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Pathway Description
Metabolism and Physiological Effects of Vanillic Acid
Homo sapiens
Category:
Metabolite Pathway
Sub-Category:
Metabolic
Created: 2023-08-31
Last Updated: 2023-11-27
Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavouring and scent agent that produces a pleasant, creamy odour. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea, and vanilla-flavoured confectionary. Vanillic acid selectively and specifically inhibits 5'nucleotidase activity. Vanillic acid is a microbial metabolite found in Amycolatopsis, Delftia, and Pseudomonas. Vanillin is toxic to the cells and hence it is subject to catabolism caused by the oxidative activity of this protein. This is undesired from the production point of view of this important compound. The deletion mutant of this protein can be used in production of natural vanillin by microbial fermentation from ferulic acid at final concentrations and molar yields on an industrial scale. The enzyme vanillin dehydrogenase in Amycolatopsis species catalyzes NAD+-dependent oxidation of vanillin to vanillate. Oxidates also other aromatic aldehydes including benzaldehyde, coniferyl aldehyde and cinnamaldehyde, but has a preference for vanillin. Vanillin is produced via the breakdown of phenylalanine.
References
Metabolism and Physiological Effects of Vanillic Acid References
Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015.
Pubmed: 26317986
Wishart DS, Guo A, Oler E, Wang F, Anjum A, Peters H, Dizon R, Sayeeda Z, Tian S, Lee BL, Berjanskii M, Mah R, Yamamoto M, Jovel J, Torres-Calzada C, Hiebert-Giesbrecht M, Lui VW, Varshavi D, Varshavi D, Allen D, Arndt D, Khetarpal N, Sivakumaran A, Harford K, Sanford S, Yee K, Cao X, Budinski Z, Liigand J, Zhang L, Zheng J, Mandal R, Karu N, Dambrova M, Schioth HB, Greiner R, Gautam V: HMDB 5.0: the Human Metabolome Database for 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D622-D631. doi: 10.1093/nar/gkab1062.
Pubmed: 34986597
Fleige C, Hansen G, Kroll J, Steinbuchel A: Investigation of the Amycolatopsis sp. strain ATCC 39116 vanillin dehydrogenase and its impact on the biotechnical production of vanillin. Appl Environ Microbiol. 2013 Jan;79(1):81-90. doi: 10.1128/AEM.02358-12. Epub 2012 Oct 12.
Pubmed: 23064333
Gallage NJ, Hansen EH, Kannangara R, Olsen CE, Motawia MS, Jorgensen K, Holme I, Hebelstrup K, Grisoni M, Moller BL: Vanillin formation from ferulic acid in Vanilla planifolia is catalysed by a single enzyme. Nat Commun. 2014 Jun 19;5:4037. doi: 10.1038/ncomms5037.
Pubmed: 24941968
Achterholt S, Priefert H, Steinbuchel A: Identification of Amycolatopsis sp. strain HR167 genes, involved in the bioconversion of ferulic acid to vanillin. Appl Microbiol Biotechnol. 2000 Dec;54(6):799-807. doi: 10.1007/s002530000431.
Pubmed: 11152072
Overhage J, Priefert H, Steinbuchel A: Biochemical and genetic analyses of ferulic acid catabolism in Pseudomonas sp. Strain HR199. Appl Environ Microbiol. 1999 Nov;65(11):4837-47. doi: 10.1128/AEM.65.11.4837-4847.1999.
Pubmed: 10543794
Plaggenborg R, Steinbuchel A, Priefert H: The coenzyme A-dependent, non-beta-oxidation pathway and not direct deacetylation is the major route for ferulic acid degradation in Delftia acidovorans. FEMS Microbiol Lett. 2001 Nov 27;205(1):9-16. doi: 10.1111/j.1574-6968.2001.tb10918.x.
Pubmed: 11728709
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016.
Pubmed: 34755880
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