Isolation of ciliatamide D from a marine sponge Stelletta sp. and a reinvestigation of the configuration of ciliatamide A

J Nat Prod. 2013 Apr 26;76(4):755-8. doi: 10.1021/np300878b. Epub 2013 Mar 6.

Abstract

A new lipopeptide, ciliatamide D (1), was isolated from a marine sponge Stelletta sp., collected at Oshimashinsone, together with the known compound ciliatamide A (2). Ciliatamide D (1) is a congener of 2, in which N-Me-Phe is replaced by N-Me-Met(O). Marfey's analysis of the acid hydrolysate of 1 demonstrated that the two constituent amino acids were both in the l-form. This result prompted us to carefully investigate the configuration of 2, resulting in the assignment of the l-form for both residues.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Lipopeptides / chemistry*
  • Lipopeptides / isolation & purification*
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oceans and Seas
  • Porifera / chemistry*
  • Stereoisomerism

Substances

  • Lipopeptides
  • ciliatamide A