Cytochalasin Derivatives from the Endozoic Curvularia verruculosa CS-129, a Fungus Isolated from the Deep-Sea Squat Lobster Shinkaia crosnieri Living in the Cold Seep Environment,Journal of Natural Products

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Cytochalasin Derivatives from the Endozoic Curvularia verruculosa CS-129, a Fungus Isolated from the Deep-Sea Squat Lobster Shinkaia crosnieri Living in the Cold Seep Environment
Journal of Natural Products ( IF 3.3 ) Pub Date : 2021-11-30 , DOI: 10.1021/acs.jnatprod.1c00907
Xue-Yi Hu _{1,

2} , Chen-Yin Wang ₃ , Xiao-Ming Li ₁ , Sui-Qun Yang ₁ , Xin Li ₁ , Bin-Gui Wang _{1,

2,

4} , Shu-Yi Si ₃ , Ling-Hong Meng _{1,

4}

Affiliation

A new cytochalasin dimer, verruculoid A (1), three new cytochalasin derivatives, including 12-nor-cytochalasin F (2), 22-methoxycytochalasin B₆ (3), and 19-hydroxycytochalasin B (4), and 20-deoxycytochalasin B (5), a synthetic product obtained as a natural product for the first time, together with four known analogues (6–9), were isolated and identified from the culture extract of Curvularia verruculosa CS-129, an endozoic fungus obtained from the inner fresh tissue of the deep-sea squat lobster Shinkaia crosnieri, which was collected from the cold seep area of the South China Sea. Structurally, verruculoid A (1) represents the first cytochalasin homodimer containing a thioether bridge, while 12-nor-cytochalasin F (2) is the first 12-nor-cytochalasin derivative. Their structures were elucidated by detailed interpretation of the NMR spectroscopic and mass spectrometric data. X-ray crystallographic analysis and ECD calculations confirmed their structures and absolute configurations. Compound 1 displayed activity against the human pathogenic bacterium Escherichia coli (MIC = 2 μg/mL), while compounds 4, 8, and 9 showed cytotoxicity against three tumor cell lines (HCT-116, HepG-2, and MCF-7) with IC₅₀ values from 5.2 to 12 μM. The structure–activity relationship was briefly discussed.

中文翻译：

来自内生代疣状弯曲菌 CS-129 的细胞松弛素衍生物，这是一种从生活在冷泉环境中的深海蹲龙虾 Shinkaia crosnieri 中分离出来的真菌

一种新的细胞松弛素二聚体，verruculoid A ( 1 )，三种新的细胞松弛素衍生物，包括 12-nor-cytochalasin F ( 2 )、22-methoxycytochalasin B ₆ ( 3 )、19-hydroxycytochalasin B ( 4 ) 和 20-deoxycytochalasin B ( 5 ) 是首次作为天然产物获得的合成产品，连同四种已知的类似物 ( 6 – 9 )，从疣状弯孢菌CS-129的培养提取物中分离和鉴定，这是一种从内部获得的内生真菌。深海大龙虾Shinkaia crosnieri的新鲜组织，采集自南海冷泉区。在结构上，verruculoid A ( 1 ) 代表第一个含有硫醚桥的细胞松弛素同源二聚体，而 12-nor-cytochalasin F ( 2 ) 是第一个 12-nor-cytochalasin 衍生物。通过对 NMR 光谱和质谱数据的详细解释，阐明了它们的结构。X 射线晶体学分析和 ECD 计算证实了它们的结构和绝对构型。化合物1显示出对人类致病菌大肠杆菌的活性 (MIC = 2 μg/mL)，而化合物4、8和9显示对三种肿瘤细胞系（HCT-116、HepG-2 和 MCF-7）的细胞毒性，IC ₅₀值为 5.2 至 12 μM。简要讨论了构效关系。

更新日期：2021-12-24

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