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
MODULE      ath_M00039  Monolignol biosynthesis, phenylalanine/tyrosine => monolignol [PATH:ath00940]
            ath_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:ath00940]
DBLINKS     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   PMID:14729911
  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   PMID:14551235
  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   PMID:15878986
  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   PMID:12242395
  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   PMID:14612585
  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   PMID:14568076
  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   PMID:10934215
  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   PMID:16027976
  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   PMID:10692459
  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   PMID:12009990
  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   PMID:12084820
  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
REL_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
///
