潘其明, 马双刚, 李勇, 张丹, 孙华, 侯琦, 陈晓光, 庾石山. 三脉马钱茎枝中酚苷类成分及其生物活性研究J. 药学学报, 2023, 58(1): 170-179. DOI: 10.16438/j.0513-4870.2022-0797
引用本文: 潘其明, 马双刚, 李勇, 张丹, 孙华, 侯琦, 陈晓光, 庾石山. 三脉马钱茎枝中酚苷类成分及其生物活性研究J. 药学学报, 2023, 58(1): 170-179. DOI: 10.16438/j.0513-4870.2022-0797
PAN Qi-ming, MA Shuang-gang, LI Yong, ZHANG Dan, SUN Hua, HOU Qi, CHEN Xiao-guang, YU Shi-shan. Phenolic glycosides from the stems and twigs of Strychnos cathayensis and their biological activitiesJ. Acta Pharmaceutica Sinica, 2023, 58(1): 170-179. DOI: 10.16438/j.0513-4870.2022-0797
Citation: PAN Qi-ming, MA Shuang-gang, LI Yong, ZHANG Dan, SUN Hua, HOU Qi, CHEN Xiao-guang, YU Shi-shan. Phenolic glycosides from the stems and twigs of Strychnos cathayensis and their biological activitiesJ. Acta Pharmaceutica Sinica, 2023, 58(1): 170-179. DOI: 10.16438/j.0513-4870.2022-0797

三脉马钱茎枝中酚苷类成分及其生物活性研究

Phenolic glycosides from the stems and twigs of Strychnos cathayensis and their biological activities

  • 摘要: 应用大孔树脂、硅胶、ODS、Sephadex LH-20柱色谱和半制备HPLC对三脉马钱茎枝95%乙醇提取物的正丁醇部位进行分离纯化, 分离得到14个化合物, 通过高分辨质谱、核磁共振波谱和文献数据分析, 分别鉴定为: 4-O-β-D-吡喃阿洛糖基香草酸乙酯(1)、4-O-β-D-吡喃阿洛糖基香草酸正丁酯(2)、4-O-(6′-O-丁香酰基)-β-D-吡喃阿洛糖基香草酸正丁酯(3)、4-O-(6′-O-香草酰基)-β-D-吡喃阿洛糖基香草酸正丁酯(4)、4-O-(6′-O-丁香酰基)-β-D-吡喃葡萄糖基香草酸正丁酯(5)、4-O-α-L-吡喃鼠李糖基丁香酸正丁酯(6)、3-甲氧基-4-β-D-吡喃阿洛糖氧基苯甲酸甲酯(7)、金钱松苷B (8)、丁香酸丁酯(9)、丁香酸葡萄糖苷(10)、丁香酸甲酯(11)、香草酸甲酯(12)、威灵仙苷C (13) 和小木通苷A (14), 其中化合物1~6为酚酸乙酯或正丁酯的人工产物。需要指出的是, 化合物34的生源前体4-O-(6′-O-丁香酰基)-β-D-吡喃阿洛糖基香草酸和4-O-(6′-O-香草酰基)-β-D-吡喃阿洛糖基香草酸均为新化合物。化合物1~13的体外活性评价表明, 在10 μmol·L-1的浓度下, 化合物126~10均具有潜在的肝细胞保护活性, 细胞存活率由扑热息痛模型组的45.4%提高到53.6%~55.5%; 化合物4具有一定的抗炎作用, 其一氧化氮生成抑制率为74.6%; 化合物35具有潜在抗氧化活性, 在10 μmol·L-1的浓度下, 丙二醛生成抑制率分别为53.2%和56.1%。

     

    Abstract: Fourteen compounds were isolated from the n-butanol fraction of the 95% aqueous ethanol extract of the stems and twigs of Strychnos cathayensis by D101 macroporous resin, silica gel, ODS, Sephadex LH-20 column chromatography, and semipreparative RP-HPLC. Their structures were elucidated as ethyl 4-O-β-D-allopyranosyl-vanillate (1), n-butyl 4-O-β-D-allopyranosyl-vanillate (2), n-butyl 4-O-(6′-O-syringoyl)-β-D-allopyranosyl-vanillate (3), n-butyl 4-O-(6′-O-vanilloyl)-β-D-allopyranosyl-vanillate (4), n-butyl 4-O-(6′-O-syringoyl)-β-D-glucopyranosyl-vanillate (5), n-butyl 4-O-α-L-rhamnopyranosyl-syringate (6), methyl 3-methoxy-4-(β-D-allopyranosyloxy) benzoate (7), pseudolaroside B (8), butyl syringate (9), glucosyringic acid (10), methyl syringate (11), methyl 4-hydroxy-3-methoxybenzoate (12), clemochinenoside C (13), and clemoarmanoside A (14), respectively, on the basis of spectroscopic data interpretation and by comparison with literature information. Compounds 1-6 are artificial products of phenolic acid esterified by ethanol or n-butanol. It is noted that the precursors (4-O-(6′-O-syringoyl)-β-D-allopyranosyl-vanillic acid and 4-O-(6′-O-vanilloyl)-β-D-allopyranosyl-vanillic acid) of compounds 3 and 4 are new compounds. The hepatoprotective, anti-inflammatory, antioxidant and cytotoxic activities of compounds 1-13 were evaluated in vitro at a concentration of 10 μmol·L-1. Compounds 1, 2 and 6-10 exhibited potential hepatic protection effects with cell survival rates ranging from 53.6% to 55.5% (acetaminophen, 45.4% at 8 mmol·L-1). Compound 4 demonstrated anti-inflammatory activity with nitric oxide inhibitory rate of 74.6%. Compounds 3 and 5 showed potential antioxidant activities with malondialdehyde inhibitory rates of 53.2% and 56.1%, respectively.

     

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