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Triple quadrupole tandem mass spectrometry of sesquiterpene lactones: a study of goyazensolide and its congeners
Author(s) -
Crotti Antônio E. M.,
Lopes João L. C.,
Lopes Norberto P.
Publication year - 2005
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.877
Subject(s) - chemistry , sesquiterpene , tandem , mass spectrometry , tandem mass spectrometry , triple quadrupole mass spectrometer , quadrupole , selected reaction monitoring , stereochemistry , chromatography , aerospace engineering , physics , atomic physics , engineering
Electrospray ionization tandem mass spectrometry (ESI‐MS/MS) was used to investigate the fragmentation pattern of ten sesquiterpene lactones of the goyazensolide type under low‐energy collision‐induced dissociation (CID) using a triple quadrupole mass spectrometer. The analysis revealed that loss of CO 2 [M + H − 44] + is the predominant process for compounds that exhibit a hydroxyl at C‐8. In contrast, compounds with different acyloxy groups at C‐8 fragment by means of elimination of the corresponding carboxylic acids [M + H − (R 2 CO 2 H)] + and consecutive losses of CO and H 2 O. Our results also demonstrate the influence of both the stereochemistry of the acyloxy group at C‐8 on the relative abundances of product ions and the hydroxyl at C‐15, which creates an additional pathway, resulting in highly diagnostic product ions. This work clearly demonstrates the utility of tandem quadrupole low‐resolution mass spectrometry for studies on the rationalization of the fragmentation of a series of compounds with a highly conserved core structure, but differing in substituent groups. Copyright © 2005 John Wiley & Sons, Ltd.