Substrates: questin and 7-demethyl-neosulochrin are detected in strain FVL2, the latter is another isomer arising from ring cleavage between C-10/C-10a at the other side of the anthraquinone, forming the carboxylic group at ring A Products: -
Substrates: questin and 7-demethyl-neosulochrin are detected in strain FVL2, the latter is another isomer arising from ring cleavage between C-10/C-10a at the other side of the anthraquinone, forming the carboxylic group at ring A Products: -
the organism is cultured on rice medium, and the secondary metabolites are analysed by chromatographic separation delivering three newly identified natural products, 7-demethyl-neosulochrin, fumigaclavine, and N-benzoyl-tryptophan together with further 14 metabolites, 1-O-methyl-sulochrin-4'-sulfate, questin, laccaic acid, isorhodoptilometrin, fumigaclavine A, fumigaclavine C, fumitremorgin C, fumigaquinazoline C, tryptoquivaline J, trypacidin, 3'-O-demethyl-sulochrin, 1-O-methyl-sulochrin, protocatechuic acid, and vermelone. The chemical structures of the three newly identified metabolites are determined by NMR spectroscopy and ESI HR mass spectrometry. The discovery of the seco-anthraquinone 7-demethyl-neosulochrin reveals a second type of ring cleavage by a questin oxygenase. Except for the moderate activity of trypacidin against Staphylococcus aureus, 7-demethyl-neosulochrin, 1-O-methyl-sulochrin, 1-O-methyl-sulochrin-4'-sulfate, isorhodoptilometrin, fumigaclavine A, fumigaclavine C, fumigaquinazoline C, tryptoquivaline J, 3'-O-demethyl-sulochrin and vermelone are inactive in the agar diffusion assay against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and Candida albicans. Demethylneosulochrin, 1-O-methyl-sulochrin-4'-sulfate, 1-O-methyl-sulochrin, fumigaclavine I, and 3-O-demethyl-sulochrin are tested additionally against the human leukemia HL-60 cell line but display no cytotoxicity
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