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Article: Degradation of substituted indoles by an indole-degrading methanogenic consortium

TitleDegradation of substituted indoles by an indole-degrading methanogenic consortium
Authors
Issue Date1991
Citation
Applied And Environmental Microbiology, 1991, v. 57 n. 9, p. 2622-2627 How to Cite?
AbstractDegradation of indole by an indole-degrading methanogenic consortium enriched from sewage sludge proceeded through a two-step hydroxylation pathway yielding oxindole and isatin. The ability of this consortium to hydroxylate and subsequently degrade substituted indoles was investigated. Of the substituted indoles tested, the consortium was able to transform or degrade 3-methylindole and 3-indolyl acetate. Oxindole, 3-methyloxindole, and indoxyl were identified as metabolites of indole, 3-methylindole, and 3-indolyl acetate degradation, respectively. Isatin (indole-2,3-dione) was produced as an intermediate when the consortium was amended with oxindole, providing evidence that degradation of indole proceeded through successive hydroxylation of the 2- and 3-positions prior to ring cleavage between the C-2 and C-3 atoms on the pyrrole ring of indole. The presence of a methyl group (-CH3) at either the 1- or 2-position of indole inhibited the initial hydroxylation reaction. The substituted indole, 3-methylindole, was hydroxylated in the 2-position but not in the 3-position and could not be further metabolized through the oxindole-isatin pathway. Indoxyl (indole-3-one), the deacetylated product of 3-indolyl acetate, was not hydroxylated in the 2-position and thus was not further metabolized by the consortium. When an H atom or electron-donating group (i.e., -CH3) was present at the 3-position, hydroxylation proceeded at the 2-position, but the presence of electron-withdrawing substituent groups (i.e., -OH or -COOH) at the 3-position inhibited hydroxylation.
Persistent Identifierhttp://hdl.handle.net/10722/178505
ISSN
2015 Impact Factor: 3.823
2015 SCImago Journal Rankings: 1.891
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorGu, JDen_US
dc.contributor.authorBerry, DFen_US
dc.date.accessioned2012-12-19T09:48:05Z-
dc.date.available2012-12-19T09:48:05Z-
dc.date.issued1991en_US
dc.identifier.citationApplied And Environmental Microbiology, 1991, v. 57 n. 9, p. 2622-2627en_US
dc.identifier.issn0099-2240en_US
dc.identifier.urihttp://hdl.handle.net/10722/178505-
dc.description.abstractDegradation of indole by an indole-degrading methanogenic consortium enriched from sewage sludge proceeded through a two-step hydroxylation pathway yielding oxindole and isatin. The ability of this consortium to hydroxylate and subsequently degrade substituted indoles was investigated. Of the substituted indoles tested, the consortium was able to transform or degrade 3-methylindole and 3-indolyl acetate. Oxindole, 3-methyloxindole, and indoxyl were identified as metabolites of indole, 3-methylindole, and 3-indolyl acetate degradation, respectively. Isatin (indole-2,3-dione) was produced as an intermediate when the consortium was amended with oxindole, providing evidence that degradation of indole proceeded through successive hydroxylation of the 2- and 3-positions prior to ring cleavage between the C-2 and C-3 atoms on the pyrrole ring of indole. The presence of a methyl group (-CH3) at either the 1- or 2-position of indole inhibited the initial hydroxylation reaction. The substituted indole, 3-methylindole, was hydroxylated in the 2-position but not in the 3-position and could not be further metabolized through the oxindole-isatin pathway. Indoxyl (indole-3-one), the deacetylated product of 3-indolyl acetate, was not hydroxylated in the 2-position and thus was not further metabolized by the consortium. When an H atom or electron-donating group (i.e., -CH3) was present at the 3-position, hydroxylation proceeded at the 2-position, but the presence of electron-withdrawing substituent groups (i.e., -OH or -COOH) at the 3-position inhibited hydroxylation.en_US
dc.languageengen_US
dc.relation.ispartofApplied and Environmental Microbiologyen_US
dc.subject.meshBiodegradation, Environmentalen_US
dc.subject.meshEuryarchaeota - Isolation & Purification - Metabolismen_US
dc.subject.meshHydroxylationen_US
dc.subject.meshIndoleacetic Acids - Metabolismen_US
dc.subject.meshIndoles - Metabolismen_US
dc.subject.meshSewageen_US
dc.subject.meshSkatole - Metabolismen_US
dc.subject.meshWater Microbiologyen_US
dc.titleDegradation of substituted indoles by an indole-degrading methanogenic consortiumen_US
dc.typeArticleen_US
dc.identifier.emailGu, JD: jdgu@hkucc.hku.hken_US
dc.identifier.authorityGu, JD=rp00701en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.pmid1768136-
dc.identifier.scopuseid_2-s2.0-0025809737en_US
dc.identifier.volume57en_US
dc.identifier.issue9en_US
dc.identifier.spage2622en_US
dc.identifier.epage2627en_US
dc.identifier.isiWOS:A1991GF76900030-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridGu, JD=7403129601en_US
dc.identifier.scopusauthoridBerry, DF=7402256759en_US

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