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(Z)-8-dodecenyl acetate: the major component of the female sex pheromone of Cryptophlebia batrachopa, a Tortricid pest of macadamia in Malawi (1984)

Hall, David R. ; Beevor, Peter S. ; Cork, Alan ; [et al.]

Springer

Entomologia experimentalis et applicata 35 (1984), S. 33-36

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ISSN: 1570-7458

Keywords: Sex pheromone ; (Z)-8-dodecenyl acetate ; (E)-8-dodecenyl acetate ; Tortricidae ; Cryptophlebia batrachopa ; Cryptophlebia leucotreta ; Opogona spp.

Source: Springer Online Journal Archives 1860-2000

Topics: Biology

Description / Table of Contents: Résumé Les produits recueillis par lavages de l'ovipositeur de Cryptophlebia batrachopa Meyr. (Lep. Tortricidae) ont été analysés par chromatographie gazeuse (GC) associée à l'électroantennographie (EAG) et la GC à haute résolution. Le principal constituant actif en EAG provenant des lavages s'est révélé être le (Z)-8-dodécényl acétate avec moins de 0,5% de l'isomère E. L'analyse GC de ces produits de lavage de C. leucotreta ont confirmé la présence d'à peu près les mêmes quantités de (Z) et (E)-8-dodécényl acétates (Persoons et al., 1977). Quand des essais sur le terrain ont été effectués au Malawi, où existent les deux espèces de Cryptophlebia, avec du (Z)-8-dodécényl acétate et des mélanges comprenant jusqu'à 50% de l'isomère E, des mâles de C. batrachopa ont seuls été capturés dans des pièges contenant 10% ou moins de l'isomère E; les captures les plus élevées ont été obtenues avec l'isomère Z pur. A l'opposé, surtout des mâles de C. leucotreta ont été capturés dans des pièges garnis avec plus de 10% d'isomère E, et aucune capture n'a été obtenue avec l'isomère Z pur. Des mâles d'Opogona spp. ont été attirés par du (Z)-8-dodécényl acétate contenant 1% de l'isomère E.

Notes: Abstract Ovipositor washings from virgin female Cryptophlebia batrachopa (Meyrick) (Lepidoptera: Tortricidae) were analysed by gas chromatography (GC) linked to electroantennography (EAG) and by high-resolution GC. The major EAG-active component in ovipositor washings was shown to be (Z)-8-dodecenyl acetate with less than 0.5% of the E isomer. GC analysis of ovipositor washings from C. leucotreta confirmed the presence of approximately equal amounts of (Z)- and (E)-8-dodecenyl acetates (Persoons et al., 1977). When pure (Z)-8-dodecenyl acetate and mixtures containing up to 50% of the E isomer were tested in the field in Malawi where both Cryptophlebia species occurred, C. batrachopa male moths were caught only in traps baited with 10% or less of the E isomer and highest catches were recorded for the pure Z isomer. By contrast C. leucotretra males were caught predominantly by traps baited with more than 10% E isomer and no catches were recorded for the pure Z isomer. (Z)-8-dodecenyl acetate containing 1% of the E isomer was found to attract male moths of Opogona spp.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00343454

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Identification of components of the female sex pheromone of the potato tuber moth, Scrobipalpopsis solanivora (1985)

Nesbitt, Brenda F. ; Beevor, Peter S. ; Cork, Alan ; [et al.]

Springer

Entomologia experimentalis et applicata 38 (1985), S. 81-85

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ISSN: 1570-7458

Keywords: Scrobipalpopsis solanivora ; Lepidoptera ; Gelechiidae ; sex pheromone ; (E)-3-dodecenyl acetate ; (Z)-3-dodecenyl acetate

Source: Springer Online Journal Archives 1860-2000

Topics: Biology

Description / Table of Contents: Résumé S. solanivora est l'un des plus importants lépidoptères détruisant les pommes de terre en Amérique Centrale. L'analyse par chromatographie en phase gazeuse (GC) des produits obtenus par lavage de l'ovipositeur de femelles vierges, associée à des électro-anténnogrammes (EAG) a révélé un composé actif unique en EAG. Les durées de rétention pour ce constituant correspondaient à celles des acétates monoinsaturés à 12 carbones, et les analyses sur colonne GC liées avec une phase liquide cristal ont montré un pic principal correspondant à l'acétate (E)-3-dodécénul et un pic secondaire, correspondant à l'isomère Z, et au niveau de 2,5% du pic principal. L'acétate dodécyl a aussi été décelé en quantités variables, approximativement 10% du pic principal. Dans la nature, des pièges contenant de l'acétate (E)-3-dodécényl, seul ou mélangé avec 1 ou 2% de l'isomère Z, ont capturé autant des mâles de S. solanivora que des pièges contenant des femelles vierges, et certaines indications montrent que l'addition de 5% de l'isomère Z réduit les captures.

Notes: Abstract The sex pheromone produced by virgin female S. solanivora moths has been shown to contain (E)-3-dodecenyl acetate with approximately 2% of the Z isomer by electroantennography and gas chromatography. In the field, traps baited with (E)-3-dodecenyl acetate alone or in combination with 1% or 2% of the Z isomer caught at least as many male S. solanivora moths as those baited with virgin female moths, and there was some evidence that addition of 5% of the Z isomer reduced catches.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00163356

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3

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Components of the female sex pheromone of the yellow stem borer, Scirpophaga incertulas (1985)

Cork, Alan ; Beevor, Peter S. ; Hall, David R. ; [et al.]

Springer

Entomologia experimentalis et applicata 37 (1985), S. 149-153

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ISSN: 1570-7458

Keywords: Scirpophaga incertulas ; sex pheromone ; (Z)-9-Hexadecenal ; (Z)-11-Hexadecenal ; (Z)-11-Hexadecen-1-ol

Source: Springer Online Journal Archives 1860-2000

Topics: Biology

Description / Table of Contents: Résumé Des produits provenant du lavage d l'ovipositeur et des substances volatiles de femelles vierges de S. incertulas Walker (Lep.: Pyralidae) ont été examinées en chromatographie en phase gazeuse (GC) avecélectroantennogramme simultané(EAG). Deux réponses EAG ont été enregistrées à des temps de rétention correspondant à ceux des aldéhydes monoinsaturés 16 carbones et des alcools monoinsaturés 16 carbones. L'analyse des produits provenant du lavage de l'ovipositeur en colonnes GC capillaires à haute résolution a donné des pics correspondant aux (Z)-11-hexadécenal, (Z)-9-hexadécenal, (Z)-11-hexadecen-1-ol et à l'hexadecanal. Les réponses EAG de mâles de S. incertulas aux isomères synthétiques d'hexadécenal étaient plus intenses pour les isomères (Z)-11 et (E)-11. Des essais en champ aux Philippines ont montré que les pièges contenant un mélange de (Z)-11-hexadécenal et de (Z)-9-hexadécenal dans le rapport natural 3/ 1 capturaient plus de mâles de S. incertulas que ceux contenant une femelle vierge. L'addition au mélange de (Z)-11-hexadecen-1-ol réduit les captures.

Notes: Abstract Ovipositor washings and volatiles from virgin female Scirpophaga incertulas (Walker) (Lepidoptera: Pyralidae) were analysed by gas chromatography (GC) linked to electroantennography (EAG). Two EAG responses were observed at retention times consistent with those of monounsaturated 16-carbon aldehydes and monounsaturated 16-carbon alcohols. Analysis of ovipositor washings on high-resolution, capillary GC columns showed peaks which cochromatographed with (Z)-11-hexadecenal, (Z)-9-hexadecenal, (Z)-11-hexadecen-1-ol and hexadecanal. EAG responses of male S. incertulas to synthetic hexadecenal isomers were greatest for the (Z)-11 and (Z)-11 isomers. Field tests in the Philippines showed that traps baited with a mixture of (Z)-11-hexadecenal and (Z)-9-hexadecenal in the naturally occurring 3:1 ratio caught significantly more male S. incertulas moths than those baited with a virgin female moth. Addition of (Z)-11-hexadecen-1-ol to this mixture reduced trap catches.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00188203

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4

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Sex pheromones of rice moth,Corcyra cephalonica Stainton (1987)

Zagatti, Pierre ; Kunesch, Gerhard ; Ramiandrasoa, Florence ; [et al.]

Springer

Journal of chemical ecology 13 (1987), S. 1561-1573

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ISSN: 1573-1561

Keywords: Male pheromone ; olfactometer ; identification ; synthesis ; farnesal ; Lepidoptera ; Pyralidae ; Galleriinae ; Corcyra cephalonica ; rice moth ; 3,7,1 1-trimethyl-2,6,10-dodecatrienal

Source: Springer Online Journal Archives 1860-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Abstract Behavioral observations of the rice moth (Corcyra cephalonica, Pyralidae, Galleriinae) in the laboratory have shown that a male wing-gland pheromone induces attraction of female moths. This pheromone was identified as a blend of (E,E) and (Z,E)-farnesal. Wing-gland extracts or synthetic compounds were shown to be attractive to females by inducing walking.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00980200

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Identification and Field Evaluation of Components of Female Sex Pheromone of Millet Stem Borer, Coniesta ignefusalis (1999)

Beevor, Peter S. ; Youm, Ousmane ; Hall, David R. ; [et al.]

Springer

Journal of chemical ecology 25 (1999), S. 2643-2663

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ISSN: 1573-1561

Keywords: Coniesta ignefusalis ; Acigona ignefusalis ; Lepidoptera ; Pyralidae ; sex pheromone ; (Z)-7-dodecen-1-ol ; (Z)-5-decen-1-ol ; (Z)-7-dodecenal ; (Z)-7-dodecenyl acetate ; (Z)-9-tetradecen-1-ol

Source: Springer Online Journal Archives 1860-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Abstract Five active compounds were detected during analyses of ovipositor washings and effluvia from virgin female Coniesta ignefusalis moths by gas chromatography (GC) linked to electroantennographic (EAG) recording from a male moth. These were identified as (Z)-7-dodecen-1-ol (Z7–12:OH), (Z)-5-decen-1-ol (Z5–10:OH), (Z)-7-dodecenal (Z7–12:Ald), (Z)-7-dodecenyl acetate (Z7–12:Ac), and (Z)-9-tetradecen-1-ol (Z9–14:OH) by comparison of their GC retention times, mass spectra, and EAG activities with those of synthetic standards. Laboratory tests of dispensers for these compounds showed that release rates from polyethylene vials increased to relatively uniform values after three to four days, but release from septa was very rapid and nonuniform and decreased to low levels after two to three days. Trapping tests in Niger showed that the major component, Z7–12:OH, and two of the minor components, Z5–10:OH and Z7–12:Ald, were essential for attraction of male C. ignefusalis moths. The most attractive blend contained these three components in a 100:5:3.3 ratio in a polyethylene vial, which emitted the components in similar proportions to those produced by the female C. ignefusalis moth. Water traps baited with this blend containing 1 mg of Z7–12:OH caught more male C. ignefusalis moths than traps baited with newly emerged female moths. Addition of up to 10% of the corresponding E isomers of the pheromone components had no effect on catches, but addition of the other two minor components detected, Z7–12:Ac and/or Z9–14:OH, to the attractive blend at naturally occurring levels caused significant reductions in trap catch.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1023/A:1020839221609

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Pheromone synthesis, CXXVI. Synthesis and biological activity of four stereoisomers of 6,10,14-trimethyl-2-pentadecanol, the female-produced sex pheromone of rice moth (Corcyra cephalonica) (1991)

Mori, Kenji ; Harada, Hironori ; Zagatti, Pierre ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1991 (1991), S. 259-267

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ISSN: 0170-2041

Keywords: Alcohols, branched and chiral ; Grignard coupling ; Pheromones ; Sulfone, alkylation of ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The synthesis of four stereoisomers of the female-produced sex pheromone [(2R,6R,10R)-, (2S,6R,10R)-, (2S,6S,10S)-, and (2R,6S,10S)-1a] of the rice moth (Corcyra cephalonica) was achieved by starting from (R)-2a, (R)- or (S)-3a, and (R)- or (S)-4 and using alkylation of alkyl phenyl sulfones as the coupling reaction. Behavioral bioassay of each isomer revealed (2R,6R,10R)-1a to be eight times more active than a diastereomeric mixture of equal amounts of the eight possible stereoisomers, indicating that (2R,6R,10R)-1a is probably the natural pheromone or at least the major component of the female blend. Electrophysiological bioassay also confirmed the high activity of (2R,6R,10R)-1a.

Additional Material: 2 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199119910144

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Ligand deconstruction: Why some fragment binding positions are conserved and others are not (2015)

Kozakov, Dima ; Hall, David R. ; Jehle, Stefan ; [et al.]

National Academy of Sciences

In: PNAS - Proceedings of the National Academy of Sciences of the United States of America. 2015; 112(20): E2585-E2594. Published 2015 Apr 27. doi: 10.1073/pnas.1501567112.

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Publication Date: 2015-04-27

Description: Fragment-based drug discovery (FBDD) relies on the premise that the fragment binding mode will be conserved on subsequent expansion to a larger ligand. However, no general condition has been established to explain when fragment binding modes will be conserved. We show that a remarkably simple condition can be developed in terms of how fragments coincide with binding energy hot spots—regions of the protein where interactions with a ligand contribute substantial binding free energy—the locations of which can easily be determined computationally. Because a substantial fraction of the free energy of ligand binding comes from interacting with the residues in the energetically most important hot spot, a ligand moiety that sufficiently overlaps with this region will retain its location even when other parts of the ligand are removed. This hypothesis is supported by eight case studies. The condition helps identify whether a protein is suitable for FBDD, predicts the size of fragments required for screening, and determines whether a fragment hit can be extended into a higher affinity ligand. Our results show that ligand binding sites can usefully be thought of in terms of an anchor site, which is the top-ranked hot spot and dominates the free energy of binding, surrounded by a number of weaker satellite sites that confer improved affinity and selectivity for a particular ligand and that it is the intrinsic binding potential of the protein surface that determines whether it can serve as a robust binding site for a suitably optimized ligand.

Print ISSN: 0027-8424

Electronic ISSN: 1091-6490

Topics: Biology , Medicine , Natural Sciences in General

Published by National Academy of Sciences

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Exploring the structural origins of cryptic sites on proteins (2018)

Beglov, Dmitri ; Hall, David R. ; Wakefield, Amanda E. ; [et al.]

National Academy of Sciences

In: PNAS - Proceedings of the National Academy of Sciences of the United States of America. 2018; 115(15): E3416-E3425. Published 2018 Mar 26. doi: 10.1073/pnas.1711490115.

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Publication Date: 2018-03-26

Description: Molecular dynamics (MD) simulations of proteins reveal the existence of many transient surface pockets; however, the factors determining what small subset of these represent druggable or functionally relevant ligand binding sites, called “cryptic sites,” are not understood. Here, we examine multiple X-ray structures for a set of proteins with validated cryptic sites, using the computational hot spot identification tool FTMap. The results show that cryptic sites in ligand-free structures generally have a strong binding energy hot spot very close by. As expected, regions around cryptic sites exhibit above-average flexibility, and close to 50% of the proteins studied here have unbound structures that could accommodate the ligand without clashes. Nevertheless, the strong hot spot neighboring each cryptic site is almost always exploited by the bound ligand, suggesting that binding may frequently involve an induced fit component. We additionally evaluated the structural basis for cryptic site formation, by comparing unbound to bound structures. Cryptic sites are most frequently occluded in the unbound structure by intrusion of loops (22.5%), side chains (19.4%), or in some cases entire helices (5.4%), but motions that create sites that are too open can also eliminate pockets (19.4%). The flexibility of cryptic sites frequently leads to missing side chains or loops (12%) that are particularly evident in low resolution crystal structures. An interesting observation is that cryptic sites formed solely by the movement of side chains, or of backbone segments with fewer than five residues, result only in low affinity binding sites with limited use for drug discovery.

Print ISSN: 0027-8424

Electronic ISSN: 1091-6490

Topics: Biology , Medicine , Natural Sciences in General