四数九里香中的咔唑类生物碱成分及其细胞毒活性研究
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摘要
为阐明民族药四数九里香Murraya tetramera Huang的药效物质基础,本研究使用色谱分离技术从其醇提取物中分离纯化得7个咔唑类生物碱和1个甾体类化合物,运用波谱方法鉴定为β-谷甾醇(1)、1-甲基-3-丙酰基咔唑(2)、1-甲氧基-3-乙基咔唑(3)、1-甲氧基-3-甲酰基咔唑(4)、1-甲氧基-3-甲基咔唑(5)、1-羧基甲酯-3-甲基咔唑(6)、1-羧基甲酯-3-乙基咔唑(7)、mananimbine(8)。除了化合物1,其他化合物为首次从该植物中分离得到;化合物2～5、7对SMMC-7721的IC50分别为40. 93±0. 66、46. 03±2. 05、114. 21±5. 67、15. 79±0. 99、185. 1±0. 44。结果表明化合物2～5、7对SMMC-7721显现很好的细胞毒活性。
The Carbazole alkaloids from Murraya tetramera Huang and their cytotoxic activities were investigated in this study. The ethanol extract from Murraya tetramera Huang were separated by chromatographic techniques. The structures of these compounds were identified by1 H NMR,3 C NMR,HSQC,HMBC. they were β-sitosterol(1),1-methyl-3-propionylcarbazole(2),1-methoxy-3-ethylCarbazole(3),1-methoxy-3-formylcarbazole(4),1-methoxy-3-methylcarbazole(5),1-carboxymethylester-3-methylcarbazole(6),1-carboxymethylester-3-ethylcar-bazole(7),manembine(8). All of these compounds were isolated from this plant for the first time except compound(1). The IC50 of compound 2,3,4,5,and 7 against SMMC-7721 was40. 93 ± 0. 66,46. 03 ± 2. 05,114. 21 ± 5. 67,15. 79 ± 0. 99 and 185. 1 ± 0. 44,respectively. The compound(2),(3),(4),(5),(7),showed good cytotoxic activities against SMMC-7721.
The Carbazole alkaloids from Murraya tetramera Huang and their cytotoxic activities were investigated in this study. The ethanol extract from Murraya tetramera Huang were separated by chromatographic techniques. The structures of these compounds were identified by1 H NMR,3 C NMR,HSQC,HMBC. they were β-sitosterol(1),1-methyl-3-propionylcarbazole(2),1-methoxy-3-ethylCarbazole(3),1-methoxy-3-formylcarbazole(4),1-methoxy-3-methylcarbazole(5),1-carboxymethylester-3-methylcarbazole(6),1-carboxymethylester-3-ethylcar-bazole(7),manembine(8). All of these compounds were isolated from this plant for the first time except compound(1). The IC50 of compound 2,3,4,5,and 7 against SMMC-7721 was40. 93 ± 0. 66,46. 03 ± 2. 05,114. 21 ± 5. 67,15. 79 ± 0. 99 and 185. 1 ± 0. 44,respectively. The compound(2),(3),(4),(5),(7),showed good cytotoxic activities against SMMC-7721.
引文
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2 Guo P,Liu H,Zhu HJ,et al.Research progress on chemical constituents and biological activities of Murraya exotica[J].Drugs&Clinic(现代药物与临床),2015,30:1172-1178.
3 Tang QL,Lu YQ,Luo YP.Progress on research of Murraya paniculata[J].J Anhui Agric Sci(安徽农业科学),2009,37:11523-11525+11529.
4 Du LF,Yang J,Chai X,et al.Chemical constituents from the fruits of Rubus chingii Hu[J].Nat Prod Res Dev(天然产物研究与开发),2014,26:1957-1960.
5 Mahmoud M,Fumihide T,Tomihisa O.Unitque phenyl ether type biflavonnids,zizyflavosides A and B with Biomo/eiic synthesis for zizyflavoside A[J].Heterocycles,2010,81:2497-2509.
6 Nguyen MC,Tran QH,Tran VS,et al.A new dimericcarbazole alkaloid from glycosmis tenocarpa roots[J].CPB(化学与药物通报),2004,52:1175-1178.
7 Adilah S,Kartini A,Mohd AN,et al.Chemical constituents from the roots of malayan murraya koenigii(Rutaceae).malaysian[J].Chem J,2016,18:118-123.
8 Benavides A,Peralta J,Delgado F,et al.Total synthesis of the natural carbazoles murrayanine and murrayafoline A,based on the regioselective diels-alder addition of exo-2-oxazolidinone dienes[J].Synthesis,2005,36:2499-2504.
9 M Mukhlesur Rahman,Alexander I Gray A.benzoisofuranone derivative and carbazole alkaloids from Murraya koenigii and their antimicrobial activity[J].Phyto Chem,2005,66:1601-1606.
10 Deng HD,Mei WL,Zuo WJ,et al.Antibacterial Components from Peels of Clausena lansium(Lour.)Skeels[J].J Trop and Subt Bot(热带亚热带植物学报),2014,22:195-200.
11 Zuck,Karina,Tawnya,et al.Siamenol,a new carbazole alkaloid from Murraya siamensis[J].J Nat Prod,2000,63.427-428.
12 He ZM,Bai B,Wang H,et al.The antitumous and antiviral activity of total flavonoids from Senecio scandensmn vitro[J].Chin Tradit Pat Med(中成药),2010,32:2045-2047.