CN106866611A - 元宝草中具有抗艾滋病毒活性的化合物及分离制备和用途 - Google Patents

元宝草中具有抗艾滋病毒活性的化合物及分离制备和用途 Download PDF

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CN106866611A
CN106866611A CN201610989986.9A CN201610989986A CN106866611A CN 106866611 A CN106866611 A CN 106866611A CN 201610989986 A CN201610989986 A CN 201610989986A CN 106866611 A CN106866611 A CN 106866611A
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张勇慧
薛永波
朱虎成
陈春梅
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Huazhong University of Science and Technology
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Abstract

本发明属于医药技术领域，具体涉及从藤黄科金丝桃属植物元宝草的地上部分提取分离得到的新化合物的活性及结构，提供了新化合物的分离纯化制备方法，揭示了新化合物所具有的抗艾滋病毒活性的，特别是其中的新化合物1和2对HIV‑1(LAI)毒株表现出良好的抑制活性。本发明为开发新的抗艾滋病毒药物提供了备选化合物，对藤黄科植物的开发利用具有非常重要的意义。

Description

元宝草中具有抗艾滋病毒活性的化合物及分离制备和用途
本专利申请是申请号为2014106745446的发明专利申请的分案申请，2014106745446号专利申请的申请日为2014年11月21日，其发明名称为：元宝草中具有抗肿瘤和抗HIV活性的化合物及分离制备和用途。
技术领域
本发明属于医药技术领域，涉及化合物1-30的分离制备方法及用途。具体涉及分离纯化过程，结构确证，抗肿瘤细胞增殖作用和抗艾滋病毒活性等。
背景技术
元宝草为藤黄科(Guttiferae)金丝桃属(Hypericum)植物元宝草(Hypericumsampsonii Hance)，别名对叶草、合掌草、叶抱枝、穿心草等。该植物为多年生草本，高约0.2–0.8米，全体无毛。茎单一或少数，圆柱形，无腺点，上部分枝。叶对生，无柄，其基部完全合生为一体而茎贯穿其中心。花直径6–15毫米，花梗长约2–3毫米。蒴果宽卵珠形至或宽或狭的卵珠状圆锥形，长6–9毫米，宽4–5毫米，散布有卵珠状黄褐色囊状腺体。种子黄褐色，长卵柱形，长约1毫米，两侧无龙骨状突起，顶端无附属物，表面有明显的细蜂窝纹。花期5–6月，果期7–8月。元宝草在我国分布广泛，产于陕西至江南各省。一般生于路旁、山坡、草地、灌丛、田边、沟边等处，海拔0–1200米。日本、越南(北部)、缅甸(东部)、印度(东北部)也有分布，但是较少。作为传统中草药，民间以元宝草全草入药，该药具有凉血止血、清热解毒、活血调经、祛风通络的作用。可用于治疗吐血、咯血、创伤出血、肠炎、痢疾、乳痈、痈肿疔毒、烫伤、蛇咬伤、月经不调、风湿痹痛等。
研究人员对该植物化学成分进行了较为细致的研究，这些研究结果表明，元宝草化学成分主要包括多环多异戊烯基间苯三酚衍生物(PPAPs)、二蒽酮、口山酮、黄酮和二苯甲酮类化合物，此外还有植物甾醇、苯甲酸、咖啡酸、挥发油等。在这些已经分离鉴定的化合物中，包括了近四十个PPAPs，是元宝草主要的化学成分。对这些化合物的活性研究表明，他们具有抗肿瘤、抗菌、抗病毒等多种药理作用。
近年来，癌症和艾滋病患者的不断增加，已成为威胁动物和人类生命安全的最主要的原因。寻找安全有效的治疗癌症和艾滋病毒的药物是天然产物的研究热点之一，因此，从藤黄科金丝桃属植物元宝草中寻找具有抗肿瘤和抗艾滋病毒的新的天然产物具有非常重要的意义。
发明内容
本发明的目的是提供具有抗肿瘤和抗艾滋病毒活性的新的间苯三酚类化合物的来源以及分离纯化方法及其潜在应用价值。
本发明的间苯三酚类化合物，其结构式如式(1)；
本发明人通过对藤黄科金丝桃属植物元宝草的乙醇提取物进行分离纯化，得到30个新化合物。运用多种波谱分析方法和其他手段，确定其结构为间苯三酚类化合物，具体结构如式(1)所示。通过对所有新化合物的抗肿瘤活性评价，发现化合物16-20对白血病细胞HL-60，人肝癌细胞SMMC-7721，人肺癌细胞A-549，人乳腺癌细胞MCF-7，人结肠癌细胞SW480中的部分细胞表现出良好的活性，可以作为治疗抗肿瘤细胞药物开发的先导化合物。通过对化合物1和2的抗艾滋病毒活性测试，发现化合物1和2对HIV-1(LAI)毒株表现出良好的抑制活性，可以作为治疗艾滋病毒的先导化合物进行开发。
本发明的第二个目的是提供式(1)中所示化合物1-30在制备抗肿瘤药物中的应用。
本发明的第三个目的是提供式(1)中所示化合物1和2在制备抗艾滋病毒药物的应用。
附图说明
图1：化合物13的实验ECD和计算ECD对比图；
图2：化合物13及16-20的ECD对比图。
具体实施方式
实施例1：新化合物16-20的制备和结构鉴定。
(一)如式(1)所示化合物16-20的制备
1.提取分离
干燥的元宝草地上部分，切碎后用多功能提取罐用95％乙醇提取，每次100升左右于45℃下提取10小时，重复提取4次，减压回收溶剂得总浸膏。将总浸膏悬浮于水中，依次用石油醚和氯仿萃取得到石油醚部位和氯仿部位。石油醚部位进行硅胶柱层析(100-200目，5kg)，石油醚：丙酮梯度洗脱(100:0→0:100)，用TLC检测合并类似部分，得到6个组分。部分Ⅲ以硅胶划段，之后反复交替使用硅胶、ODS、Sephadex LH-20和反相HPLC纯化得到化合物16。部分Ⅳ以硅胶划段，之后反复交替使用硅胶、ODS、Sephadex LH-20和反相HPLC纯化得到化合物17-18。部分Ⅴ以ODS划段，之后反复交替使用硅胶、ODS、Sephadex LH-20和反相HPLC纯化得到化合物19。氯仿部位进行硅胶柱层析(100–200目，6kg)，石油醚：丙酮梯度洗脱(100:0→0:100)，用TLC检测合并类似部分，得到6个组分(ⅰ–ⅵ)，部分ⅱ用硅胶划段，之后反复交替使用硅胶、ODS、Sephadex LH-20和反相HPLC纯化得到化合物20。
如式1所示化合物16-20结构鉴定
对化合物16-20进行质谱，紫外光谱，红外光谱，旋光，核磁共振(见表1和表2)，圆二色谱和计算圆二色谱等数据测试，从而确定化合物的结构。
化合物16:Colorless oil,(c＝0.10,CHCl3)；UV(CH3OH)λmax(logε)＝204(4.22),248(3.95),and 275(3.88)nm；IR νmax＝3421,1722,1696,and 1626cm–1；for 1HNMR(400MHz)and 13C NMR(100MHz)data see Tables1 and 2；HRESIMS[M+Na]+m/z641.3431(calcd C38H50O7Na for 641.3454).化合物16绝对构型的确定是通过计算ECD和比较ECD来确定的，如图1和图2所示。
化合物17:Colorless oil,(c＝0.12,CHCl3)；UV(CH3OH)λmax(logε)＝205(4.01),247(3.73),and 277(3.65)nm；IR νmax＝3454,1728,1697,and 1626cm–1；for 1HNMR(400MHz)and 13C NMR(100MHz)data see Tables1 and 2；HRESIMS[M+Na]+m/z641.3431(calcd C38H50O7Na for641.3454).化合物17的绝对构型是通过与化合物13的ECD对比来确定的，如图1和图2所示。
化合物18:Colorless oil,(c＝0.32,CH3OH)；UV(CH3OH)λmax(logε)＝205(4.46),248(4.17),and 277(4.15)nm；IR νmax＝3518,1728,1698,and 1627cm–1；for 1HNMR(400MHz)and 13C NMR(100MHz)data see Tables1 and 2；HRESIMS[M+Na]+m/z641.3429(calcd C38H50O7Na for641.3454).化合物18的绝对构型是通过与化合物13的ECD对比来确定的，如图1和图2所示。
化合物19:Colorless oil,(c＝0.37,CHCl3)；UV(CH3OH)λmax(logε)＝203(4.25),247(4.00),and 274(3.88)nm；IR νmax＝3419,1734,and 1700cm–1；for 1H NMR(400MHz)and 13C NMR(100MHz)data see Table 1and 2；HRESIMS[M+Na]+m/z 657.3380(calcd C38H50O8Na for657.3403).化合物19的绝对构型是通过与化合物13的ECD对比来确定的，如图1和图2所示。
化合物20:Colorless oil,(c＝0.10,CH3OH)；UV(CH3OH)λmax(logε)＝203(4.39),248(4.04),and 277(3.95)nm；IR νmax＝3423,1728,1697,and 1626cm–1；for 1HNMR(400MHz)and 13C NMR(100MHz)data see Tables 1and 2；HRESIMS[M+Na]+m/z657.3383(calcd C38H50O8Na for 657.3403).化合物20的绝对构型是通过与化合物13的ECD对比来确定的，如图1和图2所示。
实施例2：化合物16-20对白血病细胞HL-60，人肝癌细胞SMMC-7721，人肺癌细胞A-549，人乳腺癌细胞MCF-7，人结肠癌细胞SW480活性细胞的抑制活性。
化合物16-20的抗肿瘤活性通过MTS法对白血病细胞HL-60，人肝癌细胞SMMC-7721，人肺癌细胞A-549，人乳腺癌细胞MCF-7，人结肠癌细胞SW480五种人体肿瘤细胞进行评价。结果如表3所示：
实施例3：化合物1和2对HIV-1型的抑制活性。
选用HIV-1(LAI)毒株，采用ELISA检测HIV核心蛋白P24抗原的方法，齐多夫定(AZT)为阳性药，对新化合物1，2和5进行了初步的抗HIV活性筛选(单孔，6浓度)，结果见表4。其中化合物1和2具有较好的抗病毒活性和选择指数，我们对其进行了复筛(3孔，12浓度)。结果如表4所示：
表1.化合物16–20的氢谱数据(Table 1.1H NMR Datafor Compounds 16–20)
400MHz核磁测于氘代氯仿，化学位移单位ppm(Record in CDCl3,400MHz for 1H,δin ppm)
表2.化合物16–20的碳谱数据(Table 2.13C NMR Datafor Compounds 16–20)
100MHz核磁测于氘代氯仿，化学位移单位ppm(Record in CDCl3,400MHz for 1H,δin ppm)
表3.化合物1–30细胞毒活性(Table 3Cytotoxic activities of compounds1–30)
表4.化合物1和2抗HIV活性(Table 4.Anti-HIV activities of compounds 1and2)

Claims (4)

1.具有式1之化合物1至化合物12中任一结构式所示的间苯三酚类新化合物：
2.权利要求1所述的间苯三酚类新化合物的制备方法，包括以下步骤：
(1)干燥的元宝草地上部分，切碎后用多功能提取罐用95％乙醇提取，每次100升左右于45℃下提取10小时，重复提取4次，减压回收溶剂得总浸膏；
(2)将步骤(1)总浸膏用水混悬后，用石油醚萃取得到石油醚部位；
(3)将步骤(2)所得石油醚部位进行硅胶柱层析(100-200目，5kg)，石油醚：丙酮梯度洗脱(100:0→0:100)，用TLC检测合并类似部分，得到6个组分，组分1和组分2经多步色谱分离得到式Ⅰ所示化合物1-12，所述色谱分离方法包括正相硅胶柱色谱，反相硅胶柱色谱，凝胶柱色谱，高效液相色谱。
3.权利要求1中所述的化合物1或/和2在制备抗艾滋病毒药物中的应用。
4.根据权利要求3所述的应用，其特征在于，所述的艾滋病毒为HIV-1(LAI)毒株。
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