大叶山楝根化学成分与细胞毒活性的研究
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摘要
为了解大叶山楝(Aphanamixis grandifolia Bl.)根中的抗肿瘤活性成分,利用各种色谱技术从其95%乙醇提取物中分离得到9个化合物,经波谱分析分别鉴定为:7-hydroxycadalene(1)、dregeana-1(2)、4-oxopinoresinol(3)、4-ketopinoresinol(4)、6-deoxyjacareubin(5)、schleicheol 1(6)、豆甾醇(7)、β-谷甾醇(8)和胡萝卜苷(9)。其中化合物1~6为首次从山楝属植物中分离得到,并首次报道了化合物1的碳谱数据。生物活性测试结果表明,化合物1和5对慢性髓原白血病细胞K562有生长抑制活性,化合物1、5和6对人胃癌细胞SGC-7901有生长抑制活性。
In order to understand the antitumor active ingredients of Aphanamixis grandifolia Bl., nine compounds were isolated from 95% ethanol extract of its roots. They were identifi ed as 7-hydroxycadalene(1), dregeana-1(2), 4-oxopinoresinol(3), 4-ketopinoresinol(4), 6-deoxyjacareubin(5), schleicheol 1(6), stigmasterol(7), β-sitosterol(8), and daucosterol(9) on the basis of spectral data. Compounds 1– 6 were isolated from the genus Aphanamixis for the fi rst time, and the 13 C NMR spectral data of compound 1 was reported for the fi rst time. Compounds 1 and 5 showed inhibition of the proliferation of K562 cell line, and compounds 1, 5 and 6 possessed inhibitory activity against SGC-7901 cell line.
In order to understand the antitumor active ingredients of Aphanamixis grandifolia Bl., nine compounds were isolated from 95% ethanol extract of its roots. They were identifi ed as 7-hydroxycadalene(1), dregeana-1(2), 4-oxopinoresinol(3), 4-ketopinoresinol(4), 6-deoxyjacareubin(5), schleicheol 1(6), stigmasterol(7), β-sitosterol(8), and daucosterol(9) on the basis of spectral data. Compounds 1– 6 were isolated from the genus Aphanamixis for the fi rst time, and the 13 C NMR spectral data of compound 1 was reported for the fi rst time. Compounds 1 and 5 showed inhibition of the proliferation of K562 cell line, and compounds 1, 5 and 6 possessed inhibitory activity against SGC-7901 cell line.
引文
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[2]Zhang Y,Wang J S,Luo J,et al.Novel nortriterpenoids from Aphanamixis grandifolia[J].Chem Pharm Bull,2011,59(2):282–286.
[3]Liu Q,Chen C J,Shi X,et al.Chemical constituents from Aphanamixis grandifolia[J].Chem Pharm Bull,2010,58(11):1431–1435.
[4]Zhang Y,Wang J S,Wei D D,et al.Cytotoxic tirucallane C26triterpenoids from the stem barks of Aphanamixis grandifolia[J].Phytochemistry,2010,71(17/18):2199–2204.
[5]Wang J S,Zhang Y,Luo J,et al.Complete 1H and 13C NMR data assignment of protolimonoids from the stem barks of Aphanamixis grandifolia[J].Magn Reson Chem,2011,49(7):450–457.
[6]Wang J S,Zhang Y,Wei D D,et al.Novel tirucallane-type triterpenoids from Aphanamixis grandifolia[J].Chem Biodiv,2011,8(11):2025–2034.
[7]Wang J S,Zhang Y,Wang X B,et al.A pair of tirucallane C27-triterpenoid cyclopentenone epimers from the stem barks of Aphanamixis grandifolia[J].Tetrah Lett,2012,53(14):1705–1709.
[8]Astulla A,Hirasawa Y,Rahman A,et al.Melidianolic acid A and B,new antimalarial acyclic diterpenes from Aphanamixis grandifolia[J].Nat Prod Commun,2011,6(3):323–326.
[9]Wang X Y,Tang G H,Yuan C M,et al.Studies on chemical constituents of the leaves and twigs of Aphanamixis grandifolia[J].J Yunnan Univ Trad Chin Med,2012,35(4):34–36.王小英,苑春茂,唐贵华,等.大叶山楝的化学成分研究[J].云南中医学院学报,2012,35(4):34–36.
[10]Wang X Y,Tang G H,Yuan C M,et al.Two new tirucallane triterpenoids from Aphanamixis grandifolia[J].Nat Prod Bioprospect,2012,2(5):222–226.
[11]Wang X Y,Tang G H,Yuan C M,et al.Aphagrandinoids A–D,cycloartane triterpenoids with antibacterial activities from Aphanamixis grandifolia[J].Fitoterapia,2013,85(1):64–68.
[12]Cai C H.Study on bioactive components from the twigs of Ancistrocladus tectorius[D].Hainan:Hainan University,2013:29.蔡彩虹.钩枝藤枝条的生物活性成分研究[D].海南:海南大学,2013:1–29.
[13]Dong W H,Mei W L,Zeng Y B,et al.Cardenolides from the seeds of Antiaris toxicaria and their cytotoxicity[J].J Trop Subtrop Bot,2011,19(2):171–176.董文化,梅文莉,曾艳波,等.见血封喉种子强心苷类化合物及其细胞毒活性[J].热带亚热带植物学报,2011,19(2):171–176.
[14]Sankaram A V B,Reddy N S,Shoolery J N.New sesquiterpenoids of Bombax malabaricum[J].Phytochemistry,1981,20(8):1877–1881.
[15]Zhang H P,Chen F,Wang X,et al.Complete assignments of1H and 13C NMR data for rings A,B-seco limonoids from the seed of Aphanamixis polystachya[J].Magn Reson Chem,2007,45(2):189–192.
[16]Hu Z X,Xue Y B,Yao G M,et al.Chemical constituents from the leaves of Premna microphylla Turcz[J].J Chin Pharm Sci,2013,22(5):431–434.
[17]Katakawa J,Tetsumi T,Kamei S,et al.Phenolic compounds of fruit of Coix lacryma-jobi L.[J].Nat Med,2000,54(5):257–260.
[18]Li Y Z,Li Z L,Hua H M,et al.Studies on fl avonoids from stems and leaves of Calophyllum inophyllum[J].Chin J Chin Mat Med,2007,32(8):692–694.李艳芝,李占林,华会明,等.红厚壳中黄酮类化学成分研究[J].中国中药杂志,2007,32(8):692–694.
[19]Pettit G R,Numata A,Cragg G M,et al.Isolation and structures of schleicherastatins 1–7 and schleicheols 1 and 2 from the teak forest medicinal tree Schleichera oleosa[J].J Nat Prod,2000,63(1):72–78.
[20]Wu X,Xia H L,Huang L H,et al.Study on the chemical constituents of Rhizoma cyperi[J].Chin Med Mat,2008,31(7):990–992.吴希,夏厚林,黄立华,等.香附化学成分研究[J].中药材,2008,31(7):990–992.
[21]Yu L,Mei W L,Zuo W J,et al.Antimicrobial constituents from the twigs of Trigonostemon xyphophylloides[J].Lishizhen Med Mat Med Res,2013,24(3):591–593.余丽,梅文莉,左文健,等.剑叶三宝木枝条中的抗菌活性成分研究[J].时珍国医国药,2013,24(3):591–593.
[22]Cai C H,Mei W L,Zuo W J,et al.Antibacterial components from the branches of Ancistrocladus tectorius(Lour.)Merr.[J].J Trop Subtrop Bot,2013,21(2):184–188.蔡彩虹,梅文莉,左文健,等.钩枝藤枝条中抗菌活性成分研究[J].热带亚热带植物学报,2013,21(2):184–188.