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

ABSTRACT: Three new cycloheximide congeners, 2,3-dehydro-?-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-? is important to the activities of cycloheximide congeners.

SUBMITTER: Yang L 

PROVIDER: S-EPMC5480333 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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

Yang Li L   Wu Ping P   Xue Jinghua J   Tan Huitong H   Zhang Zheng Z   Wei Xiaoyi X  

Beilstein journal of organic chemistry 20170530

Three new cycloheximide congeners, 2,3-dehydro-α-<i>epi</i>-isocycloheximide (<b>1</b>), (<i>E</i>)- and (<i>Z</i>)-2,3-dehydroanhydrocycloheximides (<b>2</b> and <b>3</b>), together with three known compounds, anhydroisoheximide (<b>4</b>), cycloheximide (<b>5</b>), and isocycloheximide (<b>6</b>), were obtained from the cultures of <i>Streptomyces</i> sp. SC0581. Their structures were elucidated by extensive spectroscopic analysis in combination with theoretical conformational analysis and ECD  ...[more]

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