CN110785181A - 从阿江榄仁的树皮制备阿江榄仁葡糖苷的标准化组合物的方法 - Google Patents

从阿江榄仁的树皮制备阿江榄仁葡糖苷的标准化组合物的方法 Download PDF

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CN110785181A
CN110785181A CN201880042024.XA CN201880042024A CN110785181A CN 110785181 A CN110785181 A CN 110785181A CN 201880042024 A CN201880042024 A CN 201880042024A CN 110785181 A CN110785181 A CN 110785181A
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M.马吉德
K.纳加布沙纳姆
B.巴特
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Sami Chemicals and Extracts Ltd
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Abstract

本发明公开了一种从阿江榄仁中分离生物活性化合物的新方法。更具体地，本发明公开了一种从阿江榄仁的树皮中分离和富集生物活性化合物Arjunic酸、阿江榄仁酸、阿江榄仁素、阿江榄仁亭、阿江榄仁葡糖苷‑I、阿江榄仁葡糖苷‑II、和儿茶素的方法。本发明还公开了一种从阿江榄仁的树皮中分离含有3％阿江榄仁葡糖苷的标准化组合物。

Description

从阿江榄仁的树皮制备阿江榄仁葡糖苷的标准化组合物的 方法
对相关申请的交叉引用
本文是2017年6月21日提交的美国临时申请号62522801的PCT申请。
发明背景
技术领域
一般地，本发明涉及来自阿江榄仁的生物活性化合物、更具体地，本发明公开了一种从阿江榄仁的树皮制备阿江榄仁葡糖苷的标准化组合物的新方法。本发明中公开的标准化组合物包括迄今为止尚未公开的促成所述组合物生物学效果的分子。
背景技术
阿江榄仁(Terminalia arjuna)或arjuna是古印度草药医学中一种众所周知的药用植物。据报道，阿江榄仁的树皮含有许多生物活性化合物，可以采割它们来治疗多种疾病。以下现有技术描述了阿江榄仁的重要生物学作用。
1.Pawar&Bhutani,Effect of oleanane triterpenoids from Terminaliaarjuna-a cardioprotective drug on the process of respiratory oxyburst,Phytomedicine,2005；25:391–393
2.Sandhu et al.,Effects of Withania somnifera(Ashwagandha)andTerminalia arjuna(Arjuna)on physical performance and cardiorespiratoryendurance in healthy young adults,Int J Ayurveda Res,2010；1(3):144–149.
3.Zafar et al.,Terminalia arjuna:Alternative Treatment forCardiovascular Diseases,Int.J.Pharm.Sci.Rev.Res.,2015；35(2):52-56.
4.Patel et al.,Development and Validation of Stability IndicatingAssay for Arjuna Caplets and Stability Studies with Concurrent PhytochemicalInvestigations,Inventi Rapid:Planta Activa,2015；1:1-5.
5.Chandra Sekhar et al.,Terminalia arjuna bark extract attenuatespicrotoxin-induced behavioral changes by activation of serotonergic,dopaminergic,GABAergic and antioxidant systems,Chinese Journal of NaturalMedicines,2017,15(8):584-596
从阿江榄仁的树皮获得的化合物阿江榄仁葡糖苷(Arjunoglucoside)在其心脏保护活性方面已经充分记载于文献中。据报道，阿江榄仁及其树皮提取物除了具有心脏保护作用外，还具有广泛的活性，例如抗癌，保肝，抗病毒，抗氧化剂，抗哮喘，避孕，抗糖尿病，伤口愈合，抗血小板和抗凝血，抗细菌和抗真菌活性等。(Saxena et al.,Cytotoxic agentsfrom Terminalia arjuna,Planta Med.2007；73(14):1486-90)。
文献中公开了许多从阿江榄仁和其他榄仁树属(Terminalia)种的树皮中分离阿江榄仁葡糖苷及其衍生物的方法。Anbalangan et al.(A.Anbalagan,Phytochemical andpharmacological studies on Terminalia arjuna(Roxb.)weight&Arnot and BorreriaHispida(Linn.)K.Schum,Ph.D Thesis,http://shodhganga.inflibnet.ac.in/bitstream/10603/4547/8/08_chapter％202.pdf(2018年6月13日访问)报道了阿江榄仁茎皮的甲醇提取物，其经硅胶苯色谱纯化，并用极性增加的溶剂(即苯、氯仿和甲醇)洗脱。从阿江榄仁的茎皮的甲醇提取物中鉴定出总共6种化合物，例如3-氧代-齐墩果-12-烯-28-酸(3-oxo-olean-12-ene-28-oic acid)，山楂酸甲酯，常春藤皂苷元甲酯(HederageninMethyl ester)，常春藤皂甙元，山楂酸和阿江榄仁酸。以下现有技术文献中描述了阿江榄仁葡糖苷的其他分离方法：
1.Tsuyuki et al.,A new triterpene compound from Terminaliaarjuna.Arjunoglucoside III.Bulletin of the chemical society of Japan,1979；52(10)；3127-3128
2.Honda et al.,Arjungenin,Arjunglucoside I,and Arjunglucoside II.ANew Triterpene and New Triterpene Glucosides from Terminalia arjuna.Bulletinof the Chemical Society of Japan,1976；49(11):3213-3218.
3.Pertuit et al.,A New Aromatic Compound from the Stem Bark ofTerminalia catappa,Nat Prod Commun.2015；10(6):1005-1007。
尽管现有文献中已经报道了分离阿江榄仁葡糖苷及其衍生物，但是发明人首次报道了一种从阿江榄仁的树皮制备阿江榄仁葡糖苷的标准化组合物的新方法。分离阿江榄仁葡糖苷及其衍生物的新方法是经济上可行且工业上可扩展的。
本发明的主要目的公开一种从阿江榄仁的树皮中分离和制备阿江榄仁葡糖苷的标准化组合物的新方法。
本发明的另一个目的公开分离和富集阿江榄仁葡糖苷的新方法。
本发明的还一个目的公开一种含有3％阿江榄仁葡糖苷的标准化组合物。
本发明实现了上述目的并提供了本发明的优势。
发明内容
本发明涉及一种从阿江榄仁中分离生物活性化合物的新方法。更具体地，本发明公开了一种从阿江榄仁的树皮中分离和富集生物活性化合物Arjunic酸(Arjunic acid)，阿江榄仁酸(Arjunolic acid)，阿江榄仁素(Arjungenin)，阿江榄仁亭(Arjunetin)，阿江榄仁葡糖苷-I，阿江榄仁葡糖苷-II，儿茶素和倍儿茶素(Gallocatechin)的方法。本发明还公开了一种从阿江榄仁的树皮中分离的含有3％阿江榄仁葡糖苷的标准化组合物。
附图说明
图1a显示了用于鉴定从阿江榄仁的树皮中分离的Arjunic酸的质子NMR谱。
图1b显示了用于鉴定从阿江榄仁的树皮中分离的Arjunic酸的碳NMR谱。
图2a显示了用于鉴定从阿江榄仁的树皮中分离的阿江榄仁酸的质子NMR谱。
图2b显示了用于鉴定从阿江榄仁的树皮中分离的阿江榄仁酸的碳NMR谱。
图3a显示了用于鉴定从阿江榄仁的树皮中分离的阿江榄仁素的质子NMR谱。
图3b显示了用于鉴定从阿江榄仁的树皮中分离的阿江榄仁素的碳NMR谱。
图4a显示了用于鉴定从阿江榄仁的树皮中分离的阿江榄仁葡糖苷-I的质子NMR谱。
图4b显示了用于鉴定从阿江榄仁的树皮中分离的阿江榄仁葡糖苷-I的碳NMR谱。
图5a显示了用于鉴定从阿江榄仁的树皮中分离的阿江榄仁葡糖苷-II的质子NMR谱。
图5b显示了用于鉴定从阿江榄仁的树皮中分离的阿江榄仁葡糖苷-II的碳NMR谱。
图6a显示了从阿江榄仁的树皮中分离的阿江榄仁葡糖苷-II甲醇提取物的HPLC色谱图。
图6b显示了从阿江榄仁的树皮中分离的浓缩的阿江榄仁葡糖苷-II的HPLC色谱图。
图7a显示了用于鉴定从阿江榄仁的树皮中分离的阿江榄仁亭的质子NMR谱。
图7b显示了用于鉴定从阿江榄仁的树皮中分离的阿江榄仁亭的碳NMR谱。
图8a显示了用于鉴定从阿江榄仁的树皮中分离的儿茶素的质子NMR谱。
图8b显示了用于鉴定从阿江榄仁的树皮中分离的儿茶素的碳NMR谱。
具体实施方式
在最优选的实施方案中，本发明公开了一种从阿江榄仁的树皮中分离阿江榄仁葡糖苷的标准化组合物的方法，所述方法包括以下步骤：
(a)将阿江榄仁树皮粉装入提取器中，
(b)对阿江榄仁树皮粉末加入3体积的乙醇或甲醇，并在65至70℃下回流3小时，
(c)过滤步骤b)的乙醇或甲醇提取物，并且在真空下浓缩以得到棕色粉末，
(d)将从步骤c)得到的粉末溶解于5体积的去矿质水中，并在50-55℃下充分搅拌1小时以得到溶液，
(e)将来自步骤d)中的溶液转移至分液漏斗中，并用2体积的溶剂萃取6次，并分离水层和有机层，
(f)收集并合并来自步骤e的溶剂级份1-6，并且在真空下浓缩以得到棕色粉末，
(g)将步骤f)的粉末装入硅胶，并用氯仿:甲醇洗脱，
(h)将来自步骤g)的化合物鉴定为以STR#1表示的Arjunic酸、以STR#2表示的阿江榄仁酸、以STR#3表示的阿江榄仁素、以STR#4代表的阿江榄仁葡糖苷-I、以STR#5表示的阿江榄仁葡糖苷-II、以STR#6表示的阿江榄仁亭、和以STR#7表示的儿茶素：：
Figure BDA0002331234550000051
在一个相关的实施方案中，步骤e)的溶剂选自下组：乙酸、丙酮、乙腈、苯、二硫化碳、四氯化碳、氯仿、环己烷、1,2-二氯乙烷、二氯甲烷、乙醚、1,2-二甲氧基乙烷、二甲基亚砜、1,4-二恶烷、乙醇、乙酸乙酯、己烷、异丙醇、甲醇、甲基乙基酮、N,N-二甲基甲酰胺、硝基甲烷、正丙醇、戊烷、吡啶、四氢呋喃、甲苯、水或其组合。在另一个相关的实施方案中，步骤e)的溶剂优选是乙酸乙酯。
在另一个优选的实施方案中，本发明公开了一种富集阿江榄仁葡糖苷II的方法，其中所述方法包括以下步骤：
(a)将阿江榄仁树皮粉装入提取器中，
(b)对阿江榄仁树皮粉加入3体积的乙醇或甲醇，并在65至70℃下回流3小时，
(c)过滤步骤b)中的乙醇或甲醇提取物，并在真空下浓缩以得到棕色粉末，通过HPLC测定阿江榄仁葡糖苷-II＝0.55％w/w，
(d)将从步骤c)获得的粉末溶解于5体积的去矿质水中，并在50-55℃下充分搅拌1小时以得到溶液，
(e)将来自步骤d)的溶液转移至分液漏斗中，并用2体积的溶剂萃取6次，并分离水层和有机层，
(f)收集并合并来自步骤e的溶剂级份1-6，并在真空下浓缩以得到棕色粉末，通过HPLC测定阿江榄仁葡糖苷-II＝20-21％w/w。
在另一个优选的实施方案中，本发明公开了包含至少3％的阿江榄仁葡糖苷的组合物，其中所述组合物包含以STR#1表示的Arjunic酸、以由STR#2表示的阿江榄仁酸、以STR#3表示的阿江榄仁素、以STR#4表示的阿江榄仁葡糖苷-I、以STR#5表示的阿江榄仁葡糖苷-II、以STR#6表示的阿江榄仁亭和以STR#7表示的儿茶素：
Figure BDA0002331234550000071
下面包括的具体实施例说明了本发明的上述最优选的实施方案。
实施例1：从阿江榄仁的树皮中分离阿江榄仁葡糖苷的方法
本发明公开了一种从阿江榄仁中分离阿江榄仁葡糖苷的方法。该方法包含以下步骤，将2kg阿江榄仁树皮粉装入提取器。然后对阿江榄仁树皮粉末中加入3体积的甲醇，并在65至70℃下回流3小时。然后，将溶液过滤并在真空条件下浓缩以得到棕色粉末，通过HPLC测定阿江榄仁葡糖苷-II＝0.55％w/w，收率约为500g(25％)。然后，将粉末溶于5体积的去矿质水中，并在50-55℃下充分搅拌1小时。然后将溶液转移至分液漏斗中，并用2体积的乙酸乙酯萃取6次，并分离水层和有机层。收集6种乙酸乙酯级份，并在真空下浓缩，获得棕色粉末，通过HPLC测定阿江榄仁葡糖苷-II＝20-21％w/w，收率约为40g。然后将粉末装入硅胶中，并用氯仿：甲醇洗脱。该级份包含Arjunic酸、阿江榄仁酸、阿江榄仁素、阿江榄仁葡糖苷-I和II、阿江榄仁亭和儿茶素。然后，使用NMR将化合物鉴定为Arjunic酸(图1a和1b)，阿江榄仁酸(图2a和2b)，阿江榄仁素(图3a和3b)，阿江榄仁葡糖苷-1(图4a和4b)，阿江榄仁葡糖苷-II(图5a，5b，6a和6b)，阿江榄仁亭(图7a和7b)和儿茶素(图8a和8b)。
还配制了一种包含至少3％阿江榄仁葡糖苷的组合物，所述组合物包含Arjunic酸、阿江榄仁酸、阿江榄仁素、阿江榄仁葡糖苷-I、阿江榄仁葡糖苷-II、阿江榄仁亭和儿茶素。
尽管本发明已经参照优选实施例进行了描述，但是本领域技术人员应当清楚地理解，本发明不限于此。而且，本发明的范围只能结合所附权利要求书进行解释。

Claims (7)

1.一种从阿江榄仁的树皮中分离阿江榄仁葡糖苷的标准化组合物的方法，所述方法包括以下步骤：
(a)将阿江榄仁树皮粉末装入提取器中，
(b)对阿江榄仁树皮粉末加入3体积的乙醇或甲醇，并在65至70℃下回流3小时，
(c)过滤步骤b)的乙醇或甲醇提取物，并且在真空下浓缩以得到棕色粉末，
(d)将从步骤c)得到的粉末溶解于5体积的去矿质水中，并在50-55℃下充分搅拌1小时以得到溶液，
(e)将来自步骤d)中的溶液转移至分液漏斗中，并用2体积的溶剂萃取6次，并分离水层和有机层，
(f)收集并合并来自步骤e的溶剂级份1-6，并且在真空下浓缩以得到棕色粉末，
(g)将步骤f)的粉末装入硅胶，并用氯仿:甲醇洗脱，
(h)将来自步骤g)的化合物鉴定为以STR#1表示的Arjunic酸、以STR#2表示的阿江榄仁酸、以STR#3表示的阿江榄仁素、以STR#4表示的阿江榄仁葡糖苷-I、以STR#5表示的阿江榄仁葡糖苷-II、以STR#6表示的阿江榄仁亭、和以STR#7表示的儿茶素：
Figure FDA0002331234540000011
Figure FDA0002331234540000021
2.根据权利要求1所述的方法，其中步骤e)的溶剂选自下组：乙酸、丙酮、乙腈、苯、二硫化碳、四氯化碳、氯仿、环己烷、1,2-二氯乙烷、二氯甲烷、乙醚、1,2-二甲氧基乙烷、二甲基亚砜、1,4-二恶烷、乙醇、乙酸乙酯、己烷、异丙醇、甲醇、甲基乙基酮、N,N-二甲基甲酰胺、硝基甲烷、正丙醇、戊烷、吡啶、四氢呋喃、甲苯、水或其组合。
3.根据权利要求1所述的方法，其中步骤e)的溶剂优选是乙酸乙酯。
4.一种富集阿江榄仁葡糖苷II的方法，所述方法包括以下步骤：
(a)将阿江榄仁树皮粉末装入提取器中，
(b)对阿江榄仁树皮粉末加入3体积的乙醇或甲醇，并在65至70℃下回流3小时，
(c)过滤步骤b)中的乙醇或甲醇提取物，并在真空下浓缩以得到棕色粉末，通过HPLC测定阿江榄仁葡糖苷-II＝0.55％w/w，
(d)将从步骤c)获得的粉末溶解于5体积的去矿质水中，并在50-55℃下充分搅拌1小时以得到溶液，
(e)将来自步骤d)的溶液转移至分液漏斗中，并用2体积的溶剂萃取6次，并分离水层和有机层，
(f)收集并合并来自步骤e的溶剂级份1-6，并在真空下浓缩以得到棕色粉末，通过HPLC测定阿江榄仁葡糖苷-II＝20-21％w/w。
5.根据权利要求4所述的方法，其中步骤e)的溶剂选自乙酸、丙酮、乙腈、苯、二硫化碳、四氯化碳、氯仿、环己烷、1,2-二氯乙烷、二氯甲烷、乙醚、1,2-二甲氧基乙烷、二甲基亚砜、1,4-二恶烷、乙醇、乙酸乙酯、己烷、异丙醇、甲醇、甲基乙基酮、N,N-二甲基甲酰胺、硝基甲烷、正丙醇、戊烷、吡啶、四氢呋喃、甲苯、水或其组合。
6.根据权利要求4所述的方法，其中步骤e)的溶剂优选是乙酸乙酯。
7.一种包含至少3％的阿江榄仁葡糖苷的组合物，其中所述组合物包含以STR#1表示的Arjunic酸、以STR#2表示的阿江榄仁酸、以STR#3表示的阿江榄仁素、以STR#4表示的阿江榄仁葡糖苷-I、以STR#5表示的阿江榄仁葡糖苷-II、以STR#6表示的阿江榄仁亭和以STR#7表示的儿茶素：
Figure FDA0002331234540000031
Figure FDA0002331234540000041
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