Cyclic and Linear Thiopeptides from Soil-Derived Streptomyces sp. CPCC 203702 with Antiviral and Antibacterial Activities,Chinese Journal of Chemistry

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Cyclic and Linear Thiopeptides from Soil-Derived Streptomyces sp. CPCC 203702 with Antiviral and Antibacterial Activities
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2021-08-27 , DOI: 10.1002/cjoc.202100496
Dewu Zhang ₁ , Yujia Wang ₁ , Xinxin Hu ₁ , Xiaoyu Wang _{1,

2} , Linzi Li _{1,

2} , Guowei Gu ₁ , Bingyuan Zhang _{1,

3} , Shan Cen ₁ , Xuefu You ₁ , Liyan Yu ₁

Affiliation

A new cyclic thiopeptide, berninamycin F (3), three new linear thiopeptides, berninamycins G—I (4—6), and two known berninamycin derivatives, berninamycins C and D (1 and 2) were isolated from Streptomyces sp. CPCC 203702. Their structures were elucidated through HRESIMS and one- and two-dimensional NMR data, and the absolute configurations were assigned using Marfey's method. Compounds 4—6 are the first examples of linear berninamycin analogs. Notably, compound 4 is the first example of linear thiopeptide with a 1-(oxazol-2-yl)ethan-1-one group, compound 6 is the first linear thiopeptide derivative with methylated oxoacetate moiety. Compounds 1—6 exhibited excellent anti-Zika virus activities with IC₅₀ values in the range of 4.4—10.5 μmol/L, which were superior to that of the positive control ribavirin (IC₅₀ = 49.2 μmol/L). Compounds 1 and 3 showed strong anti-influenza A virus activities with the IC₅₀ values of 15.6 and 3.2 μmol/L, respectively. Compound 1 exhibited good antibacterial activities against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus spp. pathogens.

中文翻译：

来自土壤来源的链霉菌属的环状和线性硫肽。具有抗病毒和抗菌活性的 CPCC 203702

从链霉菌属分离出一种新的环状硫肽，伯那霉素 F (3)，三种新的线性硫肽，伯那霉素 G-I (4-6) 和两种已知的伯那霉素衍生物，伯那霉素 C 和 D（1 和 2）。CPCC 203702。通过HRESIMS和一维和二维核磁共振数据阐明了它们的结构，并使用Marfey方法指定了绝对构型。化合物4-6是线性伯那霉素类似物的第一个例子。值得注意的是，化合物 4 是具有 1-(恶唑-2-基)ethan-1-one 基团的线性硫肽的第一个例子，化合物 6 是具有甲基化氧代乙酸酯部分的第一个线性硫肽衍生物。化合物1-6表现出优异的抗寨卡病毒活性，IC ₅₀值在4.4-10.5 μmol/L范围内，优于阳性对照病毒唑（IC ₅₀ = 49.2 μmol/L）。化合物1和3表现出很强的抗甲型流感病毒活性，IC ₅₀值分别为15.6和3.2 μmol/L。化合物1对耐甲氧西林金黄色葡萄球菌和耐万古霉素肠球菌表现出良好的抗菌活性。病原体。

更新日期：2021-08-27

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