KEGG   PATHWAY: apan00940
Entry
apan00940                   Pathway                                
Name
Phenylpropanoid biosynthesis - Andrographis paniculata
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
apan00940  Phenylpropanoid biosynthesis
apan00940

Module
apan_M00039  Monolignol biosynthesis, phenylalanine/tyrosine => monolignol [PATH:apan00940]
apan_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:apan00940]
Other DBs
GO: 0009699
Organism
Andrographis paniculata [GN:apan]
Gene
127250896  phenylalanine ammonia-lyase [KO:K10775] [EC:4.3.1.24]
127251261  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
127252199  phenylalanine ammonia-lyase-like [KO:K10775] [EC:4.3.1.24]
127251732  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
127253696  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
127255641  4-coumarate--CoA ligase-like 6 [KO:K01904] [EC:6.2.1.12]
127245898  4-coumarate--CoA ligase 2-like [KO:K01904] [EC:6.2.1.12]
127239472  probable CoA ligase CCL7 [KO:K01904] [EC:6.2.1.12]
127239775  4-coumarate--CoA ligase 2-like [KO:K01904] [EC:6.2.1.12]
127262980  4-coumarate--CoA ligase 1-like [KO:K01904] [EC:6.2.1.12]
127241060  4-coumarate--CoA ligase-like 9 [KO:K01904] [EC:6.2.1.12]
127241617  probable CoA ligase CCL7 isoform X1 [KO:K01904] [EC:6.2.1.12]
127242157  4-coumarate--CoA ligase-like 1 [KO:K01904] [EC:6.2.1.12]
127253818  probable CoA ligase CCL7 [KO:K01904] [EC:6.2.1.12]
127265255  4-coumarate--CoA ligase 1-like [KO:K01904] [EC:6.2.1.12]
127265283  4-coumarate--CoA ligase CCL1-like [KO:K01904] [EC:6.2.1.12]
127243258  4-coumarate--CoA ligase 2-like [KO:K01904] [EC:6.2.1.12]
127257730  acyltransferase GLAUCE-like [KO:K13065] [EC:2.3.1.133]
127259943  agmatine coumaroyltransferase-2-like [KO:K13065] [EC:2.3.1.133]
127261033  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
127239799  rosmarinate synthase-like [KO:K13065] [EC:2.3.1.133]
127239807  rosmarinate synthase-like [KO:K13065] [EC:2.3.1.133]
127239814  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
127240514  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
127240521  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
127262972  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
127241347  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
127241722  stemmadenine O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
127252947  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
127263580  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
127263581  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
127252996  acyltransferase GLAUCE-like [KO:K13065] [EC:2.3.1.133]
127263929  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
127264914  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
127243704  acyltransferase GLAUCE [KO:K13065] [EC:2.3.1.133]
127265536  acyltransferase GLAUCE-like [KO:K13065] [EC:2.3.1.133]
127256589  cytochrome P450 98A3-like [KO:K09754] [EC:1.14.14.96]
127260999  cytochrome P450 98A2-like [KO:K09754] [EC:1.14.14.96]
127254959  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
127261900  caffeoylshikimate esterase [KO:K18368] [EC:3.1.1.-]
127251820  caffeoylshikimate esterase-like isoform X1 [KO:K18368] [EC:3.1.1.-]
127263594  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
127242257  caffeoylshikimate esterase isoform X1 [KO:K18368] [EC:3.1.1.-]
127242808  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
127265067  caffeoylshikimate esterase-like [KO:K18368] [EC:3.1.1.-]
127255898  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
127248598  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
127260989  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
127261965  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
127251696  caffeoyl-CoA O-methyltransferase 5 [KO:K00588] [EC:2.1.1.104]
127243462  cinnamoyl-CoA reductase 1 [KO:K09753] [EC:1.2.1.44]
127266381  aldehyde dehydrogenase family 2 member C4-like [KO:K12355] [EC:1.2.1.68]
127248359  aldehyde dehydrogenase family 2 member C4-like [KO:K12355] [EC:1.2.1.68]
127251968  aldehyde dehydrogenase 1-like isoform X1 [KO:K12355] [EC:1.2.1.68]
127258627  cytochrome P450 84A1 [KO:K09755] [EC:1.14.-.-]
127250079  cytochrome P450 84A1-like [KO:K09755] [EC:1.14.-.-]
127250080  cytochrome P450 84A1-like [KO:K09755] [EC:1.14.-.-]
127252409  cytochrome P450 84A1-like [KO:K09755] [EC:1.14.-.-]
127256425  caffeic acid 3-O-methyltransferase 2 [KO:K13066] [EC:2.1.1.68 2.1.1.4]
127246917  caffeic acid 3-O-methyltransferase-like [KO:K13066] [EC:2.1.1.68 2.1.1.4]
127256070  cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
127256928  probable cinnamyl alcohol dehydrogenase 6 [KO:K00083] [EC:1.1.1.195]
127256929  probable cinnamyl alcohol dehydrogenase 6 isoform X1 [KO:K00083] [EC:1.1.1.195]
127256930  probable cinnamyl alcohol dehydrogenase 6 [KO:K00083] [EC:1.1.1.195]
127240388  probable cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
127243437  probable cinnamyl alcohol dehydrogenase 1 [KO:K00083] [EC:1.1.1.195]
127247969  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
127239844  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
127254873  berberine bridge enzyme-like 15 [KO:K22395] [EC:1.1.1.195]
127247481  1-Cys peroxiredoxin PER1 [KO:K11188] [EC:1.11.1.7 1.11.1.27 3.1.1.-]
127243893  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
127243898  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
127266044  peroxidase 27-like [KO:K00430] [EC:1.11.1.7]
127255787  peroxidase 46-like [KO:K00430] [EC:1.11.1.7]
127256366  peroxidase P7-like [KO:K00430] [EC:1.11.1.7]
127245507  peroxidase 11 [KO:K00430] [EC:1.11.1.7]
127245789  peroxidase 66 [KO:K00430] [EC:1.11.1.7]
127256494  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
127256596  peroxidase 57-like [KO:K00430] [EC:1.11.1.7]
127256679  peroxidase 16-like [KO:K00430] [EC:1.11.1.7]
127246456  peroxidase 43 [KO:K00430] [EC:1.11.1.7]
127246689  peroxidase 12 [KO:K00430] [EC:1.11.1.7]
127257372  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
127257861  peroxidase 47 [KO:K00430] [EC:1.11.1.7]
127247138  peroxidase 56-like [KO:K00430] [EC:1.11.1.7]
127247139  peroxidase 27-like [KO:K00430] [EC:1.11.1.7]
127257920  peroxidase 10-like [KO:K00430] [EC:1.11.1.7]
127258296  peroxidase 73-like [KO:K00430] [EC:1.11.1.7]
127247491  peroxidase 42 [KO:K00430] [EC:1.11.1.7]
127247654  peroxidase 19-like [KO:K00430] [EC:1.11.1.7]
127247742  peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
127247743  peroxidase 3-like [KO:K00430] [EC:1.11.1.7]
127247892  peroxidase 7-like [KO:K00430] [EC:1.11.1.7]
127247971  peroxidase 5-like [KO:K00430] [EC:1.11.1.7]
127258386  peroxidase 31 [KO:K00430] [EC:1.11.1.7]
127258568  peroxidase 72 [KO:K00430] [EC:1.11.1.7]
127248294  probable peroxidase 26 [KO:K00430] [EC:1.11.1.7]
127249244  peroxidase 24 [KO:K00430] [EC:1.11.1.7]
127260239  peroxidase 17-like [KO:K00430] [EC:1.11.1.7]
127261010  lignin-forming anionic peroxidase-like [KO:K00430] [EC:1.11.1.7]
127239332  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
127250169  peroxidase 40-like [KO:K00430] [EC:1.11.1.7]
127261756  peroxidase 6 [KO:K00430] [EC:1.11.1.7]
127239642  peroxidase 64 [KO:K00430] [EC:1.11.1.7]
127251003  cationic peroxidase 1-like [KO:K00430] [EC:1.11.1.7]
127251004  peroxidase 21 [KO:K00430] [EC:1.11.1.7]
127262363  peroxidase 43 [KO:K00430] [EC:1.11.1.7]
127262481  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
127252413  peroxidase 10-like isoform X1 [KO:K00430] [EC:1.11.1.7]
127252533  lignin-forming anionic peroxidase-like [KO:K00430] [EC:1.11.1.7]
127263465  peroxidase 25-like [KO:K00430] [EC:1.11.1.7]
127263574  peroxidase 25-like [KO:K00430] [EC:1.11.1.7]
127242125  peroxidase 55 [KO:K00430] [EC:1.11.1.7]
127242212  peroxidase 17 [KO:K00430] [EC:1.11.1.7]
127253166  peroxidase N1-like [KO:K00430] [EC:1.11.1.7]
127253483  peroxidase 60 [KO:K00430] [EC:1.11.1.7]
127253589  peroxidase 4 [KO:K00430] [EC:1.11.1.7]
127264327  peroxidase 9-like [KO:K00430] [EC:1.11.1.7]
127264355  peroxidase 64-like [KO:K00430] [EC:1.11.1.7]
127254132  putative Peroxidase 48 [KO:K00430] [EC:1.11.1.7]
127254133  putative Peroxidase 48 [KO:K00430] [EC:1.11.1.7]
127254715  peroxidase 7 [KO:K00430] [EC:1.11.1.7]
127254801  putative Peroxidase 48 [KO:K00430] [EC:1.11.1.7]
127265597  peroxidase 18-like isoform X1 [KO:K00430] [EC:1.11.1.7]
127240681  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
apan00130  Ubiquinone and other terpenoid-quinone biosynthesis
apan00400  Phenylalanine, tyrosine and tryptophan biosynthesis
apan00941  Flavonoid biosynthesis
apan00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
KO pathway
ko00940   
LinkDB

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