ID | 114072 |
タイトル別表記 | Capsaicin enhances astaxanthin action in liposomes
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著者 |
Hirai, Shota
Tokushima University
Maoka, Takashi
Research Institute for Production Development
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キーワード | Antioxidants
Astaxanthin
Liposomes
Capsaicin
Intermolecular interactions
Stereochemistry
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資料タイプ |
学術雑誌論文
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抄録 | We previously demonstrated that co-encapsulation of the potent antioxidant astaxanthin (Asx) and tocotrienols into liposomes results in synergistically higher antioxidative activity than the calculated additive activity of each individual antioxidant-containing liposome, due to intermolecular interactions between terminal ring moieties of the two antioxidants and the polyene chain and the triene moiety. We reported that intermolecular interactions depend on the stereochemistry of Asx, and change the electronic state of the Asx polyene moiety. Based on these findings, we hypothesized that antioxidants that interact with Asx at the terminal ring and polyene moieties may enhance the antioxidative activity. Herein, we selected two candidate antioxidants, capsaicin (Cap) and resveratrol, based on their structures, in which the compounds exhibit similar characteristics to tocotrienols. We evaluated the antioxidative capacities of liposomes co-encapsulating Asx and the selected candidates. Based on hydroxyl radical scavenging activity, Cap was found to synergistically enhance the antioxidative activity of Asx at an optimal Asx/Cap ratio. Intermolecular interactions between Asx and Cap are necessary for the synergistic effect, and the Asx stereoisomer 3R,3’R-form (Asx-R) was predicted to most potently interact. Liposomes co-encapsulating Asx-R and Cap exhibited clear synergistic antioxidative activity at an optimal ratio, whereas liposomes co-encapsulating the other Asx stereoisomer and Cap did not demonstrate such activity. Computational chemistry analysis showed that changes in the electronic state of the polyene moiety of Asx-R are crucial for the synergistic activity. These results suggest that antioxidants that can change the electronic state of Asx via intermolecular interactions may enhance the function of Asx.
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掲載誌名 |
Free Radical Research
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ISSN | 10715762
10292470
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cat書誌ID | AA11001805
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出版者 | Taylor & Francis
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巻 | 54
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号 | 11-12
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開始ページ | 818
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終了ページ | 828
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発行日 | 2019-11-13
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備考 | This is an Accepted Manuscript of an article published by Taylor & Francis in Free Radical Research on 13/11/2019, available online: http://www.tandfonline.com/10.1080/10715762.2019.1693042.
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言語 |
eng
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著者版フラグ |
著者版
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部局 |
薬学系
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