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MetaCyc Pathway: cutin biosynthesis
Inferred from experiment

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: BiosynthesisCell Structures BiosynthesisPlant Cell StructuresEpidermal Structures
BiosynthesisFatty Acid and Lipid Biosynthesis

Some taxa known to possess this pathway include : Arabidopsis thaliana col, Glycine max, Oryza sativa, Oryza sativa Japonica Group

Expected Taxonomic Range: Viridiplantae

The plant cuticle is a lipophilic layer that covers all above-ground epidermal surfaces of vascular plants and functions as a barrier to control the movement of gas, water and solutes, as well as protect from plant pathogens. The cuticles is composed of two main ingredients - cutin and cuticular wax.

Cutin is a polymer comprised of ω-hydroxy fatty acids and their derivatives, interlinked via ester bonds and forming a polyester polymer of indeterminate size. There are two major families of cutin monomers, comprising C16 and C18 compounds. The C16 family consists mainly of 16-hydroxypalmitate and 9,16-dihydroxypalmitate and 10,16-dihydroxypalmitate. The C18 family consists mainly of 18-hydroxyoleate, 9,10-epoxy-18-hydroxystearate, and 9,10,18-trihydroxystearate.

Cutin biosynthesis consists of sequential reactions including the activation of acyl chains to acyl-CoAs by the long-chain acyl-CoA synthetase encoded by the LACS2 gene, hydroxylation and epoxidation catalyzed by several cytochrome P450 family members, and esterification to glycerol-3-phosphate by glycerol-3-phosphate acyltransferases (GPATs) [Xue14]

Among the enzymes characterized from this pathway, the Arabidopsis CYP86A8 and CYP94C1 are fatty acid ω-hydroxylases that display distinct substrate specificities. CYP86A8 hydroxylates palmitate and stearate, but not expoxy fatty acids [Wellesen01], while CYP94C1 metabolize the latter more effectively [Kandel07]. A CYP P450 activity detected in soybean also had preference towards fatty acid epoxides [Blee93].

Note that even though 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.

Citations: [Kolattukudy96, Pollard08]

Unification Links: AraCyc:PWY-321

Revised 17-Oct-2008 by Zhang P, TAIR
Revised 23-Feb-2015 by Caspi R, SRI International


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

Kolattukudy96: Kolattukudy, P.E. (1996). "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

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

Xue14: Xue Y, Xiao S, Kim J, Lung SC, Chen L, Tanner JA, Suh MC, Chye ML (2014). "Arabidopsis membrane-associated acyl-CoA-binding protein ACBP1 is involved in stem cuticle formation." J Exp Bot 65(18);5473-83. PMID: 25053648

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). "PlantMetabolomics.org: 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

Bi13: Bi H, Wang H, Cronan JE (2013). "FabQ, a dual-function dehydratase/isomerase, circumvents the last step of the classical fatty acid synthesis cycle." Chem Biol 20(9);1157-67. PMID: 23972938

Biebl02: Biebl H, Sproer C (2002). "Taxonomy of the glycerol fermenting clostridia and description of Clostridium diolis sp. nov." Syst Appl Microbiol 25(4);491-7. PMID: 12583708

Chi09: Chi A, Rhee S (2009). "The functional annotation of Arabidopsis protein sequences was performed by BLAST queries against a reference set of experimentally verified enzymes. For each Arabidopsis sequence, the enzymatic activity of the top BLAST hit (or hits if they had equivalent E-values) was assigned to the protein if its E-value fell below a specific E-value threshold established for the corresponding enzymatic activity. Note: The annotation thresholds were established by doing a self BLAST of the reference enzyme dataset. For each enzymatic activity represented by multiple proteins, the mean E-value of all the correct hits generated by the self BLAST was selected as the cut-off. All of these means were averaged and used as the cut-off for assigning annotations for any enzymatic activities that were represented by a single protein in the reference dataset."

Dobritsa09: Dobritsa AA, Shrestha J, Morant M, Pinot F, Matsuno M, Swanson R, Moller BL, Preuss D (2009). "CYP704B1 is a long-chain fatty acid omega-hydroxylase essential for sporopollenin synthesis in pollen of Arabidopsis." Plant Physiol 151(2);574-89. PMID: 19700560

Goldfine71: Goldfine H, Panos C (1971). "Phospholipids of Clostridium butyricum. IV. Analysis of the positional isomers of monounsaturated and cyclopropane fatty acids and alk-1'-enyl ethers by capillary column chromatography." J Lipid Res 12(2);214-20. PMID: 5554109

Gross06: Gross J, Cho WK, Lezhneva L, Falk J, Krupinska K, Shinozaki K, Seki M, Herrmann RG, Meurer J (2006). "A plant locus essential for phylloquinone (vitamin K1) biosynthesis originated from a fusion of four eubacterial genes." J Biol Chem 281(25);17189-96. PMID: 16617180

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

Hunt06: Hunt MC, Rautanen A, Westin MA, Svensson LT, Alexson SE (2006). "Analysis of the mouse and human acyl-CoA thioesterase (ACOT) gene clusters shows that convergent, functional evolution results in a reduced number of human peroxisomal ACOTs." FASEB J 20(11);1855-64. PMID: 16940157

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

Jiang08: Jiang M, Chen X, Guo ZF, Cao Y, Chen M, Guo Z (2008). "Identification and Characterization of (1R,6R)-2-Succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate Synthase in the Menaquinone Biosynthesis of Escherichia coli." Biochemistry 47(11);3426-34. PMID: 18284213

Jiang09: Jiang M, Chen X, Wu XH, Chen M, Wu YD, Guo Z (2009). "Catalytic mechanism of SHCHC synthase in the menaquinone biosynthesis of Escherichia coli: identification and mutational analysis of the active site residues." Biochemistry 48(29);6921-31. PMID: 19545176

Johnston83: Johnston NC, Goldfine H (1983). "Lipid composition in the classification of the butyric acid-producing clostridia." J Gen Microbiol 129(4);1075-81. PMID: 6886674

Kuznetsova05: Kuznetsova E, Proudfoot M, Sanders SA, Reinking J, Savchenko A, Arrowsmith CH, Edwards AM, Yakunin AF (2005). "Enzyme genomics: Application of general enzymatic screens to discover new enzymes." FEMS Microbiol Rev 29(2);263-79. PMID: 15808744

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

Li10a: 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

Meganathan01: Meganathan R (2001). "Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms." Vitam Horm 61;173-218. PMID: 11153266

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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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