黑果悬钩子化学成分及其PTP1B抑制活性的研究
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摘要
目的研究黑果悬钩子Rubus caesius茎叶的化学成分及其对蛋白酪氨酸磷酸酶1B(PTP1B)的抑制活性。方法利用硅胶柱色谱、Sephadex LH-20柱色谱、半制备液相等色谱方法进行分离纯化,根据核磁共振波谱鉴定化合物结构,利用酶标仪测定不同萃取部位和单体化合物的PTP1B抑制活性。结果从黑果悬钩子茎的醋酸乙酯部位分离得到5个化合物,分别鉴定为柚皮苷(1)、芹菜素-7-O-β-D-吡喃葡萄糖苷(2)、异槲皮苷(3)、金丝桃苷(4)、(-)-表儿茶素3-O-没食子酸(5);从叶的醋酸乙酯部位分离得到2个化合物,分别鉴定为类叶升麻苷(6)、鞣花酸(7)。结论所有化合物均为首次从黑果悬钩子中分离得到。不同的萃取部位均有一定的PTP1B抑制活性,化合物6表现出较好的PTP1B抑制活性,IC_(50)为(27.41±0.61)μg/m L,推测该化合物可能是叶的醋酸乙酯部位中主要活性成分。
Objective To investigate the chemical constituents from the stem and leaves of Rubus caesius and the inhibitory activities on PTP 1B. Methods Compounds were separated and purified by silica gel column chromatography, Sephadex LH-20 column chromatography, and preparative liquid chromatography. Their structures were identified by spectral methods. The PTP1 B inhibitory activities were screened by microplate reader. Results Five compounds were obtained from the stems of R. caesius respectively, elucidated as naringin(1), apigenin-7-O-β-D-glucopyranoside(2), isoquercitrin(3), hyperoside(4), and(-)-epicatechin 3-O-gallate(ECG)(5), and two compounds were obtained from the leaves respectively, elucidated as acteoside(6) and ellagic acid(7) respectively. Conclusion Compounds 1—7 are isolated from this plant for the first time. Different fractions and compounds showed different PTP1 B inhibitory activities and acteoside showed high PTP1 B inhibitory activity with the IC_(50) value of(27.41 ± 0.61) μg/m L. This compound may be the main active composition of leaves ethyl acetate fraction.
Objective To investigate the chemical constituents from the stem and leaves of Rubus caesius and the inhibitory activities on PTP 1B. Methods Compounds were separated and purified by silica gel column chromatography, Sephadex LH-20 column chromatography, and preparative liquid chromatography. Their structures were identified by spectral methods. The PTP1 B inhibitory activities were screened by microplate reader. Results Five compounds were obtained from the stems of R. caesius respectively, elucidated as naringin(1), apigenin-7-O-β-D-glucopyranoside(2), isoquercitrin(3), hyperoside(4), and(-)-epicatechin 3-O-gallate(ECG)(5), and two compounds were obtained from the leaves respectively, elucidated as acteoside(6) and ellagic acid(7) respectively. Conclusion Compounds 1—7 are isolated from this plant for the first time. Different fractions and compounds showed different PTP1 B inhibitory activities and acteoside showed high PTP1 B inhibitory activity with the IC_(50) value of(27.41 ± 0.61) μg/m L. This compound may be the main active composition of leaves ethyl acetate fraction.
引文
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[2]孟祥娟,刘斌,热增才旦,等.悬钩子属植物化学成分及药理活性研究进展[J].天然产物研究与开发,2011,23(4):767-775.
[3]游孟涛,李亚葵,郭美丽.覆盆子二氯甲烷萃取物中的化学成分[J].第二军医大学学报,2009,30(10):1199-1202.
[4]邬美云.山莓化学成分研究[J].药学实践杂志,2011,29(4):287-291.
[5]王宝珍,解红霞.悬钩子属植物化学成分和药理作用研究新进展[J].中南药学,2014(5):466-469.
[6]韩加,刘继文.悬钩子属植物生物学作用研究进展[J].中国野生植物资源,2009,28(2):1-5.
[7]Dudzinska D,Luzak B,Boncler M,et al.CD39/NTPDase-1 expression and activity in human umbilical vein endothelial cells are differentially regulated by leaf extracts from Rubus caesius and Rubus idaeus[J].CellMol Biol Lett,2014,19(3):361-380.
[8]Dudzinska D,Bednarska K,Boncler M,et al.The influence of Rubus idaeus and Rubus caesius leaf extracts on platelet aggregation in whole blood.Cross-talk of platelets and neutrophils[J].Platelets,2016,27(5):433-439.
[9]地达尔·巴合提坚,木拉提·克扎衣别克,卡母西别克·努尔哈买提.哈萨克医常用的几种植物药及其应用[J].中国民族医药杂志,2012(5):28-32.
[10]郭寒,葛娟,何大俊,等.正交试验优化黑果悬钩子茎、叶总黄酮的提取纯化及其抗氧化活性[J].食品科学,2015,36(14):10-16.
[11]Fang L L,Cao J Q,Duan L L,et al.Protein tyrosine phosphatase 1B(PTP1B)and alpha-glucosidase inhibitory activities of Schisandra chinensis(Turcz.)Baill[J].J Funct Foods,2014,9:264-270.
[12]Negi P S,Jayaprakasha G K.Antibacterial activity of grapefruit(Citrus paradisi)peel extracts[J].Eur Food Res Technol,2001,213(6):484-487.
[13]Maltese F,Erkelens C,van der Kooy F,et al.Identification of natural epimeric flavanone glycosides by NMR spectroscopy[J].Food Chem,2009,116(2):575-579.
[14]Weber B,Herrmann M,Hartmann B,et al.HPLC/MS and HPLC/NMR as hyphenated techniques for accelerated characterization of the main constituents in Chamomile(Chamomilla recutita L.Rauschert)[J].Eur Food ResTechnol,2007,226(4):755-760.
[15]Deng S,Deng Z,Fan Y,et al.Isolation and purification of three flavonoid glycosides from the leaves of Nelumbo nucifera(Lotus)by high-speed counter-current chromatography[J].JChromatogr B,2009,877(24):2487-2492.
[16]彭冰,曾祖平,李萍,等.香鳞毛蕨中1个新的色原酮苷[J].中草药,2013,44(17):2347-2349.
[17]He D,Huang Y,Ayupbek A,et al.Separation and purification of flavonoids from black currant leaves by high-speed countercurrent chromatography and preparative HPLC[J].J Liq Chromatogr R T,2010,33(5):615-628.
[18]Zhou T,Chen B,Fan G,et al.Application of high-speed counter-current chromatography coupled with highperformance liquid chromatography-diode array detection for the preparative isolation and purification of hyperoside from Hypericum perforatum with online purity monitoring[J].J Chromatogr A,2006,1116(1/2):97-101.
[19]张玉莲,梅任强,刘熙,等.东北岩高兰化学成分研究[J].中草药,2014,45(16):2293-2298.
[20]Davis A L,Cai Y,Davies A P,et al.H-1 and C-13 NMR assignments of some green tea polyphenols[J].Magn Reson Chem,1996,34(11):887-890.
[21]Pendota S C,Aderogba M A,Ndhlala A R,et al.Antimicrobial and acetylcholinesterase inhibitory activities of Buddleja salviifolia(L.)Lam.leaf extracts and isolated compounds[J].J Ethnopharmacol,2013,148(2):515-520.
[22]Nawwar M A M,Hussein S A M,Merfort I.NMR spectral-analysis of polyphenols from punica-granatum[J].Phytochemistry,1994,36(3):793-798.
[23]Li X C,Elsohly H N,Hufford C D,et al.NMR assignments of ellagic acid derivatives[J].Magn Reson Chem,1999,37(11):856-859.