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Alkaline earth metal ion coordination increases the radical scavenging efficiency of kaempferol

机译:碱土金属离子协调增加了Kaempferol的激进清除效率

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摘要

Flavonoids are used as natural additives and antioxidants in foods, and after coordination to metal ions, as drug candidates, depending on the flavonoid structure. The rate of radical scavenging of the ubiquitous plant flavonoid kaempferol (3,5,7,4'-tetrahydroxyflavone, Kaem) was found to be significantly enhanced by coordination of Mg(II), Ca(II), Sr(II), and Ba(II) ions, whereas the radical scavenging rate of apigenin (5,7,4'-trihydroxyflavone, Api) was almost unaffected by alkaline earth metal (AEM) ions, as studied for short-lived b-carotene radical cations (beta-Car(center dot+)) formed by laser flash photolysis in chloroform/ethanol (7 : 3) and for the semi-stable 2,2-diphenyl-1-picrylhydrazyl radical, DPPH center dot, in ethanol at 25 degrees C. A 1 : 1 Mg(II)-Kaem complex was found to be in equilibrium with a 1 : 2 Mg(II)-Kaem(2) complex, while for Ca(II), Sr(II) and Ba(II), only 1 : 2 AEM(II)-Kaem complexes were detected, where all complexes showed 3hydroxyl and 4-carbonyl coordination and stability constants of higher than 10(9) L-2 mol(-2). The 1 : 2 Ca(II)-Kaem(2) complex had the highest second order rate constant for both beta-Car(center dot+) (5 x 10(8) L mol(-1) s(-1)) and DPPH center dot radical (3 x 10(5) L mol(-1) s(-1)) scavenging, which can be attributed to the optimal combination of the stronger electron withdrawing capability of the (n - 1)d orbital in the heavier AEM ions and their spatially asymmetrical structures in 1 : 2 AEM-Kaem complexes with metal ion coordination of the least steric hindrance of two perpendicular flavone backbones as ligands in the Ca(II) complex, as shown by density functional theory calculations.
机译:类黄酮用作食品天然添加剂和抗氧化剂,和协调,以金属离子后,候选药物,取决于类黄酮的结构。无处不在植物的自由基清除率类黄酮山奈酚(3,5,7,4'-四羟基,Kaem)被发现为Mg(II),钙(II),锶(II)的协调来显著增强,并且的Ba(II)离子,而芹菜素(5,7,4'-三羟基黄酮,API)的自由基清除率分别为碱土金属几乎不受影响(AEM)离子,如研究了短暂的β-胡萝卜素自由基阳离子(测试版通过在氯仿/乙醇激光闪光光解形成-Car(中心点+))(7:3)和用于半稳定在25℃下甲2,2-二苯基-1-苦基肼基,DPPH中心点,在乙醇1:1的Mg(II)-Kaem络合物被认为是处于平衡状态以1:2的Mg(II)-Kaem(2)配合物,而对于钙(II),锶(II)和Ba(II)中,仅1:2 AEM(II)检测-Kaem络合物,其中所有的复合物显示出3hydroxyl和4-羰基协调和高于10(9)稳定常数L-2摩尔(-2)。 1:2的Ca(II)-Kaem(2)复合物具有两个β-内车(中心点+)最高二级速率常数(5×10(8)L-摩尔(-1)S(1))和DPPH中心点自由基(3×10(5)L-摩尔(-1)S(-1))的清除,这可以归因于的强吸电子能力的最佳组合(N - 1)在d轨道较重AEM离子及其空间不对称结构在1:2 AEM-Kaem配合物作为配位体的Ca两个垂直黄酮骨架的至少空间位阻的金属离子配位(II)配合物,如由密度泛函理论计算。

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  • 来源
    《RSC Advances》 |2020年第50期|共13页
  • 作者单位

    Renmin Univ China Dept Chem Beijing 100872 Peoples R China;

    Renmin Univ China Dept Chem Beijing 100872 Peoples R China;

    Renmin Univ China Dept Chem Beijing 100872 Peoples R China;

    Renmin Univ China Dept Chem Beijing 100872 Peoples R China;

    Renmin Univ China Dept Chem Beijing 100872 Peoples R China;

    Renmin Univ China Dept Chem Beijing 100872 Peoples R China;

    Renmin Univ China Dept Chem Beijing 100872 Peoples R China;

    Renmin Univ China Dept Chem Beijing 100872 Peoples R China;

    Univ Copenhagen Dept Food Sci Rolighedsvej 30 DK-1958 Frederiksberg C Denmark;

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  • 正文语种 eng
  • 中图分类 化学;
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