MetaCyc Pathway: cutin biosynthesis

Pathway diagram: cutin biosynthesis

If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: cutin monomer biosynthesis

Superclasses: Biosynthesis Cell Structures Biosynthesis Plant Cell Structures Epidermal Structures
Biosynthesis Fatty Acid and Lipid Biosynthesis

Some taxa known to possess this pathway include ? : Arabidopsis thaliana col , Glycine max , Oryza sativa , Oryza sativa Japonica Group Inferred from experiment [Li10c]

Expected Taxonomic Range: Viridiplantae

Above-ground epidermal surfaces of vascular plants are covered by a lipophilic layer known as the cuticle. The cuticle functions as a barrier to control the movement of gas, water and solute, as well as plant pathogens. Plant cuticles are composed of cutin and cuticular wax. Cutin is a polymer comprised of cutin monomers that are attached to each other by an ester linkage. Cutin monomers include C16 and C18 fatty acids and their derivatives, and glycerol. Among the fatty acid derivatives, ω-hydroxy-, polyhydroxy-, and epoxy-fatty acids are typical cutin monomers.

While α,ω-dicarboxylic acids are signatures of suberin (see suberin monomers biosynthesis), and are generally found only in trace level in cutin, they count for more than 50% of cutin monomers in Arabidopsis.

Among the enzymes characterized for the pathway, the Arabidopsis CYP86A8 and CYP94C1 both catalyze ω-hydroxylation of fatty acids. However they displayed distinct substrate specificities. CYP86A8 hydroxylates palmitate and stearate, but not expoxy fatty acids [Wellesen01], while CYP94C1 metabolized the latter more effectively [Kandel07]. A CYP P450 activity detected in soybean also had preference towards fatty acid epoxides [Blee93].

Citations: [Kolattukudy, Pollard08]

Unification Links: AraCyc:PWY-321

Revised 17-Oct-2008 by Zhang P , TAIR


Blee93: Blee, Elizabeth, Schuber, Francis (1993). "Biosynthesis of cutin monomers: involvement of a lipoxygenase/peroxygenase pathway." The Plant Journal, 4(1):113-123.

Kandel07: Kandel S, Sauveplane V, Compagnon V, Franke R, Millet Y, Schreiber L, Werck-Reichhart D, Pinot F (2007). "Characterization of a methyl jasmonate and wounding-responsive cytochrome P450 of Arabidopsis thaliana catalyzing dicarboxylic fatty acid formation in vitro." FEBS J 274(19);5116-27. PMID: 17868380

Kolattukudy: Kolattukudy, P.E. "Biosynthetic pathways of cutin and waxes, and their sensitivity to environmental stresses." in: Plant Cuticles: an integrated functional approach. G. Kerstines, ed. BIOS Scientific Publishers Ltd, Oxford, UK.

Kurdyukov06: Kurdyukov S, Faust A, Trenkamp S, Bar S, Franke R, Efremova N, Tietjen K, Schreiber L, Saedler H, Yephremov A (2006). "Genetic and biochemical evidence for involvement of HOTHEAD in the biosynthesis of long-chain alpha-,omega-dicarboxylic fatty acids and formation of extracellular matrix." Planta 224(2);315-29. PMID: 16404574

Li10c: Li H, Pinot F, Sauveplane V, Werck-Reichhart D, Diehl P, Schreiber L, Franke R, Zhang P, Chen L, Gao Y, Liang W, Zhang D (2010). "Cytochrome P450 family member CYP704B2 catalyzes the {omega}-hydroxylation of fatty acids and is required for anther cutin biosynthesis and pollen exine formation in rice." Plant Cell 22(1);173-90. PMID: 20086189

Pollard08: Pollard M, Beisson F, Li Y, Ohlrogge JB (2008). "Building lipid barriers: biosynthesis of cutin and suberin." Trends Plant Sci 13(5);236-46. PMID: 18440267

Wellesen01: Wellesen K, Durst F, Pinot F, Benveniste I, Nettesheim K, Wisman E, Steiner-Lange S, Saedler H, Yephremov A (2001). "Functional analysis of the LACERATA gene of Arabidopsis provides evidence for different roles of fatty acid omega -hydroxylation in development." Proc Natl Acad Sci U S A 2001;98(17);9694-9. PMID: 11493698

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

Bais10: Bais P, Moon SM, He K, Leitao R, Dreher K, Walk T, Sucaet Y, Barkan L, Wohlgemuth G, Roth MR, Wurtele ES, Dixon P, Fiehn O, Lange BM, Shulaev V, Sumner LW, Welti R, Nikolau BJ, Rhee SY, Dickerson JA (2010). " a web portal for plant metabolomics experiments." Plant Physiol 152(4);1807-16. PMID: 20147492

Benveniste98: Benveniste I, Tijet N, Adas F, Philipps G, Salaun JP, Durst F (1998). "CYP86A1 from Arabidopsis thaliana encodes a cytochrome P450-dependent fatty acid omega-hydroxylase." Biochem Biophys Res Commun 243(3);688-93. PMID: 9500987

Hofer08: Hofer R, Briesen I, Beck M, Pinot F, Schreiber L, Franke R (2008). "The Arabidopsis cytochrome P450 CYP86A1 encodes a fatty acid omega-hydroxylase involved in suberin monomer biosynthesis." J Exp Bot 59(9);2347-60. PMID: 18544608

Huang14: Huang FC, Peter A, Schwab W (2014). "Expression and characterization of CYP52 genes involved in the biosynthesis of sophorolipid and alkane metabolism from Starmerella bombicola." Appl Environ Microbiol 80(2);766-76. PMID: 24242247

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

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

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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
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