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深海沉积物来源真菌层出镰刀菌 SD-388 中的新型抗菌硫代二酮哌嗪类化合物。

New Antibacterial Thiodiketopiperazines from the Deep Sea Sediment-Derived Fungus Epicoccum nigrum SD-388.

机构信息

Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao, 266071, P. R. China.

Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, Wenhai Road 1, Qingdao, 266237, P. R. China.

出版信息

Chem Biodivers. 2020 Aug;17(8):e2000320. doi: 10.1002/cbdv.202000320. Epub 2020 Jul 20.

DOI:10.1002/cbdv.202000320
PMID:32686343
Abstract

Two new antibacterial thiodiketopiperazine derivatives (TDKPs), 7-dehydroxyepicoccin H and 7-hydroxyeutypellazine F, along with seven known TDKP analogs, were isolated and identified from Epicoccum nigrum SD-388, a deep-sea-sediment-derived fungus. The structures of these compounds were elucidated on the basis of detailed spectroscopic analysis. The absolute configuration of 7-dehydroxyepicoccin H was established by X-ray crystallographic analysis, while 7-hydroxyeutypellazine F was determined by ECD experiment and TDDFT-ECD calculation. The antibacterial activities against human and aquatic pathogens were evaluated. 7-Dehydroxyepicoccin H and 7-hydroxyeutypellazine F displayed inhibitory activities against aquatic pathogens Vibrio vulnificus, V. alginolyticus, and Edwardsiella tarda, with MIC values ranging from 4.0 to 8.0 μg/mL.

摘要

从深海沉积物来源的真菌层出镰刀菌(Epicoccum nigrum SD-388)中分离得到了两种新的抗菌硫二酮哌嗪衍生物(TDKPs),即 7-脱氢表鬼笔环肽 H 和 7-羟基金针菌素 F,以及七种已知的 TDKP 类似物。基于详细的光谱分析阐明了这些化合物的结构。通过 X 射线晶体学分析确定了 7-脱氢表鬼笔环肽 H 的绝对构型,而 7-羟基金针菌素 F 则通过 ECD 实验和 TDDFT-ECD 计算确定。评估了它们对人类和水生病原体的抗菌活性。7-脱氢表鬼笔环肽 H 和 7-羟基金针菌素 F 对水生病原体创伤弧菌、溶藻弧菌和迟缓爱德华氏菌表现出抑制活性,MIC 值范围为 4.0 至 8.0 μg/mL。

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