Aspochalamins A-D and aspochalasin Z produced by the endosymbiotic Fungus Aspergillus niveus LU 9575. II. Structure elucidation

J Antibiot (Tokyo). 2004 Nov;57(11):715-20. doi: 10.7164/antibiotics.57.715.

Abstract

The structures of new cytochalasan fungal metabolites aspochalamins A-D have been elucidated by ESI-FTICR-MS, NMR spectroscopy, and chiral amino acid analysis. Aspochalamins A-D consist of different aspochalasin skeletons connected at position C-19 to the N terminus of the tripeptidic moiety amide anthranoyl-L-alanine-E-didehydrotryptamide. Furthermore, the structure of a new aspochalasin analog, aspochalasin Z, was derived from its molecular mass and NMR data as 10-isopropyl-14-methyl[11]-cytochalasa-6Z,13E,19E-triene-1,21-dione.

MeSH terms

  • Amino Acids / chemistry
  • Anti-Bacterial Agents / chemistry*
  • Aspergillus / chemistry
  • Aspergillus / metabolism*
  • Cytochalasins / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Ultraviolet
  • Stereoisomerism

Substances

  • Amino Acids
  • Anti-Bacterial Agents
  • Cytochalasins
  • aspochalamin A
  • aspochalamin B
  • aspochalamin C
  • aspochalamin D