Food Chemistry ( IF 8.5 ) Pub Date : 2018-06-19 , DOI: 10.1016/j.foodchem.2018.06.083 Saeed Emami , Zahra Esmaili , Gholamreza Dehghan , Maryam Bahmani , Seyedeh Mahdieh Hashemi , Hassan Mirzaei , Mohammad Shokrzadeh , Seyed Ershad Moradi
Acetophenone and its analogues are naturally-occurring compounds found in many foods and plants. In this study, a series of acetophenone benzoylhydrazones 5a-o were designed and synthesized as new potential antioxidant agents. Designed molecules contain hydrazone and phenolic hydroxyl moieties which possibly contribute to antioxidant activity. The antioxidant properties of compounds 5a-o in terms of reducing ability and radical-scavenging activity were assessed by using FRAP and DPPH tests, respectively. While the unsubstituted compound 5a had the superior capacity in the FRAP assay, the 2,4-dihydroxyacetophenone analogue 5g was the most potent radical scavenger in the DPPH method. The antioxidant potential of representative compounds 5a and 5g was further confirmed by TEAC and ORAC assays. Cell viability assays revealed that while the promising compounds 5a and 5g had no significant toxicity against HepG2 and NIH3T3 cells, they potently protected HepG2 cells against H2O2-induced oxidative damage at low concentrations. Furthermore, spectroscopic studies with different biometals demonstrated that 5g was able to interact with Cu2+ to form a 1:1 complex.
中文翻译:
苯乙酮苯甲酰hydr作为抗氧化剂:合成,体外评价及构效关系研究
苯乙酮及其类似物是在许多食品和植物中发现的天然化合物。在这项研究中,设计并合成了一系列苯乙酮苯甲酰肼5a-o作为新的潜在抗氧化剂。设计的分子包含和酚羟基部分,它们可能有助于抗氧化活性。分别通过使用FRAP和DPPH测试评估了化合物5a-o在还原能力和自由基清除活性方面的抗氧化性能。尽管未取代的化合物5a在FRAP分析中具有优异的容量,但2,4-二羟基苯乙酮类似物5g是DPPH方法中最有效的自由基清除剂。通过TEAC和ORAC分析进一步证实了代表性化合物5a和5g的抗氧化潜能。细胞活力分析表明,尽管有希望的化合物5a和5g对HepG2和NIH3T3细胞没有明显的毒性,但它们在低浓度下有效保护了HepG2细胞免受H 2 O 2诱导的氧化损伤。此外,对不同生物金属的光谱研究表明,5g能够与Cu 2+相互作用形成1:1的络合物。