Biological activity of (3R,5S,6R)- and (3S,5R,6S)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one, a pheromone ofMacrocentrus grandii (Goidanich) (Hymenoptera: Braconidae)
Biological activity of (3R,5S,6R)- and (3S,5R,6S)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one, a pheromone ofMacrocentrus grandii (Goidanich) (Hymenoptera: Braconidae)
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大甲蝽信息素(3R,5S,6R)-和(3S,5R,6S)-3,5-二甲基-6-(甲基乙基)-3,4,5,6-四氢吡喃-2-酮的生物活性
DOI：
10.1007/bf02033733
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发表时间：
1994
影响因子：
2.3
通讯作者：
Hung‐wen Liu
中科院分区：
文献类型：
--
作者：
P. Swedenborg;Richard L. Jones;Hui;I. Shin;Hung‐wen Liu
本文报道了（3R*，5S*，6 R *）-3，5-二甲基-6-（甲基乙基）-3，4，5，6-四氢吡喃-2-酮的结构鉴定。该内酯存在于男性和女性的黄蜂，实验室和现场生物测定表明，这两个来源的内酯引起飞行启动，逆风anemotaxis，和铸造在男性黄蜂。本研究对合成的（3R，5S，6 R）-和（3S，5 R，6S）-内酯对映体（分别为RSR和SRS）进行了生物活性测定。在风洞研究中，SRS对映体引起的飞行启动，逆风趋风性，并铸造的男性黄蜂可比的内酯来自男性和女性黄蜂。对RSR对映体的飞行反应平均为SRS对映体的14%。没有发现特定比例的立体异构体比单独的SRS对映体更有吸引力。田间研究表明，SRS对映体单独具有吸引雄蜂的活性。当与（Z）-4-十三烯醛（先前鉴定的雌性衍生性信息素）配对时，SRS对映体产生与（Z）-4-十三烯醛加雌性衍生内酯相当的协同反应。
In a previous study we reported identification of (3R*,5S*,6R*)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one as a component of the pheromone ofMacrocentrus grandii Goidanich. The lactone was present in male and female wasps, and laboratory and field bioassays demonstrated that both sources of the lactone elicit flight initiation, upwind anemotaxis, and casting in male wasps. In the present study, the synthetic (3R,5S,6R)- and (3S,5R,6S)-lactone enantiomers (RSR andSRS, respectively) were bioassayed for biological activity. In wind tunnel studies theSRS enantiomer elicited flight initiation, upwind anemotaxis, and casting by male wasps comparable to lactone derived from male and female wasps. Flight response to theRSR enantiomer averaged 14 percent of theSRS enantiomer. No specific ratio of the stereoisomers was found more attractive than theSRS enantiomer alone. Field studies demonstrated theSRS enantiomer was active alone in attracting male wasps. When paired with (Z)-4-tridecenal (a previously identified female-derived sex pheromone), theSRS enantiomer yielded a synergistic response comparable to (Z)-4-tridecenal plus female-derived lactone.