Antitermite activities of coumarin derivatives and scopoletin from Protium javanicum Burm. f

J Chem Ecol. 2010 Jul;36(7):720-6. doi: 10.1007/s10886-010-9807-1. Epub 2010 Jun 19.

Abstract

The antitermite (termiticidal and antifeedant) activity of Protium javanicum Burm. f. extract was investigated. The ethyl acetate fraction was active. Scopoletin (1), quercetin, and stigmasterol were isolated by bioassay-guided fractionation. Scopoletin had the highest activity among the three compounds. In order to investigate the structure-activity relationship (SAR) of the methoxy and hydroxy groups at the C-6 and C-7 positions of the coumarin skeleton, we synthesized several coumarin derivatives whose chemical structures are similar to scopoletin. Scopoletin exhibited the strongest termiticidal activity among the 10 compounds tested, followed by 6-methoxycoumarin (3), 6-hydroxycoumarin (7), and umbelliferone (8). All compounds except coumarin (9) showed antifeedant activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Burseraceae / chemistry*
  • Coumarins / chemistry*
  • Coumarins / isolation & purification
  • Insecticides / chemistry*
  • Insecticides / isolation & purification
  • Isoptera*
  • Plant Extracts / chemistry
  • Quercetin / chemistry
  • Quercetin / isolation & purification
  • Scopoletin* / chemistry
  • Scopoletin* / isolation & purification
  • Stigmasterol / chemistry
  • Stigmasterol / isolation & purification
  • Structure-Activity Relationship
  • Umbelliferones / chemistry
  • Umbelliferones / isolation & purification

Substances

  • Coumarins
  • Insecticides
  • Plant Extracts
  • Umbelliferones
  • 7-hydroxycoumarin
  • Stigmasterol
  • Quercetin
  • coumarin
  • Scopoletin