黑籽重楼化学成分及其抗肿瘤活性研究
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摘要
目的研究黑籽重楼Paris thibetica根状茎的化学成分及其抗肿瘤活性。方法综合运用正相硅胶、Sephadex LH-20、ODS-C18等柱色谱以及半制备高效液相色谱等方法进行分离纯化,并通过MS、1H-NMR、13C-NMR等波谱学方法进行结构鉴定。采用MTT法研究化合物的体外抗肿瘤活性。结果从黑籽重楼根状茎的乙醇提取物中分离得到14个化合物,分别鉴定为重楼皂苷V(1)、重楼皂苷I(2)、重楼皂苷II(3)、重楼皂苷VI(4)、偏诺皂苷元-3-O-α-L-呋喃阿拉伯糖基(1→4)-β-D-吡喃葡萄糖苷(5)、重楼皂苷H(6)、偏诺皂苷元-3-O-α-L-吡喃鼠李糖基(1→4)-[α-L-吡喃鼠李糖基(1→2)]-β-D-吡喃葡萄糖苷(7)、重楼皂苷VII(8)、parisyunnanoside G(9)、trikamsteroside E(10)、豆甾醇-3-O-β-D-吡喃葡萄糖(11)、β-谷甾醇棕榈酸酯(12)、β-香树脂醇(13)、4-羟基-5-甲基呋喃-3-羧酸(14)。结论所有化合物均为首次从黑籽重楼中分离得到,化合物10、12~14为首次从重楼属植物中分离得到。化合物1~8对人肝癌细胞BEL-7402有细胞毒活性,其中化合物3活性最好,IC50为0.48μmol/L。
Objective To investigate the chemical constituents from Paris thibetica and their antitumor activities. Methods The separations and purifications were taken by column chromatography over silica gel, Sephadex LH-20, ODS-C18, and semi-preparative HPLC. The in vitro antitumor activities of the isolated compounds were studied by MTT method. Results Fourteen compounds were isolated from ethanol extract of the rhizomes of P. thibetica, which were identified as paris saponin V(1), paris saponin I(2), paris saponin II(3), paris saponin VI(4), pennogennin-3-O-α-L-arabinofuranosyl-(1→4)-β-D-glucopyranoside(5), paris saponin H(6), pennogennin-3-O-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside(7), paris saponin VII(8), parisyunnanoside G(9), trikamsteroside E(10), stigmasterol-3-O-β-D-glucopyranoside(11), β-sitosteryl palmitate(12), β-amyrin(13), and 4-hydroxy-5-methylfuran-3-carboxylic acid(14). Conclusion All compounds are firstly reported from P. thibetica, and this is the first report of compounds 10 and 12—14 from the genus Paris L. Compounds 1—8 show cytotoxicities against BEL-7402. Among the tested compounds, compound 3 exhibits the strongest cytotoxicity with IC50 value of 0.48 μmol/L.
Objective To investigate the chemical constituents from Paris thibetica and their antitumor activities. Methods The separations and purifications were taken by column chromatography over silica gel, Sephadex LH-20, ODS-C18, and semi-preparative HPLC. The in vitro antitumor activities of the isolated compounds were studied by MTT method. Results Fourteen compounds were isolated from ethanol extract of the rhizomes of P. thibetica, which were identified as paris saponin V(1), paris saponin I(2), paris saponin II(3), paris saponin VI(4), pennogennin-3-O-α-L-arabinofuranosyl-(1→4)-β-D-glucopyranoside(5), paris saponin H(6), pennogennin-3-O-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside(7), paris saponin VII(8), parisyunnanoside G(9), trikamsteroside E(10), stigmasterol-3-O-β-D-glucopyranoside(11), β-sitosteryl palmitate(12), β-amyrin(13), and 4-hydroxy-5-methylfuran-3-carboxylic acid(14). Conclusion All compounds are firstly reported from P. thibetica, and this is the first report of compounds 10 and 12—14 from the genus Paris L. Compounds 1—8 show cytotoxicities against BEL-7402. Among the tested compounds, compound 3 exhibits the strongest cytotoxicity with IC50 value of 0.48 μmol/L.
引文
[1]王跃虎,牛红梅,张兆云,等.重楼属植物的药用价值及其化学物质基础[J].中国中药杂志,2015,40(5):833-839.
[2]赵保胜,朱寅荻,马勇,等.中药重楼研究进展[J].中国实验方剂学杂志,2011,17(11):267-270.
[3]武珊珊,高文远,段宏泉,等.重楼化学成分和药理作用研究进展[J].中草药,2004,35(3):344-347.
[4]尹鸿翔,张浩,薛丹,等.川滇地区重楼属药用植物资源质量初评[J].中国中药杂志,2007,32(13):1344-1346.
[5]唐铭霞,王丽,翁周.黑籽重楼种内AFLP遗传多样性及遗传分化研究[J].四川大学学报:自然科学版,2008,45(2):402-408.
[6]陈照,叶睿超,张瑞,等.黑籽重楼种内形态标记和ISSR标记的遗传分化研究[J].时珍国医国药,2009,20(10):2647-2649.
[7]李青,文飞燕,尹鸿翔,等.HPLC测定黑籽重楼中的皂苷含量并评价其药材质量[J].华西药学杂志,2013,28(4):395-397.
[8]刘海,黄芸,张婷,等.金线重楼的化学成分[J].中国药科大学学报,2006,37(5):409-412.
[9]黄贤校,高文远,满淑丽,等.北重楼的化学成分研究[J].中国中药杂志,2009,34(14):1812-1815.
[10]Munday S C,Wilkins A L,Miles C O,et al.Isolation and structure elucidation of dichotomin,a furostanol saponin implicated in hepatogenous photosensitization of sheep grazing Panicum dichotomiflorum[J].J Agr Food Chem,1993,41(2):267-271.
[11]Wang Y,Gao W Y,Li X,et al.Chemical constituents from the rhizome of Paris bashanensis and their cytotoxic activity[J].Lat Am J Pharm,2013,32(2):232-238.
[12]赵志勇,高文远,黄贤校,等.长药隔重楼化学成分研究[J].中草药,2011,42(10):1917-1920.
[13]陈昌祥,周俊,张玉童,等.滇产植物皂素成分的研究Ⅷ.禄劝花叶重楼的甾体皂甙[J].植物分类与资源学报,1983,5(2):219-223.
[14]陈昌祥,周俊,张玉童,等.滇重楼地上部分的甾体皂甙[J].植物分类与资源学报,1990,12(3):323-329.
[15]Kang L P,Liu Y X,Eichhorn T,et al.Polyhydroxylated steroidal glycosides from Paris polyphylla[J].J Nat Prod,2012,75(6):1201-1205.
[16]Ono M,Sugita F,Shigematsu S,et al.Three new steroid glycosides from the underground parts of Trillium kamtschaticum[J].Chem Pharm Bull,2007,55(7):1093-1096.
[17]蔡晨秋,赵明波,唐丽,等.苏木的化学成分研究[J].中草药,2012,43(2):230-233.
[18]韦建华,陈君,蔡少芳,等.倒地铃化学成分研究(I)[J].中草药,2011,42(8):1509-1511.
[19]赵军,杨伟俊,任远,等.刺山柑化学成分研究[J].天然产物研究与开发,2012,24(1):52-54.
[2]赵保胜,朱寅荻,马勇,等.中药重楼研究进展[J].中国实验方剂学杂志,2011,17(11):267-270.
[3]武珊珊,高文远,段宏泉,等.重楼化学成分和药理作用研究进展[J].中草药,2004,35(3):344-347.
[4]尹鸿翔,张浩,薛丹,等.川滇地区重楼属药用植物资源质量初评[J].中国中药杂志,2007,32(13):1344-1346.
[5]唐铭霞,王丽,翁周.黑籽重楼种内AFLP遗传多样性及遗传分化研究[J].四川大学学报:自然科学版,2008,45(2):402-408.
[6]陈照,叶睿超,张瑞,等.黑籽重楼种内形态标记和ISSR标记的遗传分化研究[J].时珍国医国药,2009,20(10):2647-2649.
[7]李青,文飞燕,尹鸿翔,等.HPLC测定黑籽重楼中的皂苷含量并评价其药材质量[J].华西药学杂志,2013,28(4):395-397.
[8]刘海,黄芸,张婷,等.金线重楼的化学成分[J].中国药科大学学报,2006,37(5):409-412.
[9]黄贤校,高文远,满淑丽,等.北重楼的化学成分研究[J].中国中药杂志,2009,34(14):1812-1815.
[10]Munday S C,Wilkins A L,Miles C O,et al.Isolation and structure elucidation of dichotomin,a furostanol saponin implicated in hepatogenous photosensitization of sheep grazing Panicum dichotomiflorum[J].J Agr Food Chem,1993,41(2):267-271.
[11]Wang Y,Gao W Y,Li X,et al.Chemical constituents from the rhizome of Paris bashanensis and their cytotoxic activity[J].Lat Am J Pharm,2013,32(2):232-238.
[12]赵志勇,高文远,黄贤校,等.长药隔重楼化学成分研究[J].中草药,2011,42(10):1917-1920.
[13]陈昌祥,周俊,张玉童,等.滇产植物皂素成分的研究Ⅷ.禄劝花叶重楼的甾体皂甙[J].植物分类与资源学报,1983,5(2):219-223.
[14]陈昌祥,周俊,张玉童,等.滇重楼地上部分的甾体皂甙[J].植物分类与资源学报,1990,12(3):323-329.
[15]Kang L P,Liu Y X,Eichhorn T,et al.Polyhydroxylated steroidal glycosides from Paris polyphylla[J].J Nat Prod,2012,75(6):1201-1205.
[16]Ono M,Sugita F,Shigematsu S,et al.Three new steroid glycosides from the underground parts of Trillium kamtschaticum[J].Chem Pharm Bull,2007,55(7):1093-1096.
[17]蔡晨秋,赵明波,唐丽,等.苏木的化学成分研究[J].中草药,2012,43(2):230-233.
[18]韦建华,陈君,蔡少芳,等.倒地铃化学成分研究(I)[J].中草药,2011,42(8):1509-1511.
[19]赵军,杨伟俊,任远,等.刺山柑化学成分研究[J].天然产物研究与开发,2012,24(1):52-54.