Bioactive seco-Sativene Sesquiterpenoids from an Artemisia desertorum Endophytic Fungus, Cochliobolus sativus

J Nat Prod. 2020 May 22;83(5):1488-1494. doi: 10.1021/acs.jnatprod.9b01148. Epub 2020 Apr 17.

Abstract

A series of seco-sativene sesquiterpenoids (1-11) including two new natural products (2 and 3), four new analogues (4-7), and six known analogues, helminthosporic acid (1), drechslerine A (8), drechslerine B (9), helminthosporol (10), helminthosporal acid (11), and isosativenediol (12), were purified from the endophytic fungus Cochliobolus sativus isolated from a desert plant, Artemisia desertorum. The stereochemistry of helminthosporic acid (1) was established for the first time by X-ray diffraction, and the structures including relative and absolute configurations of these new compounds were determined by NMR and CD spectra together with biosynthetic considerations. Compounds 5-7 are the first seco-sativene sesquiterpenoids possessing a glucose group on C-15, C-15, and C-14, respectively. Compounds 1, 7, 9, and 11 displayed strong phytotoxic effects on corn leaves by producing visible lesions, and helminthosporic acid (1) was shown to promote division of leaves and roots of Arabidopsis thaliana with a dose-dependent relationship.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arabidopsis
  • Artemisia / microbiology*
  • Ascomycota / chemistry*
  • Circular Dichroism
  • Endophytes / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plant Leaves / drug effects
  • Plant Leaves / growth & development
  • Plant Roots / drug effects
  • Plant Roots / growth & development
  • Seedlings / drug effects
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / pharmacology*
  • Spectrophotometry, Ultraviolet
  • X-Ray Diffraction
  • Zea mays / drug effects

Substances

  • Sesquiterpenes