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与霍酚相关新木脂素抗氧化剂的 ROO• 和 HOO• 自由基的反应。

Reaction with ROO• and HOO• Radicals of Honokiol-Related Neolignan Antioxidants.

机构信息

Dipartimento di Scienze Chimiche, Università di Catania, V.le A. Doria 6, 95125 Catania, Italy.

Istituto per la Sintesi Organica e la Fotoreattività (ISOF), Consiglio Nazionale delle Ricerche (CNR), Via Gobetti 101, 40129 Bologna, Italy.

出版信息

Molecules. 2023 Jan 11;28(2):735. doi: 10.3390/molecules28020735.

DOI:10.3390/molecules28020735
PMID:36677790
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9867055/
Abstract

Honokiol is a natural bisphenol neolignan present in the bark of , whose extracts have been employed in oriental medicine to treat several disorders, showing a variety of biological properties, including antitumor activity, potentially related to radical scavenging. Six bisphenol neolignans with structural motifs related to the natural bioactive honokiol were synthesized. Their chain-breaking antioxidant activity was evaluated in the presence of peroxyl (ROO•) and hydroperoxyl (HOO•) radicals by both experimental and computational methods. Depending on the number and position of the hydroxyl and alkyl groups present on the molecules, these derivatives are more or less effective than the reference natural compound. The rate constant of the reaction with ROO• radicals for compound is two orders of magnitude greater than that of honokiol. Moreover, for compounds displaying quinonic oxidized forms, we demonstrate that the addition of 1,4 cyclohexadiene, able to generate HOO• radicals, restores their antioxidant activity, because of the reducing capability of the HOO• radicals. The antioxidant activity of the oxidized compounds in combination with 1,4-cyclohexadiene is, in some cases, greater than that found for the starting compounds towards the peroxyl radicals. This synergy can be applied to maximize the performances of these new bisphenol neolignans.

摘要

和厚朴酚是厚朴树皮中的一种天然联苯二酚新木脂素，其提取物已被用于东方医学治疗多种疾病，具有多种生物活性，包括抗肿瘤活性，可能与自由基清除有关。合成了六种具有与天然生物活性和厚朴酚相关结构母核的联苯新木脂素。通过实验和计算方法，在过氧自由基（ROO•）和氢过氧自由基（HOO•）存在下，评估了它们的链断裂抗氧化活性。根据分子上羟基和烷基的数量和位置，这些衍生物的抗氧化活性或多或少优于参考天然化合物。与和厚朴酚相比，化合物与 ROO•自由基的反应速率常数高两个数量级。此外，对于显示醌式氧化形式的化合物，我们证明了添加能够生成 HOO•自由基的 1,4-环己二烯可以恢复其抗氧化活性，因为 HOO•自由基具有还原能力。在某些情况下，与起始化合物相比，氧化化合物与 1,4-环己二烯的组合的抗氧化活性对过氧自由基更大。这种协同作用可用于最大限度地提高这些新联苯新木脂素的性能。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/22c9072dd1fb/molecules-28-00735-g007.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/3d6683c5f4f8/molecules-28-00735-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/dd8a7f3902c1/molecules-28-00735-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/0861da385ff6/molecules-28-00735-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/4eb0d913399f/molecules-28-00735-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/49a121c54d1c/molecules-28-00735-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/ab386c762614/molecules-28-00735-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/b94972dd892a/molecules-28-00735-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/870ff5e53537/molecules-28-00735-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/22c9072dd1fb/molecules-28-00735-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/c0115d9e7d95/molecules-28-00735-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/a02f9a2d3692/molecules-28-00735-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/0cfcaf64a999/molecules-28-00735-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/64791272b33b/molecules-28-00735-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/3d6683c5f4f8/molecules-28-00735-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/dd8a7f3902c1/molecules-28-00735-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/0861da385ff6/molecules-28-00735-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/4eb0d913399f/molecules-28-00735-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/49a121c54d1c/molecules-28-00735-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/ab386c762614/molecules-28-00735-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/b94972dd892a/molecules-28-00735-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/870ff5e53537/molecules-28-00735-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bc33/9867055/22c9072dd1fb/molecules-28-00735-g007.jpg

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