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Antidiabetic complications and anti‐alzheimer activities of sophoflavescenol, a prenylated flavonol from Sophora flavescens , and its structure–activity relationship
Author(s) -
Jung Hyun Ah,
Jin Seong Eun,
Park JunSeong,
Choi Jae Sue
Publication year - 2011
Publication title -
phytotherapy research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.019
H-Index - 129
eISSN - 1099-1573
pISSN - 0951-418X
DOI - 10.1002/ptr.3326
Subject(s) - sophora flavescens , flavonols , aldose reductase , prenylation , chemistry , flavanone , stereochemistry , biochemistry , quercetin , traditional medicine , enzyme , flavonoid , medicine , antioxidant , chromatography , matrine
Abstract It was previously reported that prenylated flavonols from Sophora flavescens are inhibitors of rat lens aldose reductase (RLAR), human recombinant aldose reductase (HRAR), advanced glycation endproducts (AGE), β‐secretase (BACE1) and cholinesterases (ChE). Based upon structure–activity relationships, 3,4′‐dihydroxy flavonols with a prenyl or lavandulyl group substitution at the C‐8 position, and a hydroxy group at the C‐5, are important for such inhibition. In our ongoing study to isolate active principles from S. flavescens by an activity‐guided isolation procedure, further detailed phytochemical investigations of the CH 2 Cl 2 fraction were conducted via repeated chromatography over silica gel and Sephadex LH‐20 columns. This ultimately resulted in the isolation of a promising active sophoflavescenol with higher inhibitory activities among the current prenylated flavonols isolated from S. flavescens against RLAR, HRAR, AGE, BACE1 and ChEs. The results further support that 3,4′‐dihydroxy flavonols with a prenyl or lavandulyl substitution at the C‐8 position and a methoxy group at C‐5 represent a new class of RLAR, HRAR and AGE inhibitors. Nevertheless, the C‐5 hydroxyl group of prenylated flavonoids is important for inhibition of BACE1 and ChEs, indicating that the hydroxyl group at C‐5 might be the main contributor to the augmentation and/or modification of prenylated flavonol activity. Copyright © 2010 John Wiley & Sons, Ltd.