地耳草石油醚部位化学成分研究
|
摘要
目的:对地耳草石油醚部位进行化学成分研究。方法:地耳草用乙醇冷浸提取,得到粗提物,将其用石油醚萃取后采用各种层析技术进行分离纯化,并对分离得到的化合物进行结构鉴定。结果:分离得到8个单体化合物,分别为(1)2-acetyl-3,5-di-hydroxy-1-geranoxy-6-methyl-4-(2-methyl)butyryl-ben-zene,(2)Empetrikarinol A,(3)2-acetyl-3,5-dihydroxy-1-geranoxy-6-methyl-4-(2-methyl)butyryl-benzene,(4)1-(2,4,6-Thihydroxyphenyl)Butan-1-one,(5)1-(2,4,6-Thihydroxy phenyl-3-methyl)Butan-1-one,对羟基苯丙酸甲酯,O-methoxy cinnamaldehyde,对甲氧基苯甲酸。结论:化合物1-5为间苯三酚类化合物,化合物2,4,5,6,7首次从地耳草中分离得到。
Objective: To investigate the chemical components in Hypericum japonicum. Methods: The crude extract of Hypericum japonicum was obtained extracted by ethanol,and then filtrated and extracted by petroleum ether. The chemical components of petroleum ether portion were obtained by repeated extensive column chromatography( silica gel,YMC gel,Sephadex LH-20 and HPLC),and then identified by IR,NMR,HRESIMS and ECD spectroscopic analysis. Results: Totally 8 compounds were isolated from the extract of petroleum ether of Hypericum japonicum,and identified as 2-acetyl-3,5-di-hydroxy-1-geranoxy-6-methyl-4-( 2-methyl) butyryl-benzene( 1),empetrikarinol A( 2),2-acetyl-3,5-dihydroxy-1-geranoxy-6-methyl-4-( 2-methyl) butyryl-benzene( 3),1-( 2,4,6-thihydroxyphenyl) butan-1-one( 4),1-( 2,4,6-thihydroxy phenyl-3-methyl) butan-1-one( 5),methyl p-hydroxyphenylpropionate( 6),Omethoxy cinnamaldehyde( 7) and p-MBA( 8). Conclusion: The compounds 1-5 are phloroglucinol components,and compounds 2,4,5,6 and 7 are isolated from Hypericum japonicum for the first time.
Objective: To investigate the chemical components in Hypericum japonicum. Methods: The crude extract of Hypericum japonicum was obtained extracted by ethanol,and then filtrated and extracted by petroleum ether. The chemical components of petroleum ether portion were obtained by repeated extensive column chromatography( silica gel,YMC gel,Sephadex LH-20 and HPLC),and then identified by IR,NMR,HRESIMS and ECD spectroscopic analysis. Results: Totally 8 compounds were isolated from the extract of petroleum ether of Hypericum japonicum,and identified as 2-acetyl-3,5-di-hydroxy-1-geranoxy-6-methyl-4-( 2-methyl) butyryl-benzene( 1),empetrikarinol A( 2),2-acetyl-3,5-dihydroxy-1-geranoxy-6-methyl-4-( 2-methyl) butyryl-benzene( 3),1-( 2,4,6-thihydroxyphenyl) butan-1-one( 4),1-( 2,4,6-thihydroxy phenyl-3-methyl) butan-1-one( 5),methyl p-hydroxyphenylpropionate( 6),Omethoxy cinnamaldehyde( 7) and p-MBA( 8). Conclusion: The compounds 1-5 are phloroglucinol components,and compounds 2,4,5,6 and 7 are isolated from Hypericum japonicum for the first time.
引文
1 Wang N,Li PB,Wang YG,et al.Hepatoprotective effect of Hypericum japonicum extract and its fractions[J].Journal of Ethnopharmacology,2008,116(1):1-6
2 Wang XW,Mao Y,Wang NL,et al.A new phloroglucinol diglycoside derivative from Hypericum japonicum Thunb[J].Molecules,2008,13(11):2796-2803
3 Zhang SD,Yin J,Li X.et al.Jacarelhyperol A induced apoptosis in leukaemia cancer cell through inhibition the activity of Bcl-2 proteins[J].BMC-Cancer,2014,14(1):689-693
4 Wang K,Wang YY,Gao X,et al.Polycyclic polyprenylated acylphloroglucinols and cytotoxic constituents of Hypericum androsaemum[J].Chemistry&Biodiversity,2012,9(6):1213-1220
5 Tian WJ,Qiu YQ,Yao XJ,et al.Dioxasampsones A and B,two polycyclic polyprenylated acylphloroglucinols with unusual epoxyring-fused skeleton from Hypericum sampsonii[J].Organic Letters,2014,16(24):6346-6349
6 Zhang JJ,Yang J,Liao Y,et al.Hyperuralones A and B,new acylphloroglucinol derivatives with Intricately caged cores from Hypericum uralum[J].Organic Letters,2014,16(18):4912-4915
7 肖志勇,穆青.金丝桃属植物化学成分研究进展[J].天然产物研究与开发,2007,19(2):344-355
8 傅芃,张卫东,李廷钊,等.田基黄化学成分的研究[J].第二军医大学学报,2004,25(11):1274-1275
9 Takasaki M,Konoshima T,Kozuka M,et al.T Anti-tumor-promoting activities of euglobals from eucalyptus plants[J].Biological&Pharmaceutical Bulletin,1995,18:435-438
10 Hu LH,Khoo CW,Vittal JJ,et al.Phloroglucinol derivatives from Hypericum japonicum[J].Phytochemistry,2000,53(6):705-709
11 Schmidt S,Jurgenliemk G,Schmidt TJ,et al.Bi-,tri-,and polycyclic acylphloroglucinols from hypericum empetrifolium[J].Journal of Natural Products,2012,5(10):1697-1705
12 Joshi BS,Ravindranath KR.Isolation and identification of two phenolic ketones and a chromone from Dysophylla stellata Benth[J].J Chem Soc Perkon Trans 1,1977,4:433-436
13 Ma Y,Jiang JC,Tan WH,et al.Direct liquefaction of bamboo in ethanol-phenol co-solvent[J].Bio Resources,2016,11(4):9520-9532
14 刘岱琳,庞发根,张家欣,等.密花石豆兰的化学成分研究[J].中国药物化学杂志,2005,15(2):104-107
15 Huong DTL,Jo YS,Lee MK,et al.Monoamine oxidase inhibitors from Cinnamomi Cortex[J].Natural product research,2000,6(1):16-19
16 阎新佳,项峥,温静,等.中药连翘的酚酸类化学成分研究[J].中国药学杂志,2017,52(1):2105-2108
17 Kapadia GJ,Balasubramanian V,Tokuda H,et al.Anti-tumor promoting effects of naphthoquinone derivatives on short term epsteinbarr early antigen activation assay and in mouse skin carcinogenesis[J].Cancer Letters,1997,113(1-2):47-53
18 Takasaki M,Konoshima T,Etoh H,et al.Cancer chemopreventive activity of euglobal-G1 from leaves of eucalyptus grandis[J].Cancer Letters,2000,155(1):61-65
2 Wang XW,Mao Y,Wang NL,et al.A new phloroglucinol diglycoside derivative from Hypericum japonicum Thunb[J].Molecules,2008,13(11):2796-2803
3 Zhang SD,Yin J,Li X.et al.Jacarelhyperol A induced apoptosis in leukaemia cancer cell through inhibition the activity of Bcl-2 proteins[J].BMC-Cancer,2014,14(1):689-693
4 Wang K,Wang YY,Gao X,et al.Polycyclic polyprenylated acylphloroglucinols and cytotoxic constituents of Hypericum androsaemum[J].Chemistry&Biodiversity,2012,9(6):1213-1220
5 Tian WJ,Qiu YQ,Yao XJ,et al.Dioxasampsones A and B,two polycyclic polyprenylated acylphloroglucinols with unusual epoxyring-fused skeleton from Hypericum sampsonii[J].Organic Letters,2014,16(24):6346-6349
6 Zhang JJ,Yang J,Liao Y,et al.Hyperuralones A and B,new acylphloroglucinol derivatives with Intricately caged cores from Hypericum uralum[J].Organic Letters,2014,16(18):4912-4915
7 肖志勇,穆青.金丝桃属植物化学成分研究进展[J].天然产物研究与开发,2007,19(2):344-355
8 傅芃,张卫东,李廷钊,等.田基黄化学成分的研究[J].第二军医大学学报,2004,25(11):1274-1275
9 Takasaki M,Konoshima T,Kozuka M,et al.T Anti-tumor-promoting activities of euglobals from eucalyptus plants[J].Biological&Pharmaceutical Bulletin,1995,18:435-438
10 Hu LH,Khoo CW,Vittal JJ,et al.Phloroglucinol derivatives from Hypericum japonicum[J].Phytochemistry,2000,53(6):705-709
11 Schmidt S,Jurgenliemk G,Schmidt TJ,et al.Bi-,tri-,and polycyclic acylphloroglucinols from hypericum empetrifolium[J].Journal of Natural Products,2012,5(10):1697-1705
12 Joshi BS,Ravindranath KR.Isolation and identification of two phenolic ketones and a chromone from Dysophylla stellata Benth[J].J Chem Soc Perkon Trans 1,1977,4:433-436
13 Ma Y,Jiang JC,Tan WH,et al.Direct liquefaction of bamboo in ethanol-phenol co-solvent[J].Bio Resources,2016,11(4):9520-9532
14 刘岱琳,庞发根,张家欣,等.密花石豆兰的化学成分研究[J].中国药物化学杂志,2005,15(2):104-107
15 Huong DTL,Jo YS,Lee MK,et al.Monoamine oxidase inhibitors from Cinnamomi Cortex[J].Natural product research,2000,6(1):16-19
16 阎新佳,项峥,温静,等.中药连翘的酚酸类化学成分研究[J].中国药学杂志,2017,52(1):2105-2108
17 Kapadia GJ,Balasubramanian V,Tokuda H,et al.Anti-tumor promoting effects of naphthoquinone derivatives on short term epsteinbarr early antigen activation assay and in mouse skin carcinogenesis[J].Cancer Letters,1997,113(1-2):47-53
18 Takasaki M,Konoshima T,Etoh H,et al.Cancer chemopreventive activity of euglobal-G1 from leaves of eucalyptus grandis[J].Cancer Letters,2000,155(1):61-65