New Polycyclic Tetramate Macrolactam from Streptomyces sp. S001

  • Jiao Yujie ,
  • Yan Yaqian ,
  • Liu Yan ,
  • Zhu Deyu ,
  • Shen Yuemao ,
  • Li Yaoyao
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  • a Key Laboratory of Chemical Biology, School of Pharmaceutical Sciences, Shandong University, Jinan 250012;
    b School of Basic Medical Sciences, Shandong University, Jinan 250012

Received date: 2019-12-12

  Revised date: 2020-01-23

  Online published: 2020-03-04

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 81573311, 81773598), the Young Scholars Program of Shandong University (No. 2016WLJH31), the Fundamental Research Funds of Shandong University (No. 2018JC004) and the Program for Changjiang Scholars and Innovative Research Team in University (No. IRT_17R68).

Abstract

Montamide A (1), a new polycyclic tetramate macrolactam (PoTeM) with a 5/5/6 tricyclic system was isolated from recombinant strain S001-PoTeMS023, which is derived from Streptomyces sp. S001 by introducing a new PoTeM biosynthetic gene cluster cftS023. The chemical structure of 1 was elucidated by different spectroscopic techniques including HRMS, 1D and 2D-NMR and ECD spectroscopies. The antibacterial and antifungal activities of compound 1 were carried out by filter paper disc diffusion assay. The results showed that compound 1 has no effect on tested strains at 40 μg/disc. The cytotoxicity of compound 1 was evaluated by methyl thiazolyl tetrazolium (MTT) assay using doxorubicin as a positive control. Compound 1 showed weak antiproliferative activity against human lung carcinoma cell line A549 (IC50~22.6 μmol/L), and the substitution at C16 was critical for the cytotoxicity of compound 1. In addition, the biosynthetic gene cluster of compound 1 was identified and the biosynthetic pathway of compound 1 was proposed.

Cite this article

Jiao Yujie , Yan Yaqian , Liu Yan , Zhu Deyu , Shen Yuemao , Li Yaoyao . New Polycyclic Tetramate Macrolactam from Streptomyces sp. S001[J]. Chinese Journal of Organic Chemistry, 2020 , 40(6) : 1779 -1784 . DOI: 10.6023/cjoc201912017

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