Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from <i>Tristemma hirtum</i> P. Beauv (Melastomataceae)

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

doi:doi:10.11648/j.sjc.20200803.12

Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from Tristemma hirtum P. Beauv (Melastomataceae)

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

Published in Science Journal of Chemistry (Volume 8, Issue 3)

Received: 31 March 2020 Accepted: 24 April 2020 Published: 27 May 2020

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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.

Published in	Science Journal of Chemistry (Volume 8, Issue 3)
DOI	10.11648/j.sjc.20200803.12
Page(s)	48-58
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2020. Published by Science Publishing Group

Keywords

Tristemma hirtum, Phytochemistry, Structure Elucidation, Semi-synthetic Flavonoid Derivatives, Antisalmonellal Activity, Structure-Activity Relationships

References

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Joseph Nandjou Kenfack, David Tsafack Ngoudjou, Beaudelaire Kemvoufo Ponou, Jonas Kühlborn, Borice Tapondjou Tsafack, et al. (2020). Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from Tristemma hirtum P. Beauv (Melastomataceae). Science Journal of Chemistry, 8(3), 48-58. https://doi.org/10.11648/j.sjc.20200803.12

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ACS Style

Joseph Nandjou Kenfack; David Tsafack Ngoudjou; Beaudelaire Kemvoufo Ponou; Jonas Kühlborn; Borice Tapondjou Tsafack, et al. Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from Tristemma hirtum P. Beauv (Melastomataceae). Sci. J. Chem. 2020, 8(3), 48-58. doi: 10.11648/j.sjc.20200803.12

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AMA Style

Joseph Nandjou Kenfack, David Tsafack Ngoudjou, Beaudelaire Kemvoufo Ponou, Jonas Kühlborn, Borice Tapondjou Tsafack, et al. Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from Tristemma hirtum P. Beauv (Melastomataceae). Sci J Chem. 2020;8(3):48-58. doi: 10.11648/j.sjc.20200803.12

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@article{10.11648/j.sjc.20200803.12,
  author = {Joseph Nandjou Kenfack and David Tsafack Ngoudjou and Beaudelaire Kemvoufo Ponou and Jonas Kühlborn and Borice Tapondjou Tsafack and Rémy Bertrand Teponno and Till Opatz and Luciano Barboni and Donatien Gatsing and Léon Azefack Tapondjou},
  title = {Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from Tristemma hirtum P. Beauv (Melastomataceae)},
  journal = {Science Journal of Chemistry},
  volume = {8},
  number = {3},
  pages = {48-58},
  doi = {10.11648/j.sjc.20200803.12},
  url = {https://doi.org/10.11648/j.sjc.20200803.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20200803.12},
  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.},
 year = {2020}
}

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TY  - JOUR
T1  - Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from Tristemma hirtum P. Beauv (Melastomataceae)
AU  - Joseph Nandjou Kenfack
AU  - David Tsafack Ngoudjou
AU  - Beaudelaire Kemvoufo Ponou
AU  - Jonas Kühlborn
AU  - Borice Tapondjou Tsafack
AU  - Rémy Bertrand Teponno
AU  - Till Opatz
AU  - Luciano Barboni
AU  - Donatien Gatsing
AU  - Léon Azefack Tapondjou
Y1  - 2020/05/27
PY  - 2020
N1  - https://doi.org/10.11648/j.sjc.20200803.12
DO  - 10.11648/j.sjc.20200803.12
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 48
EP  - 58
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20200803.12
AB  - 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.
VL  - 8
IS  - 3
ER  -

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Author Information

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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Joseph Nandjou Kenfack, David Tsafack Ngoudjou, Beaudelaire Kemvoufo Ponou, Jonas Kühlborn, Borice Tapondjou Tsafack, et al. (2020). Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from Tristemma hirtum P. Beauv (Melastomataceae). Science Journal of Chemistry, 8(3), 48-58. https://doi.org/10.11648/j.sjc.20200803.12

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ACS Style

Joseph Nandjou Kenfack; David Tsafack Ngoudjou; Beaudelaire Kemvoufo Ponou; Jonas Kühlborn; Borice Tapondjou Tsafack, et al. Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from Tristemma hirtum P. Beauv (Melastomataceae). Sci. J. Chem. 2020, 8(3), 48-58. doi: 10.11648/j.sjc.20200803.12

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AMA Style

Joseph Nandjou Kenfack, David Tsafack Ngoudjou, Beaudelaire Kemvoufo Ponou, Jonas Kühlborn, Borice Tapondjou Tsafack, et al. Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from Tristemma hirtum P. Beauv (Melastomataceae). Sci J Chem. 2020;8(3):48-58. doi: 10.11648/j.sjc.20200803.12

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@article{10.11648/j.sjc.20200803.12,
  author = {Joseph Nandjou Kenfack and David Tsafack Ngoudjou and Beaudelaire Kemvoufo Ponou and Jonas Kühlborn and Borice Tapondjou Tsafack and Rémy Bertrand Teponno and Till Opatz and Luciano Barboni and Donatien Gatsing and Léon Azefack Tapondjou},
  title = {Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from Tristemma hirtum P. Beauv (Melastomataceae)},
  journal = {Science Journal of Chemistry},
  volume = {8},
  number = {3},
  pages = {48-58},
  doi = {10.11648/j.sjc.20200803.12},
  url = {https://doi.org/10.11648/j.sjc.20200803.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20200803.12},
  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.},
 year = {2020}
}

Copy | Download

TY  - JOUR
T1  - Antisalmonellal Activities of Extracts, Fractions, Compounds and Semi-synthetic Flavonoid Derivatives from Tristemma hirtum P. Beauv (Melastomataceae)
AU  - Joseph Nandjou Kenfack
AU  - David Tsafack Ngoudjou
AU  - Beaudelaire Kemvoufo Ponou
AU  - Jonas Kühlborn
AU  - Borice Tapondjou Tsafack
AU  - Rémy Bertrand Teponno
AU  - Till Opatz
AU  - Luciano Barboni
AU  - Donatien Gatsing
AU  - Léon Azefack Tapondjou
Y1  - 2020/05/27
PY  - 2020
N1  - https://doi.org/10.11648/j.sjc.20200803.12
DO  - 10.11648/j.sjc.20200803.12
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 48
EP  - 58
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20200803.12
AB  - 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.
VL  - 8
IS  - 3
ER  -

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