ENTRY       mtr00941                    Pathway
NAME        Flavonoid biosynthesis - Medicago truncatula (barrel medic)
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 mtr00941  Flavonoid biosynthesis
MODULE      mtr_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:mtr00941]
            mtr_M00138  Flavonoid biosynthesis, naringenin => pelargonidin [PATH:mtr00941]
            mtr_M00940  Flavanone biosynthesis, p-coumaroyl-CoA => liquiritigenin [PATH:mtr00941]
DBLINKS     GO: 0009813
ORGANISM    Medicago truncatula (barrel medic) [GN:mtr]
GENE        11419346  chalcone synthase 5 [KO:K00660] [EC:2.3.1.74]
            11411483  chalcone synthase 1A [KO:K00660] [EC:2.3.1.74]
            11439469  chalcone synthase 1B [KO:K00660] [EC:2.3.1.74]
            11438511  chalcone synthase 1A [KO:K00660] [EC:2.3.1.74]
            120577917  chalcone synthase 4 [KO:K00660] [EC:2.3.1.74]
            25499670  chalcone synthase 4 [KO:K00660] [EC:2.3.1.74]
            25494497  chalcone synthase 9 [KO:K00660] [EC:2.3.1.74]
            25494498  chalcone synthase 9 [KO:K00660] [EC:2.3.1.74]
            11436702  chalcone synthase 4 [KO:K00660] [EC:2.3.1.74]
            11428910  chalcone synthase 5 [KO:K00660] [EC:2.3.1.74]
            11442534  chalcone synthase 4 [KO:K00660] [EC:2.3.1.74]
            25489717  stilbene synthase 4 [KO:K00660] [EC:2.3.1.74]
            11424172  chalcone synthase 2 [KO:K00660] [EC:2.3.1.74]
            11418796  chalcone synthase 2 [KO:K00660] [EC:2.3.1.74]
            11421144  chalcone synthase 2 [KO:K00660] [EC:2.3.1.74]
            11420610  chalcone synthase 2 [KO:K00660] [EC:2.3.1.74]
            11420611  chalcone synthase 2 [KO:K00660] [EC:2.3.1.74]
            11440049  chalcone synthase [KO:K00660] [EC:2.3.1.74]
            11420334  chalcone synthase 8 [KO:K00660] [EC:2.3.1.74]
            11407003  chalcone synthase 4 [KO:K00660] [EC:2.3.1.74]
            25485043  chalcone synthase 8 [KO:K00660] [EC:2.3.1.74]
            25497742  chalcone--flavonone isomerase 2 [KO:K01859] [EC:5.5.1.6]
            25489829  probable chalcone--flavonone isomerase 3 [KO:K01859] [EC:5.5.1.6]
            11440740  chalcone--flavonone isomerase 1 [KO:K01859] [EC:5.5.1.6]
            11440741  chalcone--flavonone isomerase 1B-2 [KO:K01859] [EC:5.5.1.6]
            11424676  chalcone--flavonone isomerase 1B-2 [KO:K01859] [EC:5.5.1.6]
            11445536  chalcone--flavonone isomerase 2 [KO:K01859] [EC:5.5.1.6]
            11446745  chalcone--flavonone isomerase 2 [KO:K01859] [EC:5.5.1.6]
            11443565  naringenin,2-oxoglutarate 3-dioxygenase [KO:K00475] [EC:1.14.11.9]
            11408162  naringenin,2-oxoglutarate 3-dioxygenase [KO:K00475] [EC:1.14.11.9]
            25489119  naringenin,2-oxoglutarate 3-dioxygenase [KO:K00475] [EC:1.14.11.9]
            11415879  flavonol synthase/flavanone 3-hydroxylase [KO:K05278] [EC:1.14.20.6]
            11415909  flavonol synthase/flavanone 3-hydroxylase [KO:K05278] [EC:1.14.20.6]
            11435413  flavonol synthase/flavanone 3-hydroxylase [KO:K05278] [EC:1.14.20.6]
            11435414  flavonol synthase/flavanone 3-hydroxylase [KO:K05278] [EC:1.14.20.6]
            11442075  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
            25485521  cytochrome P450 CYP73A100 [KO:K00487] [EC:1.14.14.91]
            25480973  NAD(P)H-dependent 6'-deoxychalcone synthase [KO:K08243]
            11432729  NAD(P)H-dependent 6'-deoxychalcone synthase [KO:K08243]
            11419649  NAD(P)H-dependent 6'-deoxychalcone synthase [KO:K08243]
            11425292  NAD(P)H-dependent 6'-deoxychalcone synthase [KO:K08243]
            11430929  NAD(P)H-dependent 6'-deoxychalcone synthase [KO:K08243]
            25492470  cytochrome P450 93B16 [KO:K23179] [EC:1.14.19.76]
            25492471  cytochrome P450 93B16 [KO:K23179] [EC:1.14.19.76]
            25485387  cytochrome P450 93B16 [KO:K23179] [EC:1.14.19.76]
            11443726  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
            11425400  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
            25493879  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
            25488708  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
            25482168  dihydroflavonol 4-reductase [KO:K13082] [EC:1.1.1.219 1.1.1.234]
            25482169  dihydroflavonol 4-reductase [KO:K13082] [EC:1.1.1.219 1.1.1.234]
            25490447  flavonoid 3',5'-hydroxylase 1 [KO:K13083] [EC:1.14.14.81]
            25490451  flavonoid 3',5'-hydroxylase 2 [KO:K13083] [EC:1.14.14.81]
            11436267  leucoanthocyanidin dioxygenase [KO:K05277] [EC:1.14.20.4]
            25493251  anthocyanidin reductase ((2S)-flavan-3-ol-forming) [KO:K08695] [EC:1.3.1.77]
            11406967  leucoanthocyanidin reductase [KO:K13081] [EC:1.17.1.3]
            25488512  LOW QUALITY PROTEIN: UDP-glycosyltransferase 88F5 [KO:K22845] [EC:2.4.1.357]
            25488513  UDP-glycosyltransferase 88F4 isoform X2 [KO:K22845] [EC:2.4.1.357]
            11438044  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            11446414  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
            11446012  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            11443511  LOW QUALITY PROTEIN: spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            11428237  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            25491195  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            11413387  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            11431043  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            25486922  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            25487997  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            11441023  hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            11415221  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
            11439545  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            11441050  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            11437276  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            120576930  cytochrome P450 98A2 [KO:K09754] [EC:1.14.14.96]
            11407567  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
            25500555  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
            11446939  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
            25493320  flavonoid 3',5'-methyltransferase [KO:K00588] [EC:2.1.1.104]
            25493460  caffeoyl-CoA O-methyltransferase 5 [KO:K00588] [EC:2.1.1.104]
            25493461  caffeoyl-CoA O-methyltransferase 2 [KO:K00588] [EC:2.1.1.104]
            25493481  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
            25493490  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
            11439410  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 mtr00940  Phenylpropanoid biosynthesis
            mtr00943  Isoflavonoid biosynthesis
            mtr00944  Flavone and flavonol biosynthesis
KO_PATHWAY  ko00941
///
