Bipolaquinones A–J, Immunosuppressive Meroterpenoids from a Soil-Derived Bipolaris zeicola,Journal of Natural Products

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Bipolaquinones A–J, Immunosuppressive Meroterpenoids from a Soil-Derived Bipolaris zeicola
Journal of Natural Products ( IF 3.3 ) Pub Date : 2021-09-01 , DOI: 10.1021/acs.jnatprod.1c00327
Mengting Liu ₁ , Lianghu Gu ₁ , Ling Shen ₁ , Xueke Zhang ₁ , Shuang Lin ₁ , Ying Ye ₁ , Jianping Wang ₁ , Zhengxi Hu ₁ , Yonghui Zhang ₁

Affiliation

Ten new meroterpenoids, bipolaquinones A–J (1–10), and one known congener, isocochlioquinone F (11), were isolated and identified from the fermented rice cultures of a soil-derived fungus, Bipolaris zeicola. The planar structures of 1–10 were elucidated based on extensive spectroscopic analyses (including HRESIMS and 1D and 2D NMR data), and their absolute configurations were determined by single-crystal X-ray diffraction analyses, comparison of experimental electronic circular dichroism (ECD) data, ECD calculations, and hydrolysis reaction. The immunosuppressive activity assay revealed that compounds 2, 3, and 7–10 showed significant inhibitory activity against concanavalin A (ConA)-induced T lymphocyte proliferation with IC₅₀ values ranging from 4.1 to 9.4 μM, which furnished potential lead molecules for the design and development of new immunosuppressants for treating autoimmune-associated diseases.

中文翻译：

Bipolaquinones A-J，来自土壤衍生的 Bipolaris zeicola 的免疫抑制性类萜

从土壤来源的真菌Bipolaris zeicola的发酵水稻培养物中分离并鉴定出十种新的类萜，双极醌 A-J ( 1 - 10 ) 和一种已知的同源物异莨菪醌 F ( 11 ) 。的平面结构1 - 10基于广泛的分光分析（包括HRESIMS和1D和2D NMR数据），和它们的绝对构型通过单晶X射线衍射分析，实验电子圆二色性的比较来确定被阐明（ECD）数据、ECD 计算和水解反应。免疫抑制活性分析表明，化合物2、3和7– 10对刀豆球蛋白 A (ConA) 诱导的 T 淋巴细胞增殖显示出显着的抑制活性，IC ₅₀值范围为 4.1 至 9.4 μM，这为设计和开发治疗自身免疫相关疾病的新型免疫抑制剂提供了潜在的先导分子。

更新日期：2021-09-24

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