Showing papers on "Glucoside published in 1993"
TL;DR: High incorporations of deoxyloganic acid as well as of loganic acid and its 7-epimer were obtained, strongly implying that 7-ketologanic acid is an intermediate in the biosynthesis of oleosides.
84 citations
TL;DR: In this paper, four new phenylpropanoid glycosides, (+)-cyclo-olivil 6- O -β-d -glucoside, (7 S,8 R,7′ S,8′ R )-neo-OLivil 9′- O −β- d -gucosides, sinapyl alcohol 1,3′-di-O -β -d −glucopyranoside and coniferyl alcohol 1.
71 citations
TL;DR: Results indicate that GSH, cysteine, and glucose conjugation have a major role in the metabolic detoxification and selectivity mechanism of fenoxaprop-ethyl in grass species.
70 citations
TL;DR: A new carbazole alkaloid, clausine-L together with 11 known compounds, safrole, glutinol, 132-hydroxy(132-R)-pheophytin-a, methyl pheophobide-a and scopoletin, steroidal glycoside [β-sitosteryl glucoside +stigmasteryl glucosides], 2-methoxy-4-(2-propenyl)phenyl-β-d-glucoside, 2,6-dimethoxy, 4-(2
50 citations
TL;DR: The glycosidation of (+)catechin, which has five hydroxyl groups with cyclodextrin glucanotransferase (CGTase) and soluble starch has been studied and this glucoside noncompetitively inhibited the activity of tyrosinase from mushroom, but didn’t inhibit that from mouse melanoma.
Abstract: The glycosidation of (+)catechin, which has five hydroxyl groups with cyclodextrin glucanotransferase (CGTase, EC 2.4.1.19) and soluble starch has been studied. One of the transfer products was purified and its structure was determined to be (+)catechin 3ʹ-0-α-D-glucopyranoside. This glucoside noncompetitively inhibited the activity of tyrosinase from mushroom, IC50 being 5.8 mM, but didn’t inhibit that from mouse melanoma. In contrast, arbutin (hydroquinone-0-β-D-glucopyranoside) inhibited both tyrosinases.
48 citations
TL;DR: In this paper, a chemo-enzymatic approach to some 6-O-(3-arylprop-2-enoyl) derivatives of the glucoside isoquercitrin (2a) was explored to overcome the inability to directly introduce these acyl moieties by an enzyme-catalyzed reaction of 2a with the corresponding activated esters.
Abstract: A chemo-enzymatic approach to some 6″-O-(3-arylprop-2-enoyl) derivatives of the flavonol glucoside isoquercitrin (2a) was explored to overcome the inability to directly introduce these acyl moieties by an enzyme-catalyzed reaction of 2a with the corresponding activated esters This new approach was based on the regioselective introduction of a methyl malonate residue at the CH2OH of the sugar moiety by catalysis with the protease subtilisin (→ 22a) The mixed diester 22a was then subjected to chemoselective hydrolysis of the methoxycarbonyl function by another enzyme, biophine esterase (→ 23) Finally, the malonic monoester 23 was reacted in a Knoevenagel-type condensation with benzaldehyde, 4-hydroxybenzaldehyde, or 4-hydroxy-3-methoxybenzaldehyde to afford the target 6″-O-(3-arylprop-2-enoyl) isoquercitrins 2b–d
44 citations
TL;DR: Two new compounds were elucidated by spectroscopic means as 1-β- d -gluco pyranosyloxy-3-methoxy- 5-hydroxybenzene and (2R,3R)-7,4′-dihydroxy-5,3′,5′-trimethoxyflavan 3-O-gallate, were isolated from Sedum sediforme flowers as discussed by the authors.
42 citations
TL;DR: In this paper, a simple aliphatic glucoside, 3-(R)-3-β-d -glucopyranosyloxybutanolide (kinsenoside) with its congeners and a heterocyclic aromatic glucosides, β- d -glocopyranoyl-3 pyridinemethanol (nicoloside) have been isolated from whole Anoectochilus koshunensis plants.
40 citations
TL;DR: In this article, detailed and extensive nmr analyses of paederoside have been carried out resulting to allow complete assignment of all of the 1 H and 13 C signals, which provided unambiguous bases to support methyl thiocarbonate structure (3) for paederosaide, a novel natural sulfur-containing iridoid glucoside of Paederia scandens.
Abstract: Detailed and extensive nmr analyses of paederoside have been carried out resulting to allow complete assignment of all of the 1 H and 13 C signals The results provided unambiguous bases to support methyl thiocarbonate structure (3) for paederoside, a novel natural sulfur-containing iridoid glucoside of Paederia scandens
40 citations
TL;DR: In this article, four phenanthrene glucosides were isolated from tubers of Bletilla striata and the structures were elucidated as 2,7-dihydroxy-4methoxyphenanthrene-2- O -glucoside.
36 citations
TL;DR: Ginseng hairy roots showed the biotransformation abilities of glycosylation and malonylation to 18β-glycyrrhetinic acid.
TL;DR: In this paper, the structure of iridoid glucosides from Linaria japonica was determined from spectroscopic evidence, including 6β-hydroxyantirr- hide, linarioloside, 5-deoxyteuhircoside and seco -linarioside.
TL;DR: Capsaicin was converted into the corresponding glucoside when administered to cell suspension cultures of Coffea arabica cultured in a modified Murashige and Skoog’s medium with 5 μM 2,4-dichlorophenoxyacetic acid and 0.5 μM kinetin.
Abstract: Capsaicin was converted into the corresponding glucoside when administered to cell suspension cultures of Coffea arabica cultured in a modified Murashige and Skoog’s medium with 5 μM 2,4-dichlorophenoxyacetic acid and 0.5 μM kinetin. The glucoside was identified as capsaicin-β-D-glucopyranoside by FAB-MS, 1H-NMR, and hydrolysis with α- and β-glucosidases. The pungency of the glucoside was approximately 1/100 of that of capsaicin.
TL;DR: A novel phenylpropanoid glucoside, linusitamarin, was isolated from the defatted meal of flaxseed, along with a number of known compounds, and the structure was determined by spectroscopic analysis.
Abstract: From the defatted meal of flaxseed (Linum usitatissimum), a novel phenylpropanoid glucoside, linusitamarin [1], was isolated, along with a number of known compounds. The structure of 1 was determined by spectroscopic analysis.
TL;DR: The glucoside retained the antimutagenic and antimicrobial activities of vanillin and was identified as 4-formyl-2-methoxyphenyl-O-β-D-glucopyranoside by 1H-N MR, 13C-NMR, FAB-MS, and hydrolysis by α- and β-gl glucosidases.
Abstract: Vanillin was converted into the corresponding glucoside in suspension-cultured cells of Ceffea arabica. The maximum efficiency of glucosylation was 85% within 24 h after the addition of 1 mM vanillin when cultured in a modified Murashige and Skoog’s medium with 5 µM 2,4-dichlorophenoxyacetic acid and 0.5 µM kinetin. The glucoside was identified as 4-formyl-2-methoxyphenyl-O-β-D-glucopyranoside by 1H-NMR, 13C-NMR, FAB-MS, and hydrolysis by α- and β-glucosidases. It retained the antimutagenic and antimicrobial activities of vanillin.
TL;DR: The enzyme specifically hydrolysing 6-O(4-O)-IAGlucose was partially purified using fractionation by PEG 6000, followed by ion-exchange, hydrophobic interaction and gel filtration chromatography.
TL;DR: The cyanogenic glucoside prunasin (2-β- d -glucopyranosyloxy-2-phenylacetonitrile) was isolated from leaves and twigs of Olinia emarginata as mentioned in this paper.
TL;DR: Besides the known glucosides, calceolarioside D, verbascoside, cornoside and rutin, a cyclohexanone derivative, halleridone, and a new quinol glucoside are known as discussed by the authors.
TL;DR: Woodorien was the most potent inhibitor against HSV-1 among the isolated compounds and the structures of these compounds were determined by the use of NMR techniques.
Abstract: Hot aqueous and methanol extracts of the rhizomes of Woodwardia orientalis were tested for their in vitro antiviral activity against herpes simplex virus type 1 (HSV-1), poliovirus type 1, and measles virus by plaque reduction assay. The aqueous extract of W. orientalis reduced the plaque forming ability of HSV-1 and poliovirus more strongly than did the methanol extract. By bioassay-directed fractionation of the aqueous extract, a new glucoside, woodorien (1), along with five known compounds were isolated from an EtO Ac-soluble fraction that had antiviral activity. The structures of these compounds were determined by the use of two dimensional (2D) NMR techniques (1H-1H correlation spectroscopy (COSY), 1H-13C COSY and heteronuclear multiple-bond multiple-quantum coherence (HMBC)). Woodorien (1) was the most potent inhibitor against HSV-1 among the isolated compounds.
Journal Article•
TL;DR: The diuretic furosemide (Lasix) was metabolized by the fungus Cunninghamella elegans to the phase II conjugate, furoSemide acyl glucoside, which was isolated following semipreparative scale incubations of C. elegans involving glucose nutrient dosing.
Abstract: The diuretic furosemide (Lasix) was metabolized by the fungus Cunninghamella elegans (ATCC 36112) to the phase II conjugate, furosemide acyl glucoside. This metabolite was isolated following semipreparative scale incubations of C. elegans involving glucose nutrient dosing, and was characterized by NMR spectroscopy (1H and 1H/1H correlated), MS (FAB), UV, HPLC with fluorescence detection, and enzymatic treatments. The aglycone fragment of the conjugate was characterized as furosemide by treatment of the metabolite with sodium hydroxide, whereas the sugar part was identified as glucose by cleavage of the conjugate, derivatization of the released sugar, and GC/MS analysis.
TL;DR: In this paper, three bisepoxylignan glycosides were isolated from Stauntonia hexaphylla and their structures were established on the basis of spectroscopic analysis and chemical evidence, and their 1 H NMR signals were assigned in detail by means of 2D-NMR techniques.
TL;DR: From leaves of premna corymbosa var. obtusifolia, premcoryoside, a verbascoside iridoid glucoside conjugate, was isolated along with verbascosi as discussed by the authors.
Journal Article•
TL;DR: From the whole parasitic plant of Cynomorium songaricum Rupr, three ursane type triterpenes, three steroidal compounds, palmitic acid and sucrose were isolated and two compounds found in this genus for the first time.
Abstract: From the whole parasitic plant of Cynomorium songaricum Rupr. three ursane type triterpenes, three steroidal compounds, palmitic acid and sucrose were isolated. The triterpenes were identified as acetyl ursolic acid (2), ursolic acid (3) and a new compound, ursa-12-ene-28-oic acid, 3 beta-propanedioic acid monoester (1). The steroidal compounds were identified as beta-sitosterol palmitate (4), beta-sitosterol (5) and beta-sitosterol glucoside (daucosterol, 6). Compounds 2 and 5 were found in this genus for the first time.
TL;DR: The results of this study indicate that pyridoxine glucoside uses the same transport system as does pyrIDoxine, which is the rate-limiting step in metabolism of this beta-glucoside.
Abstract: Uptake of pyridoxine-5'-beta-D-glucoside by freshly isolated rat liver cells was studied at a concentration (0.5 mumol/L) approximating the physiological range of vitamin B-6 by using a membrane filtration method. Unlabeled pyridoxine glucoside was found to competitively inhibit the uptake of [4'-3H]pyridoxine but have no detectable effect on the uptake of D-[1-3H]glucose by hepatocytes. The uptake of [3H]pyridoxine glucoside by isolated rat liver cells was very similar to the uptake of [3H]pyridoxine with Kt = 13.8 mumol/L (6.3 mumol/L for pyridoxine) and Vmax = 82 pmol/(10(6) cells.min) [28 pmol/(10(6) cells.min for pyridoxine)]. The results of this study indicate that pyridoxine glucoside uses the same transport system as does pyridoxine. Upon entry to the cell, pyridoxine glucoside undergoes hydrolysis to release pyridoxine, which is the rate-limiting step in metabolism of this beta-glucoside.
TL;DR: The new quercetin 3-[2,3,4-triacetyl-α- l -arabinosyl (1→ 6)-β- d -glucoside] has been isolated together with the dihydroflavonol glucoside c.
TL;DR: In this article, the unripe fruits of Rubus sp. (Rubi Fructus, Bogbunja) have yielded β-sitosterol glucoside and four urs-12-en-28-oic acid derivatives, three of which were as their glucosides.
Abstract: The dried unripe fruits ofRubus sp. (Rubi Fructus, Bogbunja) have yielded β-sitosterol glucoside and four urs-12-en-28-oic acid derivatives, three of which were as their glucosides. They were identified as 23-hydroxytormentic acid, rosamultin, niga-ichigosides F1 and F2 on the basis of spectral data.
TL;DR: A new secoiridoid glucoside named ornoside and a new tyrosol derivative called ornosol have been isolated from Fraxinus ornus bark, along with the k
TL;DR: The structure of a novel iridoid glucoside, schismoside isolated from Schismocarpus matudai, was determined in this article, and incorporation studies indicated a bio
Patent•
28 Dec 1993
TL;DR: In this article, a new chromanol glucoside is expressed by the formula I [R, R, R and R are H or lower alkyl; R is H, lower alyl or lower acyl; X is monosaccharide residue or oligosacaride residue; (n) is integer of 0-4; (m) isinteger of 1-6], e.g. 6-hydroxy-2,5,7,8-tetramethylchroman-2-methyl-alpha-D- glucopyr
Abstract: PURPOSE:To provide a new chromanol glucoside acting as an extremely effective antioxidant in aqueous solution, having excellent thermal and pH stability and useful as a raw material for cosmetics, clothes, foods, etc. CONSTITUTION:A new chromanol glucoside is expressed by the formula I [R , R , R and R are H or lower alkyl; R is H, lower alkyl or lower acyl; X is monosaccharide residue or oligosaccharide residue; (n) is integer of 0-4; (m) is integer of 1-6], e.g. 6-hydroxy-2,5,7,8-tetramethylchroman-2-methyl-alpha-D- glucopyranoside of the formula II. The compound of the formula I can be produced by reacting a 2-substituted-alcohol of the formula III with an oligosaccharide, soluble starch, starch or cyclodextrin is the presence of an enzyme catalyzing the corresponding sugar rearrangement action.