Showing papers on "Glucoside published in 1995"
TL;DR: Investigation of an enzyme system in the xylem of Pinus contorta var latifolia Engelm revealed two major [beta]-glucosidases that efficiently hydrolyzed the native substrate, coniferin, and one was more active against synthetic glucosides.
Abstract: Coniferin, the glucoside of the monolignol coniferyl alcohol, accumulates to high levels in gymnosperms during spring-cambial reactivation. A cinnamyl alcohol glucoside/[beta]-glucosidase system is thought to play a key role in lignification by releasing the monolignol aglycones. Investigation of such an enzyme system in the xylem of Pinus contorta var latifolia Engelm. revealed two major [beta]-glucosidases. One efficiently hydrolyzed the native substrate, coniferin, and the other was more active against synthetic glucosides. The coniferin [beta]-glucosidase was purified to apparent homogeneity using anion exchange, hydrophobic interaction, and size-exclusion chromatography. The apparent native molecular weight was estimated to be 60,000. A dominant 28-kD protein and a minor 24-kD protein were detected in the purified preparation following sodium dodecyl sulfate-polyacrylamide gel electrophoresis. Immunological evidence from polyclonal antibodies directed against the synthetic N-terminal peptide of the 24-kD protein suggested that the native protein is a dimer of 28-kD subunit size. The N-terminal sequence showed that coniferin [beta]-glucosidase has high homology to known plant [beta]-glucosidases. Coniferin, syringin, and a synthetic coniferin analog were preferred substrates for the coniferin [beta]-glucosidase. In situ localization using the chromogenic coniferin analog showed the exclusive presence of [beta]-glucosidase activity in the differentiating xylem, similar to peroxidase activity.
216 citations
TL;DR: Phenolic compounds have been determined by HPLC in the flesh of olives and brines of two cultivars (Manzanilla and Hojiblanca) during Spanish-style green olive processing as mentioned in this paper.
Abstract: Phenolic compounds have been determined by HPLC in the flesh of olives and brines of two cultivars (Manzanilla and Hojiblanca) during Spanish-style green olive processing. The NaOH treatment hydrolyzed oleuropein into hydroxytyrosol (3,4-dihydroxyphenylethanol) and elenolic acid glucoside. After a rapid diffusion of hydroxytyrosol from the flesh of fruits into the brines, the concentration of the o-diphenol remained practically constant throughout the lactic acid fermentation step. In contrast, elenolic acid glucoside increased in concentration in the olive brines during the first few days of brining but disappeared after 100-200 days. Other minor phenolic compounds also diffused rapidly into the olive brines during the first few days of brining. Caffeic acid, oleuropein, and p-coumaric acid diminished in concentration throughout the fermentation period, whereas the concentration of tyrosol (4-hydroxyphenylethanol) remained constant.
141 citations
01 Jan 1995
TL;DR: In this article, Guaiacyl-type lignin polymer models were prepared from coniferin by the action of s-glucosidase and Dehydrogenation polymer peroxidase, with hydrogen peroxide generated in situ through the actions of oxygen and glucose oxidase of monolignols.
Abstract: Summary Lignin polymer model Guaiacyl-type lignin polymer models were prepared from coniferin by the action of s-glucosidase and Dehydrogenation polymer peroxidase, with hydrogen peroxide generated in situ through the action of oxygen and glucose oxidase of monolignols (DHP) Coniferin on the glucose liberated from the coniferin, Polylignols were also prepared from coniferyl alcohol using Monolignols glucoside procedures modified to more closely correspond to conditions prevailing in the cell wall environment. The structure of these novel polylignols approximated that of native lignin more closely than did the Coniferyl alcohol 13 C NMR structure of polylignols prepared by the conventional method from coniferyl alcohol.
116 citations
TL;DR: Treatment of 1-4 with dilute HCl yielded known caffeic acid tetramers [8 and 9], which were found to be less active, indicating the importance of the sodium and potassium salts to the enhanced anti-HIV activity.
Abstract: Monosodium and monopotassium salts [2-4] of isomeric caffeic acid tetramers were isolated from Arnebia euchroma as anti-HIV agents. Mixtures of dipotassium and disodium salts [1] of a caffeic acid tetramer and dipotassium and potassium-sodium salts [5] of a caffeic acid tetramer glucoside were also isolated from the active fraction. The structures of 1-5 were characterized by chemical and spectral evidence. Compounds 2-4 demonstrated potent anti-HIV activity with EC50 values of 2.8, 4.0, and 1.5 micrograms/ml, respectively. Treatment of 1-4 with dilute HCl yielded known caffeic acid tetramers [8 and 9], which were found to be less active, indicating the importance of the sodium and potassium salts to the enhanced anti-HIV activity.
90 citations
TL;DR: In this paper, the β-glucosidase-catalyzed synthesis of n-alkyl-β- d -glucose through condensation of glucose and n-alcohols with alkyl chain lengths of 6 to 12 was carried out in a biphasic system, where the organic phase consisted only of an alcohol substrate.
87 citations
TL;DR: Feeding preferences of the tested leaf beetles were strongly influenced by certain phenolic glucosides which are typical secondary compounds of willows (Salicaceae: Salix).
Abstract: The effects of individual phenolic glucosides and total glucoside fractions on the feeding behaviour of three willow-feeding leaf beetles (Coleoptera: Chrysomelidae) were tested in the laboratory. Feeding preferences of the tested leaf beetles were strongly influenced by certain phenolic glucosides which are typical secondary compounds of willows (Salicaceae: Salix).
Two of the tested leaf beetles, Galerucella lineola and Lochmaea capreae showed rather similar responses to glucoside treatments. Both of them were strongly stimulated by total glucoside fractions from Salix triandra and by its major glucoside salidroside. The third species, Phatora vitellinae, was attracted most by the fractions from S. myrsinifolia and S. pentandra, and by two related salicylate glucosides, tremulacin and salicortin. Food selection pattern of the tested beetles in the laboratory concords fairly well with their distributions in the field and with the occurrence of phenolic glucosides in their host willows. Phenolic glucoside extracts stimulated more feeding than individual pure glucosides. This indicates that different compounds have synergistic effects in the feeding behaviour of leaf beetles. Our results clearly show that willow leaf beetles select their food based on phenolic glucosides of their host plants.
86 citations
TL;DR: In this article, the structure of the new compound was elucidated on the basis of its chemical and spectral data as tetrahydro-3-hydroxy hydroxymethylene-4-(3]-polyethylene prop-1-ene)-2H-pyran-2-one.
65 citations
TL;DR: In this article, aerial parts of Stachys aegyptiaca contain the unique acylated flavonoid, diapigenin-7- O -(6″- trans, 6″- cis - p, p ′-dihydroxy- μ -truxinyl) glucoside, stachysetin, and the hitherto unknown, apigenin 7- O −(3″- p -coumaryl) glucoseside.
61 citations
TL;DR: Two new carotenoid glycosides were isolated from the astaxanthin-producing marine bacterium Agrobacterium aurantiacum, and their structures were determined by spectral means.
Abstract: Two new carotenoid glycosides, (3S,3'S)-astaxanthin-β-D-glucoside [3] and (3S,3'R)-adonixanthin-β-D-glucoside [4], were isolated from the astaxanthin-producing marine bacterium Agrobacterium aurantiacum, and their structures were determined by spectral means.
53 citations
TL;DR: An inducible intracellular beta-glucosidase from Streptomyces sp.
52 citations
TL;DR: Investigation of the effect of UV-A light intensity on growth, biopterin glucoside production and photosynthetic activity of a marine planktonic cyanobacterium isolated which is resistant to ultraviolet-A (UV-A) irradiation found that after 10 h there was a rapid increase in biopter in glucosid content.
TL;DR: Biological evaluations showed that five compounds (betulin, betulinic acid, hyperin, quercetin, and ursenaldehyde) exhibited spasmogenic activity on isolated rat fundus, and three isolates showed noncompetitive antagonism to serotonin (5-HT) on the same preparation.
Abstract: In a biological and phytochemical study on the leaves of Byrsonima crassifolia, 22 compounds were isolated and identified from a MeOH extract. Among the isolates were six triterpenes (betulinaldehyde, betulin, betulinic acid, lupeol, oleanolic acid, and ursenaldehyde), two sterols (β-sitosterol and its glucoside), six flavonoids (catechin, epicatechin, guaijaverin, hyperin, quercetin and its 3-0-[6″-galloyl]galactoside), an aromatic ester (methyl gallate), four common amino acids (alanine, aspartic acid, proline, and valine), two non-protein amino acids (pipecolic acid and 5-hydroxypipecolic acid), and a novel sulfonoglycolipid. Biological evaluations showed that five of these compounds (betulin, betulinic acid, hyperin, quercetin, and ursenaldehyde) exhibited spasmogenic activity on isolated rat fundus, and three isolates (hyperin, pipecolic acid and 5-hydroxypipecolic acid) showed noncompetitive antagonism to serotonin (5-HT) on the same preparation.
TL;DR: A new 4,5,8-trihydroxy-α-tetralone-5-O-β-D-glucoside along with 1,4,8,trihydroxynaphthalene-1-O -β -D -glucose and gallic acid were isolated from the roots of Juglans mandshurica as discussed by the authors.
Abstract: A new 4,5,8-trihydroxy-α-tetralone-5-O-β-D-glucoside along with 1,4,8-trihydroxynaphthalene-1-O-β-D-glucoside and gallic acid were isolated from the roots ofJuglans mandshurica Their structures were elucidated on the basis of spectroscopic studies
TL;DR: The complete structure of each anthocyanin was unambiguously determined by 1D- and 2D-NMR and other spectral methods.
TL;DR: Caffeic acid was glucosylated with hydroquinone glucosating enzyme (HGE) from Bacillus subtilis X-23 in order to improve its characteristics as discussed by the authors.
TL;DR: In this article, the new secoiridoid glucoside 7-E / Z -(p -coumaroyl)-5-hydroxysecologanol was found in fontanesia fortunei and F. phillyreoides.
TL;DR: Two novel anthocyanins have been isolated from red flowers of Hyacinthus orientalis cv Holly Hock, along with seven known anthOCyanins, two of which include cis - p -coumaric acid as the acyl moiety.
TL;DR: In this article, a new monocyclic C 10 iridoid glucoside was isolated from the leaves of Viburnum lantana, together with two known glucosides, dihydropenstemide and betulalbuside A. The structure of the new compound, lantanoside, was established from extensive 1 H and 13 C NMR, 1D and 2D homo-and heteronuclear correlation experiments.
TL;DR: Two new flavonol glycosides: 4′-methylquercetagetin 7-O-(6″-E- caffeoyl-β-d -glucoside ) and quercetAGetin7-O(6- acetylβ- d −glucose ) along with the 7- O -glocosides of 6-hydroxykaempferol, quercETin and quergulosum have been isolated and characterized from the leaves of Eupatorium glandulosuma as discussed by the authors.
TL;DR: In this article, six new dihydrobenzofuran neolignans were isolated from the fresh rhizomes of Coptis japonica var. dissecta, and their absolute configurations were determined by means of CD studies.
Abstract: Six new dihydrobenzofuran neolignans were isolated from the fresh rhizomes of Coptis japonica var. dissecta, together with (+)-isolariciresinol, (+)-lariciresinol glucoside, (+)-pinoresinol, (+)-pinoresinol glucoside, (+)-syringaresinol glucoside and ethyl ferulate. Their structures were determined on the basis of spectroscopic data and chemical evidence. Their absolute configurations were determined by means of CD studies.
TL;DR: In this paper, the leaves of Nyctanthes arbor-tristis were examined and a minor iridoid glucoside, arborside D, was identified as its acetyl derivative.
Abstract: Re-examination of the leaves of Nyctanthes arbor-tristis led to the isolation and identification of new minor iridoid glucoside, arborside D [1], as its acetyl derivative. The structure of the new compound was determined using spectral methods.
TL;DR: The possible biosynthetic pathway for the carotenoid glucoside ester starts with lycopene being cyclized to γ-carotene, from which myxocoxanthin is produced by hydration and desaturation.
Abstract: The precise chemical structures of two carotenoid glucoside esters, keto-myxocoxanthin glucoside ester isolated from Myxococcus sp. MY-18 and dehydrorhodopin glucoside ester from cells cultured in a nicotinecontaining medium, were determined as 1′-[(6-O-acyl-β-D-glucopyranosyl)oxy]-3′,4′-didehydro-l′,2′-dihydro-β,ψ-caroten-4-one and 1-[(6-O-acyl-β-D-glucopyranosyl)oxy]-3,4-didehydro-1,2-dihydro-ψ,ψ-carotene, respectively. They had β-D-glucoside, whose C-6 hydroxyl group was esterified. The major fatty acid was 11-methyldodecanoate with minor components of n-dodecanoate, n-tetradecanoate, and 13-methyltetradecanoate. This composition is different from that of cellular lipids, and the unusual accumulation of phytoene (more than 70% of total carotenoids) is characteristic of this strain.The possible biosynthetic pathway for the carotenoid glucoside ester starts with lycopene being cyclized to γ-carotene, from which myxocoxanthin is produced by hydration and desaturation. β-D-Glucose was attached to the carot...
TL;DR: Findings indicate that microbial and mucosal enzymes can participate in the intestinal hydrolysis of pyridoxine glucoside and that the kidney may contribute to postabsorptive hydrolyzed vitamin B-6 metabolism.
Abstract: Pyridoxine glucoside is a partially available form of vitamin B-6 present in plant-derived foods. In this set of three studies, rats were fed diets containing different concentrations of either pyridoxine or pyridoxine glucoside in the presence or absence of a fixed concentration of pyridoxine for 2 wk. The distribution of B-6 vitamers and beta-glucosidase activity in tissues was examined to determine the metabolic effects of chronic consumption of pyridoxine glucoside. Rats fed pyridoxine glucoside either with or without pyridoxine exhibited a significant increase in the amount of hepatic pyridoxine 5'-phosphate (not detected in rats fed pyridoxine alone), whereas hepatic pyridoxal 5'-phosphate was decreased with increasing dietary pyridoxine glucoside. The activity of cytosolic beta-glucosidases in small intestine and kidney was affected by the dietary concentration of both pyridoxine and pyridoxine glucoside. Enzymatic activity capable of hydrolyzing pyridoxine glucoside was found in mucosal and intraluminal fractions of small intestine and in the kidney. Other tissues examined, including liver, spleen and stomach, did not hydrolyze pyridoxine glucoside in detectable quantities. These findings indicate that microbial and mucosal enzymes can participate in the intestinal hydrolysis of pyridoxine glucoside and that the kidney may contribute to postabsorptive hydrolysis. These findings further support the observations that dietary pyridoxine glucoside influences vitamin B-6 metabolism.
TL;DR: A new esterified iridoid glucoside ring-opened between C-1 and C-2 has been isolated from the root of Patrinia scabra and characterized by intensive spectroscopic analysis as discussed by the authors.
TL;DR: The volatile substances obtained after enzymatic hydrolysis of purified polar extracts from the aerial parts of the two subspecies of Cedronella canariensis were shown to be, among others, benzyl alcohol (29.4%), chavicol (11.6%), cis-3-hexenol (9.3%), 2-phenylethanol (8.6), cis-pinocarveol (5.1%), myrtenol (2.2%), 1-phenylthanol(2.0%, tentatively), 1-oct
TL;DR: The new 5-methyl-4-hydroxy-3(2H)-furanone glucoside (psydrin) and the new (5-O-E-caffeoyl-fl- D-apio-D- furanosyl-(1 ~ 6-o-glucopyranosyl benzoic acid ester) were isolated from the leaves of Psydrax livida.
TL;DR: The finding of a 9-glucoside of 6-[(Z)-4-hydroxy-3-methyl-2-butenylamino]purine (cis-zeatin) gives proof that cis-ZEatin, a modified base in tRNA, also exists as a free substance in plants, since the glucoside cannot arise by enzymatic degradation of tRNA during plant extraction.
Abstract: A compound was isolated from potato (Solanum tuberosum L. cv Bintje) tuber sprouts by immunoaffinity chromatography with antibodies against the cytokinins zeatin riboside and isopentenyladenosine. Analysis by ultraviolet spectroscopy and gas chromatography-mass spectrometry of derivatives identified the compound as a 9-glucoside of 6-[(Z)-4-hydroxy-3-methyl-2-butenylamino]purine (cis-zeatin). N-glucosides have often been reported as metabolites of other cytokinins, but to our knowledge, they have never before been found for cis-zeatin. The finding gives proof that cis-zeatin, a modified base in tRNA, also exists as a free substance in plants, since the glucoside, unlike other tRNA-free cis-zeatins described earlier by others, cannot arise by enzymatic degradation of tRNA during plant extraction.
TL;DR: Two novel anthocyanins have been isolated from the red flowers of Hyacinthus orientalis cv Holly Hock and their complete structures were unambiguously elucidated principally by 1D and 2D NMR techniques.
TL;DR: Three glucosides (1-3), together with known phenylpropanoids and polyacetylenes were isolated from Oenanthe javanica Blume (DC) and were determined to be 2,3-methylenedioxy-5-allylphenyl beta-D-glucopyranoside, mainly by NMR techniques.
Abstract: Three glucosides (1–3), together with known phenylpropanoids and polyacetylenes were isolated from Oenanthe javanica Blume (DC.). Glucoside 1, named oenanthoside A, is a new phenylpropanoid glucoside and was determined to be 2,3-methylenedioxy-5-allylphenyl β-D-glucopyranoside, mainly by NMR techniques. Glucosides 2 and 3 were identified as eugenyl β-D-glucopyranoside and pinoresinol β-D-glucopyranoside, respectively. These were found for the first time in this plant.