CN104177240A - 分离自牛樟芝的化合物、萃取物及其用途 - Google Patents
分离自牛樟芝的化合物、萃取物及其用途 Download PDFInfo
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- CN104177240A CN104177240A CN201310204312.XA CN201310204312A CN104177240A CN 104177240 A CN104177240 A CN 104177240A CN 201310204312 A CN201310204312 A CN 201310204312A CN 104177240 A CN104177240 A CN 104177240A
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- antrodia camphorata
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- dichloromethane
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Abstract
本发明揭露一种分离自牛樟芝的化合物，以式I表示：
Description
技术领域
本发明是关于一种分离自牛樟芝的化合物、萃取物及其用途，特别是关于将该化合物及萃取物应用于抑制肿瘤生长的用途。
背景技术
牛樟芝(Antrodia camphorata)，又称樟芝、牛樟菇或红樟芝等，属于非褶菌目(Aphyllophorales)、多孔菌科(Polyporaceae)的多年生蕈菌类，为台湾特有种真菌，仅生长于台湾保育类树种-牛樟树（Cinnamoum kanehirai Hay）的中空腐朽心材内壁上。由于牛樟树分布数量极为稀少，加上人为的盗伐，使得寄生于其中方能生长的野生牛樟芝数量更形稀少，且由于其子实体生长相当缓慢，生长期亦仅在六月至十月之间，因此价格非常昂贵。
牛樟芝的子实体为多年生，无柄，呈木栓质至木质，其具强烈的樟树香气，且形态多变化，有板状、钟状、马蹄状或塔状。初生时为扁平型并呈鲜红色，之后其周边会呈现放射反卷状，并向四周扩展生长，颜色亦转变为淡红褐色或淡黄褐色，并有许多细孔，且其为牛樟芝的药用价值最丰富的部位。
在台湾民俗医学上，牛樟芝具有解毒、减轻腹泻症状、消炎、治疗肝脏相关疾病及抗癌等功用。牛樟芝如同一般食药用的蕈菇类，具有许多复杂的成分，已知的生理活性成分中，包括：三萜类化合物（triterpenoids）、多醣体（polysaccharides，如β-D-葡聚醣）、腺苷(adenosine）、维生素(如维生素B、烟碱酸)、蛋白质（含免疫球蛋白）、超氧歧化酵素（superoxide dismutase,SOD）、微量元素(如：钙、磷、锗)、核酸、固醇类以及血压稳定物质(如antodia acid)等，此些生理活性成分被认为具有抗肿瘤、增加免疫能力、抗过敏、抗病菌、抗高血压、降血糖及降胆固醇等多种功效。
牛樟芝众多成分中以三萜类化合物被研究的最多，三萜类化合物是由三十个碳元素结合成六角形或五角形天然化合物的总称，牛樟芝所具的苦味即主要来自三萜类此成分。1995年时，Cherng等人发现牛樟芝子实体萃取物中含有三种新的以麦角甾烷（ergostane）为骨架的三萜类化合物：antcin A、antcin B与antcin C（Cherng,I.H.,and Chiang,H.C.1995.Three new triterpenoids fromAntrodia cinnamomea.J.Nat.Prod.58:365-371）。Chen等人以乙醇萃取樟芝子实体后发现zhankuic acid A、zhankuic acid B及zhankuic acid C等三种三萜类化合物（Chen,C.H.,and Yang,S.W.1995.New steroid acids from Antrodiacinnamomea,－a fungus parasitic on Cinnamomum micranthum.J.Nat.Prod.58:1655-1661）。此外，Chiang等人于1995年也由子实体萃取物中发现另外三种分别为倍半萜内酯（sesquiterpene lactone）与两种双酚类衍生物的新三萜类化合物，此即antrocin,4,7-二甲氧基-5-甲基-1,3-苯并二氧环（4,7-dimethoxy-5-methy-1,3-benzodioxole）与2,2',5,5'-四甲氧基-3,4,3',4'-双-亚甲二氧基-6,6'-二甲基联苯（2,2',5,5'-teramethoxy-3,4,3',4'-bi-methylenedioxy-6,6'-dimethylbiphenyl）(Chiang,H.C.,Wu,D.P.,Cherng,I.W.,and Ueng,C.H.1995.A sesquiterpene lactone,phenyl and biphenyl compoundsfrom Antrodia cinnamomea.Phytochemistry.39:613-616)。到了1996年，Cherng等人以同样分析方法再度发现四种新的三萜类化合物：antcin E、antcin F、methyl antcinate G、methyl antcinate H（Cherng,I.H.,Wu,D.P.,and Chiang,H.C.1996.Triteroenoids from Antrodia cinnamomea.Phytochemistry.41:263-267）;而Yang等人则发现了二种以麦角甾烷为骨架的新化合物zhankuic acid D、zhankuic acid E，和三种以羊毛甾烷（lanostane）为骨架的新化合物：15α–乙酰-去氢硫色多孔菌酸（15α-acetyl-dehydrosulphurenic acid）、去氢齿孔酸（dehydroeburicoic acid）与去水硫色多孔菌酸（dehydrasulphurenic acid）（Yang,S.W.,Shen,Y.C.,and Chen,C.H.1996.Steroids and triterpenoids of Antrodiacinnamomea－a fungus parasitic on Cinnamomum micranthum.Phytochemistry.41:1389-1392）。其中，某些成分陆续被发现可能对于AMPK及TOR讯息传递路径扮演重要角色，透过AMPK的活化及对mTOR转译路径的抑制，达到对癌细胞周期中G1期的良好控制，完全阻断癌细胞周期的进展，造成一连串的癌细胞雕亡。
虽然由目前诸多的实验可得知牛樟芝萃取物具有前述功效，且其所含成分亦陆续被分析出，但牛樟芝萃取物中是否仍有其他具抗癌活性或其他医疗用途的化合物未被找出来，仍有待进一步实验研究来厘清。
发明内容
据此，本发明之一目的在提供一种分离自牛樟芝的化合物，以式I表示：
其中R1为氢或乙酰基。
较佳地，该化合物的R1为氢，以式(II)表示：
较佳地，其中该化合物的R1为乙酰基，以式(III)表示：
本发明的又一目的在于提供一种将上述化合物用于制备抑制肿瘤生长药物的用途，其中该肿瘤为肺腺癌、结肠癌、前列腺癌、及肝癌其中之一。
本发明的另一目的在于提供一种萃取自牛樟芝的萃取物，该萃取物以下列步骤进行萃取而得：取牛樟芝菌丝体、子实体或二者的混合物以10倍量的酒精抽取2次后合并浓缩得到一粗抽物，将该粗抽物以二氯甲烷/水(1:1)进行分配萃取法3次，以分为一二氯甲烷层及一水层，取该二氯甲烷层以硅胶柱层析法经过正己烷/二氯甲烷(1:4)、二氯甲烷、甲醇/二氯甲烷(5:95)的溶媒分离得到该萃取物。
附图说明
图1-图3为本发明实施例提供的Antrocamol LT1的结构鉴定；
图4-图6为本发明实施例提供的Antrocamol LT2的结构鉴定。
具体实施方式
取牛樟芝（Antrodia camphorata）菌丝体、子实体或二者的混合物(1.0kg)以10倍量的酒精抽取2次后，合并浓缩可得粗抽物约230g(LT-E)，粗抽物以二氯甲烷/水(1:1)进行分配萃取法3次，分为二氯甲烷层约102.6g(LT-E-D)及水层约127.4g(LT-E-W)，取二氯甲烷层6.0g以硅胶柱层析法经过正己烷/二氯甲烷(1:4)、二氯甲烷、甲醇/二氯甲烷(5:95)的溶媒分离，分为ANCA-E-D-1、ANCA-E-D-2、ANCA-E-D-3、ANCA-E-D-4等四层。
牛樟芝萃取物的抗癌活性
分别针对A549细胞株(肺腺癌)、CT26细胞株(结肠癌)、DU145细胞株(前列腺癌)、HepG2细胞株(肝癌)、MDCK细胞株(肾癌)、PC3细胞株(前列腺癌)进行细胞存活检测（MTT cell viability assay），结果参阅如下列表1～6。
将上述细胞株分别于适当的培养液中培养24小时。将增生后的细胞以PBS清洗一次，并以1倍的胰蛋白酶-EDTA处理细胞，随后于1,200rpm下离心5分钟，将细胞沈淀并丢弃上清液。之后加入10ml的新培养液，轻微摇晃使细胞再次悬浮，再将细胞分置于96孔微量盘内。测试时，分别于每一孔内加入0.01～200μg/ml的牛樟芝萃取物，于37℃、5%CO2下培养48小时。其后，于避光的环境下于每一孔内加入2.5mg/ml的MTT，反应4小时后再于每一孔内加入100μl的lysis buffer终止反应。最后以酵素免疫分析仪在570nm吸光波长下测定其吸光值，藉以计算细胞的存活率，并推算出其生长半抑制率所需浓度(即IC50值)所有实验资料均以平均值±标准误差表示。实验资料以配对t考验(paired-t test)进行统计分析。以p值小于0.05视为具有统计学上差异。
表1：A549细胞株(肺腺癌)
表3：DU145细胞株(前列腺癌)
表4：HepG2细胞株(肝癌)
表5：MDCK细胞株(肾癌)
表6：PC3细胞株(前列腺癌)
在表1～6中，0～25%细胞存活:+/-，25～50%细胞存活:+，50～75%细胞存活:++，75～100%细胞存活:+++，>100%细胞存活:++++。溶剂为DMSO，其IC50为2.34%，意谓当药物稀释至DMSO含量为2.34%时，会造成细胞50%死亡，此处当药物稀释至100μg/ml的DMSO含量为0.5%。ANCA-E、ANCA-E-D、ANCA-E-W、ANCA-E-D-1、ANCA-E-D-2、ANCA-E-D-3、ANCA-E-D-4、LT-80及LT-C80分别为不同的牛樟芝萃取物。
依据上列各表结果显示，其中的ANCA-E-D-2、ANCA-E-D-3、ANCA-E-D-4对于各种不同的癌细胞生长具有较佳的抑制效果。例如，其中的ANCA-E-D-2及ANCA-E-D-3对于A549细胞株(肺腺癌)、CT26细胞株(结肠癌)、DU145细胞株(前列腺癌)、HepG2细胞株(肝癌)、MDCK细胞株(肾癌)、PC3细胞株(前列腺癌)，相比于相对其他组别而言，具有相对较佳的抑制效果。而ANCA-E-D-4虽然略低于ANCA-E-D-2及ANCA-E-D-3，但对于各种肿瘤细胞亦有一定的抑制效果。据此，可将该等萃取物用于制备抑制肿瘤生长药物的用途，包括肺腺癌、结肠癌、前列腺癌、及肝癌其中之一，并可进一步纯化其中的有效单一成分。
自牛樟芝萃取制备Antrocamol LT1及Antrocamol LT2
依据上述结果，将ANCA-E-D-2及ANCA-E-D-3进一步进行纯化，将ANCA-E-D-3层经制备型逆相柱层析法(C-18逆相层析管柱)以80%MeOH/H20在18.75分钟附近可得一新化合物Antrocamol LT1约150mg，而LT-E-D-2层经制备型逆相柱层析法(C-18逆相层析管柱)以80%MeOH/H20在25.10分钟附近可得另一新化合物Antrocamol LT2约170mg。Antrocamol LT1的结构鉴定结果如下：
Antrocamol LT1为无色的液体产物，经分析该化合物的分子式为C24H38O5，分子量为406，完整中文英名称为4-羟基-2,3-二甲氧基-6-甲基-5-（9-羟基-3,7,11-三甲基-2,6,10-十二碳三烯）-2-环己烯酮、4-hydroxy-5-[9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trienyl]-2,3-dimethoxy-6-methyl-cyclohex-2-enone。
LT1结构鉴定资料(参阅附图1-图3)：1H-NMR(400MHz,CDCl3):□1.12(3H,d,J=7.2Hz,),1.61(3H,s),1.64(3H,s),1.66(3H,s),1.68(3H,s),1.72(1H,m),1.98–2.30(8H),2.51(1H,dq,J=11.6,7.2Hz),3.62(3H,s),4.02(3H,s),4.33(1H,d,J=2.8Hz),4.35(1H,dt,J=9.2,4.0Hz),5.09(1H,d,J=8.4Hz),5.14(1H,t,J=7.2Hz),5.15(1H,t,J=7.2Hz);13C-NMR(100MHz,CDCl3):□12.17(q),15.95(q),16.19(q),18.13(q),25.72(q),25.93(t),26.78(t),39.41(t),39.98(d),43.29(d),47.94(t),58.81(q),60.48(q),65.35(d),67.24(d),121.64(d),127.64(d),128.42(d),132.03(s),134.99(s),135.97(s),137.42(s),160.82(s),197.15(s)。
Antrocamol LT2(参阅附图4-图6):为无色的液体产物，经分析该化合物的分子式为C26H40O6;分子量为448，完整中文英名称为4-乙酰羧基-2,3-二甲氧基-6-甲基-5-（9-羟基-3,7,11-三甲基-2,6,10-十二碳三烯）-2-环己烯酮、4-acetoxy-5-[9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trienyl]-2,3-dimethoxy-6-methyl-cyclohex-2-enone。
LT2结构鉴定资料：1H-NMR(400MHz,CDCl3):□1.18(3H,d,J=7.2Hz,),1.54(3H,s),1.64(3H,s),1.67(3H,s),1.69(3H,s),1.72(1H,m),1.80–2.40(8H),2.50(1H,dq,J=11.6,7.2Hz),3.65(3H,s),3.98(3H,s),4.36(1H,m),5.10(1H,t,J=6.8Hz),5.12(1H,d,J=8.0Hz),5.20(1H,t,J=6.4Hz),5.72(1H,t,J=3.2Hz);13C-NMR(100MHz,CDCl3):□12.80(q),15.96(q),16.09(q),18.14(q),20.93(q),25.72(q),26.19(t),26.76(t),39.47(t),41.25(d),42.98(d),48.12(t),59.65(q),60.67(q),65.53(d),68.98(d),120.74(d),127.42(d),128.25(d),131.74(s),134.70(s),137.31(s),137.56(s),158.21(s),169.73(s),196.84(s)。
依前述实验方法进行MTT assay(在此不再重复)，利用分析仪在570nm吸光波长下测定其吸光值，藉以计算细胞的存活率，并推算出其生长半抑制率所需浓度(即IC50值)，测试Antrocamol LT1及Antrocamol LT2的抗癌活性，并与ANCA-E、ANCA-E-D及ANCA-E-D-3作比较。所有实验资料均以平均值±标准误差表示。实验资料以配对t考验(paired-t test)进行统计分析。以p值小于0.05视为具有统计学上差异。并将其半抑制浓度(IC50)整理为下表(表7)。
表7
IC50是指被抑制一半时抑制剂的浓度。IC50值通常用来衡量药物诱导细胞雕亡的能力，即诱导能力越强，数值越低。由表中结果可看出，新化合物Antrocamol LT1及Antrocamol LT2与ANCA-E、ANCA-E-D及ANCA-E-D-3等萃取物，均具有颇佳的抗癌活性。据此，可将该等化合物用于制备抑制肿瘤生长药物的用途，包括肺腺癌、结肠癌、前列腺癌、及肝癌其中之一，并可进一步发展为抗癌药物。
本发明所提供的分离自牛樟芝的化合物、萃取物及其用途确具产业上的利用价值，惟以上的叙述仅为本发明的较佳实施例说明，凡精于此项技艺者当可依据上述的说明而作其它种种的改良，惟这些改变仍属于本发明的精神及以下所界定的专利范围中。
Claims (6)
1.一种分离自牛樟芝的化合物，以式I表示：
其中R1为氢或乙酰基。
2.如申请专利范围第1项所述的化合物，其中该化合物的R1为氢，以式(II)表示：
3.如申请专利范围第1项所述的化合物，其中该化合物的R1为乙酰基，以式(III)表示：
4.一种将如申请专利范围第1项所述的化合物用于制备抑制肿瘤生长药物的用途，其中该肿瘤为肺腺癌、结肠癌、前列腺癌、及肝癌其中之一。
5.一种萃取自牛樟芝的萃取物，该萃取物以下列步骤进行萃取而得：取牛樟芝菌丝体、子实体或二者的混合物以10倍量的酒精抽取2次后合并浓缩得到一粗抽物，将该粗抽物以二氯甲烷/水(1:1)进行分配萃取法3次，以分为一二氯甲烷层及一水层，取该二氯甲烷层以硅胶柱层析法经过正己烷/二氯甲烷(1:4)、二氯甲烷、甲醇/二氯甲烷(5:95)的溶媒分离得到该萃取物。
6.一种将如申请专利范围第5项所述的萃取物用于制备抑制肿瘤生长药物的用途，其中该肿瘤为肺腺癌、结肠癌、前列腺癌、及肝癌其中之一。
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| CN107296805A (zh) * | 2016-04-14 | 2017-10-27 | 郭盈妤 | 牛樟芝化合物及其萃取物用于制备治疗及预防神经退行性疾病的药物的用途 |
| CN107397764A (zh) * | 2016-05-20 | 2017-11-28 | 台湾原生药用植物股份有限公司 | 用于辅助治疗癌症的医药组合物 |
| TWI648257B (zh) * | 2014-12-30 | 2019-01-21 | 合一生技股份有限公司 | 牛樟芝化合物、製備方法及其用途 |
| CN110337991A (zh) * | 2019-06-19 | 2019-10-18 | 三生源生物科技（天津）有限公司 | 一种基于牛樟芝提取物的肿瘤细胞抑制剂的制备及应用 |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI648257B (zh) * | 2014-12-30 | 2019-01-21 | 合一生技股份有限公司 | 牛樟芝化合物、製備方法及其用途 |
| CN105732381B (zh) * | 2014-12-30 | 2021-07-20 | 合一生技股份有限公司 | 牛樟芝提取物及其制备方法和应用 |
| CN107296805A (zh) * | 2016-04-14 | 2017-10-27 | 郭盈妤 | 牛樟芝化合物及其萃取物用于制备治疗及预防神经退行性疾病的药物的用途 |
| CN107397764A (zh) * | 2016-05-20 | 2017-11-28 | 台湾原生药用植物股份有限公司 | 用于辅助治疗癌症的医药组合物 |
| CN110337991A (zh) * | 2019-06-19 | 2019-10-18 | 三生源生物科技（天津）有限公司 | 一种基于牛樟芝提取物的肿瘤细胞抑制剂的制备及应用 |
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