Enzymatic Synthesis of Resveratrol α-Glucoside by Amylosucrase of Deinococcus geothermalis

Abstract

Glycosylation of resveratrol was carried out by using the amylosucrase of Deinococcus geothermalis, and the glycosylated products were tested for their solubility, chemical stability, and biological activities. We synthesized and identified these two major glycosylated products as resveratrol-4′-Oα-glucoside and resveratrol-3-O-α-glucoside by nuclear magnetic resonance analysis with a ratio of 5:1. The water solubilities of the two resveratrol-α-glucoside isomers (α-piceid isomers) were approximately 3.6 and 13.5 times higher than that of β-piceid and resveratrol, respectively, and they were also highly stable in buffered solutions. The antioxidant activity of the α-piceid isomers, examined by radical scavenging capability, showed it to be initially lower than that of resveratrol, but as time passed, the α-piceid isomers' activity reached a level similar to that of resveratrol. The αpiceid isomers also showed better inhibitory activity against tyrosinase and melanin synthesis in B16F10 melanoma cells than β-piceid. The cellular uptake of the α-piceid isomers, which was assessed by ultra-performance liquid chromatography (UPLC) analysis of the cell-free extracts of B16F10 melanoma cells, demonstrated that the glycosylated form of resveratrol was gradually converted to resveratrol inside the cells. These results indicate that the enzymatic glycosylation of resveratrol could be a useful method for enhancing the bioavailability of resveratrol.

The radiophiles of Deinococcaceae family: Resourceful microbes for innovative biotechnological applications

“…2019 b) with DgAS improved water solubility. Similar effect of glycation through DgAS was observed on a number of anti-inflammatory compounds (8-hydroxydaidzein, baicalein, caffeic acid phenethyl ester, quercetin), anti-neoplastic compounds (luteolin, (+)-catechin, Resveratrol, isoquercitrin, genistein, daidzein); phytoestrogen glycitein and anti-oxidant rutin ( Chang et al., 2019 ; Cho et al., 2011 ; Jang et al., 2018 ; Jung et al., 2020 ; Kim et al., 2014 , 2016 ; Moon et al., 2017 ; Moon et al., 2021 ; Rha et al., 2019 a; Rha et al., 2020 ).…”

Production of Resveratrol Glucosides and Its Cosmetic Activities

“…Although many flavone materials are available as potential pharmaceutical candidates, their application is restricted because of their poor solubility. Thus, the main aim of this study was to synthesize flavone glycosides on an industrial scale using DgAS [63,64].…”

Anticancer Activity of Continentalic Acid in B-Cell Lymphoma

“…The collected fractions (ACE-W252, 0.18 g) containing diterpenoids were concentrated with a rotary vacuum evaporator and loaded onto an ODS column (2 cm × 25 cm, YMC Co., Kyoto, Japan) with methanol/acetonitrile/0.1% trifluoroacetic acid (42.75:52.25:5, v/v/v) to obtain epi-continentalic acid (12 mg), continentalic acid (54 mg), and kaurenoic acid (30 mg). The fractions from each chromatography were analyzed by thin layer chromatography (TLC) as described previously [32] with some modifications. Each fraction was spotted directly onto TLC silica gel 60 plates (Merck, Darmstadt, Germany).…”