KEGG   PATHWAY: cmax00940
Entry
cmax00940                   Pathway                                
Name
Phenylpropanoid biosynthesis - Cucurbita maxima (winter squash)
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
cmax00940  Phenylpropanoid biosynthesis
cmax00940

Module
cmax_M00039  Monolignol biosynthesis, phenylalanine/tyrosine => monolignol [PATH:cmax00940]
cmax_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:cmax00940]
Other DBs
GO: 0009699
Organism
Cucurbita maxima (winter squash) [GN:cmax]
Gene
111466447  phenylalanine ammonia-lyase G4-like [KO:K10775] [EC:4.3.1.24]
111477962  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
111477963  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
111483977  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
111485128  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
111471134  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
111471135  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
111471136  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
111471137  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
111471138  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
111471139  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
111471140  phenylalanine ammonia-lyase [KO:K10775] [EC:4.3.1.24]
111484465  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
111499735  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
111492592  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
111491732  cytochrome P450 CYP73A100-like [KO:K00487] [EC:1.14.14.91]
111481607  4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]
111492331  4-coumarate--CoA ligase 2-like [KO:K01904] [EC:6.2.1.12]
111484944  4-coumarate--CoA ligase 1-like isoform X1 [KO:K01904] [EC:6.2.1.12]
111493400  4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]
111466820  4-coumarate--CoA ligase-like 6 isoform X1 [KO:K01904] [EC:6.2.1.12]
111488383  4-coumarate--CoA ligase 2-like [KO:K01904] [EC:6.2.1.12]
111497098  4-coumarate--CoA ligase 2-like isoform X1 [KO:K01904] [EC:6.2.1.12]
111493060  4-coumarate--CoA ligase 1-like [KO:K01904] [EC:6.2.1.12]
111482411  4-coumarate--CoA ligase 1-like [KO:K01904] [EC:6.2.1.12]
111497965  4-coumarate--CoA ligase 1-like [KO:K01904] [EC:6.2.1.12]
111497966  4-coumarate--CoA ligase 1-like [KO:K01904] [EC:6.2.1.12]
111466396  4-coumarate--CoA ligase-like 1 [KO:K01904] [EC:6.2.1.12]
111495139  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
111490339  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
111498028  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
111478230  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
111488196  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
111492737  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
111466005  spermidine hydroxycinnamoyl transferase-like isoform X1 [KO:K13065] [EC:2.3.1.133]
111472185  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
111496400  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
111482281  cytochrome P450 98A2 [KO:K09754] [EC:1.14.14.96]
111482478  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
111490153  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
111492898  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
111487110  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
111472103  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
111470490  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
111471046  caffeoyl-CoA O-methyltransferase 5 [KO:K00588] [EC:2.1.1.104]
111466357  caffeoyl-CoA O-methyltransferase-like isoform X1 [KO:K00588] [EC:2.1.1.104]
111466358  flavonoid 3',5'-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
111466359  flavonoid 3',5'-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
111486125  caffeoyl-CoA O-methyltransferase 5 [KO:K00588] [EC:2.1.1.104]
111488801  cinnamoyl-CoA reductase 1-like [KO:K09753] [EC:1.2.1.44]
111492719  cinnamoyl-CoA reductase 2-like [KO:K09753] [EC:1.2.1.44]
111481542  cinnamoyl-CoA reductase 2-like [KO:K09753] [EC:1.2.1.44]
111481543  cinnamoyl-CoA reductase 1-like [KO:K09753] [EC:1.2.1.44]
111481544  cinnamoyl-CoA reductase 2-like [KO:K09753] [EC:1.2.1.44]
111492576  cinnamoyl-CoA reductase 2-like [KO:K09753] [EC:1.2.1.44]
111485175  aldehyde dehydrogenase family 2 member C4-like [KO:K12355] [EC:1.2.1.68]
111471924  aldehyde dehydrogenase family 2 member C4-like [KO:K12355] [EC:1.2.1.68]
111469596  cytochrome P450 84A1-like [KO:K09755] [EC:1.14.-.-]
111497337  cytochrome P450 84A1 [KO:K09755] [EC:1.14.-.-]
111467633  caffeic acid 3-O-methyltransferase [KO:K13066] [EC:2.1.1.68 2.1.1.4]
111498431  caffeic acid 3-O-methyltransferase-like isoform X1 [KO:K13066] [EC:2.1.1.68 2.1.1.4]
111480679  cinnamyl alcohol dehydrogenase 1-like [KO:K00083] [EC:1.1.1.195]
111491385  probable cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
111483076  cinnamyl alcohol dehydrogenase 1-like [KO:K00083] [EC:1.1.1.195]
111470320  probable mannitol dehydrogenase [KO:K00083] [EC:1.1.1.195]
111470321  probable cinnamyl alcohol dehydrogenase 9 [KO:K00083] [EC:1.1.1.195]
111481304  probable cinnamyl alcohol dehydrogenase 6 [KO:K00083] [EC:1.1.1.195]
111499888  probable mannitol dehydrogenase [KO:K00083] [EC:1.1.1.195]
111486042  cinnamyl alcohol dehydrogenase 1-like [KO:K00083] [EC:1.1.1.195]
111495628  berberine bridge enzyme-like 13 [KO:K22395] [EC:1.1.1.195]
111490401  berberine bridge enzyme-like 13 [KO:K22395] [EC:1.1.1.195]
111477806  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
111470853  1-Cys peroxiredoxin A isoform X1 [KO:K11188] [EC:1.11.1.7 1.11.1.27 3.1.1.-]
111469851  peroxidase 41-like [KO:K00430] [EC:1.11.1.7]
111469860  peroxidase 41-like [KO:K00430] [EC:1.11.1.7]
111469882  peroxidase 63-like [KO:K00430] [EC:1.11.1.7]
111466598  peroxidase 60 [KO:K00430] [EC:1.11.1.7]
111471321  peroxidase 41-like [KO:K00430] [EC:1.11.1.7]
111471326  peroxidase 41-like [KO:K00430] [EC:1.11.1.7]
111471341  peroxidase 41-like [KO:K00430] [EC:1.11.1.7]
111485652  peroxidase 41-like [KO:K00430] [EC:1.11.1.7]
111488183  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
111488186  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
111467048  peroxidase 43 [KO:K00430] [EC:1.11.1.7]
111467055  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
111467056  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
111467057  cationic peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
111468425  putative Peroxidase 48 [KO:K00430] [EC:1.11.1.7]
111497850  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
111498310  peroxidase 21-like isoform X1 [KO:K00430] [EC:1.11.1.7]
111478718  peroxidase 73-like [KO:K00430] [EC:1.11.1.7]
111478738  peroxidase 64-like isoform X1 [KO:K00430] [EC:1.11.1.7]
111481174  peroxidase 45-like [KO:K00430] [EC:1.11.1.7]
111484413  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
111486566  lignin-forming anionic peroxidase-like [KO:K00430] [EC:1.11.1.7]
111499483  peroxidase 4-like [KO:K00430] [EC:1.11.1.7]
111499486  peroxidase 7-like [KO:K00430] [EC:1.11.1.7]
111480890  peroxidase 17 [KO:K00430] [EC:1.11.1.7]
111480902  peroxidase 46-like [KO:K00430] [EC:1.11.1.7]
111484109  peroxidase 3-like [KO:K00430] [EC:1.11.1.7]
111485229  peroxidase 25 [KO:K00430] [EC:1.11.1.7]
111468844  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
111468886  peroxidase 41-like [KO:K00430] [EC:1.11.1.7]
111477242  peroxidase 46 [KO:K00430] [EC:1.11.1.7]
111478477  peroxidase 72-like [KO:K00430] [EC:1.11.1.7]
111466206  peroxidase 51-like [KO:K00430] [EC:1.11.1.7]
111486919  peroxidase 31-like [KO:K00430] [EC:1.11.1.7]
111489047  peroxidase 55 [KO:K00430] [EC:1.11.1.7]
111486074  peroxidase 56-like [KO:K00430] [EC:1.11.1.7]
111486076  peroxidase 3-like [KO:K00430] [EC:1.11.1.7]
111486080  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
111490294  peroxidase 41-like [KO:K00430] [EC:1.11.1.7]
111468255  peroxidase P7-like [KO:K00430] [EC:1.11.1.7]
111470640  peroxidase 20 isoform X1 [KO:K00430] [EC:1.11.1.7]
111473526  peroxidase 51-like [KO:K00430] [EC:1.11.1.7]
111478056  peroxidase 10 [KO:K00430] [EC:1.11.1.7]
111498051  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
111499974  peroxidase 10-like [KO:K00430] [EC:1.11.1.7]
111499975  peroxidase 10-like [KO:K00430] [EC:1.11.1.7]
111482328  peroxidase 31-like [KO:K00430] [EC:1.11.1.7]
111483385  peroxidase 72-like [KO:K00430] [EC:1.11.1.7]
111484447  peroxidase 11 isoform X1 [KO:K00430] [EC:1.11.1.7]
111497576  probable peroxidase 61 [KO:K00430] [EC:1.11.1.7]
111483916  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
111483917  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
111488315  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
111490140  peroxidase 19 [KO:K00430] [EC:1.11.1.7]
111490143  peroxidase 7-like [KO:K00430] [EC:1.11.1.7]
111478881  peroxidase 21-like [KO:K00430] [EC:1.11.1.7]
111469836  peroxidase 3-like [KO:K00430] [EC:1.11.1.7]
111496751  peroxidase 73-like [KO:K00430] [EC:1.11.1.7]
111490832  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
111490833  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
111490834  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
111490835  peroxidase N [KO:K00430] [EC:1.11.1.7]
111490836  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
111490837  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
111490838  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
111482402  peroxidase 21-like [KO:K00430] [EC:1.11.1.7]
111467696  peroxidase 66 [KO:K00430] [EC:1.11.1.7]
111467726  peroxidase 11-like isoform X1 [KO:K00430] [EC:1.11.1.7]
111483968  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
111496276  peroxidase 64-like [KO:K00430] [EC:1.11.1.7]
111484500  peroxidase 4-like [KO:K00430] [EC:1.11.1.7]
111484501  peroxidase 4-like [KO:K00430] [EC:1.11.1.7]
111484502  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
111494232  peroxidase 40-like [KO:K00430] [EC:1.11.1.7]
111495464  peroxidase 42 [KO:K00430] [EC:1.11.1.7]
111489422  peroxidase P7-like [KO:K00430] [EC:1.11.1.7]
111492600  peroxidase P7-like [KO:K00430] [EC:1.11.1.7]
111492601  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
111494849  peroxidase 24-like [KO:K00430] [EC:1.11.1.7]
111467231  peroxidase 47 [KO:K00430] [EC:1.11.1.7]
111480828  peroxidase 72-like [KO:K00430] [EC:1.11.1.7]
111484052  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
111495304  peroxidase 65-like [KO:K00430] [EC:1.11.1.7]
111497363  peroxidase 64-like [KO:K00430] [EC:1.11.1.7]
111478455  LOW QUALITY PROTEIN: UDP-glycosyltransferase 72E1-like [KO:K12356] [EC:2.4.1.111]
111483150  anthocyanidin 3-O-glucosyltransferase 5-like [KO:K12356] [EC:2.4.1.111]
111496796  UDP-glycosyltransferase 72E1-like [KO:K12356] [EC:2.4.1.111]
111479797  anthocyanidin 3-O-glucosyltransferase 5-like [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
cmax00130  Ubiquinone and other terpenoid-quinone biosynthesis
cmax00400  Phenylalanine, tyrosine and tryptophan biosynthesis
cmax00941  Flavonoid biosynthesis
cmax00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
KO pathway
ko00940   
LinkDB

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