Psammaplin Metabolites New and Old: An NMR Study Involving Chiral Sulfur Chemistry

Sharna K. Graham; Lynette K. Lambert; Gregory K. Pierens; John N. A. Hooper; Mary J. Garson

doi:10.1071/CH09617

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Psammaplin Metabolites New and Old: An NMR Study Involving Chiral Sulfur Chemistry

Sharna K. Graham ^A , Lynette K. Lambert ^B , Gregory K. Pierens ^B , John N. A. Hooper ^C and Mary J. Garson ^A ^D

+ Author Affiliations

- Author Affiliations

^A School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.

^B Centre for Magnetic Resonance, The University of Queensland, Brisbane, Qld 4072, Australia.

^C The Queensland Museum, PO Box 3300, South Brisbane, Qld 4100, Australia.

^D Corresponding author. Email: m.garson@uq.edu.au

Australian Journal of Chemistry 63(6) 867-872 https://doi.org/10.1071/CH09617
Submitted: 30 November 2009 Accepted: 8 February 2010 Published: 11 June 2010

Abstract

The new metabolite psammaplin N (8) that contains a sulfoxide moiety has been isolated together with psammaplins A (1), I (4a), and J (2) from a specimen of the marine sponge Aplysinella rhax (order Verongida family Aplysinidae) collected in South East Queensland. An NMR study on psammaplin J reveals its facile conversion to psammaplins A and I when exposed to methanol.

Acknowledgements

We thank the School of Chemistry and Molecular Biosciences and The University of Queensland for financial support. The assistance of Dr Tri Le (NMR), Dr Andrew Piggott, and Dr Angela Salim (Institute for Molecular Bioscience) and Graham McFarlane for MS, Dr Peter Katavic (optical rotations), and the staff of Scuba World, Mooloolaba (for collection of sponge samples) is gratefully acknowledged. Permission to collect sponge samples was provided by Queensland Department of Primary Industries and Fisheries. We thank the Queensland NMR Network (QNN) for granting access to the 900 MHz NMR spectrometer.

References

Psammaplin Metabolites New and Old: An NMR Study Involving Chiral Sulfur Chemistry

Abstract

Acknowledgements

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