Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2021-07-06 , DOI: 10.1016/j.bioorg.2021.105144 Yi Guo 1 , Yunfang Cao 1 , Changxing Qi 1 , Qingyi Tong 1 , Chunmei Chen 1 , Jing Yang 2 , Hucheng Zhu 1 , Yonghui Zhang 1
Hyperformitins A–I (1–9), nine undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) with double-bond migration, along with four new isomers hyperformitins J–M (10–13), were isolated from Hypericum perforatum. Their structures and absolute configurations were determined by spectroscopic analyses including HRESIMS, IR, UV, NMR, and ECD, as well as optical rotation (OR) calculations. The absolute configurations of previously reported analogues, garsubellins D and C as well as garcinielliptones L and M, were assigned for the first time by NMR spectra and specific rotations analyses assisting with OR calculations. Selected compounds were tested for their immunosuppressive activities against lipopolysaccharide (LPS)-induced B lymphocyte proliferation. Compounds 1, 3, 4, 5, 7, and 11 showed inhibition activities against the proliferation of B lymphocyte with IC50 values ranging from 4.1 to 9.7 μM. Furthermore, the neuroprotective activities of the isolates against corticosterone (CORT)-induced injury in PC12 cells were also tested, and compounds 1, 12, and 13 exhibited neuroprotective effects with cell viabilities of 68.0%, 71.3%, and 68.4%, respectively under the concentration of 10 μM.
中文翻译:
来自贯叶连翘的具有免疫抑制活性的多环聚异戊二烯化酰基间苯三酚和先前报道的类似物的绝对构型分配
Hyperformitins A–I ( 1 – 9 )、九个未描述的多环聚异戊二烯化酰基间苯三酚 (PPAP) 具有双键迁移,以及四个新异构体 hyperformitins J–M ( 10 – 13 ),是从贯叶连翘中分离出来的. 它们的结构和绝对构型是通过光谱分析确定的,包括 HRESIMS、IR、UV、NMR 和 ECD,以及旋光度 (OR) 计算。先前报道的类似物 garsubellins D 和 C 以及 garcinielliptones L 和 M 的绝对构型首次通过 NMR 光谱和比旋光度分析来辅助或计算。测试所选化合物对脂多糖 (LPS) 诱导的 B 淋巴细胞增殖的免疫抑制活性。化合物1 , 3 , 4 , 5 , 7 , 11对B淋巴细胞增殖有抑制作用,IC 50 。值范围从4.1至9.7 μ M.此外,分离的神经保护活性对皮质酮(CORT)诱导的损伤的PC12细胞也进行了测试,和化合物1,12,和13个与68.0%细胞存活率显示出神经保护作用, 10 μ M浓度下分别为 71.3% 和 68.4% 。