KEGG   PATHWAY: ath00940
Entry
ath00940                    Pathway                                
Name
Phenylpropanoid biosynthesis - Arabidopsis thaliana (thale cress)
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
ath00940  Phenylpropanoid biosynthesis
ath00940

Module
ath_M00039  Monolignol biosynthesis, phenylalanine/tyrosine => monolignol [PATH:ath00940]
ath_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:ath00940]
Other DBs
GO: 0009699
Organism
Arabidopsis thaliana (thale cress) [GN:ath]
Gene
AT3G10340  PAL4; phenylalanine ammonia-lyase 4 [KO:K10775] [EC:4.3.1.24]
AT3G53260  PAL2; phenylalanine ammonia-lyase 2 [KO:K10775] [EC:4.3.1.24]
AT2G37040  PAL1; PHE ammonia lyase 1 [KO:K10775] [EC:4.3.1.24]
AT5G04230  PAL3; phenyl alanine ammonia-lyase 3 [KO:K10775] [EC:4.3.1.24]
AT2G30490  C4H; cinnamate-4-hydroxylase [KO:K00487] [EC:1.14.14.91]
AT4G05160  AMP-dependent synthetase and ligase family protein [KO:K01904] [EC:6.2.1.12]
AT1G65060  4CL3; 4-coumarate:CoA ligase 3 [KO:K01904] [EC:6.2.1.12]
AT1G62940  ACOS5; acyl-CoA synthetase 5 [KO:K01904] [EC:6.2.1.12]
AT3G21240  4CL2; 4-coumarate:CoA ligase 2 [KO:K01904] [EC:6.2.1.12]
AT1G51680  4CL1; 4-coumarate:CoA ligase 1 [KO:K01904] [EC:6.2.1.12]
AT3G21230  4CL5; 4-coumarate:CoA ligase 5 [KO:K01904] [EC:6.2.1.12]
AT4G19010  AMP-dependent synthetase and ligase family protein [KO:K01904] [EC:6.2.1.12]
AT5G63380  AMP-dependent synthetase and ligase family protein [KO:K01904] [EC:6.2.1.12]
AT5G48930  HCT; hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
AT2G19070  SHT; spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
AT5G57840  HXXXD-type acyl-transferase family protein [KO:K13065] [EC:2.3.1.133]
AT2G40890  CYP98A3; cytochrome P450, family 98, subfamily A, polypeptide 3 [KO:K09754] [EC:1.14.14.96]
AT1G52760  LysoPL2; lysophospholipase 2 [KO:K18368] [EC:3.1.1.-]
AT2G47630  alpha/beta-Hydrolases superfamily protein [KO:K18368] [EC:3.1.1.-]
AT2G39420  alpha/beta-Hydrolases superfamily protein [KO:K18368] [EC:3.1.1.-]
AT5G16120  alpha/beta-Hydrolases superfamily protein [KO:K18368] [EC:3.1.1.-]
AT3G62860  alpha/beta-Hydrolases superfamily protein [KO:K18368] [EC:3.1.1.-]
AT1G77420  alpha/beta-Hydrolases superfamily protein [KO:K18368] [EC:3.1.1.-]
AT3G55180  alpha/beta-Hydrolases superfamily protein [KO:K18368] [EC:3.1.1.-]
AT4G34050  CCoAOMT1; S-adenosyl-L-methionine-dependent methyltransferases superfamily protein [KO:K00588] [EC:2.1.1.104]
AT1G24735  S-adenosyl-L-methionine-dependent methyltransferases superfamily protein [KO:K00588] [EC:2.1.1.104]
AT1G67980  CCOAMT; caffeoyl-CoA 3-O-methyltransferase [KO:K00588] [EC:2.1.1.104]
AT4G26220  S-adenosyl-L-methionine-dependent methyltransferases superfamily protein [KO:K00588] [EC:2.1.1.104]
AT1G15950  CCR1; cinnamoyl coa reductase 1 [KO:K09753] [EC:1.2.1.44]
AT1G80820  CCR2; cinnamoyl coa reductase [KO:K09753] [EC:1.2.1.44]
AT3G24503  ALDH2C4; aldehyde dehydrogenase 2C4 [KO:K12355] [EC:1.2.1.68]
AT4G36220  FAH1; ferulic acid 5-hydroxylase 1 [KO:K09755] [EC:1.14.-.-]
AT5G04330  CYP84A4; Cytochrome P450 superfamily protein [KO:K09755] [EC:1.14.-.-]
AT5G54160  OMT1; O-methyltransferase 1 [KO:K13066] [EC:2.1.1.68 2.1.1.4]
AT3G19450  ATCAD4; GroES-like zinc-binding alcohol dehydrogenase family protein [KO:K00083] [EC:1.1.1.195]
AT4G34230  CAD5; cinnamyl alcohol dehydrogenase 5 [KO:K00083] [EC:1.1.1.195]
AT2G21730  CAD2; cinnamyl alcohol dehydrogenase homolog 2 [KO:K00083] [EC:1.1.1.195]
AT4G37970  CAD6; cinnamyl alcohol dehydrogenase 6 [KO:K00083] [EC:1.1.1.195]
AT2G21890  CAD3; cinnamyl alcohol dehydrogenase homolog 3 [KO:K00083] [EC:1.1.1.195]
AT1G72680  CAD1; cinnamyl-alcohol dehydrogenase [KO:K00083] [EC:1.1.1.195]
AT4G39330  CAD9; cinnamyl alcohol dehydrogenase 9 [KO:K00083] [EC:1.1.1.195]
AT4G37980  ELI3-1; cinnamyl alcohol dehydrogenase 7 [KO:K00083] [EC:1.1.1.195]
AT4G37990  ELI3-2; cinnamyl alcohol dehydrogenase 8 [KO:K00083] [EC:1.1.1.195]
AT1G30760  FAD-binding Berberine family protein [KO:K22395] [EC:1.1.1.195]
AT2G34790  MEE23; FAD-binding Berberine family protein [KO:K22395] [EC:1.1.1.195]
AT1G48130  PER1; 1-cysteine peroxiredoxin 1 [KO:K11188] [EC:1.11.1.7 1.11.1.27 3.1.1.-]
AT5G19880  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT1G49570  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT1G68850  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT1G71695  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT2G18140  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT2G18150  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT2G18980  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT2G22420  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT2G24800  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT2G34060  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT2G37130  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT2G38390  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT2G39040  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT2G41480  peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT2G43480  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT3G01190  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT3G03670  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT3G17070  Peroxidase family protein [KO:K00430] [EC:1.11.1.7]
AT3G21770  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT3G28200  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT3G49120  PRXCB; peroxidase CB [KO:K00430] [EC:1.11.1.7]
AT3G49960  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT4G08770  Prx37; Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT4G08780  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT4G11290  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT4G16270  peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT4G17690  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT4G21960  PRXR1; Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT4G26010  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT4G30170  Peroxidase family protein [KO:K00430] [EC:1.11.1.7]
AT4G31760  peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT4G33420  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT4G36430  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT4G37520  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT4G37530  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G05340  PRX52; Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G06720  PA2; peroxidase 2 [KO:K00430] [EC:1.11.1.7]
AT5G06730  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G14130  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G15180  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G17820  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G19890  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G22410  RHS18; root hair specific 18 [KO:K00430] [EC:1.11.1.7]
AT5G24070  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G40150  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G42180  PER64; Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G47000  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G51890  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G58390  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G58400  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G64100  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G64110  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G64120  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G66390  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G67400  RHS19; root hair specific 19 [KO:K00430] [EC:1.11.1.7]
AT1G05260  RCI3; Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT1G14540  PER4; Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT1G14550  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT1G24110  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT1G30870  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT1G34510  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT1G44970  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT2G38380  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT3G49110  PRXCA; peroxidase CA [KO:K00430] [EC:1.11.1.7]
AT3G32980  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT1G05240  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT4G25980  peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT1G77100  peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT3G50990  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT1G05250  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT2G35380  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G39580  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT4G33870  Peroxidase superfamily protein [KO:K00430] [EC:1.11.1.7]
AT5G26310  UGT72E3; UDP-Glycosyltransferase superfamily protein [KO:K12356] [EC:2.4.1.111]
AT3G50740  UGT72E1; UDP-glucosyl transferase 72E1 [KO:K12356] [EC:2.4.1.111]
AT5G66690  UGT72E2; UDP-Glycosyltransferase superfamily protein [KO:K12356] [EC:2.4.1.111]
AT3G21560  UGT84A2; UDP-Glycosyltransferase superfamily protein [KO:K13068] [EC:2.4.1.120]
AT5G09640  SCPL19; serine carboxypeptidase-like 19 [KO:K09756] [EC:3.4.16.- 2.3.1.91]
AT2G22990  SNG1; sinapoylglucose 1 [KO:K09757] [EC:3.4.16.- 2.3.1.92]
AT1G74540  CYP98A8; cytochrome P450, family 98, subfamily A, polypeptide 8 [KO:K15506] [EC:1.14.13.-]
AT1G74550  CYP98A9; cytochrome P450, family 98, subfamily A, polypeptide 9 [KO:K23662] [EC:1.14.13.-]
AT1G67990  TSM1; S-adenosyl-L-methionine-dependent methyltransferases superfamily protein [KO:K13067] [EC:2.1.1.-]
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
ath00130  Ubiquinone and other terpenoid-quinone biosynthesis
ath00400  Phenylalanine, tyrosine and tryptophan biosynthesis
ath00941  Flavonoid biosynthesis
ath00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
KO pathway
ko00940   
LinkDB

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