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Fatty acid neutral losses observed in tandem mass spectrometry with collision-induced dissociation allows regiochemical assignment of sulfoquinovosyl-diacylglycerols.
MedLine Citation:
PMID:  23378093     Owner:  NLM     Status:  In-Data-Review    
Abstract/OtherAbstract:
A full characterization of sulfoquinovosyldiacylglycerols (SQDGs) in the lipid extract of spinach leaves has been achieved using liquid chromatography/electrospray ionization-linear quadrupole ion trap mass spectrometry (MS). Low-energy collision-induced dissociation tandem MS (MS/MS) of the deprotonated species [M - H](-) was exploited for a detailed study of sulfolipid fragmentation. Losses of neutral fatty acids from the acyl side chains (i.e. [M - H - RCOOH](-) ) were found to prevail over ketene losses ([M - H - R'CHCO](-) ) or carboxylates of long-chain fatty acids ([RCOO](-) ), as expected for gas-phase acidity of SQDG ions. A new concerted mechanism for RCOOH elimination, based on a charge-remote fragmentation, is proposed. The preferential loss of a fatty acids molecule from the sn-1 position (i.e. [M - H - R(1) COOH](-) ) of the glycerol backbone, most likely due to kinetic control of the gas-phase fragmentation process, was exploited for the regiochemical assignment of the investigated sulfolipids. As a result, 24 SQDGs were detected and identified in the lipid extract of spinach leaves, their number and variety being unprecedented in the field of plant sulfolipids. Moreover, the prevailing presence of a palmitic acyl chain (16:0) on the glycerol sn-2 position of spinach SQDGs suggests a prokaryotic or chloroplastic path as the main route for their biosynthesis. Copyright © 2013 John Wiley & Sons, Ltd.
Authors:
Rosalia Zianni; Giuliana Bianco; Filomena Lelario; Ilario Losito; Francesco Palmisano; Tommaso R I Cataldi
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of mass spectrometry : JMS     Volume:  48     ISSN:  1096-9888     ISO Abbreviation:  J Mass Spectrom     Publication Date:  2013 Feb 
Date Detail:
Created Date:  2013-02-04     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9504818     Medline TA:  J Mass Spectrom     Country:  England    
Other Details:
Languages:  eng     Pagination:  205-15     Citation Subset:  IM    
Copyright Information:
Copyright © 2013 John Wiley & Sons, Ltd.
Affiliation:
Dipartimento di Chimica, Università degli Studi di Bari Aldo Moro, Campus Universitario, Via E. Orabona, 4-70126, Bari, Italy.
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