漆黄素与环糊精的相互作用研究
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摘要
漆黄素具有抗氧化、降肿瘤等多种生物活性功能,但其在水中溶性低、稳定性差的缺点制约了它在医药、化妆品和食品中的应用,而采用环糊精包埋是一条可行之路。采用相溶解度法比较了α-环糊精(α-CD)、β-环糊精(β-CD)、γ-环糊精(γ-CD)和麦芽糖-β-环糊精(M-β-CD)对漆黄素的包埋效果。在此基础上制备了漆黄素与M-β-CD的复合物,运用紫外(UV)、红外(IR)及X射线衍射(XRD)方法对其结构进行了表征,并采用分子对接法建立了漆黄素与环糊精复合物的三维超分子结构。结果表明:M-β-CD和β-CD对漆黄素的包合效果接近,显著优于α-CD和γ-CD。漆黄素与M-β-CD复合后,其物相发生了重大改变,分子对接分析表明,漆黄素沿M-β-CD的大口端方向进入其空腔形成复合物,该超分子结构可能通过氢键维持。
Fisetin possesses many health-promoting properties,such as antioxidant,anticancer activities. Its poor solubility and stability in water limit its application in medicines,cosmetics and foods. Its shortcomings can be overcome by complexing with cyclodextrins(CDs). But there is no systematic report about its interaction with CDs. In view of this,the effect of ɑ-cyclodextrin(α-CD),β-cyclodextrin(β-CD),γ-cyclodextrin(γ-CD) and maltosyl-β-cyclodextrin(M-β-CD) on the aqueous solubility of fisetin was compared by the phase solubility method. Then,the complex of fisetin and M-β-CD was prepared and characterized by using ultraviolet-visible spectrum(UV),ultraviolet-visible spectrum(IR)and X-ray diffraction(XRD). Based on the experimental results,the three-dimensional supermolecular structures of fisetin/CD complexes was established by using molecular docking method. It was found that the inclusion effects of M-β-CD and β-CD on fisetin were higher than those ofα-CD and β-CD. After complexing with M-β-CD,the physicochemical properties of fisetin were significantly changed,which were completely dispersed in M-β-CD. The molecular docking analysis suggested that fisetin entered the hydrophobic cavity from the wide rim of M-β-CD,and the complex was maintained by hydrogen bonding.
Fisetin possesses many health-promoting properties,such as antioxidant,anticancer activities. Its poor solubility and stability in water limit its application in medicines,cosmetics and foods. Its shortcomings can be overcome by complexing with cyclodextrins(CDs). But there is no systematic report about its interaction with CDs. In view of this,the effect of ɑ-cyclodextrin(α-CD),β-cyclodextrin(β-CD),γ-cyclodextrin(γ-CD) and maltosyl-β-cyclodextrin(M-β-CD) on the aqueous solubility of fisetin was compared by the phase solubility method. Then,the complex of fisetin and M-β-CD was prepared and characterized by using ultraviolet-visible spectrum(UV),ultraviolet-visible spectrum(IR)and X-ray diffraction(XRD). Based on the experimental results,the three-dimensional supermolecular structures of fisetin/CD complexes was established by using molecular docking method. It was found that the inclusion effects of M-β-CD and β-CD on fisetin were higher than those ofα-CD and β-CD. After complexing with M-β-CD,the physicochemical properties of fisetin were significantly changed,which were completely dispersed in M-β-CD. The molecular docking analysis suggested that fisetin entered the hydrophobic cavity from the wide rim of M-β-CD,and the complex was maintained by hydrogen bonding.
引文
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[2]徐娜,许凯扬,方芳,等.聚酰胺分离纯化黄栌叶漆黄素工艺研究[J].食品与机械,2017,33(12):160-163.
[3] DONG B,LIU C,XUE R,et al. Fisetin inhibits cardiac hypertrophy by suppressing oxidative stress[J]. The Journal of Nutritional Biochemistry,2019,62:221-229.
[4] KASHYAP D,SHARMA A,SAK K,et al. Fisetin:A bioactive phytochemical with potential for cancer prevention and pharmacotherapy[J].Life Sciences,2018,194:75-87.
[5] CHO Y,CHUNG J H,DO H J,et al. Effects of fisetin supplementation on hepatic lipogenesis and glucose metabolism in Spraue-Dawley rats fed on a high fat diet[J]. Food Chemistry,2013,139(1-4):720-727.
[6] SUVARNA V,GUJAR P,MURAHARI M. Complexation of phytochemicals with cyclodextrin derivatives-An insight[J]. Biomedicine&Pharmacotherapy,2017,88:1122-1144.
[7] PINHO E,GROOTVELD M,SOARES G,et al.Cyclodextrins as encapsulation agents for plant bioactive compounds[J].Carbohydrate Polymers,2014,101:121-135.
[8]张严,苏志,桂张灿.β-环糊精及衍生物作为生物活性分子研究进展[J].药学研究,2018,37(10):589-592.
[9]崔波,金征宇.麦芽糖基(α-1→6)β-环糊精的酶法合成和结构鉴定[J].高等学校化学学报,2007,28(2):283-285.
[10]范新景,袁超,李嘉琪,等.根皮苷与麦芽糖基-β-环糊精复合物的理化性质研究[J].现代食品科技,2016,32(3):106-112.
[11] LIU B,LI W,ZHAO J,et al. Physicochemical characterisation of the supramolecular structure of luteolin/cyclodextrin inclusion complex[J].Food Chemistry,2013,141(2):900-906.
[12]刘本国,张瑞婷,吴晓楠,等.橙皮苷/羟丙基-β-环糊精包合物的理化性质研究[J].现代食品科技,2013,29(10):2349-2352.
[13] STRA譕I譒AR M,ANDREN譒EK S,譒MIDOVNIK A. Effect ofβ-cyclodextrin on antioxidant activity of coumaric acids[J]. Food Chemistry,2008,110(3):636-642.
[14] LIU B,ZHAO J,LIU Y,et al. Physicochemical properties of the inclusion complex of puerarin and glucosyl-β-cyclodextrin[J]. Journal of Agricultural and Food Chemistry,2012,60(2):12501-12507.
[15] MORRISG M,HUEY R,LINDSTROM W,et al.Autodock4 and autodocktools4:automated docking with selective receptor flexibility[J].Journal of Computational Chemistry,2010,30(16):2785-2791.