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Three new cycloheximide congeners, 2,3-dehydro-α- epi -isocycloheximide ( 1 ), ( E )- and ( Z )-2,3-dehydroanhydrocycloheximides ( 2 and 3 ), together with three known compounds, anhydroisoheximide ( 4 ), cycloheximide ( 5 ), and isocycloheximide ( 6 ), were obtained from the cultures of Streptomyces sp. SC0581. Their structures were elucidated by extensive spectroscopic analysis in combination with theoretical conformational analysis and ECD computations. The photoinduced interconversion between 2 and 3 was observed and verified and the possible reaction path and mechanism were proposed by theoretical computations. The antifungal and cytotoxic activities of 1 - 6 were evaluated and suggested that 2,3-dehydrogenation results in the loss of the activities and supported that the OH-α is important to the activities of cycloheximide congeners.

beilstein journal of organic chemistry

Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximides