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Title: PENIFULVIN A: SESQUITERPENOID-DERIVED METABOLITE CONTAINING A NOVEL DIOXA[5,5,5,6]FENESTRANE RING SYSTEM FROM A FUNGICOLOUS ISOLATE OF PENICILLIUM GRISEOFULVUM (NRRL 35584)

Author
item SHIM, SANG HEE - UNIVERSITY OF IOWA
item SWENSON, DALE - UNIVERSITY OF IOWA
item GLOER, JAMES - UNIVERSITY OF IOWA
item Dowd, Patrick
item Wicklow, Donald

Submitted to: Organic Letters
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 2/2/2006
Publication Date: 2/11/2006
Citation: Shim, S.H., Swenson, D.C., Gloer, J.B., Dowd, P.F., Wicklow, D.T. 2006. Penifulvin A: A sesquiterpenoid-derived metabolite containing a novel dioxa[5,5,5,6]fenestrane ring system from a fungicolous isolate of Penicillium griseofulvum. Organic Letters. 8(6):1225-1228. DOI: 10.1021/o1060107c

Interpretive Summary: Fungi that parasitize and kill other fungi offer a potential source of novel antifungal agents useful to agriculture and medicine. The fungus Penicillium griseofulvum (NRRL 35584), encountered as a colonist of a wood decay fungus growing on a dead hardwood branch, collected in a montane dry forest near Kailua-Kona, Hawaii, was examined for its ability to produce antifungal agents and other bioactive metabolites. The antifungal activity of the solvent extract was ascribed to the known compound mycophenolic acid. Penifulvin A is reported as a new fungal metabolite with a previously undescribed ring system and showing significant activity against larvae of the fall armyworm (Spodoptera frugiperda), an important insect pest of corn and other crops. Insect resistance to pesticides has become increasingly problematic in recent years and new classes of environmentally friendly agricultural pesticides are also needed.

Technical Abstract: Penifulvin A (1), a new fungal metabolite with a previously undescribed ring system, has been isolated from cultures of an isolate of Penicillium griseofulvum (NRRL 35584) obtained from a white mycelial growth on a dead hardwood branch collected in a Hawaiian forest. The structure was assigned by analysis of NMR data and confirmed by single-crystal X-ray diffraction analysis. Penifulvin A (1) shows significant activity in dietary assays against the fall armyworm Spodoptera frugiperda.