Identification of a new lepidopteran sex pheromone in picogram quantities using an antennal biodetector: (8 E,10 Z)-tetradeca-8,10-dienal from Cameraria ohridella (original) (raw)
Related papers
Journal of Chemical Ecology, 2003
Gas chromatography combined with electroantennographic detection (GC-EAD), electroantennography (EAG), and wind-tunnel and field experiments were used to reinvestigate the composition of Cameraria ohridella (Lepidoptera, Gracillariidae, Lithocolletinae) sex pheromone. The GC-EAD experiments showed one EAD-active area corresponding to the major pheromone component, (8E,10Z)-tetradeca-8,10-dienal. The EAG experiments proved that (9E)-tetracedecenal and stereoisomers of (8E,10Z)-tetradeca-8,10-dienal exhibited significant electrophysiological activity and could, therefore, be considered as possible minor pheromone components. However, wind-tunnel and field experiments demonstrated that none of these compounds affect the efficacy of the main pheromone component. A monitoring system based on (8E,10Z)-tetradeca-8,10-dienal was developed and used to study the flight activity of C. ohridella.
Zeitschrift für Naturforschung. C, Journal of biosciences
Mass spectrometric investigations confirmed the structure of the female produced sex pheromone of the horse-chestnut leafminer Cameraria ohridella Desch. and Dim. to be (8E,IOZ)-8,10-tetradecadienal. Pure samples, prepared in a straightforward synthesis, were highly attractive in field tests and proved to be suitable for monitoring of flight activities and population dynamics. In mixtures with the synthetic pheromone, analogues like 9-tridecynal and 7-dodecynyl formate were shown to reduce trap catches. In electroantennographic experiments, pheromone analogues were less active than the pheromone. 9-Tridecynal was the most EAG active analogue tested, followed by 7-dodecyn-1-yl formate and 7-undecyn-1-yl formate.
Talanta, 2000
In this paper we present analytical studies of the sex pheromone components of the Egyptian armyworm Spodoptera littoralis (Lepidoptera, Noctuidae) by electroantennography (EAG) and coupled gas chromatographyelectroantennographic detection (GC-EAD). EAG responses in three different preparations, using an insect's head, an excised antenna and a live insect, have been recorded. EAG depolarizations of live insects were significantly higher than those elicited by the insect's head or the excised antenna. The responses were dose-dependent. Live insects also allowed regular pheromone stimulations for 40 min with only 38% decrease of the EAG initial depolarization. The synthetic pheromone blend elicited the highest EAG activity (2.0 9 0.3 mV), followed by the major compound (Z,E)-9,11-tetradecadienyl acetate (I) (1.54 90.1mV), and the minor components (Z)-9-tetradecenyl acetate (II), (E)-11-tetradecenyl acetate (III), tetradecyl acetate (IV) and (Z)-11-tetradecenyl acetate (V) (1.21-1.32 mV range). (Z,E)-9,12-tetradecadienyl acetate (VI), although not present in the pheromone blend of our strain, also showed an EAG activity (1.32 90.09 mV) similar to that of the monoenic components. GC-EAD responses confirmed the composition of the sex pheromone blend, the major response being elicited by the main component I followed by the other minor compounds II-V. The new dienic compound found in the female pheromone gland, (E,E)-10,12-tetradecadienyl acetate (VII), was not electrophysiologically active. Regarding sensitivity, the minimum amount detectable to elicit an antennal response in our GC-EAD system was 15 pg of the major component. In our system, which was built with cheap and easily available materials, no cooling of the effluent at the outlet of the chromatographic column is required.
The major component of sex attractant released by the virgin female of the horse-chestnut leafminer Cameraria ohridella Deschka et Dimič (Lepidoptera: Gracillariidae), which devastates horse chestnut trees in Europe, was identified in picogram quantities as (8E,10Z)-tetradeca-8,10-dien- al. The spectral methods were not used, the identification relied entirely on alternative analytical methods like 1) gas chromatography with electroantennographic detection (GC-EAD), 2) calculation of Kovats' indices of the active principle on different GC phases, and 3) construction of EAG response profiles to C12 and C14 saturated and unsaturated standards with different functional groups. The synthetic pheromone was prepared by a stereospecific synthesis and shown to be highly active for conspecific males and was proved to be fully comparable to the natural substance in all respects. The potential use of the pheromone to protect horse chestnut trees in Europe is discussed.
Pheromones in lepidopteran insects: Types, production, reception and its application
Journal of Pharmacognosy and Phytochemistry, 2017
The to semiochemicals that are released by one member of a species and evoke a specific reaction or reactions from members of the same species. Pheromones are known for both the specificity and the potency of their actions. Lepidopteran pheromones were the first to be widely studied and include a huge collection of mostly female based pheromones. Female typically produce long range, fatty acid derived molecules that function over long distances, where as male tend to produce close-range courtship compounds that are often very similar in structure to plant secondary metabolites. After knowing the nature of pheinsect’s universe is filled with many odours. One of these odours is called pheromone, a term commonly applied romones and their potential for pest control along with the future prospective of pheromone technique in agriculture in India, it is highly recommended to enhance availability of pheromone in market, invest more in research and development and introduce newly identified...
Journal of Chemical Ecology, 1979
Analysis of sex pheromone glands of the apple leafroller Bonagota cranaodes Meyrick by gas chromatography coupled with mass spectrometry or electroantennographic detection showed the presence of 14 structurally related acetates and alcohols of the chain length 10 Ð18, including the main pheromone component (E,Z)-3,5-dodecadienyl acetate (E3,Z5Ð12Ac). Male antennae responded to the main compound, its Z,Z isomer, (E,Z)-3,5-tetradecadienyl acetate (E3,Z5Ð14Ac), and the monoenes (Z)-5-dodecenyl acetate (Z5Ð12Ac) and (Z)-9-hexadecenyl acetate (Z9 Ð16Ac). Traps baited with a four-component blend of E3,Z5Ð12Ac, Z5Ð12Ac, E3,Z5Ð14Ac, and Z9 Ð16Ac in a 100:5:5:100 ratio were signiÞcantly more attractive than the main compound alone. This improved trap lure is more suitable for monitoring population densities of B. cranaodes, and for detection of the onset of the seasonal ßight period. A more complete pheromone blend is of importance also with respect to current attempts to develop mating disruption for control of this major pest of apple in Brazil.
Collection of Czechoslovak Chemical Communications, 2000
(8E,10Z)-Tetradeca-8,10-dienal (1a), sex pheromone of the horse chestnut leafminer (Cameraria ohridella; Lepidoptera, Gracillariidae), and its geometrical isomers (1b-1d) were efficiently synthesized using tetrakis(triphenylphosphine)palladium catalyzed cross-coupling reactions of alk-1-ynes or alkenyl alanes with corresponding vinyl iodides. The stereoisomeric purity of obtained tetradecadienals 1a-1d was higher than 95% (GC). Relative electroantennographic (EAG) activities of the prepared compounds 1a-1d elicited on male antennae supported the previously published identification of the C. ohridella sex pheromone.
Journal of Agricultural and Food Chemistry, 2012
The medfly( Ceratitis capitata) is one of the major agricultural pests controlled through sterile insect technique (SIT) programs. We studied the chemical composition of the volatiles released by calling males from one laboratory and two wild C. capitata populations using two-dimensional gas chromatography with time-of-flight mass spectrometric detection (GC × GC/ TOFMS) and gas chromatography with electroantennographic detection (GC-EAD). Multivariate data analyses revealed significant differences in the quantitative and qualitative composition of male chemical emanations between the three populations. The GC-EAD analyses of the male emanation of three C. capitata populations revealed 14 antenally active compounds. The volatiles isomenthone, β-pinene, ethyl octanoate, indole, geraniol, bornyl acetate, geranyl acetone, and (E)caryophyllene are newly reported EAD active constituents of the male pheromone. GC-EAD analyses of the laboratory population indicated that the males and females of C. capitata possess comparable sensitivity to male-produced volatiles. Our results are relevant to the development of a pheromone-based monitoring system and also to the SIT control program.
European Journal of Entomology, 2016
The possibility of interfering with chemical communication in insects using pheromone analogs is an interesting approach with potential use in pest management programs (Prestwich, 1987; Renou & Guerrero, 2000; Plettner, 2002). Among the structural analogs, methyl ketones (MKs) and, particularly, trifl uoromethyl ketones (TFMKs), in which the acetate group has been replaced by CH 3 CO or CF 3 CO, respectively, are good disruptants of pheromone perception in a number of lepidopteran species, such as Spodo ptera littoralis Boisduval (