title: Microbial transformations of diosgenin by the white-rot basidiomycete Coriolus versicolor.
abstract: Microbial transformation of diosgenin (3β-hydroxy-5-spirostene) using white-rot fungus Coriolus versicolor afforded four previously unreported polyhydroxylated steroids, 25(R)-spirost-5-en-3β,7α,15α,21-tetraol (5), 25(R)-spirost-5-en-3β,7β,12β,21-tetrol (6), (25R)-spirost-5-en-3β,7α,12β,21-tetraol (7), and (25R)-spirost-5-en-3β,7β,11α,21-tetraol (8), along with three known congeners, 25(R)-spirost-5-en-3β,7β-diol (2), 25(R)-spirost-5-en-3β,7β,21-triol (3), and 25(R)-spirost-5-en-3β,7β,12β-triol (4). These structures were elucidated by 1D and 2D NMR as well as HR-ESIMS analysis. In addition, we provide evidence for two new microbial hydroxylations of diosgenin: C-21 primary carbon hydroxylation and C-15 hydroxylation. The 3β-hydroxyl group and double bond in the B-ring of diosgenin were found to be important structural determinants for their activity.
authors: Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, College of Science, Northwest A & F University, Yangling 712100, Shaanxi, People's Republic of China.
authors: Guang-Wei
authors: GW
authors: Wu
authors: Jin-Ming
authors: JM
authors: Gao
authors: Xin-Wei
authors: XW
authors: Shi
authors: Qiang
authors: Q
authors: Zhang
authors: Shao-Peng
authors: SP
authors: Wei
authors: Kan
authors: K
authors: Ding
mesh_terms: D001487:Basidiomycota / Q000737:chemistry* / Q000378:metabolism; D001711:Biotransformation; D004144:Diosgenin / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D016328:NF-kappa B / Q000187:drug effects / Q000378:metabolism; D019906:Nuclear Magnetic Resonance, Biomolecular; D013256:Steroids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D016328:NF-kappa B; D013256:Steroids; D004144:Diosgenin