Abstract
An unusual polyketide with a new carbon skeleton, lindgomycin (1), and the recently described ascosetin (2) were extracted from mycelia and culture broth of different Lindgomycetaceae strains, which were isolated from a sponge of the Kiel Fjord in the Baltic Sea (Germany) and from the Antarctic. Their structures were established by spectroscopic means. In the new polyketide, two distinct domains, a bicyclic hydrocarbon and a tetramic acid, are connected by a bridging carbonyl. The tetramic acid substructure of compound 1 was proved to possess a unique 5-benzylpyrrolidine-2,4-dione unit. The combination of 5-benzylpyrrolidine-2,4-dione of compound 1 in its tetramic acid half and 3-methylbut-3-enoic acid pendant in its decalin half allow the assignment of a new carbon skeleton. The new compound 1 and ascosetin showed antibiotic activities with IC50 value of 5.1 (±0.2) µM and 3.2 (±0.4) μM, respectively, against methicillin-resistant Staphylococcus aureus.
Highlights
Marine-derived fungi living in a stressful habitat are of great interest as new, promising sources of biologically active products
The naturally occurring pyrrolidine-2,4-dione derivatives originating from a variety of marine and terrestrial species have attracted a great deal of interest due to their broad-spectrum biological activities and challenging structural complexity [13,14]
The IR spectra were run on a Perkin Elmer spectrometer with an attenuated total reflectance (ATR) unit. 1H NMR (500 MHz) and
Summary
Marine-derived fungi living in a stressful habitat are of great interest as new, promising sources of biologically active products. The fungal family Lindgomycetaceae (Pleosporales, Dothideomycetes) was introduced by Hirayama et al [8] to accommodate four new species of the genus Lindgomyces. Another three Lindgomyces species were added by Raja et al [9,10], and these authors included. The naturally occurring pyrrolidine-2,4-dione (tetramic acid) derivatives originating from a variety of marine and terrestrial species have attracted a great deal of interest due to their broad-spectrum biological activities and challenging structural complexity [13,14]. Two marine strains of the family Lindgomycetaceae were shown to exhibit a diverse chemical profile, including tetramic acid derivatives having novel structures. The new compound lindgomycin (1) and ascosetin (2) showed antibiotic activities against human and plant pathogenic microorganisms
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