Tandem mass spectrometric analysis and density functional theory calculations on the fragmentation behavior of two tetradecanoylingenol regioisomers from Euphorbia wallichii

	Tandem mass spectrometric analysis and density functional theory calculations on the fragmentation behavior of two tetradecanoylingenol regioisomers from Euphorbia wallichii
	Xia, Bing ; Xu, Kaijie ; Liu, Xin ; Chai, Yunfeng ; Sun, Cuirong ; Gu, Yucheng ; Ding, Lisheng ; Zhou, Yan
刊名	RAPID COMMUNICATIONS IN MASS SPECTROMETRY
	2012
卷号	26 期号:21 页码:2502-2508
ISSN号	0951-4198
通讯作者	Zhou, Y (reprint author), Chinese Acad Sci, Chengdu Inst Biol, Key Lab Mt Ecol Restorat & Bioresource Utilizat, Chengdu 610041, Peoples R China.
产权排序	1
英文摘要	RATIONALE Two structurally similar bioactive regioisomers, 3-O-tetradecanoylingenol and 20-O-tetradecanoylingenol, from Euphorbia wallichii presented quite different fragmentation behaviors. Revealing the related fragmentation pathways may improve the efficiency of characterization and identification of such type of compounds. METHODS The two regioisomers were subjected to collision-induced dissociation (CID) on Finnigan LCQDECA and LTQ Orbitrap XL instruments. Based on the CID results, the possible fragmentation pathways were proposed and investigated with density functional theory (DFT) calculations. RESULTS Elimination of C14H28O2 (tetradecanoic acid) for 3-O-tetradecanoylingenol and the sequential losses of C4H8 (butylene) for 20-O-tetradecanoylingenol were observed in ESI-MS/MS, witnessed also by HR-ESI-MS/MS. The fragmentation pathways were proposed and verified by calculating the activation energy of their transition states by DFT calculations. CONCLUSIONS Based on the observations, fragmentation pathways for the two regioisomers were proposed and verified by calculating the energy of the reactants, products and the corresponding transition states using DFT. This report should have value in rapid identification of the derivatives of ingenol and other regioisomers in natural products. Copyright (C) 2012 John Wiley & Sons, Ltd.
学科主题	Biochemistry & Molecular Biology; Chemistry; Spectroscopy
收录类别	SCI
资助信息	National Natural Sciences Foundation of China [30973634, 21072185]; Chinese Academy of Sciences; Syngenta PhD fellowship
语种	英语
WOS记录号	WOS:000309182200003
公开日期	2013-07-03
内容类型	期刊论文
源URL	[http://210.75.237.14/handle/351003/23875]
专题	成都生物研究所_天然产物研究
推荐引用方式 GB/T 7714	Xia, Bing,Xu, Kaijie,Liu, Xin,et al. Tandem mass spectrometric analysis and density functional theory calculations on the fragmentation behavior of two tetradecanoylingenol regioisomers from Euphorbia wallichii[J]. RAPID COMMUNICATIONS IN MASS SPECTROMETRY,2012,26(21):2502-2508.
APA	Xia, Bing.,Xu, Kaijie.,Liu, Xin.,Chai, Yunfeng.,Sun, Cuirong.,...&Zhou, Yan.(2012).Tandem mass spectrometric analysis and density functional theory calculations on the fragmentation behavior of two tetradecanoylingenol regioisomers from Euphorbia wallichii.RAPID COMMUNICATIONS IN MASS SPECTROMETRY,26(21),2502-2508.
MLA	Xia, Bing,et al."Tandem mass spectrometric analysis and density functional theory calculations on the fragmentation behavior of two tetradecanoylingenol regioisomers from Euphorbia wallichii".RAPID COMMUNICATIONS IN MASS SPECTROMETRY 26.21(2012):2502-2508.