Duan Yulin, Guo Yi, Deng Yanfang, Bu Pengfei, Shi Zhengyi, Cao Yunfang, Zhang Yeting, Hu Hong, Sun Weiguang, Qi Changxing, Zhang Yonghui
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.
J Org Chem. 2022 May 20;87(10):6824-6831. doi: 10.1021/acs.joc.2c00503. Epub 2022 May 12.
Norprzewalsone A (), a rearranged polyprenylated polycyclic acylphloroglucinol (PPAP) with a new carbon skeleton, along with a new congener, norprzewalsone B (), were isolated from . Compound possessed a new 5/6/5/6/6 pentacyclic ring system based on a spiro[cyclopentane-1,3'-tricyclo[7.4.0.0]tridecane] core, which might be derived from the common [3.3.1]-type bicyclic polyprenylated acylphloroglucinol (BPAP) via the key retro-Claisen, intramolecular cyclization, and Diels-Alder cyclization reactions. Their structures and absolute configurations were confirmed by spectroscopic data, calculated 1D NMR data with DP4+ probability analyses, and electronic circular dichroism calculations and comparison. More significantly, compound exhibited a moderate inhibitory effect on NO production in lipopolysaccharide-stimulated RAW264.7 cells.
新绿原酸A（），一种具有新碳骨架的重排多异戊烯基多环酰基间苯三酚（PPAP），与一种新的同系物新绿原酸B（）一起，从……中分离得到。化合物……具有基于螺[环戊烷-1,3'-三环[7.4.0.0]十三烷]核心的新的5/6/5/6/6五环体系，该体系可能通过关键的逆克莱森反应、分子内环化反应和狄尔斯-阿尔德环化反应，从常见的[3.3.1]-型双环多异戊烯基酰基间苯三酚（BPAP）衍生而来。通过光谱数据、经DP4+概率分析计算的一维核磁共振数据以及电子圆二色性计算和比较，确定了它们的结构和绝对构型。更重要的是，化合物……在脂多糖刺激的RAW264.7细胞中对一氧化氮的产生表现出中等程度的抑制作用。
