Bacterial oxidation of the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene

Abstract

A Beijerinckia sp. and a mutant strain, Beijerinckia sp. strain B8/36, were shown to cooxidize the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene. Both organisms oxidized acenaphthene to the same spectrum of metabolites, which included 1-acenaphthenol, 1-acenaphthenone, 1,2-acenaphthenediol, acenaphthenequinone, and a compound that was tentatively identified as 1,2-dihydroxyacenaphthylene. In contrast, acenaphthylene was oxidized to acenaphthenequinone and the compound tentatively identified as 1,2dihydroxyacenaphthylene by the wild-type strain of Beijerinckia. Both of these products were also formed when the organism was incubated with synthetic cis-1,2-acenaphthenediol. A metabolite identified as cis-1,2acenaphthenediol was formed from acenaphthylene by the mutant Beijerinckia sp. strain B8/36. Cell extracts prepared from the wild-type Beijerinckia strain contain a constitutive pyridine nucleotide-dependent dehydrogenase which can oxidize l-acenaphthenol and 9-fluorenol. The results indicate that although acenaphthene and acenaphthylene are both oxidized to acenaphthenequinone, the pathways leading to the formation of this end product are different.

Effect of Mixtures of Polycyclic Aromatic Hydrocarbons and Sediments on Fluoranthene Biodegradation Patterns

“…Second, the cometabolic compounds or inducers could be intermediates of naphthalene metabolism and not naphthalene itself. As far as could be determined from a literature search, the acenaphthene ring cleavage products are not similar to those of naphthalene [32][33][34][35], so fluoranthene degradation would not occur in the presence of acenaphthene but would occur in the presence of naphthalene.…”

Regiospecific oxidation of naphthalene and fluorene by toluene monooxygenases and engineered toluene 4‐monooxygenases of Pseudomonas mendocina KR1

“…They are commonly found in crude oil and coal tar, and are one of the largest groups of priority environmental pollutants because of their toxic, mutagenic, and carcinogenic properties (Finkelstein et al, 2003). Microbial metabolism and biodegradation of PAHs such as naphthalene, phenanthrene, and anthracene have been described previously (Cerniglia, 1984;Evans et al, 1965;Finkelstein et al, 2003;Grifoll et al, 1992;Guerin and Zones, 1988;Janikowski et al, 2002;Nojiri et al, 1999;Schocken and Gibson, 1984;Shindo et al, 2001;Yamazoe et al, 2004). These studies with PAHs may be of importance in developing remediation technologies that address environmental pollution by these chemicals.…”

Literature overview: Microbial metabolism of high molecular weight polycyclic aromatic hydrocarbons

“…Monooxygenases, also called mixed-function oxygenases, reduce dioxygen and incorporate one atom of oxygen into a hydroxyl group on the PAH substrate and the other one into water with the concomitant oxidation of NADPH (Leveau et al, 1998). Examples of monooxygenases in pyrene metabolism by bacteria include salicylate hydroxylase (Katagiri et al, 1966), salicylate 5-hydroxylase (Grund et al, 1992), and salicylaldehyde dehydrogenase (Shocken & Gibson, 1984).…”