Tao Bo, Li Yongqi, Shi Zhengyi, Duan Yulin, Guo Yi, Huang Xinye, Li Jie, Zhang Yeting, Chen Ming, Song Fei, Lan Xueqi, Sun Weiguang, Gu Lianghu, 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, 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; Department of Pharmacy, Wuhan No.1 Hospital, 215 Zhongshan Road, Wuhan 430022, Hubei, People's Republic of China.
Phytochemistry. 2024 Feb;218:113953. doi: 10.1016/j.phytochem.2023.113953. Epub 2023 Dec 13.
In this work, nine previous undescribed polycyclic polyprenylated acylphloroglucinols with adamantine/homoadamantane skeletons, cumilcinols A-I (1-9), along with six known analogues, were isolated and identified from the stems, leaves and flowers of Hypericum wilsonii. Their structures were determined by HRESIMS, NMR spectroscopic analysis, single-crystal X-ray crystallography as well as electronic circular dichroism calculations and comparisons. Compound 2 formed a unique furan ring bearing a rare acetal functionality. In bioassays, hyperacmosin G (13) could significantly inhibit the production of NO in LPS-stimulated RAW264.7 cell (IC = 4.350 ± 1.146 μM), and increased expression of related transcription factors at the gene level, inhibit the nuclear translocation of NF-κBp65, and reduce the protein expression of COX-2. Additionally, compound 5 showed significant inhibitory activity on Con A-induced T-lymphocyte proliferation (IC = 4.803 ± 3.149 μM), and treatment of 5 could reduce the increased ratio of CD4 and CD8 subpopulations induced by Con A in vitro. Those results indicated 13 possesses potential anti-inflammatory activity, and 5 exhibits a certain degree of immunosuppressive activity.
在本研究中，从金丝桃的茎、叶和花中分离并鉴定出9个以前未描述过的具有金刚烷/高金刚烷骨架的多环多异戊烯基酰基间苯三酚，即cumilcinols A - I（1 - 9），以及6个已知类似物。它们的结构通过高分辨电喷雾电离质谱（HRESIMS）、核磁共振光谱分析、单晶X射线晶体学以及电子圆二色性计算和比较来确定。化合物2形成了一个带有罕见缩醛官能团的独特呋喃环。在生物测定中，hyperacmosin G（13）能显著抑制脂多糖（LPS）刺激的RAW264.7细胞中一氧化氮（NO）的产生（IC = 4.350 ± 1.146 μM），并在基因水平上增加相关转录因子的表达，抑制核因子κB p65（NF - κBp65）的核转位，并降低环氧化酶 - 2（COX - 2）的蛋白表达。此外，化合物5对刀豆蛋白A（Con A）诱导的T淋巴细胞增殖具有显著抑制活性（IC = 4.803 ± 3.149 μM），并且用5处理可降低体外Con A诱导的CD4和CD8亚群增加的比例。这些结果表明13具有潜在的抗炎活性，而5表现出一定程度的免疫抑制活性。
