Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Bioorg Chem. 2021 Jun;111:104902. doi: 10.1016/j.bioorg.2021.104902. Epub 2021 Apr 20.
Five new 2-nor-bicyclic polyprenylated acylphloroglucinols (BPAPs), norhyperpalums A-E (1-5), three new 2,3-nor-BPAPs, norhyperpalums F-H (8-10), one new 2,3,4-nor-BPAP (13), and four known analogs (6, 7, 11 and 12) were obtained from Hypericum patulum. Their structures were confirmed by spectroscopic data, electronic circular dichroism (ECD) calculations and comparisons, quantum-chemical C NMR calculations with DP4 + probability analysis, the modified Mosher's method, Rh(OCOCF)-induced ECD, and X-ray crystallographic data. Norhyperpalums A-E (1-5) are rare 2-nor-BPAPs bearing a 6/5/5 system based on a hexacyclic-fused 1,6-dioxaspiro[4.4]nonane core, and norhyperpalums F and G (8 and 9) exhibit an unusual 6-oxabicyclo[3.2.1]octane architecture. More significantly, compound 2 displayed pronounced cytotoxicities against hepatoma cell lines by the induction of S-phase cell cycle arrest and promotion of cell apoptosis.
从贯叶连翘中分离得到了五个新的双环多聚异戊烯基酰基间苯三酚（BPAPs），即 norhyperpalums A-E（1-5），三个新的 2,3-双环 BPAPs，norhyperpalums F-H（8-10），一个新的 2,3,4-双环 BPAP（13）和四个已知类似物（6、7、11 和 12）。通过光谱数据、电子圆二色性（ECD）计算和比较、量子化学 C NMR 计算与 DP4+概率分析、改进的 Mosher 法、Rh(OCOCF)诱导的 ECD 和 X 射线晶体学数据确定了它们的结构。Norhyperpalums A-E（1-5）是罕见的 2-双环 BPAPs，具有基于六元环稠合 1,6-二氧螺[4.4]壬烷核心的 6/5/5 系统，norhyperpalums F 和 G（8 和 9）则表现出不寻常的 6-氧杂双环[3.2.1]辛烷结构。更重要的是，化合物 2 通过诱导 S 期细胞周期阻滞和促进细胞凋亡，对肝癌细胞系显示出明显的细胞毒性。
