KEGG   PATHWAY: thj00940
Entry
thj00940                    Pathway                                
Name
Phenylpropanoid biosynthesis - Tarenaya hassleriana (spider flower)
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
thj00940  Phenylpropanoid biosynthesis
thj00940

Module
thj_M00039  Monolignol biosynthesis, phenylalanine/tyrosine => monolignol [PATH:thj00940]
thj_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:thj00940]
Other DBs
GO: 0009699
Organism
Tarenaya hassleriana (spider flower) [GN:thj]
Gene
104805263  phenylalanine ammonia-lyase 1 [KO:K10775] [EC:4.3.1.24]
104806492  phenylalanine ammonia-lyase 1 [KO:K10775] [EC:4.3.1.24]
104816418  phenylalanine ammonia-lyase 4 [KO:K10775] [EC:4.3.1.24]
104823458  phenylalanine ammonia-lyase 1-like [KO:K10775] [EC:4.3.1.24]
104800793  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
104815827  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
104808912  cytochrome P450 CYP73A100-like [KO:K00487] [EC:1.14.14.91]
104798452  4-coumarate--CoA ligase-like 6 isoform X1 [KO:K01904] [EC:6.2.1.12]
104807135  4-coumarate--CoA ligase-like 1 [KO:K01904] [EC:6.2.1.12]
104806267  LOW QUALITY PROTEIN: 4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]
104812629  4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]
104821776  4-coumarate--CoA ligase 3 [KO:K01904] [EC:6.2.1.12]
104815164  4-coumarate--CoA ligase 1-like [KO:K01904] [EC:6.2.1.12]
104817929  4-coumarate--CoA ligase 4 [KO:K01904] [EC:6.2.1.12]
104799669  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
104804487  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
104809269  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
104809270  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
104812535  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
104817818  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
104819144  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
104819970  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
104814627  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
104803227  cytochrome P450 98A3 [KO:K09754] [EC:1.14.14.96]
104810496  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
104798833  caffeoylshikimate esterase-like isoform X1 [KO:K18368] [EC:3.1.1.-]
104810006  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
104817494  caffeoylshikimate esterase isoform X1 [KO:K18368] [EC:3.1.1.-]
104820948  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
104821928  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
104824251  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
104804378  caffeoyl-CoA O-methyltransferase 5 [KO:K00588] [EC:2.1.1.104]
104807886  putative caffeoyl-CoA O-methyltransferase At1g67980 isoform X1 [KO:K00588] [EC:2.1.1.104]
104811735  probable caffeoyl-CoA O-methyltransferase At4g26220 isoform X1 [KO:K00588] [EC:2.1.1.104]
104819570  caffeoyl-CoA O-methyltransferase 1 [KO:K00588] [EC:2.1.1.104]
104825058  putative caffeoyl-CoA O-methyltransferase At1g67980 [KO:K00588] [EC:2.1.1.104]
104812427  cinnamoyl-CoA reductase 1 [KO:K09753] [EC:1.2.1.44]
104826414  cinnamoyl-CoA reductase 1-like [KO:K09753] [EC:1.2.1.44]
104813587  cinnamoyl-CoA reductase 1-like isoform X1 [KO:K09753] [EC:1.2.1.44]
104804583  aldehyde dehydrogenase family 2 member C4-like [KO:K12355] [EC:1.2.1.68]
104821635  aldehyde dehydrogenase family 2 member C4-like [KO:K12355] [EC:1.2.1.68]
104821636  aldehyde dehydrogenase family 2 member C4-like [KO:K12355] [EC:1.2.1.68]
104804582  aldehyde dehydrogenase family 2 member C4 [KO:K12355] [EC:1.2.1.68]
104804535  cytochrome P450 84A1-like [KO:K09755] [EC:1.14.-.-]
104804254  cytochrome P450 84A1 [KO:K09755] [EC:1.14.-.-]
104807482  cytochrome P450 84A1-like [KO:K09755] [EC:1.14.-.-]
104804741  caffeic acid 3-O-methyltransferase-like [KO:K13066] [EC:2.1.1.68 2.1.1.4]
104802099  caffeic acid 3-O-methyltransferase-like [KO:K13066] [EC:2.1.1.68 2.1.1.4]
104799941  flavone 3'-O-methyltransferase 1-like [KO:K13066] [EC:2.1.1.68 2.1.1.4]
104799942  caffeic acid 3-O-methyltransferase-like [KO:K13066] [EC:2.1.1.68 2.1.1.4]
104799943  caffeic acid 3-O-methyltransferase-like [KO:K13066] [EC:2.1.1.68 2.1.1.4]
104811887  flavone 3'-O-methyltransferase 1 [KO:K13066] [EC:2.1.1.68 2.1.1.4]
104813820  anthranilate N-methyltransferase-like [KO:K13066] [EC:2.1.1.68 2.1.1.4]
104804389  cinnamyl alcohol dehydrogenase 5-like [KO:K00083] [EC:1.1.1.195]
104798385  probable cinnamyl alcohol dehydrogenase 1 isoform X1 [KO:K00083] [EC:1.1.1.195]
104798790  cinnamyl alcohol dehydrogenase 4 [KO:K00083] [EC:1.1.1.195]
104824830  probable cinnamyl alcohol dehydrogenase 9 [KO:K00083] [EC:1.1.1.195]
104798391  probable cinnamyl alcohol dehydrogenase 1 isoform X1 [KO:K00083] [EC:1.1.1.195]
104807239  cinnamyl alcohol dehydrogenase 5-like [KO:K00083] [EC:1.1.1.195]
104807733  probable cinnamyl alcohol dehydrogenase 9 [KO:K00083] [EC:1.1.1.195]
104814344  berberine bridge enzyme-like 5 [KO:K22395] [EC:1.1.1.195]
104798588  berberine bridge enzyme-like 4 [KO:K22395] [EC:1.1.1.195]
104821806  1-Cys peroxiredoxin PER1 [KO:K11188] [EC:1.11.1.7 1.11.1.27 3.1.1.-]
104798341  peroxidase 65-like [KO:K00430] [EC:1.11.1.7]
104798572  peroxidase 7 [KO:K00430] [EC:1.11.1.7]
104798474  peroxidase 20 isoform X1 [KO:K00430] [EC:1.11.1.7]
104801663  peroxidase 11 [KO:K00430] [EC:1.11.1.7]
104802212  peroxidase 3-like [KO:K00430] [EC:1.11.1.7]
104803672  peroxidase 47 [KO:K00430] [EC:1.11.1.7]
104803947  peroxidase 16 [KO:K00430] [EC:1.11.1.7]
104804946  peroxidase 44-like [KO:K00430] [EC:1.11.1.7]
104804991  peroxidase 64-like [KO:K00430] [EC:1.11.1.7]
104804998  peroxidase 64-like [KO:K00430] [EC:1.11.1.7]
104801750  peroxidase 44-like [KO:K00430] [EC:1.11.1.7]
104801752  peroxidase 44-like [KO:K00430] [EC:1.11.1.7]
104801753  peroxidase 44-like [KO:K00430] [EC:1.11.1.7]
104810922  peroxidase 60 [KO:K00430] [EC:1.11.1.7]
104806690  peroxidase 65-like [KO:K00430] [EC:1.11.1.7]
104804576  peroxidase 69-like [KO:K00430] [EC:1.11.1.7]
104805415  peroxidase 63-like [KO:K00430] [EC:1.11.1.7]
104807472  peroxidase 49 [KO:K00430] [EC:1.11.1.7]
104806033  peroxidase 44-like [KO:K00430] [EC:1.11.1.7]
104803484  peroxidase 16-like [KO:K00430] [EC:1.11.1.7]
104807625  peroxidase 50 [KO:K00430] [EC:1.11.1.7]
104805121  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
104800021  peroxidase 69-like [KO:K00430] [EC:1.11.1.7]
104800982  peroxidase 3 [KO:K00430] [EC:1.11.1.7]
104802539  peroxidase 30 [KO:K00430] [EC:1.11.1.7]
104799241  peroxidase C1C-like [KO:K00430] [EC:1.11.1.7]
104799242  peroxidase E5 [KO:K00430] [EC:1.11.1.7]
104799660  peroxidase E5-like [KO:K00430] [EC:1.11.1.7]
104802564  peroxidase 24 [KO:K00430] [EC:1.11.1.7]
104799291  peroxidase A2-like [KO:K00430] [EC:1.11.1.7]
104803606  peroxidase 46 [KO:K00430] [EC:1.11.1.7]
104803872  probable peroxidase 26 [KO:K00430] [EC:1.11.1.7]
104805307  peroxidase 21 [KO:K00430] [EC:1.11.1.7]
104826546  peroxidase 25 [KO:K00430] [EC:1.11.1.7]
104827253  peroxidase 57-like [KO:K00430] [EC:1.11.1.7]
104818162  probable peroxidase 61 [KO:K00430] [EC:1.11.1.7]
104819530  putative Peroxidase 48 [KO:K00430] [EC:1.11.1.7]
104820307  peroxidase 29 [KO:K00430] [EC:1.11.1.7]
104820312  peroxidase 40 isoform X1 [KO:K00430] [EC:1.11.1.7]
104815112  peroxidase N [KO:K00430] [EC:1.11.1.7]
104816519  peroxidase 52 [KO:K00430] [EC:1.11.1.7]
104819253  peroxidase 35-like [KO:K00430] [EC:1.11.1.7]
104819767  peroxidase 49 [KO:K00430] [EC:1.11.1.7]
104812072  peroxidase 13 isoform X1 [KO:K00430] [EC:1.11.1.7]
104804948  peroxidase 44-like [KO:K00430] [EC:1.11.1.7]
104820583  peroxidase 19-like [KO:K00430] [EC:1.11.1.7]
104821231  peroxidase 35-like [KO:K00430] [EC:1.11.1.7]
104821268  peroxidase 10-like [KO:K00430] [EC:1.11.1.7]
104822363  peroxidase 27-like [KO:K00430] [EC:1.11.1.7]
104819334  peroxidase 62 [KO:K00430] [EC:1.11.1.7]
104819336  peroxidase 69-like [KO:K00430] [EC:1.11.1.7]
104813112  peroxidase 42 [KO:K00430] [EC:1.11.1.7]
104814404  peroxidase 39 [KO:K00430] [EC:1.11.1.7]
104825085  peroxidase 66 [KO:K00430] [EC:1.11.1.7]
104816713  peroxidase 10 [KO:K00430] [EC:1.11.1.7]
104821377  peroxidase 57-like [KO:K00430] [EC:1.11.1.7]
104817535  peroxidase 27-like [KO:K00430] [EC:1.11.1.7]
104824885  peroxidase 17 [KO:K00430] [EC:1.11.1.7]
104822063  peroxidase 6 [KO:K00430] [EC:1.11.1.7]
104826155  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
104811054  peroxidase 37-like [KO:K00430] [EC:1.11.1.7]
104811055  peroxidase E5-like [KO:K00430] [EC:1.11.1.7]
104811056  peroxidase E5-like [KO:K00430] [EC:1.11.1.7]
104825300  peroxidase 63-like [KO:K00430] [EC:1.11.1.7]
104804559  putative Peroxidase 48 [KO:K00430] [EC:1.11.1.7]
104821306  peroxidase 72 [KO:K00430] [EC:1.11.1.7]
104822830  peroxidase 9 [KO:K00430] [EC:1.11.1.7]
104816044  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
104811773  peroxidase 43 [KO:K00430] [EC:1.11.1.7]
104821123  peroxidase 55 [KO:K00430] [EC:1.11.1.7]
104823177  peroxidase P7-like [KO:K00430] [EC:1.11.1.7]
104823712  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
104814248  peroxidase 19-like [KO:K00430] [EC:1.11.1.7]
104809847  UDP-glycosyltransferase 72E2-like [KO:K12356] [EC:2.4.1.111]
104800370  UDP-glycosyltransferase 72E1-like [KO:K12356] [EC:2.4.1.111]
104826884  UDP-glycosyltransferase 72E1 [KO:K12356] [EC:2.4.1.111]
104807550  UDP-glycosyltransferase 72D1 [KO:K12356] [EC:2.4.1.111]
104812549  cytochrome P450 98A9 [KO:K23662] [EC:1.14.13.-]
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
thj00130  Ubiquinone and other terpenoid-quinone biosynthesis
thj00400  Phenylalanine, tyrosine and tryptophan biosynthesis
thj00941  Flavonoid biosynthesis
thj00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
KO pathway
ko00940   
LinkDB

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