KEGG   PATHWAY: zof00941
Entry
zof00941                    Pathway                                
Name
Flavonoid biosynthesis - Zingiber officinale (ginger)
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
zof00941  Flavonoid biosynthesis
zof00941

Module
zof_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:zof00941]
zof_M00138  Flavonoid biosynthesis, naringenin => pelargonidin [PATH:zof00941]
Other DBs
GO: 0009813
Organism
Zingiber officinale (ginger) [GN:zof]
Gene
122025800  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
122010241  curcumin synthase 3-like [KO:K00660] [EC:2.3.1.74]
121967514  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
121981917  curcumin synthase 3-like [KO:K00660] [EC:2.3.1.74]
122020636  chalcone synthase 2 [KO:K00660] [EC:2.3.1.74]
122020773  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
122020803  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
122021216  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
122052744  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
122021907  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
121971532  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
121985757  curcumin synthase 3 [KO:K00660] [EC:2.3.1.74]
122024309  chalcone synthase 2 [KO:K00660] [EC:2.3.1.74]
122016451  curcumin synthase 3-like [KO:K00660] [EC:2.3.1.74]
122016453  curcumin synthase 3-like [KO:K00660] [EC:2.3.1.74]
122024592  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
122024797  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
121983267  phenylpropanoylacetyl-CoA synthase-like [KO:K00660] [EC:2.3.1.74]
121987822  phenylpropanoylacetyl-CoA synthase-like [KO:K00660] [EC:2.3.1.74]
122012867  phenylpropanoylacetyl-CoA synthase-like [KO:K00660] [EC:2.3.1.74]
122017888  phenylpropanoylacetyl-CoA synthase-like [KO:K00660] [EC:2.3.1.74]
121987741  chalcone isomerase-like protein 2 [KO:K01859] [EC:5.5.1.6]
121979964  chalcone--flavanone isomerase-like [KO:K01859] [EC:5.5.1.6]
121983178  chalcone isomerase-like protein 2 [KO:K01859] [EC:5.5.1.6]
121984101  chalcone--flavanone isomerase-like [KO:K01859] [EC:5.5.1.6]
122032774  flavanone 3-dioxygenase F3H1-like [KO:K00475] [EC:1.14.11.9]
122034319  flavanone 3-dioxygenase F3H1-like [KO:K00475] [EC:1.14.11.9]
121976111  flavonol synthase 1-like [KO:K05278] [EC:1.14.20.6]
121990229  flavonol synthase/flavanone 3-hydroxylase-like [KO:K05278] [EC:1.14.20.6]
121992545  flavonol synthase/flavanone 3-hydroxylase-like [KO:K05278] [EC:1.14.20.6]
121996484  flavonol synthase/flavanone 3-hydroxylase-like [KO:K05278] [EC:1.14.20.6]
121996485  flavonol synthase/flavanone 3-hydroxylase-like [KO:K05278] [EC:1.14.20.6]
121971547  flavonol synthase 1-like [KO:K05278] [EC:1.14.20.6]
122041523  cytochrome P450 CYP73A100-like [KO:K00487] [EC:1.14.14.91]
121988665  cytochrome P450 CYP73A100-like [KO:K00487] [EC:1.14.14.91]
122046034  cytochrome P450 CYP73A100-like [KO:K00487] [EC:1.14.14.91]
122031866  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
122047857  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
122034341  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
121967555  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
121997591  cytochrome P450 CYP73A100-like [KO:K00487] [EC:1.14.14.91]
122052786  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
122016214  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
122042133  flavonoid 3'-monooxygenase CYP75B137-like [KO:K05280] [EC:1.14.14.82]
121975478  flavonoid 3'-monooxygenase CYP75B137-like [KO:K05280] [EC:1.14.14.82]
122046667  flavonoid 3'-monooxygenase CYP75B137-like [KO:K05280] [EC:1.14.14.82]
121970404  flavonoid 3'-monooxygenase CYP75B137-like [KO:K05280] [EC:1.14.14.82]
122009647  dihydroflavonol 4-reductase-like [KO:K13082] [EC:1.1.1.219 1.1.1.234]
121971619  dihydroflavonol 4-reductase-like [KO:K13082] [EC:1.1.1.219 1.1.1.234]
121974447  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
121974448  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
121974449  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
121974450  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
121974453  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
122003778  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
122017925  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
121989454  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
121977250  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
121977320  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
121977321  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
122009883  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
121969329  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
121969330  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
121969331  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
121969332  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
121969333  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
121998399  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
122000196  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
122018496  leucoanthocyanidin dioxygenase-like [KO:K05277] [EC:1.14.20.4]
122022294  leucoanthocyanidin dioxygenase-like [KO:K05277] [EC:1.14.20.4]
121977884  anthocyanidin reductase ((2S)-flavan-3-ol-forming)-like isoform X1 [KO:K08695] [EC:1.3.1.77]
122011404  anthocyanidin reductase ((2S)-flavan-3-ol-forming)-like [KO:K08695] [EC:1.3.1.77]
122016036  anthocyanidin reductase ((2S)-flavan-3-ol-forming)-like [KO:K08695] [EC:1.3.1.77]
121973714  anthocyanidin reductase ((2S)-flavan-3-ol-forming)-like isoform X1 [KO:K08695] [EC:1.3.1.77]
122056268  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122056270  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122056271  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122049698  agmatine coumaroyltransferase-2-like [KO:K13065] [EC:2.3.1.133]
121968169  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
121968171  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
121968176  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
121968177  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122051739  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122051741  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122051744  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122051745  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122053667  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122053670  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122053672  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122001509  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122054777  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122040332  agmatine coumaroyltransferase-2-like [KO:K13065] [EC:2.3.1.133]
122051740  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122056267  hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
122007084  p-coumarate 3-hydroxylase-like [KO:K09754] [EC:1.14.14.96]
122030545  p-coumarate 3-hydroxylase-like [KO:K09754] [EC:1.14.14.96]
121971833  p-coumarate 3-hydroxylase-like [KO:K09754] [EC:1.14.14.96]
122002816  p-coumarate 3-hydroxylase-like [KO:K09754] [EC:1.14.14.96]
121974291  caffeoyl-CoA O-methyltransferase 4-like [KO:K00588] [EC:2.1.1.104]
121981392  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
121981393  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
121981395  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
121969176  caffeoyl-CoA O-methyltransferase 4 [KO:K00588] [EC:2.1.1.104]
121985272  caffeoyl-CoA O-methyltransferase-like [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
zof00940  Phenylpropanoid biosynthesis
zof00942  Anthocyanin biosynthesis
zof00944  Flavone and flavonol biosynthesis
KO pathway
ko00941   
LinkDB

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