Secondary Metabolites, including a New 5,6-Dihydropyran-2-One, Produced by the Fungus <i>Diplodia corticola</i>. Aphicidal Activity of the Main Metabolite, Sphaeropsidin A
Maria Michela Salvatore,
Ilaria Di Lelio,
Marina DellaGreca,
Rosario Nicoletti,
Francesco Salvatore,
Elia Russo,
Gennaro Volpe,
Andrea Becchimanzi,
Alla Eddine Mahamedi,
Akila Berraf-Tebbal,
Anna Andolfi
Affiliations
Maria Michela Salvatore
Department of Chemical Sciences, University of Naples Federico II, 80126 Naples, Italy
Ilaria Di Lelio
Department of Agriculture, University of Naples Federico II, 80055 Portici, Italy
Marina DellaGreca
Department of Chemical Sciences, University of Naples Federico II, 80126 Naples, Italy
Rosario Nicoletti
Department of Agriculture, University of Naples Federico II, 80055 Portici, Italy
Francesco Salvatore
Department of Chemical Sciences, University of Naples Federico II, 80126 Naples, Italy
Elia Russo
Department of Agriculture, University of Naples Federico II, 80055 Portici, Italy
Gennaro Volpe
Department of Agriculture, University of Naples Federico II, 80055 Portici, Italy
Andrea Becchimanzi
Department of Agriculture, University of Naples Federico II, 80055 Portici, Italy
Alla Eddine Mahamedi
Department of Biology, Faculty of Natural Sciences, Life and Earth Sciences, University of Ghardaia, Ghardaia 47000, Algeria
Akila Berraf-Tebbal
Mendeleum-Institute of Genetics, Faculty of Horticulture, Mendel University in Brno, 69144 Lednice, Czech Republic
Anna Andolfi
Department of Chemical Sciences, University of Naples Federico II, 80126 Naples, Italy
An undescribed 5,6-dihydropyran-2-one, namely diplopyrone C, was isolated and characterized from the cultures of an isolate of the fungus Diplodia corticola recovered from Quercus suber in Algeria. The structure and relative stereostructure of (5S,6S,7Z,9S,10S)-5-hydroxy-6-(2-(3-methyloxiran-2-yl)vinyl)-5,6-dihydro-2H-pyran-2-one were assigned essentially based on NMR and MS data. Furthermore, ten known compounds were isolated and identified in the same cultures. The most abundant product, the tetracyclic pimarane diterpene sphaeropsidin A, was tested for insecticidal effects against the model sucking aphid, Acyrthosiphon pisum. Results showed a toxic dose-dependent oral activity of sphaeropsidin A, with an LC50 of 9.64 mM.
