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

Isolation and Identification of the Coumarins from the Seeds of Clausena lansium and Study on Their Inhibitory Activity of α-glucosidase and Nematicidal Activity against Panagrellus redivivus

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 ofα-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,1H-NMR and 13C-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,theα-glucosidase inhibitory rates of compoundsⅠ,Ⅲ,Ⅴwere(32.4±1.9)%,(37.1±6.0)%,(39.5±1.1)%,respectively.Under 2.5 mg/mL,corrected mortality of compoundsⅠ,Ⅳwere 50.5%and 47.9%.CONCLUSIONS:CompoundsⅠ,Ⅲ,Ⅴshowα-glucosidase inhibitory activity,and compoundsⅠ,Ⅳdisplay nematicidal activity against P.redivivus.α-Glucosidase inhibitory activity of compoundsⅢ,Ⅴ,and nematicidal activity of compoundⅣare found for the first time.