Thiersinines A and B: novel antiinsectan indole diterpenoids from a new fungicolous Penicillium species (NRRL 28147)

Org Lett. 2002 Sep 5;4(18):3095-8. doi: 10.1021/ol026424a.

Abstract

[structure: see text] Two novel antiinsectan indole diterpenoids, thiersinines A (1) and B (2), along with seven known paxilline-type compounds, were isolated from organic extracts of a new Penicillium species (P. thiersii NRRL 28147). The structures of 1 and 2 were determined by analysis of 2D NMR data. Thiersinines A and B possess a unique spirocyclic subunit that is unprecedented in previously known compounds of this class. Both compounds exhibit potent activity against the fall armyworm (Spodoptera frugiperda).

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Indoles / chemistry
  • Indoles / isolation & purification*
  • Insecticides / chemistry
  • Insecticides / isolation & purification*
  • Insecticides / pharmacology
  • Nuclear Magnetic Resonance, Biomolecular
  • Penicillium / chemistry*
  • Spiro Compounds
  • Spodoptera / drug effects
  • Spodoptera / growth & development

Substances

  • Diterpenes
  • Indoles
  • Insecticides
  • Spiro Compounds
  • thiersinine A
  • thiersinine B
  • paxilline