CN106588838B - 马齿苋中羟基二氢博伏内酯及其提取分离方法 - Google Patents
马齿苋中羟基二氢博伏内酯及其提取分离方法 Download PDFInfo
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- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
本发明涉及中药提取、分离领域,尤其涉及从马齿苋中首次提取、分离和鉴别出的羟基二氢博伏内酯(hydroxydihydrobovolide)及其提取分离方法。所述的羟基二氢博伏内酯,分子式为C11H18O3,命名为5‑羟基‑3,4‑二甲基‑5‑戊烷基‑2(5H)‑呋喃酮。还提供上述不饱和内酯化合物的提取分离方法,依次采用50%乙醇回流提取、大孔吸附树脂层析、乙酸乙酯萃取、聚酰胺柱层析、硅胶柱层析、ODS中压柱分离、Sephadex LH‑20分离纯化,首次成功的从马齿苋中提取分离出α‑β‑不饱和γ‑内酯类化合物:羟基二氢博伏内酯,它具有抗炎和神经保护作用,本发明羟基二氢博伏内酯及其衍生物可以作为其他化合物合成先导物,以及新药开发和药理活性研究的原料,用于制备抗炎和神经保护的药物或保健品。
Description
技术领域
本发明涉及中药提取、分离领域,尤其涉及从马齿苋药材中提取、分离和鉴别出的羟基二氢博伏内酯及其提取分离方法。
背景技术
马齿苋(Portulaca oleracea L.),又名长命菜、马苋菜,为马齿苋科植物。马齿苋耐旱耐涝,且耐光耐阴,分布广泛,资源丰富,作为药食两用的野生植物备受关注,2015版《中华人民共和国药典》中收载马齿苋的干燥地上部分入药,具有清热解毒、凉血止血、止痢等功效,用于热毒血痢、痈肿疔疮、湿疹、丹毒、蛇虫咬伤、便血、痔血、崩漏下血等。
马齿苋现代药理学研究表明,其具有抗炎止痛、抗菌抗病毒、降血压、降血脂、抗氧化、抗癌、松弛骨骼肌和平滑肌、调节免疫功能等作用。研究表明马齿苋众多化学成分为其多样的药理作用提供了物质基础,马齿苋主要化学成分包括黄酮类、香豆素、萜类、甾类、生物碱、氨基酸、各种色素类和矿物质类等。近年来,许多学者集中于对马齿苋化学成分的含量测定,药效学及药代动力学等研究,然而,在马齿苋中从未见α-β-不饱和γ-内酯类化合物的分离及体内外分析研究报道。
发明内容
针对上述问题,本发明提供一种从马齿苋中提取的羟基二氢博伏内酯,经研究发现该不饱和内酯化合物具有抗炎和保护神经的作用;同时提供一种针对该化合物的提取分离方法,该方法简便、快速、环保,并且分离得到的化合物纯度高。
为实现上述目的,本发明提供的马齿苋中提取的羟基二氢博伏内酯(hydroxydihydrobovolide),分子式为C11H18O3,化学结构式为。
为实现上述目的,本发明还提供一种马齿苋中羟基二氢博伏内酯的提取分离方法,具体步骤为。
步骤1、取马齿苋干燥药材,采用50%乙醇回流提取,减压回收乙醇,冷却至室温,得到药液。
步骤2、将步骤1中药液,使用静态吸附的方法通过AB-8型大孔树脂,依次采用水、50%乙醇和70%乙醇梯度洗脱,将70%乙醇洗脱部位减压浓缩后,浓缩液用乙酸乙酯反复萃取,减压回收乙酸乙酯至浸膏,得到乙酸乙酯萃取物。
步骤3、将步骤2中乙酸乙酯萃取物经聚酰胺柱分离,采用乙醇-水梯度洗脱,70%乙醇部分蒸干后上硅胶柱,依次用乙酸乙酯-甲醇梯度洗脱,得到100个流份,取流份70-100减压浓缩,得到浓缩物。
步骤4、将步骤3中所得浓缩物,经预处理的ODS柱(Octadecylsilyl,十八烷基硅烷键合硅胶填料)层析分离,用甲醇-水等度洗脱得到10个部分。
步骤5、将步骤4中所得部分中6和7部分样品,经预处理的Sephadex LH-20(羟丙基葡聚糖凝胶)处理,以甲醇洗脱,最终得到来源于马齿苋的羟基二氢博伏内酯。
所述步骤1中50%乙醇的体积用量为药材的8-16倍。
所述步骤2中乙酸乙酯反复萃取的次数为3次,每次乙酸乙酯与浓缩液的体积用量的比例为1:1。
所述步骤4中的等度洗脱为甲醇-水体积比为70:30的等度洗脱。
所述ODS和Sephadex LH-20凝胶的预处理过程为甲醇浸泡过24小时,上柱,用甲醇洗至滴入水中无混浊,再以初始流动相平衡。
本发明的有益效果。
本发明中,对马齿苋醇提物进行分离、纯化,并且首次分离得到5-羟基-3,4-二甲基-5-戊烷基-2(5H)-呋喃酮,即羟基二氢博伏内酯,所述马齿苋羟基二氢博伏内酯的分离和药理活性研究未被现有论文期刊所报道;本发明提供来源于马齿苋的羟基二氢博伏内酯及一种针对本发明新化合物的提取分离方法,依次采用50%乙醇回流提取、大孔吸附树脂层析、乙酸乙酯萃取、聚酰胺柱层析、硅胶柱层析、ODS中压柱分离纯化、Sephadex LH-20纯化,成功提取分离出羟基二氢博伏内酯,该方法操作步骤仅为五步,操作方法简便及快速;提取分离过程主要采用50%乙醇提取及乙酸乙酯萃取,工艺方法环保;且经该方法分离得到的化合物纯度较高均大于90%;由于羟基二氢博伏内酯属于α-β-不饱和γ-内酯类化合物并具有显著抗肿瘤活性和抗HIV活性,因此,研究表明该化合物具有抗炎和神经保护作用,本发明的羟基二氢博伏内酯及其衍生物可以作为其他化合物合成先导物,以及新药开发和药理活性研究的原料,亦可用于制备抗炎和神经保护的药物。
附图说明
图1为本发明羟基二氢博伏内酯的高分辨质谱图。
图2为本发明羟基二氢博伏内酯1H-NMR光谱图。
图3为本发明羟基二氢博伏内酯13C-NMR光谱图。
图4为本发明羟基二氢博伏内酯的核磁共振碳谱(DEPT)光谱图。
图5为本发明羟基二氢博伏内酯的核磁共振1H-1H COSY光谱图。
图6为本发明羟基二氢博伏内酯的核磁共振HMBC光谱图。
图7为本发明羟基二氢博伏内酯的核磁共振HSQC光谱图。
图8为本发明羟基二氢博伏内酯的核磁共振NOESY光谱图。
具体实施方式
实施例1。
本实施例提供一种羟基二氢博伏内酯,分子式为C11H18O3,化学结构式为。
所述羟基二氢博伏内酯根据结构命名为5-羟基-3,4-二甲基-5-戊烷基-2(5H)-呋喃酮,表1为该不饱和内酯化合物的核磁数据:1H-NMR与13C-NMR在CDCl3中。
表1:羟基二氢博伏内酯的核磁数据。
化合物:淡黄色油状物;HR-ESI-TOF-MS给出m/z: 199.1321 [M+H]+的准分子离子峰(见图1),分子量为198.1404;结合1H-NMR,13C-NMR以及DEPT数据(见图2-4),推测该化合物可能的分子式为C11H18O3,不饱和度为3;光谱数据如下,1H-NMR(500MHz,CDCl3)δ:1.96(1H,br,H-6a),1.93(3H,d,J=0.75Hz,H-11),1.81(3H,d,J=0.85 Hz,H-12),1.77(1H,br,H-6b),1.29(2H,m,H-8,-9),1.27(2H,m,H-7),1.17(1H,br,OH),0.88(3H,t,J = 6.3 Hz,H-10)。13C-NMR(100 MHz,CDCl3)δ:172.18(C-2),157.80(C-4),125.28(C-3),107.02(C-5),35.99(C-6),31.55(C-7),22.59(C-8),22.42(C-9),13.91(C-10),10.69(C-11),8.42(C-12);1H-NMR,13C-NMR和DEPT谱显示总共有11个碳信号,包括3个甲基(C-10,-11,-12),四个亚甲基碳(C-6,-7,-8,-9)和4个季碳。其中根据化学位移,4个季碳可分别推测为1个酯羰基碳(C-2),2个烯基季碳(C-3,-4)和一个双杂原子取代季碳(C-5)。进一步结合二维H-HCOSY、HMQC、HMBC及NOESY谱分析,可对化合物碳氢信号进行全归属(见图5-8)。HMBC谱显示以下几组数据:H-11与C-3,C-4,C-5,C-12;H-12与C-2,C-3,C-4,C-11;H-10与C-8,C-9;H-8,H-9,H-10与C-7;H-8,H-9与C-10;H-8与C-9,H-9与C-8;其中H-11与C-4,H-12与C-3的耦合作用强烈说明两个甲基分别与C-4,C-3直接相连。根据H-H相关谱可知,四个亚甲基中δ1.29与δ0.87相邻,δ1.27与δ1.29相邻,δ1.93与δ1.81相邻。以上数据结合不饱和度表明呋喃环结构的存在,C-3,C-4位置上有相邻甲基取代,并且C-5与戊烷基碳链连接。C-5(107.02)的化学位移向低场移动,提示在其位置上羟基和戊烷基同时取代。NOE相关包括以下几组数据:H-6a与H-6b;H-8,H-9与H-10;H-11与H-12;H-7与H-10及羟基中的活泼氢相关。以上数据与文献报道基本一致,故化合物确定为5-羟基-3,4-二甲基-5-戊烷基-2(5H)-呋喃酮(羟基二氢博伏内酯)。
本实施例还提供上述化合物的提取分离方法,具体步骤为。
步骤1:称取马齿苋干燥药材80kg,采用50%乙醇回流提取,50%乙醇用量为药材的10倍,回流提取两次,每次2h,减压回收乙醇,放凉至室温,得药液,备用。
步骤2:将步骤1中所得药液,使用静态吸附的方法通过AB-8型大孔树脂,依次采用水,50%乙醇,70%乙醇梯度洗脱,将70%乙醇洗脱部位减压浓缩后,浓缩液用乙酸乙酯反复萃取3次,40℃以下减压回收乙酸乙酯至浸膏,得到乙酸乙酯萃取物。
步骤3:将步骤2中乙酸乙酯萃取物经聚酰胺柱分离,采用乙醇-水(0/100,30/70,50/50,70/30,90/10,v/v)梯度洗脱,70%乙醇部分蒸干后经硅胶柱层析分离,其中硅胶为200-300目,依次用乙酸乙酯-甲醇(10:1、5:1、1:1,v:v)梯度洗脱,共得到100个流份,取流份70-100减压浓缩,得到浸膏7g。
步骤4:将步骤3中浓缩所得浸膏用70%甲醇溶解,并以15000r离心处理5min后,取上清液,经预处理的ODS中压柱层析分离,其中填料粒度为20-40μm,用甲醇-水(70:30,v/v)等度洗脱(加压,使流速为1mL/min,温度为室温),得到10个部分(即洗脱得10个瓶,每瓶50mL)。
步骤5:步骤4中所得10个部分经薄层色谱,置紫外灯(365nm)下检识,6,7两个部位有明显相同的荧光斑点,将6,7部分再经预处理的Sephadex LH-20(羟丙基葡聚糖凝胶)处理,以甲醇洗脱,分别用若干个小瓶接收,最终得到一个来源于马齿苋的淡黄色油状物化合物(16mg)。
所述Sephadex LH-20凝胶的预处理过程为甲醇浸泡过24h,上柱,用甲醇洗至滴入水中无混浊,再以初始流动相平衡。经超高效液相色谱,归一法测定纯度90-99%。所述ODS的预处理过程为甲醇浸泡过24h,上柱,用甲醇洗至滴入水中无混浊,再以初始流动相平衡。
一、羟基二氢博伏内酯的抗炎作用。
1、主要材料。
1.1、药品和试剂:实验所用羟基二氢博伏内酯由上述方法制备,纯度为90-99%,精密称取,用DMSO稀释至下述各剂量组所需溶液。DMEM高糖培养基、胎牛血清(美国Hyclone公司);青霉素、链霉素(杭州四季青公司);LPS(美国Sigma公司);IL-6、TNF-α、PGE2的ELISA试剂盒(美国Cayman公司);细胞裂解液、Griess试剂(碧云天生物技术有限公司)。
1.2 细胞株:RAW264.7巨噬细胞(美国ATCC细胞库)。
1.3 分组:分为对照组、LPS组和实验组,各一组。
2 实验方法。
2.1 RAW264.7巨噬细胞培养,DMEM高糖培养基中加入l0%的胎牛血清,l%抗菌素(100U/mL 青霉素和100μg/mL 链霉素),置于37℃,5% CO2培养箱中培养。
2.2 MTT比色法测定细胞活力,上述三组分别取对数生长期RAW264.7巨噬细胞接种于96孔培养板中,细胞密度为1×104个/mL,每孔100μL,温度37℃,5%CO2条件下培养过夜后,实验组加入不同浓度的本实施例羟基二氢博伏内酯(1-100μM),孵育1h后,向LPS组和实验组分别加入终浓度为1μg/mL的LPS,另设调零组(含DMSO溶媒的培养液),每组设3个复孔,考察加入药物后对细胞的影响。上述各组细胞培养24h后,在各孔细胞中加入5 mg/mL MTT20μL,温度37℃,5%CO2条件下,继续孵育4h后,终止培养,吸弃孔内液体,每孔加入100μL二甲基亚砜(DMSO),振荡10min,使细胞内结晶充分溶解,酶标仪570nm波长处测定各孔吸光值。
2.3 利用格里斯(Griess)法测定NO的含量,考察本实施例新生物碱化合物对LPS诱导的小鼠巨噬细胞RAW264.7的NO产生量的抑制作用。小鼠巨噬细胞RAW264.7传代后,在含10%胎牛血清的高糖细胞培养基DMEM中培养,实验组加入不同浓度的本实施例羟基二氢博伏内酯(1-20μM),在37℃,5%CO2条件下孵育1h后,用LPS(终浓度为1μg/mL)诱导炎症反应,24h后收集上清液,每组处理重复3孔。Griess法测定细胞上清液中NO的含量,根据不同浓度本实施例羟基二氢博伏内酯对LPS诱导的RAW264.7细胞释放NO的影响,用以反映NO水平。
2.4 ELISA法测定炎症因子IL-6、TNF-α和炎症介质PGE2:将对数生长期RAW264.7巨噬细胞接种于24孔培养板中,细胞密度为1×105个/mL,每孔1mL,温度37℃,5% CO2条件下培养过夜,实验组加入本发明羟基二氢博伏内酯(1-20μM),培育1h后,在每孔加入LPS(终浓度为1μg/mL),共孵育24h,每组处理重复3孔。ELISA法测定马齿苋来源羟基二氢博伏内酯处理后的RAW264.7巨噬细胞分泌的IL-6、TNF-α和PGE2的含量。
3实验结果。
实验结果表明本实施例羟基二氢博伏内酯对LPS诱导的巨噬细胞RAW264.7的增殖无影响,安全无毒;并可有效抑制LPS诱导的巨噬细胞RAW264.7所产生过量炎症细胞因子IL-6、TNF-α和炎症介质NO、PGE2,且呈浓度依赖。
细胞相对存活率实验结果如表2所示。
表2:本实施例羟基二氢博伏内酯对RAW264.7巨噬细胞相对存活率的影响。
注:*P<0.05与对照组比较(高浓度组有显著性差异)。
利用格里斯(Griess)法测定NO的含量实验结果见表3。
表3:本实施例羟基二氢博伏内酯对LPS诱导的RAW264.7细胞释放NO的影响(均数±标准差,n=3)。
注:*P<0.05与对照组比较,#P<0.05与LPS组比较。
ELISA法测定炎症因子IL-6、TNF-α和炎症介质PGE2结果如表4所示。
表4:本实施例羟基二氢博伏内酯对LPS诱导的RAW264.7细胞分泌的IL-6、TNF-α和PGE2含量的影响(均数±标准差,n=3)。
注:*P<0.05与对照组比较,#P<0.05与LPS组比较。
二、羟基二氢博伏内酯的神经保护作用。
1 主要材料。
1.1 药品和试剂:实验所用羟基二氢博伏内酯由上述方法制备,纯度为90-99%,精密称取,用DMSO稀释至下述各剂量组所需溶液。DMEM高糖培养基、胎牛血清(美国Hyclone公司);青霉素、链霉素(杭州四季青公司),磷酸盐缓冲液(PBS),(武汉博士德有限公司),ROS检测试剂盒(海门碧云天试剂公司)。
1.2 细胞株:人神经母细胞瘤细胞株(SH-SY5Y、IMR-32)(中科院上海细胞库)。
1.3 分组:分为对照组、H2O2损伤模型组和实验组。
2 实验方法。
2.1 人神经母细胞培养,DMEM高糖培养基中加入l0%的胎牛血清,l%抗菌素(100U/mL 青霉素和100μg/mL链霉素),置于37℃、5%CO2培养箱中培养。
2.2 MTT比色法测定细胞活力,上述三组分别取对数生长期SH-SY5Y细胞和IMR-32细胞接种于96孔培养板中,细胞密度为1×104个/mL,每孔100μL,温度37℃,5%CO2条件下培养过夜后,实验组加入不同浓度的本发明羟基二氢博伏内酯(5-40μM),孵育1h后向H2O2组和实验组分别加入终浓度为800μM/L的H2O2,另设调零组(含DMSO溶媒的培养液),每组设3个复孔,考察加入药物后对细胞的影响。上述各组细胞培养24h后,在各孔细胞中加入5 mg/mLMTT 20μL,温度37℃,5%CO2条件下继续孵育4h后,终止培养,吸弃孔内液体,每孔加入100μL二甲基亚砜(DMSO),振荡10min,使细胞内结晶充分溶解,酶标仪450 nm波长处测定各孔吸光值(A)值,计算细胞存活率,细胞存活率=(AH2O2损伤-A空白)/(A对照-A空白)。
2.3 DCFH-DA法检测SH-SY5Y细胞和IMR-32细胞内ROS,各组细胞给予相应物质后孵育24h,孵育结束前30min,各孔加入DCFH-DA,使终浓度为10μmol/L,于37℃继续孵育30min,收集细胞,PBS洗2次,细胞计数,将各组细胞制成相同浓度的细胞悬液。取100μL细胞悬液检测荧光强度,激发波长485nm,发射波长538nm。以对照组荧光强度为100%,其余各组与对照组荧光强度相比较,计算胞内ROS变化。
2.4 INT显色反应法测定LDH的释放量,除上述对照组、H2O2损伤模型组和实验组外,另设立空白对照组(空白对照组不接种细胞),各组细胞加入相应物质培养24h,取各孔上清120μL至新的96孔板中,加60μL配好的LDH检测工作液,避光室温孵育30min,在490nm处用多功能酶标仪测定A值,计算相对于对照管的LDH释放量百分率。LDH释放率=(A给药-A空白)/(A对照-A空白)。
3 实验结果。
细胞相对存活率实验结果如表5所示。
表5:本实施例羟基二氢博伏内酯对人神经母细胞瘤细胞株SH-SY5Y和IMR-32细胞相对存活率的影响。
注:*P<0.05与H2O2损伤模型组比较。
SH-SY5Y细胞和IMR-32细胞内ROS量检测结果如表6所示。
表6:本实施例羟基二氢博伏内酯对人神经母细胞瘤细胞株SH-SY5Y和IMR-32细胞内ROS量的影响。
注:*P<0.05与对照组比较,#P<0.05与H2O2损伤模型组比较。
SH-SY5Y细胞和IMR-32细胞内LDH释放的影响结果如表7所示。
表7:本实施例羟基二氢博伏内酯对人神经母细胞瘤细胞株SH-SY5Y和IMR-32细胞内LDH释放的影响。
注:*P<0.05与对照组比较,#P<0.05与H2O2损伤模型组比较。
综上所述,本发明提供羟基二氢博伏内酯及其提取分离方法,依次采用50%乙醇回流提取、大孔吸附树脂层析、乙酸乙酯萃取、聚酰胺柱层析、硅胶柱层析、ODS中压柱分离、Sephadex LH-20纯化,成功的从马齿苋中首次分离得到羟基二氢博伏内酯,该方法简便,快速,环保,且经该方法分离得到的化合物纯度较高,从常用中药马齿苋中提取出来,其具有抗炎、神经保护作用,因此本发明羟基二氢博伏内酯及其衍生物可以作为天然产物开发中药新药,具有广阔的前景。
Claims (5)
1.马齿苋中羟基二氢博伏内酯的提取分离方法,其特征在于,具体步骤为:
步骤1、取马齿苋干燥药材,采用50%乙醇回流提取,减压回收乙醇,放凉至室温,得药液备用;
步骤2、将步骤1中药液,使用静态吸附的方法通过AB-8型大孔树脂,依次采用水,50%乙醇,70%乙醇梯度洗脱,将70%乙醇洗脱部位减压浓缩后用乙酸乙酯反复萃取,减压回收乙酸乙酯至浸膏,得到乙酸乙酯萃取物;
步骤3、将步骤2中乙酸乙酯萃取物经聚酰胺柱分离,采用乙醇-水梯度洗脱, 70%乙醇部分蒸干后上硅胶柱,依次用乙酸乙酯-甲醇梯度洗脱,得到100个流份,取流份70-100减压浓缩,得到浓缩物;
步骤4、将步骤3中所得浓缩物经预处理的ODS柱层析分离,用甲醇-水等度洗脱得到10个部分,所得的洗脱部位经薄层色谱检识,得到有明显相同的荧光斑点部分;
步骤5、将步骤4中所得部分中6和7部分样品,经Sephadex LH-20处理,以甲醇洗脱,最终得到来源于马齿苋的羟基二氢博伏内酯;
所述马齿苋的羟基二氢博伏内酯的分子式为C11H18O3,命名为5-羟基-3,4-二甲基-5-戊烷基-2(5H)-呋喃酮,化学结构式如下:
。
2.如权利要求1所述的提取分离方法,其特征在于,所述步骤1中50%乙醇回流提取两次,每次2小时,每次回流提取中50%乙醇的体积用量为药材的8-16倍。
3.如权利要求1所述的提取分离方法,其特征在于,所述步骤2中浓缩液用乙酸乙酯萃取3次,每次乙酸乙酯用量与浓缩液的体积比为1:1。
4.如权利要求1所述的提取分离方法,其特征在于,所述ODS和Sephadex LH-20凝胶的预处理过程为甲醇浸泡过24小时,上柱,用甲醇洗至滴入水中无混浊,再以初始流动相平衡。
5.如权利要求1所述的提取分离方法,其特征在于,所述步骤4中所用等度洗脱中甲醇-水体积比为70:30。
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