Identification of the Cyclase Product and its First Oxidation Product in the Biosynthesis of Fuscol and Fuscosides

Maysoon B. Saleh; Russell G. Kerr

doi:10.1071/CH10057

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Identification of the Cyclase Product and its First Oxidation Product in the Biosynthesis of Fuscol and Fuscosides

Maysoon B. Saleh ^A ^B and Russell G. Kerr ^A ^C ^D

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry and Biochemistry, Center of Excellence in Biomedical and Marine Biotechnology, Florida Atlantic University, Florida 33431, USA.

^B Current address: Faculty of Pharmacy and Medical Science, Al-Ahliyya Amman University, Amman 19328, Jordan.

^C Department of Chemistry, Department of Biomedical Sciences, Atlantic Veterinary College, University of Prince Edward Island, Charlottetown, PEI C1A 4P3, Canada.

^D Corresponding author. Email: rkerr@upei.ca

Australian Journal of Chemistry 63(6) 901-906 https://doi.org/10.1071/CH10057
Submitted: 29 January 2010 Accepted: 17 March 2010 Published: 11 June 2010

Abstract

Fuscol and the related fuscosides are diterpenes isolated from the Caribbean gorgonian Eunicea fusca, which exhibit potent anti-inflammatory activity with a selective action against leukotriene production in murine models. This report describes the isolation and characterization of the diterpene cyclase product leading to these natural products. The cyclase product has been assigned the trivial name eunicene A and was identified through a radioactivity-guided isolation. Additional biosynthetic experiments conducted by incubating a cell-free extract of E. fusca with ³H-labelled metabolites confirmed the involvement of this unsaturated hydrocarbon in the production of fuscol and fuscosides.

Acknowledgements

We gratefully acknowledge financial support from NSERC, the Canada Research Chair Program, the University of Prince Edward Island, the Atlantic Innovation Fund, the Jeanne and Jean-Louis Lévesque Foundation, and the Center of Excellence of Biomedical and Marine Biotechnology, Florida Atlantic University. High resolution mass spectrometry was performed at the University of Florida.

References

Identification of the Cyclase Product and its First Oxidation Product in the Biosynthesis of Fuscol and Fuscosides

Abstract

Acknowledgements

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