黄皮种子中香豆素类化合物的分离、鉴定及其α-葡萄糖苷酶抑制活性和全齿复活线虫致死活性研究
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摘要
目的:分离、鉴定黄皮种子中香豆素类化合物,并研究其α-葡萄糖苷酶抑制活性和全齿复活线虫致死活性。方法:采用柱层析、反相硅胶柱色谱及高效液相色谱技术对黄皮种子的香豆素类化合物进行分离、纯化,并根据理化性质和氢谱(1H-NMR)、碳谱(13C-NMR)数据进行结构鉴定。分别以阿卡波糖、阿维菌素为阳性对照,采用对硝基苯基-α-D-吡喃葡萄糖苷(PNPG)法和贝曼漏斗法分别对上述化合物进行体外α-葡萄糖苷酶抑制活性和全齿复活线虫致死活性考察。结果:从黄皮种子中共分离鉴定出7个香豆素类化合物,分别为7-羟基香豆素(Ⅰ)、黄皮呋喃香豆精(Ⅱ)、Lansiumarin-C(Ⅲ)、Claucoumarin A(Ⅳ)、ClausenalansiminA(Ⅴ)、(E,E)-8-(7-羟基-3,7-二甲基-2,5-二烯基)补骨脂(Ⅵ)、Dihydroindicolactone(Ⅶ)。在质量浓度为0.25 mg/mL时,化合物Ⅰ、Ⅲ、Ⅴ的α-葡萄糖苷酶抑制率分别为(32.4±1.9)%、(37.1±6.0)%、(39.5±1.1)%;在质量浓度为2.5 mg/mL时,化合物Ⅰ、Ⅳ的线虫校正死亡率分别为50.5%、47.9%。结论:香豆素类化合物Ⅰ、Ⅲ、Ⅴ具有α-葡萄糖苷酶抑制活性,化合物Ⅰ、Ⅳ具有全齿复活线虫致死活性。其中,化合物Ⅲ、Ⅴ的α-葡萄糖苷酶抑制活性、化合物Ⅳ的全齿复活线虫致死活性均为首次发现。
OBJECTIVE:To isolate and identify the coumarins from the seeds of Clausena lansium,and to study their inhibitory activity of α-glucosidase and nematicidal activity against Panagrellus redivivus. METHODS:Column chromatography,reversed phase silica gel column chromatography and HPLC method were used to separate and purify the coumarins from the seeds of C. lansium. The structures of compounds were identified according to physicochemical properties,1 H-NMR and13 C-NMR spectral data. Using acarbose and avermectin as positive control,PNPG and Berman funnel methods were used to investigate theα-glucosidase inhibitory activity and nematicidal activity against P. redivivus,respectively. RESULTS:Seven coumarins compounds were isolated from the seeds of C. lansium,and were identified as 7-hydroxy-1-benzopiran-2-one (Ⅰ),Wampetin (Ⅱ),Lansiumarin-C (Ⅲ),Claucoumarin A (Ⅳ),Clausenalansimin A (Ⅴ), (E,E)-8- (7-hydroxy-3,7-dimethylocta-2,5-dienyloxy)psoralen (Ⅵ),Dihydroindicolactone (Ⅶ). Under 0.25 mg/mL,the α-glucosidase inhibitory rates of compounds Ⅰ,Ⅲ,Ⅴ were (32.4±1.9)%, (37.1±6.0)%, (39.5±1.1)%,respectively. Under 2.5 mg/mL,corrected mortality of compounds Ⅰ,Ⅳwere50.5% and 47.9%. CONCLUSIONS:Compounds Ⅰ,Ⅲ,Ⅴ show α-glucosidase inhibitory activity,and compounds Ⅰ,Ⅳ display nematicidal activity against P. redivivus. α-Glucosidase inhibitory activity of compounds Ⅲ, Ⅴ, and nematicidal activity of compound Ⅳ are found for the first time.
OBJECTIVE:To isolate and identify the coumarins from the seeds of Clausena lansium,and to study their inhibitory activity of α-glucosidase and nematicidal activity against Panagrellus redivivus. METHODS:Column chromatography,reversed phase silica gel column chromatography and HPLC method were used to separate and purify the coumarins from the seeds of C. lansium. The structures of compounds were identified according to physicochemical properties,1 H-NMR and13 C-NMR spectral data. Using acarbose and avermectin as positive control,PNPG and Berman funnel methods were used to investigate theα-glucosidase inhibitory activity and nematicidal activity against P. redivivus,respectively. RESULTS:Seven coumarins compounds were isolated from the seeds of C. lansium,and were identified as 7-hydroxy-1-benzopiran-2-one (Ⅰ),Wampetin (Ⅱ),Lansiumarin-C (Ⅲ),Claucoumarin A (Ⅳ),Clausenalansimin A (Ⅴ), (E,E)-8- (7-hydroxy-3,7-dimethylocta-2,5-dienyloxy)psoralen (Ⅵ),Dihydroindicolactone (Ⅶ). Under 0.25 mg/mL,the α-glucosidase inhibitory rates of compounds Ⅰ,Ⅲ,Ⅴ were (32.4±1.9)%, (37.1±6.0)%, (39.5±1.1)%,respectively. Under 2.5 mg/mL,corrected mortality of compounds Ⅰ,Ⅳwere50.5% and 47.9%. CONCLUSIONS:Compounds Ⅰ,Ⅲ,Ⅴ show α-glucosidase inhibitory activity,and compounds Ⅰ,Ⅳ display nematicidal activity against P. redivivus. α-Glucosidase inhibitory activity of compounds Ⅲ, Ⅴ, and nematicidal activity of compound Ⅳ are found for the first time.
引文
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[15]NAM VD,TERUHISA F,HIROFUMI T,et al.Chemical composition of Clausena lansium(Lour.)Skeels leaves and antifungal activity[J].Natural Product Sciences,2016,22(1):35-40.
[16]张智圆.黄芪知母口服吸收有效成分分析鉴定及药理作用研究[D].哈尔滨:哈尔滨商业大学,2010.
[17]马青云,黄圣卓,李红芳,等.杠板归中化学成分生防活性研究[J].湖北农业科学,2013,52(21):5245-5247.
[18]申竹芳,陈其明,刘海帆,等.黄皮香豆精的降血糖作用[J].药学学报,1989,24(5):391-392.
[19]熊曼琪,张横柳,朱章志,等.黄皮叶、小叶山绿豆、广木香降血糖作用的实验研究[J].广州中医学院学报,1994,11(1):41-45.
[2]张瑞明,万树青,赵冬香.黄皮的化学成分及生物活性研究进展[J].天然产物研究与开发,2012,24(1):118-123.
[3]耿红梅,王云志,张嫡群.治疗阿尔茨海默症的天然药物[J].中国药房,2006,17(13):1019-1022.
[4]LI WS,MCCHESNEY JD,ELFERALY FS.Carbazole alkaloids from Clausena lansium[J].Phytochemistry,1991,30(1):343-346.
[5]LIU GT,LI WX,CHEN YY,et al.Hepatoprotective action of nine constituents isolated from the leaves of Clausena lansium in mice[J].Drug Dev Res,1996,39:174-178.
[6]LIN JH.Cinnamamide derivatives from Clausena lansium[J].Phytochemistry,1989,28(2):621-622.
[7]DENG HD,MEI WL,GUO ZK,et al.Monoterpenoid coumarins from the peels of Clausena lansium[J].Planta Med,2014,80(11):955-958.
[8]DENG HD,MEI WL,WANG H,et al.Carbazole alkaloids from the peels of Clausena lansium[J].J Asian Nat Prod Res,2014,16(10):1024-1028.
[9]范玉娇,陈惠琴,梅文莉,等.黄皮种子中酰胺类生物碱及其杀线虫活性研究[J].热带亚热带植物学报,2018,26(1):85-91.
[10]FAN YJ,CHEN HQ,MEI WL,et al.Nematicidal amide alkaloids from the seeds of Clausena lansium[J].Fitoterapia,2018.DOI:10.1016/j.fitote.2018.04.023.
[11]DE SáDE SOUSA NOGUEIRA TB,DE SáDE SOUSANOGUEIRA RB,E SILVA DA,et al.First chemical constituents from Cordia exaltata Lam and antimicrobial activity of two neolignans[J].Molecules,2013,18(9):11086-11099.
[12]KHAN NU,NAQVI SWI,ISHRATULLAH K.Wampetin,a furocoumarin from Clausena wampi[J].Phytochemistry,1983,22(11):2624-2625.
[13]LIU H,LI F,LI CJ,et al.Bioactive furanocoumarins from stems of Clausena lansium[J].Phytochemistry,2014.DOI:10.1016/j.phytochem.2014.08.002.
[14]RASHID MA,GRAY AI,WATERMAN PG,et al.Coumarins from Phebalium tuberculosum ssp.megaphyllum and Phebalium filifolium[J].J Nat Prod,1992,55(7):851-858.
[15]NAM VD,TERUHISA F,HIROFUMI T,et al.Chemical composition of Clausena lansium(Lour.)Skeels leaves and antifungal activity[J].Natural Product Sciences,2016,22(1):35-40.
[16]张智圆.黄芪知母口服吸收有效成分分析鉴定及药理作用研究[D].哈尔滨:哈尔滨商业大学,2010.
[17]马青云,黄圣卓,李红芳,等.杠板归中化学成分生防活性研究[J].湖北农业科学,2013,52(21):5245-5247.
[18]申竹芳,陈其明,刘海帆,等.黄皮香豆精的降血糖作用[J].药学学报,1989,24(5):391-392.
[19]熊曼琪,张横柳,朱章志,等.黄皮叶、小叶山绿豆、广木香降血糖作用的实验研究[J].广州中医学院学报,1994,11(1):41-45.