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J Biol Chem. 2019 Jul 5;294(27):10698-10707. doi: 10.1074/jbc.RA118.006956. Epub 2019 May 31.

Linoleic acid esters of hydroxy linoleic acids are anti-inflammatory lipids found in plants and mammals.

Author information

1
From the Clayton Foundation Laboratories for Peptide Biology, Salk Institute for Biological Studies, La Jolla, California 92037.
2
the Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, La Jolla, California 92093-0934.
3
the Division of Experimental Vascular Research, Department of Clinical Sciences, Lund University, Box 117, 221 00 Lund, Sweden, and.
4
Härröd Research, Frans Persons väg 6, 40229 Gothenburg, Sweden.
5
the Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, La Jolla, California 92093-0934, drsiegel@ucsd.edu.
6
From the Clayton Foundation Laboratories for Peptide Biology, Salk Institute for Biological Studies, La Jolla, California 92037, asaghatelian@salk.edu.

Abstract

Fatty acid esters of hydroxy fatty acids (FAHFAs) are a recently discovered class of biologically active lipids. Here we identify the linoleic acid ester of 13-hydroxy linoleic acid (13-LAHLA) as an anti-inflammatory lipid. An oat oil fraction and FAHFA-enriched extract from this fraction showed anti-inflammatory activity in a lipopolysaccharide-induced cytokine secretion assay. Structural studies identified three LAHLA isomers (15-, 13-, and 9-LAHLA) as being the most abundant FAHFAs in the oat oil fraction. Of these LAHLAs, 13-LAHLA is the most abundant LAHLA isomer in human serum after ingestion of liposomes made of fractionated oat oil, and it is also the most abundant endogenous LAHLA in mouse and human adipose tissue. As a result, we chemically synthesized 13-LAHLA for biological assays. 13-LAHLA suppresses lipopolysaccharide-stimulated secretion of cytokines and expression of pro-inflammatory genes. These studies identify LAHLAs as an evolutionarily conserved lipid with anti-inflammatory activity in mammalian cells.

KEYWORDS:

FAHFAs; LAHLAs; inflammation; lipid; lipid signaling; lipid structure; lipid synthesis

PMID:
31152059
PMCID:
PMC6615670
[Available on 2020-07-05]
DOI:
10.1074/jbc.RA118.006956

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