Synthesis of benzoyl esters of β-amyrin and lupeol and evaluation of their antibiofilm and antidiabetic activities

Alfred Ngenge Tamfu; Aristide Mfifen Munvera; Andreea Veronica Dediu Botezatu; Emmanuel Talla; Ozgur Ceylan; Maurice Tagatsing Fotsing; Joseph Tanyi Mbafor; Farzana Shaheen; Rodica Mihaela Dinica

Results in Chemistry (Jan 2022)

Synthesis of benzoyl esters of β-amyrin and lupeol and evaluation of their antibiofilm and antidiabetic activities

Alfred Ngenge Tamfu,
Aristide Mfifen Munvera,
Andreea Veronica Dediu Botezatu,
Emmanuel Talla,
Ozgur Ceylan,
Maurice Tagatsing Fotsing,
Joseph Tanyi Mbafor,
Farzana Shaheen,
Rodica Mihaela Dinica

Affiliations

Alfred Ngenge Tamfu: Department of Chemical Engineering, School of Chemical Engineering and Mineral Industries, University of Ngaoundere, 454 Ngaoundere Cameroon; Dunarea de Jos University, Faculty of Sciences and Environment, Department of Chemistry, Physics and Environment, Galati, 47 Domneasca Str., 800008, Galati, Romania; Food Quality and Analysis Program, Ula Ali Kocman Vocational School, Mugla Sitki Kocman University, 48000 Mugla, Turkey; Third World Center for Science and Technology, H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan; Corresponding authors at: Department of Chemical Engineering, School of Chemical Engineering and Mineral Industries, University of Ngaoundere, 454 Ngaoundere Cameroon (A. Ngenge Tamfu) and Dunarea de Jos University, Faculty of Sciences and Environment, Department of Chemistry, Physics and Environment, Galati, 47 Domneasca Str., 800008, Galati, Romania (R. Mihaela Dinica).
Aristide Mfifen Munvera: Department of Organic Chemistry, University of Yaounde 1, 812 Yaounde, Cameroon
Andreea Veronica Dediu Botezatu: Dunarea de Jos University, Faculty of Sciences and Environment, Department of Chemistry, Physics and Environment, Galati, 47 Domneasca Str., 800008, Galati, Romania
Emmanuel Talla: Department of Chemical Engineering, School of Chemical Engineering and Mineral Industries, University of Ngaoundere, 454 Ngaoundere Cameroon
Ozgur Ceylan: Food Quality and Analysis Program, Ula Ali Kocman Vocational School, Mugla Sitki Kocman University, 48000 Mugla, Turkey
Maurice Tagatsing Fotsing: Department of Organic Chemistry, University of Yaounde 1, 812 Yaounde, Cameroon
Joseph Tanyi Mbafor: Department of Organic Chemistry, University of Yaounde 1, 812 Yaounde, Cameroon
Farzana Shaheen: Third World Center for Science and Technology, H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Rodica Mihaela Dinica: Dunarea de Jos University, Faculty of Sciences and Environment, Department of Chemistry, Physics and Environment, Galati, 47 Domneasca Str., 800008, Galati, Romania; Corresponding authors at: Department of Chemical Engineering, School of Chemical Engineering and Mineral Industries, University of Ngaoundere, 454 Ngaoundere Cameroon (A. Ngenge Tamfu) and Dunarea de Jos University, Faculty of Sciences and Environment, Department of Chemistry, Physics and Environment, Galati, 47 Domneasca Str., 800008, Galati, Romania (R. Mihaela Dinica).

Journal volume & issue: Vol. 4
p. 100322

Abstract

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Diabetes as well as the enhanced microbial multidrug resistance resulting from biofilm formation, constitutes some of the major health problems around the world. Triterpenoids and their derivatives have been shown to have a great contribution in this domain. A small library of benzoyl esters of lupeol and β-amyrin was synthesized and their structures were characterized by electronic ionization mass spectrometry (EIMS). Their inhibitory potential on pathogenic bacteria biofilms, as well as their inhibitory action on α-amylase and β-glucosidase activities were evaluated. The mass fragmentation patterns from the EIMS data confirm the success of the reactions. The minimal inhibitory concentrations (MIC) varied from 250 to 1000 µg/mL in the antimicrobial activities. Biofilm inhibitory potential of the compounds on S. aureus, E. coli and C. albicans were performed at MIC and sub-MIC concentrations and the results showed concentration-dependent inhibition of biofilms. At MIC, the highest biofilm inhibition was exhibited by compound 7 on S. aureus (60.8 ± 3.2%), compound 3 on E. coli (60.5 ± 2.8%) and compound 8 on C. albicans (56.9 ± 2.5%). For all tested compounds, percentage inhibition of violacein production was 100% at MIC except for the starting compounds 1 and 2. At 24.24 µg/mL the percentage of inhibition varied from 22.9 ± 1.2% to 42.1 ± 1.0% for α-amylase inhibition and at a concentration of 10 µg/mL the percentage of inhibition varied from 49.8 ± 0.3% to 69.3 ± 1.0% for β-glucosidase inhibition. The highest inhibition was shown by compounds 7 and 8 on α-amylase and β-glucosidase assays, respectively. The results show that introduction of benzoyl ester groups at C-3 of lupeol and β-amyrin considerably improves their antibiofilm and antidiabetic potentials.

Published in Results in Chemistry

ISSN: 2211-7156 (Online)
Publisher: Elsevier
Country of publisher: Netherlands
LCC subjects: Science: Chemistry
Website: https://www.journals.elsevier.com/results-in-chemistry/

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