Dimerized sesquiterpenoid [4 + 2] adducts with ferroptosis-promoting activity from Inula britannica Linn,Phytochemistry

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Dimerized sesquiterpenoid [4 + 2] adducts with ferroptosis-promoting activity from Inula britannica Linn
Phytochemistry ( IF 3.2 ) Pub Date : 2023-12-12 , DOI: 10.1016/j.phytochem.2023.113951
Cong Guo ₁ , Hui-Jun Geng ₂ , Wen-Ji Wang ₁ , Yan-Xiang Liu ₁ , Lu Deng ₂ , Jun-Mian Tian ₁ , Jin-Ming Gao ₁ , Jiang-Jiang Tang ₁

Affiliation

Inubritanolides C and D ( and ), two sesquiterpenoid [4 + 2] adducts with unprecedented interconverting conformations of twist-chair and chair, together with two previously undescribed [4 + 2] dimers ( and ) were discovered from flowers. Dimers and have an undescribed carbon skeleton comprising of eudesmanolide and guaianolide units with the linkage mode of C-11/C-1ʹ and C-13/C-3ʹ a Diels-Alder cycloaddition reaction. Their structures were elucidated using 1D/2D NMR, X-ray diffraction, ECD, and variable-temperature NMR experiments. Dimer displayed a strong inhibitory effect on breast cancer cells by promoting lipid ROS production, showing its potential as ferroptosis inducer.

中文翻译：

来自不列颠旋覆花 (Inula Britannica Linn) 的具有促进铁死亡活性的二聚倍半萜 [4 + 2] 加合物

从花中发现了 Inubritanolides C 和 D ( 和 )，两种倍半萜类 [4 + 2] 加合物，具有前所未有的扭椅式和椅式相互转换构象，以及两个先前未描述的 [4 + 2] 二聚体 ( 和 )。二聚体，具有未描述的碳骨架，由桉树内酯和愈创木酚内酯单元组成，连接方式为C-11/C-1′和C-13/C-3′，通过狄尔斯-阿尔德环加成反应进行。使用一维/二维核磁共振、X 射线衍射、ECD 和变温核磁共振实验阐明了它们的结构。二聚体通过促进脂质 ROS 的产生，对乳腺癌细胞表现出强烈的抑制作用，显示出其作为铁死亡诱导剂的潜力。

更新日期：2023-12-12

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