ENTRY       sly00942                    Pathway
NAME        Anthocyanin biosynthesis - Solanum lycopersicum (tomato)
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
PATHWAY_MAP sly00942  Anthocyanin biosynthesis
DBLINKS     GO: 0009718
ORGANISM    Solanum lycopersicum (tomato) [GN:sly]
GENE        101260093  anthocyanidin 3-O-glucosyltransferase [KO:K12930] [EC:2.4.1.115]
            101244178  UDP-glycosyltransferase 79B6 isoform X1 [KO:K17193] [EC:2.4.2.51]
COMPOUND    C05904  Pelargonidin
            C05905  Cyanidin
            C05908  Delphinidin
            C08604  Cyanidin 3-O-glucoside
            C08620  Cyanidin 3-O-rutinoside
            C08639  Cyanidin 3,5-O-diglucoside
            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  Delphinidin 3,5-diglucoside
            C16313  Delphinidin 3-glucoside 5-caffoyl-glucoside
            C16314  Delphinidin 3,5,3'-triglucoside
            C16315  Delphinidin 3-O-rutinoside
            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   PMID:17383962
  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   PMID:16887235
  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   PMID:16945088
  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   PMID:15944692
  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   PMID:15860422
  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   PMID:15842621
  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   PMID:15509561
  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   PMID:15165190
  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 166:89-96 (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   J Mol Catal B Enzym 23:117-132 (2003)
            DOI:10.1016/S1381-1177(03)00078-X
REFERENCE   PMID:12857844
  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   PMID:12828368
  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   PMID:11598135
  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   PMID:10536025
  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   PMID:10504566
  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   PMID:12226348
  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   PMID:12242398
  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
REL_PATHWAY sly00941  Flavonoid biosynthesis
KO_PATHWAY  ko00942
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