No abstract

An antifungal isoflavone 7-0-methyl-luteone [5, 2', 4'-trihydroxy-7-methoxy-6-(3, 3-dimethylallyl) isoflavone, 2] was metabolized in cultures of Botrytis cinerea. The substrate was transformed into dihydropyrano-isoflavone [(+)-3] and 2, 3-dihydrodihydroxyprenyl-isoflavone [(-) (2S)-5] as major metabolites. A small quantity of dihydrofurano-isoflavone (4) was also yielded. However the initial intention to detecting a possible metabolic intermediate, 7-O-methyl-luteone epoxide, from 2 to 3-5 was unsuccessful.

Formation of a 2, 4-dichloro-l-nitrobenzene glutathione conjugate [S-(5-chloro-2-nitrophenyl)glutathione, 2] was confirmed in the cell-free system of Mucor javanicus which metabolizes 2, 3-and 2, 4-dichloro-l-nitrobenzenes into the corresponding chloro-methylthio-nitrobenzenes or chloro-methylthiobenzenamines. Further metabolisms of 2, the corresponding cysteine conjugate (3) and 5-chloro-2-nitrobenzenethiol (4) were investigated. Oxidation products (S-oxides and S-dioxides) of the formerly identified methylthio-containing metabolites were isolated from the growing cultures of the fungus administered 2. S-(5-Chloro-2-nitrophenyl)cysteine (3) and N-acetyl-S-(5-chloro-2-nitrophenyl)cysteine (7) were newly identified as metabolites of 2 in the resting cell system of the fungus.

Ten L-5-alkyl-and alkenylthiomethylhydantoin S-oxides (alkyl or alkenyl methyl, ethyl, propyl, isopropyl, allyl, butyl, isobutyl, sec-butyl, pentyl and hexyl) and some related compounds were prepared from L-cystine. L-5-Propylthiomethylhydantoin S-oxide (L-(+)-PHSO) was further split into L-(+)-PHSO and L-(-) PHSO.