知母须根中1个新的二苯甲酮类化合物
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摘要
采用硅胶、Sephadex LH-20结合高压半制备高效液相色谱技术研究知母Anemarrhena asphodeloides的须根中的化学成分。通过理化性质和波谱数据鉴定了5个化合物:methyl 2-[2,4-dihydroxy-3-(4-hydroxybenzoyl)-6-methoxypheyl]acetate(1)、4-[formyl-5-(methoxymethyl)-1H-pyrrol-1-yl] butanoate(2)、川芎哚(3)、丁香脂酚-4′-β-D-葡萄糖苷(4)和4′,6-dihydroxy-4-methoxybenzophenone-2-O-(2″),3-C-(1″)-1″-desoxy-α-L-fructofuranoside(5)。其中化合物1为新化合物,化合物2～5均为首次从该植物中得到。并检测新化合物1对H_2O_2诱导的SH-SY5Y细胞损伤的神经保护活性。
Five compounds were isolated from the fibrous roots of Anemarrhena asphodeloides by silica gel, Sephadex LH-20 and semi-HPLC column chromatography. On the basis of physic-chemical properties and spectroscopic data analysis, these compounds were identified as methyl 2-[2,4-dihydroxy-3-(4-hydroxybenzoyl)-6-methoxyphenyl]acetate(1), 4-[formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoate(2), perlolyrine(3),syringaresinol-4′-O-β-D-glucoside(4) and 4′,6-dihydroxy-4-methoxybenzophenone-2-O-(2″),3-C-(1″)-1″-desoxy-α-L-fructofuranoside(5). Among them, 1 was a new benzophenone. Compounds 2-5 were isolated from this plant for the first time. Compound 1 was tested for neuroprotective effects against H_2O_2-induced damage in SH-SY5 Y cells.
Five compounds were isolated from the fibrous roots of Anemarrhena asphodeloides by silica gel, Sephadex LH-20 and semi-HPLC column chromatography. On the basis of physic-chemical properties and spectroscopic data analysis, these compounds were identified as methyl 2-[2,4-dihydroxy-3-(4-hydroxybenzoyl)-6-methoxyphenyl]acetate(1), 4-[formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoate(2), perlolyrine(3),syringaresinol-4′-O-β-D-glucoside(4) and 4′,6-dihydroxy-4-methoxybenzophenone-2-O-(2″),3-C-(1″)-1″-desoxy-α-L-fructofuranoside(5). Among them, 1 was a new benzophenone. Compounds 2-5 were isolated from this plant for the first time. Compound 1 was tested for neuroprotective effects against H_2O_2-induced damage in SH-SY5 Y cells.
引文
[1] 中国药典.一部[S]. 2015.
[2] Hu H, Zhang R, Zhang Y, et al. Role of CREB in the regulatory action of sarsasapogenin on muscarinic M1 receptor density during cell aging[J]. Febs Lett, 2010, 584(8):1549.
[3] 邓云,马百平,徐秋萍,等.知母有效成分对拟痴呆模型大鼠学习记忆的影响及机制[J].中国药理学通报,2005(7):830.
[4] Lee B, Jung K, Kim D H. Timosaponin AⅢ, a saponin isolated from Anemarrhena asphodeloides, ameliorates learning and memory deficits in mice[J]. Pharm Biochem Behav, 2009, 93(2):121.
[5] Nakashima N, Kimura I, Kimura M, et al. Isolation of pseudoprototimosaponin AⅢ from rhizomes of Anemarrhena asphodeloides and its hypoglycemic activity in streptozotocin-induced diabetic mice[J]. J Nat Prod, 1993, 56(3): 345.
[6] Zhang J, Meng Z, Zhang M, et al. Effect of six steroidal saponins isolated from Anemarrhenae Rhizoma on platelet aggregation and hemolysis in human blood[J]. Clin Chim Acta, 1999, 289(1/2): 79.
[7] Kaname N, Zhang J, Meng Z,et al. Effect of timosaponin E1 and E2 on superoxide generation induced by various stimuli in human neutrophils and on platelet aggregation in human blood[J]. Clin Chim Acta, 2000, 295(1): 129.
[8] Liu Q B, Peng Y, Li L Z, et al. Steroidal saponins from Anemarrhena asphodeloides[J]. J Asian Nat Prod Res, 2013, 15(8): 891.
[9] YounU J, Lee Y S, Jeong H, et al. Identification of antiadipogenic constituents of the rhizomes of Anemarrhena asphodeloides[J]. J Nat Prod, 2009, 72(10): 1895.
[10] Bae G, Yu J R, Lee J, et al. Identification of nyasol and structurally related compounds as the active principles from Anemarrhena asphodeloides against respiratory syncytial virus (RSV)[J]. Chem Biodiver, 2007, 4(9): 2231.
[11] 邓海鸣,王蔚,黄洁英. 知母药材中芒果苷提取工艺研究[J].今日药学,2013,23(8):486.
[12] 黄琪,肖曦晨,金传山,等.知母须根化学成分研究[J].安徽中医药大学学报,2018,37(2):81.
[13] 魏树奇,崔同淑,杨继凡,等.知母须根与主根主要成分及药理作用的初步实验比较[J].中药材科技,1982(2):15.
[14] Rancon S, Chaboud A, Darbour N, et al. Natural and synthetic benzophenones: interaction with the cytosolic binding domain of P-glycoprotein[J]. Phytochemistry, 2001, 57(4): 553.
[15] Pan J, Yi X, Wang Y, et al. Benzophenones from mango leaves exhibit α-glucosidase and NO inhibitory activities[J]. J Agr Food Chem, 2016, 64(40): 7475.
[16] Chin Y W, Lim S W, Kim S H, et al. Hepatoprotective pyrrole derivatives of Lycium chinense fruits[J]. Bioorg Med Chem Lett, 2003, 13(1):79.
[17] 唐振球,王新国,杨炳友,等.接骨木果实化学成分的分离与结构鉴定[J].中国药物化学杂志,2017,27(3):225.
[18] 王明安,王明奎,彭树林,等.青檀树皮中的化学成分[J].天然产物研究与开发,2001(6):5.
[2] Hu H, Zhang R, Zhang Y, et al. Role of CREB in the regulatory action of sarsasapogenin on muscarinic M1 receptor density during cell aging[J]. Febs Lett, 2010, 584(8):1549.
[3] 邓云,马百平,徐秋萍,等.知母有效成分对拟痴呆模型大鼠学习记忆的影响及机制[J].中国药理学通报,2005(7):830.
[4] Lee B, Jung K, Kim D H. Timosaponin AⅢ, a saponin isolated from Anemarrhena asphodeloides, ameliorates learning and memory deficits in mice[J]. Pharm Biochem Behav, 2009, 93(2):121.
[5] Nakashima N, Kimura I, Kimura M, et al. Isolation of pseudoprototimosaponin AⅢ from rhizomes of Anemarrhena asphodeloides and its hypoglycemic activity in streptozotocin-induced diabetic mice[J]. J Nat Prod, 1993, 56(3): 345.
[6] Zhang J, Meng Z, Zhang M, et al. Effect of six steroidal saponins isolated from Anemarrhenae Rhizoma on platelet aggregation and hemolysis in human blood[J]. Clin Chim Acta, 1999, 289(1/2): 79.
[7] Kaname N, Zhang J, Meng Z,et al. Effect of timosaponin E1 and E2 on superoxide generation induced by various stimuli in human neutrophils and on platelet aggregation in human blood[J]. Clin Chim Acta, 2000, 295(1): 129.
[8] Liu Q B, Peng Y, Li L Z, et al. Steroidal saponins from Anemarrhena asphodeloides[J]. J Asian Nat Prod Res, 2013, 15(8): 891.
[9] YounU J, Lee Y S, Jeong H, et al. Identification of antiadipogenic constituents of the rhizomes of Anemarrhena asphodeloides[J]. J Nat Prod, 2009, 72(10): 1895.
[10] Bae G, Yu J R, Lee J, et al. Identification of nyasol and structurally related compounds as the active principles from Anemarrhena asphodeloides against respiratory syncytial virus (RSV)[J]. Chem Biodiver, 2007, 4(9): 2231.
[11] 邓海鸣,王蔚,黄洁英. 知母药材中芒果苷提取工艺研究[J].今日药学,2013,23(8):486.
[12] 黄琪,肖曦晨,金传山,等.知母须根化学成分研究[J].安徽中医药大学学报,2018,37(2):81.
[13] 魏树奇,崔同淑,杨继凡,等.知母须根与主根主要成分及药理作用的初步实验比较[J].中药材科技,1982(2):15.
[14] Rancon S, Chaboud A, Darbour N, et al. Natural and synthetic benzophenones: interaction with the cytosolic binding domain of P-glycoprotein[J]. Phytochemistry, 2001, 57(4): 553.
[15] Pan J, Yi X, Wang Y, et al. Benzophenones from mango leaves exhibit α-glucosidase and NO inhibitory activities[J]. J Agr Food Chem, 2016, 64(40): 7475.
[16] Chin Y W, Lim S W, Kim S H, et al. Hepatoprotective pyrrole derivatives of Lycium chinense fruits[J]. Bioorg Med Chem Lett, 2003, 13(1):79.
[17] 唐振球,王新国,杨炳友,等.接骨木果实化学成分的分离与结构鉴定[J].中国药物化学杂志,2017,27(3):225.
[18] 王明安,王明奎,彭树林,等.青檀树皮中的化学成分[J].天然产物研究与开发,2001(6):5.