CN108129437B - 一种黄酮化合物及其制备方法与应用 - Google Patents
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Abstract
本发明具体涉及一种黄酮化合物及其制备方法与应用，所述黄酮类化合物具有如下式I或式II所示结构：
Description
技术领域
本发明属于植物提取分离领域，具体涉及一种黄酮化合物及其制备方法与应用。
背景技术
银杏叶性平，味甘、苦、涩，归心、肺经，具有敛肺、平喘、活血化瘀、止痛的功效。银杏叶中化学成分复杂，主要的生物活性成分有黄酮类化合物、银杏内酯化合物、有机酸类等物质。其中黄酮类物质的含量较高，黄酮类化合物具有抗氧化、防止衰老、抑菌抗病毒等功效，且安全可靠，食用健康，可用于加工药品和保健食品。
对银杏叶中黄酮类化合物的研究一直是本领域的热点，本发明公开了一类新的银杏叶黄酮提取物，并从中分离得到式I、式II化合物。
发明内容
本发明提供一种银杏叶黄酮提取物，其特征在于包括如下步骤：
(1)将干燥的银杏叶粉碎，加入适量的质量分数为6-8％的β-葡萄糖糖苷酶水溶液浸泡6-8h后，再加入体积比为1：1的无水乙醇和Na2CO3溶液的混合溶液，回流提取10-12h，过滤，滤液浓缩得粗提物；
(2)步骤(1)得到的粗提物用适量的水分散后，用酸调pH至4-5后，用乙酸乙酯萃取，乙酸乙酯层浓缩后得萃取物；
(3)步骤(2)得到的萃取物经大孔树脂吸附，用体积分数为95％的乙醇洗脱3-5个柱体积，洗脱液浓缩、干燥得所述银杏叶黄酮提取物。
步骤(1)所述粉碎优选粉碎至20-80目，每千克银杏叶使用β-葡萄糖糖苷酶水溶液2.0-2.5L，每千克银杏叶使用无水乙醇4.0-5.0L，Na2CO3溶液的质量分数为3-5％；
步骤(2)中水的用量优选每克粗提物使用10-15mL水，酸优选稀盐酸、醋酸中的一种或两种，乙酸乙酯萃取优选2-3次，每次萃取使用乙酸乙酯的体积优选为水体积的2-3倍；
步骤(3)中大孔树脂的型号优选AB-8或D101型；
所述银杏叶黄酮提取物中式I、式II化合物的含量在25％以上，式I、式II结构如下：
本发明的另一实施方案提供上述银杏叶黄酮提取物在制备抗补体药物中的应用。
本发明的另一实施方案提供一种药物组合物，其特征在于所述药物组合物以上述银杏叶黄酮提取物作为有效成分。所述药物组合物还任选包括药学上可接受的药用辅料(优选稀释剂、赋形剂、载体)；还任选包括其他抗补体药物；所述药物组合物的剂型优选固体制剂或液体制剂。
本发明的另一实施方案提供一种黄酮类化合物或其药学上可接受的盐，其特征在于所述黄酮类化合物具有如下式I或式II所示结构：
本发明的另一实施方案提供上述式I或式II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，加入适量的质量分数为6-8％的β-葡萄糖糖苷酶水溶液浸泡6-8h后，再加入体积比为1：1的无水乙醇和Na2CO3溶液的混合溶液，回流提取10-12h，过滤，滤液浓缩得粗提物；
(2)步骤(1)得到的粗提物用适量的水分散后，用酸调pH至4-5后，用乙酸乙酯萃取，乙酸乙酯层浓缩后得萃取物；
(3)步骤(2)得到的萃取物经大孔树脂吸附，用体积分数为95％的乙醇洗脱3-5个柱体积，洗脱液浓缩、干燥得所述银杏叶黄酮提取物；
(4)将步骤(3)得到的银杏叶黄酮提取物先经Sephadex LH-20凝胶柱层析，洗脱剂为CH2Cl2：MeOH＝1：1，再经高效液相色谱HPLC制备得到式I和式II化合物。
步骤(1)所述粉碎优选粉碎至20-80目，每千克银杏叶使用β-葡萄糖糖苷酶水溶液2.0-2.5L，每千克银杏叶使用无水乙醇4.0-5.0L，Na2CO3溶液的质量分数为3-5％；步骤(2)中水的用量优选每克粗提物使用10-15mL水，酸优选稀盐酸、醋酸中的一种或两种，乙酸乙酯萃取优选2-3次，每次萃取使用乙酸乙酯的体积优选为水体积的2-3倍；步骤(3)中大孔树脂的型号优选AB-8或D101型；步骤(4)所述高效液相色谱的色谱条件优选色谱柱为Hypersil 300A C18，10×250mm，10μm，流速为2mL/min，流动相为MeOH∶H2O＝55∶45。
本发明的另一实施方案提供上述式I、式II化合物或其药学上可接受的盐在制备抗补体药物中的应用。
本发明的另一实施方案提供一种药物组合物，其特征在于所述药物组合物以上述式I、式II化合物或其药学上可接受的盐作为有效成分。所述药物组合物还任选包括药学上可接受的药用辅料(优选稀释剂、赋形剂、载体)；还任选包括其他抗补体药物；所述药物组合物的剂型优选固体制剂或液体制剂。
本发明中术语“药学上可接受的盐”是指非毒性的无机或有机酸和/或碱的加成盐，可参见“Salt selection for basic drugs”,Int.J.Pharm.(1986),33,201–217。
与现有技术相比，本发明利用酶解、碱醇提、调酸、乙酸乙酯萃取、大孔树脂吸附的方法，得到了一种黄酮提取物，并成功分离到了式I和式II化合物，并测试了其抗补体活性。
附图说明
图1为银杏叶黄酮提取物产品A的HPLC分析图。
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的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)取干燥的银杏叶(1.0kg)粉碎至20-80目，加入质量分数为6％的β-葡萄糖糖苷酶水溶液(2.5L)浸泡8h后，再加入体积比为1：1的无水乙醇和3％Na2CO3溶液的混合溶液(10L)，回流提取12h，过滤，滤液浓缩得粗提物11.2g；
(2)取步骤(1)得到的粗提物10g用150mL水分散后，用稀盐酸调pH至4.0-5.0后，用乙酸乙酯萃取2次，合并有机相后，浓缩得萃取物1.80g；
(3)步骤(2)得到的萃取物(1.80g)经AB-8型大孔树脂吸附，用体积分数为95％的乙醇洗脱3个柱体积，洗脱液浓缩、干燥得所述银杏叶黄酮提取物865mg，以下简称产品A。
实施例2
(1)取干燥的银杏叶(1.0kg)粉碎至20-80目，加入质量分数为8％的β-葡萄糖糖苷酶水溶液(2.0L)浸泡6h后，再加入体积比为1：1的无水乙醇和5％Na2CO3溶液的混合溶液(8L)，回流提取10h，过滤，滤液浓缩得粗提物11.8g；
(2)取步骤(1)得到的粗提物10g用100mL水分散后，用醋酸调pH至4.0-5.0后，用乙酸乙酯萃取3次，合并有机相后，浓缩得萃取物1.82g；
(3)步骤(2)得到的萃取物(1.82g)经D101型大孔树脂吸附，用体积分数为95％的乙醇洗脱5个柱体积，洗脱液浓缩、干燥得所述银杏叶黄酮提取物881mg，以下简称产品B。
实施例3
取产品A(50mg)先经Sephadex LH-20凝胶柱层析，洗脱剂为CH2Cl2：MeOH＝1：1，再经高效液相色谱HPLC制备，色谱柱为Hypersil 300AC18，10×250mm，10μm，流速为2mL/min，流动相为MeOH∶H2O＝55∶45分别得到式I化合物(7.3mg)和式II化合物(5.2mg)。
式I化合物结构确证数据：ESIMS m/z 371.1[M+H]+,1H,13C NMR数据见下表；式II化合物结构确证数据：ESIMS m/z 413.1[M+H]+,1H,13C NMR数据见下表。
式I、II的1H,13C NMR数据(Acetone-d6，400/100MHz)
实施例4
取产品B(50mg)先经Sephadex LH-20凝胶柱层析，洗脱剂为CH2Cl2：MeOH＝1：1，再经高效液相色谱HPLC制备，色谱柱为Hypersil 300A C18，10×250mm，10μm，流速为2mL/min，流动相为MeOH∶H2O＝55∶45分别得到式I化合物(7.9mg)和式II化合物(5.0mg)，结构确证数据与实施例3一致。
实施例5
分别取适量产品A、B进行HPLC分析，式I、式II化合物的总含量在26-28％。
实施例6
按照中国专利(申请号：201610384844.X)公开的经典途径补体抑制试验的方法进行测试，得出50％抑制溶血所需供试品的浓度(CH50)，见下表。
| 化合物 | CH<sub>50</sub>(mg/mL) |
| 式I | 0.106±0.012 |
| 式II | 0.182±0.019 |
| 产品A | 0.203±0.023 |
| 产品B | 0.218±0.025 |
| 肝素钠 | 0.053±0.008 |
Claims (5)
1.一种式I、式II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，加入适量的质量分数为6-8％的β-葡萄糖糖苷酶水溶液浸泡6-8h后，再加入体积比为1：1的无水乙醇和Na2CO3溶液的混合溶液，回流提取10-12h，过滤，滤液浓缩得粗提物；
(2)步骤(1)得到的粗提物用适量的水分散后，用酸调pH至4-5后，用乙酸乙酯萃取，乙酸乙酯层浓缩后得萃取物；
(3)步骤(2)得到的萃取物经大孔树脂吸附，用体积分数为95％的乙醇洗脱3-5个柱体积，洗脱液浓缩、干燥得所述银杏叶黄酮提取物；
(4)将步骤(3)得到的银杏叶黄酮提取物先经Sephadex LH-20凝胶柱层析，洗脱剂为CH2Cl2：MeOH＝1：1，再经高效液相色谱HPLC制备得到式I、式II化合物；
式I、式II结构如下：
2.权利要求1所述的制备方法，其特征在于步骤(1)所述粉碎为粉碎至20-80目，每千克银杏叶使用β-葡萄糖糖苷酶水溶液2.0-2.5L，每千克银杏叶使用无水乙醇4.0-5.0L，Na2CO3溶液的质量分数为3-5％。
3.权利要求1所述的制备方法，其特征在于步骤(2)中水的用量为每克粗提物使用10-15mL水，酸选自稀盐酸、醋酸中的一种或两种，乙酸乙酯萃取2-3次。
4.权利要求1所述的制备方法，其特征在于步骤(3)中大孔树脂的型号选自AB-8或D101型。
5.权利要求1所述的制备方法，其特征在于步骤(4)所述高效液相色谱的色谱条件选自色谱柱为Hypersil 300A C18，10×250mm，10μm，流速为2mL/min，流动相为MeOH∶H2O＝55∶45。
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