CN116621854A - 臭椿叶中萜类化合物及其制备方法和应用 - Google Patents
臭椿叶中萜类化合物及其制备方法和应用 Download PDFInfo
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Abstract
本发明涉及臭椿叶中萜类化合物及其制备方法和应用,属于医药技术领域,具体涉及从苦木科臭椿属植物臭椿叶(Ailanthus altissima)中提取分离的3个新的苦木苦味素类及4个萜类化合物,这些化合物具有良好的抗肝癌活性。另外,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,具体涉及植物臭椿的叶中制备得到的新的苦木苦味素及萜类化合物及这些化合物在抗肝癌方面的应用。
背景技术
臭椿(Ailanthus altissima(Mill.)Swingle)为苦木科(Simaroubaceae)臭椿属(Ailanthus Desf.)植物,广泛分布于我国陕西省、甘肃省、四川省、云南省等地。其根皮入药具有清热燥湿、收涩固肠的功效,主治赤白久痢、肠风下血、带下血崩、梦遗滑精等症。现代化学与药理学研究表明,臭椿中含有苦味素、甾体、香豆素、生物碱、木质素等成分,具有抗肿瘤、抗病毒抗炎、抗氧化等多种活性。
经检索,目前少有关于臭椿叶中化学成分的报道或者相关专利。
发明内容
本发明的目的在于提供一种从臭椿叶中制备得到的萜类化合物,及其制备方法和其在抗肝癌方面的应用。
本发明所述从苦木科臭椿属植物臭椿叶[Ailanthus altissima]中分离得到的3种新苦木苦味素及4种新萜类化合物结构如图所示:
本发明的制备技术方案包括如下步骤:
取干燥的臭椿叶以乙醇提取,合并提取液浓缩得浸膏,浸膏采用二氯甲烷和正丁醇萃取,并将所得组分经硅胶柱色谱,以二氯甲醇系统100:1-1:1进行等度梯度洗脱,共收集到6个组分Fr.A-F;
利用HP20,ODS柱色谱将组分Fr.C以乙醇-水系统20:80-90:10进行梯度洗脱,得6个组分Fr.C1-C6;
经硅胶柱色谱以石油醚-乙酸乙酯系统100:1-10:1进行洗脱并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.C4得到了化合物1-7。
优选地,所述臭椿叶中的萜类化合物的制备方法,采用的臭椿为苦木科苦木属植物臭椿的干燥叶[Ailanthus altissima]。
优选地,所述臭椿叶中的萜类化合物的制备方法,取干燥的臭椿叶以70-80%工业乙醇回流提取3次,每次2-3h。
优选地,所述臭椿叶中的萜类化合物的制备方法,以70:30-30:70的乙腈-水流动相分离Fr.C4。
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、计算核磁、计算ECD及X单晶衍射方法对化合物1-7的结构鉴定,相应的结构表征数据如表1-3所示,谱图如图1-11所示。
AilanlactoneA(1):黄色油状;(c0.20,MeOH);通过HRESIMS m/z459.1621[M+Na]+(calcd for C22H28NaO9,459.1626)确定分子式为C22H28O9;通过分析ailanlactone A的1HNMR、13CNMR、HSQC谱、HMBC谱、计算ECD及X单晶衍射图,确定了ailanlactone A的结构,为一个新化合物。
AilanlactoneB(2):白色无定形粉末;(c0.20,MeOH);通过HRESIMSm/z 517.2151[M+Na]+(calcd for C25H34NaO10,517.2144)确定分子式为C25H34O10;通过分析ailanlactoneB的1HNMR、13CNMR、HSQC谱、HMBC谱及计算ECD,确定了ailanlactoneB的结构,为一个新化合物。
AilanlactoneC(3):白色无定形粉末;(c0.30,MeOH);通过HRESIMSm/z 517.2151[M+Na]+(calcd for C25H34NaO9,517.2144)确定分子式为C25H34O9;通过分析ailanlactoneC的1HNMR、13CNMR、HSQC谱、HMBC谱及计算ECD,确定了ailanlactoneC的结构,为一个新化合物。
Ailanaltiolide K(4):白色无定形粉末;(c0.10,MeOH);通过HRESIMSm/z 653.4716[M+Na]+确定分子式为C36H54O9;通过分析ailanaltiolide K的1HNMR、13CNMR、HSQC谱、HMBC谱、计算ECD及X单晶衍射图,确定了ailanaltiolide K的结构,为一个新化合物。
Ailanterpene A(5):白色无定形粉末;(c0.10,MeOH);通过HRESIMSm/z 373.1632[M+Na]+(calcd for C19H26O6Na,373.1622)确定分子式为C19H26O6;通过分析ailanterpene A的1HNMR、13CNMR、HSQC谱、HMBC谱及计算ECD,确定了ailanterpene A的结构,为一个新化合物。
AilanterpeneB(6):白色无定形粉末;(c0.10,MeOH);通过HRESIMS m/z285.1096[M+Na]+确定分子式为C15H18O4;通过分析ailanterpeneB的1HNMR、13CNMR、HSQC谱、HMBC谱及计算ECD,确定了ailanterpeneB的结构,为一个新化合物。
AilanterpeneC(7):白色无定形粉末;(c0.10,MeOH);通过HRESIMSm/z 303.1572[M+Na]+(calcd for C16H24O4Na,303.1567)确定分子式为C16H24O4;通过分析ailanterpeneC的1HNMR、13CNMR、HSQC谱、HMBC谱及计算ECD,确定了ailanterpeneC的结构,为一个新化合物。
一种药物组合物,包含上述从臭椿中制备得到萜类化合物或其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臭椿中制备得到萜类化合物或其药学上可接受的盐或包含上述化合物的药物组合物在制备抗肝癌药物中的应用。
对本发明所述7个新化合物的抗肝癌活性进行了考察,化合物4对人肝癌Hep3B细胞系展现出比阳性药索拉菲尼(Sorafenib)更强的细胞毒性,因此本发明所述的化合物4具有进一步开发治疗肝癌药物的前景。
本发明相对于现有技术,具有以下有益效果: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,同时其抗肝癌活性较好,具有进一步开发的价值。
附图说明
图1化合物1的HRESIMS、1H、13C-NMR和HMBC谱;
图2化合物2的HRESIMS、1H、13C-NMR和HMBC谱;
图3化合物3的HRESIMS、1H、13C-NMR和HMBC谱;
图4化合物4的HRESIMS、1H、13C-NMR和HMBC谱;
图5化合物5的HRESIMS、1H、13C-NMR和HMBC谱;
图6化合物6的HRESIMS、1H、13C-NMR和HMBC谱;
图7化合物7的HRESIMS、1H、13C-NMR和HMBC谱;
图8化合物1-7的1H-1H COSY、HMBC相关;
图9化合物1和6的与计算13C NMR;
图10化合物6、9的X单晶数据;
图11化合物1-4,5-7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1-7的制备。
取干燥的臭椿叶以乙醇提取,合并提取液浓缩得浸膏,浸膏采用二氯甲烷和正丁醇萃取,并将所得组分经硅胶柱色谱,以二氯甲醇系统100:1-1:1进行等度梯度洗脱,共收集到6个组分Fr.A-F;
利用HP20,ODS柱色谱将组分Fr.C以乙醇-水系统20:80-90:10进行梯度洗脱,得6个组分Fr.C1-C6;
经硅胶柱色谱以石油醚-乙酸乙酯系统100:1-10:1进行洗脱并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.C4得到了化合物1-7。
实施例2
化合物1-7的抗肝癌活性考察
采用改良MTT法测试:取对数生长期的人肝癌肿瘤细胞HepG2、Hep3B,经胰酶消化后制成单细胞悬浮液,以4000个细胞/孔的细胞密度接种于96孔培养板,培养箱中培养12h后,每孔加入不同浓度(25,12.5,6.25,3.125,1.5,0.75μM)药物100μL,对照组加等体积的空白培养基,每组设3个复孔,无细胞孔为背景。置于37℃、5%CO2条件下培养48h后,每孔加MTT 20μL,继续培养4h,吸弃每孔内上清液后,加入DMSO 150μL,室温振荡,使结晶充分溶解。用酶标仪检测492nm处吸光度值(A),实验重复3次,生长抑制率(%)=[A(阴性对照)-A(加药组)]/A(阴性对照)×100%,再利用spss数据分析软件求出化合物的IC50值。
表4化合物1-7对两种人肝癌细胞的细胞毒性
实验结果如表4所示。实验结果表明,化合物4对人肝癌Hep3B细胞系展现出比阳性药索拉菲尼(Sorafenib)更强的细胞毒性,因此本发明所述的化合物4具有进一步开发治疗肝癌药物的前景
显然,本领域的技术人员可以对本发明进行各种改动和变型而不脱离本发明的精神和范围。这样,倘若本发明的这些修改和变型属于本发明权利要求及其等同技术的范围之内,则本发明也意图包含这些改动和变型在内。
Claims (9)
1.一种臭椿叶中的萜类化合物,其特征在于,所述化合物为如下所示结构中的任一种:
2.根据权利要求1所述的臭椿叶中的萜类化合物,其特征在于,所述臭椿为苦木科臭椿属植物臭椿[Ailanthusaltissima]。
3.权利要求1或权利要求2所述臭椿叶中的萜类化合物的制备方法,其特征在于,包括如下步骤:
取干燥的臭椿叶以乙醇提取,合并提取液浓缩得浸膏,浸膏采用二氯甲烷和正丁醇萃取,并将所得组分经硅胶柱色谱,以二氯甲醇系统100:1-1:1进行等度梯度洗脱,共收集到6个组分Fr.A-F;
利用HP20,ODS柱色谱将组分Fr.C以乙醇-水系统20:80-90:10进行梯度洗脱,得6个组分Fr.C1-C6;
经硅胶柱色谱以石油醚-乙酸乙酯系统100:1-10:1进行洗脱并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.C4得到了化合物1-7。
4.根据权利要求3所述臭椿叶中的萜类化合物的制备方法,其特征在于,采用的臭椿为苦木科臭椿属植物臭椿[Ailanthusaltissima]。
5.根据权利要求3所述臭椿叶中的萜类化合物的制备方法,其特征在于,取干燥的臭椿叶以70-80%工业乙醇回流提取3次,每次2-3h。
6.根据权利要求3所述臭椿叶中的萜类化合物的制备方法,其特征在于,以70:30-30:70的乙腈-水流动相分离Fr.C4。
7.一种药物组合物,其特征在于,所述药物组合物包含权利要求1或权利要求2所述臭椿叶中的萜类化合物或其药学上可接受的盐和药学上可接受的载体或赋形剂。
8.权利要求1或权利要求2所述臭椿叶中的萜类化合物或其药学上可接受的盐在制备抗肝癌药物中的应用。
9.权利要求7所述药物组合物在制备抗肝癌药物中的应用。
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SUMIEYA N. J. GROSVENOR等: "Tirucallane, Apotirucallane, and Octanorapotirucallane Triterpenes of Simarouba amara", J. NAT. PROD., vol. 69, 19 August 2006 (2006-08-19), pages 1315 - 1318 * |
ZHI-KANG DUAN等: "Discovery of Michael reaction acceptors from the leaves of Ailanthus altissima by a modified tactic", PHYTOCHEMISTRY, vol. 215, 13 September 2023 (2023-09-13), pages 4, XP087408796, DOI: 10.1016/j.phytochem.2023.113858 * |
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