Liquid chromatography-tandem mass spectrometry for the identification of L-tetrahydropalmatine metabolites in Penicillium janthinellum and rats.
L-tetrahydropalmatine (L-THP) is an active alkaloid from Stephania ainiaca Diels. In order to compare the similarities and differences of microbial and mammalian metabolisms of L-THP, the microbial transformation by Penicillium janthinellum and metabolism in rats were investigated. Biotransformation of L-THP by Penicillium janthinellum AS 3.510 resulted in the formation of three metabolites. Their structures were identified as L-corydalmine, L-corypalmine and 9-O-desmethyl-L-THP, respectively, by comprehensive nuclear magnetic resonance and mass spectrometry (MS) analysis. Six metabolites (M1-M6) were detected from the in vivo study in rats and three of which (L-corydalmine, L-corypalmine and 9-O-desmethyl-L-THP) were identified as the same compounds as those obtained from microbial metabolism by liquid chromatography-tandem mass spectrometry (LC-MS/MS) analysis and comparison with reference standards obtained from microbial metabolism. The structures of the additional three metabolites were tentatively deduced as 2-O-desmethyl-L-THP and two di-O-demethylated L-THP by LC-MS/MS analysis. Time courses of microbial and rat metabolisms of L-THP were also investigated.
Li
Li
L
Shanghai Research Center for TCM Modernization, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Zhangjiang Guo Shoujing Road 199, Shanghai 201203, People's Republic of China.
Ye
Min
M
Bi
Kaishun
K
Guo
Dean
D
D000818:Animals; D001600:Berberine Alkaloids / Q000378:metabolism* / Q000652:urine; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D005243:Feces / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry / Q000379:methods*; D010407:Penicillium / Q000378:metabolism*; D051381:Rats; D017207:Rats, Sprague-Dawley; D013056:Spectrophotometry, Ultraviolet
D001600:Berberine Alkaloids; C014215:tetrahydropalmatine