Mulberry anthocyanins exert anti-AGEs effects by selectively trapping glyoxal and structural-dependently blocking the lysyl residues of β-lactoglobulins.

桑葚花色苷通过选择性捕获乙二醛以及结构依赖性地阻断β-乳球蛋白的赖氨酰残基,从而发挥抗AGEs效应。

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2020
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Abstract
Advanced glycation end-products (AGEs), which instigate many disorders, are mostly mediated by dicarbonyl rearrangements. We studied the corresponding mechanisms of the anti-glycation effects of two anthocyanins purified from mulberry fruits, namely cyanidin 3-glucoside (C3G) and cyanidin 3-rutinoside (C3R), on glycated β-lactoglobulins (β-Lg). Both mulberry anthocyanins (MAs) inhibited the AGEs-formation in a dose-dependent manner, but the effect of C3R was significantly stronger than that of C3G (p < 0.05). MAs inhibited AGEs-formation by selectively trapping dicarbonyls, especially glyoxal. The UPLC-ESI-Q-TOF-MS results characterized that C3R formed mono- and di-glyoxal adducts, where C3G only created di-glyoxal adducts. Additionally, C3R could directly interact with some of the glycation sites of β-Lg. Overall, GO-trapping and β-Lg-MAs covalent/noncovalent binding are disclosed as the key mechanisms of the anti-AGEs activity of MAs on β-Lg, which could be valorised as effectual AGEs inhibitors in proteins-rich matrices.
晚期糖基化终末产物(AGEs)可诱发多种疾病,其形成主要由二羰基重排介导。本研究探讨了从桑葚中纯化的两种花色苷——即矢车菊素-3-葡萄糖苷(C3G)和矢车菊素-3-芸香糖苷(C3R),对糖基化β-乳球蛋白(β-Lg)抗糖基化作用的相应机制。两种桑葚花色苷(MAs)均呈剂量依赖性地抑制 AGEs 的形成,且 C3R 的抑制效果显著强于 C3G(*p* < 0.05)。MAs 通过选择性捕获二羰基化合物(尤其是乙二醛)来抑制 AGEs 的形成。UPLC-ESI-Q-TOF-MS 结果表征显示,C3R 可形成单乙二醛和双乙二醛加合物,而 C3G 仅形成双乙二醛加合物。此外,C3R 还能直接与 β-Lg 的部分糖基化位点发生相互作用。综上所述,乙二醛(GO)捕获以及 β-Lg 与 MAs 之间的共价/非共价结合被揭示为 MAs 对 β-Lg 发挥抗 AGEs 活性的关键机制,其有望作为高效的 AGEs 抑制剂在富含蛋白质的基质中得到开发利用。
Reference Key
khalifa2020mulberrybioorganic Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors
Journal Bioorganic chemistry
Year 2020
DOI
S0045-2068(19)31809-7
URL
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