A serendipitous discovery of isomotuporin-containing sponge populations of Theonella swinhoei.
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.
Wegerski
Christopher J
CJ
Department of Chemistry and Biochemistry & Institute of Marine Sciences, University of California, Santa Cruz, California 95064, USA.
Hammond
Joshua
J
Tenney
Karen
K
Matainaho
Teatulohi
T
Crews
Phillip
P
D000818:Animals; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification*; D010781:Photography; D047232:Theonella / Q000737:chemistry*
D010456:Peptides, Cyclic; C093605:motuporin