New Alkylpyridinium Anthraquinone, Isocoumarin, C-Glucosyl Resorcinol Derivative and Prenylated Pyranoxanthones from the Culture of a Marine Sponge-Associated Fungus, Aspergillus stellatus KUFA 2017

Machado, Fátima P.; Rodrigues, Inês C.; Gales, Luís; Pereira, José A.; Costa, Paulo M.; Dethoup, Tida; Mistry, Sharad; Silva, Artur M. S.; Vasconcelos, Vitor; Kijjoa, Anake

doi:10.3390/md20110672

Open AccessArticle

New Alkylpyridinium Anthraquinone, Isocoumarin, C-Glucosyl Resorcinol Derivative and Prenylated Pyranoxanthones from the Culture of a Marine Sponge-Associated Fungus, Aspergillus stellatus KUFA 2017

by

Fátima P. Machado

^1,2

,

Inês C. Rodrigues

¹

,

Luís Gales

^1,3

,

José A. Pereira

^1,2

,

Paulo M. Costa

^1,2

,

Tida Dethoup

⁴,

Sharad Mistry

⁵,

Artur M. S. Silva

⁶

,

Vitor Vasconcelos

^2,7

and

Anake Kijjoa

^1,2,*

¹

ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal

²

Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, Portugal

³

Instituto de Biologia Molecular e Celular (i3S-IBMC), Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal

⁴

Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand

⁵

Department of Chemistry, University of Leicester, University Road, Leicester LE 7 RH, UK

⁶

Departamento de Química & QOPNA, Universidade de Aveiro, 3810-193 Aveiro, Portugal

⁷

FCUP-Faculty of Sciences, University of Porto, Rua do Campo Alegre, s/n, 4169-007 Porto, Portugal

^*

Author to whom correspondence should be addressed.

Mar. Drugs 2022, 20(11), 672; https://doi.org/10.3390/md20110672

Submission received: 22 September 2022 / Revised: 25 October 2022 / Accepted: 26 October 2022 / Published: 27 October 2022

(This article belongs to the Special Issue Bioactive Secondary Metabolites of Marine Fungi)

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Abstract

An unreported isocoumarin, (3S,4R)-4-hydroxy-6-methoxymellein (2), an undescribed propylpyridinium anthraquinone (4), and an unreported C-glucosyl resorcinol derivative, acetyl carnemycin E (5c), were isolated, together with eight previously reported metabolites including p-hydroxybenzaldehyde (1), 1,3-dimethoxy-8-hydroxy-6-methylanthraquinone (3a), 1,3-dimethoxy-2,8-dihydroxy-6-methylanthraquinone (3b), emodin (3c), 5[(3E,5E)-nona-3,5-dien-1-yl]benzene (5a), carnemycin E (5b), tajixanthone hydrate (6a) and 15-acetyl tajixanthone hydrate (6b), from the ethyl acetate extract of the culture of a marine sponge-derived fungus, Aspergillus stellatus KUFA 2017. The structures of the undescribed compounds were elucidated by 1D and 2D NMR and high resolution mass spectral analyses. In the case of 2, the absolute configurations of the stereogenic carbons were determined by comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. The absolute configurations of the stereogenic carbons in 6a and 6b were also determined, for the first time, by X-ray crystallographic analysis. Compounds 2, 3a, 3b, 4, 5a, 5b, 5c, 6a, and 6b were assayed for antibacterial activity against four reference strains, viz. two Gram-positive (Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212) and two Gram-negative (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853), as well as three multidrug-resistant strains. However, only 5a exhibited significant antibacterial activity against both reference and multidrug-resistant strains. Compound 5a also showed antibiofilm activity against both reference strains of Gram-positive bacteria.

Keywords: Aspergillus stellatus; Trichocomaceae; marine sponge-associated fungus; anthraquinones; isocoumarin; C-glucosyl resorcinols; antibacterial activity; antibiofilm activity

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MDPI and ACS Style

Machado, F.P.; Rodrigues, I.C.; Gales, L.; Pereira, J.A.; Costa, P.M.; Dethoup, T.; Mistry, S.; Silva, A.M.S.; Vasconcelos, V.; Kijjoa, A. New Alkylpyridinium Anthraquinone, Isocoumarin, C-Glucosyl Resorcinol Derivative and Prenylated Pyranoxanthones from the Culture of a Marine Sponge-Associated Fungus, Aspergillus stellatus KUFA 2017. Mar. Drugs 2022, 20, 672. https://doi.org/10.3390/md20110672

AMA Style

Machado FP, Rodrigues IC, Gales L, Pereira JA, Costa PM, Dethoup T, Mistry S, Silva AMS, Vasconcelos V, Kijjoa A. New Alkylpyridinium Anthraquinone, Isocoumarin, C-Glucosyl Resorcinol Derivative and Prenylated Pyranoxanthones from the Culture of a Marine Sponge-Associated Fungus, Aspergillus stellatus KUFA 2017. Marine Drugs. 2022; 20(11):672. https://doi.org/10.3390/md20110672

Chicago/Turabian Style

Machado, Fátima P., Inês C. Rodrigues, Luís Gales, José A. Pereira, Paulo M. Costa, Tida Dethoup, Sharad Mistry, Artur M. S. Silva, Vitor Vasconcelos, and Anake Kijjoa. 2022. "New Alkylpyridinium Anthraquinone, Isocoumarin, C-Glucosyl Resorcinol Derivative and Prenylated Pyranoxanthones from the Culture of a Marine Sponge-Associated Fungus, Aspergillus stellatus KUFA 2017" Marine Drugs 20, no. 11: 672. https://doi.org/10.3390/md20110672

APA Style

Machado, F. P., Rodrigues, I. C., Gales, L., Pereira, J. A., Costa, P. M., Dethoup, T., Mistry, S., Silva, A. M. S., Vasconcelos, V., & Kijjoa, A. (2022). New Alkylpyridinium Anthraquinone, Isocoumarin, C-Glucosyl Resorcinol Derivative and Prenylated Pyranoxanthones from the Culture of a Marine Sponge-Associated Fungus, Aspergillus stellatus KUFA 2017. Marine Drugs, 20(11), 672. https://doi.org/10.3390/md20110672

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New Alkylpyridinium Anthraquinone, Isocoumarin, C-Glucosyl Resorcinol Derivative and Prenylated Pyranoxanthones from the Culture of a Marine Sponge-Associated Fungus, Aspergillus stellatus KUFA 2017

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