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Antimicrobial Properties of Natural Products (Volume Ⅱ)

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: 30 November 2024 | Viewed by 15547

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Prof. Dr. Raphaël E. Duval

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Dean, Faculty of Pharmacy, Université de Lorraine, CNRS, L2CM, 54000 Nancy, France
Interests: research of new anti-infectives; development of new strategies to fight antimicrobial resistance
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Special Issue Information

Dear Colleagues,

I have the great pleasure to invite you to contribute to the second edition of the Special Issue entitled “Antimicrobial Properties of Natural Products (Volume Ⅱ)”.

Indeed, the situation is still very worrying. Antimicrobial Resistance (AMR) continues to increase, all over the World. Having effective antimicrobial treatment to manage patients and treat infection is becoming more and more difficult, which unfortunately has resulted in an increase in the number of deaths. Thus, the latest Centers for Disease Control and Prevention (CDC) AR Threats Report estimated that “More than 2.8 million antibiotic-resistant infections occur in the United States each year, and more than 35,000 people die as a result” [1]. There is therefore always an urgent need to search for new antimicrobial molecules. In addition, natural compounds with antimicrobial activities still appear as a potential source of new antimicrobial molecules, which has not been sufficiently explored.

The aim of this Special Issue is to highlight the recent advances in research on natural products with antimicrobial properties (i.e., antibacterial, antiviral, antifungal, etc.). This Special Issue may include original research articles and reviews on the antimicrobial properties of extracts, fractions, purified compounds, synergistic mixtures against bacteria, viruses or fungi encountered in human infectious diseases in order to identify promising natural compounds that could allow us to respond to the urgency of finding new antimicrobials.

[1] CDC. Antibiotic Resistance Threats in the United States, 2019. Atlanta, GA: U.S. Department of Health and Human Services, CDC; 2019. Available online at http://www.cdc.gov/drugresistance/Biggest-Threats.html

Prof. Dr. Raphaël E. Duval
Guest Editor

Manuscript Submission Information

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Keywords

natural products
antimicrobials properties
bacteria
virus
fungi

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Antimicrobial Properties of Natural Products in Molecules (24 articles)

Published Papers (7 papers)

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Research

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18 pages, 8646 KiB

Open AccessArticle

Preliminary Screening on Antibacterial Crude Secondary Metabolites Extracted from Bacterial Symbionts and Identification of Functional Bioactive Compounds by FTIR, HPLC and Gas Chromatography–Mass Spectrometry

by Gobinath Chandrakasan, Juan Fernando García-Trejo, Ana Angelica Feregrino-Pérez, Humberto Aguirre-Becerra, Enrique Rico García and María Isabel Nieto-Ramírez

Molecules 2024, 29(12), 2914; https://doi.org/10.3390/molecules29122914 - 19 Jun 2024

Viewed by 1147

Abstract

Secondary metabolites, bioactive compounds produced by living organisms, can unveil symbiotic relationships in nature. In this study, soilborne entomopathogenic nematodes associated with symbiotic bacteria (Xenorhabdus stockiae and Photorhabdus luminescens) were extracted from solvent supernatant containing secondary metabolites, demonstrating significant inhibitory effects against E. coli, S. aureus, B. subtilus, P. mirabilis, E. faecalis, and P. stutzeri. The characterization of these secondary metabolites by Fourier transforms infrared spectroscopy revealed amine groups of proteins, hydroxyl and carboxyl groups of polyphenols, hydroxyl groups of polysaccharides, and carboxyl groups of organic acids. Furthermore, the obtained crude extracts were analyzed by high-performance liquid chromatography for the basic identification of potential bioactive peptides. Gas chromatography–mass spectrometry analysis of ethyl acetate extracts from Xenorhabdus stockiae identified major compounds including nonanoic acid derivatives, proline, paromycin, octodecanal derivatives, trioxa-5-aza-1-silabicyclo, 4-octadecenal, methyl ester, oleic acid, and 1,2-benzenedicarboxylicacid. Additional extraction from Photorhabdus luminescens yielded functional compounds such as indole-3-acetic acid, phthalic acid, 1-tetradecanol, nemorosonol, 1-eicosanol, and unsaturated fatty acids. These findings support the potential development of novel natural antimicrobial agents for future pathogen suppression. Full article

(This article belongs to the Special Issue Antimicrobial Properties of Natural Products (Volume Ⅱ))

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13 pages, 1084 KiB

Open AccessArticle

Antifungal Potential of Secondary Metabolites Derived from Arcangelisia flava (L.) Merr.: An Analysis of In Silico Enzymatic Inhibition and In Vitro Efficacy against Candida Species

by Rudi Hendra, Aulia Agustha, Neni Frimayanti, Rizky Abdulah and Hilwan Yuda Teruna

Molecules 2024, 29(10), 2373; https://doi.org/10.3390/molecules29102373 - 17 May 2024

Cited by 1 | Viewed by 997

Abstract

Considering the escalating resistance to conventional antifungal medications, it is critical to identify novel compounds that can efficiently counteract this challenge. The purpose of this research was to elucidate the fungicidal properties of secondary metabolites derived from Arcangelisia flava, with a specific focus on their efficacy against Candida species. This study utilized a combination approach comprising laboratory simulations and experiments to discern and evaluate the biologically active constituents present in the dichloromethane extract of A. flava. The in vitro experiments demonstrated that compounds 1 (palmatine) and 2 (fibraurin) exhibited antifungal properties. The compounds exhibited minimum inhibitory concentrations (MICs) ranging from 15.62 to 62.5 µg/mL against Candida sp. Moreover, compound 1 demonstrated a minimum fungicidal concentration (MFC) of 62.5 µg/mL against Candida glabrata and C. krusei. In contrast, compound 2 exhibited an MFC of 125 µg/mL against both Candida species. Based on a molecular docking study, it was shown that compounds 1 and 2 have a binding free energy of −6.6377 and −6.7075 kcal/mol, respectively, which indicates a strong affinity and specificity for fungal enzymatic targets. This study utilized pharmacophore modeling and Density Functional Theory (DFT) simulations to better understand the interaction dynamics and structural properties crucial for antifungal activity. The findings underscore the potential of secondary metabolites derived from A. flava to act as a foundation for creating novel and highly efficient antifungal treatments, specifically targeting fungal diseases resistant to existing treatment methods. Thus, the results regarding these compounds can provide references for the next stage in antifungal drug design. Further investigation is necessary to thoroughly evaluate these natural substances’ clinical feasibility and safety characteristics, which show great potential as antifungal agents. Full article

(This article belongs to the Special Issue Antimicrobial Properties of Natural Products (Volume Ⅱ))

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14 pages, 912 KiB

Open AccessArticle

Bioactive Compounds from P. pertomentellum That Regulate QS, Biofilm Formation and Virulence Factor Production of P. aeruginosa

by Lida V. Hernández-Moreno, Ludy C. Pabón-Baquero, Juliet A. Prieto-Rodriguez and Oscar J. Patiño-Ladino

Molecules 2023, 28(17), 6181; https://doi.org/10.3390/molecules28176181 - 22 Aug 2023

Cited by 2 | Viewed by 1920

Abstract

Pseudomonas aeruginosa is an opportunistic pathogen responsible for many nosocomial infections. This bacterium uses Quorum Sensing (QS) to generate antimicrobial resistance (AMR) so its disruption is considered a novel approach. The current study describes the antibiofilm and QS inhibitory potential of extract and chemical components from Piper pertomentellum. The methodo- logy included the phytochemical study on the aerial part of the species, the determination of QS inhibition efficacy on Chromobacterium violaceum and the evaluation of the effect on biofilm formation and virulence factors on P. aeruginosa. The phytochemical study led to the isolation and identification of a new piperamide (ethyltembamide 1), together with four known amides (tembamide acetate 2, cepharadione B 3, benzamide 4 and tembamide 5). The results indicated that the ethanolic extract and some fractions reduced violacein production in C. violaceum, however, only the ethanolic extract caused inhibition of biofilm formation of P. aeruginosa on polystyrene microtiter plates. Finally, the investigation determined that molecules (1–5) inhibited the formation of biofilms (50% approximately), while compounds 2–4 can inhibit pyocyanin and elastase production (30–50% approximately). In this way, the study contributes to the determination of the potential of extract and chemical constituents from P pertomentellum to regulate the QS system in P. aeruginosa. Full article

(This article belongs to the Special Issue Antimicrobial Properties of Natural Products (Volume Ⅱ))

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16 pages, 2518 KiB

Open AccessArticle

Structural Characterization, Cytotoxicity, and the Antifungal Mechanism of a Novel Peptide Extracted from Garlic (Allium sativa L.)

by Shuqin Li, Yajie Wang, Jingna Zhou, Jia Wang, Min Zhang and Haixia Chen

Molecules 2023, 28(7), 3098; https://doi.org/10.3390/molecules28073098 - 30 Mar 2023

Cited by 9 | Viewed by 2785

Abstract

Garlic (Allium sativa L.) is a traditional plant with antimicrobial activity. This study aimed to discover new antifungal peptides from garlic, identify their structure, and explore the antimicrobial mechanism. Peptides were separated by chromatography and identified by MALDI-TOF analysis. Structure and conformation were characterized by CD spectrum and NMR analysis. Mechanism studies were conducted by SEM, membrane depolarization, and transcriptomic analysis. The cytotoxicity to mammalian cells as well as drug resistance development ability were also evaluated. A novel antifungal peptide named NpRS with nine amino acids (RSLNLLMFR) was obtained. It was a kind of cationic peptide with a α-helix as the dominant conformation. NOESY correlation revealed a cyclization in the molecule. The peptide significantly inhibited the growth of Candida albicans. The mechanism study indicated that membrane destruction and the interference of ribosome-related pathways might be the main mechanisms of antifungal effects. In addition, the resistance gene CDR1 for azole was down-regulated and the drug resistance was hardly developed in 21 days by the serial passage study. The present study identified a novel antifungal garlic peptide with low toxicity and provided new mechanism information for the peptide at the gene expression level to counter drug resistance. Full article

(This article belongs to the Special Issue Antimicrobial Properties of Natural Products (Volume Ⅱ))

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14 pages, 1083 KiB

Open AccessArticle

Correlation between Chemical Profile of Georgian Propolis Extracts and Their Activity against Helicobacter pylori

by Jarosław Widelski, Piotr Okińczyc, Katarzyna Suśniak, Anna Malm, Anna Bozhadze, Malkhaz Jokhadze and Izabela Korona-Głowniak

Molecules 2023, 28(3), 1374; https://doi.org/10.3390/molecules28031374 - 1 Feb 2023

Cited by 9 | Viewed by 2994

Abstract

Helicobacter pylori (H. pylori) is considered the most common bacterial pathogen colonizing stomach mucosa of almost half the world’s population and is associated with various gastrointestinal diseases (from digestive problems and ulcers to gastric cancer). A lack of new drugs and a growing number of H. pylori antibiotic-resistant strains is a serious therapeutic problem.As a mixture of natural compounds, propolis has antimicrobial activity based on high concentrations of bioactive polyphenols (mainly flavonoids and phenolic acid derivates). The chemical composition of tested Georgian propolis is characterized by the presence of flavonoids aglycones, and phenolic acid monoesters, e.g., pinobanksin-5-methyl ether, pinobanksin, chrysin, pinocembrin, galangin, pinobanksin-3-O-acetate, pinostrobin and pinobanksin-3-O-butanoate, or isobutanoate and methoxycinnamic acid cinnamyl ester. The anti-H. pylori activity of 70% ethanol water extracts of 10 Georgian propolis samples was evaluated in vitro by MIC (minimal inhibitory concentration) against the reference strain (H. pylori ATCC 43504) and 10 clinical strains with different antibiotic-resistance patterns. The strongest anti-Helicobacter activity (MIC and MBC = 31.3 µg/mL) was observed for propolis from Orgora, Ota, and Vardzia and two from Khaheti. Lower levels of activity (MIC = 62.5 µg/mL) were found in propolis obtained from Qvakhreli and Pasanauri, while the lowest effect was observed for Norio and Mestia (MIC = 125.0 µg/mL). However, despite differences in MIC, all evaluated samples exhibited bactericidal activity. We selected the most active propolis samples for assessment of urease inhibition property. Enzyme activity was inhibited by propolis extracts, with IC₅₀ ranging from 4.01 to 1484.8 µg/mL. Principal component analysis (PCA) and hierarchical fuzzy clustering (dendrograms) coupled with matrix correlation analysis exhibited that the strongest anti-Helicobacter activity was connected with black poplar origin and high flavonoid content of propolis. Samples with lower activity contained higher presence of aspen markers and/or dominance of non-flavonoid polyphenols over flavonoids. In summary, Georgian propolis can be regarded as a source bioactive compounds that can be used as adjuvant in therapy of H. pylori infection. Full article

(This article belongs to the Special Issue Antimicrobial Properties of Natural Products (Volume Ⅱ))

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18 pages, 1137 KiB

Open AccessArticle

First Evidence of a Combination of Terpinen-4-ol and α-Terpineol as a Promising Tool against ESKAPE Pathogens

by Bianca Johansen, Raphaël E. Duval and Jean-Christophe Sergere

Molecules 2022, 27(21), 7472; https://doi.org/10.3390/molecules27217472 - 2 Nov 2022

Cited by 12 | Viewed by 3042

Abstract

Antimicrobial resistance is a major public health issue raising growing concern in the face of dwindling response options. It is therefore urgent to find new anti-infective molecules enabling us to fight effectively against ever more numerous bacterial infections caused by ever more antibiotic-resistant bacteria. In this quest for new antibacterials, essential oils (or compounds extracted from essential oils) appear to be a promising therapeutic option. In the present work, we investigate the potential antibacterial synergy between a combination of terpinen-4-ol and α-terpineol (10:1) compared to standard tea tree oil. The minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) were determined. Then, time kill assays, in vitro cytotoxicity and bactericidal activity on latent bacteria (persisters) were investigated. Finally, an in silico study of the pharmacokinetic parameters of α-terpineol was also performed. Altogether, our data demonstrate that the combination of terpinen-4-ol and α-terpineol might be a precious weapon to address ESKAPE pathogens. Full article

(This article belongs to the Special Issue Antimicrobial Properties of Natural Products (Volume Ⅱ))

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Review

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18 pages, 2707 KiB

Open AccessReview

Bioactive Secondary Metabolites from Fungi of the Genus Cytospora Ehrenb. (Ascomycota)

by Boris Yotta Kianfé, Joseph Tchamgoue, Abolfazl Narmani, Rémy Bertrand Teponno, André-Ledoux Njouonkou, Marc Stadler and Simeon Fogue Kouam

Molecules 2023, 28(7), 3120; https://doi.org/10.3390/molecules28073120 - 31 Mar 2023

Cited by 3 | Viewed by 1991

Abstract

Cytospora is a genus of fungi belonging to the Cytosporaceae family (Sordariomycetes, Ascomycota) considered as a prolific source of specialized metabolites due to their ability to produce diverse secondary metabolites with a broad range of biological activities. Since the first chemical investigation of this genus in the 1980s, further studies have led to the isolation and structural elucidation of several bioactive compounds including cytosporones, nonanolides, macrocyclic dilactones, and terpenoids. This review summarizes, for the first time, the chemical diversity of bioactive secondary metabolites from the genus Cytospora and highlights its potential as an alternative source of secondary metabolites for pharmacological studies. Moreover, this review will serve as a basis for future investigations of compounds of this genus. Full article

(This article belongs to the Special Issue Antimicrobial Properties of Natural Products (Volume Ⅱ))

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