KEGG PATHWAY: rn00940

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

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)

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

All links

Chemical reaction (101)   
   KEGG REACTION (80)   
   KEGG RCLASS (21)   
All databases (101)   

Download RDF

DBGET integrated database retrieval system