Anti-inflammatory and Quinone Reductase-Inducing Compounds from Beilschmiedia mannii

Angora Rémi Constant Ahoua; Aymeric Monteillier; Frédéric Borlat; Olivier Ciclet; Laurence Marcourt; Samad Nejad Ebrahimi; Mamidou Witabouna Koné; Bassirou Bonfoh; Philippe Christen; Muriel Cuendet

doi:10.1055/a-0798-3155

Planta Medica, Table of Contents

Planta Med 2019; 85(05): 379-384
DOI: 10.1055/a-0798-3155

Biological and Pharmacological Activity

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Anti-inflammatory and Quinone Reductase-Inducing Compounds from Beilschmiedia mannii

Angora Rémi Constant Ahoua

¹Centre Suisse de Recherches Scientifiques en Côte dʼIvoire, Abidjan, Côte dʼIvoire

,

Aymeric Monteillier

²School of pharmaceutical sciences, University of Geneva, University of Lausanne, Geneva, Switzerland

,

Frédéric Borlat

²School of pharmaceutical sciences, University of Geneva, University of Lausanne, Geneva, Switzerland

,

Olivier Ciclet

²School of pharmaceutical sciences, University of Geneva, University of Lausanne, Geneva, Switzerland

,

Laurence Marcourt

²School of pharmaceutical sciences, University of Geneva, University of Lausanne, Geneva, Switzerland

,

Samad Nejad Ebrahimi

³Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, Iran

,

Mamidou Witabouna Koné

¹Centre Suisse de Recherches Scientifiques en Côte dʼIvoire, Abidjan, Côte dʼIvoire

⁴Unité de Formation et de Recherche des Sciences de la Nature, Université Nangui Abrogoua, Abidjan, Côte dʼIvoire

,

Bassirou Bonfoh

¹Centre Suisse de Recherches Scientifiques en Côte dʼIvoire, Abidjan, Côte dʼIvoire

⁵Swiss Tropical and Public Health Institute, Basel, Switzerland

⁶Department of Epidemiology and Public Health, University of Basel, Basel, Switzerland

,

Philippe Christen

²School of pharmaceutical sciences, University of Geneva, University of Lausanne, Geneva, Switzerland

,

Muriel Cuendet

²School of pharmaceutical sciences, University of Geneva, University of Lausanne, Geneva, Switzerland

› Author Affiliations

Abstract

Previous studies on the therapeutic potential of plant species found in the diet of chimpanzees living in Taï National Park have shown that they could be potential candidates for the search of new molecules useful for humans. Based on the screening of some of these plants, the fruits of Beilschmiedia mannii, whose dichloromethane extract showed cancer chemopreventive properties, were selected. Bioactivity-guided fractionation of the extract resulted in the isolation and identification of two γ-pyrones, including desmethoxydihydromethysticin (1), found in a natural source for the first time, and a new congener, beilschmiediapyrone (2), as well as five known alkamides (3 – 7). Their structures were established by using nuclear magnetic resonance spectroscopy and mass spectrometry methods. The isolated compounds were evaluated for their cancer chemopreventive potential by using quinone reductase induction and nuclear factor-kappa B inhibition tests in Hepa 1c1c7 and HEK-293/NF-κB-Luc cells, respectively. Among them, compounds 1 and 2 were the most active. The concentrations to double the quinone reductase activity were 7.5 µM for compound 1 and 6.1 µM for compound 2. Compounds 1 and 2 inhibited nuclear factor-kappa B with IC₅₀ values of 2.1 and 3.4 µM, respectively. These results are promising with regard to cancer chemoprevention, especially because this plant is also used for cooking by the local population around the Taï forest.

Key words

Beilschmiedia mannii - Lauraceae - 5,6-dihydro-2H-pyran-2-ones - quinone reductase - NF-κB

Full Text

References

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