New Polycyclic Tetramate Macrolactam from Streptomyces sp. S001

doi:10.6023/cjoc201912017

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1779-1784.DOI: 10.6023/cjoc201912017 Previous Articles Next Articles

链霉菌S001代谢产生的多环特特拉姆酸大环内酰胺

焦玉杰^a, 颜雅倩^a, 刘焱^a, 朱德裕^b, 沈月毛^a, 李瑶瑶^a

a 山东大学药学院天然产物化学生物学教育部重点实验室济南 250012;
b 山东大学基础医学院济南 250012

收稿日期:2019-12-12 修回日期:2020-01-23 发布日期:2020-03-04
通讯作者: 沈月毛, 李瑶瑶 E-mail:yshen@sdu.edu.cn;liyaoyao@sdu.edu.cn
基金资助:
国家自然科学基金（Nos.81573311，81773598）、山东大学青年学者未来计划（No.2016WLJH31）、山东大学基本科研业务费（No.2018JC004）和教育部创新团队（No.IRT_17R68）资助项目.

New Polycyclic Tetramate Macrolactam from Streptomyces sp. S001

Jiao Yujie^a, Yan Yaqian^a, Liu Yan^a, Zhu Deyu^b, Shen Yuemao^a, Li Yaoyao^a

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:2019-12-12 Revised:2020-01-23 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).

1. 201779S.pdf(1639KB)

Abstract

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.

Key words: streptomyces, natural products, policyclic tetramate macrolactams, biosynthesis

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.

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链霉菌S001代谢产生的多环特特拉姆酸大环内酰胺

New Polycyclic Tetramate Macrolactam from Streptomyces sp. S001

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