Chirality determines pheromone activity for flour beetles

Olfactory perception and orientation behaviour of female and male flour beetles (Tribolium castaneum, T. confusum) to single stereoisomers of their aggregation pheromone revealed maximal receptor potentials and optimal attraction in response to 4R,8R-(?)-dimethyldecanal, whereas its optical antipode 4S,8S-(+)-dimethyldecanal was found to be inactive in this respect. Female flour beetles of both species were ≈ 10³ times less attracted to 4R,8S-(+)- and 4S,8R-(?)-dimethyldecanal than to 4R,8R-(?)-dimethyldecanal, while male flour beetles failed to respond to the R,S-(+)- and S,R-(?)-stereoisomers. Pheromone extracts of prothoracic femora from unmated male flour beetles elicited higher receptor potentials in the antennae of females than in those of males. The results suggest that the aggregation pheromone emitted by maleT. castaneum as well as maleT. confusum has the stereochemical structure of 4R,8R-(?)-dimethyl-decanal, which acts as sex attractant for the females and as aggregant for the males of both species.     

Rac-及S-异丙甲草胺对2种微藻毒性特征影响研究

应用急性毒性试验方法,在对映体水平上研究了除草剂Rac-及S-异丙甲草胺对斜生栅藻(Scenedesmus obliquus)和普通核小球藻(Chlorella vulgaris)的急性毒性特征及腐殖酸对除草剂毒性的影响.结果表明,Rac-及S-异丙甲草胺的急性毒性与浓度及暴露时间呈正相关,Rac-及S-异丙甲草胺对微藻细胞的急性毒性存在立体选择性差异.Rac-异丙甲草胺对普通核小球藻和斜生栅藻的EC50,96 h分别是S-异丙甲草胺的2.25和1.81倍,S-异丙甲草胺对微藻细胞的生态毒性较大,而斜生栅藻对Rac-及S-异丙甲草胺的敏感性更强,且Rac-及S-异丙甲草胺对斜生栅藻和普通核小球藻的急性毒性存在一定的线性相关性.腐殖酸的加入能够改变Rac-及S-异丙甲草胺对微藻细胞生态毒性,对S-异丙甲草胺的生态毒性的影响更为明显(P<0.05).     

镉与S-异丙甲草胺对斜生栅藻的联合毒性作用

采用毒性标准实验方法研究了Cd2+与S-异丙甲草胺单独及联合作用对斜生栅藻急性毒性、总可溶性蛋白含量、超氧化物歧化酶(SOD)活性和细胞膜通透性的影响.结果表明Cd2+与S-异丙甲草胺单独作用时EC50均随时间的延长而减小,且S-异丙甲草胺的急性毒性大于Cd2+;Cd2+、S-异丙甲草胺的EC50-24h分别为0.27 mg·L-1、0.24 mg·L-1,EC50-96h分别为0.16mg·L-1、0.13 mg·L-1.Cd2+与S-异丙甲草胺联合作用时低浓度表现为协同作用,高浓度表现为拮抗作用.暴露96 h后,Cd2+与S-异丙甲草胺单独及联合作用下,随有毒物质浓度升高,斜生栅藻总可溶性蛋白含量降低,SOD酶活性先激活后抑制,细胞膜通透性逐渐增大.     

Sex pheromone component ratios and mating isolation among three Lygus plant bug species of North America

The plant bugs Lygus hesperus, Lygus lineolaris, and Lygus elisus (Hemiptera: Miridae) are major pests of many agricultural crops in North America. Previous studies suggested that females release a sex pheromone attractive to males. Other studies showed that males and females contain microgram amounts of (E)-4-oxo-2-hexenal, hexyl butyrate, and (E)-2-hexenyl butyrate that are emitted as a defense against predators. Using gas chromatography–mass spectrometry, we found that female L. lineolaris and L. elisus have a 4:10 ratio of hexyl butyrate to (E)-2-hexenyl butyrate that is reversed from the 10:1 ratio in female L. hesperus (males of the three species have ~10:1 ratio). These reversed ratios among females of the species suggest a behavioral role. Because both sexes have nearly equal amounts of the major volatiles, females should release more to attract males. This expectation was supported because L. hesperus females released more hexyl butyrate (mean of 86 ng/h) during the night (1800–0700 hours) than did males (<1 ng/h). We used slow-rotating pairs of traps to test the attraction of species to blends of the volatiles with a subtractive method to detect synergism. Each species’ major butyrate ester was released at 3 μg/h, the minor butyrate according to its ratio, and (E)-4-oxo-2-hexenal at 2 μg/h. The resulting catches of only Lygus males suggest that (E)-4-oxo-2-hexenal is an essential sex pheromone component for all three species, (E)-2-hexenyl butyrate is essential for L. elisus and L. lineolaris, and hexyl butyrate is essential for L. hesperus. However, all three components are recognized by each species since ratios of the butyrate esters are critical for conspecific attraction and heterospecific avoidance by males and thus play a role in reproductive isolation among the three species. Because L. hesperus males and females are known to emit these major volatiles for repelling ant predators, our study links defensive allomones in Lygus bugs with an additional use as sex pheromones.     

Porous FeOx/BiVO4-δS0.08：Highly efficient photocatalysts for the degradation of Methylene Blue under visible-light illumination

Porous S-doped bismuth vanadate with an olive-like morphology and its supported iron oxide （y wt.% FeOx/BiVO4-δS0.08, y = 0.06, 0.76, and 1.40） photocatalysts were fabricated using the dodecylamine-assisted alcohol-hydrothermal and incipient wetness impregnation methods, respectively. It is shown that the y wt.% FeOx/BiVO4-δS0.08 photocatalysts contained a monoclinic scheetlite BiVO4 phase with a porous olive-like morphology, a surface area of 8.8-9.2 m^2/g, and a bandgap energy of 2.38-2.42 eV. There was co-presence of surface Bi^5＋, Bi^3＋, V^5＋, V^3＋, Fe^3＋, and Fe^2＋ species in y wt.% FeOx/BiVO4-δS0.08. The 1.40 wt.% FeOx/BiVO4-δS0.08 sample performed the best for Methylene Blue degradation under visible-light illumination. The photocatalytic mechanism was also discussed. We believe that the sulfur and FeOx co-doping, higher oxygen adspecies concentration, and lower baudgap energy were responsible for the excellent visible-light-driven catalytic activity of 1.40 wt.% FeOx/BiVO4-δS0.08.     

Anatomical localization and stereoisomeric composition of <Emphasis Type="Italic">Tribolium castaneum</Emphasis> aggregation pheromones

We report that the abdominal epidermis and associated tissues are the predominant sources of male-produced pheromones in the red flour beetle, Tribolium castaneum and, for the first time, describe the stereoisomeric composition of the natural blend of isomers of the aggregation pheromone 4,8-dimethyldecanal (DMD) in this important pest species. Quantitative analyses via gas chromatography–mass spectrometry showed that the average amount of DMD released daily by single feeding males of T. castaneum was 878 ± 72 ng (SE). Analysis of different body parts identified the abdominal epidermis as the major source of aggregation pheromone; the thorax was a minor source, while no DMD was detectable in the head. No internal organs or obvious male-specific glands were associated with pheromone deposition. Complete separation of all four stereoisomers of DMD was achieved following oxidation to the corresponding acid, derivatization with (1R, 2R)- and (1S, 2S)-2-(anthracene-2,3-dicarboximido)cyclohexanol to diastereomeric esters, and their separation on reversed-phase high-performance liquid chromatography at −54°C. Analysis of the hexane eluate from Porapak-Q-collected volatiles from feeding males revealed the presence of all four isomers (4R,8R)/(4R,8S)/(4S,8R)/(4S,8S) at a ratio of approximately 4:4:1:1. A walking orientation bioassay in a wind tunnel with various blends of the four synthetic isomers further indicated that the attractive potency of the reconstituted natural blend of 4:4:1:1 was equivalent to that of the natural pheromone and greater than that of the 1:1 blend of (4R,8R)/(4R,8S) used in commercial lures.     

Sex pheromone of orange wheat blossom midge, Sitodiplosis mosellana

 Pheromone extract of the female orange wheat blossom midge, Sitodiplosis mosellana (Géhin) (SM) (Diptera: Cecidomyiidae), was analyzed by coupled gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometry (MS), employing fused silica columns coated with DB-5, DB-210, DB-23 or SP-1000. These analyses revealed a single, EAD-active candidate pheromone which was identified as 2,7-nonanediyl dibutyrate. In experiments in wheat fields in Saskatchewan, traps baited with (2S,7S)-2,7-nonanediyl dibutyrate attracted significant numbers of male SM. The presence of other stereoisomers did not adversely affect trap captures. Facile synthesis of stereoisomeric 2,7-nonanediyl dibutyrate will facilitate the development of pheromone-based monitoring or even control of SM populations. Received: 2 March 2000 / Accepted in revised form: 18 August 2000     

一株架桥细菌的共凝集能力及强化生物膜反应器效能的研究

测定了架桥细菌Bacillus cereus G5与活性污泥中分离得到的13株土著细菌及3株复杂有机物降解菌配对组合后的共凝集能力和成膜能力.结果表明:凝集2 h和20 h时的共凝集率分别达到40%~70%和55%~80%;架桥细菌与其中15株细菌混合培养时的生物膜形成量高于单菌培养时的生物膜量.这表明在废水处理系统外G5能与土著菌和降解菌发生较强程度的共凝集,并可促进多数菌株生物膜量的增加.进一步考察了G5与3,5-二硝基苯甲酸降解菌Comamonas testosterone A3投加到序批式生物膜反应器(SBBR)中的生物强化效果.32 d的运行结果表明,同时投加A3与G5菌株的反应器,24 h时出水中3,5-二硝基苯甲酸由100.0 mg·L-1降解至10.1 mg·L-1,降解最快;3,5-硝基苯甲酸负荷由100 mg·L-1增加到1000 mg·L-1的运行过程中,平均降解率稳定在65.0%~88.1%的范围内,表现出最强的抗冲击能力;生物膜量在1.4~2.0 mg·cm-2之间,比其他两组反应器同期时的生物膜量略高.表明在废水处理系统内Bacillus cereus G5亦可能通过其广泛的共凝集能力,促进反应器中生物膜的形成,并辅助降解菌以自固定化方式定殖于生物膜,从而表现出快速的生物强化作用和较强的抗冲击能力.     

Attraction of two lacewing species to volatiles produced by host plants and aphid prey

It is well documented that host-related odors enable many species of parasitoids and predatory insects to locate their prey and prey habitats. This study reports the first characterization of prey and prey host odor reception in two species of lacewings, Chrysoperla carnea (Say) and Chrysopa oculata L. 2-Phenylethanol, one of the volatiles emitted from their preys host plants (alfalfa and corn) evoked a significant EAG response from antennae of C. carnea. Traps baited with this compound attracted high numbers of adult C. carnea, which were predominantly females. One of the sex pheromone components (1R,4aS,7S,7aR)-nepetalactol of an aphid species, Acyrthosiphon pisum (Harris) attracted only C. oculata adults. Single sensillum recordings showed that the olfactory neurons of C. carnea responded to both 2-phenylethanol and aphid sex pheromone components, but those of C. oculata only responded to the latter.     

Biosynthesis of the defensive alkaloid cicindeloine in Stenus solutus beetles

To protect themselves from predation and microorganismic infestation, rove beetles of the genus Stenus produce and store bioactive alkaloids like stenusine, 3-(2-methyl-1-butenyl)pyridine, and cicindeloine in their pygidial glands. The biosynthesis of stenusine and 3-(2-methyl-1-butenyl)pyridine was previously investigated in Stenus bimaculatus and Stenus similis, respectively. Both molecules follow the same biosynthetic pathway, where the N-heterocyclic ring is derived from l-lysine and the side chain from l-isoleucine. The different alkaloids are finally obtained by slight modifications of shared precursor molecules. The piperideine alkaloid cicindeloine occurs as a main compound additionally to (E)-3-(2-methyl-1-butenyl)pyridine and traces of stenusine in the pygidial gland secretion of Stenus cicindeloides and Stenus solutus. Feeding of S. solutus beetles with [D,¹⁵N]-labeled amino acids followed by GC/MS analysis techniques showed that cicindeloine is synthesized via the identical pathway and precursor molecules as the other two defensive alkaloids.     

(3R,4S)-Methyl-3-heptanol,the trail pheromone of the ant Leptogenys diminuta

We wish to thank Prof. V. Schurig (Tübingen) for lending us the columns for preliminary studies, and Prof. K. Mori (Tokyo), N. Frighetto and R. T. S. Frighetto (Erlangen) for optically active samples of 4-methyl-3-heptanol. This work was supported by the Deutsche Forschungsgemeinschaft.     

手性农药丁氟螨酯对斑马鱼胚胎的选择性发育毒性

近年来丁氟螨酯（CYF）对非靶标生物的发育毒性已成为一个值得关注的问题,但其对水生生物的对映选择性效应尚不清晰.为评估丁氟螨酯对斑马鱼胚胎的对映选择性毒性,通过96 h的暴露试验,研究了梯度浓度的丁氟螨酯消旋体及对映体对斑马鱼胚胎的急性毒性.此外,试验还研究了丁氟螨酯对斑马鱼胚胎孵化率、卵黄囊水肿、心包囊水肿和身体弯曲的影响.根据急性毒性结果可知,毒性大小为S-CYF > Rac-CYF > R-CYF,其中S-CYF的毒性是R-CYF的2.3倍.72 hpf,500 mg·L^-1的S-CYF可显著诱导胚胎产生卵黄囊水肿（YSE）、体轴弯曲（CB）等畸形效应（p<0.05）,而Rac-CYF降低了斑马鱼胚胎的孵化成功率.在本研究中发育毒性效应结果与急性毒性结果一致,均为S-CYF > Rac-CYF > R-CYF,表明丁氟螨酯对斑马鱼胚胎存在显著的对映选择性发育毒性,研究结果为丁氟螨酯的环境风险评估提供了理论依据.     

Chemical analysis of succinylacetone and 4-hydroxyphenyllactate in amniotic fluid using selective ion monitoring

A method for the measurement of the concentration of succinylacetone and 4-hydroxyphenyllactic acid in amniotic fluid was developed for the prenatal diagnosis of hereditary tyrosinemia. Succinylacetone was converted to 5-methyl-3-isoxazolepropionic acid and isolated with 4-hydroxyphenyllactic acid by liquid partition chromatography and the trimethylsilyl derivatives quantified by ammonia chemical ionization selected ion monitoring gas chromatography-mass spectrometry with 2-hydroxy-n-caproic acid as the internal standard. The concentration of 4-hydroxyphenyllactic acid in normal amniotic fluid was 1.97±0.75 (S.D.) μmol/l while succinylacetone was undetectable. A pregnancy at risk for tyrosinemia type II was monitored. The concentration of 4- hydroxyphenyllactic acid was within the normal range and a healthy child was born.     

废水同步脱硫脱氮关键工艺参数及微生物群落结构的研究

大量未经处理的含硫化物和硝酸盐废水的排放将带来严重的环境问题.根据以废治废原则,使用厌氧滴滤塔反应器构建的同步脱硫耦联反硝化脱氮反应(SDD)能很好的去除废水中S~(2-)和NO-x-N.其中以聚氨酯泡沫为填料的厌氧滴滤塔反应器中生物活性最强,脱氮脱硫效果最好.体系中功能菌优先将S~(2-)氧化成S0,待S~(2-)去除完全后,再进一步将S0氧化成SO_4~(2-).同时,SDD反应降解NO_3~--N的速率快于NO_2~--N.进水S/N摩尔比越大,产物中SO_4~(2-)相对含量越低.结合实际工程考虑,应控制进水S/N摩尔比在5/3~5/2之间,S~(2-)浓度控制在538 mg·L-1以下.微生物群落结构分析结果表明,Thiobacillus属在4组反应器上占绝对优势,其相对丰度均高于40%.其次相对丰度较高的Rhodanobacter、Arenimonas和Truepera属与厌氧反硝化作用密切相关.对4组反应器中微生物进行Alpha-多样性分析结果表明取得较好脱硫耦联反硝化效果的体系中物种多样性指数也较高.     

Degradation of 2-methyl-4-chlorophenoxyacetic acetic acid in air-dry soils

Two typical air-dry soils were treated with 2-methyl-4-chlorophenoxyacetic acid (MCPA) at concentrations of 10, 100, 500 and 2000 ppm, and kept in plastic containers in the open from April 1978 to November 1979 (579 days). Five samples of each soil were extracted at intervals in order to study the residues remaining using gas chromatography (GC). A very slow degradation of MCPA was observed in both soils and the compound was fully stable during winter at a temperature below 0°C.     

Biodegradation of 2-methylquinoline by Enterobacter aerogenes TJ-D isolated from activated sludge

Bacterial strain Enterobacter aerogenes TJ-D capable of utilizing 2-methylquinoline as the sole carbon and energy source was isolated from acclimated activated sludge under denitrifying conditions. The ability to degrade 2-methylquinoline by E. aerogenes TJ-D was investigated under denitrifying conditions. Under optimal conditions of temperature (35℃) and initial pH 7, 2-methylquinoline of 100 mg/L was degraded within 176 hr. The degradation of 2-methylquinoline by E. aerogenes TJ-D could be well described by the Haldane model (R² > 0.91). During the degradation period of 2-methylquinoline (initial concentration 100 mg/L), nitrate was almost completely consumed (the removal efficiency was 98.5%), while nitrite remained at low concentration (< 0.62 mg/L) during the whole denitrification period. 1,2,3,4-Tetrahydro-2-methylquinoline, 4-ethyl-benzenamine, N-butyl-benzenamine, N-ethyl-benzenamine and 2,6-diethyl-benzenamine were metabolites produced during the degradation. The degradation pathway of 2-methylquinoline by E. aerogenes TJ-D was proposed. 2-Methylquinoline is initially hydroxylated at C-4 to form 2-methyl-4-hydroxy-quinoline, and then forms 2-methyl-4-quinolinol as a result of tautomerism. Hydrogenation of the heterocyclic ring at positions 2 and 3 produces 2,3-dihydro-2-methyl-4-quinolinol. The carbon-carbon bond at position 2 and 3 in the heterocyclic ring may cleave and form 2-ethyl-N-ethyl-benzenamine. Tautomerism may result in the formation of 2,6-diethyl-benzenamine and N-butyl-benzenamine. 4-Ethyl-benzenamine and N-ethyl-benzenamine were produced as a result of losing one ethyl group from the above molecules.     

Isolation and characterization of mesophilic,oxalate-degrading<Emphasis Type="Italic"> Streptomyces</Emphasis> from plant rhizosphere and forest soils

The present work was aimed at the isolation of additional new pure cultures of oxalate-degrading Streptomyces and its preliminary characterization for further work in the field of oxalate metabolism and taxonomic studies. Mesophilic, oxalate-degrading Streptomyces were enriched and isolated from plant rhizosphere and forest soil samples. Strains were examined for cultural, morphological (spore chain morphology, spore mass colour, diffusible and melanin pigment production), physiological (antibiosis, growth in the presence of inhibitory compounds, assimilation of organic acids and enzyme substrates) and chemotaxonomic characters (cellular lipid components and diagnostic cell-wall diamino acid). The taxonomic data obtained were analysed by using the simple matching (S_SM) and Jaccard (S_J) coefficients, clustering was achieved using the UPGMA algorithm. All strains were able to utilize sodium-, potassium-, calcium- and ammonium-oxalate salts. Based on the results of numerical taxonomy, isolates were grouped into five cluster groups with a 70% S_SM similarity level. Streptomyces rochei was the most common of the cluster groups, with a Willcox probability of P>0.8. Streptomyces antibioticus, S. anulatus, S. fulvissimus, S. halstedii and S. violaceusniger are newly reported as oxalate-utilizing Streptomyces.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.     

A versatile and effective trap for detecting and monitoring stored-product coleoptera

An efficient multi-species trap of corrugated paper and utilizing plastic pitfall devices containing a vegetable-oil based food attractant, was developed for the purpose of detecting and monitoring stored-product insects. Adults of Oryzaephilus surinamensis (L.), Tribolium confusum Jacquelin duVal and larvae of Trogoderma variabile Ballion were trapped successfully in laboratory assays.Using a multiple-choice olfactometer, Tribolium confusum and Tribolium castaneum (Herbst) adults were shown to respond to 4,R-8,R-dimethyldecanal, their natural aggregation pheromone, and to distinguish between this and other diastereomers when tested simultaneously. The S-R and S-S diastereomers may be slightly inhibitory to T. castaneum response. Tribolium confusum was attracted to racemic 4, 8-dimethyldecanal applied to rubber septa lures. High doses of the pheromone reduced attraction. The pheromone is currently being used with food attractants in the trap for monitoring field populations of Tribolium and other stored-product insects.     

Skimming behaviour and spreading potential of Stenus species and Dianous coerulescens (Coleoptera: Staphylinidae)

Rove beetles of the genus Stenus Latreille and the genus Dianous Leach possess pygidial glands containing a multifunctional secretion of piperidine and pyridine-derived alkaloids as well as several terpenes. One important character of this secretion is the spreading potential of its different compounds, stenusine, norstenusine, 3-(2-methyl-1-butenyl)pyridine, cicindeloine, α-pinene, 1,8-cineole and 6-methyl-5-heptene-2-one. The individual secretion composition enables the beetles to skim rapidly and far over the water surface, even when just a small amount of secretion is emitted. Ethological investigations of several Stenus species revealed that the skimming ability, skimming velocity and the skimming behaviour differ between the Stenus species. These differences can be linked to varied habitat claims and secretion saving mechanisms. By means of tensiometer measurements using the pendant drop method, the spreading pressure of all secretion constituents as well as some naturally identical beetle secretions on the water surface could be established. The compound 3-(2-methyl-1-butenyl)pyridine excelled stenusine believed to date to be mainly responsible for skimming relating to its surface activity. The naturally identical secretions are not subject to synergistic effects of the single compounds concerning the spreading potential. Furthermore, evolutionary aspects of the Steninae’s pygidial gland secretion are discussed.     

Dissolution of different zinc salts and Zn uptake by Sedum alfredii and maize in mono- and co-cropping under hydroponic culture

Previous soil pot and field experiments demonstrated that co-cropping the hyperaccumulator Sedum alfredii with maize increased Zn phytoextraction by S. alfredii and decreased Zn uptake by maize shoots. This hydroponic experiment was conducted to investigate whether the facilitation of Zn phytoextraction by S. alfredii resulted from improved dissolution in this co-cropping system and its relation to root exudates. S. alfredii and maize were mono-and co-cropped (without a root barrier) in nutrient solution spiked with four Zn compounds, ZnS, ZnO, Zn3(PO4)2 and 5ZnO·2CO3·4H2O (represented as ZnCO3 ) at 1000 mg/L Zn for 15 days without renewal of nutrient solution after pre-culture. The root exudates were collected under incomplete sterilization and analyzed. The results indicated that the difference in Zn salts had a greater influence on the Zn concentration in maize than for S. alfredii, varying from 210-2603 mg/kg for maize shoots and 6445-12476 mg/kg for S. alfredii in the same order: ZnCO3 > ZnO >Zn3(PO4)2 > ZnS. For the four kinds of Zn sources in this experiment, co-cropping with maize did not improve Zn phytoextraction by S. alfredii. In most cases, compared to co-cropped and mono-cropped maize, mono-cropped S. alfredii resulted in the highest Zn2+ concentration in the remaining nutrient solution, and also had a higher total concentration of low molecular weight organic acids (LMWOA) and lower pH of root exudation. Root exudates did partly influence Zn hyperaccumulation in S. alfredii.