A serendipitous discovery of isomotuporin-containing sponge populations of Theonella swinhoei

Christopher J Wegerski; Joshua Hammond; Karen Tenney; Teatulohi Matainaho; Phillip Crews

doi:10.1021/np060464w

A serendipitous discovery of isomotuporin-containing sponge populations of Theonella swinhoei

J Nat Prod. 2007 Jan;70(1):89-94. doi: 10.1021/np060464w.

Authors

Christopher J Wegerski¹, Joshua Hammond, Karen Tenney, Teatulohi Matainaho, Phillip Crews

Affiliation

¹ Department of Chemistry and Biochemistry & Institute of Marine Sciences, University of California, Santa Cruz, California 95064, USA.

Abstract

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.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Animals
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Peptides, Cyclic / chemistry
Peptides, Cyclic / isolation & purification*
Photography
Theonella / chemistry*

Substances

Peptides, Cyclic
motuporin

Abstract

Publication types

MeSH terms

Substances

Grants and funding