KEGG   PATHWAY: cit00941
Entry
cit00941                    Pathway                                
Name
Flavonoid biosynthesis - Citrus sinensis (Valencia orange)
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
cit00941  Flavonoid biosynthesis
cit00941

Module
cit_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:cit00941]
cit_M00138  Flavonoid biosynthesis, naringenin => pelargonidin [PATH:cit00941]
Other DBs
GO: 0009813
Organism
Citrus sinensis (Valencia orange) [GN:cit]
Gene
102607309  CHS2; chalcone synthase 2 [KO:K00660] [EC:2.3.1.74]
102620619  chalcone synthase-like isoform X1 [KO:K00660] [EC:2.3.1.74]
102626778  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
102612856  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
102613437  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
102629616  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
102616330  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
102616623  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
102606708  chalcone synthase 1 [KO:K00660] [EC:2.3.1.74]
127899064  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
102615441  CHI; chalcone--flavanone isomerase [KO:K01859] [EC:5.5.1.6]
102613490  chalcone isomerase-like protein 2 [KO:K01859] [EC:5.5.1.6]
102617426  CitF3H; naringenin,2-oxoglutarate 3-dioxygenase-like [KO:K00475] [EC:1.14.11.9]
102626432  flavonol synthase/flavanone 3-hydroxylase [KO:K05278] [EC:1.14.20.6]
102618406  flavonol synthase/flavanone 3-hydroxylase-like [KO:K05278] [EC:1.14.20.6]
102629970  flavonol synthase/flavanone 3-hydroxylase [KO:K05278] [EC:1.14.20.6]
102578013  C4H2; cinnamate 4-hydroxylase CYP73 [KO:K00487] [EC:1.14.14.91]
102577934  C4H1; cinnamate 4-hydroxylase CYP73 [KO:K00487] [EC:1.14.14.91]
102609972  cytochrome P450 93B16-like [KO:K23179] [EC:1.14.19.76]
102611200  cytochrome P450 93B16-like [KO:K23179] [EC:1.14.19.76]
102607946  LOW QUALITY PROTEIN: 2-hydroxyisoflavanone synthase-like [KO:K23179] [EC:1.14.19.76]
102620909  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
102578060  dihydroflavonol-4-reductase [KO:K13082] [EC:1.1.1.219 1.1.1.234]
102627616  flavonoid 3',5'-hydroxylase 2-like [KO:K13083] [EC:1.14.14.81]
102577958  ANS; anthocyanidin synthase [KO:K05277] [EC:1.14.20.4]
102618954  anthocyanidin reductase ((2S)-flavan-3-ol-forming) [KO:K08695] [EC:1.3.1.77]
102621411  leucoanthocyanidin reductase-like [KO:K13081] [EC:1.17.1.3]
102623228  flavanone 7-O-glucoside 2''-O-beta-L-rhamnosyltransferase-like [KO:K13080] [EC:2.4.1.236]
102628772  UDP-glycosyltransferase 88B1-like [KO:K22845] [EC:2.4.1.357]
102617597  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
102618272  shikimate O-hydroxycinnamoyltransferase-like isoform X1 [KO:K13065] [EC:2.3.1.133]
102624810  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
102623263  stemmadenine O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
102606780  acyltransferase GLAUCE [KO:K13065] [EC:2.3.1.133]
102626487  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
102616683  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
102621641  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
102614148  shikimate O-hydroxycinnamoyltransferase-like isoform X1 [KO:K13065] [EC:2.3.1.133]
102619195  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
102625849  stemmadenine O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
102618363  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
102624577  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
102628607  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
107175441  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
102628720  shikimate O-hydroxycinnamoyltransferase-like isoform X4 [KO:K13065] [EC:2.3.1.133]
102609895  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
112498336  stemmadenine O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
107178428  stemmadenine O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
102623563  stemmadenine O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
102630515  shikimate O-hydroxycinnamoyltransferase-like isoform X1 [KO:K13065] [EC:2.3.1.133]
102611596  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
102617991  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
102624231  cytochrome P450 98A2 [KO:K09754] [EC:1.14.14.96]
102623337  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
127902134  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
102622674  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
102619432  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
102616576  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
102617076  probable caffeoyl-CoA O-methyltransferase At4g26220 isoform X1 [KO:K00588] [EC:2.1.1.104]
102617232  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
102627979  caffeoyl-CoA O-methyltransferase 5-like [KO:K00588] [EC:2.1.1.104]
112495545  caffeoyl-CoA O-methyltransferase 5-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
cit00940  Phenylpropanoid biosynthesis
cit00942  Anthocyanin biosynthesis
cit00943  Isoflavonoid biosynthesis
cit00944  Flavone and flavonol biosynthesis
KO pathway
ko00941   
LinkDB

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