A simple synthesis of 5,8,11‐eicosatrienoic acid

Parish, Harlie A.; Gilliom, Richard D.; Purcell, William P.

doi:10.1007/bf02534568

Cited by 6 publications

(2 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Materials. 5,8,11-Eicosatrienoic acid was chemically synthesized in the Department of Organic Chemistry, Flinders University, as described (11). After purification by crystallization, this compound was hydrogenated to produce chromatographically pure 5,8,11-ETrA.…”

Section: Methodsmentioning

confidence: 99%

Effect of dietary supplementation with n-9 eicosatrienoic acid on leukotriene B4 synthesis in rats: a novel approach to inhibition of eicosanoid synthesis.

James

Gibson

Neumann

et al. 1993

The Journal of Experimental Medicine

View full text Add to dashboard Cite

SummaryStudies were undertaken to assess the biochemical effects of dietary supplementation with n-9 eicosatrienoic acid (ETrA), an arachidonic acid analogue that is normally present in cell membranes at very low levels but is raised in the presence of essential fatty acid deficiency (EFAD) . The incorporation ofdietary ETiA into rat neutrophils and its effect on A23187-stimulated 5-lipoxygenase metabolism in these cells was examined; in addition, the effect of ETrA was compared with that ofanother arachidonic acid analogue, eicosapentaenoic acid (EPA), which is known to accumulate in cell membranes and inhibit synthesis of leukotriene B4 (LTB4), i product of the 5-lipoxygenase metabolic pathway. Rats were fed a defined diet that was sufficient in essential fatty acids and that contained EPA or ETrA (0.014% of energy) or no added fatty acid, for 3 wk. In the cells from ETrA-fed rats, LTB 4 synthesis was inhibited relative to control values, but synthesis of the other products of 5-lipoxygenase metabolism, 5-hydroxyeicosatetraenoic acid (5-HETE) and the all-trans isomers of LTB4, were not inhibited . This pattern indicates inhibition of LTA hydrolase in ETrA-fed rats. In EPA-fed rats, there was inhibition of LTB4 and the all-trans isomers of LTB4, but there was no inhibition of 5-HETE . This pattern indicates inhibition of LTA synthase in EPA-fed rats. The results establish that dietary ETtA effectively inhibits synthesis of the inflammatory mediator, LTB4, and suggest that ETrA may confer antiinflammatory benefits similar to those observed with EFAD or dietary fish oil (which contains EPA). Because ETrA is substantially less unsaturated than EPA, it can be expected to have greater chemical stability, which could be an important practical advantage when used as a dietary constituent or supplement .

show abstract

Section: Methodsmentioning

confidence: 99%

Effect of dietary supplementation with n-9 eicosatrienoic acid on leukotriene B4 synthesis in rats: a novel approach to inhibition of eicosanoid synthesis.

James

Gibson

Neumann

et al. 1993

The Journal of Experimental Medicine

View full text Add to dashboard Cite

show abstract

“…These deficient strains synthesize MA (25.5%) instead of ARA (Table 1 ), similar to EFA-deficiency in mammals, and MA-containing oil accumulates in the cells [ 27 , 28 ]. This MA-containing microbial oil is an alternative source of MA in addition to MA synthesized chemically [ 29 , 30 ], and has been used in the pharmacological studies described below.…”

Section: Introductionmentioning

confidence: 99%

The physiological and pathological properties of Mead acid, an endogenous multifunctional n-9 polyunsaturated fatty acid

Kawashima,

Yoshizawa

2023

Lipids Health Dis

View full text Add to dashboard Cite

Mead acid (MA, 5,8,11-eicosatrienoic acid) is an n-9 polyunsaturated fatty acid (PUFA) and a marker of essential fatty acid deficiency, but nonetheless generally draws little attention. MA is distributed in various normal tissues and can be converted to several specific lipid mediators by lipoxygenase and cyclooxygenase. Recent pathological and epidemiological studies on MA raise the possibility of its effects on inflammation, cancer, dermatitis and cystic fibrosis, suggesting it is an endogenous multifunctional PUFA. This review summarizes the biosynthesis, presence, metabolism and physiological roles of MA and its relation to various diseases, as well as the significance of MA in PUFA metabolism.

show abstract

Simple mass spectrometric differentiation of then-3,n-6 andn-9 series of methylene interrupted polyenoic acids

Fellenberg

Johnson

Poulos

et al. 1987

Biol. Mass Spectrom.

View full text Add to dashboard Cite

show abstract

A simple synthesis of 5,8,11‐eicosatrienoic acid

Cited by 6 publications

References 4 publications

Effect of dietary supplementation with n-9 eicosatrienoic acid on leukotriene B4 synthesis in rats: a novel approach to inhibition of eicosanoid synthesis.

Effect of dietary supplementation with n-9 eicosatrienoic acid on leukotriene B4 synthesis in rats: a novel approach to inhibition of eicosanoid synthesis.

The physiological and pathological properties of Mead acid, an endogenous multifunctional n-9 polyunsaturated fatty acid

Simple mass spectrometric differentiation of then-3,n-6 andn-9 series of methylene interrupted polyenoic acids

Contact Info

Product

Resources

About