| Microbial biodegradation of aromatic alkanoic naphthenic acids is affected by the degree of alkyl side chain branching. | |
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MedLine Citation:
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PMID: 20962873 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Naphthenic acids (NAs) occur naturally in oil sands and enter the environment through natural and anthropogenic processes. NAs comprise toxic carboxylic acids that are difficult to degrade. Information on NA biodegradation mechanisms is limited, and there are no studies on alkyl branched aromatic alkanoic acid biodegradation, despite their contribution to NA toxicity and recalcitrance. Increased alkyl side chain branching has been proposed to explain NA recalcitrance. Using soil enrichments, we examined the biodegradation of four aromatic alkanoic acid isomers that differed in alkyl side chain branching: (4'-n-butylphenyl)-4-butanoic acid (n-BPBA, least branched); (4'-iso-butylphenyl)-4-butanoic acid (iso-BPBA); (4'-sec-butylphenyl)-4-butanoic acid (sec-BPBA) and (4'-tert-butylphenyl)-4-butanoic acid (tert-BPBA, most branched). n-BPBA was completely metabolized within 49 days. Mass spectral analysis confirmed that the more branched isomers iso-, sec- and tert-BPBA were transformed to their butylphenylethanoic acid (BPEA) counterparts at 14 days. The BPEA metabolites were generally less toxic than BPBAs as determined by Microtox assay. n-BPEA was further transformed to a diacid, showing that carboxylation of the alkyl side chain occurred. In each case, biodegradation of the carboxyl side chain proceeded through beta-oxidation, which depended on the degree of alkyl side chain branching, and a BPBA degradation pathway is proposed. Comparison of 16S rRNA gene sequences at days 0 and 49 showed an increase and high abundance at day 49 of Pseudomonas (sec-BPBA), Burkholderia (n-, iso-, tert-BPBA) and Sphingomonas (n-, sec-BPBA). |
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Authors:
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Richard J Johnson; Ben E Smith; Paul A Sutton; Terry J McGenity; Steven J Rowland; Corinne Whitby |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2010-10-21 |
Journal Detail:
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Title: The ISME journal Volume: 5 ISSN: 1751-7370 ISO Abbreviation: ISME J Publication Date: 2011 Mar |
Date Detail:
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Created Date: 2011-02-15 Completed Date: 2012-01-20 Revised Date: 2012-03-01 |
Medline Journal Info:
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Nlm Unique ID: 101301086 Medline TA: ISME J Country: England |
Other Details:
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Languages: eng Pagination: 486-96 Citation Subset: IM |
Affiliation:
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Department of Biological Sciences, University of Essex, Wivenhoe Park, Colchester, Essex, UK. |
| Data Bank Information | |
Bank Name/Acc. No.:
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GENBANK/GU816174; GU816175; GU816176; GU816177; GU816178; GU816179; GU816180; GU816181; GU816182; GU816183; GU816184; GU816185; GU816186; GU816187; GU816188; GU816189; GU816190; GU816191; GU816192; GU816193; GU816194; GU816195; GU816196; GU816197; GU816198; GU816199; GU816200; GU816201; GU816202; GU816203; GU816204; GU816205; GU816206; GU816207; GU816208; GU816209; GU816210; GU816211; GU816212; GU816213; GU816214; GU816215; GU816216; GU816217; GU816218; GU816219; GU816220; GU816221; GU816222; GU816223; GU816224; GU816225; GU816226; GU816227; GU816228; GU816229; GU816230; GU816231; GU816232; GU816233; GU816234; GU816235; GU816236; GU816237; GU816238; GU816239; GU816240 |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Bacteria
/
classification,
genetics,
metabolism* Bacterial Load Biodegradation, Environmental Carboxylic Acids / chemistry*, metabolism* Molecular Sequence Data Phylogeny RNA, Ribosomal, 16S / genetics Soil Pollutants / chemistry*, metabolism* |
| Chemical | |
Reg. No./Substance:
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0/Carboxylic Acids; 0/RNA, Ribosomal, 16S; 0/Soil Pollutants; 1338-24-5/naphthenic acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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