Microbial biotransformation of cryptotanshinone by Cunninghamella elegans and its application for metabolite identification in rat bile.
Cryptotanshinone (1) is one of the major bioactive constituents in Salvia miltiorrhiza Bunge. Preparative-scale biotransformation of cryptotanshinone by Cunninghamella elegans (AS 3.2082) produced three new products, which were identified as (3R,15R)-3-hydroxycryptotanshinone (2), (3S,15R)-3-hydroxycryptotanshinone (3), and (4S,15R)-18-hydroxycryptotanshinone (4), respectively. The structural elucidation was based primarily on 1D and 2D NMR and HR-ESI-MS analyses. The absolute configuration of these three products was confirmed by comparison of their circular dichroism spectra with those of the known compounds. These biotransformed metabolites were used as for the comparison of in vivo metabolites in rat bile sample after intravenous administration and they are identical to three of the minor hydroxylated metabolites in vivo, which suggested that microbial biotransformation model was a useful and feasible approach for the preparation of mammalian metabolites in trace.
Sun
Jiang-Hao
JH
The State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, China.
Yang
Min
M
Ma
Xiao-Chi
XC
Kang
Jie
J
Han
Jian
J
Guo
De-An
DA
D000818:Animals; D001646:Bile / Q000737:chemistry*; D001711:Biotransformation; D020093:Cunninghamella / Q000378:metabolism*; D008297:Male; D015394:Molecular Structure; D010616:Phenanthrenes / Q000378:metabolism*; D051381:Rats; D017207:Rats, Sprague-Dawley; D027561:Salvia miltiorrhiza / Q000737:chemistry*; D013237:Stereoisomerism
D010616:Phenanthrenes; C037886:cryptotanshinone