Chemical ecology of astigmatid mites

Kuwahara, Yasumasa

doi:10.1017/cbo9780511542664.004

Cited by 56 publications

(59 citation statements)

References 85 publications

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“…The product (3) as an oil (19.1 g, 96z) was obtained in the fraction eluted with a mixture of hexane and ether. 1 a-(4-Methyl-3-pentenyl)-a-methylthio-g-butyrolactone (4). A solution of 3 (8.0 g, 60 mmol) in THF (20 ml) was slowly added to a mixed solution of LDA in heptane W THF W ethyl benzene (2 M, 40 ml) and THF (30 ml) at "789 C while stirring.…”

Section: Methodsmentioning

confidence: 99%

“…After concentration, the crude product was puriˆed in a silica gel column by eluting with a mixture of hexane and ether to give 4 as a colorless oil (7.4 g, 57z). 1 a-(4-Methyl-3-pentenyl)-a-methylsulfonyl-gbutyrolactone (5). A solution of OXONE, (1.4 g, 2.3 mmol) in water (30 ml) was added to a mixture of methanol (15 ml) and 4 (500 mg, 2.3 mmol) at 09 C, and the resulting cloudy slurry was kept for 6 hrs while stirring.…”

Section: Methodsmentioning

confidence: 99%

“…Oily yellowish product 5 (290 mg, 50z) was obtained after concentrating the extract. 1 2-(4-Methyl-3-pentenyl)-2-methylthio-1,4-butanediol (6). To a solution of a-(4-methyl-3-pentenyl)-a-methylthio-g-butyrolactone (4, 1.07 g, 5 mmol) in ether (10 ml), DIBAL (2 ml, 11 mmol) was slowly added at 09 C and the mixture stirred for 1 hr at r.t. After adding satd.…”

Section: Methodsmentioning

confidence: 99%

“…1) The alarm pheromones have been identied in 16 species, the aggregation pheromones in two species, and the sex pheromones in seven species. 1,2) Several compounds also function as anti fungal substances. [3][4][5] In the present study, two monoterpenoids were newly found from the acarid mite Schwiebea araujoae, and from an unidentiˆed Rhizoglyphus sp.…”

Section: -(4-methylmentioning

confidence: 99%

“…Diol 6 was reacted with OXONE to give 2-(4-methyl-3-pentenyl)-2-methylsulfonyl-1,4-butanediol (7, 27z), and subsequent oxidation of 7 with pyridinium dichromate (PDC) gave target compound 2 (30z). 1 H-NMR together with 13 C-NMR of synthetic 1 demonstrated the presence of a prenyl group; two methyls at dH 1.61 (3H, s) and 1.69 (3H, s), a vinyl proton at d H 5.10 (1H, br.qn) and two methylene protons at dH 2.24-2.33 (4H, m), together with a dimethyl-substituted sp 2 carbon at dC 133.9. All the other protons observed were a vinyl at dH 7.15 (1H, qn, J＝1.70 Hz) and an oxygen-substituted methylene at d H 4.77 (2H, q, J＝1.70 Hz).…”

Section: -(4-methylmentioning

confidence: 99%

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3-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,α-Acariolide and 4-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,β-Acariolide:

Tarui¹,

Mori²,

Nishida³

et al. 2002

Bioscience, Biotechnology, and Biochemistry

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A new monoterpene lactone from the acarid mite, Schwiebea araujoae, was elucidated without its isolation by GC/FT-IR and GC/MS analyses to be 3-(4-methyl-3-pentenyl)-2(5H)-furanone (1) and tentatively named as alpha,alpha-acariolide. The structure of 1 was identified by its synthesis from alpha-bromo-gamma-butyrolactone via 4 reaction steps. The synthesized compound gave the same GC/MS and GC/FT-IR spectra as those of the natural product. The other monoterpene lactone was likewise elucidated from the unidentified Rhizoglyphus mite to be 4-(4-methyl-3-pentenyl)-2(5H)-furanone (2) and named as alpha,beta-acariolide; it was also identified by its synthesis in 5 reaction steps from the same butyrolactone as the starting material. GC/MS and GC/FT-IR spectra of the preparation were identical to those of the natural product.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: -(4-methylmentioning

confidence: 99%

Section: -(4-methylmentioning

confidence: 99%

See 3 more Smart Citations

3-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,α-Acariolide and 4-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,β-Acariolide:

Tarui¹,

Mori²,

Nishida³

et al. 2002

Bioscience, Biotechnology, and Biochemistry

Self Cite

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Ultrastructure of the sexually dimorphic basitarsal glands of leg i in manaosbiid harvestmen (opiliones, laniatores)

Proud

Felgenhauer

2011

Journal of Morphology

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Chemical communication is an important aspect of arthropod biology especially for those arthropods with limited abilities to detect visual and acoustic signals. Sexually dimorphic glands are often associated with the production of pheromones, which play a role in reproductive processes. In the family Manaosbiidae (Opiliones: Laniatores), males exhibit an enlarged, swollen, often fused, and spindle-like basitarsus on leg I. In this study, we provide a novel description of the morphology and ultrastructure of the glandular structures found in the proximal swollen tarsomeres of the male manaosbiid Rhopalocranaus albilineatus Roewer, 1932 and compare the external leg I morphology with that of two other manaosbiid harvestmen (Barrona williamsi Goodnight and Goodnight, 1942 and Cranellus montgomeryi Goodnight and Goodnight, 1947). The two proximal tarsomeres of the male R. albilineatus leg I contain two large, paired, acinar glands consisting of many glandular cells. Cells empty their secretory products into a large, branched epicuticular duct, which exits the leg via a pore on the ventral region. Thus, a total of four glandular structures are present within the two swollen tarsomeres and each possesses a conducting canal and pore. Finally, we discuss possible roles of these basitarsal glands in manaosbiid reproductive biology based on the present understanding of sexually dimorphic glands in other terrestrial arthropods (i.e., insects and spiders).

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Oil gland secretions in Oribatida (Acari)

Raspotnig

2010

Trends in Acarology

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Chemical ecology of astigmatid mites

Cited by 56 publications

References 85 publications

3-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,α-Acariolide and 4-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,β-Acariolide:

3-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,α-Acariolide and 4-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,β-Acariolide:

Ultrastructure of the sexually dimorphic basitarsal glands of leg i in manaosbiid harvestmen (opiliones, laniatores)

Oil gland secretions in Oribatida (Acari)

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