title: (E)-2-(4'-Methyl-3'-pentenylidene)-4-butanolide, Named β-Acariolide: A New Monoterpene Lactone from the Mold Mite, Tyrophagus putrescentiae (Acarina: Acaridae).
abstract: Reinwestigation of the opisthonotal gland secretion of the mold mite, Tyrophagus putrescentiae, resulted in the isolation of a new monoterpene lactone, whose chemical structure was elucidated as (E)-2-(4'-methyl-3'-pentenylidene)-4-butanolide (3), to which we gave the trivial name β-acariolide in relation to β-acaridial {1, (E)-2-(4-methyl-3-pentenylidene)-butanedial}. The compound was synthesized by LiAlH3 (OEt) reduction of 1 and subsequent oxidation involving simultaneous cyclization by using Ag2CO3 on Celite. Both the E- and Z-isomers of β-acariolide (3 and 4) were also prepared by the reaction of α-ethoxaly-γ-butyrolactone (6) and 4-methyl-3-pentenal under basic conditions. Their NMR spectra were compared with each other, and the geometry of the pentenylidene double bond of the isolated compound was concluded as being E.
authors.affiliation: a Institute of Applied Biochemistry , University of Tsukuba, Tsukuba, Ibaraki 305 , Japan.
authors.forename: A
authors.initials: A
authors.lastname: Morino
authors.affiliation: a Institute of Applied Biochemistry , University of Tsukuba, Tsukuba, Ibaraki 305 , Japan.|b Division of Applied Life Sciences, Graduate School of Agriculture , Kyoto University , Sakyo-ku, Kyoto 606-01 , Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Kuwahara
authors.affiliation: a Institute of Applied Biochemistry , University of Tsukuba, Tsukuba, Ibaraki 305 , Japan.
authors.forename: S
authors.initials: S
authors.lastname: Matsuyama
authors.affiliation: a Institute of Applied Biochemistry , University of Tsukuba, Tsukuba, Ibaraki 305 , Japan.
authors.forename: T
authors.initials: T
authors.lastname: Suzuki
keywords: (E)2-(4′-methyl-3′-pentenylidene)-4-butanolide; Tyrophagus putrescentiae; opisthonotal gland; Acaridae; β-acariolide