| Fatty acid neutral losses observed in tandem mass spectrometry with collision-induced dissociation allows regiochemical assignment of sulfoquinovosyl-diacylglycerols. | |
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MedLine Citation:
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PMID: 23378093 Owner: NLM Status: In-Data-Review |
Abstract/OtherAbstract:
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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. |
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Authors:
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Rosalia Zianni; Giuliana Bianco; Filomena Lelario; Ilario Losito; Francesco Palmisano; Tommaso R I Cataldi |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Journal of mass spectrometry : JMS Volume: 48 ISSN: 1096-9888 ISO Abbreviation: J Mass Spectrom Publication Date: 2013 Feb |
Date Detail:
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Created Date: 2013-02-04 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9504818 Medline TA: J Mass Spectrom Country: England |
Other Details:
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Languages: eng Pagination: 205-15 Citation Subset: IM |
Copyright Information:
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Copyright © 2013 John Wiley & Sons, Ltd. |
Affiliation:
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Dipartimento di Chimica, Università degli Studi di Bari Aldo Moro, Campus Universitario, Via E. Orabona, 4-70126, Bari, Italy. |
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