Structural Variations to the 9-N-Methyladeninium Diterpenoid Hybrid Commonly Isolated from Agelas Sponges

Laurent Calcul; Karen Tenney; Joseline Ratnam; James H. McKerrow; Phillip Crews

doi:10.1071/CH10036

RESEARCH FRONT

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Structural Variations to the 9-N-Methyladeninium Diterpenoid Hybrid Commonly Isolated from Agelas Sponges

Laurent Calcul ^A , Karen Tenney ^A , Joseline Ratnam ^B ^C , James H. McKerrow ^B ^D and Phillip Crews ^A ^E

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry and Biochemistry, University of California, Santa Cruz, CA 95064, USA.

^B Small Molecule Discovery Center, University of California, San Francisco, CA 94158, USA.

^C Sandler Center for Basic Research in Parasitic Disease, University of California, San Francisco, CA 94143, USA.

^D Department of Pathology, University of California, San Francisco, CA 94158, USA.

^E Corresponding author. Email: phil@chemistry.ucsc.edu

Australian Journal of Chemistry 63(6) 915-921 https://doi.org/10.1071/CH10036
Submitted: 20 January 2010 Accepted: 23 March 2010 Published: 11 June 2010

Abstract

Four novel 9-N-methyladeninium diterpenoids, agelasine M (3), 2-oxo-agelasine B (4), gelasine A (5), and gelasine B (6) accompanied by the known-agelasine B (1) and F (2) were isolated from the marine sponge Agelas sp. collected in Papua New Guinea. Compounds 3–6 represent higher unsaturated 9-N-methyladeninium bicyclic diterpenoid derivatives including 5 and 6 as unusual norditerpenoid-agelasines. Their structures were elucidated through detailed physical data analyses and comparison with literature properties. All pure compounds were evaluated for inhibitory activity against Trypanosoma brucei as well as for cytotoxicity against Jurkat cells.

Acknowledgement

This research was supported by NIH grant R01-CA047135 and NMR equipment grants from NSF CHE-0342912 and NIH S10-RR19918. We thank W. Boggess at the University of Notre Dame for providing the HRESIMS data. Special thanks to E. Chen from University of California Santa Cruz for performing UV and CD measurements. We also thank L. Matainaho, University of Papua New Guinea and the crew and skipper (C. DeWit) of the M/V Golden Dawn for assistance in specimen collection.

References

Structural Variations to the 9-N-Methyladeninium Diterpenoid Hybrid Commonly Isolated from Agelas Sponges

Abstract

Acknowledgement

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