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2-Styrylchromones modulate prostaglandins production through the inhibition of COX-2
* 1 , 1 , 2 , * 3 , * 1, 4
1  LAQV, REQUIMTE, Laboratory of Applied Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, 4050-313 Porto, Portugal.
2  LAQV, REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
3  LAQV, REQUIMTE, Laboratory of Applied Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, 4050-313 Porto, Portugal
4  Faculty of Agrarian Sciences and Environment, University of the Azores, 9700-042 Angra do Heroísmo, Açores, Portugal.
Academic Editor: Alfredo Berzal-Herranz

Abstract:

2-Styrylchromones (2-SC) are heterocyclic compounds, with a structure of at least 17 carbons and a styryl group attached to a benzoannelated γ-pyrone ring. While the anti-inflammatory potential of 2-SC has become a subject of interest, their effects in inflammatory pathways are still unexplored. Therefore, to better understand 2-SC’s mechanisms of anti-inflammatory action, this study investigated the influence of 10 hydroxylated and methoxylated 2-SC on the inhibitory activity of cyclooxygenase (COX-2), through an in vitro non-cellular assay and an ex vivo assay in human whole blood, based on fluorometric detection of prostaglandin (PG) G2 and colorimetric detection of PGE2, respectively.

A 2-SC hydroxylated at C-7 and C-8 on A-ring and C-3’ and C-4’ on B-ring was the most active in the direct inhibition of COX-2 activity, whereas a 2-SC methoxylated at C-4’ on B-ring was the most active in the ex vivo inhibition of PGE2 production. The obtained results suggest that the presence of OH groups, especially at C-8 on A-ring, favor the direct inhibition of COX-2. Conversely, for inhibition of PGE2 production in a more complex matrix, human blood, it is the presence of an OCH3 at C-4’ on B-ring that seems to be important.

Keywords: 2-styrylchromones; cyclooxygenase-2; prostaglandin; structure-activity relationship
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