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Molecules 2015, 20(2), 2100-2114; doi:10.3390/molecules20022100

Metabolic Profiling of the Uncaria Hook Alkaloid Geissoschizine Methyl Ether in Rat and Human Liver Microsomes Using High-Performance Liquid Chromatography with Tandem Mass Spectrometry

1
Tsumura Research Laboratories, Tsumura & Co., 3586 Yoshiwara, Ami-machi, Inashiki-gun, Ibaraki 300-1192, Japan
2
Kampo Formulation Development Center, Tsumura & Co., 3586 Yoshiwara, Ami-machi, Inashiki-gun, Ibaraki 300-1192, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 28 November 2014 / Accepted: 19 January 2015 / Published: 27 January 2015
(This article belongs to the Section Metabolites)
View Full-Text   |   Download PDF [809 KB, uploaded 27 January 2015]   |  

Abstract

Geissoschizine methyl ether (GM) is an indole alkaloid found in Uncaria hook, which is a galenical constituent of yokukansan, a traditional Japanese medicine. GM has been identified as the active component responsible for anti-aggressive effects. In this study, the metabolic profiling of GM in rat and human liver microsomes was investigated. Thirteen metabolites of GM were elucidated and identified using a high-performance liquid chromatography with tandem mass spectrometry method, and their molecular structures were proposed on the basis of the characteristics of their precursor ions, product ions, and chromatographic retention times. There were no differences in the metabolites between the rat and human liver microsomes. Among the 13 identified metabolites, there were two demethylation metabolites, one dehydrogenation metabolite, three methylation metabolites, three oxidation metabolites, two water-adduct metabolites, one di-demethylation metabolite, and one water-adduct metabolite followed by oxidation. The metabolic pathways of GM were proposed on the basis of this study. This study will be helpful in understanding the metabolic routes of GM and related Uncaria hook alkaloids, and provide useful information on the pharmacokinetics and pharmacodynamics. This is the first report that describes the separation and identification of GM metabolites in rat and human liver microsomes. View Full-Text
Keywords: geissoschizine methyl ether; Uncaria hook; metabolic profile; LC/MS/MS; rat liver microsome; human liver microsome geissoschizine methyl ether; Uncaria hook; metabolic profile; LC/MS/MS; rat liver microsome; human liver microsome
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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. (CC BY 4.0).

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MDPI and ACS Style

Kushida, H.; Matsumoto, T.; Igarashi, Y.; Nishimura, H.; Watanabe, J.; Maemura, K.; Kase, Y. Metabolic Profiling of the Uncaria Hook Alkaloid Geissoschizine Methyl Ether in Rat and Human Liver Microsomes Using High-Performance Liquid Chromatography with Tandem Mass Spectrometry. Molecules 2015, 20, 2100-2114.

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