KEGG   PATHWAY: ccav00940
Entry
ccav00940                   Pathway                                
Name
Phenylpropanoid biosynthesis - Cynara cardunculus var. scolymus (artichoke)
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
ccav00940  Phenylpropanoid biosynthesis
ccav00940

Module
ccav_M00039  Monolignol biosynthesis, phenylalanine/tyrosine => monolignol [PATH:ccav00940]
ccav_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:ccav00940]
Other DBs
GO: 0009699
Organism
Cynara cardunculus var. scolymus (artichoke) [GN:ccav]
Gene
112508463  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
112511516  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
112521561  phenylalanine ammonia-lyase [KO:K10775] [EC:4.3.1.24]
112521371  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
112512533  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
112506479  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
112517960  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
112508847  4-coumarate--CoA ligase 1-like isoform X1 [KO:K01904] [EC:6.2.1.12]
112502163  4-coumarate--CoA ligase 2 isoform X1 [KO:K01904] [EC:6.2.1.12]
112522000  4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]
112522231  4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]
112529868  4-coumarate--CoA ligase-like 6 [KO:K01904] [EC:6.2.1.12]
112514294  4-coumarate--CoA ligase 2-like [KO:K01904] [EC:6.2.1.12]
112519731  4-coumarate--CoA ligase-like 7 [KO:K01904] [EC:6.2.1.12]
112525891  4-coumarate--CoA ligase-like 1 [KO:K01904] [EC:6.2.1.12]
112508768  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
112524489  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
112510222  omega-hydroxypalmitate O-feruloyl transferase [KO:K13065] [EC:2.3.1.133]
112509295  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
112501602  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
112504064  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
112505863  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
112505864  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
112506624  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
112514859  salutaridinol 7-O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
112516970  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
112517241  pelargonidin 3-O-(6-caffeoylglucoside) 5-O-(6-O-malonylglucoside) 4'''-malonyltransferase-like [KO:K13065] [EC:2.3.1.133]
112529806  pelargonidin 3-O-(6-caffeoylglucoside) 5-O-(6-O-malonylglucoside) 4'''-malonyltransferase-like [KO:K13065] [EC:2.3.1.133]
112514594  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
112504027  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
112512472  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
112506836  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
112509846  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
112516955  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
112511346  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
112517450  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
112525168  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
112500202  caffeoyl-CoA O-methyltransferase isoform X1 [KO:K00588] [EC:2.1.1.104]
112500219  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
112512135  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
112516496  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
112512166  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
112510259  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
112509602  cinnamoyl-CoA reductase 1-like [KO:K09753] [EC:1.2.1.44]
112506760  aldehyde dehydrogenase family 2 member C4-like isoform X1 [KO:K12355] [EC:1.2.1.68]
112516784  aldehyde dehydrogenase family 2 member C4-like [KO:K12355] [EC:1.2.1.68]
112516420  aldehyde dehydrogenase family 2 member C4-like isoform X1 [KO:K12355] [EC:1.2.1.68]
112516421  aldehyde dehydrogenase family 2 member C4-like [KO:K12355] [EC:1.2.1.68]
112515563  cytochrome P450 84A1-like [KO:K09755] [EC:1.14.-.-]
112513261  cytochrome P450 84A1-like [KO:K09755] [EC:1.14.-.-]
112502160  caffeic acid 3-O-methyltransferase [KO:K13066] [EC:2.1.1.68 2.1.1.4]
112517955  caffeic acid 3-O-methyltransferase-like [KO:K13066] [EC:2.1.1.68 2.1.1.4]
112518480  caffeic acid 3-O-methyltransferase-like [KO:K13066] [EC:2.1.1.68 2.1.1.4]
112524515  caffeic acid 3-O-methyltransferase [KO:K13066] [EC:2.1.1.68 2.1.1.4]
112507325  probable cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
112511600  probable cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
112500993  probable cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
112509274  probable cinnamyl alcohol dehydrogenase 6 [KO:K00083] [EC:1.1.1.195]
112515118  probable cinnamyl alcohol dehydrogenase [KO:K00083] [EC:1.1.1.195]
112500777  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
112500053  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
112516727  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
112521913  1-Cys peroxiredoxin [KO:K11188] [EC:1.11.1.7 1.11.1.27 3.1.1.-]
112507108  peroxidase 10-like [KO:K00430] [EC:1.11.1.7]
112510204  peroxidase 64-like [KO:K00430] [EC:1.11.1.7]
112509843  peroxidase 64-like [KO:K00430] [EC:1.11.1.7]
112509877  peroxidase 64-like [KO:K00430] [EC:1.11.1.7]
112508833  peroxidase 9-like [KO:K00430] [EC:1.11.1.7]
112502735  peroxidase 7 [KO:K00430] [EC:1.11.1.7]
112502409  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
112503338  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
112503818  cationic peroxidase 1-like isoform X1 [KO:K00430] [EC:1.11.1.7]
112505107  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
112505408  lignin-forming anionic peroxidase-like [KO:K00430] [EC:1.11.1.7]
112506185  putative Peroxidase 48 [KO:K00430] [EC:1.11.1.7]
112508036  peroxidase 43-like [KO:K00430] [EC:1.11.1.7]
112512651  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
112527448  peroxidase 3-like [KO:K00430] [EC:1.11.1.7]
112512522  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
112520976  peroxidase 60 [KO:K00430] [EC:1.11.1.7]
112512723  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
112512604  peroxidase 10-like [KO:K00430] [EC:1.11.1.7]
112524099  peroxidase 31-like [KO:K00430] [EC:1.11.1.7]
112512851  peroxidase 7-like [KO:K00430] [EC:1.11.1.7]
112519246  peroxidase N-like [KO:K00430] [EC:1.11.1.7]
112524359  peroxidase 11 [KO:K00430] [EC:1.11.1.7]
112519167  peroxidase 19 [KO:K00430] [EC:1.11.1.7]
112529558  peroxidase 20-like [KO:K00430] [EC:1.11.1.7]
112522938  lignin-forming anionic peroxidase-like [KO:K00430] [EC:1.11.1.7]
112522939  lignin-forming anionic peroxidase-like [KO:K00430] [EC:1.11.1.7]
112522940  lignin-forming anionic peroxidase-like [KO:K00430] [EC:1.11.1.7]
112525946  peroxidase 27-like [KO:K00430] [EC:1.11.1.7]
112512010  peroxidase 51-like [KO:K00430] [EC:1.11.1.7]
112512046  peroxidase N-like [KO:K00430] [EC:1.11.1.7]
112516240  peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
112516257  cationic peroxidase 2-like [KO:K00430] [EC:1.11.1.7]
112516263  peroxidase 43-like [KO:K00430] [EC:1.11.1.7]
112516267  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
112518378  peroxidase P7-like [KO:K00430] [EC:1.11.1.7]
112522515  basic peroxidase-like [KO:K00430] [EC:1.11.1.7]
112511183  peroxidase 12-like [KO:K00430] [EC:1.11.1.7]
112513213  peroxidase 4-like [KO:K00430] [EC:1.11.1.7]
112516428  peroxidase N1-like isoform X1 [KO:K00430] [EC:1.11.1.7]
112516429  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
112516449  peroxidase 25 [KO:K00430] [EC:1.11.1.7]
112516458  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
112519579  peroxidase 27-like [KO:K00430] [EC:1.11.1.7]
112528717  probable peroxidase 26 [KO:K00430] [EC:1.11.1.7]
112522681  basic peroxidase-like [KO:K00430] [EC:1.11.1.7]
112518253  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
112513129  peroxidase 31-like [KO:K00430] [EC:1.11.1.7]
112514258  peroxidase 41-like [KO:K00430] [EC:1.11.1.7]
112515271  peroxidase 72-like [KO:K00430] [EC:1.11.1.7]
112512314  peroxidase 4-like [KO:K00430] [EC:1.11.1.7]
112515437  peroxidase 72-like [KO:K00430] [EC:1.11.1.7]
112516518  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
112516536  peroxidase N1-like isoform X1 [KO:K00430] [EC:1.11.1.7]
112512393  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
112512432  peroxidase 72 [KO:K00430] [EC:1.11.1.7]
112514518  peroxidase 9-like [KO:K00430] [EC:1.11.1.7]
112516596  peroxidase 45-like [KO:K00430] [EC:1.11.1.7]
112516640  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
112516641  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
112516642  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
112521846  peroxidase 47 [KO:K00430] [EC:1.11.1.7]
112516190  peroxidase 16-like [KO:K00430] [EC:1.11.1.7]
112519367  peroxidase 27-like [KO:K00430] [EC:1.11.1.7]
112512374  peroxidase 66 [KO:K00430] [EC:1.11.1.7]
112524505  peroxidase 17 [KO:K00430] [EC:1.11.1.7]
112524521  peroxidase P7 [KO:K00430] [EC:1.11.1.7]
112526607  peroxidase 42 [KO:K00430] [EC:1.11.1.7]
112513143  peroxidase 55 [KO:K00430] [EC:1.11.1.7]
112514300  peroxidase 12-like [KO:K00430] [EC:1.11.1.7]
112515342  peroxidase 64-like [KO:K00430] [EC:1.11.1.7]
112525664  peroxidase 64-like [KO:K00430] [EC:1.11.1.7]
112512471  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
112512481  peroxidase 64-like [KO:K00430] [EC:1.11.1.7]
112514609  peroxidase 12-like [KO:K00430] [EC:1.11.1.7]
112501980  anthocyanidin 3-O-glucosyltransferase 5-like [KO:K12356] [EC:2.4.1.111]
112516999  anthocyanidin 3-O-glucosyltransferase 5-like [KO:K12356] [EC:2.4.1.111]
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
ccav00130  Ubiquinone and other terpenoid-quinone biosynthesis
ccav00400  Phenylalanine, tyrosine and tryptophan biosynthesis
ccav00941  Flavonoid biosynthesis
ccav00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
KO pathway
ko00940   
LinkDB

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