Biotransformation of Curcumenol by Mucor polymorphosporus

  • J Nat Prod. 2015 Apr 24;78(4):674-80. doi: 10.1021/np500845z.
Li-Xia Chen ,  Qian Zhao ,  Meng Zhang ,  Yan-Yan Liang ,  Jiang-Hao Ma ,  Xue Zhang ,  Li-Qin Ding  1 ,  Feng Zhao  2 ,  Feng Qiu  1
Affiliations
  • 1. ‡School of Chinese Materia Medica, Tianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Nankai District, Tianjin 300193, People's Republic of China.
  • 2. §School of Pharmacy, Yantai University, Laishan District, Yantai, 264005, People's Republic of China.
PMID: 25821895 DOI: 10.1021/np500845z
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.