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Redox and Non-Redox Mechanism of In Vitro Cyclooxygenase Inhibition by Natural Quinones.

Authors :
Landa, Premysl
Kutil, Zsofia
Temml, Veronika
Vuorinen, Anna
Malik, Jan
Dvorakova, Marcela
Marsik, Petr
Kokoska, Ladislav
Pribylova, Marie
Schuster, Daniela
Vanek, Tomas
Source :
Planta Medica; Apr2012, Vol. 78 Issue 5, p326-333, 8p
Publication Year :
2012

Abstract

In this study, ten anthra, nine naphtho, and five benzoquinone compounds of natural origin and five synthetic naphthoquinones were assessed, using an enzymatic in vitro assay, for their potential to inhibit cyclooxygenase-1 and -2 (COX-1 and COX-2), the key enzymes of the arachidonic acid cascade. IC<subscript>50</subscript> values comparable with COX reference inhibitor indomethacin were recorded for several quinones (primin, alkannin, diospyrin, juglone, 7-methyljuglone, and shikonin). For some of the compounds,we suggest the redox potential of quinones as the mechanism responsible for in vitro COX inhibition because of the quantitative correlation with their pro-oxidant effect. Structure-relationship activity studies revealed that the substitutions at positions 2 and 5 play the key roles in the COX inhibitory and pro-oxidant actions of naphthoquinones. In contrast, the redox mechanism alone could not explain the activity of primin, embelin, alkannin, and diospyrin. For these four quinones, molecular modeling suggested similar binding modes as for conventional nonsteroidal anti-inflammatory drugs (NSAIDs). [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00320943
Volume :
78
Issue :
5
Database :
Complementary Index
Journal :
Planta Medica
Publication Type :
Periodical
Accession number :
73310721
Full Text :
https://doi.org/10.1055/s-0031-1280430