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Biotransformation of isoimperatorin by Cunninghamella blakesleana AS 3.970

Author:
Yang, XiaoBo, Hou, Jie, Liu, Dan, Deng, Sa, Wang, Zhi Bin, Kuang, Hai Xue, Wang, ChangYuan, Yao, Ji Hong, Liu, Ke Xin, Ma, Xiao Chi
Source:
Journal of Molecular Catalysis. B, Enzymatic 2013 v.88 pp. 1-6
ISSN:
1381-1177
Subject:
Cunninghamella, biotransformation, catalytic activity, chemical structure, glycosylation, hydrogenation, hydroxylation, metabolites, nuclear magnetic resonance spectroscopy, spectral analysis
Abstract:
The biotransformation of isoimperatorin (1) by Cunninghamella blakesleana AS 3.970 yielded 6 novel products, 14-hydroxyl-isoimperatorin (2), 11-carbonyl-14-hydroxyl isoimperatorin (3), 11-carbonyl-14-hydroxyl-12,13-dihydrogen-iso-imperatorin (4), 14-hydroxyl-12,13-dihydrogenisoimperatorin (5), isoimperatorin-14-O-β-d-mannoside (6) and isoimperatorin-14-O-β-d-glucoside (7), respectively. The chemical structures of these metabolites were elucidated based on extensive spectral data including 2D NMR and HRMS. The hydroxylation, hydrogenation, carbonylation and glycosylation reactions of 1 by C. blakesleana AS 3.970 were observed in the present study. In addition, anti-osteoporosis activities of substrate and all transformed products were evaluated by using MC3T3-E1 cells. Our results suggested that hydroxylation or glycosylation of C-14 would enhance anti-osteoporosis activity significantly.
Agid:
855163