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Article: Relationship between structures of substituted indolic compounds and their degradation by marine anaerobic microorganisms

TitleRelationship between structures of substituted indolic compounds and their degradation by marine anaerobic microorganisms
Authors
KeywordsAnaerobic degradation
Indole
Metabolic pathway
Methanogenic condition
Substitution
Sulfate-reducing condition
Issue Date2002
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/marpolbul
Citation
Marine Pollution Bulletin, 2002, v. 45 n. 1-12, p. 379-384 How to Cite?
AbstractDegradation of selected indolic compounds including indole, 1-methylindole, 2-methylindole, and 3-methylindole was assessed under methanogenic and sulfate-reducing conditions using the serum-bottle anaerobic technique and marine sediment from Victoria Harbour, Hong Kong as an inoculum. Our results showed that indole degradation was achieved in 28 days by a methanogenic consortium and 35 days by a sulfate-reducing consortium. During degradation under both conditions, two intermediates were isolated, purified and identified as oxindole and isatin (indole-2,3-dione) suggesting that both methanogenic and sulfate-reducing bacteria use an identical degradation pathway. Degradation processes followed two steps of oxidation accomplished by hydroxylation and then dehydrogenation at 2- and then 3-position sequentially prior to the cleavage of the pyrrole ring between 2- and 3-positions. However, none of 1-methylindole or 2-methylindole was degraded under any conditions. 3-Methylindole (3-methyl-1H-indole, skatole) was transformed under methanogenic conditions and mineralized only under sulfate-reducing conditions. It is clear that methyl substitution on 1- or 2-position inhibits the initial attack by hydroxylation enzymes making them more persistent in the environment and posing longer toxic impact. © 2002 Elsevier Science Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/73401
ISSN
2015 Impact Factor: 3.099
2015 SCImago Journal Rankings: 1.264
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorGu, JDen_HK
dc.contributor.authorFan, Yen_HK
dc.contributor.authorShi, Hen_HK
dc.date.accessioned2010-09-06T06:50:55Z-
dc.date.available2010-09-06T06:50:55Z-
dc.date.issued2002en_HK
dc.identifier.citationMarine Pollution Bulletin, 2002, v. 45 n. 1-12, p. 379-384en_HK
dc.identifier.issn0025-326Xen_HK
dc.identifier.urihttp://hdl.handle.net/10722/73401-
dc.description.abstractDegradation of selected indolic compounds including indole, 1-methylindole, 2-methylindole, and 3-methylindole was assessed under methanogenic and sulfate-reducing conditions using the serum-bottle anaerobic technique and marine sediment from Victoria Harbour, Hong Kong as an inoculum. Our results showed that indole degradation was achieved in 28 days by a methanogenic consortium and 35 days by a sulfate-reducing consortium. During degradation under both conditions, two intermediates were isolated, purified and identified as oxindole and isatin (indole-2,3-dione) suggesting that both methanogenic and sulfate-reducing bacteria use an identical degradation pathway. Degradation processes followed two steps of oxidation accomplished by hydroxylation and then dehydrogenation at 2- and then 3-position sequentially prior to the cleavage of the pyrrole ring between 2- and 3-positions. However, none of 1-methylindole or 2-methylindole was degraded under any conditions. 3-Methylindole (3-methyl-1H-indole, skatole) was transformed under methanogenic conditions and mineralized only under sulfate-reducing conditions. It is clear that methyl substitution on 1- or 2-position inhibits the initial attack by hydroxylation enzymes making them more persistent in the environment and posing longer toxic impact. © 2002 Elsevier Science Ltd. All rights reserved.en_HK
dc.languageengen_HK
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/marpolbulen_HK
dc.relation.ispartofMarine Pollution Bulletinen_HK
dc.subjectAnaerobic degradationen_HK
dc.subjectIndoleen_HK
dc.subjectMetabolic pathwayen_HK
dc.subjectMethanogenic conditionen_HK
dc.subjectSubstitutionen_HK
dc.subjectSulfate-reducing conditionen_HK
dc.titleRelationship between structures of substituted indolic compounds and their degradation by marine anaerobic microorganismsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0025-326X&volume=45&spage=379&epage=384&date=2002&atitle=Relationship+between+structures+of+substituted+indolic+compounds+and+their+degradation+by+marine+anaerobic+microorganismsen_HK
dc.identifier.emailGu, JD: jdgu@hkucc.hku.hken_HK
dc.identifier.authorityGu, JD=rp00701en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/S0025-326X(02)00091-7en_HK
dc.identifier.pmid12398409en_HK
dc.identifier.scopuseid_2-s2.0-0036741558en_HK
dc.identifier.hkuros76361en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0036741558&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume45en_HK
dc.identifier.issue1-12en_HK
dc.identifier.spage379en_HK
dc.identifier.epage384en_HK
dc.identifier.isiWOS:000178336300049-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridGu, JD=7403129601en_HK
dc.identifier.scopusauthoridFan, Y=20734044200en_HK
dc.identifier.scopusauthoridShi, H=8379847000en_HK

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