KEGG   PATHWAY: rn00940
Entry
rn00940                     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
rn00940  Phenylpropanoid biosynthesis
rn00940

Module
M00039  Monolignol biosynthesis, phenylalanine/tyrosine => monolignol [PATH:rn00940]
M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:rn00940]
Other DBs
GO: 0009699
Reaction
R00697  L-phenylalanine ammonia-lyase (trans-cinnamate-forming)
R00737  L-tyrosine ammonia-lyase (trans-p-hydroxycinnamate-forming)
R01615  4-hydroxycinnamyl aldehyde:NADP+ oxidoreductase (CoA-hydroxycinnamoylating)
R01616  4-coumarate:CoA ligase (AMP-forming)
R01941  caffeic aldehyde:NADP+ oxidoreductase (CoA-caffeoylating)
R01942  S-adenosyl-L-methionine:caffeoyl-CoA 3-O-methyltransferase
R01943  caffeate:CoA ligase (AMP-forming); 3,4-dihydroxy-trans-cinnamate:CoA ligase (AMP-forming)
R01945  caffeoyl-CoA:quinate O-(3,4-dihydroxycinnamoyl)transferase
R02193  coniferyl aldehyde:NADP+ oxidoreductase (CoA-feruloylating)
R02194  ferulate:CoA ligase (AMP-forming)
R02220  sinapoyl aldehyde:NADP+ oxidoreductase (CoA-sinapoylating)
R02221  sinapate:CoA ligase (AMP-forming)
R02253  trans-cinnamate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (4-hydroxylating)
R02255  trans-cinnamate:CoA ligase (AMP-forming)
R02379  S-adenosyl-L-methionine:3,4-dihydroxy-trans-cinnamate 3-O-methyltransferase
R02380  UDPglucose:sinapate D-glucosyltransferase
R02381  sinapoylcholine sinapohydrolase
R02416  4-coumaroyl-CoA:shikimate O-(hydroxycinnamoyl)transferase
R02506  cinnamaldehyde:NADP+ oxidoreductase (CoA-cinnamoylating)
R02593  coniferyl alcohol:NADP+ oxidoreductase
R02594  UDPglucose:coniferyl-alcohol 4'-beta-D-glucosyltransferase
R02595  coniferin beta-D-glucosidase
R02596  donor:hydrogen-peroxide oxidoreductase
R02952  phenylacrylic acid decarboxylase
R03075  1-O-(4-hydroxy-3,5-dimethoxycinnamoyl)-beta-D-glucose:choline 1-O-(4-hydroxy-3,5-dimethoxycinnamoyl)transferase
R03323  1-O-sinapoyl-beta-D-glucose:(S)-malate O-sinapoyltransferase
R03365  3,4-dihydroxy-trans-cinnamate:oxygen 3,4-oxidoreductase (decyclizing)
R03366  S-adenosyl-L-methionine:3,4-dihydroxy-trans-cinnamate 3-O-methyltransferase
R03367  
R03604  syringin beta-D-glucosidase
R03605  UDPglucose:coniferyl-alcohol 4'-beta-D-glucosyltransferase
R03918  sinapyl alcohol:NADP+ oxidoreductase
R03919  donor:hydrogen-peroxide oxidoreductase
R04005  UDPglucose:coniferyl-alcohol 4'-beta-D-glucosyltransferase
R04006  4-hydroxycinnamyl alcohol 4-D-glucoside beta-D-glucosidase
R04007  donor:hydrogen-peroxide oxidoreductase
R04342  trans-5-O-(4-coumaroyl)-D-quinate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R05700  coniferyl aldehyde:NAD oxidoreductase
R05701  coniferyl aldehyde:NADP oxidoreductase
R06569  cinnamaldehyde:NADP+ oxidoreductase (CoA-cinnamoylating)
R06570  cinnamyl-alcohol:NADP+ oxidoreductase
R06571  cinnamyl-alcohol:NADP+ oxidoreductase
R06572  
R06573  
R06574  caffeic aldehyde:3,4-dihydroxy-trans-cinnamate 3-O-methyltransferase
R06575  S-adenosyl-L-methionine:3,4-dihydroxy-trans-cinnamate 3-O-methyltransferase
R06576  S-adenosyl-L-methionine:3,4-dihydroxy-trans-cinnamate 3-O-methyltransferase
R06577  S-adenosyl-L-methionine:3,4-dihydroxy-trans-cinnamate 3-O-methyltransferase
R06578  S-adenosyl-L-methionine:caffeoyl-CoA 3-O-methyltransferase
R06579  
R06580  
R06582  trans-5-O-(4-coumaroyl)-D-shikimate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R06583  4-coumarate:CoA ligase (AMP-forming)
R06584  
R07240  S-adenosyl-L-methionine:isoeugenol O-methyltransferase
R07432  p-coumaroyl-CoA:quinate hydroxycinnamoyltransferase
R07433  5-O-caffeoylshikimic acid:shikimate hydroxycinnamoyltransferase
R07436  p-coumaroyl-CoA:caffeoyl-CoA 3-hydroxylase
R07437  4-coumaryl alcohol:NADP+ oxidoreductase
R07440  
R07441  sinapoyl aldehyde:NAD oxidoreductase
R07442  sinapoyl aldehyde:NADP oxidoreductase
R07443  donor:hydrogen-peroxide oxidoreductase
R07826  p-coumarate 3-hydroxylase
R08815  cinnamoyl-CoA,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (4-hydroxylating)
R08983  
R08984  
R08985  
R08986  
R08987  
R09931  eugenol:NADP+ oxidoreductase (coniferyl acetate reducing)
R10248  eugenol:NADP+ oxidoreductase (coniferyl ester reducing)
R10249  chavicol:NADP+ oxidoreductase
R10250  S-adenosyl-L-methionine:eugenol O-methyltransferase
R10251  S-adenosyl-L-methionine:chavicol O-methyltransferase
R10252  S-adenosyl-L-methionine:trans-anol O-methyltransferase
R10253  
R10254  
R10289  isochavicol:NADP+ oxidoreductase
R10701  
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
Related
pathway
rn00130  Ubiquinone and other terpenoid-quinone biosynthesis
rn00400  Phenylalanine, tyrosine and tryptophan biosynthesis
rn00941  Flavonoid biosynthesis
rn00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
KO pathway
ko00940   

DBGET integrated database retrieval system