Li Yan-Hong, Bai Xi-Shan, Yang Xiu-Xia, Li Yu-Xiao, Li Hong-Rui, Wang Zi-Liang, Wang Wei, Tian Kai, Huang Xiang-Zhong
Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, School of Ethnic Medicine, Yunnan Minzu University, Kunming, 650504, Yunnan, China.
Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, School of Ethnic Medicine, Yunnan Minzu University, Kunming, 650504, Yunnan, China.
Phytochemistry. 2023 Oct;214:113795. doi: 10.1016/j.phytochem.2023.113795. Epub 2023 Jul 23.
Herein, five undescribed oleanane-type triterpenoid saponins, namely, psammosaponins A-E, along with nine known compounds, were isolated from the roots of Psammosilene tunicoides. Moreover, part of the ethanolic extract of P. tunicoides was acid-hydrolyzed and three aglycones were isolated from the resulting hydrolysate. The structures of all compounds were established through extensive analysis involving 1D and 2D NMR experiments, HRESIMS measurements, chemical derivatization, and comparison of spectroscopic data with the values reported in the literature. In all, 10 of the isolated saponins and the three aglycones were evaluated in the acetic acid-induced writhing model for their antinociceptive activity. At a dose of 40 mg/kg, these compounds exhibited significant inhibitory effects on the mouse writhing response, with inhibitions ranging from 31.9% to 79.3%. In addition, the structure-activity relationships of the isolates were discussed. Among the isolates, quillaic acid 3-O-glucuronide and 16α-hydroxygypsogenic acid showed better antinociceptive activity with inhibitions of 79.3% and 73.7%, respectively. Both isolates also exhibited antinociceptive activities in hot plate and formalin tests on mice. Their antinociceptive mechanism was explored in lipopolysaccharide-stimulated RAW 264.7 cells. These isolates could significantly inhibit the production of nitric oxide and interleukin-6 and downregulate the expression levels of inducible NO synthase, COX-1, and COX-2.
本文从金铁锁（Psammosilene tunicoides）根部分离得到5个未被描述的齐墩果烷型三萜皂苷，即金铁锁皂苷A - E，以及9个已知化合物。此外，将金铁锁的部分乙醇提取物进行酸水解，并从水解产物中分离得到3种苷元。所有化合物的结构通过1D和2D NMR实验、高分辨电喷雾电离质谱（HRESIMS）测定、化学衍生化以及与文献报道值的光谱数据比较进行了广泛分析得以确定。总共对分离得到的10种皂苷和3种苷元在醋酸诱导扭体模型中进行了抗伤害感受活性评价。在40 mg/kg剂量下，这些化合物对小鼠扭体反应表现出显著抑制作用，抑制率在31.9%至79.3%之间。此外，还讨论了分离物的构效关系。在分离物中，奎诺酸3 - O - 葡萄糖醛酸苷和16α - 羟基绞股蓝皂苷元表现出较好的抗伤害感受活性，抑制率分别为79.3%和73.7%。这两种分离物在小鼠热板和福尔马林试验中也表现出抗伤害感受活性。在脂多糖刺激的RAW 264.7细胞中探究了它们的抗伤害感受机制。这些分离物可显著抑制一氧化氮和白细胞介素 - 6的产生，并下调诱导型一氧化氮合酶、COX - 1和COX - 2的表达水平。
