CN112294781A - 丁内酯代谢酮i在制备抗肿瘤药物中的应用 - Google Patents
丁内酯代谢酮i在制备抗肿瘤药物中的应用 Download PDFInfo
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Abstract
本发明属于医药技术领域,具体为丁内酯代谢酮I在制备抗肿瘤药物中的应用。该化合物具有显著抗肿瘤的作用;且制备该化合物的原料资源丰富,提取分离方法简单,生产成本低。
Description
技术领域
本发明属于医药技术领域,具体为丁内酯代谢酮I在制备抗肿瘤药物中的应用。
背景技术
丁内酯-I(Butyrolactone I)是曲霉属真菌土曲霉Aspergillus terreus的主要活性次级代谢产物,1977年Kiriyama首先从真菌Aspergillus terreus var.africanusIFO 8835中分离得到,因其结构中具有五元不饱和内酯环,故将其命名为butyrolactoneI。已有文献报道butyrolactone I具有明确的选择性细胞周期依赖性激酶(CDK)抑制活性,其对cdc2和CDK2的体外抑制作用机理也被阐明,是潜在的抗肿瘤候选药物。butyrolactoneI及其衍生物也被证明是一类多效的天然活性物质,具有广泛的药理活性。
我们通过给大鼠口服butyrolactone I后,收集其尿液和粪便,利用各种化学及色谱手段,分离和鉴定butyrolactone I在体内的代谢产物,推测butyrolactone I在体内的转化过程,同时测定这些代谢产物的药理活性,其中从代谢产物中分离得到的丁内酯代谢酮I具备较好药理活性,前期药效研究发现该化合物具有抗抗氧化(CN201910558609.3,一种二苯酮类化合物及其制备方法和应用),在此基础上我们对丁内酯代谢酮I在抗肿瘤方面进行研究,同样体现出显著的抗肿瘤活性。
发明内容
本发明的目的在于提供丁内酯代谢酮I在制备抗肿瘤药物中的应用。
丁内酯代谢酮I在制备抗肿瘤药物中的应用,丁内酯代谢酮I的结构式如式(I)所示:
丁内酯代谢酮I的制备方法如下:
(1)提取:Wistar大鼠40只,雌雄各半,200±20g,动物适应性饲养1周后,灌胃给药40mg·kg-1,分别置于大鼠代谢笼中,1只/笼,收集24h的粪便。实验期间以淀粉馒头喂食大鼠,饮用水喂以4%生理盐水,1%葡萄糖溶液。每天早上收集24h的粪便保存于-80℃冰箱。累积灌胃给药4周,每天给药一次。从粪便的乙酸乙酯萃取物中共得到浸膏8g。
(2)分离:将上述浸膏应用硅胶柱层析,以体积比为100:0-100:50的二氯甲烷-甲醇***梯度洗脱,薄层层析检测,收集含有新化合物的流分,再经体积比为100:0-0:100的石油醚-乙酸乙酯***梯度洗脱,最后经C18反相柱层析制备液相制备,以体积比为68:32的甲醇-水进行洗脱,得到新化合物丁内酯代谢酮I。
丁内酯代谢酮I,无色油状物(甲醇),UV(MeOH)λmax在209nm处。HR-ESI-MS在m/z333.1447处给出[M+Na]+峰,推测分子式为C20H22O3。1H-NMR和13C-NMR数据见表1。
表1丁内酯代谢酮I1H和13C核磁共振数据
丁内酯代谢酮I结构解析:
如图1-5所示,丁内酯代谢酮I的1H NMR、13C NMR、2D-NMR(HSQC、HMBC)谱,以及HR-ESI-MS谱得知化合物结构。具体地说:
无色油状物(甲醇),UV(MeOH)λmax:209nm。红外光谱(IR)提示结构中存在羟基(3431cm-1)、双键(1638cm-1)等官能团。HR-ESI-MS在m/z 333.1447处给出[M+Na]+峰(calcd.333.1467),确定其分子式为C20H22O3。
1H-NMR(400MHz,DMSO-d6)谱中芳香区给出一组AA′BB′偶合***的质子信号δH6.91(2H,d,J=8.4Hz,H-2′,6′)、6.68(2H,d,J=8.4Hz,H-3′,5′),推测存在对位取代苯的结构;δH 6.76(1H,dd,J=8.0,2.0Hz,H-6″)、6.75(1H,d,J=2.0Hz,H-2″)、6.70(1H,d,J=8.0Hz,H-5″),提示存在一个1,3,4-三取代苯环结构。由两个甲基信号δH 1.65(3H,s,H-10″)和1.67(3H,s,H-11″),一个双键氢信号δH5.23(1H,t,J=7.2Hz,H-8″)及与之相偶合的氢信号δH 3.16(2H,d,J=7.2Hz,H-7″),推测存在一个异戊烯基片段。
13C-NMR(100MHz,DMSO-d6)谱给出14个芳香或双键碳信号,符合以上推测的两个苯环片段和异戊烯基片段的碳的个数,与butyrolactone I相比,化合物丁内酯代谢酮I减少了-COOCH3和内酯结构片段的碳信号,出现了酮羰基碳信号δC 206.9(C-2)和两个亚甲基碳信号δC 47.8(C-1)、48.0(C-3)。以上信息推测内酯环开环,发生脱羧重排。
HSQC谱给出结构中所有氢碳直接相连的信息,如表1所示。
HMBC谱中,质子信号δH 3.61(2H,s,H-1)与碳信号δC 206.9(C-2)、125.2(C-1')、130.9(C-2')相关,δH 3.59(2H,s,H-3)与碳信号δC 206.9(C-2)、128.2(C-6”)和C-2′(δc130.9)相关H-7″(δH 3.16)与碳信号C-4″(δc 154.0),C-3″(δc 127.8)和C-8″(δc 123.3)相关,H-10″(δH 1.67)与C-9″(δc 131.5)和C-8″(δc 123.3)相关,H-11″(δH 1.65)与C-9″(δc 131.5)和C-8″(δc 123.3)相关,活泼氢信号4′-OH(δH 9.21)与C-4′(δc 156.5)和C-5′(δc 115.6)相关,4″-OH(δH 9.19)与C-4″(δc 154.0)和C-5″(δc 115.1)相关。确定化合物的结构为1-(4-hydroxy-3-(3-methylbut-2-enyl)phenyl)-3-(4-hydroxyphenyl)propan-2-one。
附图说明
图1丁内酯代谢酮I的1H NMR谱;
图2丁内酯代谢酮I的13C NMR谱;
图3丁内酯代谢酮I的HSQC谱;
图4丁内酯代谢酮I的HMBC谱;
图5丁内酯代谢酮I的HR-ESI-MS谱。
具体实施方式
下面通过实施例进一步描述本发明,使本专业技术更全面地理解本发明,但不以任何方式限制本发明。
实施例1
Wistar大鼠40只,雌雄各半,200±20g,动物适应性饲养1周后,灌胃给药40mg·kg-1,分别置于大鼠代谢笼中,1只/笼,收集24h的尿液与粪便。实验期间以淀粉馒头喂食大鼠,饮用水喂以4%生理盐水,1%葡萄糖溶液。每天早上收集24h的粪便保存于-80℃冰箱。累积灌胃给药4周,每天给药一次,共给药约14g。从粪便的乙酸乙酯萃取物中共得到浸膏8g。将浸膏用硅胶柱层析,以体积比为100:0-100:50的二氯甲烷-甲醇***梯度洗脱,薄层层析检测,收集含有新化合物的流分,再经体积比为100:0-0:100的石油醚-乙酸乙酯***梯度洗脱,最后经C18反相柱层析制备液相制备,以体积比为68:32的甲醇-水进行洗脱,流速3ml/min,检测波长210nm,得到丁内酯代谢酮I 80mg。
实施例2
丁内酯代谢酮I体外抗肿瘤试验
采用MTT法测定细胞的增殖活性。分别取对数生长期的肿瘤细胞包括HepG-2(人肝癌细胞),A549(人肺癌细胞),SGC-7901(人胃癌细胞),MCF-7(人乳腺癌细胞),LOVO(人肠癌细胞)进行消化,得到细胞悬液后计数,按照计数结果将细胞浓度调整为大约1×105个/mL,以每孔100μL分别接种于96孔板中,在5%CO2,37℃条件下的细胞培养箱中培养24h后,将上清液吸弃。随后加入以0.8%DMSO溶解且培养基稀释所得的不同浓度的阳性对照药(羟基喜树碱)以及丁内酯代谢酮I(设置5个浓度,分别为5,10,20,40,80μg/mL)加入到96孔板中,空白对照组加等体积培养基,每孔100μL,每个浓度梯度设置5个复孔,于5%CO2,37℃细胞培养箱中培养24h。最后,将PBS(磷酸缓冲液)稀释好的MTT(5mg/mL)20μL加入96孔板,继续培养4h,最后移除上清液,每孔加150μL DMSO,震荡10分钟,用酶标仪在490nm波长下测定其吸光度OD值,计算样品的半数抑制浓度(IC50)。
按以下公式计算药物对肿瘤细胞体外增殖的抑制率(Inhibition Rate,IR%)
IR%=(1-ODsample/ODcontrol)×100%
用ICP1.0.0软件计算药物的半数抑制浓度(IC50)。
实验结果(见表2)表明:丁内酯代谢酮I对以上各种肿瘤细胞均有不同程度的抑制作用。抑制强度由强到弱依次为SGC-7901、HepG-2、MCF-7、A549、LOVO细胞。
尽管本发明的实施方案已公开如上,但其并不仅仅限于说明书和实施方式中所列运用,它完全可以被适用于各种适合本发明的领域,对于熟悉本领域的人员而言,可容易地实现另外的修改,因此在不背离权利要求及等同范围所限定的一般概念下,本发明并不限于特定的细节。
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CN115232096A (zh) * | 2022-06-15 | 2022-10-25 | 福建卫生职业技术学院 | 源于细曲霉的内酯类化合物及其制备方法和在抗人肝癌药物中的应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110478338A (zh) * | 2019-09-24 | 2019-11-22 | 哈尔滨商业大学 | 丁内酯代谢酮i在降低血脂中的应用 |
CN110585181A (zh) * | 2019-10-15 | 2019-12-20 | 哈尔滨商业大学 | 丁内酯代谢酮i在抗炎中的应用 |
-
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110478338A (zh) * | 2019-09-24 | 2019-11-22 | 哈尔滨商业大学 | 丁内酯代谢酮i在降低血脂中的应用 |
CN110585181A (zh) * | 2019-10-15 | 2019-12-20 | 哈尔滨商业大学 | 丁内酯代谢酮i在抗炎中的应用 |
Non-Patent Citations (4)
Title |
---|
DA SILVA, IGOR PEREIRA ET AL.: "Bioactive compounds of Aspergillus terreus-F7, an endophytic fungus from Hyptis suaveolens (L.) Poit", 《WORLD JOURNAL OF MICROBIOLOGY & BIOTECHNOLOGY》 * |
LIU, B ET AL.: "A new benzophenone with biological activities from metabolites of butyrolactone I in rat faeces", 《NATURAL PRODUCT RESEARCH》 * |
NISHIO, K ET AL.: "Antitumor effects of butyrolactone I, a selective cdc2 kinase inhibitor, on human lung cancer cell lines", 《ANTICANCER RESEARCH》 * |
SHEN, YI ET AL.: "Butyrolactone and Cycloheptanetrione from Mangrove-Associated Fungus Aspergillus terreus", 《CHEMICAL & PHARMACEUTICAL BULLETIN》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115232096A (zh) * | 2022-06-15 | 2022-10-25 | 福建卫生职业技术学院 | 源于细曲霉的内酯类化合物及其制备方法和在抗人肝癌药物中的应用 |
CN115232096B (zh) * | 2022-06-15 | 2023-05-05 | 福建卫生职业技术学院 | 源于细曲霉的内酯类化合物及其制备方法和在抗人肝癌药物中的应用 |
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