Sex pheromones and reproductive isolation of the lesser peachtree borer and the peachtree borer

(E,Z)-3,13-octadecadien-1-ol acetate, and (Z,Z)-3,13-octadecadien-1-ol acetate, isolated from the female lesser peachtree borer, Synanthedon pictipes (Grote and Robinson), and the female peachtree borer, Sanninoidea exitiosa (Say), respectively, strongly attract the respective males of these species in field bioassays. These compounds are the largest pheromones isolated thus far from a lepidopterous species. Sanninoidea exitiosa males did not respond to the synthesized (E,Z)-isomer, and low concentrations of it in the synthesized (Z,Z)-isomer did not interfere with their response to the (Z,Z)-isomer. In contrast, even very low concentrations of the (Z,Z)-isomer (1 percent) in the (E,Z)-isomer significantly inhibited the response of Synanthedon pictipes males.     

Insect sex pheromones: minor amount of opposite geometrical isomer critical to attraction

(Z)-II-Tetradecenyl acetate is the reported sex pheromone of European corn borer and redbanded leafroller moths. However, geometrically pure preparations of the compound are weakly attractive to these species. Presence of the E geometrical isomer in the Z is necessary for maximum sex attraction and these moths are "tuned" to respond optimally to specific proportions of Z to E. This discovery is important to considerations of moth pheromonal specificity, evolution, and in application of knowledge of the pheromones to insect-pest suppression.     

Sex pheromone of the codling moth: structure and synthesis

The structure of a sex pheromone of the codling moth. Laspeyresia pomonella (L.), has been determined by spectrometric and chemical degradative techniques and by synthesis to be (2Z, 6E)-7-methyl-3-propyl-2,6-decadien-1-ol. In field cage tests the synthesized sex pheromone was as attractive as the natural, but neither was as attractive as ten virgin females per trap.     

沙棘木蠹蛾性信息素林间诱蛾活性试验

为比较沙棘木蠹蛾性信息素不同配方的诱集效果,该文利用人工合成的性信息素组分顺7-十四碳烯乙酸酯(Z7-14:Ac)、反3-十四碳烯乙酸酯(E3-14:Ac) 和反7-十四碳烯乙酸酯(E7-14:Ac)按照不同比例配置的4种配方进行了野外诱集试验.结果表明:4组不同配方的性信息素均具有较强的诱集效果,其中平均诱蛾量最高的达17头/诱捕器,日诱蛾量最高的为11头/d,持效期达26 d,不同配方的有效诱捕距离分别达100和150 m.通过比较两种不同诱捕器的野外诱集效果发现:沙棘木蠹蛾实用新型诱捕器的诱蛾效果稍差于三角形诱捕器,但其具有使用方便、易于操作、可长时间使用等特点,诱捕器的最佳悬挂高度为1 m.用性信息素诱杀害虫作为一种高效、无毒、无污染的新方法为沙棘木蠹蛾的综合防治提供了一条崭新的途径.      

Analysis of sex pheromone production and field trapping of the Asian corn borer(Ostrinia furnacalis Guenée) in Xinjiang,China

Identifying the sex pheromone systems of local pest populations facilitates their management, especially for moth species that show significant geographic variation in sex pheromone communication. We investigated the pheromone production and behavioral responses of the Asian corn borer(Ostrinia furnacalis Guenée; ACB) in Xinjiang, China. The ACB produces three compounds:(Z)-12-tetradecenyl acetate(Z12-14:Ac) and(E)-12-tetradecenyl acetate(E12-14:Ac)which are two sex pheromone compounds, and n-te...     

European corn borer: pheromone polymorphism or sibling species?

Electrophoretic analyses of the (Z) and (E) pheromone-attracted males of Ostrinia nubilalis (Hübner), the European corn borer, in an area of coexistence indicate that these strains are not freely interbreeding. Although the populations are morphologically indistinguishable, studies of allozyme, pheromone, and hybridization suggest that the (Z) and (E) entities are genetically differentiated, perhaps to the status of semi- or sibling species.     

Sex attractant of sugar beet wireworm: identification and biological activity

The sex attractant produced by adult females of the sugar beet wire-worm, Limonius californicus (Mannerheim) has been isolated and identified as valeric acid. In the laboratory, male wireworm beetles are repelled by the pure attractant but are drawn with intense sexual excitement to its dilute solutions; in the field, male beetles are lured from a distance of 12 meters. The pheromone occurs in unusually large amounts in the female's body.     

Sex attractant pheromone of the house fly: isolation, identification and synthesis

A sex pheromone isolated from the cuticle and feces of the female house fly attracts the male fly; it has been identified as (Z)-9-tricosene. Chemical and biological comparisons of the natural and synthesized compounds show that they are identical.     

Sex pheromone of the winter moth, a geometrid with unusually low temperature precopulatory responses

The sex pheromone for the winter moth, Operophtera brumata (L.), has been identified as the novel compound (Z,Z,Z)-1,3,6,9-nonadecatetraene. The male moths respond to the pheromone at low temperatures (4 degrees to 15 degrees C) and exhibit an upper response limit that coincides with the lower response limit for other reported moth sex pheromone systems. The pheromone attracted two other geometrid species, O. bruceata (Bruce spanworm) and O. occidentalis.     

马铃薯甲虫对植物挥发物和聚集素的触角电位反应

马铃薯甲虫是马铃薯上一种最主要的毁灭性害虫,在我国属于入侵性害虫。试验对已报道的马铃薯甲虫寄主植物挥发物成分和马铃薯甲虫聚集素进行了触角电位（EAG）测定。结果表明：原液、1／10原液、1／100原液3个浓度均为（E）-2-己烯-1．醇、1-己醇、2-苯乙醇和聚集素的EAG反应最明显,马铃薯甲虫雄虫对里那醇、壬醛、水杨酸甲酯和苯乙酸甲酯原液的EAG反应值明显大于雌虫。该研究结果可为开发马铃薯甲虫田间引诱剂提供理论依据。     

沙柳木蠹蛾性信息素的化学合成

沙柳木蠹蛾是荒漠区灌木林的主要钻蛀性害虫之一,可利用性信息素对其进行生物防治。对沙柳木蠹蛾的性信息素主成分顺-7-十四碳烯-1-醇乙酸酯(Z7-14:OAC)和顺-5-十四碳烯-1-醇乙酸酯(Z5-14:OAC)进行了立体选择性合成,其中,Z7-14:OAC采用炔化物反应引入炔基,经过顺式或反式还原得到相应的不饱和醇类化合物,再酯化为所需的乙酸酯;Z5-14:OAC的合成是将四氢吡喃直接开环制得溴代戊醇乙酸酯,再通过Wittig反应与正壬醛偶联成不饱和酯类化合物。产物经红外光谱仪(IR)和气质联用(GC-MS)确认,可用于该虫的诱杀、交配干扰和虫情测报。     

梨小食心虫性诱剂次级成分诱蛾活性研究

梨小食心虫性信息素的主要组分为顺-8-十二碳烯醇乙酸酯(Z8-12Ac),但有报道反-8-十二碳烯醇乙酸酯(E8-12Ac)也为活性组分。以辛二醇和正丁醛等为原料,以二甲基亚砜为溶剂,通过wittig试剂合成E8-12Ac,于不同地点进行田间试验。结果表明:当Z8-12Ac、E8-12Ac与顺-8-十二碳烯醇(Z8-12Ac)含量比为90∶4∶6与94∶0∶6时,诱捕效果最好,其中配比94∶0∶6诱捕虫量最多。结果显示,E8-12Ac无明显的诱蛾活性,Z8-12OH对诱蛾具有增效作用。     

Synthetic Juvenile Hormone: Induction of Sex Pheromone Production in Ips confusus

Topical application of 25, 50, or 100 micrograms of 10,11-epoxy-farnesenic acid methyl ester in peanut oil induced male Ips confusus to produce sex pheromone in the hindgut Malpighian tubule region. Twenty-four hours aftertreatment of male beetles with 100 micrograms of hormone, their hindgut Malpighian tubule extract was more attractive to female beetles in a laboratory bioassay than was extract from males producing pheromone naturally in ponderosa pine logs.     

Sexual role reversal in mate-finding strategies of the cabbage looper moth

The mate-finding behavior of the cabbage looper moth Trichoplusia ni (Lepidoptera: Noctuidae) includes both female- and male-produced sex pheromones used in distinct mate-finding strategies. Both sexes release multicomponent pheromones attractive to the opposite sex. Male pheromone is comprised of d-linalool, m-cresol, and p-cresol released from abdominal hair pencils. Males exposed to host plant odor or to the female sex pheromone (Z)-7-dodecen-1-ol acetate are more attractive to females, suggesting stimulation of male pheromone release.     

Sex Pheromones: (E,E)-8,10-Dodecadien-1-ol in the Codling Moth

Although (E,E)-8,10-Dodecadien-l-ol was reported to be a sex pheromone of the codling moth [Laspeyresia pomonella (L.)], its presence in the moth was questioned, mainly because it has not been isolated. A computerized search of data from gas chromatography-mass spectrometry of a partially purified extract equivalent to 45 abdominal tips of female moths produced a mass spectrum that matched that of the authentic coinpound. Other data also confirmed the presence of the compound.     

绿盲蝽对寄主植物花器挥发性成分的电生理和风洞行为反应

为了揭示绿盲蝽与寄主植物间的化学通讯机制,采用触角电位(EAG)和风洞技术,测定了绿盲蝽雌、雄成虫对寄主植物花器挥发物的电生理和风洞行为反应。结果表明:除间二甲苯外,绿盲蝽雌、雄成虫对a-蒎烯、乙酸叶醇酯和松油烯均产生明显的EAG反应;风洞试验结果表明,绿盲蝽雌、雄成虫对乙酸叶醇酯的定向行为反应均较强,且与对照化合物苯乙酮和顺-3-己烯醇无显著差异。乙酸叶醇酯等植物花器挥发性成分可能在绿盲蝽寄主定位过程中起着重要作用。     

枣粘虫成虫性引诱的初步研究

枣粘虫是我国红枣产区的重要害虫。为探求防治新途径,对成虫生物学与性引诱进行了初步研究。枣粘虫一年发生三代,各代成虫发生的始、盛、末期分别为:第一代3/上——4/上—4/下;第二代6/上——6/中——6/下;第三代7/上——7/下——8/中。雌雄性比在0.86∶1和1.19∶1之间。一般雄蛾羽化早於雌蛾。95％以上成虫集中于早晨5——8时进行交尾。雌雄多次交尾,雌蛾平均1.48次,雄蛾3次。成虫寿命一般为一周左右,雌蛾寿命长於雄蛾。田间性诱试验表明:活雌蛾性诱以3头和5头的雌当量效果最好;粗提液以乙醚为溶剂的诱蛾数量最高;摘取腺体以羽化后48小时摘取的诱捕效果较好。通过对雌蛾性腺体所产生的性信息素进行EAG——GC以及色质联仪分析,初步确定枣粘虫性信息素的成份是一元不饱和十二碳烯醇乙酸酯的多元体系。经微量臭氧化测定,双键位置在7位和9位。田间生测表明以反、顺——9——十二碳烯醇酯(E、Z——9—C_(12)∶OAC)在比例为80∶20和83∶17时对雄蛾的诱捕效果最高。     

小菜蛾性信息素与性信息素结合蛋白、受体蛋白结合机理研究

【目的】研究小菜蛾性信息素与性信息素结合蛋白、受体蛋白之间作用的关键氨基酸残基和作用力类型,揭示小菜蛾识别性信息素的分子机制,为开发新型性诱剂和小菜蛾的无害化防治提供新思路。【方法】运用Discovery Studio 2.5对小菜蛾性信息素结合蛋白PxylPBP2和受体蛋白PxylOR4进行同源建模,运用程序包中LibDock模块进行分子对接,运用Calculate Energy模块计算复合物结合自由能,分析性信息素Z9-14∶AC与PxylPBP2和PxylOR4的结合模式及相互作用力。【结果】Thr9是PxylPBP2与Z9-14∶AC形成氢键的关键氨基酸残基,Z9-14∶AC易与PxylOR4中的Leu残基产生疏水作用力;PxylPBP2与Z9-14∶AC结合的主要驱动力是静电力,PxylOR4与Z9-14∶AC结合的主要驱动力是范德华力,溶剂化能均抑制Z9-14∶AC与PxylPBP2和Z9-14∶AC与PxylOR4的结合。【结论】小菜蛾性信息素受体蛋白和性信息素结合蛋白在识别和结合性信息素分子方面存在明显差异,性信息素受体蛋白与性信息素反应更灵敏、形成的复合物更稳定。     

茶尺蠖信息素结合蛋白PBP2的基因克隆、原核表达及其结合功能

【目的】茶尺蠖(Ectropis obliqua)是中国茶区主要的鳞翅目害虫,其幼虫暴食性常给茶园带来巨大损失。鳞翅目昆虫雌雄个体间普遍存在着性信息素通讯环节,而茶尺蠖性信息素识别途径一直鲜有报道。论文旨在通过对茶尺蠖性信息素识别过程中的结合蛋白基因进行鉴定和功能研究,为茶尺蠖性信息素化学通讯和嗅觉信息识别传递机制提供理论依据。【方法】利用RT-PCR技术对从雄虫触角转录组数据中首次鉴定和发现的一个茶尺蠖信息素结合蛋白基因(pheromone-binding protein,PBP)2(EoblPBP2)进行全长cDNA序列克隆(Gen Bank登录号为KX421383)后,将该基因与pET32a载体连接构建表达载体。随后向导入pET32a/EoblPBP2表达质粒的大肠杆菌BL21(DE3)中对其表达载体加入终浓度1 mmol·L~(-1)的IPTG进行蛋白的诱导表达,进一步利用镍NTA琼脂糖凝胶柱和含有咪唑的上清缓冲液分离目的蛋白,以PBS缓冲液作为透析液纯化得到高浓度重组蛋白。最后通过荧光竞争法,利用N-苯基-1-萘胺(N-phenyl-1-naphthylamine,1-NPN)作为荧光报告子以放大荧光信号,随后向重组蛋白与1-NPN混合体系中分别加入(Z,Z,Z)-3,6,9-十八碳三烯以及10种测试气味后经过分子荧光光度计扫描得到相对荧光值,计算各配基的解离常数KD,研究重组蛋白与茶尺蠖性信息素和茶树挥发物的生理功能。【结果】EoblPBP2全长为492 bp,编码了163个氨基酸,蛋白相对分子质量为15.9kD,等电点为4.983,具有保守的6个半胱氨酸,根据分子进化树分析其应归属于昆虫PBPs家族。结合功能结果显示,10种测试气味均能将1-NPN与茶尺蠖EoblPBP2重组蛋白的混合体系于420 nm处的相对荧光值降至50%以下。其中β-紫罗兰酮、邻苯二甲酸二丁酯、苯乙醛、癸醛和反-2-癸烯醛等5种茶树挥发物质与EoblPBP2重组蛋白的结合能力较强,解离常数KD分别为7.923、14.830、30.368、28.068和27.597μmol·L~(-1)。而性信息素成分之一的(Z,Z,Z)-3,6,9-十八碳三烯与EoblPBP2的解离常数KD仅为172.591μmol·L~(-1),仅小于苯甲醇的解离常数KD 230.880μmol·L~(-1),而远远大于上述5种气味物质。表明EoblPBP2重组蛋白具有茶尺蠖性信息素成分((Z,Z,Z)-3,6,9-十八碳三烯)和植物挥发物质广谱结合能力,而其与性信息素的亲和力弱于大部分测试植物挥发物。【结论】EoblPBP2能与包括性信息素成分在内的多种植物挥发物结合,可能是一种具备特殊复合功能的信息素结合蛋白,可用之进一步研究茶尺蠖的性信息素识别和传递途径。     

Sex Pheromone Biosynthesis in Trichoplusia ni: Key Steps Involve Delta-11 Desaturation and Chain-Shortening

In addition to the primary pheromone component (Z)-7-dodecenyl acetate, the sex pheromone gland of Trichoplusia ni contains the immediate fatty acyl precursor (Z)-7-dodecenoate and a large quantity of (Z)-11-hexadecenoate. Labeling experiments showed that (Z)-11-hexadecenoate is chain-shortened to (Z)-9-tetradecenoate, and that this in turn is chain-shortened to (Z)-7-dodecenoate. The same mechanism appears to explain the sex pheromone compositions of many other moth species.