藤黄和双籽藤黄化学成分及抗肿瘤活性研究
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摘要
藤黄为藤黄科藤黄属植物藤黄(Garcinia hanburyi Hook.f.)的胶质树脂。味酸涩,有毒,具消肿化毒之功效。藤黄始载于《海药本草》,生于热带地区,广东和广西有少量栽培,主要分布于印度和泰国。双籽藤黄(Garcinia tetralata C.Y.Wu)主要分布于我国云南省南部和西南部地区,有关双籽藤黄的化学成分和药理作用研究国内外尚未见报道。本文在综述了藤黄属植物化学成分和药理活性研究的基础上,对藤黄树脂和双籽藤黄的茎皮进行了系统的化学成分研究,并对从藤黄中分离得到的部分单体化合物进行了体外抗肿瘤活性研究。
利用多种色谱分离技术,从藤黄树脂的氯仿提取物中,共分离得到17个化合物。通过理化常数测定、波谱分析等方法,鉴定了其结构。它们分别是:2α-羟基-3β-乙酰氧基-羽扇豆-20(29)-烯-28酸(1),3-O-(4′-乙酰氧基)-α-L-吡喃阿拉伯糖-齐墩果酸(2),藤黄醛(3),forbesione(4),hanburin(5),desoxygambogenin(6),isogambogenin(7),desoxymorellin(8),isomorellin(9),β-morellic acid(10),α-morellic acid(11),gambogellic acid(12),藤黄酸(13),30-羟基藤黄酸(14),白桦脂酸(15),messagenic acid(16)和β-谷甾醇(17)。其中化合物1、2、3为未见文献报道的新化合物,化合物16为首次从该属植物中分离得到,化合物15～17为首次从该种植物中分离得到。
利用多种色谱分离技术,从双籽藤黄茎皮的95%乙醇提取物中,共分离得到22个化合物。通过理化常数测定、波谱分析等方法,鉴定了其中20个化合物的结构。它们分别是:3β-羟基-18β,19β-环氧-羽扇豆烷(18),tetralataxanthone(19),2-(1′,1′-dimethylprop-2′-enyl)-1,4,5-trihydroxy-9H-xanthen-9-one(20),6-desoxyjacareubin(21),toxyloxanthone A(22),globuxanthone(23),1,7-二羟基(口山)酮(24),subelliptenone H(25),6-deoxyjacreubin(26),buchanaxanthone(27),garciniaxanthone H(28),6,11-dihydroxy-2,2-dimethyl-pyrano[3,2-c]xanthen-7(2H)-one(29),subelliptenone G(30),1,4-二羟基-5,6-二甲氧基(口山)酮(31),1,2,5-三羟基(口山)酮(32),2,6-二羟基-1,5-二甲氧基(口山)酮(33),morolic acid acetate(34),苔色酸甲酯(35),montroumarin(36)和β-谷甾醇(37)。其中化合物18,19为未见文献报道的新化合物,化合物34～36为首次从该属植物中分离得到,化合物20～37为首次从该种植物中分离得到,
对从藤黄树脂中分离得到的部分单体化合物进行了体外抗肿瘤活性研究。结果显示:笼状多异戊烯基(口山)酮类化合物对鼠源性白血病细胞P388和P388/ADR具有一定的生长抑制作用。其中,化合物14对P388细胞的抑制活性最强,而化合物5最弱;化合物12对P388/ADR细胞的抑制活性最强,而化合物3最弱。综合这两种细胞测试结果,可以看出化合物12和13在所有分离得到的笼状多异戊烯基(口山)酮类化合物中活性是最强的。初步的构效关系研究表明,此类结构中吡喃环的存在可以增加化合物对P388细胞的生长抑制作用(3,12～14),若该吡喃环的2位连有异戊烯基,则活性更强;对于母核上无吡喃环取代的笼状多异戊烯基(口山)酮类化合物,5位香叶基(C_(10))的存在可以增强化合物对P388细胞的生长抑制活性(6～7)。通过对人类白血病细胞HL-60、NB4、U937、K562进行体外测试,发现从藤黄中分离得到的两个新三萜类化合物1和2在不同浓度下都具有细胞生长抑制作用,其中,化合物2对上述细胞的抑制作用强于化合物1。为了确定化合物1和2对HL-60细胞生长抑制作用是否是由于细胞凋亡所引起,通过吖啶橙(AO)和溴化乙啶(EB)染色后的形态计数以及流式检测(FACS),我们对两个新三萜类化合物的凋亡诱导作用进行了考察,结果表明化合物1和2对HL-60细胞均能诱导产生凋亡作用。
通过对藤黄中笼状多异戊烯基(口山)酮类化合物的研究,并结合文献检索,总结了该类化合物的结构和波谱学特征。
Garcinia hanburyi Hook.f.,a plant belonging to the family of Guttiferae,is distributed throughout Thailand,Cambodia,and the southern part of China.Its resin is used as a dye and as a folk medicine for purgative and for the treatment of infected wounds,and has been developed as an anti-tumor drug in China.G.tetralata is distributed in the Yunnan province of China.No previous phytochemical investigations were focused on G.tetralata.Based on the review on the chemical constituents and pharmacological research of Garcinia,the chemical constituents of Garcinia hanburyi and G.tetralata and their antitumor activities were researched.
By means of many different chromatographic methods such as silica gel, Sephadex LH-20,ODS column chromatography,and preparative TLC,17 compounds were isolated from the resin of Garcinia hanburyi.By physico-chemical data and spectral methods,these compounds were identified as 2α-hydroxy-3β-O-acetyl-lup-20(29)-en-28-oic acid(1),3-O-(4'-O-acetyl)-α-L-arabinopyranosyl-oleanolic acid(2),gambogic aldehyde(3),forbesione(4),hanburin (5),desoxygambogenin(6),isogambogenin(7),desoxymorellin(8),isomorellin(9),β-morellic acid(10),α-morellic acid(11),gambogellic acid(12),gambogic acid(13), 30-hydroxygambogic acid(14),betulinic acid(15),messagenic acid(16),andβ-sitosterol(17).Among them,compounds 1～3 are determined as new compounds, compound 16 is obtained from genus Garcinia for the first time.
By means of many different chromatographic methods,22 compounds were isolated from the barks of Garcinia tetralata.Twenty of them were characterized by physico-chemical data and spectral methods,and they were 3β-hydroxy-18β, 19β-epoxy-lupane(18),tetralataxanthone(19),2-(1',1'-dimethylprop-2'-enyl)-1,4, 5-trihydroxy-9H-xanthen-9-one(20),6-desoxyjacareubin(21),toxyloxanthone A(22), globuxanthone(23),1,7-dihydroxyxanthone(24),subelliptenone H(25), 6-deoxyjacreubin(26),buchanaxanthone(27),garciniaxanthone H(28),6, 11-dihydroxy-2,2-dimethyl-pyrano[3,2-c]xanthen-7(2H)-one(29),subelliptenone G (30),1,4-dihydroxy-5,6-dimethoxyxanthone(31),1,2,5-trihydroxyxanthone(32),2, 6-dihydroxy-1,5-dimethoxyxanthone(33),morolic acid acetate(34),methyl orsellinate(35),montroumarin(36),andβ-sitosterol(37).Among them,compounds 18 and 19 are determined as new compounds,compounds 34～36 are isolated from genus Garcinia for the first time.
The antitumor activities of the two new triterpenoids and twelve caged polyprenylated xanthones isolated from the resin of Garcinia hanburyi were tested.It was found that all caged polyprenylated xanthones inhibited cell growth with different activities against P388 and P388/ADR cells,in which compounds 12 and 13 were the most potent.The structure-activity relationship of caged polyprenylated xanthones was discussed.The results showed that the presence of pyran-ring in the molecular might have an important role in inhibiting P388 cell line.If the pyran-ring had 2-isoprenyl group,the activity would be enhanced.To the xanthones which had not a pyran-ring(6～7),those with the substituent of 5-geranyl group could have better activity in inhibiting P388 cell line.By testing in human leukemia HL-60,NB4,U937, K562 cells,it was found that two new triterpenes were effective cell growth inhibitors. Compound 2 showed more potent activity than compound 1.The apoptotic effects in HL-60 cells were also examined by morphological observation after AO and EB staining and FACS analysis.The two new triterpenoids induced HL-60 cells to undergo apoptosis in a dose- and time-dependent manner.
On the basis of the research on caged polyprenylated xanthones isolated from the resin of Garcinia hanburyi and the related literatures,an overview on the spectral and structural characteristics of caged polyprenylated xanthones was taken.
利用多种色谱分离技术,从藤黄树脂的氯仿提取物中,共分离得到17个化合物。通过理化常数测定、波谱分析等方法,鉴定了其结构。它们分别是:2α-羟基-3β-乙酰氧基-羽扇豆-20(29)-烯-28酸(1),3-O-(4′-乙酰氧基)-α-L-吡喃阿拉伯糖-齐墩果酸(2),藤黄醛(3),forbesione(4),hanburin(5),desoxygambogenin(6),isogambogenin(7),desoxymorellin(8),isomorellin(9),β-morellic acid(10),α-morellic acid(11),gambogellic acid(12),藤黄酸(13),30-羟基藤黄酸(14),白桦脂酸(15),messagenic acid(16)和β-谷甾醇(17)。其中化合物1、2、3为未见文献报道的新化合物,化合物16为首次从该属植物中分离得到,化合物15～17为首次从该种植物中分离得到。
利用多种色谱分离技术,从双籽藤黄茎皮的95%乙醇提取物中,共分离得到22个化合物。通过理化常数测定、波谱分析等方法,鉴定了其中20个化合物的结构。它们分别是:3β-羟基-18β,19β-环氧-羽扇豆烷(18),tetralataxanthone(19),2-(1′,1′-dimethylprop-2′-enyl)-1,4,5-trihydroxy-9H-xanthen-9-one(20),6-desoxyjacareubin(21),toxyloxanthone A(22),globuxanthone(23),1,7-二羟基(口山)酮(24),subelliptenone H(25),6-deoxyjacreubin(26),buchanaxanthone(27),garciniaxanthone H(28),6,11-dihydroxy-2,2-dimethyl-pyrano[3,2-c]xanthen-7(2H)-one(29),subelliptenone G(30),1,4-二羟基-5,6-二甲氧基(口山)酮(31),1,2,5-三羟基(口山)酮(32),2,6-二羟基-1,5-二甲氧基(口山)酮(33),morolic acid acetate(34),苔色酸甲酯(35),montroumarin(36)和β-谷甾醇(37)。其中化合物18,19为未见文献报道的新化合物,化合物34～36为首次从该属植物中分离得到,化合物20～37为首次从该种植物中分离得到,
对从藤黄树脂中分离得到的部分单体化合物进行了体外抗肿瘤活性研究。结果显示:笼状多异戊烯基(口山)酮类化合物对鼠源性白血病细胞P388和P388/ADR具有一定的生长抑制作用。其中,化合物14对P388细胞的抑制活性最强,而化合物5最弱;化合物12对P388/ADR细胞的抑制活性最强,而化合物3最弱。综合这两种细胞测试结果,可以看出化合物12和13在所有分离得到的笼状多异戊烯基(口山)酮类化合物中活性是最强的。初步的构效关系研究表明,此类结构中吡喃环的存在可以增加化合物对P388细胞的生长抑制作用(3,12～14),若该吡喃环的2位连有异戊烯基,则活性更强;对于母核上无吡喃环取代的笼状多异戊烯基(口山)酮类化合物,5位香叶基(C_(10))的存在可以增强化合物对P388细胞的生长抑制活性(6～7)。通过对人类白血病细胞HL-60、NB4、U937、K562进行体外测试,发现从藤黄中分离得到的两个新三萜类化合物1和2在不同浓度下都具有细胞生长抑制作用,其中,化合物2对上述细胞的抑制作用强于化合物1。为了确定化合物1和2对HL-60细胞生长抑制作用是否是由于细胞凋亡所引起,通过吖啶橙(AO)和溴化乙啶(EB)染色后的形态计数以及流式检测(FACS),我们对两个新三萜类化合物的凋亡诱导作用进行了考察,结果表明化合物1和2对HL-60细胞均能诱导产生凋亡作用。
通过对藤黄中笼状多异戊烯基(口山)酮类化合物的研究,并结合文献检索,总结了该类化合物的结构和波谱学特征。
Garcinia hanburyi Hook.f.,a plant belonging to the family of Guttiferae,is distributed throughout Thailand,Cambodia,and the southern part of China.Its resin is used as a dye and as a folk medicine for purgative and for the treatment of infected wounds,and has been developed as an anti-tumor drug in China.G.tetralata is distributed in the Yunnan province of China.No previous phytochemical investigations were focused on G.tetralata.Based on the review on the chemical constituents and pharmacological research of Garcinia,the chemical constituents of Garcinia hanburyi and G.tetralata and their antitumor activities were researched.
By means of many different chromatographic methods such as silica gel, Sephadex LH-20,ODS column chromatography,and preparative TLC,17 compounds were isolated from the resin of Garcinia hanburyi.By physico-chemical data and spectral methods,these compounds were identified as 2α-hydroxy-3β-O-acetyl-lup-20(29)-en-28-oic acid(1),3-O-(4'-O-acetyl)-α-L-arabinopyranosyl-oleanolic acid(2),gambogic aldehyde(3),forbesione(4),hanburin (5),desoxygambogenin(6),isogambogenin(7),desoxymorellin(8),isomorellin(9),β-morellic acid(10),α-morellic acid(11),gambogellic acid(12),gambogic acid(13), 30-hydroxygambogic acid(14),betulinic acid(15),messagenic acid(16),andβ-sitosterol(17).Among them,compounds 1～3 are determined as new compounds, compound 16 is obtained from genus Garcinia for the first time.
By means of many different chromatographic methods,22 compounds were isolated from the barks of Garcinia tetralata.Twenty of them were characterized by physico-chemical data and spectral methods,and they were 3β-hydroxy-18β, 19β-epoxy-lupane(18),tetralataxanthone(19),2-(1',1'-dimethylprop-2'-enyl)-1,4, 5-trihydroxy-9H-xanthen-9-one(20),6-desoxyjacareubin(21),toxyloxanthone A(22), globuxanthone(23),1,7-dihydroxyxanthone(24),subelliptenone H(25), 6-deoxyjacreubin(26),buchanaxanthone(27),garciniaxanthone H(28),6, 11-dihydroxy-2,2-dimethyl-pyrano[3,2-c]xanthen-7(2H)-one(29),subelliptenone G (30),1,4-dihydroxy-5,6-dimethoxyxanthone(31),1,2,5-trihydroxyxanthone(32),2, 6-dihydroxy-1,5-dimethoxyxanthone(33),morolic acid acetate(34),methyl orsellinate(35),montroumarin(36),andβ-sitosterol(37).Among them,compounds 18 and 19 are determined as new compounds,compounds 34～36 are isolated from genus Garcinia for the first time.
The antitumor activities of the two new triterpenoids and twelve caged polyprenylated xanthones isolated from the resin of Garcinia hanburyi were tested.It was found that all caged polyprenylated xanthones inhibited cell growth with different activities against P388 and P388/ADR cells,in which compounds 12 and 13 were the most potent.The structure-activity relationship of caged polyprenylated xanthones was discussed.The results showed that the presence of pyran-ring in the molecular might have an important role in inhibiting P388 cell line.If the pyran-ring had 2-isoprenyl group,the activity would be enhanced.To the xanthones which had not a pyran-ring(6～7),those with the substituent of 5-geranyl group could have better activity in inhibiting P388 cell line.By testing in human leukemia HL-60,NB4,U937, K562 cells,it was found that two new triterpenes were effective cell growth inhibitors. Compound 2 showed more potent activity than compound 1.The apoptotic effects in HL-60 cells were also examined by morphological observation after AO and EB staining and FACS analysis.The two new triterpenoids induced HL-60 cells to undergo apoptosis in a dose- and time-dependent manner.
On the basis of the research on caged polyprenylated xanthones isolated from the resin of Garcinia hanburyi and the related literatures,an overview on the spectral and structural characteristics of caged polyprenylated xanthones was taken.
引文
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