Neral (the Alarm Pheromone) Biosynthesis via the Mevalonate Pathway, Evidenced by D-Glucose-1-13C Feeding in Carpoglyphus lactis and 13C Incorporation into Other Opisthonotal Gland Exudates1

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  • Morita Atsushi
    Laboratory of Chemical Ecology, Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University
  • Mori Naoki
    Laboratory of Chemical Ecology, Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University
  • Nishida Ritsuo
    Laboratory of Chemical Ecology, Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University
  • Hirai Nobuhiro
    International Innovation Center, Kyoto University
  • Kuwahara Yasumasa
    Laboratory of Chemical Ecology, Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University

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  • Neral (the alarm pheromone) biosynthesis via the mevalonate pathway, evidenced by d-glucose-1-13C feeding in Carpoglyphus lactis and 13C incorporation into other opisthonotal gland exudates

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The monoterpene neral [(Z)-3,7-dimethyl-2,6-octadienal], an alarm pheromone, has been identified as a major component of the opisthonotal gland exudates of Carpoglyphus lactis, together with tridecane and (Z,Z)-6,9-heptadecadiene. The CDCl3 extract of mites fed D-glucose-1-13C for 30 days was found to have 13C atoms at positions 2, 4, 6 and 8–10 by 13C-NMR analysis. The compound neral was, therefore, concluded to be produced via the mevalonate pathway from 2-13C-acetyl-CoA by glycolysis. After seven days of feeding on D-glucose-1-13C, at least one 13C atom was incorporated in 51.6% of neral molecules. Likewise, 51.8% of tridecane, 42.5% of (Z,Z)-6,9-heptadecadiene, 39.5% of γ-acaridial and 33.4% of neryl formate, were also labeled, while squalene was not labeled, indicative of its origin, the culture medium.

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