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United States Department of Agriculture

Agricultural Research Service

Research Project: DISCOVERY AND DEVELOPMENT OF NATURAL PRODUCTS FOR PHARMACEUTICAL AND AGRICHEMICAL APPLICATIONS

Location: Natural Products Utilization Research

Title: Beyond Polymaxenolide: Cembrane-Africanane Terpenoids from the Hybrid Soft Coral Sinularia maxima x S. polydactyla

Authors
item Kamel, Haidy -
item Ding, Yuanqing -
item Li, Xing-Cong -
item Ferreira, Daneel -
item Fronczek, Frank -
item Slattery, Marc -

Submitted to: Journal of Natural Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: March 18, 2009
Publication Date: May 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.

Last Modified: 7/30/2014
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