School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, China.
J Nat Med. 2018 Jun;72(3):808-815. doi: 10.1007/s11418-018-1208-8. Epub 2018 Apr 5.
Two new dyhydrophaseic acid glucoside isomers, (1'S, 3'R, 5'S, 8'R, 2Z, 4E)-dihydrophaseic acid-3'-O-β-D-glucopyranoside (2) and (1'R, 3'S, 5'R, 8'R, 2Z, 4E)-dihydrophaseic acid-3'-O-β-D-glucopyranoside (4), together with 10 known compounds [myo-inositol (1), 3,4-dihydroxybenzoic acid (3), 3-O-galloyl quinic acid (5), ellagic acid (6), gallic acid (7), ethyl gallate (8), scopoletin (9), ellagic acid-4-O-β-D-glucopyranoside (10), ellagic acid-4-O-α-L-rhamnopyranoside (11), and isocorilagin (12)] were isolated from the chloroform extract of Canarium album Raeusch fruits by repeated chromatography on macroporous adsorption resin, silica gel, Sephadex LH-20, Toyopearl HW-40F, and reverse-phase C18 columns, etc. Their structures and absolute configurations were determined by comprehensive analysis of 1D- and 2D-nuclear magnetic resonance (NMR), high-resolution electron spray ionization mass spectrometry (HR-ESI-MS), ESI-MS, optical rotation, circular dichroism spectra, and comparison of NMR data with data of known compounds. Bioassay of their anti-influenza virus A activities showed that compounds 9 and 12 displayed a significant inhibitory effect with IC values of 22.9 ± 3.7 and 5.42 ± 0.97 μg/ml, respectively.
从橄榄果实的氯仿提取物中，通过反复的大孔吸附树脂、硅胶、Sephadex LH-20、Toyopearl HW-40F 和反相 C18 柱等层析分离，得到了两个新的二氢相位酸葡萄糖苷异构体[(1'S, 3'R, 5'S, 8'R, 2Z, 4E)-二氢相位酸-3'-O-β-D-吡喃葡萄糖苷（2）和(1'R, 3'S, 5'R, 8'R, 2Z, 4E)-二氢相位酸-3'-O-β-D-吡喃葡萄糖苷（4）]，以及 10 个已知化合物[肌醇（1）、3,4-二羟基苯甲酸（3）、3-O-没食子酰奎宁酸（5）、鞣花酸（6）、没食子酸（7）、没食子酸乙酯（8）、东莨菪素（9）、鞣花酸-4-O-β-D-吡喃葡萄糖苷（10）、鞣花酸-4-O-α-L-鼠李吡喃糖苷（11）和异柯里拉京（12）]。通过综合分析 1D 和 2D 核磁共振（NMR）、高分辨电子喷雾电离质谱（HR-ESI-MS）、电喷雾质谱（ESI-MS）、旋光、圆二色谱和与已知化合物 NMR 数据的比较，确定了它们的结构和绝对构型。抗流感病毒 A 活性的生物测定表明，化合物 9 和 12 具有显著的抑制作用，IC 值分别为 22.9±3.7 和 5.42±0.97μg/ml。
