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Molecules 2017, 22(4), 489; doi:10.3390/molecules22040489

Metabolic Profile of Skimmianine in Rats Determined by Ultra-Performance Liquid Chromatography Coupled with Quadrupole Time-of-Flight Tandem Mass Spectrometry

1
Key Laboratory of Ministry of Education, Research Center of Chinese Herbal Resources and Engineering, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
2
School of Chinese Materia Medica, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
*
Author to whom correspondence should be addressed.
Academic Editor: Marcello Iriti
Received: 25 January 2017 / Revised: 5 March 2017 / Accepted: 15 March 2017 / Published: 23 March 2017
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Abstract

Skimmianine is a furoquinoline alkaloid present mainly in the Rutaceae family. It has been reported to have analgesic, antispastic, sedative, anti-inflammatory, and other pharmacologic activities. Despite its critical pharmacological function, its metabolite profiling is still unclear. In this study, the in vivo metabolite profiling of skimmianine in rats was investigated using ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UPLC/Q-TOF-MS). The metabolites were predicted using MetabolitePilotTM software. These predicted metabolites were further analyzed by MS2 spectra, and compared with the detailed fragmentation pathway of the skimmianine standard and literature data. A total of 16 metabolites were identified for the first time in rat plasma, urine, and feces samples after oral administration of skimmianine. Skimmianine underwent extensive Phase I and Phase II metabolism in rats. The Phase I biotransformations of skimmianine consist of epoxidation of olefin on its furan ring (M1) followed by the hydrolysis of the epoxide ring (M4), hydroxylation (M2, M3), O-demethylation (M5-M7), didemethylation (M14–M16). The Phase II biotransformations include glucuronide conjugation (M8–M10) and sulfate conjugation (M11–M13). The epoxidation of 2,3-olefinic bond followed by the hydrolysis of the epoxide ring and O-demethylation were the major metabolic pathways of skimmianine. The results provide key information for understanding the biotransformation processes of skimmianine and the related furoquinoline alkaloids. View Full-Text
Keywords: skimmianine; metabolites; UPLC/Q-TOF-MS; furoquinoline skimmianine; metabolites; UPLC/Q-TOF-MS; furoquinoline
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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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Huang, A.; Xu, H.; Zhan, R.; Chen, W.; Liu, J.; Chi, Y.; Chen, D.; Ji, X.; Luo, C. Metabolic Profile of Skimmianine in Rats Determined by Ultra-Performance Liquid Chromatography Coupled with Quadrupole Time-of-Flight Tandem Mass Spectrometry. Molecules 2017, 22, 489.

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