羌活中香豆素类化学成分及其抗氧化活性研究
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摘要
目的研究羌活Notopterygium incisum中的香豆素类化学成分及其抗氧化活性。方法采用重结晶、硅胶柱色谱、SephadexLH-20柱色谱以及制备HPLC等多种分离手段进行分离纯化,通过现代波谱学方法鉴定结构,并采用DPPH法和ABTS法对分离得到的化合物进行抗氧化活性测试。结果从羌活70%乙醇提取物中的二氯甲烷萃取层分离得到10个化合物,分别鉴定为佛手酚(1)、中甸前胡素(2)、镰叶芹二醇(3)、苯乙基阿魏酸酯(4)、丝立尼亭(5)、拱当归素(6)、羌活酚(7)、紫花前胡苷元(8)、(+)-cis-khellactone(9)、水合氧化前胡素(10),并经2种不同的方法测试了这类化合物的抗氧化活性。结论化合物2、6为首次从该植物中分离得到;经DPPH法和ABTS法测试发现化合物1和7具有较强的抗氧化能力;构效关系分析发现5位上具有-OH,多烯烃结构的呋喃环香豆素具有比其他香豆素类化合物更强的抗氧化活性。
Objective To investigate the coumarin compounds from Notopterygium incisum and their anti-oxidant activities.Methods The coumarin compounds and their analogues were separated and purified by recrystallization, silica gel column chromatography, Sephadex LH-20 column chromatography, and preparative HPLC. The structure was identified by modern spectroscopy. The isolated compound was tested for anti-oxidant activity by DPPH and ABTS assay. Results Ten compounds were isolated from the dichloromethane extraction layer of 70% ethanol extract, which were identified as bergaptol(1), d-laserpitin(2),falcarindiol(3), phenethyl ferulate(4), selinidin(5), archangelicin(6), notoptol(7), nodakenetin(8),(+)-cis-khellactone(9), and oxypeucedanin hydrate(10). The anti-oxidant activity of these compounds was tested by DPPH and ABTS methods. Conclusion Compounds 2 and 6 are isolated from this plant for the first time. Compounds 1 and 7 have shown the strongest anti-oxidant activity.The structure-activity relationship(SAR) studies revealed the-OH and unsaturated double bond on C-5′ in the aromatic ring significantly improved the anti-oxidant activity than other coumarin compounds.
Objective To investigate the coumarin compounds from Notopterygium incisum and their anti-oxidant activities.Methods The coumarin compounds and their analogues were separated and purified by recrystallization, silica gel column chromatography, Sephadex LH-20 column chromatography, and preparative HPLC. The structure was identified by modern spectroscopy. The isolated compound was tested for anti-oxidant activity by DPPH and ABTS assay. Results Ten compounds were isolated from the dichloromethane extraction layer of 70% ethanol extract, which were identified as bergaptol(1), d-laserpitin(2),falcarindiol(3), phenethyl ferulate(4), selinidin(5), archangelicin(6), notoptol(7), nodakenetin(8),(+)-cis-khellactone(9), and oxypeucedanin hydrate(10). The anti-oxidant activity of these compounds was tested by DPPH and ABTS methods. Conclusion Compounds 2 and 6 are isolated from this plant for the first time. Compounds 1 and 7 have shown the strongest anti-oxidant activity.The structure-activity relationship(SAR) studies revealed the-OH and unsaturated double bond on C-5′ in the aromatic ring significantly improved the anti-oxidant activity than other coumarin compounds.
引文
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[17]蒋晓文,白俊鹏,田星,等.牛蒡根中黄酮苷类化学成分及其抗氧化活性构效关系的研究[J].中草药,2016,47(5):726-731.
[18]Ng T B,Liu F,Wang Z T.Antioxidative activity of natural products from plants[J].Life Sci,2000,66(8):709-723.
[19]李颖仪,蔡先东.香豆素的药理研究进展[J].中药材,2004,27(3):218-222.
[20]Upritchard J E,Schuurman C R W C,Wiersma A,et al.Spread supplemented with moderate doses of vitamin Eand carotenoids reduces lipid peroxidation in healthy,nonsmoking adults[J].Am J Clin Nutr,2003,78(5):985-992.
[2]肖永庆,孙友富,刘晓宏.羌活化学成分研究[J].中国中药杂志,1994,19(7):421-422.
[3]李丽梅,梁宝德,俞绍文,等.羌活的化学成分[J].中国天然药物,2007,5(5):351-354.
[4]王曙,王天志.宽叶羌活化学成分研究[J].中国中药杂志,1996,21(5):295-296.
[5]肖培根.新编中药志(第一卷)[M].北京:化学工业出版社,2002.
[6]张惠源,王克勤.中国常用中药材[M].北京:科学出版社,1995.
[7]肖永庆,马场色办江,谷口雅颜,等.中药羌活中的香豆素[J].药学学报,1995,30(4):274-279.
[8]杨秀伟,严仲铠,顾哲明,等.羌活化学成分的研究[J].中草药,1993,24(10):507-511.
[9]饶高雄,钮芳娣,孙汉董.中甸前胡的化学成分研究[J].云南植物研究,1990,12(4):434-438.
[10]常新亮,马云保,张雪梅,等.川芎化学成分研究[J].中国中药杂志,2007,32(15):1533-1536.
[11]张梅,周忠玉,任慧,等.紫茎泽兰中的酚类化学成分[J].热带亚热带植物学报,2013,21(1):63-68.
[12]Steck W,Mazure K M.Identification of natural coumarins by NMR spectroscopy[J].Lloydia,1972,35(4):418-439.
[13]肖永庆,谷口雅颜,刘晓宏,等.中药羌活中的香豆素[J].药学学报,1996,30(4):274-279.
[14]Liu A L,Liu B,Qin H L,et al.Anti-influenza virus activities of flavonoids from the medicinal plant Elsholtzia rugulosa[J].Planta Med,2008,74(8):847-851.
[15]Takata M,Okuyama T,Shibata S.Studies on coumarins of a Chinese drug“qian-hu”VIII.Structures of new coumarin-glycosides of“bai-hua qian-hu”[J].Planta Med,1988,54(4):323-327.
[16]张涵庆,袁昌齐,陈桂英,等.杭白芷根化学成分的研究[J].中国药学杂志,1980,15(9):2-4.
[17]蒋晓文,白俊鹏,田星,等.牛蒡根中黄酮苷类化学成分及其抗氧化活性构效关系的研究[J].中草药,2016,47(5):726-731.
[18]Ng T B,Liu F,Wang Z T.Antioxidative activity of natural products from plants[J].Life Sci,2000,66(8):709-723.
[19]李颖仪,蔡先东.香豆素的药理研究进展[J].中药材,2004,27(3):218-222.
[20]Upritchard J E,Schuurman C R W C,Wiersma A,et al.Spread supplemented with moderate doses of vitamin Eand carotenoids reduces lipid peroxidation in healthy,nonsmoking adults[J].Am J Clin Nutr,2003,78(5):985-992.