青花椒生物碱类化学成分及生物活性研究
|
摘要
目的研究青花椒Zanthoxylum schinifolium生物碱类化学成分及其生物活性。方法采用正相硅胶、Sephadex LH-20、重结晶、半制备HPLC等色谱方法进行分离纯化,通过理化性质及波谱数据鉴定化合物结构,并通过MTS法对化合物进行细胞毒活性筛选。结果从青花椒根部的醋酸乙酯提取物中分离得到9个生物碱,分别鉴定为白藓碱(1)、茵芋碱(2)、青花椒碱(3)、6-甲氧基-呋喃喹诺酮(4)、(+)-(S)-异普拉得斯碱(5)、(+)-(S)-阿瑞罗甫碱(6)、(-)-(S)-日立宁(7)、加锡弥罗果碱(8)、(-)-(S)-丙酮基白屈菜赤碱(9)。结论化合物4为新的天然产物,化合物5～9为首次从该植物中分离得到。其中化合物9能够抑制人支气管上皮细胞的生长,对肿瘤细胞HL-60、SMMC-7721和A-549细胞株具有潜在的细胞毒活性。
Objective To study the chemical structure and bioactivity of the alkaloids from Zanthoxylum schinifolium. Methods The alkaloids were isolated and purified by silica gel, Sephadex LH-20 column chromatography, recrystallization, and semi-preparetive HPLC. Their structures were elucidated by physical and spectroscopic analysis. The cytotoxic activity of these compounds were tested by MTS. Results Nine alkaloids were obtained and identified as dictamnine(1), skimmianine(2), schinifoline(3),6-methoxy-furanoquinolone(4),(+)-(S)-isoplatydesmine(5),(+)-(S)-araliopsine(6),(-)-(S)-ribalinine(7),(-)-(S)-edulinine(8), and(-)-(S)-6-acetonyldihydrochelerythrine(9). Conclusion Compound 4 is a new natural product and compounds 5—9 are isolated from this plant for the first time. Compound 9 has potential cytotoxicity towards HL-60, SMMC-7721, and A549.
Objective To study the chemical structure and bioactivity of the alkaloids from Zanthoxylum schinifolium. Methods The alkaloids were isolated and purified by silica gel, Sephadex LH-20 column chromatography, recrystallization, and semi-preparetive HPLC. Their structures were elucidated by physical and spectroscopic analysis. The cytotoxic activity of these compounds were tested by MTS. Results Nine alkaloids were obtained and identified as dictamnine(1), skimmianine(2), schinifoline(3),6-methoxy-furanoquinolone(4),(+)-(S)-isoplatydesmine(5),(+)-(S)-araliopsine(6),(-)-(S)-ribalinine(7),(-)-(S)-edulinine(8), and(-)-(S)-6-acetonyldihydrochelerythrine(9). Conclusion Compound 4 is a new natural product and compounds 5—9 are isolated from this plant for the first time. Compound 9 has potential cytotoxicity towards HL-60, SMMC-7721, and A549.
引文
[1]孙小文,段志兴.花椒属药用植物研究进展[J].药学学报,1996,31(3):231-240.
[2]Yang X.Aroma constituents and alkylamides of red and green huajiao(Zanthoxylum bungeanum and Zanthoxylum schinifolium)[J].J Agric Food Chem,2008,56(5):1689-1696.
[3]Hu J,Zhang W D,Shen Y H,et al.Two novel alkaloids from Zanthoxylum nitidum[J].Helv Chim Acta,2010,90(4):720-722.
[4]王宇,巨勇,王钊.花椒属植物中生物活性成分研究近况[J].中草药,2002,33(7):666-670.
[5]Tan G T,Pezzuto J M,Kinghorn A D,et al.ChemInform Abstract:Evaluation of natural products as inhibitors of human immunodeficiency virus type 1(HIV-1)reverse transcriptase[J].J Nat Prod,1991,22(31):143-154.
[6]Cheng M J,Wu C C,Tsai I L,et al.Chemical and antiplatelet constituents from the stem of Zanthoxylum beecheyanum[J].JChin Chem Soc,2004,5A(51):1065-1072.
[7]潘竞先,白青,姚冰,等.崖椒茎的化学成分[J].植物资源与环境,1993,2(3):26-28.
[8]Rahman M M,Islam M A,Khondkar P,et al.Alkaloids and lignans from Zanthoxylum budrunga(Rutaceae)[J].Biochem Syst Ecol,2005,33(1):91-96.
[9]Tantapakul C,Phakhodee W,Ritthiwigrom T,et al.Antibacterial compounds from Zanthoxylum rhetsa[J].Arch Pharm Res,2012,35(7):1139-1142.
[10]Brown N M D,Grundon M F,Harrison D M,et al.Quinoline alkaloids-XXI.The 13C NMR spectra of hemiterpenoid alkaloids and related prenyl-quiolines[J].Tetrahedron,1980,36(24):3579-3584.
[11]De Moura N F,Ribeiro H B,Machado E C S,et al.Benzophenanthridine alkaloids from Zanthoxylum rhoifolium[J].Phytochemistry,1997,46(8):1443-1446.
[12]Jackson G E,Campbell W E,Davidowitz B.Two dimensional NMR study of 8-methoxyflindersine,skimmianine and monocrotaline[J].Spectroscopy Lett,1990,23(8):971-982.
[13]Wang D,Gao C,Liu S,et al.Structure investigation of a new alkaloid from Zanthoxylum schinifolium Sieb et Zucc[J].Chem Res Chin U,1991,7(2):124-128.
[14]Grundon M F,Mc Corkindale N J,Rodger M N.The synthesis of furano[3′,2′,3,4]quinolines and the structure ofdictamnic acid[J].J Chem Soc,1955(0),4284-4290.
[15]Wabo H K,Tane P,Connolly J D,et al.Tabouensinium chloride,a novel quaternary pyranoquinoline alkaloid from Araliopsis tabouensis[J].Nat Prod Res,2005,19(6):591-595.
[16]Boyd D R,Sharma N D,Barr S A,et al.Chem Inform Abstract:Synthesis-and absolute stereochemistry assignment of enantiopure dihydrofuroand dihydropyranoquinoline alkaloids[J].J Chem Soc Perkin Trans,2000,32(20):3397-3405.
[17]Chang Z Q,Liu F,Wang S L,et al.Studies on the chemical constituents of Zanthoxylum simulans Hance[J].Acta Pharm Sin,1981,16(5):394-396.
[18]Rollinger J M,Schuster D,Danzl B,et al.In silico target fishing for rationalized ligand discovery exemplified on constituents of Ruta graveolens[J].Planta Med,2009,75(3):195-204.
[19]Yang X,Feng Y,Duffy S,et al.A new quinoline epoxide from the Australian plant Drummondita calida[J].Planta Med,2011,77(14):1644-1647.
[20]Chen J J,Fang H Y,Duh C Y,et al.New indolopyridoquinazoline benzocphen-anthridines and cytotoxic constitutents from Zanthoxylum integrifoliolum[J].Planta Med,2005,71(5):470-475.
[21]Fotie J,Bohle D S,Olivier M,et al.Trypanocidal and antileishmanial dihydrochelerythrine derivatives from Garcinia lucida[J].J Nat Prod,2007,70(10):1650-1653.
[22]Feng F,Ye F Z,Li C L,et al.Two new benzo phenanthridine isoquinoline alkaloids from Macleaya cordata[J].J Nat Med,2012,10(5):378-282.
[23]Chen J J,Lin Y H,Daya S H,et al.New benzenoids and anti-inflammatory constituents from Zanthoxylum nitidum[J].Food Chem,2011,125(2):282-287.
[24]Mansoor T A,Borralho P M,Luo X,et al.6-Acetonyldihydrochelerythrine is a potent inducer of apoptosis in HCT116 and SW620 colon cancer cells[J].JNat Prod,2014,77(8):1825-1830.
[2]Yang X.Aroma constituents and alkylamides of red and green huajiao(Zanthoxylum bungeanum and Zanthoxylum schinifolium)[J].J Agric Food Chem,2008,56(5):1689-1696.
[3]Hu J,Zhang W D,Shen Y H,et al.Two novel alkaloids from Zanthoxylum nitidum[J].Helv Chim Acta,2010,90(4):720-722.
[4]王宇,巨勇,王钊.花椒属植物中生物活性成分研究近况[J].中草药,2002,33(7):666-670.
[5]Tan G T,Pezzuto J M,Kinghorn A D,et al.ChemInform Abstract:Evaluation of natural products as inhibitors of human immunodeficiency virus type 1(HIV-1)reverse transcriptase[J].J Nat Prod,1991,22(31):143-154.
[6]Cheng M J,Wu C C,Tsai I L,et al.Chemical and antiplatelet constituents from the stem of Zanthoxylum beecheyanum[J].JChin Chem Soc,2004,5A(51):1065-1072.
[7]潘竞先,白青,姚冰,等.崖椒茎的化学成分[J].植物资源与环境,1993,2(3):26-28.
[8]Rahman M M,Islam M A,Khondkar P,et al.Alkaloids and lignans from Zanthoxylum budrunga(Rutaceae)[J].Biochem Syst Ecol,2005,33(1):91-96.
[9]Tantapakul C,Phakhodee W,Ritthiwigrom T,et al.Antibacterial compounds from Zanthoxylum rhetsa[J].Arch Pharm Res,2012,35(7):1139-1142.
[10]Brown N M D,Grundon M F,Harrison D M,et al.Quinoline alkaloids-XXI.The 13C NMR spectra of hemiterpenoid alkaloids and related prenyl-quiolines[J].Tetrahedron,1980,36(24):3579-3584.
[11]De Moura N F,Ribeiro H B,Machado E C S,et al.Benzophenanthridine alkaloids from Zanthoxylum rhoifolium[J].Phytochemistry,1997,46(8):1443-1446.
[12]Jackson G E,Campbell W E,Davidowitz B.Two dimensional NMR study of 8-methoxyflindersine,skimmianine and monocrotaline[J].Spectroscopy Lett,1990,23(8):971-982.
[13]Wang D,Gao C,Liu S,et al.Structure investigation of a new alkaloid from Zanthoxylum schinifolium Sieb et Zucc[J].Chem Res Chin U,1991,7(2):124-128.
[14]Grundon M F,Mc Corkindale N J,Rodger M N.The synthesis of furano[3′,2′,3,4]quinolines and the structure ofdictamnic acid[J].J Chem Soc,1955(0),4284-4290.
[15]Wabo H K,Tane P,Connolly J D,et al.Tabouensinium chloride,a novel quaternary pyranoquinoline alkaloid from Araliopsis tabouensis[J].Nat Prod Res,2005,19(6):591-595.
[16]Boyd D R,Sharma N D,Barr S A,et al.Chem Inform Abstract:Synthesis-and absolute stereochemistry assignment of enantiopure dihydrofuroand dihydropyranoquinoline alkaloids[J].J Chem Soc Perkin Trans,2000,32(20):3397-3405.
[17]Chang Z Q,Liu F,Wang S L,et al.Studies on the chemical constituents of Zanthoxylum simulans Hance[J].Acta Pharm Sin,1981,16(5):394-396.
[18]Rollinger J M,Schuster D,Danzl B,et al.In silico target fishing for rationalized ligand discovery exemplified on constituents of Ruta graveolens[J].Planta Med,2009,75(3):195-204.
[19]Yang X,Feng Y,Duffy S,et al.A new quinoline epoxide from the Australian plant Drummondita calida[J].Planta Med,2011,77(14):1644-1647.
[20]Chen J J,Fang H Y,Duh C Y,et al.New indolopyridoquinazoline benzocphen-anthridines and cytotoxic constitutents from Zanthoxylum integrifoliolum[J].Planta Med,2005,71(5):470-475.
[21]Fotie J,Bohle D S,Olivier M,et al.Trypanocidal and antileishmanial dihydrochelerythrine derivatives from Garcinia lucida[J].J Nat Prod,2007,70(10):1650-1653.
[22]Feng F,Ye F Z,Li C L,et al.Two new benzo phenanthridine isoquinoline alkaloids from Macleaya cordata[J].J Nat Med,2012,10(5):378-282.
[23]Chen J J,Lin Y H,Daya S H,et al.New benzenoids and anti-inflammatory constituents from Zanthoxylum nitidum[J].Food Chem,2011,125(2):282-287.
[24]Mansoor T A,Borralho P M,Luo X,et al.6-Acetonyldihydrochelerythrine is a potent inducer of apoptosis in HCT116 and SW620 colon cancer cells[J].JNat Prod,2014,77(8):1825-1830.