Polyunsaturated fatty acids metabolites

Gree, D., R. Gree, A. Boukerh, and M. Laahassi, Synthesis of Fluorinated Analogs of Polyunsaturated Fatty Acid Metabolites (4 HNE, 13 MODE), Tetrahedron Lett. 38 6209-6212 (1997). 

Figure 11.1 Representative secondary metabolites produced by Streptomyces ceolicolor and other microorganisms, including aromatic polyketides actinorhodin and tetrohydroxynaphthalene (a), side-rophore desferrioxamines (b), polyunsaturated fatty acid eicosapentaenoic acid (c) and terpenoids beta-...

Processes including thrombosis, inflammation, wound healing, and allergy are modulated by oxygenated metabolites of arachidonate and related polyunsaturated fatty acids that are collectively... 

Ziboh, V.A., Miller, C.C., and Cho, Y., Metabolism of polyunsaturated fatty acids by skin epidermal enzymes generation of antiinflammatory and antiproliferative metabolites, Am. J. Clin. Nutr., 71, 361S, 2000. 

Because arachidonic acid and compounds of the 2 series are predominant in humans, we direct our consideration primarily to these compounds, keeping in mind that biologically active 1 and 3 series compounds are also produced. Likewise, it is far beyond the scope of our discussion here to consider all the possible products of the C20 polyunsaturated fatty acids and their metabolites. 

According to the reports describing metabolic pathways involved in the conversion of linoleic acid to trihydroxy fatty acids, several intermediate reaction products, such as trihydroxy-, hydroperoxy-, dihydroxy-, and hydroxyepoxy-octadecenoate, were involved (Kato et al., 1984,1986). Those metabolites of linoleic acid showed distinct biological functions according to their intermediate structures, including mono-, di-, trihydroxy-octadecenoic acid, and hydroperoxy-, epoxy-forms (Kato et al., 1984 Blair, 2001 Gobel et al., 2002 Hou and Forman, 2000). In an effort to understand the overall mechanism involved in the varied biological functions of the complicated reaction metabolites of bio-converted polyunsaturated fatty acids, Kim et al. (2006) studied the oxidative activities on fish oil, of crude extracts produced by PR3 from... 

Yao J, Stanley JA, Reddy RD, Keshavan MS, Pettegrew JW. 2002. Correlations between peripheral polyunsaturated fatty acid content and in vivo membrane phospholipid metabolites. Biol Psychiatry 52 823-830. 

The potential consequences of the peroxidation of membrane lipids include loss of polyunsaturated fatty acids, decreased lipid fluidity, altered membrane permeability, effects on membrane-associated enzymes, altered ion transport, release of material from subcellular compartments, and the generation of cytotoxic metabolites of lipid hydroperoxides. The physiological significance of lipid peroxidation products is shown in Table 1. 

So far as polyunsaturated fatty acids are concerned, it is now considered that n-6 acids (linoleic and its metabolites) should not exceed present levels of around 6% of energy and that the n-6/n-3 ratio should be 5 1 or lower. There have even been serious claims that linoleic acid should not exceed 3% of energy (175). Some countries, including the United States, have a very low intake of n-3 acids and possibly an excessive intake of n-6 acids leading to a high n-6/n-3 ratio (18, 19). 

In an attempt to assess the functional adequacy of vitamins and trace elements involved in antioxidant pathways, products of oxidative metabolism can be measured. Those frequently used are malondialdehyde or F2 isoprostanes, both of which give an indication of oxidation of polyunsaturated fatty acids within cells. Increasing the provision of individual antioxidants or cocktails of vitamins and trace elements can lead to a reduction in production of these metabolites that can be measured in serum or urine. Such tests have not yet reached widespread application primarily because the interpretation of results is difficult. Also, knowledge of the appropriate amount of oxidative activity that is linked to particular outcomes has not yet been identified. This is especially hnportant since there have been few clinical studies demonstrating benefit from provision of increased amounts of antioxidants. ... 

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