School of Physical and Chemical Sciences Te Kura Matū Seminar Series

GAME OF TERPENES: STRUCTURES, STEREOCHEMISTRY AND CHEMICAL ECOLOGY OF NUDIBRANCH METABOLITES

Speaker

Professor Mary J Garson

Institute

School of Chemistry and Molecular Biosciences, University of Queensland, Australia

Time & Place

Wed, 26 Sep 2018 12:00:00 NZST in Room 701, Level 7, WEST Building

All are welcome

Abstract

Nudibranchs, the “butterflies” of the ocean, are a group of brightly-coloured marine molluscs that are the source of diverse bioactive natural products. This talk will describe how an ecological study on chemical defense in nudibranchs led to the isolation and characterization of new terpene metabolites with extensively-rearranged carbon skeletons. Case studies that will be discussed include new isocyanoterpenes from Phyllidia ocellata and from Phyllidiella pustulosa, and epoxy-substituted norditerpenes from Goniobranchus splendidus. NOESY data run at 700 or 900 MHz, together with detailed conformational analysis informed by molecular modeling and DFT calculations, enables assignment of individual configurations. The antimalarial, antifungal and cytotoxic activities of selected metabolites have been explored. The chemistry data are reviewed in an ecological context.

This seminar is part of The Royal Society of Chemistry Australasian Lecture Series 2018 

Selected Publications:

Winters, A. E., White, A. M., Dewi, A. S., Mudianta, I. M., Wilson, N. G., Forster, L. C., Garson, M. J., Cheney, K. L. J. Chem. Ecol., 44, 384-396. 2018.

White, A. M., Dao, K., Vrublauskas, D., Könst, Z., Pierens, G. K., Mándi, A., Andrews, K. T., Skinner-Adams, T., Clarke, M. S., Narbutas, P. T., Sim, D. C.-M., Cheney, K. L., Kurtán, T., Garson, M. J., Vanderwal, C. D. J. Org. Chem., 82, 13313-13323. 2017.

Forster, L. C., Pierens, G. K., White, A. M., Cheney, K. L., Dewapriya, P., Capon, R. J., Garson, M. J. ACS Omega., 2, 2672-2677. 2017.

Cheney, K. L., White, A. M., Mudianta, I. M., Winters, A. E., Quezada, M., Capon, R. J., Mollo, E., Garson, M. J. PLoSOne, e0145134. 2016.

White, A. M., Pierens, G. K., Skinner-Adams, T., Andrews, K. T., Bernhardt, P. V., Krenske, E. A., Mollo, E., Garson, M. J. J. Nat. Prod., 78, 1422-1427. 2015.

 

Biography

I was an Overseas Research Fellow of the Royal Society in Rome, Italy (1977-1978), a Research Fellow at New Hall, Cambridge (1978-1981) and a Queen Elizabeth II Research Fellow at James Cook University of North Queensland (1983-1985). I have worked in the UK pharmaceutical industry (Smith Kline Beecham) and previously held a lecturing position at The University of Wollongong (1986-1990). I joined The University of Queensland in 1990.