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MetaCyc Chimeric Pathway: superpathway of anthocyanin biosynthesis (from cyanidin and cyanidin 3-O-glucoside)

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

Superclasses: Biosynthesis Secondary Metabolites Biosynthesis Phenylpropanoid Derivatives Biosynthesis Flavonoids Biosynthesis Anthocyanins Biosynthesis
Superpathways

Some taxa known to possess parts of the pathway include ? : Glandularia x hybrida , Ipomoea nil , Ipomoea purpurea , Perilla frutescens , Rosa hybrid cultivar , Salvia splendens , Vitis vinifera

Expected Taxonomic Range: Spermatophyta

Note: This is a chimeric pathway, comprising reactions from multiple organisms, and typically will not occur in its entirety in a single organism. The taxa listed here are likely to catalyze only subsets of the reactions depicted in this pathway.

Summary:
General Background

The superpathway of anthocyanin biosynthesis that originates from cyanidin and cyanidin 3-O-glucoside comprises the formation of compounds such as rose anthocyanin, anthocyanidin sophoroside and shisonin. Those anthocyanins are flower pigments that contribute to a wide variation of colors in many species representing various structures that range from simple anthocyanin diglucosides to more complex polyacylated anthocyanins.

Rose anthocyanins are based on the simple structure of cyanidin 3,5-diglucoside. This anthocyanin is obviously potent enough to provide the wide spectrum of colors found in roses. Like the anthocyanidin 3-glucoside in other plants (compare anthocyanin biosynthesis (cyanidin 3-O-glucoside), anthocyanin biosynthesis (delphinidin 3-O-glucoside)) the anthocyanidin 3,5-diglucoside constitutes the first stable anthocyanin in roses and contributes to its solubility in the vacuole [Heller94, WinkelShirley02]. Insofar the pathway described here is unique to the rose family.

Antocyanidins often occur as sophorosides, i.e. diglucosides that consist of glucose attached to the 2''-O-position of the 3-O-glucose moiety of anthocyanidins. The anthocyanidin that confers the bright blue color to Ipomoea nil (a member of the Convolvulacea) is a sophoroside that forms a complex with several caffeoyl residues, known as Wedding Bells anthocyanin (HBA). Reddish-brown flowers of dusky mutants of Ipomoea nil contain Heavenly Blue antocyanin (WBA) representing the most favorite flower hue for Japanese floriculturists [Morita05].

Shisonin, a mono-malonylated anthocyanin, has been found in high amounts in Labiatae. Together with the bi-malonylated anthocyanin salvianin (salvianin biosynthesis) shisonin constitutes a major flower pigment in that genus [Lu02a]. Both anthocyanins occur predominantly in different species, i.e. shisonin in Perilla [Yamazaki03b] and salvianin in Salvia [Kondo89] and share key enzymatic steps of their respective biosyntheses comprising glucosylation and aromatic and aliphatic acylation.

About This Pathway

Rose anthocyanin: The formation of cyanidin 3,5-diglucoside in roses is catalyzed by a distinctive enzyme that is able to glucosylate both the flavonoid A-ring 5-O-position and the 3-O-position of the flavonoid C-ring. In contrast to the two single glucosyltransferases involved in the generation of anthocyanin 3,5-diglucoside in other plants this unique enzyme possesses both catalytic activities and also changes the order of glucosylation [Ogata05]. The first intermediate in this pathway is the unstable anthocyanidin-5-O-glucoside which is subsequently further glucosylated to form the stable cyanidin 3,5-diglucoside.

Anthocyanin sophoroside: The crucial step in the formation of anthocyanidin sophoroside as precursors for HBA and WBA in Ipomoea is catalyzed by the anthocyanidin 3-O-glucoside 2-O''-glucosyltransferase (3GGT). The enzyme adds glucose to anthocyanidin 3-glucosides at the 2''-O-position of the glucose moiety forming the corresponding sophorosides. Although the enzyme accepts all three major anthocyanidin 3-O-glucoside, anthocyanidin 3,5-diglucoside are not suitable substrates for the 3GGT [Morita05].

Shisonin: The formation of shisonin, the precursor for the aliphatic acylation with malonyl-CoA to form malonylshisonin is carried out by 3-aromatic acylation of cyanindin 3-O-glucoside with p-coumaric acid [Fujiwara98] [YonekuraSakakib00] followed by the 5-O-glucosylation of the anthocyanin. The exact biosynthetic route towards shisonin is still a matter of debate and the actual succession of 5-O-glucosylation and 3-O-acylation remains to be demonstrated. The anthocyanin-5-O-glucoside-6'''-O-malonyltransferase [Suzuki03] that produces malonylshisonin expresses a high affinity towards both pelargonidin (salvianin biosynthesis) and cyanidin (shisonin biosynthesis) derived anthocyanidin intermediates forming the corresponding aromatic and aliphatic acylated compounds.

Subpathways: rose anthocyanin biosynthesis I (via cyanidin 5-O-β-D-glucoside)

Unification Links: PlantCyc:PWY-5313

Credits:
Created 07-Sep-2006 by Foerster H , TAIR


References

Fujiwara98: Fujiwara H, Tanaka Y, Fukui Y, Ashikari T, Yamaguchi M, Kusumi T (1998). "Purification and characterization of anthocyanin 3-aromatic acyltransferase from Perilla frutescens." Plant Science, 137, 87-94.

Heller94: Heller W, Forkmann G (1994). "Biosynthesis of flavonoids." In: Harborne JB (editor) The flavonoids. Advances in research since 1986. Chapman & Hall, London Glasgow New York Tokyo Melbourne Madras, 499-537.

Kondo89: Kondo T, Yoshikane M, Goto T (1989). "Structure of anthocyanins in scarlet, purple, and blue flowers of salvia." Tetrahedron Letters, 30(48), 6729-6732.

Lu02a: Lu Y, Foo LY (2002). "Polyphenolics of Salvia--a review." Phytochemistry 59(2);117-40. PMID: 11809447

Morita05: Morita Y, Hoshino A, Kikuchi Y, Okuhara H, Ono E, Tanaka Y, Fukui Y, Saito N, Nitasaka E, Noguchi H, Iida S (2005). "Japanese morning glory dusky mutants displaying reddish-brown or purplish-gray flowers are deficient in a novel glycosylation enzyme for anthocyanin biosynthesis, UDP-glucose:anthocyanidin 3-O-glucoside-2''-O-glucosyltransferase, due to 4-bp insertions in the gene." Plant J 42(3);353-63. PMID: 15842621

Ogata05: Ogata J, Kanno Y, Itoh Y, Tsugawa H, Suzuki M (2005). "Plant biochemistry: anthocyanin biosynthesis in roses." Nature 435(7043);757-8. PMID: 15944692

Suzuki03: Suzuki H, Nakayama T, Nishino T (2003). "Proposed mechanism and functional amino acid residues of malonyl-CoA:anthocyanin 5-O-glucoside-6'''-O-malonyltransferase from flowers of Salvia splendens, a member of the versatile plant acyltransferase family." Biochemistry 42(6);1764-71. PMID: 12578391

WinkelShirley02: Winkel-Shirley B (2002). "Biosynthesis of flavonoids and effects of stress." Curr Opin Plant Biol 5(3);218-23. PMID: 11960739

Yamazaki03b: Yamazaki M, Nakajima J, Yamanashi M, Sugiyama M, Makita Y, Springob K, Awazuhara M, Saito K (2003). "Metabolomics and differential gene expression in anthocyanin chemo-varietal forms of Perilla frutescens." Phytochemistry 62(6);987-95. PMID: 12590125

YonekuraSakakib00: Yonekura-Sakakibara K, Tanaka Y, Fukuchi-Mizutani M, Fujiwara H, Fukui Y, Ashikari T, Murakami Y, Yamaguchi M, Kusumi T (2000). "Molecular and biochemical characterization of a novel hydroxycinnamoyl-CoA: anthocyanin 3-O-glucoside-6"-O-acyltransferase from Perilla frutescens." Plant Cell Physiol 41(4);495-502. PMID: 10845463

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

Ford98: Ford CM, Boss PK, Hoj PB (1998). "Cloning and characterization of Vitis vinifera UDP-glucose:flavonoid 3-O-glucosyltransferase, a homologue of the enzyme encoded by the maize Bronze-1 locus that may primarily serve to glucosylate anthocyanidins in vivo." J Biol Chem 273(15);9224-33. PMID: 9535914

FukuchiMizutani11: Fukuchi-Mizutani M, Akagi M, Ishiguro K, Katsumoto Y, Fukui Y, Togami J, Nakamura N, Tanaka Y (2011). "Biochemical and molecular characterization of anthocyanidin/flavonol 3-glucosylation pathways in Rosa x hybrida." Plant biotechnology 28:239-244.

Hall12: Hall D, Yuan XX, Murata J, De Luca V (2012). "Molecular cloning and biochemical characterization of the UDP-glucose: flavonoid 3-O-glucosyltransferase from Concord grape (Vitis labrusca)." Phytochemistry 74;90-9. PMID: 22098678

Hennayake06: Hennayake CK, Takagi S, Nishimura K, Kanechi M, Uno Y, Inagaki N (2006). "Differential expression of anthocyanin biosynthesis genes in suspension culture cells of Rosa hybrida cv. Charleston." Plant biotechnology 23: 379-385.

Hennayake07: Hennayake CK, Kanechi M, Uno Y, Inagaki N (2007). "Differential Expression of Anthocyanin Biosynthetic Genes in 'Charleston' Roses." Acta Hort. 760:643-650.

Kubo04: Kubo A, Arai Y, Nagashima S, Yoshikawa T (2004). "Alteration of sugar donor specificities of plant glycosyltransferases by a single point mutation." Arch Biochem Biophys 429(2);198-203. PMID: 15313223

Kubo07: Kubo H, Nawa N, Lupsea SA (2007). "Anthocyaninless1 gene of Arabidopsis thaliana encodes a UDP-glucose:flavonoid-3-O-glucosyltransferase." J Plant Res 120(3);445-9. PMID: 17277900

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

Lazarowski03: Lazarowski ER, Shea DA, Boucher RC, Harden TK (2003). "Release of cellular UDP-glucose as a potential extracellular signaling molecule." Mol Pharmacol 63(5);1190-7. PMID: 12695547

Ogata98: Ogata J, Teramoto S, Yoshitama K (1998). "Isolation and Characterization of UDP-glucose: Cyanidin 3-O-glucosyltransferase from the Flower Buds of Senecio x hybridus." J. Plant Res. 111:213-216.

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

Sui11: Sui X, Gao X, Ao M, Wang Q, Yang D, Wang M, Fu Y, Wang L (2011). "cDNA cloning and characterization of UDP-glucose: anthocyanidin 3-O-glucosyltransferase in Freesia hybrida." Plant Cell Rep 30(7);1209-18. PMID: 21318353

Suzuki01a: Suzuki H, Nakayama T, Yonekura-Sakakibara K, Fukui Y, Nakamura N, Nakao M, Tanaka Y, Yamaguchi MA, Kusumi T, Nishino T (2001). "Malonyl-CoA:anthocyanin 5-O-glucoside-6"'-O-malonyltransferase from scarlet sage (Salvia splendens) flowers. Enzyme purification, gene cloning, expression, and characterization." J Biol Chem 276(52);49013-9. PMID: 11598135

Tohge05: Tohge T, Nishiyama Y, Hirai MY, Yano M, Nakajima J, Awazuhara M, Inoue E, Takahashi H, Goodenowe DB, Kitayama M, Noji M, Yamazaki M, Saito K (2005). "Functional genomics by integrated analysis of metabolome and transcriptome of Arabidopsis plants over-expressing an MYB transcription factor." Plant J 42(2);218-35. PMID: 15807784

Yamazaki99: Yamazaki M, Gong Z, Fukuchi-Mizutani M, Fukui Y, Tanaka Y, Kusumi T, Saito K (1999). "Molecular cloning and biochemical characterization of a novel anthocyanin 5-O-glucosyltransferase by mRNA differential display for plant forms regarding anthocyanin." J Biol Chem 274(11);7405-11. PMID: 10066805


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 Sun Nov 23, 2014, biocyc14.