{"title":"关于潜在海洋氧杂蒽酮抗氧化活性的理论研究。","authors":"Phan Thi Thuy, Nguyen Xuan Ha","doi":"10.1080/10715762.2024.2438918","DOIUrl":null,"url":null,"abstract":"<p><p>In this study, a quantum chemical exploration was conducted to assess the antioxidant activity of xanthones isolated from marine sources, focusing on thermodynamics and kinetics within simulated physiological environments. DFT analysis revealed that xanthones such as 1,4,7-trihydroxy-6-methylxanthone (<b>1</b>), 1,4,5-trihydroxy-2-methylxanthone (<b>2</b>), arthone C (<b>3</b>), 2,3,4,6,8-pentahydroxy-1-methylxanthone (<b>4</b>), sterigmatocystin (<b>5</b>), oxisterigmatocystin C (<b>6</b>), and oxisterigmatocystin D (<b>7</b>) favor the SPLET pathway in water and the FHT pathway in lipid environments. The kinetic study of these xanthones reacting with the hydroperoxyl radical (HOO•) was conducted using the formal hydrogen atom transfer (FHT) mechanism and the single electron transfer (SET) mechanism. The results showed that compounds <b>1</b>-<b>4</b> exhibited antioxidant activities in aqueous environments surpassing that of the reference compound Trolox, with rate constants ranging from 2.02 x 10<sup>5</sup> to 9.44 x 10<sup>7</sup> M<sup>-1</sup>·s<sup>-1</sup>. In lipid environments, compounds <b>1</b> and <b>2</b> also demonstrated higher rate constants than Trolox. Additionally, molecular docking and molecular dynamics analysis suggested that xanthones <b>1</b>-<b>7</b> potentially inhibit the pro-oxidant effect of the Keap1 enzyme, highlighting their promise as both antiradicals and enzyme inhibitors.</p>","PeriodicalId":12411,"journal":{"name":"Free Radical Research","volume":" ","pages":"1-15"},"PeriodicalIF":3.6000,"publicationDate":"2024-12-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Theoretical studies on the antioxidant activity of potential marine xanthones.\",\"authors\":\"Phan Thi Thuy, Nguyen Xuan Ha\",\"doi\":\"10.1080/10715762.2024.2438918\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>In this study, a quantum chemical exploration was conducted to assess the antioxidant activity of xanthones isolated from marine sources, focusing on thermodynamics and kinetics within simulated physiological environments. DFT analysis revealed that xanthones such as 1,4,7-trihydroxy-6-methylxanthone (<b>1</b>), 1,4,5-trihydroxy-2-methylxanthone (<b>2</b>), arthone C (<b>3</b>), 2,3,4,6,8-pentahydroxy-1-methylxanthone (<b>4</b>), sterigmatocystin (<b>5</b>), oxisterigmatocystin C (<b>6</b>), and oxisterigmatocystin D (<b>7</b>) favor the SPLET pathway in water and the FHT pathway in lipid environments. The kinetic study of these xanthones reacting with the hydroperoxyl radical (HOO•) was conducted using the formal hydrogen atom transfer (FHT) mechanism and the single electron transfer (SET) mechanism. The results showed that compounds <b>1</b>-<b>4</b> exhibited antioxidant activities in aqueous environments surpassing that of the reference compound Trolox, with rate constants ranging from 2.02 x 10<sup>5</sup> to 9.44 x 10<sup>7</sup> M<sup>-1</sup>·s<sup>-1</sup>. In lipid environments, compounds <b>1</b> and <b>2</b> also demonstrated higher rate constants than Trolox. Additionally, molecular docking and molecular dynamics analysis suggested that xanthones <b>1</b>-<b>7</b> potentially inhibit the pro-oxidant effect of the Keap1 enzyme, highlighting their promise as both antiradicals and enzyme inhibitors.</p>\",\"PeriodicalId\":12411,\"journal\":{\"name\":\"Free Radical Research\",\"volume\":\" \",\"pages\":\"1-15\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2024-12-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Free Radical Research\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://doi.org/10.1080/10715762.2024.2438918\",\"RegionNum\":3,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Free Radical Research","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1080/10715762.2024.2438918","RegionNum":3,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Theoretical studies on the antioxidant activity of potential marine xanthones.
In this study, a quantum chemical exploration was conducted to assess the antioxidant activity of xanthones isolated from marine sources, focusing on thermodynamics and kinetics within simulated physiological environments. DFT analysis revealed that xanthones such as 1,4,7-trihydroxy-6-methylxanthone (1), 1,4,5-trihydroxy-2-methylxanthone (2), arthone C (3), 2,3,4,6,8-pentahydroxy-1-methylxanthone (4), sterigmatocystin (5), oxisterigmatocystin C (6), and oxisterigmatocystin D (7) favor the SPLET pathway in water and the FHT pathway in lipid environments. The kinetic study of these xanthones reacting with the hydroperoxyl radical (HOO•) was conducted using the formal hydrogen atom transfer (FHT) mechanism and the single electron transfer (SET) mechanism. The results showed that compounds 1-4 exhibited antioxidant activities in aqueous environments surpassing that of the reference compound Trolox, with rate constants ranging from 2.02 x 105 to 9.44 x 107 M-1·s-1. In lipid environments, compounds 1 and 2 also demonstrated higher rate constants than Trolox. Additionally, molecular docking and molecular dynamics analysis suggested that xanthones 1-7 potentially inhibit the pro-oxidant effect of the Keap1 enzyme, highlighting their promise as both antiradicals and enzyme inhibitors.
期刊介绍:
Free Radical Research publishes high-quality research papers, hypotheses and reviews in free radicals and other reactive species in biological, clinical, environmental and other systems; redox signalling; antioxidants, including diet-derived antioxidants and other relevant aspects of human nutrition; and oxidative damage, mechanisms and measurement.