| Lipid Markers of Geometrical Radical Stress: Synthesis of Mono-Trans Cholesteryl Ester Isomers and Detection in Human Plasma. | |
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MedLine Citation:
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PMID: 21851063 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Heteroatom-centered free radicals are able to transform cis unsaturated fatty acids to the thermodynamically more stable, but unnatural, trans configuration. The "geometrical" radical stress can be estimated in biological samples using trans fatty acid isomers as lipid markers. Regioselectivity is an important feature of the "geometrical" radical stress, since the supramolecular organization of the polyunsaturated fatty acid moieties of phospholipids can bring to preferential mono-trans isomer formation. The regioisomer recognition is a crucial step, which is helped by appropriate molecular libraries available through radical-based synthetic meth-odologies. Cholesteryl linoleate and arachidonate esters are interesting targets for their biochemical connection with membrane phos-pholipid turnover and their well-known roles in cardiovascular health. The synthesis of mono-trans isomers of PUFA cholesteryl esters was achieved by a thiyl radical-catalyzed cis-trans isomerization. Valuable NMR, IR and Raman spectroscopic data have been collected for promising application in metabolomics and lipidomics. The identification of mono-trans cholesteryl ester isomers was carried out in human plasma by GC, Raman and IR analyses, evidencing for the first time the presence of specific regiosiomers connected to free radical stress. This work contributes to highlight the chemical biology approach for the access to molecular libraries applicable to biomarker development, and the cis-trans isomerization as a relevant process to be integrated in the puzzling scenario of free radical-mediated lipid modifications. |
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Authors:
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Michele Melchiorre; Armida Torreggiani; Chryssostomos Chatgilialoglu; Carla Ferreri |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-8-17 |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: - ISSN: 1520-5126 ISO Abbreviation: - Publication Date: 2011 Aug |
Date Detail:
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Created Date: 2011-8-19 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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