Prey-rolling behavior of coatis (Nasua spp.) is elicited by benzoquinones from millipedes

Coatis (Nasua spp.), gregarious, omnivorous carnivores that range in forests from the southwestern USA to south America, dispatch millipedes by rolling them on the ground using rapid, alternating movements of their forepaws. Prey rolling of millipedes is thought to stimulate the depletion of their defensive secretions and to wipe off secretions before millipedes are consumed. We report that prey-rolling behavior in Nasua spp. is elicited by 1,4-benzoquinone; 2-methyl-1,4-benzoquinone; and 2-methoxy-3-methyl-1,4-benzoquinone, the chief components of the defensive secretions of julidan, spirobolidan, and spirostreptidan millipedes. Chemicals elaborated for defense sometimes evolutionarily “backfire,” providing cues to predators on the presence or identity of prey. The elicitation of prey-rolling behavior in Nasua spp. by benzoquinones illustrates this effect for millipedes (and possibly other arthropods) that defensively discharge these compounds.     

Associative learning of odor with food- or blood-meal by Culex quinquefasciatus Say (Diptera: Culicidae)

The ability of many insects to learn has been documented. However, a limited number of studies examining associative learning in medically important arthropods has been published. Investigations into the associative learning capabilities of Culex quinquefasciatus Say were conducted by adapting methods commonly used in experiments involving Hymenoptera. Male and female mosquitoes were able to learn a conditioned stimulus that consisted of an odor not normally encountered in nature (synthetic strawberry or vanilla extracts) in association with an unconditioned stimulus consisting of either a sugar (males and females) or blood (females) meal. Such information could lead to a better understanding of the ability of mosquitoes to locate and select host and food resources in nature.     

华北区域大气中羰基化合物体积分数水平及化学反应活性

为了解华北区域光化学污染特征,于2018年5月至2019年4月在石家庄和兴隆地区利用2,4-二硝基苯肼（DNPH）对空气中的羰基化合物进行采样,并利用高效液相色谱对采集样品进行分析,以了解该区域羰基化合物的组成、体积分数、来源、·OH损耗速率和臭氧生成潜势.本研究共测定了13种含羰基的挥发性有机物,其中体积分数最高的3种物质为丙酮、甲醛和乙醛[石家庄地区：（6.46±5.25）×10^-9、（3.76±2.29）×10^-9和（2.65±1.74）×10^-9;兴隆地区：（1.85±1.27）×10^-9、（1.29±1.02）×10^-9和（0.72±0.48）×10^-9];C1/C2和C2/C3值表明石家庄地区工业化水平较高,受机动车尾气和化石燃料燃烧等人为排放影响较明显;兴隆地区采样点处于背景区域,受自然源影响较大;石家庄地区对L_·OH贡献最大的3种物质分别为乙醛（1.77 s^-1）、甲醛（1.57 s^-1）和丁醛（0.42 s^-1）;兴隆地区对L_·OH贡献最大的3种物质为分别为甲醛（0.53 s^-1）、乙醛（0.47 s^-1）和丁醛（0.12 s^-1）;对O₃生成贡献最大的羰基化合物物种为甲醛和乙醛[石家庄地区：34.61×10^-9（以O₃计,下同）和16.73×10^-9;兴隆地区：11.77×10^-9和4.47×10^-9],且甲醛的最大臭氧生成潜势估算（OFP）远高于乙醛.     

腐殖质及其模型化合物的H2O2光化学生成研究

在模拟太阳光下研究了多种腐殖质及其模型化合物的过氧化氢（H₂O₂）生成动力学,并对其生成机制进行了探讨.结果表明不同来源或不同形式的腐殖质在模拟太阳光照射下均能产生H₂O₂.不同腐殖质生成H₂O₂速率差异不大,范围为6.379~15.784nmol/（L·min）,腐殖酸生成H₂O₂速率略快于富里酸.对于腐殖质模型化合物,邻苯二酚、间苯二酚、对苯二酚、苯醌、邻茴香胺、对茴香胺、水杨酸和2,6-二甲氧基-1,4-苯醌等8种模型化合物没有产生明显的H₂O₂,而藜芦醇、对氨基苯甲酸、3,5-二羟基苯甲酸（DHBA）、2,5-二羟基-1,4-苯醌、苯酚、苯甲酸和苯胺等7种化合物均可检测到H₂O₂产生.但其产生H₂O₂的速率差异较大,相差1~2个数量级,生成H₂O₂速率最快的化合物为2,5-二羟基-1,4-苯醌和DHBA,较慢的为苯酚、苯甲酸和对氨基苯甲酸.基于腐殖质生成H₂O₂机制,推测典型模型化合物DHBA的H₂O₂生成机制可能为光照条件下该化合物跃迁为单重激发态,该激发态发生分子内电子转移,生成还原性自由基中间体,该中间体和O₂反应,生成了超氧负离子（O₂·^-）,随后与水中H⁺反应生成了H₂O₂.     

Essential host plant cues in the grapevine moth

Host plant odours attract gravid insect females for oviposition. The identification of these plant volatile compounds is essential for our understanding of plant–insect relationships and contributes to plant breeding for improved resistance against insects. Chemical analysis of grape headspace and subsequent behavioural studies in the wind tunnel show that host finding in grapevine moth Lobesia botrana is encoded by a ratio-specific blend of three ubiquitous plant volatiles. The odour signal that attracts mated females to grape consists of the terpenoids (E)-β-caryophyllene, (E)-β-farnesene and (E)-4,8-dimethyl-1,3,7-nonatriene. These compounds represent only a fraction of the volatiles released by grapes, and they are widespread compounds known throughout the plant kingdom. Specificity may be achieved by the blend ratio, which was 100:78:9 in grape headspace. This blend elicited anemotactic behaviour in moths at remarkably small amounts. Females were attracted at release rates of only a few nanograms per minute, at levels nearly as low as those known for the attraction of male moths to the female sex pheromones.     

腐殖质及其模型化合物的H2O2光化学生成研究

在模拟太阳光下研究了多种腐殖质及其模型化合物的过氧化氢（H₂O₂）生成动力学,并对其生成机制进行了探讨.结果表明不同来源或不同形式的腐殖质在模拟太阳光照射下均能产生H₂O₂.不同腐殖质生成H₂O₂速率差异不大,范围为6.379~15.784nmol/（L·min）,腐殖酸生成H₂O₂速率略快于富里酸.对于腐殖质模型化合物,邻苯二酚、间苯二酚、对苯二酚、苯醌、邻茴香胺、对茴香胺、水杨酸和2,6-二甲氧基-1,4-苯醌等8种模型化合物没有产生明显的H₂O₂,而藜芦醇、对氨基苯甲酸、3,5-二羟基苯甲酸（DHBA）、2,5-二羟基-1,4-苯醌、苯酚、苯甲酸和苯胺等7种化合物均可检测到H₂O₂产生.但其产生H₂O₂的速率差异较大,相差1~2个数量级,生成H₂O₂速率最快的化合物为2,5-二羟基-1,4-苯醌和DHBA,较慢的为苯酚、苯甲酸和对氨基苯甲酸.基于腐殖质生成H₂O₂机制,推测典型模型化合物DHBA的H₂O₂生成机制可能为光照条件下该化合物跃迁为单重激发态,该激发态发生分子内电子转移,生成还原性自由基中间体,该中间体和O₂反应,生成了超氧负离子（O₂·^-）,随后与水中H⁺反应生成了H₂O₂.     

2-Nitroethenylbenzenes as natural products in millipede defense secretions

The white millipede Eucondylodesmus elegans Miyosi (Polydesmida: Doratodesmidae) secretes odoriferous droplets from the glands on both lateral surfaces of its body segments. The secretion was shown to be composed of a mixture of (1E)- and (1Z)-2-nitroethenylbenzenes (2-3 microg per millipede), identified by GC/MS analyses and synthesis. This is the first identification of these compounds as natural products. A granulated sugar block baited with the synthetic compound (more than 0.71 microg) demonstrated repellent activity against foraging wild ants, indicating that the compound functioned as a defense substance against potential predators. alpha,beta,2,3,4,5,6-d7-(1E)-2-Nitroethenylbenzene was detected by GC/MS analysis in the millipede secretion after feeding with alpha,beta,beta,2,3,4,5,6-d8-L-phenylalanine, indicating that L-phenylalanine is the precursor of these compounds.     

Identification of sex pheromone components of the pea midge, Contarinia pisi (Diptera: Cecidomyiidae)

 Three components in extract of pheromone glands of female pea midges, Contarinia pisi, were found to be active on male pea midge antennae by coupled gas chromatographic-electroantennographic detection. The EAD active components were identified as 2-acetoxytridecane, (2S,11S)-diacetoxytridecane, and (2S,12S)-diacetoxytridecane. A blend of these compounds proved to be highly attractive to males in windtunnel experiments. Received: 12 November 1998 / Accepted in revised form: 26 january 1999     

Products and mechanisms of the reactions of the nitrate radical (NO3) with isoprene, 1,3-butadiene and 2,3-dimethyl-1,3-butadiene in air

Products and mechanisms of the reaction of NO₃ with isoprene have been studied under simulated atmospheric conditions with in situ FTIR spectroscopy as analytical technique. The study addressed also the reactions of NO₃ with 1,3-butadiene and 2,3-dimethyl-1,3-butadiene as well as with the deuterated species 1,1,4,4-d₄-1,3-butadiene, d₆-1,3-butadiene and 4,4-d₂-2-methyl-1,3-butadiene (d₂-isoprene). The dienes examined apparently follow very similar reaction pathways. The decay of the intermediate peroxynitrates formed after the addition of NO₃ to one of the methylene groups, leads to unsaturated ketone-nitrate, aldehyde-nitrate, alcohol-nitrate and perhaps also dinitrate species. The yield of unsubstituted carbonyl compounds was insignificant in the reactions of NO₃ with 1,3-butadiene and isoprene. In the case of isoprene, NO₃ reacts adding preferentially to the 1-position and 3-methyl-4-nitroxy-2-butenal appears to be the main product. 1,3-Butadiene predominantly reacts with NO₃ via trans-1,4-addition and 1,2-addition while the cis-1,4-addition path is of minor importance. trans-4-Nitroxy-2-butenal and 1-nitroxy-3-buten-2-one were found as main products. Contrary to the daytime OH-initiated degradation of isoprene, the nighttime oxidation of isoprene by NO₃ leads to formation of large quantities of organic nitrate compounds; this may have consequences for the tropospheric NO_y budget as briefly discussed.     

Identification and electrophysiological studies of (4S,5S)-5-hydroxy-4-methyl-3-heptanone and 4-methyl-3,5-heptanedione in male lucerne weevils

An investigation to identify a sex or aggregation pheromone of Sitona discoideus Gyllenhål (Coleoptera: Curculionidae) is presented. Antenna flicking and attraction behaviors evoked by conspecifics of both sexes were recorded in arena bioassays, where attraction of females to males was observed. Air entrainment of both males and females was conducted in separate chambers. Gas chromatographic–mass spectrometric analysis of headspace volatiles revealed that two male-specific compounds, 4-methyl-3,5-heptanedione (major) and (4S,5S)-5-hydroxy-4-methyl-3-heptanone (minor), were emitted during the autumnal post-aestivatory flight period. The stereoisomers of the minor component were separated by enantioselective gas chromatography and their absolute configurations assigned by NMR (diastereomers) and the known preference of enantioselective transesterification reactions catalyzed by Candida antarctica lipase B. Electroantennogram and single sensillum recording studies indicate that 4-methyl-3,5-heptanedione as well as all individual stereoisomers of 5-hydroxy-4-methyl-3-heptanone are detected by the antennae of male and female S. discoideus. Further, single sensillum recordings suggest that both sexes of S. discoideus have specialized olfactory receptor neurons (ORNs) for detecting 4-methyl-3,5-heptanedione and different populations of stereoselective ORNs for detecting the stereoisomers of 5-hydroxy-4-methyl-3-heptanone. Some of these stereoselective ORNs appear to be sex-specific in S. discoideus.     

Evidence for contact sex recognition pheromone of the Asian longhorned beetle,<Emphasis Type="Italic"> Anoplophora glabripennis</Emphasis> (Coleoptera: Cerambycidae)

Field observations of the Asian longhorned beetle (Anoplophora glabripennis) mating behavior in China suggested that a female-produced contact pheromone was almost certainly involved in sex recognition. Gas chromatography–mass spectrometry (GC-MS) analysis of A. glabripennis adults' whole body cuticular extracts indicates that a series of long-chain hydrocarbons comprise the cuticular waxes of both sexes. Although for the most part the GC profiles are similar for the two sexes, five monounsaturated compounds were consistently more abundant in samples from females than in those from males. These compounds were identified as (Z)-9-tricosene, (Z)-9-pentacosene, (Z)-7-pentacosene, (Z)-9-heptacosene, and (Z)-7-heptacosene in the approximate ratio of 1:2:2:8:1, respectively. Antennal and palpi contact to a polypropylene micro-centrifuge tube coated with a synthetic mixture of the five compounds stimulated copulatory behavior in males.Electronic Supplementary Material  Supplementary material is available for this article if you access the article at . A link in the frame on the left on that page takes you directly to the supplementary material.     

拟柱孢藻生长及碱性磷酸酶活性对不同磷浓度和磷形态响应的株系间差异

拟柱孢藻(Cylindrospermopsis raciborskii)是热带地区普遍存在的蓝藻种类,近年来广泛扩张到温带地区水体,耐受低磷环境和多生态型的存在被认为是该藻能成功入侵的重要原因.为进一步了解不同藻株对磷波动的生理响应是否存在差异,本研究以广东省镇海水库分离的4株拟柱孢藻(N1、 N8、 N9和N10)为材料,观测它们的生长和碱性磷酸酶(ALP)活性在不同无机磷(Pi)浓度(HP=7.13 mg·L~(-1)、 MP=0.64 mg·L~(-1)、 LP=0.03 mg·L~(-1))和磷形态[磷酸氢二钾(K_2HPO_4)、焦磷酸钾(K_4P_2O_7)、三聚磷酸钾(K_5P_3O_(10))、 D-葡萄糖-6-磷酸(D-G-6-P)、三磷酸腺苷(ATP)、环磷酸腺苷(cAMP)]的变化.结果表明, 4株拟柱孢藻的生长对Pi浓度变化的响应基本一致,即它们的生物量都随Pi浓度的升高而增加,而ALP活性则反之;无论在LP、MP或HP条件下,N8藻株的ALP活性均显著低于其他3藻株,表明该藻株更能适应环境中的磷波动.在不同磷源培养下,拟柱孢藻N8和N9在3种无机磷下的生物量显著高于3种有机磷组,两者的比生长速率在K_2HPO_4最高,在ATP中最低,这表明拟柱孢藻偏好无机磷,但也能利用有机磷生长;在有机磷源条件下,N8藻株在ATP中的ALP活性显著高于其他2种有机磷,而N9藻株的ALP活性在3种有机磷培养下无显著差异,这表明N8藻株对无机磷缺乏的响应较N9藻株更为敏感.本结果表明来源于同一水库的拟柱孢藻藻株间存在显著差异,其中N8藻株对磷浓度变化的适应及响应能力均高于其它藻株.株系差异性的存在有利于拟柱孢藻适应各种环境变化,增强自身的竞争优势.     

(<Emphasis Type="Italic">Z</Emphasis>)-9-tricosene identified in rectal gland extracts of <Emphasis Type="Italic">Bactrocera oleae</Emphasis> males: first evidence of a male-produced female attractant in olive fruit fly

It is well-known that Bactrocera oleae (olive fruit fly) females attract conspecific males by using 1,7-dioxaspiro[5,5]undecane (1) as the main component of their sex pheromone, and that 1 is produced in the female rectal gland. Although some authors have claimed that B. oleae males also attract females, to date no male-produced female attractants have been found in this species. In this paper, we report the first identification of a substance unique to males and able to attract females. The findings of the study include the following: (1) females responded in a bioassay to hexane extracts obtained from rectal glands of 15-day-old B. oleae males, (2) the presence of (Z)-9-tricosene (2) was consistently and unambiguously identified in these extracts using gas chromatography (GC) and GC-mass spectrometry methods, (3) in preliminary bioactivity tests, low doses (equivalent to a few males) of chemically and stereoisomerically pure synthetic (Z)-9-tricosene (2) attracted olive fruit fly females. Interestingly, compound 2, commonly called muscalure, is also a well-known component of the house fly (Musca domestica) sex pheromone.     

Gustatory receptor neuron responds to DEET and other insect repellents in the yellow-fever mosquito, Aedes aegypti

Three gustatory receptor neurons were characterized for contact chemoreceptive sensilla on the labella of female yellow-fever mosquitoes, Aedes aegypti. The neuron with the smallest amplitude spike responded to the feeding deterrent, quinine, as well as N,N-diethyl-3-methylbenzamide and other insect repellents. Two other neurons with differing spikes responded to salt (NaCl) and sucrose. This is the first report of a gustatory receptor neuron specific for insect repellents in mosquitoes and may provide a tool for screening chemicals to discover novel or improved feeding deterrents and repellents for use in the management of arthropod disease vectors.     

Changes in Age-Related Reproductive Tactics in the Female of the Butterfly, Eurema hecabe

The occurrence of mate solicitation by virgin females was investigated in the butterfly Eurema hecabe. Young (1-day-old) virgin females rarely showed mate solicitation to male model, however, old (at least 6-day-old) virgin females frequently showed such flight. The duration of solicitation was significantly longer in older females than in younger ones. The age-related behavioral change occurs with female oogenesis (Hiroki and Kato 1996), and such behavior may thus be a result of female adaptation to maximize their fecundity. Received: 6 November 1997 / Accepted in revised form: 29 June 1998     

Reversed sex change by widowed males in polygynous and protogynous fishes: female removal experiments in the field

Sex change, either protogyny (female to male) or protandry (male to female), is well known among fishes, but evidence of bidirectional sex change or reversed sex change in natural populations is still very limited. This is the first report on female removal experiments for polygnous and protogynous fish species to induce reversed sex change in the widowed males in the field. We removed all of the females and juveniles from the territories of dominant males in the cleaner wrasse Labroides dimidiatus (Labridae) and the rusty angelfish Centropyge ferrugata (Pomacanthidae) on the coral reefs of Okinawa. In both species, if new females or juveniles did not immigrate into the territories of the widowed males, some of them emigrated to form male–male pairs. When a male–male pair formed, the smaller, subordinate partner began to perform female sexual behaviours (n = 4 in L. dimidiatus; n = 2 in C. ferrugata) and, finally, released eggs (n = 1, respectively). Thus, the reversed sex change occurred in the widowed males according to the change of their social status. These results suggest that such female removal experiments will contribute to the discovery of reversed sex change in the field also in other polygnous and protogynous species.     

Evidence for a male-produced pheromone in <Emphasis Type="Italic">Tetropium fuscum</Emphasis> (F.) and <Emphasis Type="Italic">Tetropium cinnamopterum</Emphasis> (Kirby) (Coleoptera: Cerambycidae)

(E)-6,10-dimethyl-5,9-undecadien-2-ol (geranyl acetol), termed here fuscol, was identified as a male-produced pheromone emitted by Tetropium fuscum (F.) and Tetropium cinnamopterum Kirby. In field experiments, traps baited with synthetic fuscol alone were not significantly attractive, but the combination of fuscol plus host volatiles (a synthetic blend of monoterpenes plus ethanol) attracted significantly more male and female T. fuscum and female T. cinnamopterum than did host volatiles alone. This is the first homoterpenoid alcohol to be described in the Cerambycidae, and the first pheromone reported from the sub-family Spondylidinae.     

Efficient Transmission of an Introduced Pathogen Via an Ancient Insect-Fungus Association

 In Cupressus sempervirens the association between seed insects and tree pathogens has resulted in optimal exploitation of the cones. A fungus-infected cone can be inhabited by the nymphs of a true seed bug (Orsillus maculatus), the adults of which may carry a heavy spore load at emergence. Cones are infected when eggs are laid within the cone, most frequently via the emergence holes of a seed wasp (Megastigmus wachtli). This symbiotic association evolved with the nonaggressive fungus Pestalotiopsis funerea within the natural range of the cypress. When the aggressive cypress canker disease (Seiridium cardinale) was introduced into Europe, it was transmitted by O. maculatus to cones usually colonized by Pestalotiopsis funerea, with disastrous consequences for the regeneration and survival of C. sempervirens in the entire Mediterranean area. Received: 30 November 1998 / Accepted in revised form: 17 May 1999     

臭氧耦合陶瓷膜过滤对膜性能及出水消毒副产物的影响

利用臭氧（O₃）-陶瓷膜过滤（CMF）处理常规工艺出水,研究了不同O₃-CMF耦合方式对膜性能和消毒副产物（DBPs）的影响.结果表明,与单独CMF相比,异位O₃-CMF和原位O₃-CMF均可以有效缓解膜污染,原位O₃-CMF控制效果最佳.异位O₃-CMF对进水（常规工艺出水） DOC去除率（26.25%）略高于原位O₃-CMF（22.31%）,但是其SUVA去除率（83.91%）明显低于原位O₃-CMF（93.10%）.羟基自由基（·OH）生成特征表明原位O₃-CMF可促进O₃产生更多的·OH.在O₃、·OH氧化和陶瓷膜截留协同作用下,异位O₃-CMF和原位O₃-CMF出水中总荧光响应强度和相对分子质量大于0.3×10³,有机物含量降低,进而使得出水中含碳消毒副产物（C-DBPs）生成量分别降低了21.86%和32.35%,含氮消毒副产物（N-DBPs）生成量分别降低了16.16%和19.13%.但O₃和·OH氧化后生成的小分子有机物因难以被CM截留导致其在出水中含量增加,进而增加了卤代酮（HKs）、水合氯醛（CH）和三卤硝基甲烷（THNMs）的产生.本研究对于不同O₃-CMF方式下O₃与CM的协同机制的探讨,改善膜性能和提升DBPs前体物的去除具有一定指导意义.     

Mastrus ridibundus parasitoids eavesdrop on cocoon-spinning codling moth, Cydia pomonella, larvae

Cocoon-spinning larvae of the codling moth, Cydia pomonella L. (Lepidoptera: Olethreutidae) employ a pheromone that attracts or arrests conspecifics seeking pupation sites. Such intraspecific communication signals are important cues for illicit receivers such as parasitoids to exploit. We tested the hypothesis that the prepupal C. pomonella parasitoid Mastrus ridibundus Gravenhorst (Hymenoptera: Ichneumonidae) exploits the larval aggregation pheromone to locate host prepupae. In laboratory olfactometer experiments, female M. ridibundus were attracted to 3-day-old cocoons containing C. pomonella larvae or prepupae. Older cocoons containing C. pomonella pupae, or larvae and prepupae excised from cocoons, were not attractive. In gas chromatographic-electroantennographic detection (GC-EAD) analyses of bioactive Porapak Q extract of cocoon-derived airborne semiochemicals, ten compounds elicited responses from female M. ridibundus antennae. Comparative GC-mass spectrometry of authentic standards and cocoon-volatiles determined that these compounds were 3-carene, myrcene, heptanal, octanal, nonanal, decanal, (E)-2-octenal, (E)-2-nonenal, sulcatone, and geranylacetone. A synthetic 11-component blend consisting of these ten EAD-active compounds plus EAD-inactive (+)-limonene (the most abundant cocoon-derived volatile) was as effective as Porapak Q cocoon extract in attracting both female M. ridibundus and C. pomonella larvae seeking pupation sites. Only three components could be deleted from the 11-component blend without diminishing its attractiveness to M. ridibundus, which underlines the complexity of information received and processed during foraging for hosts. Mastrus ridibundus obviously eavesdrop on the pheromonal communication signals of C. pomonella larvae that reliably indicate host presence.

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