title: Biotransformation of Curcumenol by Mucor polymorphosporus.
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.
authors.forename: Li-Xia
authors.initials: LX
authors.lastname: Chen
authors.forename: Qian
authors.initials: Q
authors.lastname: Zhao
authors.forename: Meng
authors.initials: M
authors.lastname: Zhang
authors.forename: Yan-Yan
authors.initials: YY
authors.lastname: Liang
authors.forename: Jiang-Hao
authors.initials: JH
authors.lastname: Ma
authors.forename: Xue
authors.initials: X
authors.lastname: Zhang
authors.affiliation: ‡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.
authors.forename: Li-Qin
authors.initials: LQ
authors.lastname: Ding
authors.affiliation: §School of Pharmacy, Yantai University, Laishan District, Yantai, 264005, People's Republic of China.
authors.forename: Feng
authors.initials: F
authors.lastname: Zhao
authors.affiliation: ‡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.
authors.forename: Feng
authors.initials: F
authors.lastname: Qiu
mesh_terms: D000818:Animals; D055162:Biocatalysis; D001711:Biotransformation; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D009089:Mucor / Q000378:metabolism*; D009569:Nitric Oxide / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D012717:Sesquiterpenes / Q000737:chemistry*
chemical_list: D008070:Lipopolysaccharides; D012717:Sesquiterpenes; C552245:curcumenol; D009569:Nitric Oxide