Role of Sulphur and Heavier Chalcogens on the Antioxidant Power and Bioactivity of Natural Phenolic Compounds.
Role of Sulphur and Heavier Chalcogens on the Antioxidant Power and Bioactivity of Natural Phenolic Compounds.
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硫和重硫族元素对天然酚类化合物的抗氧化能力和生物活性的作用。
DOI：
10.3390/biom12010090
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发表时间：
2022-01-06
期刊：
影响因子：
5.5
通讯作者：
Napolitano A
中科院分区：
文献类型：
--
作者：
Alfieri ML;Panzella L;Amorati R;Cariola A;Valgimigli L;Napolitano A
天然酚类的活性主要与其抗氧化潜力有关，但最终表现为各种生物效应。对这些种类繁多的化合物进行分子支架操作是目前追求的增强或调节其性质的方法。在酚类化合物上插入含S/Se/Te取代基，可通过与取代位点和几何约束有关的电子效应和立体电子效应，提高/降低它们的H-给体/受体能力。在白藜芦醇或阿魏酸中的氧到硫/硒的电子等排置换导致相对于母体酚的自由基清除活性的增加。受维生素E和黄酮类化合物的启发，人们已经制备了几种硫族取代苯酚，在某些情况下，它们被证明是断链抗氧化剂，比天然对应物要好得多。儿茶酚与生物硫醇（半胱氨酸、谷胱甘肽、二氢硫辛酸）的缀合容易通过添加到相应的邻醌来实现。具有增强的抗氧化活性的化合物的值得注意的实例是人类代谢物5-S-半胱氨酰多巴，由于强铁（III）结合而具有高铁诱导的脂质过氧化抑制活性，5-S-谷胱甘肽白藜芦醇是亚硝化过程的最有效抑制剂，以及5-S-硫辛酰羟基酪醇，以及在各种细胞模型中被证明是有价值的氧化应激保护剂的其多硫化物。已使用不同的方法来评价这些化合物对母体化合物的抗氧化能力。这些包括脂质过氧化烷基过氧自由基的抑制动力学，自由基清除的常见化学测定，模型系统的OH·介导的羟基化/氧化的抑制，铁或铜还原能力，亚硝化物种的清除。此外，计算方法使研究人员能够确定硫属元素改性酚醛树脂的OH基团的键解离焓值，并预测性能最佳的衍生物。最后，含硒和碲的化合物作为谷胱甘肽过氧化物酶的模拟物的活性已被评估，连同其他生物活性，包括在各种细胞模型中的抗癌作用和（神经）保护作用。这些和其他成就进行了讨论和合理化，以指导该领域的未来发展。
The activity of natural phenols is primarily associated to their antioxidant potential, but is ultimately expressed in a variety of biological effects. Molecular scaffold manipulation of this large variety of compounds is a currently pursued approach to boost or modulate their properties. Insertion of S/Se/Te containing substituents on phenols may increase/decrease their H-donor/acceptor ability by electronic and stereo-electronic effects related to the site of substitution and geometrical constrains. Oxygen to sulphur/selenium isosteric replacement in resveratrol or ferulic acid leads to an increase in the radical scavenging activity with respect to the parent phenol. Several chalcogen-substituted phenols inspired by Vitamin E and flavonoids have been prepared, which in some cases prove to be chain-breaking antioxidants, far better than the natural counterparts. Conjugation of catechols with biological thiols (cysteine, glutathione, dihydrolipoic acid) is easily achieved by addition to the corresponding ortho-quinones. Noticeable examples of compounds with potentiated antioxidant activities are the human metabolite 5-S-cysteinyldopa, with high iron-induced lipid peroxidation inhibitory activity, due to strong iron (III) binding, 5-S-glutathionylpiceatannol a most effective inhibitor of nitrosation processes, and 5-S-lipoylhydroxytyrosol, and its polysulfides that proved valuable oxidative-stress protective agents in various cellular models. Different methodologies have been used for evaluation of the antioxidant power of these compounds against the parent compounds. These include kinetics of inhibition of lipid peroxidation alkylperoxyl radicals, common chemical assays of radical scavenging, inhibition of the OH• mediated hydroxylation/oxidation of model systems, ferric- or copper-reducing power, scavenging of nitrosating species. In addition, computational methods allowed researchers to determine the Bond Dissociation Enthalpy values of the OH groups of chalcogen modified phenolics and predict the best performing derivative. Finally, the activity of Se and Te containing compounds as mimic of glutathione peroxidase has been evaluated, together with other biological activities including anticancer action and (neuro)protective effects in various cellular models. These and other achievements are discussed and rationalized to guide future development in the field.
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影响因子：
4
作者：
Carugo O;Resnati G;Metrangolo P
通讯作者：
Metrangolo P
DOI：
10.3390/molecules200813894
发表时间：
2015-07-31
期刊：
Molecules (Basel, Switzerland)
影响因子：
--
作者：
Estevam EC;Witek K;Faulstich L;Nasim MJ;Latacz G;Domínguez-Álvarez E;Kieć-Kononowicz K;Demasi M;Handzlik J;Jacob C
通讯作者：
Jacob C
影响因子：
6.1
作者：
Amorati, Riccardo;Valgimigli, Luca
通讯作者：
Valgimigli, Luca
影响因子：
4.3
作者：
Amorati, Riccardo;Valgimigli, Luca;Engman, Lars
通讯作者：
Engman, Lars
影响因子：
3.6
作者：
Amorati, Riccardo;Valgimigli, Luca;d'Ischia, Marco
通讯作者：
d'Ischia, Marco