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ARS Home » Pacific West Area » Pullman, Washington » Plant Germplasm Introduction and Testing Research » Research » Publications at this Location » Publication #130706
Title: NOVEL BIOACTIVE BREVIANE SPIRODITERPENOIDS FROM PENICILLIUM BREVICOMPACTUM DIERCKX.

Author
item MACIAS, F. - UNIV. OF CADIZ (SPAIN)
item CUTLER, H. - MERCER UNIVERSITY
item CUTLER, S. - MERCER UNIVERSITY
item Dugan, Frank
item HILL, R. - HORTRESEARCH, RUAKURA, NZ

Submitted to: Journal of Organic Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 1/1/2000
Publication Date: 2/7/2000
Citation: Macias, F.A., Cutler, H.G., Cutler, S.J., Dugan, F.M., Hill, R.A. 2000. Novel bioactive breviane spiroditerpenoids from penicillium brevicompactum dierckx.. Journal of Organic Chemistry. 65:9039-9046.

Interpretive Summary: The genus Penicillium is noted for producing a variety of bioactive chemicals. Penicillium brevicompactum produces compounds which have anti-plant, anti-insect and anti-fungal properties. Investigations of the properties of these chemicals are important because of the potential for use as new agrochemicals. The subjects of this research, all in a class of chemicals called spiroditerpenoids, are designated as breviones. Breviones were strongly inhibitory to growth of young wheat leaves at very low concentrations. The structures of these brevione compounds are described and illustrated in detail.

Technical Abstract: The structures of four new, naturally occurring bioactive spiroditerpenoids, (+)-breviones B, C, D, and E, potential allelopathic agents, have been determined from extracts of semisolid fermented Penicillium brevicompactum Dierckx. The structures display the novel breviane spiroditerpenoid skeleton. Structure elucidation was performed by chemical transformations and by homo- and heteronuclear 2D-NMR spectral data. On the basis of combined studies of the theoretical conformations and NOEDIFF data, their relative stereochemistry is proposed. A mixed biogenesis for this novel family of spiroditerpenoids is tendered. The levels of activity shown by breviones B, C, and E in the etiolated wheat coleoptiles bioassay, especially breviones E (100% inhibition) and C (80% inhibition) both at 10-4 M, suggest them as lead compounds for new agrochemicals.