Iminolactones from Schizophyllum commune

J Nat Prod. 2015 May 22;78(5):1165-8. doi: 10.1021/np500836y. Epub 2015 May 7.

Abstract

Schizines A (1) and B (2), the first naturally occurring iminolactones (3,6-dihydro-2H-1,4-oxazin-2-one derivatives) to be reported, have been isolated from the fruiting bodies of Schizophyllym commune. In principle the 2-oxazinone moiety might have been formed by a reaction between the amino acid phenylalanine or tryptophan and an 2α-hydroxy-1-ketomarasmone. The alkaloids are unusual in that the carboxyl group of the amino acid precursor is preserved during the biosynthesis. The compounds showed some inhibition of the growth of cancer cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Denmark
  • Drug Screening Assays, Antitumor
  • Female
  • Fruiting Bodies, Fungal / chemistry
  • Humans
  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Lactones / pharmacology
  • Male
  • Molecular Structure
  • Oxazines / chemistry
  • Oxazines / isolation & purification*
  • Oxazines / pharmacology
  • Phenylalanine / metabolism
  • Schizophyllum / chemistry*
  • Tryptophan / metabolism

Substances

  • Alkaloids
  • Antineoplastic Agents
  • Lactones
  • Oxazines
  • schizine A
  • schizine B
  • Phenylalanine
  • Tryptophan