藏药印度獐芽菜石油醚部位化学成分及体外活性研究
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摘要
采用各种柱色谱以及重结晶等方法对印度獐芽菜石油醚萃取部位进行化学成分研究。通过理化性质和波谱数据分析鉴定了15个化合物,包括8个酮,2个三萜,1个裂环烯醚萜,1个香豆素和3个其他类化合物,分别为1,8-二羟基-3,5-二甲氧基酮(1)、1-羟基-3,7,8-三甲氧基酮(2)、1,8-二羟基-3,5,7-三甲氧基酮(3)、1-羟基-3,5,7,8-四甲氧基酮(4)、1,5,8-三羟基-3-甲氧基酮(5)、1-羟基-3,7-二甲氧基酮(6)、1,8-二羟基-3,7-二甲氧基酮(7)、1-羟基-3,5-二甲氧基酮(8)、古柯二醇(9)、齐墩果酸(10)、(±)-龙胆内酯(11)、东莨菪内酯(12)、芥子醛(13)、丁香醛(14)、β-谷甾醇(15)。其中化合物3,4,9,11~14为首次从该植物中分离得到,化合物9和12为首次从獐芽菜属中发现。对5个量大酮1,2,5,7,8进行体外活性测试,结果显示其在最高浓度50μmol·L~(-1)对胰腺癌细胞SW1990和Bx PC-3的增殖和过氧化氢(H_2O_2)诱导的人脐静脉融合细胞EA.hy926氧化应激损伤均无明显作用。
The present work is to study the chemical constituents from petroleum ether fraction of Tibetan medicine Swertia chirayita by column chromatography and recrystallization. The structures were identified by physical and chemical properties and spectral data as swerchirin( 1),decussatin( 2),1,8-dihydroxy-3,5,7-trimethoxyxanthone( 3),1-hydroxy-3,5,7,8-tetramethoxyxanthone( 4),bellidifolin( 5),1-hydroxy-3,7-dimethoxyxanthone( 6),methylswertianin( 7),1-hydroxy-3,5-dimethoxyxanthone( 8),erythrodiol( 9),oleanolic acid( 10),gnetiolactone( 11),scopoletin( 12),sinapaldehyde( 13),syringaldehyde( 14),and β-sitosterol( 15).Compounds 3,4,9,11-14 were isolated from S. chirayita for the first time. Compounds 9 and 12 were firstly isolated from the genus Swertia. The cytotoxic activities of compounds 1,2,5,7 and 8 against human pancreatic cancer cell lines SW1990 and Bx PC-3,and the protective effects of these compounds against hydrogen peroxide( H_2O_2)-induced oxidative stress in human endothelium-derived EA. hy926 were investigated in vitro. The results showed no obvious effect at the high concentration of 50 μmol·L~(-1)
The present work is to study the chemical constituents from petroleum ether fraction of Tibetan medicine Swertia chirayita by column chromatography and recrystallization. The structures were identified by physical and chemical properties and spectral data as swerchirin( 1),decussatin( 2),1,8-dihydroxy-3,5,7-trimethoxyxanthone( 3),1-hydroxy-3,5,7,8-tetramethoxyxanthone( 4),bellidifolin( 5),1-hydroxy-3,7-dimethoxyxanthone( 6),methylswertianin( 7),1-hydroxy-3,5-dimethoxyxanthone( 8),erythrodiol( 9),oleanolic acid( 10),gnetiolactone( 11),scopoletin( 12),sinapaldehyde( 13),syringaldehyde( 14),and β-sitosterol( 15).Compounds 3,4,9,11-14 were isolated from S. chirayita for the first time. Compounds 9 and 12 were firstly isolated from the genus Swertia. The cytotoxic activities of compounds 1,2,5,7 and 8 against human pancreatic cancer cell lines SW1990 and Bx PC-3,and the protective effects of these compounds against hydrogen peroxide( H_2O_2)-induced oxidative stress in human endothelium-derived EA. hy926 were investigated in vitro. The results showed no obvious effect at the high concentration of 50 μmol·L~(-1)
引文
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[2]钟国跃,阳勇,冯婷婷,等.常用藏药“蒂达”(藏茵陈)基原物种药用合理性及资源利用价值评价[J].中国中药杂志,2012,37(17):2639.
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[6]靳有才,魏立新,林蓉香,等.印度獐牙菜化学成分和药理作用研究进展[J].中国生化药物杂志,2010,31(6):431.
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[12]Fukamiya N,Okano M,Kondo K,et al.Xanthones from Swertia punicea[J].J Nat Prod,1990,53(6):1543.
[13]Mahendran G,Manoj M,Rajendra Prasad K.J,et al.Evaluation of anti-inflammatory and antinoceceptive activity of xanthones from Swertia corymbosa(Griseb.)Wight ex C.B.Clarke[J].Int J Pharm Pharm Sci,2013,5(3):523.
[14]匡海学,吴高松,刘华,等.尖叶假龙胆中酮类成分的分离与鉴定[J].中国中药杂志,2016,41(12):2280.
[15]Monte F J Q,Soares F P,Braz-Filho R.A xanthone from Shultesia guianensis[J].Fitoterapia,2001,72:715.
[16]谭桂山,徐康平,徐平声,等.川东獐牙菜化学成分研究[J].药学学报,2002,37(8):630.
[17]李兆云,王志远,肖怀,等.显脉璋牙菜的化学成分研究[J].中国药房,2016,27(15):2107.
[18]符春丽,彭燕,陈紫云,等.番石榴叶化学成分的研究[J].中药材,2016,39(12):2783.
[19]Thanakijcharoenpath W,Theanphong O.Triterpenoids from the stem of Diospyros glandulosa[J].Thai J Pham Sci,2007(31):1.
[20]Kakuda R,Machida K,Yaoita Y,et al.Studies on the constituents of Gentiana species.Ⅱ.1)A new triterpenoid,and(S)-(+)-and(R)-(-)-gentiolactones from Gentiana lutea[J].Chem Pharm Bull,2003,51(7):885.
[21]Chaves O S,Teles Y C F,Monteiro M M O,et al.Alkaloids and phenolic compounds from Sida rhombifolia L.(Malvaceae)and vasorelaxant activity of two indoquinoline alkaloids[J].Molecules,2017,22(1):94.
[22]柳继锋,张雪梅,施瑶,等.红茴香根茎的化学成分研究[J].中国中药杂志,2010,35(17):2281.
[23]李艳茸,李春,王智民,等.藏药甘青乌头化学成分研究(Ⅲ)[J].中国中药杂志,2014,39(7):1163.
[24]Li J,Ge R,Zhao C,et al.Farrerol regulates occludin expression in hydrogen peroxide-induced EA.hy926 cells by modulating ERK1/2 activity[J].Eur J Pharmacol,2014,734:9.
[25]Hajimehdipoor H,Sadeghi Z,Elmi S,et al.Protective effects of Swertia longifolia Boiss,and its active compound,swerchirin,on paracetamol-induced hepatotoxicity in mice[J].J Pharm Pharmacol,2006,58(2):277.
[26]Basnet P,Kadota S,Shimizu M,et al.Bellidifolin:a potent hypoglycemic agent in streptozotocin(STZ)-induced diabetic rats from Swertia japonica[J].Planta Med,1994,60:507.
[2]钟国跃,阳勇,冯婷婷,等.常用藏药“蒂达”(藏茵陈)基原物种药用合理性及资源利用价值评价[J].中国中药杂志,2012,37(17):2639.
[3]Joshi P,Dhawan V.Swertia chirayita-an overview[J].Curr Sci,2005,89(4):635.
[4]Kumar V,Staden J V.A review of Swertia chirayita(Gentianaceae)as a traditional medicinal plant[J].Front Pharmacol,2016,6(308):1.
[5]Zhou N J,Geng C A,Huang X Y,et al.Anti-hepatitis B virus active constituents from Swertia chirayita[J].Fitoterapia,2015,100:27.
[6]靳有才,魏立新,林蓉香,等.印度獐牙菜化学成分和药理作用研究进展[J].中国生化药物杂志,2010,31(6):431.
[7]Karan M,Vasisht T,Handa S S.Antihepatotoxic activity of Swerti chirata on carbon tetra-chloride induced hepatotoxicity in rats[J].Phytother Res,1999,13(1):24.
[8]Balasundari P,Singh P,Kavimani S.Scavenging of xanthone from Swertia chirata and tumor cell growth inhibition[J].Main Group Chem,2005,4(3):177.
[9]Uvarani C,Chandraprakash K,Sankaran M,et al.Antioxidant and structure-activity relationships of five tetraoxygenated xanthones from Swertia minor(Griscb.)Knobl[J].Nat Prod Rec,2012,26(13):1265.
[10]李旭山,江志勇,王福生,等.青叶胆化学成分研究[J].中国中药杂志,2008,33(23):2790.
[11]何康,曹团武,王洪玲,等.狭叶獐牙菜的化学成分研究[J].中国中药杂志,2015,40(18):3603.
[12]Fukamiya N,Okano M,Kondo K,et al.Xanthones from Swertia punicea[J].J Nat Prod,1990,53(6):1543.
[13]Mahendran G,Manoj M,Rajendra Prasad K.J,et al.Evaluation of anti-inflammatory and antinoceceptive activity of xanthones from Swertia corymbosa(Griseb.)Wight ex C.B.Clarke[J].Int J Pharm Pharm Sci,2013,5(3):523.
[14]匡海学,吴高松,刘华,等.尖叶假龙胆中酮类成分的分离与鉴定[J].中国中药杂志,2016,41(12):2280.
[15]Monte F J Q,Soares F P,Braz-Filho R.A xanthone from Shultesia guianensis[J].Fitoterapia,2001,72:715.
[16]谭桂山,徐康平,徐平声,等.川东獐牙菜化学成分研究[J].药学学报,2002,37(8):630.
[17]李兆云,王志远,肖怀,等.显脉璋牙菜的化学成分研究[J].中国药房,2016,27(15):2107.
[18]符春丽,彭燕,陈紫云,等.番石榴叶化学成分的研究[J].中药材,2016,39(12):2783.
[19]Thanakijcharoenpath W,Theanphong O.Triterpenoids from the stem of Diospyros glandulosa[J].Thai J Pham Sci,2007(31):1.
[20]Kakuda R,Machida K,Yaoita Y,et al.Studies on the constituents of Gentiana species.Ⅱ.1)A new triterpenoid,and(S)-(+)-and(R)-(-)-gentiolactones from Gentiana lutea[J].Chem Pharm Bull,2003,51(7):885.
[21]Chaves O S,Teles Y C F,Monteiro M M O,et al.Alkaloids and phenolic compounds from Sida rhombifolia L.(Malvaceae)and vasorelaxant activity of two indoquinoline alkaloids[J].Molecules,2017,22(1):94.
[22]柳继锋,张雪梅,施瑶,等.红茴香根茎的化学成分研究[J].中国中药杂志,2010,35(17):2281.
[23]李艳茸,李春,王智民,等.藏药甘青乌头化学成分研究(Ⅲ)[J].中国中药杂志,2014,39(7):1163.
[24]Li J,Ge R,Zhao C,et al.Farrerol regulates occludin expression in hydrogen peroxide-induced EA.hy926 cells by modulating ERK1/2 activity[J].Eur J Pharmacol,2014,734:9.
[25]Hajimehdipoor H,Sadeghi Z,Elmi S,et al.Protective effects of Swertia longifolia Boiss,and its active compound,swerchirin,on paracetamol-induced hepatotoxicity in mice[J].J Pharm Pharmacol,2006,58(2):277.
[26]Basnet P,Kadota S,Shimizu M,et al.Bellidifolin:a potent hypoglycemic agent in streptozotocin(STZ)-induced diabetic rats from Swertia japonica[J].Planta Med,1994,60:507.