Aplysiols C–E, Brominated Triterpene Polyethers from the Marine Alga Chondria armata and a Revision of the Structure of Aplysiol B

Antonius R. B. Ola; Anna-Marie Babey; Cherie Motti; Bruce F. Bowden

doi:10.1071/CH10081

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Aplysiols C–E, Brominated Triterpene Polyethers from the Marine Alga Chondria armata and a Revision of the Structure of Aplysiol B

Antonius R. B. Ola ^A , Anna-Marie Babey ^B , Cherie Motti ^C and Bruce F. Bowden ^A ^D

+ Author Affiliations

- Author Affiliations

^A Chemistry, School of Pharmacy and Molecular Sciences, James Cook University, Townsville, Qld 4811, Australia.

^B Physiology and Pharmacology, School of Veterinary and Biomedical Sciences, James Cook University, Townsville, Qld 4811, Australia.

^C Australian Institute of Marine Sciences, PO Box 155, Townsville MC, Townsville, Qld 4810, Australia.

^D Corresponding author. Email: bruce.bowden@jcu.edu.au

Australian Journal of Chemistry 63(6) 907-914 https://doi.org/10.1071/CH10081
Submitted: 12 February 2010 Accepted: 15 March 2010 Published: 11 June 2010

Abstract

Three new brominated triterpene polyethers, aplysiols C–E (1–3), were isolated from extracts of the red alga Chondria armata. Structures were determined by comparison with the closely related metabolite, aplysiol B, which was previously reported from the anaspidean mollusc Aplysia dactylomela. The relative stereochemistry of the tetracyclic ring system was determined from 1D gradient selective NOESY experiments and from biogenetic considerations that support a revision of the stereochemistry proposed for aplysiol B. In addition, three known brominated C₁₅ acetogenin acetylenic ethers: (–)-pinnatifidenyne, (+)-laurenyne, and (+)-obtusenyne, two brominated diterpenes: (–)-ent-angasiol and (–)-ent-angasiol acetate, and the symmetrical halogenated triterpene polyether intricatetraol were isolated.

Acknowledgements

The authors express appreciation to AUSAID for the award of an APS postgraduate studies scholarships to A. R. B. Ola. We are also grateful to Professor Rocky DeNys for the Chondria armata collection and to Dr Ian Price for taxonomy of Chondria armata samples collected previously.

References

Aplysiols C–E, Brominated Triterpene Polyethers from the Marine Alga Chondria armata and a Revision of the Structure of Aplysiol B

Abstract

Acknowledgements

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