CN110139647A - 包含木蝴蝶素a的组合物及其提取方法 - Google Patents

包含木蝴蝶素a的组合物及其提取方法 Download PDF

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CN110139647A
CN110139647A CN201780070049.6A CN201780070049A CN110139647A CN 110139647 A CN110139647 A CN 110139647A CN 201780070049 A CN201780070049 A CN 201780070049A CN 110139647 A CN110139647 A CN 110139647A
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chrysin
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M.马吉德
K.纳加布胡沙纳姆
B.布哈特
A.潘德
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Abstract

公开了包含从木蝴蝶的树皮分离的生物活性物质木蝴蝶素A、黄芩素、白杨素及其葡糖苷酸木蝴蝶素A‑7‑葡糖苷酸、黄芩素‑7‑葡糖苷酸和白杨素‑7‑葡糖苷酸的组合物，以及分离所述活性成分的方法。

Description

包含木蝴蝶素A的组合物及其提取方法
相关专利申请的交叉引用
这是一项要求2016年11月11日提交的美国临时专利申请第62420676号的优先权的PCT申请。
发明背景
发明领域
本发明大体上涉及木蝴蝶。更具体地，本发明涉及从木蝴蝶分离生物活性物质木蝴蝶素A、黄芩素和白杨素及其葡糖苷酸。
现有技术说明
木蝴蝶(紫崴科，Oroxylum indicum或Broken bones tree)广泛分布于东南亚，其是阿育吠陀医学体系中的一种重要草药。据报道，该植物的根和树皮具有广谱的药物特性(Deka et al.,Oroxylumindicum–a medicinal plant of North East India:Anoverview of its nutritional,remedial,and prophylactic properties,Journal ofApplied Pharmaceutical Science,2013,Vol.3(Suppl 1),S104-S112)。从该植物中分离出的许多种重要黄酮，即，木蝴蝶素A(Oroxylin A)、黄芩素(Baicalein)、白杨素(Chrysin)、黄芩苷(Baicalin)、野黄芩苷(Scutellarin)、高车前素(Hispidulin)及其衍生物，均归因于其药理学特性，其中许多仍有待评估。因此，仍有未满足的工业需求以分离和鉴定存在于木蝴蝶中重要活性物从而验证其治疗潜力。
先前的研究已能够成功地分离出植物中存在的重要生物活性物质。Rao et al.在美国专利7,855,200中公开了用于分离生物活性物质木蝴蝶素A、黄芩素、白杨素的己烷和丙酮介导的方法。然而这些方法要么昂贵耗时，要么在工业上不可行。因此，存在对既经济又在工业上可行的新方法的技术需要。本发明通过公开一种用于从木蝴蝶分离生物活性物质的新方法而解决了这个问题。
本发明的主要目的是公开一种用于从木蝴蝶分离生物活性物质木蝴蝶素A、黄芩素、白杨素及其葡糖苷酸的非显而易见和工业上可用的方法。
本发明的另一个目的是公开一种包含木蝴蝶素A、黄芩素、白杨素及其葡糖苷酸的新组合物。
本发明实现了上述目的并提供了其他相关优点。
发明内容
本发明公开了一种从木蝴蝶的树皮分离生物活性物质木蝴蝶素A、黄芩素、白杨素及其葡糖苷酸木蝴蝶素A-7-葡糖苷酸、黄芩素7–葡糖苷酸和白杨素7-葡糖苷酸的方法。本发明还公开了包含所述生物活性物质木蝴蝶素A、黄芩素、白杨素及其葡糖苷酸组分木蝴蝶素A-7-葡糖苷酸、黄芩素-7-葡糖苷酸和白杨素-7-葡糖苷酸的组合物。
附图简要说明
图1显示了用于鉴定从木蝴蝶的树皮分离的木蝴蝶素A、黄芩素和白杨素的HPLC色谱图
图2显示了用于鉴定从木蝴蝶的树皮分离的木蝴蝶素A的质子NMR谱。
图3显示了用于鉴定从木蝴蝶的树皮分离的木蝴蝶素A的碳NMR谱。
图4显示了从木蝴蝶的树皮分离的木蝴蝶素A的质谱数据。
图5显示了用于鉴定从木蝴蝶的树皮分离的黄芩素的质子NMR谱。
图6显示了用于鉴定从木蝴蝶的树皮分离的黄芩素的碳NMR谱。
图7显示了从木蝴蝶的树皮分离的黄芩素的质谱数据。
图8显示了用于鉴定从木蝴蝶的树皮分离的白杨素的质子NMR谱。
图9显示了用于鉴定从木蝴蝶的树皮分离的白杨素的碳NMR谱。
图10显示了从木蝴蝶的树皮分离的白杨素的质谱数据。
图11显示了用于鉴定从木蝴蝶的树皮分离的木蝴蝶素A-7-葡糖苷酸、黄芩素-7-葡糖苷酸和白杨素-7-葡糖苷酸的HPLC色谱图。
图12显示了用于鉴定从木蝴蝶的树皮分离的木蝴蝶素A-7-葡糖苷酸质子NMR谱。
图13显示了用于鉴定从木蝴蝶的树皮分离的木蝴蝶素A-7-葡糖苷酸的碳NMR谱。
图14显示了从木蝴蝶的树皮分离的黄芩素-7-葡糖苷酸的质谱数据。
图15显示了用于鉴定从木蝴蝶的树皮分离的黄芩素-7-葡糖苷酸的质子NMR谱。
图16显示了用于鉴定从木蝴蝶的树皮分离的黄芩素-7-葡糖苷酸的碳NMR谱。
图17显示了从木蝴蝶的树皮分离的黄芩素-7-葡糖苷酸的质谱数据。
图18显示了用于鉴定从木蝴蝶的树皮分离的白杨素-7-葡糖苷酸的质子NMR谱。
图19显示了用于鉴定从木蝴蝶的树皮分离的白杨素-7-葡糖苷酸的碳NMR谱。
图20显示了从木蝴蝶的树皮分离的白杨素-7-葡糖苷酸的质谱数据。
最优选实施方式的说明
本发明公开了一种从木蝴蝶提取包含木蝴蝶素A及其葡糖苷酸的组合物的方法，所述方法包括以下步骤：
a)将木蝴蝶的树皮切割、干燥和粉碎成细粉；
b)用80％(v/v)甲醇提取100kg步骤a)中的细分以得到水性甲醇提取物；
c)将步骤b)的水性甲醇提取物溶解在水中获得浑浊的溶液(turbid solution)；
d)使用有机溶剂提取步骤c)中的浑浊的溶液；
e)浓缩并干燥步骤d)中的溶剂部分以获得黄棕色粉末；
f)使用HPLC、NMR和质谱表征步骤d)的粉末中存在的生物活性物质，其中木蝴蝶素A表示为STR#1，黄芩素表示为STR#2，且白杨素表示为STR#3：
g)浓缩并干燥步骤d)中的水性部分以得到棕色粉末。
h)使用HPLC、NMR和质谱表征步骤g)的粉末中存在的生物活性物质，木蝴蝶素A-7-葡糖苷酸表示为STR#4，黄芩素-7-葡糖苷酸表示为STR#5，且白杨素-7-葡糖苷酸表示为STR#6；
在相关实施方式中，步骤d)的溶剂选自下组：己烷、乙酸乙酯、甲醇、乙醇、氯仿、丁醇和丙酮。在另一个相关实施方式中，步骤d)的溶剂优选为乙酸乙酯。
在另一个实施方式中，本发明公开了一种包含从木蝴蝶的树皮分离的不少于10％的木蝴蝶素A、不少于10％的黄芩素和不少于2％的白杨素的组合物。在其他具体实施方式中，本发明公开了一种包含从木蝴蝶的树皮分离的约10％-15％的木蝴蝶素A、约10％-25％的黄芩素和约2％-10％的白杨素的组合物。
在另一个相关实施方式中，本发明公开了一种包含从木蝴蝶的树皮分离的不少于0.5％的木蝴蝶素A-7-葡糖苷酸、不少于2％的黄芩素-7-葡糖苷酸和不少于0.5％的白杨素-7-葡糖苷酸的组合物。在本发明的又一个特定实施方式中，本发明公开了一种包含从木蝴蝶的树皮分离的约0.5％-8％的木蝴蝶素A-7-葡糖苷酸、约2％-10％的黄芩素-7-葡糖苷酸和约0.5％-5％的白杨素-7-葡糖苷酸的组合物。
加入了本发明的技术特征和技术效果的上述最优选的实施方式通过下文中的说明性实施例来解释。
实施例1：从木蝴蝶分离生物活性物质并对其进行鉴定
木蝴蝶广泛分布于东南亚。为分离和鉴定植物中存在的生物活性物质，将树皮切割、干燥和粉碎成细粉。用80％(v/v)甲醇提取100kg细分以得到水性甲醇提取物。将其进一步溶解在水中以得到浑浊的溶液(turbid solution)。将浑浊的溶液用乙酸乙酯进一步提取。分离乙酸乙酯部分，浓缩并干燥以获得黄棕色粉末。使用HPLC分离和鉴定黄棕色粉末中存在的生物活性物质(图1)，使用NMR和质谱进一步将其表征为分别以STR#1、STR#2、STR#3表示的木蝴蝶素A(图2–4)、黄芩素(图5-7)和白杨素(图8-10)。
进一步浓缩和干燥水性部分以获得棕色粉末。使用HPLC分离和鉴定棕色粉末中存在的生物活性物质(水性部分)(图11)，使用NMR和质谱进一步将其表征为分别以STR#4表示的木蝴蝶素A-7-葡糖苷酸(图12-14)、以STR#5表示的黄芩素-7-葡糖苷酸(图15-17)和以STR#6表示的白杨素-7-葡糖苷酸(图18-20)。
从木蝴蝶分离的生物活性物质的含量在表1中列出。
表1：乙酸乙酯部分和水溶性部分中鉴定分子的含量
根据前述公开和教导，本发明的其他修改和变化对于本领域技术人员而言将是显而易见的。因此，虽然本文仅具体描述了本发明的某些实施方案，但显而易见的是，在不脱离本发明的精神和范围的情况下，可对其进行许多修改。

Claims (7)

1.一种从木蝴蝶提取包含木蝴蝶素A及其葡糖苷酸的组合物的方法，所述方法包括以下步骤：
a)将木蝴蝶的树皮切割、干燥和粉碎为细粉；
b)用80％(v/v)甲醇提取100kg步骤a)的细粉以获得水性甲醇提取物；
c)将步骤b)的水性甲醇提取物溶解在水中以产生浑浊的溶液；
d)使用有机溶剂提取步骤c)的浑浊的溶液；
e)浓缩并干燥步骤d)的溶剂部分以获得黄棕色的粉末；
f)使用HPLC、NMR和质谱表征步骤d)的粉末中存在的生物活性物质，木蝴蝶素A以STR#1表示，黄芩素以STR#2表示，白杨素以STR#3表示：
g)浓缩和干燥步骤d)的水性部分以获得棕色粉末；
h)使用HPLC、NMR和质谱表征步骤g)的粉末中存在的生物活性物质，木蝴蝶素A-7-葡糖苷酸以STR#4表示，黄芩素-7-葡糖苷酸以STR#5表示，白杨素-7-葡糖苷酸以STR#6表示：
2.如权利要求1所述的方法，其中步骤d)的有机溶剂选自己烷、乙酸乙酯、甲醇、乙醇、氯仿、丁醇和丙酮。
3.如权利要求1所述的方法，其中步骤d)的有机溶剂优选为乙酸乙酯。
4.组合物，其包含从木蝴蝶的树皮分离的不少于10％的木蝴蝶素A、不少于10％的黄芩素和不少于2％的白杨素。
5.如权利要求4所述的组合物，其中所述组合物包含从木蝴蝶的树皮分离的10％-15％的木蝴蝶素A、10％-25％的黄芩素和2％-10％的白杨素。
6.组合物，其包含从木蝴蝶的树皮分离的不少于0.5％的木蝴蝶素A-7-葡糖苷酸、不少于2％的黄芩素-7-葡糖苷酸和不少于0.5％的白杨素-7-葡糖苷酸。
7.如权利要求6所述的组合物，其中所述组合物包含从木蝴蝶的树皮分离的0.5％-8％的木蝴蝶素A-7-葡糖苷酸、2％-10％的黄芩素-7-葡糖苷酸和0.5％-5％的白杨素-7-葡糖苷酸。
CN201780070049.6A 2016-11-11 2017-11-07 包含木蝴蝶素a的组合物及其提取方法 Active CN110139647B (zh)

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