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

被引：90

作者：

Kolar, Matthew J. ^{[1
,5
]}

Konduri, Srihari ^{[2
]}

Chang, Tina ^{[1
]}

Wang, Huijing ^{[2
]}

McNerlin, Clare ^{[2
]}

Ohlsson, Lena ^{[3
]}

Harrod, Magnus ^{[4
]}

Siegel, Dionicio ^{[2
]}

Saghatelian, Alan ^{[1
]}

机构：

[1] Clayton Fdn Labs Peptide Biol, Salk Inst Biol Studies, 10010 N Torrey Pines Rd, La Jolla, CA 92037 USA

[2] Univ Calif San Diego, Skaggs Sch Pharm & Pharmaceut Sci, 9500 Gilman Dr, La Jolla, CA 92093 USA

[3] Lund Univ, Dept Clin Sci, Div Expt Vasc Res, Box 117, S-22100 Lund, Sweden

[4] Harrod Res, Frans Persons Vag 6, S-40229 Gothenburg, Sweden

[5] Univ Calif San Diego, Sch Med, 9500 Gilman Dr, La Jolla, CA 92093 USA

来源：

JOURNAL OF BIOLOGICAL CHEMISTRY | 2019年 / 294卷 / 27期

基金：

美国国家卫生研究院;

关键词：

lipid; lipid structure; lipid synthesis; lipid signaling; inflammation; FAHFAs; LAHLAs; FATTY-ACIDS; NITRIC-OXIDE; STEREOSELECTIVE-SYNTHESIS; PHENOLIC-ACIDS; AVENANTHRAMIDES; FAHFAS; ACTIVATION; COX-2; OATS; LPS;

D O I：

10.1074/jbc.RA118.006956

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：10698 / 10707

页数：10

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