Fungal metabolism of acenaphthene by Cunninghamella elegans

Abstract

The filamentous fungus Cunninghamella elegans ATCC 36112 metabolized within 72 h of incubation approximately 64% of the [1,8-14Clacenaphthene 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-1,2dihydroxyacenaphthene (1.8%). Parallel experiments with rat liver microsomes indicated that the major metabolite formed from acenaphthene by rat liver microsomes was l-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.

Lignin Peroxidase Oxidation of Aromatic Compounds in Systems Containing Organic Solvents

“…The mass spectra of the two products from acenaphthene matched those of 1-acenaphthenone and 1-acenaphthenol given by Pothuluri et al (33). The product of dibenzothiophene oxidation by lignin peroxidase was its sulfoxide, as determined by comparing the GC-mass spectrometry analysis with a sample of authentic dibenzothiophene sulfoxide.…”

“…1-Acenaphthenol and 1-acenaphthenone were the oxidation products from acenaphthene treatment with lignin peroxidase and hydrogen peroxide (Fig. 3), and these products were detected as metabolites of acenaphthene in a Cunninghamella elegans culture (33). Pyrenediones were also found by Hammel et al (22) as major products of pyrene oxidation by lignin peroxidase, and 3,4-pyrene-dihydrodiols were produced during the degradation of pyrene by a Mycobacterium sp.…”

“…The ability of ligninolytic fungi to attack organic pollutants and xenobiotics has been studied (14,18,29), and the capacity to biotransform and biodegrade PAHs has been investigated. Among the PAHs studied are acenaphthene (33), anthracene (20), benzo[a]pyrene (2,36), biphenyl (41), fluoranthrene (32), fluorene (16), methylanthracenes (6), phenanthrene (19,29,38), pyrene (22,25), some monoaromatic compounds (47), and the PAH components of the anthracene oil from coal tar distillation (1).…”

Structural elucidation of phase I and II metabolites of bupivacaine in horse urine and fungi of the Cunninghamella species using liquid chromatography/multi‐stage mass spectrometry

“…Several studies have investigated the biotransformation of drugs by fungi [11][12][13][14][15][16][17][18][19] and it has been shown that some of these organisms produce mammalian metabolites. [11,[14][15][16][17][18][19] Examples of metabolic transformations in Cunninghamella fungi are the phase I reactions hydroxylation, [14] epoxidation, [14] N-oxidation, [20] N-dealkylation, [15] O-demethylation, [15] and deamination, [15] as well as the phase II reactions glucuronic acid conjugation, [21] sulfate conjugation, [21] glucoside conjugation, [13] and riboside conjugation. [13] This fungal genus has been found to express either a cytochrome P450 [22] or a similar enzymatic system.…”

Isolation and Characterization of a Novel Atrazine Metabolite Produced by the Fungus Pleurotus pulmonarius , 2-Chloro-4-Ethylamino-6-(1-Hydroxyisopropyl)Amino-1,3,5-Triazine

“…Other fungi have shown the ability to hydroxylate a wide range of pesticides, mainly by ring hydroxylation, including carbaryl, phenoxyacetic acid, and 2,4-dichlorophenoxyacetic acid (4). In recent years, the hydroxylation of polyaromatic hydrocarbons has also been demonstrated (21). Aliphatic hydroxylation has been less reported in fungal xenobiotic transformation, although hydroxylation of carbaryl by several soil fungi, producing a hydroxymethyl metabolite, has been demonstrated (5).…”