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Characterization of C‐glycosyl quinochalcones in Carthamus tinctorius L. by ultraperformance liquid chromatography coupled with quadrupole‐time‐of‐flight mass spectrometry
Author(s) -
Jin Yu,
Zhang Xiuli,
Shi Hui,
Xiao Yuansheng,
Ke Yanxiong,
Xue Xingya,
Zhang Feifang,
Liang Xinmiao
Publication year - 2008
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.3468
Subject(s) - chemistry , glycosyl , carthamus , fragmentation (computing) , mass spectrometry , ion , cleavage (geology) , chromatography , polyatomic ion , stereochemistry , analytical chemistry (journal) , organic chemistry , medicine , geotechnical engineering , fracture (geology) , computer science , engineering , traditional medicine , operating system
C‐Glycosyl quinochalcones are unique components in Carthamus tinctorius L. The reported C‐glycosyl quinochalcones have the same quinochalcone skeleton with a hydroxyl group at the 5'‐position and a glucose linked to this position with a carbon–carbon bond. In this study, the standard hydroxysafflor yellow A and water‐extracted fraction of Carthamus tinctorius L. were analyzed by ultraperformance liquid chromatography coupled with quadrupole‐time‐of‐flight mass spectrometry (UPLC/Q‐TOFMS) in both positive and negative ion modes. The fragmentation pathways of C‐glycosyl quinochalcones were interpreted and validated by accurate mass measurement. Their fragmentation showed a special cleavage at the C–C bond except for the typical internal cleavage at the sugar moiety of other C‐glycosyl flavonoids. In positive ion mode, cleavage of the 5'‐glucose produced an [M+H–162] + ion by a neutral loss, while cleavage of the 5'‐glucose in negative ion mode led to an [MH–163] − . ion by radical cleavage. The cleavage from the carbonyl group produced fragment ions containing an A or a B ring. The fragment ions containing an A ring were common product ions of seven compounds in both ion modes, and fragment ions containing the B ring were used to judge the different substituent groups at the 3'‐position. The fragmentation patterns of seven structurally related C‐glycosyl quinochalcones were analyzed systematically and the formation of the fragment ions in two modes is explained in detail in this report. UPLC/Q‐TOFMS is an effective tool for characterizing a complex sample, which gives higher resolution separation and generates accurate mass measurement of the product ions. Copyright © 2008 John Wiley & Sons, Ltd.