CN112220934A - 一种包埋白藜芦醇及其制备方法 - Google Patents
一种包埋白藜芦醇及其制备方法 Download PDFInfo
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- CN112220934A CN112220934A CN202011000493.0A CN202011000493A CN112220934A CN 112220934 A CN112220934 A CN 112220934A CN 202011000493 A CN202011000493 A CN 202011000493A CN 112220934 A CN112220934 A CN 112220934A
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- resveratrol
- quaternary ammonium
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- glycol chitosan
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Abstract
本发明公开了一种包埋白藜芦醇的制备方法，其特征在于，包括如下步骤：步骤S1、超支化乙二醇壳聚糖季铵盐的制备，步骤S2、超支化乙二醇壳聚糖季铵甘草盐的制备，步骤S3、复合物的制备。本发明还提供了一种根据所述一种包埋白藜芦醇的制备方法制备得到的包埋白藜芦醇。本发明公开的包埋白藜芦醇水溶性更好，性能稳定性更佳，包埋率更高，成本更低廉，使用更加绿色安全。
Description
技术领域
本发明涉及复合材料技术领域，尤其涉及一种包埋白藜芦醇及其制备方法。
背景技术
白藜芦醇是一种含有芪类结构的非黄酮类多酚化合物，是植物在逆境刺激或非胁迫条件下产生的植物次生代谢产物，是医药、化工、食品、化妆品方面的主要原料，主要存在于葡萄、花生、虎杖和桑葚等植物中。研究表明，白藜芦醇具有多种生物活性具有抗氧化、抗癌、抗菌、抗炎、心血管保护、调剂血脂和治疗糖尿病等诸多生理药理活性；此外白藜芦醇还对骨质疏松、痤疮及老年痴呆症有预防作用，具有抗病毒及免疫调节的药理作用。
白藜芦醇是一种对光照非常敏感的化合物，暴露在日光下一个小时，就会有超过80％的反式白藜芦醇转变为顺式。白藜芦醇也会发生氧化现象，产生氧自由基以及复杂的半醌和醌类化合物，这些物质都具有细胞毒性。并且白藜芦醇的水溶性差、代谢速度快，使其在工业中的应用受到了很大的限制，口服吸收较差，生物利用度较低，紫外照射下易发生异构化，难以达到预期的治疗效果。
对白藜芦醇进行包埋是对其保护、消化以及增加生物利用度的一种有效手段。天然的生物大分子(如蛋白质、多糖等)不但具有高的营养价值，而且具有多种功能特性，已被广泛用作包埋技术中的原料。目前所使用的包埋技术主要有微胶囊技术和包结络合法等，在国外，Tan等人制备了β-胡萝卜素纳米乳液使β-胡萝卜素的保留率有所提高，Misiuk等人使羟丙基β-环糊精与盐酸曲唑酮络合，成功提高了盐酸曲唑酮的生物利用度；在国内，胡富强等以明胶、阿拉伯胶为壁材，采用复凝聚法制备微胶囊，制得的微胶囊中β-胡萝卜素的稳定性大大增加。左爱仁等以明胶和蔗糖等多种配方作为壁材制备番茄红素微胶囊，提高了番茄红素的保留率。但目前包埋形式的缺点是包埋率低、成本高、非绿色等。
申请号为201910464538.0的中国发明专利涉及复合材料技术领域，尤其涉及一种包埋白藜芦醇的制备方法。该发明提供了一种包埋白藜芦醇的制备方法，其特征在于，包括以下步骤：步骤1：氯乙酸水溶液加入β-环糊精的碱溶液中得到混合溶液，在所述混合溶液中加入甲醇，沉淀，得到羧甲基-β-环糊精；步骤2：将壳聚糖盐酸盐溶液与羧甲基-β-环糊精混合，滴加戊二醛溶液，搅拌，得到羧甲基-β-环糊精壳聚糖盐酸盐纳米溶液；步骤3：将所述羧甲基-β-环糊精壳聚糖盐酸盐纳米溶液和白藜芦醇溶液混合，调节至中性得到包埋白藜芦醇。该发明提供的一种包埋白藜芦醇的制备方法，解决了现有的包埋天然多酚物质方法不适用大工业生产且应用限制较多的技术问题。然而，其水溶解性能还有待进一步提高，过程中使用的戊二醛环保性不好。
因此，开发一种水溶性更好，性能稳定性更佳，包埋率更高，成本更低廉，制备过程更加绿色安全的包埋白藜芦醇符合市场需求，具有广泛的市场价值和应用前景，对促进包埋技术的发展具有非常重要的意义。
发明内容
本发明目的是为了克服现有技术的不足而提供一种包埋白藜芦醇及其制备方法，该制备方法简单，生产流程短，生产效率和产品产率高，价格低廉；通过这种制备方法制备得到的包埋白藜芦醇水溶性更好，性能稳定性更佳，包埋率更高，成本更低廉，使用更加绿色安全。
为达到上述目的，本发明采用的技术方案是：一种包埋白藜芦醇的制备方法，其特征在于，包括如下步骤：
步骤S1、超支化乙二醇壳聚糖季铵盐的制备：将超支化乙二醇壳聚糖、季铵盐试剂加入到有机溶剂中，在40-60℃下搅拌反应4-6小时，后旋蒸除去溶剂，并用乙醚洗涤产物3-7次，后旋蒸除去乙醚，得到超支化乙二醇壳聚糖季铵盐；
步骤S2、超支化乙二醇壳聚糖季铵甘草盐的制备：将经过步骤S1制成的超支化乙二醇壳聚糖季铵盐、甘草酸加入到水中，在50-70℃下搅拌反应4-6次，后旋蒸除去水，得到超支化乙二醇壳聚糖季铵甘草盐；
步骤S3、复合物的制备：将白藜芦醇加入到醇溶剂中配制成白藜芦醇溶液，然后向其中加入经过步骤S2制成的超支化乙二醇壳聚糖季铵甘草盐、茶多酚壳聚糖纳米粒、磺丁基-β-环糊精，搅拌30-40分钟，后冷冻干燥，制成包埋白藜芦醇。
优选的，步骤S1中所述超支化乙二醇壳聚糖、季铵盐试剂、有机溶剂的质量比为1:(0.3-0.5):(5-10)。
优选的，所述季铵盐试剂为3-氯-L-丙氨酸、2-氯丙酰甘氨酸、2-氯丙酰苷氨酸中的至少一种。
优选的，所述有机溶剂为四氢呋喃、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺中的任意一种。
优选的，所述超支化乙二醇壳聚糖的制备方法参见申请号为200610011756.1的中国发明专利实施例1。
优选的，步骤S2中所述超支化乙二醇壳聚糖季铵盐、甘草酸、水的质量比为1:(0.1-0.2):(5-10)。
优选的，步骤S3中所述白藜芦醇溶液的质量百分浓度为20-40％。
优选的，步骤S3中所述醇溶剂为乙醇、异丙醇、甘油中的至少一种。
优选的，步骤S3中所述白藜芦醇溶液、超支化乙二醇壳聚糖季铵甘草盐、茶多酚壳聚糖纳米粒、磺丁基-β-环糊精的质量比为2:1:(0.1-0.3):0.3。
优选的，所述茶多酚壳聚糖纳米粒的制备方法参见申请号为201710666255.5的中国发明专利实施例1。
本发明的另一个目的，在于提供一种根据所述一种包埋白藜芦醇的制备方法制备得到的包埋白藜芦醇。
由于上述技术方案运用，本发明与现有技术相比具有下列优点：本发明提供一种包埋白藜芦醇及其制备方法，该制备方法简单，生产流程短，生产效率和产品产率高，价格低廉；通过这种制备方法制备得到的包埋白藜芦醇水溶性更好，性能稳定性更佳，包埋率更高，成本更低廉，使用更加绿色安全。
具体实施方式
下面将结合对本发明优选实施方案进行详细说明。
一种包埋白藜芦醇的制备方法，其特征在于，包括如下步骤：
步骤S1、超支化乙二醇壳聚糖季铵盐的制备：将超支化乙二醇壳聚糖、季铵盐试剂加入到有机溶剂中，在40-60℃下搅拌反应4-6小时，后旋蒸除去溶剂，并用乙醚洗涤产物3-7次，后旋蒸除去乙醚，得到超支化乙二醇壳聚糖季铵盐；
步骤S2、超支化乙二醇壳聚糖季铵甘草盐的制备：将经过步骤S1制成的超支化乙二醇壳聚糖季铵盐、甘草酸加入到水中，在50-70℃下搅拌反应4-6次，后旋蒸除去水，得到超支化乙二醇壳聚糖季铵甘草盐；
步骤S3、复合物的制备：将白藜芦醇加入到醇溶剂中配制成白藜芦醇溶液，然后向其中加入经过步骤S2制成的超支化乙二醇壳聚糖季铵甘草盐、茶多酚壳聚糖纳米粒、磺丁基-β-环糊精，搅拌30-40分钟，后冷冻干燥，制成包埋白藜芦醇。
优选的，步骤S1中所述超支化乙二醇壳聚糖、季铵盐试剂、有机溶剂的质量比为1:(0.3-0.5):(5-10)。
优选的，所述季铵盐试剂为3-氯-L-丙氨酸、2-氯丙酰甘氨酸、2-氯丙酰苷氨酸中的至少一种。
优选的，所述有机溶剂为四氢呋喃、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺中的任意一种。
优选的，所述超支化乙二醇壳聚糖的制备方法参见申请号为200610011756.1的中国发明专利实施例1。
优选的，步骤S2中所述超支化乙二醇壳聚糖季铵盐、甘草酸、水的质量比为1:(0.1-0.2):(5-10)。
优选的，步骤S3中所述白藜芦醇溶液的质量百分浓度为20-40％。
优选的，步骤S3中所述醇溶剂为乙醇、异丙醇、甘油中的至少一种。
优选的，步骤S3中所述白藜芦醇溶液、超支化乙二醇壳聚糖季铵甘草盐、茶多酚壳聚糖纳米粒、磺丁基-β-环糊精的质量比为2:1:(0.1-0.3):0.3。
优选的，所述茶多酚壳聚糖纳米粒的制备方法参见申请号为201710666255.5的中国发明专利实施例1。
本发明的另一个目的，在于提供一种根据所述一种包埋白藜芦醇的制备方法制备得到的包埋白藜芦醇。
由于上述技术方案运用，本发明与现有技术相比具有下列优点：本发明提供一种包埋白藜芦醇及其制备方法，该制备方法简单，生产流程短，生产效率和产品产率高，价格低廉；通过这种制备方法制备得到的包埋白藜芦醇水溶性更好，性能稳定性更佳，包埋率更高，成本更低廉，使用更加绿色安全。
下面将结合具体实施例对本发明进行进一步描述，但本发明的保护范围并不仅限于此：
实施例1
实施例1提供一种包埋白藜芦醇的制备方法，其特征在于，包括如下步骤：
步骤S1、超支化乙二醇壳聚糖季铵盐的制备：将超支化乙二醇壳聚糖、季铵盐试剂加入到有机溶剂中，在40℃下搅拌反应4小时，后旋蒸除去溶剂，并用乙醚洗涤产物3次，后旋蒸除去乙醚，得到超支化乙二醇壳聚糖季铵盐；
步骤S2、超支化乙二醇壳聚糖季铵甘草盐的制备：将经过步骤S1制成的超支化乙二醇壳聚糖季铵盐、甘草酸加入到水中，在50℃下搅拌反应4次，后旋蒸除去水，得到超支化乙二醇壳聚糖季铵甘草盐；
步骤S3、复合物的制备：将白藜芦醇加入到醇溶剂中配制成白藜芦醇溶液，然后向其中加入经过步骤S2制成的超支化乙二醇壳聚糖季铵甘草盐、茶多酚壳聚糖纳米粒、磺丁基-β-环糊精，搅拌30分钟，后冷冻干燥，制成包埋白藜芦醇。
步骤S1中所述超支化乙二醇壳聚糖、季铵盐试剂、有机溶剂的质量比为1:0.3:5；所述季铵盐试剂为3-氯-L-丙氨酸；所述有机溶剂为四氢呋喃。
步骤S2中所述超支化乙二醇壳聚糖季铵盐、甘草酸、水的质量比为1:0.1:5。
步骤S3中所述白藜芦醇溶液的质量百分浓度为20％；步骤S3中所述醇溶剂为乙醇。
步骤S3中所述白藜芦醇溶液、超支化乙二醇壳聚糖季铵甘草盐、茶多酚壳聚糖纳米粒、磺丁基-β-环糊精的质量比为2:1:0.1:0.3。
一种根据所述一种包埋白藜芦醇的制备方法制备得到的包埋白藜芦醇。
实施例2
实施例2提供一种包埋白藜芦醇，其配方和制备方法与实施例1基本相同，不同的是，步骤S1中所述超支化乙二醇壳聚糖、季铵盐试剂、有机溶剂的质量比为1:0.35:6；所述季铵盐试剂为2-氯丙酰甘氨酸；步骤S2中所述超支化乙二醇壳聚糖季铵盐、甘草酸、水的质量比为1:0.13:6.5；步骤S3中所述白藜芦醇溶液、超支化乙二醇壳聚糖季铵甘草盐、茶多酚壳聚糖纳米粒、磺丁基-β-环糊精的质量比为2:1:0.15:0.3。
实施例3
实施例3提供一种包埋白藜芦醇，其配方和制备方法与实施例1基本相同，不同的是，步骤S1中所述超支化乙二醇壳聚糖、季铵盐试剂、有机溶剂的质量比为1:0.4:7.5；所述季铵盐试剂为2-氯丙酰苷氨酸；步骤S2中所述超支化乙二醇壳聚糖季铵盐、甘草酸、水的质量比为1:0.15:7.5；步骤S3中所述白藜芦醇溶液、超支化乙二醇壳聚糖季铵甘草盐、茶多酚壳聚糖纳米粒、磺丁基-β-环糊精的质量比为2:1:0.2:0.3。
实施例4
实施例4提供一种包埋白藜芦醇，其配方和制备方法与实施例1基本相同，不同的是，步骤S1中所述超支化乙二醇壳聚糖、季铵盐试剂、有机溶剂的质量比为1:0.45:9；所述季铵盐试剂为3-氯-L-丙氨酸、2-氯丙酰甘氨酸、2-氯丙酰苷氨酸按质量比1:2:3混合而成；步骤S2中所述超支化乙二醇壳聚糖季铵盐、甘草酸、水的质量比为1:0.18:9；步骤S3中所述白藜芦醇溶液、超支化乙二醇壳聚糖季铵甘草盐、茶多酚壳聚糖纳米粒、磺丁基-β-环糊精的质量比为2:1:0.28:0.3。
实施例5
实施例5提供一种包埋白藜芦醇，其配方和制备方法与实施例1基本相同，不同的是，步骤S1中所述超支化乙二醇壳聚糖、季铵盐试剂、有机溶剂的质量比为1:0.5:10；所述季铵盐试剂为2-氯丙酰甘氨酸；步骤S2中所述超支化乙二醇壳聚糖季铵盐、甘草酸、水的质量比为1:0.2:10；步骤S3中所述白藜芦醇溶液、超支化乙二醇壳聚糖季铵甘草盐、茶多酚壳聚糖纳米粒、磺丁基-β-环糊精的质量比为2:1:0.3:0.3。
对比例1
对比例1提供一种包埋白藜芦醇，其配方和制备方法与实施例1基本相同，不同的是没有添加磺丁基-β-环糊精。
对比例2
对比例2提供一种包埋白藜芦醇，其配方和制备方法与实施例1基本相同，不同的是没有添加茶多酚壳聚糖纳米粒。
对比例3
对比例3提供一种包埋白藜芦醇，其配方和制备方法与实施例1基本相同，不同的是用超支化乙二醇壳聚糖季铵盐代替超支化乙二醇壳聚糖季铵甘草盐。
为了进一步说明本发明各实施例涉及到的包埋白藜芦醇的有益技术效果，对各例涉及到的无包埋白藜芦醇进行相关性能测试，测试方法参见相应国标，测试结果见表1。
表1
| 项目 | PDI | 在水中分散能力(％) | 包埋率(％) |
| 实施例1 | 0.055 | 20.2 | 50.34 |
| 实施例2 | 0.051 | 21.3 | 50.78 |
| 实施例3 | 0.047 | 21.9 | 50.97 |
| 实施例4 | 0.043 | 22.4 | 51.04 |
| 实施例5 | 0.040 | 22.7 | 51.43 |
| 对比例1 | 0.078 | 14.7 | 45.54 |
| 对比例2 | 0.074 | 15.6 | 46.32 |
| 对比例3 | 0.065 | 16.9 | 48.18 |
从表1可以看出，本发明实施例公开的包埋白藜芦醇具有更好的分散度和颗粒分布，且负载率和包埋率更高，这是各组分协同作用的结果。
上述实施例只为说明本发明的技术构思及特点，其目的在于让熟悉此项技术的人士能够了解本发明的内容并据以实施，并不能以此限制本发明的保护范围，凡根据依据本发明精神实质所作的等效变化或修饰，都应涵盖在本发明的保护范围之内。
Claims (9)
1.一种包埋白藜芦醇的制备方法，其特征在于，包括如下步骤：
步骤S1、超支化乙二醇壳聚糖季铵盐的制备：将超支化乙二醇壳聚糖、季铵盐试剂加入到有机溶剂中，在40-60℃下搅拌反应4-6小时，后旋蒸除去溶剂，并用乙醚洗涤产物3-7次，后旋蒸除去乙醚，得到超支化乙二醇壳聚糖季铵盐；
步骤S2、超支化乙二醇壳聚糖季铵甘草盐的制备：将经过步骤S1制成的超支化乙二醇壳聚糖季铵盐、甘草酸加入到水中，在50-70℃下搅拌反应4-6次，后旋蒸除去水，得到超支化乙二醇壳聚糖季铵甘草盐；
步骤S3、复合物的制备：将白藜芦醇加入到醇溶剂中配制成白藜芦醇溶液，然后向其中加入经过步骤S2制成的超支化乙二醇壳聚糖季铵甘草盐、茶多酚壳聚糖纳米粒、磺丁基-β-环糊精，搅拌30-40分钟，后冷冻干燥，制成包埋白藜芦醇。
2.根据权利要求1所述的一种包埋白藜芦醇的制备方法，其特征在于，步骤S1中所述超支化乙二醇壳聚糖、季铵盐试剂、有机溶剂的质量比为1:(0.3-0.5):(5-10)。
3.根据权利要求1所述的一种包埋白藜芦醇的制备方法，其特征在于，所述季铵盐试剂为3-氯-L-丙氨酸、2-氯丙酰甘氨酸、2-氯丙酰苷氨酸中的至少一种。
4.根据权利要求1所述的一种包埋白藜芦醇的制备方法，其特征在于，所述有机溶剂为四氢呋喃、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺中的任意一种。
5.根据权利要求1所述的一种包埋白藜芦醇的制备方法，其特征在于，步骤S2中所述超支化乙二醇壳聚糖季铵盐、甘草酸、水的质量比为1:(0.1-0.2):(5-10)。
6.根据权利要求1所述的一种包埋白藜芦醇的制备方法，其特征在于，步骤S3中所述白藜芦醇溶液的质量百分浓度为20-40％。
7.根据权利要求1所述的一种包埋白藜芦醇的制备方法，其特征在于，步骤S3中所述醇溶剂为乙醇、异丙醇、甘油中的至少一种。
8.根据权利要求1所述的一种包埋白藜芦醇的制备方法，其特征在于，步骤S3中所述白藜芦醇溶液、超支化乙二醇壳聚糖季铵甘草盐、茶多酚壳聚糖纳米粒、磺丁基-β-环糊精的质量比为2:1:(0.1-0.3):0.3。
9.一种根据权利要求1-8任一项所述的一种包埋白藜芦醇的制备方法制备得到的包埋白藜芦醇。
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| CN110101871A (zh) * | 2019-05-30 | 2019-08-09 | 广东工业大学 | 一种包埋白藜芦醇的制备方法 |
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