Stereochemistry of Female-Specific Normonoterpenes, Sex Pheromone Candidates from the Acarid Mite,<i>Tyreophagus</i>sp. (Astigmata: Acaridae)

Shimizu, Nobuhiro; Miwa, Kuniaki; Noge, Koji; Yakumaru, Ryota; Mori, Naoki; Kuwahara, Yasumasa

doi:10.1271/bbb.90364

Cited by 3 publications

(3 citation statements)

References 15 publications

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“…The enantioselective biosynthesis of pheromones appears to be significant for the behavior and specific discrimination of insects. 19,20) Thus, despite the analysis of DHS extract of male C. psidii was not performed in the chiral column, the presence of enantiomeric pure papayanal is reinforced by biogenetic reasons. In two other Curculionidae species, papaya weevil (Pseudopiazurus obesus), 21) and banded pine weevil (Pissodes castaneus), 22) the mixture of (1R,2S)-(+)-grandisal and (1R,2S)-(+)-grandisol, aldehyde and alcohol, were identified as aggregation pheromones.…”

Section: Discussionmentioning

confidence: 99%

(1R,2S,6R)-Papayanal: a new male-specific volatile compound released by the guava weevilConotrachelus psidii(Coleoptera: Curculionidae)

Romero-Frías

Murata²,

Bento

et al. 2016

Bioscience, Biotechnology, and Biochemistry

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The guava weevil, Conotrachelus psidii is an aggressive pest of guava (Psidium guajava L.) that causes irreparable damages inside the fruit. The volatile compounds of male and female insects were separately collected by headspace solid-phase microextraction or with dynamic headspace collection on a polymer sorbent, and comparatively analyzed by GC-MS. (1R,2S,6R)-2-Hydroxymethyl-2,6-dimethyl-3-oxabicyclo[4.2.0]octane (papayanol), and (1R,2S,6R)-2,6-dimethyl-3-oxabicyclo[4.2.0]octane-2-carbaldehyde (papayanal) were identified (ratio of 9:1, respectively) as male-specific guava weevil volatiles. Papayanal structure was confirmed by comparison of spectroscopic (EIMS) and chromatographic (retention time) data with those of the synthetic pure compound. The behavioral response of the above-mentioned compounds was studied in a Y-tube olfactometer bioassay, and their role as aggregation pheromone candidate components was suggested in this species.

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Section: Discussionmentioning

confidence: 99%

(1R,2S,6R)-Papayanal: a new male-specific volatile compound released by the guava weevilConotrachelus psidii(Coleoptera: Curculionidae)

Romero-Frías

Murata²,

Bento

et al. 2016

Bioscience, Biotechnology, and Biochemistry

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“…Table 5 shows methyl-branched carboxylic acids and their structure-related compounds (82)(83)(84)(85)(86)(87)(88)(89)(90)(91)(92)(93)(94)(95)(96)(97)(98) that act as insect pheromones. Carboxylic acids and their ester derivatives with one, two, or three methyl branch(es) in a C 5 -C 15 main chain have been identied from insects, mainly in Coleoptera.…”

Section: Carboxylic Acids and Their Derivativesmentioning

confidence: 99%

“…Aer the methylation of 3,5-heptadedione, the (4S,5R)-and (4S,5R)-isomers of sitophinone (67) were synthesized by reductions utilizing KRED-A1C and KRED-119, respectively, in the presence of a glucose/glucose hydrogenase system for NADPH recycling (R-5-3). 205 For the syntheses of sitophilate (82), stegobinone (103), and stegobiol (104), the 2S,3R conguration was formed by the reduction of methyl 2-methyl-3-oxopentanoate with KRED-A1B and B1E. 250,306 On the other hand, its enantioselective fungal reduction with a strain of Aureobasidium pullulans formed the (2S,3S)-isomer.…”

Section: Application Of Stereoselective Reactionsmentioning

confidence: 99%

Chiral methyl-branched pheromones

Ando

Yamakawa

2015

Nat. Prod. Rep.

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Insect pheromones are some of the most interesting natural products because they are utilized for interspecific communication between various insects, such as beetles, moths, ants, and cockroaches. A large number of compounds of many kinds have been identified as pheromone components, reflecting the diversity of insect species. While this review deals only with chiral methyl-branched pheromones, the chemical structures of more than one hundred non-terpene compounds have been determined by applying excellent analytical techniques. Furthermore, their stereoselective syntheses have been achieved by employing trustworthy chiral sources and ingenious enantioselective reactions. The information has been reviewed here not only to make them available for new research but also to understand the characteristic chemical structures of the chiral pheromones. Since biosynthetic studies are still limited, it might be meaningful to examine whether the structures, particularly the positions and configurations of the branched methyl groups, are correlated with the taxonomy of the pheromone producers and also with the function of the pheromones in communication systems.

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Male-Produced Aggregation Pheromone of Coffee Bean Weevil, Araecerus fasciculatus

et al. 2017

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The coffee bean weevil (CBW), Araecerus fasciculatus (De Geer, 1775), is a cosmopolitan stored-product pest, especially in tropical and subtropical areas. Previous reports showed evidence for aggregation behavior of CBW and this study aimed to identify and evaluate the aggregation pheromone of this pest. Whole-body solvent extractions were analyzed by coupled gas chromatography-mass spectrometry and comparison of male and female extracts showed a male-specific compound which was identified as squalene, 2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene. This compound was shown to attract male and female CBW in Y-tube olfactometer and storage trap assays. The longevity of septum lures was also evaluated in a warehouse. Squalene could be useful in monitoring and controlling this pest.

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Stereochemistry of Female-Specific Normonoterpenes, Sex Pheromone Candidates from the Acarid Mite,Tyreophagussp. (Astigmata: Acaridae)

Cited by 3 publications

References 15 publications

(1R,2S,6R)-Papayanal: a new male-specific volatile compound released by the guava weevilConotrachelus psidii(Coleoptera: Curculionidae)

(1R,2S,6R)-Papayanal: a new male-specific volatile compound released by the guava weevilConotrachelus psidii(Coleoptera: Curculionidae)

Chiral methyl-branched pheromones

Male-Produced Aggregation Pheromone of Coffee Bean Weevil, Araecerus fasciculatus

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