Electrospray ionization mass spectra of piperazimycins A and B and gamma-butyrolactones from a marine-derived Streptomyces sp

J Antibiot (Tokyo). 2008 Dec;61(12):736-46. doi: 10.1038/ja.2008.87.

Abstract

Chemical investigation of the marine-derived Streptomyces sp. Act8015 led to the isolation of two cyclic peptide antibiotics, piperazimycins A and B (1a, 1b). Their structures were confirmed on the basis of a detailed HRESI-MS/MS analysis. Additionally, a new butanolide, 4,10-dihydroxy-10-methyl-dodecan-4-olide (2), and the respective acid, 4,10-dihydroxy-10-methyl-dodecanoic acid (3a) were identified. Further isolated compounds were staurosporin, adenine, indole-3-carboxylic acid, ferulic acid, tryptophol, and three gamma-butyrolactones: virginiae butanolide E (4e) and Graefe's Factors I (4f) and III (4g). The structures of 2 and 3a were confirmed by detailed 1D and 2D NMR studies and MS spectra and by comparison with related structures. A full signal assignment of virginiae butanolide E (4e) is reported here for the first time.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / isolation & purification*
  • Depsipeptides / chemistry
  • Depsipeptides / isolation & purification*
  • Magnetic Resonance Spectroscopy
  • Spectrometry, Mass, Electrospray Ionization
  • Streptomyces / chemistry*
  • Streptomyces / isolation & purification
  • Water Microbiology*

Substances

  • Depsipeptides
  • piperazimycin A
  • piperazimycin B
  • 4-Butyrolactone