Syntheses of α-tocopheryl glycosides by glucosidases

Ponrasu, Thangavel; Charles, Rajachristu Einstein; Sivakumar, Ramaiah; Divakar, Soundar

doi:10.1007/s10529-008-9702-9

Cited by 15 publications

(12 citation statements)

References 18 publications

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“…The 13 C-NMR spectrum of 4 exhibited the anomeric carbon signal at δ 100.7 (Table 1). This 13 C chemical shift of the anomeric carbon at δ 100.7 indicates the presence of O-glucoside in the structure of 4 [32][33][34]. From the coupling pattern of the proton signals and the chemical shifts of the carbon resonances due to the sugar moiety (Table 1), the sugar component in 4 was determined to be β-D-glucopyranose.…”

Section: Glycosylation Of Oxyresveratrol (1) and Gnetol (2) By Culturmentioning

confidence: 94%

Glycosylation of Stilbene Compounds by Cultured Plant Cells

et al. 2020

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Oxyresveratrol and gnetol are naturally occurring stilbene compounds, which have diverse pharmacological activities. The water-insolubility of these compounds limits their further pharmacological exploitation. The glycosylation of bioactive compounds can enhance their water-solubility, physicochemical stability, intestinal absorption, and biological half-life, and improve their bio- and pharmacological properties. Plant cell cultures are ideal systems for propagating rare plants and for studying the biosynthesis of secondary metabolites. Furthermore, the biotransformation of various organic compounds has been investigated as a target in the biotechnological application of plant cell culture systems. Cultured plant cells can glycosylate not only endogenous metabolic intermediates but also xenobiotics. In plants, glycosylation reaction acts for decreasing the toxicity of xenobiotics. There have been a few studies of glycosylation of exogenously administrated stilbene compounds at their 3- and 4′-positions by cultured plant cells of Ipomoea batatas and Strophanthus gratus so far. However, little attention has been paid to the glycosylation of 2′-hydroxy group of stilbene compounds by cultured plant cells. In this work, it is described that oxyresveratrol (3,5,2′,4′–tetrahydroxystilbene) was transformed to 3-, 2′-, and 4′-β-glucosides of oxyresveratrol by biotransformation with cultured Phytolacca americana cells. On the other hand, gnetol (3,5,2′,6′–tetrahydroxystilbene) was converted into 2′-β-glucoside of gnetol by cultured P. americana cells. Oxyresveratrol 2′-β-glucoside and gnetol 2′-β-glucoside are two new compounds. This paper reports, for the first time, the glycosylation of stilbene compounds at their 2′-position by cultured plant cells.

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Section: Glycosylation Of Oxyresveratrol (1) and Gnetol (2) By Culturmentioning

confidence: 94%

Glycosylation of Stilbene Compounds by Cultured Plant Cells

et al. 2020

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“…The 1 H and 13 C NMR data ( Table 3) of 8 showed great similarity to those of model compound, a-tocopherol. 28 Careful comparison of the NMR data of 8 and a-tocopherol revealed that significant differences between them resided in the nature of the substituents at C-21 on the side chain (-H in a-tocopherol; -OH in 8) and at C-4 on the benzene ring where the hydroxyl group in a-tocopherol was replaced by a 3,5-dimethylphenoxyl group in 8. The assignments of the 3,5-dimethylphenoxyl group in 8 were established by the 1 H and 13 C NMR data (Table 3), together with the HMBC correlations (Fig.…”

Section: Structure Elucidation Of New Compoundsmentioning

confidence: 99%

Bioactive constituents from the green alga Caulerpa racemosa

Yang

Liu

Liang

et al. 2015

Bioorganic & Medicinal Chemistry

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“…Enzymatic glycosylation can be effected by glucosidases (Sivakumar et al 2006;Vijayakumar et al 2006). Glucosidases are hydrolytic in nature, but unusual conditions involving organic solvents with little quantity of water, direct the enzymes towards glycosylation (Ponrasu et al 2008).…”

Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis of cholecalciferol glycosides using β-glucosidase from sweet almond

Manohar

Divakar

2010

J Food Sci Technol

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β-Glucosidase from sweet almond (Amygdalus communis var. 'Dulcis') entrapped on to calcium alginate beads catalysed the synthesis of water soluble 17-O-(Dglucopyranosyl)cholecalciferol. Optimum conditions for the reaction were: 60% (w/w D-glucose) β-glucosidase, 0.12 mM pH 6 phosphate buffer and 30 h incubation period. β-Glucosidase also catalyzed the reaction with D-glucose 2, D-galactose 3, D-mannose 4 and D-fructose 5 with generally low yields in the range of 3-14%. Both α/β anomers of Dglucose 2, D-galactose 3 and D-mannose 4 reacted, of which the former two formed C6-O derivatives also.

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Syntheses of α-tocopheryl glycosides by glucosidases

Cited by 15 publications

References 18 publications

Glycosylation of Stilbene Compounds by Cultured Plant Cells

Glycosylation of Stilbene Compounds by Cultured Plant Cells

Bioactive constituents from the green alga Caulerpa racemosa

Enzymatic synthesis of cholecalciferol glycosides using β-glucosidase from sweet almond

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