CN115521245B - 马齿苋中一种生物碱类化合物及其提取分离方法与应用 - Google Patents
马齿苋中一种生物碱类化合物及其提取分离方法与应用 Download PDFInfo
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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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- C07D213/65—One oxygen atom attached in position 3 or 5
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- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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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、分离和鉴别出的一种生物碱类化合物及其提取分离方法。所述的生物碱类化合物,分子式为C8H9NO3,命名为(5‑hydroxypyridin‑2‑yl)methyl acetate,还提供上述生物碱类化合物的提取分离方法,依次采用乙醇提取,水煎煮提取、乙酸乙酯萃取、聚酰胺柱、ODS中压柱、Sephadex LH‑20纯化及HPLC分离制备。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得生物碱类化合物。该化合物具有潜在的抗炎活性,可作为新药开发和药理活性研究的原料,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
马齿苋是一年生植物,有黑色小种子和黄色或白色花朵,广泛分布于世界各地,特别是热带和亚热带地区。它被认为是最常用的天然药物之一,被称为“万能药”。同时,作为药食同源植物,马齿苋经常被添加到沙拉或汤中,略带咸酸味。马齿苋收载于2020版《中华人民共和国药典》,具有清热解毒、凉血止血、止痢等功效,它可以治疗各种疾病,如呼吸系统疾病,皮肤病,胃肠病,肝,肾病等。马齿苋具有多种生物活性,如抗炎、抗胆碱酯酶、抗氧化、抗菌、抗肿瘤、免疫调节活性等。此外,它可以治疗多种疾病,包括呼吸系统疾病、肝脏炎症、皮肤病、胃肠道疾病、肾脏和膀胱溃疡等。近年从马齿苋中分离出多种活性成分,包括生物碱、有机酸、黄酮、呋喃等,其中生物碱是马齿苋的主要成分,目前已知的生物碱类成分主要包括去甲肾上腺素、尿囊素、多巴胺、金莲花碱、胸腺嘧啶、尿嘧啶、腺嘌呤腺苷和酰胺类生物碱等。
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生物碱类化合物,经研究发现本发明的一种生物碱类化合物具有抗炎作用,同时提供一种针对本发明一种生物碱类化合物的简便、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,本发明提供一种从马齿苋药材中分离出的生物碱类化合物,分子式为C8H9NO3,命名为(5-hydroxypyridin-2-yl)methyl acetate,其化学结构式如下:
。
为实现本发明的上述目的,本发明还提供马齿苋中一种生物碱类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,用乙醇提取,捞出后用水煎煮提取,水提物用乙酸乙酯萃取,得到水层提取物,减压浓缩至干,得粗提物;
步骤2、将步骤1中粗提物用热水溶解,经聚酰胺柱分离,采用乙醇:水梯度洗脱,将20%乙醇洗脱部分合并蒸干,得浓缩物备用;
步骤3、将步骤2中所得物经预处理的ODS柱层析分离,用甲醇:水梯度洗脱,经薄层色谱进行检测,显色,合并显色部位,经减压浓缩至干,备用;
步骤4、将步骤3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5、将步骤4中所得物再经预处理的ODS柱层析分离,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,显色,将显色部位减压浓缩至干,得到浓缩物备用;
步骤6、将步骤5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,最终得到本发明所述的新化合物。
进一步地,所述步骤1中水煎煮提取两次,每次煎煮2小时,水用量为药材的10倍。
进一步地,所述步骤2中聚酰胺柱分离依次用体积比为20:80、70:30的乙醇:水梯度洗脱。
进一步地,所述步骤3中ODS柱层析分离依次用水,体积比为30:70、50:50、70:30、100:0甲醇:水梯度洗脱,所述步骤5中用体积比为20∶80、40:60、60:40、80:20甲醇∶水梯度洗脱。
进一步地,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,以初始流动相平衡。
进一步地,所述步骤4中所用流动相洗脱程序为等度洗脱。
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30:70。
本发明还提供了一种上述所述的马齿苋中生物碱类化合物的用途,其特征在于,所述用途可用于制备抗炎的药物或保健品。
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,依次采用乙醇提取,水煎煮提取、聚酰胺柱分离、ODS中压柱、Sephadex LH-20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六步,操作方法简便及快速,提取分离过程主要采用水提取,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,亦可用于制备抗炎药物。
附图说明
图1为本发明新生物碱类化合物(5-hydroxypyridin-2-yl)methyl acetate的1H-NMR光谱图。
图2为本发明新生物碱类化合物(5-hydroxypyridin-2-yl)methyl acetate的13C-NMR光谱图。
图3为本发明新生物碱类化合物(5-hydroxypyridin-2-yl)methyl acetate的DEPT 135光谱图。
图4为本发明新生物碱类化合物(5-hydroxypyridin-2-yl)methyl acetate的1H-1H COSY光谱图。
图5为本发明新生物碱类化合物(5-hydroxypyridin-2-yl)methylmethylcarbamate的HSQC光谱图。
图6为本发明新生物碱类化合物(5-hydroxypyridin-2-yl)methyl acetate的HMBC光谱图。
图7为本发明新生物碱类化合物(5-hydroxypyridin-2-yl)methyl acetate的ROESY光谱图。
图8为本发明新生物碱类化合物(5-hydroxypyridin-2-yl)methyl acetate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。
本发明提供一种生物碱类化合物,分子式分别为C8H9NO3,命名为(5-hydroxypyridin-2-yl)methyl acetate,化学结构式为:
。
所述生物碱类化合物根据结构命名为(5-hydroxypyridin-2-yl)methylacetate,表1为该一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:本发明一种生物碱类化合物(5-hydroxypyridin-2-yl)methyl acetate的核磁数据。
。
本发明生物碱类化合物(5-hydroxypyridin-2-yl)methyl acetate结构鉴定与推导。
(5-hydroxypyridin-2-yl)methyl acetate为黄色粉末,易溶于甲醇,不溶、微溶于水。点样于硅胶薄层板后,喷稀碘化铋钾试液斑点显橘黄色,提示该化合物为生物碱成分。UHPLC-ESI-QTOF/MS谱给出m/z:168.0651 [M + H]+的准分子离子峰,分子量为167.0582。结合1H-NMR,13C-NMR以及DEPT数据,推测该化合物可能的分子式为C8H9NO3,不饱和度为5。根据13C-NMR和DEPT-135谱图,该化合物中存在11个碳信号,包括1个甲基(δC20.9)、1个亚甲基(δC 67.4)、3个次甲基(δC 125.3、124.9、138.2)、3个季碳(δC 172.6、147.5、155.6)。根据13C-NMR信号δC 20.9(CH3)、δC 172.6(C-1)、δC 67.4(C-3)以及HMBC相关性提示,H-3(δH 0.53)和CH3均与C-1相关,推断出化合物中存在一个乙酸甲酯基团。此外,1H-NMR信号δH 5.77 (1H, d, J = 8.5Hz, H-3′)、δH 5.67 (1H, dd, J = 8.5, 2.3Hz, H-4′), δH 6.5 (1H, d, J = 2.3 Hz, H-6′)、以及H-3′到C-5′(δC 155.6)、H-4′到C-2′(δC147.5)、H-6′到C-4′(δC 124.9)的相关性提示该结构中存在典型的ABX系统。13C-NMR信号δC155.6(C-5′)、δC 138.2(C-6′)和C-2′位于低场区域,表明C-5′与羟基相连,C-6′和C-2′都与N相连。此外,HMBC相关性提示,H-3′与C-3相关,表明苯环在C-3与乙酸甲酯相连。因此,该化合物被鉴定为(5-hydroxypyridin-2-yl)methyl acetate。
本发明还提供上述一种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,采用乙醇提取,捞出后采用水煎煮提取,水用量为药材的10倍,煎煮提取两次,每次煎煮2h,水提液滤过,合并滤液,用乙酸乙酯萃取,得到水层提取物,减压浓缩至干,得粗提物。
步骤2:将步骤1中所得粗提物热水溶解,经聚酰胺柱分离,采用乙醇∶水(20:80、70:30,v/v)的梯度洗脱,将20%(体积百分数)乙醇洗脱部分合并蒸干,得浓缩物备用。
步骤3:将步骤2中浓缩物经预处理的ODS中压柱层析分离,其中填料粒度为40μm~70μm,采用甲醇:水(30:70、50:50、70:30、100:0,v/v)梯度洗脱(加压,使流速为1mL/min,温度为室温),得到4个部位(即梯度洗脱得4个瓶,每瓶200mL),显色,留下显色的第1个部位,并于室温以上,50℃以下减压浓缩至干,备用。
步骤4:将步骤3中所得显色部位经预处理的Sephadex LH-20柱层析,以甲醇等度洗脱,得到5个部位(即等度洗脱得5个瓶,每瓶20mL),经薄层色谱进行检测,显色,留下显色的第1~2部位,50℃以下减压浓缩至干,备用。
步骤5:将步骤4中所得物再经预处理的ODS中压柱层析分离,其中填料粒度为40μm~70μm,用甲醇:水(20:80、40:60、60:40、80:20、100:0,v/v)梯度洗脱(加压,使流速为1mL/min,温度为室温),得到10个部位(即梯度洗脱得10个瓶,每瓶100mL),经薄层色谱进行检测,显色,留下显色的第2~5个部位,50℃以下减压浓缩至干,备用。
步骤6:将步骤5中所得显色部位经HPLC分离制备,以甲醇和0.1%甲酸(30∶70,v/v)作为流动相,检测波长为210nm和280nm,分离制备得到本发明一种生物碱类化合物,归一法测定纯度均为90%~99%。
所述ODS和Sephadex LH-20凝胶的预处理过甲醇浸泡过24h,上柱,初始流动相平衡。
本发明生物碱类化合物的抗炎作用。
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-1β、TNF-α的ELISA试剂盒(美国Cayman公司);细胞裂解液。
1.2 细胞株:RAW264.7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 CCK8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发明一种生物碱类化合物(5-hydroxypyridin-2-yl)methylacetate(1μM~20μM),孵育1h后向LPS组和实验组分别加入浓度为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CCK8,温度37℃,5%CO2条件下继续孵育4h后,酶标仪450nm波长处测定各孔吸光值。
2.3 ELISA法测定炎症因子IL-1β和TNF-α: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,实验组加入本发明生物碱类化合物(5-hydroxypyridin-2-yl)methyl acetate(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法测定马齿苋来源新化合物处理后的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-1β和TNF-α炎症介质,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。
。
注:*P<0.05与对照组比较(高浓度组有显著性差异)。
ELISA法测定炎症因子IL-1β和TNF-α炎症介质结果如表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。
。
注:#P<0.05与对照组比较,*P<0.05与LPS组比较,均数±SD,n=3。
综上所述,本发明提供特殊化合物及其提取分离方法,依次采用水回流提取、聚酰胺柱层析、ODS中压柱、葡聚糖凝胶柱层析及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,因此本发明特殊化合物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 (4)
1.一种马齿苋药材中生物碱类化合物的提取分离方法,其特征在于,所述提取分离方法的具体步骤包括:
步骤1、取马齿苋干燥药材,用乙醇提取,捞出后用水煎煮提取,水提物用乙酸乙酯萃取,得到水层提取物,减压浓缩至干,得粗提物;
步骤2、将步骤1中粗提物用热水溶解,经聚酰胺柱分离,采用体积比为20:80、70:30的乙醇:水梯度洗脱,将体积百分数为20%乙醇洗脱部分合并蒸干,得浓缩物备用;
步骤3、将步骤2中所得物经预处理的ODS柱层析分离,用体积比为30:70、50:50、70:30、100:0的甲醇:水梯度洗脱,经薄层色谱进行检测,显色,合并显色部位,经减压浓缩至干,备用;
步骤4、将步骤3中所得浓缩物经预处理的Sephadex LH-20层析分离,用甲醇等度洗脱,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5、将步骤4中所得物再经预处理的ODS柱层析分离,用体积比为20:80、40:60、60:40、80:20的甲醇:水梯度洗脱,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6、将步骤5中所得浓缩物通过HPLC分离制备,以体积比为30:70的甲醇:0.1%甲酸为流动相进行等度洗脱,最终得到所述的化合物;
所述化合物的分子式为:C8H9NO3,并且根据结构命名为(5-hydroxypyridin-2-yl)methyl acetate,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中水提取两次,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ODS和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。
4.一种如权利要求1所述的马齿苋药材中生物碱类化合物的提取分离方法提取的生物碱类化合物在制备抗炎药物中的应用。
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CN106946766A (zh) * | 2017-05-11 | 2017-07-14 | 辽宁中医药大学 | 马齿苋中生物碱化合物及其提取分离方法 |
CN107459477A (zh) * | 2017-08-22 | 2017-12-12 | 辽宁中医药大学 | 一种马齿苋中异吲哚生物碱类化合物及其提取分离方法 |
CN109824568A (zh) * | 2019-04-03 | 2019-05-31 | 辽宁中医药大学 | 马齿苋中两种吲哚类新生物碱化合物及其提取分离方法与应用 |
CN110272369A (zh) * | 2019-07-16 | 2019-09-24 | 辽宁中医药大学 | 马齿苋中一种吡咯二羧酸类化合物及其提取分离方法与用途 |
CN111303154A (zh) * | 2020-03-12 | 2020-06-19 | 辽宁中医药大学 | 马齿苋中一种具有抗炎活性生物碱及其提取分离方法与用途 |
CN113264886A (zh) * | 2021-06-09 | 2021-08-17 | 辽宁中医药大学 | 马齿苋中一种哒嗪类化合物的提取分离方法及其应用 |
CN113264828A (zh) * | 2021-06-09 | 2021-08-17 | 辽宁中医药大学 | 马齿苋中一种苯甲酸类化合物及其提取分离方法 |
CN113698446A (zh) * | 2021-10-19 | 2021-11-26 | 辽宁中医药大学 | 马齿苋中一种生物碱类化合物及其提取分离方法 |
CN113968862A (zh) * | 2021-11-23 | 2022-01-25 | 辽宁中医药大学 | 马齿苋中两种新生物碱及其提取分离方法 |
CN114213473A (zh) * | 2021-10-19 | 2022-03-22 | 辽宁中医药大学 | 马齿苋中三种生物碱类化合物及其提取分离方法 |
CN114369076A (zh) * | 2021-06-09 | 2022-04-19 | 辽宁中医药大学 | 马齿苋中两种茚类化合物及其提取分离方法 |
CN114989084A (zh) * | 2022-06-16 | 2022-09-02 | 辽宁中医药大学 | 马齿苋中一种四氢异喹啉类生物碱的提取分离方法及其应用 |
CN114989064A (zh) * | 2022-06-16 | 2022-09-02 | 辽宁中医药大学 | 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 |
-
2022
- 2022-10-19 CN CN202211278130.2A patent/CN115521245B/zh active Active
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106946766A (zh) * | 2017-05-11 | 2017-07-14 | 辽宁中医药大学 | 马齿苋中生物碱化合物及其提取分离方法 |
CN107459477A (zh) * | 2017-08-22 | 2017-12-12 | 辽宁中医药大学 | 一种马齿苋中异吲哚生物碱类化合物及其提取分离方法 |
CN109824568A (zh) * | 2019-04-03 | 2019-05-31 | 辽宁中医药大学 | 马齿苋中两种吲哚类新生物碱化合物及其提取分离方法与应用 |
CN110272369A (zh) * | 2019-07-16 | 2019-09-24 | 辽宁中医药大学 | 马齿苋中一种吡咯二羧酸类化合物及其提取分离方法与用途 |
CN111303154A (zh) * | 2020-03-12 | 2020-06-19 | 辽宁中医药大学 | 马齿苋中一种具有抗炎活性生物碱及其提取分离方法与用途 |
CN113264828A (zh) * | 2021-06-09 | 2021-08-17 | 辽宁中医药大学 | 马齿苋中一种苯甲酸类化合物及其提取分离方法 |
CN113264886A (zh) * | 2021-06-09 | 2021-08-17 | 辽宁中医药大学 | 马齿苋中一种哒嗪类化合物的提取分离方法及其应用 |
CN114369076A (zh) * | 2021-06-09 | 2022-04-19 | 辽宁中医药大学 | 马齿苋中两种茚类化合物及其提取分离方法 |
CN113698446A (zh) * | 2021-10-19 | 2021-11-26 | 辽宁中医药大学 | 马齿苋中一种生物碱类化合物及其提取分离方法 |
CN114213473A (zh) * | 2021-10-19 | 2022-03-22 | 辽宁中医药大学 | 马齿苋中三种生物碱类化合物及其提取分离方法 |
CN113968862A (zh) * | 2021-11-23 | 2022-01-25 | 辽宁中医药大学 | 马齿苋中两种新生物碱及其提取分离方法 |
CN114989084A (zh) * | 2022-06-16 | 2022-09-02 | 辽宁中医药大学 | 马齿苋中一种四氢异喹啉类生物碱的提取分离方法及其应用 |
CN114989064A (zh) * | 2022-06-16 | 2022-09-02 | 辽宁中医药大学 | 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 |
Non-Patent Citations (1)
Title |
---|
A synthesis of 6- and 4-(hydroxymethyl) derivatives of pyridin-3-ols;Deady, Leslie W.等;《Australian Journal of Chemistry》;第36卷(第12期);2565-2568 * |
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