3-(4-methyl-3-pentenyl)-2(5H)-furanone, alpha,alpha-acariolide and 4-(4-methyl-3-pentenyl)-2(5H)-furanone, alpha,beta-acariolide: New monoterpene lactones from the astigmatid mites, Schwiebea araujoae and Rhizoglyphus sp. (Astigmata: Acaridae)

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 a,a-acariolide. The structure of 1 was identified by its synthesis from alpha-bromo-g-buty...

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Published inBioscience, biotechnology, and biochemistry Vol. 66; no. 1; pp. 135 - 140
Main Authors Tarui, H. (Kyoto Univ. (Japan)), Mori, N, Nishida, R, Okabe, K, Kuwahara, Y
Format Journal Article
LanguageEnglish
Published Tokyo Japan Society for Bioscience Biotechnology and Agrochemistry 01.01.2002
Subjects
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - analysis
ANALYTICAL METHODS
Animal and plant ecology
Animal, plant and microbial ecology
Animals
Autoecology
Biological and medical sciences
CHEMICAL STRUCTURE
CHEMICAL SYNTHESIS
Fundamental and applied biological sciences. Psychology
Furans - analysis
LACTONES
Lactones - analysis
Mites - chemistry
Molecular Structure
MONOTERPENES
Protozoa. Invertebrata
RHIZOGLYPHUS
Terpenes - analysis
Acaridae
Acariformes
Arachnida
Chemical analysis
Acari
Arthropoda
Interspecific comparison
Acaridida
Lactone
Monoterpene
Invertebrata
Semiochemicals
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Summary: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 a,a-acariolide. The structure of 1 was identified by its synthesis from alpha-bromo-g-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.
Bibliography:2002003866
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ISSN:0916-8451
1347-6947
DOI:10.1271/bbb.66.135