The antifungal activity and biotransformation of diisophorone by the fungus Aspergillus niger

Abstract

The microbial transformation of racemic diisophorone was investigated using the plant pathogen Aspergillus niger as a biocatalyst. Incubation of diisophorone with Aspergillus niger gave 8α-hydroxydiisophorone, 10-hydroxydiisophorone and 17-hydroxydiisophorone on the basis of their spectroscopic data including two-dimensional NMR analysis, nOe and an X-ray crystallographic study. The antifungal activity of diisophorone against Aspergillus niger was also examined.

Biosorption potential of Neurospora crassa cells for decolorization of Acid Red 57 (AR57) dye

“…Media 24 and growth conditions for N. crassa 23,25 were described in our previous studies and the biosorbent was prepared as follows: The live N. crassa cells were filtered after 7 days of growth, spread on Petri dishes and dried in an oven at 60…”

Biotransformations of organic compounds mediated by cultures of Aspergillus niger

“…(±)-Diisophorone (CLXVIII), which has antifungal activity, is hydroxylated by A. niger ATCC 10549 at three different sites to produce the optically active derivatives 8α-hydroxydiisophorone (CLXIX), 10-hydroxydiisophorone (CLXX), and 17-hydroxydiisophorone (CLXXI) (Kiran et al 2004). …”

Biotransformation of racemic diisophorone by Cephalosporium aphidicola and Neurospora crassa

“…The position of the newly introduced hydroxyl group was established by unambiguous assigments of all carbons and protons through combined use of Heteronuclear Correlation (HETCOR) and Heteronuclear Multi Bond Coherence (HMBC) spectra and by comparing the 13 C-NMR and the DEPT spectra of the metabolite with that of diisophorone and its known metabolites obtained by Aspergillus niger (Kiran et al 2004a). The methylene signal at d C 46.3 ppm assigned to C-8 in diisophorone was not present in the 13 C-NMR and the DEPT spectra of the metabolite, indicating that hydroxyl group was inserted at C-8.…”

“…The synthesis of racemic diisophorone was achieved by cyclization of isophorone with solid NaOH in toluene under reflux (Kiran et al 2004a).…”

“…Preparation of analogues of racemic diisophorone by the microbiological hydroxylation is an attractive target for assessing their biological activity as potential anti-microbial agents since diisophorone exhibited good antifungal activity against Aspergillus niger which causes a black mould on certain types of fruits and vegetables such as peanuts, grapes and tomatoes. The hydroxylation of diisophorone by A. niger afforded the 8a-, 10-and 17-monohydroxy derivatives (Kiran et al 2004a).…”