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Metabolites 2012, 2(1), 214-220; doi:10.3390/metabo2010214

Article

Atlantinone A, a Meroterpenoid Produced by Penicillium ribeum and Several Cheese Associated Penicillium Species

Petur W. Dalsgaard ¹ , Bent O. Petersen ² , Jens Ø. Duus ³ , Christian Zidorn ⁴ , Jens C. Frisvad ⁵ , Carsten Christophersen ⁶  and Thomas O. Larsen ^5,*

¹ Department of Forensic Medicine, University of Copenhagen, Frederik V’s Vej 11, DK-2100 Copenhagen, Denmark ² Carlsberg Laboratory, Gamle Carlsbergvej 10, DK-2500 Valby, Denmark ³ Munkehøjvænge 31, 3520 Farum, Denmark ⁴ Institut für Pharmazie, Leopold-Franzens-Universität, Innrain 52, A-6020 Innsbruck, Austria ⁵ Center for Microbial Biotechnology, DTU Systems Biology, Building 221, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark ⁶ Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen, Denmark

* Author to whom correspondence should be addressed.

Received: 7 November 2011; in revised form: 30 December 2011 / Accepted: 10 February 2012 / Published: 23 February 2012

(This article belongs to the Special Issue Secondary Metabolites and Metabolism)

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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.

Keywords: Penicillium ribeum; atlantinone A; andrastin; psychrotolerant; cheese associated fungi

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