title: Bridged Epipolythiodiketopiperazines from Penicillium raciborskii, an Endophytic Fungus of Rhododendron tomentosum Harmaja.
abstract: 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.
authors.affiliation: Admescope Ltd. , Typpitie 1, Oulu, Finland , FIN-90620.
authors.forename: Marena
authors.initials: M
authors.lastname: Kajula
authors.forename: Joshua M
authors.initials: JM
authors.lastname: Ward
authors.forename: Ari
authors.initials: A
authors.lastname: Turpeinen
authors.forename: Mysore V
authors.initials: MV
authors.lastname: Tejesvi
authors.affiliation: Admescope Ltd. , Typpitie 1, Oulu, Finland , FIN-90620.
authors.forename: Juho
authors.initials: J
authors.lastname: Hokkanen
authors.affiliation: Admescope Ltd. , Typpitie 1, Oulu, Finland , FIN-90620.
authors.forename: Ari
authors.initials: A
authors.lastname: Tolonen
authors.affiliation: Nanoscience Center, Department of Biological and Environmental Science, University of Jyväskylä , P.O. Box 35, Jyväskylä, Finland , FIN-40014.
authors.forename: Heikki
authors.initials: H
authors.lastname: Häkkänen
authors.affiliation: Department of Pharmaceutical Microbiology, Institute for Medical Microbiology and Immunology , Meckenheimer Allee 168, 53115 Bonn, Germany.
authors.forename: Pere
authors.initials: P
authors.lastname: Picart
authors.affiliation: Nanoscience Center, Department of Biological and Environmental Science, University of Jyväskylä , P.O. Box 35, Jyväskylä, Finland , FIN-40014.
authors.forename: Janne
authors.initials: J
authors.lastname: Ihalainen
authors.affiliation: Department of Pharmaceutical Microbiology, Institute for Medical Microbiology and Immunology , Meckenheimer Allee 168, 53115 Bonn, Germany.
authors.forename: Hans-Georg
authors.initials: HG
authors.lastname: Sahl
authors.forename: Anna Maria
authors.initials: AM
authors.lastname: Pirttilä
authors.forename: Sampo
authors.initials: S
authors.lastname: Mattila
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D010879:Piperazines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029793:Rhododendron / Q000382:microbiology*
chemical_list: D000935:Antifungal Agents; D010879:Piperazines; C555444:epipolythiodiketopiperazine; C000610246:outovirin A; C000610247:outovirin B; C000610248:outovirin C; C036710:gliovirin