Insect growth inhibition, antifeedant and antifungal activity of compounds isolated/derived from Zingiber officinale Roscoe (ginger) rhizomes.
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).
Agarwal
M
M
Division of Agricultural Chemicals, Indian Agricultural Research Institute, New Delhi-110 012, India.
Walia
S
S
Dhingra
S
S
Khambay
B P
BP
D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology*; D002396:Catechols / Q000138:chemical synthesis / Q000494:pharmacology; D005233:Fatty Alcohols / Q000302:isolation & purification / Q000494:pharmacology; D005247:Feeding Behavior / Q000187:drug effects; D020939:Zingiber officinale / Q000737:chemistry*; D006139:Guaiacol / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D007300:Insect Control / Q000379:methods; D007306:Insecticides / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology*; D007814:Larva / Q000254:growth & development; D007915:Lepidoptera / Q000254:growth & development*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009153:Mutagens / Q000302:isolation & purification / Q000494:pharmacology; D010946:Plants, Medicinal; D013343:Styrenes / Q000138:chemical synthesis / Q000494:pharmacology
D000935:Antifungal Agents; D002396:Catechols; D005233:Fatty Alcohols; D007306:Insecticides; D009153:Mutagens; D013343:Styrenes; C013738:zingerone; D006139:Guaiacol; C040115:shogaol; C052933:methyl-3-methoxy-4-hydroxystyryl ketone; C007845:gingerol