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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 20221

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Prof. Dr. Robert John Capon

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Institute for Molecular Bioscience, The University of Queensland, St. Lucia, QLD 4072, Australia
Interests: biodiscovery; marine and microbial natural products chemistry; biomimetic synthesis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

This Special Issue will feature original articles on microbial natural products from both bacteria and fungi, covering such topics as their detection, production, dereplication, prioritization, isolation, spectroscopic and chemical analysis, structure elucidation, biosynthesis, synthesis, and chemical and biological properties. The issue also encourages reviews on key topics in microbial natural products science, inclusive of the diversity of novel structure classes and functionality, geographic and taxonomic distribution, chemical ecology, biological properties, biosynthesis, and synthesis, and extending to applications in medicine, animal health, and crop and environmental protection. This Special Issue is an opportunity to celebrate all aspects of remarkable molecules made by microbes.

Prof. Dr. Robert John Capon
Guest Editor

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Keywords

microbial natural products
bacteria
fungi
novel scaffolds and functionality
structure elucidation
biosynthesis
chemical properties
biological properties

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Published Papers (6 papers)

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Research

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15 pages, 8368 KiB

Open AccessArticle

Antimicrobial Natural Products from Plant Pathogenic Fungi

by Melissa M. Cadelis, Steven A. Li, Shara J. van de Pas, Alex Grey, Daniel Mulholland, Bevan S. Weir, Brent R. Copp and Siouxsie Wiles

Molecules 2023, 28(3), 1142; https://doi.org/10.3390/molecules28031142 - 23 Jan 2023

Cited by 4 | Viewed by 2759

Abstract

Isolates of a variety of fungal plant pathogens (Alternaria radicina ICMP 5619, Cercospora beticola ICMP 15907, Dactylonectria macrodidyma ICMP 16789, D. torresensis ICMP 20542, Ilyonectria europaea ICMP 16794, and I. liriodendra ICMP 16795) were screened for antimicrobial activity against the human pathogenic bacteria Acinetobacter baumannii, Pseudomonas aeruginosa, Escherichia coli, Mycobacterium abscessus, and M. marinum and were found to have some activity. Investigation of the secondary metabolites of these fungal isolates led to the isolation of ten natural products (1–10) of which one was novel, (E)-4,7-dihydroxyoct-2-enoic acid (1). Structure elucidation of all natural products was achieved by a combination of NMR spectroscopy and mass spectrometry. We also investigated the antimicrobial activity of a number of the isolated natural products. While we did not find (E)-4,7-dihydroxyoct-2-enoic acid (1) to have any activity against the bacteria and fungi in our assays, we did find that cercosporin (7) exhibited potent activity against Methicillin resistant Staphylococcus aureus (MRSA), dehydro-curvularin (6) and radicicol (10) exhibited antimycobacterial activity against M. marinum, and brefeldin A (8) and radicicol (10) exhibited antifungal activity against Candida albicans. Investigation of the cytotoxicity and haemolytic activities of these natural products (6–8 and 10) found that only one of the four active compounds, radicicol (10), was non-cytotoxic and non-haemolytic. Full article

(This article belongs to the Special Issue Microbial Natural Products 2022)

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17 pages, 2654 KiB

Open AccessArticle

Molecular Networking and Cultivation Profiling Reveals Diverse Natural Product Classes from an Australian Soil-Derived Fungus Aspergillus sp. CMB-MRF324

by Taizong Wu, Angela A. Salim, Paul V. Bernhardt and Robert J. Capon

Molecules 2022, 27(24), 9066; https://doi.org/10.3390/molecules27249066 - 19 Dec 2022

Cited by 2 | Viewed by 1989

Abstract

This study showcases the application of an integrated workflow of molecular networking chemical profiling (GNPS), together with miniaturized microbioreactor cultivation profiling (MATRIX) to successfully detect, dereplicate, prioritize, optimize the production, isolate, characterize, and identify a diverse selection of new chemically labile natural products from the Queensland sheep pasture soil-derived fungus Aspergillus sp. CMB-MRF324. More specifically, we report the new tryptamine enamino tripeptide aspergillamides E–F (7–8), dihydroquinoline-2-one aflaquinolones H–I (11–12), and prenylated phenylbutyrolactone aspulvinone Y (14), along with an array of known co-metabolites, including asterriquinones SU5228 (9) and CT5 (10), terrecyclic acid A (13), and aspulvinones N-CR (15), B (16), D (17), and H (18). Structure elucidation was achieved by a combination of detailed spectroscopic and chemical analysis, biosynthetic considerations, and in the case of 11, an X-ray crystallographic analysis. Full article

(This article belongs to the Special Issue Microbial Natural Products 2022)

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13 pages, 1134 KiB

Open AccessArticle

Trichoderma versus Fusarium—Inhibition of Pathogen Growth and Mycotoxin Biosynthesis

by Marta Modrzewska, Lidia Błaszczyk, Łukasz Stępień, Monika Urbaniak, Agnieszka Waśkiewicz, Tomoya Yoshinari and Marcin Bryła

Molecules 2022, 27(23), 8146; https://doi.org/10.3390/molecules27238146 - 23 Nov 2022

Cited by 16 | Viewed by 3434

Abstract

This study evaluated the ability of selected strains of Trichoderma viride, T. viridescens, and T. atroviride to inhibit mycelium growth and the biosynthesis of mycotoxins deoxynivalenol (DON), nivalenol (NIV), zearalenone (ZEN), α-(α-ZOL) and β-zearalenol (β-ZOL) by selected strains of Fusarium culmorum and F. cerealis. For this purpose, an in vitro experiment was carried out on solid substrates (PDA and rice). After 5 days of co-culture, it was found that all Trichoderma strains used in the experiment significantly inhibited the growth of Fusarium mycelium. Qualitative assessment of pathogen–antagonist interactions showed that Trichoderma colonized 75% to 100% of the medium surface (depending on the species and strain of the antagonist and the pathogen) and was also able to grow over the mycelium of the pathogen and sporulate. The rate of inhibition of Fusarium mycelium growth by Trichoderma ranged from approximately 24% to 66%. When Fusarium and Trichoderma were co-cultured on rice, Trichoderma strains were found to inhibit DON biosynthesis by about 73% to 98%, NIV by about 87% to 100%, and ZEN by about 12% to 100%, depending on the pathogen and antagonist strain. A glycosylated form of DON was detected in the co-culture of F. culmorum and Trichoderma, whereas it was absent in cultures of the pathogen alone, thus suggesting that Trichoderma is able to glycosylate DON. The results also suggest that a strain of T. viride is able to convert ZEN into its hydroxylated derivative, β-ZOL. Full article

(This article belongs to the Special Issue Microbial Natural Products 2022)

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8 pages, 713 KiB

Open AccessArticle

Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina

by Marte Jenssen, Venke Kristoffersen, Kumar Motiram-Corral, Johan Isaksson, Teppo Rämä, Jeanette H. Andersen, Espen H. Hansen and Kine Østnes Hansen

Molecules 2021, 26(24), 7560; https://doi.org/10.3390/molecules26247560 - 13 Dec 2021

Cited by 5 | Viewed by 2860

Abstract

As part of our search for bioactive metabolites from understudied marine microorganisms, the new chlorinated metabolite chlovalicin B (1) was isolated from liquid cultures of the marine basidiomycete Digitatispora marina, which was collected and isolated from driftwood found at Vannøya, Norway. The structure of the novel compound was elucidated by spectroscopic methods including 1D and 2D NMR and analysis of HRMS data, revealing that 1 shares its molecular scaffold with a previously isolated compound, chlovalicin. This represents the first compound isolated from the Digitatispora genus, and the first reported fumagillin/ovalicin-like compound isolated from Basidiomycota. Compound 1 was evaluated for antibacterial activities against a panel of five bacteria, its ability to inhibit bacterial biofilm formation, for antifungal activity against Candida albicans, and for cytotoxic activities against malignant and non-malignant human cell lines. Compound 1 displayed weak cytotoxic activity against the human melanoma cell line A2058 (~50% survival at 50 µM). No activity was detected against biofilm formation or C. albicans at 50 µM, or against bacterial growth at 100 µM nor against the production of cytokines by the human acute monocytic leukemia cell line THP-1 at 50 µM. Full article

(This article belongs to the Special Issue Microbial Natural Products 2022)

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Review

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45 pages, 23764 KiB

Open AccessReview

Halogenation in Fungi: What Do We Know and What Remains to Be Discovered?

by Bastien Cochereau, Laurence Meslet-Cladière, Yves François Pouchus, Olivier Grovel and Catherine Roullier

Molecules 2022, 27(10), 3157; https://doi.org/10.3390/molecules27103157 - 14 May 2022

Cited by 10 | Viewed by 4369

Abstract

In nature, living organisms produce a wide variety of specialized metabolites to perform many biological functions. Among these specialized metabolites, some carry halogen atoms on their structure, which can modify their chemical characteristics. Research into this type of molecule has focused on how organisms incorporate these atoms into specialized metabolites. Several families of enzymes have been described gathering metalloenzymes, flavoproteins, or S-adenosyl-L-methionine (SAM) enzymes that can incorporate these atoms into different types of chemical structures. However, even though the first halogenation enzyme was discovered in a fungus, this clade is still lagging behind other clades such as bacteria, where many enzymes have been discovered. This review will therefore focus on all halogenation enzymes that have been described in fungi and their associated metabolites by searching for proteins available in databases, but also by using all the available fungal genomes. In the second part of the review, the chemical diversity of halogenated molecules found in fungi will be discussed. This will allow the highlighting of halogenation mechanisms that are still unknown today, therefore, highlighting potentially new unknown halogenation enzymes. Full article

(This article belongs to the Special Issue Microbial Natural Products 2022)

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44 pages, 5686 KiB

Open AccessFeature PaperReview

Bioactive Compounds from Terrestrial and Marine-Derived Fungi of the Genus Neosartorya †

by Joana D. M. de Sá, Decha Kumla, Tida Dethoup and Anake Kijjoa

Molecules 2022, 27(7), 2351; https://doi.org/10.3390/molecules27072351 - 6 Apr 2022

Cited by 12 | Viewed by 3887

Abstract

Fungi comprise the second most species-rich organism group after that of insects. Recent estimates hypothesized that the currently reported fungal species range from 3.5 to 5.1 million types worldwide. Fungi can grow in a wide range of habitats, from the desert to the depths of the sea. Most develop in terrestrial environments, but several species live only in aquatic habitats, and some live in symbiotic relationships with plants, animals, or other fungi. Fungi have been proved to be a rich source of biologically active natural products, some of which are clinically important drugs such as the β-lactam antibiotics, penicillin and cephalosporin, the immunosuppressant, cyclosporine, and the cholesterol-lowering drugs, compactin and lovastatin. Given the estimates of fungal biodiversity, it is easy to perceive that only a small fraction of fungi worldwide have ever been investigated regarding the production of biologically valuable compounds. Traditionally, fungi are classified primarily based on the structures associated with sexual reproduction. Thus, the genus Neosartorya (Family Trichocomaceae) is the telemorphic (sexual state) of the Aspergillus section known as Fumigati, which produces both a sexual state with ascospores and an asexual state with conidiospores, while the Aspergillus species produces only conidiospores. However, according to the Melbourne Code of nomenclature, only the genus name Aspergillus is to be used for both sexual and asexual states. Consequently, the genus name Neosartorya was no longer to be used after 1 January 2013. Nevertheless, the genus name Neosartorya is still used for the fungi that had already been taxonomically classified before the new rule was in force. Another aspect is that despite the small number of species (23 species) in the genus Neosartorya, and although less than half of them have been investigated chemically, the chemical diversity of this genus is impressive. Many chemical classes of compounds, some of which have unique scaffolds, such as indole alkaloids, peptides, meroterpenes, and polyketides, have been reported from its terrestrial, marine-derived, and endophytic species. Though the biological and pharmacological activities of a small fraction of the isolated metabolites have been investigated due to the available assay systems, they exhibited relevant biological and pharmacological activities, such as anticancer, antibacterial, antiplasmodial, lipid-lowering, and enzyme-inhibitory activities. Full article

(This article belongs to the Special Issue Microbial Natural Products 2022)

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