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MetaCyc Pathway: salicylate degradation I

Enzyme View:

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: Degradation/Utilization/Assimilation Aromatic Compounds Degradation Salicylate Degradation

Some taxa known to possess this pathway include ? : Pseudomonas nitroreducens , Pseudomonas putida PpG7 , Pseudomonas reinekei , Pseudomonas stutzeri AN10 , Trichosporon cutaneum

Expected Taxonomic Range: Bacteria , Fungi

Summary:
General Background

Salicylate is a key phenolic compound biosynthesized by many plants and some microorganisms. It is a member of an important anti-inflammatory drug class used widely in human medicine. In microorganisms salicylate is a biosynthetic precursor of secondary metabolites and siderophores, and a regulator of antibiotic efflux [Nair05]. In plants salicylate may be converted by glucosylation, esterification, or methylation to physiologically active derivatives [Lee95]. The source of the name salicylate (salicylic acid) comes from the name of the willow tree, Salix, from whose bark it can be obtained.

For examples of salicylate biosynthetic pathways, see pyochelin biosynthesis, yersiniabactin biosynthesis, salicylate biosynthesis I, salicylate biosynthesis II, salicylate glucosides biosynthesis I, salicylate glucosides biosynthesis III and volatile benzenoid biosynthesis I (ester formation) [Iwasaki10].

In bacteria, salicylate can be degraded through several pathways including oxidation to catechol followed by aromatic ring cleavage (pathway salicylate degradation I), oxidation to gentisate followed by aromatic ring cleavage (pathway salicylate degradation II), direct fission of salicylate (see salicylate 1,2-dioxygenase), and degradation after CoA derivative formation). salicylate is also an intermediate in naphthalene degradation (aerobic).

In yeast, earlier work on Trichosporon cutaneum showed salicylate oxidation to catechol [Anderson80, Sze84]. In a more recent report using Trichosporon moniliiforme WU-0401 a novel pathway of salicylate degradation via phenol was elucidated (pathway salicylate degradation III) [Iwasaki10].

About This Pathway

In this pathway salicylate, which is also an intermediate in the degradation of naphthalene, is degraded via catechol, a common intermediate in the degradation of many aromatic compounds, including benzoate, benzene and phenol.

Catechol can be subject to either intradiol cleavage by a catechol 1,2-dioxygenase (the ortho cleavage pathway) or extradiol cleavage by a catechol 2,3-dioxygenase (the meta cleavage pathway).

This pathway has been demonstrated in both bacteria [Yamamoto65, Bosch99, Camara07] and fungi [Sze84].

Superpathways: superpathway of salicylate degradation , superpathway of aromatic compound degradation via 2-oxopent-4-enoate , naphthalene degradation to acetyl-CoA

Variants: salicylate degradation II , salicylate degradation III , salicylate degradation IV

Credits:
Created 26-Mar-2009 by Caspi R , SRI International


References

Anderson80: Anderson JJ, Dagley S (1980). "Catabolism of aromatic acids in Trichosporon cutaneum." J Bacteriol 141(2);534-43. PMID: 7364712

Bosch99: Bosch R, Moore ER, Garcia-Valdes E, Pieper DH (1999). "NahW, a novel, inducible salicylate hydroxylase involved in mineralization of naphthalene by Pseudomonas stutzeri AN10." J Bacteriol 181(8);2315-22. PMID: 10197990

Camara07: Camara B, Bielecki P, Kaminski F, dos Santos VM, Plumeier I, Nikodem P, Pieper DH (2007). "A gene cluster involved in degradation of substituted salicylates via ortho cleavage in Pseudomonas sp. strain MT1 encodes enzymes specifically adapted for transformation of 4-methylcatechol and 3-methylmuconate." J Bacteriol 189(5);1664-74. PMID: 17172348

Iwasaki10: Iwasaki Y, Gunji H, Kino K, Hattori T, Ishii Y, Kirimura K (2010). "Novel metabolic pathway for salicylate biodegradation via phenol in yeast Trichosporon moniliiforme." Biodegradation 21(4);557-64. PMID: 20020317

Lee95: Lee HI, Leon J, Raskin I (1995). "Biosynthesis and metabolism of salicylic acid." Proc Natl Acad Sci U S A 92(10);4076-9. PMID: 11607533

Nair05: Nair BM, Joachimiak LA, Chattopadhyay S, Montano I, Burns JL (2005). "Conservation of a novel protein associated with an antibiotic efflux operon in Burkholderia cenocepacia." FEMS Microbiol Lett 245(2);337-44. PMID: 15837391

Sze84: Sze IS, Dagley S (1984). "Properties of salicylate hydroxylase and hydroxyquinol 1,2-dioxygenase purified from Trichosporon cutaneum." J Bacteriol 159(1);353-9. PMID: 6539772

Yamamoto65: Yamamoto, S., Katagiri, M., Maeno, H., Hayaishi, O. (1965). "Salicylate hydroxylase, a monooxygenase requiring flavin adenine dinucleotide. I. Purification and general properties." J Biol Chem 240: 3408-13. PMID: 14321380

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Bosch00: Bosch R, Garcia-Valdes E, Moore ER (2000). "Complete nucleotide sequence and evolutionary significance of a chromosomally encoded naphthalene-degradation lower pathway from Pseudomonas stutzeri AN10." Gene 245(1);65-74. PMID: 10713446

Kohler93: Kohler HP, Schmid A, van der Maarel M (1993). "Metabolism of 2,2'-dihydroxybiphenyl by Pseudomonas sp. strain HBP1: production and consumption of 2,2',3-trihydroxybiphenyl." J Bacteriol 175(6);1621-8. PMID: 8449871

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Nikodem03: Nikodem P, Hecht V, Schlomann M, Pieper DH (2003). "New bacterial pathway for 4- and 5-chlorosalicylate degradation via 4-chlorocatechol and maleylacetate in Pseudomonas sp. strain MT1." J Bacteriol 185(23);6790-800. PMID: 14617643

You90: You IS, Murray RI, Jollie D, Gunsalus IC (1990). "Purification and characterization of salicylate hydroxylase from Pseudomonas putida PpG7." Biochem Biophys Res Commun 169(3);1049-54. PMID: 2363715


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Thu Dec 18, 2014, biocyc13.