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|
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 [Lee95e]. 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.
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
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
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
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
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
©2014 SRI International, 333 Ravenswood Avenue, Menlo Park, CA 94025-3493