Submitted to: Tetrahedron Letters
Publication Type: Other
Publication Acceptance Date: 2/2/2000
Publication Date: 3/1/2000
Citation: Macias, F.A., Varela, R.M., Simonet, A.M., Cutler, H.G., Cutler, S.J., Ross, S.A., Dunbar, D.C., Dugan, F.M., Hill, R.A. 2000. (+)-brevione a. the first memeber of a novel fmaily of bioactive spiroditerpenoids isolated from penicillium brevicompactum dierckx. Tetrahedron Letters. 41(15):2683-2686. Interpretive Summary: An isolate provisionally identified as Penicillium brevicompactum was isolated from leaf litter in New Zealand, and culture extracts of the fungus were screened for novel compounds. The genus Penicillium has long been documented as a source of bioactive metabolites. In this instance, a new compound (given the name Brevione A) was found to inhibit the growth of young wheat leaves. Such inhibitions are called allelopathy; and the study of the chemicals involved and the mechanisms of their interactions with plants and microbes are of importance in the search for alternative pesticides. This short communication draws to the attention of the scientific community the existence of a new class of compounds, those with a certain type of chemical skeleton called by the authors "breviane."
Technical Abstract: (+)-Brevione A, the first member of anovel family of bioactive spiroditerpenoids, a potential allelopathic agent, has been isolated from the ethyl acetate fractions of the aqueous acetone extracts of semi- solid fermented Penicillium brevicompatum Dierckx. This sturcture displays an unusual novel spiroditerpenoid skeleton of breviane. The structure elucidation of brevione A was performed by homo- and hetero- nuclear 2D-NMR spectral data. On the basis of combined studies of the theroretical conformations and NOEDIFF data, its relative stereochemistry is proposed.