Caryophyllene Sesquiterpenoids from a Fungicolous Isolate of Pestalotia sp.

IH Hwang; JB Gloer; DT Wicklow

doi:10.1055/s-0033-1348652

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Planta Med 2013; 79 - PL11
DOI: 10.1055/s-0033-1348652

Caryophyllene Sesquiterpenoids from a Fungicolous Isolate of Pestalotia sp.

IH Hwang ¹, JB Gloer ¹, DT Wicklow ²

¹Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA
²Bacterial Foodborne Pathogens & Mycology Research Unit, Agricultural Research Service, National Center for Agricultural Utilization Research, USDA, Peoria, IL 61604

Congress Abstract

The ethyl acetate extract from cultures of a fungicolous isolate of Pestalotia sp. (MYC-709) obtained from the surface of a polypore collected in Georgia showed antifungal activity towards Aspergillus flavus and Fusarium verticillioides. ¹H NMR data for the acetonitrile-soluble portion indicated the presence of numerous caryophyllene-type sesquiterpenoids. Chemical investigation of this extract afforded four known caryophyllene sesquiterpenoids (6-hydroxypunctaporonins A, B, and E, and fuscoatrol A) and seven new analogues. The new compounds encountered included 13-hydroxy analogues of 6-hydroxypunctaporonins A, B, and E, and a 6-hydroxy analogue of punctaporonin D. Ketone-containing analogues of 6-hydroxypunctaporonin A and fuscoatrol A and a 9-methoxy derivative of 6-hydroxypunctaporonin D were also obtained. The structures of these compounds were assigned by analysis of 2D NMR and HRESIMS data.