Biomimetic nitration of conjugated linoleic acid: formation and characterization of naturally occurring conjugated nitrodienes.

The Journal of Organic Chemistry
Steven R WoodcockBruce A Freeman

Abstract

Nitro-conjugated linoleic acids (NO2-cLA), endogenous nitrodiene lipids which act as inflammatory signaling mediators, were isolated and single isomers purified from the biomimetic acidic nitration products of conjugated linoleic acid (CLA). Structures were elucidated by means of detailed NMR and HPLC-MS/MS spectroscopic analysis and the relative double bond configurations assigned. Additional synthetic methods produced useful quantities and similar isomeric distributions of these unusual and reactive compounds for biological studies and isotopic standards, and the potential conversion of nitro-linoleic to nitro-conjugated linoleic acids was explored via a facile base-catalyzed isomerization. This represents one of the few descriptions of naturally occurring conjugated nitro dienes (in particular, 1-nitro 1,3-diene), an unusual and highly reactive motif with few biological examples extant.

References

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Jul 3, 2013·Prostaglandins, Leukotrienes, and Essential Fatty Acids·Maria Cristina MeleSebastiano Banni

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Citations

Dec 29, 2016·Nitric Oxide : Biology and Chemistry·María N PadillaJuan B Barroso
Dec 4, 2016·Journal of Lipid Research·Marco FazzariBruce A Freeman
Dec 8, 2016·The Journal of Biological Chemistry·Lucía TurellFrancisco J Schopfer
Oct 31, 2020·The Journal of Biological Chemistry·Mara CarreñoAna Denicola
Jan 18, 2021·The Journal of Biological Chemistry·Mara CarreñoAna Denicola

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