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MetaCyc Pathway: chlorogenic acid biosynthesis I

Enzyme View:

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.

Superclasses: Biosynthesis Secondary Metabolites Biosynthesis Phenylpropanoid Derivatives Biosynthesis Cinnamates Biosynthesis

Some taxa known to possess this pathway include ? : Coffea arabica , Coffea canephora

Expected Taxonomic Range: Rubiaceae , Viridiplantae

Summary:
Chlorogenic acids (CGAs) are a group of soluble phenolic compounds that are produced by a variety of plants, including Coffea canephora (robusta coffee).

CGAs include esters formed between certain hydroxycinnamic acids and quinate or its derivative shikimate. The most common CGA compound is 5-caffeoylquinate (5-CQA) [Mahesh07]. Other main groups of CGAs identified in green coffee beans include other CQA isomers, as well as dicaffeoylquinic and feruloylquinic acid isomers [Campa03].

CGAs fulfil various physiological roles in plants. For example, they are known to be involved in the protection of plants from abiotic stresses such as UV damage [Burchard00] and in increased resistance to bacterial infections [Niggeweg04].

Biosynthesis of 5-CQA can be catalyzed by the cytochrome P450 enzyme, CYP98A36. However, that enzyme can only hydroxylate the chlorogenic acid precursor 4-coumaroyl quinate. Another enzyme, CYP98A35, is able to metabolize both 4-coumaroyl quinate and 4-coumaroylshikimate with the same efficiency.

CGA biosynthesis and accumulation occurred mainly in the shoot tip and in the phloem of the vascular bundles. The biosynthetic activity of chlorogenic acids was clearly reduced in ripening and ripe seeds, especially in Coffea canephora [Koshiro]. An alternate pathway for CGA biosynthesis is described in chlorogenic acid biosynthesis II.

Credits:
Created 13-Sep-2008 by Pujar A , Boyce Thompson Institute


References

Burchard00: Burchard P, Bilger W, Weissenbock G (2000). "Contribution of hydroxycinnamates and flavonoids to epidermal shielding of UV-A and UV-B radiation in developing rye primary leaves as assessed by ultraviolet-induced chlorophyll fluorescence measurements." Plant, Cell and Environment 23(12);1373-1380.

Campa03: Campa C, Noirot M, Bourgeois M, Pervent M, Ky CL, Chrestin H, Hamon S, de Kochko A (2003). "Genetic mapping of a caffeoyl-coenzyme A 3-O-methyltransferase gene in coffee trees. Impact on chlorogenic acid content." Theor Appl Genet 107(4);751-6. PMID: 12861362

Koshiro: Koshiro Y, Jackson MC, Katahira R, Wang ML, Nagai C, Ashihara H "Biosynthesis of chlorogenic acids in growing and ripening fruits of Coffea arabica and Coffea canephora plants." Z Naturforsch [C] 62(9-10);731-42. PMID: 18069248

Mahesh07: Mahesh V, Million-Rousseau R, Ullmann P, Chabrillange N, Bustamante J, Mondolot L, Morant M, Noirot M, Hamon S, de Kochko A, Werck-Reichhart D, Campa C (2007). "Functional characterization of two p-coumaroyl ester 3'-hydroxylase genes from coffee tree: evidence of a candidate for chlorogenic acid biosynthesis." Plant Mol Biol 64(1-2);145-59. PMID: 17333503

Niggeweg04: Niggeweg R, Michael AJ, Martin C (2004). "Engineering plants with increased levels of the antioxidant chlorogenic acid." Nat Biotechnol 22(6);746-54. PMID: 15107863

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

Boerjan03: Boerjan W, Ralph J, Baucher M (2003). "Lignin biosynthesis." Annu Rev Plant Biol 54;519-46. PMID: 14503002

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.

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

Hoffmann03: Hoffmann L, Maury S, Martz F, Geoffroy P, Legrand M (2003). "Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism." J Biol Chem 278(1);95-103. PMID: 12381722

Hoffmann04: Hoffmann L, Besseau S, Geoffroy P, Ritzenthaler C, Meyer D, Lapierre C, Pollet B, Legrand M (2004). "Silencing of hydroxycinnamoyl-coenzyme A shikimate/quinate hydroxycinnamoyltransferase affects phenylpropanoid biosynthesis." Plant Cell 16(6);1446-65. PMID: 15161961

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

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

Kopycki08: Kopycki JG, Rauh D, Chumanevich AA, Neumann P, Vogt T, Stubbs MT (2008). "Biochemical and structural analysis of substrate promiscuity in plant Mg2+-dependent O-methyltransferases." J Mol Biol 378(1);154-64. PMID: 18342334

Kuhnl87: Kuhnl T, Koch U, Heller W, Wellmann E (1987). "Chlorogenic acid biosynthesis: characterization of a light-induced microsomal 5-O-(4-coumaroyl)-D-quinate/shikimate 3'-hydroxylase from carrot (Daucus carota L.) cell suspension cultures." Arch Biochem Biophys 258(1);226-32. PMID: 2821918

Lallemand12: Lallemand LA, McCarthy JG, McSweeney S, McCarthy AA (2012). "Purification, crystallization and preliminary X-ray diffraction analysis of a hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyltransferase (HCT) from Coffea canephora involved in chlorogenic acid biosynthesis." Acta Crystallogr Sect F Struct Biol Cryst Commun 68(Pt 7);824-8. PMID: 22750875

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

Lepelley07: Lepelley, M, Simkina, A, Cheminadea, G, Cailleta, V, Tremillon, N, McCarthy, J (2007). "Chlorogenic acid synthesis in coffee: An analysis of CGA content and real-time RT-PCR expression of HCT, HQT, C3H1, and CCoAOMT1 genes during grain development in C. canephora." Plant Science, 172, 978-996.

Lin13a: Lin Y, Sun X, Yuan Q, Yan Y (2013). "Combinatorial biosynthesis of plant-specific coumarins in bacteria." Metab Eng 18;69-77. PMID: 23644174

Rommens08: Rommens CM, Richael CM, Yan H, Navarre DA, Ye J, Krucker M, Swords K (2008). "Engineered native pathways for high kaempferol and caffeoylquinate production in potato." Plant Biotechnol J 6(9);870-86. PMID: 18662373

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

Schoch01: Schoch G, Goepfert S, Morant M, Hehn A, Meyer D, Ullmann P, Werck-Reichhart D (2001). "CYP98A3 from Arabidopsis thaliana is a 3'-hydroxylase of phenolic esters, a missing link in the phenylpropanoid pathway." J Biol Chem 276(39);36566-74. PMID: 11429408

Sullivan09: Sullivan M (2009). "A novel red clover hydroxycinnamoyl transferase has enzymatic activities consistent with a role in phaselic Acid biosynthesis." Plant Physiol 150(4);1866-79. PMID: 19525325

Wils13: Wils CR, Brandt W, Manke K, Vogt T (2013). "A single amino acid determines position specificity of an Arabidopsis thaliana CCoAOMT-like O-methyltransferase." FEBS Lett 587(6);683-9. PMID: 23416302


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 18.5 on Fri Nov 28, 2014, biocyc14.