CN107998137B - 1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖的用途 - Google Patents

1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖的用途 Download PDF

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CN107998137B
CN107998137B CN201711352933.7A CN201711352933A CN107998137B CN 107998137 B CN107998137 B CN 107998137B CN 201711352933 A CN201711352933 A CN 201711352933A CN 107998137 B CN107998137 B CN 107998137B
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苏艳芳
栗章彭
魏子烨
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Tianjin University
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Abstract

本发明公开了1，3，4‑三‑O‑(E)‑咖啡酰基‑β‑D‑葡萄吡喃糖在制备降糖药或食品的用途，所述1，3，4‑三‑O‑(E)‑咖啡酰基‑β‑D‑葡萄吡喃糖如式(I)所示：

Description

1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖的用途
技术领域
本发明涉及从植物中提取1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖在制备降糖药或食品的用途。
背景技术
假升麻(Aruncus sylvester Kostel.)，属蔷薇科(Rosaceae)绣线菊亚科(Spiraeoideae Agardh) 假升麻属(Aruncus Adans.)。假升麻的干燥根被称为“金毛三七”，常常作为中国传统中药应用于治疗肌肉劳损，有舒筋活络的功效。
中国专利ZL201310134172.3公开了抗氧化活性化合物及用途，其中一种抗氧化活性化合物为1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖，并公开了其“在制备抗氧化药物、食品或化妆品中的应用。”目前，尚未有该化合物抗α-葡萄糖苷酶生物活性的报道。
发明内容
本发明的目的在于提供1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖在制备降糖药或食品的用途。
本发明的技术方案概述如下：
1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖在制备降糖药或食品的用途，所述1，3，4- 三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖如式(I)所示：
Figure BDA0001510597600000011
实验证明，1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖对α-葡萄糖苷酶抑制活性远优于阿卡波糖。可以制备降糖药或降糖食品。
具体实施方式
下面对过具体实施例对本发明作进一步的说明。
实施例1
式I所示的1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖的制备按照中国专利ZL201310134172.3说明书实施例1制备。
实施例1
本发明是以假升麻干燥块根为原料，粉碎，依次用2.5倍量的体积浓度为95％、95％和60％的乙醇水溶液回流提取3次，每次2小时，过滤，合并提取液，减压回收至无醇味，残留物分散至蒸馏水中配成体积浓度为40％的水混悬液，依次用石油醚，乙酸乙酯进行萃取，乙酸乙酯萃取部分减压回收至干，经多次硅胶柱色谱，聚酰胺柱色谱，得到两种苯丙素类化合物，采用了核磁共振光谱技术，确定了该化合物的结构。得到化合物I和化合物II。
物理常数光谱数据如下：
化合物I：黄色无定形粉末，MeOH；分子式C33H30O15；1H and 13C NMR：见表1and表2.
表1化合物I的氢谱数据
Figure BDA0001510597600000021
表2化合物I的碳谱数据
实施例2
α-葡萄糖苷酶抑制活性的测定方法
反应溶液的制备
配制磷酸缓冲液：称取1.167g的磷酸氢二钾和0.9118的磷酸二氢钾，加适量蒸馏水溶解，再用容量瓶定容至100mL，配置成pH＝6.8的磷酸盐缓冲液，备用。
配制底物PNPG(4-硝基苯基-α-D-吡喃葡萄糖苷)溶液：称取90.375mg PNPG，加适量磷酸盐缓冲液(pH＝6.8)溶解，再用容量瓶准确定容到25mL，配制成12mmol/L的母液。再将母液稀释成4mmol/L的溶液，备用。
配制α-葡萄糖苷酶的酶溶液：将冻干酶粉(酶活力为14u/mg)用磷酸缓冲液(pH＝6.8) 溶解，配制成0.15u/mL的母液，备用。
配制Na2CO3溶液：称取2.12g无水Na2CO3于烧杯中，加适量蒸馏水溶解，并再用容量瓶定容至100mL，备用。
配制待测样品溶液(抑制剂)：精确称取1mg的1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖样品，加适量5％的DMSO水溶液(v/v)溶解，再用容量瓶定容至10mL，配制成100 μg/mL的母液。将母液用5％的DMSO水溶液(v/v)分别稀释成0.5、1.0、1.5、2.0、2.5μg/mL 五个不同梯度的标准品溶液，备用。
实验分为药物反应组、药物对照组、空白反应组和空白对照组，各反应物按下表中剂量在EP管中进行加样，每组3个平行。依次加入磷酸盐缓冲液、酶溶液、待测样品溶液和5％DMSO水溶液，混合均匀后于37℃水浴保温10min。结束后，取出，加入PNPG溶液，充分混匀后于37℃水浴反应30min。结束后加入200μL的Na2CO3溶液中止反应。然后在紫外波长405nm处测定每组样品的吸光度，每组样品平行测定3次，取其均值。按式(1) 计算各待测样品对DPPH自由基的清除率。
Figure BDA0001510597600000031
式中：A1为药物反应组吸光度；A2为药物对照组吸光度；A3空白反应组吸光度；A4为空白对照组吸光度。
表3各组添加试剂及其计量(单位：μL)
Figure BDA0001510597600000041
表4 1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖的实验测定结果
Figure BDA0001510597600000042
表5阿卡波糖的实验测定结果
Figure BDA0001510597600000051
将所得数据绘制浓度-吸光度曲线，拟合曲线方程，得到IC50值(半数抑制率)，以阿卡波糖的IC50值为阳性对照。结果表明，1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖具有很强的α-葡萄糖苷酶抑制活性，可应用于抗糖尿病的食品和药品的制备。
表6 1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖IC50值

Claims (1)

1.1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖作为唯一活性成分在制备降血糖药物或辅助降血糖食品中的用途，所述1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖如式(I)所示：
Figure FDA0002302519470000011
CN201711352933.7A 2017-12-15 2017-12-15 1，3，4-三-O-(E)-咖啡酰基-β-D-葡萄吡喃糖的用途 Expired - Fee Related CN107998137B (zh)

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Citations (6)

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Publication number Priority date Publication date Assignee Title
KR20100086680A (ko) * 2009-01-23 2010-08-02 한국과학기술연구원 능실로부터 분리된 신규 화합물 및 이를 함유하는 항산화 조성물
CN101829228A (zh) * 2010-05-20 2010-09-15 邓振全 地黄皂甙的提取方法
JP2011037800A (ja) * 2009-08-18 2011-02-24 Aomori Univ Of Health & Welfare アピオス花を用いた血糖値上昇抑制物質および糖尿病予防用食品素材
JP2014087364A (ja) * 2014-01-08 2014-05-15 Aomori Univ Of Health & Welfare 食用アピオス花、食品素材、血糖値上昇抑制効果具有物、血糖値上昇抑制物質およびアピオス花の使用方法
CN104109180A (zh) * 2013-04-16 2014-10-22 天津大学 抗氧化活性化合物及用途
CN104961779A (zh) * 2015-05-25 2015-10-07 天津科技大学 一种含咖啡酰基的鞣质衍生物及其制备工艺和应用

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20100086680A (ko) * 2009-01-23 2010-08-02 한국과학기술연구원 능실로부터 분리된 신규 화합물 및 이를 함유하는 항산화 조성물
JP2011037800A (ja) * 2009-08-18 2011-02-24 Aomori Univ Of Health & Welfare アピオス花を用いた血糖値上昇抑制物質および糖尿病予防用食品素材
CN101829228A (zh) * 2010-05-20 2010-09-15 邓振全 地黄皂甙的提取方法
CN104109180A (zh) * 2013-04-16 2014-10-22 天津大学 抗氧化活性化合物及用途
JP2014087364A (ja) * 2014-01-08 2014-05-15 Aomori Univ Of Health & Welfare 食用アピオス花、食品素材、血糖値上昇抑制効果具有物、血糖値上昇抑制物質およびアピオス花の使用方法
CN104961779A (zh) * 2015-05-25 2015-10-07 天津科技大学 一种含咖啡酰基的鞣质衍生物及其制备工艺和应用

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