MetaCyc Pathway: suberin monomers biosynthesis

Pathway diagram: suberin monomers biosynthesis

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

Superclasses: Biosynthesis Cell Structures Biosynthesis Plant Cell Structures
Metabolic Clusters

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

Expected Taxonomic Range: Tracheophyta

Suberin is a polymeric plant cell wall constituent mainly found in the epidermal tissues of underground plant parts. Suberin consists of two domains, a polyaromatic and a polyaliphatic domain. The polyaromatics are predominately located within the primary cell wall, and the polyaliphatics are located between the primary cell wall and the plasmalemma. The two domains are supposed to be cross-linked. The exact qualitative and quantitative composition of suberin monomers varies in different species. The major monomers found in the potato tuber polyaliphatics are ω-hydroxyacids (mainly 18-hydroxyoleate) and α,ω-diacids (mainly α,ω-9Z-octadecenedioate). The monomers of the polyaromatics are hydroxycinnamic acids and derivatives. N-feruloyltyramine is a major aromatic monomer found in suberized potato tubers. In addition to the aromatics and aliphatics components, glycerol has been reported a major suberin component in potato. The role of glycerol is proposed to interlink aliphatic monomers, and possibly also to link polyaliphatics to polyaromatics, during suberin polymer assembly. The polymerization step of aromatic monomers has been shown to involve a peroxidase reaction.

Note that the biosynthesis of suberin aliphatic monomers shares the same upstream reactions with cutin biosynthesis, and the biosynthesis of aromatics shares the same upstream reactions with lignin biosynthesis. Although both suberin and cutin contain aliphatic monomers, suberin differs from cutin by the chain length of aliphatic monomers, which can range from C16 to C32.

The pathway depicted here represents the biosynthesis of the major suberin monomers, namely 18-hydroxyoleate, α,ω-9Z-octadecenedioate, and N-feruloyltyramine, characterized in potato, as well as very long chain aliphatic monomers found in many plants. It also shows the production of 16-hydroxypalmitate, a precursor of an important component of aromatic suberin in Arabidopsis [Molina09, Gou09].

Citations: [P80, M98, Graca00, Jonathan96, Compagnon09]

Unification Links: AraCyc:PWY-1121

Revised 10-Feb-2011 by Zhang P


Compagnon09: Compagnon V, Diehl P, Benveniste I, Meyer D, Schaller H, Schreiber L, Franke R, Pinot F (2009). "CYP86B1 is required for very long chain omega-hydroxyacid and alpha, omega -dicarboxylic acid synthesis in root and seed suberin polyester." Plant Physiol 150(4);1831-43. PMID: 19525321

Gou09: Gou JY, Yu XH, Liu CJ (2009). "A hydroxycinnamoyltransferase responsible for synthesizing suberin aromatics in Arabidopsis." Proc Natl Acad Sci U S A 106(44);18855-60. PMID: 19846769

Graca00: Graca J, Pereira H (2000). "Suberin structure in potato periderm: glycerol, long-chain monomers, and glyceryl and feruloyl dimers." J Agric Food Chem 48(11);5476-83. PMID: 11087505

Jonathan96: Jonathan Negrel, Brigitte Pollet, Catherine Lapierre "Ether-linked ferulic acid amides in natural and wound periderms of potato tuber." Phytochemistry, 1996, 43(6):1195-1199.

M98: M.A. Bernards, N.G. Lewis "Macromolecular aromatics in suberized tissue." Phytochemistry, 1998, 47(6): 915-933.

Molina09: Molina I, Li-Beisson Y, Beisson F, Ohlrogge JB, Pollard M (2009). "Identification of an Arabidopsis feruloyl-coenzyme A transferase required for suberin synthesis." Plant Physiol 151(3);1317-28. PMID: 19759341

P80: P.E. Kolattukudy "The Biochemistry of Plants: a comprehensive treatise P.K. Stumpf and E.E. Conn (editors)." 1980, 4:571-646.

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

Bhuiya09: Bhuiya MW, Liu CJ (2009). "A cost-effective colorimetric assay for phenolic O-methyltransferases and characterization of caffeate 3-O-methyltransferases from Populus trichocarpa." Anal Biochem 384(1);151-8. PMID: 18926792

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

Curry99: Curry, J, Aluru, M, Mendoza, M, Nevarez, J, Melendrez, M, O' Connell, M. A (1999). "Transcripts for posssible capsaicinoid biosynthetic genes are differentially accumulated in pungent and non-pungent Capsicum." Plant Science, 148, 47-57.

Ehlting99: Ehlting J, Buttner D, Wang Q, Douglas CJ, Somssich IE, Kombrink E (1999). "Three 4-coumarate:coenzyme A ligases in Arabidopsis thaliana represent two evolutionarily divergent classes in angiosperms." Plant J 1999;19(1);9-20. PMID: 10417722

Franke02: Franke R, Humphreys JM, Hemm MR, Denault JW, Ruegger MO, Cusumano JC, Chapple C (2002). "The Arabidopsis REF8 gene encodes the 3-hydroxylase of phenylpropanoid metabolism." Plant J 30(1);33-45. PMID: 11967091

Franke02a: Franke R, Hemm MR, Denault JW, Ruegger MO, Humphreys JM, Chapple C (2002). "Changes in secondary metabolism and deposition of an unusual lignin in the ref8 mutant of Arabidopsis." Plant J 30(1);47-59. PMID: 11967092

Grienenberger09: Grienenberger E, Besseau S, Geoffroy P, Debayle D, Heintz D, Lapierre C, Pollet B, Heitz T, Legrand M (2009). "A BAHD acyltransferase is expressed in the tapetum of Arabidopsis anthers and is involved in the synthesis of hydroxycinnamoyl spermidines." Plant J 58(2);246-59. PMID: 19077165

Hamberger04: Hamberger B, Hahlbrock K (2004). "The 4-coumarate:CoA ligase gene family in Arabidopsis thaliana comprises one rare, sinapate-activating and three commonly occurring isoenzymes." Proc Natl Acad Sci U S A 101(7);2209-14. PMID: 14769935

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

Hohlfeld95: Hohlfeld H, Schurmann W, Scheel D, Strack D (1995). "Partial Purification and Characterization of Hydroxycinnamoyl-Coenzyme A:Tyramine Hydroxycinnamoyltransferase from Cell Suspension Cultures of Solanum tuberosum." Plant Physiol 107(2);545-552. PMID: 12228382

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

Humphreys99: Humphreys JM, Hemm MR, Chapple C (1999). "New routes for lignin biosynthesis defined by biochemical characterization of recombinant ferulate 5-hydroxylase, a multifunctional cytochrome P450-dependent monooxygenase." Proc Natl Acad Sci U S A 1999;96(18);10045-50. PMID: 10468559

Ibdah03: Ibdah M, Zhang XH, Schmidt J, Vogt T (2003). "A novel Mg(2+)-dependent O-methyltransferase in the phenylpropanoid metabolism of Mesembryanthemum crystallinum." J Biol Chem 278(45);43961-72. PMID: 12941960

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

Kai08: Kai K, Mizutani M, Kawamura N, Yamamoto R, Tamai M, Yamaguchi H, Sakata K, Shimizu B (2008). "Scopoletin is biosynthesized via ortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabidopsis thaliana." Plant J 55(6);989-99. PMID: 18547395

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

Kim01: Kim SH, Virmani D, Wake K, MacDonald K, Kronstad JW, Ellis BE (2001). "Cloning and disruption of a phenylalanine ammonia-lyase gene from Ustilago maydis." Curr Genet 40(1);40-8. PMID: 11570515

Klempien12: Klempien A, Kaminaga Y, Qualley A, Nagegowda DA, Widhalm JR, Orlova I, Shasany AK, Taguchi G, Kish CM, Cooper BR, D'Auria JC, Rhodes D, Pichersky E, Dudareva N (2012). "Contribution of CoA ligases to benzenoid biosynthesis in petunia flowers." Plant Cell 24(5);2015-30. PMID: 22649270

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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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