Abstract
Atlantinone A has been isolated from the psychrotolerant fungus Penicillium ribeum. The exact structure of the compound was confirmed by mass spectrometric and 1- and 2D NMR experiments. Atlantinone A was originally only produced upon chemical epigenetic manipulation of P. hirayamae, however in this study the compound was found to be produced at standard growth conditions by the following species; P. solitum, P. discolor, P. commune, P. caseifulvum, P. palitans, P. novae-zeelandiae and P. monticola. A biosynthetic pathway to atlantinone A starting from andrastin A is proposed.
Highlights
Meroterpenoids such as the andrastins and the citreohybridones are interesting as examples of mixed polyketide-terpenoid biosynthesis [1,2,3] and they often have biological activities [3,4,5,6,7]
An EtOAc extract of Penicillium ribeum (IBT 16537) was separated by high-speed countercurrent chromatography (HSCCC), and through UV-guided fractionation the fifth HSCCC fraction was further purified by HPLC to afford pure 2 (6.8 mg)
Atlantinone A (2) exhibited a molecular ion in HREIMS corresponding to the molecular formula
Summary
Meroterpenoids such as the andrastins and the citreohybridones are interesting as examples of mixed polyketide-terpenoid biosynthesis [1,2,3] and they often have biological activities [3,4,5,6,7]. The andrastins and citreohybridones were originally isolated from hybrid strains of Penicillium sp. P. albocoremium [10], and psychrotolerant strains of P. crustosum from arctic ice [11]. The newly arctic described fungus P. ribeum [12,13], was found to produce a metabolite with the UVspectrum of andrastin A, but with a different retention time and molecular mass. The data for the compound matched those of the newly reported compound atlantinone A [14], which we have confirmed by isolation and structure elucidation. HPLC-UV-MS analysis demonstrated that several species within genus Penicillium produce the compound under standard laboratory conditions
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