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

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

  • Beilstein J Org Chem. 2017 May 30:13:1039-1049. doi: 10.3762/bjoc.13.103.
Li Yang 1 2,  Ping Wu 1,  Jinghua Xue 1,  Huitong Tan 1,  Zheng Zhang 1,  Xiaoyi Wei 1
Affiliations

Affiliations

  • 1 Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Digital Botanical Garden, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, China.
  • 2 University of Chinese Academy of Sciences, Yuquanlu 19A, Beijing 100049, China.
PMID: 28684983 DOI: 10.3762/bjoc.13.103
Abstract

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.

Keywords

E/Z photoisomerization; Streptomyces sp; antifungal activity; cycloheximide derivatives; theoretical conformational analysis.

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