期刊
MOLECULES
卷 22, 期 7, 页码 -出版社
MDPI
DOI: 10.3390/molecules22071230
关键词
prenylated flavonoids; xanthohumol; microbial glycosylation; glycosides; human serum albumin; cyclooxygenases; COX-1; COX-2
资金
- (Polish) National Science Centre [2015/17/D/NZ9/02060]
- Wroclaw Centre of Biotechnology, programme The Leading National Research Centre (KNOW)
The synthesis of different classes of prenylated aglycones (alpha,beta-dihydroxanthohumol (2) and (Z)-6,4'-dihydroxy-4-methoxy-7-prenylaurone (3)) was performed in one step reactions from xanthohumol (1)-major prenylated chalcone naturally occurring in hops. Obtained flavonoids (2-3) and xanthohumol (1) were used as substrates for regioselective fungal glycosylation catalyzed by two Absidia species and Beauveria bassiana. As a result six glycosides (4-9) were formed, of which four glycosides (6-9) have not been published so far. The influence of flavonoid skeleton and the presence of glucopyranose and 4-O-methylglucopyranose moiety in flavonoid molecule on binding to main protein in plasma, human serum albumin (HSA), and inhibition of cyclooxygenases COX-1 and COX-2 were investigated. Results showed that chalcone (1) had the highest binding affinity to HSA (8.624 x 104 M-1) of all tested compounds. It has also exhibited the highest inhibition of cyclooxygenases activity, and it was a two-fold stronger inhibitor than alpha,beta-dihydrochalcone (2) and aurone (3). The presence of sugar moiety in flavonoid molecule caused the loss of HSA binding activity as well as the decrease in inhibition of cyclooxygenases activity.
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