Microbial transformation of epothilone A by Aspergillus niger AS 3.739.
The microbiological transformation of epothilone A (1) by Aspergillus niger AS 3.739 afforded four main metabolites. Their structures were elucidated by (1)H, (13)C NMR and HSQC, COSY, HMBC, and NOESY spectra as trans-12,13-hydroxylated epothilone A (2), cis-12,13-hydroxylated epothilone A (3), trans-12,15-epoxidated epothilone A (4), and cis-12,15-epoxidated epothilone A (5). All four compounds were firstly found based on their stereochemistry. These new compounds displayed cytotoxicity against human breast carcinoma cells MCF-7 with IC(50) 9.88 microg/ml of 2, 2.52 microg/ml of 3, 9.88 microg/ml of 4, and 5.68 microg/ml of 5.
Beijing Institute of Radiation Medicine, Beijing, China.
Yan-Liang
YL
Wang
He
H
Wang
Yu-Xin
YX
Lu
Xiao-Chen
XC
Cheng
Li-Li
LL
Han
Shou-Jun
SJ
Yuan
De-Xuan
DX
Yang
Qing-Lin
QL
Zhang
Chu-Tse
CT
Wu
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000378:metabolism*; D001234:Aspergillus niger / Q000378:metabolism*; D001711:Biotransformation; D004354:Drug Screening Assays, Antitumor; D034261:Epothilones / Q000737:chemistry / Q000378:metabolism*; D005260:Female; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D000972:Antineoplastic Agents, Phytogenic; D034261:Epothilones; C093787:epothilone A