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Applied and Environmental Microbiology, February 2009, p. 998-1004, Vol. 75, No. 4
0099-2240/09/$08.00+0     doi:10.1128/AEM.01870-08
Copyright © 2009, American Society for Microbiology. All Rights Reserved.

Metabolism of Hydroxylated and Fluorinated Benzoates by Syntrophus aciditrophicus and Detection of a Fluorodiene Metabolite{triangledown}

Housna Mouttaki,1 Mark A. Nanny,2 and Michael J. McInerney1*

Department of Botany and Microbiology,1 Department of Civil and Environmental Engineering, University of Oklahoma, Norman, Oklahoma2

Received 12 August 2008/ Accepted 18 December 2008

Transformations of 2-hydroxybenzoate and fluorobenzoate isomers were investigated in the strictly anaerobic Syntrophus aciditrophicus to gain insight into the initial steps of the metabolism of aromatic acids. 2-Hydroxybenzoate was metabolized to methane and acetate by S. aciditrophicus and Methanospirillum hungatei cocultures and reduced to cyclohexane carboxylate by pure cultures of S. aciditrophicus when grown in the presence of crotonate. Under both conditions, transient accumulation of benzoate but not phenol was observed, indicating that dehydroxylation occurred prior to ring reduction. Pure cultures of S. aciditrophicus reductively dehalogenated 3-fluorobenzoate with the stoichiometric accumulation of benzoate and fluorine. 3-Fluorobenzoate-degrading cultures produced a metabolite that had a fragmentation pattern almost identical to that of the trimethylsilyl (TMS) derivative of 3-fluorobenzoate but with a mass increase of 2 units. When cells were incubated with deuterated water, this metabolite had a mass increase of 3 or 4 units relative to the TMS derivative of 3-fluorobenzoate. 19F nuclear magnetic resonance spectroscopy (19F NMR) detected a metabolite in fluorobenzoate-degrading cultures with two double bonds, either 1-carboxyl-3-fluoro-2,6-cyclohexadiene or 1-carboxyl-3-fluoro-3,6-cyclohexadiene. The mass spectral and NMR data are consistent with the addition of two hydrogen or deuterium atoms to 3-fluorobenzoate, forming a 3-fluorocyclohexadiene metabolite. The production of a diene metabolite provides evidence that S. aciditrophicus contains dearomatizing reductase that uses two electrons to dearomatize the aromatic ring.

* Corresponding author. Mailing address: Department of Botany and Microbiology, University of Oklahoma, 770 Van Vleet Oval, Norman, OK 73019. Phone: (405) 325-6050. Fax: (405) 325-7619. E-mail: mcinerney{at}ou.edu

{triangledown} Published ahead of print on 29 December 2008.

Applied and Environmental Microbiology, February 2009, p. 998-1004, Vol. 75, No. 4
0099-2240/09/$08.00+0     doi:10.1128/AEM.01870-08
Copyright © 2009, American Society for Microbiology. All Rights Reserved.





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