Chemical ecology of astigmatid mites. LVIII. 2-Hydroxy-6-methylbenzaldehyde: Female sex pheromone of Cosmoglyphus hughesi Samsinak(Acari: Acaridae).

Ryono, Atsushi; Mori, Naoki; Okabe, Kimiko; Kuwahara, Yasumasa

doi:10.1303/aez.2001.77

Cited by 15 publications

(12 citation statements)

References 16 publications

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“…Other than S-isorobinal, the following compounds have been identified as sex pheromones from nine species other than the present study; 2-hydroxy-6-methylbenzaldehyde (HMB) in Acarus immobilis Griffiths (Sato et al 1993), in Cosmoglyphus hughesi Samsˇinˇa´k (Ryono et al 2001), in Aleuroglyphus ovatus Troupeau (Kuwahara et al 1992a) and in Dermatophagoides farinae Hughes (Tatami et al 2001), undecane in C. rodriguezi Samsˇinˇa´k (Mori et al 1995), (2R,3R)-epoxyneral in Caloglyphus sp. MJ (Mori et al 1996), rosefuran in Caloglyphus sp.…”

Section: Discussionmentioning

confidence: 59%

S-isorobinal as the female sex pheromone from an alarm pheromone emitting mite, Rhizoglyphus setosus

et al. 2005

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The female sex pheromone of Rhizoglyphus setosus Manson (Astigmata: Acaridae) was identified as S-isorobinal (4S-4-isopropenyl-3-oxo-1-cyclohexene-1-carboxyaldehyde), which stimulated males sexually and enhanced the frequency of the male's tapping and mounting behavior. Although the female hexane extract indicated no sign of sex pheromone activity against tested males, possibly due to the presence of the alarm pheromone neryl formate, an SiO2 column fraction containing isorobinal elicited sex pheromone activity at a dose of one female equivalent. The stereochemistry of natural isorobinal was identified as S by an HPLC using a chiral column. Both S- and R-isorobinals exhibited maximum activity at the same dose of 1 and 10 ng with a convex dose-response relationship. Amounts of S-isorobinal were determined to be 11.7 +/- 1.0 ng per female and 6.4 +/- 1.3 ng per male by GLC. This is the second example of two pheromones (the alarm pheromone neryl formate, and the sex pheromone S-isorobinal) demonstrated to be components of the same opisthonotal gland secretion.

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Section: Discussionmentioning

confidence: 59%

S-isorobinal as the female sex pheromone from an alarm pheromone emitting mite, Rhizoglyphus setosus

et al. 2005

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“…Neral also serves as a sex pheromone in some other Astigmata (Hiraoka et al 2002). The aromatic compound 2,6-HMBD-in C. gigantea showing strong alarm pheromonal activity-possesses either alarm pheromonal or sex pheromonal properties in certain astigmatid mite species (Leal et al 1988;Kuwahara et al 1992;Sato et al 1993;Ryono et al 2001). Since these ''astigmatid compounds'' are widespread in Oribatida, we should expect to frequently find semiochemical roles of oil glands in the latter group as well.…”

Section: Chemoreceptionmentioning

confidence: 99%

Chemical alarm and defence in the oribatid mite Collohmannia gigantea (Acari: Oribatida)

Raspotnig

2006

Exp Appl Acarol

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The multicomponent oil gland secretion of Collohmannia gigantea, a middle-derivative mixonomatan oribatid mite, is demonstrated to possess alarm pheromonal and allomonal properties. Four components of the secretion, namely the monoterpenes neryl formate, neral, geranial and the aromatic 2-hydroxy- 6-methyl-benzaldehyde (2,6-HMBD), showed moderate to strong alarm pheromonal activity in adult mites. Naturally elicited response is due to neral (about 50% of the secretion) and probably 2,6-HMBD (only 5% of the secretion, but strong alarm pheromonal activity). This is the second report of an alarm pheromone in Oribatida. Tridecane and pentadecane (=the hydrocarbon fraction of the secretion) did not evoke evident behavioural reactions, and most likely serve as solvents and spreading agents for the pheromonal-active components. Alarm reactions were characterized by a short recognition phase (waving movements with legs I), followed by shrinking back and panic escape from the scent source. In addition, all six components of the oil gland secretion, including the hydrocarbons, exhibited strong allomonal properties against a model oribatid predator, the scydmaenid beetle, Euconnus (Tetramelus) oblongus. Considering the widespread semiochemical properties of oil gland secretions in astigmatid mites (=a highly derivative oribatid group), these results furnish evidence for a phylogenetically early origin of defensive and communicative roles of oil gland secretions in oribatids. These roles include alarm communication, defence and the production of anti-fungal compounds.

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“…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%

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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Chemical ecology of astigmatid mites. LVIII. 2-Hydroxy-6-methylbenzaldehyde: Female sex pheromone of Cosmoglyphus hughesi Samsinak(Acari: Acaridae).

Cited by 15 publications

References 16 publications

S-isorobinal as the female sex pheromone from an alarm pheromone emitting mite, Rhizoglyphus setosus

S-isorobinal as the female sex pheromone from an alarm pheromone emitting mite, Rhizoglyphus setosus

Chemical alarm and defence in the oribatid mite Collohmannia gigantea (Acari: Oribatida)

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

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