Females of the Bumblebee Parasite, Aphomia sociella, Excite Males Using a Courtship Pheromone

Kindl, Jiří; Jiroš, Pavel; Kalinová, Blanka; Žáček, Petr; Valterová, Irena

doi:10.1007/s10886-012-0100-3

Cited by 8 publications

(8 citation statements)

References 32 publications

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“…GC×GC/TOFMS has been widely used for the analysis of volatile organic compounds (VOCs), especially insect pheromones. , Because calling adults were emitted and produced in quite low quantitation, some compounds were not detected through gas chromatography–mass spectrometry (GC-MS); , therefore, GC×GC/TOFMS was superior to 1D GC and was shown to be a superior analytical technique, especially for the separation of compounds and detection sensitivity, etc. , …”

Section: Results and Discussionmentioning

confidence: 99%

Analysis of Tea Geometrid (Ectropis grisescens) Pheromone Gland Extracts Using GC-EAD and GC×GC/TOFMS

Xiao

et al. 2016

J. Agric. Food Chem.

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The tea geometrid, Ectropis grisescens Warren, is one of the most severe defoliator insect pests in tea plantations, China. The use of insecticides, etc., is forbidden on organic tea plantations. No female-produced sex pheromones of E. grisescens had been previously identified. In the present study, female gland extracts were analyzed by gas chromatography coupled with electroantennographic detection (GC-EAD) and two-dimensional gas chromatography (GC×GC) using a time-of-flight mass spectrometric detector (TOFMS). Two components, (Z,Z,Z)-3,6,9-octadecatriene (Z3Z6Z9-18:Hy) and (Z,Z)-3,9-6,7-epoxyoctadecadiene (Z3Z9-6,7-epo-18:Hy), were identified from pheromone gland extracts, and their electrophysiological and behavioral activity evaluated. Under laboratory conditions, Z3Z9-6,7-epo-18:Hy elicited a stronger electrophysiological response than Z3Z6Z9-18:Hy. In the field, traps baited with Z3Z9-6,7-epo-18:Hy alone showed better results than traps baited with Z3Z6Z9-18:Hy, and the binary mixture of Z3Z9-6,7-epo-18:Hy and Z3Z6Z9-18:Hy in a ratio of 4:1 (approximate ratio of females emitting pheromone) caught more males than the single components or any other blends. This study showed that Z3Z6Z9-18:Hy and Z3Z9-6,7-epo-18:Hy are the sex pheromone components of E. grisescens and that they prove useful in developing alternative management tools for the pest.

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Section: Results and Discussionmentioning

confidence: 99%

Analysis of Tea Geometrid (Ectropis grisescens) Pheromone Gland Extracts Using GC-EAD and GC×GC/TOFMS

Xiao

et al. 2016

J. Agric. Food Chem.

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“…Synthesis of (Z)-9-hydroxy-6-nonenoic acid(18)Identification of compounds D and E. Compounds D and E were readily identified as 6,10,14trimethylpentadecan-2-ol (D, 37), a known pheromone compound present in various Lepidoptera, including butterflies(Nesbitt et al 1986;Nieberding et al 2008;Kindl et al 2012;Hedenström et al 2014), and 2-heptadecanol (E, 39).Identification of compounds F and G.A group of compounds (F, G) eluted much later and were characterized by a poor peak shape(Figure 3a), indicating a functional group such as an alcohol, acid, or both. Their mass spectra combined spectral features of fatty acids and compounds B and C. Methylation transformed these compounds into methyl esters, showing their high content in the extract (Figure 3b).…”

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confidence: 99%

Chemistry of the Androconial Secretion of the Ithomiine Butterfly Oleria onega

et al. 2019

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“…Similar problems occurred during the purification of the female extract where TMPD-ol dominates over TMPD-one. Since the source of female pheromone is not known 3 , extract of whole female bodies was used. Purification of TMPD-one and TMPD-ol from the females was more difficult due to a higher contamination resulting from body extraction compared to gland extraction in males.…”

Section: Resultsmentioning

confidence: 99%

“…preparation of reference compounds. (2R/S,6R/S,10R/S)-6,10,14-Trimethylpentadecan-2-ol (2E,7 R/S,11 R/S)- (3,7,11,15)-Tetramethyl-2-hexadecen-1-ol ((2E,7R/S,11R/S)-phytol) (SigmaAldrich) was oxidized at room temperature by sodium periodate and catalytic amount of ruthenium (III) chloride ( Fig. 1A), the obtained ketone was reduced with LiAlH 4 in diethyl ether resulting in a mixture of eight isomers of TMPD-ol ( Fig.…”

Section: Stereochemical Analysismentioning

confidence: 99%

Stereochemistry of two pheromonal components of the bumblebee wax moth, Aphomia sociella

Wallin

Kalinová

Kindl

et al. 2020

Sci Rep

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the bumblebee wax moth, Aphomia sociella, is a parasite of bumblebees. in this species, males produce sexual pheromone to attract females, while females produce an aphrodisiac pheromone that initiates male courtship. Both pheromones contain 6,10,14-trimethylpentadecan-2-one (TMPD-one) and the corresponding alcohol, 6,10,14-trimethylpentadecan-2-ol (TMPD-ol) in sex specific quantities. Male sex pheromone consists of 7 components with TMPD-one as a minor one and traces of TMPD-ol. In female aphrodisiac pheromone, TMPD-ol is the major component, while TMPD-one is present in traces. Here we report on the absolute configuration of TMPD-one in male sex pheromone and TMPD-ol in female aphrodisiac pheromone of A. sociella. The configuration was determined from GC/MS of prepared (S)-acetoxypropionyl esters of TMPD-ol. TMPD-one was first reduced to the alcohol that was then derivatized with (S)-acetoxypropionyl chloride. The GC/MS data of obtained diastereoisomers were compared with synthetic standards. The absolute configuration of TMPD-one in the male pheromone was (6R,10R). The configuration of TMPD-ol in the female pheromone was (2R,6R,10R). Electrophysiological experiments showed that TMPD-one and TMPD-ol are perceived by both sexes. the synthetic standards of naturally produced stereoisomers elicited higher responses than mixtures of all stereoisomers. The stereochemistry plays an important role in the pheromone communication 1. Therefore, it is of great importance to determine the stereoisomeric composition of pheromonal components. Aphomia sociella L. (Pyralidae, Galleriinae) is a parasite of bumblebees. Unlike most Lepidoptera, the reproductive behavior of A. sociella is initiated by males and except chemical communication (sex pheromone) it includes also an ultrasonic part. The male sex pheromone attracts females from a distance, while ultrasonic signaling urges females to accept mating 2. Females produce aphrodisiac pheromone, which initiates male courtship behavior 3. Male pheromone is a multicomponent blend consisting of (Z)-nona-2,6-dien-4-olide and mellein as major components, and 1-hexanol, 2-phenylethanol, (Z)-nona-6-en-4-olide, and 6,10,14-trimethylpentadecan-2-one (TMPD-one, trivial names phytone or hexahydrofarnesylacetone) as minor components 4,5. In female aphrodisiac pheromone, 6,10,14-tri methylpentadecan-2-ol (TMPD-ol) represents the major component with TMPD-one and hexan-1-ol as minor ones 3. TMPD-one has been found earlier within male sex pheromone of other Galleriinae, such as Galleria mellonella 6 and Tirathaba mundella 7. TMPD-ol plays a role in the communication of another species of this family, Corcyra cephalonica, where females utilize TMPD-ol for attracting males 8. Both TMPD-one and TMPD-ol are chiral compounds, but in none Galleriinae species, the absolute configuration has been reported. The stereochemistry of these two compounds was determined in other insects beside Galleriinae. TMPD-ol in Bicyclus butterflies has been determined after (S)-2-acetoxypropionyl derivatization and the f...

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Females of the Bumblebee Parasite, Aphomia sociella, Excite Males Using a Courtship Pheromone

Cited by 8 publications

References 32 publications

Analysis of Tea Geometrid (Ectropis grisescens) Pheromone Gland Extracts Using GC-EAD and GC×GC/TOFMS

Analysis of Tea Geometrid (Ectropis grisescens) Pheromone Gland Extracts Using GC-EAD and GC×GC/TOFMS

Chemistry of the Androconial Secretion of the Ithomiine Butterfly Oleria onega

Stereochemistry of two pheromonal components of the bumblebee wax moth, Aphomia sociella

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