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Antioxidant properties of novel curcumin analogues: A combined experimental and computational study
Journal of Food Biochemistry ( IF 3.5 ) Pub Date : 2020-12-19 , DOI: 10.1111/jfbc.13584
Adriana Slavova-Kazakova 1 , Silvia Angelova 2 , Davide Fabbri 3 , Maria Antonietta Dettori 3 , Vessela D Kancheva 1 , Giovanna Delogu 3
Affiliation  

The multi‐target activity of curcumin makes it a promising pharmacological lead for structural modifications focused on the preparation of new better therapeutics with improved bioavailability. A possible modification is to “decompose” the parent curcumin structure into constituent units and to build up curcumin analogues with biphenyl structural moiety. The antioxidant properties of the so‐called “monomers” (m1–m3) and “dimers” (d1–d3) are studied experimentally and computationally. Their protective effects as chain‐breaking antioxidants are investigated for the individual compounds and in binary/ternary compositions with α‐tocopherol (TOH) and ascorbyl palmitate (AscPH). All monomers manifest significant synergism up to 70% in mixtures with TOH. Synergistic effects are found for the ternary compositions of monomeric analogues upon addition to the binary mixture of standard antioxidants (TOH + AscPH). Dimers with biphenyl skeleton manifest a lower potential in compositions under lipid oxidation conditions. DFT computations provide a detailed insight into the structure and antiradical properties of the curcumin analogues and standard antioxidants.

中文翻译:

新型姜黄素类似物的抗氧化性能:结合实验和计算研究

姜黄素的多靶点活性使其成为结构修饰的有希望的药理学线索,其重点是制备具有更高生物利用度的新的更好的疗法。一种可能的修饰是将母体姜黄素结构“分解”为组成单元,并建立具有联苯结构部分的姜黄素类似物。通过实验和计算研究了所谓的“单体”(m1-m3)和“二聚物”(d1-d3)的抗氧化性能。研究了它们作为单独的化合物以及与α-生育酚(TOH)和抗坏血酸棕榈酸酯(AscPH)形成的二元/三元组合物作为链断裂抗氧化剂的保护作用。与TOH的混合物中,所有单体均显示出高达70%的显着协同作用。加入标准抗氧化剂(TOH + AscPH)的二元混合物后,发现单体类似物的三元组合物具有协同作用。具有联苯骨架的二聚体在脂质氧化条件下在组合物中表现出较低的潜力。DFT计算提供了对姜黄素类似物和标准抗氧化剂的结构和抗自由基性能的详细了解。
更新日期:2021-01-19
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