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Literature DB >> 7138006

Metabolism of 7-methylbenz[a]anthracene and 7-hydroxymethylbenz[a]anthracene by Cunninghamella elegans.

Abstract

The fungal metabolism of 7-methylbenz[a]anthracene (7-MBA) and 7-hydroxymethylbenz[a]anthracene (7-OHMBA) was studied. 7-MBA was metabolized by Cunninghamella elegans to form 7-OHMBA-trans-8,9-dihydrodiol and 7-OHMBA-trans-3,4-dihydrodiol as the predominant metabolites. Other metabolites were identified as 7-OHMBA, 7-MBA-trans-8,9-dihydrodiol and 7-MBA-trans-3,4-dihydrodiol, and 7-MBA-8,9,10,11-tetraol. Incubation of 7-OHMBA with C. elegans cells indicated that 7-OHMBA-trans-8,9-dihydrodiol and 7-OHMBA-trans-3,4-dihydrodiol were major metabolites. The metabolism of 7-MBA by rat liver microsomes from 3-methylcholanthrene-treated rats showed that the metabolites were qualitatively similar to those formed by C. elegans, except additional dihydrodiol metabolites were formed at the 5,6 and 10,11 positions. The metabolites formed were isolated by high-performance liquid chromatography and identified by comparing their chromatographic, UV-visible absorption and mass spectral properties with those of reference compounds.

Entities: Chemical Species

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Year: 1982 PMID： 7138006 PMCID： PMC242076 DOI： 10.1128/aem.44.3.682-689.1982

Source DB: PubMed Journal: Appl Environ Microbiol ISSN： 0099-2240 Impact factor: 4.792

14 in total

1. The metabolic activation of 7-methylbenz(a)anthracene in mouse skin.

Authors: B Tierney; A Hewer; C Walsh; P L Grover; P Sims
Journal: Chem Biol Interact Date: 1977-08 Impact factor: 5.192

2. The metabolic activation of 7-methylbenz(a)anthracene: the induction of malignant transformation and mutation in mammalian cells by non-K-region dihydrodiols.

Authors: H Marquardt; S Baker; B Tierney; P L Grover; P Sims
Journal: Int J Cancer Date: 1977-06-15 Impact factor: 7.396

3. Stereochemistry of the hydrolysis products and their acetonides of two stereoisomeric benzo[a]pyrene 7,8-diol 9,10-epoxides.

Authors: S K Yang; D W McCourt; H V Gelboin; J R Miller; P P Roller
Journal: J Am Chem Soc Date: 1977-07-20 Impact factor: 15.419

4. High microsome-mediated mutagenicity of the 3,4-dihydrodiol of 7-methylbenz[a]anthracene in S. typhimurium TA 98.

Authors: C Malaveille; B Tierney; P L Grover; P Sims; H Bartsch
Journal: Biochem Biophys Res Commun Date: 1977-03-21 Impact factor: 3.575

5. Arene oxides: a new aspect of drug metabolism.

Authors: D M Jerina; J W Daly
Journal: Science Date: 1974-08-16 Impact factor: 47.728

6. Studies on the metabolism of 7-methylbenz-[a]anthracene and 7,12-dimethylbenz[1]anthracene and its hydroxymethyl derivatives in rat liver and adrenal homogenates.

Authors: P Sims
Journal: Biochem Pharmacol Date: 1970-07 Impact factor: 5.858

7. Metabolic activation of polycyclic hydrocarbons. Fluorescence spectral evidence is consistent with metabolism at the 1,2- and 3,4-double bonds of 7-methylbenz[a]anthracene.

Authors: P Vigny; M Duquesne; H Coulomb; C Lacombe
Journal: FEBS Lett Date: 1977-03-15 Impact factor: 4.124

8. Stereoselective fungal metabolism of 7,12-dimethylbenz[a]anthracene: identification and enantiomeric resolution of a K-region dihydrodiol.

Authors: D C McMillan; P P Fu; C E Cerniglia
Journal: Appl Environ Microbiol Date: 1987-10 Impact factor: 4.792

8 in total

Metabolism of 7-methylbenz[a]anthracene and 7-hydroxymethylbenz[a]anthracene by Cunninghamella elegans.

1. The metabolic activation of 7-methylbenz(a)anthracene in mouse skin.

2. The metabolic activation of 7-methylbenz(a)anthracene: the induction of malignant transformation and mutation in mammalian cells by non-K-region dihydrodiols.

3. Stereochemistry of the hydrolysis products and their acetonides of two stereoisomeric benzo[a]pyrene 7,8-diol 9,10-epoxides.

4. High microsome-mediated mutagenicity of the 3,4-dihydrodiol of 7-methylbenz[a]anthracene in S. typhimurium TA 98.

5. Arene oxides: a new aspect of drug metabolism.

6. Studies on the metabolism of 7-methylbenz-[a]anthracene and 7,12-dimethylbenz[1]anthracene and its hydroxymethyl derivatives in rat liver and adrenal homogenates.

7. Metabolic activation of polycyclic hydrocarbons. Fluorescence spectral evidence is consistent with metabolism at the 1,2- and 3,4-double bonds of 7-methylbenz[a]anthracene.

8. The preparation of dihydrodiols from 7-methylbenz[a]-anthracene.

9. The metabolism of 7- and 12-methylbenz[a]anthracene and their derivatives.

10. Oxidation of benzo[a]pyrene by the filamentous fungus Cunninghamella elegans.

1. Fungal Metabolism of n-Alkylbenzenes.

2. Stereoselective fungal metabolism of methylated anthracenes.

3. Regio- and stereoselective metabolism of 7,12-dimethylbenz[a]anthracene by Mycobacterium vanbaalenii PYR-1.

4. Metabolism of 7,12-dimethylbenz[a]anthracene by Cunninghamella elegans.

5. Regio- and stereo-selective metabolism of 4-methylbenz[a]anthracene by the fungus Cunninghamella elegans.

6. Stereoselective metabolism of anthracene and phenanthrene by the fungus Cunninghamella elegans.

Review 7. Detoxification of polycyclic aromatic hydrocarbons by fungi.

8. Stereoselective fungal metabolism of 7,12-dimethylbenz[a]anthracene: identification and enantiomeric resolution of a K-region dihydrodiol.