Submitted to: Journal of Natural Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 3/18/2009
Publication Date: 5/22/2009
Citation: Kamel, H.N., Ding, Y., Li, X., Ferreira, D., Fronczek, F.R., Slattery, M. 2009. Beyond Polymaxenolide: Cembrane-Africanane Terpenoids from the Hybrid Soft Coral Sinularia maxima x S. polydactyla. Journal of Natural Products. 72:900-905. Interpretive Summary: This paper describes the isolation and structure elucidation of five novel cembrane-Africanane terpenoids from the hybrid soft coral Sinularia maxima × S. polydactyla. The absolute configuration of the compounds was established by X-ray diffraction analysis and theoretical calculations of electronic circular dichroism spectra.
Technical Abstract: The effects of natural hybridization on secondary metabolite production and diversification have only recently been studied in plants and have essentially been overlooked in marine organisms. Chemical investigation of the hybrid soft coral Sinularia maxima × S. polydactyla resulted in the isolation of five new terpenoids, 7E-polymaxenolide (1), 7E-5-epipolymaxenolide (2), and polymaxenolides A-C (3-5), possessing a cembrane-africanane skeleton. Their structures were established by detailed analysis of NMR and MS data. The contentious issue of defining the absolute configuration at the stereogenic centers of the conformationally mobile cembrane macrocyclic ring was addressed by joint application of electronic circular dichroism and X-ray diffraction analyses.