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. 1992 Nov;58(11):3654–3659. doi: 10.1128/aem.58.11.3654-3659.1992

Fungal metabolism of acenaphthene by Cunninghamella elegans.

J V Pothuluri 1, J P Freeman 1, F E Evans 1, C E Cerniglia 1
PMCID: PMC183157  PMID: 1482186

Abstract

The filamentous fungus Cunninghamella elegans ATCC 36112 metabolized within 72 h of incubation approximately 64% of the [1,8-14C]acenaphthene added. The radioactive metabolites were extracted with ethyl acetate and separated by thin-layer chromatography and reversed-phase high-performance liquid chromatography. Seven metabolites were identified by 1H nuclear magnetic resonance, UV, and mass spectral techniques as 6-hydroxyacenaphthenone (24.8%), 1,2-acenaphthenedione (19.9%), trans-1,2-dihydroxyacenaphthene (10.3%), 1,5-dihydroxyacenaphthene (2.7%), 1-acenaphthenol (2.4%), 1-acenaphthenone (2.1%), and cis-1,2-dihydroxyacenaphthene (1.8%). Parallel experiments with rat liver microsomes indicated that the major metabolite formed from acenaphthene by rat liver microsomes was 1-acenaphthenone. The fungal metabolism of acenaphthene was similar to bacterial and mammalian metabolism, since the primary site of enzymatic attack was on the two carbons of the five-member ring.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. CLEARY G. J. Discreet separation of polycyclic hydrocarbons in air borne particulates usin very long alumina columns. J Chromatogr. 1962 Oct;9:204–215. doi: 10.1016/s0021-9673(00)80761-x. [DOI] [PubMed] [Google Scholar]
  2. Cairns M. A., Nebeker A. V. Toxicity of acenaphthene and isophorone to early life stages of fathead minnows. Arch Environ Contam Toxicol. 1982 Nov;11(6):703–707. doi: 10.1007/BF01059158. [DOI] [PubMed] [Google Scholar]
  3. Cerniglia C. E., Althaus J. R., Evans F. E., Freeman J. P., Mitchum R. K., Yang S. K. Stereochemistry and evidence for an arene oxide-NIH shift pathway in the fungal metabolism of naphthalene. Chem Biol Interact. 1983 Apr-May;44(1-2):119–132. doi: 10.1016/0009-2797(83)90134-5. [DOI] [PubMed] [Google Scholar]
  4. Cerniglia C. E., Dodge R. H., Gibson D. T. Fungal oxidation of 3-methylcholanthrene: formation of proximate carcinogenic metabolites of 3-methylcholanthrene. Chem Biol Interact. 1982 Jan;38(2):161–173. doi: 10.1016/0009-2797(82)90037-0. [DOI] [PubMed] [Google Scholar]
  5. Cerniglia C. E., Kelly D. W., Freeman J. P., Miller D. W. Microbial metabolism of pyrene. Chem Biol Interact. 1986 Feb;57(2):203–216. doi: 10.1016/0009-2797(86)90038-4. [DOI] [PubMed] [Google Scholar]
  6. Cerniglia C. E., Miller D. W., Yang S. K., Freeman J. P. Effects of a fluoro substituent on the fungal metabolism of 1-fluoronaphthalene. Appl Environ Microbiol. 1984 Aug;48(2):294–300. doi: 10.1128/aem.48.2.294-300.1984. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Drummond E. C., Callaghan P., Hopkins R. P. Metabolic dehydrogenation of cis- and trans-acenaphthene-1,2-diol. Xenobiotica. 1972 Nov;2(6):529–538. doi: 10.3109/00498257209111081. [DOI] [PubMed] [Google Scholar]
  8. Grimmer G., Böhnke H., Glaser A. Investigation on the carcinogen burden by air pollution in man. XV. Polycyclic aromatic hydrocarbons in automobile exhaust gas--an inventory. Zentralbl Bakteriol Orig B. 1977 May;164(3):218–234. [PubMed] [Google Scholar]
  9. Hopkins R. P. Microsomal ring-fission of cis- and trans-acenaphthene-1,2-diol. Biochem J. 1968 Jul;108(4):577–582. doi: 10.1042/bj1080577. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Hopkins R. P., Young L. Biochemical studies of toxic agents. Metabolic ring-fission of cis- and trans-acenaphthene-1,2-diol. Biochem J. 1966 Jan;98(1):19–24. doi: 10.1042/bj0980019. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Mihelcic J. R., Luthy R. G. Microbial degradation of acenaphthene and naphthalene under denitrification conditions in soil-water systems. Appl Environ Microbiol. 1988 May;54(5):1188–1198. doi: 10.1128/aem.54.5.1188-1198.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Millner G. C., Fu P. P., Cerniglia C. E. Microbial transformation of 6-nitrobenzo[a]pyrene. J Toxicol Environ Health. 1986;19(4):519–530. doi: 10.1080/15287398609530949. [DOI] [PubMed] [Google Scholar]
  13. Pothuluri J. V., Freeman J. P., Evans F. E., Cerniglia C. E. Fungal transformation of fluoranthene. Appl Environ Microbiol. 1990 Oct;56(10):2974–2983. doi: 10.1128/aem.56.10.2974-2983.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Pothuluri J. V., Heflich R. H., Fu P. P., Cerniglia C. E. Fungal metabolism and detoxification of fluoranthene. Appl Environ Microbiol. 1992 Mar;58(3):937–941. doi: 10.1128/aem.58.3.937-941.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Schocken M. J., Gibson D. T. Bacterial oxidation of the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene. Appl Environ Microbiol. 1984 Jul;48(1):10–16. doi: 10.1128/aem.48.1.10-16.1984. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Simmons C. J., Hopkins R. P., Callaghan P. Metabolic oxidation of acenaphthen-1-ol. Xenobiotica. 1973 Oct;3(10):633–642. doi: 10.3109/00498257309151587. [DOI] [PubMed] [Google Scholar]
  17. Sutherland J. B. Detoxification of polycyclic aromatic hydrocarbons by fungi. J Ind Microbiol. 1992 Jan;9(1):53–61. doi: 10.1007/BF01576368. [DOI] [PubMed] [Google Scholar]

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