(1S,3R)-cis-Chrysanthemyl Tiglate: Sex Pheromone of the Striped Mealybug, Ferrisia virgata
(1S,3R)-cis-Chrysanthemyl Tiglate: Sex Pheromone of the Striped Mealybug, Ferrisia virgata
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(1S,3R)-cis-Chrysanthemyl Tiglate：条纹粉蚧 Ferrisia virgata 的性信息素
DOI：
10.1007/s10886-017-0879-z
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发表时间：
2017
影响因子：
2.3
通讯作者：
Ichiki Ryoko T.
中科院分区：
文献类型：
--
作者：
Tabata Jun;Ichiki Ryoko T.
菊酸(2，2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic酸)的衍生物是在除虫菊属植物中发现的经典的天然拟除虫菊酯类化合物，具有杀虫活性。菊酸具有两个不对称碳，有四个可能的立体异构体，大多数天然拟除虫菊酯都有(1R，3R)-易位。有趣的是，菊花酸相关的结构也在昆虫性信息素中被发现；(1R，3R)-trans-(2，2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl)methanol(菊花醇)的羧酸酯已经从两个粉虱物种中被报道。在本研究中，从条纹粉虱Frisia virgata(Cockerell)中发现了另一种菊花醇，作为其信息素。通过气相色谱-质谱联用、核磁共振、高效液相色谱手性固定相色谱柱和标准品的分析，确定该信息素为(1S，3R)-(−)-顺式菊花酯。在温室捕集生物测定中，(1S，3R)-对映体对成年雄虫有很强的诱集作用，而其他对映体的活性很弱。菊花酸相关结构的构型在自然界中似乎相对稀缺，这是节肢动物报告的第一个例子。
Derivatives of 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid (chrysanthemic acid) are classic natural pyrethroids discovered in pyrethrum plants and show insecticidal activity. Chrysanthemic acid, with two asymmetric carbons, has four possible stereoisomers, and most natural pyrethroids have the (1R,3R)-transconfiguration. Interestingly, chrysanthemic acid–related structures are also found in insect sex pheromones; carboxylic esters of (1R,3R)-trans-(2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl)methanol (chrysanthemyl alcohol) have been reported from two mealybug species. In the present study, another ester of chrysanthemyl alcohol was discovered from the striped mealybug,Ferrisia virgata(Cockerell), as its pheromone. By means of gas chromatography–mass spectrometry, nuclear magnetic resonance spectrometry, and high-performance liquid chromatography analyses using a chiral stationary phase column and authentic standards, the pheromone was identified as (1S,3R)-(−)-cis-chrysanthemyl tiglate. The (1S,3R)-enantiomer strongly attracted adult males in a greenhouse trapping bioassay, whereas the other enantiomers showed only weak activity. Thecisconfiguration of the chrysanthemic acid–related structure appears to be relatively scarce in nature, and this is the first example reported from arthropods.