title: Insect growth inhibition, antifeedant and antifungal activity of compounds isolated/derived from Zingiber officinale Roscoe (ginger) rhizomes.
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).
authors.affiliation: Division of Agricultural Chemicals, Indian Agricultural Research Institute, New Delhi-110 012, India.
authors.forename: M
authors.initials: M
authors.lastname: Agarwal
authors.forename: S
authors.initials: S
authors.lastname: Walia
authors.forename: S
authors.initials: S
authors.lastname: Dhingra
authors.forename: B P
authors.initials: BP
authors.lastname: Khambay
mesh_terms: 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
chemical_list: 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