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Constituents of the Stem Bark of Trichilia monadelpha (Thonn.) J. J. De Wilde (Meliaceae) and Their Antibacterial and Antiplasmodial Activities

The chemical investigation of the EtOH extract from the stem bark of Trichilia monadelpha (Thonn.) J. J. De Wilde afforded two new limonoids (1 and 2): 24-acetoxy-21,25-dihydroxy-21,23-epoxytirucall-7-en-3-one (1) and (6R)-1-O-deacetylkhayanolide E (2), together with eleven known compounds (3–13), i...

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Autores principales: Djoumessi, Arnauld Kenfack, Nono, Raymond Ngansop, Neumann, Beate, Stammler, Hans-Georg, Bitchagno, Gabin Thierry Mbahbou, Efange, Noella Molisa, Nkenfou, Celine Nguefeu, Ayong, Lawrence, Lenta, Bruno Ndjakou, Sewald, Norbert, Nkeng-Efouet-Alango, Pépin, Chouna, Jean Rodolphe
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9966138/
https://www.ncbi.nlm.nih.gov/pubmed/36837917
http://dx.doi.org/10.3390/metabo13020298
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author Djoumessi, Arnauld Kenfack
Nono, Raymond Ngansop
Neumann, Beate
Stammler, Hans-Georg
Bitchagno, Gabin Thierry Mbahbou
Efange, Noella Molisa
Nkenfou, Celine Nguefeu
Ayong, Lawrence
Lenta, Bruno Ndjakou
Sewald, Norbert
Nkeng-Efouet-Alango, Pépin
Chouna, Jean Rodolphe
author_facet Djoumessi, Arnauld Kenfack
Nono, Raymond Ngansop
Neumann, Beate
Stammler, Hans-Georg
Bitchagno, Gabin Thierry Mbahbou
Efange, Noella Molisa
Nkenfou, Celine Nguefeu
Ayong, Lawrence
Lenta, Bruno Ndjakou
Sewald, Norbert
Nkeng-Efouet-Alango, Pépin
Chouna, Jean Rodolphe
author_sort Djoumessi, Arnauld Kenfack
collection PubMed
description The chemical investigation of the EtOH extract from the stem bark of Trichilia monadelpha (Thonn.) J. J. De Wilde afforded two new limonoids (1 and 2): 24-acetoxy-21,25-dihydroxy-21,23-epoxytirucall-7-en-3-one (1) and (6R)-1-O-deacetylkhayanolide E (2), together with eleven known compounds (3–13), including additional limonoids, flavonoids, triterpenoids, steroids, and fatty acid. Their structures were determined using 1D- and 2D-NMR experiments, ESI mass spectrometry, and single crystal X-ray diffraction analysis. The antibacterial and antiplasmodial activities of the extracts, sub-extracts, fractions, and some of the isolated compounds were evaluated in known pathogenic strains, including Staphylococcus aureus and Plasmodium falciparum. Fraction E (n-Hex/EtOAc 30:70, v/v) showed significant activity against S. aureus ATCC 25923 with a MIC value of 3.90 µg/mL, while one of its constituents (epicatechin (9)) exhibited significant activity with MIC values of 7.80 µg/mL. Interestingly, grandifotane A (6) (IC(50) = 1.37 µM) and khayanolide D (5) (IC(50) = 1.68 µM) were highly active against the chloroquine-sensitive/sulfadoxine-resistant plasmodium falciparum 3D7 strain, unlike their corresponding plant extract and fractions.
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spelling pubmed-99661382023-02-26 Constituents of the Stem Bark of Trichilia monadelpha (Thonn.) J. J. De Wilde (Meliaceae) and Their Antibacterial and Antiplasmodial Activities Djoumessi, Arnauld Kenfack Nono, Raymond Ngansop Neumann, Beate Stammler, Hans-Georg Bitchagno, Gabin Thierry Mbahbou Efange, Noella Molisa Nkenfou, Celine Nguefeu Ayong, Lawrence Lenta, Bruno Ndjakou Sewald, Norbert Nkeng-Efouet-Alango, Pépin Chouna, Jean Rodolphe Metabolites Article The chemical investigation of the EtOH extract from the stem bark of Trichilia monadelpha (Thonn.) J. J. De Wilde afforded two new limonoids (1 and 2): 24-acetoxy-21,25-dihydroxy-21,23-epoxytirucall-7-en-3-one (1) and (6R)-1-O-deacetylkhayanolide E (2), together with eleven known compounds (3–13), including additional limonoids, flavonoids, triterpenoids, steroids, and fatty acid. Their structures were determined using 1D- and 2D-NMR experiments, ESI mass spectrometry, and single crystal X-ray diffraction analysis. The antibacterial and antiplasmodial activities of the extracts, sub-extracts, fractions, and some of the isolated compounds were evaluated in known pathogenic strains, including Staphylococcus aureus and Plasmodium falciparum. Fraction E (n-Hex/EtOAc 30:70, v/v) showed significant activity against S. aureus ATCC 25923 with a MIC value of 3.90 µg/mL, while one of its constituents (epicatechin (9)) exhibited significant activity with MIC values of 7.80 µg/mL. Interestingly, grandifotane A (6) (IC(50) = 1.37 µM) and khayanolide D (5) (IC(50) = 1.68 µM) were highly active against the chloroquine-sensitive/sulfadoxine-resistant plasmodium falciparum 3D7 strain, unlike their corresponding plant extract and fractions. MDPI 2023-02-17 /pmc/articles/PMC9966138/ /pubmed/36837917 http://dx.doi.org/10.3390/metabo13020298 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Djoumessi, Arnauld Kenfack
Nono, Raymond Ngansop
Neumann, Beate
Stammler, Hans-Georg
Bitchagno, Gabin Thierry Mbahbou
Efange, Noella Molisa
Nkenfou, Celine Nguefeu
Ayong, Lawrence
Lenta, Bruno Ndjakou
Sewald, Norbert
Nkeng-Efouet-Alango, Pépin
Chouna, Jean Rodolphe
Constituents of the Stem Bark of Trichilia monadelpha (Thonn.) J. J. De Wilde (Meliaceae) and Their Antibacterial and Antiplasmodial Activities
title Constituents of the Stem Bark of Trichilia monadelpha (Thonn.) J. J. De Wilde (Meliaceae) and Their Antibacterial and Antiplasmodial Activities
title_full Constituents of the Stem Bark of Trichilia monadelpha (Thonn.) J. J. De Wilde (Meliaceae) and Their Antibacterial and Antiplasmodial Activities
title_fullStr Constituents of the Stem Bark of Trichilia monadelpha (Thonn.) J. J. De Wilde (Meliaceae) and Their Antibacterial and Antiplasmodial Activities
title_full_unstemmed Constituents of the Stem Bark of Trichilia monadelpha (Thonn.) J. J. De Wilde (Meliaceae) and Their Antibacterial and Antiplasmodial Activities
title_short Constituents of the Stem Bark of Trichilia monadelpha (Thonn.) J. J. De Wilde (Meliaceae) and Their Antibacterial and Antiplasmodial Activities
title_sort constituents of the stem bark of trichilia monadelpha (thonn.) j. j. de wilde (meliaceae) and their antibacterial and antiplasmodial activities
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9966138/
https://www.ncbi.nlm.nih.gov/pubmed/36837917
http://dx.doi.org/10.3390/metabo13020298
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