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Molecules 2012, 17(10), 11712-11720; doi:10.3390/molecules171011712
Article

Identification of Three New N-Demethylated and O-Demethyled Bisbenzylisoquinoline Alkaloid Metabolites of Isoliensinine from Dog Hepatic Microsomes

, ,  and *
Department of Pharmaceutical Analysis and Drug Metabolism, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, Zhejiang, China
* Author to whom correspondence should be addressed.
Received: 20 August 2012 / Revised: 24 September 2012 / Accepted: 26 September 2012 / Published: 1 October 2012
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Isoliensinine, a natural phenolic bisbenzyltetrahydroisoquinoline alkaloid, has received considerable attention for its potential biological effects such as antioxidant and anti-HIV activities. From the dog hepatic microsomes of isoliensinine, three new N-demethylated and O-demethylated metabolites, 2-N-desmethyl-isoliensinine (M1), 2'-N-desmethylisoliensinine (M2), and 2'-N-6-O-didesmethylisoliensinine (M3), were identified by high-performance liquid chromatography and data-dependent electrospray ionization tandem mass spectrometry. Possible metabolic pathways for isoliensinine have been proposed. The result should prove very helpful for evaluation of the drug-like properties of isoliensinine and other bisbenzylisoquinoline alkaloids.
Keywords: bisbenzylisoquinoline alkaloids; demethylation; HPLC; isoliensinine; microsomes; tandem mass spectrometry bisbenzylisoquinoline alkaloids; demethylation; HPLC; isoliensinine; microsomes; tandem mass spectrometry
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Zhou, H.; Li, L.; Jiang, H.; Zeng, S. Identification of Three New N-Demethylated and O-Demethyled Bisbenzylisoquinoline Alkaloid Metabolites of Isoliensinine from Dog Hepatic Microsomes. Molecules 2012, 17, 11712-11720.

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