Two new icosapentaenoic acids from the temperate red seaweedPtilota filicina J. Agardh

Two new fatty acid metabolites, 5(Z),7(E),9(E),14(Z),17(Z)-icosapentaenoic acid and 5(E),7(E),9(E),14(Z),17(Z)-icosapentaenoic acid, have been isolated from the temperate red marine alga,Ptilota filicina (Ceramiales, Rhodophyta). The structures of these new compounds, isolated as their methyl ester derivatives, have been deduced from detailed¹H nuclear magnetic resonance (NMR),¹³C NMR and 2D-NMR analyses as well as comparisons to known compounds.     

Isolation and structures of two divinyl ether fatty acids from <Emphasis Type="Italic">Clematis vitalba</Emphasis>

[1-14C]Linolenic acid was incubated with a homogenate of leaves of Clematis vitalba, a plant belonging to the Ranunculaceae family. Analysis of the reaction product by reversed-phase high-performance liquid radiochromatography demonstrated the presence of the following labeled oxylipins: 12-oxo-10, 15(Z)-phytodienoic acid, 9(S)-hydroxy-10(E), 12(Z), 15(Z)-octadecatrienoic acid, omega5(Z)-etherolenic acid, and 9-[1'(E), 3'(Z),6'(Z)-nonatrienyloxy]-8(Z)-nonenoic acid [8(Z)-colnelenic acid]. The last compound was a new divinyl ether FA, and an analogous compound, i.e., 9-[1'(E),3'(Z)-nonadienyloxy]-8(Z)-nonenoic acid [8(Z)-colneleic acid], was obtained following incubation of linoleic acid with the Clematis homogenate. Structures of the two divinyl ethers were assigned by spectral and chromatographic comparison with authentic compounds prepared synthetically using previously described methodology. Separate incubation of the 9- and 13-hydroperoxides of linolenic acid demonstrated that the first hydroperoxide served as the precursor of 8(Z)-colnelenic acid and indicated the presence in C. vitalba of a new divinyl ether synthase acting on 9-lipoxygenase-generated hydroperoxides. A close structural relationship between this enzyme and the well-studied divinyl ether synthase in the potato and tomato seems likely.     

Heritable Variation in the Sex Pheromone of the Almond Moth, Cadra cautella

The sex pheromone of the female almond moth, Cadra cautella, constitutes a highly variable signal. Age and period of the L/D cycle had significant effects on the variation in titers of (Z,E)-9,12-tetradecadienyl acetate (Z9,E12-14:Ac) and (Z)-9-tetradecenyl acetate (Z9-14:Ac) and the ratio of Z9,E12-14:Ac to Z9-14:Ac. Across age classes, minimum and maximum mean titers (ng +/- SE) of Z9,E12-14:Ac and Z9-14:Ac ranged from 8.7 +/- 0.46 to 21 +/- 1.0 and from 2.0 +/- 0.14 to 2.9 +/- 0.15, respectively; the mean ratio of Z9,E12-14:Ac to Z9-14:Ac ranged from 5.2 +/- 0.21 to 11 +/- 0.40. The titers of Z9,E12-14:Ac and Z9-14:Ac and the ratio of Z9,E12-14:Ac to Z9-14:Ac were highest at the onset of the scotophase and lowest at the onset of the photophase. Similarly, the titer of Z9,E12-14:Ac and the ratio of Z9,E12-14:Ac to Z9-14:Ac were highest in females sampled 1 d postemergence and declined over all age classes. The titer of Z9-14:Ac increased from day 1 to day 2, and then declined to levels equivalent to day 1. Analysis of pupal and adult mass demonstrated a positive correlation (r = 0.874, P < 0.001); however, the titer of neither Z9,E12-14:Ac or Z9-14:Ac nor the ratio of Z9,E12-14:Ac to Z9-14:Ac were significantly correlated with pupal mass. Age-related variations in pheromone titer and ratios were heritable. The narrow-sense heritability of the observed variation in 1-d-old females, 1 hr into the scotophase is 1.2 +/- 0.32, 0.75 +/- 0.24, and 0.46 +/- 0.17 for the titer of Z9,E12-14:Ac and Z9-14:Ac and the ratio of Z9,E12-14:Ac to Z9-14:Ac, respectively. A significant additive genetic correlation was observed between that of Z9,E12-14:Ac and Z9-14:Ac, but not between that of either Z9,E12-14:Ac or Z9-14:Ac and the ratio of Z9,E12-14:Ac to Z9-14:Ac. The results of the genetic analyses suggest that the traits of titer of Z9,E12-14:Ac and Z9-14:Ac have a greater potential to respond to selection than the trait of ratio of Z9,E12-14:Ac to Z9-14:Ac.     

Synthesis of 3-oxalinolenic acid and β-oxidation-resistant 3-oxa-oxylipins

3-Oxalinolenic acid (3-oxa-9(Z), 12(Z), 15(Z)-octadecatrienoic acid or (6(Z), 9(Z), 12(Z)-pentadecatrienyloxy)acetic acid) was synthesized from 5(Z), 8(Z), 11(Z), 14(Z), 17(Z)-eicosapentaenoic acid by a sequence involving the C15 aldehyde 3(Z), 6(Z), 9(Z), 12(Z)-pentadecatetraenal as a key intermediate. Conversion of the aldehyde by isomerization and two steps of reduction afforded 6(Z), 9(Z), 12(Z)-pentadecatrienol, which was coupled to bromoacetate to afford after purification by HPLC >99%-pure 3-oxalinolenic acid in 10–15% overall yield. 3-Oxalinolenic acid was efficiently oxygenated by soybean lipoxygenase-1 into 3-oxa-13(S)-hydroperoxy-9(Z), 11(E), 15(Z)-octadecatrienoic acid, and this hydroperoxide could be further converted chemically into 3-oxa-13(S)-hydroxy-9(Z), 11(E), 15(Z)-octadecatrienoic acid and 3-oxa-13-oxo-9(Z), 11(E), 15(Z)-octadecatrienoic acid. The 3-oxa-hydroperoxide also served as the substrate for the plant enzymes allene oxide synthase, divinyl ether synthase, and hydroperoxide lyase to produce 3-oxa-12-oxo-10, 15(Z)-phytodienoic acid and other 3-oxa-oxylipins that were characterized by MS, 3-Oxalinolenic acid was not oxygenated by 9-lipoxygenase from tomato but was converted at a slow rate into 3-oxa-9(S)-hydroperoxy-10(E), 12(Z), 15(Z)-octadecatrienoic acid by recombinant maize 9-lipoxygenase. Recombinant α-dioxygenase-1 from Arabidopsis thaliana catalyzed the conversion of 3-oxalinolenic acid into a 2-hydroperoxide, which underwent spontaneous degradation into a mixture of 6,9,12-pentadecatrienol and 6,9,12-pentadecatrienyl formate. A novel α-dioxygenase from the moss Physcomitrella patens was cloned and expressed and was found to display the same activity with 3-oxalinolenic acid as Arabidopsis thaliana α-dioxygenase-1. Lipoxygenase-generated 3-oxa-oxylipins are resistant toward β-oxidation and have the potential for displaying enhanced biological activity in situations where activity is limited by metabolic degradation.     

Major Sex Pheromone Components of the Australian Gum Leaf Skeletonizer Uraba lugens: (10E,12Z)-Hexadecadien-1-yl Acetate and (10E,12Z)-Hexadecadien-1-ol

Two sex pheromone components of the gum leaf skeletonizer, Uraba lugens (Lepidoptera: Nolidae), recently established in New Zealand, were identified. Gas chromatography (GC) electroantennographic detection analyses of female pheromone gland extracts gave three compounds that consistently elicited antennal responses. Chemical analyses, using GC and GC-mass spectrometry, in conjunction with 4-methyl-1,2,4-triazoline-3,5-dione and dimethyldisulfide derivatizations, identified these compounds as (10E,12Z)-hexadecadien-1-yl acetate (E10,Z12-16:Ac), (10E,12Z)-hexadecadien-1-ol (E10,Z12-16:OH), and (Z)-11-hexadecen-1-yl acetate (Z11-16:Ac). A trapping trial in Queensland, Australia, in 2002, indicated that a blend of the two major components E10,Z12-16:Ac and E10,Z12-16:OH could attract gum leaf skeletonizer males. In the same trial, E10,Z12-16:Ac alone trapped large numbers of an unidentified nolid, Nola spp. Further trials in Auckland, New Zealand established that these two components were sufficient and necessary for trap catch of males; adding minor gland components, (10E,12E)-hexadecadien-1-yl acetate (E10,E12-16:Ac), Z11-16:Ac, or octadecan-1-ol (18:OH), to the two-component lure did not result in increased trap catches. Behavioral observations and gland analyses of the Auckland population revealed that female moths begin calling soon after emergence, with peak calling and pheromone production occurring 7 hr into the scotophase. Analysis of gland extract at two-hourly intervals during the first activity period showed that the ratio of E10,Z12-16:Ac to E10,Z12-16:OH (mean of 86: 14, respectively) and pheromone titer were fairly constant. No qualitative or quantitative differences in pheromone components were detected between gland extracts from Tasmanian univoltine and Auckland bivoltine populations of U. lugens.     

Facile one-pot synthesis of N-acyl-1H-1,2,3-benzotriazoles from internal and terminal olefinic fatty acids and their antimicrobial screening

N-acyl-1H-1,2,3-benzotriazoles were prepared in good yields by the reaction of benzotriazole and thionyl chloride with olefinic fatty acids under mild reaction conditions. The new compounds 1-(undec-10-enoyl)-1H-1,2,3-benzotriazole (5a),1-[(Z)-octadec-9-enoyl]-1H-1,2,3-benzotriazole (5b), 1-[(9Z,12R)-12-hydroxyoctadec-9-enoyl]-1H-1,2,3-benzotriazole (5c), 1-[(9R,12Z)-9-hydroxyoctadec-12-enoyl]-1H-1,2,3-benzotriazole (5d) formed were characterized on the basis of elemental analysis and spectral data. All the newly synthesized compounds (5a-5d) were screened for their antimicrobial activity and showed good antifungal activity.     

Flavour Deterioration of Soya-bean Oil: Identification of Intense Odour Compounds Formed during Flavour Reversion

Aroma dilution analysis of a volatile concentrate isolated from reverted soya-bean oil resulted in 11 odour compounds having high aroma values. Nine of these compounds were identified as: 3(Z)-hexenal, octanal, 1-octen-3-one, 1,5(Z)-octadien-3-one, nonanal, 2(E)-nonenal, 2(Z)-nonenal, 3(Z)-nonenal and 2(E),6(Z)-nonadienal. 3(Z)-Hexenal, the C₉-aldehydes and the two vinyl ketones contribute with high aroma values to the beany, grassy odour note of the reversion flavour.     

Chemical, Electrophysiological, and Behavioral Investigations on the Sex Pheromone of Lackey Moth, Malacosoma neustrium

The lackey moth Malacosoma neustrium (L.) (Lepidoptera Lasiocampidae) is a common pest of many forest and cultivated broadleaf trees. Analysis by GC-EAD of gland extracts and female effluvia showed the presence of two active peaks that were characterized as (E,Z)-5,7-dodecadienal (E5,Z7-12:Ald) and (E,Z)-5,7-dodecadienol (E5,Z7-12:OH) according to their GC retention times, mass spectra, and electroantennographic activity. (E,Z)-5,7-dodecadienyl acetate (E5,Z7-12:Ac) was also detected in the gland extracts. The average amounts of E5,Z7-12:Ald, E5,Z7-12:OH, and E5,Z7-12:Ac extracted from an abdominal tip were 113.2 +/- 22.0 ng, 29.9 +/- 6.2 ng, and 11.6 +/- 2.0 ng, respectively. In the effluvia from single females, on the average, 1.9 +/- 0.7 ng/min of aldehyde and 0.3 +/- 0.1 ng/min of alcohol were collected. In wind tunnel tests, male behavioral sequences elicited by E5,Z7-12:Ald alone or in 3:1 and 9:1 blends with the corresponding alcohol were similar to those evoked by one female equivalent of sex pheromone gland extract. Field trapping experiments showed that E5,Z7-12:Ald is essential to attract male moths. On adding E5,Z7-12:OH to E5,Z7-12:Ald in 1:3 and 1:9 ratios, male attraction slightly increased whereas in a 1:1 ratio, the attractiveness of E5,Z7-12:Ald was reduced.     

罗红霉素相关物的制备

引言罗红霉素(roxithromycin)又名9-O-甲氧乙氧甲基肟红霉素,是红霉素的衍生物,是20世纪80年代初开发的十四元环口服用大环内酯类抗生素,1988年首次在法国上市。它是广谱抗生素,除了对敏感的革兰阳性菌、革兰阴性菌和厌氧菌有效,对军团菌、支原体、衣原体等也有效[1-3],并且对胃酸稳定、吸收率高、疗效好、不良反应小,     

Attraction of pea mothCydia nigricana F. (Lepidoptera: Tortricidae) to female sex pheromone (E,E)-8,10-dodecadien-1-YL acetate,is inhibited by geometric isomersE,Z, Z,E, andZ,Z

Field attraction ofCydia nigricana males to synthetic female sex pheromone (E,E)-8,10-dodecadien-1-yl acetate, formulated on red rubber septa, declined continuously during two weeks. This was due to isomerization of (E,E)-8,10-dodecadien-1-yl acetate: eight days after application of purifiedE,E isomer, the proportion ofE,Z;Z,E; andZ,Z isomers in rubber septa aged in the laboratory was 4%; a 5% addition of any one of these isomers to fresh lures of (E,E)-8,10-dodecadien-1-yl acetate significantly reduced male attraction. Stereospecific syntheses of (E,Z)-, (Z,E)-, and (Z,Z)-8,10-dodecadien-1-yl acetate are described. The pheromone gland ofCydia nigricana contains 0.8 ng/female of (E,E)-8,10-dodecadien-1-yl acetate, accompanied by three monounsaturated acetates, (E)-9-dodecen-1-yl acetate, (Z)-5-tetradecen-1-yl acetate, and (Z)-7-tetradecen-1-yl acetate (0.1 ng/female each). These compounds did not augment male trap catch when added to (E,E)-8,10-dodecadien-1-yl acetate.     

Three new and bioactive icosanoids from the temperate red marine algaFarlowia mollis

Three new dihydroxyicosanoids, 12(R),13(R)-dihydroxyicosa-5(Z), 8(Z),10(E),14(Z)-tetraenoic acid, 12(R),13(R)-dihydroxyicosa-5(Z), 8(Z),10(E),10(Z),17(Z)-pentaenoic acid and 10(R^*),11(R^*)-dihydroxyoctadeca-6(Z),8(E),12(Z)-trienoic acid, have been isolated from a previously unstudied temperate red marine alga,Farlowia mollis (Cryptonemiales, Rhodophyta). The structures of these new metabolites have been deduced from detailed nuclear magnetic resonance and mass spectrometry analyses on stabilized diacetate-methyl esters and stereochemistry deduced by¹H NMR couplings and CD analysis of a dibenzoate derivative. Collectively, these new natural products modulate fMLP-induced superoxide anion generation in human neutrophils, inhibit the conversion of arachidonic acid to lipoxygenase products by human neutrophils, and inhibit the functioning of the dog kidney Na⁺/K⁺ ATPase.     

Reexamination of the Female Sex Pheromone of the Sweet Potato Vine Borer Moth: Identification and Field Evaluation of a Tricosatriene

The sweet potato vine borer moth, Omphisa anastomosalis (Pyraloidea: Crambidae), is a serious pest in tropical and subtropical Asia-Pacific regions. In previous work using a population from Okinawa, Japan, (10E,14E)-10,14-hexadecadienal (E10,E14-16:Ald) was identified as the major pheromone component, with hexadecanal, (E)-10-hexadecenal, and (E)-14-hexadecenal as minor components. However, traps baited with the synthetic compounds were less effective at attracting males in the field than those baited with virgin females. While Pyraloidea females usually produce only Type I pheromone components (unsaturated fatty alcohols and their derivatives), the pheromones of some Pyraloidea species have been shown to involve a combination of both Type I and Type II components (unsaturated hydrocarbons and their epoxides). We examined an extract of the pheromone glands of female O. anastomosalis from Vietnam by gas chromatography coupled to mass spectrometry and detected (3Z,6Z,9Z)-3,6,9-tricosatriene (Z3,Z6,Z9-23:H) in addition to the compounds identified previously. All four isomers of 10,14–16:Ald were synthesized. A mixture of synthetic E10,E14-16:Ald and Z3,Z6,Z9-23:H in a ratio of 1:0.2–1:2 was attractive to male moths in Vietnam, indicating the strong synergistic effect of the Type II compound. Addition of the other minor pheromone components to the binary blend did not increase the number of male moths captured. Combinations of Z3,Z6,Z9-23:H with the other three geometrical isomers of E10,E14-16:Ald attracted no males, further substantiating the 10E,14E configuration of the natural diene component. E10,E14-16:Ald mixed with other polyunsaturated hydrocarbons showed that mixtures that included a C₂₁ triene, a C₂₂ triene, or a C₂₃ pentaene attracted as many males as did the mixture with Z3,Z6,Z9-23:H. The identification of a highly attractive sex pheromone will help in developing efficient strategies for monitoring and control of O. anastomosalis populations in sweet potato fields.     

发酵新鲜鸢尾香气成分分析

采用同时蒸馏萃取装置提取挥发油并用气相色谱-质谱联用仪对经发酵的新鲜鸢尾根茎挥发性香味化合物进行了分离和鉴定,分离并鉴定出 69个组分,占峰面积的 84 .24%,并用面积归一化法测定了各种成分的质量分数,其主要香气成分为:w( 3- 甲基 -2 -丁烯醛 ) =0. 14%、w〔(Z) 3 -己烯醛〕=0. 09%、w〔(Z)- 2 庚烯醛〕=0.07%、w〔(E) 2- 癸烯醛〕=0 .08%、w〔(E,E) -2, 4 -癸二烯醛〕=0 .06%、w(辛酸 ) =0. 52%、w(癸酸 ) =0 66%、w(十二酸) =0. 57%、w(2, 4 二羟基 3, 6 -二甲基苯甲酸) =0. 13%、w(十四酸) =7 .76%、w(十五酸 ) =0 .19%、w(1, 2- 苯二甲酸) =0 .14%、w(9- 十六碳烯酸) =0. 37%、w(十六酸 ) =11. 25%、w(十七酸 ) =0 .21%、w-〔(Z,Z) 9, 12 -十八碳二烯酸〕=26. 09%、w〔(E) 9 十八碳烯酸〕=9. 58%、w(蒿醇) =0. 20%、w(环橙花叔醇 ) =0 88%、w(1- 二十二醇) =0 .20%、w(2- 十四烷氧乙醇 ) =0. 15%、w(3, 7, 11 -三甲基- 2, 6- 十二碳二烯 1 醇 ) = 0 08%、w(蒿酮) =0 .04%、w〔1 ( 4 -羟基- 3- 甲氧苯基 )乙酮〕= 2 .69%、w〔4- ( 2, 5, 6, 6 -四甲基环己 1 烯基 )丁- 2- 酮〕=0. 12%、w(5 甲基α 紫罗兰酮) =1 .22%、w〔1- (3, 4- 二甲氧苯基) 乙酮〕=0. 47%、w(3, 5, 5- 三甲基 -2- 环己烯-     

Syntheses of pure (9Z, 11Z), (9E, 11E), (9E, 11Z), and (9Z,11E)-9,11-hexadecadienals-possible candidate pheromones

The title compounds were prepared by six different routes, and recommendations are given for the more convenient procedures in laboratory-scale syntheses. Modifications in the literature preparations of the 9E,11E and 9E,11Z isomers are described. Baseline separation of a prepared mixture of all four isomers of the (9Z, 11Z), (9E, 11E), (9E, 11Z), and (9Z, 11E)-9,11-hexadecadienals was achieved using GC methods with standard capillary columns. [¹³C]NMR spectroscopy of the alkene carbon atoms clearly differentiates between theZ,Z, E,E and eitherE,Z orZ,E isomers of the precursor dienols and thus of the dienals.     

(Z)-5-甲基-3-苯硫甲叉基-4,5-二氢呋喃-2-酮和(Z)-5-甲基-3-苯硫甲基-5-氢呋喃-2-酮简便合成

以3-苯硫基丙块1为原料经5步反应合成了(Z)-5-甲基-3苯硫甲基-5-氢呋喃-2-酮8和(Z)-5-甲基-3-苯硫甲叉基4,5-二氢呋喃-2-酮9。合成的关键步骤是在三甲基氯硅烷(TMSCl)/NaI/H2O/CH3CN体系中5-苯硫基-3-戊炔-2-酮3一步完成的碘氢化和去共轭反应。     

The preparation and characterization of the methoxy derivatives of polyunsaturated fatty acids: Stabilized product analogs of lipoxygenase catalysis

The products from the action of soybean lipoxygenase on a series of polyunsaturated fatty acids have been converted in 2 steps into the corresponding methoxy derivatives. The product hydroperoxides were reduced in situ to alcohols with sodium borohydride. The ethers were generated by treatment of the alcohols with sodium hydride and methyl iodide in tetrahydrofuran. 13-Methoxy-9(Z),11(E)-octadecadienoic, 15-methoxy-11(Z),13(E)-eicosadienoic and 15-methoxy-5(Z),8(Z),11(Z), 13(E)-eicosatetraenoic acids were thus prepared. The methyl ethers were analyzed and the structures established by high performance liquid chromatography, nuclear magnetic resonance and infrared spectrometry, polarimetry and mass spectroscopy (as methyl esters). The methylation reaction proceeds without molecular rearrangements or racemiziation.     

(E4,Z9)-TETRADECADIENAL, A SEX PHEROMONE FOR THREE NORTH AMERICAN MOTH SPECIES IN THE GENUS Saturnia

The lepidopteran genus Saturnia has three representatives in North America, S. walterorum, S. mendocino, and S. albofasciata. (E4,Z9)-Tetradecadienal (E4,Z9–14 : Ald) was identified as a sex pheromone component for all three species by combinations of coupled gas chromatography–electroantennogram detection (GC-EAD), GC–mass spectrometry (MS), and field trials. In field trials, all three species were strongly attracted to (E4,Z9–14 : Ald) as a single component. Small amounts of (Z)-9-tetradecenal (Z9–14 : Ald) also were found in extracts of all three species, but blends of this compound with E4,Z9–14 : Ald were no more attractive to male moths than E4,Z9–14 : Ald alone. Extracts of pheromone glands of female S. walterorum occasionally contained a third, trace compound eliciting responses from male antennae in GC-EAD experiments, but this compound was not identified. It is suggested that the three species can use the same, single component as a sex attractant because the flight period of S. albofasciata (fall) is different than that of the other two species (spring), whereas the geographic distributions of S. mendocino and S. walterorum overlap over only small portions of their ranges. Furthermore, the latter two species readily hybridize, so there may be minimal fitness cost to cross-attraction.     

Potential for Use of Synthetic Sex Pheromone for Mating Disruption of the Olive Pyralid Moth, Euzophera pinguis

The potential for pheromone-based mating disruption of the olive pyralid moth (OPM), Euzophera pinguis, in olive groves was investigated during the second flight period in small-plot trials in 2002. The female of this species emits a blend of (9Z,12E)-tetradecadien-1-ol and (9Z,12E)-tetradecadienyl acetate, which were synthesized for field tests. Mating disruption efficacy in 0.8-ha trials was evaluated using two parameters: reduction of male capture in pheromone traps and reduction of infestation in infestation-prone sites. White rubber septa containing 10 mg of pheromone blend as disruptant were applied at a density of 50 septa/ha for each treatment. Mean catches of E. pinguis males in pheromone traps were greatly reduced (> 95%) in pheromone-treated plots relative to similar traps placed in control plots. In addition, significant reductions were recorded (35-40%) in the oviposition and infestation levels during pheromone treatment. The total amount of pheromone blend released from disruption dispensers during the field trials was estimated to average 5.4 mg/ha/day, over 56 days.     

Flight Tunnel Response of Male European Corn Borer Moths to Cross-Specific Mixtures of European and Asian Corn Borer Sex Pheromones: Evidence Supporting a Critical Stage in Evolution of a New Communication System

Previous flight tunnel studies showed that 3–5 % of male European corn borer (ECB) moths, Ostrinia nubilalis, could fly upwind and make contact with sources releasing the sex pheromone of the closely related Asian corn borer (ACB), Ostrina furnacalis, [2:1 (Z)-12-tetradecenyl acetate (Z12-14:OAc) : (E)-12-teradecenyl acetate (E12-14:OAc)] and that 2–4 % of ACB males could similarly fly upwind to the sex pheromone blends of the ECB Z- [97:3 (Z)-tetradecenyl acetate (Z11-14:OAc) : (E)-tetradecenyl acetate (E11-14:Ac)] and E-strains (1:99 Z/E11-14:OAc) pheromones. The results supported the hypothesis that the evolution of the ACB pheromone system from an ECB-like ancestor included a stage in which males could be attracted to the unusual females emitting Z12- and E12-14:OAc while retaining their responsiveness to the ancestral pheromone blend of Z11- and E11-14:OAc. Here, we showed further that ECB E-strain males exhibited upwind oriented flight and source contacts to sources containing all combinations of ECB and ACB components. Maximal response levels were observed with the E-strain 99:1 E11/Z11-14:OAc blend, and high response levels also were observed with two other blends containing E11-14:OAc as the major component (E11:E12 and E11:Z12). Upwind flight and source contact also occurred at lower levels with the remaining blend combinations in which Z11-, E12-, or Z12-14:OAc was the major component. Our current results support the hypothesis concerning the evolution of ACB from an ECB-like ancester by showing that males were able to respond to females producing either the 12–14:Ac isomers, 11–14:Ac isomers, or even mixtures of all four components     

The aggregation pheromone of <Emphasis Type="Italic">Diorhabda elongata</Emphasis>, a biological control agent of saltcedar(<Emphasis Type="Italic">Tamarix</Emphasis> spp.): identification of two behaviorally active components

The leaf beetle Diorhabda elongata Brullé (Coleoptera: Chrysomelidae)has been introduced as a biological control agent for saltcedars, Tamarix spp., an exotic, invasive weedy tree in the western United State. Gas chromatographic (GC) analysis of volatiles collected from feeding male or female beetles, or saltcedar foliage alone, showed two components produced almost exclusively by males. These compounds elicited responses from antennae of male and female beetles in GC-electroantennographic detection (EAD) analyses. The compounds were identified as (2E,4Z)-2,4-heptadienal (1) and (2E,4Z)-2,4- heptadien-1-ol (2) by GC-mass spectrometry (MS), and confirmed with authentic standards. The two compounds were also detected at trace levels from feeding females and foliage controls, but the amounts from feeding males were 8-40 times higher, typically 55-125 ng per day per male. The amounts of 1 and 2 in collections from females did not differ significantly from amounts collected from control foliage. In field trials, 2 as a single component was as attractive as a 1:1 blend of 1 and 2. Compound 1 as a single component was more attractive than controls, but much less attractive than 2 or the blend. Males and femaleswere attracted in about equal numbers, indicating that this is an aggregation pheromone.Mention of trade names or commercial products in this article is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the U.S. Department of Agriculture.