Docosahexaenoic acid methyl

Samadi P., Gregoire L., Rouillard C., Bedard P. J., Di Paolo T., and Levesque D. (2006). Docosahexaenoic acid reduces levodopa-induced dyskinesias in l-methyl-4-phenyl-l,2,3,6-tetrahydropyridine monkeys. Ann. Neurol. 59 282-288. 

DNP dinitrophenyl CBZ carbobenzoxy OBzl benzylesters /3NA naphthyl amide TCP tetrachlorofluorescein amaryllis alkaloids crinine, powelline, and crinamidine vinca alkaloids vincamine and vincine structural isomers 2- and 6-nitro-3-acetamido-4-chlorobenzoic acid stereoisomers 4-methoxymethyl-l-methyl-cyclohexane carboxylic acid fish oil mixture of docosahexaenoic acid and eicosapentaenoic acid NDGA nordihydroguaiaretic acid. 

Nishikawa M, Kimura S, Akaike N. Facilitatory effect of docosahexaenoic acid on N-methyl-D-aspartate response in pyramidal neurones of rat cerebral cortex. J Physiol 1994 475 83-93. 

FIGURE 1.21 Effect of initial molar ratio of various fatty acid esters to a-CD on the inclusion fraction of fatty acid esters in a-CD. O CAPME, A CPRME, MYRME, <> LINME, V EPAEE, DHAEE. Abbreviations CAPME, -caproic acid methyl ester CPRME, n-caprylic acid methyl ester LINME, linoleic acid methyl ester EPAEE, ethyl eicosapentae-noate DHAEE, ethyl docosahexaenoate. (From Yoshii, H. et ah, Oyo Toshitsu Kagaku, 42, 243, 1995. With permission.)... 

Derivatization of Fatty Acids Derivatized fatty acids have been analyzed to improve ionization and fragmentation characteristics. The FAB spectra of these derivatives are structurally more informative, and fragmentations predominantly occur via CRF processes. One such example is the application of aminoethyl-triphenylphosphonium (AETPP) bromide derivatives to characterize fatty acids structurally by FAB-MS/MS [12]. Other examples include derivatives of aminon-aphthalenesulfonic acid (ANSA), aminobenzenesulfonic acid (ABSA), picolinyl ester, yV-methyl-2-alkylimidazoline (MIM), and dimethyl- (DMAE) and trimethy-laminoethyl (TMAE) esters [8, and references therein], ESI-MS/MS spectra of underivatized and ANSA derivatives of docosahexaenoic acid are compared in Figure 12.8. 

Figure 1.2 High-performance thin-layer chromatogram of methyl esters of fatty acids, showing separation based on unsaturation. The plates were developed in the solvent system hexane/ diethyl ether, 92 8 vol./vol. a = a standard mixture of tetracosaenoic (24 1 vol./vol.) and docosahexaenoic (22 6 vol./vol.) fatty acid methyl esters b = sea scallop lipids c = dogfish liver d = menhaden e = redfish f=rapeseed g = cod liver. Reproduced with permission from Shantha, N. C. and Ackman, R. G., Silica gel thin-layer chromatographic method for concentration of longer-chain polyunsaturated fatty acids from food and marine lipids, Canadian Institute oj Food Science and Technology Journal, 24, 156-60, 1991.

Figure 13.10. Biosynthesis of fatty acids. In plants, oleate (18 1) formed by desaturation of stearate (18 0) can undergo further desaturation to linoleate (18 2) and linolenate (18 3). The introduction of a new double bond occurs in the -direction, between existing double bond and the terminal methyl group. In animals, the n-6 and n-3 polyunsaturated fatty acids undergo sequential desaturation and elongation to produce arachidonic acid (20 4 n-6), eicosapentaenoic acid (20 5 n-3) and docosahexaenoic acid (22 6 n-3). The introduction of a new double bond occurs in the A-direction, between the existing double bond and the carboxyl group.

Omega-3 fatty acids as DHA (docosahexaenoic acid) and EPA (eicosapen-taenoic acid) are known for their wholesome impact on blood circulation. Eskimo people do not often suffer heart attacks despite of the fatty nourishment. This is due to the Omega-3 fatty acids present in the polar fish. As the glycerides cannot be distilled they are first converted into methyl- and/or ethyl-esters. Distillation... 

The polyunsaturated fatty acids, which were first recognized by Burr and Burr (1930) as possessing biopotency in curing or preventing the fat-deficiency disease produced by the rigid exclusion of fat from the diet, were linoleic add, 9,12-octadecadienoic acid, linohnic add, 9,12,15-octadecatrienoic acid, and arachidonic add, 5,8,11,14-eicosatetraenoic acid. Hume et al. (1938) reported that a docosahexaenoic acid of unknown structure possesses-similar biological activity. Moreover, methyl linoleate and linoleyl alcohol, 9,12-octadecadienol, were found by Turpeinen (1937, 1938) to possess biopotency, presumably because they are converted to arachidonic acid in the body in the course of their intermediary metabolism. 

Radiation Biochemistry of Lipids. The rancidity that develops in stored fish is the result of oxidative reactions. Work being done with methyl docosahexaenoate shows that irradiation per se does not cause observable or measurable changes in this long-chain fatty acid ester. However, changes involving fatty acids go on at a higher rate in irradiated fishery products than in the nonirradiated counterparts (16). 

Fig. 1. Three biosynthetic pathways for major polyunsaturated fatty acids in mammals (desaturation, chain-elongation and chain-shortening steps). The site of desaturase action is shown by A9, A6, or A5. The major polyunsaturated fatty acids found in tissue lipids are linoleic (LA), arachidonic (ARA), docosapentaenoic (DPA), a-linolenic (ALA), eicosapentaenoic (EPA) and docosahexaenoic (DHA) acids. Fatty acids are designated by the carbon chains the number of double bonds, and the position of the first double bond from the methyl terminus, as n-9, n-7, n-6, or n-3. Typical foods enriched with the indicated fatty acids are also shown.

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