Polycyclic Tetramate Macrolactams from the Marine-Derived Actinoalloteichus cyanogriseus WH1-2216-6

doi:10.6023/cjoc201703048

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (9): 2352-2360.DOI: 10.6023/cjoc201703048 Previous Articles Next Articles

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海洋异壁放线菌WH1-2216-6产生的多环含特特拉姆酸大环内酰胺

梅显贵^a, 王立平^b, 王冬阳^a, 范杰^a, 朱伟明^a

a 中国海洋大学医药学院海洋药物教育部重点实验室青岛 266003;
b 贵州医科大学药物植物功效与利用国家重点实验室贵阳 550014

收稿日期:2017-03-28 修回日期:2017-04-27 发布日期:2017-05-10
通讯作者: 朱伟明 E-mail:weimingzhu@ouc.edu.cn
基金资助:
国家自然科学基金（Nos.81561148012，41376148）和国家自然科学基金-广东联合基金（No.U1501221）资助项目.

Polycyclic Tetramate Macrolactams from the Marine-Derived Actinoalloteichus cyanogriseus WH1-2216-6

Mei Xiangui^a, Wang Liping^b, Wang Dongyang^a, Fan Jie^a, Zhu Weiming^a

a Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003;
b State Key Laborataory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014

Received:2017-03-28 Revised:2017-04-27 Published:2017-05-10
Contact: 10.6023/cjoc201703048 E-mail:weimingzhu@ouc.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 81561148012, 41376148) and the National Natural Science Foundation of China-Guangdong Fund Joint Project (No. U1501221).

1. Polycyclic Tetramate Macrolactams from the Marine-Derived Actinoalloteichus cyanogriseus WH1-2216-6.PDF(6285KB)

Abstract

From the fermentation broth of the marine-derived Actinoalloteichus cyanogriseus WH1-2216-6, a new 5,5,6-polycyclic tetramate macrolactam (PTM) named 16-hydroxymaltophilin (1) was isolated and identified along with five known analouges, dihydromaltophilin (2), 4-deoxydihydromaltophilin (3), maltophilin (4), xanthobaccin C (5) and FI-2 (6), by means of UV-guided isolation as well as the spectroscopic identification. The cytotoxicities of compounds 1~5 were tested against the human normal hepatic cell line (L-02) and the seven human cancer cell lines, A549, MCF-7, Jurkat, BXPC-3, HCT-116, PANC-1 and K562. The results showed that compounds 1~5 were active against the above human cancer cell lines with the IC₅₀ values of 0.1~9.7 μmol·L^-1, among which the new compound 1 was the lowest toxic to L-02 cell and the most selective to Jurkat, HCT-116 and BXPC-3 cells with the selection index (SI) of 31.5, 41.4 and 52.4, respectively. The antifungal activities of 1~6 against Aspergillus fumigatus AF293 were also tested by two-fold dilution method. Compounds 2 and 4 were active against A. fumigatus AF293 with the minimum inhibitory concentration (MIC) values of 3.04 and 6.12 μmol·L^-1, respectively. To the best of our knowledge, this is the first time to report the antifungal activity of 5,5,6-PTMs against A. fumigatus AF293. Apart from the cytotoxicity of compounds 2 and 3 against A549 and MCF-7 tumor cells lines, the other cytotoxicities were reported here for the first time, indicating the potential use of PTMs as the antitumor and antifungal lead compounds against A. fumigatus.

Key words: polycyclic tetramate macrolactams, Actinoalloteichus cyanogriseus, antitumor, antifugus

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Mei Xiangui, Wang Liping, Wang Dongyang, Fan Jie, Zhu Weiming. Polycyclic Tetramate Macrolactams from the Marine-Derived Actinoalloteichus cyanogriseus WH1-2216-6[J]. Chin. J. Org. Chem., 2017, 37(9): 2352-2360.

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海洋异壁放线菌WH1-2216-6产生的多环含特特拉姆酸大环内酰胺

Polycyclic Tetramate Macrolactams from the Marine-Derived Actinoalloteichus cyanogriseus WH1-2216-6

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