Concise Synthesis of (8Z,11Z,14Z)-8,11,14-Heptadecatrienal, (7Z,10Z,13Z)-7,10,13-Hexadecatrienal,and (8Z,11Z)-8,11-Heptadecadienal,Components of the Essential Oil of Marine Green Alga Ulva pertusa

The long-chain aldehydes, (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, were concisely synthesized by using Grignard coupling, catalytic hydrogenation with the Lindlar catalyst, and oxidation with Dess–Martin periodinane as the key steps. Particularly, (8Z,11Z,14Z)-8,11,14-heptadecatrienal and (7Z,10Z,13Z)-7,10,13-hexadecatrienal both possessed a seaweed-like odor.     

Synthesis of (6Z,9Z,11E)-octadecatrienoic and (8Z,11Z,13E)-eicosatrienoic acids and their [1-(14)C]-radiolabeled analogs

In order to study the metabolic pathway and the physiological effects of 9c,11t-18:2 (major isomer of conjugated linoleic acid) and its C(18:3) and C(20:3) metabolites, 6c,9c,11t-18:3 and 8c,11c,13t-20:3 and their [1-(14)C]-radiolabeled analogs were prepared stereoselectively by total synthesis. The 8c,11c,13t-20:3 was obtained in 11 steps. The synthesis involves a highly stereoselective Wittig reaction between 3-(t-butyldiphenylsilyloxy)propanal and the ylide of 7-(2-tetrahydropyranyloxy)heptanylphosphonium salt which gave (3Z)-1-(t-butyldiphenylsilyloxy)-10-(2-tetrahydropyranyloxy)dec-3-ene in a first step. Then the t-butyldiphenylsilyl derivative was deprotected selectively and the resulting alcohol function was converted via a bromide into a phosphonium salt. The second stereoselective Wittig condensation between the phosphonium salt and commercial (2E)-non-2-enal under cis-olefinic conditions using Lithium hexamethyldisilazide as base afforded the (7Z,10Z,12E)-1-(2-tetrahydropyranyloxy)nonadeca-7,10,12-triene in a very good isomeric purity. The intermediate product was brominated and transformed by reaction with magnesium into Grignard reagent, which was one-carbon elongated by unlabeled or labeled carbon dioxide to obtain the 8c,11c,13t-20:3 in good isomeric purity (95%) and high radiochemical purity for its [1-(14)C]-radiolabeled analog (99%). 6c,9c,11t-18:3 was synthesized in a similar way by using 5-(2-tetrahydropyranyloxy)pentanylphosphonium salt in place of 7-(2-tetrahydropyranyloxy)heptanylphosphonium salt in a first step. Other reactions were unchanged and products were obtained in similar yields. Similar to 8c,11c,13t-20:3, the 6c,9c,11t-18:3 was obtained in a very good isomeric purity (95%) and its [1-(14)C]-radiolabeled analog in a high radiochemical purity (95%).     

Sequential substitution of 1,2-dichloro-ethene: a convenient stereoselective route to (9Z,11E)-, (10E,12Z)- and (10Z,12Z)-

Conjugated linoleic acid (CLA) isomers are present in human foods derived from milk or ruminant meat. To study their metabolism, (9Z,11E)-, (10E,12Z)- and (10Z,12Z)-[1-(14)C]-octadecadienoic acids with high radiochemical and isomeric purities (>98%) were prepared by stereoselective multi-step syntheses involving sequential substitution of 1,2-dichloro-ethene. In the case of the (9Z,11E) isomer, a first metal-catalyzed cross-coupling reaction between (E)-1,2-dichloro-ethene and 2-non-8-ynyloxy-tetrahydro-pyran, obtained from 7-bromo-heptan-1-ol, gave a conjugated chloroenyne. A second coupling reaction with hexylmagnesium bromide provided a heptadecenynyl derivative. Stereoselective reduction of the triple bond and bromination afforded (7E,9Z)-17-bromo-heptadeca-7,9-diene. Formation of the Grignard reagent and carbonation with 14CO(2) gave (9Z,11E)-[1-(14)C]-octadeca-9,11-dienoic acid (overall yield from 7-bromo-heptan-1-ol, 14.4%). (10E,12Z)- and (10Z,12Z)-[1-(14)C]-octadeca-10,12-dienoic acids were synthesized by the same methodology using 1-heptyne, 8-bromo-octan-1-ol and, respectively, (E)-1,2-dichloro-ethene and its (Z) isomer (overall yield from 8-bromo-octan-1-ol, 13.1% (10E,12Z); 17.2% (10Z,12Z)). Impurities (<2% if present) were identified as being (E,E) CLA isomers and were removed by RP-HPLC. Metabolism studies in animal are in progress.     

Distribution of an enzyme system producing seaweed flavor: conversion of fatty acids to long-chain aldehydes in seaweeds

The long chain aldehyde-forming enzyme (LCAE) activity that catalyzes formation of long chain aldehydes, such as (8Z, 11Z, 14Z)-heptadecatrienal, (8Z, 11Z)-heptadecadienal, (8Z)-heptadermal, (7Z, 10Z, 13Z)-hexadecatrienal and pentadecanal from linolenic acid, linoleic acid, oleic acid and palmitic acid, in that order, occurs in a wide range of green, brown and red seaweeds. The LCAE activity increased with maturation of juvenile fronds of Enteromorpha sp. in culture. Thus, cultivation of seaweeds for flavor foods is of interest. The release of long chain aldehydes from the thallus into the medium was confirmed by a quantitative high performance liquid chromatography of volatile compounds, using a closed loop stripping technique, during the culture of the green alga, Ulva pertusa. This finding suggests physiological roles of long chain aldehydes and LCAE activity in marine ecosystems.     

10,20-Methanorhodopsins: (7E,9E,13E)-10,20-methanorhodopsin and (7E,9Z,13Z)-10,20-methanorhodopsin. 11-cis-locked rhodopsin analog pigments with unusual thermal and photo-stability

Synthesis of the retinal analog, 10,20-methanoretinal (R6), where the 11Z conformation is locked in a six-membered ring, yielded four stereoisomers (7E,9E,13E, 7E,9E,13Z, 7E,9Z,13E and 7E,9Z,13Z). These four isomers were separated by straight-phase isocratic HPLC and identified by 1H-NMR and NOE analysis. All isomers smoothly recombined with bovine opsin at a relatively high rate (5-10% of that of the natural chromophore 11Z-retinal). The corresponding 13E and 13Z isomers yielded identical analog pigments, probably due to rapid thermal isomerization around the C13 = C14 double bond. The (7E,9E)-isomers produced a pigment with maximal absorbance at 510 nm, while the pigment produced from the (7E,9Z)-isomers had maximal absorbance at 494 nm. Based upon kinetic considerations, the chromophore structure in the 510-nm-absorbing pigment should be (7E,9E,13E), i.e. equivalent to 11Z-retinal and rhodopsin, while the chromophore structure in the 494-nm-absorbing pigment should be (7E,9Z,13Z), i.e. equivalent to (9Z,11Z,13Z)-rhodopsin, an isorhodopsin analog. In analogy to the 11-cis-locked rhodopsin analogs Rh5 and Rh7, the 510-nm-absorbing pigment, (7E,9E,13E)-10,20-methanorhodopsin, was dubbed Rh6 and the 494-nm-absorbing pigment. (7E,9Z,13Z)-10,20-methanorhodopsin, was dubbed Iso6. The opsin shift of Rh6 (2660 cm-1) is practically identical to that of rhodopsin itself (2650 cm-1). Rh6 and Iso6 are nearly as stable as rhodopsin towards hydroxylamine and solubilization in detergent solution and could be easily purified and reconstituted into proteoliposomes by established procedures. Due to the 11-cis-lock, Rh6 is much less photolabile (bleaching rate less than 1%) than rhodopsin, but it is not completely photostable, probably since photoisomerization around the C7 = C8, C9 = C10 and C13 = C14 bonds is allowed. Illumination of either Rh6 or Iso6 does not generate the common photointermediates but instead produces a complex pattern of photochemical transitions, which during continuous illumination leads to the same final steady state, absorbing at 498 nm. This process is accompanied by a slow but steady loss of pigment, probably due to hydrolytic release of chromophore, which is markedly accelerated in the presence of hydroxylamine. In a physiological assay (light-dependent activation of rod cGMP phosphodiesterase) Rh6 is only marginally active and this probably reflects conformational changes accompanying the above-mentioned photochemical transitions. This supports the concept that normal rhodopsin-based phototransduction requires 11Z to all-E isomerization.(ABSTRACT TRUNCATED AT 400 WORDS)     

11(R),12(S),15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid: an endothelium-derived 15-lipoxygenase metabolite that relaxes rabbit aorta

Previous studies indicate that 11,12,15-trihydroxyeicosatrienoic acid (11,12,15-THETA), an endothelium-derived hyperpolarizing factor in the rabbit aorta, mediates a portion of the relaxation response to acetylcholine by sequential metabolism of arachidonic acid by 15-lipoxygenase, hydroperoxide isomerase, and epoxide hydrolase. To determine the stereochemical configuration of the endothelial 11,12,15-THETA, its activity and chromatographic migration were compared with activity and migration of eight chemically synthesized stereoisomers of 11,12,15(S)-THETA. Of the eight isomers, only 11(R),12(S),15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid comigrated with the biological 11,12,15-THETA on reverse- and normal-phase HPLC and gas chromatography. The same THETA isomer (10(-7)-10(-4) M) relaxed the rabbit aorta in a concentration-related manner (maximum relaxation = 69 +/- 5%). These relaxations were blocked by apamin (10(-7) M), an inhibitor of small-conductance Ca2+-activated K+ channels. In comparison, 11(S),12(R),15(S),5(Z),8(Z),13(E)-THETA (10(-4) M) relaxed the aorta by 22%. The other six stereoisomers were inactive in this assay. With use of the whole cell patch-clamp technique, it was shown that 10(-4) M 11(R),12(S),15(S),5(Z),8(Z),13(E)-THETA increased outward K+ current in isolated aortic smooth muscle cells by 119 +/- 36% at +60 mV, whereas 10(-4) M 11(R),12(R),15(S),5(Z),8(Z),13(E)-THETA increased outward K+ current by only 20 +/- 2%. The 11(R),12(S),15(S),5(Z),8(Z),13(E)-THETA-stimulated increase in K+ current was blocked by pretreatment with apamin. These studies suggest that 11(R),12(S),15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid is the active stereoisomer produced by the rabbit aorta. It relaxes smooth muscle by activating K+ channels. The specific structural and stereochemical requirements for K+ channel activation suggest that a specific binding site or receptor of 11,12,15-THETA is involved in these actions.     

合成性信息素对柑桔潜叶蛾的田间引诱作用

目前柑桔潜叶蛾的防治主要依赖化学农药, 而且生产中缺少有效测报技术。为此, 我们于2009年6月30日至10月6日在浙江宁波通过有机合成柑桔潜叶蛾Phyllocnistis citrella（鳞翅目, 细蛾科）的3种性信息素化合物顺7, 顺11, 反13-十六碳三烯醛、顺7, 顺11-十六碳二烯醛和顺7-十六碳烯醛, 配制成不同浓度比例的混合物, 进行田间试验比较其引诱活性。结果表明, 单一的顺7, 顺11, 反13-十六碳三烯醛对柑桔潜叶蛾雄蛾就可以显示较强的引诱作用, 而顺7, 顺11-十六碳二烯醛单一成分没有引诱活性, 顺7, 顺11, 反13-十六碳三烯醛与顺7, 顺11-十六碳二烯醛的二元混合物30∶1~3∶1之间活性较强, 而在30∶1的质量比例时诱虫量最高。含顺7-十六碳烯醛的三元混合物, 当顺7, 顺11, 反13-十六碳三烯醛∶顺7, 顺11-十六碳二烯醛∶顺7-十六碳烯醛三者比例为100∶10∶3时有显著增效作用。剂量与诱捕活性试验显示每枚诱芯1 mg顺7, 顺11, 反13-十六碳三烯醛的剂量引诱作用最强, 随浓度降低, 引诱作用下降。诱捕器在0.8~1.5 m之间的不同悬挂高度对诱捕数量无显著影响。结果说明, 顺7, 顺11, 反13-十六碳三烯醛、顺7, 顺11-十六碳二烯醛和顺7-十六碳烯醛组成的三元混合物诱芯可以作为柑桔潜叶蛾的诱杀技术并应用于其生物防治和预测测报。     

Stereoselective synthesis of (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid,and their [1-14C]-radiolabeled analogs

To study the metabolic fate of conjugated linoleic acid isomers, we synthesized, in seven steps, from 1-heptyne, (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid, and their [1-(14)C]-analogs. In the case of (6Z,10E,12Z)-octadecatrienoic acid, a series of palladium-catalyzed cross-coupling reactions between 1-heptyne and (E)-1,2-dichloro-ethene, a coupling reaction with a Grignard reagent and cleavage of the dioxolane gave (E)-dodec-4-en-6-ynal 3. Stereoselective Wittig reaction between aldehyde 3 and triphenyl-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phosphonium provided a dienyne. Stereocontrolled reduction of the triple bond and replacement of the tetrahydropyranyl group by a bromine gave (5Z,9E,11Z)-1-bromo-heptadeca-5,9,11-triene 10. Formation of the alkenyl lithium derivative and carbonation with CO(2) furnished (6Z,10E,12Z)-octadecatrienoic acid. (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid was obtained by the same route but using triphenyl-[5-(tetrahydro-pyran-2-yloxy)-heptyl]-phosphonium iodide for the Wittig reaction. [1-(14)C]-analogs were obtained from the bromides by carbonation with (14)CO2. In all cases, chemical or radiochemical purities were found to be better than 95% after purification by flash chromatography on silica gel (>99% after additional purification by RP-HPLC). Metabolism studies in animals are in progress.     

A simple method for the preparation of (5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid enantiomers and the corresponding 14,15-dehydro analogues: role of the 16-hydroxy group for the lipoxygenase reaction

(5Z,8Z,11Z,13E)-15-Hydroxy-5,8,11,13-eicosatetraenoic acid (15-HETE) is not well oxygenated by arachidonate 15-lipoxygenases because of two structural reasons: (i) it contains a hydrophilic OH-group in close proximity to its methyl end and (ii) it lacks the bisallylic methylene at C(13). We synthesized racemic (5Z,8Z,11Z,14Z)-16-hydroxy-5,8,11,14-eicosatetraenoic acid (16-HETE) which still contains the bisallylic C(13), separated the enantiomers reaching an optical purity of >99% and tested them as substrates for 5- and 15-lipoxygenases. Our synthetic pathway, which is based on stereospecific hydrogenation of a polyacetylenic precursor, yielded substantial amounts (30%) of 14,15-dehydro-16-HETE in addition to 16-HETE. When 16-HETE was tested as lipoxygenase substrate, we found that it is well oxygenated by the soybean 15-lipoxygenase and by the recombinant human 5-lipoxygenase. Analysis of the reaction products suggested an arachidonic acid-like alignment at the active site of the two enzymes. In contrast, the product pattern of 16-HETE methyl ester oxygenation by the soybean lipoxygenase (5-lipoxygenation) may be explained by an inverse head to tail substrate orientation.     

Free radical oxidation of coriolic acid (13-(S)-hydroxy-9Z,11E-octadecadienoic acid)

The reaction of (13S,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid (1a), one of the major peroxidation products of linoleic acid and an important physiological mediator, with the Fenton reagent (Fe(2+)/EDTA/H(2)O(2)) was investigated. In phosphate buffer, pH 7.4, the reaction proceeded with >80% substrate consumption after 4h to give a defined pattern of products, the major of which were isolated as methyl esters and were subjected to complete spectral characterization. The less polar product was identified as (9Z,11E)-13-oxo-9,11-octadecadienoate (2) methyl ester (40% yield). Based on 2D NMR analysis the other two major products were formulated as (11E)-9,10-epoxy-13-hydroxy-11-octadecenoate (3) methyl ester (15% yield) and (10E)-9-hydroxy-13-oxo-10-octadecenoate (4) methyl ester (10% yield). Mechanistic experiments, including deuterium labeling, were consistent with a free radical oxidation pathway involving as the primary event H-atom abstraction at C-13, as inferred from loss of the original S configuration in the reaction products. Overall, these results provide the first insight into the products formed by oxidation of 1a with the Fenton reagent, and hint at novel formation pathways of the hydroxyepoxide 3 and hydroxyketone 4 of potential (patho)physiological relevance in settings of oxidative stress.     

Preparation of Four Geometric Isomers of (11E)-4,6,11-Hexadecatrienal and Their Effect toward Male Eri-Silk Moths

Four geometric isomers of (11E)-4,6,11-hexadecatrienal were prepared, and their pheromone activity towards male eri-silk moths was evaluated. The EAG activity of each isomer was determined by the EAG-GLC method in order of increasing activity to be (4Z,6E,11E)- and (4E,6E,11E)?? (4E,6Z,11E) ?? (4Z,6Z,11E)-hexadecatrienal.     

Large-scale preparation of (9Z,12E)-[1-(13)C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1-(13)C]-octadeca-9,12,15-trienoic acid and their [1-(13)C] all-cis isomers

Several grams of labelled trans linoleic and linolenic acids with high chemical and isomeric purities (>97%) have been prepared for human metabolism studies. A total of 12.5 g of (9Z, 12E)-[1-(13)C]-octadeca-9,12-dienoic acid and 6.3 g of (9Z,12Z, 15E)-[1-(13)C]-octadeca-9,12,15-trienoic acid were obtained in, respectively, seven steps (7.8% overall yield) and 11 steps (7% overall yield) from 7-bromo-heptan-1-ol. The trans bromo precursors used for the labelling were synthesised by using copper-catalysed couplings. The trans fatty acids were then obtained via the nitrile derivatives. A total of 23.5 g of (9Z,12Z)-[1-(13)C]-octadeca-9, 12-dienoic acid and 10.4 g of (9Z,12Z,15Z)-[1-(13)C]-octadeca-9,12, 15-trienoic acid were prepared in five steps in, respectively, 32 and 18% overall yield. Large quantities of bromo and chloro precursors were synthesised from the commercially available acid according to Barton's procedure. In all cases, the main impurities (>0.5%) of each labelled fatty acid have been characterised.     

Sex attractant for Diloba caeruleocephala (L.), (Lep., Dilobidae) - (Z)-8-tridecenyl acetate

For seven homologous compounds, the highest electro-antennography responses from male Diloba caeruleocephala (L.) were elicited by ( Z )-5-decenyl acetate ( Z )-7-dodecenyl acetate and ( Z )-8-tridecenyl acetate. The ( Z )-8-tridecenyl acetate caused significant attraction of males of this species in the field, in both Bulgaria and Hungary. ( Z )-10-pentadecenyl acetate, when added as a 10% admixture to the latter, acted as an attractant inhibitor. In Bulgaria, the flight period of this species, as established by means of pheromone traps, commenced at the beginning of September and lasted until the middle of October.     

(10E,12Z,15Z)-9-hydroxy-10,12,15-octadecatrienoic acid methyl ester as an anti-inflammatory compound from Ehretia dicksonii

The methanol extract of Ehretia dicksonii provided (10E, 12Z, 15Z)-9-hydroxy-10,12,15-octadecatrienoic acid methyl ester (1) which was isolated as an anti-inflammatory compound. Compound 1 suppressed 12-Otetradecanoyl-phorbol-13-acetate (TPA)-induced inflammation on mouse ears at a dose of 500 microg (the inhibitory effect (IE) was 43%). Linolenic acid methyl ester did not inhibit this inflammation at the same dose. However, the related compounds of 1, (9Z,11E)-13hydroxy-9,11-octadecadienoic acid (5) and (9Z,llE)13-oxo-9,11-octadecadienoic acid (6), showed potent activity (IE500 microg of 63% and 79%, respectively). Compounds 1, 4 ((9Z, 12Z, 14E)-16-hydroxy-9,12,14-octadecatrienoic acid), 5 and 6 also showed inhibitory activity toward soybean lipoxygenase at a concentration of 10 microg/ml.     

Synthesis of (8Z,11Z,14Z)-eicosatrien-5-ynoic (5,6-dehydroarachidonic) acid and its transformation into [5,6-3H]arachidonic acid and [5,6-3H]prostaglandins E2 and F2 alpha

8Z,11Z,14Z-Eicosatriene-5-ynoic acid and its tritium-labelled analogue, [5,6-3H]arachidonic acid, have been synthesized on the basis of acetylenic compounds. [5,6-3H]Arachidonic acid has been used as substrate for the enzymatic synthesis of [5,6-3H]PGE2 and [5,6-3H]PGF2 alpha.     

Localization of lipids containing (Z)-11-eicosenoic acid and (Z)-13-docosenoic acid in Tropaeolum majus

(Z)-11-Eicosenoic (gondoic) and (Z)-13-docosenoic (erucic) acids were found in large proportions as constituent fatty acids of the triglycerides and polar lipids in seeds and petals of Tropaeolum majus. In the lipids of the other floral organs as well as in those of vegetative organs, only traces of these fatty acids were detected. During seed germination, the proportions of the two fatty acids did not change. (Z)-9,12- Octadecadienoic (linoleic) and (Z)-9,12,15-octadecatrienoic (linolenic) acids, which occurred only in traces in lipids of the seeds, were major constituent fatty acids of lipids in floral and vegetative organs as well as those of callus cultures.     

First total syntheses of (Z)-15-methyl-10-hexadecenoic acid and the (Z)-13-methyl-8-tetradecenoic acid

The first total syntheses for the (Z)-15-methyl-10-hexadecenoic acid and the (Z)-13-methyl-8-tetradecenoic acid were accomplished in seven steps and in 31-32% overall yields. The (trimethylsilyl)acetylene was the key reagent in both syntheses. It is proposed that the best synthetic strategy towards monounsaturated iso methyl-branched fatty acids with double bonds close to the omega end of the acyl chain is first acetylide coupling of (trimethylsilyl)acetylene to a long-chain bifunctional bromoalkane followed by a second acetylide coupling to a short-chain iso bromoalkane, since higher yields are thus obtained. Spectral data is also presented for the first time for these two unusual fatty acids with potential as biomarkers and as topoisomerase I inhibitors.     

A co-attractant mixture of (Z)-11-tetradecenyl acetate and (Z)-9-dodecenyl acetate for Neocalyptis angustilineata and Homona magnanima

While monitoring for the seasonal occurrence of the tea tortrix moth, Homona magnanima Diakonoff (Lepidoptera: Tortricidae), a number of Neocalyptis angustilineata (Walsingham) were attracted to traps baited with H. magnanima attractant, a 9:1 blend of (Z)-11-tetradecenyl acetate (Z11-14Ac) and (Z)-9-dodecenyl acetate (Z9-12Ac). We evaluated a 1:1 blend (1 mg) and a 9:1 blend (1 mg) of Z11-14Ac and Z9-12Ac for their attractiveness to the two moth species. H. magnanima was attracted only to the 9:1 blend. However, N. angustilineata was equally attracted to both blends. Thus, we report the 9:1 blend as a co-attractant for N. angustilineata and H. magnanima. This blend is the first finding for the attractant for N. angustilineata.     

Detection of sex pheromone components in Manduca sexta (L.).

The ability of olfactory receptor neurons to detect female-produced sex pheromone components and a limited sample of potential host plant odours was studied by single-sensillum recordings from olfactory sensilla present on male and female antennae in Manduca sexta. The majority of pheromone-sensitive receptor neurons examined in males was specialized for detection of the two major pheromone components, E10,Z12-hexadecadienal and E10,E12,Z14-hexadecatrienal or E10,E12,E14-hexadecatrienal. New olfactory receptor neurons tuned to the minor components E10,E12-hexadecadienal and Z11-hexadecenal were found. In females, olfactory receptor neurons specific to Z11-hexadecanal were discovered. Pheromone components and host volatiles were detected by separate sets of receptor neurons.     

(Z)-11-Hexadecenyl compounds as attractants for male microlepidoptera of the subfamilies Argyresthiinae, Glyphipteryginae, and Crambinae

Traps baited with Z11-16:Ac, Z11-16:Ald, Z11-16:OH, and Z13-18:Ac, singly or in mixtures, were tested for their attractivity for males of microlepidoptera in an apple orchard, a mixed deciduous forest, and a coniferous forest. In particular, Z11-16:Ac and Z11-16: Ald attracted some Crambinae, one Glyphipteryx species, and several species of Argyresthia, including the injurous species A. fundella (on fir), A. conjugella (on apple), A. pruniella (on cherry), and A. thuiella (on Thuja).

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Attraction sexuelle de microlépidoptères des sous-familles Argyresthiinae, Glyphipteryginae et Crambinae par des hexadécènes 11Z

Résumé L'attraction de microlépidoptères par des hexadécènes 11Z a été examinée en 1982 et 1983 à l'aide de pièges sexuels placés dans différents biotopes de Hollande. Ces pièges contenaient différents mélanges synthétiques d'acétoxy-1-hexadécènes 11Z (Z11-16:Ac), d'hexadécènal 11Z (Z11-16:Ald), d'hexadécénol 11Z (Z11-16:OH) et d'acétoxyl-1-octadécène 13Z (Z13-18:Ac). Les pièges étaient placés dans un verger de pommiers, dans un bois de feuillus aux essences diverses et dans un bois de résineux. Des mâles de 10 espèces de lépidoptères ont été capturés avec ces mélanges, parmi lesquels ceux de 3 espèces de Pyralidae, d'une espèce du genre Glyphipteryx et de 6 espèces du genre Argyresthia. Parmi les Argyresthia, certaines espèces sont considérées comme des déprédateurs: A. fundella sur sapin (Abies), A. conjugella sur pommier (Malus), A. pruniella sur cerisier (Prunus) et A. thuiella sur Thuja. Enfin, un tableau fournit 28 produits contenant des hexadécènes Z11 actuellement connus comme attractifs sexuels de microlépidoptères; la majorité des espèces appartient aux sous-familles Crambinae, Argyresthiinae, Glyphipteryginae et Acrolepiinae.