CN101308068B - 黄酮类化合物的应用 - Google Patents
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Abstract
本发明涉及黄酮类化合物的应用。提供了黄酮类化合物槲皮素、儿茶素、黄芩素或汉黄芩素用于基质辅助激光解吸电离飞行时间质谱的基质。所述的黄酮类化合物苯环上含有邻位的羟基和羰基，这些羟基和羰基、羟基和羟基之间能以氢键方式在分子内形成稳定的六元环或五元环结构，有利于所述的黄酮类化合物作为基质与分析物之间进行的质子交换。所述的黄酮类化合物作为基质，由于酸性较弱，能够高效、快速地应用于多糖、静电复合物、有机无机配合物和C60衍生物等难以表征样品的分析，解决了某些在常用酸性基质中稳定性差、易受环境影响而发生复合物解离、甚至化学键断裂的样品分子量及结构分析的难题。
Description
技术领域
本发明涉及黄酮类化合物的应用。
技术背景
基质是MALDI-TOF质谱分析最重要的部分，是MALDI-TOF质谱分析能否成功的关键。高效基质的发现和使用可以扩展MALDI-TOF质谱的应用范围。自二十世纪八十年代，Tanaka和Hillenkamp分别采用金属粉末与甘油的混合物和烟酸作为基质并成功分析了多肽和蛋白之后，基质的筛选、使用和基质的作用机理就成为人们研究的热点。
总结多年来诸多研究者对MALDI-TOF质谱基质的探索，发现一种有效的基质应该具备以下特点：
(1)能有效地稀释和分散样品分子；
(2)基质在所使用的激光波长区域有较强的吸收(常用的N2激光器的激光波长为337nm)；
(3)基质和样品能溶于同种溶剂(这一点可以用不同的点样方法来克服)；
(4)具有真空稳定性，不易在真空中很快挥发；
(5)能够对生物样品中的缓冲溶液及无机盐类有一定的抵抗作用；
(6)促使样品离子化；
(7)不直接与样品发生化学反应；
(8)在高温下易升华；
(9)在激光照射下，在分子内和分子间能够发生阳离子转移反应。
到目前为止，文献所报道的基质一般为含芳香环或不饱和结构和羟基、氨基和羧基等官能团的有机小分子化合物，且为数不多。这很难满足日常工作中性质各异分析物的分析需要，尤其是那些在酸性环境中不稳定的样品，利用MALDI-TOF质谱很难得到理想的结果。
发明内容
结合基质的应用现状和作为基质应具备的条件，发明人对多种仅含有-OH基团而不含有-COOH基团的弱酸性芳香类物质进行了筛选研究，讨论了它们成为基质的可能性以及它们在MALDI-TOF质谱实验中的应用表现。
在常用的有效基质芥子酸(SA)、α-氰基-4-羟基肉桂酸(CHCA)、阿魏酸(FA)、2，5-二羟基苯甲酸(DHB)、全反式视黄酸(RTA)、2-(4-羟基苯基偶氮苯甲酸)(HABA)和反式-3-吲哚丙烯酸(IAA)的分子结构中存在苯环和丙烯酸形成的共扼体系，这些共扼体系能使这些基质化合物对紫外区337nm激光有较强的吸收。在DHB、3-羟基吡啶甲酸(3-HPA)和2，4，6-三羟基苯乙酮(THAP)等分子中的苯环上含有邻位的羟基和羰基，它们之间以氢键方式在分子内形成稳定的六元环结构，这有利于样品和基质之间的质子转移。在这些基质分子中包含1个以上的羟基、羧基、氨基等基团。根据上述情况，一种有机物能否成为一种有效的基质应该具备以下条件：
(1)结构中包含共轭体系，对紫外区的激光有较强的吸收；
(2)结构中芳环的相邻位置上的羟基和羰基可以通过氢键的方式形成稳定的六元环，有利于基质与分析物之间进行质子交换。
结合作为有效基质所具备的条件，本发明选择黄酮类化合物用于基质辅助激光解吸电离飞行时间质谱的基质；所述的黄酮类化合物为(1)槲皮素、(2)儿茶素、(3)黄芩素或(4)汉黄芩素；它们的结构分别如下：
黄酮类化合物用于基质辅助激光解吸电离飞行时间质谱的基质的用法的步骤和条件如下：分别称取每份槲皮素、儿茶素、黄芩素或汉黄芩素各1mg，并且每一种分别称取3份，然后分别把每份溶于100μL甲醇、乙醇或丙酮中，得到12种溶液，在分别振荡至充分溶解，离心取上清液保存；
分别取上述槲皮素、儿茶素、黄芩素或汉黄芩素的12种溶液各1μL，点在100孔的不锈钢靶上，待风干后，将样品靶送入离子源，进行MALDI-TOF质谱实验。
有益效果：从上述的黄酮类化合物的结构，不难发现，在这些黄酮类化合物中不仅能以氢键的形式形成六元环，还可以形成同样稳定的五元环，这有利于它们与分析物之间进行的质子交换。因此，选择槲皮素、儿茶素、黄芩素或汉黄芩素黄酮类化合物用于基质辅助激光解吸电离飞行时间质谱的基质，分析了在常用的酸性基质中出现稳定性差、易受环境影响而发生作用力消失、甚至化学键断裂等现象的样品。
在MALDI-TOF MS中，槲皮素、儿茶素、黄芩素或汉黄芩素，在合适的溶剂条件下能够作为多糖、静电复合物、有机无机配合物和C60衍生物等有效的基质，其效果比常用的酸性基质效果好很多，与THAP这种弱酸性基质效果相当。这解决了在常用的酸性基质中稳定性差、易受环境影响而发生作用力消失、甚至化学键断裂等样品分子量及结构分析的难题，同时也在一定程度上拓宽了利用MALDI-TOF MS研究的范围。
附图说明
图1、2、3和4分别是槲皮素、儿茶素、黄芩素或汉黄芩素在没有加入其它任何基质条件下的MALDI-TOF质谱。
表1.槲皮素、儿茶素、黄芩素或汉黄芩素与DHB、THAP在三种溶剂中作基质，对多糖、静电复合物、有机无机配合物和C60衍生物进行的MALDI-TOF质谱分析结果对比。
具体实施方式
实施例1：
分别称取每份槲皮素、儿茶素、黄芩素或汉黄芩素各1mg，并且每一种分别称取3份，然后分别把每份溶于100μL甲醇、乙醇或丙酮中，得到12种溶液，再分别振荡至充分溶解，离心取上清液保存；
分别取上述槲皮素、儿茶素、黄芩素或汉黄芩素的12种溶液各1μL，点在100孔的不锈钢靶上，待风干后将样品靶送入离子源，进行MALDI-TOF质谱实验。
得到的谱图显示溶剂对四种黄酮类化合物的出峰情况影响较小，而且出峰情况比较简单，这满足了成为有效基质的必备条件。如图1-4是槲皮素、儿茶素、黄芩素或汉黄芩素，在甲醇溶液中的MALDI-TOF质谱图。在图1-3中出现了三个主要的峰，它们从左至右分别是槲皮素、儿茶素和黄芩素的脱去一个水分子的质子化峰、质子化峰和钠离子化峰。图4中出现了两个主要的峰，它们从左至右分别是汉黄芩素质子化峰和汉黄芩素的钠离子化峰，而脱去一分子水的质子化峰的丰度很低。
实施例2：分别称取DHB和THAP各1mg，并且每一种称量3份，
把每份DHB和THAP分别溶于100μL甲醇、乙醇或丙酮中，得到6种溶液，再分别得到振荡至充分溶解，分别离心取上清液保存；
多糖用超纯水(请给所谓超纯水的表征指标值！)配成4mg/mL的溶液，分别以实例1中的槲皮素、儿茶素、黄芩素或汉黄芩素的12种溶液与DHB、THAP两种基质的6种溶液作为基质进行对比分析，取所有的基质溶液1μL点在100孔的不锈钢靶上，待风干后，在这些基质上层点上1μL的多糖溶液，待风干后将样品靶送入离子源，利用MALDI-TOF质谱对比分析。结果参见表1。
实施例3：
有机无机配合物以氯仿为溶剂，配成5mg/mL的溶液。分别以实例1中的槲皮素、儿茶素、黄芩素或汉黄芩素的12种溶液与实例2中DHB、THAP两种基质的6种溶液作为基质进行对比分析，取所有的基质溶液1μL点在100孔的不锈钢靶上，待风干后，在这些基质上层点上1μL的有机无机配合物溶液，待风干后将样品靶送入离子源，利用MALDI-TOF质谱对比分析。结果参见表1。
实施例4：静电复合物以氯仿为溶剂，配成5mg/mL的溶液。分别以实例1中的槲皮素、儿茶素、黄芩素或汉黄芩素的12种溶液与实例2中DHB、THAP两种基质的6种溶液作为基质进行对比分析，取所有的基质溶液1μL点在100孔的不锈钢靶上，待风干后，在这些基质上层点上1μL的静电复合物溶液，待风干后将样品靶送入离子源，利用MALDI-TOF质谱对比分析。结果参见表1。
实施例5：
C60的衍生物溶于甲苯，配成2mg/mL的溶液。分别以实例1中的槲皮素、儿茶素、黄芩素或汉黄芩素的12种溶液与实例2中DHB、THAP两种基质的6种溶液作为基质进行对比分析，取所有的基质溶液1μL点在100孔的不锈钢靶上，待风干后，在这些基质上层点上1μL的C60的衍生物溶液，待风干后将样品靶送入离子源，利用MALDI-TOF质谱对比分析。结果参见表1。
表1.
Q：槲皮素；C：儿茶素；B：黄芩素；W：汉黄芩素；“+”代表在相应的条件下能够得到良好的谱图，“0”代表在相应的条件下能够得到一般的谱图，“-”代表在相应的条件下谱图效果很差或者得不到分析结果。
Claims (1)
1.黄酮类化合物的应用，其特征在于，黄酮类化合物作为基质辅助激光解吸电离飞行时间质谱的基质；所述的黄酮类化合物为(1)槲皮素、(2)儿茶素、(3)黄芩素或(4)汉黄芩素；它们的结构分别如下：
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