Two new seco-polycyclic polyprenylated acylphloroglucinol from Hypericum sampsonii,Organic & Biomolecular Chemistry

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Two new seco-polycyclic polyprenylated acylphloroglucinol from Hypericum sampsonii
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-11-12 , DOI: 10.1039/d0ob02072a
Zi-Zhen Zhang ₁ , Yan-Rong Zeng , Ya-Nan Li , Zhan-Xing Hu , Lie-Jun Huang , Wei Gu , Xiao-Jiang Hao , Chun-Mao Yuan

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Hypsampsone A (1) and hyperhexanone F (2), two novel seco-polycyclic polyprenylated acylphloroglucinols, were isolated from Hypericum sampsonii. Hypsampsone A (1) features the first spirocyclic system fused with 5/6/5/5 tetracyclic skeleton. Hyperhexanone F (2) represents the second novel 1,2-seco-bicyclo[3.3.1]-PPAP skeleton. Their structures were established by extensive spectroscopic analysis, computer-assisted structure elucidation software, and calculated electronic circular dichroism spectra. A plausible biogenetic pathway of 1 was also proposed. Compounds 1 and 2 showed moderate multidrug resistance reversal activity to adriamycin (ADR) resistant cancer cell lines, HepG2/ADR and MCF-7/ADR, with the fold-reversals ranging from 16 to 38 at noncytotoxic concentration of 10 μM.

中文翻译：

来自金丝桃属植物金丝桃属植物的两种新型的多环多环戊二烯丙基酰基间苯三酚

hypsampsone A（1）和hyperhexanone F（2），两个新颖的山高多环多prenynylated acylphloroglucinols，从金丝桃属植物。Hypsampsone A（1）具有与5/6/5/5四环骨架融合的第一个螺环系统。高己酮F（2）代表第二个新颖的1,2-seco-双环[3.3.1] -PPAP骨架。通过广泛的光谱分析，计算机辅助的结构解析软件和计算的电子圆二色性光谱，确定了它们的结构。还提出了一个合理的生物遗传途径1。化合物1和2 对抗阿霉素（ADR）的癌细胞系HepG2 / ADR和MCF-7 / ADR具有中等程度的多药耐药逆转活性，在10μM的非细胞毒性浓度下，逆转倍数范围为16至38。

更新日期：2020-11-12

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