Insect growth inhibition, antifeedant and antifungal activity of compounds isolated/derived from Zingiber officinale Roscoe (ginger) rhizomes

Pest Manag Sci. 2001 Mar;57(3):289-300. doi: 10.1002/ps.263.

Abstract

Fresh rhizomes of Zingiber officinale (ginger), when subjected to steam distillation, yielded ginger oil in which curcumene was found to be the major constituent. The thermally labile zingiberene-rich fraction was obtained from its diethyl ether extract. Column chromatography of ginger oleoresin furnished a fraction from which [6]-gingerol was obtained by preparative TLC. Naturally occurring [6]-dehydroshogaol was synthesised following condensation of dehydrozingerone with hexanal, whereas zingerone and 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)butane were obtained by hydrogenation of dehydrozingerone with 10% Pd/C. The structures of the compounds were established by 1H NMR, 13C NMR and mass (EI-MS and ES-MS) spectral analysis. The test compounds exhibited moderate insect growth regulatory (IGR) and antifeedant activity against Spilosoma obliqua, and significant antifungal activity against Rhizoctonia solani. Among the various compounds, [6]-dehydroshogaol exhibited maximum IGR activity (EC50 3.55 mg ml-1), while dehydrozingerone imparted maximum antifungal activity (EC50 86.49 mg litre-1).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology*
  • Catechols / chemical synthesis
  • Catechols / pharmacology
  • Fatty Alcohols / isolation & purification
  • Fatty Alcohols / pharmacology
  • Feeding Behavior / drug effects
  • Guaiacol / analogs & derivatives
  • Guaiacol / chemical synthesis
  • Guaiacol / pharmacology
  • Insect Control / methods
  • Insecticides / chemical synthesis
  • Insecticides / isolation & purification
  • Insecticides / pharmacology*
  • Larva / growth & development
  • Lepidoptera / growth & development*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mutagens / isolation & purification
  • Mutagens / pharmacology
  • Plants, Medicinal*
  • Styrenes / chemical synthesis
  • Styrenes / pharmacology
  • Zingiber officinale / chemistry*

Substances

  • Antifungal Agents
  • Catechols
  • Fatty Alcohols
  • Insecticides
  • Mutagens
  • Styrenes
  • zingerone
  • Guaiacol
  • shogaol
  • methyl-3-methoxy-4-hydroxystyryl ketone
  • gingerol