民族药四数九里香的化学成分及其细胞毒活性研究
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摘要
为了阐明民族药四数九里香Murraya tetramera Huang的药效物质基础,课题组使用色谱技术从其醇提取物中分离得14个化合物;运用~1H NMR、~(13)C NMR波谱方法和文献数据对比鉴定为正24烷酸(1)、9,13,17,21-tetramethyl-5-docosenoic acid(2)、3-O-β-D-吡喃葡萄糖基-山奈酚甙(3)、补骨脂素(4)、紫苏醛(5)、槲皮素(6)、methyl salicylate glucoside(7)、(9S,10R,11E,13R,15Z)-9,10,13-trihydroxyoctadeca-11,15-dienoic Acid(8)、2-isopropyl-5-methylphenol(9)、β-胡萝卜甘(10)、7-羟基香豆素(11)、七叶内酯(12)、β-谷甾醇醋酸酯(13)、山奈酚(14)。除了化合物4、6外,其他化合物为首次从该植物中分离得到。同时,研究各化合物对5株肿瘤细胞的体外生长抑制作用。与阳性对照组比较,结果表明:化合物3、4、5、6、7、8、10、11、12、13、14对白血病HL60显现良好的细胞毒活性;化合物1～14对肺腺癌A549的的细胞毒活性低于阳性对照组;化合物6、13、14对肝癌SMMC7721显现良好的细胞毒活性;化合物1、2、3、6、7、9、11、12对乳腺癌MCF7显现良好的细胞毒活性;化合物1～14对结肠癌SW480的细胞毒活性低于阳性对照组。
The compounds from Murraya tetramera Huang and their cytotoxic activities were investigated in this study.The ethanol extract from M.tetramera Huang were separated by chromatographic techniques.The structures of these compounds were identified by ~1H-NMR,′~3C-NMR.They were n-24 alkanoic acid(1),9,13,17,21-tetramethyl-5-docosenoic acid(2),3-O-β-D-glucopyranosyl-kaempferol glycoside(3),psoralen(4),perillaldehyde(5),quercetin(6),methyl salicylate glucoside(7),(9S,10R,11E,13R,15Z)-9,10,13-trihydroxyoctadeca-11,15-dienoic acid(8),2-isopropyl-5-methylphenol(9),β-sitosterol-3-O-β-D-glucopy-ranosyl(10),7-hydroxycoumarin(11),esculetin(12),β-sitosterol acetate(13),kaempferol(14).All of these compounds were isolated from this plant for the first time except compound(4) and(6).The cell inhibition rates of compounds against 5 tumor cells in vitro were studied.Compared with the positive control group,the results showed that the cell inhibition rates of compounds 3,4,5,6,7,8,10,11,12,13 and 14 showed good cytotoxicity to HL60,The cell inhibition rates of compounds 6,13 and 14 showed good cytotoxicity to SMMC7721,Compounds 1,2,3,6,7,9,11,12 showed good cytotoxicity to MCF7,and compounds 1-14 showed good cytotoxicity to A549 and MCF7.The cell inhibition rates of compounds 1-14,against A549 and SW480 were lower than the positive control group.
The compounds from Murraya tetramera Huang and their cytotoxic activities were investigated in this study.The ethanol extract from M.tetramera Huang were separated by chromatographic techniques.The structures of these compounds were identified by ~1H-NMR,′~3C-NMR.They were n-24 alkanoic acid(1),9,13,17,21-tetramethyl-5-docosenoic acid(2),3-O-β-D-glucopyranosyl-kaempferol glycoside(3),psoralen(4),perillaldehyde(5),quercetin(6),methyl salicylate glucoside(7),(9S,10R,11E,13R,15Z)-9,10,13-trihydroxyoctadeca-11,15-dienoic acid(8),2-isopropyl-5-methylphenol(9),β-sitosterol-3-O-β-D-glucopy-ranosyl(10),7-hydroxycoumarin(11),esculetin(12),β-sitosterol acetate(13),kaempferol(14).All of these compounds were isolated from this plant for the first time except compound(4) and(6).The cell inhibition rates of compounds against 5 tumor cells in vitro were studied.Compared with the positive control group,the results showed that the cell inhibition rates of compounds 3,4,5,6,7,8,10,11,12,13 and 14 showed good cytotoxicity to HL60,The cell inhibition rates of compounds 6,13 and 14 showed good cytotoxicity to SMMC7721,Compounds 1,2,3,6,7,9,11,12 showed good cytotoxicity to MCF7,and compounds 1-14 showed good cytotoxicity to A549 and MCF7.The cell inhibition rates of compounds 1-14,against A549 and SW480 were lower than the positive control group.
引文
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18 Chen YG,Zhan EY,Chen HF.Saponins with low sugar chain from the leaves of Panax notoginseng(Burk)F.H.Chen.[J].J Chin Med Mat(中药材),2002,25:176-178.
19 Sun BH,Wu YQ,Gao HY,et al.Chemical constituents of Fagopyrum tataricum(L.)Gaertn[J].J Shenyang Pharm Univ(沈阳药科大学学报),2008,7:541-543.
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22 Min BS,Miyuki T,Chao-Mei MA,et al.Kaempferol acetylrhamnosides from the rhizome of Dryopteris crassirhizoma and their inhibitory effects on three different activities of human immunodeficiency virus-1 reverse transcriptase[J].Chem & Pharm Bulletin,2001,49:546-550.
2 Liu JL,Wang SR,Chen QH.Isolation,purification and analysis of The Polysaccharide and Proteinpoly saccharide of Murraya paniculata[J].Chin Biochem J(生物化学杂志),1989,5(1):33-38.
3 Chen Y,Zhang YQ,Qian BC,et al.Pharmacological study of geraniol[J].Chin Tradi Pat Med(中成药),1980,12(1):26-28.
4 Mao ZZ,Huang B Yu ZB.Anti-inflammatory of analgesic effects of volatile oil from Murraya tetramera Huang[J].Yunnan J Tradi Chin Med Mat Med (云南中医中药杂志),2011,8:74-75.
5 Yang QB,Huang XQ,Huang ZL,et al.Effect of Murraya tetramera Huang on blood lipid regulation and hemorheology in hyperlipidemia mice[J].J Liaoning Univ Trad Chin Med (辽宁中医药大学报),2017,6:37-40.
6 Jiang PC,Li J,Yang HC,et al.HPLC determination of meranzin and phebalosin in Murraya exotica L.[J].Chin J Tradit Chin Med Pharm(中华中医药杂志),2012,27:169-171.
7 Run JH,Ma YD,Wang XZ,et al.HPLC determination of flavonoids in leaves of Murraya paniculata L.Jack[J].Chin J Pharm Anal(药物分析杂志),2008,28:1630-1632.
8 Ya QK,Lu WJ,Chen JY,et al.Study on the chemical constituent from Murraya tetramera Huang[J].Guangxi Sci(广西科学),2010,17:347-348.
9 Chung IM,Ali M,Khanh TD,et al.New stigmastane steroids constituents from rice hulls of Oryza sativa and inhibitory activity on radish seed[J].Bulletin Korean Chem Socy,2006,27:93-98.
10 Tomá? R,Valery MD.Isoprenoid polyunsaturated fatty acids from freshwater sponges[J].J Nat Pro,1993,56:1898-1901.
11 Wang GJ,Tsai TH,Lin LC.Prenylflavonol,acylated flavonol glycosides and related compounds from Epimedium sagittatum[J].Phytochem,2007,68:2455-2464.
12 Wang CW,Chen GY,Song XP,et al.Chemical constituents from roots of Millettia speciosa[J].Chin Trad Herb Drugs(中草药),2014,45:1515-1520.
13 Craveiro AA,Vieira IGP.Synthesis of (-)-juvabione and (-)-epi-juvabione[J].J Brazilian Chem Soci,1992,3:124-126.
14 Shao LL,Xu DP.Antioxidant activity and composition of Camellia Been Pollen[J].Nat Prod Res Dev(天然产物研究与开发),2016,28:1919-1923.
15 Zhang Y,Zhang Y,Liu LL,et al.Chemical constituents study on the leaves of Mangifera indica[J].J Trop Subtrop Bot,2014,22:185-189.
16 Sun ZP,Gui LP,Guo YQ,et al.Isolation and identification of chemical constituents from the whole plants of Ajuga decumbens[J].J Shenyang Pharm Univ(沈阳药科大学学报),2012,201:758-764.
17 Lee HK,Lee HS.Toxicities of active constituent isolated from Thymus vulgaris flowers and its structural derivatives against Tribolium castaneum(Herbst)[J].Applied Biological Chem,2016,59:821-826.
18 Chen YG,Zhan EY,Chen HF.Saponins with low sugar chain from the leaves of Panax notoginseng(Burk)F.H.Chen.[J].J Chin Med Mat(中药材),2002,25:176-178.
19 Sun BH,Wu YQ,Gao HY,et al.Chemical constituents of Fagopyrum tataricum(L.)Gaertn[J].J Shenyang Pharm Univ(沈阳药科大学学报),2008,7:541-543.
20 Yu HW.Chemical components of Goldfussia yunnanensis,Camchayaloloana and Evodia vestia[D].Chengdu:Chengdu Institute of Biology,Chinese Academy of Sciences(中国科学院成都生物研究所),2008.
21 Guo GM,Li W,Jiang Z.Sterol compounds from Wikstroemia indica(L.)C.A.May[J].J Mountain Agric & Bio(山地农业生物),2012,31(1):77-79.
22 Min BS,Miyuki T,Chao-Mei MA,et al.Kaempferol acetylrhamnosides from the rhizome of Dryopteris crassirhizoma and their inhibitory effects on three different activities of human immunodeficiency virus-1 reverse transcriptase[J].Chem & Pharm Bulletin,2001,49:546-550.