Citation: 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 shu

New Polycyclic Tetramate Macrolactam from Streptomyces sp. S001

Jiao Yujie ¹ ,
Yan Yaqian ¹ ,
Liu Yan ¹ ,
Zhu Deyu ² ,
Shen Yuemao ^1,, ,
Li Yaoyao ^1,,

a.
Key Laboratory of Chemical Biology, School of Pharmaceutical Sciences, Shandong University, Jinan 250012
b.
School of Basic Medical Sciences, Shandong University, Jinan 250012

Corresponding author: Shen Yuemao, yshen@sdu.edu.cn Li Yaoyao, liyaoyao@sdu.edu.cn
Received Date: 12 December 2019
Revised Date: 23 January 2020
Available Online: 26 April 2020
Fund Project: the National Natural Science Foundation of China 81773598the National Natural Science Foundation of China 81573311the Program for Changjiang Scholars and Innovative Research Team in University IRT_17R68Project 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)the Young Scholars Program of Shandong University 2016WLJH31the Fundamental Research Funds of Shandong University 2018JC004

Figures(4)

Montamide A (1), a new polycyclic tetramate macrolactam (PoTeM) with a 5/5/6 tricyclic system was isolated from recombinant strain S001-PoTeM_S023, which is derived from Streptomyces sp. S001 by introducing a new PoTeM biosynthetic gene cluster cft_S023. 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.
- streptomyces,
- natural products,
- policyclic tetramate macrolactams,
- biosynthesis
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