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甜叶菊中高度氧化的半日花烷二萜类化合物及其抗动脉粥样硬化活性。

Highly Oxygenated Labdane Diterpenoids from Stevia rebaudiana and Their Anti-Atherosclerosis Activities.

作者信息

Cheng Bin, Fang Fei, Zhou Qin-Tao, Li Yan, Wu Xue-Wen, Zhao Xue-Rong, Bi De-Wen, Zhang Xing-Jie, Zhang Rui-Han, Ji Xu, Li Xiao-Li, Cao Guang, Xiao Wei-Lie

机构信息

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Characteristic Plant Extraction Laboratory, Yunnan Provincial Center for Research & Development of Natural Products, School of Pharmacy and School of Chemical Science and Technology, Yunnan University, Kunming, 650500, P. R. China.

State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan University, Kunming, 650091, P. R. China.

出版信息

Chem Biodivers. 2023 Jan;20(1):e202200999. doi: 10.1002/cbdv.202200999. Epub 2022 Dec 21.

Abstract

Five unknown labdane diterpenoids Stevelins A-E (1-5), three known labdane diterpenoids (6-8) and three labdane norditerpenoids (9-11) were isolated from the Stevia rebaudiana. The structures were determined primarily via NMR spectroscopic data and HR-ESI-MS experiments. X-ray crystallography using CuK radiation was used to determine the absolute configurations of 1, and the absolute configurations of 2-5 were deduced by electronic circular dichroism (ECD) calculations. The potential anti-atherosclerosis activities of all compounds were evaluated by measuring their inhibitory effects on the macrophage foam cell formation. As a result, most isolated compounds could significantly inhibit oxidized low-density lipoprotein (ox-LDL)-induced macrophage foam cell formation, which suggests that these compounds may be promising candidates in the treatment for atherosclerosis.

摘要

从甜叶菊中分离出了5种未知的半日花烷二萜类化合物甜叶菊素A - E(1 - 5)、3种已知的半日花烷二萜类化合物(6 - 8)和3种半日花烷降二萜类化合物(9 - 11)。其结构主要通过核磁共振光谱数据和高分辨电喷雾电离质谱实验确定。使用CuK辐射的X射线晶体学用于确定1的绝对构型,2 - 5的绝对构型通过电子圆二色光谱(ECD)计算推导得出。通过测量所有化合物对巨噬细胞泡沫细胞形成的抑制作用来评估其潜在的抗动脉粥样硬化活性。结果表明,大多数分离出的化合物能够显著抑制氧化型低密度脂蛋白(ox - LDL)诱导的巨噬细胞泡沫细胞形成,这表明这些化合物可能是治疗动脉粥样硬化的有前景的候选药物。

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