Tetrahedron Letters ( IF 1.8 ) Pub Date : 2020-12-18 , DOI: 10.1016/j.tetlet.2020.152733 Yanrong Zeng , Jue Yang , Yanan Li , Wei Gu , Liejun Huang , Ping Yi , Chunmao Yuan , Xiaojiang Hao
Four highly modified polycyclic polyprenylated acylphloroglucinols (PPAPs) with an unusual 6,5,5-tricyclic system, hypermogins A–D (1–4), together with one known analogue (5), were isolated from the flowers of Hypericum monogynum. From a possible biogenic synthesis pathway analysis, compounds 2 and 3 could be obtained by oxidation of a double bond and hydrolysis for 1 and 5. In addition, compound 3 might undergo a pinacol rearrangement to produce compound 4. The structures of the isolates were determined by comprehensive MS, NMR spectroscopy and electronic circular dichroism (ECD) calculations. All compounds significantly reversed multidrug resistance in MCF-7/ADR cells.
中文翻译:
Hypermogins A–D,来自金丝桃属植物金丝桃属植物的四种高度修饰的多环多戊烯基化酰基单糖醇
四个高度改性的聚环polyprenylated acylphloroglucinols(PPAPs)配有一个不寻常的6,5,5三环系统,hypermogins A-d(1 - 4),其中一个已知的类似物(一起5),是从的花中分离金丝桃monogynum。从可能的生物合成途径分析中,化合物2和3可以通过双键的氧化和1和5的水解获得。此外,化合物3可能会进行频哪醇重排以生成化合物4。分离物的结构通过综合质谱,核磁共振光谱和电子圆二色性(ECD)计算确定。所有化合物均显着逆转了MCF-7 / ADR细胞的多药耐药性。