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Insect Antifeedant Benzofurans from Pericallis Species.

Carmen E Díaz1, Braulio M Fraga1, Adriana G Portero1

  • 1Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas (CSIC), Avda. Astrofísico F. Sánchez 3, 38206 La Laguna, Tenerife, Spain.

Molecules (Basel, Switzerland)
|February 11, 2023
PubMed
Summary

This study isolated new benzofurans from Pericallis species and tested their antifeedant properties against Spodoptera littoralis. Certain compounds showed significant insecticidal activity without toxicity.

Keywords:
Pericallisaerial partsand post-ingestive activityantifeedantbenzofuransbiotransformationtransformed roots

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Area of Science:

  • Phytochemistry
  • Natural Products Chemistry
  • Insect Chemical Ecology

Background:

  • Benzofurans are a class of natural products with diverse biological activities.
  • Pericallis species are known sources of various secondary metabolites, including benzofurans.
  • Understanding the chemical ecology of plant-insect interactions is crucial for developing sustainable pest management strategies.

Purpose of the Study:

  • To isolate and characterize new benzofuran derivatives from Pericallis species.
  • To evaluate the antifeedant and postingestive effects of isolated benzofurans against the insect Spodoptera littoralis.
  • To investigate the biotransformation of a key benzofuran, 6-hydroxytremetone, using Mucor plumbeus.

Main Methods:

  • Isolation and structure elucidation of benzofurans using chromatographic and spectroscopic techniques (NMR, MS).
  • Bioassays to determine antifeedant activity against Spodoptera littoralis larvae.
  • Evaluation of postingestive toxicity of active compounds.
  • Biotransformation studies using the fungus Mucor plumbeus.

Main Results:

  • Seven new benzofurans were isolated and characterized, along with several known compounds.
  • Benzofurans from the tremetone, euparin, and eupachinin series exhibited antifeedant activity against Spodoptera littoralis.
  • 3-ethoxy-hydroxy-tremetone (4) was the most potent antifeedant. Compounds 4, 11, and 12 showed antifeedant effects without postingestive toxicity.
  • Biotransformation of 6-hydroxytremetone yielded inactive glucosylated products.

Conclusions:

  • Pericallis species are a rich source of structurally diverse benzofurans with significant insect antifeedant properties.
  • Specific benzofuran structures, particularly from the tremetone series, show promise as natural insecticides.
  • Further research into the structure-activity relationships of these compounds could lead to novel pest control agents.