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Title: CARYOPHYLLENE SESQUITERPENOIDS FROM A FUNGICOLOUS ISOLATE OF PESTALOTIOPSIS DISSEMINATA (THUEM.) STEY.

Author
item DEYRUP, STEPHEN - UNIVERSITY OF IOWA
item SWENSON, DALE - 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: 2/16/2006
Publication Date: 3/11/2006
Citation: Deyrup, S.T., Swenson, D.C., Gloer, J.B., Wicklow, D.T. 2006. Caryophyllene sesquiterpenoids from a fungicolous isolate of Pestalotiopsis disseminata (Thuem.) Stey. Journal of Natural Products. 69:608-611.

Interpretive Summary: Fungi that parasitize and kill other fungi offer a potential source of novel antifungal agents useful to agriculture and medicine. The fungus Pestalotiopsis disseminata (NRRL 36915), encountered as a colonist of an unidentified pyrenomycete growing on a dead hardwood branch in a hardwood swamp within Reed Bingham State Park near Adel, Georgia, was examined for its ability to produce antifungal agents and other bioactive metabolites. Three new analogs of hydroxypunctaporin are reported, two of which showed activity against Bacillus subtilis and Staphylococcus aureus. These compounds do not explain the antifungal activity of the fermentation extract.

Technical Abstract: Three new caryophyllene-type sesquiterpene alcohols, 6-hydroxypunctaporonin E (1), 6-hydroxypunctaporonin B (2), and 6-hydroxypunctaporonin A (3), have been isolated from cultures of the fungicolous fungus Pestalotiopsis disseminata (Thuem.) Stey. The structures of 1-3 were determined mainly by analysis of 1D and 2D NMR data. The structure and absolute stereochemistry of 6-hydroxypunctaporonin E (1) was confirmed through X-ray crystallography of its mono-bromobenzoate derivative. Compounds 1 and 2 showed activity against Gram-positive bacteria.