Screening and Structural Characterization of α-Glucosidase Inhibitors from Hawthorn Leaf Flavonoids Extract by Ultrafiltration LC-DAD-MSn and SORI-CID FTICR MS

Screening and Structural Characterization of α-Glucosidase Inhibitors from Hawthorn Leaf Flavonoids Extract by Ultrafiltration LC-DAD-MSn and SORI-CID FTICR MS
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DOI:
10.1016/j.jasms.2009.04.003
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发表时间:
2009-08-01
影响因子:
3.2
通讯作者:
Liu, Shuying
Liu, Shuying
中科院分区:
化学3区
文献类型:
--
作者:
Li, Huilin;Song, Fengrui;Liu, Shuying

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采用体外α-葡萄糖苷酶抑制试验和超滤液相色谱-光电二极管阵列检测-电喷雾串联质谱(LC-DAD-ESI-MSn)相结合的方法,从山楂叶黄酮提取物(HLFE)中筛选α-葡萄糖苷酶抑制剂。结果表明,从HLFE中鉴定出4个α-葡萄糖苷酶抑制剂化合物,其结构分别为槲皮素-3-O-rha-(1-4)-glc-rha和C-糖基黄酮(牡荆素-2“-O-葡萄糖苷,牡荆素-2“-O-鼠李糖苷和牡荆素)的高分辨持续非共振辐射碰撞诱导解离通过傅里叶变换离子回旋共振质谱法(FTICR MS)获得的(SORI-CID)数据。几个其他的C-糖基黄酮(牡荆素,异牡荆素,Orientin,isoorientation)和它们的苷元芹菜素和木犀草素进行了评估,在体外测定,并发现具有很强的α-葡萄糖苷酶抑制活性,以及。此外,黄酮类化合物上的取代基对酶抑制活性有很大的影响。特别是黄酮B环的C-3 ′-OH增加了α-葡萄糖苷酶抑制活性,而A环C-6或C-8的C-糖基化减弱了抑制活性。(J Am Soc Mass Spectrom 2009,20,1496-1503)(C)2009年美国质谱学会
In vitro a-glucosidase inhibition assays and ultrafiltration liquid chromatography with photodiode array detection coupled to electrospray ionization tandem mass spectrometry (ultrafiltration LC-DAD-ESI-MSn) were combined to screen a-glucosidase inhibitors from hawthorn leaf flavonoids extract (HLFE). As a result, four compounds were identified as alpha-glucosidase inhibitors in the HLFE, and their structures were confirmed to be quercetin-3-O-rha-(1-4)-glc-rha and C-glycosylflavones (vitexin-2 ''-O-glucoside, vitexin-2 ''-O-rhamnoside and vitexin) by high-resolution sustained off resonance irradiation collision-induced dissociation (SORI-CID) data obtained by Fourier transform ion cyclotron resonance mass spectrometry (FTICR MS). Several other C-glycosylflavones (vitexin, isovitexin, orientin, isooriention) and their aglycones apigenin and luteolin were evaluated by in vitro assays, and were found to possess strong alpha-glucosidase inhibitory activities as well. Moreover, the substituent groups on the flavones had a great impact on the enzyme inhibition activity. C-3'-OH of the B-ring of flavones in particular increased the alpha-glucosidase inhibition activity, whereas C-glycosylations at C-6 or C-8 of the A ring weakened the inhibition activity. (J Am Soc Mass Spectrom 2009, 20, 1496-1503) (C) 2009 American Society for Mass Spectrometry