Prenylated phenylbutyrolactones from cultures of a marine sponge-associated fungus Aspergillus flavipes KUFA1152. (May 2021)

• Record Type: Journal Article
• Authors: Machado, Fátima P.; Kumla, Decha; Pereira, José A.; Sousa, Emilia; Dethoup, Tida; Freitas-Silva, Joana; Costa, Paulo M.; Mistry, Sharad; Silva, Artur M.S.; Kijjoa, Anake
• Is Part Of: Phytochemistry. Volume 185(2021)
• Publication Date: 2021-05
• Subjects: Aspergillus flavipes KUFA1152 -- Trichocomaceae -- Marine sponge-associated fungus -- Mycale sp. -- Prenylated phenylbutyrolactones -- Aspulvinones -- Antibacterial activity -- Antibiofilm activity; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2021.112709
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Four undescribed prenylated phenylbutyrolactones, aspulvinones R, S, T and U, were isolated together with the previously reported aspulvinones A, B′, H and 4-hydroxy-3, 5- bis (3-methylbut-2-en-1-yl)benzaldehyde, from cultures of the marine sponge-derived fungus Aspergillus flavipes KUFA1152. The structures of the undescribed compounds were established on the basis of extensive analysis of 1D and 2D NMR and HRMS spectra. In the case of aspulvinone T, the absolute configuration of its stereogenic carbon was established by comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. The structure of the previously reported compounds were elucidated by 1D and 2D NMR analysis as well as comparison of their 1 H or/and 13 C NMR data with those reported in the literature. Aspulvinones B', H, R, S, T and a mixture of aspulvinones A and U exhibited antibacterial activity against reference strains and multidrug-resistant isolates from the environment as well as capacity to inhibit biofilm formation in the reference strains. However, none of the tested compounds showed potential synergy with clinically relevant antibiotics on multidrug-resistant isolates. Graphical abstract: Image 1 Highlights: Aspergillus flavipes was isolated from the marine sponge Mycale sp . Prenylated phenylbutyrolactones, aspulvinones R, S, T and U were isolated. The absolute configuration of the stereogenic carbon of aspulvinone T was determined. The aspulvinones were tested for antibacterial and antibiofilm activities.