@phdthesis{oai:tsukuba.repo.nii.ac.jp:00008558, author = {Suzuki, Takahisa and 鈴木, 隆久}, month = {}, note = {Biologically active substances produced by the flour beetles, Tribolium, castaneum, and T. confusum were investigates. Seven unsaturated hydrocarbons were identified as 1-pentadecene, 1-heptadecene, 1,8-heptadecadiene, 1-tetradecene 1-hexadecene, 1,8-heptadecadiene, 1-tetradecene, 1-hexadecene, 1,6-pentadecadiene adn heptadecatriene by GLC, GLC-MS, NMR, IR and micro-ozonolysis. This is the first report on the presence of these compounds in T. castaneum, and the last four compounds were also identified for the first time in T. confusum. These compounds are strong repellents for the both species or each other. These hydorcarbons may serve as alarm pheromones or overcrowding factors. Further 2'-hydorxy-4'-methoxypropiophenone (Ⅰ) was isolated from both the adult flour beetles on the basis of NMR, MS, IR spectra and synthesis of it. The yield of this compound was about 1 μg/beetle for both species. This is the first report on the isolation of this compound from living organism. THe biological activity of this compound remains obscure. Male-secreted aggregation pheromone of both flour beetles was studied, and 760 μg of the pheromone was isolated from total 240,000 male equivalents (6,000 males x 40 days) of T. castaneum by air extraction method using Porapak Q colums. THe pheromone was identified as 4,8-dimenthy1-decanal by GLC, GLC-MS, NMR and hydrogenolytic gas chromatography, and its structure was confirmed by synthesis. The synthetic pheromone was attractive to both sexes at the level of 100 ng/disk, whereas the natural pheromone showed stronger attractancy even at lower amounts (1.5-15 ng/disk). The positive biological activity of the synthetic pheromone, though less active than the natural pheromone due to racemic mixture, would provide an additional proof for the proposed structure of the natural pheromone. Several analogues of the pheromone (racemic) were prepared, and sturcture-activity relationships among them were tested. The presence of methyl groups at C-4 and C-8 positions was indispensable for attractancy. The absolute configuration of the natural pheromone remains to be decided by preparation of four optical isomers. The synthetic work is now in progress., 1982}, school = {筑波大学, University of Tsukuba}, title = {Biologically active substances produced by the flour beetles, tribolium, castaneum and T. confusum}, year = {1982} }