| Entry |
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| Name |
Stilbenoid, diarylheptanoid and gingerol biosynthesis
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| 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.
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| Class |
Metabolism; Biosynthesis of other secondary metabolites
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| Pathway map |
| Stilbenoid, diarylheptanoid and gingerol biosynthesis |
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| Reaction |
| Malonyl-CoA:4-coumaroyl-CoA malonyltransferase (cyclizing) | | S-Adenosyl-L-methionine:caffeoyl-CoA 3-O-methyltransferase | | Caffeoyl-CoA:quinate O-(3,4-dihydroxycinnamoyl)transferase | | 4-Coumaroyl-CoA:shikimate O-(hydroxycinnamoyl)transferase | | Malonyl-CoA:cinnamoyl-CoA malonyltransferase (cyclizing) | | | | trans-5-O-(4-coumaroyl)-D-quinate,NADPH:oxygen oxidoreductase (3'-hydorxylating) | | trans-5-O-(4-coumaroyl)-D-shikimate,NADPH:oxygen oxidoreductase (3'-hydorxylating) | | p-coumaroyl-CoA:quinate hydroxycinnamoyltransferase | | 5-O-caffeoylshikimic acid:shikimate hydroxycinnamoyltransferase | | p-coumaroyl-CoA:caffeoyl-CoA 3-hydroxylase | | | | | | | | | | | | | | | | S-adenosyl-L-methionine:1-(3,4-dihydroxyphenyl)-1-decene-3,5-dione O-methyltransferase | | S-adenosyl-L-methionine:1-(3,4-Dihydroxyphenyl)-5-hydroxy-3-decanone O-methyltransferase | | p-coumaroyl-CoA:malonyl-CoA C-coumaroyltransferase (decarboxylating) | | feruloyl-CoA:malonyl-CoA C-feruloyltransferase (decarboxylating) | | p-coumaroyl-CoA:p-coumaroyl-diketide-CoA C-coumaroyltransferase (thioester-hydrolysing and decarboxylating) | | feruloyl-CoA:p-Coumaroyl-diketide-CoA C-feruloyltransferase (thioester-hydrolysing and decarboxylating) | | p-coumaroyl-CoA:feruloyl-diketide-CoA C-coumaroyltransferase (thioester-hydrolysing and decarboxylating) | | feruloyl-CoA:feruloylacetyl-CoA feruloyltransferase (curcumin-forming) | | | | | | UDP-glucose:curcumin glucosyltransferase | | UDP-glucose:curcumin-monoglucoside glucosyltransferase | | trans-cinnamate,NADPH:oxygen oxidoreductase (4-hydroxylating) | | S-adenosyl-L-methionine:trans-resveratrol 3,5-O-dimethyltransferase |
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| Compound |
| p-Coumaroyl-CoA | | Caffeoyl-CoA | | Feruloyl-CoA | | Cinnamoyl-CoA | | Chlorogenate | | Pinosylvin | | 4-Coumaroylshikimate | | Resveratrol | | Piceatannol | | Pterostilbene | | 5-O-Caffeoylshikimic acid | | Curcumin | | [6]-Gingerol | | p-Coumaroyl quinic acid | | p-Coumaroyl-diketide-CoA | | Feruloyl-diketide-CoA | | Demethoxycurcumin | | Bisdemethoxycurcumin | | 1-(4-Hydroxyphenyl)-1-decene-3,5-dione | | 1-(3,4-Dihydroxyphenyl)-1-decene-3,5-dione | | 1-Dehydro-[6]-gingerdione | | 5-Hydroxy-1-(4-hydroxyphenyl)-3-decanone | | 1-(3,4-Dihydroxyphenyl)-5-hydroxy-3-decanone | | Curcumin monoglucoside | | Curcumin diglucoside |
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| Reference |
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| Authors |
Katsuyama Y, Kita T, Funa N, Horinouchi S |
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| Title |
Curcuminoid biosynthesis by two type III polyketide synthases in the herb Curcuma longa. |
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| Journal |
J Biol Chem 284:11160-70 (2009) |
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| Reference |
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| Authors |
Ramirez-Ahumada Mdel C, Timmermann BN, Gang DR |
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| Title |
Biosynthesis of curcuminoids and gingerols in turmeric (Curcuma longa) and ginger (Zingiber officinale): identification of curcuminoid synthase and hydroxycinnamoyl-CoA thioesterases. |
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| Journal |
Phytochemistry 67:2017-29 (2006) |
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| Reference |
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| Authors |
Masada S, Terasaka K, Mizukami H |
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| 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. |
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| Journal |
FEBS Lett 581:2605-10 (2007) |
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| KO pathway |
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