Fragmentation pathways of oxygenated tetracyclic triterpenoids and their application in the qualitative analysis of Ganoderma lucidum by multistage tandem mass spectrometry

doi:10.1002/rcm.4989

	Fragmentation pathways of oxygenated tetracyclic triterpenoids and their application in the qualitative analysis of Ganoderma lucidum by multistage tandem mass spectrometry
	Cheng, Chun-Ru; Yang, Min; Wu, Zhi-Yuan; Wang, Yang; Zeng, Feng; Wu, Wan-Ying; Guan, Shu-Hong; Guo, De-An
刊名	RAPID COMMUNICATIONS IN MASS SPECTROMETRY
	2011-05-15
卷号	25 期号:9 页码:1323-1335
ISSN号	0951-4198
DOI	10.1002/rcm.4989
文献子类	Article
英文摘要	The fragmentation pathways of oxygenated tetracyclic triterpenoids from Ganoderma lucidum were systematically studied based on interpreting the mass spectra of 44 known triterpenoids using a combination of multistage tandem mass spectrometry (MS(n)) experiments and high-resolution mass spectrometry (HRMS) analysis. In negative ion mode, the fragmentation pathways of triterpenoid acids are rather characteristic. After the prominent loss of H(2)O or CO(2), cleavages take place on the A, B, C and D rings. Interestingly, the cleavage mode is highly dependent on the positions of the carbonyl groups and hydroxyl groups in the tetracyclic skeleton. Characteristic cleavage of ring A occurs in 7-oxo-11-H or 7-oxo-11-hydroxy derivatives; characteristic cleavage of ring B occurs in the 7-oxo-11-hydroxy derivatives; characteristic cleavage of ring C occurs in the 7-hydroxy-15-oxo derivatives; while the cleavage of ring D can be observed in the majority of the compounds investigated. The odd-electron species, which disobey the 'even-electron rule', are also observed and discussed in this paper. These phenomena provide an easy way to determine the tetracyclic skeleton and distinguish the isomers of the triterpenoids from each other. What is more, the fragmentation pathways of triterpenoid alcohols were also investigated in positive ion mode. The accurate masses of the product ions were determined using quadrupole orthogonal time-of-flight (QTOF) instruments. Finally, the fragmentation rules were applied to identify the components of G. lucidum. As a result, 73 triterpenoids including 11 new ones were identified. The triterpenoids were classified into six subclasses according to their different fragmentation behaviors. The application of tandem mass spectrometry was further explored. Copyright (C) 2011 John Wiley & Sons, Ltd.
资助项目	National Natural Science Foundation of China (NNSFC)[30701077] ; National Science & Technology Major Project 'Key New Drug Creation and Manufacturing Program', China[2009ZX09308-005] ; National Science & Technology Major Project 'Key New Drug Creation and Manufacturing Program', China[2009ZX09311-001] ; National Science & Technology Major Project 'Key New Drug Creation and Manufacturing Program', China[2009ZX09502-020] ; National Science & Technology Major Project 'Key New Drug Creation and Manufacturing Program', China[2009ZX09304-002] ; ministry of Sciences and Technology of China[2006BAI08B03-03] ; Chinese Academy Sciences[KSCX2-YW-R-166]
WOS关键词	EVEN-ELECTRON RULE ; LC-MS ; EXTRACTS ; IDENTIFICATION ; SPECTRA ; LIBRARY
WOS研究方向	Biochemistry & Molecular Biology ; Chemistry ; Spectroscopy
语种	英语
出版者	WILEY-BLACKWELL
WOS记录号	WOS:000290452600025
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/278526]
专题	成果转移转化处上海中药现代化研究中心
通讯作者	Guo, De-An
作者单位	Chinese Acad Sci, Shanghai Res Ctr Modernizat Tradit Chinese Med, Shanghai Inst Mat Med, Natl Engn Lab TCM Standardizat Technol,Shanghai I, Shanghai 201203, Peoples R China
推荐引用方式 GB/T 7714	Cheng, Chun-Ru,Yang, Min,Wu, Zhi-Yuan,et al. Fragmentation pathways of oxygenated tetracyclic triterpenoids and their application in the qualitative analysis of Ganoderma lucidum by multistage tandem mass spectrometry[J]. RAPID COMMUNICATIONS IN MASS SPECTROMETRY,2011,25(9):1323-1335.
APA	Cheng, Chun-Ru.,Yang, Min.,Wu, Zhi-Yuan.,Wang, Yang.,Zeng, Feng.,...&Guo, De-An.(2011).Fragmentation pathways of oxygenated tetracyclic triterpenoids and their application in the qualitative analysis of Ganoderma lucidum by multistage tandem mass spectrometry.RAPID COMMUNICATIONS IN MASS SPECTROMETRY,25(9),1323-1335.
MLA	Cheng, Chun-Ru,et al."Fragmentation pathways of oxygenated tetracyclic triterpenoids and their application in the qualitative analysis of Ganoderma lucidum by multistage tandem mass spectrometry".RAPID COMMUNICATIONS IN MASS SPECTROMETRY 25.9(2011):1323-1335.