Hyalachelins A-C, unusual siderophores isolated from the terrestrial myxobacterium Hyalangium minutum

Org Lett. 2014 Aug 15;16(16):4130-3. doi: 10.1021/ol501826a. Epub 2014 Jul 24.

Abstract

Three new siderophores, termed hyalachelins A-C (1-3), were isolated from the terrestrial myxobacterium Hyalangium minutum. Their structures were determined by 2D NMR and HR-MS/MS experiments, and their stereochemical configuration was established by a combination of NMR data, quantum mechanical calculations, and circular dichroism experiments. Hyalachelins are unusual catecholate-type siderophores that bear a 3,7,8-trihydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid. Their iron chelating activities were evaluated in a CAS assay showing EC50 values of ∼30 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Molecular Structure
  • Myxococcales / chemistry*
  • Nuclear Magnetic Resonance, Biomolecular
  • Siderophores / chemistry*
  • Siderophores / isolation & purification*
  • Tetrahydroisoquinolines / chemistry
  • Tetrahydroisoquinolines / isolation & purification*

Substances

  • Siderophores
  • Tetrahydroisoquinolines
  • hyalachelin A
  • hyalachelin B
  • hyalachelin C
  • 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid