Neohydroxyaspergillic acid

Weiss, U., F. Strelitz, H. Flon and I. N. Asheshov Antibiotic compounds with action against bacterial viruses — neohydroxyaspergillic acid. Arch. Biochem. Biophys. 74, 150 (1958). 

Neohydroxyaspergillic acid (7/ 6,193), l-hydroxy-6-(l-hydroxy-2-methyl-propyl)-3-isobuty 1-2(1 7/)-pyrazinone, an Aspergillus sp metabolite.78,727... 

Hydroxy-5-(1 -hydroxy-2 -methylpropyl)-2-isobutylpyrazine 1,4-dioxide was deoxygenated by titanium trichloride in dry tetrahydrofuran under nitrogen at room temperature to give 2-hydroxy-6-(r-hydroxy-2 -methylpropyl)-3-isobutyl-pyrazine 1 oxide (DL-neohydroxyaspergillic acid) (760a). 

Weiss et al. (1958) found that filtrates of cultures of A, sclerotiorum, strain Asp. 485, grown with aeration on papain broth medium, pH 7.0, for approximately 2 days at room temperature (starting with an inoculum of actively growing cultures), contained an antibiotic effective against some bacteria, fungi and viruses. The yield of purified antibiotic was approximately 110 mg/Uter of culture. The antibiotic was isomeric with hydroxyaspergilUc acid and had similar, but not identical properties, so it was named neohydroxyaspergillic acid. 

The reviewer finds that the conditions necessary for the biosynthesis of neoaspergillic acid or neohydroxyaspergillic acid in cultures of A. sclerotiorum have not been investigated systematically, and that it is not known whether modifications in the media or in the strain of the organism would affect the production of these antibiotics. In any case, the conditions described for the production of these antibiotics gives one no clue as to their routes of biosynthesis. 

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