CN101716262B - Extract from Iris tenuifolia, preparation method and application thereof - Google Patents
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Abstract
Description
技术领域 technical field
本发明涉及一种来自细叶鸢尾的提取物及其制备方法与应用。The invention relates to an extract from Iris tenifolia and its preparation method and application.
背景技术 Background technique
老年痴呆症(AD)是在老年人群中引起痴呆的一种渐进性的神经变性疾病。不同的病理学信号和渐进性的老年斑沉积以及导致神经元退化神经元纤维缠结伴随着认知力和记忆力的衰退。AD的一个典型特征是跨膜糖蛋白β-淀粉体前身蛋白(βAPP)水解而来的amyloid-βpeptide(Aβ)(淀粉样-β肽链(Aβ))累积。两种主要的Aβ(Alzheimer’s β-amyloid)变体分别由40和42个氨基酸构成,他们促进前炎症反应,激活神经毒害通路,导致脑细胞功能异常甚至死亡。有关研究表明当Aβ以纤丝形式聚合时,其在细胞和体内均有神经毒害作用。因此,找到可以阻止Aβ聚集的小分子化合物在AD治疗中变得很有价值(Ce′line Rivie`re etc,Inhibitoryactivity of stilbenes on Alzheimer’s β-amyloid fibrils in vitro,Bioorganic & MedicinalChemistry 15(2007)1160-1167)。Alzheimer's disease (AD) is a progressive neurodegenerative disease that causes dementia in the elderly population. Different pathological signatures and progressive deposition of senile plaques and neurofibrillary tangles leading to neuronal degeneration accompany cognitive and memory decline. A typical feature of AD is the accumulation of amyloid-β peptide (Aβ) (amyloid-β peptide chain (Aβ)) derived from the hydrolysis of the transmembrane glycoprotein β-amyloid precursor protein (βAPP). The two main Aβ (Alzheimer's β-amyloid) variants consist of 40 and 42 amino acids, respectively, and they promote pro-inflammatory responses and activate neurotoxic pathways that lead to abnormal function and even death of brain cells. Relevant studies have shown that when Aβ aggregates in the form of fibrils, it has neurotoxic effects both in cells and in vivo. Therefore, finding small molecular compounds that can prevent Aβ aggregation has become very valuable in AD treatment (Ce'line Rivie`re etc, Inhibitory activity of stilbenes on Alzheimer's β-amyloid fibrils in vitro, Bioorganic & Medicinal Chemistry 15(2007) 1160- 1167).
目前对老年痴呆症的治疗主要有四大类药物,分别为胆碱脂酶抑制剂、抗氧化剂药物、激素替代治疗药物及非甾体抗炎药,但这些药物在一定程度上都存在风险或限制。目前筛选研究具有抑制Aβ聚集的小分子先导化合物,成为研制治疗老年痴呆症的热点之一。At present, there are four main types of drugs for the treatment of Alzheimer's disease, namely cholinesterase inhibitors, antioxidant drugs, hormone replacement therapy drugs and non-steroidal anti-inflammatory drugs, but these drugs have risks or risks to a certain extent. limit. At present, the screening and research of small molecular lead compounds that can inhibit Aβ aggregation has become one of the hotspots in the development of treatment for Alzheimer's disease.
鸢尾科鸢尾属植物。在我国主要分布在西南、西北和东北地区。该属约有300个种,广泛的分布于世界各地,中国约有60个种及13个变种,(Mahmood U,KaulVK,Jirovetz L.Alkylated benzoquinones from Iris kumaonensis.Phytochemistry,2002,2(61):923-926.Qin MJ,Xu LS,Tanaka T,et al.A preliminarystudy on thedistribution pattern of isoflavones in rhizomes of Iris from China and its systematicsignificance.Acta Phyto Sinica,2000,38:343-349.)该属植物已被作为传统的民间药物,用来治疗多种疾病,例如,癌症、炎症、细菌和病毒感染。目前,从鸢尾属分离得到的化合物具有抗肿瘤、抗氧化、抗疟原虫和抗结核等作用(1.Atta-ur-RahmnM,et al.Anti-inflammatory isoflavonoids from the rhizomes of Iris germanica.Journalof Ethnopharmacology,2003,86:177-180.2.Bonfils JP et al.Cytotoxicity of iridals,triterpenoids from Iris.on human tumor cell lines A2780 andK562.Planta Med,2001,67:79-82)。Plants of the genus Iridaceae. In my country, it is mainly distributed in the southwest, northwest and northeast regions. There are about 300 species in this genus, which are widely distributed all over the world. There are about 60 species and 13 varieties in China, (Mahmood U, KaulVK, Jirovetz L. Alkylated benzoquinones from Iris kumaonensis. Phytochemistry, 2002, 2(61): 923-926. Qin MJ, Xu LS, Tanaka T, et al. A preliminary study on the distribution pattern of isoflavones in rhizomes of Iris from China and its systematic significance. Acta Phyto Sinica, 2000, 38: 343-349.) This genus has been It is used as a traditional folk medicine to treat a variety of diseases such as cancer, inflammation, bacterial and viral infections. At present, compounds isolated from Iris have anti-tumor, anti-oxidation, anti-plasmodium and anti-tuberculosis effects (1.Atta-ur-RahmnM, et al.Anti-inflammatory isoflavonoids from the rhizomes of Iris germanica.Journal of Ethnopharmacology, 2003, 86: 177-180.2. Bonfils JP et al. Cytotoxicity of iridals, triterpenoids from Iris. on human tumor cell lines A2780 and K562. Planta Med, 2001, 67: 79-82).
细叶鸢尾(Iris tenuifolia),为鸢尾科鸢尾属植物,其化学成分已有一定的报道,(1.Kojima,K.,Gombosurengyin,P.,Ondogyni,P.,Begzsurengyin,D.,Zevgeegyin,O.,Hatano,K.,Ogihara,Y.Flavanones from Iris tenuifolia.Phytochemistry,1997,44(4):711-714;2.M.I.Choudhary,S.Hareem and H.Siddiqui,et al.A benzil andisoflavone from Iris tenuifolia,Phytochemistry,2008,69,1880-1885)。我们继续研究该植物的化学成分,分离、鉴定了一个新的化合物;生物活性实验表明:该化合物能够阻止Aβ聚集,预示对老年痴呆症有一定的疗效。Iris tenuifolia (Iris tenuifolia), is Iridaceae Iris plant, its chemical composition has certain reports, (1.Kojima, K., Gombosurengyin, P., Ondogyni, P., Begzsurengyin, D., Zevgeegyin, O ., Hatano, K., Ogihara, Y. Flavanones from Iris tenuifolia. Phytochemistry, 1997, 44(4): 711-714; 2.M.I.Choudhary, S.Hareem and H.Siddiqui, et al.A benzil andisoflavone from Iris tenuifolia, Phytochemistry, 2008, 69, 1880-1885). We continued to study the chemical components of this plant, and isolated and identified a new compound; biological activity experiments showed that this compound can prevent Aβ aggregation, which indicates that it has certain curative effect on Alzheimer's disease.
发明内容 Contents of the invention
本发明的目的在于提供一种来自细叶鸢尾的提取物的制备方法。The object of the present invention is to provide a preparation method of the extract from Iris tenifolia.
本发明提供的制备方法包括以下步骤:The preparation method provided by the invention comprises the following steps:
1)取细叶鸢尾地下部分,用无水甲醇提取,收集提取液,再去除所述提取液的无水甲醇,得到细叶鸢尾地下部分总提取物;1) taking the underground part of Iris tenifolia, extracting it with anhydrous methanol, collecting the extract, and then removing the anhydrous methanol in the extract to obtain the total extract of the underground part of Iris tenifolia;
2)将步骤1)得到的细叶鸢尾地下部分总提取物溶于水中,再加入氯仿进行氯仿萃取,收集氯仿相,再去除所述氯仿相中的氯仿,得到本发明保护的提取物。2) Dissolving the total extract of the underground part of Iris tenifolia obtained in step 1) in water, adding chloroform for chloroform extraction, collecting the chloroform phase, and removing the chloroform in the chloroform phase to obtain the protected extract of the present invention.
进一步,上述步骤1)中,所述提取重复3次。Further, in the above step 1), the extraction is repeated 3 times.
上述步骤2)中,氯仿萃取可重复5次。In the above step 2), the chloroform extraction can be repeated 5 times.
上述方法制备的提取物也属于本发明的保护范围之内。The extract prepared by the above method also falls within the protection scope of the present invention.
上述的提取物在制备阻止Aβ聚集产品中的应用也属于本发明的保护范围之内。The application of the above-mentioned extracts in the preparation of Aβ aggregation-preventing products also falls within the protection scope of the present invention.
进一步,上述产品可以是药物。Further, the above-mentioned product may be a drug.
上述的提取物在制备治疗老年痴呆症的药物中的应用也属于本发明的保护范围之内。The application of the above-mentioned extracts in the preparation of medicaments for treating Alzheimer's disease also falls within the protection scope of the present invention.
本发明的又一目的在于提供一种治疗老年痴呆症的药物。Another object of the present invention is to provide a medicine for treating senile dementia.
本发明提供的治疗老年痴呆症的药物,其活性成分是上述的提取物。The medicament for treating senile dementia provided by the present invention has an active ingredient of the above-mentioned extract.
实验证明:本发明提供的提取物可以阻止Aβ聚集(缠结)。因为Aβ聚集是老年痴呆症的一个典型特征,因此本发明提供的提取物可用来治疗老年痴呆症。Experiments have proved that the extract provided by the invention can prevent Aβ aggregation (entanglement). Because Aβ aggregation is a typical feature of senile dementia, the extract provided by the invention can be used to treat senile dementia.
附图说明 Description of drawings
图1为本发明中化合物制备流程图。Fig. 1 is the flow chart of compound preparation in the present invention.
图2为本发明的提取物使Aβ缠结程度下降的结果图,其中aggregates表示未加样品的对照组;9为本发明的提取物,10为水相提取物,图2的纵坐标是将对照组的荧光强度记作1,其余组的荧光强度与对照组的荧光强度的比为相应纵坐标。Fig. 2 is the result figure that the extract of the present invention makes Aβ entanglement degree decline, and wherein aggregates represents the control group that does not add sample; 9 is the extract of the present invention, and 10 is the aqueous phase extract, and the ordinate of Fig. 2 is the The fluorescence intensity of the control group is recorded as 1, and the ratio of the fluorescence intensity of the other groups to the fluorescence intensity of the control group is the corresponding ordinate.
具体实施方式 Detailed ways
实施例1、一种具有抑制淀粉样蛋白β聚集作用的化合物1的制备:Example 1. Preparation of a
一、化合物1的制备1. Preparation of
制备流程如图1所示。The preparation process is shown in Figure 1.
1)无水甲醇浸泡1) Soak in anhydrous methanol
取1661g新鲜细叶鸢尾地下部分,用无水甲醇室温浸泡处理三次(每次5L无水甲醇/1kg材料),三次提取液合并,用旋转蒸发仪回收甲醇,得到细叶鸢尾地下部分的总提取物241.8g。Get 1661g of fresh underground part of Iris tenifolia, soak it with anhydrous methanol at room temperature for three times (each time 5L anhydrous methanol/1kg material), combine the three extracts, reclaim methanol with a rotary evaporator, and obtain the total extraction of the underground part of Iris tenifolia Compound 241.8g.
2)氯仿萃取2) Chloroform extraction
将步骤1)得到的提取物溶解于300mL蒸馏水,移入1000mL分液漏斗中,加入等体积的氯仿进行萃取,萃取共进行5次,合并氯仿萃取液,用旋转蒸发仪将氯仿萃取液中的氯仿回收,得到细叶鸢尾地下部分的氯仿提取物198.6g,同时收集水相提取物23.2g。该氯仿提取物也即本发明提供的提取物。The extract obtained in step 1) was dissolved in 300mL distilled water, moved into a 1000mL separatory funnel, added an equal volume of chloroform for extraction, the extraction was carried out 5 times, combined the chloroform extracts, and used a rotary evaporator to remove the chloroform in the chloroform extracts. Recover, obtain the 198.6g of the chloroform extract of the underground part of Iris tenifolia, and collect 23.2g of the aqueous phase extract at the same time. The chloroform extract is also the extract provided by the present invention.
实验例2、本发明提供的提取物抑制淀粉样蛋白β聚集作用的活性评价Experimental example 2, activity evaluation of the extract provided by the present invention in inhibiting amyloid β aggregation
将实施例1得到的氯仿提取物和水相提取物进行下面的活性分析。The chloroform extract and aqueous phase extract obtained in Example 1 were subjected to the following activity analysis.
试剂来源:Aβ蛋白(1-40,M=4329.84)购自瑞士Bachem公司,硫磺素T(Tht)购自Sigma公司Reagent source: Aβ protein (1-40, M=4329.84) was purchased from Bachem Company of Switzerland, Thioflavin T (Tht) was purchased from Sigma Company
活性评价实验方法参照文献Ce′line Rivie`re etc.Inhibitory activity of stilbenes onAlzheimer’s-amyloid fibrils in vitro,Bioorganic & Medicinal Chemistry15:1160-1167(2007)进行,具体步骤如下:The activity evaluation experiment method refers to the literature Ce'line Rivie`re etc. Inhibitory activity of stilbenes on Alzheimer's-amyloid fibrils in vitro, Bioorganic & Medicinal Chemistry15: 1160-1167 (2007), the specific steps are as follows:
1、Aβ缠结1. Aβ tangle
1mgAβ蛋白+2mlPBS(磷酸缓冲液,PH=7.4),得到0.5mg/ml的Aβ溶液,加入EDTA(1mM)促进缠结,在37℃,300rmp,孵育72h,在-80℃冰箱中保存。1mg Aβ protein + 2ml PBS (phosphate buffer, PH = 7.4) to obtain a 0.5mg/ml Aβ solution, add EDTA (1mM) to promote entanglement, incubate at 37°C, 300rmp for 72h, and store in a -80°C refrigerator.
2、硫磺素T(Tht)的配制2. Preparation of Thioflavin T (Tht)
配成300uM的Tht,备用,在4℃冰箱中保存,荧光测量时,需要稀释到3uM。Make up 300uM Tht, store it in a refrigerator at 4°C for later use, and dilute it to 3uM when measuring fluorescence.
3、样品+Aβ3. Sample + Aβ
向tube管中加入20ul浓度为20uM的Aβ溶液(步骤1保存的Aβ溶液稀释成20uM)和2ul的样品1或者样品2,充分混匀,37℃,孵育30分钟。样品1是将实施例1得到的氯仿提取物溶于二甲基亚砜(DMSO),形成10ug/ml的溶液;样品2是将实施例1得到的水相提取物溶于二甲基亚砜(DMSO),形成10ug/ml的溶液。Add 20ul of Aβ solution with a concentration of 20uM (the Aβ solution saved in
4、荧光测量4. Fluorescence measurement
取1500ul的3uM的Tht于新的tube管中,加入15ul步骤3中孵育好的混合物进行荧光测量,激发波长:442nm,测定波长:480nm。Take 1500ul of 3uM Tht in a new tube, add 15ul of the mixture incubated in step 3 for fluorescence measurement, excitation wavelength: 442nm, measurement wavelength: 480nm.
统计方法:用SPSS统计软件方差分析,**P<0.001。Statistical method: SPSS statistical software analysis of variance, **P<0.001.
实验重复3次,实验结果如图5所示,氯仿提取物的实验组中Aβ的缠结度显著下降,而水相提取物作用微弱,说明本发明提供的氯仿提取物可以阻止Aβ聚集。因为Aβ聚集是老年痴呆症的一个典型特征,因此本发明提供的提取物可用来治疗老年痴呆症。The experiment was repeated 3 times, and the experimental results are shown in Figure 5. The degree of entanglement of Aβ in the experimental group of the chloroform extract decreased significantly, while the effect of the aqueous phase extract was weak, indicating that the chloroform extract provided by the present invention can prevent the aggregation of Aβ. Because Aβ aggregation is a typical feature of senile dementia, the extract provided by the invention can be used to treat senile dementia.
Claims (8)
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