CN114989064B - 马齿苋中一种新型吡咯生物碱类化合物及其提取分离方法 - Google Patents
马齿苋中一种新型吡咯生物碱类化合物及其提取分离方法 Download PDFInfo
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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提取、分离和鉴别出的吡咯生物碱类化合物及其提取分离方法。所述的吡咯生物碱类化合物,分子式为C5H5NO2,命名为olerapyrrole B。还提供上述吡咯生物碱类化合物的提取分离方法,依次采用50%乙醇回流提取、硅胶柱层析、SI正相硅胶中压柱、Sephadex LH‑20及HPLC进行分离纯化与制备。其结构采用1H NMR、13C NMR及二维NMR波谱解析的方法确定为一种新的吡咯生物碱类化合物。该化合物具有潜在的抗炎活性,并提供制备方法,为开发新药和开发新成分提供先导物和理论依据。
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、分离和鉴别出的一种生物碱类化合物及其提取分离方法。
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。马齿苋性喜肥沃土壤,耐旱亦耐涝,生命力强,分布广泛,资源丰富,而以我国东北部的更为常见。马齿苋既可入药,又可食用,是我国卫生部划定的药食同源的野生植物之一。2020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。
现代药理学研究表明,马齿苋具有降血脂、降血糖、抗炎、抗氧化、抗肿瘤、抗动脉粥样硬化、松弛或兴奋平滑肌及增强免疫力等功效。研究表明马齿苋中所含多种化学成分与其多样的药理作用息息相关,其主要化学成分包括:黄酮类、生物碱类、萜类、香豆素类、有机酸类、挥发油、多糖、氨基酸、各种色素类和矿物质类等。其中生物碱是马齿苋中的一大类活性成分,目前已报道的生物碱类成分有去甲肾上腺素、多巴胺、少量多巴、腺苷、尿嘧啶、腺嘌呤、N,N-二环己基脲、尿囊素、N-反式-阿魏酰基酪胺;还有环二肽生物碱和酰胺类生物碱:马齿苋酰胺A-I、K、L、N-S。
目前从马齿苋中分离出的化学成分大多数是已知的,且结构新颖性较低,因此,对马齿苋中新化合物的开发和分离是亟待需要的。
发明内容
针对上述问题,本发明提供从马齿苋中提取的一种新型吡咯生物碱类化合物,经研究发现本发明的一种吡咯生物碱类化合物具有抗炎的作用,同时提供一种针对本发明新化合物的简便、快速、环保、纯度高的提取分离方法。
为实现本发明的上述目的,本发明提供一种吡咯生物碱类化合物,分子式为C5H5NO2,命名为olerapyrrole B,化学结构式为:
。
为实现本发明的上述目的,本发明还提供马齿苋中新生物碱类化合物olerapyrrole B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%乙醇回流提取两次,醇提液滤过,合并滤液直接加热浓缩,放凉至室温,得药液备用;
步骤2、将步骤1中药液蒸干后上硅胶柱,用乙酸乙酯洗脱,减压回收乙酸乙酯至浸膏,得到乙酸乙酯提取物;
步骤3、将步骤2中所得物经SI正相硅胶柱层析分离,填料粒度为40μm,用乙酸乙酯、乙酸乙酯-甲醇、甲醇进行梯度洗脱,得到若干洗脱部位,经薄层色谱进行检测,显色,将显色部位减压浓缩至干,得到浓缩物备用;
步骤4、将步骤3中所得浓缩物再经SI正相硅胶柱层析分离,填料粒度为40μm,用环己烷-乙酸乙酯、乙酸乙酯、乙酸乙酯-甲醇、甲醇梯度洗脱,得到若干洗脱部位,经薄层色谱进行检测,显色,将显色部位减压浓缩至干,得到浓缩物备用;
步骤5、将步骤4中所得浓缩物经预处理的Sephadex LH-20(羟丙基葡聚糖凝胶)层析分离,用甲醇洗脱,经薄层色谱进行检测,显色,将显色的洗脱部位分别减压浓缩至干,得浓缩物备用;
步骤6、将步骤5中所得浓缩物经SI正相硅胶柱层析分离,填料粒度为40μm,经环己烷-乙酸乙酯、乙酸乙酯、乙酸乙酯-甲醇、甲醇进行梯度洗脱,得到若干洗脱部位,经薄层色谱进行检测,显色,将显色部位减压浓缩至干,得到浓缩物备用;
步骤7、将步骤6中所得浓缩物通过HPLC(高效液相)分离制备,以甲醇-0.1%甲酸水为流动相进行等度洗脱,最终得到本发明所述的新化合物。
所述Sephadex LH-20凝胶的预处理过程为甲醇浸泡过24小时,上柱,以初始流动相平衡。
与现有技术相比本发明的有益效果。
本发明中所述马齿苋中一种生物碱类化合物的分离和药理活性研究未被发现有论文期刊所报道;本发明提供来源于马齿苋的一种生物碱类化合物及一种针对本发明新化合物的提取分离方法,依次采用乙醇煎煮提取、硅胶柱层析、正相硅胶柱、Sephadex LH-20、正相硅胶柱及HPLC进行分离纯化与制备,成功提取分离出一种新的生物碱类化合物,该方法操作步骤仅为七步,操作方法简便及快速,提取分离过程主要采用乙醇提取,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%,此外经研究表明以上化合物具有抗炎作用,因此本发明一种生物碱化合物及其盐和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,亦可用于制备抗炎的药物。
附图说明
图1为本发明生物碱类化合物olerapyrrole B的1H-NMR光谱图。
图2为本发明生物碱类化合物olerapyrrole B的1H-NMR光谱图局部放大图。
图3为本发明生物碱类化合物olerapyrrole B的13C-NMR光谱图。
图4为本发明生物碱类化合物olerapyrrole B的13C-NMR光谱图局部放大图。
图5为本发明生物碱类化合物olerapyrrole B的核磁共振1H-1HCOSY光谱图。
图6为本发明物碱类化合物olerapyrrole B的核磁共振HMBC光谱图。
图7为本发明物碱类化合物olerapyrrole B的高分辨质谱图。
具体实施方式
下面结合具体实施例对本发明做详细的说明。
实施例1。
本发明提供一种生物碱类化合物,分子式为C5H5NO2,命名为olerapyrrole B,化学结构式为:
。
所述一种类化生物碱物根据结构命名为olerapyrrole B,表1为该生物碱类化合物的核磁数据:1H-NMR与13C-NMR在DMSO-
d 6中。
表1:本发明生物碱类化合物olerapyrrole B的核磁数据。
。
本发明一种生物碱类化合物olerapyrrole B的结构鉴定与推导。
olerapyrrole B:棕色油状物。点样于硅胶薄层板后,喷稀碘化铋钾试液斑点显橙色,提示该化合物为生物碱成分。HRESI(+)TOFMS给出m/z: 110.0247 [M+H]+的准分子离子峰,分子量为110.0244。结合1H-NMR和13C-NMR数据,推测该化合物可能的分子式为C5H5NO2,不饱和度为3。13C-NMR谱显示5个碳信号,分别为1个羰基碳(δ:162.8)、1个季碳(δ:147.5),3个CH(δ:147.7;118.5;113.0)。一个CHδ:147.7处于低场可能与N相连,1个季碳δ:147.5化学位移较大,推测与OH相连,13C-NMR谱可见两个信号较低的双键碳δ:118.5,113.5。1H-NMR谱显示三个次甲基信号δ6.56(1H,dd,J=1.62,3.48),δ7.16(1H,dd,J=0.66,1.62),δ7.69(1H,q,J=0.66,3.48)。依据HMBC谱的相关性,H-3与C-2,C-4,C-5相关,H-4与C-2,C-3,C-5相关,H-5与C-1',C-2,C-3,C-5相关,且C-5(δ147.7)处于低场,推测可能与N相连,且N上连接CHO以及C-1。根据1H-1H COSY谱可知,δH6.56、δH7.16与δH7.69互相耦合。
根据以上信息,可确定此生物碱类化合物为上述结构。
本发明还提供上述此生物碱类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250kg,采用50%乙醇回流提取,水用量为药材的10倍,乙醇回流提取两次,每次煎煮2h,提取液滤过,合并滤液,100℃加热浓缩至20Kg,放凉至室温,得药液备用。
步骤2:将步骤1中所得药液蒸干后经硅胶柱层析分离,用乙酸乙酯等度洗脱,其中硅胶为100-200目,40℃以下减压回收乙酸乙酯至浸膏,得到乙酸乙酯提取物。
步骤3:将步骤2中所得物经SI正相硅胶柱层析分离,填料粒度为40μm,依次用乙酸乙酯,乙酸乙酯-甲醇(5/1,2/1,v/v),甲醇梯度洗脱,加压,使流速为1mL/min,温度为室温,其中SI正相硅胶粒度为40μm。得到10个部位(即梯度洗脱得10个瓶,每瓶1000mL),经薄层色谱进行检测,显色,将显色部位减压浓缩至干,得到浓缩物备用。
步骤4:将步骤3中所得浓缩物再经SI正相硅胶柱层析分离。填料粒度为40μm,依次用环己烷-乙酸乙酯(5/1,1/1,v/v)、乙酸乙酯、乙酸乙酯-甲醇(5/1,v/v)、甲醇梯度洗脱,得到13个洗脱部位(即梯度洗脱得13个瓶,每瓶500mL),经薄层色谱进行检测,显色,将显色部位减压浓缩至干,得到浓缩物备用。
步骤5:将步骤4中所得浓缩物经预处理的Sephadex LH-20(羟丙基葡聚糖凝胶)层析分离,用甲醇洗脱,得到10个洗脱部位(即共得到10个瓶,每瓶120mL)经薄层色谱进行检测,显色,将显色的洗脱部位分别减压浓缩至干,得浓缩物备用。
步骤6:将步骤5中所得浓缩物经SI正相硅胶柱层析分离,填料粒度为40μm,经环己烷-乙酸乙酯(5/1,1/1,v/v),乙酸乙酯,乙酸乙酯-甲醇(5/1,1/1,v/v),甲醇梯度洗脱,加压,使流速为1mL/min,温度为室温,其中填料粒度为40μm,得到8个部位(即梯度洗脱得8个瓶,每瓶50mL),经薄层色谱进行检测,显色,将显色部位减压浓缩至干,得到浓缩物备用。
步骤7:将步骤6中所得浓缩物通过HPLC(高效液相)分离制备,以甲醇-0.1%甲酸水(30/70,v/v)为流动相进行等度洗脱,检测波长为210nm和254nm,分离制备得到本发明所述的新化合物,归一化法测定纯度为99%。
所述Sephadex LH-20凝胶的预处理过程为甲醇浸泡过24小时,上柱,以初始流动相平衡。
实施例2 本发明新化合物的抗炎作用。
1、主要材料。
1.1 药品和试剂:实验所用新化合物由上述方法制备,纯度为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-1
β和TNF-
α的ELISA试剂盒(美国Cayman公司);细胞裂解液(碧云天生物技术有限公司)。
1.2 细胞株:RAW 264.7巨噬细胞(美国ATCC细胞库)。
1.3 分组:对照组、LPS组和实验组,各一组。
2 实验方法。
2.1 细胞培养,DMEM高糖培养基,加入10%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:RAW 264.7细胞系在含有10%热灭活胎牛血清(FBS)和抗生素(100U/mL青霉素和100μg/mL链霉素)的DMEM中在37℃和5%CO2的湿化培养箱中培养。通过3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide(MTT)测定法评估细胞活力。然后将RAW264.7细胞以1×104个细胞/孔的密度接种在96孔板中,随后在有或没有各种浓度(5、10、25、50和100μM)的新化合物的情况下在培养箱中预孵育1小时,然后加入1μg/mL LPS孵育24小时。处理后除去培养基并与5mg/mL MTT溶液在37℃下孵育4小时。弃去上清液,将甲臜溶解在150μL DMSO中。使用BIO-TEK酶标仪在570nm处检测吸光度值,而未处理组的吸光度为100%。
2.3 ELISA法测定炎症因子IL-1
β和TNF-
α:将对数生长期RAW264.7巨噬细胞接种于96孔培养板中,细胞密度为1×105个/mL,每孔1mL,温度37℃,5%CO2条件下培养过夜,实验组加入本发明的新化合物olerapyrrole B(1μM~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法测定该马齿苋来源新化合物处理后的RAW264.7巨噬细胞分泌的IL-1
β和TNF-
α的含量。
3实验结果。
实验结果表明本发明新生物碱化合物对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-1
β和TNF-α,且呈浓度依赖。
细胞相对存活率实验结果如表2所示。
表2:本发明对RAW264.7巨噬细胞相对存活率的影响。
。
ELISA法测定炎症因子IL-1
β和TNF-α结果如表3所示。
表3:本发明对LPS诱导的RAW264.7细胞分泌的IL-1
β和TNF-α含量的影响(均数±标准差,n=3)。
。
综上所述,本发明提供特殊化合物及其提取分离方法,依次采用50%乙醇回流提取、硅胶柱层析、SI正相硅胶中压柱层析、Sephadex LH-20及HPLC分离纯化,成功的分离得到一种新化合物,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,由于所得化合物化学结构独特,从常用中药马齿苋中提取出来,其具有抗炎作用,因此本发明的新化合物olerapyrrole B及其盐和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 (6)
1.一种从马齿苋药材中分离出的吡咯生物碱类化合物的提取分离方法,其特征在于,具体步骤为:
步骤1、取马齿苋干燥药材,采用50%乙醇提取,醇提液滤过,合并滤液直接加热浓缩,放凉至室温,得药液备用;
步骤2、将步骤1中药液蒸干后上硅胶柱,用乙酸乙酯洗脱,减压回收乙酸乙酯至浸膏,得到乙酸乙酯提取物;
步骤3、将步骤2中所得物经SI正相硅胶柱层析分离,填料粒度为40μm,用乙酸乙酯、体积比为5∶1和2∶1的乙酸乙酯∶甲醇、甲醇进行梯度洗脱,得到若干洗脱部位,经薄层色谱进行检测,显色,将显色部位减压浓缩至干,得到浓缩物备用;加压,使流速为1mL/min,温度为室温;
步骤4、将步骤3中所得浓缩物再经SI正相硅胶柱层析分离,填料粒度为40μm,用体积比为5∶1和1∶1的环己烷∶乙酸乙酯、乙酸乙酯、体积比为5∶1的乙酸乙酯∶甲醇、甲醇进行梯度洗脱,得到若干洗脱部位,经薄层色谱进行检测,显色,将显色部位减压浓缩至干,得到浓缩物备用;加压,使流速为1mL/min,温度为室温;
步骤5、将步骤4中所得浓缩物经预处理的Sephadex LH-20层析分离,用甲醇洗脱,经薄层色谱进行检测,显色,将显色的洗脱部位分别减压浓缩至干,得浓缩物备用;
步骤6、将步骤5中所得浓缩物经SI正相硅胶柱层析分离,填料粒度为40μm,用体积比为5∶1的环己烷∶乙酸乙酯、乙酸乙酯、体积比为5∶1,1∶1的乙酸乙酯∶甲醇、甲醇进行梯度洗脱,得到若干洗脱部位,经薄层色谱进行检测,显色,将显色部位减压浓缩至干,得到浓缩物备用;加压,使流速为1mL/min,温度为室温;
步骤7、将步骤6中所得浓缩物通过HPLC分离制备,以甲醇∶0.1%甲酸水为流动相进行等度洗脱,最终得到所述的化合物,分子式为:C5H5NO2,并且根据结构命名为olerapyrrole B,其化学结构式如下:
。
2.如权利要求1所述提取分离方法,其特征在于,所述步骤1中乙醇回流提取两次,每次煎煮2小时,水用量为药材的10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中所用流动相洗脱程序为等度洗脱。
4.如权利要求1所述的提取分离方法,其特征在于,步骤5中的Sephadex LH-20凝胶的预处理过程为甲醇浸泡过24小时,上柱,以初始流动相平衡,所用流动相洗脱程序为等度洗脱。
5.如权利要求1所述的提取分离方法,其特征在于,步骤7中所用甲醇∶0.1%甲酸等度洗脱中甲醇和水的体积比为30∶70。
6.一种从马齿苋药材中分离出的吡咯生物碱类化合物在制备抗炎药物中的应用;所述化合物分子式为:C5H5NO2,并且根据结构命名为olerapyrrole B,其化学结构式如下:
。
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