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Pathway Description
Stilbenoid, Diarylheptanoid, and Gingerol Biosynthesis
Arabidopsis thaliana
Metabolic Pathway
Stilbenoids are a family of phenylpropanoids which contain a 1,2-diphenylethylene moiety that exist in the plant kingdom and have a variety of biological functions (PMID: 23014926). Diarylheptanoids are another group of phenylpropanoids that are found in plants which have a 1,7-diphenylheptane skeleton (PMID: 21121274). Gingerols are a group of compounds containing a gingerol moiety, some of which are known to be useful for medication purposes (PMID: 26228533). In Arabidopsis, the stilbenoid, diarylheptanoid, and gingerol biosynthesis pathway takes place in the endoplasmic reticulum. This pathway involves coumaroyl-CoA sourced either directly from phenylpropanoid biosynthesis or derived from cinnamoyl-CoA in a reaction catalyzed by cinnamate-4-hydroxylase. Removal of a CoA group from coumaroyl-CoA and a reaction of coumaroyl-CoA with either shikimic acid or quinic acid produces 4-coumaroylshikimic acid or coumaroyl quinic acid. This is catalyzed by hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase. CYP98A3 enzyme catalyzes hydroxylation of the products to produce caffeoylshikimic acid or chlorogenic acid respectively. Further reaction of products with CoA, catalyzed again by hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase, produces caffeoyl-CoA. Caffeoyl-CoA is then reacted with S-adenosyl-L-methionine to produce feruloyl-CoA with catalyzation by caffeoyl-CoA O-methyltransferase. 1-dehydro-6-gingerdione and 6-gingerol may then be further derived from feruloyl-CoA.
References
Stilbenoid, Diarylheptanoid, and Gingerol Biosynthesis References
Schoch G, Goepfert S, Morant M, Hehn A, Meyer D, Ullmann P, Werck-Reichhart D: CYP98A3 from Arabidopsis thaliana is a 3'-hydroxylase of phenolic esters, a missing link in the phenylpropanoid pathway. J Biol Chem. 2001 Sep 28;276(39):36566-74. doi: 10.1074/jbc.M104047200. Epub 2001 Jun 27.
Pubmed: 11429408
Hoffmann L, Besseau S, Geoffroy P, Ritzenthaler C, Meyer D, Lapierre C, Pollet B, Legrand M: Silencing of hydroxycinnamoyl-coenzyme A shikimate/quinate hydroxycinnamoyltransferase affects phenylpropanoid biosynthesis. Plant Cell. 2004 Jun;16(6):1446-65. doi: 10.1105/tpc.020297. Epub 2004 May 25.
Pubmed: 15161961
Kai K, Mizutani M, Kawamura N, Yamamoto R, Tamai M, Yamaguchi H, Sakata K, Shimizu B: Scopoletin is biosynthesized via ortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabidopsis thaliana. Plant J. 2008 Sep;55(6):989-99. doi: 10.1111/j.1365-313X.2008.03568.x. Epub 2008 Jun 10.
Pubmed: 18547395
Riviere C, Pawlus AD, Merillon JM: Natural stilbenoids: distribution in the plant kingdom and chemotaxonomic interest in Vitaceae. Nat Prod Rep. 2012 Nov;29(11):1317-33. doi: 10.1039/c2np20049j.
Pubmed: 23014926
Lv H, She G: Naturally occurring diarylheptanoids. Nat Prod Commun. 2010 Oct;5(10):1687-708.
Pubmed: 21121274
Semwal RB, Semwal DK, Combrinck S, Viljoen AM: Gingerols and shogaols: Important nutraceutical principles from ginger. Phytochemistry. 2015 Sep;117:554-68. doi: 10.1016/j.phytochem.2015.07.012. Epub 2015 Jul 27.
Pubmed: 26228533
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