Showing papers on "Glucoside published in 2007"
01 Jan 2007
TL;DR: This chapter gives a comprehensive coverage toSalicylic acid, a natural product of phenylpropanoid metabolism, which has direct involvement in plant growth, thermogenesis, flower induction and uptake of ions.
Abstract: Salicylic acid (SA) is a phenolic derivative, distributed in a wide range of plant species. It is a natural product of phenylpropanoid metabolism. Decarboxylation of transcinnamic acid to benzoic acid and its subsequent 2-hydroxylation results to SA. It undergoes metabolism by conjugating with glucose to SA glucoside and an ester. SA has direct involvement in plant growth, thermogenesis, flower induction and uptake of ions. It affects ethylene biosynthesis, stomatal movement and also reverses the effects of ABA on leaf abscission. Enhancement of the level of chlorophyll and carotenoid pigments, photosynthetic rate and modifying the activity of some of the important enzymes are other roles assigned to SA. This chapter gives a comprehensive coverage to all the above aspects.
178 citations
TL;DR: In this article, high performance liquid chromatography with diode array detection (HPLC-DAD) was performed to characterize the presence of phenolic compounds in Andean purple corn.
170 citations
TL;DR: In this paper, Naringenin, kaempferol and methanol extracts were found to be active as radical-scavengers with IC 50 values of 052mM, 815μM, 107 mM, 358 mm, 721 mM and 659 mM.
127 citations
TL;DR: A microwave-assisted extraction method has been applied for the first time to the extraction of the main lignan, secoisolariciresinol diglucoside (SDG), and the two most concentrated hydroxycinnamic acid glucosides in flaxseed and the results demonstrated that MAE was more effective in terms of both yield and time consumption.
Abstract: A microwave-assisted extraction (MAE) method has been applied for the first time to the extraction of the main lignan, secoisolariciresinol diglucoside (SDG), and the two most concentrated hydroxycinnamic acid glucosides in flaxseed. The effects of microwave power, extraction time and alkaline treatment were investigated. It was shown that a 3 min MAE resulted in an SDG content of 16.1+/-0.4 mg/g, a p-coumaric acid glucoside content of 3.7+/-0.2 mg/g and a ferulic acid glucoside content of 4.1+/-0.2 mg/g. These values were compared with those obtained using conventional extraction methods and the results demonstrated that MAE was more effective in terms of both yield and time consumption.
118 citations
TL;DR: Biotransformation of piceid in Polygonum cuspidatum to resveratrol by Aspergillus oryzae was investigated and it was found that biotransformation is a better method to increase the yield of resver atrol because of its high yield and mild conditions.
Abstract: Biotransformation of piceid in Polygonum cuspidatum to resveratrol by Aspergillus oryzae was investigated in this study. Resveratrol is widely used in medicine, food, and cosmetic because of its pharmacological properties. However, it has a much lower content in plants compared with its glucoside piceid, which has a much lower bioavailability. Traditionally, the aglycone is acquired by acid or enzymatic hydrolysis of its glucoside, but the violent condition and the acid pollution in hydrolytic reaction and the high cost of the enzyme limit their industrial development. In this paper, fermentation of P. cuspidatum by A. oryzae was successfully performed, during which, piceid was converted to resveratrol with the highest yield of trans-resveratrol 1.35%, 3.6 times higher than that obtained from raw herb by microwave-assisted extraction. Scale-up production was also performed and the yield of trans-resveratrol was 3.1 times higher after 24 h incubation. Therefore, biotransformation is a better method to increase the yield of resveratrol because of its high yield and mild conditions.
83 citations
TL;DR: High performance liquid chromatography method has been developed for simultaneous quantification of limonoid aglycones and glucosides on a reversed phase C18 column using a binary solvent system, coupled with diode array detector, andLimonin and limonin glucoside were found to be the predominant limonoids aglycone and glucose in all tested samples.
66 citations
TL;DR: A novel transglycosylation reaction by a recombinant sucrose phosphorylase from Bifidobacterium longum was used to produce a stable l-ascorbic acid derivative.
Abstract: 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-α-d-glucopyranosyl-l-ascorbic acid by LC-MS/MS analysis.
63 citations
TL;DR: A new compound resulting from the oxidative degradation of maldivin 3-O-glucoside under acid conditions was detected in a wine model solution stored under 90 and 25 degrees C.
Abstract: A new compound resulting from the oxidative degradation of maldivin 3-O-glucoside under acid conditions was detected in a wine model solution stored under 90 and 25 degrees C. It was isolated by semipreparative HPLC, and its structure was elucidated by UV-vis spectra, mass spectrometry (LC/MS), and NMR spectroscopy (1-D and 2-D). The compound was identified as 8-beta-d-glucopyranosyl-2,4-dihydroxy-6-oxo-cyclohexa-2,4-dienyl acetic acid (anthocyanone A), which results from nucleophilic attack of hydrogen peroxide to maldivin 3-O-glucoside through a Baeyer-Villiger oxidation followed by other oxidations steps.
56 citations
TL;DR: In this paper, citrus limonoids and aglycones were extracted from citrus seeds and the structures of the isolated compounds were confirmed by NMR spectra, and they were tested for O-dealkylase and hydroxylase activities of human cytochrome P450 (CYP) isoenzymes.
Abstract: Recent studies demonstrated that citrus limonoids and flavonoids possess numerous health promoting properties. In the present study, glucosides of limonoids and flavonoids were purified from citrus molasses and limonoid aglycones from citrus seeds. Glucosides were separated on styrene (divinylbenzene), Q-sepharose resins with increasing concentration of sodium chloride. A pH-dependent cold precipitation was carried out for the isolation of naringin in large quantity. Major aglycones such as limonin and nomilin were isolated from seeds by direct crystallization and minor limonoids were purified by vacuum liquid chromatography. The structures of the isolated compounds were confirmed by NMR spectra. Individual limonoids were tested for O-dealkylase and hydroxylase activities of human cytochrome P450 (CYP) isoenzymes such as CYP1A2, CYP1B1, CYP3A4 and CYP19, using ethoxyresorufin, methoxyresorufin and dibenzylfluorescein as substrates. Partial to high inhibition of CYPs was observed in dose-dependent assays. Significant (P < 0.001) reductions in enzyme activities were observed with purified compounds above 2 µmol. Kinetic analyses indicated that limonin glucoside inhibited CYP19 competitively (IC50, 7.1 µ mol L−1), whereas Nomilinic acid glucoside inhibited it noncompetitively (IC50, 9.4 µ mol−1). Nomilinic acid glucoside was the most potent limonoid, with an overall IC50 of < 10 µ mol, for all the enzymes tested. The differential inhibition of CYPs can be ascribed to structural variations of the limonoid nucleus. Limonoid inhibition of key CYPs involved in carcinogenesis supports growing evidence that citrus limonoids act as anticancer agents. Copyright © 2007 Society of Chemical Industry
51 citations
TL;DR: In this paper, a bioassay-guided fractionation of 95% EtOH extract from the roots of Dipsacus asper lead to the isolation of some phenolic acids (caffeic acid, 2,6-dihydroxycinnamic acid, vanillic acid) as the major active components, and five new iridoid glucoside dimers.
Abstract: Bioassay-guided fractionation of 95% EtOH extract from the roots of Dipsacus asper lead to the isolation of some phenolic acids (caffeic acid, 2,6-dihydroxycinnamic acid, vanillic acid, 2′-O-caffeoyl-D-glucopyranoside ester, and caffeoylquinic acid) as the major active components, and five new iridoid glucoside dimers (1—5) and one new iridoid glucoside monomer (6), other known iridoid glycosides loganin, cantleyoside, triplostoside A, lisianthioside, 6′-O-β-D-apiofuranosyl sweroside, as well as triterpenoids oleanic acid and akebiasaponin D. The structures of new compounds 1—6 were determined as dipsanosides C (1), D (2), E (3), F (4), G (5), and 3′-O-β-D-glucopyranosyl sweroside (6) by spectroscopic, including 1D and 2D NMR techniques, and chemical methods.
38 citations
TL;DR: Arbutin glucoside (4-hydroxyphenyl β-isomaltoside) exhibited slower effects on 1,1-diphenyl-2-picrylhydrazyl radical scavenging and similar effects on tyrosinase inhibition, and increased inhibitory effect on matrix metalloproteinase-1 production induced by UVB than arbutin.
Abstract: Two arbutin glucosides were synthesized via the acceptor reaction of a glucansucrase from Leuconostoc mesenteroides B-1299CB with arbutin and sucrose. The glucosides were purified by Bio-gel P-2 column chromatography and high-performance liquid chromatography, and the structures were elucidated as 4-hydroxyphenyl β-isomaltoside (arbutin-G1), 4-hydroxyphenyl β-isomaltotrioside (arbutin-G2), according to the results of 1H, 13C, heteronuclear single-quantum coherence, 1H-1H COSY, and heteronuclear multiple-bond correlation analyses. Arbutin glucoside (4-hydroxyphenyl β-isomaltoside) exhibited slower effects on 1,1-diphenyl-2-picrylhydrazyl radical scavenging and similar effects on tyrosinase inhibition, and increased inhibitory effect on matrix metalloproteinase-1 production induced by UVB than arbutin.
TL;DR: A rapid metabolisation of coniferin into lignans and neolignans is suggested and the capacity of flax cells to operate different types of couplings is indicated.
TL;DR: In this article, the anti-oxidant activity of the methanol extract of the leaves of Halleria lucida utilizing the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay was determined and characterised.
TL;DR: Two new phenyldihydronaphthalene-type lignan glucosides, vitecannasides A and B, were isolated from the fruit of Vitex cannabifolia Sieb and exhibited stronger activity than that of l-cysteine.
Abstract: Two new phenyldihydronaphthalene-type lignan glucosides, vitecannasides A (1) and B (2) were isolated from the fruit of Vitex cannabifolia Sieb. et. Zucc. (Verbenaceae) along with the six known lignan derivatives (3-8), four known iridoid glucosides (9-12), three known flavonoids (13-15), and one known phenylbutanone glucoside (16). Their chemical structures were determined on the basis of spectroscopic data as well as chemical evidence. The scavenging effect of 1, 2, and 11-16 on the stable free radical 1,1-diphenyl-2-picrylhydrazyl was examined. Compounds 1, 2, 14, and 15 exhibited stronger activity than that of L: -cysteine. Especially, 14 and 15 showed more potent activity than that of alpha-tocopherol.
TL;DR: Proximate values of the protein, oil and carbohydrate content of the seeds suggest that they may be adequate for the formulation of animal feeds, and the mineral elements present suggest that the seeds could contribute partially to the overall daily intake of these elements, subject to knowledge of the levels of the possible toxic substances.
Abstract: The seeds of the fruits of some wild plants; Cassipourea congoensis (Tunti), Nuclea latifolia (Luzzi), Deterium microcarpum (Tallow), Balanites aegytiaca (Betu), and Gemlin arborea (Melina) were analysed to establish their proximate compositions and the physico-chemical characteristics of the oils. The physico-chemical characteristics measured include saponification value (SV), iodine value (IV), peroxide value (PV), acid value (AV) and percentage free fatty acid (%FFA). Refractive index was the physical parameter measured. The iodine values of the oils were not greater than 88 g/100 g but the saponification values were in the range 122 ± 0.14 to 201 ± 0.05 mg KOH. Proximate values of the protein, oil and carbohydrate content of the seeds suggest that they may be adequate for the formulation of animal feeds. The mineral elements present also suggest that the seeds could contribute partially to the overall daily intake of these elements, subject to knowledge of the levels of the possible toxic substances. The vitamins (A and C) found to be present in the seeds are low, though could alleviate the symptoms associated with these vitamins. The cyanogenetic glucoside contents in the seeds were analyzed to establish their proximate composition. Qualitative and quantitative chemical analysis showed that all the samples studied contain hydrogen cyanide (HCN) in the form of cyanogenetic glucoside in quantities varying from 2.51 ± 0.31 mg/100g of dried sample for D. microcarpum to 3.75 ± 0.02 mg/100g for G. arborea. The aglycone for all the glucoside detected was found to be benzaldehyde.
TL;DR: In this article, a reversed-phase HPLC analysis of methanol extract of the seeds of Centaurea montana afforded a flavanone, montanoside (4), six epoxylignans, berchemol (7), berchemolate 4′- O -β-d-glucoside (5), pinoresinol (10), pinoreinol 4- O −β- d -glucose (8), pinOREINOL 4,4′-di-O -β -d -glocoside
Abstract: Reversed-phase HPLC analysis of the methanol extract of the seeds of Centaurea montana afforded a flavanone, montanoside ( 4 ), six epoxylignans, berchemol ( 7 ), berchemol 4′- O -β- d -glucoside ( 5 ), pinoresinol ( 10 ), pinoresinol 4- O -β- d -glucoside ( 8 ), pinoresinol 4,4′-di- O -β- d -glucoside ( 6 ), pinoresinol 4- O -apiose-(1→2)-β- d -glucoside ( 9 ), two quinic acid derivatives, trans -3- O - p -coumaroylquinic acid ( 1 ), cis -3- O - p -coumaroylquinic acid ( 2 ), and eight indole alkaloids, tryptamine ( 3 ), N -(4-hydroxycinnamoyl)-5-hydroxytryptamine ( 11 ), cis - N -(4-hydroxycinnamoyl)-5-hydroxytryptamine ( 12 ), centcyamine ( 16 ), cis -centcyamine ( 17 ), moschamine ( 13 ), cis -moschamine ( 14 ) and a dimeric indole alkaloid, montamine ( 15 ). While the structures of two new compounds, montanoside ( 4 ) and montamine ( 15 ), were established unequivocally by UV, IR, MS and a series of 1D and 2D NMR analyses, all known compounds were identified by comparison of their spectroscopic data with literature data. The antioxidant properties of these compounds were assessed by the DPPH assay, and their toxicity towards brine shrimps and cytotoxicity against CaCo-2 colon cancer cells were evaluated by the brine shrimp lethality and the MTT cytotoxicity assays, respectively. The novel dimer, montamine ( 15 ), showed significant in vitro anticolon cancer activity (IC 50 =43.9 μM) while that of the monomer, moschamine ( 13 ), was of a moderate level (IC 50 =81.0 μM).
TL;DR: From the aerial parts of Anthemis tinctoria L. pallida DC, one new cyclitol glucoside, conduritol F-1-O-(6′-O-E-p-caffeoyl)-β-d-glucopyranoside, has been isolated together with four flavonoids, nicotiflorin, which showed a strong scavenging effect in the DPPH radical assay.
Abstract: From the aerial parts of Anthemis tinctoria L. subsp. tinctoria var. pallida DC. (Asteraceae), one new cyclitol glucoside, conduritol F-1-O-(6'-O-E-p-caffeoyl)-beta-D-glucopyranoside (1), has been isolated together with four flavonoids, nicotiflorin (2), isoquercitrin (3), rutin (4) and patulitrin (5). The structures of the isolated compounds were established by means of NMR, MS, and UV spectral analyses. Methanolic extract and pure isolated compounds were examined for their free radical, scavenging activity, using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free stable radical, and for their inhibitory activity toward soybean lipoxygenase, using linoleic acid as substrate. Compounds 1 and 5 showed a strong scavenging effect in the DPPH radical assay. In addition 5 also exhibited high inhibitory activity on soybean lipoxygenase.
Patent•
05 Apr 2007TL;DR: In this paper, a method for producing isolated limonoid glucoside compounds is described, which includes extracting a quantity of defatted citrus seed powder with a solvent, filtering the resulting extract to yield a particle free extract and concentrating the extract to produce a concentrate.
Abstract: A method for producing isolated limonoid glucoside compounds is disclosed which includes extracting a quantity of defatted citrus seed powder with a solvent, filtering the resulting extract to yield a particle free extract and concentrating the particle free extract to yield a concentrate. The concentrate is loaded onto an ion exchange column that is coupled to an adsorption column. The ion exchange column is washed with deionized water and the eluate from the ion exchange column is passed through the adsorption column. The adsorption column is then eluted using a series of mobile phases in which composition of each successive mobile phase is graduated. A series of eluate fractions are collected from the adsorption column and concentrated to produce isolated crystals of limonin glucoside, deacetyl nomilinic acid glucoside and isoobacunoic acid glucoside.
TL;DR: A method for estimating the total limonoid aglycone and glucoside concentrations in Citrus samples in terms of limonin andLimonin glucosides equivalents is presented.
Abstract: A method for estimating the total limonoid aglycone and glucoside concentrations in Citrus samples in terms of limonin and limonin glucoside equivalents is presented. The method consists of extraction followed by colorimetric quantification. The colorimetric quantification was based on the formation of red to orange colored derivatives resulting from the treatment of limonin, limonin glucoside, or a fruit extract with 4-(dimethylamino)benzaldehyde (DMAB) in the presence of perchloric and acetic acids. Absorbance maxima for the limonin and limonin glucoside derivatives were found to be 470 and 503 nm, respectively. The influence of DMAB concentration, reaction time, and solvent composition on color development and sensitivity were investigated and optimal assay conditions established. With a microplate format under these conditions, the limits of detection and quantification were determined to be 0.25 and 0.50 microg/mL for limonin and 0.50 and 1.0 microg/mL for limonin glucoside.
TL;DR: The GC-MS identification of several abundant long-chain aliphatic n-alkyl caffeates, together with other phydroxycinnamic acid esters, in the dichloromethane extracts of the bark of Acacia dealbata and A. melanoxylon, is reported.
Abstract: The GC-MS identification of several abundant long-chain aliphatic n-alkyl caffeates, together with other phydroxycinnamic acid esters, in the dichloromethane extracts of the bark of Acacia dealbata and A melanoxylon, is reported In addition, the unambiguous differentiation between two delta7-steryl glucosides (namely, spinasteryl glucoside and dihydrospinasteryl glucosides) and the homologous delta5-steryl glucosides was achieved based on the EI-MS fragmentation features of their trimethylsilyl derivatives
TL;DR: Calligonolides A and B, two new butanolides, and a new steroidal ester, 3, have been isolated from the whole plant of Calligonum polygonoides together with four known compounds, tetracosan‐4‐olide, β‐sitosterol and its glucoside, and ursolic acid.
Abstract: Calligonolides A (1) and B (2), two new butanolides, and a new steroidal ester, 3, have been isolated from the whole plant of Calligonum polygonoides, together with four known compounds, tetracosan-4-olide, beta-sitosterol and its glucoside, and ursolic acid. Their structures were elucidated by spectroscopic and mass-spectrometric studies. Compounds 1-3 showed moderate inhibitory potential against lipoxygenase from soybean.
TL;DR: In this article, a new iridoid glucoside, lamalbidic acid (7), was isolated from Eremostachys moluccelloides and its choline salt 7a together with six known iridoids, including 5-deoxysesamoside (1), 6β-hydroxy-7-epiloganin (2), lamalbide (3), shanzhiside methyl ester (4), sesamosaide (5), and 5deoxypulchelloside I (6).
Abstract: From the aerial parts of Eremostachys moluccelloidesBunge, a new iridoid glucoside, lamalbidic acid (7), was isolated as its choline salt 7a together with six known iridoid glucosides, 5-deoxysesamoside (1), 6β-hydroxy-7-epiloganin (2), lamalbide (3), shanzhiside methyl ester (4), sesamoside (5), and 5-deoxypulchelloside I (6). The structures of 7a and 7 (obtained from 7a) were elucidated by spectroscopic (UV, IR, 1D- and 2D-NMR, and ESI-MS) methods.
TL;DR: A new glucoside ester, named flacourside, has been isolated together with known methyl 6-O-(E)-p-coumaroyl glucopyranoside and 6 O(E)-m-p-Coumaroysl-β-d-glucopyranose from the n-butanol extract of fruit juice of the Flacourtia indica as mentioned in this paper.
TL;DR: A yeast strain for alkyl glucoside synthesis is constructed by genetically inducing the display of β-glucosidase 1 (BGL1) from the filamentous fungus Aspergillus aculeatus No.
Abstract: For efficient alkyl glucoside production from cellooligosaccharides, we constructed a yeast strain for alkyl glucoside synthesis by genetically inducing the display of β-glucosidase 1 (BGL1) from the filamentous fungus Aspergillus aculeatus No. F-50 on the cell surface. The localization of BGL1 on the cell surface was confirmed by immunofluorescence microscopy. The yeast strain displaying BGL1 catalyzed alkyl glucoside synthesis from p-nitrophenyl β- d -glucoside and primary alcohols. The highest yield of alkyl glucoside was 27.3% of the total sugar. The substrate specificities of the BGL1-displaying yeast strain and almond β-glucosidase were compared using different-chain-length cellooligosaccharides. The BGL1-displaying yeast showed efficient alkyl glucoside production from not only glucose but also cellohexaose. This yeast is applicable as a whole-cell biocatalyst for alkyl glucoside production from cellulose hydrolysates.
TL;DR: In this paper, α-glucosidase assisted transglycosylation between arbutin as acceptor and sucrose as donor molecules, respectively, was used to synthesize 4.4-hydroxyphenyl-β-isomaltoside.
TL;DR: Further extensive isolation work on the 1-BuOH-soluble fraction of a MeOH extract of Tricalysia dubia afforded five new ent-kaurane glucosides and one new labdane glucOSide, together with a known megastigmane glucoside, sammangaoside B (1), and monoterpene glucOSides (2, 3).
Abstract: Further extensive isolation work on the 1-BuOH-soluble fraction of a MeOH extract of Tricalysia dubia afforded five new ent-kaurane glucosides (4-8) and one new labdane glucoside (9), together with a known megastigmane glucoside, sammangaoside B (1), and monoterpene glucosides (2, 3). The structures of the new compounds were elucidated by analyses of one- and two-dimensional NMR spectroscopic data. The absolute configuration of the 9-position of sammangaoside B was revised to S and its total stereochemistry was established by the modified Mosher's method.
TL;DR: The structure of the new compound was determined to be β-sitosterol glucoside-3’-0-hexacosanoicate based on chemical and spectroscopic analyses and it was found to exhibit a significant inhibitory effect on the complement system activated by the classical pathway.
Abstract: A novel acylated sterol glucoside (1) along with four known compounds, β-amyrin acetate (2), 3β,24-dihydroxytaraxer-14-ene (3), cleomiscosin A (4), and deomiscosin C (5), were isolated from the leaf and twig ofAcer okamotoanum Nakai (Aceraceae). The structure of the new compound was determined to be β-sitosterol glucoside-3’-0-hexacosanoicate based on chemical and spectroscopic analyses. In addition, the novel compound was found to exhibit a significant inhibitory effect (IC50 value of 0.2 (μM) on the complement system activated by the classical pathway.
TL;DR: The work at hand describes the production of the zearAlenone (ZON) metabolites zearalenone-4-glucoside, a-zearalinol- 4-gl Sucoside (oc-ZOL-4G) and ß-zEARalenol-4 -glucOSide (ß-Z OL-4g) and the identity and purity of the substances were confirmed by13C-and1H-N
Abstract: The work at hand describes the production of the zearalenone (ZON) metabolites zearalenone-4-glucoside (ZON-4G), a-zearalenol-4-glucoside (oc-ZOL-4G) and s-zearalenol-4-glucoside (s-ZOL-4G). In a first step a genetically modified yeast strain, expressing theArabidopsis thaliana UDP-glu-cosyltransferase UGT73C6, was treated with ZON to produce ZON-4G. The substance was purified by solid phase extraction and subsequent reversed phase preparative HPLC prior to the reduction with sodium borohydride to yield 0C-ZOL-4G and s-ZOL-4G. The identity and purity of the substances were confirmed by13C-and1H-NMR as well as by HPLC-UV. In total, 50 mg of ZON were used to produce 5 mg of a-ZOL-4G with a purity of 98%, 6 mg of s-ZOL-4G with a purity of 99% and 5 mg of ZON-4G with a purity of 99%.
TL;DR: A new complex tannin, cowaniin was isolated from the leaves and stems of Cowania mexicana (Rosaceae), and its structure was characterized as novel C-glucosidic tann in dimer linked through (+)-catechin on the basis of spectral and chemical evidence.
Abstract: A new complex tannin, cowaniin (1) was isolated from the leaves and stems of Cowania mexicana (Rosaceae), and its structure was characterized as novel C-glucosidic tannin dimer linked through (+)-catechin on the basis of spectral and chemical evidence. The inhibitory effect on activation of the Epstein-Barr virus early antigen was assessed for cowaniin. Six known polyphenols and related compounds, including a nitrile glucoside, purshianin, were also characterized.