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Bridged Epipolythiodiketopiperazines from Penicillium raciborskii, an Endophytic Fungus of Rhododendron tomentosum Harmaja

Three new epithiodiketopiperazine natural products [outovirin A (1), outovirin B (2), and outovirin C (3)] resembling the antifungal natural product gliovirin have been identified in extracts of Penicillium raciborskii, an endophytic fungus isolated from Rhododendron tomentosum. The compounds are un...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2016-04, Vol.79 (4), p.685-690
Main Authors: Kajula, Marena, Ward, Joshua M, Turpeinen, Ari, Tejesvi, Mysore V, Hokkanen, Juho, Tolonen, Ari, Häkkänen, Heikki, Picart, Pere, Ihalainen, Janne, Sahl, Hans-Georg, Pirttilä, Anna Maria, Mattila, Sampo
Format: Article
Language:English
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Summary:Three new epithiodiketopiperazine natural products [outovirin A (1), outovirin B (2), and outovirin C (3)] resembling the antifungal natural product gliovirin have been identified in extracts of Penicillium raciborskii, an endophytic fungus isolated from Rhododendron tomentosum. The compounds are unusual for their class in that they possess sulfide bridges between α- and β-carbons rather than the typical α–α bridging. To our knowledge, outovirin A represents the first reported naturally produced epimonothio­diketopiperazine, and antifungal outovirin C is the first reported trisulfide gliovirin-like compound. This report describes the identification and structural elucidation of the compounds by LC-MS/MS and NMR.
ISSN:0163-3864
1520-6025
DOI:10.1021/np500822k