Synthesis and Investigation of Flavanone Derivatives as Potential New Anti-Inflammatory Agents - Institut Pasteur de Nouvelle-Calédonie Access content directly
Journal Articles Molecules Year : 2022

Synthesis and Investigation of Flavanone Derivatives as Potential New Anti-Inflammatory Agents

Abstract

Flavonoids are polyphenols with broad known pharmacological properties. A series of 2,3-dihydroflavanone derivatives were thus synthesized and investigated for their anti-inflammatory activities. The target flavanones were prepared through cyclization of 2′-hydroxychalcone derivatives, the later obtained by Claisen–Schmidt condensation. Since nitric oxide (NO) represents an important inflammatory mediator, the effects of various flavanones on the NO production in the LPS-induced RAW 264.7 macrophage were assessed in vitro using the Griess test. The most active compounds were flavanone (4G), 2′-carboxy-5,7-dimethoxy-flavanone (4F), 4′-bromo-5,7-dimethoxy-flavanone (4D), and 2′-carboxyflavanone (4J), with IC50 values of 0.603, 0.906, 1.030, and 1.830 µg/mL, respectively. In comparison, pinocembrin achieved an IC50 value of 203.60 µg/mL. Thus, the derivatives synthesized in this work had a higher NO inhibition capacity compared to pinocembrin, demonstrating the importance of pharmacomodulation to improve the biological potential of natural molecules. SARs suggested that the use of a carboxyl-group in the meta-position of the B-ring increases biological activity, whereas compounds carrying halogen substituents in the para-position were less active. The addition of methoxy-groups in the meta-position of the A-ring somewhat decreased the activity. This study successfully identified new bioactive flavanones as promising candidates for the development of new anti-inflammatory agents.
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hal-03603587 , version 1 (14-03-2022)

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Cynthia Sinyeue, Mariko Matsui, Michael Oelgemöller, Frédérique Bregier, Vincent Chaleix, et al.. Synthesis and Investigation of Flavanone Derivatives as Potential New Anti-Inflammatory Agents. Molecules, 2022, 27 (6), pp.1781. ⟨10.3390/molecules27061781⟩. ⟨hal-03603587⟩
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