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Radiolytic cyclization products of phloridzin as potent anti-glycation agents
Chemistry & Biodiversity ( IF 2.9 ) Pub Date : 2020-08-21 , DOI: 10.1002/cbdv.202000305
Gyeong Han Jeong 1 , Tae Hoon Kim 1
Affiliation  

The current research examined for radiolytic structure modification and improved bioefficacy of phloridzin by γ‐ray, subsequent to a 50 kGy irradiation dose. Structures of the unusual degraded products phlorocyclin, isophlorocyclin, and radiophlorisin were determined spectroscopically, by detailed nuclear magnetic resonance (NMR) and mass spectrometry (MS). Additionally, absolute configuration of the novel cyclized phlorocyclin and isophlorocyclin were proposed by circular dichroism (CD) spectrum analysis. Among the compounds tested, phlorocyclin and isophlorocyclin exhibit potent antidiabetic complication capacities toward advanced glycation end products (AGEs) formation inhibition assay, with IC50 values of 9.1±0.5 and 13.8±0.7 μM, respectively. Furthermore, the predominantly formed products phlorocyclin and isophlorocyclin exerted significantly enhanced DPPH radical scavenging activity compared to the parent phloridzin. These results indicate that γ‐ray mediated cyclization of phloridzin exerts a positive influence on the bioactivity.

中文翻译:

根皮苷的辐射环化产物作为有效的抗糖化剂

目前的研究检查了在 50 kGy 辐射剂量后通过 γ 射线对根皮苷进行辐射分解结构修饰和提高生物功效。通过详细的核磁共振 (NMR) 和质谱 (MS) 光谱法确定了不寻常的降解产物 phlorocyclin、isophlorocyclin 和 radiophlorisin 的结构。此外,通过圆二色性 (CD) 光谱分析提出了新型环化根际环素和异环素的绝对构型。在测试的化合物中,间苯二酚和异氯环素对晚期糖基化终产物 (AGEs) 形成抑制试验表现出有效的抗糖尿病并发症能力,IC50 值分别为 9.1±0.5 和 13.8±0.7 μM。此外,与母体根皮苷相比,主要形成的产物根皮环素和异氯环素具有显着增强的 DPPH 自由基清除活性。这些结果表明,γ射线介导的根皮苷环化对生物活性产生了积极的影响。
更新日期:2020-08-21
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