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(+)-乙酸龙脑酯和相关化合物对美洲大蠊的性信息素活性。

Sex pheromonal activity of (+)-bornyl acetate and related compounds to the American cockroach.

机构信息

Mitsubishi-Kasei Institute of Life Sciences, 11 Minamiooya, Machida-shi, 194, Tokyo, Japan.

出版信息

J Chem Ecol. 1983 Mar;9(3):433-48. doi: 10.1007/BF00988460.

DOI:10.1007/BF00988460
PMID:24407410
Abstract

Many compounds related to (+)-bornyl acetate (a sex phero-mone mimic of the American cockroach) were synthesized and tested for sex pheromonal activity. All compounds except for esters of (+)- and (-)-borneol were inactive, whereas (+)-bornyl acetate (Ib) and propionate (Ic) showed the activity at 0.05 mg. Although (-)-bornyl propionate (IVc) is the enantiomer of Ic, it exhibited weak activity at 0.5 mg dose. On the basis of the behavioral assay results, important chemical factors in Ib for pheromonal activity were elucidated and are discussed in connection with another mimic, (+)-trans-verbenyl acetate. The M/ F ratio index in EAG was evaluated for both active and inactive compounds. The index demonstrated a good correlation with the behavioral activity.

摘要

许多与(+)-莰烯乙酸酯(美洲大蠊性信息素类似物)相关的化合物被合成并测试了其性信息素活性。除了(+)-和(-)-龙脑醇的酯之外,所有化合物均没有活性,而(+)-莰烯乙酸酯(Ib)和丙酸酯(Ic)在 0.05mg 时表现出活性。尽管(-)-莰烯丙酸酯(IVc)是 Ic 的对映异构体,但在 0.5mg 剂量时表现出较弱的活性。基于行为测定结果,阐明了 Ib 中对信息素活性很重要的化学因素,并与另一种类似物(+)-反式马鞭烯醇乙酸酯进行了讨论。EAG 中对活性和非活性化合物进行了 M/F 比值指数评估。该指数与行为活性有很好的相关性。

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本文引用的文献

1
Sex pheromonal activity of (+)-trans-verbenyl acetate and related compounds to the american cockroach,Periplaneta americana L.(+)-反式马鞭草烯醇乙酸酯及相关化合物对美洲大蠊(Periplaneta americana L.)的性信息素活性
J Chem Ecol. 1981 Sep;7(5):853-65. doi: 10.1007/BF00992383.
2
Structural significance of the alkyl substituent at the C-4 of (+)-trans-verbenyl acetate in sex pheromonal activity of the American cockroach.(+)-反式马鞭烯醇乙酸酯 C-4 位烷基取代基在美洲大蠊性信息素活性中的结构意义。
J Chem Ecol. 1982 May;8(5):883-95. doi: 10.1007/BF00994789.
3
Studies on sex pheromone of American cockroach, with emphasis on structure elucidation of periplanone-A.
J Chem Ecol. 1991 Apr;17(4):695-706. doi: 10.1007/BF00994193.
美洲大蠊性信息素的研究,重点在于 elucidation 结构periplanone-A。
J Chem Ecol. 1982 Feb;8(2):439-51. doi: 10.1007/BF00987792.
4
Structural significance of the geminal-dimethyl group of (+)-trans-verbenyl acetate, sex pheromone mimic of the American cockroach.(+)-反式马鞭烯醇乙酸酯的偕二甲基结构意义,美洲大蠊性信息素类似物。
J Chem Ecol. 1983 Apr;9(4):533-49. doi: 10.1007/BF00990225.
5
Sex pheromone mimics of the American cockroach.美洲大蠊的性信息素类似物。
Nature. 1971 Jul 23;232(5308):259-61. doi: 10.1038/232259a0.