KEGG   PATHWAY: ppp00940
Entry
ppp00940                    Pathway                                
Name
Phenylpropanoid biosynthesis - Physcomitrium patens (spreading earthmoss)
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
ppp00940  Phenylpropanoid biosynthesis
ppp00940

Module
ppp_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:ppp00940]
Other DBs
GO: 0009699
Organism
Physcomitrium patens (spreading earthmoss) [GN:ppp]
Gene
112273833  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
112273834  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
112278877  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
112276937  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
112277636  phenylalanine ammonia-lyase class 1-like [KO:K10775] [EC:4.3.1.24]
112285521  phenylalanine ammonia-lyase class 1-like [KO:K10775] [EC:4.3.1.24]
112290398  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
112290843  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
112291346  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
112286715  phenylalanine ammonia-lyase class 1-like [KO:K10775] [EC:4.3.1.24]
112287672  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
112295966  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
112294398  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
112277388  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
112281483  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
112279424  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
112290352  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
112272825  4-coumarate--CoA ligase-like [KO:K01904] [EC:6.2.1.12]
112279854  4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]
112279622  4-coumarate--CoA ligase-like 1 [KO:K01904] [EC:6.2.1.12]
112273830  4-coumarate--CoA ligase-like [KO:K01904] [EC:6.2.1.12]
112274681  4-coumarate--CoA ligase-like [KO:K01904] [EC:6.2.1.12]
112295246  4-coumarate--CoA ligase-like [KO:K01904] [EC:6.2.1.12]
112286600  4-coumarate--CoA ligase-like 5 [KO:K01904] [EC:6.2.1.12]
112290518  4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]
112285944  4-coumarate--CoA ligase-like 1 [KO:K01904] [EC:6.2.1.12]
112274047  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
112275159  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
112275054  agmatine hydroxycinnamoyltransferase 1-like [KO:K13065] [EC:2.3.1.133]
112275357  agmatine hydroxycinnamoyltransferase 1-like [KO:K13065] [EC:2.3.1.133]
112278540  hydroxycinnamoyltransferase 1-like [KO:K13065] [EC:2.3.1.133]
112278247  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
112280237  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
112282400  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
112284629  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
112293457  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
112275074  cytochrome P450 98A3-like [KO:K09754] [EC:1.14.14.96]
112272719  caffeoylshikimate esterase-like isoform X1 [KO:K18368] [EC:3.1.1.-]
112284351  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
112275260  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
112276043  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
112284247  cinnamoyl-CoA reductase 1-like isoform X1 [KO:K09753] [EC:1.2.1.44]
112284670  cinnamoyl-CoA reductase 1-like [KO:K09753] [EC:1.2.1.44]
112288176  cinnamoyl-CoA reductase 1-like isoform X1 [KO:K09753] [EC:1.2.1.44]
112293893  cinnamoyl-CoA reductase 1-like [KO:K09753] [EC:1.2.1.44]
112289725  caffeic acid 3-O-methyltransferase-like isoform X1 [KO:K13066] [EC:2.1.1.68 2.1.1.4]
112288207  caffeic acid 3-O-methyltransferase-like isoform X1 [KO:K13066] [EC:2.1.1.68 2.1.1.4]
112275486  probable cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
112274798  probable 1-Cys peroxiredoxin [KO:K11188] [EC:1.11.1.7 1.11.1.27 3.1.1.-]
112287677  peroxiredoxin-6-like [KO:K11188] [EC:1.11.1.7 1.11.1.27 3.1.1.-]
112272846  peroxidase 21-like [KO:K00430] [EC:1.11.1.7]
112273326  peroxidase 29-like isoform X1 [KO:K00430] [EC:1.11.1.7]
112274794  cationic peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
112276077  peroxidase 29-like [KO:K00430] [EC:1.11.1.7]
112276330  peroxidase P7-like [KO:K00430] [EC:1.11.1.7]
112277786  peroxidase P7-like [KO:K00430] [EC:1.11.1.7]
112277663  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
112277664  peroxidase 71-like [KO:K00430] [EC:1.11.1.7]
112276690  cationic peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
112277702  peroxidase E5-like [KO:K00430] [EC:1.11.1.7]
112277719  peroxidase 64-like isoform X1 [KO:K00430] [EC:1.11.1.7]
112277729  peroxidase 64-like isoform X1 [KO:K00430] [EC:1.11.1.7]
112277751  peroxidase 71-like [KO:K00430] [EC:1.11.1.7]
112277762  peroxidase 64-like isoform X1 [KO:K00430] [EC:1.11.1.7]
112277763  peroxidase 64-like isoform X1 [KO:K00430] [EC:1.11.1.7]
112277764  peroxidase 64-like isoform X1 [KO:K00430] [EC:1.11.1.7]
112276679  cationic peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
112279619  peroxidase A2-like [KO:K00430] [EC:1.11.1.7]
112279620  peroxidase 57-like [KO:K00430] [EC:1.11.1.7]
112276527  peroxidase 29-like [KO:K00430] [EC:1.11.1.7]
112279744  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
112280849  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
112280888  peroxidase P7-like [KO:K00430] [EC:1.11.1.7]
112280638  peroxidase 27-like [KO:K00430] [EC:1.11.1.7]
112279657  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
112279353  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
112279707  peroxidase 71-like [KO:K00430] [EC:1.11.1.7]
112280862  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
112281233  peroxidase P7-like [KO:K00430] [EC:1.11.1.7]
112281067  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
112281919  peroxidase P7-like [KO:K00430] [EC:1.11.1.7]
112281405  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
112281425  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
112280037  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
112283945  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
112285503  peroxidase 71-like [KO:K00430] [EC:1.11.1.7]
112285504  peroxidase 71-like [KO:K00430] [EC:1.11.1.7]
112285738  peroxidase 29-like [KO:K00430] [EC:1.11.1.7]
112285339  peroxidase P7-like [KO:K00430] [EC:1.11.1.7]
112285549  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
112285389  peroxidase 57-like [KO:K00430] [EC:1.11.1.7]
112285948  peroxidase 29-like [KO:K00430] [EC:1.11.1.7]
112286261  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
112287252  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
112289371  peroxidase 57-like [KO:K00430] [EC:1.11.1.7]
112289414  peroxidase P7-like [KO:K00430] [EC:1.11.1.7]
112290278  peroxidase 3-like [KO:K00430] [EC:1.11.1.7]
112290333  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
112289218  peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
112289228  peroxidase 63-like isoform X1 [KO:K00430] [EC:1.11.1.7]
112292076  peroxidase 21-like isoform X1 [KO:K00430] [EC:1.11.1.7]
112292162  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
112293028  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
112294427  peroxidase A2-like isoform X1 [KO:K00430] [EC:1.11.1.7]
112295827  peroxidase 55-like [KO:K00430] [EC:1.11.1.7]
112277837  peroxidase 66-like [KO:K00430] [EC:1.11.1.7]
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
ppp00130  Ubiquinone and other terpenoid-quinone biosynthesis
ppp00400  Phenylalanine, tyrosine and tryptophan biosynthesis
ppp00941  Flavonoid biosynthesis
ppp00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
KO pathway
ko00940   
LinkDB

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