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

SYSNO ASEP	0380682
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Redox and Non-Redox Mechanism of In Vitro Cyclooxygenase Inhibition by Natural Quinones
Author(s)	Landa, Přemysl (UEB-Q)_{RID, ORCID} Kutil, Zsófia (UEB-Q) Tremml, V. (AT) Vuorien, A. (AT) Malík, J. (CZ) Dvořáková, Marcela (UEB-Q)_{RID, ORCID} Maršík, Petr (UEB-Q)_{RID, ORCID} Kokoška, L. (CZ) Přibylová, Marie (UEB-Q) Schuster, D. (AT) Vaněk, Tomáš (UEB-Q)_{RID, ORCID}
Source Title	Planta medica - ISSN 0032-0943 Roč. 78, č. 4 (2012), s. 326-333
Number of pages	8 s.
Language	eng - English
Country	DE - Germany
Keywords	inflammation ; prostaglandin synthase ; structure-activity relationship
Subject RIV	GM - Food Processing
R&D Projects	GP525/09/P528 GA ČR - Czech Science Foundation (CSF)
	ME08070 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
CEZ	AV0Z50380511 - UEB-Q (2005-2011)
UT WOS	000301343700005
DOI	10.1055/s-0031-1280430
Annotation	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. IC50 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 that the redox potential of quinones as the mechanisms responsible for in vitro COX inhibition because of 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 activity of primin, embelin, alkannin, and diospyrin. For these four quinones, molecular modeling suggested similar binding modes as for conventional non-steroidal anti-inflammatory drugs (NSAIDs).
Workplace	Institute of Experimental Botany
Contact	David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469
Year of Publishing	2013

Number of the records: 1