title: Lasioderma chemistry sex pheromone of cigarette beetle (Lasioderma serricorne F.).
abstract: A chemical study of the sex pheromone of the cigarette beetle was carried out. Seven components were isolated from active fractions of column chromatography of the female extract, and their structures were elucidated by spectroscopic evidence and confirmed by synthesis to be (4S,6S,7S)-4,6-di-methyl-7-hydroxynonan-3-one (serricornin) (I), 2,6-diethyl-3,5-dimethyl-3,4-dihydro-2H-pyran (anhydroserricornin) (II), 4,6-dimethylnonan-3,7-dione (III), 4,6-dimethylnonan-3,7-diol (IV), 4,6-dimethyl-7-hydroxy-4-nonen-3-one (V), (2S,3R)-2,3-dihydro-3,5-dimethyl-2-ethyl-6-(l-methyl-2-oxobutyl)-4H-pyran-4-one (serricorone) (VI) and (2S,3R)-2,3-dihydro-3,5-dimethyl-2-ethyl-6-(1-methyl-2-hydroxybutyl)-4H-pyran-4-one (serricorole) (VII).These structural features suggested that the occurrence of these components might be related to the polyketide biosynthesis. The behavioral bioassay and BAG experiments revealed the biological role of each component in the copulatory behavior of this insect.
authors: Central Research Institute, The Japan Tobacco and Salt Public Corporation, 6-2 Umegaoka, Midori-ku, 227, Yokohama, Japan.
authors: T
authors: T
authors: Chuman
authors: K
authors: K
authors: Mochizuki
authors: M
authors: M
authors: Mori
authors: M
authors: M
authors: Kohno
authors: K
authors: K
authors: Kato
authors: M
authors: M
authors: Noguchi