(11Z)-hexadec-11-enal enhances the attractiveness of Diatraea saccharalis main pheromone component in wind tunnel experiments

Abstract:  GC-EAD and GC-MS analysis of pheromone gland extracts of sugarcane borer, Diatraea saccharalis , revealed two antennally active compounds, (9 Z ,11 E )-hexadeca-9,1-dienal and (11 Z )-hexadec-11-enal, in approximately 10 : 1 ratio. Various doses of identified compounds were investigated in wind tunnel experiments individually and in a 10 : 1 ratio. At all tested doses (9 Z ,11 E )-hexadeca-9,1-dienal alone elicited upwind orientation and source location only in a minority of tested males. An admixture of (11 Z )-hex-11-enal enhanced the attractiveness of (9 Z ,11 E )-hexadeca-9,11-dienal significantly. This two-component blend (100 pg) was as attractive as natural pheromone extracted from three female pheromone glands. The data suggest that (11 Z )-hexadec-11-enal is a part of the D. saccharalis sex pheromone.     

笋秀夜蛾雄蛾对性信息素化合物的电生理和行为反应

利用气质联用仪对笋秀夜蛾雌蛾性腺体粗提物成分进行了分析比对,通过触角电位(EAG)试验研究了笋秀夜蛾雄成虫对性信息素组分的电生理反应,以Y形嗅觉仪进行了室内和林间的行为生测.结果表明： 雌蛾性腺体粗提物中顺11-十六碳乙酸酯(Z11-16:Ac)和顺11-十六碳烯醇(Z11-16:OH)为笋秀夜蛾性信息素活性组分,性腺粗提物、两种化合物及其混合物均能激发雄蛾明显的EAG反应,且EAG反应值随性信息素组分浓度增加而增加.Z11-16:Ac和Z11-16:OH按57∶43配置成的二元混合物所激发的EAG反应强于同等剂量下的单一组分.室内的行为生测和林间诱捕试验结果与EAG反应基本一致,Z11-16:Ac+Z11-16:OH(57∶43)混合物对雄蛾引诱力最强,在林间单诱捕器(诱芯浓度为10⁴ng·μL^-1)的平均诱捕量达到(48.5±6.7)头.     

小地老虎雄蛾对雌蛾性信息的EAG反应

利用触角电位记录（EAG）技术,测定了小地老虎Agrotis ypsilon (Rottemberg) 雄蛾对性信息素标准化合物Z7-12：Ac（A）、Z9-14：Ac（B）、Z11-16：Ac（C）、Z5-10：Ac（D）和Z8-12：Ac（E）的EAG反应。结果表明：这些标准化合物均能引起EAG反应,其中组分A（Z7-12：Ac）引起的反应最强,为5.65 mV,组分B（Z9-14：Ac）和C（Z11-16：Ac）居中; 组分D（Z5-10：Ac）的EAG反应值最小,为2.50 mV。二元混合物、三元混合物、四元混合物和全组分的EAG反应较高,其EAG反应值均显著高于单组分的反应值。三元混合物ABC的反应值最高,与5头雌蛾腺体的正己烷浸提液的EAG值相当。在使用剂量为0.01 ng～100 μg反应内,小地老虎雄蛾触角对性信息素各组分及其混合物的剂量反应曲线大致呈“S”形。从不同日龄雄蛾对标准化合物的反应中,发现在羽化后第3天达到最高值,之后则随日龄增加EAG反应降低。     

粘虫雄蛾触角对其性信息素的电生理反应

用自行组装的触角电位仪,测定了粘虫Mythimna separata雄蛾蛾龄对标准化合物顺-11-十六碳烯醛(Z11-16：A1d)、顺-9-十六碳烯醛(Z9-16:Ald)和十六碳醛(16：A1d)的EAG反应的影响,分析了雄蛾触角对3种标准化合物的剂量-反应关系,发现粘虫雄蛾对Zll-16,Ald和Z9-16：Ald的剂量-反应曲线呈现出典型的“S”型,并且反应阐值较低。而对16：A1d几乎没有反应。最为重要的是检测了粘虫雄蛾对雌蛾腺体提取物的EAG反应,反应值的大小与样品中所提取的雌蛾腺体数目成正比。通过检测粘虫雄蛾对羽化不同天数,以及同一天羽化、在暗期不同时辰提取的雌蛾腺体提取物的EAG反应,证实了粘虫雄蛾的反应曲线与雌蛾释放性信息素的时辰节律呈正相关。还比较了烟青虫和粘虫雄蛾对粘虫雌蛾腺体提取物的EAG反应,间接证实了粘虫雌蛾腺体提取物中可能含有次要组分Z9-16;A1d。     

Sex pheromone analysis and effective attraction of males of the cabbage webworm,Hellula undalis,inhabiting the Mekong Delta of Vietnam

Hellula undalis is a harmful insect pest of green mustard in the Mekong Delta of Vietnam. In order to establish a tool for a sustainable pest control program, the sex pheromone of H. undalis inhabiting the Mekong Delta was examined. GC-EAD and GC–MS analyses of pheromone gland extracts from the virgin females elucidated three new components, (Z)-11-tetradecenyl acetate (Z11-14:OAc), (Z)-11-hexadecenal (Z11-16:Ald), and (11E,13E)-11,13-hexadecadien-1-ol, in addition to the known pheromone component (11E,13E)-11,13-hexadecadienal (E11,E13-16:Ald). Double bond positions of the two monoenyl components were determined by GC–MS analysis of the pheromone extract treated with dimethyl disulfide. On the other hand, GC–MS analysis of the female body extract detected the unsaturated hydrocarbon (3Z,6Z,9Z)-3,6,9-tricosatriene (Z3,Z6,Z9-23:H). Field examinations of their synthetic compounds indicated the significant role of E11,E13-16:Ald as a major component and a clear synergistic effect of the two monoenyl compounds as a minor component. Although the 3:3:7 mixture of Z11-14:OAc, E11-16:Ald, and E11,E13-16:Ald captured the largest number of males among the tested mixtures, the activity was still quite a bit lower than that of virgin females. However, the 3:3:7:1 mixture, which was prepared by adding a small amount of Z3,Z6,Z9-23:H to the 3:3:7 ternary lure, succeeded in attracting males more powerfully than the females did. This strong synergistic effect was not observed when the triene was added to unmixed E11,E13-16:Ald, indicating important roles of not only the triene but also the two monoenyl compounds as natural pheromone components.     

Reidentification of the female sex pheromone of the Indian meal moth, Plodia interpunctella: evidence for a four-component pheromone blend

Pheromone gland extracts from calling female Plodia interpunctella contained at least seven compounds that consistently elicited electroantennographic responses from male antennae upon gas chromatographic analysis. Three of these compounds were found to be the previously identified gland constituents, i.e., (Z,E)-9,12-tetradecadienyl acetate (Z9,E12-14:OAc), (Z,E)-9,12-tetradecadienal (Z9,E12-14:Ald) and (Z,E)-9,12-tetradecadienol (Z9,E12-14:OH). A fourth EAD-active compound was identified as (Z)-9-tetradecenyl acetate (Z9-14:OAc). The homologue (Z)-11-hexadecenyl acetate (Z11-16:OAc) was also identified in the extracts, but showed no EAD activity. The identity of all five compounds was confirmed by comparison of GC retention times and mass spectra with those of synthetic standards. In flight tunnel tests there were no significant differences in response of male P. interpunctella to the bait containing all four EAD-active compounds and the responses to female gland extacts. A behavioural assay of different two-compound blends in the flight tunnel showed that only addition of the corresponding aldehyde to the major pheromone component Z9,E12-14:OAc raised the male response. A subtractive assay, however, revealed that the exclusion of any of the compounds from the complete four-compound blend reduced its activity significantly. We thus conclude that the female-produced sex pheromone of P. interpunctella consists of at least four components, i.e., Z9,E12-14:OAc, Z9,E12-14:Ald, Z9,E12-14:OH and Z9-14:OAc.In a field trapping test performed in a storage facility, the four-component blend attracted significantly more males of P. interpunctella than traps baited with Z9,E12-14:OAc alone. In contrast, the highest number of Ephestia kuehniella males was found in the traps baited with this major component, suggesting that the secondary pheromone components contribute to the species specificity of the blend.     

Electrophysiological and behavioral responses of a parasitic wasp to plant volatiles induced by two leaf miner species

In the present study, Y-tube olfactometric assays demonstrated that headspace volatile extracts collected from leaf miner-damaged, or artificially damaged, bean plants were more attractive to naive females of the parasitoid insect Opius dissitus than those collected from healthy plants. Headspace extracts from both Liriomyza huidobrensis and Liriomyza sativae second-instar larvae-damaged beans were analyzed by coupled gas chromatography-electroantennographic detection (GC-EAD). Of nine EAD-active volatiles identified, (3E)-4,8-dimethyl-1,3,7-nonatriene, (3Z)-hexenyl acetate, (syn)-2-methylpropanal oxime, and (syn)-2-methylbutanal oxime were the most abundant compounds that evoked significant electroantennogram (EAG) responses. Compounds (3Z)-hexen-1-ol, (anti)-2-methylbutanal oxime, linalool, beta-caryophyllene, and (3E,7E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene also elicited clear EAG responses but were present in smaller amounts. Choice experiments in a Y-tube olfactometer indicated that synthetic versions of (3Z)-hexen-1-ol, 2-methylpropanal oxime, 2-methylbutanal oxime, 3-methylbutanal oxime, linalool, (E,E)-alpha-farnesene, and (3E,7E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene were attractive individually, while (3Z)-hexenyl acetate and (3E)-4,8-dimethyl-1,3,7-nonatriene were unattractive at concentrations similar to those obtained from the headspace collection. Moreover, a blend of nine EAD-active volatiles was significantly more attractive relative to hexane (solvent). A mixture of oximes, tereponids, and green leaf volatiles may facilitate host location by female O. dissitus.     

斜纹夜蛾性信息素通讯系统

采用单雌腺体微量分析技术,对斜纹夜蛾(中国种群)雌蛾腺体的组份进行鉴定,并研究了各组份的个体差异及释放规律,测试了雄蛾对各组份及其混合物的触角电位反应。雌蛾腺体内含有4个组份：Z9, E11-14∶Ac(A)、Z9, E12-14∶Ac(B)、Z9-14∶Ac© 和E11-14∶Ac(D),其比例为100∶27∶20∶27。     

Behavioural effects of minor sex pheromone components in Brazilian apple leafroller Bonagota cranaodes (Lep., Tortricidae)

Abstract:  The behavioural response of Brazilian apple leafroller males, Bonagota cranaodes (Meyrick), to natural and synthetic sex pheromone was studied in a wind tunnel. Calling females elicited upwind flights followed by landing and wingfanning at the source in 72% of the males tested. Female gland extracts, with the main compound ( E , Z )3,5dodecadienyl acetate released at 100 pg/min, attracted 57% of the males to the source. Few males (1%) were attracted to the main compound alone, released at the same rate. Even a synthetic blend of all five gland compounds eliciting an antennal response, formulated according to their proportion in female gland extracts, was barely attractive (7%). Comparison of this synthetic blend and female gland extracts indicates a behavioural role of other gland compounds. Male attraction was significantly increased (34%) in response to a 100 : 5 : 5 : 5-blend of the main compound and three minor gland compounds, ( Z )-5-dodecenyl acetate, ( E , Z )-3,5-tetradecadienyl acetate, and ( Z )-9-hexadecenyl acetate.     

大螟雄蛾触角对性外激素及其类似物的电生理反应

电生理试验显示出:大螟Sesamia inferens(Walker)雄蛾触角对Z11-16:Ac(A)oZ11-16:OH(B)激起强烈的触角电位(EAG)反应,Z11-16:ALD?,E11-16:Ac(D),Z9-14:Ac(E)和Z7-12:Ac(F)四种化合物也能激起较强的EAG反应;A化合物的刺激阈比B高,此两种化合物5:5比例时,激起的反应最强烈。电生理的试验推测,雄蛾触角对A和B两种化合物的感受,是通过触角内两种不同类型的嗅觉感受器。A和B不同比例混合后,田间诱蛾试验证明:在9:1,8:2,5:5的比例时,其诱蛾量远远超过单独的A化合物;E加入A与B的混合物中,起抑制诱蛾的效果,上述试验表明,Z11-16:OH是大螟的性诱剂。     

Antennal sensitivity to female sex pheromone compounds of Spodoptera frugiperda males (Lepidoptera: Noctuidae) and associated field behaviour

The fall armyworm (FAW), Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctuidae), is one of the most important insect pests of corn, sorghum, rice, and grasses. The sex pheromone produced by S. frugiperda is composed of a mixture of esters. In this study, I determined the antennal responses of FAW males from 22 populations in Mexico to the components of the sex pheromone of this species: (Z)-7-dodecenyl acetate (Z7-12:OAc), (Z)-9-tetradecenyl acetate (Z9-14:OAc), and (Z)-11-hexadecenyl acetate (Z11-16:OAc) at four doses (0.01, 0.1, 1, and 10 μg). In addition, I evaluated the behavioural activity of single compounds in the field. The largest antennal responses of FAW males from all the sampled regions were elicited by Z9-14:OAc (all doses evaluated) and Z7-12:OAc (0.01, 0.1, and 1 μg). The male antennal responses evoked by Z11-16:OAc were smaller but similar to responses to Z7-12:OAc at lower doses (0.01 and 0.1 μg). In the field test, Z9-14:OAc produced significantly higher captures of S. frugiperda males compared to Z7-12:AOc and Z11-16:OAc. Antennal responses were related to captures obtained in the field, supported by the positive correlation of these variables [electroantennography (EAG) response and behaviour], with the exception of Z7-12:OAc, which elicited relatively large EAG responses but did not produce high captures of S. frugiperda. These results are of importance to agriculture, enabling the implementation of better methods of monitoring and controlling this pest, and support the suggestion that a mixture of Z9-14:OAc and Z7-12:OAc could represent an effective attractant for all evaluated populations of S. frugiperda in Mexico.     

棉铃虫齿唇姬蜂对植物挥发物和寄主性信息素腺体化合物的EAG反应

测试了棉铃虫齿唇姬蜂Campoletis chlorideae Uchida对58种植物挥发物和5种寄主性信息素腺体化合物的EAG反应。在100 μg的刺激剂量下,棉铃虫齿唇姬蜂对C₅～C₇脂肪醇的EAG反应最强,碳链延长或缩短都将导致反应的降低;对脂肪醛、酮、酸和酯都有一定的反应。棉铃虫齿唇姬蜂对萜烯的EAG反应很低,对氧化萜的反应普遍升高。3种芳香化合物均可激起棉铃虫齿唇姬蜂较强的EAG反应。剂量反应曲线表明,具有EAG活性的化合物激起的反应强度与化合物的剂量呈正相关,而2种萜烯——α-蒎烯和反式石竹烯,在测定的剂量范围内EAG活性都很低。棉铃虫齿唇姬蜂对寄主性信息素腺体化合物也有EAG反应,用100 μg和1 000 μg的寄主性信息素刺激,雄蜂的反应可比雌蜂的反应高出1倍。对植物挥发物在棉铃虫齿唇姬蜂寻找寄主中的作用进行了讨论。     

苹毛丽金龟对植物挥发物成分的触角电位及行为反应

为筛选适宜的苹毛丽金龟Proagopertha lucidula (Faldermann)引诱剂化学物质, 对已报道的金龟子科两性引诱剂单一组分进行了触角电位（EAG）和Y型嗅觉仪中的嗅觉反应测定。结果表明: 在10 μg刺激剂量下测试的11 种植物挥发物中, 只有顺-3-己烯-1-醇、香叶醇、茴香脑和丁香酚有明确的EAG反应值, 其他7种化合物具有弱反应值。剂量反应曲线表明, 具有明确的EAG活性的4种化合物激发的反应强度与化合物的剂量呈正相关。在Y型嗅觉仪中, 顺-3-己烯-1-醇、香叶醇、茴香脑和丁香酚4种化合物在1, 10, 100 μg剂量下的行为反应百分率都显著高于对照溶剂正己烷, 且雌雄之间无显著差异。该研究结果可为开发苹毛丽金龟田间引诱剂奠定基础。     

Sex pheromone of the butterbur borer, Ostrinia zaguliaevi

The sex pheromone blend of the butterbur borer, Ostrinia zaguliaevi (Lepidoptera: Pyralidae) was analyzed by means of gas chromatography-electroantennographic detection (GC-EAD), GC-mass spectrometry and a series of wind-tunnel bioassays. Four EAD-active compounds were detected in the female sex pheromone gland extract, and these were identified as tetradecyl acetate (14:OAc), (Z)-9-tetradecenyl acetate (Z9-14:OAc), (E)-11-tetradecenyl acetate (E11-14:OAc) and (Z)-11-tetradecenyl acetate (Z11-14:OAc). The average amounts ± s.d. of the four compounds in a single sex pheromone gland were 7.9±3.7 ng, 10.1±3.2 ng, 1.1±0.5 ng and 11.6±5.1 ng, respectively. In a wind-tunnel bioassay, the ternary blend of Z9-, E11- and Z11-14:OAc at a ratio found in the sex pheromone gland (45:5:50) elicited the same behavioral responses from the males as did virgin females and pheromone gland extract. Removal of any single compound from the ternary blend significantly diminished the pheromonal activity, whereas addition of 14:OAc to the ternary blend had no effect on the males' behavioral responses. Therefore, it was concluded that the sex pheromone blend of O. zaguliaevi is composed of Z9-14:OAc, E11-14:OAc and Z11-14:OAc at a ratio of 45:5:50.     

槐庶尺蛾性信息素腺体EAG活性成分绝对构型的鉴定(英文)

槐庶尺蛾Semiothisa cinerearia Bremer et Grey （鳞翅目： 尺蛾科）是我国北方国槐Sophora japonica L.上的重要食叶害虫。本研究的主要目的是阐明槐庶尺蛾性信息素成分化学结构的绝对构型, 为在城市地区环境友好地防控槐庶尺蛾的为害提供一种新方法。经与标准品比较气相色谱保留时间和质谱特征离子, 从槐庶尺蛾处女雌蛾（2-3日龄）性信息素腺体溶剂提取物中检测到顺6, 顺9-顺-3, 4-环氧-十七碳二烯烃和顺3, 顺6, 顺9-3, 6, 9-十七碳三烯烃2种成分, 在腺体中以100∶4.8±1.3 （N=12）的比例存在。槐庶尺蛾性信息素腺体提取物进一步经手性毛细管色谱柱（CycloSil-B, 30 m×0.25 mm×0.25 μm 液膜厚）分离, 在优化的程序升温条件下发现腺体成分顺6, 顺9-顺-3, 4-环氧-十七碳二烯烃具有3R, 4S的绝对构型。两种合成的对映异构体混合物顺6, 顺9-3R, 4S-环氧-十七碳二烯烃和顺6, 顺9-3S, 4R-环氧-十七碳二烯烃以1.28∶1的比例加到腺体提取物中, 比例变为1.55∶1。根据这一分析, 腺体成分顺6, 顺9-顺-3, 4-环氧-十七碳二烯烃进一步确认具有3R, 4S的绝对构型。该研究结论将为生产上研发高效的槐庶尺蛾性信息素诱芯奠定坚实的基础。     

Inter- and intraspecific activities of compounds derived from sex pheromone glands of currant borer, Synanthedon tipuliformis (Clerck) (Lepidoptera: Sesiidae)

Gas chromatography and mass spectrometry analyses of crude sex pheromone gland extracts revealed that virgin Synanthedon tipuliformis (Clerck), currant borer (Lepidoptera: Sesiidae) females, produced 6 compounds, structurally related to sex pheromone components of clearwing moths. By comparison of retention times and mass spectra of natural products with corresponding properties of synthetic standards, these compounds were identified as: (2E,13Z)-octadeca-2,13-dien-1-yl acetate (E2,Z13-18:OAc), (3E,13Z)-octadeca-3,13-dien-1-yl acetate (E3,Z13-18:OAc), (13Z)-octadec-13-en-1-yl acetate (Z13-18:OAc), (2E,13Z)-octadeca-2,13-dien-1-ol (E2,Z13-18:OH), (13Z)-octadec-13-en-1-ol (Z13-18:OH) and octadecan-1-ol (18:OH) in the ratio 100:0.7:2.7:3.2:traces:traces. The first 3 compounds were previously known to occur in the sex pheromone gland extracts of currant borers, while the last 3 chemicals are now reported for the first time. Trapping tests carried out in the black currant field revealed that E2,Z13-18:OAc, when tested separately, attracted S. tipuliformis males, while addition of E3,Z13-18:OAc to the main component increased the effectiveness of E2,Z13-18:OAc over seven times. The attractiveness of 6 component lures did not differ significantly from the one of the binary mixture, confirming that E2,Z13-18:OAc and E3,Z13-18:OAc in the ratio100:0.7 are essential sex pheromone components of S. tipuliformis. Trapping tests carried out at the dwelling place of Synanthedon scoliaeformis (Borkhausen) (Lepidoptera: Sesiidae) revealed that, in addition to intraspecific synergistic effect, E3,Z13-18:OAc increased the specificity of the pheromone signal of S. tipuliformis, acting by intraspecific mode as an attraction antagonist against S. scoliaeformis males. By this way, it ensured the specificity of the sex attraction signal of the currant borer. Consequently, both compounds E2,Z13-18:OAc and E3,Z13-18:OAc have to be present in pheromone formulations used for monitoring and/or control of S. tipuliformis to avoid effecting non-target species. Other compounds identified from the sex pheromone gland of S. tipuliformis did not show any significant interspecific activity for males of S. scoliaeformis, however, they provide a basis to achieve specificity of a pheromone signal of S. tipuliformis and could act as attraction antagonists against other clearwing moth species which, like S. tipuliformis, employ E2,Z13-18:OAc as their sex pheromone component.     

Female Attacus atlas respond to pheromones of Antheraea polyphemus: a comparative electrophysiological and biochemical study

Female Attacus atlas respond electrophysiologically to both of the Antheraea polyphemus pheromone components (E,Z)-6,11-hexadecadienyl acetate and (E,Z)-6,11-hexadecadienal. Moreover, they possess a pheromone-binding protein (PBP) and general odorant-binding proteins (GOBPs), as well as a pheromone-degrading sensillar esterase and aldehyde oxidase enzymes. They show no electroantennogram responses to their own gland extract. In contrast, female A. polyphemus do not respond to their own or to A. atlas pheromone. Male A. atlas do not detect any of the A. polyphemus compounds but only the conspecific female gland extracts. Both male A. atlas and female A. polyphemus possess PBP and GOBP but lack the pheromone-degrading esterases of male Antheraea. The results indicate that the two species use quite distinct classes of chemicals as pheromones. In spite of this, the N-terminal amino acid sequences of the PBPs show homology of 68%.     

Identification of a pheromone blend attractive to Manduca sexta (L.) males in a wind tunnel

Analyses of solvent rinses of the external surfaces of pheromone glands excised from calling female tobacco hornworm moths, Manduca sexta (L.), revealed the presence of the following compounds: (Z)-9-hexadecenal, (Z)-11-hexadecenal, (E)-11-hexadecenal, hexadecanal, (E,Z)-10,12-hexadecadienal, (E,E)-10,12-hexadecadienal, (E,E,Z)-10,12,14-hexadecatrienal, (E,E,E,)-10,12,14-hexadecatrienal, (Z)-11-octadecenal, (Z)-13-octadecenal, octadecanal, and (Z,Z)-11,13-octadecadienal. The two trienals were identified by mass and PMR spectral analyses and by ozonolyses, and their structures were confirmed by synthesis. In a wind tunnel male tobacco hornworm moths exhibit the same behaviors in response to a synthetic blend of all of the components, the gland rinse, or a calling female. Both (E,Z)-10,12-hexadecadienal and (E,E,Z)-10,12,14-hexadecatrienal are required to stimulate males to complete the characteristic behavioral sequence: anemotaxis, approaching and touching the pheromone source, and bending their abdomens in apparent copulatory attempts. The other components of the blend may play more subtle roles.     

Synthesis, structural identification and biological activity of 11,12-dihydroxyeicosatetraenoic acids formed in human platelets

An enantiospecific route for the synthesis of 11,12-dihydroxyeicosatetraenoic acids was developed and used to synthesize 11,12-dihydroxy-5(Z),7(E),9(E),14(Z)-eicosatetraenoic acids. The 11,12-DHETEs were synthesized with the stereochemistry of the hydroxyl group being 11(R),12(S) and 11(S),12(S). The synthetic compounds were used to elucidate the structure of 11,12-DHETEs formed in human platelets by comparison of the chromatographic retention time in HPLC and GC as well as their ion fragmentation pattern in GC-MS. The major 11,12-DHETE formed in human platelets was found to be identical with 11(R),12(S)-dihydroxy-5(Z),7(E),9(E),14(Z)-eicosatetraenoic acid. Two more compounds were tentatively identified as 11(S),12(S)-dihydroxy-5(Z),7(E),9(E),14(Z)-eicosatetraenoic acid and 11,12-dihydroxy-5(E),7(E),9(E),14(Z)-eicosatetraenoic acid. Furthermore, the 11(S),12(S)-dihydroxy-5(Z),7(E),9(E),14(Z)-eicosatetraenoic acid was found to possess biological activity on neutrophil functional responses. However, the major compound, 11(R),12(S)-dihydroxy-5(Z),7(E),9(E),14(Z)-eicosatetraenoic acid, formed in platelets lacks biological activity in the test systems used. The present data further support that 11,12-dihydroxy-eicosatetraenoic acids are formed in human platelets via a leukotriene like mechanism presumably by the 12-lipoxygenase. Furthermore, the biological effects of one of the compounds showed a unique activity profile compared to other lipoxygenase products.     

黄杨绢野螟雌蛾性信息素的鉴定及诱蛾活性

【目的】研究旨在深入探讨中国黄杨绢野Diaphania perspectalis 的雌蛾性信息素组成及诱蛾活性。【方法】利用气质联用仪（GC-MS）对黄杨绢野螟正常型性成熟雌蛾的性腺体提取物和合成标样比较分析,并用反-11-十六碳烯醛(E11-16:Ald) 、顺-11-十六碳烯醛（Z-11-16:Ald）、顺-9-十六碳烯醛（Z-9-16:Ald)、顺-11-十六碳烯醇（Z-11-16:OH)等物质进行触角的电生理测定,最后开展田间诱集比较试验以筛选出最佳性信息素混合物。【结果】Z-11-16:Ald为中国黄杨绢野螟正常型性信息素主要组分,E-11-16:Ald的含量极低,Z-11-16:OH未检测到。正常型雄性黄杨绢野螟触角对Z-11-16:Ald, E-11-16:Ald, Z-9-16:Ald和Z-11-16:OH产生强烈的EAG反应,并随着浓度的提高而显著增加;而对Z-11-16:Ac和E-11-16:Ac的嗅觉反应较弱,低于对植物绿叶气味顺3-己烯乙酸酯（Z-3-6:Ac）的反应。单一Z-1-16:Ald对正常型雄性黄杨绢野螟具有强烈的诱集效果,加入E-11-16:Ald有一定的增效作用,但在统计上则不显著。单一Z-11-16:Ald组分对黑化型雄性黄杨绢野螟无引诱活性,必需加入一定比例的E-11-16:Ald才显示诱蛾活性。Z-11-16:Ald:E-11-16:Ald的比例为250 μg:250 μg时诱集到的黑化型雄性黄杨绢野螟数量最多,而Z-11-16:Ald:E-11-16:Ald的比例为429 μg:71 μg时则诱集到的正常型雄性黄杨绢野螟数量最多。同时,单一Z-11-16:Ald也可引诱大量雄性粘虫Mythimna separata,但E-11-16:Ald抑制其活性。【结论】中国黄杨绢野螟的性信息素主成分是Z-11-16:Ald,单一组分即可在田间强烈引诱雄蛾,E-11-16:Ald的功能只起到微弱的增效作用,但也可能起种的专一性的作用。正常型与黑化型黄杨绢野螟对性信息素的嗅觉反应存在差异,黑化型黄杨绢野螟的性信息素接近日本种,即性信息素组成为Z-11-16:Ald和E-11-16:Ald 的混合物,其比例为1:1,且E-11-16:Ald为必需。