KEGG   PATHWAY: pda00941
Entry
pda00941                    Pathway                                
Name
Flavonoid biosynthesis - Phoenix dactylifera (date palm)
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
pda00941  Flavonoid biosynthesis
pda00941

Module
pda_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:pda00941]
pda_M00138  Flavonoid biosynthesis, naringenin => pelargonidin [PATH:pda00941]
Other DBs
GO: 0009813
Organism
Phoenix dactylifera (date palm) [GN:pda]
Gene
103712379  chalcone synthase 1 [KO:K00660] [EC:2.3.1.74]
103723569  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
103720326  chalcone synthase C2 [KO:K00660] [EC:2.3.1.74]
103720741  chalcone synthase 3 [KO:K00660] [EC:2.3.1.74]
103720740  LOW QUALITY PROTEIN: chalcone synthase 3 [KO:K00660] [EC:2.3.1.74]
103698502  chalcone synthase 3-like [KO:K00660] [EC:2.3.1.74]
103700702  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
120105391  chalcone synthase 3 [KO:K00660] [EC:2.3.1.74]
120111374  chalcone synthase 3-like [KO:K00660] [EC:2.3.1.74]
120111375  chalcone synthase 3-like [KO:K00660] [EC:2.3.1.74]
120111376  chalcone synthase 3-like [KO:K00660] [EC:2.3.1.74]
120111590  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
120111592  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
120111595  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
120111596  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
103696411  chalcone--flavonone isomerase [KO:K01859] [EC:5.5.1.6]
108511484  chalcone--flavonone isomerase-like [KO:K01859] [EC:5.5.1.6]
103721160  probable chalcone--flavonone isomerase 3 [KO:K01859] [EC:5.5.1.6]
103708901  probable chalcone--flavonone isomerase 3 [KO:K01859] [EC:5.5.1.6]
103708217  flavanone 3-dioxygenase F3H1-like [KO:K00475] [EC:1.14.11.9]
103697163  flavanone 3-dioxygenase F3H1-like [KO:K00475] [EC:1.14.11.9]
120108474  flavanone 3-dioxygenase F3H1-like [KO:K00475] [EC:1.14.11.9]
103712517  flavonol synthase 1 [KO:K05278] [EC:1.14.20.6]
103702142  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
103702256  cytochrome P450 CYP73A100-like [KO:K00487] [EC:1.14.14.91]
103722165  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
103713131  cytochrome P450 CYP73A100-like [KO:K00487] [EC:1.14.14.91]
103706246  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
103708914  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
120110174  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
103710250  flavonoid 3'-monooxygenase CYP75B137-like [KO:K05280] [EC:1.14.14.82]
103708250  flavonoid 3'-monooxygenase CYP75B137-like [KO:K05280] [EC:1.14.14.82]
103712715  dihydroflavonol 4-reductase [KO:K13082] [EC:1.1.1.219 1.1.1.234]
103706786  flavonoid 3',5'-hydroxylase-like [KO:K13083] [EC:1.14.14.81]
103706219  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
103713287  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
103719265  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
120110262  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
103702795  anthocyanin synthase-like [KO:K05277] [EC:1.14.20.4]
103696959  anthocyanin synthase-like isoform X1 [KO:K05277] [EC:1.14.20.4]
103698208  anthocyanidin reductase ((2S)-flavan-3-ol-forming) [KO:K08695] [EC:1.3.1.77]
103696132  leucoanthocyanidin reductase-like [KO:K13081] [EC:1.17.1.3]
103700891  leucoanthocyanidin reductase-like [KO:K13081] [EC:1.17.1.3]
103697376  putrescine hydroxycinnamoyltransferase 1-like [KO:K13065] [EC:2.3.1.133]
103697378  putrescine hydroxycinnamoyltransferase 1-like [KO:K13065] [EC:2.3.1.133]
103699039  putrescine hydroxycinnamoyltransferase 1-like [KO:K13065] [EC:2.3.1.133]
103707445  putrescine hydroxycinnamoyltransferase 1-like [KO:K13065] [EC:2.3.1.133]
103707448  hydroxycinnamoyltransferase isoform X2 [KO:K13065] [EC:2.3.1.133]
103712513  LOW QUALITY PROTEIN: salutaridinol 7-O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
103710206  agmatine coumaroyltransferase-2-like [KO:K13065] [EC:2.3.1.133]
103716242  fatty alcohol:caffeoyl-CoA acyltransferase [KO:K13065] [EC:2.3.1.133]
103705056  p-coumarate 3-hydroxylase-like [KO:K09754] [EC:1.14.14.96]
103706282  p-coumarate 3-hydroxylase-like [KO:K09754] [EC:1.14.14.96]
103713767  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
103722553  norbelladine 4'-O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
103710057  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
103701551  norbelladine 4'-O-methyltransferase-like isoform X1 [KO:K00588] [EC:2.1.1.104]
103701552  norbelladine 4'-O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
120107377  norbelladine 4'-O-methyltransferase 2-like isoform X1 [KO:K00588] [EC:2.1.1.104]
120107378  norbelladine 4'-O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
120113086  norbelladine 4'-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
pda00940  Phenylpropanoid biosynthesis
pda00942  Anthocyanin biosynthesis
pda00944  Flavone and flavonol biosynthesis
KO pathway
ko00941   
LinkDB

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