夹竹桃蚧的性信息素：一种不寻常的官能化环丁烷的结构表征及绝对构型
Sex pheromone of the oleander scale, Aspidiotus nerii: structural characterization and absolute configuration of an unusual functionalized cyclobutane.
作者信息
Einhorn J, Guerrero A, Ducrot P H, Boyer F D, Gieselmann M, Roelofs W
机构信息
Unite de Phytopharmacie et Mediateurs Chimiques, Institut National de la Recherche Agronomique, route de St Cyr, 78026 Versailles Cedex, France.
出版信息
Proc Natl Acad Sci U S A. 1998 Aug 18;95(17):9867-72. doi: 10.1073/pnas.95.17.9867.
The sex pheromone emitted by the female oleander scale, Aspidiotus nerii (Homoptera, Diaspididae), has been isolated and characterized as (1R, 2S)-cis-2-isopropenyl-1-(4'-methyl-4'-penten-1'-yl)cyclobutaneethanol acetate by using advanced MS and NMR spectroscopic methods, as well as a variety of microderivatization sequences. The structure has been confirmed by stereo- and enantioselective synthesis of the four possible stereoisomers. The absolute configuration has been determined by comparison of the activity of the cis (1S,2R) and (1R, 2S) enantiomers with that exhibited by the natural material in greenhouse bioassays and field tests. The structure of this sesquiterpenoid pheromone is new in the coccids and in the pheromone field in general.
通过使用先进的质谱和核磁共振光谱方法以及各种微衍生化序列，已从夹竹桃圆盾蚧（同翅目，盾蚧科）雌虫中分离出性信息素，并将其鉴定为（1R，2S）-顺式-2-异丙烯基-1-（4'-甲基-4'-戊烯-1'-基）环丁烷乙醇乙酸酯。通过对四种可能的立体异构体进行立体和对映选择性合成，证实了该结构。通过比较顺式（1S，2R）和（1R，2S）对映体与天然物质在温室生物测定和田间试验中表现出的活性，确定了绝对构型。这种倍半萜类信息素的结构在蚧虫类以及整个信息素领域都是新的。
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