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Stereospecificity in algal oxidation of the carcinogen benzo(a)pyrene

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Summary

The green algaSelenastrum capricornutum Printz metabolizes benzo(a)pyrene to vicinal dihydrodiols. Two metabolites isolated from algal medium extracts have been identified ascis-4,5-dihydroxy-4,5-dihydrobenzo(a)pyrene andcis-7,8-dihydroxy-7,8-dihydro-benzo(a)pyrene. Notrans-dihydrodiols have been found. This stereospecificity is unlike that seen in fungal and mammalian systems, in which polycyclic aromatic compounds are metabolized totrans-dihydrodiols.

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References

  1. Zedeck, M. S., J. envir. Path. Toxic.3 (1980) 537.

    CAS  Google Scholar 

  2. Selkirk, J. K., and Macleod, M. C., Bioscience32 (1982) 601.

    Article  CAS  Google Scholar 

  3. Heidelberger, C., A. Rev. Biochem.44 (1975) 79.

    Article  CAS  Google Scholar 

  4. Huberman, E., Sachs, L., Yang, S. K., and Gelboin, H. V., Proc. natl. Acad. Sci. USA73 (1976) 607.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Gelboin, H. V., Physiol. Rev.60 (1980) 1107.

    Article  CAS  PubMed  Google Scholar 

  6. Yang, S. K., McCourt, D. W., Roller, P. P., and Gelboin, H. V., Proc. natl Acad. Sci. USA73 (1976) 2594.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Sims, P., and Grover, P. L., Adv. Cancer Res.20 (1974) 165.

    Article  CAS  PubMed  Google Scholar 

  8. Fu, P. P., and Yang, S. K., Biochem. biophys. Res. Commun.109 (1982) 927.

    Article  CAS  PubMed  Google Scholar 

  9. Cerniglia, C. E., Rev. biochem. Toxic.3 (1981) 321, and references therein.

    CAS  Google Scholar 

  10. Higashi, K., Nakashima, K., Karasaki, Y., Fukunaga, M., and Mizuguchi, Y., Biochem. int.2 (1981) 373.

    CAS  Google Scholar 

  11. Trench, Th. v.d., and Sandermann, H. Jr, FEBS Lett.119 (1980) 227.

    Article  Google Scholar 

  12. Warshawsky, D., Cody, T., Radike, M., Smiddy, B. A., and Nagel, B., in: Polynuclear Aromatic Hydrocarbons: Formation, Metabolism and Measurement, p. 1235. Eds M. Cooke and A. J. Dennis. Battelle Press, Columbus, Ohio 1983.

    Google Scholar 

  13. Miller, W. E., Green, J. C., and Shiroyama, T., EPA-600/19-18-018, EPA Environmental Research Lab., Corvallis, Oregon 1978.

  14. Schoeny, R., and Warshawsky, D., Teratogenesis, Carcinogenesis, and Mutagenesis13 (1983) 151.

    Article  Google Scholar 

  15. Cis- andtrans-dihydrodiol standards were obtained from the NCI Chemical Carcinogen Reference Standard Repository.

  16. Kolattukudy, P. E., and Brown, L., Archs Biochem. Biophys.166 (1975) 599.

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Department of Environmental Health, University of Cincinnati, 45267, Cincinnati, Ohio, USA

    B. Lindquist & D. Warshawsky

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  1. B. Lindquist
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  2. D. Warshawsky
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Acknowledgments. We thank Drs Martha Radike, Terence Cody, and Thomas Keenan for discussions and suggestions regarding the manuscript, and Mary Trentman for technical assistance. Supported by graduate fellowship from the Ryan Foundation, and by USEPA Grant 808459.

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Lindquist, B., Warshawsky, D. Stereospecificity in algal oxidation of the carcinogen benzo(a)pyrene. Experientia 41, 767–769 (1985). https://doi.org/10.1007/BF02012587

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