CN113968862A - 马齿苋中两种新生物碱及其提取分离方法 - Google Patents
马齿苋中两种新生物碱及其提取分离方法 Download PDFInfo
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- CN113968862A CN113968862A CN202111394357.9A CN202111394357A CN113968862A CN 113968862 A CN113968862 A CN 113968862A CN 202111394357 A CN202111394357 A CN 202111394357A CN 113968862 A CN113968862 A CN 113968862A
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- 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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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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、分离和鉴别出的两种新生物碱及其提取分离方法。所述的两种新化合物,分子式为C5H6N4O、C6H6N2O4,并且根据结构命名为3‑amino‑1,3,4‑triazabicyclo[3.2.1]octa‑4,6‑dien‑8‑one(1)、2‑(dicarboxyamino)‑1H‑pyrrole(2)。还提供上述新生物碱的提取分离方法,依次采用水煎煮提取、硅胶柱层析、聚酰胺柱层析,ODS柱层析,Sephadex LH‑20及HPLC进行分离纯化与制备,成功的分离得到此两种新化合物。其结构采用1H‑NMR、13C‑NMR及二维核磁波谱解析的方法确定为一种新化合物。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、分离和鉴别出的新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。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。
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、香豆素类、萜类、甾类、有机酸类、挥发油、生物碱类、氨基酸类、各种色素类和矿物质类等。其中生物碱是马齿苋中一类主要的化学成分,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-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,本发明提供两种生物碱及其提取分离方法,具体为从马齿苋中提取的新化合物,经研究发现本发明的新化合物具有抗炎、抗肿瘤的作用,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。
为了实现上述目的,本发明提供了如下技术方案。
本发明提供两种从马齿苋药材中分离出的生物碱类化合物,其特征在于,所述生物碱类化合物包括如下两种:
分子式分别为C5H6N4O、C6H6N2O4,并且根据结构命名为3-amino-1,3,4-triazabicyclo[3.2.1]octa-4,6-dien-8-one(1)、2-(dicarboxyamino)-1H-pyrrole(2),化学结构式为:
为实现本发明的上述目的,本发明还提供一种马齿苋中新化合物的提取分离方法,具体步骤为:
步骤1:取马齿苋干燥药材,采用水煎煮提取两次,水提液过滤,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中的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中所得物再经硅胶柱进行层析分离,用乙酸乙酯、乙酸乙酯:甲醇、甲醇进行洗脱,得到若干洗脱部位,经薄层色谱进行检测、显色,将各显色的洗脱部位分别减压浓缩至干,得到浓缩物备用;
步骤4:将步骤3中所得物再经预处理的ODS柱进行层析分离,用甲醇∶水梯度洗脱,得到若干洗脱部位,经薄层色谱进行检测及显色,将各显色的洗脱部位分别减压浓缩至干,得到浓缩物备用;
步骤5:将步骤4中所得物再经预处理的葡聚糖凝胶柱层析分离,用甲醇洗脱,得到若干洗脱部位,经薄层色谱进行检测,显色,合并显色的洗脱部位,将合并后的洗脱部位经减压浓缩至干,备用;
步骤6:将步骤5中的浓缩物通过HPLC分离制备,以甲醇∶0.1%甲酸水为流动相进行等度洗脱,最终得到本发明所述的两种生物碱类化合物。
进一步地,所述步骤1中水煎煮提取两次,每次2小时,水用量为药材的10倍。
进一步地,所述步骤2中所用乙酸乙酯洗脱程序为等度洗脱。
进一步地,所述步骤3中的硅胶层析分离用乙酸乙酯、体积比为5:1、3:1和1:1的乙酸乙酯::甲醇、甲醇进行梯度洗脱。
进一步地,所述步骤4中的ODS柱层析分离用体积比为50∶50、60∶40、70∶30、80∶20、90∶10和100∶0甲醇∶水梯度洗脱,洗脱条件为加压,使流速为1mL/min,温度为室温,其中填料粒度为20μm~40μm。
进一步地,所述步骤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。
进一步地,所用步骤5中所用甲醇等度洗脱。
进一步地,所述步骤6中所用甲醇∶0.1%甲酸等度洗脱中甲醇和水的体积比为5∶95(1)、30∶70(2),保留时间分别为7.806min(1)、3.397min(2)。
本发明还提供了如上所述从马齿苋药材中分离出的两种生物碱在制备抗炎药物或保健品药物中的应用。
与现有技术相比本发明的有益效果。
本发明中所述马齿苋新化合物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新化合物及一种针对本发明新化合物的提取分离方法,依次采用水煎煮提取、硅胶柱层析、Sephadex LH-20及HPLC进行分离纯化与制备,成功提取分离出新生物碱类化合物。该方法操作步骤仅为六步,操作方法简便及快速,提取分离过程主要采用水煎煮提取及乙酸乙酯洗脱,工艺方法环保,且经该方法分离得到的化合物纯度较高且大于90%。此外经研究表明该新化合物具有抗炎作用,因此本发明新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,亦可用于制备抗炎药物。
附图说明
图1为本发明新化合物Compound1的高分辨质谱图。
图2为本发明新化合物Compound1的1H-NMR光谱图。
图3为本发明新化合物Compound1的13C-NMR光谱图。
图4为本发明新化合物Compound1的DEPT135光谱图。
图5为本发明新化合物Compound1的1H-1HCOSY光谱图。
图6为本发明新化合物Compound1的HMBC光谱图。
图7为本发明新化合物Compound2的高分辨质谱图。
图8为本发明新化合物Compound2的1H-NMR光谱图。
图9为本发明新化合物Compound2的13C-NMR光谱图。
图10为本发明新化合物Compound2的1H-1H COSY光谱图。
图11为本发明新化合物Compound2的HMBC光谱图。
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。
本发明提供生物碱类化合物,分子式分别为C5H6N4O、C6H6N2O4,并且根据结构命名为3-amino-1,3,4-triazabicyclo[3.2.1]octa-4,6-dien-8-one(1)、2-(dicarboxyamino)-1H-pyrrole(2),化学结构式分别为:
表1为两种生物碱类化合物的核磁数据:1H-NMR与13C-NMR在MeOD-d 4中。
表1:本发明Compound 1~2的核磁数据
本发明化合物结构鉴定参阅图1~图11。
本发明一种新化合物Compound 1的结构鉴定及推导。
Compound 1:淡黄色油状物,在薄层板上用碘化铋钾试剂喷洒后呈现橙色。UHPLC-ESI-QTOF/MS给出m/z:137.0473[M-H]-的准分子离子峰,理论值为137.0468,其分子式被确定为C5H6N4O,不饱和度为5。1H-NMR谱中显示了三个氢信号,包括两个烯烃甲基信号δH 7.10(1H,d,J = 3.42 Hz),δH 6.43(1H,d,J = 3.42 Hz),以及一个亚甲基信号δH 4.55(2H,s)。13C-NMR和DEPT135光谱说明存在一个在δC 160.3处的羰基信号,一个在δC 146.9处的季碳信号,在δC 119.4和δC110.3处的两个烯烃甲基信号,以及一个在δC 57.7处的亚甲基信号。1H-1HCOSY谱中H-6(δH 7.10)和H-7(δH 6.43)的强相关信号以及1H-NMR谱中的H-6和H-7的耦合常数证明两个烯氢位于相邻位置。在HMBC谱中,H-6和H-7都与C-8(δC 160.3)相关,H-6和H-7都与C-5(δC 146.9)相关,并且H-6和H-7的耦合常数为3.42 Hz,由此,我们可以推断出该结构存在五元环。根据H-2与C-7和8的相关性以及H-2(δH 4.55)和H-7的化学位移,说明存在H-2和H-7与同一个N原子相连,并且H-2在两个N原子之间。C-5的化学位移证明C-5与另一个N原子相连。由此可确定此新化合物为上述结构。
Compound 2:白色粉末,在薄层板板上用碘化铋钾试剂喷洒时呈现橙色。UHPLC-ESI-QTOF/MS给出m/z 169.0253[M-H]-的准分子离子峰,理论值为169.0254,其分子式被确定为C6H6N2O4,不饱和度为5。1H-NMR谱证明存在三个烯烃甲基信号,分别为δH 7.69(1H,dd,J= 0.66,1.62 Hz),δH 7.16(1H,dd,J = 0.66,3.48 Hz)和δH 6.56(1H,q,J = 1.62,3.48Hz)。13C-NMR谱显示,在δC 162.8处有一个羧基信号,在δC 133.5处有一个季碳信号,在δC147.7、118.5和113.0处有三个烯烃类甲基信号。从1H-1H COSY谱中的三个烯烃氢的强关联性和1H NMR谱中的烯烃氢的峰形可以判断出有三个相连的烯烃氢存在。根据H-4和H-5的耦合常数为3.48 Hz,证明存在一个五元环。在HMBC谱中,有相关信号显示H-3(δH 7.69)与C-2(δC 133.5)相关,H-5(δH 7.16)与C-2相关,H-3与羧酸碳质子(δC 162.8)相关。根据C-2的化学位移(δC 133.5),可以推断出它与N原子相连。根据该化合物的负离子UHPLC-ESI-QTOF/MS中的分子离子峰,可以确定两个羧基在1'位置与N原子相连,由此可确定此新化合物为上述结构。
本发明还提供上述两种新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150kg,采用水煎煮提取,水用量为药材的10倍,水煎煮提取两次,每次2h,直接加热浓缩,放凉至室温,得药液备用;
步骤2:将步骤1中所得药液部分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中乙酸乙酯提取物经硅胶柱分离,采用乙酸乙酯、乙酸乙酯:甲醇(5:1、3:1、1:1)、甲醇的梯度洗脱程序进行梯度洗脱,其中硅胶为200-300目。得到27个部位(即梯度洗脱得27个瓶,每瓶200mL),经薄层色谱进行检测、显色,留下显色的第10部位,50℃以下减压浓缩至干,备用。;
步骤4:将步骤3中所得的第10部位再经预处理的ODS中压柱层析分离,其中填料粒度为20μm~40μm,用甲醇∶水(50∶50、60∶40、70∶30、80∶20、90∶10、100∶0,v/v)梯度洗脱(加压,使流速为1mL/min,温度为室温),得到6个部位(即梯度洗脱得6个瓶,每瓶200mL),经薄层色谱进行检测、显色,留下显色的50%甲醇部位,50℃以下减压浓缩至干,备用;
步骤5:将步骤4中所得的第50%甲醇部位再经预处理的葡聚糖凝胶柱层析分离,用甲醇洗脱,得到22个洗脱部位(即共得到22个瓶,每瓶50mL),经薄层色谱进行检测,显色,将显色的18-21部位合并,50℃以下减压浓缩至干,备用;
步骤6:将步骤5中所得的显色部位经HPLC分离制备,以甲醇∶0.1%甲酸水为流动相等度洗脱,检测波长为210nm和254nm,分离制备得到本发明新化合物,归一法测定纯度为98%。
所述ODS与葡聚糖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浑浊,再以初始流动相平衡。
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:实验所用新生物碱化合物由上述方法制备,纯度均大于97%,精密称取,用DMSO和PBS稀释至下述各剂量组所需溶液。胎牛血清(美国Gibco公司);CCK-8试剂盒(美国Boster公司);DMSO(美国Sigma-Aldrich公司);DMEM高糖培养基、LPS、IL-1β和TNF-α的ELISA试剂盒(索莱宝科技有限公司);青霉素、链霉素(杭州四季青公司);PBS(北京中杉金桥生物技术有限公司)。
1.2 细胞株:RAW264.7巨噬细胞(美国ATCC细胞库)。
1.3 分组:分为正常组、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 CCK-8试剂法测定细胞活力:上述各组分别取对数生长期的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样品溶液(5μM~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10μL的CCK-8,温度37℃,5%CO2条件下继续孵育4h后,用酶标仪在570nm波长处测定各孔吸光值。
2.3 ELISA法测定炎症因子IL-1β、TNF-α:将对数生长期的RAW264.7巨噬细胞接种于96孔培养板中,细胞密度为2×105个/mL,每孔1mL,温度37℃,5%CO2条件下培养过夜,实验组加入不同浓度样品溶液(1μM~20μM)培育1h后,在每孔加入LPS(终浓度为1μg/mL),共孵育3.25h,每组设3个复孔。ELISA法测定四种来源于马齿苋的新生物碱类化合物处理后的RAW264.7巨噬细胞分泌的IL-1β和TNF-α的含量。
3 实验结果。
实验结果表明本发明的新化合物对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-1β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-1β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-1β和TNF-α含量的影响
综上所述,本发明提供马齿苋中新生物碱及其提取分离方法,依次采用水煎煮提取、硅胶柱层析、Sephadex LH-20及HPLC进行分离纯化与制备,成功的分离得到该新化合物。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,因此本发明的新生物碱可以作为天然产物开发中药新药,具有广阔的前景。
Claims (10)
2.一种如权利要求1所述的从马齿苋药材中分离出的两种生物碱的提取分离方法,其特征在于,提取分离方法的具体步骤为:
步骤1:取马齿苋干燥药材,采用水煎煮提取两次,水提液过滤,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中的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中所得物再经硅胶柱进行层析分离,用乙酸乙酯、乙酸乙酯:甲醇、甲醇进行洗脱,得到若干洗脱部位,经薄层色谱进行检测、显色,将各显色的洗脱部位分别减压浓缩至干,得到浓缩物备用;
步骤4:将步骤3中所得物再经预处理的ODS柱进行层析分离,用甲醇∶水梯度洗脱,得到若干洗脱部位,经薄层色谱进行检测及显色,将各显色的洗脱部位分别减压浓缩至干,得到浓缩物备用;
步骤5:将步骤4中所得物再经预处理的葡聚糖凝胶柱层析分离,用甲醇洗脱,得到若干洗脱部位,经薄层色谱进行检测,显色,合并显色的洗脱部位,将合并后的洗脱部位经减压浓缩至干,备用;
步骤6:将步骤5中的浓缩物通过HPLC分离制备,以甲醇∶0.1%甲酸水为流动相进行等度洗脱,最终得到本发明所述的新化合物。
3.如权利要求2所述提取分离方法,其特征在于,所述步骤1中回流提取两次,每次2小时,水用量为药材的10倍。
4.如权利要求2所述的提取分离方法,其特征在于,所述步骤2中所用乙酸乙酯洗脱程序为等度洗脱。
5.如权利要求2所述的提取分离方法,其特征在于,步骤3中的硅胶层析分离用乙酸乙酯、体积比为5:1、3:1和1:1的乙酸乙酯:甲醇、甲醇进行梯度洗脱。
6.如权利要求2所述的提取分离方法,其特征在于,步骤4中的ODS柱层析分离用体积比为50∶50、60∶40、70∶30、80∶20、90∶10和100∶0甲醇∶水梯度洗脱;洗脱条件为加压,使流速为1mL/min,温度为室温;其中填料粒度为20μm~40μm。
7.如权利要求2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。
8.如权利要求2所述的提取分离方法,其特征在于,步骤5中所用甲醇等度洗脱。
9.如权利要求2所述的提取分离方法,其特征在于,所述步骤6中所用甲醇∶0.1%甲酸等度洗脱中甲醇和水的体积比为5∶95(1)、30∶70(2);保留时间分别为7.806min(1)、3.397min(2)。
10.如权利要求1所述从马齿苋药材中分离出的两种生物碱在制备抗炎药物或保健品药物中的应用。
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