ENTRY       gmx00945                    Pathway
NAME        Stilbenoid, diarylheptanoid and gingerol biosynthesis - Glycine max (soybean)
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 gmx00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
ORGANISM    Glycine max (soybean) [GN:gmx]
GENE        100499623  C4H; trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
            100818985  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
            100812188  C4H1; cinnamate 4-hydroxylase [KO:K00487] [EC:1.14.14.91]
            100806561  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            100820075  shikimate O-hydroxycinnamoyltransferase isoform X3 [KO:K13065] [EC:2.3.1.133]
            100499712  omega-hydroxypalmitate O-feruloyl transferase [KO:K13065] [EC:2.3.1.133]
            100777157  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100777680  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100779280  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100779814  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100792323  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
            100814459  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100804886  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100805962  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100801695  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
            100801923  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            100787038  spermidine hydroxycinnamoyl transferase isoform X2 [KO:K13065] [EC:2.3.1.133]
            100802888  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100803418  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100778626  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100780971  omega-hydroxypalmitate O-feruloyl transferase [KO:K13065] [EC:2.3.1.133]
            100819383  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100775549  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100805510  fatty alcohol:caffeoyl-CoA acyltransferase [KO:K13065] [EC:2.3.1.133]
            100777007  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100777532  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100779652  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100305576  omega-hydroxypalmitate O-feruloyl transferase [KO:K13065] [EC:2.3.1.133]
            100788434  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100789491  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            102668997  vinorine synthase [KO:K13065] [EC:2.3.1.133]
            100802808  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100778266  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            102663900  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            102670206  stemmadenine O-acetyltransferase isoform X1 [KO:K13065] [EC:2.3.1.133]
            100811080  cytochrome P450 98A2 [KO:K09754] [EC:1.14.14.96]
            606506  CYP98A2; cytochrome P450 98A2 [KO:K09754] [EC:1.14.14.96]
            100500657  putative caffeoyl-CoA 3-O-methyltransferase [KO:K00588] [EC:2.1.1.104]
            100779260  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
            100811247  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
            100780516  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
            100792717  OMT5; anthocyanin 3'-O-methyltransferase [KO:K00588] [EC:2.1.1.104]
            100800911  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
            100795229  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
            100813350  flavonoid 3',5'-methyltransferase isoform X2 [KO:K00588] [EC:2.1.1.104]
            100305498  SOMT-9; O-methyltransferase SOMT-9 isoform 1 [KO:K00588] [EC:2.1.1.104]
            100799303  S-adenosyl-L-methionine-dependent methyltransferases superfamily protein [KO:K00588] [EC:2.1.1.104]
            100795858  caffeoyl-CoA O-methyltransferase 5 [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 gmx00940  Phenylpropanoid biosynthesis
KO_PATHWAY  ko00945
///
