New microbiological transformations of steroids by Streptomyces virginiae IBL-14.
A bacterium Streptomyces virginiae IBL-14 capable of effective degradation of diosgenin was isolated from activated sludge for treatment of waste from a steroidal drug factory. From the culture broth of diosgenin degradation, 11 compounds were purified and then identified, eight of which were previously unidentified compounds including 1-dehydroisonuatigenone [VI], nuatigenone [VIII], 1-dehydronuatigenone [X], 26-acetyl-nuatigenone [XII], 6-methoxy-6-dehydrodiosgenone [XIII], 6-methoxy-6-dehydroisonuatigenone [XIV], 6-methoxy-6-dehydronuatigenone [XV], and 6-dimethoxy-7alpha-hydroxyldiosgenone [XVI]. Additionally, two important microbial transformations of diosgenin (6-methoxylation and C25-tertiary carbon hydroxylation) were found. Two valuable chemical reactions of the steroids (structural rearrangement and esterification)were also confirmed. As a result, a new metabolic pathway of diosgenin metabolism was postulated.
Wang
Feng-Qing
FQ
State Key Laboratory of Bioreactor Engineering, New World Institute of Biotechnology, East China University of Science and Technology, Shanghai 200237, China.
Zhang
Cheng-Gang
CG
Li
Bo
B
Wei
Dong-Zhi
DZ
Tong
Wang-Yu
WY
D001419:Bacteria / Q000187:drug effects; D001711:Biotransformation; D002244:Carbon / Q000737:chemistry; D002621:Chemistry / Q000379:methods; D004144:Diosgenin / Q000032:analysis* / Q000737:chemistry; D004345:Drug Industry; D004951:Esterification; D007220:Industrial Waste; D008956:Models, Chemical; D011208:Powders; D012722:Sewage; D013256:Steroids / Q000737:chemistry*; D013302:Streptomyces / Q000378:metabolism*
D007220:Industrial Waste; D011208:Powders; D012722:Sewage; D013256:Steroids; D002244:Carbon; D004144:Diosgenin