邱成省, 王吉, 穆利萍, 张荣平, 陈兴龙. 益智的化学成分及其神经保护作用J. 药学学报, 2023, 58(9): 2746-2753. DOI: 10.16438/j.0513-4870.2023-0080
引用本文: 邱成省, 王吉, 穆利萍, 张荣平, 陈兴龙. 益智的化学成分及其神经保护作用J. 药学学报, 2023, 58(9): 2746-2753. DOI: 10.16438/j.0513-4870.2023-0080
QIU Cheng-xing, WANG Ji, MU Li-ping, ZHANG Rong-ping, CHEN Xing-long. Chemical constituents from the fruits of Alpinia oxyphylla and their neuroprotective effectsJ. Acta Pharmaceutica Sinica, 2023, 58(9): 2746-2753. DOI: 10.16438/j.0513-4870.2023-0080
Citation: QIU Cheng-xing, WANG Ji, MU Li-ping, ZHANG Rong-ping, CHEN Xing-long. Chemical constituents from the fruits of Alpinia oxyphylla and their neuroprotective effectsJ. Acta Pharmaceutica Sinica, 2023, 58(9): 2746-2753. DOI: 10.16438/j.0513-4870.2023-0080

益智的化学成分及其神经保护作用

Chemical constituents from the fruits of Alpinia oxyphylla and their neuroprotective effects

  • 摘要: 采用正相硅胶、MCI、RP-18、Sephadex LH-20、制备薄层色谱及半制备HPLC等分离手段, 并结合HR-ESI-MS、NMR、ECD、X-单晶衍射等结构鉴定方法, 从益智干燥果实90%乙醇提取物的乙酸乙酯部位中分离得到14个化合物, 分别鉴定为: (2R, 5R, 7R, 10S)-2, 7-dihydroxyl-eudesmane-3(4), 11(12)-diene (1)、α-rotunol (2)、diketone I (3)、(1S, 4S, 5R, 7S)-1-hydroxyl-eremophilane-9(10), 11(12)-diene-8-one (4)、cyperusol A1 (5)、(6R, 9S, 10S)-10-hydroxyl-11, 12, 13-trinor-cadinane-4(5)-ene-3-one (6)、(2E, 4E)-6-hydroxy-2, 6-dimethylhepta-2, 4-dienal (7)、益智醇(8)、益智酮A (9)、(5R)-5-羟基-1, 7-二苯基-3-庚酮(10)、(5S)-5-羟基-7-(4″-羟基)-苯基-1-苯基-3-庚酮(11)、(5S)-5-羟基-7-(4″-羟基-3″-甲氧基)-苯基-1-苯基-3-庚酮(12)、7-(4″-羟基-3″-甲氧基)-苯基-1-苯基-3, 5-庚二酮(13)、bis-(2-ethylhexyl) terephthalate (14)。化合物1~6为倍半萜类化合物, 其中化合物1为新的桉烷型倍半萜类化合物, 化合物7为单萜类化合物, 化合物8~13为二苯基庚烷类化合物, 化合物2~614为首次从益智中分离得到。H2O2氧化损伤SH-SY5Y细胞实验表明, 化合物2671213在低、中浓度下具有神经保护作用, 尤其是化合物6在低、中、高浓度下细胞存活率均高于阳性药表没食子儿茶素没食子酸酯(EGCG), 显示较好的神经保护作用。

     

    Abstract: Fourteen compounds were isolated from the ethyl acetate fraction of 90% EtOH extracts of the dried fruits of Alpinia oxyphylla by silica gel, MCI, RP-18, Sephadex LH-20, TLC and semi-preparative HPLC column chromatography. Their structures were identified by HR-ESI-MS, UV, IR, NMR, ECD and X ray single crystal diffraction spectroscopic data as: (2R, 5R, 7R, 10S)-2, 7-dihydroxyl-eudesmane-3(4), 11(12)-diene (1), α-rotunol (2), diketone I (3), (1S, 4S, 5R, 7S)-1-hydroxyl-eremophilane-9(10), 11(12)-diene-8-one (4), cyperusol A1 (5), (6R, 9S, 10S)-10-hydroxyl-11, 12, 13-trinor-cadinane-4(5)-ene-3-one (6), (2E, 4E)-6-hydroxy-2, 6-dimethylhepta-2, 4-dienal (7), oxyphyllacinol (8), yakuchinone A (9), (5R)-5-hydroxy-1, 7-diphenylhept-3-heptanone (10), (5S)-5-hydroxy-7-(4″-hydroxyphenyl)-1-phenylhept-3-heptanone (11), (5S)-5-hydroxy-7-(4″-hydroxyl-3″-methoxyphenyl)-1-phenyl-3-heptanone (12), 7-(4″-hydroxy-3″-methoxyphenyl)-1-phenyl-3, 5-heptadione (13), bis-(2-ethylhexyl) terephthalate (14). Compounds 1-6 were sesquiterpenoids in which compound 1 is a new eudesmane sesquiterpenoid and compound 7 was a monoterpenoid. Compounds 8-13 were diarylheptanoids, and compounds 2-6 and 14 were isolated from A.oxyphylla for the first time. The experiments on H2O2 induced SH-SY5Y cells showed that compounds 2, 6, 7, 12 and 13 had neuroprotective effects at low and medium concentrations. In particular, compound 6 showed obvious neuroprotective effect at low, medium and high concentrations whose cell viability was higher than that of the positive control.

     

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