KEGG   PATHWAY: rn00945
Entry
rn00945                     Pathway                                

Name
Stilbenoid, diarylheptanoid and gingerol biosynthesis
Description
Stilbenoids are a group of phenolic compounds, biosynthetically interrelated through their common origin from a C6-C2-C6 intermediate, such as resveratol found in grapes. Stilbenoids can also exist as glycosides (e.g., piceid). Combretastatins are potentially useful stilbenoid natural products with known antitumor activity. Diarylheptanoid is a compound group having phenyl rings at 1,7 positions of n-heptane (C6-C7-C6), such as curcumin found in the ginger family. [6]-Gingerol is a major active component of ginger and has diverse pharmacologic effects.
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
rn00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
rn00945

Reaction
R01614  Malonyl-CoA:4-coumaroyl-CoA malonyltransferase (cyclizing)
R01942  S-Adenosyl-L-methionine:caffeoyl-CoA 3-O-methyltransferase
R01945  Caffeoyl-CoA:quinate O-(3,4-dihydroxycinnamoyl)transferase
R02416  4-Coumaroyl-CoA:shikimate O-(hydroxycinnamoyl)transferase
R02505  Malonyl-CoA:cinnamoyl-CoA malonyltransferase (cyclizing)
R04257   
R04342  trans-5-O-(4-coumaroyl)-D-quinate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R06582  trans-5-O-(4-coumaroyl)-D-shikimate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R07432  p-coumaroyl-CoA:quinate hydroxycinnamoyltransferase
R07433  5-O-caffeoylshikimic acid:shikimate hydroxycinnamoyltransferase
R07436  p-coumaroyl-CoA:caffeoyl-CoA 3-hydroxylase
R08796   
R08797   
R08798   
R08799   
R08800   
R08801   
R08802   
R08803  S-adenosyl-L-methionine:1-(3,4-dihydroxyphenyl)-1-decene-3,5-dione O-methyltransferase
R08804  S-adenosyl-L-methionine:1-(3,4-Dihydroxyphenyl)-5-hydroxy-3-decanone O-methyltransferase
R08805  p-coumaroyl-CoA:malonyl-CoA C-coumaroyltransferase (decarboxylating)
R08806  feruloyl-CoA:malonyl-CoA C-feruloyltransferase (decarboxylating)
R08807  p-coumaroyl-CoA:p-coumaroyl-diketide-CoA C-coumaroyltransferase (thioester-hydrolysing and decarboxylating)
R08808  feruloyl-CoA:p-Coumaroyl-diketide-CoA C-feruloyltransferase (thioester-hydrolysing and decarboxylating)
R08809  p-coumaroyl-CoA:feruloyl-diketide-CoA C-coumaroyltransferase (thioester-hydrolysing and decarboxylating)
R08810  feruloyl-CoA:feruloylacetyl-CoA feruloyltransferase (curcumin-forming)
R08811   
R08812   
R08813  UDP-glucose:curcumin glucosyltransferase
R08814  UDP-glucose:curcumin-monoglucoside glucosyltransferase
R08815  cinnamoyl-CoA,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (4-hydroxylating)
R09872  S-adenosyl-L-methionine:trans-resveratrol 3,5-O-dimethyltransferase
R10233  4-coumaroyl-CoA:malonyl-CoA 4-coumaryltransferase (bisdemethoxycurcumin-forming)
Compound
C00223  p-Coumaroyl-CoA
C00323  Caffeoyl-CoA
C00406  Feruloyl-CoA
C00540  Cinnamoyl-CoA
C00852  Chlorogenate
C01745  Pinosylvin
C02947  4-Coumaroylshikimate
C03582  Resveratrol
C05901  Piceatannol
C10287  Pterostilbene
C10434  5-O-Caffeoylshikimic acid
C10443  Curcumin
C10462  [6]-Gingerol
C12208  p-Coumaroyl quinic acid
C17740  p-Coumaroyl-diketide-CoA
C17741  Feruloyl-diketide-CoA
C17742  Demethoxycurcumin
C17743  Bisdemethoxycurcumin
C17744  1-(4-Hydroxyphenyl)-1-decene-3,5-dione
C17745  1-(3,4-Dihydroxyphenyl)-1-decene-3,5-dione
C17746  1-Dehydro-[6]-gingerdione
C17747  5-Hydroxy-1-(4-hydroxyphenyl)-3-decanone
C17748  1-(3,4-Dihydroxyphenyl)-5-hydroxy-3-decanone
C17749  Curcumin monoglucoside
C17750  Curcumin diglucoside
Reference
  Authors
Katsuyama Y, Kita T, Funa N, Horinouchi S
  Title
Curcuminoid biosynthesis by two type III polyketide synthases in the herb Curcuma longa.
  Journal
J Biol Chem 284:11160-70 (2009)
DOI:10.1074/jbc.M900070200
Reference
  Authors
Ramirez-Ahumada Mdel C, Timmermann BN, Gang DR
  Title
Biosynthesis of curcuminoids and gingerols in turmeric (Curcuma longa) and ginger (Zingiber officinale): identification of curcuminoid synthase and hydroxycinnamoyl-CoA thioesterases.
  Journal
Phytochemistry 67:2017-29 (2006)
DOI:10.1016/j.phytochem.2006.06.028
Reference
  Authors
Masada S, Terasaka K, Mizukami H
  Title
A single amino acid in the PSPG-box plays an important role in the catalytic function of CaUGT2 (Curcumin glucosyltransferase), a Group D Family 1 glucosyltransferase from Catharanthus roseus.
  Journal
FEBS Lett 581:2605-10 (2007)
DOI:10.1016/j.febslet.2007.05.002
Related
pathway
rn00940  Phenylpropanoid biosynthesis
KO pathway
ko00945   

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