{"title":"有机锗化合物 3-(三羟基锗基)丙酸对果糖诱导的氨基化合物糖化的抑制作用。","authors":"Mika Masaki , Yasuhiro Shimada , Tomoya Takeda , Hisashi Aso , Takashi Nakamura","doi":"10.1016/j.carres.2024.109191","DOIUrl":null,"url":null,"abstract":"<div><p>3-(Trihydroxygermyl)propanoic acid (THGP), a hydrolysate of poly-<em>trans</em>-[(2-carboxyethyl)germasesquioxane] (Ge-132, also known as repagermanium), can inhibit glycation between glucose/ribose and amino compounds. In addition, THGP may inhibit glycation by inhibiting reactions that occur after Amadori rearrangement and inducing the reversible solubilization of AGEs. In this study, we first investigated the effects and mechanisms on the glycation of fructose and amino compounds by THGP, as a greater reactivity was obtained with fructose than with glucose. Unlike other anti-glycation materials, THGP can form a complex with fructose, the initial compound of glycation. THGP also inhibited the production of AGEs and suppressed the reduction of fructose in a reaction between fructose and arginine. These results indicate that THGP forms a complex with cyclic fructose possessing a <em>cis</em>-diol structure at a reducing end, and that it suppresses the ring-opening of fructose and the progress of the initial glycation reaction. We next tried to evaluate the suppressive effect of glucosyl hesperidin (GHes) and THGP on the reaction of glycation between fructose and collagen. Both compounds effectively reduced the production of AGEs individually, and the combination of them led to a synergistic suppression. 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In addition, THGP may inhibit glycation by inhibiting reactions that occur after Amadori rearrangement and inducing the reversible solubilization of AGEs. In this study, we first investigated the effects and mechanisms on the glycation of fructose and amino compounds by THGP, as a greater reactivity was obtained with fructose than with glucose. Unlike other anti-glycation materials, THGP can form a complex with fructose, the initial compound of glycation. THGP also inhibited the production of AGEs and suppressed the reduction of fructose in a reaction between fructose and arginine. These results indicate that THGP forms a complex with cyclic fructose possessing a <em>cis</em>-diol structure at a reducing end, and that it suppresses the ring-opening of fructose and the progress of the initial glycation reaction. We next tried to evaluate the suppressive effect of glucosyl hesperidin (GHes) and THGP on the reaction of glycation between fructose and collagen. 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引用次数: 0
摘要
3-(三羟基胚芽)丙酸(THGP)是聚反式-[(2-羧乙基)胚芽酶二氧杂环](Ge-132,又称雷帕锗)的水解物,可抑制葡萄糖/核糖与氨基化合物之间的糖化反应。此外,THGP 还可通过抑制阿莫多利重排后发生的反应和诱导 AGEs 的可逆溶解来抑制糖化。在本研究中,我们首先研究了 THGP 对果糖和氨基化合物糖化的影响和机制,因为与葡萄糖相比,THGP 对果糖的反应活性更大。与其他抗糖化材料不同,THGP 能与糖化的初始化合物果糖形成复合物。THGP 还能抑制 AGE 的生成,并抑制果糖与精氨酸反应中果糖的还原。这些结果表明,THGP 在还原端与具有顺式二醇结构的环果糖形成复合物,它抑制了果糖的开环和初始糖化反应的进展。接下来,我们尝试评估葡萄糖基橙皮甙(GHes)和 THGP 对果糖和胶原蛋白之间糖化反应的抑制作用。这两种化合物单独使用都能有效减少 AGEs 的产生,而联合使用则能产生协同抑制作用。因此,通过与其他抗糖化材料结合使用,THGP 可协同发挥抑制糖化的作用,从而抑制 AGE 的产生。
Inhibitory effect of organogermanium compound 3-(trihydroxygermyl)propanoic acid on fructose-induced glycation of amino compounds
3-(Trihydroxygermyl)propanoic acid (THGP), a hydrolysate of poly-trans-[(2-carboxyethyl)germasesquioxane] (Ge-132, also known as repagermanium), can inhibit glycation between glucose/ribose and amino compounds. In addition, THGP may inhibit glycation by inhibiting reactions that occur after Amadori rearrangement and inducing the reversible solubilization of AGEs. In this study, we first investigated the effects and mechanisms on the glycation of fructose and amino compounds by THGP, as a greater reactivity was obtained with fructose than with glucose. Unlike other anti-glycation materials, THGP can form a complex with fructose, the initial compound of glycation. THGP also inhibited the production of AGEs and suppressed the reduction of fructose in a reaction between fructose and arginine. These results indicate that THGP forms a complex with cyclic fructose possessing a cis-diol structure at a reducing end, and that it suppresses the ring-opening of fructose and the progress of the initial glycation reaction. We next tried to evaluate the suppressive effect of glucosyl hesperidin (GHes) and THGP on the reaction of glycation between fructose and collagen. Both compounds effectively reduced the production of AGEs individually, and the combination of them led to a synergistic suppression. Therefore, through combination with other antiglycation materials, THGP may cooperatively exhibit glycation-inhibitory effects and be able to suppress the AGE production.
期刊介绍:
Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects.
Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence.
Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".