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Inhibitory action of (4S,6S,7R)-isomer to pheromonal activity of serricornin, (4S,6S,7S)-7-Hydroxy-4,6-dimethyl-3-nonanone (1986)

Mori, M. ; Mochizuki, K. ; Kohno, M. ; [et al.]

Springer

Journal of chemical ecology 12 (1986), S. 83-89

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ISSN: 1573-1561

Keywords: Sex pheromone ; cigarette beetle ; Lasioderma serricorne (F.) ; Coleoptera ; Anobiidae ; serricornin ; 7-hydroxy-4,6-dimethyl-3-nonanone ; inhibitory action of diastereoisomer

Source: Springer Online Journal Archives 1860-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Abstract By adding the effects of a series of the stereoisomers to the pheromonal activity of serricornin, (4S,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone, the sex pheromone of the cigarette beetleLasioderma serricorne (F.) was investigated. The experiments using synthetic enantiomeric mixtures and optically active stereoisomers showed that the (4S,6S,7R)-isomer inhibited significantly the pheromonal activity of serricornin.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF01045592

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Absolute configuration of mosquito oviposition attractant pheromone, 6-acetoxy-5-hexadecanolide (1985)

Laurence, B. R. ; Mori, K. ; Otsuka, T. ; [et al.]

Springer

Journal of chemical ecology 11 (1985), S. 643-648

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ISSN: 1573-1561

Keywords: Mosquito ; Culex pipiens fatigans ; Diptera ; Culicidae ; oviposition ; attractant ; pheromone ; chiral chromatography ; acetoxyhexadecanolide

Source: Springer Online Journal Archives 1860-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Abstract 6-Acetoxy-5-hexadecanolide (Ia) in the oviposition attractant pheromone released from egg apical droplets of the mosquitoCulex pipiens fatigans Wied. is shown to be the (−)-(5R,6S)- enantiomer. Identification was by chromatography of the 6-trifluoroacetoxy derivatives of the natural pheromone and of the synthetic (−)-(5R,6S)- (Ib) and (+)-(5S,6R)- (IIb) enantiomers on a capillary column having a chiral stationary phase comprising a derivative of (1S,3S)-chrysanthemic acid. The synthetic (−)-(5R,6S)- enantiomer (Ia) attracted oviposition of four fold more mosquito egg rafts than the control (P 〈 0.01) whereas for the (5S,6R)- enantiomer (IIa) there was no statistically significant oviposition attraction.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00988573

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Reinvestigation of anhydroserricornin, (2S,3S)-2,6-diethyl-3,5-dimethyl-3,4-dihydro-2H-pyran, as a sex pheromone component for male cigarette beetle (1986)

Mochizuki, K. ; Mori, M. ; Chuman, T. ; [et al.]

Springer

Journal of chemical ecology 12 (1986), S. 179-186

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ISSN: 1573-1561

Keywords: Sex pheromone ; cigarette beetle ; Lasioderma serricorne (F.) ; Coleoptera ; Anobiidae ; serricornin ; 7-hydroxy-4,6-dimethyl-3-nonanone ; anhydroserricornin ; 2,6-diethyl-3,5-dimethyl-3,4-dihydro-2H-pyran

Source: Springer Online Journal Archives 1860-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Abstract Reinvestigation of the pheromonal activity of anhydroserricornin, (2S,3S)-2,6-diethyl-3,5-dimethyl-3,4-dihydro-2H-pyran, showed that the magnitude of its activity was less than 1/103 of that of serricornin, 7-hydroxy-4,6-dimethyl-3-nonanone, the sex pheromone of the cigarette beetleLasioderma serricorne (F.). Neither a synergistic nor an inhibitory effect of anhydroserricornin addition on the action of serricornin was observed.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF01045601

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