KEGG   PATHWAY: spen00941
Entry
spen00941                   Pathway                                
Name
Flavonoid biosynthesis - Solanum pennellii
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
spen00941  Flavonoid biosynthesis
spen00941

Module
spen_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:spen00941]
spen_M00138  Flavonoid biosynthesis, naringenin => pelargonidin [PATH:spen00941]
Other DBs
GO: 0009813
Organism
Solanum pennellii [GN:spen]
Gene
107006636  chalcone synthase J-like [KO:K00660] [EC:2.3.1.74]
107020692  chalcone synthase 2 [KO:K00660] [EC:2.3.1.74]
107031578  chalcone synthase 1B [KO:K00660] [EC:2.3.1.74]
107020878  chalcone synthase B [KO:K00660] [EC:2.3.1.74]
107019217  chalcone--flavonone isomerase-like [KO:K01859] [EC:5.5.1.6]
107020630  chalcone--flavonone isomerase-like [KO:K01859] [EC:5.5.1.6]
107018616  probable chalcone--flavonone isomerase 3 [KO:K01859] [EC:5.5.1.6]
107011910  naringenin,2-oxoglutarate 3-dioxygenase [KO:K00475] [EC:1.14.11.9]
107004995  flavonol synthase/flavanone 3-hydroxylase [KO:K05278] [EC:1.14.20.6]
107020510  cytochrome P450 CYP73A100-like [KO:K00487] [EC:1.14.14.91]
114073827  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
107022866  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
107015315  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
107010988  dihydroflavonol 4-reductase [KO:K13082] [EC:1.1.1.219 1.1.1.234]
107005054  flavonoid 3',5'-hydroxylase [KO:K13083] [EC:1.14.14.81]
107027946  leucoanthocyanidin dioxygenase [KO:K05277] [EC:1.14.20.4]
107012467  anthocyanidin reductase ((2S)-flavan-3-ol-forming) [KO:K08695] [EC:1.3.1.77]
114077302  leucoanthocyanidin reductase-like [KO:K13081] [EC:1.17.1.3]
107016413  acylsugar acyltransferase 3-like [KO:K13065] [EC:2.3.1.133]
107024739  acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
107024740  acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
107025914  acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
107006388  agmatine coumaroyltransferase-2-like [KO:K13065] [EC:2.3.1.133]
107019786  LOW QUALITY PROTEIN: BAHD acyltransferase BIA1-like [KO:K13065] [EC:2.3.1.133]
107026059  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
107006773  acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
107006805  pelargonidin 3-O-(6-caffeoylglucoside) 5-O-(6-O-malonylglucoside) 4'''-malonyltransferase-like [KO:K13065] [EC:2.3.1.133]
107028136  acylsugar acyltransferase 3-like [KO:K13065] [EC:2.3.1.133]
107006883  acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
107025455  acylsugar acyltransferase 3-like [KO:K13065] [EC:2.3.1.133]
107006919  acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
107006924  acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
107006971  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
107019270  vinorine synthase [KO:K13065] [EC:2.3.1.133]
107014577  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
107029716  acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
107005264  acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
107004172  agmatine hydroxycinnamoyltransferase 1-like [KO:K13065] [EC:2.3.1.133]
107004234  agmatine coumaroyltransferase-2-like [KO:K13065] [EC:2.3.1.133]
107004785  LOW QUALITY PROTEIN: BAHD acyltransferase At5g47980-like [KO:K13065] [EC:2.3.1.133]
107004898  fatty alcohol:caffeoyl-CoA acyltransferase [KO:K13065] [EC:2.3.1.133]
107022615  agmatine hydroxycinnamoyltransferase 1-like [KO:K13065] [EC:2.3.1.133]
107024411  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
107025597  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
107025607  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
107025644  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
107002593  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
107001769  cytochrome P450 98A3-like [KO:K09754] [EC:1.14.14.96]
107001863  cytochrome P450 98A3-like [KO:K09754] [EC:1.14.14.96]
107008188  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
107028331  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
107013906  LOW QUALITY PROTEIN: probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
107008953  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
107009496  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
107010763  caffeoyl-CoA O-methyltransferase 6 [KO:K00588] [EC:2.1.1.104]
107032120  caffeoyl-CoA O-methyltransferase 5-like [KO:K00588] [EC:2.1.1.104]
107015723  probable caffeoyl-CoA O-methyltransferase At4g26220 isoform X1 [KO:K00588] [EC:2.1.1.104]
107020048  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
107020068  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
107020085  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
  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
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
  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
  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
  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
  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
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
  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
  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
Related
pathway
spen00940  Phenylpropanoid biosynthesis
spen00942  Anthocyanin biosynthesis
spen00943  Isoflavonoid biosynthesis
spen00944  Flavone and flavonol biosynthesis
KO pathway
ko00941   
LinkDB

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