Antibacterial Secondary Metabolites from Marine-Derived Fungus Aspergillus sp. IMCASMF180035

Abstract

Four new secondary metabolites, including one spiro[anthracenone-xanthene] derivative aspergiloxathene A (1), one penicillide analogue, Δ2′-1′-dehydropenicillide (2), and two new phthalide derivatives, 5-methyl-3-methoxyepicoccone (3) and 7-carboxy-4-hydroxy-6-methoxy-5-methylphthalide (4), together with four known compounds, yicathin C (5), dehydropenicillide (6), 3-methoxyepicoccone (7), 4-hydroxy-6-methoxy-5-methylphthalide (8), were identified from the marine-derived fungus Aspergillus sp. IMCASMF180035. Their structures were determined by spectroscopic data, including high-resolution electrospray ionization mass spectrometry (HRESIMS), 1D and 2D nuclear magnetic resonance (NMR) techniques. Compound 1 was identified as the first jointed molecule by xanthene and anthracenone moieties possessing an unprecedented carbon skeleton with spiro-ring system. All compounds were evaluated activities against Staphylococcus aureus, methicillin resistant S. aureus (MRSA), Escherichia coli, Escherichia faecium, Pseudomonas aeruginosa, and Helicobacter pylori. Compound 1 showed significant inhibitory effects against S. aureus and MRSA, with minimum inhibitory concentration (MIC) values of 5.60 and 22.40 µM. Compounds 2 and 6 exhibited potent antibacterial activities against H. pylori, with MIC values of 21.73 and 21.61 µM, respectively.

New Secondary Metabolites from the Marine-Derived Fungus Talaromyces mangshanicus BTBU20211089

“…Seven new compounds, talaromanloid A (1), talaromydene (2), 10-hydroxy-8-demethyltalaromydine and 11-hydroxy-8-demethyltalaromydine (3 and 4), talaromylectone (5), and ditalaromylectones A and B (6 and 7), and seven known compounds (8)(9)(10)(11)(12)(13)(14) were isolated from the marine-derived fungus Talaromyces mangshanicus BTBU20211089. The structures of the new compounds were elucidated by detailed spectroscopic analysis.…”

“…Seven known compounds, including 3-(propan-2-ylidene)-pyrrolidine-2, 5-dione ( 8), (E)-3-(2,5-dioxo-3-(propan-2-ylidene)pyrrolidin-1-yl)acrylic acid (9), nafuredin (10), dehydroaustinol (11), austinolide (12), altenusin (13), and 5 -methoxy-6-methyl-biphenyl-3,4,3triol ( 14), were identified by comparing the NMR data with the corresponding reported data.…”

“…During our ongoing investigations into bioactive natural products from marinederived microorganisms [10][11][12][13], a fungal strain of Talaromyces mangshanicus BTBU20211089, which was isolated from a sediment sample collected from the South China Sea, was found to be active against Candida albicans. Chemical investigation of this fungus cultured in rice solid media led to the isolation and identification of seven new compounds, namely, talaromanloid A (1), talaromydene (2), 10-hydroxy-8-demethyltalaromydine and 11-hydroxyd-8-emethyltalaromydine (3 and 4), talaromylectone (5), and ditalaromylectones A and B (6 and 7), together with seven known compounds.…”

“…Chemical investigation of this fungus cultured in rice solid media led to the isolation and identification of seven new compounds, namely, talaromanloid A (1), talaromydene (2), 10-hydroxy-8-demethyltalaromydine and 11-hydroxyd-8-emethyltalaromydine (3 and 4), talaromylectone (5), and ditalaromylectones A and B (6 and 7), together with seven known compounds. The known compounds were determined to be 3-(propan-2-ylidene)-pyrrolidine-2, 5-dione (8) [14], (E)-3-(2,5-dioxo-3-(propan-2-ylidene)pyrrolidin-1-yl)acrylic acid (9) [15], nafuredin (10) [16], dehydroaustinol (11) [17], austinolide (12) [18], altenusin (13), and 5 -methoxy-6-methyl-biphenyl-3,4,3 -triol (14) [19] (Figure 1). Here, we report the isolation, structure elucidation, and bioactivities of these compounds.…”

“…Here, we report the isolation, structure elucidation, and bioactivities of these compounds. droaustinol (11) [17], austinolide (12) [18], altenusin (13), and 5′-methoxy-6-methyl-biphenyl-3,4,3′-triol ( 14) [19] (Figure 1). Here, we report the isolation, structure elucidation, and bioactivities of these compounds.…”