Abstract
Three novel compounds, 4-methyl-candidusin A (1), aspetritone A (2) and aspetritone B (3), were obtained from the culture of a coral-derived fungus Aspergillus tritici SP2-8-1, together with fifteen known compounds (4–18). Their structures, including absolute configurations, were assigned based on NMR, MS, and time-dependent density functional theory (TD-DFT) ECD calculations. Compounds 2 and 5 exhibited better activities against methicillin-resistant strains of S. aureus (MRSA) ATCC 43300 and MRSA CGMCC 1.12409 than the positive control chloramphenicol. Compound 5 displayed stronger anti-MRSA and lower cytotoxic activities than 2, and showed stronger antibacterial activities against strains of Vibrio vulnificus, Vibrio rotiferianus, and Vibrio campbellii than the other compounds. Compounds 2 and 10 exhibited significantly stronger cytotoxic activities against human cancer cell lines HeLa, A549, and Hep G2 than the other compounds. Preliminary structure–activity relationship studies indicated that prenylation of terphenyllin or candidusin and the tetrahydrobenzene moiety in anthraquinone derivatives may influence their bioactivity.
Highlights
To date, approximately 70,000 species of fungi have been characterized [1]
Metabolites isolated from species of the genus Aspergillus have continually attracted the interest of pharmacologists due to their broad array of biological activities and their structural diversity
Analysis of 1D NMR, 1 H-1 H COSY, heteronuclear single quantum correlation (HSQC), and heteronuclear multiple bond correlation (HMBC) data revealed the presence of one 2,3-dihydroxy-3-methylbutane unit and one pentasubstituted naphthoquinone moiety
Summary
Approximately 70,000 species of fungi have been characterized [1]. About 1500 species of marine-derived fungi were mentioned, mainly from coastal ecosystems [1]. The fungal sources of novel metabolites have broadened from saprophytic terrestrial strains to marine habitats and living plants with their endophytes [2]. Metabolites isolated from species of the genus Aspergillus have continually attracted the interest of pharmacologists due to their broad array of biological activities and their structural diversity. Studieson onthe thebioactive bioactiveconstituents constituentsofof its novel compounds, compounds,4-methyl-candidusin. Aspetritone (3), together with known fifteen analogues, known analogues, prenylcandidusin andand aspetritone. B (3),Btogether with fifteen includingincluding prenylcandidusin derivatives derivatives (4–5), candidusin (6–7), terphenyllin and anthraquinone (4–5), candidusin derivativesderivatives (6–7), terphenyllin derivativesderivatives (8–14), and(8–14), anthraquinone derivatives derivatives (15–18)
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