The Hudrlik–Peterson Reaction of Secondary cis-TMS-Epoxy Alcohols and its Application to the Synthesis of the Fatty Acid Intermediates

As an extension of the study on the Hudrlik–Peterson reaction of trans-TMS-epoxy alcohols with lithium acetylides, four cis-TMS-epoxy alcohols possessing different alkyl substituents were subjected to the reaction with TMS-acetylide. The reaction completed in 1 h at 0 °C to afford cis-enynyl alcohols in good yields. The results indicated that cis-TMS-epoxy alcohols had higher reactivity than the trans-isomers. Anions derived from 1-heptyne and phenylacetylene participated in the reaction as well. The reaction was applied to optically active cis-TMS-epoxy alcohols, and the resulting enynyl alcohols were transformed to the synthetic intermediates of protectin D1, maresin 1, resolvin E1, and leukotriene B4.

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

Journal of Experimental Medicine ◽

10.1084/jem.178.6.2261 ◽

1993 ◽

Vol 178 (6) ◽

pp. 2261-2265 ◽

Cited By ~ 35

Author(s):

M J James ◽

R A Gibson ◽

M A Neumann ◽

L G Cleland

Keyword(s):

Arachidonic Acid ◽

Fatty Acid ◽

Cell Membranes ◽

Essential Fatty Acids ◽

Dietary Supplementation ◽

Eicosatrienoic Acid ◽

Leukotriene B4 ◽

Trans Isomers ◽

Practical Advantage ◽

Acid Analogue

Studies 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 of dietary ETrA 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 of another arachidonic acid analogue, eicosapentaenoic acid (EPA), which is known to accumulate in cell membranes and inhibit synthesis of leukotriene B4 (LTB4) a 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, LTB4 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 ETrA 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.

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PSVII-18 Fatty acid composition of the longissimus muscle from Angus and Wagyu sired cattle at the 6th and 12th rib location

Journal of Animal Science ◽

10.1093/jas/skaa054.366 ◽

2020 ◽

Vol 98 (Supplement_3) ◽

pp. 211-212

Author(s):

Jerad Jaborek ◽

Francis L Fluharty ◽

Alejandro E Relling

Keyword(s):

Fatty Acid ◽

Mixed Model ◽

Random Effect ◽

Repeated Measurements ◽

Longissimus Muscle ◽

Trans Isomers ◽

Fa Composition ◽

Effect Of Treatment ◽

Similar Body ◽

Location Interaction

Abstract The fatty acid (FA) composition of the longissimus muscle (LM) of Angus and Wagyu sired cattle raised to a similar body weight (612 kg) were compared at the 6th and 12th rib locations. Angus sired steers represented T1, cattle from a Wagyu sire selected for growth represented T2, and cattle from a Wagyu sire selected for marbling represented T3. Data were analyzed mixed model with repeated measurements on animal (LM location); the model include the fixed effect of treatment, LM location, and their interaction, and random effect of sex. The percentage of 16:0, 18:1cis9, 18:3, and monounsaturated FA (MUFA) exhibited a treatment*LM location interaction (P ≤ 0.7), where T2 cattle had a greater percentage of 16:0 and a lesser percentage of 18:1cis9, 18:3, and MUFA at the 12th rib vs. 6th rib location compared with T1 and T3 cattle. The percentage of total FA lipid, polyunsaturated FA(PUFA), and PUFA:SFA ratio in the LM were greater (P ≤ 0.02) for T3 cattle compared with T1 and T2 cattle. The percentage of 18:0 was greater (P ≤ 0.01) for T1 cattle compared with T2 and T3 cattle, while T1 cattle had a greater (P ≤ 0.01) percentage of saturated FA (SFA) compared to T3 cattle. The percentage of 18:1cis9, other 18:1cis isomers, 18:2, MUFA, and MUFA:SFA ratio were greater (P ≤ 0.02) for T3 cattle compared with T1 cattle, with T2 cattle being intermediate. The percentage of total FA lipid, 18:0, 18:1 trans isomers, and SFA were greater (P ≤ 0.01) at the 6th rib LM location, while 14:1, 18:cis9, other 18:1 cis isomers, MUFA, MUFA:SFA, and PUFA:SFA ratio were greater (P ≤ 0.02) at the 12th rib LM location

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