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Low energy induced homolytic fragmentation of flavonol 3-O-glycosides by negative electrospray ionization tandem mass spectrometry
Yang, Wen-Zhi1; Qiao, Xue1; Bo, Tao2; Wang, Qing1; Guo, De-An1; Ye, Min1
刊名RAPID COMMUNICATIONS IN MASS SPECTROMETRY
2014-02-28
DOI10.1002/rcm.6794
28期:4页:385-395
收录类别SCI
文章类型Article
WOS标题词Science & Technology
类目[WOS]Biochemical Research Methods ; Chemistry, Analytical ; Spectroscopy
研究领域[WOS]Biochemistry & Molecular Biology ; Chemistry ; Spectroscopy
关键词[WOS]COLLISION-INDUCED DISSOCIATION ; STRUCTURAL-CHARACTERIZATION ; ION ELECTROSPRAY ; O-GLYCOSIDES ; GLYCOSYLATION ; DIFFERENTIATION ; EXTRACTION ; SEPARATION ; CLEAVAGE
英文摘要

RATIONALENegative ESI-QIT-MS of several subtypes of flavonoid O-glycosides is known to produce deprotonated molecular ions which undergo homolytic fragmentation at the glycosidic bond upon collision-induced dissociation (CID). However, these subtypes have never been simultaneously compared under unified MS conditions.

METHODSThe (-)-ESI-MSn fragmentations of 69 flavonoid O-glycosides, involving eight subtypes, were analyzed using a quadrupole ion-trap mass spectrometer with collision energies varying from 18-44%. Factors influencing the homolytic glycosidic bond fragmentation, such as collision energy, hydroxylation of aglycone, and glycosylation pattern, were comprehensively studied.

RESULTSUnder the unified CID-QIT-MS2 conditions, the precursor deprotonated molecular ions [M-H](-) for 3-O-glycosyl, 3,7-di-O-glycosyl and 3,6,7-tri-O-glycosyl flavonols experienced homolytic fragmentation at the glycosidic bond and generated the radical aglycone ion [Y-0-H](-center dot). This gas-phase CID fragmentation behavior was not observed for the other subtypes. A general trend was found that hydroxyl substitution at C-6, glycosylation at C-6/C-7, and acetylation of the saccharide moiety remarkably suppressed this fragmentation. In addition, flavonol 3-O-diglycosides (disaccharides) possessing a 12 glycosidic bond generated more abundant [Y-0-H](-center dot) product ions than those with a 13 or 16 bond. The terminal sugar triggered the homolytic fragmentation in the order Rha>Xyl>Glc. Moreover, new counterexamples were found for previously reported fragmentation rules.

CONCLUSIONSThe low-energy CID homolytic fragmentation was diagnostic for structural identification of flavonol 3-O-glycosides. We have summarized key factors affecting this fragmentation. The results could be useful for rapid characterization of flavonoid O-glycosides in complicated herbal extracts. Copyright (c) 2014 John Wiley & Sons, Ltd.

语种英语
WOS记录号WOS:000329308100008
引用统计
被引频次:19[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/54331
专题北京大学药学院
作者单位1.Agilent Technol, Beijing 100102, Peoples R China
2.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
Yang, Wen-Zhi,Qiao, Xue,Bo, Tao,et al. Low energy induced homolytic fragmentation of flavonol 3-O-glycosides by negative electrospray ionization tandem mass spectrometry[J]. RAPID COMMUNICATIONS IN MASS SPECTROMETRY,2014,28(4):385-395.
APA Yang, Wen-Zhi,Qiao, Xue,Bo, Tao,Wang, Qing,Guo, De-An,&Ye, Min.(2014).Low energy induced homolytic fragmentation of flavonol 3-O-glycosides by negative electrospray ionization tandem mass spectrometry.RAPID COMMUNICATIONS IN MASS SPECTROMETRY,28(4),385-395.
MLA Yang, Wen-Zhi,et al."Low energy induced homolytic fragmentation of flavonol 3-O-glycosides by negative electrospray ionization tandem mass spectrometry".RAPID COMMUNICATIONS IN MASS SPECTROMETRY 28.4(2014):385-395.
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