Unsaturated fatty acid derivatives

Li Y, Ishibashi M, Sasaki T, Kobayashi J (1995) New Bromine-Containing Unsaturated Fatty Acid Derivatives from the Okinawan Marine Sponge Xestospongia sp. J Chem Res (S) 126... 

Prostaglandins are unsaturated fatty acid derivatives that act on the tissues in which they are synthesized and are rapidly metabolized to inactive products at the site of action. The biosynthesis and actions of the prostaglandins are presented on p. 402 and Figure 39.3. 

Yunoki, K., Hirose, S., Ohnishi, M. (2007) Ethyl esterification of long-chain unsaturated fatty acids derived from grape must by yeast during alcoholic fermentation. Bioscience Biotechrutl-ogy and Biochemistry, 71, 3105-3109. 

Baker PRS, Lin Y, Schopfer FJ, Woodcock SR, Groeger AL, Batthyany C, Swooney S, Long MH, lies KE, Baker LMS, Branchaud BP, Chen Y, Freeman BA. Fatty acid transduction of nitric oxide signaling Multiple nitrated unsaturated fatty acid derivatives exist in human blood and urine and serve as endogenous peroxisome proliferator-activated receptor ligands. J. Biol. Chem. 2005 280 42464-42475. 

Eicosanoids (prostaglandins, thromboxanes, leuko-trienes, lipoxins) is the name given to a group of 20-carbon unsaturated fatty acids derived principally from arachidorric acid in cell walls. They are shortlived, extremely potent and formed in almost every tissue in the body. Eicosanoids are involved in most types of inflammation and it is on manipulation of their biosynthesis that most present anti-inflammatory therapy is based. Their biosynthetic paths appear in Figure 15.1 and are amplified by the following account. 

The determination of the sites of the C—C double bonds in unsaturated fatty acid derivatives and other lipids plays an outstanding role in the analytical application of mass spectrometry. Much work has been published on the localization of double bonds in... 

The determination of the sites of the C—C double bonds in unsaturated fatty acid derivatives and other lipids plays an outstanding role in the analytical application of mass spectrometry. Much work has been published on the localization of double bonds in monoolefins, and a number of extensive reviews has appeared on the topic . Two major methodologies have been employed. In the first one, unsaturated C—C bonds are converted to appropriate derivatives by synthesis in the liquid phase, which are then subjected to mass spectrometric analysis mostly by using standard El techniques. These methods will be mentioned only briefly in the next section, including some recent work which has not yet been mentioned in the reviews. The second methodology takes advantage of the bimolecular reactivity of neutral olefins with ionic reagents in the gas phase,... 

Fig. 1. Pathways for the production of unsaturated fatty acids derived from linolenate (18 3), linoleate (18 2), oleate (18 1), and palmitoleate (16 1).

The metathesis of triacylglycerols and unsaturated fatty acid derivatives has emerged as a powerful tool in synthetic organic chemistry. The metathesis approaches most commonly applied in oleochemistry are... 

It appears likely that silver ion HPLC will soon begin to supplant TLC procedures. As the author has reviewed the technique in some detail elsewhere [168], some salient references only together with important developments of a more recent date are given here. Several groups have reported successful separations of unsaturated fatty acid derivatives on micro-particulate silica gel impregnated with silver nitrate [88,372,378,379,685,814]. It appears that the most suitable grade of silica gel for the purpose Is one with a large pore size. Unfortunately, silver... 

Hydroperoxides from unsaturated fatty acid derivatives have been examined by direct-probe chemical ionisation MS [716,717]. 

Radical deoxygenation of the cw-unsaturated fatty acid derivative with tris(trimethylsilyl)silane gives methyl triacont-21-frawy-enoate together with the saturated compound (eq 4). If the reaction is carried out with tri- -butyltin hydride, the configuration remains unchanged. ... 

Figure 5 Can a plant KAS use cis A3-Cio as a substrate for unsaturated fatty acyl chains This compound is formed in E. coli by the isomerase activity of the fabA encoded dehydrase, which as the plant dehydrase synthesizes trans A2-Cio used in synthesis of saturated fatty acids If both fabA activities (broken arrows) function in transgenic rape seeds, and the rape KAS can use the cis A3-Cio substrate then the E. coli specific unsaturated fatty acyl chains, cis A9-Ci6 and cis A1 l-Cig (right side), as well as the plant unsaturated fatty acids derived from Cl 6- and Cl 8-acyl chains (left side) will be synthesized.

Claeys, M. Nizigiyimana, L. Van den Heuvel, H. Derrick, P. J. Mechanistic aspects of charge-remote fragmentation in saturated and mono-unsaturated fatty acid derivatives. Evidence for homolytic cleavage. Rapid Commun. Mass Spec. 1996, 10, 770-774. 

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