A Serendipitous Discovery of Isomotuporin-Containing Sponge Populations of Theonella swinhoei

Christopher J. Wegerski,† Joshua Hammond,† Karen Tenney,† Teatulohi Matainaho,§ and Phillip Crews*†
Department of Chemistry and Biochemistry & Institute of Marine Sciences, University of California, Santa Cruz, California 95064, and Discipline of Pharmacology, School of Medicine and Health Sciences, University of Papua New Guinea, National Capital District, Papua New Guinea
J. Nat. Prod., 2007, 70 (1), pp 89–94
DOI: 10.1021/np060464w
Publication Date (Web): December 14, 2006
Copyright © 2007 American Chemical Society and American Society of Pharmacognosy
†

 University of California Santa Cruz.

,
§

 University of Papua New Guinea.

,
*

 To whom correspondence should be addressed. Tel:  831-459-2603. E-mail:  phil@chemistry.ucsc.edu.

Abstract

Abstract Image

An in-depth LCMS examination of 14 different collections of Indo-Pacific Theonella swinhoei sponges resulted in the discovery of four diastereomeric analogues of the cyclic pentapeptide motuporin. These motuporin analogues all contain a novel 2R configuration for the Adda amino acid. Additionally, one analogue has a unique nonoxygenated Adda amino acid. In all, 15 different compounds were observed by LCMS or isolated. The stereochemistries of the constituent amino acids were determined through a combination of the advanced Marfey technique and 1H NMR data.

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History

  • Published In Issue January 26, 2007
  • Received September 20, 2006

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