Australian Journal of Chemistry Australian Journal of Chemistry Society
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9-(5‘-Deoxy-5’-thio-β-d-xylofuranosyl)adenine Disulfide from the Southern Australian Marine Sponge Trachycladus laevispirulifer: the First Natural Occurrence of a Nucleoside Disulfide

Chongsheng Peng A B , G. M. Kamal B. Gunaherath A C , Andrew M. Piggott A , Zeinab Khalil A , Melissa Conte A and Robert J. Capon A D
+ Author Affiliations
- Author Affiliations

A Institute for Molecular Bioscience, The University of Queensland, St. Lucia, Qld 4072, Australia.

B School of Pharmacy, Shanghai Jiaotong University, Shanghai, 200240, China.

C Department of Chemistry, The Open University of Sri Lanka, Nawala, Nugegoda, Sri Lanka.

D Corresponding author. Email: r.capon@uq.edu.au

Australian Journal of Chemistry 63(6) 873-876 https://doi.org/10.1071/CH09645
Submitted: 10 December 2009  Accepted: 5 February 2010   Published: 11 June 2010

Abstract

Chemical fractionation of a southern Australian marine sponge, Trachycladus laevispirulifer, yielded 9-(5′-deoxy-5′-thio-β-d-xylofuranosyl)adenine disulfide as the first recorded natural occurrence of a nucleoside disulfide, and only the second of a xylo-nucleoside. Structure elucidation of the disulfide was achieved by detailed spectroscopic analysis and comparison to synthetic model compounds. The antibacterial, antifungal, and anticancer properties of the disulfide are documented and the literature surrounding natural and synthetic thionucleosides is reviewed.


Acknowledgements

The authors thank K. Smith (Victorian Department of Primary Industries) for assistance in specimen collection and L. Goudie (Museum Victoria) for sponge taxonomy. This research was funded in part by the Australian Research Council, with support from PharmaMar (Madrid, Spain).


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