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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Electrospray ionization tandem mass spectrometry of deprotonated dihydrobenzofuran neolignans

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Author(s):
Dias, Herbert J. [1] ; Crevelin, Eduardo J. [1] ; Palaretti, Vinicius [1] ; Vessecchi, Ricardo [1] ; Crotti, Antonio E. M. [1]
Total Authors: 5
Affiliation:
[1] Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Dept Quim, BR-14040901 Ribeirao Preto, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: RAPID COMMUNICATIONS IN MASS SPECTROMETRY; v. 35, n. 3 FEB 15 2021.
Web of Science Citations: 1
Abstract

Rationale Although dihydrobenzofuran neolignans (DBNs) display a wide diversity of biological activities, the identification of their in vivo metabolites using liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) remains a challenge to be overcome. Recently, ESI-MS/MS data of protonated DBNs have been reported, but they were shown to be limited due to the scarcity of diagnostic ions. Methods The gas-phase fragmentation pathways of a series of biologically active synthetic benzofuran neolignans (BNs) and DBNs were elucidated by means of negative ESI accurate-mass tandem and sequential mass spectrometry, and thermochemical data estimated using computational chemistry and the B3LYP/6-31+G(d,p) model. Results Deprotonated DBNs produced more diagnostic product ions than the corresponding protonated molecules. Moreover, a series of odd-electron product ions (radical anions) were detected, which has not been reported for protonated DBNs. Direct C2H3O2 center dot elimination from the precursor ion (deprotonated molecule) only occurred for the BNs and can help to distinguish these compounds from the DBNs. The mechanism through which the {[}M - H - CH3OH](-) ion is formed is strongly dependent on specific structural features. Conclusions The negative ion mode provides much more information than the positive ion mode (at least one diagnostic product ion was detected for all the analyzed compounds) and does not require the use of additives to produce the precursor ions (deprotonated molecules). (AU)

FAPESP's process: 13/20094-0 - Evaluation of the anti-parasitary and insecticidal activities of benzofuran derivatives, and study of their gas-phase fragmentation reactions using tandem mass spectrometry
Grantee:Antônio Eduardo Miller Crotti
Support Opportunities: Regular Research Grants