Triple quadrupole tandem mass spectrometry of sesquiterpene lactones: a study of goyazensolide and its congeners

✍ Scribed by Antônio E. M. Crotti; João L. C. Lopes; Norberto P. Lopes

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 117 KB
• Volume: 40
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/jms.877

✦ Synopsis

Abstract

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.