Significance of chirality in pheromone science

Pheromones play important roles in chemical communication among organisms. Various chiral and non-racemic pheromones have been identified since the late 1960s. Their enantioselective syntheses could establish the absolute configuration of the naturally occurring pheromones and clarified the relationships between absolute configuration and bioactivity. For example, neither the (R)- nor (S)-enantiomer of sulcatol, the aggregation pheromone of an ambrosia beetle Gnathotrichus sulcatus, is behaviorally active, while their mixture is bioactive. In the case of olean, the olive fruit fly pheromone, its (R)-isomer is active for the males, and the (S)-isomer is active for the females. About 140 chiral pheromones are reviewed with regard to their stereochemistry–bioactivity relationships. Problems encountered in studying chirality of pheromones were examined and analyzed to think about possible future directions in pheromone science.     

蛾类性信息素生物合成途径及其调控

蛾类通过产生和识别物种特异性性信息素来引发后续交配行为,因此它在两性交配行为中至关重要.它们具有不同碳链长度、末端官能团、不同双键位置和构型等化学结构特征,本文详细讨论了不同蛾类性信息素的合成途径以及催化每一步反应的相关酶系,列举了15种夜蛾科不同亚科常见物种的性信息素组分及其比例,总结了产生特定比例性信息素的可能原因,查阅了夜蛾科不同物种已经鉴别的性信息素,并按照不同亚科、不同官能团和碳链长度对其进行分类,归纳了同一物种及其亲缘物种性信息素组分和比例的变异,总结了产生变异的分子机理,讨论了性信息素变异和物种进化的关系.最后以生物合成激活神经肽(PBAN)为主, 介绍了其调控途径和机制.本文旨在以不同的蛾类性信息素合成途径为线索,从共有合成途径出发深入了解其规律和共性,从特异合成途径出发探究物种间的进化和变异,展望未来的研究方向及其应用.     

白蚁信息素研究进展

白蚁是最古老的社会性昆虫, 其社会性的维持需要信息素的相互作用。本文回顾了近年来国内外白蚁信息素研究的最新进展, 内容涉及白蚁踪迹信息素、 性信息素、 告警信息素和促食信息素的功能、 化学成分及产生信息素的外分泌腺。白蚁分泌信息素的腺体主要有背板腺、 腹板腺、 后腹板腺、 额腺和唾腺。绝大多数白蚁信息素是挥发性物质。白蚁在化学通讯上存在节俭策略, 即同一种化合物由不同的白蚁种类的不同外分泌腺分泌, 可具有不同的功能。总结了各类信息素在白蚁物种间、 同一物种的品级间和性别间的异同和作用方式, 强调了白蚁信息素的反应阈值、 最佳浓度、 有效期和物种特异性对其功能的影响。目前对白蚁信息素的研究尚处于起步阶段, 其研究成果对等翅目系统发育研究和白蚁防治具有重要的意义。文章最后展望了白蚁信息素在白蚁防治上的应用前景。     

昆虫聚集信息素

昆虫聚集信息素是昆虫重要的信息化学物质之一,对昆虫的聚集行为有重要意义。近三十年来,国外鉴定了多种昆虫聚集信息素,主要成分为一些烃、醇、醛、酮、酯、酸、酸酐、胺以及腈类化合物,但其在有害生物可持续治理中的应用潜能尚未充分利用;昆虫聚集信息素的来源多样,除蛹外,多个虫态均有聚集信息素释放,有些学者甚至把一些寄主释放的挥发物作为聚集信息素的组分;同种昆虫,不同生理状态,其聚集信息素可以完全不同或同一信息化学物质的功能不同;但是,并非所有昆虫的聚集行为均为聚集信息素调节,利他素、性信息素以及报警信息素等其它信息化学物质均能导致一些昆虫的聚集。本文综述了5目17科55种昆虫的聚集信息素。     

蛾类昆虫性信息素受体及其作用机理

蛾类昆虫性信息素受体首先从烟芽夜蛾Heliothis virescens和家蚕Bombyx mori中鉴定出来, 到目前为止已经克隆得到了19种蛾类昆虫的几十种性信息素受体基因, 并且这些基因在系统发育树中聚成一个亚群。性信息素受体从蛾类蛹期开始表达, 主要表达在雄性触角的毛形感器中, 少部分受体在雌性触角、 雄性触角其他感器以及身体其他部位中也有表达。大部分蛾类性信息素受体的配体并不是单一的, 而是能够对多种性信息素组分有反应, 部分性信息素受体还能够识别性信息素以外的其他物质, 还有一部分性信息素受体的识别配体目前尚不清楚。另外发现在雌性蛾类触角中也存在一些嗅觉受体能够识别雄性分泌的性信息素。在蛾类性信息素受体与性信息素识别的过程中, 性信息素结合蛋白不仅能够特异性地运送配体到嗅觉神经元树状突上, 还能够提高性信息素与性信息素受体之间的结合效率。另外, OrCo类受体与性信息素受体共表达在嗅觉神经元中, 在蛾类性信息素受体与配体的识别过程中扮演了重要角色。但是蛾类信息素对神经元刺激的终止并非由性信息素受体控制, 而是由细胞中的气味降解酶等其他因子调控。蛾类性信息素受体研究中还有很多疑问需要解答, 其过程可能比我们想象的更为复杂。     

Effect of Trail Bifurcation Asymmetry and Pheromone Presence or Absence on Trail Choice by Lasius niger Ants

During foraging, ant workers are known to make use of multiple information sources, such as private information (personal memory) and social information (trail pheromones). Environmental effects on foraging, and how these interact with other information sources, have, however, been little studied. One environmental effect is trail bifurcation asymmetry. Ants forage on branching trail networks and must often decide which branch to take at a junction (bifurcation). This is an important decision, as finding food sources relies on making the correct choices at bifurcations. Bifurcation angle may provide important information when making this choice. We used a Y‐maze with a pivoting 90° bifurcation to study trail choice of Lasius niger foragers at varying branch asymmetries (0°, [both branches 45° from straight ahead], 30° [branches at 30° and 60° from straight ahead], 45°, 60° and 90° [one branch straight ahead, the other at 90°]). The experiment was carried out either with equal amounts of trail pheromone on both branches of the bifurcation or with pheromone present on only one branch. Our results show that with equal pheromone, trail asymmetry has a significant effect on trail choice. Ants preferentially follow the branch deviating least from straight, and this effect increases as asymmetry increases (47% at 0°, 54% at 30°, 57% at 45°, 66% at 60° and 73% at 90°). However, when pheromone is only present on one branch, the graded effect of asymmetry disappears. Overall, however, there is an effect of asymmetry as the preference of ants for the pheromone‐marked branch over the unmarked branch is reduced from 65%, when it is the less deviating branch, to 53%, when it is the more deviating branch. These results demonstrate that trail asymmetry influences ant decision‐making at bifurcations and that this information interacts with trail pheromone presence in a non‐hierarchical manner.     

蛾类性信息素研究进展

蛾类是昆虫性信息素中研究较多的类群,已有565种的性信息素成份被鉴定,其相关研究在害虫监测和防治上得到实际应用的同时,已涉及到生态、生化、遗传等诸多方面,特别是在物种多样性的化学表达及物种的生殖隔离现象的分子水平的表达上,提供了研究的典范。本文将介绍蛾类性信息素的多样性、性信息素化学结构鉴定、微量成分的作用、合成性信息素的利用、性信息素生物合成酶、性信息素生产的调节机制及性信息素的感受机制等方面的研究现状和存在的问题。     

日本松干蚧性信息素光学异构体的引诱活性

对合成的日本松干蚧Matscoccus matsumurse(kuwana)性信息素4、6、10、12-四甲基-反2、反4-十三碳二烯-7-酮1所有四个光学活性异构体,进行了诱虫活性测定和林间诱捕试验。结果表明,只有6R、10R-4、6、10、12-四甲基-反2 反4-十三碳二烯-7-酮对日本松干蚧雄成虫具有强烈引诱活性,被确定为该虫天然性信息素的绝对构型。     

Does the scent of a potential mate prevent the resorption of oocytes by apoptosis in Nauphoeta cinerea?

Abstract  We expect organisms to have evolved mechanisms to gather and use the information available within their environments, to steer resource investment decisions toward the traits that will give the greatest fitness returns. Pheromones are social signals, a common purpose of which is to act as indicators of mate presence. Consequently, pheromones have the potential to act as signals to increase or maintain reproductive investment over that of competing life-history traits. In the cockroach, Nauphoeta cinerea (Oliver), females pay costs of maintaining investment in reproduction when there are no males, and males produce pheromones that are known to effect female reproductive outcomes. Whether the pheromones have an influence on resource physiology is unknown. We subjected newly eclosed females to either a synthetic blend of male pheromones or control. We dissected females at 7, 12, 17 or 22 days. We measured apoptosis levels and size of all oocytes within the vitellerium, and measured dry fat body mass. Synthetic male pheromone blend did not have an effect on any measure of female reproductive or somatic resource physiology. Although negative results are always problematic, the success of the synthetic pheromone method in the past suggests that females may be insensitive to male pheromones in the pre-oviposition period, and may rely on mating stimulus rather than pheromone as the cue for oocyte maintenance and growth. Previous studies reporting effects of male pheromones on female reproduction suggest that the period of pheromone sensitivity may be between mating and birth.     

蛾类昆虫雄性信息素及其功能

昆虫性信息素是两性通讯系统的基础,其中雄性信息素的研究相对较少。本文综述了蛾类昆虫雄性信息素的研究进展。迄今已鉴定出40余种蛾类昆虫的雄性信息素,其行为学功能主要有对雌性的引诱和激欲、对同种雄性的抑制及种间隔离等。     

Biosynthetic pathways of the pheromone of the Egyptian armyworm Spodoptera littoralis

Abstract Most insect pheromones comprise multicomponent blends of geometric or optical isomers, and one major question is how insects produce species‐specific ratios of components for successful reproductive isolation. Key enzymes suggested to be involved in pheromone biosynthesis are acetyl‐coenzyme A carboxylase and fatty acyl synthetase, chain‐shortening enzymes, desaturases, elongases, reductases, oxidases, and alcohol acetyl transferases. The female pheromone composition of the Egyptian armyworm Spodoptera littoralis (Boisd.) is highly dependent on the origin of the strain. In this review, we present a summary of the different reported pheromone compositions of the moth, including from our recent studies on this subject, as well as the biosynthetic routes to the different components and the molecular approaches involved. In addition, the key role played in the proposed biosynthetic pathways by a number of important biosynthetic enzymes, such as chain shortening enzymes, desaturases and alcohol acetyl transferases, is outlined, as well as the latest developments on the inhibition of these enzymes.     

Pheromonal control: reconciling physiological mechanism with signalling theory

Pheromones are intraspecific chemical signals. They can have profound effects on the behaviour and/or physiology of the receiver, and it is still common to hear pheromones described as controlling of the behaviour of the receiver. The discussion of pheromonal control arose initially from a close association between hormones and pheromones in the comparative physiological literature, but the concept of a controlling pheromone is at odds with contemporary signal evolution theory, which predicts that a manipulative pheromonal signal negatively affecting the receiver's fitness should not be stable over evolutionary time. Here we discuss the meaning of pheromonal control, and the ecological circumstances by which it might be supported. We argue that in discussing pheromonal control it is important to differentiate between control applied to the effects of a pheromone on a receiver's physiology (proximate control), and control applied to the effects of a pheromone on a receiver's fitness (ultimate control). Critically, a pheromone signal affecting change in the receiver's behaviour or physiology need not necessarily manipulate the fitness of a receiver. In cases where pheromonal signalling does lead to a reduction in the fitness of the receiver, the signalling system would be stable if the pheromone were an honest signal of a social environment that disadvantages the receiver, and the physiological and behavioural changes observed in the receiver were an adaptive response to the new social circumstances communicated by the pheromone.     

桃园中食心虫单一性诱芯及其复合配置的诱蛾效率比较

【目的】明确两种食心虫性诱芯复合配置的诱蛾效果,提高其监测或防治效率及其绿色环保化水平,为果树生产中食心虫的高效监测和绿色防控提供科学依据。【方法】田间系统调查研究了梨小食心虫(以下简称"梨小")、桃小食心虫(以下简称"桃小")单一性诱芯及其复合配置3种处理的诱蛾效率,并利用"Y"型嗅觉仪比较研究了其间梨小雄蛾趋向性的差异。【结果】(1)梨小和桃小性单一诱芯及其复合配置对梨小均具有引诱作用,其诱蛾总量依次为8 238.33、1 451.67、8 321.67头/诱捕器,其中第1、2、3代时复合配置诱蛾量最大,越冬代和第4代时梨小单一性诱芯诱蛾量最大,而各世代桃小单一性诱芯诱蛾量均最低。梨小单一性诱芯及其复合配置均监测到5个梨小发生高峰,且峰期基本一致,但复合配置的峰日诱蛾量均较高;桃小单一性诱芯仅监测到3个梨小发生高峰,且峰日诱蛾量亦较低。(2)桃小单一性诱芯及其复合配置对桃小均具有引诱作用,其诱蛾总量依次为4.00、2.33头/诱捕器,而梨小单一性诱芯对桃小无引诱作用。(3)"Y"型嗅觉仪研究发现,梨小食心虫对梨小和桃小各单一性诱芯及其复合配置均具有趋向作用,其趋向率依次为50.67%、8.67%、53.33%。【结论】梨小和桃小单一性诱芯复合配置对梨小诱捕量有微增效作用,而对桃小诱捕量有一定干扰作用,但影响均不显著。据此,该复合配置可用于桃园中梨小和桃小的监测与防控。     

Moth sex pheromones affect interspecific competition among sympatric species and possibly population distribution by modulating pre-mating behavior

Premating behaviors mediated by pheromones play pivotal roles in animal mating choices. In natural populations of the striped stem borer Chilo suppressalis and the rice leaf roller Cnaphalocrocis medinalis in the rice field habitat, we discovered that Z11-16:Ald, a major component of the C. suppressalis pheromone, modulated the premating behavior of C. medinalis. Z11-16:Ald evoked a strong olfactory response in male antennae and strongly inhibited the sex pheromone trapping of male C. medinalis in the field. The functions of three C. medinalis sex pheromone receptor genes (CmedPR1–3) were verified through heterologous expression in Xenopus oocytes. CmedPR1 responded to Z11-18:OH and Z11-18:Ald, as well as the interspecific pheromone compound Z11-16:Ac of sympatric species; CmedPR2 responded to Z13-18:OH and Z13-18:Ald, as well as the sex pheromone compounds Z11-16:Ald and Z9-16:Ald of sympatric species; and CmedPR3 responded to Z11-18:OH and Z13-18:OH, as well as the interspecific pheromones Z11-16:OH, Z9-16:Ald, Z11-16:Ac, and Z11-16:Ald of sympatric species. Thus, CmedPR2 and CmedPR3 share the ligand Z11-16:Ald, which is not a component of the C. medinalis sex pheromone. Therefore, the sex pheromones of interspecific species affected the input of neural signals by stimulating the sex pheromone receptors on the antennae of male C. medinalis moths, thereby inhibiting the olfactory responses of the male moths to the sex pheromones. Our results demonstrate chemical communication among sympatric species in the rice field habitat, the recognition of intra- and interspecific sex pheromones by olfactory receptors, and how insect premating behaviors are modulated to possibly affect resource partitioning.     

白蚁信息素研究进展

采用信息素防治白蚁这种世界性害虫是当前白蚁研究的一大热点。本文从化学和生物两个方面总结了几十年来国内外白蚁信息素及其类似物研究进展。讨论了影响信息素活性的几个因素。并根据最新的研究情况,对今后的信息素及其类似物的理论研究和应用情况进行了展望。     

半翅目昆虫性信息素的研究进展

本文主要从半翅目昆虫性信息素的提取鉴定方法、分泌部位、性信息素成分、在防治中的应用以及存在的问题等几个方面综述了半翅目昆虫性信息素的研究进展。     

The sixth transmembrane region of a pheromone G-protein coupled receptor,Map3, is implicated in discrimination of closely related pheromones in Schizosaccharomyces pombe

Most sexually reproducing organisms have the ability to recognize individuals of the same species. In ascomycete fungi including yeasts, mating between cells of opposite mating type depends on the molecular recognition of two peptidyl mating pheromones by their corresponding G-protein coupled receptors (GPCRs). Although such pheromone/receptor systems are likely to function in both mate choice and prezygotic isolation, very few studies have focused on the stringency of pheromone receptors. The fission yeast Schizosaccharomyces pombe has two mating types, Plus (P) and Minus (M). Here, we investigated the stringency of the two GPCRs, Mam2 and Map3, for their respective pheromones, P-factor and M-factor, in fission yeast. First, we switched GPCRs between S. pombe and the closely related species Schizosaccharomyces octosporus, which showed that SoMam2 (Mam2 of S. octosporus) is partially functional in S. pombe, whereas SoMap3 (Map3 of S. octosporus) is not interchangeable. Next, we swapped individual domains of Mam2 and Map3 with the respective domains in SoMam2 and SoMap3, which revealed differences between the receptors both in the intracellular regions that regulate the downstream signaling of pheromones and in the activation by the pheromone. In particular, we demonstrated that two amino acid residues of Map3, F214 and F215, are key residues important for discrimination of closely related M-factors. Thus, the differences in these two GPCRs might reflect the significantly distinct stringency/flexibility of their respective pheromone/receptor systems; nevertheless, species-specific pheromone recognition remains incomplete.     

Molecular elements of pheromone detection in the female moth,Heliothis virescens

Pheromones play pivotal roles in the reproductive behavior of moths, most prominently for the mate finding of male moths. Accordingly, the molecular basis for the detection of female‐released pheromones by male moths has been studied in great detail. In contrast, little is known about how females can detect pheromone components released by themselves or by conspecifics. In this study, we assessed the antenna of female Heliothis virescens for elements of pheromone detection. In accordance with previous findings that female antennae respond to the sex pheromone component (Z)‐9‐tetradecenal, we identified olfactory sensory neurons that express its cognate receptor, the receptor type HR6. All HR6 cells coexpressed the “sensory neuron membrane protein 1” (SNMP1) and were associated with supporting cells expressing the pheromone‐binding proteins PBP1 and PBP2. These features are reminiscent to male antennae and point to congruent mechanisms for pheromone detection in the two sexes. Further analysis of the SNMP1‐expressing cells revealed a higher number in females compared to males. Moreover, in females, the SNMP1 neurons were arranged in clusters, which project their dendrites into a common sensillum, whereas in males there were only solitary SNMP1‐neurons and only 1 per sensillum. Not all SNMP1 positive cells in female antennae expressed HR6 but instead the putative pheromone receptors HR11 and HR18, respectively. Neurons expressing 1 of the 3 receptor types were assigned to different sensilla. Together the data indicate that on the antenna of females, sensory neurons in a subset of sensilla trichodea are equipped with molecular elements, which render them responsive to pheromones.     

A receptor and binding protein interplay in the detection of a distinct pheromone component in the silkmoth Antheraea polyphemus

Male moths respond to conspecific female-released pheromones with remarkable sensitivity and specificity, due to highly specialized chemosensory neurons in their antennae. In Antheraea silkmoths, three types of sensory neurons have been described, each responsive to one of three pheromone components. Since also three different pheromone binding proteins (PBPs) have been identified, the antenna of Antheraea seems to provide a unique model system for detailed analyzes of the interplay between the various elements underlying pheromone reception. Efforts to identify pheromone receptors of Antheraea polyphemus have led to the identification of a candidate pheromone receptor (ApolOR1). This receptor was found predominantly expressed in male antennae, specifically in neurons located beneath pheromone-sensitive sensilla trichodea. The ApolOR1-expressing cells were found to be surrounded by supporting cells co-expressing all three ApolPBPs. The response spectrum of ApolOR1 was assessed by means of calcium imaging using HEK293-cells stably expressing the receptor. It was found that at nanomolar concentrations ApolOR1-cells responded to all three pheromones when the compounds were solubilized by DMSO and also when DMSO was substituted by one of the three PBPs. However, at picomolar concentrations, cells responded only in the presence of the subtype ApolPBP2 and the pheromone (E,Z)-6,11-hexadecadienal. These results are indicative of a specific interplay of a distinct pheromone component with an appropriate binding protein and its related receptor subtype, which may be considered as basis for the remarkable sensitivity and specificity of the pheromone detection system.     

The receptor channel formed by ppk25, ppk29 and ppk23 can sense the Drosophila female pheromone 7,11‐heptacosadiene

In Drosophila, pheromones play a crucial role in regulating courtship behaviors. In males, female aphrodisiac pheromones promote male‐female courtship, and male antiaphrodisiac pheromones inhibit male‐male courtship. Previous studies have reported that receptor proteins belonging to the pickpocket (ppk) family, ionotropic receptor family and gustatory receptor family are required for pheromone detection and normal courtship. However, none of them has been shown to be sufficient for sensing pheromones after ectopic expression in originally unresponsive cells. “M” cells are activated by male antiaphrodisiac pheromones but not female aphrodisiac pheromones, and the activated cells inhibit male‐male courtship. In our study, male flies with ectopic expression of ppk25, ppk29 and ppk23 in “M” cells showed decreased male‐female courtship. Using an in vivo calcium imaging approach, we found that the “M” cells expressing these three ppks were significantly activated by the female aphrodisiac pheromone 7,11‐heptacosadiene (7,11‐HD). Our results indicate that a sodium channel consisting, at minimum, of ppk25, ppk29 and ppk23, can sense 7,11‐HD, most likely as a receptor. Our findings may help us gain insights into the molecular mechanisms of pheromonal functions.