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

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

doi:10.1016/j.rechem.2022.100322

Cited by 19 publications

(14 citation statements)

References 39 publications

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“…The β-glucosidase inhibition test was assessed as previously described [62]. Briefly, a reaction mixture was obtained from 15 µL phosphate buffer (pH 5.0), 20 µL p-nitrophenylβ-D-glucopyranoside (1mg/mL, Sigma-Aldrich ® ) and 20 µL sample or positive control at different concentrations.…”

Section: In Vitro Evaluation Of the Antidiabetic Activitymentioning

confidence: 99%

Cucumis metuliferus L. Fruits Extract with Antioxidant, Anti-Inflammatory, and Antidiabetic Properties as Source of Ursolic Acid

et al. 2023

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To identify healthy, nutritious, and sustainable plant-based products rich in biologically active compounds, this present study was conducted, and the phytochemical composition and biological properties of the hydroethanolic ultrasound-assisted extract of the fruits of Cucumis metuliferus were investigated. Cucumis metuliferus is an unexplored fruit of a climbing plant in the Cucurbitaceae family, widely distributed in the tropical and subtropical regions of sub-Saharan Africa and whose nutritional and medicinal benefits are well known in African countries, especially. Therefore, its cultivation in other regions could influence chemical composition. The structural identification of the compounds from the hydroethanolic extract from Cucumis metuliferus fruits grown in Romania was carried out by chromatographic techniques (HPLC). The main compounds identified were catechin, oleanolic acid, ursolic acid, p-coumaric acid, and epicatechin. Subsequently, a method was proposed to isolate and characterize ursolic acid, one of the major compounds. The obtained results show that the hydroethanolic extract is rich in antioxidant compounds evaluated using the DPPH radical inhibition method (IC50 = 32.74 ± 0.02 µg/mL) and ABTS cation radical inhibition method (IC50 = 11.37 ± 0.07 µg/mL). It also demonstrate in vitro anti-inflammatory activities, such as anti-lipoxygenase (IC50 = 32.90 ± 0.05 µg/mL) and anti-proteinase (IC50 = 16.34 ± 0.07 µg/mL), and antidiabetic properties by inhibiting α-amylase (IC50 = 429.541 ± 0.25 µg/mL) and β-glucosidase activity (IC50 = 385.685 ± 0.76 µg/mL). Therefore, C. metuliferus fruits could be effectively used in the development of various health-promoting products, being not only appetizing, with spectacular appearance and with extended storage life, but also curative and healthy.

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Section: In Vitro Evaluation Of the Antidiabetic Activitymentioning

confidence: 99%

Cucumis metuliferus L. Fruits Extract with Antioxidant, Anti-Inflammatory, and Antidiabetic Properties as Source of Ursolic Acid

et al. 2023

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“…12,15 This EPS selfsecreted polymer matrix provides a scaffold and protective barrier to embedded cells against various stresses such as bacteriophages and host immune responses making them able to resist antimicrobial treatments up to 1000 times more than their planktonic counterparts. [37][38][39] Biofilms contribute to chronic infections that are difficult to treat with ordinary antibiotics. 40 Thus, the inhibition of biofilm production and QS can disrupt the development of the protective three-dimensional structure providing a lead-way for the development of new antiinfective agents.…”

Section: Introductionmentioning

confidence: 99%

Biofilm Disruption and Virulence Attenuation Effects of Essential Oil From Endemic Algerian Cistus munbyi (Cistaceae) Against Clinical Strains of Pseudomonas aeruginosa

Benaissa,

Khadir,

Tamfu

et al. 2024

Natural Product Communications

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Background: Pseudomonas aeruginosa is an opportunistic, resistant and highly pathogenic bacteria, responsible for severe nosocomial infections in humans. There is need to search new antimicrobials to target P. aeruginosa strains. Cistus munbyi is used in traditional medicine to manage infections. Objectives: This work aims to investigate the antimicrobial, antibiofilm and other antivirulence effects of essential oil from C. munbyi against P. aeruginosa. Materials and methods: Essential oil (EO) was prepared by hydro-distillation from C. munbyi, characterized by GC–MS and evaluated for its antimicrobial, antibiofilm and anti-virulence effects against clinical isolates of P. aeruginosa. Results: 100% of compounds were identified with Terpinen-4-ol (33.20%), Sabinene (13.20%), α-Thujene (11.30%), and p-Cymene (9.94%) being the major constituents. The EO had good antimicrobial activity determined by diameters of inhibition zones and broth dilution. At minimal inhibitory concentration (MIC), the EO eliminated more that 70% of young biofilms in 19 strains out of 24 tested strains while at 2MIC, only one strain had biofilm inhibition below 70%. The EO eliminated more than 50% of mature biofilms in 13 strains out of 24 tested. Biofilm disruption was concentration-dependent at sub-MIC and indicated good potential of C. munbyi EO as P. aeruginosa antibiofilm agent. Scanning electron microscopy (SEM) images revealed that untreated colonies had a well-developed biofilm while there was significant reduction of biofilms with distorted architecture and cell shrinkage upon treatment with EO. The C. munbyi EO at MIC and sub-MIC was able to reduce quorum-sensing (QS) virulence factors such as pyocyanin production, exopolysaccharides matrix and elastase secretion. Significant QS revealed by reduction of violacein in C. violaceum (CV12472 and CV026) was observed. Conclusion: The overall results show good anti-pseudomonal effects of C. munbyi EO which makes it a potential agent to reduce the spread of infections and resistance to antibiotics from P. aeruginosa strains.

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“…Despite the development of conventional antimicrobials as solutions, there is a multidrug-resistant pattern in Gram-positive and Gram-negative bacteria, as well as in fungi, resulting in difficult-to-treat or even untreatable infections. 10,[12][13][14] Millions of people suffer from microbial infections, some of which are caused by resistant strains, accounting for millions of deaths worldwide each year. 15 Bacterial biofilms are responsible for approximately 80% of severe and recurrent microbial infections in humans, and microbial cells living within biofilms maybe 10-1000 times more resistant to antibiotics than their planktonic counterparts.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a new diarylhydrazone derivative and an evaluation of its in vitro biofilm inhibition and quorum sensing disruption along with a molecular docking study

Boudiba

Tamfu

Hanini

et al. 2023

Journal of Chemical Research

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Molecules that target quorum sensing and biofilm inhibition are useful antimicrobials. In this regard, a new diarylhydrazone was synthesized and characterized using infrared, high-resolution mass spectrometry and nuclear magnetic resonance experiments as N-[( E)-4-bromo-2,5-diheptyloxybenzylideneamino]-2,4-dinitroaniline (BHBANA). Minimal inhibitory concentrations (MICs) vary from 0.625 to 2.5 mg mL−1. This compound was screened in vitro for its inhibition of quorum sensing–mediated violacein production by Chromobacterium violaceum CV12472 at MIC and sub-MIC and showed percentage inhibition varying from 100% at MIC to 5.7% ± 0.2% at MIC/32. Against Chromobacterium violaceum CV026, BHBANA exhibited anti-quorum-sensing zone diameters of 10.5 ± 0.3 mm and 7.0 ± 0.1 mm at MIC and MIC/2, respectively. BHBANA shows concentration-dependent inhibition of swarming motility on flagellated Pseudomonas aeruginosa PA01 with the highest % inhibition of 28.30% ± 0.50% μg mL−1 at MIC. The product inhibits biofilm formation, with the best biofilm inhibition being observed against Staphylococcus aureus varying from 72.24% ± 0.86% (MIC) to 09.82% ± 0.10% (MIC/8). Molecular docking studies carried out utilizing the Schrodinger software identified interactions between BHBANA and different receptor compartments of Chromobacterium violaceum, which can block pathogenic gene expression. The results suggest the potential of BHBANA in reducing microbial virulence.

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

Cited by 19 publications

References 39 publications

Cucumis metuliferus L. Fruits Extract with Antioxidant, Anti-Inflammatory, and Antidiabetic Properties as Source of Ursolic Acid

Cucumis metuliferus L. Fruits Extract with Antioxidant, Anti-Inflammatory, and Antidiabetic Properties as Source of Ursolic Acid

Biofilm Disruption and Virulence Attenuation Effects of Essential Oil From Endemic Algerian Cistus munbyi (Cistaceae) Against Clinical Strains of Pseudomonas aeruginosa

Synthesis of a new diarylhydrazone derivative and an evaluation of its in vitro biofilm inhibition and quorum sensing disruption along with a molecular docking study

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