Differentiation between 3,4- and 4,15-Epoxyeudesmanolides by Electrospray Ionization Tandem Mass Spectrometry
Joint Authors
Crotti, Antônio Eduardo Miller
Dias, Herbert Júnior
Stefani, Ricardo
Tomaz, José Carlos
Vessecchi, Ricardo
Source
Journal of Analytical Methods in Chemistry
Issue
Vol. 2017, Issue 2017 (31 Dec. 2017), pp.1-9, 9 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2017-11-06
Country of Publication
Egypt
No. of Pages
9
Main Subjects
Abstract EN
We investigated the fragmentation of the eudesmanolide-type sesquiterpene lactones 1α-(4-hydroxymethacryloyloxy)-3α,4α-epoxy-8α-hydroxyeudesm-11(13)-6α,12-olide (1) and 1α-(2,3-epoxyangeloyloxy)-4α,15-epoxy-8α-hydroxyeudesm-11(13)-6α,12-olide (2) by electrospray ionization tandem mass spectrometry (ESI-MS/MS).
The elimination of the different ester substituent at C(1) directly from protonated 1 and 2 (A) led to the formation of two regioisomer product ions B (A − RCO2H).
Further fragmentation of B resulted from consecutive eliminations of H2O and CO molecules.
However, we identified four product ions that allowed for the differentiation between 3,4- and 4,15-epoxyeudesmanolides.
The formation of these diagnostic ions was associated with the C(3)–O bond of compound 1, which propitiates the participation of the lone pair of the oxygen epoxide in the formation of B through a Grob-Wharton-type fragmentation, then resulting in an alternative fragmentation pathway.
These data can be useful for the fast differentiation between epoxyeudesmanolide regioisomers directly from Dimerostemma extracts by liquid chromatography-tandem mass spectrometry (LC-MS/MS), as an alternative to NMR, or even for quantitation studies of these compounds using multiple reaction monitoring (MRM) scan.
American Psychological Association (APA)
Dias, Herbert Júnior& Stefani, Ricardo& Tomaz, José Carlos& Vessecchi, Ricardo& Crotti, Antônio Eduardo Miller. 2017. Differentiation between 3,4- and 4,15-Epoxyeudesmanolides by Electrospray Ionization Tandem Mass Spectrometry. Journal of Analytical Methods in Chemistry،Vol. 2017, no. 2017, pp.1-9.
https://search.emarefa.net/detail/BIM-1170318
Modern Language Association (MLA)
Dias, Herbert Júnior…[et al.]. Differentiation between 3,4- and 4,15-Epoxyeudesmanolides by Electrospray Ionization Tandem Mass Spectrometry. Journal of Analytical Methods in Chemistry No. 2017 (2017), pp.1-9.
https://search.emarefa.net/detail/BIM-1170318
American Medical Association (AMA)
Dias, Herbert Júnior& Stefani, Ricardo& Tomaz, José Carlos& Vessecchi, Ricardo& Crotti, Antônio Eduardo Miller. Differentiation between 3,4- and 4,15-Epoxyeudesmanolides by Electrospray Ionization Tandem Mass Spectrometry. Journal of Analytical Methods in Chemistry. 2017. Vol. 2017, no. 2017, pp.1-9.
https://search.emarefa.net/detail/BIM-1170318
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-1170318