Novel stachyflin derivatives from Stachybotrys sp. RF-7260. Fermentation, isolation, structure elucidation and biological activities

J Antibiot (Tokyo). 2002 Mar;55(3):239-48. doi: 10.7164/antibiotics.55.239.

Abstract

Stachybotrys sp. RF-7260 was found to produce stachyflins, novel anti-influenza virus agents, under solid-state fermentation conditions. Feeding DL-lysine to a culture of Stachybotrys sp. RF-7260 induced the formation of the novel compounds, SQ-02-S-L2 and -L1, and feeding DL-valine the formation of SQ-02-S-VI and -V2. The structures of these metabolites were determined by detailed 2D NMR analyses in comparison with acetylstachyflin. SQ-02-S-L2 and -L1 have the lysine moiety and SQ-02-S-V1 has the valine moiety. SQ-02-S-V2 has an amidine moiety instead of the lactam moiety in acetylstachyflin. SQ-02-S-L2, -L1 and -V1, substituted on the lactam amide hydrogen, displayed only a low level of the antiviral activity. However, deacetyl SQ-02-S-V2 showed potent antiviral activity similar to stachyflin.

MeSH terms

  • Animals
  • Antiviral Agents / chemistry*
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology
  • Cattle
  • Cell Line
  • Fermentation
  • Heterocyclic Compounds, 4 or More Rings / chemistry*
  • Heterocyclic Compounds, 4 or More Rings / isolation & purification
  • Heterocyclic Compounds, 4 or More Rings / pharmacology
  • Indoles / chemistry*
  • Indoles / isolation & purification
  • Indoles / pharmacology
  • Influenza A virus / drug effects
  • Kidney / cytology
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Stachybotrys / metabolism*
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Heterocyclic Compounds, 4 or More Rings
  • Indoles
  • Sesquiterpenes
  • stachyflin