KEGG   PATHWAY: ko00942Help
Entry
ko00942                     Pathway                                

Name
Anthocyanin biosynthesis
Description
Anthocyanidins (aglycones) and anthocyanins (glycosides) are common plant pigments and belong to a structural subclass of flavonoids characterized by a 2-phenylbenzopyrylium unit. They are derived along the flavonoid modification pathways and further separated into three types, pelargonidin, cyanidin, and delphinidin, due to the different number of hydroxyl groups in the phenyl group.
Class
Metabolism; Biosynthesis of other secondary metabolites
BRITE hierarchy
Pathway map
ko00942  Anthocyanin biosynthesis
ko00942

Ortholog table
Other DBs
BSID: 96861
GO: 0009718
Orthology
K12930  anthocyanidin 3-O-glucosyltransferase [EC:2.4.1.115]
K12931  anthocyanin 3-O-glucoside-6''-O-malonyltransferase [EC:2.3.1.171]
K12932  anthocyanidin 3-O-glucoside-3'',6''-O-dimalonyltransferase [EC:2.3.1.-]
K12933  anthocyanidin 3-O-glucoside 2''-O-glucosyltransferase [EC:2.4.1.297]
K17192  cyanidin 3-O-glucoside 7-O-glucosyltransferase (acyl-glucose) [EC:2.4.1.300]
K17193  anthocyanidin 3-O-glucoside 2'''-O-xylosyltransferase [EC:2.4.2.51]
K21383  anthocyanidin 3-O-glucoside 6''-O-acyltransferase [EC:2.3.1.215]
K12934  anthocyanin 5-O-glucoside-6'''-O-malonyltransferase [EC:2.3.1.172]
K12935  anthocyanin 5-O-glucoside-4'''-O-malonyltransferase [EC:2.3.1.214]
K12338  anthocyanidin 3-O-glucoside 5-O-glucosyltransferase [EC:2.4.1.298]
K17194  cyanidin 3-O-glucoside 5-O-glucosyltransferase (acyl-glucose) [EC:2.4.1.299]
K12936  anthocyanin 5-aromatic acyltransferase [EC:2.3.1.153]
K12937  cyanidin-3-O-glucoside 2''-O-glucuronosyltransferase [EC:2.4.1.254]
K12938  anthocyanidin 5,3-O-glucosyltransferase [EC:2.4.1.-]
K12939  anthocyanin 3'-O-beta-glucosyltransferase [EC:2.4.1.238]
Compound
C05904  Pelargonidin
C05905  Cyanidin
C05908  Delphinidin
C08604  Chrysanthemin
C08620  Cyanidin 3-O-rutinoside
C08639  Cyanin
C08641  Gentiodelphin
C08725  Pelargonin
C12095  Cyanidin 3-O-(6-O-p-coumaroyl)glucoside
C12096  Cyanidin 3-O-(6-O-p-coumaroyl)glucoside-5-O-glucoside
C12137  Pelargonidin 3-O-glucoside
C12138  Delphinidin 3-O-glucoside
C12139  Petunidin 3-O-glucoside
C12140  Malvidin 3-O-glucoside
C12141  Peonidin 3-O-glucoside
C12640  Pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside
C12641  4'''-Demalonylsalvianin
C12642  Pelargonidin 3-O-(6-O-malonyl-beta-D-glucoside)
C12643  Cyanidin 3-O-(6-O-malonyl-beta-D-glucoside)
C12644  Pelargonidin 3-O-rutinoside
C12645  Pelargonidin 3-O-rutinoside 5-O-beta-D-glucoside
C12646  Cyanidin 3-O-rutinoside 5-O-beta-D-glucoside
C12647  Salvianin
C16288  Pelargonidin 3-O-3'',6''-O-dimalonylglucoside
C16289  Cyanidin 3-O-3'',6''-O-dimalonylglucoside
C16290  Delphinidin 3-O-3'',6''-O-dimalonylglucoside
C16292  Cyanidin-3-(p-coumaroyl)-rutinoside-5-glucoside
C16293  Peonidin-3-(p-coumaroyl)-rutinoside-5-glucoside
C16294  Delphinidin-3-(p-coumaroyl)-rutinoside-5-glucoside
C16295  Petunidin-3-(p-coumaroyl)-rutinoside-5-glucoside
C16296  Malvidin-3-(p-coumaroyl)-rutinoside-5-glucoside
C16297  Pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside)
C16298  Cyanidin 5-O-glucoside
C16299  Malonylshisonin
C16301  Delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside
C16302  Ternatin A1
C16303  Ternatin C5
C16304  Delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside
C16305  Pelargonidin 3-O-sophoroside
C16306  Cyanidin 3-O-sophoroside
C16307  Delphinidin 3-O-sophoroside
C16312  Delphin
C16313  Delphinidin 3-glucoside 5-caffoyl-glucoside
C16314  Delphinidin 3,5,3'-triglucoside
C16315  Tulipanin
C16349  Pelargonidin 3-O-beta-D-glucoside 5-O-(6-coumaroyl-beta-D-glucoside)
C16350  Cyanidin 3-O-beta-D-glucoside 5-O-(6-coumaroyl-beta-D-glucoside)
C16351  Delphinidin 3-O-beta-D-glucoside 5-O-(6-coumaroyl-beta-D-glucoside)
C16354  Albireodelphin
C16367  Delphinidin 3-O-(6-caffeoyl-beta-D-glucoside)
C16368  Pelargonidin 3-(6-p-coumaroyl)glucoside
C16369  Cyanidin 3-(6-p-caffeoyl)glucoside
C16370  Delphinidin 3-(6-p-coumaroyl)glucoside
C16371  Pelargonidin 3-glucoside 5-caffeoylglucoside
C16372  Cyanidin 3-glucoside 5-caffeoylglucoside
C16373  Cyanidin-3-O-(6''-O-malonyl-2''-O-glucuronyl)glucoside
C19762  Cyanidin 3-O-(2-O-beta-D-glucuronosyl)-beta-D-glucoside
C20469  Cyanidin 3,7-di-O-beta-D-glucoside
C20489  Pelargonidin 3-O-beta-D-sambubioside
C20490  Cyanidin 3-O-beta-D-sambubioside
C20491  Delphinidin 3-O-beta-D-sambubioside
C20492  Pelargonidin 5-O-beta-D-glucoside 3-O-beta-D-sambubioside
C20493  Cyanidin 5-O-beta-D-glucoside 3-O-beta-D-sambubioside
C20494  Delphinidin 5-O-beta-D-glucoside 3-O-beta-D-sambubioside
C20495  Pelargonidin 3,7-di-O-beta-D-glucoside
C20496  Delphinidin 3,7-di-O-beta-D-glucoside
Reference
  Authors
Unno H, Ichimaida F, Suzuki H, Takahashi S, Tanaka Y, Saito A, Nishino T, Kusunoki M, Nakayama T.
  Title
Structural and mutational studies of anthocyanin malonyltransferases establish the features of BAHD enzyme catalysis.
  Journal
J Biol Chem 282:15812-22 (2007)
DOI:10.1074/jbc.M700638200
Reference
  Authors
Kogawa K, Kazuma K, Kato N, Noda N, Suzuki M.
  Title
Biosynthesis of malonylated flavonoid glycosides on the basis of malonyltransferase activity in the petals of Clitoria ternatea.
  Journal
J Plant Physiol 164:886-94 (2007)
DOI:10.1016/j.jplph.2006.05.006
Reference
  Authors
Tsai CJ, Harding SA, Tschaplinski TJ, Lindroth RL, Yuan Y.
  Title
Genome-wide analysis of the structural genes regulating defense phenylpropanoid metabolism in Populus.
  Journal
New Phytol 172:47-62 (2006)
DOI:10.1111/j.1469-8137.2006.01798.x
Reference
  Authors
Ogata J, Kanno Y, Itoh Y, Tsugawa H, Suzuki M.
  Title
Plant biochemistry: anthocyanin biosynthesis in roses.
  Journal
Nature 435:757-8 (2005)
DOI:10.1038/nature435757a
Reference
  Authors
Bowles D, Isayenkova J, Lim EK, Poppenberger B.
  Title
Glycosyltransferases: managers of small molecules.
  Journal
Curr Opin Plant Biol 8:254-63 (2005)
DOI:10.1016/j.pbi.2005.03.007
Reference
  Authors
Morita Y, Hoshino A, Kikuchi Y, Okuhara H, Ono E, Tanaka Y, Fukui Y, Saito N, Nitasaka E, Noguchi H, Iida S.
  Title
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.
  Journal
Plant J 42:353-63 (2005)
DOI:10.1111/j.1365-313X.2005.02383.x
Reference
  Authors
Sawada S, Suzuki H, Ichimaida F, Yamaguchi MA, Iwashita T, Fukui Y, Hemmi H, Nishino T, Nakayama T.
  Title
UDP-glucuronic acid:anthocyanin glucuronosyltransferase from red daisy (Bellis perennis) flowers. Enzymology and phylogenetics of a novel glucuronosyltransferase involved in flower pigment biosynthesis.
  Journal
J Biol Chem 280:899-906 (2005)
DOI:10.1074/jbc.M410537200
Reference
  Authors
Suzuki H, Sawada S, Watanabe K, Nagae S, Yamaguchi MA, Nakayama T, Nishino T.
  Title
Identification and characterization of a novel anthocyanin malonyltransferase from scarlet sage (Salvia splendens) flowers: an enzyme that is phylogenetically separated from other anthocyanin acyltransferases.
  Journal
Plant J 38:994-1003 (2004)
DOI:10.1111/j.1365-313X.2004.02101.x
Reference
  Authors
Suzuki H, Nakayama T, Yamaguchi M, Nishino T.
  Title
cDNA cloning and characterization of two Dendranthema x morifolium anthocyanin malonyltransferases with different functional activities.
  Journal
Plant Sci 166(1):89-96 (2004)
DOI:10.1016/j.plantsci.2003.08.010
Reference
  Authors
Nakayama T, Suzuki H, Nishino T.
  Title
Anthocyanin acyltransferases: specificities, mechanism, phylogenetics, and applications.
  Journal
Journal of Molecular Catalysis B: Enzymatic 23(2-6):117-132 (2003)
DOI:10.1016/S1381-1177(03)00078-X
Reference
  Authors
Fukuchi-Mizutani M, Okuhara H, Fukui Y, Nakao M, Katsumoto Y, Yonekura-Sakakibara K, Kusumi T, Hase T, Tanaka Y.
  Title
Biochemical and molecular characterization of a novel UDP-glucose:anthocyanin 3'-O-glucosyltransferase, a key enzyme for blue anthocyanin biosynthesis, from gentian.
  Journal
Plant Physiol 132:1652-63 (2003)
DOI:10.1104/pp.102.018242
Reference
  Authors
Springob K, Nakajima J, Yamazaki M, Saito K.
  Title
Recent advances in the biosynthesis and accumulation of anthocyanins.
  Journal
Nat Prod Rep 20:288-303 (2003)
DOI:10.1039/b109542k
Reference
  Authors
Suzuki H, Nakayama T, Yonekura-Sakakibara K, Fukui Y, Nakamura N, Nakao M, Tanaka Y, Yamaguchi MA, Kusumi T, Nishino T
  Title
Malonyl-CoA:anthocyanin 5-O-glucoside-6"'-O-malonyltransferase from scarlet sage (Salvia splendens) flowers. Enzyme purification, gene cloning, expression, and characterization.
  Journal
J Biol Chem 276:49013-9 (2001)
DOI:10.1074/jbc.M108444200
Reference
  Authors
Burbulis IE, Winkel-Shirley B.
  Title
Interactions among enzymes of the Arabidopsis flavonoid biosynthetic pathway.
  Journal
Proc Natl Acad Sci U S A 96:12929-34 (1999)
DOI:10.1073/pnas.96.22.12929
Reference
  Authors
Brugliera F, Barri-Rewell G, Holton TA, Mason JG.
  Title
Isolation and characterization of a flavonoid 3'-hydroxylase cDNA clone corresponding to the Ht1 locus of Petunia hybrida.
  Journal
Plant J 19:441-51 (1999)
DOI:10.1046/j.1365-313X.1999.00539.x
Reference
  Authors
Boss PK, Davies C, Robinson SP.
  Title
Analysis of the Expression of Anthocyanin Pathway Genes in Developing Vitis vinifera L. cv Shiraz Grape Berries and the Implications for Pathway Regulation.
  Journal
Plant Physiol 111:1059-1066 (1996)
DOI:10.1104/pp.111.4.1059
Reference
  Authors
Holton TA, Cornish EC.
  Title
Genetics and Biochemistry of Anthocyanin Biosynthesis.
  Journal
Plant Cell 7:1071-1083 (1995)
DOI:10.1105/tpc.7.7.1071
Reference
PMID:8130799
  Authors
Kroon J, Souer E, de Graaff A, Xue Y, Mol J, Koes R.
  Title
Cloning and structural analysis of the anthocyanin pigmentation locus Rt of Petunia hybrida: characterization of insertion sequences in two mutant alleles.
  Journal
Plant J 5:69-80 (1994)
DOI:10.1046/j.1365-313X.1994.5010069.x

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