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Microbial Natural Products: A Promising Source for Medical Application

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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: closed (31 December 2022) | Viewed by 41788

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Prof. Dr. Anna Malm

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Guest Editor

Department of Pharmaceutical Microbiology, Medical University of Lublin, Chodzki Str. 1, 20-093 Lublin, Poland
Interests: medical microbiology; antimicrobial compounds of synthetic and natural origin; human microbiota
Special Issues, Collections and Topics in MDPI journals

Dr. Olga V. Efremenkova

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Guest Editor

Department of Microbiology; Gause Institute of New Antibiotics, Moscow, Russia
Interests: natural antibiotics; bacteria, actinomycetes; fungi as producers of antibiotics; isolation of microorganisms from different ecosystems

Special Issue Information

Dear Colleagues,

We are pleased to invite you to contribute to this Special Issue, “Microbial Natural Products: A Promising Source for Medical Application”. Microorganisms create a rich but not fully explored reservoir of several natural compounds with a broad spectrum of biological and pharmacological activity. Both primary and secondary microbial metabolites possess potential benefits for human health.

This Special Issue aims to extensively study the meaning of microbial natural products and their potential application as food supplements, functional food and/or medicines in the prophylaxis and treatment of several disorders, especially those that constitute a significant epidemiological problem in the 21st century, e.g., infectious, metabolic and neurological diseases, as well as cancer.

In this Special Issue, short communications, original research articles and reviews in the field of microbiology, biotechnology, pharmacology, biopharmacy and/or food sciences are welcome. Research areas may include, but are not limited to, the following: microbial natural compounds as antimicrobial, anticancer and neuroprotective agents, as well as gut microbiota compounds for prevention and therapeutic purposes.

We look forward to receiving your contributions.

Prof. Dr. Anna Malm
Dr. Olga V. Efremenkova
Guest Editors

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

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Keywords

microorganisms
primary and secondary metabolites
antimicrobial and anticancer agents
neuroprotective agents
gut microbiota compounds
food supplements
functional food
medicines

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Microbial Natural Products: A Promising Source for Medical Application (2nd Edition) in Molecules (5 articles)

Published Papers (11 papers)

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Research

Jump to: Review

16 pages, 4242 KiB

Open AccessFeature PaperArticle

Chemical and Biological Studies of Endophytes Isolated from Marchantia polymorpha

by Mateusz Stelmasiewicz, Łukasz Świątek and Agnieszka Ludwiczuk

Molecules 2023, 28(5), 2202; https://doi.org/10.3390/molecules28052202 - 27 Feb 2023

Cited by 6 | Viewed by 2586

Abstract

Natural bioresources, predominantly plants, have always been regarded as the richest source of drugs for diseases threatening humanity. Additionally, microorganism-originating metabolites have been extensively explored as weapons against bacterial, fungal, and viral infections. However, the biological potential of metabolites produced by plant endophytes still remains understudied, despite significant efforts reflected in recently published papers. Thus, our goal was to evaluate the metabolites produced by endophytes isolated from Marchantia polymorpha and to study their biological properties, namely anticancer and antiviral potential. The cytotoxicity and anticancer potential were assessed using the microculture tetrazolium technique (MTT) against non-cancerous VERO cells and cancer cells—namely the HeLa, RKO, and FaDu cell lines. The antiviral potential was tested against the human herpesvirus type-1 replicating in VERO cells by observing the influence of the extract on the virus-infected cells and measuring the viral infectious titer and viral load. The most characteristic metabolites identified in the ethyl acetate extract and fractions obtained by use of centrifugal partition chromatography (CPC) were volatile cyclic dipeptides, cyclo(l-phenylalanyl-l-prolyl), cyclo(l-leucyl-l-prolyl), and their stereoisomers. In addition to the diketopiperazine derivatives, this liverwort endophyte also produced arylethylamides and fatty acids amides. The presence of N-phenethylacetamide and oleic acid amide was confirmed. The endophyte extract and isolated fractions showed a potential selective anticancer influence on all tested cancer cell lines. Moreover, the extract and the first separated fraction noticeably diminished the formation of the HHV-1-induced cytopathic effect and reduced the virus infectious titer by 0.61–1.16 log and the viral load by 0.93–1.03 log. Endophytic organisms produced metabolites with potential anticancer and antiviral activity; thus, future studies should aim to isolate pure compounds and evaluate their biological activities. Full article

(This article belongs to the Special Issue Microbial Natural Products: A Promising Source for Medical Application)

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13 pages, 2106 KiB

Open AccessArticle

Antibacterial Activity of Peptide Derivatives of Phosphinothricin against Multidrug-Resistant Klebsiella pneumoniae

by Marija V. Demiankova, Fabio Giovannercole, Maxim A. Khomutov, Arthur I. Salikhov, Laura Onillon, Vladimir T. Valuev-Elliston, Byazilya F. Vasilieva, Elena N. Khurs, Nina I. Gabrielyan, Sergey N. Kochetkov, Olga V. Efremenkova, Daniela De Biase and Alex R. Khomutov

Molecules 2023, 28(3), 1234; https://doi.org/10.3390/molecules28031234 - 27 Jan 2023

Cited by 4 | Viewed by 2486

Abstract

The fast spread of bacteria that are resistant to many classes of antibiotics (multidrug resistant) is a global threat to human and animal health with a worrisome scenario ahead. Novel therapeutical strategies are of crucial importance to combat this phenomenon. For this purpose, we investigated the antimicrobial properties of the naturally occurring tripeptide Bialaphos and a dipeptide L-leucyl-L-phosphinoithricin, the synthesis and diastereomers separation of which are herein described. We demonstrate that these compounds are effective on clinical isolates of the human pathogen Klebsiella pneumoniae, causing hospital-acquired and community-acquired infections. The tested isolates were remarkable for their resistance to more than 20 commercial antibiotics of different classes. Based on previous literature data and our experiments consisting of glutamine supplementation, we suggest that both compounds release phosphinothricin—a well-known nanomolar inhibitor of glutamine synthetase—after their penetration in the bacterial cells; and, in this way, exert their antibacterial effect by negatively affecting nitrogen assimilation in this pathogen. Full article

(This article belongs to the Special Issue Microbial Natural Products: A Promising Source for Medical Application)

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18 pages, 2521 KiB

Open AccessArticle

Metabolomic Strategy to Characterize the Profile of Secondary Metabolites in Aspergillus aculeatus DL1011 Regulated by Chemical Epigenetic Agents

by Xuan Shi, Yu Sun, Junhui Liu, Wencai Liu, Yan Xing, Zhilong Xiu and Yuesheng Dong

Molecules 2023, 28(1), 218; https://doi.org/10.3390/molecules28010218 - 26 Dec 2022

Cited by 2 | Viewed by 2257

Abstract

Chemical epigenetic regulation (CER) is an effective method to activate the silent pathway of fungal secondary metabolite synthesis. However, conventional methods for CER study are laborious and time-consuming. In the meantime, the overall profile of the secondary metabolites in the fungi treated by the CER reagent is not well characterized. In this study, suberohydroxamic acid (SBHA), a histone deacetylase inhibitor, was added to a culture of Aspergillus aculeatus DL1011 and a new strategy based on LC-MS/MS analysis integrated with various metabolomic tools (MetaboAnalyst, MS-DIAL, SIRIUS and GNPS) was developed to characterize the profile of induced metabolites. As a result, 13.6%, 29.5% and 27.2% of metabolites were identified as newly biosynthesized, increasing and decreasing in abundance by CER, respectively. The structures of the 18 newly induced secondary metabolites were further identified by the new strategy to demonstrate that 72.2% of them (1 novel compound and 12 known compounds) were first discovered in A. aculeatus upon SBHA treatment. The accuracy of the new approach was confirmed by purification and NMR data analysis of major newly biosynthesized secondary metabolites. The bioassay showed that the newly biosynthesized compounds, roseopurpurin analogues, showed selective activities against DPPH scavenging, cytotoxicity and SHP1 inhibition. Our research demonstrated that CER was beneficial for changing the secondary metabolic profile of fungi and was an effective means of increasing the diversity of active metabolites. Our work also supplied a metabolomic strategy to characterize the profile changes and determine the newly induced compounds in the secondary metabolites of fungi treated with the chemical epigenetic regulator. Full article

(This article belongs to the Special Issue Microbial Natural Products: A Promising Source for Medical Application)

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16 pages, 1736 KiB

Open AccessArticle

Exploring Peptaibol’s Profile, Antifungal, and Antitumor Activity of Emericellipsin A of Emericellopsis Species from Soda and Saline Soils

by Anastasia E. Kuvarina, Irina A. Gavryushina, Maxim A. Sykonnikov, Tatiana A. Efimenko, Natalia N. Markelova, Elena N. Bilanenko, Sofiya A. Bondarenko, Lyudmila Y. Kokaeva, Alla V. Timofeeva, Marina V. Serebryakova, Anna S. Barashkova, Eugene A. Rogozhin, Marina L. Georgieva and Vera S. Sadykova

Molecules 2022, 27(5), 1736; https://doi.org/10.3390/molecules27051736 - 7 Mar 2022

Cited by 11 | Viewed by 2694

Abstract

Features of the biochemical adaptations of alkaliphilic fungi to exist in extreme environments could promote the production of active antibiotic compounds with the potential to control microorganisms, causing infections associated with health care. Thirty-eight alkaliphilic and alkalitolerant Emericellopsis strains (E. alkalina, E. cf. maritima, E. cf. terricola, Emericellopsis sp.) isolated from different saline soda soils and belonging to marine, terrestrial, and soda soil ecological clades were investigated for emericellipsin A (EmiA) biosynthesis, an antifungal peptaibol previously described for Emericellopsis alkalina. The analysis of the Emericellopsis sp. strains belonging to marine and terrestrial clades from chloride soils revealed another novel form with a mass of 1032.7 Da, defined by MALDI-TOF Ms/Ms spectrometers, as the EmiA lacked a hydroxyl (dEmiA). EmiA displayed strong inhibitory effects on cell proliferation and viability of HCT 116 cells in a dose- and time-dependent manners and induced apoptosis. Full article

(This article belongs to the Special Issue Microbial Natural Products: A Promising Source for Medical Application)

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12 pages, 1050 KiB

Open AccessArticle

OSMAC Strategy Integrated with Molecular Networking for Accessing Griseofulvin Derivatives from Endophytic Fungi of Moquiniastrum polymorphum (Asteraceae)

by Victor F. Farinella, Eunizinis S. Kawafune, Marcelo M. P. Tangerina, Helori V. Domingos, Leticia V. Costa-Lotufo and Marcelo J. P. Ferreira

Molecules 2021, 26(23), 7316; https://doi.org/10.3390/molecules26237316 - 2 Dec 2021

Cited by 7 | Viewed by 2983

Abstract

Three endophytic fungi isolated from Moquiniastrum polymorphum (Less.) G. Sancho (Asteraceae) were cultivated using the one strain many compounds (OSMAC) strategy to evaluate the production of griseofulvin derivatives. Extracts obtained were analyzed by HPLC–MS/MS and the chromatographic and spectrometric data used to elaborate a feature-based molecular network (FBMN) through the GNPS platform. This approach allowed the observation of differences such as medium-specific and strain-specific production of griseofulvin derivatives and variations of cytotoxic activity in most extracts. To evaluate the efficiency of the OSMAC approach allied with FBMN analysis in the prospection of compounds of biotechnological interest, griseofulvin and 7-dechlorogriseofulvin were isolated, and the relative concentrations were estimated in all culture media using HPLC–UV, allowing for the inference of the best strain–medium combinations to maximize its production. Malt extract-peptone broth and Wickerham broth media produced the highest concentrations of both secondary metabolites. Full article

(This article belongs to the Special Issue Microbial Natural Products: A Promising Source for Medical Application)

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Review

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23 pages, 1118 KiB

Open AccessReview

Microbial Secondary Metabolites via Fermentation Approaches for Dietary Supplementation Formulations

by Alexandru Vasile Rusu, Monica Trif and João Miguel Rocha

Molecules 2023, 28(16), 6020; https://doi.org/10.3390/molecules28166020 - 11 Aug 2023

Cited by 10 | Viewed by 4236

Abstract

Food supplementation formulations refer to products that are designed to provide additional nutrients to the diet. Vitamins, dietary fibers, minerals and other functional compounds (such as antioxidants) are concentrated in dietary supplements. Specific amounts of dietary compounds are given to the body through food supplements, and these include as well so-called non-essential compounds such as secondary plant bioactive components or microbial natural products in addition to nutrients in the narrower sense. A significant social challenge represents how to moderately use the natural resources in light of the growing world population. In terms of economic production of (especially natural) bioactive molecules, ways of white biotechnology production with various microorganisms have recently been intensively explored. In the current review other relevant dietary supplements and natural substances (e.g., vitamins, amino acids, antioxidants) used in production of dietary supplements formulations and their microbial natural production via fermentative biotechnological approaches are briefly reviewed. Biotechnology plays a crucial role in optimizing fermentation conditions to maximize the yield and quality of the target compounds. Advantages of microbial production include the ability to use renewable feedstocks, high production yields, and the potential for cost-effective large-scale production. Additionally, it can be more environmentally friendly compared to chemical synthesis, as it reduces the reliance on petrochemicals and minimizes waste generation. Educating consumers about the benefits, safety, and production methods of microbial products in general is crucial. Providing clear and accurate information about the science behind microbial production can help address any concerns or misconceptions consumers may have. Full article

(This article belongs to the Special Issue Microbial Natural Products: A Promising Source for Medical Application)

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19 pages, 3377 KiB

Open AccessReview

Bioactive Compounds Produced by Endophytic Microorganisms Associated with Bryophytes—The “Bryendophytes”

by Mateusz Stelmasiewicz, Łukasz Świątek, Simon Gibbons and Agnieszka Ludwiczuk

Molecules 2023, 28(7), 3246; https://doi.org/10.3390/molecules28073246 - 5 Apr 2023

Cited by 6 | Viewed by 3618

Abstract

The mutualistic coexistence between the host and endophyte is diverse and complex, including host growth regulation, the exchange of substances like nutrients or biostimulants, and protection from microbial or herbivore attack. The latter is commonly associated with the production by endophytes of bioactive natural products, which also possess multiple activities, including antibacterial, insecticidal, antioxidant, antitumor, and antidiabetic properties, making them interesting and valuable model substances for future development into drugs. The endophytes of higher plants have been extensively studied, but there is a dearth of information on the biodiversity of endophytic microorganisms associated with bryophytes and, more importantly, their bioactive metabolites. For the first time, we name bryophyte endophytes “bryendophytes” to elaborate on this important and productive source of biota. In this review, we summarize the current knowledge on the diversity of compounds produced by endophytes, emphasizing bioactive molecules from bryendophytes. Moreover, the isolation methods and biodiversity of bryendophytes from mosses, liverworts, and hornworts are described. Full article

(This article belongs to the Special Issue Microbial Natural Products: A Promising Source for Medical Application)

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33 pages, 902 KiB

Open AccessReview

The Role of Probiotics and Their Metabolites in the Treatment of Depression

by Monika Elżbieta Jach, Anna Serefko, Aleksandra Szopa, Ewa Sajnaga, Hieronim Golczyk, Leandro Soares Santos, Kinga Borowicz-Reutt and Elwira Sieniawska

Molecules 2023, 28(7), 3213; https://doi.org/10.3390/molecules28073213 - 4 Apr 2023

Cited by 15 | Viewed by 6497

Abstract

Depression is a common and complex mental and emotional disorder that causes disability, morbidity, and quite often mortality around the world. Depression is closely related to several physical and metabolic conditions causing metabolic depression. Studies have indicated that there is a relationship between the intestinal microbiota and the brain, known as the gut–brain axis. While this microbiota–gut–brain connection is disturbed, dysfunctions of the brain, immune system, endocrine system, and gastrointestinal tract occur. Numerous studies show that intestinal dysbiosis characterized by abnormal microbiota and dysfunction of the microbiota–gut–brain axis could be a direct cause of mental and emotional disorders. Traditional treatment of depression includes psychotherapy and pharmacotherapy, and it mainly targets the brain. However, restoration of the intestinal microbiota and functions of the gut–brain axis via using probiotics, their metabolites, prebiotics, and healthy diet may alleviate depressive symptoms. Administration of probiotics labeled as psychobiotics and their metabolites as metabiotics, especially as an adjuvant to antidepressants, improves mental disorders. It is a new approach to the prevention, management, and treatment of mental and emotional illnesses, particularly major depressive disorder and metabolic depression. For the effectiveness of antidepressant therapy, psychobiotics should be administered at a dose higher than 1 billion CFU/day for at least 8 weeks. Full article

(This article belongs to the Special Issue Microbial Natural Products: A Promising Source for Medical Application)

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23 pages, 3459 KiB

Open AccessReview

Microorganisms for Ginsenosides Biosynthesis: Recent Progress, Challenges, and Perspectives

by Luan Luong Chu, Nguyen Quang Huy and Nguyen Huu Tung

Molecules 2023, 28(3), 1437; https://doi.org/10.3390/molecules28031437 - 2 Feb 2023

Cited by 14 | Viewed by 3380

Abstract

Ginsenosides are major bioactive compounds present in the Panax species. Ginsenosides exhibit various pharmaceutical properties, including anticancer, anti-inflammatory, antimetastatic, hypertension, and neurodegenerative disorder activities. Although several commercial products have been presented on the market, most of the current chemical processes have an unfriendly environment and a high cost of downstream processing. Compared to plant extraction, microbial production exhibits high efficiency, high selectivity, and saves time for the manufacturing of industrial products. To reach the full potential of the pharmaceutical resource of ginsenoside, a suitable microorganism has been developed as a novel approach. In this review, cell biological mechanisms in anticancer activities and the present state of research on the production of ginsenosides are summarized. Microbial hosts, including native endophytes and engineered microbes, have been used as novel and promising approaches. Furthermore, the present challenges and perspectives of using microbial hosts to produce ginsenosides have been discussed. Full article

(This article belongs to the Special Issue Microbial Natural Products: A Promising Source for Medical Application)

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25 pages, 3833 KiB

Open AccessReview

Endophytes, a Potential Source of Bioactive Compounds to Curtail the Formation–Accumulation of Advanced Glycation End Products: A Review

by Lory Sthephany Rochín-Hernández, Lory Jhenifer Rochín-Hernández and Luis Bernardo Flores-Cotera

Molecules 2022, 27(14), 4469; https://doi.org/10.3390/molecules27144469 - 13 Jul 2022

Cited by 8 | Viewed by 2945

Abstract

Endophytes, microorganisms that live in the internal tissues and organs of the plants, are known to produce numerous bioactive compounds, including, at times, some phytochemicals of their host plant. For such reason, endophytes have been quoted as a potential source for discovering bioactive compounds, particularly, of medical interest. Currently, many non-communicable diseases are threatening global human health, noticeably: diabetes, neurodegenerative diseases, cancer, and other ailment related to chronic inflammation and ageing. Intriguingly, the pathogenesis and development of these diseases have been linked to an excessive formation and accumulation of advanced glycation end products (AGEs). AGEs are a heterogeneous group of compounds that can alter the conformation, function, and lifetime of proteins. Therefore, compounds that prevent the formation and consequent accumulation of AGEs (AntiAGEs compounds) could be useful to delay the progress of some chronic diseases, and/or harmful effects of undue AGEs accumulation. Despite the remarkable ability of endophytes to produce bioactive compounds, most of the natural antiAGEs compounds reported in the literature are derived from plants. Accordingly, this work covers 26 plant antiAGEs compounds and some derivatives that have been reported as endophytic metabolites, and discusses the importance, possible advantages, and challenges of using endophytes as a potential source of antiAGEs compounds. Full article

(This article belongs to the Special Issue Microbial Natural Products: A Promising Source for Medical Application)

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22 pages, 870 KiB

Open AccessReview

Yarrowia lipolytica as an Alternative and Valuable Source of Nutritional and Bioactive Compounds for Humans

by Monika Elżbieta Jach and Anna Malm

Molecules 2022, 27(7), 2300; https://doi.org/10.3390/molecules27072300 - 1 Apr 2022

Cited by 45 | Viewed by 6560

Abstract

Yarrowia lipolytica, an oleagineous species of yeast, is a carrier of various important nutrients. The biomass of this yeast is an extensive source of protein, exogenous amino acids, bioavailable essenctial trace minerals, and lipid compounds as mainly unsaturated fatty acids. The biomass also contains B vitamins, including vitamin B12, and many other bioactive components. Therefore, Y. lipolytica biomass can be used in food supplements for humans as safe and nutritional additives for maintaining the homeostasis of the organism, including for vegans and vegetarians, athletes, people after recovery, and people at risk of B vitamin deficiencies. Full article

(This article belongs to the Special Issue Microbial Natural Products: A Promising Source for Medical Application)

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