Revised structure of cyclolithistide A, a cyclic depsipeptide from the marine sponge Discodermia japonica

J Nat Prod. 2014 Jan 24;77(1):154-8. doi: 10.1021/np400668k. Epub 2013 Dec 13.

Abstract

A cyclic peptide was isolated from the deep-sea marine sponge Discodermia japonica, and its NMR spectroscopic data were identical to those reported for cyclolithistide A, a known antifungal depsipeptide. However, the interresidue HMBC correlations suggested that the amino acid sequence was different from that of the original structure. Moreover, chiral-phase GC-MS, combined with Marfey's analysis, indicated that the absolute configurations of three amino acids were also antipodal. Here, we propose the revised structure of cyclolithistide A and address the configuration of the previously unassigned 4-amino-3,5-dihydroxyhexanoic acid (Adha) moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Antifungal Agents / chemistry*
  • Antifungal Agents / isolation & purification
  • Depsipeptides / chemistry*
  • Depsipeptides / isolation & purification
  • Gas Chromatography-Mass Spectrometry
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry*

Substances

  • Antifungal Agents
  • Depsipeptides
  • cyclolithistide A
  • romidepsin