Secondary Metabolites, including a New 5,6-Dihydropyran-2-One, Produced by the Fungus Diplodia corticola . Aphicidal Activity of the Main Metabolite, Sphaeropsidin A.
Maria Michela SalvatoreIlaria Di LelioMarina DellaGrecaRosario NicolettiFrancesco SalvatoreElia RussoGennaro VolpeAndrea BecchimanziAlla Eddine MahamediAkila Berraf-TebbalAndolfi AnnaPublished in: Molecules (Basel, Switzerland) (2022)
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 (5 S ,6S,7 Z ,9 S ,10 S )-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 LC 50 of 9.64 mM.