ENTRY       osa00945                    Pathway
NAME        Stilbenoid, diarylheptanoid and gingerol biosynthesis - Oryza sativa japonica (Japanese rice) (RefSeq)
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 osa00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
ORGANISM    Oryza sativa japonica (Japanese rice) (RefSeq) [GN:osa]
GENE        4338409  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
            4329324  cytochrome P450 CYP73A100 [KO:K00487] [EC:1.14.14.91]
            4329329  cytochrome P450 CYP73A100 [KO:K00487] [EC:1.14.14.91]
            9270590  LOW QUALITY PROTEIN: trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
            4342896  bisdemethoxycurcumin synthase [KO:K17212] [EC:2.3.1.211]
            107276120  bisdemethoxycurcumin synthase-like [KO:K17212] [EC:2.3.1.211]
            4338103  bisdemethoxycurcumin synthase-like [KO:K17212] [EC:2.3.1.211]
            4343313  chalcone synthase 1 [KO:K17212] [EC:2.3.1.211]
            4348146  bisdemethoxycurcumin synthase-like [KO:K17212] [EC:2.3.1.211]
            4348180  chalcone synthase 2 [KO:K17212] [EC:2.3.1.211]
            107278066  chalcone synthase 1-like [KO:K17212] [EC:2.3.1.211]
            4350633  bisdemethoxycurcumin synthase-like [KO:K17212] [EC:2.3.1.211]
            4343431  bisdemethoxycurcumin synthase-like [KO:K17212] [EC:2.3.1.211]
            4343430  bisdemethoxycurcumin synthase-like [KO:K17212] [EC:2.3.1.211]
            4343432  bisdemethoxycurcumin synthase-like [KO:K17212] [EC:2.3.1.211]
            4350635  bisdemethoxycurcumin synthase-like [KO:K17212] [EC:2.3.1.211]
            107276706  bisdemethoxycurcumin synthase-like [KO:K17212] [EC:2.3.1.211]
            4350634  bisdemethoxycurcumin synthase-like [KO:K17212] [EC:2.3.1.211]
            107276873  bisdemethoxycurcumin synthase-like [KO:K17212] [EC:2.3.1.211]
            4346205  shikimate O-hydroxycinnamoyltransferase isoform X1 [KO:K13065] [EC:2.3.1.133]
            4340333  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            4347092  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            4339188  cytochrome P450 98A1 [KO:K09754] [EC:1.14.14.96]
            4340240  caffeoyl-CoA O-methyltransferase 1 [KO:K00588] [EC:2.1.1.104]
            4347397  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
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   PMID:19258320
  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   PMID:16890967
  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   PMID:17509574
  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
REL_PATHWAY osa00940  Phenylpropanoid biosynthesis
KO_PATHWAY  ko00945
///
