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黄头云杉锯蝇性信息素的碳氢化合物成分:一系列(Z,Z)-9,19-二烯。

Hydrocarbon components of the yellowheaded spruce sawfly sex pheromone : A series of (Z, Z)-9, 19 dienes.

机构信息

Department of Entomology, Fisheries, and Wildlife, University of Minnesota, 55108, St. Paul, Minnesota.

出版信息

J Chem Ecol. 1982 Jan;8(1):95-114. doi: 10.1007/BF00984008.

DOI:10.1007/BF00984008
PMID:24414587
Abstract

The primary sex pheromone of the yellowheaded spruce sawfly,Pikonema alaskensis (Rohwer) (Hymenoptera: Tenthredinidae), was found to include a series of straight-chain hydrocarbon dienes, all with the double bonds in the 9 and 19 positions and all with the (Z, Z) configuration. The major components, of 29, 31, 33, 35, and 37 carbon atoms, were synthesized. In the field and the greenhouse, the synthetic dienes were far above control levels in activity but, at least during the first hours of bioassay, were somewhat less active than the female-derived materials on a weight basis. In the field, a mixture of all five synthetic dienes, in the proportions found in the females, was more attractive than any single one, on a mole basis. In addition, (Z, Z)-9,19 dienes of 28, 30, 32, 34, 36, 38, and 39 carbons have been detected in females in minor amounts. The first five were bioassayed, and each was found to be similar in activity to the 35-carbon component when compared on a weight basis. The synthetic dienes, while active by themselves, were strongly synergized by two, more polar, Florisil fractions derived from females. Experimental design considerations are discussed.

摘要

黄头云杉扁叶蜂(Pikonema alaskensis)(膜翅目:扁叶蜂科)的主要性信息素被发现包含一系列直链碳氢二烯,所有的双键都在 9 位和 19 位,并且都具有(Z,Z)构型。主要成分有 29、31、33、35 和 37 个碳原子,已被合成。在野外和温室中,合成的二烯在活性方面远远高于对照水平,但至少在生物测定的最初几个小时内,按重量计,其活性略低于雌性来源的物质。在野外,按雌性中发现的比例混合所有五种合成二烯,在摩尔基础上比任何单一一种都更具吸引力。此外,在雌性中还检测到少量的(Z,Z)-9,19-二烯,其碳数分别为 28、30、32、34、36、38 和 39。前五种进行了生物测定,发现它们在按重量计与 35 碳成分进行比较时,其活性相似。尽管合成的二烯本身具有活性,但它们被两种更具极性的佛罗里硅土(Florisil)馏分强烈增效,这两种馏分是从雌性中提取的。讨论了实验设计的考虑因素。

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本文引用的文献

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2
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Science. 1971 Oct 1;174(4004):76-8. doi: 10.1126/science.174.4004.76.
3
Sex pheromone specificity in the pine sawflies: interchange of acid moieties in an ester.松叶蜂中的性信息素特异性:酯中酸性部分的互换
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4
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J Chem Ecol. 1983 Sep;9(9):1343-52. doi: 10.1007/BF00994803.
5
(Z)-10-nonadecenal: A pheromonally active air oxidation product of (Z,Z)-9,19 dienes in yellowheaded spruce sawfly.(Z)-10-壬醛:黄头松叶蜂 (Z,Z)-9,19-二烯在空气中的氧化产物,具有信息素活性。
J Chem Ecol. 1983 Sep;9(9):1333-41. doi: 10.1007/BF00994802.
6
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7
(Z)-4-Tridecenal, a pheromonally active air oxidation product from a series of (Z,Z)-9,13 dienes inMacrocentrus grandii Goidanich (Hymenoptera: Braconidae).(Z)-4-十三碳醛,一种源自大造周氏啮小蜂(膜翅目:姬小蜂科)中一系列(Z,Z)-9,13-二烯的具有性信息素活性的空气氧化产物。
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