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J Agric Food Chem. 2017 Apr 5;65(13):2760-2767. doi: 10.1021/acs.jafc.7b00501. Epub 2017 Mar 24.

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.

Author information

1
Department of Food Science and Nutrition, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.
2
Center for Aging and Health Care, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.
3
Department of Life Science, Hallym University , 1 Hallymdaehak-gil, Chuncheon, Gwangwon-do 24252, South Korea.
4
Division of Strategic Food Research, Korea Food Research Institute , Gyeonggi 13539, South Korea.

Abstract

Kaempferol-3-O-β-d-glucopyranoside (astragalin, AS), a major flavonoid that exists in various plants, exerts antioxidant, antitumor, 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 antioxidative 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.

KEYWORDS:

aldose reductase; anti-inflammatory; astragalin; glucanotransferase; solubility; transglycosylation

PMID:
28300406
DOI:
10.1021/acs.jafc.7b00501
[Indexed for MEDLINE]

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