CN109232506A - 一种银杏叶来源的聚酮类化合物及其作为抗病毒药物的应用 - Google Patents
一种银杏叶来源的聚酮类化合物及其作为抗病毒药物的应用 Download PDFInfo
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Abstract
本发明涉及一种银杏叶来源的聚酮类化合物及其作为抗病毒药物的应用，所述聚酮类化合物具有式I所示结构：
Description
技术领域
本发明属于药用植物提取领域，具体涉及一种银杏叶来源的聚酮类化合物及其作为抗病毒药物的应用。
背景技术
银杏树又称白果树，目前主要分布于山东、江苏、广西、安徽、浙江、湖北等地，银杏的根、果、叶均可作为药用，也可食用。其中银杏叶在药用方面应用广泛，表现出多种药理活性，如抗氧化、扩张血管、改善记忆等，临床则被应用于质量肾病、冠心病、心绞痛、糖尿病等。银杏叶中主要的活性成分为银杏黄酮和萜类内脂。本发明首次从银杏叶中分离得到一种聚酮类化合物。
发明内容
本发明提供一种银杏叶来源的聚酮类化合物或其药学上可接受的盐，其特征在于所述聚酮类化合物具有式I所示结构：
本发明提供一种制备上述银杏叶来源的聚酮类化合物的方法，其特征在于包括如下步骤：
(1)将干燥的银杏叶粉碎后，用体积分数为60％的乙醇溶液加热至回流温度提取5h后，过滤、滤液经减压浓缩得粗提物；
(2)将步骤(1)得到的粗提物先经减压硅胶柱层析，采用石油醚-乙酸乙酯混合溶剂作为洗脱剂进行梯度洗脱，洗脱梯度分别为100:0、90:10、80:20、70:30、60:40，50:50、40:60、30:70、20:80、10:90、0:100，每个梯度收集三个柱体积，将洗脱梯度为70:30～60:40的洗脱液合并，浓缩得组分A；
(3)将步骤(2)得到的组分A先经正相硅胶柱层析，洗脱剂为石油醚：乙酸乙酯＝2.5:1的混合溶剂，洗脱5个柱体积，合并第3-5柱体积的洗脱液，减压浓缩后再经SephadexLH-20凝胶柱层析，洗脱剂为CHCl3:MeOH＝1:1的混合溶剂，洗脱4个柱体积，合并第3-4个柱体积的洗脱液，减压浓缩后再经高效液相色谱HPLC制备得式I化合物。
上述制备方法，步骤(1)中银杏叶粉碎后的粒度优选为20-80目，所述乙醇溶液的用量为每千克银杏叶(干重)使用3L乙醇溶液；步骤(2)所述减压正相硅胶柱层析使用的硅胶优选100-200目硅胶；步骤(3)中所述正相硅胶柱层析使用的硅胶优选200-300目硅胶；所述高效液相色谱HPLC制备的色谱条件为：色谱柱为Agilent C18,9.4×250mm，7μm，流速为2mL/min，流动相为MeOH∶H2O＝60∶40。
本发明色谱分离中所有涉及洗脱剂或流动相比例均为体积比。
本发明的另一实施方案提供上述银杏叶来源的聚酮类化合物(式I化合物)或其药学上可接受的盐在制备抗病毒药物中的应用。
本发明的另一实施方案提供上述银杏叶来源的聚酮类化合物(式I化合物)或其药学上可接受的盐在制备抗EV71药物中的应用。
本发明的另一实施方案提供上述银杏叶来源的聚酮类化合物(式I化合物)或其药学上可接受的盐在制备预防和/或治疗由EV71感染引起的疾病的药物中的应用。
具体实施方式
为了便于对本发明的进一步理解，下面提供的实施例对其做了更详细的说明。但是这些实施例仅供更好地理解发明而并非用来限定本发明的范围或实施原则，本发明的实施方式不限于以下内容。
实施例1
(1)将干燥的银杏叶(2.0kg)粉碎后(20-80目)，用体积分数为60％的乙醇溶液(6.0L)加热至回流温度提取5h后，过滤、滤液经减压浓缩得粗提物(约220g)；
(2)将步骤(1)得到的粗提物先经减压硅胶柱层析(100-200目硅胶)，采用石油醚-乙酸乙酯混合溶剂作为洗脱剂进行梯度洗脱，洗脱梯度分别为100:0、90:10、80:20、70:30、60:40，50:50、40:60、30:70、20:80、10:90、0:100，每个梯度收集三个柱体积，将洗脱梯度为70:30～60:40的洗脱液合并，浓缩得组分A(6.25g)；
(3)将步骤(2)得到的组分A先经正相硅胶柱层析(200-300目硅胶)，洗脱剂为石油醚：乙酸乙酯＝2.5:1的混合溶剂，洗脱5个柱体积，合并第3-5柱体积的洗脱液，减压浓缩后再经Sephadex LH-20凝胶柱层析，洗脱剂为CHCl3:MeOH＝1:1的混合溶剂，洗脱4个柱体积，合并第3-4个柱体积的洗脱液，减压浓缩后再经高效液相色谱HPLC制备(色谱柱为AgilentC18,9.4×250mm，7μm，流速为2mL/min，流动相为MeOH∶H2O＝60∶40)即得式I化合物(18mg)。
式I化合物：淡黄色粉末，1H NMR(500MHz,acetone-d6)δ:13.77(1H,brs,8-OH),12.07(1H,brs,1′-OH),11.67(1H,brs,1-OH),7.50(1H,d,J＝8.5Hz,H-3),7.48(1H,d,J＝8.5Hz,H-3′),6.57(2H,d,J＝8.5Hz,H-4,4′),4.08(1H,d,J＝1.5Hz,H-5′),3.96(1H,d,J＝10.5Hz,H-5),3.69(3H,s,H-13),3.65(6H,d,H-13′,14′),3.48(1H,d,J＝17.5Hz,H1-8a′),3.18(1H,d,J＝17.5Hz,H2-8a′),2.73(1H,m,H-6),2.59(1H,m,H-6′),2.47(2H,m,H-7),2.36(2H,m,H-7′),1.15(3H,d,J＝5.5Hz,H-11),1.07(3H,d,J＝6.5Hz,H-11′)；13C NMR(125MHz,acetone-d6)δ:197.9(C,C-9′),188.6(C,C-9),178.8(C,C-8),173.4(C,C-8′),171.2(C,C-12′),171.0(C,C-12),160.2(C,C-1),160.1(C,C-1′),159.9(C,C-4a),159.6(C,C-4a′),141.5(CH,C-3′),141.2(CH,C-3),118.3(C,C-2),118.0(C,C-2′),108.4(CH,C-4),108.1(CH,C-4′),107.9(C,C-9a),107.5(C,C-9a′),102.8(C,C-8a),88.8(C,C-10a′),86.2(C,C-10a),76.9(CH,C-5′),76.4(CH,C-5),53.3(CH3,C-13),53.0(CH3,C-13′),51.7(CH3,C-14′),41.0(CH2,C-7′),40.5(CH2,C-8a′),36.7(CH2,C-7),32.1(CH,C-6′),30.7(CH,C-6),18.3(CH3,C-11),14.5(CH3,C-11′).
实施例2抗病毒活性测试
采用细胞病变抑制作用(CPE)对肠道病毒71(EV71)进行体外抗病毒活性测试，方法如下：
将培养成单层的Vero细胞用胰酶消化后，接种于96孔板中，长成单层备用，将EV71病毒接种于Vero细胞上，加2％血清1640培养液后置37℃、5％CO2条件下培养，出现90％以上的病变后，反复冻融3次后吹打离心，定量分装，-80℃冰箱冻存备用，式I化合物与利巴韦林每管以10μL DMSO溶解后，加入200μL的2％1640培养液，并连续10次2倍比稀释，共10个稀释度，然后横向接种于96孔板中的单层细胞上，11列为病毒对照、12列为细胞对照，37℃、5％CO2培养，每小时观察病变，连续观察24h。病毒对照出现90％以上的病变后，将板孔内液体吸弃，加1％中性红染色，在540nm波长测定OD值，用Reed-Muench方法计算药物半数中毒浓度(TC50)、半数有效浓度(IC50)，观察药物抑杀病毒的效果。结果如下：
| 受试样品 | TC<sub>50</sub>(μM) | IC<sub>50</sub>(μM) |
| 式I化合物 | >100 | 25 |
| 利巴韦林 | >100 | >100 |
Claims (7)
1.一种银杏叶来源的聚酮类化合物或其药学上可接受的盐，其特征在于所述聚酮类化合物具有式I所示结构：
2.权利要求1所述的式I化合物的制备方法，其特征在于包括如下步骤：
(1)将干燥的银杏叶粉碎后，用体积分数为60％的乙醇溶液加热至回流温度提取5h后，过滤、滤液经减压浓缩得粗提物；
(2)将步骤(1)得到的粗提物先经减压硅胶柱层析，采用石油醚-乙酸乙酯混合溶剂作为洗脱剂进行梯度洗脱，洗脱梯度分别为100:0、90:10、80:20、70:30、60:40，50:50、40:60、30:70、20:80、10:90、0:100，每个梯度收集三个柱体积，将洗脱梯度为70:30～60:40的洗脱液合并，浓缩得组分A；
(3)将步骤(2)得到的组分A先经正相硅胶柱层析，洗脱剂为石油醚：乙酸乙酯＝2.5:1的混合溶剂，洗脱5个柱体积，合并第3-5柱体积的洗脱液，减压浓缩后再经Sephadex LH-20凝胶柱层析，洗脱剂为CHCl3:MeOH＝1:1的混合溶剂，洗脱4个柱体积，合并第3-4个柱体积的洗脱液，减压浓缩后再经高效液相色谱HPLC制备得式I化合物。
3.权利要求2所述的制备方法，其特征在于步骤(1)中银杏叶粉碎后的粒度优选为20-80目，所述乙醇溶液的用量为每千克银杏叶(干重)使用3L乙醇溶液；步骤(3)中所述高效液相色谱HPLC制备的色谱条件为：色谱柱为Agilent C18,9.4×250mm，7μm，流速为2mL/min，流动相为MeOH∶H2O＝60∶40。
4.权利要求2-3任一项所述的制备方法，其特征在于步骤(2)所述减压正相硅胶柱层析使用的硅胶优选100-200目硅胶；步骤(3)中所述正相硅胶柱层析使用的硅胶优选200-300目硅胶。
5.权利要求1所述的银杏叶来源的聚酮类化合物或其药学上可接受的盐在制备抗病毒药物中的应用。
6.权利要求1所述的银杏叶来源的聚酮类化合物或其药学上可接受的盐在制备抗EV71药物中的应用。
7.权利要求1所述的银杏叶来源的聚酮类化合物或其药学上可接受的盐在制备预防和/或治疗由EV71感染引起的疾病的药物中的应用。
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| CN109020946B (zh) * | 2018-11-05 | 2020-04-24 | 扬州工业职业技术学院 | 一种大规模制备银杏叶来源的聚酮类化合物的方法 |
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