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  • 1
    Electronic Resource
    Electronic Resource
    Developmental expression of a novel Kexin family protease, PACE4E, in the rat olfactory system (1997)
    Springer
    Histochemistry and cell biology 108 (1997), S. 95-103 
    Details
    ISSN: 1432-119X
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract  PACE4 is a mammalian Kexin family protease that is involved in the maturation of precursor proteins. Four PACE4 isoforms have been identified. We identified a novel PACE4 isoform, PACE4E, from a human cerebellum cDNA library, which possesses a hydrophobic cluster in its C-terminus participating in membrane association. The size of PACE4E mRNA from adult rat brain was estimated by Northern blotting to be 4.4 kb. In situ hybridization histochemistry revealed that the highest level of PACE4E mRNA was expressed in the mitral cells of the adult rat olfactory bulb (OB). The OB is a unique sensory organ in that it has a lifelong regenerating capacity and it affects brain development. We further analyzed the expression of PACE4E mRNA in the developing olfactory system. On day 13.5 of gestation, PACE4E mRNA was expressed at high levels in the neuroepithelium of the forebrain vesicle (FV), olfactory epithelium, and cells in the fiber bundles projecting to the FV. As development proceeded, PACE4E mRNA was expressed in developing mitral cells but decreased in the olfactory epithelium. In the newborn, its expression was confined to the mitral cells in both the main and accessory OB and in some periglomerular cells, as shown in adult rats. The spatio-temporal expression of PACE4E suggests that it plays a role in the establishment and maintenance of the olfactory receptor system.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004180050150
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  • 2
    Electronic Resource
    Electronic Resource
    Male pheromone of swift moth,Hepialus hecta L. (Lepidoptera: Hepialidae) (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 3511-3521 
    Details
    ISSN: 1573-1561
    Keywords: Hepialus ; Lepidoptera ; Hepialidae ; swift moth ; pheromone ; dihydropyrone ; 2,9-dioxabicyclo[3.3.1] nonane ; behavior ; electrophysiology
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract (R)-6-Ethyl-2-methyl-2,3-dihydro-4H-pyran-4-one, (1R,3S,5R)-3-ethyl-1,8-dimethyl-2,9-dioxabicyclo[3.3. 1]non-7-ene, and (1R,3S,5R)-3-ethyl-1,8-dimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-one represent the main components in the male pheromone of the swift moth,Hepialus hecta. The amounts of the three components were 40, 5, and 5 μg per male, respectively. Structure elucidation of the compounds was based on spectroscopic data as compared to synthetic reference samples. The absolute configurations were determined by gas chromatography on chiral stationary phases; optically active samples served as reference compounds. Electrophysiological and behavioral experiments with natural material and synthetic samples clearly showed the three heterocyclic compounds to act as pheromones. (E, E)-α-Farnesene represents the main component of the scent secretion of maleHepialus humuli.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00982114
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  • 3
    Electronic Resource
    Electronic Resource
    Andrena wilkella male bees discriminate between enantiomers of cephalic secretion components (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 429-441 
    Details
    ISSN: 1573-1561
    Keywords: Enantiomer discrimination ; male patrolling ; odor marking ; Hymenoptera ; Apoidea ; Andrena wilkella ; bee ; EAG ; spiroacetal ; absolute configuration ; 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Diastereomers of the spiroacetal, 2,8-dimethyl-1,7-dioxaspiro [5.5]undecane, represent main components of the cephalic secretion from males of the solitary bee,Andrena wilkella. The major compound proved to be of high enantiomeric purity, showing (2S,6R,8S) configuration. Only the naturally occurring enantiomer attracted patrolling males in the field; its antipode was behaviorally inactive and in a racemic mixture did not inhibit response. The (E,Z) diastereomers were also found to be almost inactive. EAG studies gave the same result as the behavioral tests. The biological function of the spiroacetal is discussed in view of the evolution of the mating behavior inA. wilkella.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01021775
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  • 4
    Electronic Resource
    Electronic Resource
    Grain weevil,Sitophilus granarius (L.): Antennal and behavioral responses to male-produced volatiles (1996)
    Springer
    Journal of chemical ecology 22 (1996), S. 1639-1654 
    Details
    ISSN: 1573-1561
    Keywords: Sitophilus granarius ; grain weevil ; Coleoptera ; aggregation pheromone ; electroantennogram ; coupled GC-EAG ; behavioral bioassay ; circular dichroism
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Coupled GC-EAG techniques have been applied to the study of volatiles from the grain weevil,Sitophilus granarius. for the first time. The size of EAG response was independent of the sex of the responding insect but was consistently larger to extracts of males than those of females. This difference was reflected in a behavioral preference for the male extracts by mated adults of both sexes tested together and virgin adults of both sexes tested separately. The GC-EAG results provide evidence for two materials that are released specifically by the males. Using circular dichroism. one has been found to be identical stereochemically with the (2S,3R)-sitophilate reported by others as the aggregation pheromone in a different strain. This enhances the prospects for the development of a single pheromone lure that would be generally applicable whatever the origin of the strain. The small amount of sitophilate found in the males suggests that it is not stored in large amounts. The other material, present in such a small amount that it has yet to be fully characterized, elicits a higher antennal activity than sitophilate and may have a significant role to play in enhancing the trap catch of this economically important pest.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02272404
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  • 5
    Electronic Resource
    Electronic Resource
    Specificity of Pheromonal and Kairomonal Response of the Israeli Pine Bast Scale Matsucoccus josephi and Its Predator Elatophilus hebraicus (2000)
    Springer
    Journal of chemical ecology 26 (2000), S. 1649-1657 
    Details
    ISSN: 1573-1561
    Keywords: Matsucoccus josephi ; Homoptera ; Matsucoccidae ; Elatophilus hebraicus ; Hemiptera ; Anthocoridae ; sex pheromone ; kairomone ; analog
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract It has been demonstrated previously that the sex pheromone of the Israeli pine bast scale, Matsucoccus josephi, (2E,5R,6E,8E)-5,7-dimethyl2,6,8-decatrien-4-one (1) is also a potent kairomone of the scale insect's predator Elatophilus hebraicus. Surprisingly, the sex pheromones of M. feytaudi (2) and M. matsumurae (3) also attract E. hebraicus. These results have prompted us to prepare a series of analogs of 1 with variations in the two moieties attached to the C=O group (4–9) in order to probe the structure–activity relationship of the pheromonal/kairomonal response of M. josephi and E. hebraicus. The most selective and active pheromone analog is 8, attracting only M. josephi males and the most selective and active kairomone analog is the M. feytaudi pheromone 2, attracting only adults of E. hebraicus. A dose–response field test of these analogs and the chiral and racemic M. josephi pheromone 1 indicates that the specificity is maintained at a broad range between 25 and 400 μg corresponding to 1. Analog 5, which is neither a parapheromone nor a kairomone, and analog 8, which is only a parapheromone, are not inhibitory to M. josephi or to E. hebraicus. Our study indicates that alterations in the diene side chain of 1, common to all three Matsucoccus pheromones, strongly reduce the kairomonal activity while structural changes in the second side chain significantly reduce the pheromonal activity. The discovery of selective analogs of 1 has practical implications and enables specific monitoring of M. josephi or E. hebraicus. Particularly important is the possibility to mass-trap males of M. josephi without reducing the population of E. hebraicus.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1005538929610
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  • 6
    Electronic Resource
    Electronic Resource
    Perception byTrogoderma species of chirality and methyl branching at a site far removed from a functional group in a pheromone component (1980)
    Springer
    Journal of chemical ecology 6 (1980), S. 911-917 
    Details
    ISSN: 1573-1561
    Keywords: Trogoderma species ; trogodermal ; enantiomers ; chiral center ; geometric isomers ; methyl branching ; (Z)- or (E)-14-methyl-8-hexadecenal ; dermestid beetles ; Coleoptera ; Dermestidae ; pheromone ; chemoreception ; olfaction ; (Z)-hexadecenal
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Responses to enantiomers of (Z)- and (E)-trogodermal (14-methyl-8-hexadecenal) suggest that fourTrogoderma species utilize the (R)-(−) configuration at C-14. Removal of the C-14 methyl branch decreased the response. These results demonstrate the high specificity associated with the configuration at a chiral center, or the methyl branch, distant in terms of numbers of bonds from a functional group.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00990475
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  • 7
    Electronic Resource
    Electronic Resource
    Receptor chirality and behavioral specificity of the boll weevil,Anthonomus grandis Boh. (Coleoptera: Curculionidae), for its pheromone, (+)-grandisol (1989)
    Springer
    Journal of chemical ecology 15 (1989), S. 517-528 
    Details
    ISSN: 1573-1561
    Keywords: Boll weevil ; olfaction ; receptor cell ; Anthonomus grandis ; Coleoptera ; Curculionidae ; enantiomer ; grandisol ; chirality ; electroantennogram ; aggregation pheromone ; neurobiology ; structure-activity
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Electrophysiological recordings from antennal olfactory receptors and field behavioral experiments showed both male and female boll weevils,Anthonomus grandis Boh. (Coleoptera: Curculionidae), to respond specifically to (+)-grandisol, an enantiomer of compound I of the boll weevil aggregation pheromone. Single-cell recordings revealed antennal olfactory neurons in both male and female weevils keyed to (+)-grandisol. Electroantennograms in response to serial dilutions of the grandisol enaniiomers showed a threshold 100 to 1000 times lower for (+)-grandisol relative to its antipode. In field behavioral experiments, both sexes were significantly more attracted to (+)-grandisol in combination with the three other pheromone components than the combination with (−)-grandisol. When (−)-grandisol was placed with the (+)-enantiomer at equal dosages, a slight although statistically insignificant inhibition occurred. Subsequent field tests showed that the low level of attraction exhibited by (−)-grandisol in combination with the other three pheromone components could be attributed to the other three components alone. These results are in contrast with an earlier study, which found (−)-grandisol to be as attractive as the (+)-enantiomer.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01014697
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  • 8
    Electronic Resource
    Electronic Resource
    Electroantennograms by mountain pine beetles,Dendroctonus ponderosae Hopkins, exposed to selected chiral semiochemicals (1989)
    Springer
    Journal of chemical ecology 15 (1989), S. 2089-2099 
    Details
    ISSN: 1573-1561
    Keywords: Olfaction ; chirality ; pheromone ; semiochemical ; enantiomer ; bark beetle ; electrophysiology ; electroantennogram ; mountain pine beetle ; Dendroctonus ponderosae ; Coleoptera ; Scolytidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Electroantennograms (EAGs) were recorded fromD. ponderosae to the enantiomers of the terpenoid bark-beetle pheromonestrans-verbenol,cis-verbenol, verbenone, and the bicyclic ketals frontalin,exo-brevicomin, andendo-brevicomin. Male and female responses to enantiomers of the terpenoids differed significantly only at the two highest concentrations. No sex differences were seen in response to the bicyclic ketals. Significantly different responses to the enantiomers of all the chemicals, except frontalin, were noted over at least part of the dosage-response ranges tested. The negative antipode for all of the terpenoids elicited higher responses, while for the bicyclic ketals, the positive antipode effected the largest responses except for the two highest concentrations ofexo-brevicomin.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01207440
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  • 9
    Electronic Resource
    Electronic Resource
    Flight-mediated attraction ofBiprorulus bibax breddin (Hemiptera: Pentatomidae) to natural and synthetic aggregation pheromone (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 71-80 
    Details
    ISSN: 1573-1561
    Keywords: Aggregation pheromone ; B. bibax ; Citrus ; Hemiptera ; Pentatomidae ; dorsal abdominal gland ; hemiacetal
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The attraction of female spined citrus bugs,Biprorulus bibax, to natural and synthetic aggregation pheromone was studied using an olfactometer and a large flight cage. No locomotory response by postdiapause, prereproductive females to heptane extracts of male dorsal abdominal glands (DAGs) (site of pheromone production) was recorded in the olfactometer study. However, postdiapause, prereproductive females showed significant attraction to sites baited with DAG extracts in the flight cage (1.9–3.0 times that of unbaited sites). Prereproductive and reproductive females showed greatest attraction to sites baited with a synthetic blend of pheromone [(3R,4S,1′E-3,4-bis(1′-butenyl)tetrahydro-2-furanol, linalool, farnesol, nerolidol] (2.3–4.7 times the attraction of unbaited sites). Females also responded significantly to sites baited with the hemiacetal major component alone (1.7–2.2×). Diapausing females collected from fall populations did not respond to natural or synthetic pheromone baits. Potential applications of the synthetic aggregation pheromone are discussed with respect toB. bibax management.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02065991
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  • 10
    Electronic Resource
    Electronic Resource
    Bisabolene epoxides in sex pheromone innezara viridula (L.) (Heteroptera: Pentatomidae): Role ofcis isomer and relation to specificity of pheromone (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 3133-3147 
    Details
    ISSN: 1573-1561
    Keywords: Nezara viridula ; Heteroptera ; Pentatomidae ; sex pheromone ; trans- andcis-(Z)-α-bisabolene epoxides ; interindividual variation ; bioassay ; pheromonal specificity ; isomer ; enantiomer
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Thetrans- andcis-(Z)-α-bisabolene epoxides (trans- andcis-(Z)-αBE) are the main components of the male sex pheromone inNezara viridula. The role of thecis isomer and the importance of thecis/trans proportion for the activity and the specificity of the pheromone are not clearly elucidated and were studied here. Interindividual variation of thecis/trans proportion produced by males was studied by individual hexanic extracts in two strains originating from the south of France (SF) and French West Indies (FWI). Thetrans isomer composed 42–82% of bisabolene epoxides in SF males and 74–94% of bisabolene epoxides in FWI males. Means (± SD) significantly differ between SF (62.8%±8.4) and FWI (82.4%±5.9) males in spite of this interindividual variation. Different isomers of bisabolene epoxide were synthesized and their EAG activity on female antennae was compared. Racemictrans- andcis-(Z)-αBE elicited low EAGs, not different from the nonnaturaltrans andcis (E)-αBE that were inactive on behavior. Behavioral tests revealed that racemictrans- andcis-(Z)-αBE attracted 45% (P〈0.05) and 25% (P〈0.05) of females, respectively. The same levels of attraction were obtained with (−) enantiomers oftrans- andcis-(Z)-αBE, which attracted 40% (P〈0.05) and 20% (P〉0.05) of the females, respectively. Binary blends containing 75/25, 50/50, and 25/75 proportions ofcis/trans isomers were more attractive thantrans-(Z)-αBE alone and response of females to the 25%cis/75%trans blend was significantly more important than the response totrans-isomer alone (P〈0.05). The importance of thecis/trans proportion in relation with the specificity of the male pheromone is discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02033716
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