The Ammosamides: Structures of Cell Cycle Modulators from a Marine-Derived Streptomyces Species

Authors

  • Chambers C. Hughes Dr.,

    1. Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California at San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0204 (USA), Fax: (+1) 858-534-1318
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  • John B. MacMillan Dr.,

    1. Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California at San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0204 (USA), Fax: (+1) 858-534-1318
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  • Susana P. Gaudêncio Dr.,

    1. Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California at San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0204 (USA), Fax: (+1) 858-534-1318
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  • Paul R. Jensen Dr.,

    1. Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California at San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0204 (USA), Fax: (+1) 858-534-1318
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  • William Fenical Prof.

    1. Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California at San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0204 (USA), Fax: (+1) 858-534-1318
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  • This work was supported by a grant from the US National Cancer Institute, NIH under grant CA44848 (to W.F.). S.P.G. is grateful to the Fundação para a Ciência e Tecnologia, Portugal, for a postdoc fellowship. The authors thank Arnold Rheingold (UCSD) for X-ray diffraction data, Lisa Zeigler and Wolf Wrasidlo (UCSD Cancer Center) for in vitro cytotoxicity data, and Michelle Leibrand for help with purification.

Abstract

original image

From the ocean: Ammosamides A (1) and B (2) were isolated from a marine-derived Streptomyces species collected in the Bahamas. The structures of these chlorinated tricyclic pyrroloquinoline alkaloids were solved using X-ray crystallographic techniques. Ammosamide A (1) was shown to contain an unusual thio-γ-lactam ring. Both metabolites show specific nanomolar cytotoxicity against selected cancer cell lines.

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