Nazumazoles A-C, Cyclic Pentapeptides Dimerized through a Disulfide Bond from the Marine Sponge Theonella swinhoei

Org Lett. 2015 Jun 5;17(11):2646-8. doi: 10.1021/acs.orglett.5b01020. Epub 2015 May 11.

Abstract

A mixture of nazumazoles A-C (1-3) was purified from the extract of the marine sponge Theonella swinhoei. The mixture was eluted as an extraordinarily broad peak in the reversed-phase HPLC. The structures of nazumazoles were determined by interpretation of the NMR data and chemical degradations. Nazumazoles contain one residue each of alanine-derived oxazole and α-keto-β-amino acid residue. Nazumazoles exhibited cytotoxicity against P388 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Dimerization
  • Disulfides / chemistry*
  • Molecular Conformation
  • Oxazoles / chemistry
  • Oxazoles / isolation & purification*
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Theonella / chemistry*

Substances

  • Disulfides
  • Oxazoles
  • Peptides, Cyclic
  • nazumazole A
  • nazumazole B
  • nazumazole C