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Cyclamenols E and F, two diastereoisomeric bicyclic macrolactams with a cyclopentane moiety from an Antarctic Streptomyces species

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Abstract

Cyclamenols E (1) and F (2), two bicyclic macrolactams possessing a cyclopentane moiety, were isolated from the Antarctic Streptomyces sp. OUCMDZ-4348. Their structures, including absolute configurations, were determined by spectroscopic analysis, chemical derivatization, and ECD calculation. Treatment of compound 1 with 2,2-dimethoxypropane and pyridinium p-toluenesulfonate in acetone/DMF led to the formation of acetonide 1a with an unexpected skeleton. Compound 1 showed moderate inhibitory activity against the gastric carcinoma cell line N87 with an IC50 value of 9.8 μM, but no cytotoxicity was observed on the other 25 cancer cell lines tested.

Graphical abstract: Cyclamenols E and F, two diastereoisomeric bicyclic macrolactams with a cyclopentane moiety from an Antarctic Streptomyces species

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Publication details

The article was received on 04 Oct 2019, accepted on 30 Nov 2019 and first published on 02 Dec 2019


Article type: Research Article
DOI: 10.1039/C9QO01215J
Org. Chem. Front., 2020, Advance Article

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    Cyclamenols E and F, two diastereoisomeric bicyclic macrolactams with a cyclopentane moiety from an Antarctic Streptomyces species

    J. Shen, J. Wang, H. Chen, Y. Wang, W. Zhu and P. Fu, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01215J

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