/P342L and two single: G222M and N221S) were produced in E. coli, and purified to apparent homogeneity. Thermostability, measured as Tm by differential scanning calorimetry (101.9°C for wt), was kept in the mutated variants and significant decrease (?T of 5 - 10°C) was only observed for the triple mutants. The exchanged residue(s) in the respective mutant resulted in variations in KM and turnover. The KM-value was only changed in variants mutated at position 221 (N221S) and was in all cases monitored as a 2-3 × increase for pNPGlc, while the KM decreased a corresponding extent for Q3. Turnover was only significantly changed using pNPGlc, and was decreased 2-3 × in variants mutated at position 222, while the single, double and triple mutated variants carrying a mutation at position 221 (N221S) increased turnover up to 3.5 × compared to the wild type. Modelling showed that the mutation at position 221, may alter the position of N291 resulting in increased hydrogen bonding of Q3 (at a position corresponding to the +1 subsite) which may explain the decrease in KM for this substrate. Conclusion These results show that residues at the +2 subsite are interesting targets for mutagenesis and mutations at these positions can directly or indirectly affect both KM and turnover. An affinity change, leading to a decreased KM, can be explained by an altered position of N291, while the changes in turnover are more difficult to explain and may be the result of smaller conformational changes in the active site.

2011-01-01

320

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

1992-01-01

321

Partial amino acid sequence and mRNA analysis of cytosolic pyridoxine-beta-D-glucoside hydrolase from porcine intestinal mucosa: proposed derivation from the lactase-phlorizin hydrolase gene.  

PubMed

We have previously identified and purified a novel beta-glucosidase, designated PNGH (pyridoxine-5'-beta-D-glucoside hydrolase), from the cytosolic fraction of pig intestinal mucosal. PNGH catalyses the hydrolysis of PNG (pyridoxine-5'-beta-D-glucoside), a plant derivative of vitamin B6 that exhibits partial nutritional bioavailability in humans and animals. Preliminary amino acid sequence analysis indicated regions of close similarity of PNGH to the precursor form of LPH (lactase-phlorizin hydrolase), the beta-glucosidase localized to the brush-border membrane. We report in the present study amino acid sequence data for PNGH and results of Northern blot analyses, upon which we propose a common genomic origin of PNGH and LPH. Internal Edman sequencing of the PNGH band isolated by SDS/PAGE yielded data for 16 peptides, averaging 10.8 amino acids in length. These peptides from PNGH (approx. 140 kDa) were highly similar to sequences existing over most of the length of the >200 kDa precursor of rabbit LPH; however, we found no PNGH sequences that corresponded to approx. 350 amino acids between positions 463 and 812 of the LPH precursor, a region encoded by exon 7 of the LPH precursor gene (amino acids 568-784), and no sequences that corresponded to regions near the N-terminus. MS analysis of tryptic peptides yielded 25 peptides, averaging 15 amino acids, with masses that matched segments of the rabbit LPH precursor. Northern blot analysis of pig and human small intestinal polyadenylated mRNA using a non-specific LPH cDNA probe showed an expected approx. 6 kb transcript of the LPH precursor, but also an approx. 4 kb transcript that was consistent with the size predicted from the PNGH protein mass. Using a probe specific to the region encoded by exon 7, hybridization occurred only with the 6 kb transcript. Based on these observations, we propose that both PNGH and LPH enzymes have the same genomic origin, but differ in transcriptional and, possibly, post-translational processing. PMID:14972028

Tseung, Chi-Wah; McMahon, Laura G; Vázquez, Jorge; Pohl, Jan; Gregory, Jesse F

2004-05-15

322

Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin  

Microsoft Academic Search

A cDNA encoding the multifunctional cytochrome P450, CYP71E1, involved in the biosynthesis of the cyanogenic glucoside dhurrin from Sorghum bicolor (L.) Moench was isolated. A PCR approach based on three consensus sequences of A-type cytochromes P450 – (V\\/I)KEX(L\\/F)R, FXPERF, and PFGXGRRXCXG – was applied. Three novel cytochromes P450 (CYP71E1, CYP98, and CYP99) in addition to a PCR fragment encoding sorghum

Søren Bak; Rachel Alice Kahn; Hanne Linde Nielsen; Birger Lindberg Møller; Barbara Ann Halkier

1998-01-01

323

Labdane diterpenes from Otostegia fruticosa.  

PubMed

The new labdane diterpenes otostegin A (2), otostegin B (6) and 15-epi-otostegin B (7) were isolated from the aerial parts of Otostegia. fruticosa, besides the previously known labdanes preleoheterin (1), leoheterin (3), leopersin C and 15-epi-leopersin C (4, 5), ballonigrin (9) and vulgarol (11), along with the iridoid glucoside 8-O-acetylharpagide (10). The structure elucidation of all the isolated compounds was based on their spectral data and chemical derivatization. PMID:11014264

Al-Musayeib, N M; Abbas, F A; Ahmad, M S; Mossa, J S; El-Feraly, F S

2000-08-01

324

Phytochemical constituents and hepatoprotective activity of Viburnum tinus  

Microsoft Academic Search

From the leaves of Viburnum tinus L. (Adoxaceae) two acylated iridoid glucosides (viburtinoside A and B), a coumarin diglucoside scopoletin 7-O-?-d-sophoroside and a natural occurred dinicotinic acid ester 2,6-di-C-methyl-nicotinic acid 3,5-diethyl ester were isolated. In addition to these, 10 known compounds were isolated, namely two bidesmosidic saponins, a hexamethoxy-flavone and five flavonol glycosides, as well as suspensolide A and oleanolic

Mona A. Mohamed; Mohamed S. A. Marzouk; Fatma A. Moharram; Mortada M. El-Sayed; Ayman R. Baiuomy

2005-01-01

325

Transcriptome profiling and digital gene expression analysis of Fallopia multiflora to discover putative genes involved in the biosynthesis of 2,3,5,4'-tetrahydroxy stilbene-2-O-?-d-glucoside.  

PubMed

The compound 2,3,5,4'-tetrahydroxy stilbene-2-O-ß-d-glucoside (THSG) synthesized by Fallopia multiflora (F. multiflora) exhibits pharmacological potency. However, the mechanistic details of its biosynthesis pathway are still vague. To clear this ambiguity, we performed de novo transcriptome assembly and digital gene expression (DGE) profiling analyses of F. multiflora using the Illumina RNA-seq system. RNA-seq generated approximately 70million high-quality reads that were assembled into 65,653 unigenes (mean length=750bp), including 26,670 clusters and 38,983 singletons. A total of 48,173 (73.4%) unigenes were annotated using public protein databases with a cut-off e-value above 10(-5). Furthermore, we investigated the transcriptome difference of four different F. multiflora tissues using DGE profiling. Variations in gene expression were identified based on comparisons of transcriptomes from various parts of a high-level THSG- and a low-level THSG-producing F. multiflora plant. Clusters with similar differential expression patterns and enriched metabolic pathways with regard to the differentially expressed genes putatively involved in THSG biosynthesis were revealed for the first time. Our data provides the most comprehensive sequence resource regarding F. multiflora so far. Taken together, the results of this study considerably extend the knowledge on THSG production. PMID:24967942

Zhao, Wei; Xia, Wanxia; Li, Jiewen; Sheng, Shujing; Lei, Lei; Zhao, Shujing

2014-08-15

326

(+)-Syringaresinol-di-O-beta-D-glucoside, a phenolic compound from Acanthopanax senticosus Harms, suppresses proinflammatory mediators in SW982 human synovial sarcoma cells by inhibiting activating protein-1 and/or nuclear factor-kappaB activities.  

PubMed

(+)-Syringaresinol-di-O-beta-D-glucoside (SR), syringin, and isofraxidin isolated from the stem bark of Acanthopanax senticosus Harms are its major constituents. The present work was undertaken to analyze effects of these compounds on inflammatory functions in SW982 human synovial sarcoma cell system. When cells were exposed to SR, syringin, or isofraxidin, only isofraxidin had significant inhibitory effects on cell growth, although a slight inhibition was observed at the highest concentration of SR. SR suppressed the production of IL-6 at lower concentrations than syringin and isofraxidin. SR and syringin significantly suppressed the production of prostaglandin E(2), while isofraxidin suppressed only slightly. SR was more potent than syringin and isofraxidin at inhibiting the expression of IL-1beta, IL-6, cyclooxygenase (COX)-2 and matrix metalloproteinases (MMP)-1 mRNA, but was less potent than syringin at inhibiting the expression of MMP-2. We further demonstrated that SR significantly reduced MMP-1 promoter luciferase activity and DNA-binding activity of transcriptional factors AP-1 and NF-kappaB. Taken together, these results suggest that SR, an active component of the stem bark of A. senticosus, modulates the inflammatory process involved in arthritis by suppressing various gene expression through inhibiting AP-1 and/or NF-kappaB activities. PMID:17561367

Yamazaki, T; Shimosaka, S; Sasaki, H; Matsumura, T; Tukiyama, T; Tokiwa, T

2007-12-01

327

The biosynthesis of cyanogenic glucosides in higher plants. The (E)- and (Z)-isomers of p-hydroxyphenylacetaldehyde oxime as intermediates in the biosynthesis of dhurrin in Sorghum bicolor (L. ) Moench  

SciTech Connect

The biosynthesis of the tyrosine-derived cyanogenic glucoside dhurrin has been studied with a microsomal preparation obtained from etiolated seedlings of sorghum. The biosynthetic pathway involves tyrosine, N-hydroxytyrosine, and p-hydroxyphenylacetaldehyde oxime as early intermediates. The use of deuterium-labeled tyrosine and mass spectrometric analyses demonstrate that the alpha-hydrogen atom of tyrosine is retained in the conversion of tyrosine to p-hydroxyphenylacetaldehyde oxime. This excludes p-hydroxyphenylpyruvic acid oxime as intermediate in the pathway. A high pressure liquid chromatography method was developed to separate the (E)- and (Z)-isomers of p-hydroxyphenylacetaldehyde oxime. The microsomal enzyme system was found to produce initially the (E)-isomer of p-hydroxyphenylacetaldehyde oxime. An isomerase then converts the (E)-isomer to the (Z)-isomer, which is the isomer preferentially utilized by the microsomal enzyme system in the subsequent biosynthetic reactions. The (E)-isomer produced in situ is more efficiently converted to the (Z)-isomer than exogenously added (E)-isomer and may thus be metabolically channeled.

Halkier, B.A.; Olsen, C.E.; Moller, B.L. (Royal Veterinary and Agricultural Univ., Frederiksberg C (Denmark))

1989-11-25

328

[Chemical and biological evaluation of the effect of plant extracts against Plasmodium berghei].  

PubMed

Extracts from thirteen species of plants were evaluated by "in vivo" antimalarial test against plasmodium berghei effects. Significant activities were observed in the ethyl acetate and aqueous extracts, elaborated of Cedrela tonduzii leaves, Trichilia havanensis and Trichilia americana barks, Neurolaena lobata and Gliricidia sepium leaves and Duranta repens fruits. Compounds identified include flavanoids, coumarins, mellilotic acid and iridoids which some kind of biodynamic activity has previously been reported. The flavone quercetin 1 purified from C. tonduzii gave strong antimalarial activity, however, its respective glucosides (quercetin 3-glucoside 2 y robinine 7) showed little significant activity. PMID:9246360

Castro, O; Barrios, M; Chinchilla, M; Guerrero, O

1996-08-01

329

Cyanidin 3-glucoside protects 3T3-L1 adipocytes against H2O2- or TNF-alpha-induced insulin resistance by inhibiting c-Jun NH2-terminal kinase activation.  

PubMed

Anthocyanins are naturally occurring plant pigments and exhibit an array of pharmacological properties. Our previous study showed that black rice pigment extract rich in anthocyanin prevents and ameliorates high-fructose-induced insulin resistance in rats. In present study, cyanidin 3-glucoside (Cy-3-G), a typical anthocyanin most abundant in black rice was used to examine its protective effect on insulin sensitivity in 3T3-L1 adipocytes exposed to H(2)O(2) (generated by adding glucose oxidase to the medium) or tumor necrosis factor alpha (TNF-alpha). Twelve-hour exposure of 3T3-L1 adipocytes to H(2)O(2) or TNF-alpha resulted in the increase of c-Jun NH(2)-terminal kinase (JNK) activation and insulin receptor substrate 1 (IRS1) serine 307 phosphorylation, concomitantly with the decrease in insulin-stimulated IRS1 tyrosine phosphorylation and cellular glucose uptake. Blocking JNK expression using RNA interference efficiently prevented the H(2)O(2)- or TNF-alpha-induced defects in insulin action. Pretreatment of cells with Cy-3-G reduced the intracellular production of reactive oxygen species, the activation of JNK, and attenuated H(2)O(2)- or TNF-alpha-induced insulin resistance in a dose-dependent manner. In parallel, N-acetyl-cysteine, an antioxidant compound, did not exhibit an attenuation of TNF-alpha-induced insulin resistance. Taken together, these results indicated that Cy-3-G exerts a protective role against H(2)O(2)- or TNF-alpha-induced insulin resistance in 3T3-L1 adipocytes by inhibiting the JNK signal pathway. PMID:18179781

Guo, Honghui; Ling, Wenhua; Wang, Qing; Liu, Chi; Hu, Yan; Xia, Min

2008-03-15

330

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.

1988-04-19

331

A 3D-RISM-SCF method with dual solvent boxes for a highly polarized system: application to 1,6-anhydrosugar formation reaction of phenyl ?- and ?-D-glucosides under basic conditions.  

PubMed

One of the difficulties in application of the usual reference interaction site model self-consistent field (RISM-SCF) method to a highly polarized and bulky system arises from the approximate evaluation of electrostatic potential (ESP) with pure point charges. To improve this ESP evaluation, the ESP near a solute is directly calculated with a solute electronic wavefunction, that distant from a solute is approximately calculated with solute point charges, and they are connected with a switching function. To evaluate the fine solvation structure near the solute by incorporating the long-range solute-solvent Coulombic interaction with low computational cost, we introduced the dual solvent box protocol; one small box with the fine spacing is employed for the first and the second solvation shells and the other large box with the normal spacing is employed for long-range solute-solvent interaction. The levoglucosan formation from phenyl ?- and ?-d-glucosides under basic conditions is successfully inspected by this 3D-RISM-SCF method at the MP2 and SCS-MP2 levels, though the 1D-RISM-SCF could not be applied to this reaction due to the presence of highly polarized and bulky species. This 3D-RISM-SCF calculation reproduces the experimentally reported higher reactivity of the ?-anomer. The 3D-RISM-SCF-calculated activation free energy for the ?-anomer is closer to the experimental value than the PCM-calculated one. Interestingly, the solvation effect increases the difference in reactivity between these two anomers. The reason is successfully elucidated with 3D-RISM-SCF-calculated microscopic solvation structure and decomposition analysis of solute-solvent interaction. PMID:23525092

Aono, Shinji; Hosoya, Takashi; Sakaki, Shigeyoshi

2013-05-01

332

2-Nitro-3-(p-hydroxyphenyl)propionate and aci-1-nitro-2-(p-hydroxyphenyl)ethane, two intermediates in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L. ) Moench  

SciTech Connect

The biosynthetic pathway for the cyanogenic glucoside dhurrin derived from tyrosine has been studied in vitro by using ({sup 18}O)oxygen and a microsomal enzyme system obtained from etiolated sorghum seedlings. The products formed were purified by HPLC and TLC, and the incorporation of ({sup 18}O)oxygen was monitored by mass spectrometry. In the presence of NADPH and ({sup 18}O)dioxygen, L-tyrosine is converted to (E)- and (Z)-p-hydroxyphenylacetaldhyde oxime with quantitative incorporation of an ({sup 18}O)oxygen atom into the oxime function. These data demonstrate that the conversion of N-hydroxytyrosine to p-hydroxyphenylacetaldehyde oxime involves additional N-hydroxylation and N-oxidation reactions giving rise to the formation of 2-nitro-3-(p-hydroxyphenyl)propionate, which by decarboxylation produces aci-1-nitro-2-(p-hydroxyphenyl)ethane. Both compounds are additional intermediates in the pathway. The two ({sup 18}O)oxygen atoms introduced by the N-hydroxylations are enzymatically distinguishable as demonstrated by the specific loss of the oxygen atom introduced by the first N-hydroxylation reaction in the subsequent conversion of aci-1-nitro-2-(p-hydroxyphenyl)ethane to (E)-p-hydroxyphenylacetaldehyde oxime. A high flux of intermediates through the microsomal enzyme system is obtained with N-hydroxytyrosine as a substrate. This renders the conversion of the aci-nitro compound rate limiting and results in its release from the active site of the enzyme system and accumulation of the tautomeric nitro compound.

Halkier, B.A.; Lykkesfeldt, J.; Moller, B.L. (Royal Veterinary and Agricultural Univ., Copenhagen (Denmark))

1991-01-15

333

The biosynthesis of cyanogenic glucosides in higher plants. Identification of three hydroxylation steps in the biosynthesis of dhurrin in Sorghum bicolor (L. ) Moench and the involvement of 1-ACI-nitro-2-(p-hydroxyphenyl)ethane as an intermediate  

SciTech Connect

N-Hydroxytyrosine, (E)- and (Z)-p-hydroxyphenyl-acetaldehyde oxime, p-hydroxyphenylacetonitrile, and p-hydroxymandelonitrile are established intermediates in the biosynthesis of the tyrosine-derived cyanogenic glucoside dhurrin. Simultaneous measurements of oxygen consumption and biosynthetic activity using a microsomal enzyme system isolated from etiolated sorghum seedlings demonstrate a requirement for three oxygen molecules in the conversion of tyrosine to p-hydroxymandelonitrile. Two oxygen molecules are consumed in the conversion of tyrosine to (E)-p-hydroxyphenylacetaldehyde oxime, indicating the existence of a previously undetected hydroxylation step in addition to that resulting in the formation of N-hydroxytyrosine. Radioactively labeled 1-nitro-2-(p-hydroxyphenyl)ethane was chemically synthesized and tested as a possible intermediate. Biosynthetic experiments demonstrate that the microsomal enzyme system metabolizes the nitro compound to the subsequent intermediates in dhurrin synthesis (Km = 0.05 mM; Vmax = 14 nmol/mg of protein/h). Low amounts of 1-nitro-2-(p-hydroxyphenyl)ethane are produced in the microsomal reaction mixtures when tyrosine is used as substrate. These data support the involvement of 1-nitro-2-(p-hydroxyphenyl)ethane or more likely its aci-nitro tautomer as an intermediate between N-hydroxytyrosine and p-hydroxyphenylacetaldehyde oxime. The conversion of (E)-p-hydroxyphenylacetaldehydeoxime to p-hydroxymandelonitrile requires a single oxygen molecule. The oxygen molecule is utilized for hydroxylation of p-hydroxyphenylacetonitrile into p-hydroxymandelonitrile. This indicates that the conversion of p-hydroxyphenylacetaldehyde oxime into p-hydroxyphenylacetonitrile proceeds by a simple dehydration reaction.

Halkier, B.A.; Moller, B.L. (Royal Veterinary and Agricultural Univ., Copenhagen (Denmark))

1990-12-05

334

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

1993-01-01

335

Cytotoxicity studies of semi-synthetic derivatives of theveside derived from the aqueous extract of leaves of 'suicide tree' Cerbera odollam.  

PubMed

We report the isolation of two known iridoid glucosides theviridoside (1) and theveside (2) from the aqueous extract of leaves of Cerbera odollam and semi-synthetic derivatisation of theveside prepared in a single step under protection group-free conditions. Derivatives 2a-j were evaluated for cytotoxicity towards five human cancer cell lines of different origins, namely SKBR3 (breast), HeLa (cervical), A375 (skin), HepG2 (liver) and HCT-116 (colon), and IC50 values were determined. Derivatives 2b and 2h exhibited moderate cytotoxicity against HCT-116 and A375 cell lines, respectively. PMID:24805359

Gorantla, Jaggaiah N; Vellekkatt, Jamsheena; Nath, Lekshmi R; Anto, Ruby John; Lankalapalli, Ravi S

2014-09-01

336

Bioactive iridoids and a new lignan from Allamanda cathartica and Himatanthus fallax from the Suriname rainforest.  

PubMed

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

1997-12-01

337

Oleuropein, a non-toxic olive iridoid, is an anti-tumor agent and cytoskeleton disruptor  

Microsoft Academic Search

Oleuropein, a non-toxic secoiridoid derived from the olive tree, is a powerful antioxidant and anti-angiogenic agent. Here, we show it to be a potent anti-cancer compound, directly disrupting actin filaments in cells and in a cell-free assay. Oleuropein inhibited the proliferation and migration of advanced-grade tumor cell lines in a dose-responsive manner. In a novel tube-disruption assay, Oleuropein irreversibly rounded

Hamdi K.. Hamdi; Raquel Castellon

2005-01-01

338

Oleuropein, a non-toxic olive iridoid, is an anti-tumor agent and cytoskeleton disruptor.  

PubMed

Oleuropein, a non-toxic secoiridoid derived from the olive tree, is a powerful antioxidant and anti-angiogenic agent. Here, we show it to be a potent anti-cancer compound, directly disrupting actin filaments in cells and in a cell-free assay. Oleuropein inhibited the proliferation and migration of advanced-grade tumor cell lines in a dose-responsive manner. In a novel tube-disruption assay, Oleuropein irreversibly rounded cancer cells, preventing their replication, motility, and invasiveness; these effects were reversible in normal cells. When administered orally to mice that developed spontaneous tumors, Oleuropein completely regressed tumors in 9-12 days. When tumors were resected prior to complete regression, they lacked cohesiveness and had a crumbly consistency. No viable cells could be recovered from these tumors. These observations elevate Oleuropein from a non-toxic antioxidant into a potent anti-tumor agent with direct effects against tumor cells. Our data may also explain the cancer-protective effects of the olive-rich Mediterranean diet. PMID:16024000

Hamdi, Hamdi K; Castellon, Raquel

2005-09-01

339

Cytotoxicity and in vitro susceptibility of Entamoeba histolytica to Morinda morindoides leaf extracts and its isolated constituents.  

PubMed

An aqueous decotion (dried extract), an 80% MeOH extract from Morinda morindoides leaves, and 10 flavonoids and 4 iridoids isolated from the 80% MeOH extract were evaluated in vitro for their potential antiamoebic activity and their cytotoxic effect against MT-4 cells. Results indicated that the aqueous decoction and the 80% MeOH extract exhibited an interesting antiamoebic activity with IC(50) values of 3.1 +/- 1.7 and 1.7 +/- 0.6 microg/ml, respectively. Apigenin-7-O-glucoside and luteolin-7-O-glucoside exhibited a moderate antiamoebic activity with IC(50) values of 22.3 +/- 3.2 and 37.4 +/- 2.7 microg/ml, respectively. Kaempferol (IC(50) = 10.3 +/- 2.3 microg/ml), apigenin (IC(50) = 12.7 +/- 4.3 microg/ml), and luteolin (IC(50) = 17.8 +/- 4.3 microg/ml) showed a more pronounced activity than their corresponding glycosides. All tested iridoids displayed a very good activity with IC(50) values less than 10 microg/ml. The most active iridoids were epoxygaertneroside (IC(50) = 1.3 +/- 0.4 microg/ml) and methoxygaertneroside (IC(50) = 2.3. +/- 0.7), followed by gaertneroside and gaertneric acid with IC(50) values of 4.3 +/- 1.8 and 7.1 +/- 1.4 microg/ml, respectively. Except quercetin and quercetin-7,4'-dimethylether which have shown a cytotoxic effect with IC(50) ranging from 14 to 22 microg/ml. No correlation could be deduced between the observed antiamoebic and cytotoxic activity of these tested samples. A structure-activity relationship for isolated compounds is discussed. These findings support the medicinal report for the traditional use of Morinda morindoides leaves for the treatment of amoebiasis. PMID:16603327

Cimanga, R K; Kambu, K; Tona, L; Hermans, N; Apers, S; Totté, J; Pieters, L; Vlietinck, A J

2006-08-11

340

Host Shifts from Lamiales to Brassicaceae in the Sawfly Genus Athalia  

PubMed Central

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.

Opitz, Sebastian E. W.; Boeve, Jean-Luc; Nagy, Zoltan Tamas; Sonet, Gontran; Koch, Frank; Muller, Caroline

2012-01-01

341

Megastigmane glucosides from Equisetum debile and E. diffusum.  

PubMed

A new megastigmane diglucoside, (3S,5R,6S,7E,9S)-megastigman-7-ene-5,6-epoxy-3,9-diol 3,9-O-beta-D-diglucopyranoside (3), was isolated from the aerial portion of Equisetum debile along with macarangioside D (debiloside A), sammangaoside A, (6R,9S)-3-oxo-alpha-ionol 9-O-beta-D-glucopyranoside, debiloside B, kaempferol 3-O-sophoroside, kaempferol 3,7-O-beta-D-diglucopyranoside, kaempferol 3-O-sophoroside-7-O-beta-D-glucopyranoside, phenylethyl O-beta-D-glucopyranoside, (Z)-3-hexenyl O-beta-D-glucopyranoside, (7S,8R)-dehydrodiconiferyl 4-O-beta-D-glucopyranoside, and L-tryptophan. The absolute configuration at C-6 of the original structure of debilo-side A was revised to 6R-configuration, and was identical with macarangioside D (1). From the aerial portion of E. diffusum, four compounds, sammangaoside A, kaempferol 3-O-sophoroside and L-tryptophan and (3S,5R,6S,7E,9S)-megastigman-7-ene-5,6-epoxy-3,9-diol 3-O-beta-D-glucopyranoside were identified. The spectroscopic data of (3S,5R,6S,7E,9S)-megastigman-7-ene-5,6-epoxy-3,9-diol 3-O-beta-D-glucopyranoside (13) were found to be identical with corchoionoside A (9R-isomeric compound). The structure of corchoionoside A was also discussed. Structure determinations were based on physical data and spectroscopic evidence. PMID:17666861

Kanchanapoom, Tripetch; Otsuka, Hideaki; Ruchirawat, Somsak

2007-08-01

342

Hemiterpene glucosides and other constituents from Spiraea canescens.  

PubMed

Five glycosides, 2-(trans-cinnamoyloxy-methyl)-1-butene-4-O-beta-D-glucopyranoside (1), 4-(6'-O-trans-cinnamoyl)-(2-hydroxymethyl-4-hydroxy-butenyl-beta-D-glucopyranoside (2), 6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside (3), 6'-O-(4-methoxy-trans-cinnamoyl) alpha/beta-D-glucopyranose (4) 6'-O-(4''-methoxy-trans-cinnamoyl)-kaempferol-3-beta-D-glucopyranoside (7) along with six known compounds, (+)-isolariciresinol 3a-O-beta-D-glucopyranoside (8) (+)-lyoniresinol 3a-O-beta-D-glucopyranoside (9), apigenin 7-O-beta-D-glucopyranoside (10), quercetin 3-O-beta-D-glucopyranoside (11), 6'-O-cinnamoyl-alpha/beta-D-glucopyranose (6) 6'-O-p-coumaroyl-alpha/beta-D-glucopyranose (5) were isolated from the whole plant of Spiraea canescens. Some of these compounds showed potent radical scavenging activity in relevant non-physiological assays. Their structures were determined by NMR spectroscopic and CID mass spectrometric techniques. PMID:19747701

Choudhary, M Iqbal; Naheed, Nadra; Abbaskhan, Ahmed; Ali, Sajjad; Atta-ur-Rahman

2009-01-01

343

Isovitexin o-glucosides from Aquilegia vulgaris L.  

PubMed

4'-O-beta-glucopyranoside of isovitexin from the leaves with stems and 4'-O-delta-glucopyranoside of -2"-O-beta-glucopyranosylisovitexin from the flowers of Aquilegia vulgnris L. were isolated. The structures of the compounds were determined by chemical and spectroscopic methods. PMID:11693732

Bylka, W

2001-01-01

344

Two new steroidal glucosides from Tribulus terrestris L.  

PubMed

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

2009-06-01

345

A new eudesmane sesquiterpene glucoside from Liriope muscari fibrous roots.  

PubMed

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

2011-01-01

346

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

1997-01-01

347

Identification of TLC markers and quantification by HPLC-MS of various constituents in noni fruit powder and commercial noni-derived products.  

PubMed

The composition of noni (Morinda citrifolia) products has been investigated. TLC profiles of several commercial juices and capsules were compared. 3-Methyl-1,3-butanediol was identified as a typical marker in noni juices. The presence of sorbic acid (E200) was detected in one juice declared as additive free. Quantitative data have been obtained by HPLC-MS. A method for the quantification of characteristic noni constituents, such as iridoid glucosides, scopoletin, rutin, fatty acid glucosides, and anthraquinones, was developed and validated. The separation was performed on a C18 column with a gradient of acetonitrile in water containing 0.1% formic acid. Detection was carried out with ESI-MS in the negative ion mode. Significant differences were observed between the products. Asperulosidic acid, deacetylasperulosidic acid, and rutin were present in all samples analyzed, but their concentrations differed considerably between the products. Fatty acid glucosides, noniosides B and C, were present in capsules and most juices. Scopoletin was mainly found in juices. The anthraquinone alizarin, which has been reported from roots and leaves, was not detected in the samples investigated. PMID:17696360

Potterat, Olivier; Felten, Roger Von; Dalsgaard, Petur W; Hamburger, Matthias

2007-09-01

348

Phytochemical analysis, biological evaluation and micromorphological study of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande endemic to central Apennines, Italy.  

PubMed

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 (IC?? 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

2013-10-01

349

Hedyotis diffusa water extract diminished the cytotoxic effects of chemotherapy drugs against human breast cancer MCF7 cells.  

PubMed

Hedyotis diffusa is a Chinese herbal medicine widely used in combination with other herbal medicines such as Scutellaria barbata to treat various types of cancer. Late-stage and recurrent cancer patients usually use H. diffusa during chemotherapy in expecting to achieve additive or synergistic therapeutic effects. Several classes of active ingredients, including anthraquinones, iridoid glucosides and stigmasterols. have been isolated and characterized from H. diffusa. In the current study, we isolated alkaloid/flavonoid from H diffusa and showed that the crude alkaloid/flavonoid extract rather than its three major components possessed antitumor activity against human breast cancer cell line MCF7. Co-administration of H. diffusa water extract diminished the cytotoxicities of chemotherapy drugs doxorubicin, cyclophosphamide and docetaxel towards the MCF7 cells, implicating that H. diffusa should not be used during breast cancer chemotherapy. PMID:25026725

Dong, Qiulin; Ling, Binbing; Gao, Bosong; Maley, Jason; Sammynaiken, Ramaswami; Yang, Jian

2014-05-01

350

Comparison between HPLC and HPTLC-densitometry for the determination of harpagoside from Harpagophytum procumbens CO(2)-extracts.  

PubMed

Carbon dioxide (CO(2)) extracts of the secondary roots of Harpagophytum procumbens were quantified by high performance liquid chromatography (HPLC) and high performance thin layer chromatography (HPTLC). An isocratic HPLC method was used for the quantification of the iridoid glucoside harpagoside at 278 nm. A HPTLC assay was developed for the determination of harpagoside after coloration at 509 nm. The diode array detection of both analytical assays were used to examine the purity of harpagoside peaks and compared with the standards, respectively. The assays provide good accuracy, reproducibility and selectivity for the quantitative analysis of harpagoside. The harpagoside contents of 15 different CO(2)-extracts were compared by HPLC and HPTLC-densitometry. The quantitative results of both analytical methods did not show any statistical significance between each other, although a trend to slightly lower mean values could be found for the HPTLC method. PMID:15797807

Günther, M; Schmidt, P C

2005-04-01

351

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

2012-01-01

352

Isolation of two new ionone glucosides from quince (Cydonia oblonga Mill.) leaves.  

PubMed

The 9-O-beta-D-glucopyranosides of (6R)-3-oxo-4-hydroxy-7,8-dihydro-alpha-ionol 1 and 3-oxo-5,6-epoxy-beta-ionol 2 were isolated from quince leaves. The glycosidic extract was obtained by XAD-2 adsorption and MeOH elution. After DCCC separation and flash chromatography, purification by high performance liquid chromatography was carried out. The novel quince leaf constituents were characterized as peracetates 1a and 2a. PMID:11990428

Lutz-Röder, Andrea; Schneider, Marc; Winterhalter, Peter

2002-04-01

353

Biodegradability of antineoplastic compounds in screening tests: influence of glucosidation and of stereochemistry.  

PubMed

Some pharmaceuticals such as antineoplastics are carcinogenic, mutagenic, teratogenic and fetotoxic. Antineoplastics and their metabolites are excreted by patients into waste water. In laboratory testing the frequently used isomeric anti-tumour agents cyclophosphamide (CP) and ifosfamide (IF) were shown to be not biodegradable. They are not eliminated in municipal sewage treatment plants and therefore detected in their effluents. Structural related compounds are beta-D-glucosylisophosphoramidmustard (beta-D-Glc-IPM; INN = glufosfamide) and beta-L-glucosylisophosphoramidmustard (beta-L-Glc-IPM). beta-L-Glc-IPM has no antineoplastic effects whereas beta-D-Glc-IPM is active against tumours. In contrast to IF and CP and almost all other investigated antineoplastics beta-D-Glc-IPM is inherently biodegradable. Improved biodegradability of beta-D-Glc-IPM compared to IF shows that reducing the impact of pharmaceuticals on the aquatic environment is feasible by changing the chemical structure of a given compound exerting a similar mode of action and therapeutic activity. Stereochemistry may be crucial for pharmaceutical activity of the compounds as well as for its biodegradability in the environment. PMID:10705555

Kümmerer, K; al-Ahmad, A; Bertram, B; Wiessler, M

2000-04-01

354

Distribution of iridiod glucosides and anti-oxidant compounds in Spathodea campanulata parts.  

PubMed

The antioxidant principles isolated from the various parts of the plant are verminoside (leaf, stem bark and flowers; EC(50) = 2.04 µg/ml), Specioside (flowers; EC(50) = 17.44 µg/ml), Kampeferol diglucoside (leaf; EC(50) = 8.87 µg/ml) and Caffeic acid (leaf and fruits). The non anti-oxidant components isolated in the study include ajugol (stem bark and fruits) and phytol (leaf). PMID:22238480

Elusiyan, C A; Ani, N C; Adewunmi, C O; Olugbade, T A

2011-01-01

355

Biosynthesis of Mustard Oil Glucosides. Vi. Biosynthesis of Glucobarbarin in Reseda Luteola L.  

National Technical Information Service (NTIS)

A number of C(14)-labelled compounds were fed to Reseda luteola L.; after a 24-hour period of metabolism, the thioglucoside aglycone (5-phenyl-2-oxazolidinethione) was isolated and its specific activity determined. In some instances the aglycone was degra...

E. W. Underhill

1964-01-01

356

Bone mineralization enhancing activity of a methoxyellagic acid glucoside from a Feijoa sellowiana leaf extract.  

PubMed

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

2009-02-01

357

A cyanoallyl glucoside from Alliaria petiolata, as a feeding deterrent for larvae of Pieris napi oleracea.  

PubMed

Alliarinoside, a feeding inhibitor against early instar larvae of Pieris napi oleracea, was isolated from the foliage of Alliaria petiolata and characterized as (2Z)-4-(beta-D-glucopyranosyloxy)-2-butenenitrile (1) by spectroscopic methods. The structural assignment was confirmed by synthesis of peracetylated alliarinoside (2) and its 2E isomer (3). A sample of synthetic 1 was isolated by preparative HPLC from the hydrolysis of the 2Z acetate. Feeding inhibition assays showed comparable activity for the synthetic and natural glycosides. PMID:11325224

Haribal, M; Yang, Z; Attygalle, A B; Renwick, J A; Meinwald, J

2001-04-01

358

A new stilbene glucoside gallate from the roots of Polygonum multiflorum.  

PubMed

A new stilbenoid (1) was isolated from the root extract of Polygonum multiflorum together with eight known constituents (2-9). The chemical structure of 1 was established as the 6''-O-monogalloyl ester of (E)-2,3,4',5-beta-tetrahydroxystilbene-2-beta-D-glucopyranoside based on physicochemical and spectroscopic analyses, particularly by NMR spectroscopic data, i.e., COSY, HMQC and HMBC. Compound 1 weakly inhibited acetylcholinesterase in vitro. PMID:18958411

Kim, Hyun Ki; Choi, Yeon Hee; Choi, Jae Seok; Choi, Sang Un; Kim, Young Sup; Lee, Kang Ro; Kim, Young-Kyoon; Ryu, Shi Yong

2008-10-01

359

A new phenylpropanoid glucoside from the aerial parts of Lygodium japonicum  

Microsoft Academic Search

A new compound, 4-O-caffeoyl-d-glucopyranose (1), and a new natural product, 3-O-caffeoyl-d-glucopyranose (2), together with six known compounds (3–8) were isolated from the aerial parts of Lygodium japonicum. Their structures were elucidated on the basis of extensive spectroscopic data analyses. The oxygen radical absorbance capacity assay was applied to evaluate their antioxidative capacities in vitro, which revealed that 1–8 showed strong

Ying-Hui Duan; Yi Dai; Rong-Rong He; Hiroshi Kurihara; Yao-Lan Li; Xin-Sheng Yao

2012-01-01

360

A new phenylpropanoid glucoside from the aerial parts of Lygodium japonicum.  

PubMed

A new compound, 4-O-caffeoyl-D-glucopyranose (1), and a new natural product, 3-O-caffeoyl-D-glucopyranose (2), together with six known compounds (3-8) were isolated from the aerial parts of Lygodium japonicum. Their structures were elucidated on the basis of extensive spectroscopic data analyses. The oxygen radical absorbance capacity assay was applied to evaluate their antioxidative capacities in vitro, which revealed that 1-8 showed strong antioxidative properties. PMID:22251217

Duan, Ying-Hui; Dai, Yi; He, Rong-Rong; Kurihara, Hiroshi; Li, Yao-Lan; Yao, Xin-Sheng

2012-01-01

361

Cytopiloyne, a polyacetylenic glucoside, prevents type 1 diabetes in nonobese diabetic mice.  

PubMed

Some polyacetylenes from the plant Bidens pilosa have been reported to treat diabetes. In this study, we report that the cytopiloyne from B. pilosa, which is structurally different from the above-mentioned polyacetylenes and inhibits CD4(+) T cell proliferation, effectively prevents the development of diabetes in nonobese diabetic mice as evidenced by a normal level of blood glucose and insulin and normal pancreatic islet architecture. Cytopiloyne also suppresses the differentiation of type 1 Th cells but promotes that of type 2 Th cells, which is consistent with it enhancing GATA-3 transcription. Also, long-term application of cytopiloyne significantly decreases the level of CD4(+) T cells inside pancreatic lymph nodes and spleens but does not compromise total Ab responses mediated by T cells. Coculture assays imply that this decrease in CD4(+) T cells involves the Fas ligand/Fas pathway. Overall, our results suggest that cytopiloyne prevents type 1 diabetes mainly via T cell regulation. PMID:17513748

Chang, Cicero Lee-Tian; Chang, Shu-Lin; Lee, Yi-Mei; Chiang, Yi-Ming; Chuang, Da-Yung; Kuo, Hui-Kai; Yang, Wen-Chin

2007-06-01

362

Benzylbenzoate and norlignan glucosides from Curculigo pilosa: structural analysis and in vitro vascular activity  

Microsoft Academic Search

From the rhizomes of Curculigo pilosa, two benzylbenzoate diglucosides, piloside A and piloside B, and a glucosyl-fused norlignan, pilosidine, previously obtained only as the tetra-O-methyl derivative, were isolated. Pilosidine showed facilitating effect on adrenaline evoked contractions in rabbit aorta isolated preparations.

Giovanna Palazzino; Corrado Galeffi; Elena Federici; Franco Delle Monache; Maria Francesca Cometa; Maura Palmery

2000-01-01

363

Nitrophenyl glucoside hydrolysis as a potential time-temperature integrator reaction  

Microsoft Academic Search

Hydrolysis of p-nitrophenyl ?-d-glucopyranoside (NPG) in borate buffer, pH 11.0, has been investigated as a potential chemical time-temperature integrator (TTI) reaction. The yellow nitrophenolate ion produced on hydrolysis was shown to be highly stable and to follow first order kinetics of formation. The temperature coefficient of the reaction rate (z-value) was found to be 21.7 (± 1.2) °C over the

J. B. Adams; F. M. Langley

1998-01-01

364

Acute, chronic and terminal toxicity to 4'-demethylepipodophyllotoxin thenylidene glucoside (VM26) in mice.  

PubMed

The development of toxicity to 4'-demethylepipodophyllotoxin-9-(4,6,-O-thenylidene-beta-glucopyranoside) an epipodophyllotoxin with oncolytic activity, was characterized in mice treated three times at 3-day intervals with 10 mg of drug i.p. per kg of body weight. Changes in organ function and general metabolism were determined by measuring 18 constituents of blood for up to 10 weeks after drug administration. The results indicate three distinct phases of toxicity to 4'-demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-beta-glucopyranoside). Acute toxicity developed within the first 10 days and was expressed by a depressed hematocrit and elevated plasma levels of glutamate-pyruvate transaminase, glutamate-oxaloacetate transaminase, lactic dehydrogenase, amylase, lipase, and uric acid. By 4 weeks, levels ahd returned to normal. The acute phase was followed by a chronic phase, which was characterized by progressive decreases in plasma levels of glucose, cholesterol, albumin, and total protein. Finally, about 7 weeks after treatment, a terminal phase indicated by correlated increases in glutamate-pyruvate transaminase, glutamate-oxaloacetate transaminase, lactic dehydrogenase, and blood urea nitrogen became apparent. Plasma levels of creatine phosphokinase, calcium, inorganic phosphate, total bilirubin, ketones, and alkaline phosphatase did not change. Although the pancreas liver and marrow were all affected during acute toxicity, boserved changes in blood components during the chronic and terminal phases correlate best with continued hepatotoxicity. The present evidence on delayed toxicity to 4'-demethylepipodophyllotoxin 9-(4,6-o-2-thenylidene-beta-D-glucopyranoside) is most compatible with irreversible hepatotoxocity which leads to metabolic deficiencies and terminates in death of mice. PMID:1131830

Hacker, M; Roberts, D W

1975-07-01

365

A cardiac glucoside with in vitro anti-HIV activity isolated from Elaeodendron croceum  

Microsoft Academic Search

Human immunodeficiency virus (HIV) affects more than 40 million people worldwide and more than 5 million in South Africa alone. There is no cure for the disease yet, and novel effective drugs need to be discovered to make any progress in combating the disease. Twelve extracts from indigenous South African plants were analysed, of which Elaeodendron croceum showed potent inhibition

Gerhard Prinsloo; J. J. Marion Meyer; Ahmed A. Hussein; Eduardo Munoz; Rocio Sanchez

2010-01-01

366

Hydrolysis of Oleuropein by Lactobacillus plantarum Strains Associated with Olive Fermentation  

PubMed Central

Oleuropein (Chemical Abstracts Service registry number 32619-42-4), a bitter-tasting secoiridoid glucoside commonly found in leaves of the olive tree as well as in olives (Olea europaea L.), was found to be hydrolyzed by the ?-glucosidase (EC 3.2.1.2.1) produced by oleuropeinolytic Lactobacillus plantarum-type strains. Three strains, designated B17, B20, and B21, were isolated from the brine of naturally ripe olives not treated with alkali. These strains were rod-shaped forms, grown at a pH 3.5 limit, and tolerated 1% oleuropein and 8% NaCl in the growth medium. The ?-glucosidase produced hydrolyzed 5-bromo-4-chloro-3-indolyl-?-d-glucopy-ranoside as well as oleuropein. The presence of 2% glucose in the medium inhibited activity by 40 to 50%, depending on the bacterial strain. Chromatographic analysis of the trimethylsilyl derivatives of the products obtained after 7 days of incubation at 30°C of strain B21 showed all the hydrolysis products of oleuropein, i.e., aglycone, iridoid monoterpen, and 3,4-dihydroxyphenylethanol (hydroxytyrosol). Oleuropein and its aglycone after 21 days of incubation decreased to trace levels with the simultaneous increase in concentration of ?-3,4-dihydroxyphenylethanol. Images

Ciafardini, G.; Marsilio, V.; Lanza, B.; Pozzi, N.

1994-01-01

367

Catalpol Ameliorates Sodium Taurocholate-Induced Acute Pancreatitis in Rats via Inhibiting Activation of Nuclear Factor Kappa B.  

PubMed

Catalpol, an iridoid glucoside extracted from the traditional Chinese herbal medicine, Rehmannia glutinosa, is reported to exert neuroprotective, anti-inflammatory, anti-tumor and anti-apoptotic effects. The main aim of the present study was to investigate whether catalpol ameliorates experimental acute pancreatitis (AP) induced by sodium taurocholate (STC). AP was induced in rats via retrograde injection of 4% STC (0.1 mL/100 g) into the biliopancreatic duct. Rats were pre-treated with saline or catalpol (50 mg/kg) 2 h before STC injection. At 12, 24 and 48 h after injection, the severity of AP was evaluated using biochemical and morphological analyses. Pretreatment with catalpol led to a significant reduction in serum amylase and lipase activities, pancreatic histological damage, myeloperoxidase (MPO) activity, interleukin (IL)-1?, IL-6 and TNF-? levels, and activation of nuclear factor kappa B (NF-?B). Moreover, administration of catalpol increased the viability of pancreatic acinar cells and inhibited NF-?B expression in vitro. Our results collectively support the potential of catalpol as a highly effective therapeutic agent for treatment of AP. PMID:25000266

Xiao, Wen Qin; Yin, Guo Jian; Fan, Yu Ting; Qiu, Lei; Cang, Xiao Feng; Yu, Ge; Hu, Yan Ling; Xing, Miao; Wu, De Qing; Wang, Xing Peng; Hu, Guo Yong; Wan, Rong

2014-01-01

368

Picroside II protects cardiomyocytes from hypoxia/reoxygenation-induced apoptosis by activating the PI3K/Akt and CREB pathways.  

PubMed

Picroside II, an iridoid glucoside found in the root of Picrorhiza scrophulariiflora Pennell (Scrophulariaceae), has been demonstrated to reduce apoptosis in neuronal cells and other cell types. However, whether picroside II has a protective effect against cardiomyocyte apoptosis is poorly understood. In the present study, we investigated the cardioprotective role of picroside II and the underlying mechanisms in hypoxia/reoxygenation-induced cardiomyocyte apoptosis. The pretreatment with picroside II markedly attenuated hypoxia/reoxygenation-induced cell damage dose-dependently, which was evident by the increased cell viability and the corresponding decrease in lactate dehydrogenase release (LDH). The pretreatment with picroside II inhibited apoptosis confirmed by Annexin V-FITC staining, Hoechst 33258 nuclear staining and by assessment of caspase-3 activity. In addition, we found that picroside II not only increased the expression of Bcl-2, while decreasing Bax expression, but also augmented Akt and cAMP response element-binding protein (CREB) phosphorylation and ultimately inhibited hypoxia/reoxygenation-induced apoptosis. Furthermore, the protective effects of picroside II were abrogated by pretreatment of the cells with wortmannin or LY294002, a specific PI3K inhibitor. The present study suggests that picroside II inhibits hypoxia/reoxygenation-induced apoptosis in cardiomyocytes by activating the PI3K/Akt and CREB pathways and modulating expression of Bcl-2 and Bax. PMID:22581361

Meng, Fan-Ji; Jiao, Su-Min; Yu, Bo

2012-08-01

369

Selective MAO-B inhibitors: a lesson from natural products.  

PubMed

Monoamine oxidases (MAOs) are mitochondrial bound enzymes, which catalyze the oxidative deamination of monoamine neurotransmitters. Inside the brain, MAOs are present in two isoforms: MAO-A and MAO-B. The activity of MAO-B is generally higher in patients affected by neurodegenerative diseases like Alzheimer's and Parkinson's. Therefore, the search for potent and selective MAO-B inhibitors is still a challenge for medicinal chemists. Nature has always been a source of inspiration for the discovery of new lead compounds. Moreover, natural medicine is a major component in all traditional medicine systems. In this review, we present the latest discoveries in the search for selective MAO-B inhibitors from natural sources. For clarity, compounds have been classified on the basis of structural analogy or source: flavonoids, xanthones, tannins, proanthocyanidins, iridoid glucosides, curcumin, alkaloids, cannabinoids, and natural sources extracts. MAO inhibition values reported in the text are not always consistent due to the high variability of MAO sources (bovine, pig, rat brain or liver, and human) and to the heterogeneity of the experimental protocols used. PMID:24218136

Carradori, Simone; D'Ascenzio, Melissa; Chimenti, Paola; Secci, Daniela; Bolasco, Adriana

2014-02-01

370

A new heptasubstituted (E)-aurone glucoside and other aromatic compounds of Gomphrena agrestis with biological activity.  

PubMed

A new aurone 1 and two known substances, aurantiamide acetate (2) and tiliroside (3), were isolated from the ethanolic extract of Gomphrena agrestis. The structural determination of 1 was based on spectroscopic and spectrometric data. The substance was defined as (E)-3'-O-beta-D-glucopyranosyl-4,5,6,4'-tetrahydroxy-7,2'-dimethoxyaurone. Biological activity of the ethanolic crude extract and isolated compounds against bacteria, fungi and Leishmania amazonensis amastigotes was evaluated. This appears to be the first report documenting aurone and aurantiamide compounds in the Amaranthaceae family. In the evaluation of biological activity the ethanolic extract of G. agrestis and compounds 1, 2, and 3 were shown to be active mainly against Staphylococcus aureus, Staphylococcus epidermidis and Pseudomonas aeruginosa. PMID:15813368

Ferreira, Eliane O; Salvador, Marcos J; Pral, Elizabeth M F; Alfieri, Silvia C; Ito, Izabel Y; Dias, Diones A

2004-01-01

371

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

2010-01-01

372

Atomistic simulation studies of the ?/?-glucoside and galactoside in anhydrous bilayers: effect of the anomeric and epimeric configurations.  

PubMed

Fully atomistic molecular dynamics simulation studies of thermotropic bilayers were performed using a set of glycosides namely n-octyl-?-D-glucopyranoside (?-C8Glc), n-octyl-?-D-glucopyranoside (?-C8Glc), n-octyl-?-D-galactopyranoside (?-C8Gal), and n-octyl-?-D-galactopyranoside (?-C8Gal) to investigate the stereochemical relationship of the epimeric/anomeric quartet liner glycolipids with the same octyl chain group. The results showed that, the anomeric stereochemistry or the axial/equatorial orientation of C1-O1 (?/?) is an important factor controlling the area and d-spacing of glycolipid bilayer systems in the thermotropic phase. The head group tilt angle and the chain ordering properties are affected by the anomeric effect. In addition, the L(C) phase of ?-C8Gal, is tilting less compared to those in the fluid L(?). The stereochemistry of the C4-epimeric (axial/equatorial) and anomeric (?/?) centers simultaneously influence the inter-molecular hydrogen bond. Thus, the trend in the values of the hydrogen bond for these glycosides is ?-C8Gal?>??-C8Glc?>??-C8Glc?>??-C8Gal. The four bilayer systems showed anomalous diffusion behavior with an observed trend for the diffusion coefficients; and this trend is ?-C8Gal?>??-C8Glc?>??-C8Gal?>??-C8Glc. The "bent" configuration of the ?-anomer results in an increase of the hydrophobic area, chain vibration and chain disorganization. Since thermal energy is dispensed more entropically for the chain region, the overall molecular diffusion decreases. PMID:24623320

Ahmadi, Sara; Manickam Achari, Vijayan; Nguan, Hockseng; Hashim, Rauzah

2014-03-01

373

An on-line method for pressurized hot water extraction and enzymatic hydrolysis of quercetin glucosides from onions.  

PubMed

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

2013-06-27

374

Bioavailability of C-linked dihydrochalcone and flavanone glucosides in humans following ingestion of unfermented and fermented rooibos teas.  

PubMed

High-performance liquid chromatography-mass spectrometry (HPLC-MS(n)) detected aspalathin and nothofagin, C-glycosides of apigenin and luteolin, and four eriodictyol-C-glycoside isomers in unfermented and fermented rooibos teas. The fermented drink contained 10-fold higher levels of aspalathin and nothofagin and a 4-fold lower eriodictyol-C-glycoside content than the fermented tea. The total flavonoid contents in 500 mL servings of the teas were 84 (fermented) and 159 mumol (unfermented). Following the ingestion of 500 mL of the teas by 10 volunteers, 0-24 h urine and plasma samples were collected for analysis. HPLC-MS(n) identified eight metabolites in urine. These were O-linked methyl, sulfate, and glucuronide metabolites of aspalathin and an eriodictyol-O-sulfate. The main compound excreted was an O-methyl-aspalathin-O-glucuronide (229 nmol) following ingestion of the unfermented drink and eriodictyol-O-sulfate (68 nmol) after ingestion of the fermented beverage. The overall metabolite levels excreted were 82 and 352 nmol, accounting for 0.09 and 0.22% of the flavonoids in the fermented and unfermented drinks, respectively. Most of the aspalathin metabolites were excreted within 5 h of tea consumption, suggesting absorption in the small intestine. Urinary excretion of the eriodictyol-O-sulfate occurred mainly during the 5-12 h collection period, indicative of absorption in the large intestine. Despite exhaustive searches, no flavonoid metabolites were detected in plasma. PMID:19534535

Stalmach, Angélique; Mullen, William; Pecorari, Monia; Serafini, Mauro; Crozier, Alan

2009-08-12

375

New dammarane-type glucosides as potential activators of AMP-activated protein kinase (AMPK) from Gynostemma pentaphyllum  

Microsoft Academic Search

AMP-activated protein kinase (AMPK) is a key sensor and regulator of glucose, lipid, and energy metabolism throughout the body. Activation of AMPK improves metabolic abnormalities associated with metabolic diseases including obesity and type-2 diabetes. The oriental traditional medicinal herbal plant, Gynostemma pentaphyllum, has shown a wide range of beneficial effects on glucose and lipid metabolism. In this study, we found

Phi Hung Nguyen; Rehman Gauhar; Seung Lark Hwang; Trong Tuan Dao; Dong Chan Park; Ji Eun Kim; Hebok Song; Tae Lin Huh; Won Keun Oh

2011-01-01

376

Cyanidin3Glucoside Reverses Ethanol-Induced Inhibition of Neurite Outgrowth: Role of Glycogen Synthase Kinase 3 Beta  

Microsoft Academic Search

Ethanol is a potent teratogen for the developing central nervous system (CNS), and fetal alcohol syndrome (FAS) is the most\\u000a common nonhereditary cause of mental retardation. Ethanol disrupts neuronal differentiation and maturation. It is important\\u000a to identify agents that provide neuroprotection against ethanol neurotoxicity. Using an in vitro neuronal model, mouse Neuro2a\\u000a (N2a) neuroblastoma cells, we demonstrated that ethanol inhibited

Gang Chen; Kimberly A. Bower; Mei Xu; Min Ding; Xianglin Shi; Zun-Ji Ke; Jia Luo

2009-01-01

377

Biosynthesis of Mustard Oil Glucosides: V. Formation of Gluconasturtiin from L-Gammaphenylbutyrine-C(14)-n(15) in Watercress.  

National Technical Information Service (NTIS)

C(14)-Labelled compounds were fed to watercress (Nasturtium officinale R. Br.) and their efficiency as precursors of the aglycone portion of gluconasturtiin compared. Phenylalanine-2- and -3-C(14) and sodium acetate-2-C(14) were efficient precursors of th...

E. W. Underhill

1964-01-01

378

Synthesis of rhamnosylated diosgenyl glucosides as mimetics of cytostatic steroidal saponins from Ornithogalum saindersiae and Galtonia candicans.  

PubMed

The synthesis of mimetic of the steroid saponins 1 and 2 was investigated. As a substitute for the complex 22-homo-23-nor-steroid moieties A and B in 1 and 2 diosgenin was introduced. The silyl protected thioorthoester 20 was successfully employed for glucosylation. After selective 2--deacetylation, the glucosylated diosgenyl acceptor 23 was rhamnosylated. The 4---methoxybenzoylated donor 12 gave only minor yields. By using the tri--benzoyl protected donor 15 the [small alpha]--rhamnopyranosyl-(1[rightward arrow]2)-[small beta]--glucopyranosyl-(1[rightward arrow]3[small beta])-diosgenin derivative 25 was obtained. PMID:14685308

Suhr, Rene; Pfefferkorn, Pascal; Weingarten, Saskia; Thiem, Joachim

2003-12-21

379

Characterization of sterol glucosyltransferase from Salinispora tropica CNB-440: potential enzyme for the biosynthesis of sitosteryl glucoside.  

PubMed

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

2013-04-10

380

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

2007-01-01

381

Regulators of cell division in plant tissues. XXX. Cytokinin metabolism in relation to radish cotyledon expansion and senescence  

Microsoft Academic Search

Kinetic studies of formation of glucosides of 6-benzylaminopurine (BAP) in excised radish cotyledons indicated that the 3-,\\u000a 7-, and 9-glucosides (N-glucosides) were each formed directly from BAP. The 7- and 9-glucosides of BAP and the 7-glucoside\\u000a of zeatin exhibited great stability in the cotyledons, but the 3-glucoside was converted to free BAP and to the 7- and 9-glucosides\\u000a of BAP.

D. S. Letham; B. I. Gollnow

1985-01-01

382

Phytochemical composition of polar fraction of Stachys germanica L. subsp. salviifolia (Ten.) Gams, a typical plant of Majella National Park.  

PubMed

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

2013-01-01

383

Boschniakia rossica prevents the carbon tetrachloride-induced hepatotoxicity in rat.  

PubMed

The present study was undertaken to investigate the hepatoprotective effect of Boschniakia rossica extract (BRE), rich in phenylpropanoid glycoside and iridoid glucoside, on CCl(4)-induced liver damage. Male Wistar rats were randomly divided into six groups of ten each. While the first group was maintained as normal control, groups II-VI were administered 0.5 ml/kg CCl(4) (model), 100mg/kg BRE plus CCl(4), 200mg/kg BRE plus CCl(4), 50mg/kg silymarin plus CCl(4) and 200mg/kg BRE, respectively. CCl(4) challenge not only elevated the serum marker enzyme activities and reduced albumin (ALB) level but also increased liver oxidative stress, as evidenced by elevated lipid hydroperoxide (LOOH) and malondialdehyde (MDA) concentrations, combined with suppressed potential of hepatic antioxidative defense system including superoxide dismutase (SOD), glutathione peroxidase (GPx) activities and reduced glutathione (GSH) content. Furthermore, serum tumor necrosis factor-? (TNF-?), hepatic nitrite level, inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein contents were elevated while cytochrome P450 2E1 (CYP2E1) expression and function were inhibited. Preadministration of BRE not only reversed the significant changes in serum toxicity markers, hepatic oxidative stress, xenobiotic metabolizing enzymes and proinflammatory mediators induced by CCl(4) but also restored liver CYP2E1 level and function. Interestingly, the protein expression of heme oxygenase-1 (HO-1) was further elevated by BRE treatment, which was markedly increased after CCl(4) challenge. These results demonstrate that BRE exhibits protective effect on CCl(4)-induced acute hepatic injury via, at least in part, reduced oxidative stress, suppressed inflammatory responses and induced HO-1 protein expression combined with improved CYP2E1 level and function in liver. PMID:19836219

Quan, Jishu; Yin, Xuezhe; Xu, Huixian

2011-01-01

384

A review of phytotherapy of gout: perspective of new pharmacological treatments.  

PubMed

The purpose of this review article is to outline plants currently used and those with high promise for the development of anti-gout products. All relevant literature databases were searched up to 25 March 2013. The search terms were 'gout', 'gouty arthritis', 'hyperuricemia', 'uric acid', 'xanthine oxidase (XO) inhibitor', 'uricosuric', 'urate transporter 1(URAT1)' and 'glucose transporter 9 (GLUT9)'. Herbal keywords included 'herbal medicine', 'medicinal plant', 'natural products', 'phytomedicine' and 'phytotherapy'. 'antiinflammatory effect' combined with the words 'interleukin-6 (IL-6)', 'interleukin-8 (IL-8)', 'interleukin-1beta (IL-1beta)', and 'tumor necrosis factor alpha (TNF-alpha)'. XO inhibitory effect, uricosuric action, and anti-inflammatory effects were the key outcomes. Numerous agents derived from plants have anti-gout potential. In in vitro studies, flavonoids, alkaloids, essential oils, phenolic compounds, tannins, iridoid glucosides, and coumarins show the potential of anti-gout effects by their XO inhibitory action, while lignans, triterpenoids and xanthophyll are acting through their anti-inflammatory effects. In animal studies, essential oils, lignans, and tannins show dual effects including reduction of uric acid generation and uricosuric action. Alkaloids reveal inhibit uric acid generation, show anti-inflammatory effects, or a combination of the two. Phenolic compounds and flavonoids inhibit uric acid production, show uricosuric anti-inflammatory effects. In the rare human studies, colchicine from Colchicum autumnale showed anti-inflammatory effects while for other plant extracts, although revealing anti-gout potential, further phytochemical investigations are needed to identify their active constituents. Besides, the plants which give antioxidant activities are much potent in the management of gout and need to be further investigated. The current review is a detailed discussion of the potential of medicinal plants for treatment of gout. PMID:24791587

Ling, X; Bochu, W

2014-04-01

385

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

2012-01-01

386

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

Microsoft Academic Search

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.

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

2007-01-01

387

Expression of the stilbene synthase (StSy) gene from grapevine in transgenic white poplar results in high accumulation of the antioxidant resveratrol glucosides  

Microsoft Academic Search

When present, stilbene synthase leads to the production of resveratrol\\u000a compounds, which are major components of the phytoalexin response\\u000a against fungal pathogens of the plant and are highly bioactive\\u000a substances of pharmaceutical interest. White poplar ( Populus alba L.)\\u000a was transformed with a construct containing a cDNA insert encoding\\u000a stilbene synthase from grapevine ( Vitis vinifera L.), under the control

Achille Giorcelli; Francesca Sparvoli; Fulvio Mattivi; Aldo Tava; Alma Balestrazzi; Urska Vrhovsek; Paolo Calligari; Roberto Bollini; Massimo Confalonieri

2004-01-01

388

Identification of benzophenone C-glucosides from mango tree leaves and their inhibitory effect on triglyceride accumulation in 3T3-L1 adipocytes.  

PubMed

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

2011-11-01

389

beta-D-Glucoside suppresses tumor necrosis factor-induced activation of nuclear transcription factor kappaB but potentiates apoptosis.  

PubMed

Mangiferin, a natural polyphenol is known to exhibit anti-inflammatory, antioxidant, and antiviral effects. However the molecular mechanism underlying these effects has not been well characterized. Because NF-kappaB plays an important role in these processes, it is possible that mangiferin modulates NF-kappaB activation. Our results show that mangiferin blocks tumor necrosis factor (TNF)-induced NF-kappaB activation and NF-kappaB-dependent genes like ICAM1 and COX2. The effect was mediated through inhibition of IKK activation and subsequent blocking of phosphorylation and degradation of IkappaBalpha. In addition, mangiferin inhibits TNF-induced p65 phosphorylation as well as translocation to the nucleus and also inhibits NF-kappaB activation induced by other inflammatory agents like PMA, ceramide, and SA-LPS. Mangiferin, similar to the other known antioxidants, NAC and PDTC, inhibits TNF-induced reactive oxygen intermediate (ROI) generation. Since intracellular glutathione (GSH) levels are known to modulate NF-kappaB levels, we measured the levels of GSH. Mangiferin enhances glutathione level by almost 2-fold more than other anti-oxidants, and at the same time it decreases the levels of GSSG and increases the activity of catalase. Depletion of GSH by buthionine sulfoximine led to a significant reversal of mangiferin effect. Hence mangiferin with its ability to inhibit NF-kappaB and increase the intracellular GSH levels may prove to be a potent drug for anti-inflammatory and antioxidant therapy. Mangiferin-mediated down-regulation of NF-kappaB also potentiates chemotherapeutic agent-mediated cell death, suggesting a role in combination therapy for cancer. PMID:15161907

Sarkar, Abira; Sreenivasan, Yashin; Ramesh, Govindarajan T; Manna, Sunil K

2004-08-01

390

Engineering the cytokinin-glucoside specificity of the maize ?-D-glucosidase Zm-p60.1 using site-directed random mutagenesis.  

PubMed

The maize ?-D-glucosidase Zm-p60.1 releases active cytokinins from their storage/transport forms, and its over-expression in tobacco disrupts zeatin metabolism. The role of the active-site microenvironment in fine-tuning Zm-p60.1 substrate specificity has been explored, particularly in the W373K mutant, using site-directed random mutagenesis to investigate the influence of amino acid changes around the 373 position. Two triple (P372T/W373K/M376L and P372S/W373K/M376L) and three double mutants (P372T/W373K, P372S/W373K and W373K/M376L) were prepared. Their catalytic parameters with two artificial substrates show tight interdependence between substrate catalysis and protein structure. P372T/W373K/M376L exhibited the most significant effect on natural substrate specificity: the ratio of hydrolysis of cis-zeatin-O-?-D-glucopyranoside versus the trans-zeatin-O-?-D-glucopyranoside shifted from 1.3 in wild-type to 9.4 in favor of the cis- isomer. The P372T and M376L mutations in P372T/W373K/M376L also significantly restored the hydrolytic velocity of the W373K mutant, up to 60% of wild-type velocity with cis-zeatin-O-?-D-glucopyranoside. These findings reveal complex relationships among amino acid residues that modulate substrate specificity and show the utility of site-directed random mutagenesis for changing and/or fine-tuning enzymes. Preferential cleavage of specific isomer-conjugates and the capacity to manipulate such preferences will allow the development of powerful tools for detailed probing and fine-tuning of cytokinin metabolism in planta. PMID:22079107

Filipi, Tomáš; Mazura, Pavel; Janda, Lubomír; Kiran, Nagavalli S; Brzobohatý, B?etislav

2012-02-01

391

Verbascoside and luteolin-5- O- ?- d-glucoside isolated from Halleria lucida L. exhibit antagonistic anti-oxidant properties in vitro  

Microsoft Academic Search

The purpose of this investigation was to determine and characterise the anti-oxidant activity of the methanol extract of the leaves of Halleria lucida utilizing the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay. The methanol extract of the leaves of H. lucida displayed promising anti-oxidant activity with an IC50 value of 8.49±0.12 ?g\\/ml and was subsequently subjected to activity-guided fractionation resulting in the isolation of a

Y. Frum; A. M. Viljoen; F. R. Van Heerden

2007-01-01

392

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

2013-01-01

393

Downregulation of a Pathogen-Responsive Tobacco UDP-Glc:Phenylpropanoid Glucosyltransferase Reduces Scopoletin Glucoside Accumulation, Enhances Oxidative Stress, and Weakens Virus Resistance  

Microsoft Academic Search

Plant UDP-Glc:phenylpropanoid glucosyltransferases (UGTs) catalyze the transfer of Glc from UDP-Glc to numerous substrates and regulate the activity of compounds that play important roles in plant defense against pathogens. We previously characterized two tobacco salicylic acid- and pathogen-inducible UGTs (TOGTs) that act very efficiently on the hydroxycoumarin scopoletin and on hydroxycinnamic acids. To identify the physiological roles of these UGTs

Julie Chong; Rachel Baltz; Corinne Schmitt; Roland Beffa; Bernard Fritig; Patrick Saindrenan; Aventis CropScience

2002-01-01

394

A Novel Sinorhizobium meliloti Operon Encodes an a-Glucosidase and a Periplasmic-Binding-Protein-Dependent Transport System for a-Glucosides  

Microsoft Academic Search

The most abundant carbon source transported into legume root nodules is photosynthetically produced sucrose, yet the importance of its metabolism by rhizobia in planta is not yet known. To identify genes involved in sucrose uptake and hydrolysis, we screened a Sinorhizobium meliloti genomic library and discovered a segment of S. meliloti DNA which allows Ralstonia eutropha to grow on the

LAURA B. WILLIS; GRAHAM C. WALKER

1999-01-01

395

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

2010-01-01

396

A 7-Deoxyloganetic Acid Glucosyltransferase Contributes a Key Step in Secologanin Biosynthesis in Madagascar Periwinkle[C][W][OPEN  

PubMed Central

Iridoids form a broad and versatile class of biologically active molecules found in thousands of plant species. In addition to the many hundreds of iridoids occurring in plants, some iridoids, such as secologanin, serve as key building blocks in the biosynthesis of thousands of monoterpene indole alkaloids (MIAs) and many quinoline alkaloids. This study describes the molecular cloning and functional characterization of three iridoid glucosyltransfeases (UDP-SUGAR GLYCOSYLTRANSFERASE6 [UGT6], UGT7, and UGT8) from Madagascar periwinkle (Catharanthus roseus) with remarkably different catalytic efficiencies. Biochemical analyses reveal that UGT8 possessed a high catalytic efficiency toward its exclusive iridoid substrate, 7-deoxyloganetic acid, making it better suited for the biosynthesis of iridoids in periwinkle than the other two iridoid glucosyltransfeases. The role of UGT8 in the fourth to last step in secologanin biosynthesis was confirmed by virus-induced gene silencing in periwinkle plants, which reduced expression of this gene and resulted in a large decline in secologanin and MIA accumulation within silenced plants. Localization studies of UGT8 using a carborundum abrasion method for RNA extraction show that its expression occurs preferentially within periwinkle leaves rather than in epidermal cells, and in situ hybridization studies confirm that UGT8 is preferentially expressed in internal phloem associated parenchyma cells of periwinkle species.

Asada, Keisuke; Salim, Vonny; Masada-Atsumi, Sayaka; Edmunds, Elizabeth; Nagatoshi, Mai; Terasaka, Kazuyoshi; Mizukami, Hajime; De Luca, Vincenzo

2013-01-01

397

The Effects of Plantago major on the Activation of the Neutrophil Respiratory Burst.  

PubMed

Plantago major is a common plant that grows worldwide in temperate zones and is found in fields, lawns, and on the roadsides. Its leaves and seeds have been used in almost all parts of the world for centuries as a wound healer, analgesic, antioxidant, and antibiotic, as well as an immune system modulator, antiviral, antifungal, and anti-inflammatory agent. Baicalein and aucubin are the two most biologically active components of P. major, and both have been shown to have antioxidant, anti-inflammatory, and anticancer properties. Neutrophils have a pivotal role in wound healing and inflammation. Their principal mechanism of host defense is the killing of pathogens via the production of reactive oxygen species (ROS). The aim of the present study was to determine the in vitro effects of P. major extract, baicalein, and aucubin on human neutrophil respiratory burst activity. The cytotoxicity of the agents was assessed by lactate dehydrogenase (LDH) assays. A standard luminol-dependent chemiluminescence (CL) assay was utilized to monitor the respiratory burst of the neutrophils after exposure to P. major extract and its two active ingredients, baicalein and aucubin. Three replicates per group were included in each of the three runs of the experiments and analysis of variance (ANOVA) was used for statistical analysis. P. major and baicalein were not toxic to the cells at any of the concentrations examined. Aucubin was toxic to the cells only at the highest concentration tested (P = 0.0081). However, genistein was toxic to the cells at all of the concentrations examined except for the lowest concentration of 16.9 ?g/ml (P = 0.985). P. major (-0.10 ± 0.11), aucubin (0.06 ± 0.16), baicalein (-0.10 ± 0.11), and genistein (-0.18 ± 0.07) all significantly (P < 0.0001) inhibited ROS production from the neutrophils. P. major extract inhibited neutrophil ROS production, as did aucubin and baicalein. Therefore, these components should be investigated further with relation to the regulation of destructive ROS production in conditions such as periodontal disease. PMID:24716188

Reina, Elaine; Al-Shibani, Nouf; Allam, Eman; Gregson, Karen S; Kowolik, Michael; Windsor, L Jack

2013-10-01

398

Constituents of Cissus quadrangularis.  

PubMed

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

2007-05-20

399

Polar constituents of celery seed  

Microsoft Academic Search

From the water-soluble portion of the methanol extract of celery seed (fruit of Apium graveolens L.) five sesquiterpenoid glucosides (celerioside A–E) and three phthalide glycosides (celephtalide A–C) were isolated together with six aromatic compound glucosides, two norcarotenoid glucosides and a lignan glucoside. Their structures were determined by spectral investigations.

Junichi Kitajima; Toru Ishikawa; Mitsuru Satoh

2003-01-01

400

Chemosystematics of some Indian members of the Acanthaceae  

Microsoft Academic Search

Fifty-eight taxa belonging to 3 subfamilies of Acanthaceae have been screened for leaf flavonoids, phenolic acids and aucubins.\\u000a The patterns of distribution of leaf phenolics among the taxa investigated suggest that: (i) there are 3 well-defined taxonomic\\u000a groups; (ii) the treatment of Thunbergiaceae as distinct from Acanthaceae (Sensu stricto) is justified; (iii) Nelsonioideae appears to be an intermediate link between

M Daniel; S D Sabnis

1987-01-01

401

Leaf chemistry and foliage avoidance by the thrips Frankliniella occidentalis and Heliothrips haemorrhoidalis in glasshouse collections.  

PubMed

Observational studies on foliage avoidance by the polyphagous thrips species Frankliniella occidentalis (Pergande) and Heliothrips haemorrhoidalis (Bouché) (Thysanoptera: Thripidae) identified six non-host species (Allagopappus dichotomus (Asteraceae), Gardenia posoquerioides (Rubiaceae), Plectranthus aff. barbatus, Plectranthus strigosus, Plectranthus zuluensis (Lamiaceae), and Sclerochiton harveyanus (Acanthaceae) among plants growing within a major glasshouse botanical collection. The effects of sequentially obtained acetone and aqueous methanol leaf extracts on mortality in first instar Frankliniella occidentalis were assessed. The acetone leaf extract of Sclerochiton harveyanus, which had the highest activity against the thrips, yielded four new iridoids, sclerochitonosides A-C, and sclerochitonoside B 4'-methyl ether. Mortality of F. occidentalis was increased on exposure to all four iridoids, and the most active iridoid was sclerochitonoside A (8-epiloganic acid 4'-hydroxyphenylethyl ester). Choice experiments demonstrated that this compound did not significantly deter H. haemorrhoidalis from treated leaf surfaces. The significance of iridoids in the defense mechanism of plants against thrips is discussed. PMID:21331569

Brown, Alison S Scott; Veitch, Nigel C; Simmonds, Monique S J

2011-03-01

402

Cardiac stimulant activity of bark and wood of Premna serratifolia  

Microsoft Academic Search

Premna serratifolia Lin., (Verbenaceae) contains alkaloids and iridoid glycoside and is believed to prevent cardiovascular disease. The stem- bark and stem-wood were extracted with 95% ethanol and distilled water. These extracts were screened for their effects by \\

Rekha Rajendran; Suseela L; Meenakshi Sundaram R; Saleem Basha N

2008-01-01

403

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

2005-01-01

404

Secoiridoid constituents from the fruits of Ligustrum lucidum.  

PubMed

Two secoiridoid glucosides, lucidumosides A and B, as well as six known glucosides, oleoside dimethyl ester, ligustroside, oleuropein, nuezhenide, isonuezhenide, and neonuezhenide, were isolated from the fruits of Ligustrum lucidum. Their structures were elucidated by spectroscopic methods. PMID:11249095

He, Z D; Dong, H; Xu, H X; Ye, W C; Sun, H D; But, P P

2001-02-01

405

Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase  

Microsoft Academic Search

Lactase phlorizin hydrolase (LPH; EC 3.2.1.62) is a membrane-bound, family 1 ?-glycosidase found on the brush border of the mammalian small intestine. LPH, purified from sheep small intestine, was capable of hydrolysing a range of flavonol and isoflavone glycosides. The catalytic efficiency (kcat\\/Km) for the hydrolysis of quercetin-4?-glucoside, quercetin-3-glucoside, genistein-7-glucoside and daidzein-7-glucoside was 170, 137, 77 and 14 (mM?1 s?1)

Andrea J Day; Juan C D??az; Paul A Kroon; Russell Mclauchlan; Craig B Faulds; Geoff W Plumb; Michael R. A Morgan; Gary Williamson

2000-01-01

406

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.  

PubMed

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

2013-03-15

407

Hydrogen-bond network in cyclodecaamylose hydrate at 20 K; neutron diffraction study of novel structural motifs band-flip and kink in alpha-(1-->4)-D-glucoside oligosaccharides.  

PubMed

A single-crystal neutron diffraction study of cyclodecaamylose (CA10) was carried out at 20 K. CA10 crystallizes with 27.18 water molecules [(C(6)H(10)O(5))(10).27.18H(2)O] in space group C2 with unit-cell constants a = 29.31 (5), b = 9.976 (10), c = 19.34 (2) A, beta = 121.07 (2) degrees. The asymmetric unit contains a half molecule of CA10 and 13.59 water molecules, the other half being related by a crystallographic twofold rotation axis. All H atoms except two water H atoms could be located from difference neutron-density maps; structure refinement converged at R = 0.635. Two of the five CH(2)-O6 groups and one of the 15 O2, O3 hydroxyl groups of CA10 are twofold orientationally disordered. A total of 13.59 water molecules in the asymmetric unit are distributed over 23 positions; 20 of which are in the CA10 cavity, and the other three occupy intermolecular interstices. Of the 123 symmetry-independent hydrogen bonds, 25 (= 20%) are three-centered and 7 (= 6%) are four-centered. Water molecules and O-H groups of CA10 form an extended network with cooperative O-H...O-H...O-H hydrogen bonds. They are arranged in 11 polygons with three, four, five, six and eight O-H bonds and in homodromic, antidromic and heterodromic arrangements. Nine polygons are located within the cavity and the others are outside. PMID:11717483

Imamura, K; Nimz, O; Jacob, J; Myles, D; Mason, S A; Kitamura, S; Aree, T; Saenger, W

2001-12-01

408

Distribution of free and glycosylated sterols within Cycas micronesica plants  

Microsoft Academic Search

Flour derived from Cycas micronesica seeds was once the dominant source of starch for Guam's residents. Cycad consumption has been linked to high incidence of human neurodegenerative diseases. We determined the distribution of the sterols stigmasterol and ?-sitosterol and their derived glucosides stigmasterol ?-d-glucoside and ?-sitosterol ?-d-glucoside among various plant parts because they have been identified in cycad flour and

Thomas E. Marler; Christopher A. Shaw

2010-01-01

409

Furanoflavonoid glycosides from Pongamia pinnata fruits.  

PubMed

Pongamia pinnata fruits afforded three new furanoflavonoid glucosides, pongamosides A-C (1-3), and a new flavonol glucoside, pongamoside D (4). The structures of these compounds were established on the basis of spectroscopic studies. This is the first time that furanoflavone glucosides have been found as naturally occurring compounds. PMID:15081295

Ahmad, Ghufran; Yadav, Prem P; Maurya, Rakesh

2004-04-01

410

Quercetin triglycoside from Capparis spinosa.  

PubMed

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'"-alpha-L-rhamnosyl-6"-beta-D-glucosyl]-beta-D-glucoside (1). PMID:11449469

Sharaf, M; el-Ansari, M A; Saleh, N A

2000-02-01

411

Using reversed phase high performance liquid chromatography to study the complexation of anthocyanins with ?-cyclodextrin  

NASA Astrophysics Data System (ADS)

It is shown by means of reversed phase high performance liquid chromatography (RP HPLC) with mobile phases containing additions of ?-cyclodextrin that 5-glucosides of cyanidin and pelargonidin form stronger inclusion complexes than 3-glucosides; this is explained by the steric interference of the glucoside radical.

Deineka, V. I.; Lapshova, M. S.; Deineka, L. A.

2014-06-01

412

Two new flavonoids from Origanum vulgare  

Microsoft Academic Search

In addition to the major constituents apigenin, luteolin, salvagenin, cirsimartin, diosmetin, desmethoxycentauridin, 5-hydroxy-6,7,3?,4?-tetramethoxy-abigenin, apigenin 7-O-glucoside, luteolin 7-O-glucoside, luteolin 7-O-glucoside-6??-methylester, two new flavonoids were isolated, in minor concentration, and identified as luteolin 7-O-?-L-rhamnoside-4?-O-?-D-glucoside and quercetin 3-O-?-D-glucoside-4?-O-?-L-rhamnoside from the methanolic extract of Origanum vulgare L. The structures were determined by conventional analytical methods and confirmed by MS and NMR spectral analysis.

Usama W. Hawas; S. K. El-Desoky; S. A. Kawashty; M. Sharaf

2008-01-01

413

Quantification of flavonoids in black rice by liquid chromatography-negative electrospray ionization tandem mass spectrometry.  

PubMed

Systematic identification and structural characterization of flavonoids and their glycosides in bran extracts of seven Thai black rice varieties were performed by sequential uses of reversed-phase HPLC with a photodiode array detector and a combined electrospray ionization tandem mass spectrometer. Eleven flavonoids were detected, and six of these were found for the first time in rice bran. These were taxifolin-7-O-glucoside, myricetin-7-O-glucoside, isorhamnetin-3-O-acetylglucoside, isorhamnetin-7-O-rutinoside, 5,6,3',4',5'-pentahydroxyflavone-7-O-gluc