KEGG   PATHWAY: tcc00940
Entry
tcc00940                    Pathway                                
Name
Phenylpropanoid biosynthesis - Theobroma cacao (cacao)
Description
Phenylpropanoids are a group of plant secondary metabolites derived from phenylalanine and having a wide variety of functions both as structural and signaling molecules. Phenylalanine is first converted to cinnamic acid by deamination. It is followed by hydroxylation and frequent methylation to generate coumaric acid and other acids with a phenylpropane (C6-C3) unit. Reduction of the CoA-activated carboxyl groups of these acids results in the corresponding aldehydes and alcohols. The alcohols are called monolignols, the starting compounds for biosynthesis of lignin.
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
tcc00940  Phenylpropanoid biosynthesis
tcc00940

Module
tcc_M00039  Monolignol biosynthesis, phenylalanine/tyrosine => monolignol [PATH:tcc00940]
tcc_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:tcc00940]
Other DBs
GO: 0009699
Organism
Theobroma cacao (cacao) [GN:tcc]
Gene
18590901  phenylalanine ammonia-lyase [KO:K10775] [EC:4.3.1.24]
18597973  phenylalanine ammonia-lyase [KO:K10775] [EC:4.3.1.24]
18586419  phenylalanine ammonia-lyase G4 [KO:K10775] [EC:4.3.1.24]
18589488  cytochrome P450 CYP73A100 [KO:K00487] [EC:1.14.14.91]
18591096  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
18587499  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
18589246  4-coumarate--CoA ligase 1 [KO:K01904] [EC:6.2.1.12]
18600949  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
18606860  4-coumarate--CoA ligase-like 6 [KO:K01904] [EC:6.2.1.12]
18599509  4-coumarate--CoA ligase 2 [KO:K01904] [EC:6.2.1.12]
18596332  4-coumarate--CoA ligase 1 [KO:K01904] [EC:6.2.1.12]
18608984  4-coumarate--CoA ligase-like 1 [KO:K01904] [EC:6.2.1.12]
18598026  4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]
18590950  4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]
18605066  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
18587818  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
18587819  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
108660761  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
108660776  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
18609668  vinorine synthase [KO:K13065] [EC:2.3.1.133]
18609669  vinorine synthase [KO:K13065] [EC:2.3.1.133]
18605051  vinorine synthase [KO:K13065] [EC:2.3.1.133]
18605052  vinorine synthase [KO:K13065] [EC:2.3.1.133]
18605054  vinorine synthase [KO:K13065] [EC:2.3.1.133]
18602309  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
18587820  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
18587816  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
108662026  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
18599181  vinorine synthase [KO:K13065] [EC:2.3.1.133]
18597945  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
18597944  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
18599886  vinorine synthase [KO:K13065] [EC:2.3.1.133]
18598473  omega-hydroxypalmitate O-feruloyl transferase [KO:K13065] [EC:2.3.1.133]
18595464  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
18586507  vinorine synthase [KO:K13065] [EC:2.3.1.133]
18598608  cytochrome P450 98A2 [KO:K09754] [EC:1.14.14.96]
18613566  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
18595801  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
18586259  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
18609234  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
18602052  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
18611157  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
18607959  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
18609021  flavonoid 3',5'-methyltransferase [KO:K00588] [EC:2.1.1.104]
18610037  putative caffeoyl-CoA O-methyltransferase At1g67980 [KO:K00588] [EC:2.1.1.104]
18602545  flavonoid 3',5'-methyltransferase [KO:K00588] [EC:2.1.1.104]
18588443  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
18595421  cinnamoyl-CoA reductase 1 [KO:K09753] [EC:1.2.1.44]
18588624  aldehyde dehydrogenase family 2 member C4 [KO:K12355] [EC:1.2.1.68]
18607698  cytochrome P450 84A1 [KO:K09755] [EC:1.14.-.-]
108661886  caffeic acid 3-O-methyltransferase-like [KO:K13066] [EC:2.1.1.68 2.1.1.4]
18599828  caffeic acid 3-O-methyltransferase [KO:K13066] [EC:2.1.1.68 2.1.1.4]
18605934  caffeic acid 3-O-methyltransferase 1 [KO:K13066] [EC:2.1.1.68 2.1.1.4]
18601594  caffeic acid 3-O-methyltransferase [KO:K13066] [EC:2.1.1.68 2.1.1.4]
18589884  caffeic acid 3-O-methyltransferase [KO:K13066] [EC:2.1.1.68 2.1.1.4]
18589881  caffeic acid 3-O-methyltransferase [KO:K13066] [EC:2.1.1.68 2.1.1.4]
18605869  caffeic acid 3-O-methyltransferase [KO:K13066] [EC:2.1.1.68 2.1.1.4]
18599823  caffeic acid 3-O-methyltransferase [KO:K13066] [EC:2.1.1.68 2.1.1.4]
18592353  caffeic acid 3-O-methyltransferase [KO:K13066] [EC:2.1.1.68 2.1.1.4]
108663133  caffeic acid 3-O-methyltransferase-like [KO:K13066] [EC:2.1.1.68 2.1.1.4]
18587033  caffeic acid 3-O-methyltransferase [KO:K13066] [EC:2.1.1.68 2.1.1.4]
18507240  caffeic acid 3-O-methyltransferase [KO:K13066] [EC:2.1.1.68 2.1.1.4]
18608008  cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
18605911  probable cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
18591600  probable cinnamyl alcohol dehydrogenase 6 [KO:K00083] [EC:1.1.1.195]
18611738  probable cinnamyl alcohol dehydrogenase 9 [KO:K00083] [EC:1.1.1.195]
18611202  cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
18595172  flavin-dependent oxidoreductase FOX2 [KO:K22395] [EC:1.1.1.195]
18595174  flavin-dependent oxidoreductase FOX2 [KO:K22395] [EC:1.1.1.195]
18603742  1-Cys peroxiredoxin [KO:K11188] [EC:1.11.1.7 1.11.1.27 3.1.1.-]
108663485  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
18589668  peroxidase N [KO:K00430] [EC:1.11.1.7]
18587622  peroxidase 16 [KO:K00430] [EC:1.11.1.7]
18589661  peroxidase 15 [KO:K00430] [EC:1.11.1.7]
18597922  peroxidase 21 [KO:K00430] [EC:1.11.1.7]
18591067  peroxidase 4 [KO:K00430] [EC:1.11.1.7]
18588760  peroxidase 25 [KO:K00430] [EC:1.11.1.7]
18600622  peroxidase 5 [KO:K00430] [EC:1.11.1.7]
18587674  peroxidase 46 [KO:K00430] [EC:1.11.1.7]
18599128  peroxidase A2 [KO:K00430] [EC:1.11.1.7]
108663501  peroxidase 4-like [KO:K00430] [EC:1.11.1.7]
18612010  peroxidase 47 [KO:K00430] [EC:1.11.1.7]
18613454  peroxidase 3 [KO:K00430] [EC:1.11.1.7]
18610851  peroxidase 72 [KO:K00430] [EC:1.11.1.7]
18609925  lignin-forming anionic peroxidase [KO:K00430] [EC:1.11.1.7]
18605468  peroxidase 66 [KO:K00430] [EC:1.11.1.7]
18609928  lignin-forming anionic peroxidase [KO:K00430] [EC:1.11.1.7]
18608318  peroxidase N1 [KO:K00430] [EC:1.11.1.7]
18609921  lignin-forming anionic peroxidase [KO:K00430] [EC:1.11.1.7]
18610075  peroxidase 3 [KO:K00430] [EC:1.11.1.7]
18608315  cationic peroxidase 2 [KO:K00430] [EC:1.11.1.7]
18606092  peroxidase 20 [KO:K00430] [EC:1.11.1.7]
18609365  peroxidase 31 [KO:K00430] [EC:1.11.1.7]
18608316  peroxidase N1 [KO:K00430] [EC:1.11.1.7]
18610076  peroxidase 27 [KO:K00430] [EC:1.11.1.7]
18607886  peroxidase 10 [KO:K00430] [EC:1.11.1.7]
18610125  peroxidase 11 [KO:K00430] [EC:1.11.1.7]
18609926  lignin-forming anionic peroxidase [KO:K00430] [EC:1.11.1.7]
18608317  cationic peroxidase 2 [KO:K00430] [EC:1.11.1.7]
18610717  peroxidase 64 [KO:K00430] [EC:1.11.1.7]
18611523  peroxidase 17 [KO:K00430] [EC:1.11.1.7]
18612072  peroxidase P7 [KO:K00430] [EC:1.11.1.7]
18611259  peroxidase 73 [KO:K00430] [EC:1.11.1.7]
18611081  peroxidase 10 [KO:K00430] [EC:1.11.1.7]
18608319  peroxidase N1 [KO:K00430] [EC:1.11.1.7]
18608320  cationic peroxidase 2 [KO:K00430] [EC:1.11.1.7]
18608323  peroxidase N1 [KO:K00430] [EC:1.11.1.7]
18607361  peroxidase 43 [KO:K00430] [EC:1.11.1.7]
18602223  peroxidase 70 [KO:K00430] [EC:1.11.1.7]
18603838  peroxidase 31 [KO:K00430] [EC:1.11.1.7]
18589667  lignin-forming anionic peroxidase [KO:K00430] [EC:1.11.1.7]
18590293  peroxidase 60 [KO:K00430] [EC:1.11.1.7]
18602422  probable peroxidase 61 [KO:K00430] [EC:1.11.1.7]
18602263  cationic peroxidase 1 [KO:K00430] [EC:1.11.1.7]
18602262  peroxidase 70 [KO:K00430] [EC:1.11.1.7]
18600699  peroxidase 31 [KO:K00430] [EC:1.11.1.7]
18605873  peroxidase 5 [KO:K00430] [EC:1.11.1.7]
18602261  peroxidase 70 [KO:K00430] [EC:1.11.1.7]
18589326  peroxidase 45 [KO:K00430] [EC:1.11.1.7]
18601033  peroxidase 55 [KO:K00430] [EC:1.11.1.7]
18603497  peroxidase 5 [KO:K00430] [EC:1.11.1.7]
18589666  peroxidase 15 [KO:K00430] [EC:1.11.1.7]
18603662  peroxidase 29 [KO:K00430] [EC:1.11.1.7]
108661676  peroxidase 55-like [KO:K00430] [EC:1.11.1.7]
18601034  peroxidase 55 [KO:K00430] [EC:1.11.1.7]
18603684  peroxidase 40 [KO:K00430] [EC:1.11.1.7]
18599776  peroxidase 44 [KO:K00430] [EC:1.11.1.7]
18594731  putative Peroxidase 48 [KO:K00430] [EC:1.11.1.7]
18597147  peroxidase 42 [KO:K00430] [EC:1.11.1.7]
18591452  peroxidase 9 [KO:K00430] [EC:1.11.1.7]
108660418  peroxidase 19 [KO:K00430] [EC:1.11.1.7]
18591603  peroxidase 64 [KO:K00430] [EC:1.11.1.7]
18592677  peroxidase 12 [KO:K00430] [EC:1.11.1.7]
18587397  peroxidase P7 [KO:K00430] [EC:1.11.1.7]
18587400  peroxidase P7 [KO:K00430] [EC:1.11.1.7]
18595928  putative Peroxidase 48 [KO:K00430] [EC:1.11.1.7]
18587406  peroxidase 4 [KO:K00430] [EC:1.11.1.7]
18592526  peroxidase 13 [KO:K00430] [EC:1.11.1.7]
18610982  anthocyanidin 3-O-glucosyltransferase 5 [KO:K12356] [EC:2.4.1.111]
18610980  UDP-glycosyltransferase 72E1 [KO:K12356] [EC:2.4.1.111]
18610979  UDP-glycosyltransferase 72E1 [KO:K12356] [EC:2.4.1.111]
18610983  anthocyanidin 3-O-glucosyltransferase 5 [KO:K12356] [EC:2.4.1.111]
18610981  UDP-glycosyltransferase 72E1 [KO:K12356] [EC:2.4.1.111]
18610985  anthocyanidin 3-O-glucosyltransferase 5 [KO:K12356] [EC:2.4.1.111]
18610978  anthocyanidin 3-O-glucosyltransferase 5 [KO:K12356] [EC:2.4.1.111]
Compound
C00079  L-Phenylalanine
C00082  L-Tyrosine
C00223  p-Coumaroyl-CoA
C00315  Spermidine
C00323  Caffeoyl-CoA
C00406  Feruloyl-CoA
C00411  Sinapoyl-CoA
C00423  trans-Cinnamate
C00482  Sinapate
C00540  Cinnamoyl-CoA
C00590  Coniferyl alcohol
C00761  Coniferin
C00811  4-Coumarate
C00852  Chlorogenate
C00903  Cinnamaldehyde
C00933  Sinapine
C01175  1-O-Sinapoyl-beta-D-glucose
C01197  Caffeate
C01494  Ferulate
C01533  Syringin
C02325  Sinapyl alcohol
C02646  4-Coumaryl alcohol
C02666  Coniferyl aldehyde
C02887  Sinapoyl malate
C02947  4-Coumaroylshikimate
C04366  3-(2-Carboxyethenyl)-cis,cis-muconate
C05608  4-Hydroxycinnamyl aldehyde
C05610  Sinapoyl aldehyde
C05619  5-Hydroxyferulic acid
C05627  4-Hydroxystyrene
C05855  4-Hydroxycinnamyl alcohol 4-D-glucoside
C06224  3,4-Dihydroxystyrene
C10428  Anethole
C10434  5-O-Caffeoylshikimic acid
C10452  Estragole
C10453  Eugenol
C10454  Methyleugenol
C10469  Isoeugenol
C10478  Methylisoeugenol
C10945  Caffeic aldehyde
C12203  5-Hydroxyferuloyl-CoA
C12204  5-Hydroxyconiferaldehyde
C12205  5-Hydroxyconiferyl alcohol
C12206  Caffeyl alcohol
C12208  p-Coumaroyl quinic acid
C15804  p-Hydroxyphenyl lignin
C15805  Guaiacyl lignin
C15806  Syringyl lignin
C15807  5-Hydroxy-guaiacyl lignin
C16930  Chavicol
C18069  N1,N5,N10-Tricoumaroyl spermidine
C18070  N1,N5,N10-Tricaffeoyl spermidine
C18071  N1,N5,N10-Triferuloyl spermidine
C18072  N1,N5,N10-Tri(hydroxyferuloyl) spermidine
C18073  N1,N5-Di(hydroxyferuloyl)-N10-sinapoyl spermidine
C20225  Coniferyl acetate
C20464  Isochavicol
C20465  Coumaryl acetate
Reference
  Authors
Nair RB, Bastress KL, Ruegger MO, Denault JW, Chapple C.
  Title
The Arabidopsis thaliana REDUCED EPIDERMAL FLUORESCENCE1 gene encodes an aldehyde dehydrogenase involved in ferulic acid and sinapic acid biosynthesis.
  Journal
Plant Cell 16:544-54 (2004)
DOI:10.1105/tpc.017509
Reference
  Authors
Baucher M, Halpin C, Petit-Conil M, Boerjan W.
  Title
Lignin: genetic engineering and impact on pulping.
  Journal
Crit Rev Biochem Mol Biol 38:305-50 (2003)
DOI:10.1080/10409230391036757
Reference
  Authors
Rogers LA, Dubos C, Cullis IF, Surman C, Poole M, Willment J, Mansfield SD, Campbell MM.
  Title
Light, the circadian clock, and sugar perception in the control of lignin biosynthesis.
  Journal
J Exp Bot 56:1651-63 (2005)
DOI:10.1093/jxb/eri162
Reference
  Authors
Whetten R, Sederoff R.
  Title
Lignin Biosynthesis.
  Journal
Plant Cell 7:1001-1013 (1995)
DOI:10.1105/tpc.7.7.1001
Reference
PMID:8972602
  Authors
Lorenzen M, Racicot V, Strack D, Chapple C.
  Title
Sinapic acid ester metabolism in wild type and a sinapoylglucose-accumulating mutant of arabidopsis.
  Journal
Plant Physiol 112:1625-30 (1996)
DOI:10.1104/pp.112.4.1625
Reference
PMID:1477555
  Authors
Chapple CC, Vogt T, Ellis BE, Somerville CR.
  Title
An Arabidopsis mutant defective in the general phenylpropanoid pathway.
  Journal
Plant Cell 4:1413-24 (1992)
DOI:10.1105/tpc.4.11.1413
Reference
  Authors
Raes J, Rohde A, Christensen JH, Van de Peer Y, Boerjan W.
  Title
Genome-wide characterization of the lignification toolbox in Arabidopsis.
  Journal
Plant Physiol 133:1051-71 (2003)
DOI:10.1104/pp.103.026484
Reference
  Authors
Costa MA, Collins RE, Anterola AM, Cochrane FC, Davin LB, Lewis NG.
  Title
An in silico assessment of gene function and organization of the phenylpropanoid pathway metabolic networks in Arabidopsis thaliana and limitations thereof.
  Journal
Phytochemistry 64:1097-112 (2003)
DOI:10.1016/S0031-9422(03)00517-X
Reference
  Authors
Meyermans H, Morreel K, Lapierre C, Pollet B, De Bruyn A, Busson R, Herdewijn P, Devreese B, Van Beeumen J, Marita JM, Ralph J, Chen C, Burggraeve B, Van Montagu M, Messens E, Boerjan W.
  Title
Modifications in lignin and accumulation of phenolic glucosides in poplar xylem upon down-regulation of caffeoyl-coenzyme A O-methyltransferase, an enzyme involved in lignin biosynthesis.
  Journal
J Biol Chem 275:36899-909 (2000)
DOI:10.1074/jbc.M006915200
Reference
  Authors
Gachon CM, Langlois-Meurinne M, Henry Y, Saindrenan P.
  Title
Transcriptional co-regulation of secondary metabolism enzymes in Arabidopsis: functional and evolutionary implications.
  Journal
Plant Mol Biol 58:229-45 (2005)
DOI:10.1007/s11103-005-5346-5
Reference
  Authors
Li L, Popko JL, Umezawa T, Chiang VL.
  Title
5-hydroxyconiferyl aldehyde modulates enzymatic methylation for syringyl monolignol formation, a new view of monolignol biosynthesis in angiosperms.
  Journal
J Biol Chem 275:6537-45 (2000)
DOI:10.1074/jbc.275.9.6537
Reference
  Authors
Yamauchi K, Yasuda S, Fukushima K.
  Title
Evidence for the biosynthetic pathway from sinapic acid to syringyl lignin using labeled sinapic acid with stable isotope at both methoxy groups in Robinia pseudoacacia and Nerium indicum.
  Journal
J Agric Food Chem 50:3222-7 (2002)
DOI:10.1021/jf011565x
Reference
  Authors
Eckardt NA.
  Title
Probing the mysteries of lignin biosynthesis: the crystal structure of caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase provides new insights.
  Journal
Plant Cell 14:1185-9 (2002)
DOI:10.1105/tpc.140610
Related
pathway
tcc00130  Ubiquinone and other terpenoid-quinone biosynthesis
tcc00400  Phenylalanine, tyrosine and tryptophan biosynthesis
tcc00941  Flavonoid biosynthesis
tcc00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
KO pathway
ko00940   
LinkDB

DBGET integrated database retrieval system