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

Khaled A. Shaaban, Mohamed Shaaban, Petrea Facey, Serge Fotso, Holm Frauendorf, Elisabeth Helmke, Armin Maier, Heinz H. Fiebig, Hartmut Laatsch

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Chemical investigation of the marine-derived Streptomyces sp. Act8015 led to the isolation of two cyclic peptide antibiotics, piperazimycins A and B (la, lb). 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 y-butyrolactones: virginiae butanolide E (4e) and Graefe's Factors I (4f) and III (4g). The structures of 2 and 3a were confirmed by detailed ID 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.

Original languageEnglish
Pages (from-to)736-746
Number of pages11
JournalJournal of Antibiotics
Volume61
Issue number12
DOIs
StatePublished - Dec 2008

Bibliographical note

Funding Information:
Acknowledgements We thank Mr. R. Machinek for NMR measurements, F. Lissy for biological activity tests and A. Kohl for technical assistance. P. Facey thanks the Alexander von Humboldt Foundation (AvH) for a research fellowship. Financial support from the BMBF (Project No. 03F0415A) is gratefully acknowledged.

Keywords

  • Marine-derived streptomyces sp
  • Piperazimycins
  • γ-butyrolactones

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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