The role of n-3 PUFA-derived fatty acid derivatives and their oxygenated metabolites in the modulation of inflammation

被引:83
作者
de Bus, Ian [1 ,2 ]
Witkamp, Renger [1 ]
Zuilhof, Han [2 ,3 ,4 ]
Albada, Bauke [2 ]
Balvers, Michiel [1 ]
机构
[1] Wageningen Univ & Res, Div Human Nutr, Nutr & Pharmacol Grp, Stippeneng 4, NL-6708 WE Wageningen, Netherlands
[2] Wageningen Univ & Res, Lab Organ Chem, Stippeneng 4, NL-6708 WE Wageningen, Netherlands
[3] Tianjin Univ, Sch Pharmaceut Sci & Technol, 92 Weijin Rd, Tianjin, Peoples R China
[4] King Abdulaziz Univ, Dept Chem & Mat Engn, Jeddah, Saudi Arabia
关键词
PUFA; Endocannabinoid; Inflammation; Oxygenation; Chemical probes; PROSTAGLANDIN E-2 ETHANOLAMIDE; CLICK CHEMISTRY; FISH-OIL; N-DOCOSAHEXAENOYLETHANOLAMINE; CANNABINOID RECEPTORS; RHEUMATOID-ARTHRITIS; CHEMICAL PROBES; DOUBLE-BLIND; BRAIN LEVELS; RAT-BRAIN;
D O I
10.1016/j.prostaglandins.2019.106351
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
Notwithstanding the ongoing debate on their full potential in health and disease, there is general consensus that n-3 PUFAs play important physiological roles. Increasing dietary n-3 PUFA intake results in increased DHA and EPA content in cell membranes as well as an increase in n-3 derived oxylipin and -endocannabinoid concentrations, like fatty acid amides and glycerol-esters. These shifts are believed to (partly) explain the pharmacological and anti-inflammatory effects of n-3 PUFAs. Recent studies discovered that n-3 PUFA-derived endocannabinoids can be further metabolized by the oxidative enzymes CYP-450, LOX and COX, similar to the n-6 derived endocannabinoids. Interestingly, these oxidized n-3 PUFA derived endocannabinoids of eicosapentaenoyl ethanolamide (EPEA) and docosahexaenoyl ethanolamide (DHEA) have higher anti-inflammatory and anti-proliferative potential than their precursors. In this review, an overview of recently discovered n-3 PUFA derived endocannabinoids and their metabolites is provided. In addition, the use of chemical probes will be presented as a promising technique to study the n-3 PUFA and n-3 PUFA metabolism within the field of lipid biochemistry.
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页数:12
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