Calyxamides A and B, cytotoxic cyclic peptides from the marine sponge Discodermia calyx

J Nat Prod. 2012 Feb 24;75(2):290-4. doi: 10.1021/np2009187. Epub 2012 Jan 25.

Abstract

Cyclic peptides containing 5-hydroxytryptophan and thiazole moieties were isolated from the marine sponge Discodermia calyx collected near Shikine-jima Island, Japan. The structures of calyxamides A (1) and B (2), including the absolute configurations of all amino acids, were elucidated by spectroscopic analyses and degradation experiments. The structures are similar to keramamides F and G, previously isolated from Theonella sp. The analysis of the 16S rDNA sequences obtained from the metagenomic DNA of D. calyx revealed the presence of Candidatus Entotheonella sp., an unculturable δ-proteobacterium inhabiting the Theonella genus and implicated in the biosynthesis of bioactive peptides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids
  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Drug Screening Assays, Antitumor
  • Japan
  • Leukemia P388
  • Molecular Structure
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / pharmacology*
  • Porifera / chemistry*
  • Theonella / chemistry

Substances

  • Amino Acids
  • Antineoplastic Agents
  • Peptides, Cyclic
  • calyxamide A
  • calyxamide B