化学
环丙烷
壬烷
立体化学
绝对构型
竞争行为
位阻效应
戒指(化学)
有机化学
心理学
精神科
侵略
作者
Li Shen,Xiang Zou,Wan-Shan Li,Attila Mándi,Tibor Kurtán,Jun Wu
标识
DOI:10.1016/j.bioorg.2021.104888
摘要
Two unprecedented limonoids incorporating a sterically encumbered cyclopropane ring, named granatripodins A (1) and B (2), featuring the presence of a tricyclo[3.3.1.02,8]nonane motif, were obtained from seeds of the Thai Xylocarpus granatum. The planar structures and absolute configurations of these limonoids were unambiguously established by NMR investigations, TDDFT-ECD and DFT-NMR calculations, and single-crystal X-ray diffraction analysis (Cu Kα). Most notably, granatripodin A (1) exhibited agonistic effects on human pregnane-X-receptor at the concentration of 100.0 nM. The biosynthetic origins of these limonoids via a radical cascade reaction are proposed. This study exemplifies a universal approach for the stereochemical assignment of polycyclic compounds with a cyclopropane-embedded cage scaffold.
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