New paspalinine derivatives with antiinsectan activity from the sclerotia of Aspergillus nomius

Tetrahedron Letters
1993.0

Abstract

14Hydroxypaspahnine (3) and 14-(N;N-Dimcthyl-~v~yl0xy~~e (4) have been isolated from the sclerotia of Aspergillns twmiu,r, and identified by analysis of 2D NMR data. Both compuunds cause cu. 90% reduction in weight gain in Essays against the corn calwolm ~efjwv~ zeu at the loo ppm (dry weight) dietary level, Paspalinine causes no effect at this concentration.studio of Aspergilius sclerotia as potential sources of new natural products with antiinsecuul e@eets and other bioactivities continue to afford a variety of novel metabolites with activity against insect&~* Most of them compounds are indole-deriv~ and several of them contain pmviously in&scribed or ram ring systems. For example, our earlier studi& of sclemtial me&o&es from Aspsrgirrus twmir&r Kmzman, Horn, and He&ltine (NRRL 13137) led to the isolation of nomininc (1) and apcmominc (2). both of which exhibit activity against the corn earworm Helicovetpu zeu. Putther studies of A. llomius metabolites are ongoing, and two new compounds (3 and 4) have now been isolated Them metabolites are closely related to the tremorgen paspalinine (5)3 originally isolated from C&zviceps paspuli, but 3 and 4 are much mom effective than paspahnii in assays against H. zeu. Compound 4 contains an unusual N,N-dimethylvalyl unit, an amino acyl residue mported from only one other natural source. Details of the isolation, structtue elucidation, and biological 'activity of compounds 3 and 4 are pmsented here.

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