CN113788867A - 一种新型的叶黄素水溶性衍生物及其制备工艺 - Google Patents
一种新型的叶黄素水溶性衍生物及其制备工艺 Download PDFInfo
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Abstract
本发明涉及一种新型的叶黄素水溶性衍生物及其制备工艺。主要通过叶黄素和水苏糖进行酯化反应,制备新型的叶黄素水溶性衍生物。与叶黄素原药相比,本发明制备的新型叶黄素水溶性衍生物具有较好的亲水性能和生物可利用性,并保持了叶黄素原有的生物活性,可添加到多种剂型或多功能食品中。此外,本发明制备工艺流程简单,周期短,成本低,易于扩大,易于产业化的优点。
Description
技术领域
本发明涉及化学合成和改善难溶药物水溶性技术领域,主要涉及
一种新型的叶黄素水溶性衍生物及其制备工艺,提供新型水溶性叶黄素化合物,改善其水溶性和生物利用度。
背景技术
叶黄素是天然存在的抗氧化剂,在临床上已经应用于防治老年性黄斑病变、治疗青光眼、白内障的辅助药物,同时在保健食品领域也被大众认可。对于叶黄素而言,多为口服给药。然而叶黄素要通过胃肠道被吸收,必须先客人付其溶解度差的问题,因此,改善叶黄素的口服生物利用度具有十分重要的意义。
水苏糖无毒、可做保健食品或作为食品添加剂使用。水苏糖是近年来食品市场上比较受欢迎的一种新型微生态健康食品,它是一种能显著促进双歧杆菌增殖的功能性低聚糖,能够有效地促进人体内双歧杆菌的增殖,酸化肠道,具有抑制腐败物生成和胆固醇升高等改善肠道环境的效用,对防病、抗病和美容具有显著作用,被誉为“超强双歧因子”。
发明内容
基于上述事实,本发明选择水苏糖对叶黄素结构进行修饰,在保持原有活性的基础上,使得叶黄素的水溶性和生物利用度都得到了显著的改善。并对新型的叶黄素水溶性衍生物进行了全面表征。水苏糖对叶黄素进行修饰,本工艺具有操作简单,制备周期短,成本低,易于扩大,易于产业化的优点。
本发明制备的新型的叶黄素水溶性衍生物及其制备工艺,合成步骤如下:
合成路线:首先,叶黄素与琥珀酸酐以一定摩尔比加入溶剂体系内,搅拌至溶解,在一定温度下反应一段时间后,叶黄素通过与琥珀酸酐键合,在叶黄素分子上引入羧基基团;然后在反应体系中加入催化剂活化羧基,活化结束后,反应体系中加入水苏糖,与其糖分子中的羟基进行酯化反应;反应结束后,在反应体系中加入另一种溶剂,通过反溶剂重结晶的方式分离合成产物,反溶剂清洗产物数次,将产物分散在水中,冷冻干燥后,获得新型的叶黄素水溶性衍生物。
所述叶黄素与琥珀酸酐的摩尔比是1:0.25-1:2。
所述溶剂体系为二甲基亚砜(DMSO)。
所述叶黄素与琥珀酸酐的反应温度优选35-45℃;反应时间优选24-36h。
所述催化剂为1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸(EDC) 和4-二甲氨基吡啶(DMAP),优选摩尔比为琥珀酸酐:EDC:DMAP=1:1:1。
所述的水苏糖的纯度≥85%,叶黄素与水苏糖的摩尔为1:0.0.25-1:2。
所述反应体系中加入水苏糖后,优选反应温度为28-35℃。
所述反溶剂为乙醇。
所述的新型的叶黄素水溶性衍生物红外光谱中在1744cm-1和1153cm-1处有特征峰。
所述的新型的叶黄素水溶性衍生物1H核磁共振光谱中在4.95ppm和5.4 ppm处有特征峰。
本发明的优点:
1.本发明选用修饰叶黄素结构的物质水苏糖,无毒副作用,生物降解性好,生物相容性高,利于肠道的吸收适合应用于口服药制备中。
2.本发明为改善难溶性药物生物利用度的研究工作提供了新的思路。
3.本发明使用的溶剂均属于无毒或低毒性,不易伤害实验人员,不易污染环境。
4.本发明工艺流程简单,易于放大至产业化生产。
5.本发明所需的设备简单且价格低廉,不需要很高的制备成本。
附图说明
图1是叶黄素原药(a)和本发明制备的叶黄素水溶性衍生物(b)的形貌对比图;
图2是叶黄素原药(a)、本发明制备的叶黄素水溶性衍生物(b)以及叶黄素与水苏糖的物理混合物(c)的XRD检测图;
图3叶黄素原药(a)、水苏糖(b)以及本发明制备的叶黄素水溶性衍生物(c)的1H-NMR检测图;
图4叶黄素原药(a)、叶黄素与水苏糖的物理混合物(b)以及本发明制备的叶黄素水溶性衍生物(c)的溶出曲线图;
图5叶黄素原药(a)、叶黄素与水苏糖的物理混合物(b)以及本发明制备的叶黄素水溶性衍生物(c)的血药浓度曲线图;
具体实施方案
此处所描述的具体实施例仅用以解释本发明,提供在制备过程中较好的实施例,但并不用于限定本发明。
实例1:
首先精确称量一定摩尔比的叶黄素与琥珀酸酐(摩尔比为1:1)。以二甲基亚砜(DMSO)为反应溶剂,在40℃下搅拌12h。在催化剂催化条件下,将称量好的水苏糖(摩尔比,叶黄素:水苏糖=1:0.25)加入反应体系中,在25℃下搅拌24h。所得反应溶液采用反溶剂法(乙醇为反溶剂)得到目标化合物。将最终所得沉淀物进行冻干处理。制备所得叶黄素水溶性衍生物的得率为30.23%。实例2:
首先精确称量一定摩尔比的叶黄素与琥珀酸酐(摩尔比为1:1)。以二甲基亚砜(DMSO)为反应溶剂,在40℃下搅拌12h。在催化剂催化条件下,将称量好的水苏糖(摩尔比,叶黄素:水苏糖=1:0.5)加入反应体系中,在25℃下搅拌24h。所得反应溶液采用反溶剂法(乙醇为反溶剂)得到目标化合物。将最终所得沉淀物进行冻干处理。制备所得叶黄素水溶性衍生物的得率为59.78%。
实例3:
首先精确称量一定摩尔比的叶黄素与琥珀酸酐(摩尔比为1:1)。以二甲基亚砜(DMSO)为反应溶剂,在40℃下搅拌12h。在催化剂催化条件下,将称量好的水苏糖(摩尔比,叶黄素:水苏糖=1:1)加入反应体系中,在25℃下搅拌 24h。所得反应溶液采用反溶剂法(乙醇为反溶剂)得到目标化合物。将最终所得沉淀物进行冻干处理。制备所得叶黄素水溶性衍生物的得率为51.47%。
Claims (10)
2.根据权利要求1中所述的一种新型的叶黄素水溶性衍生物及其制备工艺,其特征在于,所述叶黄素与琥珀酸酐的摩尔比是1:0.1-1:3。
3.根据权利要求1中所述的一种新型的叶黄素水溶性衍生物及其制备工艺,其特征在于,所述溶剂体系为二甲基亚砜(DMSO)。
4.根据权利要求1中所述的一种新型的叶黄素水溶性衍生物及其制备工艺,其特征在于,所述叶黄素与琥珀酸酐的反应温度为30-60℃,反应时间为12-48h。
5.根据权利要求1中所述的一种新型的叶黄素水溶性衍生物及其制备工艺,其特征在于,所述催化剂为1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐(EDC)和4-二甲氨基吡啶(DMAP),投料比例以琥珀酸酐的添加量为参考,摩尔比为琥珀酸酐:EDC:DMAP=1:1.5:1.5。
6.根据权利要求1中所述的一种新型的叶黄素水溶性衍生物及其制备工艺,其特征在于,所述水苏糖的纯度≥85%,叶黄素与水苏糖的摩尔比为1:0.1-1:3。
7.根据权利要求1中所述的一种新型的叶黄素水溶性衍生物及其制备工艺,其特征在于,反应体系中加入水苏糖后,所述反应温度为25-40℃。
8.根据权利要求1中所述的一种新型的叶黄素水溶性衍生物及其制备工艺,其特征在于,所述反溶剂为乙醇。
9.根据权利要求1中所述的一种新型的叶黄素水溶性衍生物及其制备工艺,其特征在于,获得的新型的叶黄素水溶性衍生物红外光谱中在1744cm-1和1153cm-1处有特征峰。
10.根据权利要求1中所述的一种新型的叶黄素水溶性衍生物及其制备工艺,其特征在于,获得的新型的叶黄素水溶性衍生物1H核磁共振光谱中在4.95ppm和5.4ppm处有特征峰。
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