横坑切梢小蠹对植物挥发物的电生理和行为反应

为筛选出适宜配制横坑切梢小蠹(Tomicus minor Hartig)引诱剂的有效化合物,测定了横坑切梢小蠹雌、雄成虫对寄主云南松主要挥发性化合物的触角电位(EAG)和行为反应。结果表明:与对照相比,在10 g·L-1浓度刺激下所测试的9种植物挥发物都能引起横坑切梢小蠹雌、雄虫触角的EAG反应,且触角对不同挥发物的EAG反应差异显著(P0.05),其中雌、雄虫对(+)-α-蒎烯、(+)-柠檬烯、(+)-3-蒈烯、β-蒎烯和异松油烯的EAG反应较强;在剂量反应试验中,雌、雄虫的EAG反应都随着(+)-α-蒎烯、(+)-柠檬烯、(+)-3-蒈烯和β-蒎烯浓度的增加而增强,当浓度增加到10 g·L-1时,EAG反应最强;而雌、雄虫对异松油烯的EAG反应在1 g·L-1最强;除(+)-柠檬烯没有明显的定向作用外,(+)-α-蒎烯、β-蒎烯、(+)-3-蒈烯和异松油烯对横坑切梢小蠹均表现出了明显的引诱作用;行为反应多重比较表明,(+)-α-蒎烯在10 g·L-1浓度下对雌雄虫的引诱作用最大。该研究结果可为开发横坑切梢小蠹林间引诱剂提供参考。     

油松萜烯成分变化与红脂大小蠹的反应特性

采用顶空采样方法,比较健康油松、人工损伤油松以及抗性油松在单萜烯成分组成上的差异。GC-MS分析表明,在自然状况下,油松树干释放的萜烯类成分很少,以α-蒎烯占绝对优势(>97%);人工损伤后,油松萜烯类成分明显增多,除α-蒎烯为主要成分外,还包括β-蒎烯、月桂烯、柠檬烯、萜品油烯、β-水芹烯、长叶烯等;而抗性油松萜烯类成分更为复杂。对3类油松主要单萜类成分的相对含量方差分析表明,α-蒎烯的相对含量呈显著降低;3-蒈烯在损伤寄主中相对含量最高,在抗性寄主中相对含量与自然状态下没有差异。柠檬烯、莰烯、萜品油烯在抗性寄主中相对比率显著增加。而β-蒎烯、月桂烯、β-水芹烯相对含量在3个处理中变化不大。在此基础上,比较红脂大小蠹Dendroctonus valens LeConte对油松主要单萜类成分的触角电位及嗅觉行为反应。结果表明,室内触角电位、嗅觉试验与先前林间试验结果相一致,即红脂大小蠹对(+)-3-蒈烯表现出最强的电生理和行为反应。对R-(+)-α-蒎烯和S-(-)-α-蒎烯研究发现,红脂大小蠹对α-蒎烯2个对映体的触角电位、嗅觉行为无显著不同。结合油松单萜类含量变化特点与红脂大小蠹行为反应,认为3-蒈烯相对含量上升可能作为易感寄主特点;而柠檬烯、莰烯、萜品油烯相对比率增加则代表了抗性或者非适合寄主的特征。     

华山松大小蠹对几种寄主挥发物组分的EAG和行为反应

为筛选适宜配制华山松大小蠹(Dendroctonus armandi)引诱剂的有效化学成分,用触角电位仪和Y型嗅觉仪测定了华山松大小蠹雌、雄虫对华山松挥发物主要成分的触角电生理(EAG)和行为反应.结果表明:在0.01、0.1、1、10、100 μg 5种刺激剂量下,7种化合物在特定浓度下均有明确的EAG反应;雌、雄虫对月桂烯、(+)-3-蒈烯、β-石竹烯3种化合物及雄虫对(+)-α-蒎烯、柠檬烯的EAG相对电位的最大值均出现在10μg刺激条件下;在10 μg刺激剂量条件下,雌虫对(+)-α-蒎烯、β-蒎烯和(+)-3-蒈烯有明显的正趋向反应,正趋向率均高于72%且显著高于雄成虫对3种挥发物的正趋向率;在1 μg刺激下,只有雄虫对(+)-3-蒈烯有一定正趋向反应;而在100μg条件下,(-)-α-蒎烯对雌、雄虫均有一定驱避作用.该研究结果可为开发华山松大小蠹林间引诱剂提供借鉴.     

被害马尾松（Pinus massoniana）针叶挥发性物质的提取、鉴定及蚕饰腹寄蝇（Blepharipa zebina）的电生理活性

试验使用动态顶空吸附的方法,提取了被害马尾松(Pinus massoniana)针叶挥发物,并通过气相色谱-质谱联用仪(GC-MS)及标准样品进行鉴定。结果表明,被害马尾松针叶挥发性物质主要包括绿叶挥发物、单萜、含氧单萜及倍半萜等四大类物质;挥发物中以单萜的含量最高,其它3类物质含量较低。通过触角电位图(EAG)技术,测定了23种挥发性物质标准样品的石蜡油溶液对蚕饰腹寄蝇(Blepharipa zebina)雌蝇的电生理活性。结果表明,蚕饰腹寄蝇雌蝇对α-蒎烯、β-蒎烯、长叶烯、莰烯、乙酸冰片酯等的相对触角电位反应值与湿润空气对照相比并无显著差异;雌蝇对其它刺激物的相对触角电位反应值与湿润空气对照相比均存在显著差异。同时测定了雌蝇对8种标样,在5个浓度系列下的剂量-反应,并分析了反应阈值。结果表明,蚕饰腹寄蝇雌蝇对顺-3-己烯-1-醇和里哪醇的反应阈值为0.1μg/μl,对壬醛的反应阈值为1μg/μl,对柠檬烯、α-水芹烯、2,6-二甲基-2,4,6-辛三烯、β-石竹烯4种物质的反应阈值为100μg/μl,而对α-蒎烯,在测试的剂量范围内不存在反应阈值。在确定对蚕饰腹寄蝇有生理活性的物质成分和分析反应阈值的基础上,对寄生蝇类定位寄主的机制进行了讨论。     

松墨天牛成虫对幼虫虫粪挥发性物质的触角电位反应及林间驱避试验

为了研制松墨天牛Monochamus alternatus Hope驱避剂,本文利用触角电位技术和田间试验的方法研究了松墨天牛雌雄成虫对幼虫虫粪挥发性物质的触角电位反应及幼虫虫粪己烷提取物、合成化合物混合物的林间驱避作用。结果表明：α-蒎烯、β-蒎烯、3-蒈烯、柠檬烯和长叶烯均能引起松墨天牛雌雄成虫一定的触角电生理反应,而4-甲基-2,6-二叔丁基苯酚不能引起松墨天牛雌雄成虫的触角电生理反应。林间驱避试验结果说明,幼虫虫粪的己烷提取物处理过的树干上的刻槽数明显少于对照树干上的刻槽数,二者具有极显著差异;有合成化合物的混合物存在的诱捕器诱捕到的雌虫数（平均值3.80±1.02）与对照诱捕到的雌虫数（平均值16.80±1.16）差异极显著。结果显示α-蒎烯、β-蒎烯、3-蒈烯、柠檬烯、长叶烯和4-甲基-2,6-二叔丁基苯酚的混合物对松墨天牛雌虫具有驱避作用,有望开发出一类新的驱避剂。     

几种抗氧化剂对单萜烯稳定性及其对松墨天牛诱捕效果的影响

[目的]评价6种抗氧化剂对单萜烯类化合物稳定性的影响及其在野外条件下单萜烯对松墨天牛Monochamus alternatus Hope成虫的诱杀效果.[方法]采用水浴锅加热加速氧化法,以气相色谱法测定含量,研究不同抗氧化剂对α-蒎烯、β-蒎烯和月桂烯稳定性的影响,并进行林间松墨天牛的诱捕试验.[结果]在供试的6种抗氧化剂中,TBHQ对单萜烯的保护效果最显著(P＜0.05).浓度对单萜烯的保护效果影响显著(F=6.631,P=0.007),其中浓度为0.03％的保护效果最显著(P＜0.05).抗氧化剂对α-蒎烯、β-蒎烯和月桂烯的保护效果存在显著差别(F=3.231,P=0.031),抗氧化剂对β-蒎烯的保护效果最显著(P＜0.05).野外诱捕实验表明添加抗氧化剂0.03％TBHQ的单萜烯(α-蒎烯:β-蒎烯:月桂烯=50:40:10)对松墨天牛野外诱捕持效期明显延长,持效期延长不少于30d.[结论]添加抗氧化剂可保护单萜烯,维持单萜烯在野外条件下的稳定性,保持引诱剂成分的稳定性与持效性,延长单萜烯类昆虫引诱剂在野外诱捕害虫的持效期.     

滇产云南松、思茅松松针油的化学成分

云南松(Pinus yunnanensis Fr.)和思茅松〔Pinus kesiya Royle ex Gord.var.langbianensis(A.Chev.)Gaussen〕为云南针叶林主要树种。我们已研究了思茅松松节油的化学成分,为松针油利用提供科学数据,比较松节油与松针油化学成分的同异,并考察α-蒎烯,β-蒎烯的含量与分布的关系,本文用气相色谱/质谱/计算机联用仪,对滇南到滇中水平分布及由低到高垂直分布的八个云南松和九个思茅松松针油油样进行了定性、定量分析。     

马尾松毛虫对马尾松和湿地松的选择与适应研究

用马尾松老叶、新叶,湿地松老叶、新叶,当年生马尾松新叶、湿地松新叶和当年生以20％和40％β-蒎烯处理过的马尾松新叶作食料饲养马尾松毛虫。结果表明：马尾松毛虫幼虫在第1代发生期取食马尾松老叶、马尾松新叶、湿地松老叶和湿地松新叶等4种不同质量的食料后,因其食料中10种必需氨基酸含量和挥发性物质β-蒎烯含量的不同,导致幼虫的存活率差异显著。其中,取食马尾松老叶的幼虫成活率最高（44％）,依次为马尾松新叶（32.7％）、湿地松老叶（4％）,而取食湿地松新叶的幼虫全部死亡。通过马尾松针叶增加外援β-蒎烯喂养马尾松毛虫实验,表明增加了外源β-蒎烯的松针饲养的马尾松毛虫幼虫与用同样松针未增加外源β-蒎烯饲养的幼虫相比,死亡率明显提高;松树中β-蒎烯含量的增加与幼虫成活率呈显著负相关。由此,我们阐明了马尾松与湿地松对马尾松毛虫的抗虫机制。     

柞蚕雌蛾性信息素及其类似物的结构和活性关系的电生理学研究

本文用电生理学的单细胞记录方法,研究了柞蚕雄蛾(Antheraea pernyi)触角的毛形感器对雌蛾性信息素及相应的几何异构体、光学异构体的反应特性;测定了剂量-反应曲线.研究结果表明:信息化合物的双键构型及光学特性对触角电位(以EAG表示)活性大小有重要影响.     

青杨脊虎天牛对植物源挥发物的EAG和行为反应

测定了青杨脊虎天牛Xylotrechus rusticus （L.）雌、雄成虫对其寄主杨树中的水杨醛（0.95 μmol/μL）和非寄主植物中0.3 μmol/μL的叶绿醇、0.4 μmol/μL的水芹烯和0.6 μmol/μL的 R 型α-蒎烯、S 型α-蒎烯、S型β-蒎烯、3-蒈烯、罗勒烯、香草烯和松节油等10种植物挥发性气味物质的触角电位（EAG）反应。结果表明,与对照相比,这10种植物挥发物多能引起成虫明显的EAG反应( P<0.05,P<0.01 ),其中雌虫对松节油、水杨醛、R 型α-蒎烯和 S 型α-蒎烯的EAG反应较强; 雄虫对 R 型α-蒎烯的EAG反应最强,松节油次之。根据雌虫对这10种挥发物EAG反应的强弱,进一步测定了雌虫对0.00006、0.0006、0.006、0.06、0.6、0.12 μmol/μL的松节油、R 型α-蒎烯、S 型α-蒎烯以及0.000095、0.00095、0.0095、0.095、0.95、0.19 μmol/μL的水杨醛的EAG和行为反应。结果表明,雌虫对松节油、水杨醛和 R 型α-蒎烯的EAG反应随气味物质浓度的增加而增加,水杨醛浓度增加到0.95 μmol/μL、松节油和 R 型α-蒎烯浓度增加到0.6 μmol/μL以后,EAG反应值趋于平稳;对 S 型α-蒎烯的反应随浓度的增加而呈线性增加。水杨醛浓度低于0.095时,对雌虫没有明显的定向作用( P>0.05 ),高于此浓度时表现为驱避作用( P<0.05 ); 松节油在浓度低于或等于0.6 μmol/μL时对雌虫表现为驱避作用,浓度为0.6时驱避效果最佳（ P<0.01 ）。雌虫对 R 型α-蒎烯和 S 型α-蒎烯没有明显的定向行为反应。     

Effect of pinene isomers on germination and growth of maize

Terpenes, secondary metabolites that are present in the essential oils of aromatic plants, are responsible for the biochemical interaction between plants, known as allelopathy. Monoterpenes are a major component of essential oils. Pinene is a monoterpene well-known for its phytotoxic action, but little is known about the allelopathic effect of its isomers. The aim of this study is to determine the effect of pinene's structural isomers and enantioisomers [(−)-α-pinene; (+)-α-pinene; (−)-β-pinene and (+)-β-pinene] at 0.16 mM, on certain physiological parameters (growth, dry weight, phenol, photosynthetic pigments and abscisic acid content) in both the germination and growth of maize (Zea mays L.). In germination bioassays, neither of the α-pinene stereoisomers showed change when compared to the control with respect to seed vigour; but root growth was increased, while β-pinene (racemic mixture) inhibited germination and plant length. In the growth bioassay, all of the pinene isomers decreased the plant length. In general, β-pinene terpene was more phytotoxic than α-pinene in both bioassays. Differences in germination and growth of maize treated with the pinene isomers can be attributed to different action mechanisms which depends both on the growth phases of maize and on the particular pinene isomers.     

黄荆中β-石竹烯对棉蚜的毒力和作用机理

为明确泰山野生黄荆Vitex negundo种子中的有效杀虫活性成分、杀虫作用及其毒理机制,本研究采用硅胶柱层析,GC-MS技术和生物活性追踪方法,测定了泰山黄荆种子中的杀虫活性成分;采用生物测定和生化分析法,研究了黄荆中的β-石竹烯和α-蒎烯对棉蚜Aphis gossypii的毒力及作用机制。结果表明：通过三级柱层析从黄荆中分离得到对棉蚜毒力高的馏分β-石竹烯和α-蒎烯,其含量分别达7.68%和5.45%。β-石竹烯和α-蒎烯对棉蚜的触杀毒力都较高,并以β-石竹烯的毒力最高,LD₅₀为0.65×10^-1 μg/头。β-石竹烯和α-蒎烯对棉蚜均具有强烈的忌避作用,处理棉蚜24 h的AFC₅₀分别为0.80×10³和0.89×10³ mg/L,其中也以β-石竹烯的忌避毒力最大。β-石竹烯和α-蒎烯以亚致死剂量处理棉蚜,对其繁殖力、排蜜频率和排蜜量均有显著不利影响。β-石竹烯和α-蒎烯处理棉蚜或离体酶,对乙酰胆碱酯酶、多酚氧化酶、羧酸酯酶和谷胱甘肽-S-转移酶都有明显抑制作用。结果显示β-石竹烯和α-蒎烯是黄荆种子提取物中的重要杀虫活性成分,并且其致毒机制存在多样性,开发应用价值大。     

黄荆精油对玉米象的杀虫活性成分、毒力及作用机制

为明确黄荆精油及其主要成分作为储粮保护剂的开发利用价值,采用水蒸气蒸馏法从泰山黄荆Vitex negundo Linn.叶片中提取精油,利用GC-MS技术进行了成分分析鉴定,研究了黄荆精油及其主要成分桉树脑和α-蒎烯对玉米象 Sitophilus zeamais Motschulsky 成虫的毒力及作用机制。结果表明: 黄荆精油中含量大于0.3%的成分有31种,其中石竹烯、桉树脑和α-蒎烯的含量分别为35.97%,8.21%和0.69%。桉树脑、α-蒎烯和黄荆精油对玉米象成虫的综合杀虫毒力都较高,并以桉树脑的毒力最高,LC₅₀为0.7171 g·kg^-1;在2.0 g·kg^-1剂量下,桉树脑、α-蒎烯和黄荆精油对玉米象种群的抑制率分别达100％,85.45％和89.73％;3种药剂对玉米象72 h触杀LC₅₀分别为0.2690,0.7529 和0.2969 mg·cm^-2,毒力都很高;3种药剂在4 g·kg^-1剂量下,对玉米象的驱避率分别为96.49%,84.26％和90.61%,防虫作用大;3种药剂对玉米象72 h的熏蒸LC₅₀分别为14.053, 28.648 和21.429 μL·L^-1,熏蒸杀虫毒力较高,其中以桉树脑的毒力最高。3种药剂对玉米象有干扰呼吸的作用,对离体乙酰胆碱酯酶、过氧化氢酶和羧酸酯酶都有抑制作用。这些结果明黄荆精油及其主要成分的作用机制具有多样性。     

Influence of environmental factors on content and composition of essential oil from common juniper ripe berry cones (Juniperus communis L.)

Abstract

The present study evaluated the influence of some environmental factors on the quantity and composition of essential oil (EO) in ripe berry cones of Juniperus communis L. The berry cones were collected from juniper shrubs growing wild at five localities of north-east Slovakia during the years 2012–2014. The EO yield ranged from 0.4 to 1.9%, depending on the locality and year. In the EO, eight monoterpenes (α-pinene, β-pinene, β-myrcene, sabinene, limonene, terpinene-4-ol, borneol, bornylacetate) and one sesquiterpene (β-caryophyllene) were identified. The dominant component was the monoterpene α-pinene, ranging from 31.0 to 49.0%. The amount and composition of the EO was affected by soil composition (content of humus and pH) and topographic environmental factors, including air temperature and precipitation. According to the composition of the EO, the studied juniper shrubs belong to the α-pinene chemotype.     

Biosynthesis of chiral α- and β-pinenes in pinus species

C-3 of (+) and (?)-α-pinene and of (?)-β-pinene biosynthesized in several Pinus species was derived from C-2 of mevalonate; and the hydrogen at C-5 in all the isomers was derived from that at C-6 in nerol. This pattern is consistent with two routes for bicyclization of the acyclic biosynthetic precursor: one leads to (?)-β-pinene and the other to (+)-α-pinene of opposite absolute configuration. (?)-α-Pinene probably results from subsequent isomerisation of the (?)-β-isomer, and (very small) amounts of (+)-β-pinene result from similar (unfavoured thermodynamically) isomerisation of the (+)-α-isomer.     

Key structural features in cis-carane, (+)-3-carene,cis-pinane, (+)-α-pinene,and (−)-β-pinene influencing red turpentine beetle primary attraction when released with ethanol

1. In US Pacific Northwest ponderosa pine forests the primary attraction order shown previously for red turpentine beetle, Dendroctonus valens (Coleoptera: Curculionidae: Scolytinae), is (−)-β-pinene+ethanol > (+)-3-carene+ethanol > (+)-α-pinene+ethanol. The monoterpenes are bicyclic C₁₀H₁₆ isomers containing one 6-carbon ring with one double bond. Both pinenes have a 4-carbon second ring and differ only by their endocyclic or exocyclic double bond. The (+)-3-carene second ring has 3-carbons; its double bond is endocyclic like (+)-α-pinene.
2. Ring system and double bond influences on primary attraction were evaluated by hydrogenating (+)-3-carene and (+)-α-pinene to cis-carane and cis-pinane, respectively. Field test primary attraction strengths were (−)-β-pinene+ethanol > cis-carane+ethanol > cis-pinane+ethanol > ethanol.
3. In combination with ethanol (i) a double bond is not required in either ring system to attract D. valens, (ii) the cis-carane bicyclic 3, 6-carbon ring system provides stronger beetle attraction than the cis-pinane 4, 6-carbon bicyclic ring system, and likely structural basis for stronger (+)-3-carene attraction over (+)-α-pinene, (iii) adding an exocyclic double bond to the 4, 6-carbon ring system elevates attraction above the 3, 6-carbon ring system with no double bond, and (iv) the 4, 6-carbon ring system is a much stronger attractant with an exocyclic rather than endocyclic double bond.

     

Red turpentine beetle primary attraction to β-pinene or 3-carene (with and without ethanol) varies in western US pine forests

1. Lure attraction strength for red turpentine beetle, Dendroctonus valens (Coleoptera: Curculionidae: Scolytinae) observed previously in US Pacific Northwest ponderosa pine forests is (−)-β-pinene+ethanol > (+)-3-carene+ethanol, but untested elsewhere in its western US range. Thus, both were tested with (−)-β-pinene, (+)-3-carene, ethanol, and a blank in Oregon and California sites burned by wildfire, whereas in Arizona the first four lures were tested in a thinned-unburned site.
2. The D. valens responses in burned Oregon and California sites were similar, (−)-β-pinene+ethanol > (−)-β-pinene > 3-carene = 3-carene+ethanol > ethanol > blank, whereas in the cut-unburned Arizona site it was 3-carene+ethanol > 3-carene = (−)-β-pinene+ethanol > (−)-β-pinene. Whether this variation was influenced by beetle genetic differences, or chemical and physical parameters in the different environments and remaining stressed host resources 1-year post disturbance warrants additional study.
3. Responses to (−)-β-pinene varied, from a stronger attractant than (+)-3-carene in Oregon and California, to a weaker lure than (+)-3-carene in Arizona. This (−)-β-pinene variability was minimized when released in combination with ethanol, making (−)-β-pinene+ethanol the most consistent attractant of those tested across the three states, and a reliable lure for detection, monitoring, and management projects for D. valens in western US pine forests.

     

外来入侵害虫红脂大小蠹对寄主挥发物的反应

2002年,利用寄主挥发性物质(+)-α-蒎烯、(-)-β-蒎烯、3-蒈烯和(-)柠檬烯按不同配比制成诱芯,采用自行研制的挥发物释放装置,在山西省关帝山森林经营局西葫芦林场对危害油松Pinus tabulaeformis Carr.的重大外来入侵林业害虫红脂大小蠹Dendroctomus valens LeConte进行了引诱试验。结果表明,3蒈烯对红脂大小蠹的引诱作用最强,明显优于单独使用(+)-α-蒎烯和(-)-β-蒎烯的诱虫效果,也比北美应用的标准诱芯［(+)- α蒎烯(-)-β-蒎烯与3-蒈烯的比例为1∶1∶1］效果好;在标准诱芯中加入油松另一主要成分-(-)柠檬烯会明显降低诱虫效果。红脂大小蠹引诱剂最佳释放量为150 mg/d。该研究不仅对我国红脂大小蠹的监控具有实际应用意义,也从理论上探讨了红脂大小蠹与寄主油松协同进化的化学生态学过程。     

红脂大小蠹后肠挥发性物质的鉴定、触角电位和室内趋向实验

对外来松树害虫红脂大小蠹Dendroctonus valens LeConte的信息化学物质进行了研究。通过GC-MS测定,鉴定出红脂大小蠹后肠挥发性物质中除了含有松树挥发性物质α-蒎烯、β-蒎烯、3-蒈烯、月桂烯和柠檬烯外,还含有马鞭草烯醇和马鞭草烯酮;利用触角电位技术,对马鞭草烯醇、马鞭草烯酮以及在林间引诱效果最好的3-(+)-蒈烯进行了触角电生理测试;利用Y-型双向选择嗅觉仪对这些物质进行了室内趋向实验。实验结果表明: 1 μg的马鞭草烯醇、马鞭草烯酮和3-(+）-蒈烯引起雌雄触角的电位反应分别达416 μV/470 μV、597 μV/630 μV和926 μV/1 099 μV。浓度为1 μL/mL的马鞭草烯酮引起红脂大小蠹的正趋向反应,而在100 μL/mL浓度下引起红脂大小蠹的负趋向反应;在1 μL/mL的浓度下,3-(+ )-蒈烯引起了红脂大小蠹正趋向反应,而马鞭草烯醇则对红脂大小蠹具有驱避作用,说明这些物质在红脂大小蠹搜寻寄主和调节虫口密度方面起着重要作用。