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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
1   Centre Suisse de Recherches Scientifiques en Côte dʼIvoire, Abidjan, Côte dʼIvoire
,
Aymeric Monteillier
2   School of pharmaceutical sciences, University of Geneva, University of Lausanne, Geneva, Switzerland
,
Frédéric Borlat
2   School of pharmaceutical sciences, University of Geneva, University of Lausanne, Geneva, Switzerland
,
Olivier Ciclet
2   School of pharmaceutical sciences, University of Geneva, University of Lausanne, Geneva, Switzerland
,
Laurence Marcourt
2   School of pharmaceutical sciences, University of Geneva, University of Lausanne, Geneva, Switzerland
,
Samad Nejad Ebrahimi
3   Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, Iran
,
Mamidou Witabouna Koné
1   Centre Suisse de Recherches Scientifiques en Côte dʼIvoire, Abidjan, Côte dʼIvoire
4   Unité de Formation et de Recherche des Sciences de la Nature, Université Nangui Abrogoua, Abidjan, Côte dʼIvoire
,
Bassirou Bonfoh
1   Centre Suisse de Recherches Scientifiques en Côte dʼIvoire, Abidjan, Côte dʼIvoire
5   Swiss Tropical and Public Health Institute, Basel, Switzerland
6   Department of Epidemiology and Public Health, University of Basel, Basel, Switzerland
,
Philippe Christen
2   School of pharmaceutical sciences, University of Geneva, University of Lausanne, Geneva, Switzerland
,
Muriel Cuendet
2   School of pharmaceutical sciences, University of Geneva, University of Lausanne, Geneva, Switzerland
› Author Affiliations
Further Information

Publication History

received 28 June 2018
revised 06 November 2018

accepted 12 November 2018

Publication Date:
22 November 2018 (online)

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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

Supporting Information

    The biological activity of the DCM extract and fractions from B. mannii, and dose-response curves of compounds inducing QR activity and inhibiting NF-κB are available as Supporting Information.

  • Supporting Information
 

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