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|
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.
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
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
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.
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
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