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MetaCyc Pathway: calendate biosynthesis

Pathway diagram: calendate biosynthesis

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: calendic acid biosynthesis

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

Some taxa known to possess this pathway include ? : Calendula officinalis

Expected Taxonomic Range: Magnoliophyta

Summary:
Seed oils of a few plant species are enriched in conjugated fatty aids, which are fatty acids containing conjugated or non-methylene-interrupted double bonds. Because conjugated double bonds have high rates of oxidation, seed oils rich in conjugated double bonds are used commercially as drying agents in paints and varnishes.

The conjugated double bonds are introduced by "conjugases", divergent forms of FAD2 (EC 1.14.19.f, acyl-lipid ω-6 desaturase (cytochrome b5)). Conjugases act on fatty acids bound to phosphatidylcholine as substrates, as has been shown for FAD2 enzymes, and modify an existing double bond to produce the conjugated double bonds with or without introducing a new double bond.

Calendate ((8E,10E,12Z)-octadeca-8,10,12-trienoate) is a conjugated form of linoleate. It is a major fatty acid component of the seed oil of Calendula officinalis, an annual flowering plant in which calendate comprises more than 40% of the seed lipid fatty acids.

Calendate is derived from linoleate by a fatty acid conjugase that converts a cis Δ9 double bond into a conjugated trans-trans double bond system [Cahoon01, Qiu01].

Credits:
Created 10-Oct-2006 by Zhang P , TAIR
Revised 22-Dec-2014 by Caspi R , SRI International


References

Cahoon01: Cahoon EB, Ripp KG, Hall SE, Kinney AJ (2001). "Formation of conjugated delta8,delta10-double bonds by delta12-oleic-acid desaturase-related enzymes: biosynthetic origin of calendic acid." J Biol Chem 276(4);2637-43. PMID: 11067856

Qiu01: Qiu X, Reed DW, Hong H, MacKenzie SL, Covello PS (2001). "Identification and analysis of a gene from Calendula officinalis encoding a fatty acid conjugase." Plant Physiol 125(2);847-55. PMID: 11161042

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

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


Report Errors or Provide Feedback
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 Wed Apr 1, 2015, biocyc14.