| Title: | Inhibition of male response of drugstore beetles to stegobinone by its isomer |
| Author(s): | Kodama H; Mochizuki K; Kohno M; Ohnishi A; Kuwahara Y; |
| Address: | "Central Research Institute, Japan Tobacco Inc., Umegaoka 6-2, Midori-ku, 227, Yokohama, Japan" |
| ISSN/ISBN: | 0098-0331 (Print) 0098-0331 (Linking) |
| Abstract: | "Stegobinone, (2S, 3R, 1'R)-2,3,-dihy dro-2,3,5-trimethyl-6-(1'-methyl-2'-oxobutyl)-4H-pyran-4-one, the sex pheromone of drugstore beetles (Stegobium paniceum L.), elicited the pheromonal response from the males of the species in our bioassay system; however, the synthesized diastereomeric mixture of this compound was actually inactive to the males. Although the stegobinone isolated from the beetles of this species had significant activity, its enantiomeric [(+/-)-2S,3R,1'S-] and diatereomeric [(+/-)-2S,3S,1'RS-] isomers were inactive. Adding the (+/-)-2S,3R,1'S isomer to stegobinone significantly reduced the male response. Furthermore, the activity of Stegobinone vanished on keeping it at room temperature for two weeks. In such a stored stegobinone sample, the presence of 2S,3R,1'S isomer, the inhibitory component, was confirmed. This isomer might be produced by C-1' epimerization during storage" |
| Notes: | "PubMed-not-MEDLINEKodama, H Mochizuki, K Kohno, M Ohnishi, A Kuwahara, Y eng 1987/08/01 J Chem Ecol. 1987 Aug; 13(8):1859-69. doi: 10.1007/BF01013235" |
