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Marine Drugs
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Fungal Natural Products: An Ongoing Source for New Drug Leads
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Fungal Natural Products: An Ongoing Source for New Drug Leads

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (20 April 2021) | Viewed by 26540

Special Issue Editor

Dr. Zeinab Khalil

E-Mail Website
Guest Editor
Institute for Molecular Bioscience, The University of Queensland, Brisbane Qld 4072 Australia
Interests: Marine Sponge; Marine Fungi; Microbiology; Chemical Analysis; Organic Chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Natural products continue to play a crucial role in the discovery of new drugs and drug leads. Biodiscovery from microbial resources can be described as the exploration of microbial metabolic products that provide important benefits to the fields of medicine, agriculture, and biotechnology. Fungi play a vital role in microbial discovery as it produces a variety of secondary metabolites (such as polyketides, non-ribosomal peptides and terpenes) associated with an array of biological activities such as anticancer, antibiotics, etc. Due to the promising biological properties of the fungal metabolites, they represent a promising lead in the discovery and development of drugs.

Dr. Zeinab Khalil
Guest Editor

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. Marine Drugs is an international peer-reviewed open access monthly 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 2900 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

  • natural products
  • microbial resources
  • fungal metabolites
  • discovery and development of drugs

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Published Papers (7 papers)

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Research

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16 pages, 1593 KiB  
Article
Application of Feature-Based Molecular Networking for Comparative Metabolomics and Targeted Isolation of Stereoisomers from Algicolous Fungi
by Bicheng Fan, Laura Grauso, Fengjie Li, Silvia Scarpato, Alfonso Mangoni and Deniz Tasdemir
Mar. Drugs 2022, 20(3), 210; https://doi.org/10.3390/md20030210 - 16 Mar 2022
Cited by 8 | Viewed by 3678
Abstract
Seaweed endophytic (algicolous) fungi are talented producers of bioactive natural products. We have previously isolated two strains of the endophytic fungus, Pyrenochaetopsis sp. FVE-001 and FVE-087, from the thalli of the brown alga Fucus vesiculosus. Initial chemical studies yielded four new decalinoylspirotetramic [...] Read more.
Seaweed endophytic (algicolous) fungi are talented producers of bioactive natural products. We have previously isolated two strains of the endophytic fungus, Pyrenochaetopsis sp. FVE-001 and FVE-087, from the thalli of the brown alga Fucus vesiculosus. Initial chemical studies yielded four new decalinoylspirotetramic acid derivatives with antimelanoma activity, namely pyrenosetins A–C (1–3) from Pyrenochaetopsis sp. strain FVE-001, and pyrenosetin D (4) from strain FVE-087. In this study, we applied a comparative metabolomics study employing HRMS/MS based feature-based molecular networking (FB MN) on both Pyrenochaetopsis strains. A higher chemical capacity in production of decalin derivatives was observed in Pyrenochaetopsis sp. FVE-087. Notably, several decalins showed different retention times despite the same MS data and MS/MS fragmentation pattern with the previously isolated pyrenosetins, indicating they may be their stereoisomers. FB MN-based targeted isolation studies coupled with antimelanoma activity testing on the strain FVE-087 afforded two new stereoisomers, pyrenosetins E (5) and F (6). Extensive NMR spectroscopy including DFT computational studies, HR-ESIMS, and Mosher’s ester method were used in the structure elucidation of compounds 5 and 6. The 3’R,5’R stereochemistry determined for compound 6 was identical to that previously reported for pyrenosetin C (3), whose stereochemistry was revised as 3’S,5’R in this study. Pyrenosetin E (5) inhibited the growth of human malignant melanoma cells (A-375) with an IC50 value of 40.9 μM, while 6 was inactive. This study points out significant variations in the chemical repertoire of two closely related fungal strains and the versatility of FB MN in identification and targeted isolation of stereoisomers. It also confirms that the little-known fungal genus Pyrenochaetopsis is a prolific source of complex decalinoylspirotetramic acid derivatives. Full article
(This article belongs to the Special Issue Fungal Natural Products: An Ongoing Source for New Drug Leads)
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15 pages, 1989 KiB  
Article
Precursor-Directed Biosynthesis Mediated Amplification of Minor Aza Phenylpropanoid Piperazines in an Australian Marine Fish-Gut-Derived Fungus, Chrysosporium sp. CMB-F214
by Ahmed H. Elbanna, Amila Agampodi Dewa, Zeinab G. Khalil and Robert J. Capon
Mar. Drugs 2021, 19(9), 478; https://doi.org/10.3390/md19090478 - 25 Aug 2021
Cited by 9 | Viewed by 2707
Abstract
Chemical analysis of an M1 agar plate cultivation of a marine fish-gut-derived fungus, Chrysosporium sp. CMB-F214, revealed the known chrysosporazines A–D (11–14) in addition to a suite of very minor aza analogues 1–6. A microbioreactor (MATRIX) [...] Read more.
Chemical analysis of an M1 agar plate cultivation of a marine fish-gut-derived fungus, Chrysosporium sp. CMB-F214, revealed the known chrysosporazines A–D (11–14) in addition to a suite of very minor aza analogues 1–6. A microbioreactor (MATRIX) cultivation profiling analysis failed to deliver cultivation conditions that significantly improved the yields of 1–6; however, it did reveal that M2 agar cultivation produced the new natural product 15. A precursor-directed biosynthesis strategy adopting supplementation of a CMB-F214 M1 solid agar culture with sodium nicotinate enhanced production of otherwise inaccessible azachrysposorazines A1 (1), A2 (2), B1 (3), C1 (4), C2 (5) and D1 (6), in addition to four new chrysosporazines; chrysosporazines N–P (7–9) and spirochrysosporazine A (10). Structures inclusive of absolute configurations were assigned to 1–15 based on detailed spectroscopic and chemical analyses, and biosynthetic considerations. Non-cytotoxic to human carcinoma cells, azachrysosporazies 1–5 were capable of reversing doxorubicin resistance in P-glycoprotein (P-gp)-overexpressing human colon carcinoma cells (SW620 Ad300), with optimum activity exhibited by the C-2′ substituted analogues 3–5. Full article
(This article belongs to the Special Issue Fungal Natural Products: An Ongoing Source for New Drug Leads)
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10 pages, 1377 KiB  
Article
New Isocoumarin Analogues from the Marine-Derived Fungus Paraphoma sp. CUGBMF180003
by Xiuli Xu, Jiangpeng Li, Kai Zhang, Shangzhu Wei, Rui Lin, Steven W. Polyak, Na Yang and Fuhang Song
Mar. Drugs 2021, 19(6), 313; https://doi.org/10.3390/md19060313 - 28 May 2021
Cited by 13 | Viewed by 3012
Abstract
Nine new secondary metabolites, including six isocoumarin analogues, 7-hydroxyoospolactone (1), 7-methoxyoospolactone (2), 7-methoxy-9-hydroxyoospolactone (3), 10-acetoxy-9-hydroxyoospolactone (4), 6-dehydroxysescandelin (5), parapholactone (6), and three compounds with a rare skeleton of isocoumarin coupled with [...] Read more.
Nine new secondary metabolites, including six isocoumarin analogues, 7-hydroxyoospolactone (1), 7-methoxyoospolactone (2), 7-methoxy-9-hydroxyoospolactone (3), 10-acetoxy-9-hydroxyoospolactone (4), 6-dehydroxysescandelin (5), parapholactone (6), and three compounds with a rare skeleton of isocoumarin coupled with phenylethylamine, namely paraphamide A (12), paraphamide B (13), and paraphamide C (14), together with five known compounds, oospolactone (7), 8-O-methyloospolactone (8), 10-hydroxyoospolactone (9), 9,10-dihydroxyoospolactone (10), and oospoglycol (11), were isolated and identified from the marine-derived fungus Paraphoma sp. CUGBMF180003. Their chemical structures were determined using spectroscopic data, including HRESIMS and 1D and 2D NMR techniques. Furthermore, the stereogenic carbons in 5 and 14 were determined by comparing the experimental and calculated electronic circular dichroism (ECD) spectra. The carbon skeleton of 12–14 was identified as the first example of isocoumarin coupled with phenylethylamine derivatives. All of these compounds were examined for antimicrobial activities against Candida albicans and Staphylococcus aureus. Both 1 and 6 showed antibacterial activity against S. aureus with MIC values of 12.5 μg/mL. Full article
(This article belongs to the Special Issue Fungal Natural Products: An Ongoing Source for New Drug Leads)
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22 pages, 7800 KiB  
Article
OVAT Analysis and Response Surface Methodology Based on Nutrient Sources for Optimization of Pigment Production in the Marine-Derived Fungus Talaromyces albobiverticillius 30548 Submerged Fermentation
by Mekala Venkatachalam, Alain Shum-Chéong-Sing, Yanis Caro, Laurent Dufossé and Mireille Fouillaud
Mar. Drugs 2021, 19(5), 248; https://doi.org/10.3390/md19050248 - 27 Apr 2021
Cited by 14 | Viewed by 4022
Abstract
Pigment production from filamentous fungi is gaining interest due to the diversity of fungal species, the variety of compounds synthesized, and the possibility of controlled massive productions. The Talaromyces species produce a large panel of metabolites, including Monascus-like azaphilone pigments, with potential use [...] Read more.
Pigment production from filamentous fungi is gaining interest due to the diversity of fungal species, the variety of compounds synthesized, and the possibility of controlled massive productions. The Talaromyces species produce a large panel of metabolites, including Monascus-like azaphilone pigments, with potential use as natural colorants in industrial applications. Optimizing pigment production from fungal strains grown on different carbon and nitrogen sources, using statistical methods, is widespread nowadays. The present work is the first in an attempt to optimize pigments production in a culture of the marine-derived T. albobiverticillius 30548, under the influence of several nutrients sources. Nutrient combinations were screened through the one-variable-at-a-time (OVAT) analysis. Sucrose combined with yeast extract provided a maximum yield of orange pigments (OPY) and red pigments (RPY) (respectively, 1.39 g/L quinizarin equivalent and 2.44 g/L Red Yeast pigment equivalent), as well as higher dry biomass (DBW) (6.60 g/L). Significant medium components (yeast extract, K2HPO4 and MgSO4·7H2O) were also identified from one-variable-at-a-time (OVAT) analysis for pigment and biomass production. A five-level central composite design (CCD) and a response surface methodology (RSM) were applied to evaluate the optimal concentrations and interactive effects between selected nutrients. The experimental results were well fitted with the chosen statistical model. The predicted maximum response for OPY (1.43 g/L), RPY (2.59 g/L), and DBW (15.98 g/L) were obtained at 3 g/L yeast extract, 1 g/L K2HPO4, and 0.2 g/L MgSO4·7H2O. Such optimization is of great significance for the selection of key nutrients and their concentrations in order to increase the pigment production at a pilot or industrial scale. Full article
(This article belongs to the Special Issue Fungal Natural Products: An Ongoing Source for New Drug Leads)
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18 pages, 3105 KiB  
Article
Heteroexpression of Aspergillus nidulans laeA in Marine-Derived Fungi Triggers Upregulation of Secondary Metabolite Biosynthetic Genes
by Ishrat Khan, Wan-Lin Xie, Yu-Chao Yu, Huan Sheng, Yan Xu, Jia-Qi Wang, Sanjit Chandra Debnath, Jin-Zhong Xu, Dao-Qiong Zheng, Wan-Jing Ding and Pin-Mei Wang
Mar. Drugs 2020, 18(12), 652; https://doi.org/10.3390/md18120652 - 18 Dec 2020
Cited by 10 | Viewed by 4250
Abstract
Fungi are a prospective resource of bioactive compounds, but conventional methods of drug discovery are not effective enough to fully explore their metabolic potential. This study aimed to develop an easily attainable method to elicit the metabolic potential of fungi using Aspergillus nidulans [...] Read more.
Fungi are a prospective resource of bioactive compounds, but conventional methods of drug discovery are not effective enough to fully explore their metabolic potential. This study aimed to develop an easily attainable method to elicit the metabolic potential of fungi using Aspergillus nidulans laeA as a transcription regulation tool. In this study, functional analysis of Aspergillus nidulans laeA (AnLaeA) and Aspergillus sp. Z5 laeA (Az5LaeA) was done in the fungus Aspergillus sp. Z5. Heterologous AnLaeA-and native Az5LaeA-overexpression exhibited similar phenotypic effects and caused an increase in production of a bioactive compound diorcinol in Aspergillus sp. Z5, which proved the conserved function of this global regulator. In particular, heteroexpression of AnLaeA showed a significant impact on the expression of velvet complex genes, diorcinol synthesis-related genes, and different transcription factors (TFs). Moreover, heteroexpression of AnLaeA influenced the whole genome gene expression of Aspergillus sp. Z5 and triggered the upregulation of many genes. Overall, these findings suggest that heteroexpression of AnLaeA in fungi serves as a simple and easy method to explore their metabolic potential. In relation to this, AnLaeA was overexpressed in the fungus Penicillium sp. LC1-4, which resulted in increased production of quinolactacin A. Full article
(This article belongs to the Special Issue Fungal Natural Products: An Ongoing Source for New Drug Leads)
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10 pages, 1309 KiB  
Article
Absolute Configurations and Chitinase Inhibitions of Quinazoline-Containing Diketopiperazines from the Marine-Derived Fungus Penicillium polonicum
by Xing-Chen Guo, Ya-Hui Zhang, Wen-Bin Gao, Li Pan, Hua-Jie Zhu and Fei Cao
Mar. Drugs 2020, 18(9), 479; https://doi.org/10.3390/md18090479 - 21 Sep 2020
Cited by 26 | Viewed by 2951
Abstract
Three new quinazoline-containing diketopiperazines, polonimides A–C (1–3), along with four analogues (4–7), were obtained from the marine-derived fungus Penicillium polonicum. Among them, 2 and 4, 3 and 5 were epimers, respectively, resulting the [...] Read more.
Three new quinazoline-containing diketopiperazines, polonimides A–C (1–3), along with four analogues (4–7), were obtained from the marine-derived fungus Penicillium polonicum. Among them, 2 and 4, 3 and 5 were epimers, respectively, resulting the difficulty in the determination of their configurations. The configurations of 1–3 were determined by 1D nuclear overhauser effect (NOE), Marfey and electron circular dichroism (ECD) methods. Nuclear magnetic resonance (NMR) calculation with the combination of DP4plus probability method was used to distinguish the absolute configurations of C-3 in 3 and 5. All of 1–7 were tested for their chitinase inhibitory activity against OfHex1 and OfChi-h and cytotoxicity against A549, HGC-27 and UMUC-3 cell lines. Compounds 1–7 exhibited weak activity towards OfHex1 and strong activity towards OfChi-h at a concentration of 10.0 μM, with the inhibition rates of 0.7%–10.3% and 79.1%–95.4%, respectively. Interestingly, 1–7 showed low cytotoxicity against A549, HGC-27 and UMUC-3 cell lines, suggesting that good prospect of this cluster of metabolites for drug discovery. Full article
(This article belongs to the Special Issue Fungal Natural Products: An Ongoing Source for New Drug Leads)
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Review

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25 pages, 7049 KiB  
Review
Methods in Microbial Biodiscovery
by Angela A. Salim, Zeinab G. Khalil, Ahmed H. Elbanna, Taizong Wu and Robert J. Capon
Mar. Drugs 2021, 19(9), 503; https://doi.org/10.3390/md19090503 - 3 Sep 2021
Cited by 21 | Viewed by 4819
Abstract
This review presents an account of the microbial biodiscovery methodology developed and applied in our laboratory at The University of Queensland, Institute for Molecular Bioscience, with examples drawn from our experiences studying natural products produced by Australian marine-derived (and terrestrial) fungi and bacteria. [...] Read more.
This review presents an account of the microbial biodiscovery methodology developed and applied in our laboratory at The University of Queensland, Institute for Molecular Bioscience, with examples drawn from our experiences studying natural products produced by Australian marine-derived (and terrestrial) fungi and bacteria. Full article
(This article belongs to the Special Issue Fungal Natural Products: An Ongoing Source for New Drug Leads)
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