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  • Food Science, Agricultural, Medicinal and Pharmaceutical Chemistry  (7)
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  • 1
    Electronic Resource
    Electronic Resource
    Correlation between glycerolipids and pheromone aldehydes in the sex pheromone gland of female tobacco hornworm moths, Manduca sexta (L.) (1995)
    New York, NY [u.a.] : Wiley-Blackwell
    Archives of Insect Biochemistry and Physiology 30 (1995), S. 321-336 
    Details
    ISSN: 0739-4462
    Keywords: triacylglycerols ; pheromone aldehydes ; sex pheromone gland ; Manduca sexta ; Chemistry ; Food Science, Agricultural, Medicinal and Pharmaceutical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology
    Notes: Analysis by TLC and HPLC revealed that the triacylglycerols comprise the most abundant lipid class in the sex pheromone glands of Manduca sexta females. Also, conjugated olefinic acyl analogs of the major pheromone aldehydes occur principally in the triacylglycerols. The amount of triacylglycerols with conjugated diene acyl moieties significantly decreased when the period of pheromone production was extended by 7 h beyond the normal period of pheromone production by 3 injections of pheromone biosynthesis activating neuropeptide (PBAN) at 3 h intervals. This decrease indicates that the triacylglycerols stored in the gland may serve as major sources of pheromone precursors in the biosynthesis of the sex pheromone aldehydes. Furthermore, analysis of pheromone aldehydes and triacylglycerols in the gland from moths treated with PBAN showed that the proportions of the triacylglycerols with conjugated diene moieties were closely correlated with the proportions of aldehydes found in the same gland. This correlation suggests that the proportions of fatty acids bound to certain triacylglycerols regulates the proportions of aldehydes in biosynthesis of the pheromone blend in M. sexta. © 1995 Wiley-Liss, Inc.This article is a US Government work and, as such, is in the public domain in the United States of America.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/arch.940300403
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  • 2
    Electronic Resource
    Electronic Resource
    Sex pheromone blend of Manduca sexta: Responses of central olfactory interneurons to antennal stimulation in male moths (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Archives of Insect Biochemistry and Physiology 10 (1989), S. 281-291 
    Details
    ISSN: 0739-4462
    Keywords: antennal lobe ; electrophysiology ; olfaction ; Chemistry ; Food Science, Agricultural, Medicinal and Pharmaceutical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology
    Notes: Recently, chemical analysis of solvent rinses of the external surfaces of pheromone glands from female Manduca sexta revealed a blend of 12 aldehydes, including the previously identified sex pheromone component, (E,Z)-10,12-hexadecadienal (bombykal). Previous electrophysiological studies showed that olfactory (deutocerebral) interneurons in the antennal lobes of males exhibited a wide range of responsiveness to pheromonal stimulation of the ipsilateral antenna. These experiments were performed with crude extracts of pheromone glands as well as two synthetic compounds: the major pheromone component, bombykal, and (E,Z)-11,13-pentadecadienal, a mimic of a second component of the female's pheromone blend. Using intracellular methods, we have now reexamined similar olfactory interneurons, using each of the 12 chemically identified components as well as synthetic blends of various combinations of them. Eight of the 12 components isolated from female glands elicited some form of response in olfactory interneurons in males. In accordance with biochemical and behavioral data, the most potent are bombykal and two trienals, (E,E,E)- and (E,E,Z)-10,12,14-hexadecatrienal. We also conclude that the C15 dienal is selective for one of the trienal receptors on the antenna, but is much less potent than the natural trienal stimulant.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/arch.940100404
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  • 3
    Electronic Resource
    Electronic Resource
    Semiochemically mediated foraging behavior in beneficial parasitic insects (1993)
    New York, NY [u.a.] : Wiley-Blackwell
    Archives of Insect Biochemistry and Physiology 22 (1993), S. 385-391 
    Details
    ISSN: 0739-4462
    Keywords: parasitoid ; plant-insect interactions ; learning ; biological control ; Chemistry ; Food Science, Agricultural, Medicinal and Pharmaceutical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology
    Notes: Chemical cues enable female parasitic wasps to locate the eggs, larvae, or other life stages of the insects in or on which they place their eggs. These chemical signals, or semiochemicals, may be produced by the hosts and/or by the plants on which the hosts feed. The composition of the chemical signal often differs with different species of hosts or with different plants. New evidence suggests that the wasps exploit semiochemicals emitted by plants in response to insect herbivore feeding. The wasps learn to respond to the different blends of chemicals that indicate the location of their hosts and they can be trained to respond to a specific odor blend. Thus, it may be possible to increase their effectiveness for biological control by conditioning them, prior to their release, to search for a target pest in a particular crop. © 1993 Wiley-Liss, Inc.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/arch.940220307
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  • 4
    Electronic Resource
    Electronic Resource
    PBAN regulation of pheromone biosynthesis in female tobacco hornworm moths,Manduca sexta (L.) (1995)
    New York, NY [u.a.] : Wiley-Blackwell
    Archives of Insect Biochemistry and Physiology 29 (1995), S. 35-44 
    Details
    ISSN: 0739-4462
    Keywords: PBAN ; fatty acyl precursor ; Manduca sexta ; sex pheromone ; aldehydes ; Chemistry ; Food Science, Agricultural, Medicinal and Pharmaceutical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology
    Notes: Manduca sexta females that were decapitated produced no pheromone during the scotophase following decapitation, indicating that they were free of pheromone biosynthesis activating neuropeptide (PBAN). When deuterated hexadecanoic or (Z)-11-hexadecenoic acid was applied to the sex pheromone glands of decapitated or intact females of the same age, and allowed to incubate in vivo for 24 h, deuterium labeled Δ-11- and Δ-10, 12-unsaturated 16-carbon fatty acids were produced in both types of females. Injection of PBAN into intact or decapitated females 23 h after application of labeled acids had no effect on the production of unsaturated labeled fatty acids. However, deuterium labeled aldehydes were produced only in females that were injected with PBAN. Therefore, in this species, PBAN activates the process by which fatty acyl precursors in the pheromone gland are converted into the pheromonal aldehydes. © 1995 Wiley-Liss, Inc.This article is a US Government work and, as such, is in the public domain in the United States of America.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/arch.940290105
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  • 5
    Electronic Resource
    Electronic Resource
    Identification of a pheromone blend attractive to Manduca sexta (L.) males in a wind tunnel (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Archives of Insect Biochemistry and Physiology 10 (1989), S. 255-271 
    Details
    ISSN: 0739-4462
    Keywords: insect behavior ; aldehydes ; 10 ; 12 ; 14-hexadecatrienal ; tobacco hornworm ; Sphingidae ; Chemistry ; Food Science, Agricultural, Medicinal and Pharmaceutical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology
    Notes: Analyses of solvent rinses of the external surfaces of pheromone glands excised from calling female tobacco hornworm moths, Manduca sexta (L.), revealed the presence of the following compounds: (Z)-9-hexadecenal, (Z)-11-hexadecenal, (E)-11-hexadecenal, hexadecanal, (E,Z)-10,12-hexadecadienal, (E,E)-10,12-hexadecadienal, (E,E,Z)-10,12,14-hexadecatrienal, (E,E,E,)-10,12,14-hexadecatrienal, (Z)-11-octadecenal, (Z)-13-octadecenal, octadecanal, and (Z,Z)-11,13-octadecadienal. The two trienals were identified by mass and PMR spectral analyses and by ozonolyses, and their structures were confirmed by synthesis. In a wind tunnel male tobacco hornworm moths exhibit the same behaviors in response to a synthetic blend of all of the components, the gland rinse, or a calling female. Both (E,Z)-10,12-hexadecadienal and (E,E,Z)-10,12,14-hexadecatrienal are required to stimulate males to complete the characteristic behavioral sequence: anemotaxis, approaching and touching the pheromone source, and bending their abdomens in apparent copulatory attempts. The other components of the blend may play more subtle roles.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/arch.940100402
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  • 6
    Electronic Resource
    Electronic Resource
    Pheromone receptor cells in the male moth Manduca sexta (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Archives of Insect Biochemistry and Physiology 10 (1989), S. 273-279 
    Details
    ISSN: 0739-4462
    Keywords: olfaction ; sex pheromone ; electrophysiology ; antenna ; Chemistry ; Food Science, Agricultural, Medicinal and Pharmaceutical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology
    Notes: Three types of pheromone receptor cells have been identified by electrophysiological recording from single antennal sensilla trichodea of the male sphinx moth Manduca sexta. These cells responded best to the pheromone components (E,Z)-10,12-hexadecadienal (type A receptor cell), (E,E,Z)-10,12,14-hexadecatrienal (type B), and (E,E,E)-10,12,14-hexadecatrienal (type C). Cell type B also responded to (E,Z)-11,13-pentadecadienal, which has been used experimentally as a pheromone substitute. In recordings from 20 trichoid hairs, 17 were found to be innervated by one cell of type A and one of type B; 3 trichoid hairs had cell types A and C.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/arch.940100403
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  • 7
    Electronic Resource
    Electronic Resource
    Characterization of oxidase(s) associated with the sex pheromone gland in Manduca sexta (L.) females (1995)
    New York, NY [u.a.] : Wiley-Blackwell
    Archives of Insect Biochemistry and Physiology 29 (1995), S. 243-257 
    Details
    ISSN: 0739-4462
    Keywords: pheromone biosynthesis ; aldehydes ; alcohols ; oxidase inhibitor ; piperonyl butoxide ; Chemistry ; Food Science, Agricultural, Medicinal and Pharmaceutical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology
    Notes: An oxidase that converts primary aliphatic alcohols into aldehydes was discovered in the cuticle of the sex pheromone gland and in the papillae anales on the tip of the abdomen of Manduca sexta females. Oxidase activity was not found in the epidermal cells of the pheromone gland where fatty acid precursors of the pheromonal aldehydes are found. This oxidase requires oxygen and water to function and appears to have a rather broad substrate specificity. The activity of the oxidase is reduced by the application of piperonyl butoxide, which also interferes with the PBAN induced production of the natural pheromone aldehydes. However, endogenous alcohols cannot be found in the pheromone gland. Thus, it is not yet clear whether or not the oxidase is involved in the terminal step of biosynthesis of the pheromone aldehydes in M. sexta females. © Wiley-Liss, Inc.This article is a U.S. Government work and, a such, is in the public domain in the United States of America.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/arch.940290303
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