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Enzymatic synthesis of a novel kaempferol-3-O-β-D-glucopyranosyl-(1→4)-O-α-D-glucopyranoside using cyclodextrin glucanotransferase, and its inhibitory effects on aldose reductase, inflammation, and oxidative stress.

Enzymatic synthesis of a novel kaempferol-3-O-β-D-glucopyranosyl-(1→4)-O-α-D-glucopyranoside using cyclodextrin glucanotransferase, and its inhibitory effects on aldose reductase, inflammation, and oxidative stress.
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Choung WJ, Hwang SH, Ko DS, Kim SB, Kim SH, Jeon SH, Choi HD, Lim SS, Shim JH,


Choung WJ, Hwang SH, Ko DS, Kim SB, Kim SH, Jeon SH, Choi HD, Lim SS, Shim JH, (click to view)

Choung WJ, Hwang SH, Ko DS, Kim SB, Kim SH, Jeon SH, Choi HD, Lim SS, Shim JH,

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Journal of agricultural and food chemistry 2017 03 16() doi 10.1021/acs.jafc.7b00501

Abstract

Kaempferol-3-O-β-D-glucopyranoside (astragalin, AS), a major flavonoid that exists in various plants, exerts anti-oxidant, anti-tumor, anti-human immunodeficiency virus (HIV), and anti-inflammatory effects. However, the low water solubility of AS limits its use. In this study, we used cyclodextrin glucanotransferase (CGTase) with maltose (G2) as a donor molecule to enzymatically modify AS to improve its water solubility and physiochemical properties. We isolated the glycosylated astragalin (G1-AS) and identified the structure of G1-AS as kaempferol-3-O-β-D-glucopyranosyl-(1→4)-O-α-D-glucopyranoside, where one glucose residue was transferred to AS. G1-AS retained the anti-oxidative activity of the original AS compound; however, the solubility of G1-AS was 65-fold higher than that of AS. In addition, G1-AS showed enhanced anti-inflammatory effects and aldose reductase inhibitory activity compared to AS when applied to rat lenses.

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