CN1304591C - 一种提高黄酮苷元极性的方法 - Google Patents
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Abstract
本发明公开了一种提高黄酮苷元极性的方法,是将黄酮苷元、葡萄糖苷酶和糖基底物在90%以下浓度的乙醇水溶液中进行反应;所述黄酮苷元为槲皮素或山萘酚,所述糖基底物为糊精、淀粉或麦芽糖。所述反应温度为20-90℃,反应时间为1-30小时。本发明可显著提高槲皮素和山萘酚等黄酮苷元的水溶性,使其在工业生产中易被水或乙醇等极性溶剂溶解,作为医药产品的槲皮素苷和山萘酚苷与槲皮素、山萘酚相比,更易被机体利用;还可提高天然产物中黄酮类物质的提取率,从而降低其提取过程中的乙醇用量;此外,本发明还提高了总黄酮及纯黄酮制品的可加工性,同时可扩大其实际应用范围。
Description
技术领域
本发明涉及一种提高化合物极性的方法,特别是涉及一种提高黄酮苷元极性的方法。
背景技术
黄酮苷元是黄酮类化合物(Flavonoid compounds)的一种主要存在形式。
槲皮素(Quercetin)和山萘酚(Kaempferol)是黄酮苷元的代表性物质,它们均是以C6-C3-C6为基本结构的脂溶性化合物,极性低,只溶于乙酸乙酯、氯仿、乙醚等非极性溶剂。目前,槲皮素和山萘酚主要来源于天然产物的提取。
槲皮素的分子式为C15H10O5,其化学结构式如式I所示,它及其衍生物具有多种生理活性,如具有抗癌、抗病毒、治疗心血管疾病等药理作用。它们在植物界分布广泛,其中槲皮素广泛存在于植物的花、叶、果实中。药用植物如槐花、侧柏叶、高良姜、款冬花、桑寄生和三七都含有槲皮素,尤其是荞麦、沙棘、山楂和洋葱中槲皮素的含量最高。国内外学者对于槲皮素及其衍生物的提取、纯制、药理和临床进行了大量的研究。在实际应用中,槲皮素多以苷类形式如芦丁、槲皮苷、金丝桃苷等被使用。从药代动力学的角度来看,槲皮素苷比槲皮素在体内更容易被吸收,在药理研究中也显示出同样的生理活性。现有生产槲皮素的方法中多使用丙酮、丁酮作为溶剂进行提取,但这些有机溶剂对机体会产生有害作用,且将其用于工业化生产会产生安全性低、污染严重、成本高等问题。为了避免使用对机体有害的有机溶剂,在饮料和医药品的提取过程中多用醇水作为溶剂。但由于天然的槲皮素极性低,在实际应用中需要使用60%以上含醇水溶液,导致乙醇用量大,生产成本高。
(式I)
山萘酚的分子式为C15H10O6,其化学结构式如式II所示,它及其衍生物在植物界分布广泛,且具有抗菌消炎等药理作用,很多中药如菟丝子、贯叶连翘、香椿、莲须、三棱、山楂、南葶苈子和灯盏细辛都含有山萘酚。由于山萘酚的极性较低,在乙醇水溶剂中难以溶解,在实际生产中,山萘酚的极性越大越好。
因此,为了扩大槲皮素、山萘酚等黄酮苷元的应用范围及其在机体中的利用效率,迫切需要一种提高其极性的方法。
发明内容
本发明的目的是提供一种提高黄酮苷元极性的方法。
本发明所提供的提高黄酮苷元极性的方法,是将黄酮苷元、转苷酶和糖基底物在浓度为0%-90%的乙醇水溶液中进行反应。
所述黄酮苷元的来源是广泛的,可以是纯化的,可以是化学合成的,也可以是含有黄酮苷元的天然产物。
所述黄酮苷元与乙醇水溶液的重量体积比为0.03-0.07克/100毫升。
所述乙醇水溶液的pH值为2-9,乙醇的浓度优选为40%。
所述反应温度为20-90℃,反应时间为1-30小时。
所述转苷酶可为任意一种转苷酶,优选为葡萄糖苷酶,更优选为spirizyme plus葡萄糖苷酶、suhong475葡萄糖苷酶。所述乙醇水溶液中转苷酶的终浓度1600-1900 IU/100mL。
所述黄酮苷元与糖基底物的重量份数比为1∶4.5-5。
所述糖基底物可为糊精、淀粉或麦芽糖。
本发明尤其适用于槲皮素,山萘酚和含有槲皮素或山萘酚的天然产物。
本发明提供了一种应用转苷酶反应使槲皮素、山萘酚等黄酮苷元单体转变为相应的黄酮苷以提高其极性的方法。在转苷酶的作用下,糖基底物中糖基被转移到黄酮苷元的羟基基团上,从而生产出极性增强的苷类物质。本发明可显著提高槲皮素和山萘酚等黄酮苷元的水溶性,使其在工业生产中易被水或乙醇等极性溶剂溶解,作为医药产品的槲皮素苷和山萘酚苷与槲皮素、山萘酚相比,更易被机体利用;还可提高天然产物中黄酮类物质的提取率,从而降低其提取过程中的乙醇用量;此外,本发明还提高了总黄酮及纯黄酮制品的可加工性,同时可扩大其实际应用范围。
附图说明
图1为槲皮素转苷产物用乙酸乙酯萃取液分析结果
图2为山萘酚转苷产物用乙酸乙酯萃取液分析结果
具体实施方式
下述实施例中所用方法如无特别说明均为常规方法。
实施例1、提高槲皮素的极性
向1000mL三角瓶中,加入0.025g槲皮素、0.1125g麦芽糖及50mL 30%乙醇水溶液,用1N NaOH溶液调pH值至6.0,然后加入penicillium decumbens葡萄糖苷酶溶液(6.23IU/mL)0.5mL,最后,在50℃、200rpm下,搅拌反应30小时。反应结束后,用相同体积的乙酸乙酯萃取反应产物(以芦丁为阳性对照),萃取液以GF254硅胶板(10cm×20cm)、苯∶乙酸乙酯∶丙酮∶乙酸=10∶8∶2∶2为流动相展开,在365nm紫外灯下观察荧光并用TLC方法进行定性定量分析,结果如图1所示(1.Rf槲皮素=0.68,
2.Rf槲皮素转苷产物=0.30,3.Rf芦丁=0.01),表明通过转苷反应产生了极性大于槲皮素的槲皮素苷,使其在工业生产中易被水或乙醇等极性溶剂所溶解,反应机理可用下述化学方程式表示:
实施例2、提高山萘酚的极性
向1000mL三角瓶中,加入0.015g山萘酚、0.072g麦芽糖及50mL 60%乙醇水溶液,用1N NaOH溶液调pH值至9.0,然后加入spirizyme plus葡萄糖苷酶(标准活力400AGU/g)2.0mL,在30℃、200rpm下,搅拌反应1小时。反应结束后,用相同体积的乙酸乙酯萃取(以芦丁为阳性对照),萃取液以GF254硅胶板(10cm×20cm)、苯∶乙酸乙酯∶丙酮∶乙酸=10∶8∶2∶2为流动相展开,在365nm紫外灯下观察荧光并用TLC方法进行定性定量分析,结果如图2所示(1.Rf山萘酚=0.87,2.Rf山萘酚转苷产物=0.10,3.Rf芦丁=0.01),表明通过转苷反应之后产生了极性大于山萘酚的山萘酚苷,使其在工业生产中易被水或乙醇等极性溶剂所溶解,反应机理可用下述化学方程式表示:
实施例3、提高槲皮素的极性
向1000mL三角瓶中,加入0.025g槲皮素、0.125g麦芽糖及50mL 30%乙醇水溶液,用1N NaOH溶液调pH值至2.0,然后加入suhong475葡萄糖苷酶(标准活力475AGU/g)0.5mL,在90℃,200rpm下,搅拌反应30小时。反应结束后,用相同体积乙酸乙酯萃取(以芦丁为阳性对照),萃取液以GF254硅胶板(10cm×20cm)、苯∶乙酸乙酯∶丙酮∶乙酸=10∶8∶2∶2为流动相展开,在365nm紫外灯下观察荧光并用TLC方法进行定性定量分析,结果如图1所示(1.Rf槲皮素=0.68,2.Rf槲皮素转苷产物=0.30,3.Rf芦丁=0.01),表明通过转苷反应产生了极性大于槲皮素的槲皮素苷,使其在工业生产中易被水或乙醇等极性溶剂所溶解,反应机理与实施例1相同。
实施例4、提高山萘酚的极性
向1000mL三角瓶中,加入0.035g山萘酚、0.168g麦芽糖及50mL 10%乙醇水溶液,用1N NaOH溶液调pH值至6.0,然后加入suhong475葡萄糖苷酶(标准活力475AGU/g)0.5mL,在50℃、200rpm下,搅拌反应20小时。反应结束后,用相同体积乙酸乙酯萃取(以芦丁为阳性对照),萃取液以GF254硅胶板(10cm×20cm)、苯∶乙酸乙酯∶丙酮∶乙酸=10∶8∶2∶2为流动相展开,在365nm紫外灯下观察荧光并用TLC方法进行定性定量分析,结果如图2所示(1.Rf山萘酚=0.87,2.Rf山萘酚转苷产物=0.10,3.Rf芦丁=0.01),表明通过转苷反应之后产生了极性大于山萘酚的山萘酚苷,使其在工业生产中易被水或乙醇等极性溶剂所溶解,反应机理与实施例2相同。
Claims (7)
1、一种提高黄酮苷元极性的方法,是将黄酮苷元、葡萄糖苷酶和糖基底物在90%以下浓度的乙醇水溶液中进行反应;所述黄酮苷元为槲皮素或山萘酚,所述糖基底物为糊精、淀粉或麦芽糖。
2、根据权利要求1所述的提高黄酮苷元极性的方法,其特征在于:所述黄酮苷元与乙醇水溶液的重量体积比为0.03-0.07克/100毫升。
3、根据权利要求1所述的提高黄酮苷元极性的方法,其特征在于:所述乙醇水溶液的pH值为2-9,乙醇的浓度为40%。
4、根据权利要求1所述的提高黄酮苷元极性的方法,其特征在于:所述反应温度为20-90℃,反应时间为1-30小时。
5、根据权利要求1所述的提高黄酮苷元极性的方法,其特征在于:所述葡萄糖苷酶为spirizyme plus葡萄糖苷酶或suhong475葡萄糖苷酶。
6、根据权利要求5所述的提高黄酮苷元极性的方法,其特征在于:所述乙醇水溶液中葡萄糖苷酶的终浓度为1600-1900IU/100mL。
7、根据权利要求1-6任一所述的提高黄酮苷元极性的方法,其特征在于:所述黄酮苷元与糖基底物的重量份数比为1∶4.5-5。
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