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学科主题: 药学
题名:
Low energy induced homolytic fragmentation of flavonol 3-O-glycosides by negative electrospray ionization tandem mass spectrometry
作者: Yang, Wen-Zhi1; Qiao, Xue1; Bo, Tao2; Wang, Qing1; Guo, De-An1; Ye, Min1
刊名: RAPID COMMUNICATIONS IN MASS SPECTROMETRY
发表日期: 2014-02-28
DOI: 10.1002/rcm.6794
卷: 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
所属项目编号: 81222054 ; NCET-11-0019
项目资助者: National Natural Science Foundation of China ; Program for New Century Excellent Talents in University from the Chinese Ministry of Education
WOS记录号: WOS:000329308100008
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/54331
Appears in Collections:北京大学药学院_期刊论文

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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

Recommended Citation:
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.
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