Abstract
A new verrucosidin derivative, methyl isoverrucosidinol (1), was isolated from the marine fungus Penicillium sp. Y-50-10, dwelling in sulfur rich sediment in the Kueishantao hydrothermal vents off Taiwan. The structure was established by spectroscopic means including HRMS and 2D-NMR spectroscopic analysis. The absolute configuration was defined mainly by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Among hitherto known compounds with a verrucosidine backbone isolated from natural resource, compound 1 represents the first example of a new conformational isomer of its skeleton, exhibiting antibiotic activity against Bacillus subtilis with MIC value 32 μg/mL.
Highlights
Marine microorganisms have been under the spotlight of scientists during the last decade due to their tremendous abilities of generating exceptional and potent natural products [1,2]
Tetracycline was used as a positive control against E. coli, S. aureus and B. subtilis which showed MIC values of 2, 2, 1 μg/mL, respectively
Due to the duplication in the isolation of secondary metabolites from terrestrial sources, the marine world can be considered as the sole source of novel compounds with beneficial applications in the medical sector
Summary
Marine microorganisms have been under the spotlight of scientists during the last decade due to their tremendous abilities of generating exceptional and potent natural products [1,2]. It was proven that marine fungi can produce an assortment of secondary metabolites, protecting them from predators as well as acting as effective ways of communication between species [4,5]. As a consequence, these adaptation strategies which enable the production of distinctive compounds with new chemical structures can exhibit substantial bioactivities against pathogens [6]. An unusual conformational isomer of verrucosidin backbone, methyl isoverrucosidinol (1) (Figure 1), was isolated from the fermentation of the hydrothermal vent fungi, Penicillium sp.
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