MetaCyc Pathway: trans-cinnamoyl-CoA biosynthesis

Enzyme View:

Pathway diagram: trans-cinnamoyl-CoA 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: (E)-cinnamoyl-CoA biosynthesis, trans-cinnamoyl-coenzyme A biosynthesis, cinnamoyl-CoA biosynthesis

Superclasses: Biosynthesis Aromatic Compounds Biosynthesis
Biosynthesis Secondary Metabolites Biosynthesis Phenylpropanoid Derivatives Biosynthesis Cinnamates Biosynthesis

Some taxa known to possess this pathway include ? : Arabidopsis thaliana col , Catharanthus roseus , Cucumis sativus , Hypericum androsaemum , Hypericum calycinum , Nicotiana tabacum , Petunia x hybrida , Streptomyces maritimus

Expected Taxonomic Range: Bacteria , Embryophyta

General Background

(E)-cinnamoyl-CoA and the closely related compound, 4-coumaryl-CoA are important precursors to a number of compound classes, including phenylpropanoids, flavonoids, and volatile benzenoids in plants and polyketides in plants and bacteria [Moore02, Katsuyama09a]. Members of these classes can play many roles, for instance as defense, signaling, pigment, and aroma compounds.

About This Pathway

Both (E)-cinnamoyl-CoA and 4-coumaryl-CoA are derived from trans-cinnamate produced from L-phenylalanine by the activity of a phenylalanine ammonia lysase (PAL). Their only structural difference is the presence of a hydroxyl group in the 4-position on the benzene ring. If the hydroxyl group is added directly to trans-cinnamate, then 4-coumaryl-CoA can be made without a (E)-cinnamoyl-CoA intermediate (see phenylpropanoid biosynthesis, initial reactions and phenylpropanoid biosynthesis). However, as shown in this pathway, trans-cinnamate can be also be a direct substrate for a CoA ligase. In some cases, the (E)-cinnamoyl-CoA generated by this enzyme may be used directly in secondary metabolic pathways (e.g. benzoate biosynthesis I (CoA-dependent, β-oxidative), pinobanksin biosynthesis), however, it may also be used to produce 4-coumaryl-CoA through a late hydroxylation (e.g. curcuminoid biosynthesis).

Although PAL has been well-characterized in plants since its initial discovery in 1961 [Koukol61], it wasn't until much later than an enzyme believed to be responsible for catalyzing the second step in this pathway was first identified in bacteria [Moore02].

In plants, the first step in this pathway is often rate limiting, for example, in the production of flavonoids. Therefore, expression levels and activity levels of PAL are often highly regulated and changes are induced by different stresses (rev. in [MacDonald07], ex. in [Liu06a]).

Citations: [Xiang02]

Superpathways: hyperxanthone E biosynthesis , benzoate biosynthesis I (CoA-dependent, β-oxidative) , curcuminoid biosynthesis , benzoate biosynthesis III (CoA-dependent, non-β-oxidative)

Unification Links: PlantCyc:PWY-6457

Created 10-Mar-2010 by Dreher KA , TAIR


Guranowski10: Guranowski A, Wojdyla AM, Zimny J, Wypijewska A, Kowalska J, Jemielity J, Davis RE, Bieganowski P (2010). "Dual activity of certain HIT-proteins: A. thaliana Hint4 and C. elegans DcpS act on adenosine 5'-phosphosulfate as hydrolases (forming AMP) and as phosphorylases (forming ADP)." FEBS Lett 584(1);93-8. PMID: 19896942

Katsuyama09a: Katsuyama Y, Kita T, Funa N, Horinouchi S (2009). "Curcuminoid biosynthesis by two type III polyketide synthases in the herb Curcuma longa." J Biol Chem 284(17);11160-70. PMID: 19258320

Koukol61: Koukol, J., Conn, E.E. (1961). "The metabolism of aromatic compounds in higher plants. IV. Purification and properties of the phenylalanine deaminase of Hordeum vulgare." J Biol Chem 236;2692-8. PMID: 14458851

Liu06a: Liu R, Xu S, Li J, Hu Y, Lin Z (2006). "Expression profile of a PAL gene from Astragalus membranaceus var. Mongholicus and its crucial role in flux into flavonoid biosynthesis." Plant Cell Rep 25(7);705-10. PMID: 16456646

MacDonald07: MacDonald MJ, D'Cunha GB (2007). "A modern view of phenylalanine ammonia lyase." Biochem Cell Biol 85(3);273-82. PMID: 17612622

Moore02: Moore BS, Hertweck C, Hopke JN, Izumikawa M, Kalaitzis JA, Nilsen G, O'Hare T, Piel J, Shipley PR, Xiang L, Austin MB, Noel JP (2002). "Plant-like biosynthetic pathways in bacteria: from benzoic acid to chalcone." J Nat Prod 65(12);1956-62. PMID: 12502351

Xiang02: Xiang L, Moore BS (2002). "Inactivation, complementation, and heterologous expression of encP, a novel bacterial phenylalanine ammonia-lyase gene." J Biol Chem 277(36);32505-9. PMID: 12082112

Xiang03: Xiang L, Moore BS (2003). "Characterization of benzoyl coenzyme A biosynthesis genes in the enterocin-producing bacterium "Streptomyces maritimus"." J Bacteriol 185(2);399-404. PMID: 12511484

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

Abd02: Abd El-Mawla AM, Beerhues L (2002). "Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum." Planta 214(5);727-33. PMID: 11882941

Colquhoun12: Colquhoun TA, Marciniak DM, Wedde AE, Kim JY, Schwieterman ML, Levin LA, Van Moerkercke A, Schuurink RC, Clark DG (2012). "A peroxisomally localized acyl-activating enzyme is required for volatile benzenoid formation in a Petuniaxhybrida cv. 'Mitchell Diploid' flower." J Exp Bot 63(13);4821-33. PMID: 22771854

Gaid12: Gaid MM, Sircar D, Muller A, Beuerle T, Liu B, Ernst L, Hansch R, Beerhues L (2012). "Cinnamate:CoA Ligase Initiates the Biosynthesis of a Benzoate-Derived Xanthone Phytoalexin in Hypericum calycinum Cell Cultures." Plant Physiol 160(3);1267-80. PMID: 22992510

Hertweck01: Hertweck C, Jarvis AP, Xiang L, Moore BS, Oldham NJ (2001). "A mechanism of benzoic acid biosynthesis in plants and bacteria that mirrors fatty acid beta-oxidation." Chembiochem 2(10);784-6. PMID: 11948863

Kim01b: 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

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

Piel00: Piel J, Hertweck C, Shipley PR, Hunt DM, Newman MS, Moore BS (2000). "Cloning, sequencing and analysis of the enterocin biosynthesis gene cluster from the marine isolate 'Streptomyces maritimus': evidence for the derailment of an aromatic polyketide synthase." Chem Biol 7(12);943-55. PMID: 11137817

Rubio06: Rubio S, Larson TR, Gonzalez-Guzman M, Alejandro S, Graham IA, Serrano R, Rodriguez PL (2006). "An Arabidopsis mutant impaired in coenzyme A biosynthesis is sugar dependent for seedling establishment." Plant Physiol 140(3);830-43. PMID: 16415216

Van09: Van Moerkercke A, Schauvinhold I, Pichersky E, Haring MA, Schuurink RC (2009). "A plant thiolase involved in benzoic acid biosynthesis and volatile benzenoid production." Plant J 60(2);292-302. PMID: 19659733

Vannelli07: Vannelli T, Wei Qi W, Sweigard J, Gatenby AA, Sariaslani FS (2007). "Production of p-hydroxycinnamic acid from glucose in Saccharomyces cerevisiae and Escherichia coli by expression of heterologous genes from plants and fungi." Metab Eng 9(2);142-51. PMID: 17204442

Wanner95: Wanner LA, Li G, Ware D, Somssich IE, Davis KR (1995). "The phenylalanine ammonia-lyase gene family in Arabidopsis thaliana." Plant Mol Biol 1995;27(2);327-38. PMID: 7888622

Xiang02a: Xiang L, Kalaitzis JA, Nilsen G, Chen L, Moore BS (2002). "Mutational analysis of the enterocin favorskii biosynthetic rearrangement." Org Lett 4(6);957-60. PMID: 11893195

Xue07: Xue Z, McCluskey M, Cantera K, Sariaslani FS, Huang L (2007). "Identification, characterization and functional expression of a tyrosine ammonia-lyase and its mutants from the photosynthetic bacterium Rhodobacter sphaeroides." J Ind Microbiol Biotechnol 34(9);599-604. PMID: 17602252

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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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