Issue 2, 2020
From the journal:

Organic Chemistry Frontiers

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

Jingjing Shen,ab   Jie Wang,ab   Hao Chen,c   Yi Wang,ab   Weiming Zhu ORCID logo *ab  and  Peng Fu ORCID logo *ab  

* Corresponding authors

a Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
E-mail: fupeng@ouc.edu.cn, weimingzhu@ouc.edu.cn

b Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology (Qingdao), Qingdao 266003, China

c Key Laboratory of Marine Bioactive Substances, First Institute of Oceanography, Ministry of Natural Resources of China, Qingdao 266061, China

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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Article information

DOI
https://doi.org/10.1039/C9QO01215J
Article type
Research Article
Submitted
04 Oct 2019
Accepted
30 Nov 2019
First published
02 Dec 2019

Org. Chem. Front., 2020,7, 310-317

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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, 7, 310 DOI: 10.1039/C9QO01215J

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