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Molecules 2016, 21(4), 437; doi:10.3390/molecules21040437

Identification of Oxygenated Fatty Acid as a Side Chain of Lipo-Alkaloids in Aconitum carmichaelii by UHPLC-Q-TOF-MS and a Database

1
State Key Laboratory of Quality Research in Chinese Medicine, Macau Institute for Applied Research in Medicine and Health, Macau University of Science and Technology, Avenida Wai Long, Taipa, Macao, China
2
School of Chinese Medicines, Macau University of Science and Technology, Avenida Wai Long, Taipa, Macao, China
3
International Institute for Translational Chinese Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
4
School of Basic Medicinal Sciences and Nursing, Chengdu University, Chengdu 610106, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 18 February 2016 / Revised: 24 March 2016 / Accepted: 28 March 2016 / Published: 31 March 2016
(This article belongs to the Collection Herbal Medicine Research)
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Abstract

Lipo-alkaloid is a kind of C19-norditerpenoid alkaloid usually found in Aconitum species. Structurally, they contain an aconitane skeleton and one or two fatty acid moieties of 3–25 carbon chains with 1–6 unsaturated degrees. Analysis of the lipo-alkaloids in roots of Aconitum carmichaelii resulted in the isolation of six known pure lipo-alkaloids (A1–A6) and a lipo-alkaloid mixture (A7). The mixture shared the same aconitane skeleton of 14-benzoylmesaconine, but their side chains were determined to be 9-hydroxy-octadecadienoic acid, 13-hydroxy-octadecadienoic acid and 10-hydroxy-octadecadienoic acid, respectively, by MS/MS analysis after alkaline hydrolysis. To our knowledge, this is the first time of the reporting of the oxygenated fatty acids as the side chains in naturally-occurring lipo-alkaloids. In order to identify more lipo-alkaloids, a compound database was established based on various combinations between the aconitane skeleton and the fatty acid chain, and then, the identification of lipo-alkaloids was conducted using the database, UHPLC-Q-TOF-MS and MS/MS. Finally, 148 lipo-alkaloids were identified from A. carmichaelii after intensive MS/MS analysis, including 93 potential new compounds and 38 compounds with oxygenated fatty acid moieties. View Full-Text
Keywords: Aconitum carmichaelii; lipo-alkaloids; C19-aconitane skeletons; oxygenated fatty acids; UHPLC-Q-TOF-MS Aconitum carmichaelii; lipo-alkaloids; C19-aconitane skeletons; oxygenated fatty acids; UHPLC-Q-TOF-MS
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Liang, Y.; Wu, J.-L.; Leung, E.L.-H.; Zhou, H.; Liu, Z.; Yan, G.; Liu, Y.; Liu, L.; Li, N. Identification of Oxygenated Fatty Acid as a Side Chain of Lipo-Alkaloids in Aconitum carmichaelii by UHPLC-Q-TOF-MS and a Database. Molecules 2016, 21, 437.

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