Linoleic acid esters of hydroxy linoleic acids are anti-inflammatory lipids found in plants and mammals.
Adipose Tissue
/ chemistry
Animals
Anti-Inflammatory Agents
/ analysis
Avena
/ chemistry
Cell Proliferation
/ drug effects
Chromatography, High Pressure Liquid
Cytokines
/ metabolism
Esters
/ chemistry
Humans
Linoleic Acids
/ chemistry
Lipopolysaccharides
/ toxicity
Macrophages
/ cytology
Mass Spectrometry
Mice
Plant Oils
/ chemistry
RAW 264.7 Cells
Stereoisomerism
FAHFAs
LAHLAs
inflammation
lipid
lipid signaling
lipid structure
lipid synthesis
Journal
The Journal of biological chemistry
ISSN: 1083-351X
Titre abrégé: J Biol Chem
Pays: United States
ID NLM: 2985121R
Informations de publication
Date de publication:
05 07 2019
05 07 2019
Historique:
received:
02
12
2018
revised:
29
05
2019
pubmed:
4
6
2019
medline:
11
3
2020
entrez:
2
6
2019
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 31152059
pii: S0021-9258(20)31858-5
doi: 10.1074/jbc.RA118.006956
pmc: PMC6615670
doi:
Substances chimiques
Anti-Inflammatory Agents
0
Cytokines
0
Esters
0
Linoleic Acids
0
Lipopolysaccharides
0
Plant Oils
0
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
10698-10707Subventions
Organisme : NIH HHS
ID : S10 OD021815
Pays : United States
Organisme : NIDDK NIH HHS
ID : R56 DK110150
Pays : United States
Organisme : NIDDK NIH HHS
ID : R01 DK106210
Pays : United States
Organisme : NIDDK NIH HHS
ID : F30 DK112604
Pays : United States
Organisme : NIDDK NIH HHS
ID : RC2 DK114785
Pays : United States
Organisme : NIGMS NIH HHS
ID : T32 GM007198
Pays : United States
Organisme : NCI NIH HHS
ID : P30 CA014195
Pays : United States
Informations de copyright
© 2019 Kolar et al.
Références
Science. 2001 Nov 30;294(5548):1871-5
pubmed: 11729303
EMBO J. 2002 Sep 16;21(18):4831-40
pubmed: 12234923
Nature. 2003 Mar 13;422(6928):173-6
pubmed: 12629551
J Physiol Pharmacol. 2003 Dec;54(4):469-87
pubmed: 14726604
J Nutr. 2004 Jun;134(6):1459-66
pubmed: 15173412
J Agric Food Chem. 2005 Oct 19;53(21):8290-5
pubmed: 16218677
J Drugs Dermatol. 2007 Feb;6(2):167-70
pubmed: 17373175
Biol Pharm Bull. 2007 Dec;30(12):2345-51
pubmed: 18057724
Lipids. 2008 Jun;43(6):533-48
pubmed: 18481134
Chem Phys Lipids. 2009 Mar;158(1):39-45
pubmed: 19146841
Cell. 2010 Sep 3;142(5):687-98
pubmed: 20813258
Clin Cosmet Investig Dermatol. 2012;5:183-93
pubmed: 23204849
Cell. 2014 Oct 9;159(2):318-32
pubmed: 25303528
Food Nutr Res. 2014 Oct 06;58:null
pubmed: 25317122
J Drugs Dermatol. 2015 Jan;14(1):43-8
pubmed: 25607907
J Cheminform. 2015 Nov 16;7:53
pubmed: 26579213
Nat Protoc. 2016 Apr;11(4):747-63
pubmed: 26985573
Nat Chem Biol. 2016 May;12(5):367-372
pubmed: 27018888
Diabetes. 2016 Sep;65(9):2580-90
pubmed: 27313314
Biochemistry. 2016 Aug 23;55(33):4636-41
pubmed: 27509211
J Biol Chem. 2016 Oct 14;291(42):22207-22217
pubmed: 27573241
Org Biomol Chem. 2016 Oct 14;14(38):9012-20
pubmed: 27603797
J Am Chem Soc. 2017 Apr 5;139(13):4943-4947
pubmed: 28350171
Cell Metab. 2018 Feb 6;27(2):419-427.e4
pubmed: 29414687
Anal Chem. 2018 Apr 17;90(8):5358-5365
pubmed: 29578702
Anal Chem. 2018 Aug 21;90(16):10056-10063
pubmed: 30052436
Anal Bioanal Chem. 2018 Nov;410(28):7415-7428
pubmed: 30255325
J Biol Chem. 1993 Jun 15;268(17):12231-4
pubmed: 7685338
J Biol Chem. 1997 Feb 7;272(6):3137-40
pubmed: 9013544
Annu Rev Immunol. 1997;15:323-50
pubmed: 9143691
Lipids. 1998 Apr;33(4):355-63
pubmed: 9590622