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Natural Products from Fungi
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Natural Products from Fungi

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

Deadline for manuscript submissions: closed (31 August 2020) | Viewed by 28409

Special Issue Editor

Dr. Francisco Leon

E-Mail Website
Guest Editor
Department of Drug Discovery and Biomedical Sciences, College of Pharmacy, University of South Carolina, Columbia, SC 29208, USA
Interests: natural products chemistry; synthesis of natural products; medicinal chemistry; alkaloids
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The kingdom fungi are largely established as one of the major biodiverse assets of our natural resources. These organisms can be unicellular or multicellular and exist/survive in all the environments on earth: terrestrial soil, aquatic sea, freshwater, and in extreme habitats on the planet. They play a significant role serving as symbiotic, parasitic, and/or mutualistic organisms, providing extraordinary properties. Several fungi engage in pharmaceutical industry, enzymes, food, and some take part in biotechnology, while some are sources of natural products with diverse chemical entities and wide applications.

This Special Issue is dedicated to the contributions (reviews, full articles, communications) of these important organisms on several aspects which include, but are not limited to isolation and structural elucidation of undescribed bioactive secondary metabolites, biosynthetic studies and applications, total syntheses of secondary fungal metabolites and derivatives, as well as new methodologies involving novel therapeutic agents involving organisms of these kingdom.

Dr. Francisco Leon
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

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.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • fungi metabolites
  • natural products
  • fungi bioactive compounds
  • biotechnology
  • synthesis of fungal metabolites
  • derivatization

Published Papers (7 papers)

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Research

12 pages, 1038 KiB  
Article
Effect of Strain, Wood Substrate and Cold Treatment on the Yield and β-Glucan Content of Ganoderma lucidum Fruiting Bodies
by Marta Cortina-Escribano, Juha-Matti Pihlava, Jari Miina, Pyry Veteli, Riikka Linnakoski and Henri Vanhanen
Molecules 2020, 25(20), 4732; https://doi.org/10.3390/molecules25204732 - 15 Oct 2020
Cited by 14 | Viewed by 4042
Abstract
Wood residues from forestry industries can be potential raw materials for specialty and edible mushroom production. The aim of this study was to evaluate the suitability of wood residues for the cultivation of Ganoderma lucidum originating from boreal forests. The substrates tested included [...] Read more.
Wood residues from forestry industries can be potential raw materials for specialty and edible mushroom production. The aim of this study was to evaluate the suitability of wood residues for the cultivation of Ganoderma lucidum originating from boreal forests. The substrates tested included sawdust and wood chips of Betula spp., Populus tremula, Picea abies, Pinus sylvestris and Larix sp. The suitability of the substrates and the ability of the strains to develop fruiting bodies and produce β-glucan were evaluated. Fruiting body formation was supported by applying two different cold shock treatments to substrate bags. The highest yields were observed with MUS192 strain and Betula spp. and P. tremula wood-based substrates. β-Glucan content in the fruiting bodies was highest with the MUS75 and P. tremula wood-based substrate. Based on these findings, the combination of P. tremula wood residues and the MUS192 strain is proposed to enhance the yield and β-glucan content of the fruiting bodies. A cold treatment of 5 °C is suggested to induce primordia formation and to increase fruiting probability. This is the first time that strains of G. lucidum originating from boreal forests have been compared and successfully cultivated simulating commercial indoor cultivation. Full article
(This article belongs to the Special Issue Natural Products from Fungi)
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18 pages, 2629 KiB  
Article
Biocatalytic Potential of Native Basidiomycetes from Colombia for Flavour/Aroma Production
by David A. Jaramillo, María J. Méndez, Gabriela Vargas, Elena E. Stashenko, Aída-M. Vasco-Palacios, Andrés Ceballos and Nelson H. Caicedo
Molecules 2020, 25(18), 4344; https://doi.org/10.3390/molecules25184344 - 22 Sep 2020
Cited by 9 | Viewed by 4376
Abstract
Aromas and flavours can be produced from fungi by either de novo synthesis or biotransformation processes. Herein, the biocatalytic potential of seven basidiomycete species from Colombia fungal strains isolated as endophytes or basidioma was evaluated. Ganoderma webenarium, Ganoderma chocoense, and Ganoderma [...] Read more.
Aromas and flavours can be produced from fungi by either de novo synthesis or biotransformation processes. Herein, the biocatalytic potential of seven basidiomycete species from Colombia fungal strains isolated as endophytes or basidioma was evaluated. Ganoderma webenarium, Ganoderma chocoense, and Ganoderma stipitatum were the most potent strains capable of decolourizing β,β-carotene as evidence of their potential as biocatalysts for de novo aroma synthesis. Since a species’ biocatalytic potential cannot solely be determined via qualitative screening using β,β-carotene biotransformation processes, we focused on using α-pinene biotransformation with mycelium as a measure of catalytic potential. Here, two strains of Trametes elegans—namely, the endophytic (ET-06) and basidioma (EBB-046) strains—were screened. Herein, T. elegans is reported for the first time as a novel biocatalyst for the oxidation of α-pinene, with a product yield of 2.9 mg of cis-Verbenol per gram of dry weight mycelia used. The EBB-046 strain generated flavour compounds via the biotransformation of a Cape gooseberry medium and de novo synthesis in submerged cultures. Three aroma-producing compounds were identified via GC–MS—namely, methyl-3-methoxy-4H-pyran-4-one, hexahydro-3-(methylpropyl)-pyrrolo[1,2-a]pyrazine-1,4-dione, and hexahydro-3-(methylphenyl)-pyrrolo[1,2-a]pyrazine-1,4-dione. Full article
(This article belongs to the Special Issue Natural Products from Fungi)
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12 pages, 4709 KiB  
Article
Identification and Quantification of a Phytotoxic Metabolite from Alternaria dauci
by Martha Leyte-Lugo, Pascal Richomme, Pascal Poupard and Luis M. Peña-Rodriguez
Molecules 2020, 25(17), 4003; https://doi.org/10.3390/molecules25174003 - 2 Sep 2020
Cited by 14 | Viewed by 3146
Abstract
Alternaria dauci is the causal agent of Alternaria leaf blight (ALB) in carrot (Daucus carota) crops around the world. However, to date, A. dauci has received limited attention in its production of phytotoxic metabolites. In this investigation, the bioassay-guided isolation of [...] Read more.
Alternaria dauci is the causal agent of Alternaria leaf blight (ALB) in carrot (Daucus carota) crops around the world. However, to date, A. dauci has received limited attention in its production of phytotoxic metabolites. In this investigation, the bioassay-guided isolation of the extract from liquid cultures of A. dauci resulted in the isolation of two metabolites identified as α-acetylorcinol (1) and p-hydroxybenzoic acid (2), based on their spectroscopic data and results from chemical correlation reactions. Testing of both metabolites in different assays showed an important phytotoxic activity for p-hydroxybenzoic acid (2) when tested in the leaf-spot assay on parsley (Petroselinum crispum), in the leaf infiltration assay on tobacco (Nicotiana alata) and marigold (Tagetes erecta), and in the immersion assay on parsley and parsnip (Pastinaca sativa) leaves. Quantification of the two metabolites in the crude extract of A. dauci kept at different times showed that p-hydroxybenzoic acid (2) is one of the first metabolites to be synthesized by the pathogen, suggesting that this salicylic acid derivative could play an important role in the pathogenicity of the fungus. Full article
(This article belongs to the Special Issue Natural Products from Fungi)
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9 pages, 1526 KiB  
Article
HPLC-DAD-Guided Isolation of Diversified Chaetoglobosins from the Coral-Associated Fungus Chaetomium globosum C2F17
by Xiao-Wei Luo, Cheng-Hai Gao, Hu-Mu Lu, Jia-Min Wang, Zi-Qi Su, Hua-Ming Tao, Xue-Feng Zhou, Bin Yang and Yong-Hong Liu
Molecules 2020, 25(5), 1237; https://doi.org/10.3390/molecules25051237 - 9 Mar 2020
Cited by 16 | Viewed by 3414
Abstract
Cytochalasans have continuously aroused considerable attention among the chemistry and pharmacology communities due to their structural complexities and pharmacological significances. Sixteen structurally diverse chaetoglobosins, 10-(indol-3-yl)-[13]cytochalasans, including a new one, 6-O-methyl-chaetoglobosin Q (1), were isolated from the coral-associated fungus Chaetomium [...] Read more.
Cytochalasans have continuously aroused considerable attention among the chemistry and pharmacology communities due to their structural complexities and pharmacological significances. Sixteen structurally diverse chaetoglobosins, 10-(indol-3-yl)-[13]cytochalasans, including a new one, 6-O-methyl-chaetoglobosin Q (1), were isolated from the coral-associated fungus Chaetomium globosum C2F17. Their structures were accomplished by extensive spectroscopic analysis combined with single-crystal X-ray crystallography and ECD calculations. Meanwhile, the structures and absolute configurations of the previously reported compounds 6, 12, and 13 were confirmed by single-crystal X-ray analysis for the first time. Chaetoglobosins E (6) and Fex (11) showed significant cytotoxicity against a panel of cancer cell lines, K562, A549, Huh7, H1975, MCF-7, U937, BGC823, HL60, Hela, and MOLT-4, with the IC50 values ranging from 1.4 μM to 9.2 μM. Full article
(This article belongs to the Special Issue Natural Products from Fungi)
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9 pages, 1071 KiB  
Article
Alpha-Glucosidase- and Lipase-Inhibitory Phenalenones from a New Species of Pseudolophiostoma Originating from Thailand
by Allan Patrick G. Macabeo, Luis Agustin E. Pilapil, Katherine Yasmin M. Garcia, Mark Tristan J. Quimque, Chayanard Phukhamsakda, Allaine Jean C. Cruz, Kevin D. Hyde and Marc Stadler
Molecules 2020, 25(4), 965; https://doi.org/10.3390/molecules25040965 - 20 Feb 2020
Cited by 17 | Viewed by 5089
Abstract
The alpha-glucosidase- and lipase-inhibitory activities of three phenalenones (1–3) and one phenylpropanoid (4) from the ethyl acetate extracts of a Pseudolophiosptoma sp. are described. They represent the first secondary metabolites reported from the genus Pseudolophiostoma. Scleroderolide [...] Read more.
The alpha-glucosidase- and lipase-inhibitory activities of three phenalenones (1–3) and one phenylpropanoid (4) from the ethyl acetate extracts of a Pseudolophiosptoma sp. are described. They represent the first secondary metabolites reported from the genus Pseudolophiostoma. Scleroderolide (1) and sclerodione (2) exhibited potent α-glucosidase- and porcine-lipase-inhibitory activity during primary screening, with better IC50 values compared to the positive controls, N-deoxynojirimycin and orlistat. In silico techniques were employed to validate the probable biological targets and elucidate the mechanism of actions of phenalenones 1 and 2. Both compounds exhibited strong binding affinities to both alpha-glucosidase and porcine lipase through H-bonding and π–π interactions. Interestingly, favorable in silico ADME (absorption, distribution, metabolism, and excretion) properties such as gastrointestinal absorption were also predicted using software. Full article
(This article belongs to the Special Issue Natural Products from Fungi)
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33 pages, 6269 KiB  
Article
Differences in Production, Composition, and Antioxidant Activities of Exopolymeric Substances (EPS) Obtained from Cultures of Endophytic Fusarium culmorum Strains with Different Effects on Cereals
by Jolanta Jaroszuk-Ściseł, Artur Nowak, Iwona Komaniecka, Adam Choma, Anna Jarosz-Wilkołazka, Monika Osińska-Jaroszuk, Renata Tyśkiewicz, Adrian Wiater and Jerzy Rogalski
Molecules 2020, 25(3), 616; https://doi.org/10.3390/molecules25030616 - 30 Jan 2020
Cited by 18 | Viewed by 3910
Abstract
Exopolymeric substances (EPS) can determine plant-microorganism interactions and have great potential as bioactive compounds. The different amounts of EPS obtained from cultures of three endophytic Fusarium culmorum strains with different aggressiveness—growth promoting (PGPF), deleterious (DRMO), and pathogenic towards cereal plants—depended on growth conditions. [...] Read more.
Exopolymeric substances (EPS) can determine plant-microorganism interactions and have great potential as bioactive compounds. The different amounts of EPS obtained from cultures of three endophytic Fusarium culmorum strains with different aggressiveness—growth promoting (PGPF), deleterious (DRMO), and pathogenic towards cereal plants—depended on growth conditions. The EPS concentrations (under optimized culture conditions) were the lowest (0.2 g/L) in the PGPF, about three times higher in the DRMO, and five times higher in the pathogen culture. The EPS of these strains differed in the content of proteins, phenolic components, total sugars, glycosidic linkages, and sugar composition (glucose, mannose, galactose, and smaller quantities of arabinose, galactosamine, and glucosamine). The pathogen EPS exhibited the highest total sugar and mannose concentration. FTIR analysis confirmed the β configuration of the sugars. The EPS differed in the number and weight of polysaccharidic subfractions. The EPS of PGPF and DRMO had two subfractions and the pathogen EPS exhibited a subfraction with the lowest weight (5 kDa). The three EPS preparations (ethanol-precipitated EP, crude C, and proteolysed P) had antioxidant activity (particularly high for the EP-EPS soluble in high concentrations). The EP-EPS of the PGPF strain had the highest antioxidant activity, most likely associated with the highest content of phenolic compounds in this EPS. Full article
(This article belongs to the Special Issue Natural Products from Fungi)
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8 pages, 1610 KiB  
Article
Antimicrobial Secondary Metabolites from the Seawater-Derived Fungus Aspergillus sydowii SW9
by Yu-Jing Liu, Jian-Long Zhang, Chen Li, Xue-Gen Mu, Xiao-Li Liu, Lei Wang, Yan-Cui Zhao, Peng Zhang, Xiao-Dong Li and Xing-Xiao Zhang
Molecules 2019, 24(24), 4596; https://doi.org/10.3390/molecules24244596 - 16 Dec 2019
Cited by 16 | Viewed by 3322
Abstract
Marine-derived fungi are considered to be valuable producers of bioactive secondary metabolites used as lead compounds with medicinal importance. In this study, chemical investigation of the seawater-derived fungus Aspergillus sydowii SW9 led to the isolation and identification of one new quinazolinone alkaloid, 2-(4-hydroxybenzyl)-4-(3-acetyl)quinazolin-one [...] Read more.
Marine-derived fungi are considered to be valuable producers of bioactive secondary metabolites used as lead compounds with medicinal importance. In this study, chemical investigation of the seawater-derived fungus Aspergillus sydowii SW9 led to the isolation and identification of one new quinazolinone alkaloid, 2-(4-hydroxybenzyl)-4-(3-acetyl)quinazolin-one (1), one new aromatic bisabolene-type sesquiterpenoid, (2) and one new chorismic acid analogue (3), as well as two known alkaloids (compounds 4 and 5). Their structures were determined by extensive 1D/2D NMR and mass spectrometric data, and the absolute configurations of 2 and 3 were assigned by the analysis of ECD spectra aided by quantum chemical computations. Compounds 1, 2, and 4 exhibited selective inhibitory activities against the human pathogenic bacteria Escherichia coli, Staphylococcus aureus, S. epidermidis, and Streptococcus pneumoniae, with MIC values ranging from 2.0 to 16 μg/mL. Full article
(This article belongs to the Special Issue Natural Products from Fungi)
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