Eutypellazines N-S, new thiodiketopiperazines from a deep sea sediment derived fungus Eutypella sp with anti-VRE activities

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Article

Niu, Siwen^1,2  Liu, Dong¹  Shao, Zongze²  Proksch, Peter³  Lin, Wenhan¹ 

[1] Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

[2] SOA, Inst Oceanog 3, Key Lab Marine Biogenet Resources, Xiamen 361005, Peoples R China

[3] Heinrich Heine Univ, Inst Pharmaceut Biol & Biotechnol, D-40225 Dusseldorf, Germany

关键词: Marine fungus;    Eutypella sp.;    Eutypellazines N-S;    Biogenetic postulation;    Structural elucidation;    Anti-VRE activity;   

DOI  :  10.1016/j.tetlet.2017.08.015

来源: Elsevier

【 摘 要 】

Chemical investigation of a deep sea sediment derived fungus Eutypella sp. MCCC 3A00281 resulted in the isolation of six new thiodiketopiperazine alkaloids, namely eutypellazines N-S (1-6). Their structures were elucidated on the basis of the extensive NMR and mass spectroscopic analysis, including the ECD data for the determination of absolute configuration. The structures of eutypellazines N-P (1-3) were characteristic of unique spirocyclic skeletons, while eutypellazines N-O bearing a spirocyclic tetrahydrobenzothiophene motif were found from wide type fungus for the first time. The biogenetic generation of the spirocyclic skeletons was postulated. Compounds 3-5 exhibited inhibitory effects against vancomycin-resistant enterococci (VRE), suggesting that they may be the potential inhibitors toward drug resistant pathogenic bacteria after the structural modification. (C) 2017 Elsevier Ltd. All rights reserved.

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