Chenopodolin: a phytotoxic unrearranged ent-pimaradiene diterpene produced by Phoma chenopodicola, a fungal pathogen for Chenopodium album biocontrol

J Nat Prod. 2013 Jul 26;76(7):1291-7. doi: 10.1021/np400218z. Epub 2013 Jun 20.

Abstract

A new phytotoxic unrearranged ent-pimaradiene diterpene, named chenopodolin, was isolated from the liquid culture of Phoma chenopodicola, a fungal pathogen proposed for the biological control of Chenopodium album, a common worldwide weed of arable crops such as sugar beet and maize. The structure of chenopodolin was established by spectroscopic, X-ray, and chemical methods as (1S,2S,3S,4S,5S,9R,10S,12S,13S)-1,12-acetoxy-2,3-hydroxy-6-oxopimara-7(8),15-dien-18-oic acid 2,18-lactone. At a concentration of 2 mg/mL, the toxin caused necrotic lesions on Mercurialis annua, Cirsium arvense, and Setaria viride. Five derivatives were prepared by chemical modification of chenopodolin functionalities, and some structure-activity relationships are discussed.

MeSH terms

  • Bacillus subtilis / drug effects
  • Beta vulgaris / drug effects
  • Chenopodium album / drug effects
  • Chenopodium album / microbiology
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Dose-Response Relationship, Drug
  • Fungi / chemistry*
  • Geotrichum / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / microbiology
  • Stereoisomerism
  • Structure-Activity Relationship
  • Zea mays / drug effects

Substances

  • Diterpenes
  • chenopodolin