Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from Tristemma hirtum P. Beauv (Melastomataceae)
Science Journal of Chemistry
Volume 8, Issue 3, June 2020, Pages: 48-58
Received: Mar. 31, 2020; Accepted: Apr. 24, 2020; Published: May 27, 2020
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Authors
Joseph Nandjou Kenfack, Research Unit of Environmental and Applied Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, Dschang, Cameroon
David Tsafack Ngoudjou, Research Unit of Microbiology and Antimicrobial Substances, Department of Biochemistry, Faculty of Science, University of Dschang, Dschang, Cameroon
Beaudelaire Kemvoufo Ponou, Research Unit of Environmental and Applied Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, Dschang, Cameroon
Jonas Kühlborn, Johannes Gutenberg University Mainz, Institute of Organic Chemistry, Mainz, Germany
Borice Tapondjou Tsafack, Research Unit of Environmental and Applied Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, Dschang, Cameroon
Rémy Bertrand Teponno, Research Unit of Environmental and Applied Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, Dschang, Cameroon
Till Opatz, Johannes Gutenberg University Mainz, Institute of Organic Chemistry, Mainz, Germany
Luciano Barboni, School of Science and Technology, Chemistry Division, University of Camerino, Camerino, Italy
Donatien Gatsing, Research Unit of Microbiology and Antimicrobial Substances, Department of Biochemistry, Faculty of Science, University of Dschang, Dschang, Cameroon
Léon Azefack Tapondjou, Research Unit of Environmental and Applied Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, Dschang, Cameroon
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Abstract
The development and spread of resistance to currently available antibiotics is a major drawback in the treatment of microbial infections. Salmonellosis for example remains among the most common cause of morbidity and mortality in developing countries. This study aimed to evaluate the antisalmonellal potential of extracts, fractions, isolated compounds and semi-synthetic flavonoids from Tristemma hirtum P. Beauv. Bioguided fractionation by column chromatography of the EtOAc and n -BuOH fractions led to the isolation of eleven compounds including two new esterified glucuronide flavonoids namely: luteolin-3′-O-β-D-glucuronopyranosylbutyl ester (1), a mixture of compound 1 and quercetin-3-O-β-D-glucuronopyranosylbutyl ester (2). Chemical transformation mainly based on the prenylation of 6-hydroxyapigenin-7-O-β-D-glucopyranoside (5) afforded four new semi-synthetic flavonoid derivatives namely: 6, 4'-O-diprenylapigenin-7-O-β-D-glucopyranoside (5a), 8-C-prenyl-6, 4'-O-diprenylapigenin-7-O-β-D-glucopyranoside (5b), 8-C-prenyl-4'-O-prenylapigenin-7-O-β-D-glucopyranoside (5c), 4'-O-prenylapigenin-7-O-β-D-glucopyranoside (5d). The chemical structures of these compounds were assigned using NMR techniques, mass spectrometry and by comparison of their data with reported ones. The antisalmonellal activity was assessed by determining the Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) using serial microdilution methods. The results showed that the MeOH extract and EtOAc fraction were active against all the bacteria tested with MICs ranging from 24 to 1536 µg/mL. Seven isolated compounds and three semi-synthetic compounds tested showed MIC values ranging from 16 to 256 µg/mL. Compounds 1, 3, 5a, 5c and 11 displayed the most potent antisalmonellal properties but were generally less potent than those of reference drugs. The activity of extracts and isolated compounds could be used as the starting point for the development of alternative phytodrugs against salmonellosis.
Keywords
Tristemma hirtum, Phytochemistry, Structure Elucidation, Semi-synthetic Flavonoid Derivatives, Antisalmonellal Activity, Structure-Activity Relationships
To cite this article
Joseph Nandjou Kenfack, David Tsafack Ngoudjou, Beaudelaire Kemvoufo Ponou, Jonas Kühlborn, Borice Tapondjou Tsafack, Rémy Bertrand Teponno, Till Opatz, Luciano Barboni, Donatien Gatsing, Léon Azefack Tapondjou, Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from Tristemma hirtum P. Beauv (Melastomataceae), Science Journal of Chemistry. Vol. 8, No. 3, 2020, pp. 48-58. doi: 10.11648/j.sjc.20200803.12
Copyright
Copyright © 2020 Authors retain the copyright of this article.
This article is an open access article distributed under the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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