WS9326H, an Antiangiogenic Pyrazolone-Bearing Peptide from an Intertidal Mudflat Actinomycete

Org Lett. 2018 Apr 6;20(7):1999-2002. doi: 10.1021/acs.orglett.8b00546. Epub 2018 Mar 20.

Abstract

WS9326H (1), a new cyclic peptide, was isolated from a mudflat-derived Streptomyces strain. Based on analysis by 1D/2D NMR, UV spectroscopy, and mass spectrometry, compound 1 was determined to have the gross structure of a cyclic heptapeptide bearing an unprecedented pyrazolone ring connected to a d-arabinitol via an amide bond. The absolute configuration of 1 was established by multistep chemical derivatizations, comprehensive NMR, and LC/MS analyses of the derivatives and quantum mechanics-based computational methods. WS9326H (1) displayed significant antiangiogenesis activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Actinobacteria*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Peptides
  • Pyrazolones
  • Streptomyces

Substances

  • Peptides
  • Pyrazolones