CN107441770A - 黄酮化合物的萃取方法以及苯基键合硅胶固相萃取柱 - Google Patents
黄酮化合物的萃取方法以及苯基键合硅胶固相萃取柱 Download PDFInfo
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims abstract description 178
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 82
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- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 claims description 4
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Classifications
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Abstract
本发明提供了一种苯基键合硅胶固相萃取柱,其具有空腔柱管(1),所述空腔柱管(1)在内部设置有上筛板(2)和下筛板(4),在所述上筛板(2)和下筛板(4)之间填充有填料(3),所述填料为苯基键合硅胶。本发明还提供了所述苯基键合硅胶固相萃取柱的制备方法、使用所述苯基键合硅胶固相萃取柱对黄酮化合物进行固相萃取的方法、以及使用高效液相色谱对使用所述苯基键合硅胶固相萃取柱萃取的黄酮化合物进行检测的方法。
Description
技术领域
本发明涉及一种黄酮化合物的萃取方法,具体而言涉及一种使用苯基键合硅胶固相萃取柱对黄酮化合物进行萃取的方法,属于分析化学领域。本发明还涉及一种新型苯基键合硅胶固相萃取柱。
背景技术
黄酮是一类天然多酚类物质,广泛存在于植物组织中,具有清除自由基、抗氧化、抗肿瘤、杀菌、保肝、增强免疫力等多种功能,在天然药物化学中占有重要位置。日常生活中,保健食品或药物中多有黄酮存在。开发准确测定黄酮含量的富集检测方法,对于确保黄酮产品质量具有重要的意义。
固相萃取技术作为一项以固体材料为吸附剂,萃取分离液态样品中被分析物的技术,具有富集倍数高、有机溶剂耗量少、操作简单等优点,非常适合复杂样品中微量被分析物的富集与检测。固相萃取技术的核心是萃取材料,其性能直接决定了萃取效果。近年来,随着材料科学的发展,不同类型的萃取材料层出不穷,例如石墨烯、离子液体、金属有机骨架材料、限进材料等材料的应用使得固相萃取技术取得了长足发展。
在硅胶表面键合不同化学官能团是制备固相萃取材料的常用方式,其中,碳十八键合硅胶是最常用的且已经商品化的固相萃取材料。然而,碳十八键合硅胶与被分析物之间仅存在着单一的疏水作用,难以有效萃取极性较强的黄酮分子。现有技术中,已经有非专利文献1通过制备硝基吲哚键合硅胶,有效萃取了水溶液中的黄酮分子,然而,该方法中所使用的硝基吲哚键合硅胶合成方法较为复杂,萃取材料成本较高。因此,本领域中对于开发制备方法简单易行、成本较低的同时,具有较高黄酮化合物萃取效率的固相萃取材料仍存在实际需求。
非专利文献1:N.Wang,X.J.Liang,Q.Li,Y.Liao and S.J.Shao,Nitro-substituted 3,3’-bis(indolyl)methanemodified silica gel as a sorbent forsolid-phase extraction of flavonoids.RSC Adv.,2015,5,15500-15506.
发明内容
为解决上述课题,发明人经过潜心研究与大量实验,出人意料地发现,通过以苯基三氯硅烷为基质,制备苯基键合硅胶,并使用该苯基键合硅胶制成苯基键合硅胶固相萃取柱,可以高效地萃取黄酮化合物,并且该苯基键合硅胶固相萃取柱还具有制备方法简单易行、成本较低的优势,从而完成了本发明。
在第一方面,本发明提供了一种苯基键合硅胶固相萃取柱,其具有空腔柱管1,所述空腔柱管1在内部设置有上筛板2和下筛板4,在所述上筛板2和下筛板4之间填充有填料3,所述填料为苯基键合硅胶。
在优选的实施方式中,所述填料3的粒径为50~80μm,使用量为80~120mg,优选100mg;所述填料3的比表面积为>300m2/g。
在进一步优选的实施方式中,所述空腔柱管1为玻璃空腔柱管或聚丙烯空腔柱管;所述空腔柱管1的形状为圆柱形,其容积为6mL;所述空腔柱管1的内径为1-1.5cm,优选1.3cm。
在进一步优选的实施方式中,所述上筛板2和所述下筛板4的直径与所述空腔柱管1的内径相一致;所述上筛板2和所述下筛板4具有筛孔,所述筛孔的孔径为3-10μm、优选5μm;和/或所述上筛板2和所述下筛板4的厚度为1~2mm。
在第二方面,本发明提供了所述苯基键合硅胶固相萃取柱的制备方法,所述方法包括以下步骤:
(a)将硅胶置于非极性溶剂中,加入苯基三氯硅烷和催化剂,在搅拌下加热回流直至反应完成,随后经纯化处理获得苯基键合硅胶;
(b)将苯基键合硅胶装入固相萃取柱管,以筛板压实,制成所述苯基键合硅胶固相萃取柱。
在优选的实施方式中,所述步骤(a)中,所述非极性溶剂为甲苯,所述催化剂为吡啶。
在进一步优选的实施方式中,以100mL甲苯计算,所述硅胶的使用量为2.0-4.0g,优选3.0g;所述苯基三氯硅烷的使用量为0.75-1.5mL,优选1mL;所述吡啶的添加量为0.08-0.12mL,优选0.1mL;所述加热回流进行10-15h,优选12h;所述纯化处理包括离心处理、依次以乙醇和水洗涤和烘干。
在第三方面,本发明还提供了一种使用本发明的苯基键合硅胶固相萃取柱对黄酮化合物进行萃取的方法,所述方法包括以下步骤:
(1)以甲醇和水对本发明的苯基键合硅胶固相萃取柱进行淋洗和活化;
(2)通过泵驱动使待测黄酮工作液通过苯基键合硅胶固相萃取柱;
(3)使用甲醇通过苯基键合硅胶固相萃取柱进行洗脱,获得洗脱液。
在优选的实施方式中,所述步骤(1)中,所述甲醇和水的使用量分别为5mL;所述步骤(2)中,所述泵为蠕动泵;所述待测黄酮工作液的用量为20~150mL,优选50mL,且在事先被调整至pH值4~5、优选pH值4.0的状态;所述待测黄酮工作液通过所述苯基键合硅胶固相萃取柱的流速为1.5~2.0mL/min,优选2.0mL/min;所述步骤(3)中,所述甲醇的使用量为1.0mL,所述流速为不超过0.4mL/min、优选0.4mL/min。
在另一方面,本发明还涉及使用高效液相色谱对上述洗脱液中的黄酮化合物进行检测的方法。
在优选的实施方式中,所述高效液相色谱的色谱条件为:ODS分析柱(150mm×4.6mm I.D.);以甲醇与H3PO4水溶液[0.2wt%]为流动相A与B进行梯度洗脱:0-0.5min为0.51-12.5min为12.51-25min为流动相流速:1.0mL/min;柱温:25℃;进样体积:20μL;紫外检测器,波长360nm。
与现有技术相比,本发明提供了一种新的苯基键合硅胶固相萃取柱,其具有制备简便易行、成本低廉的优点,并且通过该苯基键合硅胶固相萃取柱能够简便快捷的对黄酮化合物进行萃取,并且可随后用于色谱检测。该方法具有宽的线性范围、低的检出限,可适用于多种实际样品中黄酮化合物的富集检测,因此有着良好的性能和广阔的应用前景。
附图说明
图1示出了本发明的苯基键合硅胶固相萃取柱的结构示意图。
图2示出了实施例2制备的苯基键合硅胶的扫描电镜图片。
图3示出了苯基键合硅胶和硅胶基质的红外光谱。
图4A-4C示出了固相萃取的操作参数以及黄酮工作液的pH值与萃取效率之间的关系。
图5A-5C示出了洗脱步骤的参数与萃取效率之间的关系。
具体实施方式
对于本领域技术人员而言已知的是,苯基三氯硅烷是一种简单的、常见的硅烷试剂,发明人首次发现,以其为反应物制备的苯基键合硅胶,从理论上可以有效的萃取黄酮化合物,这可能是由于苯环的存在,与黄酮分子之间具有π-π相互作用的结果。
实施例
接下来,通过实施例对本发明进行进一步详细地说明,但本发明不仅限于这些实施例。
在以下实施例中所使用的试剂如下:
硅胶,200~300目,青岛邦凯分离材料有限公司;苯基三氯硅烷,分析纯,上海麦克林生化科技有限公司;吡啶、甲苯,分析纯,国药集团化学试剂有限公司;磷酸,分析纯,白银良友化学试剂有限公司;乙酸,分析纯,天津化学试剂二厂;甲醇,分析纯,山东禹王集团;槲皮素(QUE)、木犀草素(LUT)、异鼠李素(IRA)和山奈酚(KAE)(分析纯、上海安耐吉化学)。
固相萃取仪,禾工科技,中国;高效液相色谱仪,安捷伦1100,美国;扫描电镜,JSM-6701F,日本;比表面积/孔径分析仪,ASAP2010,美国;元素分析仪,Hanau,德国;红外光谱仪,Nexus 870,美国。
实施例1 苯基键合硅胶固相萃取柱
在本实施例中对本发明的苯基键合硅胶固相萃取柱进行说明。
如图1所示,本实施例的苯基键合硅胶固相萃取柱具有圆柱形玻璃空腔柱管1,其容积为6mL,内径为1.3cm;所述空腔柱管1在内部设置有厚1mm、直径与所述空腔柱管1的内径相一致的上筛板2和下筛板4,所述上筛板2和所述下筛板4具有筛孔,所述筛孔的孔径为5μm;在所述上筛板2和下筛板4之间填充有填料3,所述填料为苯基键合硅胶。
在本实施例中,所述填料3的粒径为50~80μm,使用量为100mg;所述填料3的比表面积为320m2/g。
实施例2 苯基键合硅胶的制备
本实施例中,苯基键合硅胶的制备通过以下步骤进行:称取3.0g硅胶置于100mL甲苯中,加入1mL苯基三氯硅烷,再加入0.1mL吡啶作为催化剂,将上述体系搅拌均匀,加热回流12h,完成反应。离心处理产物,乙醇、水反复洗涤,真空干燥箱烘干,获得苯基键合硅胶。
图2示出了实施例2制备的苯基键合硅胶的扫描电镜图片。可以看出,苯基键合硅胶的尺寸在50~80μm之间,与硅胶基质的目数(200~300目)相互对应。同时,可以看到,苯基键合硅胶的表面非常粗糙,有许多纳米级小孔,说明苯基键合硅胶的比表面积较大。
表1列出了苯基键合硅胶的比表面积、孔径和元素分析结果。可以看到,苯基键合硅胶的比表面积高达319.78m2/g。根据碳含量和比表面积,可以推算出每平方米硅胶表面键合了4.12μmol的苯基。此外,苯基键合硅胶的孔径和比表面积均小于硅胶基质,其原因在于,苯基的存在占据了一定的孔隙体积,导致孔径和比表面积均相应减小。
表1 比表面积/孔径与元素分析结果
图3示出了苯基键合硅胶和硅胶基质的红外光谱,通过比较可以看出,苯基键合硅胶相较于硅胶基质在699.12,739.27和1433.58波数多了吸收峰。其中,699.12、739.27属于苯基的碳氢键伸缩振动,1433.58属于苯环的骨架振动,该结果进一步证实了苯基成功的键合在了硅胶基质表面。
实施例3 苯基键合硅胶固相萃取柱的制备
在本实施例中,在实施例1中所述的已装配有下筛板4的圆柱形玻璃空腔柱管1中,装入100mg的实施例1中制备的苯基键合硅胶作为填料3,随后装配上筛板2,压实,获得苯基键合硅胶固相萃取柱。
制备例4 黄酮工作液的制备
将槲皮素(QUE)、木犀草素(LUT)、异鼠李素(IRA)和山奈酚(KAE)4种黄酮分子混合溶解在同一甲醇溶剂中,浓度均为0.1mg/mL,并调节pH值至4.0,作为母液储存于冰箱中,备用。将母液用蒸馏水稀释至不同浓度,作为工作液使用。
实施例5 黄酮化合物的固相萃取
本实施例中,首先,分别用5mL甲醇和5mL水对实施例3制备的苯基键合硅胶固相萃取柱进行淋洗、活化,并排空蠕动泵;然后,以蠕动泵驱动50mL的制备例4中制备的黄酮工作液通过苯基键合硅胶固相萃取柱,流速2.0mL/min,使黄酮分子吸附在固相萃取材料表面;随后,以蠕动泵驱动1mL甲醇进行洗脱,流速0.4mL/min,获得洗脱液。
在上述实施例中,申请人还对固相萃取的操作参数以及黄酮工作液的pH值进行了以下考量:
(1)上样体积
在萃取过程中,上样体积是一项重要参数。一般而言,上样体积越大,富集倍数越高、检出限也就越低,但操作时间也越长;上样体积越小,富集倍数越低、检出限也就越高,但操作时间也越短。在本实施例中,将黄酮工作液的浓度固定为50.0μg/L,依次考察了20、50、100、150、200、250mL上样体积条件下黄酮化合物的萃取回收率。从图4A中可以发现,上样体积在20~150mL之间,萃取回收率较高且变化不大,超过150mL,回收率降低,该结果说明最大上样体积为150mL。作为在萃取实验中选择的最终上样体积应小于150mL,以确保高回收率。此外,在上样体积的选择方面,还应该兼顾富集倍数与操作时间。比如选择100mL作为上样体积,那么富集倍数就是100(洗脱体积假定为1mL),较高,但操作时间将会延长至100min(洗脱速度假定为1mL/min),较为耗时。综合考虑富集倍数与操作时间,最终选择50mL作为最终上样体积。
(2)黄酮工作液pH值
作为一类天然多酚类物质,黄酮分子在水溶液中的存在形式受pH值的影响较大,也因此,工作液的pH值影响着黄酮分子的萃取回收率。图4B示出了不同pH值条件下黄酮分子的萃取回收率。从图中可以看出,在pH值4.0处,黄酮分子回收率最高,这是由于在该pH值条件下,黄酮分子在水溶液中主要以分子形式存在,溶解度较低,可以较容易吸附在苯基键合硅胶表面,所以回收率高;在pH值大于4.0处,回收率降低,其原因在于黄酮分子在水溶液中主要以离子形式存在,溶解度较大,难以有效吸附在苯基键合硅胶表面,所以回收率降低;在pH值小于4.0处,黄酮分子的回收率也较低,其原因在于过多的酸分子会占据苯基键合硅胶表面的吸附位点,导致黄酮分子吸附量下降,所有回收率也较低。经综合优化考量,申请人选择4.0作为上样工作液的pH值。
(3)上样速度
图4C示出了上样速度对黄酮萃取回收率的影响。可以看出,上样速度在2.0mL/min以内,黄酮分子的萃取回收率较高且变化不大;上样速度高于2.0mL/min,回收率降低,这是由于上样速度过快,导致黄酮分子没有充分的机会与苯基键合硅胶相互作用,不能被有效吸附,因此回收率降低。经综合考量时间成本与回收率的平衡,优选上样速度为2.0mL/min。
进一步地,申请人还对洗脱步骤的参数进行了以下研究:
(4)洗脱剂的选择
在萃取实验中,需要选择适当的洗脱剂,以确保黄酮分子可以从苯基键合硅胶表面充分的洗脱下来。申请人考察了甲醇、乙醇、丙酮、乙腈和含1.0%乙酸的甲醇溶液作为洗脱剂时的萃取回收率,结果示于图5A中。
根据图5A可见,甲醇和含乙酸的甲醇溶液[w(乙酸)=1.0%]作为洗脱剂,黄酮的萃取回收率最高且差别不大,而其余有机溶剂均难以有效洗脱黄酮分子。从洗脱剂成本、操作复杂度和萃取回收率等方面综合考虑,优选使用甲醇作为黄酮化合物的洗脱剂。
(5)洗脱体积
以甲醇进行洗脱时,洗脱体积要尽可能的小,以提高富集倍数,同时,也节约溶剂耗量;另一方面,洗脱体积应当足以确保黄酮分子被充分洗脱。
图5B示出了不同甲醇体积下的黄酮分子的萃取回收率。可以看出,当洗脱体积高于1.0mL时,回收率较高且变化不大,但当低于1.0mL时,回收率则显著较低。因此,选择1.0mL作为优选的洗脱体积。
(6)洗脱速度
洗脱速度也是一项重要的洗脱参数。当速度较小时,尽管耗费时间较长,然而洗脱剂可以充分的接触黄酮分子,从而可以有效的将黄酮分子从苯基键合硅胶表面洗脱下来,回收率较高;而当速度过快时,洗脱剂难以充分的接触黄酮分子,所以,也难以有效的将黄酮分子从萃取材料表面洗脱下来,回收率较低。
图5C示出了在不同洗脱速度下,黄酮分子的萃取回收率。可以看出,当洗脱速度在0.4mL/min以内,萃取回收率较高,当超过0.4mL/min,回收率开始下降。因此,综合考虑时间成本与洗脱效率,优选洗脱速度为0.4mL/min。
实施例6 黄酮化合物的检测
在本实施例中,使用高效液相色谱对实施例5获得的洗脱液中的黄酮化合物进行检测,检测条件使用如下的色谱条件:
ODS分析柱(150mm×4.6mm I.D.);以甲醇与H3PO4水溶液[0.2wt%]为流动相A与B进行梯度洗脱:0-0.5min为0.51-12.5min为12.51-25min为流动相流速:1.0mL/min;柱温:25℃;进样体积:20μL;紫外检测器,波长360nm。
在本实施例中,申请人进一步地对前述固相萃取分析的结果进行了评价。
配置系列不同浓度的黄酮分子工作液,在前述优选的萃取参数条件下,以本发明的苯基键合硅胶萃取柱对上述工作液中的黄酮化合物进行萃取,并通过高效液相色谱进行检测,随后对检测结果进行评价,结果示于表2中。
从表2的结果可以看出,本发明的苯基键合硅基萃取黄酮化合物的分析方法具有宽的线性范围,在1~200μg/L之间,且线性关系良好,线性相关系数(R)在0.9991~0.9999之间;黄酮分子的检出限也较低,为0.25μg/L。单根萃取小柱的重复性良好,相对标准偏差在7.2%~9.4%之间,萃取小柱之间的重现性也较好,相对标准偏差在8.4%~10.3%之间。上述结果说明,所建立的苯基键合硅胶固相萃取方法适用于黄酮化合物的富集与检测。
表2 苯基键合硅胶萃取黄酮化合物的检测结果评价
实施例7 实际样品的分析
本实施例中,利用实施例6的方法对红葡萄果汁与蜂蜜花茶(来源于当地超市)两种实际样品中的黄酮化合物进行了检测分析,检测结果示于表3中。
从表3的结果可以看出,在红葡萄果汁中检测出了槲皮素19.9mg/L和异鼠李素13.1mg/L,在蜂蜜花茶中没有检测到黄酮化合物。为进一步证实该实验方法的可靠性,往两种饮料中均添加20μg/L的4种黄酮模型化合物,计算加标回收率。结果表明,4种黄酮化合物的加标回收率均在89.2-92.4%之间,证实了苯基键合硅胶萃取分析实际样品中的黄酮化合物是有效、可靠的。
表3 实际样品中黄酮化合物的检测与加标回收率
ND=未检出
工业实用性
与现有技术相比,本发明提供了一种新的苯基键合硅胶固相萃取柱,其具有制备简便易行、成本低廉的优点,并且通过该苯基键合硅胶固相萃取柱能够简便快捷的对黄酮化合物进行萃取,并且可随后用于色谱检测。该方法具有宽的线性范围、低的检出限,可适用于多种实际样品中黄酮化合物的富集检测,因此有着良好的性能和广阔的应用前景。
Claims (10)
1.一种苯基键合硅胶固相萃取柱,其具有空腔柱管(1),所述空腔柱管(1)在内部设置有上筛板(2)和下筛板(4),在所述上筛板(2)和下筛板(4)之间填充有填料(3),所述填料为苯基键合硅胶。
2.如权利要求1所述的苯基键合硅胶固相萃取柱,其特征在于,所述填料(3)的粒径为50~80μm,使用量为80~120mg,优选100mg;所述填料(3)的比表面积为>300m2/g。
3.如权利要求1或2所述的苯基键合硅胶固相萃取柱,其特征在于,所述空腔柱管(1)为玻璃空腔柱管或聚丙烯空腔柱管;所述空腔柱管(1)的形状为圆柱形,其容积为6mL;所述空腔柱管(1)的内径为1-1.5cm,优选1.3cm。
4.如权利要求3所述的苯基键合硅胶固相萃取柱,其特征在于,所述上筛板(2)和所述下筛板(4)的直径与所述空腔柱管(1)的内径相一致;所述上筛板(2)和所述下筛板(4)具有筛孔,所述筛孔的孔径为3-10μm、优选5μm;和/或所述上筛板(2)和所述下筛板(4)的厚度为1~2mm。
5.权利要求1-4中任一项所述的苯基键合硅胶固相萃取柱的制备方法,所述方法包括以下步骤:
(a)将硅胶置于非极性溶剂中,加入苯基三氯硅烷和催化剂,在搅拌下加热回流直至反应完成,随后经纯化处理获得苯基键合硅胶;
(b)将苯基键合硅胶装入固相萃取柱管,以筛板压实,制成所述苯基键合硅胶固相萃取柱。
6.如权利要求5所述的方法,其特征在于,所述步骤(a)中,所述非极性溶剂为甲苯,所述催化剂为吡啶。
7.如权利要求5或6所述的方法,其特征在于,以100mL甲苯计算,所述硅胶的使用量为2.0-4.0g,优选3.0g;所述苯基三氯硅烷的使用量为0.75-1.5mL,优选1mL;所述吡啶的添加量为0.08-0.12mL,优选0.1mL;所述加热回流进行10-15h,优选12h;所述纯化处理包括离心处理、依次以乙醇和水洗涤和烘干。
8.使用权利要求1-4中任一项所述的苯基键合硅胶固相萃取柱对黄酮化合物进行萃取的方法,所述方法包括以下步骤:
(1)以甲醇和水对本发明的苯基键合硅胶固相萃取柱进行淋洗和活化;
(2)通过泵驱动使待测黄酮工作液通过苯基键合硅胶固相萃取柱;
(3)使用甲醇通过苯基键合硅胶固相萃取柱进行洗脱,获得洗脱液。
9.如权利要求8所述的方法,其特征在于,所述步骤(1)中,所述甲醇和水的使用量分别为5mL;所述步骤(2)中,所述泵为蠕动泵;所述待测黄酮工作液的用量为20~150mL,优选50mL,且在事先被调整至pH值4~5、优选pH值4.0的状态;所述待测黄酮工作液通过所述苯基键合硅胶固相萃取柱的流速为1.5~2.0mL/min,优选2.0mL/min;所述步骤(3)中,所述甲醇的使用量为1.0mL,所述流速为不超过0.4mL/min、优选0.4mL/min。
10.使用高效液相色谱对权利要求8或9所述的洗脱液中的黄酮化合物进行检测的方法,所述方法使用如下色谱条件:
ODS分析柱(150mm×4.6mm I.D.);以甲醇与H3PO4水溶液[0.2wt%]为流动相A与B进行梯度洗脱:0-0.5min为0.51-12.5min为12.51-25min为流动相流速:1.0mL/min;柱温:25℃;进样体积:20μL;紫外检测器,波长360nm。
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