Degradation of Phenanthrene and Anthracene by Cell Suspensions ofMycobacteriumsp. Strain PYR-1

Applied and Environmental Microbiology - Tập 67 Số 4 - Trang 1476-1483 - 2001
Joanna D. Moody1, James P. Freeman2, Daniel R. Doerge3, Carl E. Cerniglia1
1Division of Microbiology,1
2Division of Chemistry,2 and
3Division of Biochemical Toxicology,3 National Center for Toxicological Research, U.S. Food and Drug Administration, Jefferson, Arkansas 72079

Tóm tắt

ABSTRACTCultures ofMycobacteriumsp. strain PYR-1 were dosed with anthracene or phenanthrene and after 14 days of incubation had degraded 92 and 90% of the added anthracene and phenanthrene, respectively. The metabolites were extracted and identified by UV-visible light absorption, high-pressure liquid chromatography retention times, mass spectrometry,1H and13C nuclear magnetic resonance spectrometry, and comparison to authentic compounds and literature data. Neutral-pH ethyl acetate extracts from anthracene-incubated cells showed four metabolites, identified ascis-1,2-dihydroxy-1,2-dihydroanthracene, 6,7-benzocoumarin, 1-methoxy-2-hydroxyanthracene, and 9,10-anthraquinone. A novel anthracene ring fission product was isolated from acidified culture media and was identified as 3-(2-carboxyvinyl)naphthalene-2-carboxylic acid. 6,7-Benzocoumarin was also found in that extract. WhenMycobacteriumsp. strain PYR-1 was grown in the presence of phenanthrene, three neutral metabolites were identified ascis- andtrans-9,10-dihydroxy-9,10-dihydrophenanthrene andcis-3,4-dihydroxy-3,4-dihydrophenanthrene. Phenanthrene ring fission products, isolated from acid extracts, were identified as 2,2′-diphenic acid, 1-hydroxynaphthoic acid, and phthalic acid. The data point to the existence, next to already known routes for both gram-negative and gram-positive bacteria, of alternative pathways that might be due to the presence of different dioxygenases or to a relaxed specificity of the same dioxygenase for initial attack on polycyclic aromatic hydrocarbons.

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Tài liệu tham khảo

10.1039/p19750002506

10.1128/AEM.66.2.518-523.2000

10.1128/aem.62.7.2547-2553.1996

10.1128/aem.59.6.1927-1930.1993

10.1007/BF00170638

10.1007/BF00129093

10.1016/0076-6879(90)88027-8

10.1128/aem.47.1.119-124.1984

10.1128/AEM.65.2.549-552.1999

10.1007/s002530050822

10.1042/bj0950819

Fernley H. N. Griffiths E. Evans W. C. Oxidative metabolism of phenanthrene and anthracene by soil bacteria: the initial ring-fission step. Biochem. J. 91 1964 15p 16p

10.1128/aem.60.5.1687-1689.1994

10.1128/aem.57.12.3462-3469.1991

10.1002/etc.5620140304

10.1128/aem.54.4.937-944.1988

10.1128/aem.54.6.1612-1614.1988

10.1128/aem.55.8.1968-1973.1989

10.1128/aem.54.10.2549-2555.1988

10.1128/aem.54.10.2556-2565.1988

10.1007/BF00249119

10.1021/ja00435a035

10.1128/aem.62.7.2311-2316.1996

10.1128/JB.182.8.2059-2067.2000

10.1007/BF00186971

10.1007/BF01575598

10.1080/15320389509383482

10.1007/BF00119765

10.1128/aem.57.3.636-641.1991

10.1128/aem.59.3.800-806.1993

10.1111/j.1574-6968.1997.tb12613.x

10.1080/00021369.1976.10862190

10.1128/aem.43.2.454-457.1982

10.1099/00207713-46-3-683

10.1111/j.1574-6968.1997.tb10462.x

10.1128/aem.59.6.1938-1942.1993

10.1128/aem.58.4.1351-1359.1992

Pouchert C. J. Behnke J. The Aldrich library of 13C and 1H FT NMR spectra 1st ed. 2 1993 1311B Aldrich Chemical Company, Inc. Milwaukee, Wis

Rafii F. Butler W. R. Cerniglia C. E. Differentiation of a rapidly growing, scotochromogenic, polycyclic-aromatic-hydrocarbon-metabolizing strain of Mycobacterium sp. from other known Mycobacterium species. Arch. Microbiol. 157 1992 512 520

10.1016/S0045-6535(97)10240-5

10.1080/10406639608544657

10.1128/JB.182.8.2134-2141.2000

10.1128/aem.59.6.1931-1937.1993

10.1128/aem.62.1.13-19.1996

10.1007/BF00248965

10.1016/S0953-7562(09)81100-3

10.1128/aem.59.7.2145-2149.1993

Sutherland J. B. Rafii F. Khan A. A. Cerniglia C. E. Mechanisms of polycyclic aromatic hydrocarbon degradation Microbial transformation and degradation of toxic organic chemicals. Young L. Y. Cerniglia C. E. 1995 169 306 Wiley-Liss New York N.Y

10.1007/BF00191198

10.1139/w99-017

10.1007/BF00167921

10.1111/j.1574-6968.1995.tb07701.x

10.1007/BF00903787

10.1007/BF00180583

10.1016/0269-7491(93)90206-4

10.1128/jb.176.8.2158-2164.1994

10.1038/sj.jim.2900475

10.1111/j.1749-6632.1994.tb47410.x

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Applied and Environmental Microbiology

Tập 67 Số 4

1476-1483

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