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The secondary metabolites of the alga-derived fungus Aspergillus niveoglaucus КММ 4176 and their antimicrobial and antibiofilm activities

The Journal of Antibiotics volume 78, pages 314–329 (2025)Cite this article

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Abstract

Marine alga-derived fungal strain КММ 4176 was identified as Aspergillus niveoglaucus based on ITS region BenA, CaM and RPB2 gene sequence analysis. The anthraquinone derivatives emodin anthrone (1) and 4-hydroxyemodin anthrone (2), chromone derivative aloesone (3), and indole diketopiperazine alkaloid neoechinulin B (4) were isolated from the ethyl acetate extract of this fungus. In addition, UPLC MS data analysis of the KMM 4176 extract showed the presence of 17 echinulin-family alkaloids, as well as their biogenetic precursor cyclo(l-alanyl-l-tryptophyl) and a number of polyketide compounds. Emodin anthrone and 4-hydroxyemodin anthrone were found as inhibitors of biofilm formation by Staphylococcus aureus with half-maximal inhibitory concentrations (IC50) of 5.5 µM and 23.7 µM, respectively. Moreover, emodin anthrone (1) and 4-hydroxyemodin anthrone (2) inhibited staphylococcal sortase A activity with IC50 of 9.2 µM and 37.6 µM, respectively. Aloesone (3) also inhibited S. aureus biofilm formation but was less active. The first data on neoechinulin B (4) antibiofilm activity and sortase A inhibition were obtained. The positive effects of the isolated compounds on the growth of HaCaT keratinocytes infected with S. aureus were also observed.

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Acknowledgements

This study was carried out using the equipment of the Collective Facilities Center “The Far Eastern Center for Structural Molecular Research (NMR/MS) PIBOC FEB RAS” and using the Collective Facilities Center “Collection of Marine Microorganisms PIBOC FEB RAS”. The authors thank Technoinfo company (https://technoinfo.ru) and personally Alexander Smirnov for the opportunity to use the real-time cell imager JuLiStage for this research.

Funding

This research was funded by a grant from the Ministry of Science and Higher Education of Russian Federation 15.BRK.21.0004 (Contract No.: 075-15-2021-1052).

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  1. These authors contributed equally: Nadezhda P. Shlyk, Ekaterina A. Yurchenko

Authors and Affiliations

  1. G.B. Elyakov Paсific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-letiya Vladivostoka, Vladivostok, 690022, Russian Federation

    Nadezhda P. Shlyk, Ekaterina A. Yurchenko, Elena V. Leshchenko, Ekaterina A. Chingizova, Artur R. Chingizov, Viktoria E. Chausova, Natalya N. Kirichuk, Yuliya V. Khudyakova, Mikhail V. Pivkin, Alexandr S. Antonov, Roman S. Popov, Marina P. Isaeva & Anton N. Yurchenko

  2. Far Eastern Federal University, Vladivostok, 690922, Russian Federation

    Nadezhda P. Shlyk

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Shlyk, N.P., Yurchenko, E.A., Leshchenko, E.V. et al. The secondary metabolites of the alga-derived fungus Aspergillus niveoglaucus КММ 4176 and their antimicrobial and antibiofilm activities. J Antibiot 78, 314–329 (2025). https://doi.org/10.1038/s41429-025-00811-0

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