ChemInform Abstract: Regio‐ and Stereochemical Study of Sex Pheromone of Pine Sawfly; Diprion nipponica.

Tai, Akira; Syouno, Emi; Tanaka, Kazuki; Fujita, Morifumi; Sügimura, Takashi; Higashiura, Yasutomo; Kakizaki, Masashi; Hara, Hideho; Naito, Tikahiko

doi:10.1002/chin.200219236

Cited by 6 publications

(8 citation statements)

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“…The yield of a colorless oil of 99% purity was 141 mg (6%, 98% enantiomeric purity). Spectroscopic data correlated well with literature data (NIST 2002;Tai et al 2002) 7, 39.5, 33.1, 32.6, 30.6, 20.3, 19.8, 14.6 ppm. Total yield from (2R)-methyl-1-pentanol was 4%.…”

Section: Identification Of Compounds Produced By Metasternalsupporting

confidence: 68%

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Behavioral and Electrophysiological Responses of Triatoma brasiliensis Males to Volatiles Produced in the Metasternal Glands of Females

Vitta

Bohman²,

Unelius

et al. 2009

J Chem Ecol

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In many insects, mate finding is mediated by volatile sex pheromones, but evidence for this phenomenon in triatomines (Heteroptera: Reduviidae) is still fragmentary. Recently, it was shown that metasternal glands (MGs) are involved in producing signals related to the sexual communication of Triatoma infestans and Rhodnius prolixus. Based on this, we tested whether MG volatiles could be involved in the sexual communication of Triatoma brasiliensis. Odor-mediated orientation responses were studied by using a T-tube olfactometer. These tests showed that males exhibit positive anemotaxis when confronted with adult odor-laden air currents. Moreover, females that had their metasternal glands occluded did not elicit significant orientation by males. Compounds produced by the MGs of T. brasiliensis females were identified by means of SPME, GC-FID, and GC-MS, with achiral and chiral columns. All substances identified were ketones and alcohols, and similar compound profiles were found in the secretions produced by both sexes. The most abundant compounds identified were 3-pentanone, followed by (4R)-methyl-1-heptanol, 3-pentanol, and (2S)-methyl-1-butanol. In addition, GC-EAD recordings showed that the antennae of males responded to several of the main components of female MG secretions. Our results showed that compounds produced by the MGs of T. brasiliensis females are involved in the sexual communication of this species.

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Section: Identification Of Compounds Produced By Metasternalsupporting

confidence: 68%

“…(4R)-Methyl-1-heptanol This chiral alcohol was synthesized from (2R)-methyl-1-pentanol by malonate ester synthesis (Barth and Effenberger 1993;Hedenström et al 2002;Tai et al 2002).…”

Section: Identification Of Compounds Produced By Metasternalmentioning

confidence: 99%

Behavioral and Electrophysiological Responses of Triatoma brasiliensis Males to Volatiles Produced in the Metasternal Glands of Females

Vitta

Bohman²,

Unelius

et al. 2009

J Chem Ecol

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“…Most of these pheromones have been reported in the Diprionidae and are made up of various methyl branched acetate or propionate products of diprionol (Jewett et al 1976;Ahlgren et al 1979;Anderbrant et al 1992Anderbrant et al , 2000Anderbrant et al , 2005Bergström et al 1995Bergström et al , 1998Chen et al 1997;Tai et al 1998Tai et al , 2002Wassgren et al 2000;Ostrand et al 2003;Hedenström et al 2006). Acantholyda erythrocephala differs from diprionids in that its pheromone, (Z)-6,14-pentadecadienal, and likely pheromone precursor, (Z,Z)-1,9,15-pentacosatriene, are both simple unbranched straight chain hydrocarbons.…”

Section: Discussionmentioning

confidence: 95%

Sex Pheromone of the Pine False Webworm Acantholyda erythrocephala

et al. 2009

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Females of the pine false webworm Acantholyda erythrocephala (L) produce the sex pheromone (Z)-6, 14-pentadecadienal, which attracts flying males in the field. By using gas chromatography coupled with electroantennographic detection (GC-EAD) and mass spectrometry (GC-MS), we detected (Z)-6,14-pentadecadienal in volatile collections and in whole body extracts of female A. erythrocephala. Females, but not males, also exhibited a 25-carbon cuticular hydrocarbon, (Z,Z)-1,9,15-pentacosatriene, which can oxidize to (Z)-6,14-pentadecadienal upon exposure to air and sunlight. (Z,Z)-1,9,15-Pentacosatriene and (Z)-6,14-pentadecadienal identifications were corroborated by comparison with synthetic standards. (Z)-6, 14-Pentadecadienal is the second pheromone identified for pamphilliid sawflies, and the first to elicit strong field attraction, and thus offer potential as a pheromone lure to aid in control of this forest pest.

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“…All diprionid (Hymenoptera: Diprionidae) pheromones reported to date are esters of branched 12-to 17-carbon alcohols, with two to four stereogenic centers (Anderbrant, 1999;Wassgren et al, 2000;Tai et al, 2002;Hedenström et al, 2006Hedenström et al, , 2009. Usually, only one of the four to sixteen possible stereoisomers is attractive to sawflies and, for several species, the presence of other isomers, even in small amounts, counteracts the attraction (for a review of diprionid pheromones, see Anderbrant, 1993Anderbrant, , 1999.…”

Section: Introductionmentioning

confidence: 96%

Field Response of Male Pine Sawflies, Neodiprion sertifer (Diprionidae), to Sex Pheromone Analogs in Japan and Sweden

et al. 2010

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The pine sawfly Neodiprion sertifer (Geoffroy) uses the acetate or propionate of (2S,3S,7S)-3,7-dimethyl-2-pentadecanol (diprionol) as pheromone components, with the (2S,3R,7R)-isomer being antagonistic, synergistic, or inactive according to the population tested. In this study, we tested the attraction of males to the acetates of three analogs of diprionol, each missing one methyl group, viz. (2S,7S)-7-methyl-2-pentadecanol, (2S,6S)-2,6-dimethyl-1-tetradecanol, and (2S,3S)-3-methyl-2-pentadecanol. None of the analogs alone, or in combination with diprionol acetate, was attractive in Sweden, even at 100 times the amount of diprionol acetate attractive to N. sertifer. In Japan, the acetate of (2S,3S)-3-methyl-2-pentadecanol attracted males when tested in amounts 10-20 times higher than the acetate pheromone component. The acetate esters of the (2S,3R)-analog and the (2S,3R,7R)-isomer of diprionol also were tested in combination with the pheromone compound (acetate ester). Both compounds caused an almost total trap-catch reduction in Sweden, whereas in Japan they appear to have relatively little effect on trap capture when added to diprionol acetate. Butyrate and iso-butyrate esters of diprionol were unattractive to N. sertifer in Sweden. In summary, there exists geographic variation in N. sertifer in responses to both diprionyl acetate and some of its analogs.

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ChemInform Abstract: Regio‐ and Stereochemical Study of Sex Pheromone of Pine Sawfly; Diprion nipponica.

Cited by 6 publications

References 1 publication

Behavioral and Electrophysiological Responses of Triatoma brasiliensis Males to Volatiles Produced in the Metasternal Glands of Females

Behavioral and Electrophysiological Responses of Triatoma brasiliensis Males to Volatiles Produced in the Metasternal Glands of Females

Sex Pheromone of the Pine False Webworm Acantholyda erythrocephala

Field Response of Male Pine Sawflies, Neodiprion sertifer (Diprionidae), to Sex Pheromone Analogs in Japan and Sweden

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