Conversion of 1-benzoylindole by Aspergillus strains

Abstract

Biotransformation of 1-benzoylindole (BI) by the strains Aspergillus flavus VKM F-1024 and Aspergillus oryzae VKM F-44 was studied. The major metabolites isolated were identified as 4-hydroxyindole (4-HI), 5-hydroxyindole (5-HI), 4-hydroxy- -benzoylindole, 4-hydroxy-1-(4'-hydroxy)-benzoylindole and indole. The structure of the metabolites was determined by mass spectrometry and proton nuclear magnetic resonance spectroscopy. The pathways of BI metabolism via initial monohydroxylation at C-4 and C-5 followed by cleavage of the benzoyl substituent to yield 4-HI and 5-HI were proposed. Indole was formed as a by-product, and its role as a potent inhibitor of BI hydroxylation at C-4 and C-5 is discussed.

Oxytrofalcatins A–F, N-benzoylindole analogues from the roots of Oxytropis falcata (Leguminosae)

“…Detailed examination of the UV, IR, 1 H and 13 C NMR spectra (Tables 1 and 2) of compounds 1-6 suggested that they were structurally closely related to one other. (Sukhodolskaya et al, 2000), which together with an intense fragment ion at m/z 77 [C 6 H 5 ] + indicated the presence of a benzoyl group. The 1 H NMR spectrum (Table 1) showed all 10 aromatic signals arising from three separate spin systems, where the resonances at d H 8.06 (2H, br d, J = 7.6 Hz, H-2 0 , 6 0 ) and 7.51 (3H, m, H-3 0 , 4 0 , 5 0 ) strongly supported the presence of a monosubstituted benzoyl moiety.…”

“…A careful literature search has established a limited number of articles describing EIMS fragmentary data for N-benzoylindoles (Sukhodolskaya et al, 2000;Liou et al, 2004). Upon fragmentation, the molecular ions of compounds 1-6 yielded two major fragments: F1 (the indole part) and F2 (the benzoyl part).…”

Hydroxylation of carbazoles by Aspergillus flavus VKM F-1024

“…For example, the composition of N-methylcarbazole products by Cunninghamella strains was different as compared with that of CZ [15,16]. The N-benzoyl substitution of indole allowed the obtaining of 4-hydroxyindole [17]. We expected that the change in electron densities within CZ nucleus by Nsubstitution would influence the fate of hydroxylation.…”

“…The pathway included the introduction of hydroxyl function in position 4 of BI followed by the cleavage of benzoyl substitute. 5-Hydroxyindole was detected as a minor metabolite [17].…”

Use of Aspergillus wentii for biosorption of methylene blue from aqueous solution

“…wentii (ATCC #10584) was maintained on Potato Dextro Agar slants and grown on a Potato Dextro Agar solid medium for 7 days. Then, the fungus was cultivated in a liquid growth medium composed of 30 g of glucose, 2.0 g of (NH4)2HPO4, 1.0 g of K2HPO4, 0.5 g of KCl, 3 g of CaCO3, 0.5 g of MgSO4.7H2O and 0.01 g of FeSO4.7H2O in a liter of distilled water (Sukhodolskaya et al, 2000). The pH of the growth medium was adjusted to 5.30 using 1 N HCl before autoclaving.…”