榅桲籽的化学成分及其PTP1B抑制活性
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摘要
采用硅胶、Sephadex LH-20及半制备液相等多种色谱方法从榅桲种子中分离得到11个化合物,利用UV、1D、2D NMR、HR-ESI-MS等波谱技术分别鉴定为5,7-二羟基-2-正二十五烷基色烯-4-酮(1)、乌苏酸(2)、委陵菜酸(3)、齐墩果酸(4)、β-胡萝卜苷(5)、β-谷甾醇(6)、苦杏仁苷(7)、芦丁(8)、山柰酚(9)、槲皮素(10)和异槲皮素(11)。其中化合物1为新化合物, 3和5为首次从榅桲属中分离得到,其他成分均为首次从榅桲籽中分离得到。用体外PTP1B抑制活性实验,化合物1～4和8对PTP1B有抑制活性,其IC50值分别为0.465、16.14、28.96、23.78和11.70μmol·L~(-1)。
The chemical constituents of Cydonia oblonga(Quince) seeds were investigated using chromato‐graphic methods, including silica gel, Sephadex LH-20 and semi-preparative-HPLC. Eleven compounds were isolated and their structures were elucidated on 1 D or 2 D NMR, and HR-ESI-MS. These analyses have lead to identification of 5,7-dihydroxy-2-n-pentacosanyl chromen-4-one(1), ursolic acid(2), tormentic acid(3), oleanolic acid(4), β-daucosterol(5), β-sitosterol(6), amygdalin(7), rutin(8), kaempferol(9), quercetin(10) and isoquer‐citrin(11). Among these, compound 1 is a new compound, and compounds 3, 5 were isolated from this plant for the first time. Compounds 1-4 and 8 showed significant PTP1 B inhibitory activities with IC50 value of 0.465,16.14, 28.96, 23.78 and 11.70 μmol·L~(-1), respectively.
The chemical constituents of Cydonia oblonga(Quince) seeds were investigated using chromato‐graphic methods, including silica gel, Sephadex LH-20 and semi-preparative-HPLC. Eleven compounds were isolated and their structures were elucidated on 1 D or 2 D NMR, and HR-ESI-MS. These analyses have lead to identification of 5,7-dihydroxy-2-n-pentacosanyl chromen-4-one(1), ursolic acid(2), tormentic acid(3), oleanolic acid(4), β-daucosterol(5), β-sitosterol(6), amygdalin(7), rutin(8), kaempferol(9), quercetin(10) and isoquer‐citrin(11). Among these, compound 1 is a new compound, and compounds 3, 5 were isolated from this plant for the first time. Compounds 1-4 and 8 showed significant PTP1 B inhibitory activities with IC50 value of 0.465,16.14, 28.96, 23.78 and 11.70 μmol·L~(-1), respectively.
引文
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[2]Chinese Pharmacopoeia Commission.The Pharmaceutical Standards of Sanitary Ministry of People's Republic of China(中华人民共和国卫生部药品标准)[S].Urumqi:Xinjiang Health Technology Press,1999:104-105.
[3]Editorial Committee of Chinese Medical Encyclopedia.Encyclo‐pedia of Chinese Medicine(中国医学百科全书)[M].Shanghai:Shanghai Science and Technology Press,2005:177.
[4]Silva BM,Andrade PB,Seabra RM,et al.Composition of Quince(Cydonia oblonga Miller)seeds:phenolics,organic acids and free amino acids[J].Nat Prod Res,2005,19:275-281.
[5]Federico F,Silva BM,Andrade PB,et al.Approach to the study of C-glycosyl flavones by ion trap HPLC-PAD-ESI/MS/MS:application to seeds of Quince(Cydonia oblonga)[J].Phyto‐chem Anal,2003,14:352-359.
[6]Hajinisa,Wang Q,Aisa AA,et al.Fatty acid composition in seeds oil of Cydonia oblonga Mill.analyzed by GC/MS[J].Lishizhen Med Mater Med Res(时珍国医国药),2011,22:2665-2666.
[7]Silva BM,Andrade PB,Valent?o P,et al.Quince(Cydonia oblonga Miller)fruit(pulp,peel,and seed)and jam:antioxidant activity[J].J Agric Food Chem,2004,52:4405-4712.
[8]Magalhaes AS,Silva BM,Pereira JA,et al.Protective effect of Quince(Cydonia oblonga Miller)fruit against oxidative hemolysis of human erythrocytes[J].Food Chem Toxicol,2009,47:1372-1377.
[9]Carvalho M,Silva BM,Silva R,et al.First report on Cydonia oblonga Miller anticancer potential:differential antiproliferative effect against human kidney and colon cancer cells[J].J Agric Food Chem,2010,58:3366-3370.
[10]Ali AH,Hibatoallah K,Amir J,et al.Healing effect of quince seed mucilage on T-2 toxin-induced dermal toxicity in rabbit[J].Exp Toxicol Pathol,2012,64:181-186.
[11]Amina M,Buzore A,Zhao HQ,et al.Screening PTP1Binhibitory activities of extracts from Cydonia oblonga fruits and seeds[J].Northwest Pharm J(西北药学杂志),2017,32:400-402.
[12]Huang M,Xu J,Fan L,et al.Design,synthesis and antidiabetic activities of 5-arylmethylene thiazolidine-2,4-dione derivatives[J].Acta Pharm Sin(药学学报),2017,52:1287-1298.
[13]Zhao HQ,Xin XL,Aisa AA,et al.Screening study on the hypoglycemic fraction from Cichorum glandulosum Boiss.et Huet[J].Lishizhen Med Mater Med Res(时珍国医国药),2012,23:794-797.
[14]Cui L,Li Zh,Sun YN,et al.Protein tyrosine phosphatase 1Binhibitory activity of iridoid glucosides isolated from Plantago asiatica[J].J Yanbian Univ(延边大学学报自然科学版),2011,37:180-183.