Docosahexaenoic acid-derived fatty acid esters of hydroxy fatty acids (FAHFAS) with anti-inflammatory properties

Diabetes

Volumn 65, Issue 9, 2016, Pages 2580-2590

  Kuda, Ondrej ^a   Brezinova, Marie ^a   Rombaldova, Martina ^a   Slavikova, Barbora ^b   Posta, Martin ^b   Beier, Petr ^b   Janovska, Petra ^a   Veleba, Jiri ^c   Kopecky, Jan ^a,c   Kudova, Eva ^b   Pelikanova, Terezie ^c  

^a INSTITUTE OF PHYSIOLOGY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^c INSTITUTE FOR CLINICAL AND EXPERIMENTAL MEDICINE   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

13 HYDROXYOCTADECADIENOIC ACID; 14 HYDROXYDOCOSAHEXAENOIC ACID; 9 HYDROXYOCTADECADIENOIC ACID; CD59 ANTIGEN; CELL PROTEIN; DOCOSAHEXAENOIC ACID; FATTY ACID ESTER; HYDROXY FATTY ACID; ICOSAPENTAENOIC ACID; LINOLEIC ACID; LIPOPOLYSACCHARIDE; METFORMIN; OMEGA 3 FATTY ACID; RESOLVIN; UNCLASSIFIED DRUG; ZYMOSAN; 14-HYDROXYDOCOSAHEXAENOIC ACID; ANTIINFLAMMATORY AGENT; ESTER; UNSATURATED FATTY ACID;

ADIPOCYTE; ADULT; AGED; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; EPIDIDYMAL WHITE ADIPOSE TISSUE; HUMAN; HUMAN CELL; INSULIN RESISTANCE; INTERSCAPULAR BROWN ADIPOSE TISSUE; LIPIDOMICS; LIQUID CHROMATOGRAPHY; MACROPHAGE ACTIVATION; MALE; MOUSE; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; OBESITY; PHAGOCYTOSIS; PRIORITY JOURNAL; SUBCUTANEOUS WHITE ADIPOSE TISSUE; TANDEM MASS SPECTROMETRY; WHITE ADIPOSE TISSUE; 3T3-L1 CELL LINE; ANIMAL; C57BL MOUSE; CELL CULTURE; CHEMISTRY; DRUG EFFECTS; IMMUNOLOGY; INFLAMMATION; METABOLISM; PHYSIOLOGY;

3T3-L1 CELLS; ADIPOCYTES; ADIPOSE TISSUE, WHITE; ANIMALS; ANTI-INFLAMMATORY AGENTS; CELLS, CULTURED; DIABETES MELLITUS, TYPE 2; DOCOSAHEXAENOIC ACIDS; ESTERS; FATTY ACIDS, UNSATURATED; HUMANS; INFLAMMATION; INSULIN RESISTANCE; LINOLEIC ACID; LIPOPOLYSACCHARIDES; MACROPHAGE ACTIVATION; MALE; MICE; MICE, INBRED C57BL; OBESITY; PHAGOCYTOSIS;

EID: 84983523949     PISSN: 00121797     EISSN: 1939327X     Source Type: Journal    
DOI: 10.2337/db16-0385     Document Type: Article

References (50)

1. Masoodi M, Kuda O, Rossmeisl M, Flachs P, Kopecky J. Lipid signaling in adipose tissue: connecting inflammation and metabolism. Biochim Biophys Acta 2015;1851:503-518
2. Flachs P, Rossmeisl M, Kuda O, Kopecky J. Stimulation of mitochondrial oxidative capacity in white fat independent of UCP1: a key to lean phenotype. Biochim Biophys Acta 2013;1831:986-1003
3. Iyer A, Fairlie DP, Prins JB, Hammock BD, Brown L. Inflammatory lipid mediators in adipocyte function and obesity. Nat Rev Endocrinol 2010;6:71-82
4. Wahli W, Michalik L. PPARs at the crossroads of lipid signaling and inflammation. Trends Endocrinol Metab 2012;23:351-363
5. Trujillo ME, Scherer PE. Adipose tissue-derived factors: impact on health and disease. Endocr Rev 2006;27:762-778
6. Sell H, Habich C, Eckel J. Adaptive immunity in obesity and insulin resistance. Nat Rev Endocrinol 2012;8:709-716
7. Yore MM, Syed I, Moraes-Vieira PM, et al. Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell 2014;159:318-332
8. Cao H, Gerhold K, Mayers JR, Wiest MM, Watkins SM, Hotamisligil GS. Identification of a lipokine, a lipid hormone linking adipose tissue to systemic metabolism. Cell 2008;134:933-944
9. Czech MP, Tencerova M, Pedersen DJ, Aouadi M. Insulin signalling mechanisms for triacylglycerol storage. Diabetologia 2013;56:949-964
10. Herman MA, Peroni OD, Villoria J, et al. A novel ChREBP isoform in adipose tissue regulates systemic glucose metabolism. Nature 2012;484:333-338
11. Pedersen DJ, Guilherme A, Danai LV, et al. A major role of insulin in promoting obesity-associated adipose tissue inflammation. Mol Metab 2015;4:507-518
12. Nadler ST, Stoehr JP, Schueler KL, Tanimoto G, Yandell BS, Attie AD. The expression of adipogenic genes is decreased in obesity and diabetes mellitus. Proc Natl Acad Sci USA 2000;97:11371-11376
13. Parsons WH, Kolar MJ, Kamat SS, et al. AIG1 and ADTRP are atypical integral membrane hydrolases that degrade bioactive FAHFAs. Nat Chem Biol 2016;12:367-372
14. Zerkowski JA. Estolides: from structure and function to structured and functionalized. Lipid Technol 2008;20:253-256
15. McLean S, Davies NW, Nichols DS, Mcleod BJ. Triacylglycerol estolides, a new class of mammalian lipids, in the paracloacal gland of the brushtail possum (Trichosurus vulpecula). Lipids 2015;50:591-604
16. Ma Y, Kind T, Vaniya A, Gennity I, Fahrmann JF, Fiehn O. An in silico MS/MS library for automatic annotation of novel FAHFA lipids. J Cheminform 2015;7:53
17. Fitzgibbons TP, Czech MP. Emerging evidence for beneficial macrophage functions in atherosclerosis and obesity-induced insulin resistance. J Mol Med (Berl) 2016;94:267-275
18. Hotamisligil GS, Shargill NS, Spiegelman BM. Adipose expression of tumor necrosis factor-alpha: direct role in obesity-linked insulin resistance. Science 1993;259:87-91
19. Shoelson SE, Lee J, Yuan M. Inflammation and the IKK beta/I kappa B/NFkappa B axis in obesity- and diet-induced insulin resistance. Int J Obes Relat Metab Disord 2003;27(Suppl 3):S49-S52
20. Weisberg SP, McCann D, Desai M, Rosenbaum M, Leibel RL, Ferrante AW Jr. Obesity is associated with macrophage accumulation in adipose tissue. J Clin Invest 2003;112:1796-1808
21. Kuda O, Jelenik T, Jilkova Z, et al. n-3 fatty acids and rosiglitazone improve insulin sensitivity through additive stimulatory effects on muscle glycogen synthesis in mice fed a high-fat diet. Diabetologia 2009;52:941-951
22. Calder PC. Marine omega-3 fatty acids and inflammatory processes: effects, mechanisms and clinical relevance. Biochim Biophys Acta 2015;1851:469-484
23. Flachs P, Rossmeisl M, Kopecky J. The effect of n-3 fatty acids on glucose homeostasis and insulin sensitivity. Physiol Res 2014;63(Suppl. 1):S93-S118
24. Hellmann J, Tang Y, Kosuri M, Bhatnagar A, Spite M. Resolvin D1 decreases adipose tissue macrophage accumulation and improves insulin sensitivity in obese-diabetic mice. FASEB J 2011;25:2399-2407
25. Titos E, Rius B, González-Périz A, et al. Resolvin D1 and its precursor docosahexaenoic acid promote resolution of adipose tissue inflammation by eliciting macrophage polarization toward an M2-like phenotype. J Immunol 2011; 187:5408-5418
26. Kuda O, Rombaldova M, Janovska P, Flachs P, Kopecky J. Cell type-specific modulation of lipid mediator's formation in murine adipose tissue by omega-3 fatty acids. Biochem Biophys Res Commun 2016;469:731-736
27. Rossmeisl M, Jilkova ZM, Kuda O, et al. Metabolic effects of n-3 PUFA as phospholipids are superior to triglycerides in mice fed a high-fat diet: possible role of endocannabinoids. PLoS One 2012;7:e38834
28. Spencer M, Finlin BS, Unal R, et al. Omega-3 fatty acids reduce adipose tissue macrophages in human subjects with insulin resistance. Diabetes 2013; 62:1709-1717
29. Oh DY, Talukdar S, Bae EJ, et al. GPR120 is an omega-3 fatty acid receptor mediating potent anti-inflammatory and insulin-sensitizing effects. Cell 2010; 142:687-698
30. Oh da Y, Walenta E, Akiyama TE, et al. A Gpr120-selective agonist improves insulin resistance and chronic inflammation in obese mice. Nat Med 2014;20: 942-947
31. Serhan CN, Chiang N, Dalli J. The resolution code of acute inflammation: novel pro-resolving lipid mediators in resolution. Semin Immunol 2015;27:200-215
32. Clària J, Nguyen BT, Madenci AL, Ozaki CK, Serhan CN. Diversity of lipid mediators in human adipose tissue depots. Am J Physiol Cell Physiol 2013;304: C1141-C1149
33. White PJ, St-Pierre P, Charbonneau A, et al. Protectin DX alleviates insulin resistance by activating a myokine-liver glucoregulatory axis. Nat Med 2014;20: 664-669
34. Veleba J, Kopecky J Jr, Janovska P, et al. Combined intervention with pioglitazone and n-3 fatty acids in metformin-treated type 2 diabetic patients: improvement of lipid metabolism. Nutr Metab (Lond) 2015;12:52
35. Kuda O, Jenkins CM, Skinner JR, et al. CD36 protein is involved in storeoperated calcium flux, phospholipase A2 activation, and production of prostaglandin E2. J Biol Chem 2011;286:17785-17795
36. Suh JH, Kim RY, Lee DS. A new metabolomic assay to examine inflammation and redox pathways following LPS challenge. J Inflamm (Lond) 2012; 9:37
37. Becker K, Schroecksnadel S, Gostner J, et al. Comparison of in vitro tests for antioxidant and immunomodulatory capacities of compounds. Phytomedicine 2014;21:164-171
38. Neises B, Steglich W. Simple method for the esterification of carboxylic acids. Angew Chem Int Ed Engl 1978;17:522-524
39. Morgan AH, Hammond VJ, Morgan L, et al. Quantitative assays for esterified oxylipins generated by immune cells. Nat Protoc 2010;5:1919-1931
40. Krishnamoorthy S, Recchiuti A, Chiang N, et al. Resolvin D1 binds human phagocytes with evidence for proresolving receptors. Proc Natl Acad Sci USA 2010;107:1660-1665
41. Colas RA, Shinohara M, Dalli J, Chiang N, Serhan CN. Identification and signature profiles for pro-resolving and inflammatory lipid mediators in human tissue. Am J Physiol Cell Physiol 2014;307:C39-C54
42. Derogis PB, Freitas FP, Marques AS, et al. The development of a specific and sensitive LC-MS-based method for the detection and quantification of hydroperoxy- and hydroxydocosahexaenoic acids as a tool for lipidomic analysis. PLoS One 2013;8:e77561
43. Serhan CN, Petasis NA. Resolvins and protectins in inflammation resolution. Chem Rev 2011;111:5922-5943
44. Soliman H, Mediavilla-Varela M, Antonia S. Indoleamine 2,3-dioxygenase: is it an immune suppressor? Cancer J 2010;16:354-359
45. Fitzgerald J, Colas R, Shinohara M, Dalli J, Serhan CN. Lipid Mediator Metabololipidomics LC-MS-MS Spectra Book 2014. Available from https://research.bwhanesthesia.org/site-assets/51520d191eea6679ce000001/serhan-lab/spectrabook-cb460aacacb011b96d8215b8091c3b8e.pdf [Internet], 2014. Boston, MA, Center for Experimental Therapeutics and Reperfusion Injury, Harvard Institute of Medicine, Brigham and Women's Hospital and Harvard Medical School. Accessed 1 June 2014
46. Hung AM, Booker C, Ellis CD, et al. Omega-3 fatty acids inhibit the up-regulation of endothelial chemokines in maintenance hemodialysis patients. Nephrol Dial Transplant 2015;30:266-274
47. Mozaffarian D, Lemaitre RN, King IB, et al. Plasma phospholipid long-chain ω-3 fatty acids and total and cause-specific mortality in older adults: a cohort study. Ann Intern Med 2013;158:515-525
48. Scorletti E, Bhatia L, McCormick KG, et al.; WELCOME Study. Effects of purified eicosapentaenoic and docosahexaenoic acids in nonalcoholic fatty liver disease: results from the Welcome∗ study. Hepatology 2014;60:1211-1221
49. Kris-Etherton PM, Harris WS, Appel LJ; AHA Nutrition Committee. American Heart Association. Omega-3 fatty acids and cardiovascular disease: new recommendations from the American Heart Association. Arterioscler Thromb Vasc Biol 2003;23:151-152
50. Wu JH, Cahill LE, Mozaffarian D. Effect of fish oil on circulating adiponectin: a systematic review and meta-analysis of randomized controlled trials. J Clin Endocrinol Metab 2013;98:2451-2459