CN106543244B - 半乳糖型红景天苷及其衍生物的制备方法 - Google Patents
半乳糖型红景天苷及其衍生物的制备方法 Download PDFInfo
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- CN106543244B CN106543244B CN201610979793.5A CN201610979793A CN106543244B CN 106543244 B CN106543244 B CN 106543244B CN 201610979793 A CN201610979793 A CN 201610979793A CN 106543244 B CN106543244 B CN 106543244B
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Abstract
本发明涉及半乳糖型红景天苷及其衍生物的制备方法,包括如下步骤:(1)采用磷酸缓冲液配制乳糖浓度为0.1M~1M、对羟基苯乙醇浓度为0.05M~0.5M、β‑半乳糖苷酶浓度为0.004mg~4mg/mL的反应体系;(2)将反应体系于30~50℃条件下反应5~30分钟,终止反应,固液分离,取上清液;(3)将上清液,经分离、干燥后,制得半乳糖型红景天苷及其衍生物。该方法底物便宜,反应快速,操作简便,省时省力,生产成本低,应用前景广阔。
Description
技术领域
本发明涉及半乳糖型红景天苷及其衍生物的制备方法,特别涉及一种利用β-半乳糖苷酶合成对羟基苯乙基半乳糖苷及其衍生物的方法,属于糖工程技术领域。
技术背景
红景天苷天然存在于药用植物红景天中,其化学结构是对羟基苯乙基-O-β-D-葡萄糖苷,具有重要的药理学功能,具有神经保护、心血管保护、延缓衰老、抗疲劳、抗氧化、抗肿瘤、抗凝血、抗病毒、抗微波辐射等方面的作用,在中药及护肤品中均有少量添加,应用潜力巨大。目前发现半乳糖苷型的红景天苷即对羟基苯乙基-β-D-半乳糖苷,在神经保护和抗氧化方面更优于红景天苷。
半乳糖型红景天苷可由化学法合成获得,如公开号为CN102241710A(申请号为201110100667.5)的中国专利申请,公开了以2,3,4,6-四-O-乙酰基-α-溴代半乳糖和对羟基苯乙醇为原料来制备半乳糖型红景天苷的方法,将原料以碳酸银、碘为催化剂,无水硫酸钙为除水剂,分子筛用于吸附小分子溴化氢、水,避光及干燥的惰性气体保护下,溶解于相应的非质子性有机溶剂中,在15~45℃下进行反应,得到中间体乙酰化半乳糖苷;将所得中间体在含有强碱性物质的试剂中进行脱乙酰保护基,溶剂选择为甲醇、乙醇、四氢呋喃或者***,反应时间为2~6h,反应温度为10~40℃;将所得粗品用高效液相法、柱层析法或者溶剂重结晶法纯化得到红景天苷类似物。该方法耗时繁琐,并且涉及到一系列有机溶剂的使用。
相比于化学法,生物酶法能够催化一步反应合成糖苷,底物简单,反应快速,环境友好,但目前所报道的真菌来源的酶合成半乳糖型红景天苷的产率仅有10.9%,且产物单一。
发明内容
本发明针对现有技术的不足,提供一种半乳糖型红景天苷及其衍生物的制备方法。
一种半乳糖型红景天苷,对羟基苯乙基-O-β-半乳糖苷,分子式为C14H20O7,化学结构式如下:
一种半乳糖型红景天苷衍生物,对羟基苯乙基-O-β-半乳糖基-1,6-β-半乳糖苷,分子式为C20H30O12,化学结构式如下:
一种半乳糖型红景天苷衍生物,对羟基苯乙基-O-β-半乳糖基-1,3-β-半乳糖苷,分子式为C20H30O12,化学结构式如下:
上述半乳糖型红景天苷及其衍生物的制备方法,包括如下步骤:
(1)采用磷酸缓冲液配制乳糖浓度为0.1M~1M、对羟基苯乙醇浓度为0.05M~0.5M、β-半乳糖苷酶浓度为0.004mg~4mg/mL的反应体系;
所述步骤(1)中的β-半乳糖苷酶溶液中的β-半乳糖苷酶为中国专利文献CN1786170A(申请号200510044897.9)中记载氨基酸序列如SEQ ID NO.1所示的β-半乳糖苷酶;
(2)将步骤(1)制得的反应体系于30~50℃条件下反应5~30分钟,煮沸终止反应,固液分离,取上清液;
(3)将步骤(2)制得的上清液,经分离、干燥后,制得半乳糖型红景天苷及其衍生物。
根据本发明优选的,所述步骤(1)中的磷酸缓冲液为浓度10~100mM,pH6~8的磷酸钾缓冲溶液;根据本发明进一步优选的,所述步骤(1)中的缓冲液为50mM、pH7.0的磷酸钾缓冲液。
根据本发明优选的,所述步骤(2)中的反应条件为50℃反应10分钟。
根据本发明优选的,所述步骤(2)中的煮沸终止反应条件为100℃煮沸5分钟。
根据本发明优选的,所述步骤(3)中的分离为用规格15mmID×100cm的Bio-gel P2色谱柱进行色谱分离,以水为流动相,样品上样量为1~2mL,洗脱流速为0.2~0.3mL/分钟,分别收集84~108min、120~200min的洗脱样品,分别制得半乳糖型红景天苷和半乳糖型红景天苷衍生物I与半乳糖型红景天苷衍生物II的混合物;薄层层析分离半乳糖型红景天苷衍生物I与半乳糖型红景天苷衍生物II的混合物,制得半乳糖型红景天苷衍生物I和半乳糖型红景天苷衍生物II。
进一步优选的,所述色谱分离的样品上样量为1mL,洗脱流速为0.2mL/分钟。
进一步优选的,所述薄层层析分离为制备型薄层层析板分离,型号Silica gel60F254(Merck,Germany)。
进一步优选的,所述薄层层析分离的步骤如下:
薄层层析板点样后在展层剂中展开,雾喷显色剂后,于120℃烘烤5分钟使糖斑点显色。
最优的,所述展层剂由正丁醇、无水乙醇和水按体积比5:3:2混合配制;显色剂是由体积百分比为20%的硫酸溶液配制的质量浓度为0.5%的3,5-二羟基甲苯溶液。
根据本发明优选的,所述步骤(3)中的干燥为冷冻干燥。
有益效果
1、本发明公开了采用酶法合成半乳糖型红景天苷及其衍生物的方法,应用特定的细菌来源的β-半乳糖苷酶以廉价乳糖为糖基供体、对羟基苯乙醇为糖基受体,一步高效合成多种化合物;
2、本发明所述的半乳糖型红景天苷制备方法底物便宜,反应快速,条件温和,产物分离纯化简单,操作简便,比化学法合成省时省力,大大降低了生产成本,应用前景广阔;此外本发明还同时提供了两种新的半乳糖型红景天苷衍生物,在新药筛选方面具有潜在的应用价值;
3、本发明应用细菌来源的阴沟肠杆菌β-半乳糖苷酶催化乳糖和对羟基苯乙醇底物进行半乳糖基化反应,得到的半乳糖型红景天苷产率比现有酶法合成提高了近3倍。
附图说明
图1为半乳糖型红景天苷的质谱图;
图2为半乳糖型红景天苷的氢谱;
图3为半乳糖型红景天苷的碳谱;
图4为半乳糖型红景天苷的氢氢相关图谱;
图5为半乳糖型红景天苷的碳氢直接相关图谱;
图6为半乳糖型红景天苷的碳氢远程相关图谱;
图7为对羟基苯乙基-O-β-半乳糖基-1,6-β-半乳糖苷的质谱图;
图8为对羟基苯乙基-O-β-半乳糖基-1,6-β-半乳糖苷的氢谱;
图9为对羟基苯乙基-O-β-半乳糖基-1,6-β-半乳糖苷的碳谱;
图10为对羟基苯乙基-O-β-半乳糖基-1,6-β-半乳糖苷的氢氢相关图谱;
图11为对羟基苯乙基-O-β-半乳糖基-1,6-β-半乳糖苷的碳氢直接相关图谱;
图12为对羟基苯乙基-O-β-半乳糖基-1,6-β-半乳糖苷的碳氢远程相关图谱;
图13为对羟基苯乙基-O-β-半乳糖基-1,3-β-半乳糖苷的质谱图;
图14为对羟基苯乙基-O-β-半乳糖基-1,3-β-半乳糖苷的氢谱;
图15为对羟基苯乙基-O-β-半乳糖基-1,3-β-半乳糖苷的碳谱;
图16为对羟基苯乙基-O-β-半乳糖基-1,3-β-半乳糖苷的氢氢相关图谱;
图17为对羟基苯乙基-O-β-半乳糖基-1,3-β-半乳糖苷的碳氢直接相关图谱;
图18为对羟基苯乙基-O-β-半乳糖基-1,3-β-半乳糖苷的碳氢远程相关图谱;
具体实施方式
下面结合实施例对本发明做进一步说明,但本发明所保护范围不限于此。
实施例
半乳糖型红景天苷及其衍生物的制备方法,包括如下步骤:
(1)采用浓度50mM、pH7.0的磷酸缓冲液分别配制乳糖浓度为1M,对羟基苯乙醇浓度为0.25M、β-半乳糖苷酶浓度为0.4mg/mL的反应体系;
所述步骤(1)中的β-半乳糖苷酶为中国专利文献CN1786170A(申请号200510044897.9)中记载氨基酸序列如SEQ ID NO.1所示的β-半乳糖苷酶;
(2)将步骤(1)制得的反应体系于50℃条件下反应5分钟,100℃煮沸10分钟终止反应,10000转/分钟离心20分钟,取上清液;高效液相色谱分析,该反应所产生的半乳糖型红景天苷及其衍生物的总产率为50.0%,其中半乳糖型红景天苷占39.4%,两种衍生物占10.6%.
上述高效液相色谱分析所用设备及条件如下:
安捷伦(Agilent)1200型高压液相色谱仪;安捷伦G1314B紫外检测器;Agilent TCC18分析柱(4.6×250mm);流动相为甲醇/水(10:90,v/v);流速为1.0mL/min,柱温25℃;结果分析软件为Agilent Chemstation B.04.01版。反应液按1:1(v/v)的比例加水稀释,煮沸离心后上清用0.22μm的滤膜过滤后,进样分析。
(3)将步骤(2)制得的上清液,用规格15mm ID×100cm的Bio-gel P2色谱柱进行色谱分离,以水为流动相,样品上样量为1mL,洗脱流速为0.2mL/分钟,收集洗脱样品,薄层层析检测,合并迁移距离相同的糖苷产物;然后干燥,制得半乳糖型红景天苷;同时合并两种半乳糖型红景天苷衍生物的洗脱液,浓缩后再进一步通过制备薄层层析分离。样品在制备薄层层析板(PLC Silica gel 60F254,Merck)点样展层,展层结束后,在层析板上每隔10cm取1cm宽的条形小板显色,判定目标糖类在层析板上的位置。然后刮取层析板未显色区域含目标糖苷的硅胶粉末,将其重新溶解于水中,离心取上清,冷冻干燥后分别获得两种迁移率不同的粉末即两种半乳糖型红景天苷衍生物,标记为半乳糖型红景天苷衍生物I和半乳糖型红景天苷衍生物II。
所述薄层层析分离的步骤如下:
薄层层析板点样后在展层剂中展开,雾喷显色剂后,于120℃烘烤5分钟使糖斑点显色;
上述展层剂由正丁醇、无水乙醇和水按体积比5:3:2混合配制;显色剂是由体积百分比为20%的硫酸溶液配制的质量浓度为0.5%的3,5-二羟基甲苯溶液。
(4)半乳糖型红景天苷的结构鉴定
取上述制得的半乳糖型红景天苷的粉末加水稀释后进行质谱分析,目标产物的特征分子离子峰[M+Na]+为m/z 323.2274,[M+K]+为m/z 339.0907,[M+NH4]+为m/z 318.1261(如图1所示),判断产物分子量约为300,与预期产物分子量一致。
将5mg上述制得的半乳糖型红景天苷溶于氘代水中,进行核磁解析,综合氢谱(如图2所示)、碳谱(如图3所示)、氢氢相关谱(COSY)(如图4所示)、碳氢直接相关谱(HSQC)(如图5所示)、碳氢远程相关谱(HMBC)(如图6所示),确定各位置碳氢的化学位移和偶合常数,鉴定新合成的产物结构为对羟基苯乙基-O-β-半乳糖苷。1H NMR图谱上化学位移4.21ppm可观测到半乳糖异头质子的特征双峰信号,偶合常数为7.9Hz,推断半乳糖基通过β-键与对羟基苯乙基分子相连,在HMBC图中可以观测到对羟基苯乙基的C-8(δ70.79)与半乳糖异头质子H-1′(δ4.21)存在耦合信号,证实了β-半乳糖苷键的存在。
(5)半乳糖型红景天苷衍生物I的结构鉴定
取上述制得的半乳糖型红景天苷衍生物I的粉末加水稀释后进行质谱分析,目标产物的特征分子离子峰[M+Na]+为m/z 485.14(如图7所示),判断产物分子量约为462,与预期产物分子量一致。
将5mg上述制得的半乳糖型红景天苷的衍生物溶于氘代水中,进行核磁解析,综合氢谱(如图8所示)、碳谱(如图9所示)、氢氢相关谱(COSY)(如图10所示)、碳氢直接相关谱(HSQC)(如图11所示)、碳氢远程相关谱(HMBC)(如图12所示),确定各位置碳氢的化学位移和偶合常数,鉴定新合成的产物结构为对羟基苯乙基-O-β-半乳糖基-1,6-β-半乳糖苷。1HNMR图谱上化学位移4.25ppm、4.28ppm可分别观测到两个半乳糖异头质子的特征双峰信号,偶合常数分别为7.8Hz、7.9Hz,推断半乳糖形成的糖苷键为β-型,在HMBC图中可以观测到半乳糖型红景天苷半乳糖基的C′-6(δ68.70)与非还原端半乳糖基异头质子H-1″(δ4.28)存在耦合信号,证实了β-1,6半乳糖苷键的存在。
(6)半乳糖型红景天苷衍生物II的结构鉴定
取上述制得的半乳糖型红景天苷衍生物II的粉末加水稀释后进行质谱分析,目标产物的特征分子离子峰[M+Na]+为m/z 485.14(如图13所示),判断产物分子量约为462,与预期产物分子量一致。
将5mg上述制得的半乳糖型红景天苷衍生物II溶于氘代水中,进行核磁解析,综合氢谱(如图14所示)、碳谱(如图15所示)、氢氢相关谱(COSY)(如图16所示)、碳氢直接相关谱(HSQC)(如图17所示)、碳氢远程相关谱(HMBC)(如图18所示),确定各位置碳氢的化学位移和偶合常数,鉴定新合成的产物结构为对羟基苯乙基-O-β-半乳糖基-1,3-β-半乳糖苷。1HNMR图谱上化学位移4.42ppm、4.29ppm可观测到两个半乳糖异头质子的特征双峰信号,偶合常数分别为7.7Hz、8.0Hz,推断半乳糖形成的糖苷键为β-型,在HMBC图中可以观测到半乳糖型红景天苷半乳糖基的C′-3(δ82.22)与非还原端半乳糖基异头质子H-1″(δ4.42)存在偶合信号,证实了β-1,3半乳糖苷键的存在。
上述质谱分析所用仪器为岛津LCMS-IT-TOF质谱仪(日本);核磁分析所用仪器为Agilent DD2 600MHz核磁共振波谱仪(美国)。
SEQUENCE LISTING
<110> 山东大学
<120> 半乳糖型红景天苷及其衍生物的制备方法
<160> 1
<170> PatentIn version 3.5
<210> 1
<211> 1029
<212> PRT
<213> Enterobacter cloacae
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Claims (11)
1.一种半乳糖型红景天苷及其衍生物的制备方法,其特征在于,包括如下步骤:
(1)采用磷酸缓冲液配制乳糖浓度为0.1M~1M、对羟基苯乙醇浓度为0.05 M~0.5M、β-半乳糖苷酶浓度为0.004mg~4mg /mL的反应体系;
所述步骤(1)中的β-半乳糖苷酶溶液中的β-半乳糖苷酶氨基酸序列如SEQ ID NO.1所示的β-半乳糖苷酶;
(2)将步骤(1)制得的反应体系于30~50℃条件下反应5~30分钟,煮沸终止反应,固液分离,取上清液;
(3)将步骤(2)制得的上清液,经分离、干燥后,制得半乳糖型红景天苷及其衍生物;
所述半乳糖型红景天苷,命名为:对羟基苯乙基-O-β-半乳糖苷,分子式为C14H20O7,化学结构式如下:
所述半乳糖型红景天苷的衍生物为半乳糖型红景天苷衍生物I,命名为:对羟基苯乙基-O-β-半乳糖基-1,6-β-半乳糖苷,分子式为C20H30O12,化学结构式如下:
所述半乳糖型红景天苷的衍生物为半乳糖型红景天苷衍生物II,命名为:对羟基苯乙基-O-β-半乳糖基-1,3-β-半乳糖苷,分子式为C20H30O12,化学结构式如下:
。
2.如权利要求1所述的制备方法,其特征在于,所述步骤(1)中的磷酸缓冲液为浓度10~100mM,pH6~8的磷酸钾缓冲溶液。
3.如权利要求2所述的制备方法,其特征在于,所述步骤(1)中的缓冲液为50mM、pH7.0的磷酸钾缓冲液。
4.如权利要求1所述的制备方法,其特征在于,所述步骤(2)中的反应条件为50℃反应10分钟。
5.如权利要求1所述的制备方法,其特征在于,所述步骤(2)中的煮沸终止反应条件为100℃煮沸5分钟。
6.如权利要求1所述的制备方法,其特征在于,所述步骤(3)中的分离为用规格15mm ID×100cm的Bio-gel P2色谱柱进行色谱分离,以水为流动相,样品上样量为1~2mL,洗脱流速为0.2~0.3 mL/分钟,分别收集84~108min、120~200min的洗脱样品,分别制得半乳糖型红景天苷和半乳糖型红景天苷衍生物 I与半乳糖型红景天苷衍生物 II的混合物;薄层层析分离半乳糖型红景天苷衍生物 I与半乳糖型红景天苷衍生物 II的混合物,制得半乳糖型红景天苷衍生物 I和半乳糖型红景天苷衍生物 II。
7.如权利要求6所述的制备方法,其特征在于,所述色谱分离的样品上样量为1mL,洗脱流速为0.2mL/分钟。
8.如权利要求6所述的制备方法,其特征在于,所述薄层层析分离为制备型薄层层析板分离,型号Silica gel 60 F254。
9.如权利要求6所述的制备方法,其特征在于,所述薄层层析分离的步骤如下:
薄层层析板点样后在展层剂中展开,雾喷显色剂后,于120℃烘烤5分钟使糖斑点显色。
10.如权利要求9所述的制备方法,其特征在于,所述展层剂由正丁醇、无水乙醇和水按体积比5:3:2混合配制;显色剂是由体积百分比为20%的硫酸溶液配制的质量浓度为0.5%的3,5-二羟基甲苯溶液。
11.如权利要求1所述的制备方法,其特征在于,所述步骤(3)中的干燥为冷冻干燥。
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