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Antimalarial Peptides from Marine Cyanobacteria: Isolation and Structural Elucidation of Gallinamide A

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Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, La Jolla, California 92093, Instituto de Investigaciones Científicas Avanzados y Servicios de Alta Tecnología, INDICASAT, Clayton, Edificio 175, PO Box 7250, Panamá 5, Panamá, Department of Global Health, College of Public Health, University of South Florida, 3720 Spectrum Boulevard, Suite 304, Tampa, Florida 33612, and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California at San Diego, La Jolla, California 92093
* To whom correspondence should be addressed. Tel: (831) 459-3014. Fax: (831) 459-2935. E-mail: [email protected]
†Scripps Institution of Oceanography.
‡INDICASAT, Panamá.
§University of South Florida.
⊥Skaggs School of Pharmacy and Pharmaceutical Sciences.
∥Current address: Department of Chemistry and Biochemistry, University of California, Santa Cruz.
Cite this: J. Nat. Prod. 2009, 72, 1, 14–17
Publication Date (Web):December 31, 2008
https://doi.org/10.1021/np8003529
Copyright © 2008 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    As part of a continuing program to identify novel treatments for neglected parasitic diseases, the Panama International Cooperative Biodiversity Group (ICBG) program has been investigating the antimalarial potential of secondary metabolites from Panamanian marine cyanobacteria. From over 60 strains of cyanobacteria evaluated in our biological screens, the organic extract of a Schizothrix species from a tropical reef near Piedras Gallinas (Caribbean coast of Panama) showed potent initial antimalarial activity against the W2 chloroquine-resistant strain of Plasmodium falciparum. Bioassay-guided fractionation followed by 2D NMR analysis afforded the planar structure of a new and highly functionalized linear peptide, gallinamide A. Subsequent degradation and derivatization methods were used to determine the absolute configuration at most stereogenic centers in this unusual new metabolite.

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    1H and 13C NMR spectra of 1, interpretation of ROESY correlations for the Apa subunit, complete biological screening data, and a color photograph of the field-collected Schizothrix sp. This material is available free of charge via the Internet at http://pubs.acs.org.

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