Hydroxylation of carbazoles by Aspergillus flavus VKM F-1024

Abstract

Carbazole was metabolized by Aspergillus flavus VKM F-1024 forming few monohydroxylated products. The structure of metabolites was determined by TLC, GC, MS and 1 H NMR analyses. 3-Hydroxycarbazole was revealed as a major bioconversion product, 1-hydroxy-and 2-hydroxycarbazoles were observed as minor products. In the presence of 1-benzoylindole, the hydroxylation position shifted toward preferable accumulation of 2-hydroxycarbazole and the formation of 2,6-and 2,7-dihydroxycarbazoles. This effect and microbial formation of these metabolites have never been reported before. At the conversion of Nacetyl-and N-benzoylcarbazoles, carbazole was the major product, while 1-, 2-and 3-monohydroxycarbazoles were formed in small amounts.

First evidence of mineralization of petroleum asphaltenes by a strain of Neosartorya fischeri

“…Aspergillus sp. are not especially known as good hydrocarbon degraders (Sutherland, 1992), nevertheless there are reports on their capacity to degrade aliphatic hydrocarbons (Markovetz et al ., 1968; Voigt et al ., 1981; Amin and Modi, 1987; Volke‐Sepúlveda et al ., 2006), polycyclic aromatic hydrocarbons (Ghosh et al ., 1983; Yogambal and Karegoudar, 1997; Salicis et al ., 1999; Garon et al ., 2000; Capotorti et al ., 2004; Naranjo et al ., 2007), carbazole (Lobastova et al ., 2004) and petroleum derived complex mixtures (Elshafie et al ., 2007; Itah et al ., 2009; Okoro and Amund, 2010). In addition, there is experimental evidence that the monooxygenase system cytochrome P450 is involved in the metabolism of these substrates (Dutta et al ., 1983; Baillie et al ., 1996; Prenafeta‐Boldú et al ., 2001; Vatsyayan et al ., 2008).…”

Pollutant Degrading Enzyme: Catalytic Mechanisms and Their Expanded Applications

“…Carbazole is a kind of chemical feedstock for the production of dyes, reagents, insecticides. However, the biotransformation of carbazole to hydroxy-carbazole is of great interest because hydroxylated carbazole derivatives are value-added substances in the pharmaceutical industry [ 70 ]. Bacterial dioxygenases, such as biphenyl dioxygenase and naphthalene 1,2-dioxygenase often catalyze the oxidation of aromatic hydrocarbons and related heterocycles, including carbazole [ 71 ].…”

10.17686/sced_rusnauka_2014-1382

“…Гриб Aspergillus flavus VKM F-1024 в течение двух суток превращал карбазол (CXXX) в три гидроксилированных производных -3-гидроксикарбазол (CXXXI), как основной продукт и в небольших количествах 1-гидроксикарбазол (CXXXV) и 2-гидроксикарбазол (CXXXVIII) (Lobastova et al, 2004):…”

“…Растущая культура C. echinulata превращала N-метилкарбазол (CXXXIX) в карбазол (CXXX), N-гидроксиметил карбазол (CXL), 3-гидроксикарбазол (CXXXI) и 3-гидрокси-Nгидроксиметил карбазол (CXLI) (Yang, Davis, 1992). сопровождались образованием карбазола (CXXX), как основного продукта, и небольших количеств 1-, 2-, и 3гидроксикарбазолов (CXXXV, CXXXVIII и CXXXI) (Lobastova et al, 2004):…”