ENTRY       sly00941                    Pathway
NAME        Flavonoid biosynthesis - Solanum lycopersicum (tomato)
DESCRIPTION Flavonoids are a major class of plant secondary metabolites that serves a multitude of functions including pigments and antioxidant activity. Flavonoids are synthesized from phenylpropanoid derivatives by condensation with malonyl-CoA. For example, condensation of p-coumaroyl-CoA (C6-C3) with three malonyl-CoA (C3) molecules results in naringenin chalcone with a diphenylpropane (C6-C3-C6) unit, which is converted to naringenin with the flavone (2-phenylchromen-4-one) backbone by conjugate ring closure. These and further modifications yield a variety of structural forms including chalcones, flavanones, dihyroflavonols, and flavans, anthocyanins, flavones and flavonols, and isoflavonoids.
CLASS       Metabolism; Biosynthesis of other secondary metabolites
PATHWAY_MAP sly00941  Flavonoid biosynthesis
MODULE      sly_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:sly00941]
            sly_M00138  Flavonoid biosynthesis, naringenin => pelargonidin [PATH:sly00941]
DBLINKS     GO: 0009813
ORGANISM    Solanum lycopersicum (tomato) [GN:sly]
GENE        778294  CHS1; chalcone synthase 1 [KO:K00660] [EC:2.3.1.74]
            101245061  chalcone synthase B [KO:K00660] [EC:2.3.1.74]
            101266107  chalcone synthase J-like [KO:K00660] [EC:2.3.1.74]
            778295  CHS2; chalcone synthase 2 [KO:K00660] [EC:2.3.1.74]
            101263032  LOW QUALITY PROTEIN: chalcone synthase J [KO:K00660] [EC:2.3.1.74]
            101249265  CHI1; chalcone--flavonone isomerase [KO:K01859] [EC:5.5.1.6]
            101250693  chalcone--flavonone isomerase [KO:K01859] [EC:5.5.1.6]
            101266223  probable chalcone--flavonone isomerase 3 [KO:K01859] [EC:5.5.1.6]
            100736482  F3H; flavanone 3-dioxygenase [KO:K00475] [EC:1.14.11.9]
            101249699  flavonol synthase/flavanone 3-hydroxylase [KO:K05278] [EC:1.14.20.6]
            101244196  trans-cinnamate 4-monooxygenase isoform X2 [KO:K00487] [EC:1.14.14.91]
            101244496  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
            101262919  cytochrome P450 CYP73A100 [KO:K00487] [EC:1.14.14.91]
            101266618  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
            544150  dihydroflavonol 4-reductase [KO:K13082] [EC:1.1.1.219 1.1.1.234]
            100736504  F3'5'H; flavonoid 3'5' hydroxylase [KO:K13083] [EC:1.14.14.81]
            101251607  leucoanthocyanidin dioxygenase isoform X1 [KO:K05277] [EC:1.14.20.4]
            101263493  anthocyanidin reductase ((2S)-flavan-3-ol-forming) [KO:K08695] [EC:1.3.1.77]
            104645412  BAHD acyltransferase At5g47980-like isoform X1 [KO:K13065] [EC:2.3.1.133]
            544249  hqt; hydroxycinnamoyl CoA quinate transferase [KO:K13065] [EC:2.3.1.133]
            100191129  anthocyanin acyltransferase [KO:K13065] [EC:2.3.1.133]
            101055588  AT1; AT1 protein [KO:K13065] [EC:2.3.1.133]
            101055589  AT3; AT3 protein [KO:K13065] [EC:2.3.1.133]
            101256271  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            101244961  agmatine coumaroyltransferase-2 [KO:K13065] [EC:2.3.1.133]
            101249389  acylsugar acyltransferase 3-like [KO:K13065] [EC:2.3.1.133]
            101253286  vinorine synthase [KO:K13065] [EC:2.3.1.133]
            101266953  vinorine synthase [KO:K13065] [EC:2.3.1.133]
            101253503  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
            101245674  acylsugar acyltransferase 3-like [KO:K13065] [EC:2.3.1.133]
            101248691  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            101253556  agmatine hydroxycinnamoyltransferase 1-like [KO:K13065] [EC:2.3.1.133]
            101253859  agmatine hydroxycinnamoyltransferase 1-like [KO:K13065] [EC:2.3.1.133]
            101267379  agmatine coumaroyltransferase-2-like [KO:K13065] [EC:2.3.1.133]
            101260610  acetyl-CoA-benzylalcohol acetyltransferase [KO:K13065] [EC:2.3.1.133]
            101254278  pelargonidin 3-O-(6-caffeoylglucoside) 5-O-(6-O-malonylglucoside) 4'''-malonyltransferase-like [KO:K13065] [EC:2.3.1.133]
            101249696  fatty alcohol:caffeoyl-CoA acyltransferase [KO:K13065] [EC:2.3.1.133]
            101267215  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
            104648251  salutaridinol 7-O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
            104648161  salutaridinol 7-O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
            112941247  deacetylvindoline O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
            101246092  cytochrome P450 98A2 [KO:K09754] [EC:1.14.14.96]
            101261765  cytochrome P450 98A3 [KO:K09754] [EC:1.14.14.96]
            101247849  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
            101262063  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
            101262367  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
            101252173  probable caffeoyl-CoA O-methyltransferase At4g26220 isoform X1 [KO:K00588] [EC:2.1.1.104]
            101265690  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
            101253032  caffeoyl-CoA O-methyltransferase 5 [KO:K00588] [EC:2.1.1.104]
            101255734  AnthOMT; flavonoid 3',5'-methyltransferase [KO:K00588] [EC:2.1.1.104]
            101260278  caffeoyl-CoA O-methyltransferase 6 [KO:K00588] [EC:2.1.1.104]
            101266196  probable caffeoyl-CoA O-methyltransferase At4g26220 isoform X1 [KO:K00588] [EC:2.1.1.104]
            101245167  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
            101248393  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
            101248678  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
            101265187  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
            101265977  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
            101253088  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
            101264010  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
COMPOUND    C00223  p-Coumaroyl-CoA
            C00323  Caffeoyl-CoA
            C00389  Quercetin
            C00406  Feruloyl-CoA
            C00509  Naringenin
            C00540  Cinnamoyl-CoA
            C00774  Phloretin
            C00852  Chlorogenate
            C00974  Dihydrokaempferol
            C01378  Fustin
            C01460  Vitexin
            C01477  Apigenin
            C01514  Luteolin
            C01604  Phlorizin
            C01617  Taxifolin
            C01709  Hesperetin
            C02906  Dihydromyricetin
            C02947  4-Coumaroylshikimate
            C03648  cis-3,4-Leucopelargonidin
            C05334  Isosakuranetin
            C05631  Eriodictyol
            C05903  Kaempferol
            C05904  Pelargonidin
            C05905  Cyanidin
            C05906  Leucocyanidin
            C05907  Luteoforol
            C05908  Delphinidin
            C05909  Leucodelphinidin
            C05911  Pentahydroxyflavanone
            C06561  Naringenin chalcone
            C06562  (+)-Catechin
            C08578  Butein
            C08650  Isoliquiritigenin
            C09099  Naringenin 7-O-beta-D-glucoside
            C09320  Afzelechin
            C09614  Butin
            C09727  (-)-Epicatechin
            C09736  Fisetinidol-4beta-ol
            C09751  Garbanzol
            C09756  Homoeriodictyol
            C09762  Liquiritigenin
            C09789  Naringin
            C09806  Neohesperidin
            C09826  Pinobanksin
            C09827  Pinocembrin
            C09833  Sakuranetin
            C10028  Chrysin
            C10044  Galangin
            C10107  Myricetin
            C10192  Tricetin
            C10434  5-O-Caffeoylshikimic acid
            C12123  7,4'-Dihydroxyflavone
            C12124  Apiforol
            C12127  (+)-Gallocatechin
            C12128  (-)-Epiafzelechin
            C12136  (-)-Epigallocatechin
            C12208  p-Coumaroyl quinic acid
            C15525  Eriodictyol chalcone
            C16404  Pinocembrin chalcone
            C16405  Homoeriodictyol chalcone
            C16406  Phlorizin chalcone
            C16407  2',4,4',6'-Tetrahydroxychalcone 4'-O-glucoside
            C16408  2',3,4,4',6'-Peptahydroxychalcone 4'-O-glucoside
            C16409  Aureusidin 6-O-glucoside
            C16410  Bracteatin 6-O-glucoside
            C16415  5-Deoxyleucopelargonidin
            C16416  Desmethylxanthohumol
            C16417  Xanthohumol
            C16418  Pinobanksin 3-O-acetate
            C16419  Pinostrobin
            C16422  Hesperetin 7-O-glucoside
            C16492  8-C-Glucosylnaringenin
            C21913  Dihydro-4-coumaroyl-CoA
            C22048  4-O-Methylxanthohumol
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:16367960
  AUTHORS   Ono E, Hatayama M, Isono Y, Sato T, Watanabe R, Yonekura-Sakakibara K, Fukuchi-Mizutani M, Tanaka Y, Kusumi T, Nishino T, Nakayama T.
  TITLE     Localization of a flavonoid biosynthetic polyphenol oxidase in vacuoles.
  JOURNAL   Plant J 45:133-43 (2006)
            DOI:10.1111/j.1365-313X.2005.02625.x
REFERENCE   PMID:16774647
  AUTHORS   Morreel K, Goeminne G, Storme V, Sterck L, Ralph J, Coppieters W, Breyne P, Steenackers M, Georges M, Messens E, Boerjan W.
  TITLE     Genetical metabolomics of flavonoid biosynthesis in Populus: a case study.
  JOURNAL   Plant J 47:224-37 (2006)
            DOI:10.1111/j.1365-313X.2006.02786.x
REFERENCE   PMID:16832053
  AUTHORS   Ono E, Fukuchi-Mizutani M, Nakamura N, Fukui Y, Yonekura-Sakakibara K, Yamaguchi M, Nakayama T, Tanaka T, Kusumi T, Tanaka Y.
  TITLE     Yellow flowers generated by expression of the aurone biosynthetic pathway.
  JOURNAL   Proc Natl Acad Sci U S A 103:11075-80 (2006)
            DOI:10.1073/pnas.0604246103
REFERENCE   
  AUTHORS   Halbwirth H, Martens S, Wienand U, Forkmann G, Stich K.
  TITLE     Synthesis of (14C)-labeled 5-deoxyflavonoids and their application in the study of dihydroflavonol/leucoanthocyanidin interconversion by dihydroflavonol 4-reductase.
  JOURNAL   Plant Sci 170:587-595 (2006)
            DOI:10.1016/j.plantsci.2005.10.013
REFERENCE   PMID:15231405
  AUTHORS   Stevens JF, Page JE.
  TITLE     Xanthohumol and related prenylflavonoids from hops and beer: to your good health!
  JOURNAL   Phytochemistry 65:1317-30 (2004)
            DOI:10.1016/j.phytochem.2004.04.025
REFERENCE   
  AUTHORS   Ogata J, Itoh Y, Ishida M, Yoshida H, Ozeki Y
  TITLE     Cloning and heterologous expression of cDNAs encoding flavonoid glucosyltransferases from Dianthus caryophyllus.
  JOURNAL   Plant Biotechnol 21:367-375 (2004)
            DOI:10.5511/plantbiotechnology.21.367
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:12644647
  AUTHORS   Shimada N, Aoki T, Sato S, Nakamura Y, Tabata S, Ayabe S.
  TITLE     A cluster of genes encodes the two types of chalcone isomerase involved in the biosynthesis of general flavonoids and legume-specific 5-deoxy(iso)flavonoids in Lotus japonicus.
  JOURNAL   Plant Physiol 131:941-51 (2003)
            DOI:10.1104/pp.004820
REFERENCE   
  AUTHORS   Halbwirth H, Martens S, Wienand U, Forkmann G, Stich K.
  TITLE     Biochemical formation of anthocyanins in silk tissue of Zea mays.
  JOURNAL   Plant Sci 164:489-495 (2003)
            DOI:10.1016/S0168-9452(02)00433-8
REFERENCE   
  AUTHORS   Martens S, Knott J, Seitz CA, Janvari L, Yu SN, Forkmann G.
  TITLE     Impact of biochemical pre-studies on specific metabolic engineering strategies of flavonoid biosynthesis in plant tissues.
  JOURNAL   Biochem Eng J 14:227-235 (2003)
            DOI:10.1016/S1369-703X(02)00224-3
REFERENCE   PMID:11073455
  AUTHORS   Nakayama T, Yonekura-Sakakibara K, Sato T, Kikuchi S, Fukui Y, Fukuchi-Mizutani M, Ueda T, Nakao M, Tanaka Y, Kusumi T, Nishino T.
  TITLE     Aureusidin synthase: a polyphenol oxidase homolog responsible for flower coloration.
  JOURNAL   Science 290:1163-6 (2000)
            DOI:10.1126/science.290.5494.1163
REFERENCE   PMID:16667183
  AUTHORS   Lewinsohn E, Britsch L, Mazur Y, Gressel J
  TITLE     Flavanone Glycoside Biosynthesis in Citrus: Chalcone Synthase, UDP-Glucose:Flavanone-7-O-Glucosyl-Transferase and -Rhamnosyl-Transferase Activities in Cell-Free Extracts.
  JOURNAL   Plant Physiol 91:1323-8 (1989)
            DOI:10.1104/pp.91.4.1323
REL_PATHWAY sly00940  Phenylpropanoid biosynthesis
            sly00942  Anthocyanin biosynthesis
            sly00943  Isoflavonoid biosynthesis
            sly00944  Flavone and flavonol biosynthesis
KO_PATHWAY  ko00941
///
