Absolute configuration of cytotoxic anthraquinones from a Brazilian cave soil‐derived fungus, <i>Aspergillus</i> sp. SDC28

Investigation of the marine sponge Agelas dispar MeOH fractions using feature-based molecular networking, dereplication, and isolation led to the discovery of new bromopyrrole-derived metabolites. An in-house library of bromopyrrole alkaloids previously isolated from A. dispar and Dictyonella sp. was utilized, along with the investigation of an MS/MS fragmentation of these compounds. Our strategy led to the isolation and identification of the disparamides A–C (1–3), with a novel carbon skeleton. Additionally, new dispyrins B–F (4–8) and nagelamides H2 and H3 (9 and 10) and known nagelamide H (11), citrinamine B (12), ageliferin (13), bromoageliferin (14), and dibromoageliferin (15) were also isolated and identified by analysis of spectroscopic data. Analysis of MS/MS fragmentation data and molecular networking analysis indicated the presence of hymenidin (16), oroidin (17), dispacamide (18), monobromodispacamide (19), keramadine (20), longamide B (21), methyl ester of longamide B (22), hanishin (23), methyl ester of 3-debromolongamide B (24), and 3-debromohanishin (25). Antibacterial activity of ageliferin (13), bromoageliferin (14), and dibromoageliferin (15) was evaluated against susceptible and multi-drug-resistant ESKAPE pathogenic bacteria Klabsiella pneumoniae, Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Acinetobacter baumannii, and Enterococcus faecalis. Dibromoageliferin (15) displayed the most potent antimicrobial activity against all tested susceptible and MDR strains. Compounds 13–15 presented no significant hemolytic activity up to 100 μM.

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“…The cytotoxicity assay using human ovarian cancer cells OVCAR3 has been performed as previously described …”

Section: Methodsmentioning

confidence: 99%

Feature-Based Molecular Networking Discovery of Bromopyrrole Alkaloids from the Marine Sponge Agelas dispar

et al. 2022

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“…Xanthocillin X inhibited the growth of the Gram-negative pathogens Acinetobacter baumannii , K. pneumoniae , and P. aeruginosa growth with MIC values of 0.125 μg/mL [ 233 ]. Gubiani et al [ 181 ] described that the soil-derived fungus Aspergillus sp SDC28, isolated from a Brazilian cave, produced the anthraquinones versicolorin C and versiconol, which were cytotoxic on human ovarian cancer cells (OVCAR3) with IC50 of 0.24 and of 1.07 μM, respectively, while the IC50 for taxol was 7 ± 2 nM. Beyond the cytotoxic effect, the study was the first one to report the spectroscopic characterization, including the absolute configuration of both anthraquinones, attesting to the relevance in drug discovery using extremophile fungi.…”

Section: Studies Of Fungal Secondary Metabolites As Cytotoxic and Ant...mentioning

confidence: 99%

Overview of Bioactive Fungal Secondary Metabolites: Cytotoxic and Antimicrobial Compounds

et al. 2022

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Microorganisms are known as important sources of natural compounds that have been studied and applied for different purposes in distinct areas. Specifically, in the pharmaceutical area, fungi have been explored mainly as sources of antibiotics, antiviral, anti-inflammatory, enzyme inhibitors, hypercholesteremic, antineoplastic/antitumor, immunomodulators, and immunosuppressants agents. However, historically, the high demand for new antimicrobial and antitumor agents has not been sufficiently attended by the drug discovery process, highlighting the relevance of intensifying studies to reach sustainable employment of the huge world biodiversity, including the microorganisms. Therefore, this review describes the main approaches and tools applied in the search for bioactive secondary metabolites, as well as presents several examples of compounds produced by different fungi species with proven pharmacological effects and additional examples of fungal cytotoxic and antimicrobial molecules. The review does not cover all fungal secondary metabolites already described; however, it presents some reports that can be useful at any phase of the drug discovery process, mainly for pharmaceutical applications.

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“…Cave fungi interact with minerals, fix nitrogen, and utilize aromatic compounds, influencing fungal metabolism and cave biogeochemistry 7 , and potentially producing novel compounds, bioactive secondary metabolites, and/or enzymes, enabling them to survive in harsh environments 9 , 10 . Most cave fungi are not native to caves and are likely introduced by humans, water, air currents, and animals, with Ascomycota being the most common phylum 11 – 13 .…”

Section: Introductionmentioning

confidence: 99%

Unravelling the hidden diversity of cave mycobiota in Thailand’s Satun Geopark

Suetrong,

Preedanon,

Kobmoo

et al. 2023

Sci Rep

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Karst caves are distinctive ecosystems that have limited nutrients, darkness, low to moderate temperatures, and high moisture levels, which allow for a diverse range of fungal communities to thrive. Despite their significance, little is understood about the fungi found in karst caves in Thailand. In 2019, we studied the cultured mycobiota from five substrate types (air, water, rock, soil/sediment, and organic debris) in two karst caves (Le Stegodon and Phu Pha Phet Caves) of the Satun UNESCO Global Geopark, southern Thailand. A cumulative count of 829 distinct fungal morphological types was identified, encompassing 319 fungal culturable were observed. Based on preliminary analyses of the internal transcribed spacer (ITS) sequence using BLAST searches, the most common phylum among the fungal morphotypes was Ascomycota, harboring 282 species in 91 genera, 93.4% of which were distributed in the classes Eurotiomycetes, Sordariomycetes, and Dothideomycetes. The most common fungal genera identified in the two karst caves were Aspergillus, Penicillium, Cladosporium, Talaromyces, Xylaria, and Trichoderma, with 45, 41, 24, 14, 14, and 6 species identified, respectively. Discovering fungi in Thai karst caves highlights the extensive fungal diversity in the Satun UNESCO Global Geopark, implying undiscovered species, and emphasizing the need for comprehensive investigations in other unexplored Thai karst caves.

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Absolute configuration of cytotoxic anthraquinones from a Brazilian cave soil‐derived fungus, Aspergillus sp. SDC28

Cited by 5 publications

References 28 publications

Feature-Based Molecular Networking Discovery of Bromopyrrole Alkaloids from the Marine Sponge Agelas dispar

Feature-Based Molecular Networking Discovery of Bromopyrrole Alkaloids from the Marine Sponge Agelas dispar

Overview of Bioactive Fungal Secondary Metabolites: Cytotoxic and Antimicrobial Compounds

Unravelling the hidden diversity of cave mycobiota in Thailand’s Satun Geopark

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