CN116919940A - 一种角豆果荚提取物二氢去氢二愈创木基醇的制备方法与应用 - Google Patents
一种角豆果荚提取物二氢去氢二愈创木基醇的制备方法与应用 Download PDFInfo
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Abstract
本发明提供一种角豆果荚提取物二氢去氢二愈创木基醇的制备方法及其应用。本发明提取物是通过对角豆树果荚的萃取提取、分离纯化得到的。本发明制备的提取物具有显著的调节血脂，改善脑缺血损伤，清除DPPH自由基和ABST自由基从而延缓血管硬化能力。为心脑血管疾病领域提供了新的选择。
Description
技术领域
本发明涉及医药和保健食品技术领域，具体涉及一种角豆树果荚提取物及其制备方法和应用。
背景技术
二氢去氢二愈创木基醇[(7S,8R)-dihydrodehydro diconiferyl alcohol]，属于苯丙素类化合物，广泛存在于植物中的一种天然成分，多报道于植物提取物成分的分析过程中发现其存在，然而针对其提取分离，还未有相关的研究，在功能应用方面，未见有明确作用的应用研究。
心脑血管疾病的形成，主要原因是供应心脏、脑的动脉，发生相应的动脉粥样硬化，形成斑块，引起血管狭窄，供血不足，引起相应的症状。而动脉粥样硬化形成的原因，主要有遗传史、高血脂、高血压、糖尿病、长期的吸烟史、肥胖，这些因素都会影响血脂的代谢，使血管内皮受损，形成明确的动脉粥样硬化。
本发明提供一种从角豆树果荚中提取制备二氢去氢二愈创木基醇的方法，得到高纯度的二氢去氢二愈创木基醇，制备方法简单易行，能耗低，无污染，原料丰富易得，适于规模化生产推广。可应用于心脑血管疾病产品的开发。
发明内容：
本发明第一目的在于提供一种角豆果荚提取物的制备方法。
本发明的第二目的在于提供该方法制备得到的角豆果荚提取物。
本发明的第三目的在于提供该角豆果荚提取物的用途。
本发明提供的角豆果荚提取物为二氢去氢二愈创木基醇，结构式：
具体的本发明提供以下技术方案：
提供经粉碎的角豆树去种子的果荚；
先用80-95％乙醇提取，再用60-75％乙醇提取，合并提取液浓缩成浸膏；
将所得浸膏用水稀释分散，经大孔吸附树脂D101吸附，先用蒸馏水洗脱除去糖类杂质；再用95％乙醇洗脱，将所得洗脱液回收溶剂；用甲醇分散，依次经石油醚、乙酸乙酯萃取；
将乙酸乙酯萃取部位回收溶剂，然后经硅胶柱、ODS、Sephadex LH-20柱色谱和半制备液相进行分离纯化，得到二氢去氢二愈创木基醇。
根据本发明实施例，所述角豆树为豆科长豆角属植物角豆树(学名:Ceratoniasiliqua Linn.)。
根据本发明实施例，角豆树去种子的果荚粉碎至40-80目，优先选60目。研究发现，在此粒径内可以充分破碎果荚细胞结构，有利于二氢去氢二愈创木基醇的充分溶出。
根据本发明实施例，先用80-95％乙醇提取，再用60-75％乙醇提取，研究发现，这样可以增加二氢去氢二愈创木基醇提取率。
根据本发明实施例，第一次用80-95％乙醇提取时，80-95％乙醇与角豆树去种子的果荚的重量比为5-10:1，研究发现，这样有利于沉淀除去部分杂质。
根据本发明实施例，第一次用80-95％乙醇提取2-3次，每次1-3小时。
根据本发明实施例，第二次用60-75％乙醇提取时，60-75％乙醇与角豆树去种子的果荚的重量比为5-10:1，研究发现，这样有利于增加二氢去氢二愈创木基醇的溶解度，提高提取率。
根据本发明实施例，第二次用60-75％乙醇提取1-2次，每次1-3小时。
研究发现，用大孔吸附树脂D101吸附可以分离可离子化物质、糖类物质、大分子物质。
研究发现，用硅胶柱、ODS柱色谱、Sephadex LH-20柱色谱和半制备液相进行分离纯化可以获得高纯度、高收率二氢去氢二愈创木基醇。
根据本发明实施例，所述半制备液相为柱Ⅰ，甲醇:纯化水＝55-45:45-55，吸收波长：280nm。
根据本发明实施例，所述半制备液相为柱Ⅱ，甲醇:纯化水＝43-48:57-52，吸收波长：280nm。
根据本发明实施例，角豆果荚中二氢去氢二愈创木基醇的提取方法，包括:
取角豆树果荚去种子，粉碎后过60-80目药筛，得到角豆树果荚粗粉。然后加入粗粉7倍重量份的95％乙醇回流提取3次(每次1.5小时)，再用粗粉8倍重量份的70％乙醇回流提取1次(1.5小时)，合并提取液浓缩得到浸膏10份重量份。用10份重量份的水将浸膏分散，经大孔吸附树脂D101进行吸附，用蒸馏水洗脱3个柱体积除去糖类等杂质，再用95％乙醇洗脱3个柱体积，回收溶剂后得到非糖类小分子部位。将得到的非糖类小分子部位用1倍重量的50％甲醇分散，依次使用石油醚、乙酸乙酯分别萃取5次，回收溶剂后分别得到石油醚部位、乙酸乙酯部位和水部位。乙酸乙酯部位经ODS色谱柱、Sephadex LH-20柱色谱和半制备液相进行分离纯化，得到二氢去氢二愈创木基醇。
上述制备方法中，获得乙酸乙酯部位物质后，流分经ODS色谱柱甲醇-水(15:85-100:0)，TLC薄层检识，合并相似流份。流分经Sephadex LH-20，二氯甲烷-甲醇(1:1)洗脱，然后用半制备液相(柱Ⅰ，甲醇:纯化水＝50:50，吸收波长：280nm；柱Ⅱ，甲醇:纯化水＝45:55，吸收波长：280nm)分离获得二氢去氢二愈创木基醇，纯度可达到99.1％，得率可达到86％。
附图说明
图1为本发明实施例1中提取物的核磁共振氢谱(1H NMR)。
图2为本发明实施例1中提取物的核磁共振碳谱(13C NMR)。
图3为本发明实施例1中提取物结构式。
具体实施方式
实施例1
取干燥的角豆树去种子果荚，粉碎得到60目粗粉，加入粗粉7倍重量的90％乙醇回流提取3次(每次1.5小时)，再用粗粉8倍重量的70％乙醇回流提取1次(1.5小时)，合并提取液浓缩得到浸膏。用10倍重量的水将浸膏分散，经大孔吸附树脂D101进行吸附，用蒸馏水洗脱3个柱体积除去糖类等杂质，再用95％乙醇洗脱3个柱体积，回收溶剂后得到非糖类小分子部位。将得到的非糖类小分子部位用4倍重量的50％甲醇分散，依次使用石油醚、乙酸乙酯分别萃取5次，回收溶剂后分别得到石油醚部位、乙酸乙酯部位和水部位。
将乙酸乙酯部位用200-300目硅胶色谱分离，依次用石油醚-乙酸乙酯(1：1→1:0)，二氯甲烷-甲醇(7:1→0:1)梯度洗脱，减压浓缩，经TLC薄层检测，合并相似流份，得到10个流份(A-J)，回收溶剂，流分F和G经ODS柱色谱甲醇-水(15:85→100:0)梯度洗脱，TLC薄层检识，合并相似流份，得到6个组分(a-e)。组分e经Sephadex LH-20，二氯甲烷-甲醇(1:1)洗脱分离，然后用半制备液相(柱Ⅰ，甲醇:纯化水＝1:1，吸收波长:280nm)分离纯化，再经过半制备液相(柱Ⅱ，甲醇:纯化水＝45:55，吸收波长:280nm)分离纯化，获得二氢去氢二愈创木基醇，纯度达到98.5％，得率达到80％。该化合物核磁共振图谱如图1(1H NMR)、图2(13CNMR)所示。
实施例2
取干燥的角豆树去种子果荚，粉碎得到80目粗粉，加入粗粉10倍重量的80％乙醇回流提取2次，每次1.5小时，再用粗粉5倍重量的60％乙醇回流提取1次，每次1.5小时，合并提取液浓缩得到浸膏。用6倍重量的水将浸膏分散，经大孔吸附树脂D101进行吸附，用蒸馏水洗脱3个柱体积除去糖类等杂质，再用95％乙醇洗脱3个柱体积，回收溶剂后得到非糖类小分子部位。将得到的非糖类小分子部位用5倍重量的50％甲醇分散，依次使用石油醚、乙酸乙酯分别萃取5次，回收溶剂后分别得到石油醚部位、乙酸乙酯部位和水部位。
将乙酸乙酯部位用200-300目硅胶色谱分离，依次用石油醚-乙酸乙酯(3：1→0:1)，二氯甲烷-甲醇(7:1→0:1)梯度洗脱，减压浓缩，经TLC薄层检测，合并相似流份，得到10个流份(A-J)，回收溶剂，流分F和G经ODS柱色谱甲醇-水(15:85→100:0)梯度洗脱，TLC薄层检识，合并相似流份，得到6个组分(a-e)。组分e经Sephadex LH-20，二氯甲烷-甲醇(1:1)洗脱分离，然后用半制备液相(柱Ⅰ，甲醇:纯化水＝1:1，吸收波长:280nm)分离纯化，再经过半制备液相(柱Ⅱ，甲醇:纯化水＝45:55，吸收波长:280nm)分离纯化，获得二氢去氢二愈创木基醇，纯度达到98.5％，得率达到82％。
实施例3
取角豆树果荚去种子，粉碎后过70目药筛，得到角豆树果荚粗粉。然后加入粗粉8倍重量的85％乙醇回流提取3次(每次1.5小时)，再用粗粉10倍重量的75％乙醇回流提取1次(1.5小时)，合并提取液浓缩得到浸膏。用5份重量份的水将浸膏分散，经大孔吸附树脂D101进行吸附，用蒸馏水洗脱3个柱体积除去糖类等杂质，再用95％乙醇洗脱3个柱体积，回收溶剂后得到非糖类小分子部位。将得到的非糖类小分子部位用2倍重量的50％甲醇分散，依次使用石油醚、乙酸乙酯分别萃取5次，回收溶剂后分别得到石油醚部位、乙酸乙酯部位和水部位。
将乙酸乙酯部位用200-300目硅胶色谱分离，依次用石油醚-乙酸乙酯(3：1→0:1)，二氯甲烷-甲醇(8:1→0:1)梯度洗脱，减压浓缩，经TLC薄层检测，合并相似流份，得到10个流份(A-J)，回收溶剂，流分F和G经ODS柱色谱甲醇-水(35:75→100:0)梯度洗脱，TLC薄层检识，合并相似流份，得到6个组分(a-e)。组分e经Sephadex LH-20，二氯甲烷-甲醇(1:1)洗脱分离，然后用半制备液相(柱Ⅰ，甲醇:纯化水＝52:48，吸收波长:280nm)分离纯化，再经过半制备液相(柱Ⅱ，甲醇:纯化水＝45:55，吸收波长:280nm)分离纯化，获得二氢去氢二愈创木基醇，纯度达到99.1％，得率达到86％。
对比例1
与实施例1相比，区别仅在于，第一次乙醇回流提取的乙醇浓度为70％。
获得二氢去氢二愈创木基醇，纯度达到52.3％，得率达到31％。
对比例2
与实施例1相比，区别仅在于，第二次乙醇回流提取的乙醇浓度为50％。
获得二氢去氢二愈创木基醇，纯度达到54.0％，得率达到37％。
对比例3
与实施例1相比，区别仅在于，粉碎得到50目粗粉。
获得二氢去氢二愈创木基醇，纯度达到51％，得率达到14.5％。
对比例4
与实施例1相比，区别仅在于，ODS柱色谱甲醇-水(15:85→10:90)洗脱。
获得二氢去氢二愈创木基醇，纯度达到53％，得率达到28％。
对比例5
与实施例1相比，区别仅在于，ODS柱色谱甲醇-水(15:85→5:95)洗脱。
获得二氢去氢二愈创木基醇，纯度达到48.4％，得率达到28.5％。
对比例6
与实施例1相比，区别仅在于，用半制备液相(柱Ⅰ，甲醇:纯化水＝48:52，吸收波长:210nm)分离，获得二氢去氢二愈创木基醇，纯度达到50.1％，得率达到23％。
对比例7
与实施例1相比，区别仅在于，用半制备液相(柱Ⅰ，甲醇:纯化水＝35:65，吸收波长:210nm)分离，获得二氢去氢二愈创木基醇，纯度达到51.2％，得率达到21.8％。
实验例1
1.降血脂效果
体重18-22g的成年雄性SPF级小鼠70只，购自北京维通利华实验动物有限公司。小鼠饲养于温度为(23±2)℃和相对湿度为50％～60％的条件下，12h光照循环，饲喂标准饲料，自由饮食和饮水。适应实验室环境1周。
将小鼠分为7组，空白组，高脂模型组，阳性组，实施例1-3组，角豆提取物组，每组10只，空白组及高脂模型组灌胃蒸馏水，阳性组灌胃15mg/kg辛伐他汀，实施例组1-3灌胃15Mg/kg的实施例1-3产物，角豆提取物组灌胃15Mg/kg乙酸乙酯部位产物(制备方法同实施例1乙酸乙酯部位)，每日一次。空白组和高脂模型饲喂标准饲料，其余组都给予高脂饲料(在标准饲料的基础上加10％猪油，2％胆固醇，0.5％的胆酸钠)连续灌胃30天。
实验结束空腹12h后采血，测定血清总胆固醇(TC)、三酰甘油(TG)、低密度脂蛋白胆固醇(LDL-C)、高密度脂蛋白胆固醇(HDL-C)。结果如表1所示。
表1角豆提取物(二氢去氢二愈创木基醇)降血脂活性实验结果(n＝10)
实验结果表明，角豆提取物(二氢去氢二愈创木基醇)能够降低高脂模型小鼠总胆固醇值、三酰甘油值及低密度脂蛋白胆固醇值，能够提高高脂模型小鼠高密度脂蛋白胆固醇值。说明角豆提取物(二氢去氢二愈创木基醇)具有调节血脂的作用。
2.对脑缺血损伤保护作用
体重1800-220g的成年雄性Wistar大鼠42只，购自北京维通利华实验动物有限公司。小鼠饲养于温度为(23±2)℃和相对湿度为50％～60％的条件下，12h光照循环，饲喂标准饲料，自由饮食和饮水。适应实验室环境1周。建立脑缺血再灌模型，分为7组，每组6只，分别为假手术组，模型对照组，阳性组，实施例1-3组，角豆提取物组。
空白组及模型组灌胃蒸馏水，阳性组灌胃25mg/kg依达拉奉，实施例组1-3灌胃25Mg/kg的实施例1-3产物，角豆提取物组灌胃25Mg/kg乙酸乙酯部位产物(制备方法同实施例1乙酸乙酯部位)，每日一次,连续灌胃14天。缺血2小时再灌注24小时后进行行为学评分(Bederson方法)，断头取脑，TTC染色，留取样本进行脑梗死体积测定。结果如表2所示。
脑梗死体积(％)＝(未损伤侧大脑面积-损伤侧非白色区面积)/(2×未损伤侧大脑面积)×100％。
表2对脑缺血损伤保护作用
| 组别 | 行为学评分(24h) | 脑水肿(％) | 脑梗死体积(％) |
| 空白组 | 0 | 0.51±0.061 | 0.56±0.17 |
| 模型组 | 2.03±0.074 | 11.08±1.268 | 34.04±1.743 |
| 阳性组 | 1.08±0.124 | 5.48±0.417 | 15.53±0.419 |
| 实施例1 | 1.30±0.079 | 9.22±0.569 | 20.51±1.211 |
| 实施例2 | 1.27±0.067 | 8.73±0.21 | 21.39±1.413 |
| 实施例3 | 1.02±0.103 | 6.32±0.331 | 17.46±1.222 |
| 角豆提取物 | 1.89±0.108 | 10.27±0.137 | 28.83±1.447 |
实验结果表明，角豆提取物(二氢去氢二愈创木基醇)能够显著缩小脑梗死体积，减轻脑水肿程度，神经行为评分明显好转。说明角豆提取物(二氢去氢二愈创木基醇)具有改善脑缺血损伤的作用。
3.自由基清除能力
将实施例1-3，角豆提取物，(制备方法同实施例1乙酸乙酯部位),维生素C(对照组)加蒸馏水至浓度为0.1mmol/L。取5支试管分别加入2ml浓度为0.15mmol/L的DPPH溶液(溶剂为无水乙醇)及2ml样品溶液，均匀避光37℃下静置30min。后于517nm处测吸光度As，平行5次。相同条件下测2ml无水乙醇及2ml样品溶液混合溶液的吸光度Ab，相同条件下测2mlDPPH溶液及2ml蒸馏水混合溶液的吸光度Ac，计算DPPH自由基清除率。
将实施例1-3，角豆提取物，(制备方法同实施例1乙酸乙酯部位),维生素C(对照组)加入70％乙醇溶液至浓度为0.1mmol/L。取5支试管分别加入2ml ABTS溶液(含7.4mmol/L的ABTS二胺盐溶液、2.6mmol/L过二硫酸钾溶液，体积比为1:1)及2ml样品溶液，均匀避光37℃下静置6min。后于734nm处测吸光度As，平行5次。相同条件下测2ml无水乙醇及2ml样品溶液混合溶液的吸光度Ab，相同条件下测2mlABST溶液及2ml蒸馏水混合溶液的吸光度Ac，计算ABST自由基清除率。
自由基清除率(％)＝(1-(As-Ab)/Ac)×100％
表3自由基清除能力
| 组别 | DPPH清除率(％) | ABST清除率(％) |
| 实施例1 | 39.58 | 43.81 |
| 实施例2 | 42.53 | 36.78 |
| 实施例3 | 51.53 | 48.59 |
| 角豆提取物 | 18.46 | 17.76 |
| 维生素C | 60.79 | 52.15 |
实验结果表明，角豆提取物(二氢去氢二愈创木基醇)具有一定的自由基清除能力，，说明角豆提取物(二氢去氢二愈创木基醇)具有抗氧化延缓血管硬化，从而预防改善心脑血管疾病的潜力。
Claims (6)
1.一种角豆果荚提取物二氢去氢二愈创木基醇在制备用于调节血脂方面的药品或/和保健品领域的应用。
2.一种角豆果荚提取物二氢去氢二愈创木基醇在制备用于改善脑缺血方面的药品或/和保健品领域的应用。
3.角豆果荚提取物二氢去氢二愈创木基醇在制备用于清除DPPH自由基和ABST自由基抗氧化方面的药品或/和保健品或/和化妆品领域的应用。
4.以上权利要求1-3所述角豆果荚提取物提取方法，其特征在于将粉碎的角豆果荚采用醇提得到浸膏，再用水将其分散，后用D101大孔吸附树脂吸附、洗脱，然后依次用石油醚、乙酸乙酯萃取得到。
5.根据权利要求4所述角豆果荚提取物制备方法，其特征在于将乙酸乙酯萃取得到的部分进一步采用硅胶柱、ODS柱色谱、SephadexLH-20柱色谱和半制备液相进行分离纯化得到高纯度，高得率的角豆果荚提取物二氢去氢二愈创木基醇。
6.一种角豆果荚提取物提取方法，其特征在于高纯度，制备方法简单易行，能耗低，无污染，原料丰富易得，适于规模化生产推广。
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