Fatty acid metabolites

Chenoweth believes that an explanation of the above results may lie in the reactions occurring before the entrance of fatty acid metabolites into the citric acid cycle. Activated acetate, i.e. acetyl coenzyme A (AcCoA) is the end-product of fatty acid metabolism prior to its condensation with oxalacetate to form citrate. Possibly fluoro-fatty acids behave like non-fluorinated fatty acids. The end-product before the oxalacetate condensation could be the same for all three fluorinated inhibitors, viz. fluoroacetyl coenzyme A (FAcCoA). Fluorocitrate could then be formed by the condensation of oxalacetate with FAcCoA, thereby blocking the citric acid cycle. The specificity of antagonisms must therefore occur before entrance of the metabolites into the citric acid cycle. 

Blood/gout/ prosta- fatty acid metabolite/involved in the control of... 

Sitachitta N, Gerwick WH (1998) Grenadadiene and Grenadamide, Cyclopropyl-Containing Fatty Acid Metabolites from the Marine Cyanobacterium Lyngbya majuscula. J Nat Prod 61 681... 

Shoeb M, Jaspars M (2003) Chlorinated C12 Fatty Acid Metabolites from the Red Alga Gracilaria verrucosa. J Nat Prod 66 1509... 

Niwa, H., Inagaki, H., and Yamada, K., Didemnilactone and neodidemnilactone, two new fatty acid metabolites possessing a 10-membered lactone from the tunicate Didemnum mosleyi (Herdman), Tetrahedron Lett., 32, 5127, 1991. 

Human serum albumin (HSA) is an important transporter of fatty acids, metabolites, drugs, and organic compounds in the circulatory system [93, 94], It is a single polypeptide chain consisting of 585 amino acids. Under physiological conditions (pH 7), HSA adopts a heart-shaped three-dimensional (3D) structure with three homologous domains I—III (Fig. 14) each domain contains two subdomains A and B, which consist of four and six a-helices, respectively [95, 96]. The X-ray structure shows that two halves of the albumin molecule... 

Ketone bodies The short chain fatty acid metabolites acetoacetate and p-hydroxybutyrate and acetone. 

It has been well established that fatty acid metabolites of LOX and cytochrome P450 are implicated in essential aspects of cellular signaling, including the induction of apoptosis. The enzymatic and non-enzymatic products of polyunsaturated fatty acids thus control cell growth and apoptosis, and the spontaneous oxidation of polyunsaturated fatty acids gives rise to reactive aldehydes and other products of lipid peroxidation that are potentially cytotoxic and which may also signal apoptosis [102]. 

The diversity associated with silyl protecting groups as well as the chemical conditions available for their removal makes them attractive alternatives to benzyl protection of the hydroxy groups of either D- or L-tartaric acid derivatives. O-isopropylidene-L-threitol (37) is mono-protected with er -butyldimethylsilyl chloride to furnish 266, which is converted in three steps to the nitrile 267. Reduction with DIBAL and Wittig olefination followed by desilylation with fluoride and Swern oxidation of the resulting alcohol provides aldehyde 268, which reacts with methyl 10-(triphenylphosphorane)-9-oxo-decanoate (269) to afford enone 270. Reduction of 270 with subsequent preparative TLC and acetal hydrolysis furnishes (9R)-271 and (9 S)-272, both interesting unsaturated trihydroxy Cig fatty acid metabolites isolated from vegetables [91] (Scheme 62). 

Sitachitta N, Gerwick WH. (1998) Grenadadiene and grenadamide, cyclopropyl-containing fatty acid metabolites from the marine cyanobacterium Lyngbya majuscula. Journal Natural Products 61 681-684. 

In other instances unsaturated fatty acids can strongly repress cerevlslae enzymic activity e.g. alcohol acetyltransferase (56), acyltransferases Involved In glycerollpld synthesis (57), fatty acid biosynthesis (In both cerevlslae and Candida llpolytlca, 58) and acetyl CoA carboxylase (59). Some enzymes are repressed by long chain fatty acids (57-59), while unsaturated compounds have specific effects in others (56). Defined mechanisms for these diverse responses are not clear, although nonspecific surfactant action Is probably rare (57) and fatty acid metabolites mediate some repressive fatty acid effects (59). 

Linoleic acid is one of the most important polyunsaturated fatty acids it is the essential lipid precursor to many vital biomolecules, such as prostaglandins, thromboxanes, lipoxins, and prostacyclins (1-5). All of these linoleic acid metabolites are unique molecules with either carbocyclic systems containing chiral carbon centers or unsaturated C-C systems of specific geometric configurations. These fatty acid metabolites perform highly specialized physiologic roles (6,7). 

Williard, D.E., Kaduce, T.L., Harmon, S.D., and Specter, A.A. (1998) Conversion of Eicosapentaenoic Acid to Chain-Shortened Omega-3 Fatty Acid Metabolites by Peroxisomal Oxidation, J. Lipid Res. 39,978-986. 

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). 

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