number of access : ?
number of downloads : ?
ID 114072
Title Alternative
Capsaicin enhances astaxanthin action in liposomes
Author
Hirai, Shota Tokushima University
Yoshida, Tatsusada Nagasaki International University KAKEN Search Researchers
Maoka, Takashi Research Institute for Production Development
Keywords
Antioxidants
Astaxanthin
Liposomes
Capsaicin
Intermolecular interactions
Stereochemistry
Content Type
Journal Article
Description
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.
Journal Title
Free Radical Research
ISSN
10715762
10292470
NCID
AA11001805
Publisher
Taylor & Francis
Published Date
2019-11-13
Remark
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.
EDB ID
DOI (Published Version)
URL ( Publisher's Version )
FullText File
frr.pdf 1.03 MB
language
eng
TextVersion
Author
departments
Pharmaceutical Sciences