Chemical ecology of astigmatid mites.

Kuwahara, Yasumasa

doi:10.1271/nogeikagaku1924.64.1754

Cited by 21 publications

(50 citation statements)

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“…S5). Collectively, the current data are consistent with the 13 C atom derived from [1][2][3][4][5][6][7][8][9][10][11][12][13] C] stearic acid as selectively present in the formyl moiety and not significantly incorporated into other carbon positions.…”

supporting

confidence: 86%

“…4). Given the rather surprising and strong [1][2][3][4][5][6][7][8][9][10][11][12][13] C enrichment measured, we present these findings as evidence that 8,11-F17 is biosynthesized without going through the process of dehomologation, which-if predominant-would oppositely remove the 1-13 C label present. We propose that this process similarly occurs for 8-F17, although we do present any parallel GC/EI-MS evidence for this example because of suboptimal ionization parameters.…”

Section: Discussionmentioning

confidence: 76%

“…One of the most widely distributed saturated hydrocarbons in the Astigmata is tridecane. With respect to unsaturated hydrocarbons, (Z)-8-heptadecene (8-C17) is widely distributed in Acaridae and Histiostomatidae, and (Z, Z)-6,9-heptadecadiene (6,9-C17) in Acaridae (2). As rarely detected chemicals in nature, 8-C17 serves as a sex pheromone in European house dust mites (Dermatophagoides pteronyssinus) (3), and similarly 6,9-C17 functions as an alarm pheromone in Tortonia sp., which attacks the nests of megachilid bees (Osmia cornifons) (4).…”

mentioning

confidence: 99%

“…Mechanisms for lipid metabolism associated with mite secretory components have been gradually clarified (5-7). After being reported as an alarm pheromone of the mold mite (Tyrophagus putrescentiae) in 1975 (8), neryl formate [(Z)-3,7-dimethyl-2,6-octadienyl formate] has been subsequently identified as an alarm pheromone in several species of acaridae (2). Lardolure [(1R,3R,5R,7R)-1,3,5,7-tetramethyldecyl formate] has been identified as an aggregation pheromone in Lardoglyphus konoi (9,10), and also shows induced activation in C. lactis, Aleuroglyphus ovatus, and T. putrescentiae (11).…”

mentioning

confidence: 99%

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Biosynthetic pathway of aliphatic formates via a Baeyer–Villiger oxidation in mechanism present in astigmatid mites

Shimizu

Sakata

Schmelz

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

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Astigmatid mites depend on bioactive glandular secretions, pheromones, and defensive agents to mediate intra- and interspecies interactions. Aliphatic formates, such as (Z,Z)-8,11-heptadecadienyl formate (8,11-F17) and (Z)-8-heptadecenyl formate (8-F17), are rarely encountered natural products that are abundant inSancassaniasp. Sasagawa (Acari: Acaridae) mite secretions. Linoleic acid and oleic acid are predicted as key intermediates in the synthesis of the closely related aliphatic formates. To gain insight in this biosynthetic pathway, acarid mite feeding experiments were conducted using13C-labeled precursors to precisely track incorporation. Analyses using13C NMR spectroscopy demonstrated that the13C-labeling pattern of the precursors was detectable on formates in exocrine secretions and likewise on fatty acids in total lipid pools. Curiously, the results demonstrated that the formates were biosynthesized without the dehomologation of corresponding fatty acids. Careful examination of the mass spectra from labeling experiments revealed that the carbonyl carbon of the formates is originally derived from the C-1 position of the fatty acids. Consistent with a Baeyer–Villiger oxidation reaction, labeling studies support the insertion of an oxygen atom between the carbonyl group and carbon chain. Empirical data support the existence of a Baeyer–Villiger monooxygenase responsible for the catalyzation of the Baeyer–Villiger oxidation. The predicted existence of a Baeyer–Villiger monooxygenase capable of converting aliphatic aldehydes to formates represents an exciting opportunity to expand the enzymatic toolbox available for controlled biochemical synthesis.

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confidence: 86%

Section: Discussionmentioning

confidence: 76%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Biosynthetic pathway of aliphatic formates via a Baeyer–Villiger oxidation in mechanism present in astigmatid mites

Shimizu

Sakata

Schmelz

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

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“…Neral is one of the most widely distributed components among astigmatid mites, and has been detected in 31 species among the 52 species investigated (Kuwahara, 1999). Five species use the compound as their alarm pheromone: Carpoglyphus lactis, Lardoglyphus konoi (Kuwahara et al, 1980b), Suidasia medanensis (Leal et al, 1989d), Glycyphagus domesticus (Kuwahara et al, 1991), Schwiebea elongata .…”

Section: Discussionmentioning

confidence: 99%

Chemical Ecology of Astigmatid Mites LXVII. Neral [3,7-dimethyl-(Z)-2,6-octadienal]: The Female Sex Pheromone of an Acarid mite, Histiogaster sp. (Acari: Acaridae).

弘之¹,

直樹²,

貴美子³

et al. 2002

J. Acarol. Soc. Jpn.

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Neral [3,7-dimethyl-(Z)-2,6-octadienal] was identified to be the female sex pheromone of the mite Histiogaster sp. (Acari: Acaridae). The species originated from a fungal Trichoderma harzianum culture in Japan. The compound aroused males to mount females. Although the compound was detected in both sexes (29.4±8.9 ng in females and 5.7±1.9 ng in males), the behavior observation suggested that males could distinguish females from males. Synthetic neral indicated the activity at 0.1-1 ng doses. On the other hand, geranial [3,7-dimethyl-(E)-2,6-octadienal, the geometrical isomer of neral at the 2-C position], did not sexually stimulate males. Males could, therefore, discriminate between neral and geranial. Escaping behavior was observed upon exposure of neral at 100 ng and of geranial at 10-100 ng doses.

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Identification of astigmatid mites using the second internal transcribed spacer (ITS2) region and its application for phylogenetic study

et al. 2005

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The second internal transcribed spacer (ITS2) of nuclear ribosomal DNA from 73 specimens of Astigmata was analyzed by PCR amplification and DNA sequencing. The length of the ITS2 region varied from 282 to 592 bp. The interspecific variation based on consensus sequences was more than 4.1%, while the intraspecific or intra-individual variation was from 0 to 5.7%. The variation between geographically separated populations (0-3.2%) was almost the same as the variation within strains. The sequences of the ITS2 region of Astigmata were concluded to be species-specific. The phylogenetic tree inferred from the ITS2 region supported Zachvatkin's morphological classification in the subfamily Rhizoglyphinae. The species-specific ITS2 sequence is useful for the species identification of astigmatid mites and for studying low-level phylogenetic relationships.

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Chemical ecology of astigmatid mites.

Cited by 21 publications

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Biosynthetic pathway of aliphatic formates via a Baeyer–Villiger oxidation in mechanism present in astigmatid mites

Biosynthetic pathway of aliphatic formates via a Baeyer–Villiger oxidation in mechanism present in astigmatid mites

Chemical Ecology of Astigmatid Mites LXVII. Neral [3,7-dimethyl-(Z)-2,6-octadienal]: The Female Sex Pheromone of an Acarid mite, Histiogaster sp. (Acari: Acaridae).

Identification of astigmatid mites using the second internal transcribed spacer (ITS2) region and its application for phylogenetic study

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