CN102267884B - 化合物及其在制备抗肿瘤药物中的应用 - Google Patents
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Abstract
本发明公开了化合物ChondrosterinA及其在制备抗肿瘤药物中的应用。本发明研究发现化合物ChondrosterinA对多种肿瘤细胞系显示出强效的细胞毒性,如:对肺癌(A549)、鼻咽癌(CNE2)和结肠癌(Lovo)3种肿瘤细胞的IC50值分别为2.452,4.963,5.49μM。表明ChondrosterinA可用于制备抗肿瘤药物,可与其他药物制成抗肿瘤药物组合物,可与药学可以接受的辅料制成注射剂、片剂、丸剂、胶囊剂、溶液、悬浮剂和乳剂等剂型;其给药途径可为经口服、静脉、肌肉或皮肤给药。
Description
技术领域
本发明涉及化合物Chondrosterin A的新用途。
背景技术
恶性肿瘤是一种严重危害人类生命健康的常见病,已成为仅次于心脑血管病的第二位死因,而且肿瘤发病率还在逐年增加。寻找和开发高效低毒的抗肿瘤药物仍然是目前攻克肿瘤的主要途径。
海洋真菌,资源丰富,它们适应了高盐低营养的海洋环境,有独特的代谢途径和遗传背景,也为人类提供了大量的陆地微生物所不能提供的活性代谢产物。近二十年来,从海洋真菌的代谢产物中分离得到了一大批新结构的化合物,结构类型有萜类、醚类、大环内酯类、生物碱类、肽类、酰胺类以及醌类等,有些具有强效抗肿瘤活性化合物,抗肿瘤机制有作用于DNA、微管、拓扑异构酶以及其他酶,作用于细胞通路诱导肿瘤细胞凋亡,诱导免疫反应或是通过改变机体内环境酸碱平衡从而抑制癌细胞生长等,这些活性物质药用前景明显,部分化合物还进入了临床前或临床试验。
我们近年开展了南海软珊瑚的共附生真菌及其活性物质研究,发现软珊瑚共附生真菌的菌株资源非常丰富,而且从中发现活性物质的几率很高。倍半萜类化合物Chondrosterin A是南海扭曲肉芝软珊瑚Sarcophyton tortuosum中分离得到的真菌Chondrostereum sp.经发酵培养产生的。化合物Chondrosterin A是新化合物,其抗肿瘤活性未见报道。
发明内容
本发明的目的在于提供一种海洋真菌新的代谢产物Chondrosterin A。
本发明所述的化合物Chondrosterin A,是具有hirsutane骨架结构的、新的倍半萜化合物,是海洋真菌Chondrostereum sp.的一个主要代谢产物。
Chondrosterin A的结构式为:
(Ⅰ)
本发明的化合物Chondrosterin A 可以从真菌,例如南海海洋软珊瑚Sarcophyton tortuosum的内生真菌Chondrostereum sp.的培养液中提取分离而得到。
本发明化合物Chondrosterin A由真菌Chondrostereum sp.发酵制备方法包括以下步骤:
a. 海洋真菌Chondrostereum sp.的种子培养:
选用PDA (potato dextro se agar) 培养基,其培养基组成为:马铃薯 200 g,葡萄糖 20 g,琼脂 20 g,海水 1 L;制成试管斜面,挑取菌株接入斜面,25-28℃培养5-7天;
b. 海洋真菌Chondrostereum sp.的发酵培养:
发酵培养基成分配比按重量比为:马铃薯 50-500,葡萄糖5-40,酵母提取物0.5-5,蛋白胨1-10,粗海盐2-50,水1000;将斜面中培养好的菌株挑入发酵培养基,于室温25-30℃静置10-40天;
c. 将上述培养好的发酵液过滤,滤除菌体,收集发酵液;
d. 发酵液用乙酸乙酯提取,合并提取液,浓缩得到总提取物;
e. 用乙酸乙酯溶解提取物,溶解物在硅胶柱中进行色谱分离,以石油醚-乙酸乙酯-甲醇梯度淋洗;
f. 收集石油醚-乙酸乙酯(2:1)得到的洗脱组分,经高效液相色谱,以乙腈-水(60:40)纯化得到化合物Chondrosterin A。
本发明研究发现化合物Chondrosterin A对多种肿瘤细胞系显示出强效的细胞毒性,如:对肺癌(A549)、鼻咽癌(CNE2)和结肠癌(Lovo)3种肿瘤细胞的IC50值分别为2.452,4.963,5.49 μM。表明化合物Chondrosterin A可用于制备抗肿瘤药物,可与其他药物制成抗肿瘤药物组合物,可与药学可以接受的辅料制成注射剂、片剂、丸剂、胶囊剂、溶液、悬浮剂和乳剂等剂型;其给药途径可为经口服、静脉、肌肉或皮肤给药。
具体实施方式
下面结合实施例对本发明作进一步说明。
实施例1:化合物Chondrosterin A的制备
a. 海洋真菌Chondrostereum sp.的种子培养:
菌种以PDA为培养基,组成为:马铃薯 200 g的水煮液,葡萄糖 10 g,琼脂 20 g,水 1 L。制成试管斜面,挑取菌株接入斜面,25-28℃培养7天后于4℃保存。
b. 海洋真菌Chondrostereum sp.的发酵培养:
发酵培养基组成为:马铃薯 200 g的水煮液,葡萄糖 10 g,粗海盐23 g,水1 L;将斜面中培养好的菌株挑入发酵培养基,于室温25-28℃静置培养30天;
c. 将上述培养好的发酵液过滤,滤除菌体,收集培养液;
d. 培养液用体积比为1:1的乙酸乙酯萃取3次,合并提取液,40℃水浴旋转蒸发浓缩得到总提取物;
e. 用乙酸乙酯溶解提取物,溶解物在硅胶柱中进行色谱分离,以石油醚-乙酸乙酯-甲醇梯度淋洗;
f. 收集由石油醚-乙酸乙酯(2:1)洗脱得到的组分,蒸除溶剂后,经高效液相色谱,以乙腈-水(60:40)纯化得到无色透明油状化合物Chondrosterin A。
化合物Chondrosterin A的试验数据:
元素分析(w %, C15H20O2):C 77.58,H 8.75,O 13.82,N 0.000;计算值:C, 77.55; H, 8.68; O, 13.77。[α]20 D = +112.5° (c = 0.024,MeOH)。UV nm (MeOH) λmax (log ε):249 (4.06)。IR υ/cm-1 (KBr):3433, 2951, 2867, 1693, 1622, 1462, 1377, 1312, 1259, 1211, 1156, 1123, 1037, 941, 864, 649, 570。LR EI MS: m/z 232, 217, 206, 199, 189, 176, 171, 165, 161, 147, 133, 122 (100%), 115, 111, 107, 91, 77, 69, 55。NMR实验数据如表1所示。
Chondrosterin A的结构与碳的位置编号
表1 Chondrosterin A的NMR数据(1H, 500MHz, 13C, 125MHz; CDCl3, TMS)
实施例2:化合物Chondrosterin A的抗肿瘤活性试验
a. 细胞株:肺癌(A549)、鼻咽癌(CNE2)和结肠癌(Lovo)3种肿瘤细胞。
b.取对数生长的上述肿瘤细胞株加入96孔板中,每孔200 μL含有3000-8000个细胞。
c.再加入药物,设8个药物浓度梯度,分别为0.06、0.025、0.098、0.391、1.563、6.25、25、100 μM,另设DMSO溶剂对照组。
d.每组设5个平行孔,置37℃培养72小时。实验终止前4小时加入10 μL 5 mg/mL MTT液,再培养4小时,弃去培养液,加入0.1 mL DMSO。
e.待结晶溶解后在酶联检测仪上双波长(570 nm,655 nm)检测每孔的OD值。按下列公式求出生长抑制率,再按BLISS法计算机程序求出半数抑制率〔IC50值〕,实验结果见表2。
细胞生长抑制率=(1-用药组平均OD值/对照组孔OD值)×100%
表2 化合物Chondrosterin A的细胞毒性试验结果
肺癌(A549) | 鼻咽癌(CNE2) | 结肠癌(Lovo) | |
半数抑制率IC50 (μM) | 2.452 | 4.963 | 5.49 |
Claims (4)
1.化合物Chondrosterin A,其结构式如式(Ⅰ)所示:
(Ⅰ)。
2.一种抗肿瘤药物组合物,其特征在于含有权利要求1所述Chondrosterin A。
3.权利要求1所述化合物Chondrosterin A在制备抗肿瘤药物中的应用。
4.如权利要求3所述的应用,其特征在于所述抗肿瘤药物的剂型为注射剂、 片剂、丸剂、胶囊剂、溶液、悬浮剂或乳剂。
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