Three novel, structurally unique spirocyclic alkaloids from the halotolerant B-17 fungal strain of Aspergillus variecolor

Chem Biodivers. 2007 Dec;4(12):2913-9. doi: 10.1002/cbdv.200790240.

Abstract

During our search for novel antitumor lead compounds from microorganisms living under extreme conditions, three novel alkaloids, variecolortides A-C (1-3), were isolated from the mycelia of the halotolerant fungal strain Aspergillus variecolor B-17. The new compounds were found to share an unprecedented 'spiro-anthronopyranoid diketopiperazine' structure, with a stable hemiaminal function, as corroborated by in-depth NMR-spectroscopic and mass-spectrometric analyses, as well as by a single-crystal X-ray analysis of 1. All compounds were shown to exhibit weak cytotoxic and antioxidant activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification*
  • Alkaloids / toxicity
  • Aspergillus / chemistry*
  • Aspergillus / classification
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Drug Resistance / drug effects*
  • Humans
  • Macrocyclic Compounds / chemistry*
  • Macrocyclic Compounds / toxicity
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Neoplasms / pathology
  • Salts / pharmacology*
  • Spiro Compounds / chemistry*
  • Spiro Compounds / toxicity

Substances

  • Alkaloids
  • Macrocyclic Compounds
  • Salts
  • Spiro Compounds