Enrichment of Polyglucosylated Isoflavones from Soybean Isoflavone Aglycones Using Optimized Amylosucrase Transglycosylation

Abstract

Isoflavones in soybeans are well-known phytoestrogens. Soy isoflavones present in conjugated forms are converted to aglycone forms during processing and storage. Isoflavone aglycones (IFAs) of soybeans in human diets have poor solubility in water, resulting in low bioavailability and bioactivity. Enzyme-mediated glycosylation is an efficient and environmentally friendly way to modify the physicochemical properties of soy IFAs. In this study, we determined the optimal reaction conditions for Deinococcus geothermalis amylosucrase-mediated α-1,4 glycosylation of IFA-rich soybean extract to improve the bioaccessibility of IFAs. The conversion yields of soy IFAs were in decreasing order as follows: genistein > daidzein > glycitein. An enzyme quantity of 5 U and donor:acceptor ratios of 1000:1 (glycitein) and 400:1 (daidzein and genistein) resulted in high conversion yield (average 95.7%). These optimal reaction conditions for transglycosylation can be used to obtain transglycosylated IFA-rich functional ingredients from soybeans.

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 ).…”

Using Amylosucrase for the Controlled Synthesis of Novel Isoquercitrin Glycosides with Different Glycosidic Linkages

“…The molecular structures of IQ glucosides synthesized by CGTase contain a series of α-1,4-glucosidic bonds from existing glucosyl moieties, resulting in augmentation of additional glucoses, such as isoquercitrin 4″,4‴-di- O -α- d -glucopyranoside and isoquercitrin 4″,4‴,4⁗-tri- O -α- d -glucopyranoside. − ASases transfer glucose from sucrose to −OHs in flavonoids such as daidzin, hydroxyflavones, isoquercitrin, and quercetin. In short, transglycosylation occurs at two target −OHs in flavonoids: the reducing end of the glucosyl moiety , and the free −OHs in flavonoids. , IQ has four free −OHs (3′, 4′, 5, and 7 positions) in the diphenyl propane backbone and four −OHs (2″, 3″, 4″, and 6″) in one glucose moiety substituted to the 3–OH of the backbone (Figure A). The one free 4′–OH of the backbone and the three free −OHs (2″, 4″, and 6′″) of the IQ glucosyl moiety are projected to bind with additional glucose molecules by DGAS on the basis of our current knowledge.…”

“…In short, transglycosylation occurs at two target −OHs in flavonoids: the reducing end of the glucosyl moiety 11,13 and the free −OHs in flavonoids. 13,22 IQ has four free −OHs (3′, 4′, 5, and 7 positions) in the diphenyl propane backbone and four −OHs (2″, 3″, 4″, and 6″) in one glucose moiety substituted to the 3−OH of the backbone (Figure 2A). The one free 4′−OH of the backbone and the three free −OHs (2″, 4″, and 6′″) of the IQ glucosyl moiety are projected to bind with additional glucose molecules by DGAS on the basis of our current knowledge.…”

The protective activity of genistein against bone and cartilage diseases

“…Genistein has a low water solubility and poor bioavailability, which have become the obstacle for genistein in developing as a potential candidate in functional foods or health-benefiting medicine. In addition, genistein can be metabolized in a short time after oral administration, leading to aberrant absorption ( Jung et al, 2020 ). Hopefully, many strategies have been developed for improvement of water solubility, bioavailability, and structural stability.…”