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Characteristic fragmentation behavior of some glucuronide‐type triterpenoid saponins using electrospray ionization tandem mass spectrometry
Author(s) -
Li Bin,
Abliz Zeper,
Fu Guangmiao,
Tang Meijun,
Yu Shishan
Publication year - 2005
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.1803
Subject(s) - chemistry , fragmentation (computing) , aglycone , tandem mass spectrometry , electrospray ionization , mass spectrometry , glycosidic bond , electrospray , chromatography , glycoconjugate , stereochemistry , glycoside , organic chemistry , biochemistry , computer science , enzyme , operating system
Abstract The fragmentation behavior of some glucuronide‐type triterpenoid saponins from Symplocos chinensis , and their analogues escin Ia and Ib, were investigated by positive ion electrospray ionization tandem mass spectrometry using a quadrupole linear ion trap mass spectrometer. The fragmentation patterns of these saponins significantly changed in accordance with structural variations in the glucuronyl residue of the oligosaccharide chain. It was found that the carboxyl group and hydroxyl group at the C‐3′ position of the glucuronyl residue were the key sites for determining the fragmentation behavior of these compounds. When the carboxyl group was esterified, only the C 2α ion, and no B 2α ion, and cationized aglycone were observed. When the hydroxyl group at C‐3′ was acylated, the inherent cross‐ring cleavage was hindered. However, glycosidic cleavages always occurred, regardless of the crucial structural variations. The results of the present studies can benefit the determination of trace triterpenoid saponins of this type in crude plant extracts, and also provide background information to aid the structural investigations of similar glycoconjugates. Copyright © 2005 John Wiley & Sons, Ltd.