ENTRY ko00940 Pathway NAME Phenylpropanoid biosynthesis 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 ko00940 Phenylpropanoid biosynthesis MODULE M00039 Monolignol biosynthesis, phenylalanine/tyrosine => monolignol [PATH:ko00940] M00137 Flavanone biosynthesis, phenylalanine => naringenin [PATH:ko00940] DBLINKS GO: 0009699 ORTHOLOGY K10775 phenylalanine ammonia-lyase [EC:4.3.1.24] K13064 phenylalanine/tyrosine ammonia-lyase [EC:4.3.1.25] K00487 trans-cinnamate 4-monooxygenase [EC:1.14.14.91] K01904 4-coumarate--CoA ligase [EC:6.2.1.12] K13065 shikimate O-hydroxycinnamoyltransferase [EC:2.3.1.133] K09754 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase [EC:1.14.14.96] K18368 caffeoylshikimate esterase [EC:3.1.1.-] K00588 caffeoyl-CoA O-methyltransferase [EC:2.1.1.104] K09753 cinnamoyl-CoA reductase [EC:1.2.1.44] K12355 coniferyl-aldehyde dehydrogenase [EC:1.2.1.68] K09755 ferulate-5-hydroxylase [EC:1.14.-.-] K13066 caffeic acid 3-O-methyltransferase / acetylserotonin O-methyltransferase [EC:2.1.1.68 2.1.1.4] K00083 cinnamyl-alcohol dehydrogenase [EC:1.1.1.195] K22395 cinnamyl-alcohol dehydrogenase [EC:1.1.1.195] K11188 peroxiredoxin 6 [EC:1.11.1.7 1.11.1.27 3.1.1.-] K00430 peroxidase [EC:1.11.1.7] K03782 catalase-peroxidase [EC:1.11.1.21] K12356 coniferyl-alcohol glucosyltransferase [EC:2.4.1.111] K17054 coniferyl alcohol acyltransferase [EC:2.3.1.-] K17055 eugenol synthase [EC:1.1.1.318] K17056 isoeugenol synthase [EC:1.1.1.319] K17057 (iso)eugenol O-methyltransferase [EC:2.1.1.146] K17058 eugenol/chavicol O-methyltransferase [EC:2.1.1.146] K17059 trans-anol O-methyltransferase [EC:2.1.1.279] K13068 sinapate 1-glucosyltransferase [EC:2.4.1.120] K09756 serine carboxypeptidase-like 19 [EC:3.4.16.- 2.3.1.91] K09757 serine carboxypeptidase-like 8 [EC:3.4.16.- 2.3.1.92] K20039 phenacrylate decarboxylase [EC:4.1.1.102] K03186 flavin prenyltransferase [EC:2.5.1.129] K13727 phenacrylate decarboxylase [EC:4.1.1.102] K15506 cytochrome P450 family 98 subfamily A8 [EC:1.14.13.-] K23662 cytochrome P450 family 98 subfamily A9 [EC:1.14.13.-] K13067 putative caffeoyl-CoA 3-O-methyltransferase [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 ko00130 Ubiquinone and other terpenoid-quinone biosynthesis ko00400 Phenylalanine, tyrosine and tryptophan biosynthesis ko00941 Flavonoid biosynthesis ko00945 Stilbenoid, diarylheptanoid and gingerol biosynthesis ///