ENTRY       zma00945                    Pathway
NAME        Stilbenoid, diarylheptanoid and gingerol biosynthesis - Zea mays (maize)
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 zma00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
ORGANISM    Zea mays (maize) [GN:zma]
GENE        100272756  putative cytochrome P450 superfamily protein [KO:K00487] [EC:1.14.14.91]
            100284998  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
            100272801  putative cytochrome P450 superfamily protein [KO:K00487] [EC:1.14.14.91]
            103636555  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
            109940988  bisdemethoxycurcumin synthase-like [KO:K17212] [EC:2.3.1.211]
            100272924  uncharacterized protein LOC100272924 [KO:K17212] [EC:2.3.1.211]
            103654409  bisdemethoxycurcumin synthase precursor [KO:K17212] [EC:2.3.1.211]
            103626945  bisdemethoxycurcumin synthase [KO:K17212] [EC:2.3.1.211]
            103654408  bisdemethoxycurcumin synthase [KO:K17212] [EC:2.3.1.211]
            103650038  bisdemethoxycurcumin synthase [KO:K17212] [EC:2.3.1.211]
            103650033  bisdemethoxycurcumin synthase [KO:K17212] [EC:2.3.1.211]
            103650032  bisdemethoxycurcumin synthase [KO:K17212] [EC:2.3.1.211]
            118476652  bisdemethoxycurcumin synthase-like [KO:K17212] [EC:2.3.1.211]
            100274269  uncharacterized protein LOC100274269 [KO:K13065] [EC:2.3.1.133]
            100279986  uncharacterized protein LOC100279986 [KO:K13065] [EC:2.3.1.133]
            100279982  Spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100281073  anthranilate N-benzoyltransferase protein 1 [KO:K13065] [EC:2.3.1.133]
            100284063  uncharacterized protein LOC100284063 [KO:K13065] [EC:2.3.1.133]
            100284770  uncharacterized protein LOC100284770 [KO:K13065] [EC:2.3.1.133]
            100304329  uncharacterized protein LOC100304329 [KO:K13065] [EC:2.3.1.133]
            100382972  uncharacterized protein LOC100382972 [KO:K13065] [EC:2.3.1.133]
            103649821  putrescine hydroxycinnamoyltransferase 1 [KO:K13065] [EC:2.3.1.133]
            103649769  putrescine hydroxycinnamoyltransferase 1 [KO:K13065] [EC:2.3.1.133]
            100501555  uncharacterized protein LOC100501555 [KO:K13065] [EC:2.3.1.133]
            103649816  putrescine hydroxycinnamoyltransferase 1 isoform X1 [KO:K13065] [EC:2.3.1.133]
            109942262  hydroxycinnamoyltransferase 4 [KO:K13065] [EC:2.3.1.133]
            109942297  hydroxycinnamoyltransferase 4 [KO:K13065] [EC:2.3.1.133]
            100191539  putative cytochrome P450 superfamily protein [KO:K09754] [EC:1.14.14.96]
            100274274  putative cytochrome P450 superfamily protein [KO:K09754] [EC:1.14.14.96]
            107282093  uncharacterized protein LOC107282093 [KO:K00588] [EC:2.1.1.104]
            100273683  caffeoyl-CoA O-methyltransferase 2 [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 zma00940  Phenylpropanoid biosynthesis
KO_PATHWAY  ko00945
///
