多花勾儿茶的化学成分及生物活性研究
摘要
勾儿茶属为鼠李科植物,全世界约有31种,主要分布于亚洲东部及东南部的温带和热带地区。我国有18种,主要分布于西南、华南、中南及华东地区。多花勾儿茶是本属的一个变种,其根部在我国民间用来治疗胆结石,胃痛和风湿关节痛等。本文对产自我国海南省尖峰岭的药用植物多花勾儿茶的根进行了化学成分和生物活性研究。
采用多种色谱方法(硅胶色谱,ODS色谱,凝胶色谱)从多花勾儿茶根的95%乙醇提取物乙酸乙酯部分分离得到了17个化合物,并运用了波谱技术(IR,MS,1D-NMR和2D-NMR)鉴定了它们的化学结构。在所得到的化合物中,12个为蒽醌类化合物,他们分别是:多花二醌A(Floribundiquinone A,1)、多花二醌B(Floribundiquinone B,2)、多花二醌C(Floribundiquinone C,3)、多花二醌D(Floribundiquinone D,4)、多花二醌E(Floribundiquinone E,5)、2-乙酰大黄素甲醚(2-acetylphyscion,6)、10-(chrysophanol-7′-yl)-10-hydroxy-chrysophanol-9-anthrane(7)、大黄素甲醚(physcion,8)、大黄酚(chrysophanol,9)、长孺孢素(Helminthosporin,10)、芦荟大黄素(aloe-emodin,11)、xanthorin12);1个二氢黄酮类化合物(2R,3R)-3,3′,5,5′,7-pentahydroxyflavanone(13):1个五环三萜类化合物羽扇豆醇(lupeol,14),还有2个甾醇类化合物β-谷甾醇(β-sitosterol,15)、胡萝卜苷(β-sitosterol-D-glucoside,16)及1个长链脂肪醇(17)。其中,1-6为新化合物,化合物7、10-13首次从该属植物中分离得到。
药理筛选实验表明,多花勾儿茶95%乙醇提取物的乙酸乙酯层和正丁醇层对半乳糖胺引起的肝细胞损伤具有明显的保护活性,细胞存活率达到了38.0%(1×10~(-4)M),对从乙酸乙酯中分离的化合物1-4、8、9也进行了保肝活性筛选,其中化合物3和4具有较强的保肝活性,细胞存活率分别达到了81.0%(1×10~(-4)M)和76.0%(1×10~(-4)M)。采用MTT法对化合物1-5、7-9、12进行四种肿瘤细胞HCT-8、Bel-7402、BGC-823、A-549和A2780的抗肿瘤药理活性筛选时,未发现有活性成分。
The genus Berchemia(Rhamnaceae) comprises about 31 species,occurring mainly in Asian,of which eighteen were distributed in the south of China.Its root was used as folk medicine to treat gall stones,stomach-ache,rheumatism and lumbago in China. The chemical constituents and bioactivities of Berchemia floribunda were studied, which was distributed in the Jianfengling of Hainan province,P.R.China.
In the course of our search for active components from 95%ethanol extration of the roots of Berchemia floribunda,17 compounds were isolated by chromatographed columns of silica gel,ODS and sephadex LH-20.Their structures were elucidated by analysis of several spectra such as UV,IR,MS,1D-NMR and 2D-NMR,as floribundiquinone A-E(1-5),and 2-acetylphyscion(6),and eleven known compounds. 10-(chrysophanol-7'-yl)-10-hydroxychrysophanol-9-anthrane(7),physcion(8), chrysophanol(9),Helminthosporin(10),aloe-emodin(11),xanthorin(12),(2R, 3R)-3,3',5,5',7-pentahydroxyflavanone(13),lupeol(14),β-sitosteol(15),β-daucosterol(16),long chain fatty(17).Among these,compounds 1-6 are six new compounds,compounds 7,10-13,were first reported from genus Berchemia.
The pharmacological experiment indicated significant hepatoprotective effects of EtOAc and n-Butanol fractions of 95%ethanol extracts against D-galactosamine-induced toxicity in WB-F344 cells,the availability of which was reached 38%at the concentration of 1×10~(-4)M in vitro.Compounds 1-4,8 and 9,isolated from the EtOAc fraction,were also monitored,among them,compounds 3 and 4 showed potent hepatoprotective effect,which availability were 81.0%and 76.0%at the concentration of 1×10~(-4)M in vitro,resepectively.Active compound was not found in pharmacological monitor experiment by MTT methods,which have cytotoxic activities against the tumor cell HCT-8,Bel-7402,BGC-823,A-549 and A2780.
采用多种色谱方法(硅胶色谱,ODS色谱,凝胶色谱)从多花勾儿茶根的95%乙醇提取物乙酸乙酯部分分离得到了17个化合物,并运用了波谱技术(IR,MS,1D-NMR和2D-NMR)鉴定了它们的化学结构。在所得到的化合物中,12个为蒽醌类化合物,他们分别是:多花二醌A(Floribundiquinone A,1)、多花二醌B(Floribundiquinone B,2)、多花二醌C(Floribundiquinone C,3)、多花二醌D(Floribundiquinone D,4)、多花二醌E(Floribundiquinone E,5)、2-乙酰大黄素甲醚(2-acetylphyscion,6)、10-(chrysophanol-7′-yl)-10-hydroxy-chrysophanol-9-anthrane(7)、大黄素甲醚(physcion,8)、大黄酚(chrysophanol,9)、长孺孢素(Helminthosporin,10)、芦荟大黄素(aloe-emodin,11)、xanthorin12);1个二氢黄酮类化合物(2R,3R)-3,3′,5,5′,7-pentahydroxyflavanone(13):1个五环三萜类化合物羽扇豆醇(lupeol,14),还有2个甾醇类化合物β-谷甾醇(β-sitosterol,15)、胡萝卜苷(β-sitosterol-D-glucoside,16)及1个长链脂肪醇(17)。其中,1-6为新化合物,化合物7、10-13首次从该属植物中分离得到。
药理筛选实验表明,多花勾儿茶95%乙醇提取物的乙酸乙酯层和正丁醇层对半乳糖胺引起的肝细胞损伤具有明显的保护活性,细胞存活率达到了38.0%(1×10~(-4)M),对从乙酸乙酯中分离的化合物1-4、8、9也进行了保肝活性筛选,其中化合物3和4具有较强的保肝活性,细胞存活率分别达到了81.0%(1×10~(-4)M)和76.0%(1×10~(-4)M)。采用MTT法对化合物1-5、7-9、12进行四种肿瘤细胞HCT-8、Bel-7402、BGC-823、A-549和A2780的抗肿瘤药理活性筛选时,未发现有活性成分。
The genus Berchemia(Rhamnaceae) comprises about 31 species,occurring mainly in Asian,of which eighteen were distributed in the south of China.Its root was used as folk medicine to treat gall stones,stomach-ache,rheumatism and lumbago in China. The chemical constituents and bioactivities of Berchemia floribunda were studied, which was distributed in the Jianfengling of Hainan province,P.R.China.
In the course of our search for active components from 95%ethanol extration of the roots of Berchemia floribunda,17 compounds were isolated by chromatographed columns of silica gel,ODS and sephadex LH-20.Their structures were elucidated by analysis of several spectra such as UV,IR,MS,1D-NMR and 2D-NMR,as floribundiquinone A-E(1-5),and 2-acetylphyscion(6),and eleven known compounds. 10-(chrysophanol-7'-yl)-10-hydroxychrysophanol-9-anthrane(7),physcion(8), chrysophanol(9),Helminthosporin(10),aloe-emodin(11),xanthorin(12),(2R, 3R)-3,3',5,5',7-pentahydroxyflavanone(13),lupeol(14),β-sitosteol(15),β-daucosterol(16),long chain fatty(17).Among these,compounds 1-6 are six new compounds,compounds 7,10-13,were first reported from genus Berchemia.
The pharmacological experiment indicated significant hepatoprotective effects of EtOAc and n-Butanol fractions of 95%ethanol extracts against D-galactosamine-induced toxicity in WB-F344 cells,the availability of which was reached 38%at the concentration of 1×10~(-4)M in vitro.Compounds 1-4,8 and 9,isolated from the EtOAc fraction,were also monitored,among them,compounds 3 and 4 showed potent hepatoprotective effect,which availability were 81.0%and 76.0%at the concentration of 1×10~(-4)M in vitro,resepectively.Active compound was not found in pharmacological monitor experiment by MTT methods,which have cytotoxic activities against the tumor cell HCT-8,Bel-7402,BGC-823,A-549 and A2780.
引文
|1]全国中草药汇编 人民卫生出版社,上册1992,777
[2]中国植物志 中国科学院中国植物志编辑委员会主编 科学出版社出版,1978.106
[3]陈立,董俊兴勾儿茶属植物化学成分及其生物活性研究进展 中草药,2006,37(4)627-630
[4]Inoue T.,Nagashima S.,Ohata S.,Shinoda M.,and Sakurai N.,Two phenol compounds from Berchemia racemosa.,Planta Med.,1990,56(1),120-1
[5]Kikuchi M.,Sato K.,Shiraishi Y.,Nakayama R.,Watanabe R.,and Sugiyama M.,Constituents of Berchemia racemosa Sieb.Et Zucc.Yakugaku Zasshi,1990,110(5),354-357
[6]Lee S.S.,Tsai F.Y.,Chen I.S.,Chemical constituents from Berchernia formosana.J.Chin.Chem.Soc.(Taipei),1995,42(1),101-105
[7]Mukhtar N.,Malik A.,Riaz N.,Iqbal K.,Tareen R.B.,Pakistolides A and B,novel enzyme inhibitory and antioxidant dimeric 4-(glucosyloxy) benzoates from Berchemia pakistanica.Helvet Chim Acta,2004,87(2),416-424
[8]Wang Y.F.,Cao J.X.,Efferth T.,Lai(3.f.,and Luo S.D.,Cytotoxic and new tetralone derivatives from Berchemia floribunda(Wall.) Brongn.Chemistry&Biodiversity,2006,3,646-653
[9]Sakurai N.,Kobayashi M.,Shigihara A.,and Inoue T.,Berchemolide,a novel dimeric vanillic acid glucoside from Berchemia racemosa.Chem.Pharm.Bull..1992,40(4),851-853
[10]Bekker R.,Smit R.S.,Brandt E.V.,and Ferreira D.Benzofuranoid with carbon frameworks reminiscent of products of benzylic acid rearrangement.Phytochemistry,1996,43(3),673-679
[11]Bekker R.,Brandt E.V.,and Ferreira D.,Absolute configuration of flavanone-benzofuranone-type biflavonoids and 2-benzyl-2-hydroxybenzofuranones.J.Chem.Soc.Perkin Trans.1,1996,2535-2540
[12]Bekker R.,Brandt E.V.,and Ferreira D.,Structure and stereochemistry of the first isoflavanone-benzofuranone biflavonoids.Tetrahedron Lett.,1998,39(35),6407-6410
[13]Bekker R.,Brandt E.V.,and Ferreira D.,Biflavonoids.Part 4:structure and stereochemistry of novel flavanone and the first isoflavanone-benzofuranone biflavonoids.Tetrahedron,1999,55(33),10005-10012
[14]Bekker R.,Ferreira D.,Swart K.J.,and Brandt E.V.,Biflavonoids.Part 5:structure and stereochemistry of the first bibenzofuranoids.Tetrahedron,2000,56(30),5297-5302
[15]杨娟,潘琪,魏东法,汪冶 光枝勾儿茶化学成分研究(Ⅱ) 中国药学杂志,2006,41(4),255-257
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[17]Inoshiri S.,Sasaki M.,Hirai Y.,Kohda H.,Otsuka H.,and Yamasaki K.,Inhibition of mast cell histamine release by 2,6-dimethoxy-p-benzoquinone isolated from Berchemia racemosa.Chem.Pharm.Bull.,1986,34(3),1333-1336
[18]Inoshiri S.,Sasaki M.,Kohda H.,Otsuka H.,and Yamasaki K.,Aromatic glycosides from Berchemia racemosa.Phytochemistry,1987,26(10),2811-2814
[19]Sakurai N.,Nagashima S.,Kawai K.and Inoue T.,A new lignan,(-)-berchemol,from Berchemia racemosa.Chem.Pharm.Bull.,1989,37(12),3311-3315
[20]Mukhtar N.,Malik A.,Iqbal K.,Tareen R.B.,Khan S.N.,Nawaz S.A.,and Choudhary M.I.Berchemins A and B:novel enzyme-inhibiting dimeric lignan glycosides from Berchemia pakistanica.Helv.Chim.Acta,2004,87(8),2050-2056
[21]Inoshiri S.,Saiki M.,Kohda H.,Otsuka H.,and Yamasaki K.,Monoterpene glucosides from Berchemia racemosa.Phytochemstry,1998,27(9),2869-2871
[22]Kumazawa N.,Ohta S.Tu S.H.,Protective effects of various methanol extracts of crude drugs on experimental hepatic injury induced by alpha-naphthyl- isothiocyanate in rats. Yakugaku zasshi, 1991, 111 (3), 199-204
[23] Sato, N., Ohta, S., Sakurai, N., Kamogawa, A., Inoue, T., and Shinoda, M., Protective effects of the stem of Berchemia racemosa Sieb. et Zucc. on experimental liver injuries. Yakugaku Zasshi, 1995,115 (4), 295-306
[24] Hwang E. I., Lee H. B., and Kim S. U. K., Screening of chitin synthase II inhibitors from medicinal and wild plants. Yakhak Hoechi, 1999, 43 (4), 502-508
[25] Gundidza M., and Sibanda M., Antimicrobial activities of Ziziphus alryssinica and Berchemia discolor. Cent. Afr. Med., 1991, 37 (3), 80-83
[26] Min B. S., Bae K., Kim Y. H., Shimotohno K., Miyashiro H., Hattori M, Inhibitory activities of Korean plants on HIV-1 protease. Natural Product Sciences, 1998,4(4), 241-244
[27] Sato T., Antitumor activity of water-soluble portion from aerial part of Berchemia racemosa SIEB. et ZUCC. and isolation of a peptide. Journal of Tohoku Pharmace- utical University, 2003, 50, 131-136
[28] Hanumaiah T., Marshall D.S., Rao B.K., Rao C.P., Rao G.S.R., Rao J.U.M., Rao K.V.J., Ronald H. Benzisochromanquinones in Ventilago species. Phytochemistry, 1985, 24, 2373-2378
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[30] Prelog V., Helmchen G, Basic principles of the CIP-system and proposals for a revision. Angew chem., Int. Ed. Engl., 1982, 21, 567-574
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[33]Tang C.P.,Yang Y.P.,Zhong Y.,Zhong Q.X.,Wu H.M.,Ye Y.,Four new naphthylisoquinline alkaloids from Ancistrocladus tectorius.J.Nat.Prod.,2000,63,1384-1387
[34]Buchanan M.S.,Gill M.,Yu J.,Pigments of fungi.XLV the cardinalins 8-12,unique pre-naphthoquinone dehydro dimers from the New Zealand toadstool Dermocybe cardinalis.Aust.J.Chem.,1997,50,1081-1089
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[2]中国植物志 中国科学院中国植物志编辑委员会主编 科学出版社出版,1978.106
[3]陈立,董俊兴勾儿茶属植物化学成分及其生物活性研究进展 中草药,2006,37(4)627-630
[4]Inoue T.,Nagashima S.,Ohata S.,Shinoda M.,and Sakurai N.,Two phenol compounds from Berchemia racemosa.,Planta Med.,1990,56(1),120-1
[5]Kikuchi M.,Sato K.,Shiraishi Y.,Nakayama R.,Watanabe R.,and Sugiyama M.,Constituents of Berchemia racemosa Sieb.Et Zucc.Yakugaku Zasshi,1990,110(5),354-357
[6]Lee S.S.,Tsai F.Y.,Chen I.S.,Chemical constituents from Berchernia formosana.J.Chin.Chem.Soc.(Taipei),1995,42(1),101-105
[7]Mukhtar N.,Malik A.,Riaz N.,Iqbal K.,Tareen R.B.,Pakistolides A and B,novel enzyme inhibitory and antioxidant dimeric 4-(glucosyloxy) benzoates from Berchemia pakistanica.Helvet Chim Acta,2004,87(2),416-424
[8]Wang Y.F.,Cao J.X.,Efferth T.,Lai(3.f.,and Luo S.D.,Cytotoxic and new tetralone derivatives from Berchemia floribunda(Wall.) Brongn.Chemistry&Biodiversity,2006,3,646-653
[9]Sakurai N.,Kobayashi M.,Shigihara A.,and Inoue T.,Berchemolide,a novel dimeric vanillic acid glucoside from Berchemia racemosa.Chem.Pharm.Bull..1992,40(4),851-853
[10]Bekker R.,Smit R.S.,Brandt E.V.,and Ferreira D.Benzofuranoid with carbon frameworks reminiscent of products of benzylic acid rearrangement.Phytochemistry,1996,43(3),673-679
[11]Bekker R.,Brandt E.V.,and Ferreira D.,Absolute configuration of flavanone-benzofuranone-type biflavonoids and 2-benzyl-2-hydroxybenzofuranones.J.Chem.Soc.Perkin Trans.1,1996,2535-2540
[12]Bekker R.,Brandt E.V.,and Ferreira D.,Structure and stereochemistry of the first isoflavanone-benzofuranone biflavonoids.Tetrahedron Lett.,1998,39(35),6407-6410
[13]Bekker R.,Brandt E.V.,and Ferreira D.,Biflavonoids.Part 4:structure and stereochemistry of novel flavanone and the first isoflavanone-benzofuranone biflavonoids.Tetrahedron,1999,55(33),10005-10012
[14]Bekker R.,Ferreira D.,Swart K.J.,and Brandt E.V.,Biflavonoids.Part 5:structure and stereochemistry of the first bibenzofuranoids.Tetrahedron,2000,56(30),5297-5302
[15]杨娟,潘琪,魏东法,汪冶 光枝勾儿茶化学成分研究(Ⅱ) 中国药学杂志,2006,41(4),255-257
[16]杨娟,段文峰,彭英,胡俊,杨小生,汪冶光枝勾儿茶化学成分研究(Ⅰ)中草药,2006,37,836-837
[17]Inoshiri S.,Sasaki M.,Hirai Y.,Kohda H.,Otsuka H.,and Yamasaki K.,Inhibition of mast cell histamine release by 2,6-dimethoxy-p-benzoquinone isolated from Berchemia racemosa.Chem.Pharm.Bull.,1986,34(3),1333-1336
[18]Inoshiri S.,Sasaki M.,Kohda H.,Otsuka H.,and Yamasaki K.,Aromatic glycosides from Berchemia racemosa.Phytochemistry,1987,26(10),2811-2814
[19]Sakurai N.,Nagashima S.,Kawai K.and Inoue T.,A new lignan,(-)-berchemol,from Berchemia racemosa.Chem.Pharm.Bull.,1989,37(12),3311-3315
[20]Mukhtar N.,Malik A.,Iqbal K.,Tareen R.B.,Khan S.N.,Nawaz S.A.,and Choudhary M.I.Berchemins A and B:novel enzyme-inhibiting dimeric lignan glycosides from Berchemia pakistanica.Helv.Chim.Acta,2004,87(8),2050-2056
[21]Inoshiri S.,Saiki M.,Kohda H.,Otsuka H.,and Yamasaki K.,Monoterpene glucosides from Berchemia racemosa.Phytochemstry,1998,27(9),2869-2871
[22]Kumazawa N.,Ohta S.Tu S.H.,Protective effects of various methanol extracts of crude drugs on experimental hepatic injury induced by alpha-naphthyl- isothiocyanate in rats. Yakugaku zasshi, 1991, 111 (3), 199-204
[23] Sato, N., Ohta, S., Sakurai, N., Kamogawa, A., Inoue, T., and Shinoda, M., Protective effects of the stem of Berchemia racemosa Sieb. et Zucc. on experimental liver injuries. Yakugaku Zasshi, 1995,115 (4), 295-306
[24] Hwang E. I., Lee H. B., and Kim S. U. K., Screening of chitin synthase II inhibitors from medicinal and wild plants. Yakhak Hoechi, 1999, 43 (4), 502-508
[25] Gundidza M., and Sibanda M., Antimicrobial activities of Ziziphus alryssinica and Berchemia discolor. Cent. Afr. Med., 1991, 37 (3), 80-83
[26] Min B. S., Bae K., Kim Y. H., Shimotohno K., Miyashiro H., Hattori M, Inhibitory activities of Korean plants on HIV-1 protease. Natural Product Sciences, 1998,4(4), 241-244
[27] Sato T., Antitumor activity of water-soluble portion from aerial part of Berchemia racemosa SIEB. et ZUCC. and isolation of a peptide. Journal of Tohoku Pharmace- utical University, 2003, 50, 131-136
[28] Hanumaiah T., Marshall D.S., Rao B.K., Rao C.P., Rao G.S.R., Rao J.U.M., Rao K.V.J., Ronald H. Benzisochromanquinones in Ventilago species. Phytochemistry, 1985, 24, 2373-2378
[29] Jammula S.R., Pepalla S.B., Telikepalli H., Rao K.V.J., Thomson R.H., Benzisochromanquinones from Ventilago goughii. Phytochemistry, 1991, 30. 3741-3744
[30] Prelog V., Helmchen G, Basic principles of the CIP-system and proposals for a revision. Angew chem., Int. Ed. Engl., 1982, 21, 567-574
[31] Buchanan M.S., Gill M., Gimenez A. J., Pigments of fungi, part 17. structure and stereochemistry of coupled pre-anthraquinones of the pseudophlegmacin type from Australian toadstools belonging to the genus Dermocybe. J. Chem. Soc. Perkin Trans 1,1999, 795-801
[32] Buchanan M.S., Gill M., Millar P., Phonh-Axa S., Raudies E., Yu J., Pigments of fungi. part 17 (5)-(+)-dermochrysone, (+)-dermolactone, dermoquinone. and related pigments;new nonaketides from the fungus Dermocybe sanguinea (sensu cleland).J.Chem.Soc.Perkin Trans 1,1990,2585-2591
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