Bipodonines A–J, a new class of natural sesquiterpenes with a 2-(tetrahydro-2H-pyran-2-yl)propan-2-ol system from the fungus Bipolaris cynodontis DJWT-01,Organic Chemistry Frontiers

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Bipodonines A–J, a new class of natural sesquiterpenes with a 2-(tetrahydro-2H-pyran-2-yl)propan-2-ol system from the fungus Bipolaris cynodontis DJWT-01
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2023-04-03 , DOI: 10.1039/d3qo00235g
Yan Shu ₁ , Shi-Yu Feng ₁ , Sheng-Qi Zhang ₁ , Xun Tian ₁ , Yun-Li Zhao ₁ , Hua-Juan Yang ₁ , Jia-Xin Wang ₁ , Gui-Ling He ₂ , Hao Zhou ₁ , Jia-Peng Wang _{1,

2} , Le Cai ₁ , Zhong-Tao Ding ₃

Affiliation

Ten novel sesquiterpenes, bipodonines A–J (1–10) with a 2-(tetrahydro-2H-pyran-2-yl)propan-2-ol system, and two known polyketide–terpenoids (11 and 12) were characterized from Bipolaris cynodontis DJWT-01. The structures of new compounds were determined using extensive spectroscopic analyses, derivative reactions, X-ray diffraction analysis, ECD data and DP4+ calculations. Further investigation showed that bipodonines A and B featuring γ- and δ-lactone might be degradative derivatives of polyketide–terpenoid 11. Compounds 5, 7 and 11 promoted the proliferation of LPS-stimulated splenic lymphocytes at 20.0 μM in vitro. Compound 11 showed potent cytotoxic activities against four cell lines and also showed antimicrobial activity against Fusarium solani and F. oxysporum with minimum inhibitory concentrations (MICs) of 4.00 and 2.00 μg mL⁻¹, respectively. The plausible biosynthetic pathways, in vitro cytotoxicity, antimicrobial, and immunomodulatory activities of these compounds are discussed.

中文翻译：

Bipodonines A-J，一类新的天然倍半萜烯，具有来自真菌 Bipolaris cynodontis DJWT-01 的 2-(tetrahydro-2H-pyran-2-yl)propan-2-ol 系统

具有 2-(tetrahydro-2 H -pyran-2-yl)propan-2-ol 系统的十种新型倍半萜烯 A-J ( 1-10 ) 和两种已知的聚酮化合物-萜类化合物 ( 11 和12 ) 的特征来自Bipolaris cynodontis DJWT-01。新化合物的结构是通过广泛的光谱分析、衍生反应、X 射线衍射分析、ECD 数据和 DP4+ 计算确定的。进一步研究表明，具有 γ- 和 δ-内酯特征的双刺多宁 A 和 B 可能是聚酮化合物-萜类化合物11的降解衍生物。化合物5、7和11在 20.0 μM 时促进 LPS 刺激的脾淋巴细胞的增殖体外。化合物11显示出针对四种细胞系的有效细胞毒活性，并且还显示出针对茄病镰刀菌和尖孢镰刀菌的抗菌活性，最低抑菌浓度 (MIC) 分别为 4.00 和 2.00 μg mL ^-1。讨论了这些化合物的合理生物合成途径、体外细胞毒性、抗菌和免疫调节活性。

更新日期：2023-04-03

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