Isolation and structure elucidation of tumescenamides A and B, two peptides produced by Streptomyces tumescens YM23-260

J Antibiot (Tokyo). 2010 Sep;63(9):549-52. doi: 10.1038/ja.2010.73. Epub 2010 Jul 7.

Abstract

Two peptides, tumescenamides A and B, were isolated from the fermentation broth of a marine bacterium, Streptomyces tumescens YM23-260. The structure of tumescenamide A was determined to be a cyclic depsipeptide consisting of α-amino-2-butenoic acid, tyrosine, valine, leucine and threonine, substituted with a 2,4-dimethylheptanoyl residue at the α-NH(2) position. Tumescenamide B possesses a 2,4,6-trimethylnonanoyl residue in place of the 2,4-dimethylheptanoyl substituent in tumescenamide A. Tumescenamide A induced reporter gene expression under the control of the insulin-degrading enzyme promoter.

MeSH terms

  • Amino Acids / analysis
  • Depsipeptides / chemistry*
  • Depsipeptides / isolation & purification*
  • Depsipeptides / metabolism
  • Depsipeptides / pharmacology
  • Genes, Reporter
  • Insulysin / biosynthesis
  • Insulysin / genetics
  • Luciferases / biosynthesis
  • Luciferases / genetics
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Promoter Regions, Genetic
  • Streptomyces / metabolism*
  • Transcriptional Activation

Substances

  • Amino Acids
  • Depsipeptides
  • Luciferases
  • Insulysin