Isolation, structure elucidation, and antibacterial evaluation of the metabolites produced by the marine-sourced Streptomyces sp. ZZ820

被引:23
作者
Yi, Wenwen [1 ]
Li, Qiao [1 ]
Song, Tengfei [1 ]
Chen, Lei [1 ]
Li, Xing-Cong [3 ]
Zhang, Zhizhen [1 ]
Lian, Xiao-Yuan [2 ]
机构
[1] Zhejiang Univ, Ocean Coll, Zhoushan Campus, Zhoushan 316021, Peoples R China
[2] Zhejiang Univ, Coll Pharmaceut Sci, Hangzhou 310058, Zhejiang, Peoples R China
[3] Univ Mississippi, Natl Ctr Nat Prod Res, Res Inst Pharmaceut Sci, Sch Pharm, University, MS 38677 USA
基金
国家重点研发计划; 中国国家自然科学基金;
关键词
Streptomyces sp. ZZ820; Marine actinomycetes; Streptoprenylindoles; Cyclooctatin analogues; Antibacterial activities; NATURAL-PRODUCTS; BETA-CARBOLINE; ALKALOIDS;
D O I
10.1016/j.tet.2019.01.025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New indole alkaloids streptoprenylindoles A-C (1-3) and diterpenoids 18-acetyl-cyclooctatin (8), 5,18-dedihydroxy-cyclooctatin (9), and 5-dehydroxy-cyclooctatin (10) were isolated from the culture of marine-derived Streptomyces sp. ZZ820, along with known 3-cyanomethyl-6-[3-methyl-2-butenyl]indole (4), N-(2-(1H-indol-3-yl)ethylacetamide (5), 1-acetyl-beta-carboline (6), indole-3-methylethanoate (7), cyclooctatin (11), and chromomycin A(3) (12). Their structures were elucidated by a combination of extensive spectroscopic analyses, ECD calculation, and the Mosher's method. Streptoprenylindoles A (1) and B (2) are enantiomers that were separated through the preparation of their Mosher esters. Three new diterpenoids (8-10) showed antibacterial activities against methicillin-resistant Staphylococcus aureus (MRSA) and Escherichia coli with MIC values of 24.11-55.12 mu M, while chromomycin A(3) (12) showed potent antibacterial activities against MRSA (MIC: 0.59 mu M) and E. coli (MIC 0.04 mu M). (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1186 / 1193
页数:8
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