Periplaneta american

In 1952, it was reported that a constituent of excretions from female American cockroaches of the species Periplaneta ameri-cana is an extraordinarily potent sex pheromone.1 Early attempts to isolate and characterize the active compounds were hampered because individual cockroaches store only minute amounts of the pheromone ( 1 pg), and a full 25 years elapsed before Persoons et al. reported the isolation of two extremely active compounds, periplanones A and B.2 The latter substance is present in larger relative measure and its germacranoid structure (1, without stereochemistry) was tentatively assigned on the basis of spectroscopic data. Thus, in 1976, the constitution of periplanone B was known but there remained a stereochemical problem of a rather serious nature. Roughly three years intervened between the report of the gross structure of periplanone B and the first total synthesis of this substance by W. C. Still at Columbia.3... 

Based on the successful series of transformations summarized in Scheme 1, Schreiber and Santini developed an efficient and elegant synthesis of periplanone B (1),8 the potent sex pheromone of the American cockroach, Periplaneta americana. This work constitutes the second total synthesis of periplanone B, and it was reported approximately five years after the landmark periplanone B synthesis by W.C. Still9 (see Chapter 13). As in the first synthesis by Still, Schreiber s approach to periplanone B takes full advantage of the facility with which functionalized 5-cyclodecen-l-one systems can be constructed via anionic oxy-Cope rearrangements of readily available divinylcyclohexanols.5 7 In addition, both syntheses of periplanone B masterfully use the conformational preferences of cyclo-decanoid frameworks to control the stereo- and regiochemical course of reactions carried out on the periphery of such ring systems.10... 

Tropomyosin is a protein found in vertebrates and invertebrates, but only the protein from invertebrates has allergic properties. It is frequently found in sea foods, such as shrimps, crabs, American lobsters. Pacific flying squids, and also in some species of cockroaches (Blattela germanica, Periplaneta americand), moths, spiders, and house dust mites (Dermatophagoides pteronyssinus, Dermatophagoides farinae) (Witteman et ah, 1994). 

Chlamys nipponensis (Japanese scallop) Mizuhopecten yessoensis (Yesso scallop) Mimachlamys nobilis Charybdis feriatus (crab) Homarus americanus (American lobster) Panulirus stimpsoni Homarus americanus (American lobster) Farfantepenaeus aztecus (pen a 1) Periplaneta americana (American cockroach) Dermatophagoides pteronyssinus (dust mite) Lepidoglyphus destructor Homo sapiens (human) Homo sapiens (human) Sus scrofa (pig) Oryctolagus cuniculus (rabbit)... 

Asturias, J. A., Gomez-Bayon, N., AriUa, M. C., Martinez, A., Palacios, R., Sanchez-Gascon, F., and Martinez, J. (1999). Molecular characterization of American cockroach tropomyosin (Periplaneta americana allergen 7), a cross-reactive aUergen. /. Immunol. 162, 4342 348. 

Singie abdominai injection of 1 mg famphur/kg BW whoie-body residues of famphur, famoxon, and /V-desmethyifamphur measured 1 h after injection AMERICAN COCKROACH, Periplaneta americana Of total amount injected, 84.6% remained after 1 h 79.4% famphur, 2.2% famoxon, and 3.1% /V-desmethylfamphur 2... 

AMERICAN COCKROACH, Periplaneta americana Baits containing 1.5% boric acid All dead in 6 days (6)... 

Hawkins, W. A. (1978). Effects of sex pheromone on locomotion in the male American cockroach, Periplaneta americana. Journal of Chemical Ecology 4 149-160. 

Isolation procedure of the sex pheromone of the American cockroach, Periplaneta americana L. Applied Entomology and Zoology 11 373-375. 

American cockroach, Periplaneta americana. Isolation and partial identification of two excitants. Proceedings of the Koninklijke Nederlandse Akademie van Weteschappen, Series C, Biological and Medical Sciences 77 201-204. 

W. J. (1976). Sex pheromones of the American cockroach, Periplaneta americana a tentative structure of periplanone-B. Tetrahedron Letters 24 2055-2058. 

Takahashi, S. and Kitamura, C. (1972). Bioassay procedure of the sex stimulant of the American cockroach, Periplaneta americana (L.) (Orthoptera Blattidae). Applied Entomology and Zoology 7 133-141. 

Wharton, M. L. and Wharton, D. R. A. (1957). The production of sex attractant substance and of oothecae by the normal and irradiated American cockroach, Periplaneta americana L. Journal of Insect Physiology 1 229-239. 

Kitabayashi A. N., Arai T., Kubo T. and Natori S. (1998) Molecular cloning of cDNA for plO, a novel protein that increases in regenerating legs of Periplaneta americana (American cockroach). Insect Biochem. Mol. Biol. 28, 785-790. 

Getz W. M. and Akers R. R (1997) Response of American cockroach (Periplaneta americana) olfactory receptors to selected alcohol odorants and their binary combinations. J. Comp. Physiol. A 180, 701-709. 

The ability of insects to withstand desiccation was recognized in the 1930s to be due to the epicuticular layer of the cuticle. Wigglesworth (1933) described a complex fatty or waxy substance in the upper layers of the cuticle which he called cuticulin . The presence of hydrocarbons in this wax of insects was suggested by Chibnall et al. (1934) and Blount et al. (1937), and over the next few decades the importance of hydrocarbons in the cuticular wax of insects was established (Baker et al., 1963 and references therein). The first relatively complete chemical analyses of the hydrocarbons from any insect, the American cockroach, Periplaneta americana (Baker et al., 1963), occurred after the development of gas-liquid chromatography (GLC). The three major components of the hydrocarbons of this insect, //-pen taco sane, 3-methylpentacosane and (Z,Z)-6,9-heptacosadiene, represent the three major classes of hydrocarbons on insects, n-alkanes, methyl-branched alkanes and alkenes. Baker and co-workers (1963) were able to identify n-pentacosane by its elution time on GLC to a standard and its inclusion in a 5-angstrom molecular sieve. 3-Methylpentacosane... 

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