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Biotransformation of Curcumenol by Mucor polymorphosporus

Author:
Chen, Li-Xia, Zhao, Qian, Zhang, Meng, Liang, Yan-Yan, Ma, Jiang-Hao, Zhang, Xue, Ding, Li-Qin, Zhao, Feng, Qiu, Feng
Source:
Journal of natural products 2015 v.78 no.4 pp. 674-680
ISSN:
1520-6025
Subject:
Mucor, biocatalysis, biotransformation, macrophages, metabolites, nitric oxide, spectral analysis
Abstract:
Biocatalysis of curcumenol (1) was performed by Mucor polymorphosporus AS 3.3443. Six metabolites including five new compounds were obtained, and their structures were elucidated as 10β-hydroxy-9,10-dihydrocurcumenol (2), 2β-hydroxycurcumenol (3), 15-hydroxycurcumenol (4), 12-hydroxycurcumenol (5), 1-hydroxy-4αH-guai-1,6,9-triene-2,8-dione (6), and 5-hydroxycarbonyl-1-oxo-3,7-dimethylindane (7) by spectroscopic analysis. M. polymorphosporus catalyzed unusual degradation and rearrangement reactions to generate a ring-contracted metabolite (7) of curcumenol (1). Curcumenol (1) and metabolites 4–7 exhibited inhibitory activities against lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophages, with 7 exhibiting more potent activity than curcumenol.
Agid:
5498147