MetaCyc Pathway: poly-hydroxy fatty acids biosynthesis

Pathway diagram: poly-hydroxy fatty acids biosynthesis

Note: a dashed line (without arrowheads) between two compound names is meant to imply that the two names are just different instantiations of the same compound -- i.e. one may be a specific name and the other a general name, or they may both represent the same compound in different stages of a polymerization-type pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: free fatty acid epoxidation via a P450

Superclasses: Biosynthesis Fatty Acid and Lipid Biosynthesis Fatty Acid Biosynthesis Unusual Fatty Acid Biosynthesis

Some taxa known to possess this pathway include ? : Arabidopsis thaliana col

Expected Taxonomic Range: Viridiplantae

An Arabidopsis cytochrome P450, CYP77A4, was shown to catalyze expoxidation of free fatty acids, the first one of its kind characterized in plants [Sauveplane09]. The epoxides can be further metabolized by epoxide hydrolases and fatty acid hydroxylases to diols and poly-hydroxy fatty acids. Some of the derived metabolites are cutin monomers, i.e. 18-hydroxy-9,10-epoxystearate (see cutin biosynthesis), some others have antifungal properties possibly involved in plant defense, i.e. 12,13,17-trihydroxyoctadeca-9-enoate [Hou00].

Created 08-Feb-2011 by Zhang P , TAIR


Hou00: Hou, CT, Forman, RJ (2000). "Growth inhibition of plant pathogenic fungi by hydroxy fatty acids." J Ind Microbiol Biotechnol, 24:275-276.

Sauveplane09: Sauveplane V, Kandel S, Kastner PE, Ehlting J, Compagnon V, Werck-Reichhart D, Pinot F (2009). "Arabidopsis thaliana CYP77A4 is the first cytochrome P450 able to catalyze the epoxidation of free fatty acids in plants." FEBS J 276(3);719-35. PMID: 19120447

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Bedord78: Bedord CJ, McMahon V, Adams B (1978). "alpha-linolenic acid biosynthesis in Cyanidium caldarium." Arch Biochem Biophys 185(1);15-20. PMID: 414660

Blee93: Blee E, Stahl U, Schuber F, Stymne S (1993). "Regio- and stereoselectivity of cytochrome P-450 and peroxygenase-dependent formation of cis-12,13-epoxy-9(Z)-octadecenoic acid (vernolic acid) in Euphorbia lagascae." Biochem Biophys Res Commun 197(2);778-84. PMID: 8267615

Jaworski74: Jaworski JG, Stumpf PK (1974). "Fat metabolism in higher plants. Properties of a soluble stearyl-acyl carrier protein desaturase from maturing Carthamus tinctorius." Arch Biochem Biophys 162(1);158-65. PMID: 4831331

Kenyon72: Kenyon CN (1972). "Fatty acid composition of unicellular strains of blue-green algae." J Bacteriol 109(2);827-34. PMID: 4621688

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Le01: Le Bouquin R, Skrabs M, Kahn R, Benveniste I, Salaun JP, Schreiber L, Durst F, Pinot F (2001). "CYP94A5, a new cytochrome P450 from Nicotiana tabacum is able to catalyze the oxidation of fatty acids to the omega-alcohol and to the corresponding diacid." Eur J Biochem 268(10);3083-90. PMID: 11358528

Lee98: Lee M, Lenman M, Banas A, Bafor M, Singh S, Schweizer M, Nilsson R, Liljenberg C, Dahlqvist A, Gummeson PO, Sjodahl S, Green A, Stymne S (1998). "Identification of non-heme diiron proteins that catalyze triple bond and epoxy group formation." Science 280(5365);915-8. PMID: 9572738

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Sun Apr 26, 2015, biocyc14.