CN116120334A - 芫花花蕾中的二萜类化合物及其制备方法和应用 - Google Patents
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Abstract
芫花花蕾中的二萜类化合物及其制备方法和应用,属于医药技术领域,具体涉及从瑞香科瑞香属植物芫花(Daphne genkwa Sieb.et Zucc.)的干燥花蕾中提取分离的4个新的二萜类化合物,该新化合物具有良好的抗肿瘤活性作用。本发明制备方法简单易行,重现性比较好,纯度较高。
Description
技术领域
本发明属于医药技术领域,具体涉及植物芫花中制备得到的新的二萜类化合物及该类化合物在抗肿瘤方面的应用。
背景技术
芫花为瑞香科(Thymelaeaceae)植物芫花(Daphne genkwa Sieb.et Zucc.)的干燥花蕾,在我国的长江流域各省和黄河流域的部分地区广泛分布。作为中药中传统的峻下逐水药,其味苦、辛,性温,有大毒,主治泻水逐饮,外用杀虫疗疮。芫花中的主要化学成分包括黄酮类、二萜类、香豆素类、甾体类、木脂素类等。其中瑞香烷型二萜类化合物因其复杂的5/7/6三环骨架多羟基取代的分子结构及其抗肿瘤、抗炎、抗HIV等广泛的活性而广受研究。
发明内容
本发明的目的在于提供一种从芫花花蕾中制备得到的二萜类化合物,以及其在抗肿瘤方面的应用。
本发明所述4种从瑞香科瑞香属植物芫花[Daphne genkwa Sieb.et Zucc.]花蕾中分离得到的新二萜类化合物的结构如下所示:
本发明的制备技术方案包括如下步骤:
取干燥的芫花花蕾以乙醇提取,合并提取液浓缩得浸膏,浸膏采用二氯甲烷萃取并将所得组分经硅胶柱色谱,以二氯甲烷-甲醇系统100:0-0:100进行等度梯度洗脱,共收集到5个组分Fr.A-Fr.E;
组分Fr.C经HP20柱色谱,以乙醇-水系统0:100-90:10进行梯度洗脱,得4个组分Fr.C1-Fr.C4;
所得组分Fr.C3经硅胶柱色谱以石油醚-乙酸乙酯系统100:1-10:1在TLC分析的基础上得到10个亚组分Fr.C3-1-Fr.C3-10;
在制备性反相高效液相色谱上使用乙腈-水的流动相来分离Fr.C3-2、Fr.C3-3和Fr.C3-4得到化合物1-4。
所述步骤中,采用的芫花为瑞香科瑞香属植物芫花[Daphne genkwa Sieb.etZucc.]的干燥花蕾。
所述步骤中,取干燥的芫花花蕾以70%-80%工业乙醇回流提取2-3次,每次2-3h。
所述步骤中,在制备性反相高效液相色谱上以85:15-65:35的乙腈-水流动相分离Fr.C3-2、Fr.C3-3和Fr.C3-4。
所得化合物经过系统结构鉴定结果如下:
利用高分辨质谱,一维NMR、二维NMR、计算ECD的方法对化合物1-4的结构鉴定,相应谱图如图1-18所示。
Yuanhuakine E(1):白色无定形粉末;HRESIMS m/z547.1920[M+Na]+(calcd for C29H32O9Na 547.1939)确定分子式为C29H32O9,通过分析yuanhuakine E的1H NMR、13C NMR、HMQC谱、HMBC谱、计算ECD,确定了yuanhuakine E的结构,为一个新化合物。
Yuanhuakine F(2):无色油状,HRESIMS m/z 557.2351[M+Na]+(calcd for C30H36O10 557.2381)确定分子式为C30H36O10,通过分析yuanhuakine F的1HNMR、13C NMR、HMQC谱、HMBC谱、计算ECD,确定了yuanhuakine F的结构,为一个新化合物。
Yuanhuakine G(3):无色油状;HRESIMS m/z 649.2942[M+Na]+(calcd for C35H46O10Na,649.2983)确定分子式为C35H46O10,通过分析该化合物的1HNMR、13C NMR、HMQC谱、HMBC谱、计算ECD,确定了化合物3的结构,为一个新化合物。
12-O-(2'E,4'Z-decadienoyl)-4-hydroxyphorbol-13-acetyl(4):无色油状; HRESIMS m/z 579.2890[M+Na]+(calcd for C32H44O8Na,579.29298)确定分子式为C32H44O8,通过分析yuanhuakine G的1H NMR、13C NMR、HMQC谱、HMBC谱、计算ECD,确定了4的结构,为一个新化合物。
对本发明所述4个新化合物的细胞毒性进行了考察,其中化合物1-4均展现出良好的细胞毒性,因此本发明所述的新二萜类化合物具有进一步开发抗肿瘤药物的前景。
一种药物组合物,包含上述从芫花花蕾中制备得到二萜类化合物1-4中任一个或多个或其在药学上可接受的盐和药学上可接受的载体或赋形剂。
本发明还提供所述从芫花花蕾中制备得到的二萜类化合物或包含上述化合物的药物组合物在制备抗肿瘤药物中的应用。
本发明的优点在于,所述化合物均为新化合物,结构新颖,且均为立体构型确定的光学纯化合物,同时其抗肿瘤活性强,具有进一步开发的价值。
表1化合物1-4的1H NMR数据(CDCl3)
表2化合物1-4的13C NMR数据(CDCl3)
附图说明
图1化合物1的HRESIMS谱;
图2化合物1的1H NMR谱(600MHz);
图3化合物1的13C NMR谱(150MHz);
图4化合物1的HMBC谱(600MHz);
图5化合物2的HRESIMS谱;
图6化合物2的1H NMR谱(600MHz);
图7化合物2的13C NMR谱(150MHz);
图8化合物2的HMBC谱(600MHz);
图9化合物3的HRESIMS谱;
图10化合物3的1H NMR谱(600MHz);
图11化合物3的13C NMR谱(150MHz);
图12化合物3的HMBC谱(600MHz);
图13化合物1的HRESIMS谱;
图14化合物1的1H NMR谱(600MHz);
图15化合物1的13C NMR谱(150MHz);
图16化合物1的HMBC谱(600MHz);
图17化合物1-4的HMBC相关;
图18化合物1-4的实测与计算ECD谱图。
具体实施方式
下面所列实施例有助于本领域技术人员更好地理解本发明,但不以任何方式限制本发明。
实施例1
化合物1-4的制备,具体操作步骤如下:
取干燥的芫花花蕾60kg以70%工业乙醇回流提取2次,每次2h,合并提取液浓缩得浸膏,浸膏采用二氯甲烷萃取并将所得组分经硅胶柱色谱,以二氯甲烷-甲醇系统100:0-0:100进行等度梯度洗脱,共收集到5个组分Fr.A-Fr.E;
组分Fr.C经HP20柱色谱,以乙醇-水系统0:100-90:10进行梯度洗脱,得4个组分Fr.C1-Fr.C4;
所得组分Fr.C3经硅胶柱色谱以石油醚-乙酸乙酯系统100:1-10:1在TLC分析的基础上得到10个亚组分Fr.C3-1-Fr.C3-10;
在制备性反相高效液相色谱上使用乙腈-水的流动(85:15-65:35)来分离Fr.C3-2、Fr.C3-3和Fr.C3-4得到化合物1(10.0mg),2(7.5mg),3(10.5mg),4(9.3mg)。
实施例2
化合物1-4的抗肿瘤的活性考察
使用MTT法测试化合物1-2对肿瘤细胞系A549,Hep3B和MCF-7的生长抑制活性。取对数生长的细胞以6×104个/mL,以每孔100μL接种于96孔板中,设置3个复孔并置于37℃、5%CO2培养箱中孵育24h。然后用不同浓度的测试化合物(0.1,1,10,50μM),加药处理48h。
药物作用48h后,将细胞与MTT溶液(0.5mg/mL)在37℃下再孵育4h。吸除培养液后每孔加入DMSO将其完全溶解,并采用酶标仪于490nm处测定吸光度。所有实验都平行进行并重复三次,设置空白组及阳性对照组结果如表3所示。
表3化合物1-4的细胞毒性(IC50 values)
aPositive controls.
Claims (9)
2.根据权利要求1所述的芫花花蕾中的二萜类化合物,其特征在于,所述芫花为瑞香科瑞香属植物芫花(Daphne genkwa Sieb.et Zucc.)。
3.一种权利要求1或2所述芫花花蕾中的二萜类化合物的制备方法,其特征在于,包括如下步骤:
取干燥的芫花花蕾以乙醇提取,合并提取液浓缩得浸膏,浸膏采用乙酸乙酯萃取并将所得组分经硅胶柱色谱,以二氯甲烷-甲醇系统100:0-0:100进行等度梯度洗脱,共收集到5个组分Fr.A-Fr.E;
组分Fr.C经HP20柱色谱,以乙醇-水系统0:100-90:10进行梯度洗脱,得4个组分Fr.C1-Fr.C4;
所得组分Fr.C3经硅胶柱色谱以石油醚-乙酸乙酯系统100:1-10:1在TLC分析的基础上得到10个亚组分Fr.C3-1-Fr.C3-10;
在制备性反相高效液相色谱上使用乙腈-水的流动相来分离Fr.C3-2、Fr.C3-3和Fr.C3-4得到化合物1-4。
4.根据权利要求3所述芫花花蕾中的二萜类化合物的制备方法,其特征在于,采用的芫花为为瑞香科瑞香属植物芫花(Daphne genkwa Sieb.et Zucc.)的干燥花蕾。
5.根据权利要求3所述芫花中的二萜类化合物的制备方法,其特征在于,取干燥的芫花花蕾以70%-80%工业乙醇回流提取2-3次,每次2-3h。
6.根据权利要求3所述唐古特瑞香中的二萜类化合物的制备方法,其特征在于,在制备性反相高效液相色谱上以85:15-65:35的乙腈-水流动相分离Fr.C3-2、Fr.C3-3和Fr.C3-4。
7.一种药物组合物,其特征在于,包含权利要求1或2所述芫花中的二萜类化合物或其在药学上可接受的盐和药学上可接受的载体或赋形剂。
8.一种权利要求1或2所述芫花中的二萜类化合物或其在药学上可接受的盐在制备抗肿瘤药物中的应用。
9.一种权利要求7所述药物组合物在制备抑制肿瘤细胞系A549,Hep3B和MCF-7活性药物中的应用。
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