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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Mycotoxin Prevention and Applied Microbiology Research » Research » Publications at this Location » Publication #198314
Title: PENIFULVINS B-E AND A NEW SILPHINENE ANALOGUE: SESQUITERPENOIDS FROM A FUNGICOLOUS ISOLATE OF PENICILLIUM GRISEOFULVUM

Author
item SHIM, SANG HEE - UNIVERSITY OF IOWA
item GLOER, JAMES - UNIVERSITY OF IOWA
item Wicklow, Donald

Submitted to: Journal of Natural Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 7/13/2006
Publication Date: 11/8/2006
Citation: Shim, S., Gloer, J.B., Wicklow, D.T. 2006. Penifulvins B-E and a new silphinene analogue: sesquiterpenoids from a fungicolous isolate of Penicillium griseofulvum. Journal of Natural Products. 69(11):1601-1605.

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. Penifulvins B-E are reported as new analogs of a recently described antiinsectan metabolite penifulvin A, while a new silphinene derivative is identified as having a novel ring system. Insect resistance to pesticides has become increasingly problematic in recent years and new classes of environmentally friendly agricultural pesticides are also needed.

Technical Abstract: Penifulvins B-E (2-5), four new sesquiterpenoids with a dioxa{5.5.5.6}fenestrane ring system, have been isolated from cultures of an isolate of Penicillium griseofulvum (NRRL 35584), together with a new silphinene derivative, 12-hydroxysilphinene-15-oic acid (6). Penifulvins B-E (2-5) are oxidized analogues of penifulvin A (1), and were identified by analysis of NMR and MS data. 12-Hydroxysilphinene-15-oic acid (6) is biogenetically similar, and penifulvins A-E are presumed to be derived from a silphinene precursor. The structures of 2-6, including absolute stereochemistry, were assigned by analysis of NMR data and application of chemical methods.