Initial oxidative and subsequent conjugative metabolites produced during the metabolism of phenanthrene by fungi

Journal of Industrial Microbiology

Volumn 16, Issue 4, 1996, Pages 205-215

  Casillas, R P ^a   Crow, S A ^a   Heinze, T M ^a   Deck, J ^a   Cerniglia, C E ^a  

^a NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

Author keywords

Conjugates; Degradation; Fungi; Metabolism; Phenanthrene

Indexed keywords

GLUCOSIDE; GLUCURONIDE; PHENANTHRENE; SULFATE;

AEROBIC METABOLISM; ARTICLE; ASPERGILLUS NIGER; BIODEGRADATION; CANDIDA; CONTROLLED STUDY; FUNGUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN;

ASPERGILLUS NIGER; BIOTRANSFORMATION; CANDIDA; FUNGI; OXIDATION-REDUCTION; PHENANTHRENES;

EID: 0029994409     PISSN: 01694146     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF01570023     Document Type: Article

References (36)

1. 18 columns. J Chromatogr 536: 245-249.
2. Boyland E and P Sims. 1962. Metabolism of polycyclic compounds. 21. The metabolism of phenanthrene in rabbits and rats: dihydrodihydroxy compounds and related glucosiduronic acids. Biochem J 84: 571-582.
3. Bruice PY, TC Bruice, PM Dansette, HG Selander, H Yagi and DM Jerina. 1976. Comparison of the mechanisms of solvolysis and rearrangement of K-region vs non-K-region arene oxides of phenanthrene. Comparative solvolytic rate constants of K-region and non-K-region arene oxides. J Am Chem Soc 98: 2965-2973.
4. Bucker M, HR Glatt, KL Platt, D Avnir, Y Ittah, J Blum and F Oesch. 1979. Mutagenicity of phenanthrene and phenanthrene K-region derivatives. Mutat Res 66: 337-348.
5. Bumpus JA. 1989. Biodegradation of polycyclic aromatic hydrocarbons by Phanerochaete chrysosporium. Appl Environ Microbiol 55: 154-158.
6. Cerniglia CE and SA Crow. 1981. Metabolism of aromatic hydrocarbons by yeasts. Arch Microbiol 129: 9-13.
7. Cerniglia CE, JP Freeman and RK Mitchum. 1982. Glucuronide and sulfate conjugation in the fungal metabolism of aromatic hydrocarbons. Appl Environ Microbiol 43: 1070-1075.
8. Cerniglia CE, KJ Lambert, DW Miller and JP Freeman. 1984. Transformation of 1- and 2-methylnaphthalene by Cunninghamella elegans. Appl Environ Microbiol 47: 111-118.
9. Cerniglia CE and SK Yang. 1984. Stereoselective metabolism of anthracene and phenanthrene by the fungus Cunninghamella elegans. Appl Environ Microbiol 47: 119-124.
10. Cerniglia CE, GL White and RH Heflich. 1985. Fungal metabolism and detoxification of polycyclic aromatic hydrocarbons. Arch Microbiol 143: 105-110.
11. Cerniglia CE, WL Campbell, JP Freeman and FE Evans. 1989. Identification of a novel metabolite in phenanthrene metabolism by the fungus Cunninghamella elegans. Appl Environ Microbiol 55: 2275-2279.
12. Cerniglia CE and MA Heitkamp. 1989. Microbial degradation of polycyclic aromatic hydrocarbons (PAH) in the aquatic environment. In: Metabolism of Polycyclic Aromatic Hydrocarbons in the Aquatic Environment (Varanasi U, ed), pp 41-68, CRC Press, Boca Raton, FL.
13. Cerniglia CE, WL Campbell, PP Fu, JP Freeman and FE Evans. 1990. Stereoselective fungal metabolism of methylated anthracenes. Appl Environ Microbiol 56: 661-668.
14. Cerniglia CE, JB Sutherland and SA Crow. 1992. Fungal metabolism of aromatic hydrocarbons. In: Microbial Degradation of Natural Products (Winkelmann G, ed), pp 193-217, VCH Verlagsgesellschaft, Weinheim.
15. 14C]phenanthrene. Biochem Pharmacol 27: 1865-1871.
16. Cripps RE and RJ Watkinson. 1978. Polycyclic aromatic hydrocarbons: metabolism and environmental aspects. In: Developments in Biodegradation of Hydrocarbons (Watkinson RG, ed), pp 113-134, Applied Science Publishers, London.
17. Fu PP, RC Harvey and FA Beland. 1978. Molecular orbital theoretical prediction of the isomeric products formed from reactions of arene oxides and related metabolites of polycyclic aromatic hydrocarbons. Tetrahedron 34: 857-866.
18. Grimmer G, H Brune, G Dettbarn, J Jacob, E Mohtashamipur, K Norpoth and R Wenzel-Hartung. 1991. Urinary and faecal excretion of phenanthrene and phenanthrols by rats following oral, intraperitoneal, or intrapulmonary application. Polycyc Arom Comp 2: 39-47.
19. Guengerich FP. 1992. Metabolic activation of carcinogens. Pharmacol Ther 54: 17-61.
20. Guengerich FP and T Shimada. 1991. Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chem Res Toxicol 4: 391-407.
21. Jerina DM, H Selander, H Yagi, MC Wells, JF Davey, V Mahadevan and DT Gibson. 1976. Dihydrodiols from anthracene and phenanthrene. J Am Chem Soc 98: 5988-5996.
22. Kadlubar FF and GJ Hammons. 1987. The role of cytochrome P-450 in the metabolism of chemical carcinogens. In: Mammalian Cytochromes P-450 (Guengerich FP, ed), pp 81-130, CRC Press, Boca Raton, FL.
23. Lau EP, L Niswander, D Watson and RR Fall. 1980. Detection of microbial glutathione-5-transferases. Abstr Fed Proc Fed Am Soc Exp Biol 479: 1696.
24. MacGillivray RA and MP Shiaris. 1993. Biotransformation of polycyclic aromatic hydrocarbons by yeasts isolated from coastal sediments. Appl Environ Microbiol 59: 1613-1618.
25. McCann J, E Choi, E Yamasaki and BN Ames. 1975. Detection of carcinogens as mutagens in the Salmonella/microsome test: assay of 300 chemicals. Proc Natl Acad Sci USA 72: 5135-5139.
26. McMillan DC, PP Fu and CE Cerniglia. 1987. Stereoselective fungal metabolism of 7,12-dimethylbenz[a]anthracene: identification and enantiomeric resolution of a K-region dihydrodiol. Appl Environ Microbiol 53: 2560-2566.
27. Millner GC, PP Fu and CE Cerniglia. 1986. Microbial transformation of 6-nitrobenzo[a]pyrene. J Toxicol Environ Health 19: 519-530.
28. Shimada T, D Pruess-Schwartz, LJ Marnett and FP Guengerich. 1989. Roles of individual human cytochrome P-450 enzymes in the bioactivation of benzo[a]pyrene, 7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene, and other dihydrodiol derivatives of polycyclic aromatic hydrocarbons. Cancer Res 49: 6304-6312.
29. Sims P. 1962. Metabolism of polycyclic compounds. The metabolism of phenanthrene in rabbits and rats: phenols and sulphuric esters. Biochem J 84: 558-563.
30. Solbakken JE and KH Palmork. 1981. Metabolism of phenanthrene in various marine animals. Comp Biochem Physiol 70: 21-26.
31. Sutherland JB. 1992. Detoxification of polycyclic aromatic hydrocarbons by fungi. J Ind Microbiol 9: 53-62.
32. Sutherland JB, PP Fu, SK Yang, LS Von Tungeln, RP Casillas, SA Crow and CE Cerniglia. 1993. Enantiomeric composition of the transdihydrodiols produced from phenanthrene by fungi. Appl Environ Microbiol 59: 2145-2149.
33. Sutherland JB, AL Selby, JP Freeman, FE Evans and CE Cerniglia. 1991. Metabolism of phenanthrene by Phanerochaete chrysosporium. Appl Environ Microbiol 57: 3310-3316.
34. Tamaki H, H Kumagai and T Tochikura. 1991. Nucleotide sequence of the yeast glutathione 5-transferase cDNA. Biochim Biophys Acta 1089: 276-279.
35. Wackett LP and DT Gibson. 1982. Metabolism of xenobiotic compounds by enzymes in cell extracts of the fungus Cunninghamella elegans. Biochem J 205: 117-122.
36. Woods LFJ and A Wiseman. 1979. Metabolism of benzo[n]pyrene by the cytochrome P-450/P-448 of Saccharomyces cerevisiae. Biochem Soc Trans 7: 124-127.