KEGG   PATHWAY: nau00941
Entry
nau00941                    Pathway                                
Name
Flavonoid biosynthesis - Nicotiana attenuata (coyote tobacco)
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
nau00941  Flavonoid biosynthesis
nau00941

Module
nau_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:nau00941]
nau_M00138  Flavonoid biosynthesis, naringenin => pelargonidin [PATH:nau00941]
Other DBs
GO: 0009813
Organism
Nicotiana attenuata (coyote tobacco) [GN:nau]
Gene
109224243  chalcone synthase G-like [KO:K00660] [EC:2.3.1.74]
109227353  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
109212385  chalcone synthase A [KO:K00660] [EC:2.3.1.74]
109215849  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
109207770  chalcone synthase 2 [KO:K00660] [EC:2.3.1.74]
109235542  chalcone--flavonone isomerase [KO:K01859] [EC:5.5.1.6]
109238661  probable chalcone--flavonone isomerase 3 [KO:K01859] [EC:5.5.1.6]
109242464  naringenin,2-oxoglutarate 3-dioxygenase [KO:K00475] [EC:1.14.11.9]
109237082  flavonol synthase/flavanone 3-hydroxylase [KO:K05278] [EC:1.14.20.6]
109229405  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
109225492  cytochrome P450 CYP73A100-like [KO:K00487] [EC:1.14.14.91]
109215399  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
109223789  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
109208181  dihydroflavonol 4-reductase [KO:K13082] [EC:1.1.1.219 1.1.1.234]
109232046  dihydroflavonol 4-reductase-like isoform X1 [KO:K13082] [EC:1.1.1.219 1.1.1.234]
109209238  flavonoid 3',5'-hydroxylase 1 [KO:K13083] [EC:1.14.14.81]
109212376  leucoanthocyanidin dioxygenase [KO:K05277] [EC:1.14.20.4]
109243327  anthocyanidin reductase ((2S)-flavan-3-ol-forming) [KO:K08695] [EC:1.3.1.77]
109235276  leucoanthocyanidin reductase-like [KO:K13081] [EC:1.17.1.3]
109236083  acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
109237576  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
109205681  agmatine coumaroyltransferase-2-like [KO:K13065] [EC:2.3.1.133]
109235639  acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
109237700  agmatine hydroxycinnamoyltransferase 1-like [KO:K13065] [EC:2.3.1.133]
109235919  acylsugar acyltransferase 3-like [KO:K13065] [EC:2.3.1.133]
109241609  acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
109209235  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
109234193  salutaridinol 7-O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
109210489  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
109212708  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
109220540  acylsugar acyltransferase 3-like [KO:K13065] [EC:2.3.1.133]
109226461  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
109229836  agmatine coumaroyltransferase-2-like [KO:K13065] [EC:2.3.1.133]
109231066  acylsugar acyltransferase 3-like [KO:K13065] [EC:2.3.1.133]
109206370  acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
109206371  acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
109207449  agmatine hydroxycinnamoyltransferase 1-like [KO:K13065] [EC:2.3.1.133]
109209745  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
109225602  acylsugar acyltransferase 3-like [KO:K13065] [EC:2.3.1.133]
109221014  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
109228215  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
109239726  cytochrome P450 98A3-like [KO:K09754] [EC:1.14.14.96]
109239730  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
109230380  caffeoyl-CoA O-methyltransferase 1-like [KO:K00588] [EC:2.1.1.104]
109232738  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
109244656  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
109230873  caffeoyl-CoA O-methyltransferase 3 [KO:K00588] [EC:2.1.1.104]
109215873  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
109236417  caffeoyl-CoA O-methyltransferase 6 [KO:K00588] [EC:2.1.1.104]
109213146  caffeoyl-CoA O-methyltransferase 5 [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
nau00940  Phenylpropanoid biosynthesis
nau00942  Anthocyanin biosynthesis
nau00943  Isoflavonoid biosynthesis
nau00944  Flavone and flavonol biosynthesis
KO pathway
ko00941   
LinkDB

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