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。     

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。     

Effects of aphid herbivory on volatile organic compounds of Artemisia annua and Chrysanthemum morifolium

We showed the effect of aphid infesting on the volatile organic compounds (VOCs) emitted by the infested Artemisia annua and Chrysanthemum morifolium cultivar ‘Nan nong hong feng’ plants by using headspace solid-phase microextraction (HS-SPME) method combined with gas chromatography mass spectrometry (GC–MS). In olfactometer bioassay experiment, aphids showed a preference for the odour of both healthy and infested chrysanthemum, while we found an opposite result in A. annua. Aphids tend to healthy plants compared with the infested, and the phenomenon became obvious with time. Different extracts were tested with the healthy plants and aphid infested plants. Eucalyptol, β-caryophyllene, (E)-β-farnesene, and germacrene D were released as the major constituents in both species. After aphid infesting, we observed a great increase in artemisia ketone and (E)-β-farnesene and a decrease in germacrene D in A. annua; comparatively, eucalyptol, isoborneol and β-caryophyllene increased in chrysanthemum. Combined with the GC–MS data and olfactometer bioassay results we concluded that (E)-β-farnesene and artemisia ketone emitted from A. annua might act as a potential volatile compound to resist aphids, and the two compounds would be useful for future ecological control of aphid in chrysanthemum cultivation.     

Volatile terpenoids from aeciospores of Cronartium fusiforme

Aeciospores of Cronartium fusiforme isolated from slash pine (Pinus elliottii) trees were analyzed for volatile terpenoids by GLC and GLC-MS. α-Pinene, β-pinene, Δ³-carene, myrcene, linonene, β-phellandrene, and δ-terpinene were the major monoterpenoid hydrocarbons present with only traces of camphene. A number of monoterpenoid alcohols were also present of which terpinen- 4-ol predominated. Among the various acyclic sesquiterpenes present, β-farnesene and β-citronellol were identified. Several aromatic compounds were also observed, including o-cresol.     

星天牛对青皮垂柳挥发物的电生理及行为反应

【目的】考察星天牛Anoplophora chinensis对不同生理状态青皮垂柳Salix ohsidare挥发物的选择偏好性,深入探究星天牛对虫害青皮垂柳与健康青皮垂柳行为选择差异的原因。【方法】利用动态顶空吸附法,分别收集虫害和健康两种生理状态下的青皮垂柳枝条挥发物,通过气相色谱 质谱联用仪(GC-MS)对收集的挥发物样品进行鉴定与分析,采用触角电位仪(EAG)和Y型嗅觉仪分别分析星天牛对挥发物样品中鉴定的主要化合物的标准化合物的电生理以及行为反应,通过大笼行为实验和林间诱捕试验分析单一挥发性化合物及其双组分和三组分配方对星天牛成虫的诱捕效果。【结果】健康青皮垂柳枝条挥发物中共鉴定出3种主要化合物,包括α-蒎烯、3-蒈烯和樟脑,而虫害青皮垂柳枝条挥发物中鉴定出5种主要化合物包括α-蒎烯、β-蒎烯、3-蒈烯、β-罗勒烯和樟脑。另外虫害青皮垂柳枝条挥发物中的樟脑含量显著高于健康青皮垂柳枝条中的,3-蒈烯在两种挥发物中含量差异不显著,而健康青皮垂柳枝条挥发物中的α-蒎烯含量显著高于虫害青皮垂柳枝条中的。EAG实验表明,星天牛成虫对α-蒎烯、3-蒈烯和β-罗勒烯3种化合物的EAG反应相对值较高,并且随这3个化合物浓度的升高而逐渐增大;星天牛成虫对β-蒎烯和樟脑的EAG反应相对值差异不大,且这2个化合物浓度变化对EAG反应相对值无明显影响。Y型嗅觉仪实验表明,在1 mg/mL浓度下,α-蒎烯、3-蒈烯和β-罗勒烯吸引星天牛雄成虫数量均显著高于对照组（石蜡油）,β-罗勒烯吸引的星天牛雌成虫数量显著高于对照组;在10 mg/mL浓度下,3-蒈烯吸引的星天牛雄成虫数量显著高于对照组。大笼行为实验表明,三组分虫害配方D(α-蒎烯∶3-蒈烯∶β-罗勒烯=42∶30∶103)、α-蒎烯和β-罗勒烯吸引的星天牛成虫数量最多,显著高于双组分健康配方H(α-蒎烯∶3-蒈烯=105∶38)和3-蒈烯吸引的成虫数量。林间诱捕试验表明,α-蒎烯和虫害配方D对星天牛成虫的诱捕效果最好,诱捕的成虫数显著高于β-罗勒烯和健康配方H诱捕的成虫数,而3-蒈烯和空白对照组没有诱捕到星天牛成虫。【结论】虫害和健康青皮垂柳枝条挥发物中共有的α-蒎烯和虫害青皮垂柳枝条挥发物中特有的β-罗勒烯是对星天牛成虫具有引诱作用的两种重要寄主植物挥发性化合物,而3-蒈烯抑制了α-蒎烯对星天牛成虫的引诱作用。我们推测,虫害青皮垂柳挥发物中特有的β 罗勒烯是造成虫害青皮垂柳比健康青皮垂柳更容易受到星天牛危害的原因之一。     

Chemical composition of the cortical essential oil from Abies balsamea

Monoterpenoids and sesquiterpene hydrocarbons of Abies balsamea cortical oleoresin (Canada balsam) were analyzed by a combination of chromatographic and spectroscopic methods. Monoterpene hydrocarbons (21%) were composed of β-pinene, α-pinene, β-phellandrene, limonene, 3-carene, myrcene and camphene (listed in order of decreasing percentages), and oxygenated monoterpenes (0·4%) contained 4,4-dimethyl-2-cyclohepten-1-one, linalool, bornyl acetate, methylthymol, citronellyl acetate, α-terpineol, piperitone, citronellal, borneol, citronellol, two unknowns, and geraniol. From the sesquiterpene hydrocarbon fraction (1·1%) were isolated: longifolene, β-bisabolene, longipinene, an unknown, sativene, cyclosativene, cis-α-bisabolene, β-himachalene, α-himachalene, β-caryophyllene, γ-humulene, farnesene, longicyclene, an unknown, and β-selinene. Both himachalenes have been identified for the first time in Pinaceae outside of Cedrus; their co-occurrence with γ-humulene, longifolene, longipinene and longicyclene supports the biosynthetic mechanism by which all of these compounds arise through initial 1/11 cyclization of tran-cis-farnesylphosphate.     

Identification des constituants de l'essence des aiguilles de Pinus pinaster

The chromatographic analysis of the volatile leaf oil of Pinus pinaster Ait. showed 42% of monoterpene hydrocarbons (α-pinene, camphene, β-pinene, myrcene, 3-carene, limonene, cis-ocimene, terpinolene, para-cymene, 35% of sesquiterpene hydrocarbons (cubebene, copaene, caryophyllene, humulene, germacrene D, α- and γ-muurolenes, δ- and γ-cadinenes) and 23% of oxygenated compounds including esters (linalyl, bornyl, geranyl, neryl and farnesyl acetates), alcohols (cis-hexenol, linalool, α-fenchol, trans-pinocarveol, terpinen-4-ol, α-terpineol, dihydrocarveol, guaiol, junenol and α-cadinol), one aldehyde (hexenal) and one ketone (piperitone). Three non terpenoid phenylethyl esters were also identified: phenylethyl isovalerate, methyl-2 burtyate and 3-3 dimethylacrylate. Some alcohols and mainly α-terpineol and linalool seemed to be formed during the steam distillation process, they were absent when the leaf oil was obtained by maceration of small portions of leaves in the usual solvents of terpenes.     

马尾松枝条挥发性组分的鉴定及松墨天牛对其触角电生理反应

为研究松墨天牛Monochamus alternatus Hope取食期引诱剂,利用气相色谱-质谱(GC-MS)联用技术并与标样核对分析了马尾松(Pinus massoniana Lamb.)枝条挥发性气味的化学组成。结果表明,马尾松1年生、2年生、3年生枝条气味均由8种萜烯类物质组成,但各组分相对含量不同。经方差分析,α-蒎烯、莰烯、β-蒎烯、柠檬烯、萜品油烯、β-石竹烯在3种枝条中的相对百分含量的差异均达到极显著水平。1年生枝条中α-蒎烯、莰烯和萜品油烯的相对含量最小,分别为20.81%、0.43%和4.74%,而β-蒎烯、月桂烯和柠檬烯的相对含量最高,分别为12.37%、4.33%和4.53%。鉴定的化合物对松墨天牛雌雄成虫的触角电生理反应的实验,结果表明,松墨天牛雌雄成虫对α-蒎烯的反应最强,对β-石竹烯的反应最弱。     

Host-locating response by the aphid parasitoid Aphidius ervi to tomato plant volatiles

Abstract

The blend of volatile compounds emitted by tomato plants (Solanum lycopersicum) infested with the potato aphid (Macrosiphum euphorbiae) has been studied comparatively with undamaged plants and aphids themselves. Aphid-infested plants were significantly more attractive towards Aphidius ervi than undamaged plants and aphids themselves. Oriented response towards host-damaged plant, from which aphids were removed just before running the bioassay, did not differ from that recorded for infested plants. Collection of the volatiles and analysis by gas chromatography revealed only quantitative differences between uninfested and aphid-infested plants. Nine compounds, α-pinene, (Z)-3-hexen-1-ol, α-phellandrene, limonene, (E)-β-ocimene, p-cymene, methyl salicylate, (E)-β-caryophyllene and an unknown compound, were emitted at higher levels from aphid-infested plants than from undamaged control plants, whilst no differences were noted for hexanal, 6-methyl-5-hepten-2-one, and humulene (=α-caryophyllene). Synthetic standards of these compounds were tested in wind tunnel bioassays and all elicited a significant increase in oriented flight and landings on the target by the aphid parasitoid Aphidius ervi. (E)-β-caryophyllene resulted the most attractive towards female wasps. These results corroborate the hypothesis that the volatiles produced by the plant in response to aphid attack derive from both jasmonic and salicylic acid pathways, and are exploited by A. ervi as olfactory cues to locate its hosts.     

Volatile compounds from some wild growing aromatic herbs of the Lamiaceae from southern France

Abstract

The composition of the volatile fraction in selected aromatic plants of the Lamiaceae from garrigue sites in southern France is described. Calamintha nepeta appeared heterogeneous. The oil was dominated by piperitone oxide, and piperitenone oxide or by pulegone and menthone. In Nepeta nepetella, nepetalactone, almost exclusively the (4a-α, 7α, 7a-β)-isomer, made up more than 85% of the essential oil. Dichloromethane extracts from Teucrium polium contained germacrene D or sabinene as main components, α-pinene, β-pinene and β-caryophyllene in varying proportions as further important constituents, and various minor components depending on the origin.     

Essential oil composition of four Lomatium Raf. species and their chemotaxonomy

The composition of the essential oils of Lomatium dasycarpum ssp. dasycarpum, Lomatium lucidum, Lomatium macrocarpum var. macrocarpum and Lomatium utriculatum is described. Identification of components was determined from their GC, GC/MS data and many were confirmed by coinjections with authentic samples. Several components were isolated by liquid and gas chromatographic techniques and their structures confirmed from their ¹H and ¹³C NMR spectral data. 2-Methyl and 3-methylbutanoates were the major components of L. dasycarpum fruits as well as stems and leaves oils. β-Phellandrene/limonene, decanal, dodecanal, bornyl acetate, germacrene D, α-humulene and bicyclogermacrene were the major components of the corresponding L. lucidum oils. α-Pinene and β-pinene were the major components of the fruit oil of L. macrocarpum. Its stem and leaf oil was rich in peucenin 7-methyl ether, β-caryophyllene, (Z)-3-hexenol, palmitic acid, linoleic acid and (E)-2-hexenal. Sabinene, (Z)-ligustilide, terpinen-4-ol, β-phellandrene/limonene, β-caryophyllene, myrcene, α-pinene and β-pinene were the major compounds in L. utriculatum fruit oil, while its stem and leaf oil was rich in (Z)-ligustilide, palmitic acid, terpinen-4-ol, linoleic acid and germacrene D. (Z)-Falcarinol was a major component of all the four root oils.     

Composition of turpentine from Pinus edulis wood oleoresin

Monoterpenoids and sesquiterpenoid hydrocarbons of Pinus edulis wood oleoresin were analyzed by chromatographic and spectroscopic methods. Monoterpenoid hydrocarbons (20·3%) were composed mainly of α-pinene, with camphene, β-pinene, 3-carene, sabinene, myrcene, limonene, β-phellandrene, trans-ocimene and terpinolene in secondary to trace amounts. Oxygenated terpenoids (0.28%) contained bornyl acetate and verbenone as major constituents, and linalool, camphor, terpinene-4-ol, citronellyl acetate, borneol, neral, α-terpineol, citronellol, nerol, and geraniol in smaller amounts. Oleoresin contained 1·1% of acetogenins, composed mainly of ethyl caprylate. Sesquiterpenoid hydrocarbons were high (5·7%) in oleoresin) and were composed of germacrene D as a major constituent (36·6%), of γ-amorphene, α-copaene, and longifolene as secondary constituents (5–20%), and β-farnesene, α- and γ-murolenes, β₁-, γ-, δ-, and ε-cadinenes, α-amorphene, δ-guaiene, sibirene, α-cubebene, β-copaene, β-ylangene, sativene, cyclosativene, β-bourbonene, α- and γ-humulenes, caryophyllene, α-longipinene and longicyclene in smaller amounts. Composition of P. edulis and of P. monophylla turpentines was found to be similar, with percentage of ethyl caprylate being the best distinguishing criterion.     

Composition and antimicrobial activity of the essential oil of six Hypericum species from Serbia

The volatile composition of six Hypericum species has been studied. The essential oils were obtained by steam distillation in 500 mL H₂O for 2 h in a modified Clevenger apparatus with a water-cooled oil receiver to reduce hydrodistillation over-heating artifacts, and their analyses were performed by GC and GC–MS. Identification of the substances was made by comparison of mass spectra and retention indices with literature records. A total of 100 different compounds were identified. The main constituents of the investigated populations of each taxon have been revealed as follows: Hypericum alpinum: (−)-β-pinene, γ-terpinene, (−)-(E)-caryophyllene; Hypericum barbatum: (−)-α-pinene, (−)-β-pinene, (−)-limonene, (−)-(E)-caryophyllene, (−)-caryophyllene oxide; Hypericum rumeliacum: (−)-α-pinene, (−)-β-pinene, (−)-limonene, Hypericum hirsutum: nonane, undecane, (−)-(E)-caryophyllene, (−)-caryophyllene oxide; Hypericum maculatum: spathulenol, globulol; Hypericum perforatum: (−)-α-pinene, (Z)-β-farnesene, germacrene D; Monoterpene hydrocarbons were shown to be the main group of the taxa belonging to the section Drosocarpium, while the taxa of section Hypericum were more rich in sesquiterpene hydrocarbons.     

Anisakis simplex s.l.: Larvicidal activity of various monoterpenic derivatives of natural origin against L3 larvae in vitro and in vivo

This paper describes the activity against Anisakis simplex s.l. L₃ larvae of six monoterpenic derivatives obtained from different essential oils, (α-pinene, β-pinene, ocimene, myrcene, geranyl acetate, and cineole). In in vitro assays, α-pinene, ocimene and cineole showed high activity at a concentration of 125 μg/mL (48 h) but only α-pinene and ocimene were active at 62.5 μg/mL. In in vivo assays, L₃ larvae and study compounds were simultaneously administered per os to Wistar rats. The most active compound was α-pinene, finding lesions in only 20% of treated rats versus 98% of controls. Further in vivo studies are required to investigate whether addition of these compounds to food could have a prophylactic effect, reducing the pathogenicity of A. simplex s.l. L₃ in humans, and to explore any possible synergy among compounds.     

Terpenes from Cantinoa (Lamiaceae) native to Rio Grande do Sul,South Brazil

Cantinoa althaeifolia, C. heterodon, C. mutabilis, C. stricta and C. sylvularum were investigated for the essential oil and exudate composition. The essential oils of these species, previously placed in the genus Hyptis, demonstrated the presence of at least 46 compounds, being β-pinene, δ-3-carene, β-caryophyllene, bicyclogermacrene, caryophyllene oxide and globulol the compounds present in higher amounts. Besides monoterpenes and sesquiterpenes, three species presented diterpenes. Kaurenoic acid was isolated from C. heterodon exudate and detected by gas chromatography in C. stricta and C. mutabilis. Although kaurane diterpenes are widely found in nature, their occurrence in Lamiaceae seems to be restricted to few genera.     

Studies on Chemical Constituents of the Essential Oil of Artemisia subdigitata Mattf by Glass Capillary Gas Chromatography

subdigitata Mattf. by glass capillary gas chromatography. Their oils were determined by retention time, standard addition method and GC-MS. 15 components have been identified i.e. α-thujene, α-pinene, camphene, sabinene, β-pinene, myrcene, δ-3-carene, β-ocimene-x, β-isopropyl phenol, limonene, γ-terpinene, terpinen-4-ol, estragolc, geraniol, methyl eugenol. Their contents have been determined.     

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.     

Essential oils of Phlomis leucophracta,Phlomis chimerae and Phlomis grandiflora var. grandiflora from Turkey

The essential oils of three species of Phlomis from Turkey, Phlomis leucophracta, Phlomis chimerae and Phlomis grandiflora var. grandiflora have been studied. The main constituents of P. leucophracta essential oil were β-caryophyllene (20.2%), α-pinene (19.2%) and limonene (11.0%). This species also contained three diterpene derivatives, 15-isopimaradiene, manoyl oxide and epi-13-manoyl oxide that summed 1.4%. In P. chimerae the principal compounds were β-caryophyllene (31.6%), α-pinene (11.0%), germacrene D (6.1%), limonene (5.5%) and linalool (4.7%). In P. grandiflora var. grandiflora, germacrene D (45.4%), β-caryophyllene (22.8%) and bicyclogermacrene (4.9%) were among the principal derivatives.     

Volatiles from spruce trap-trees detected by Ips typographus bark beetles: chemical and electrophysiological analyses

In the search for compounds that contribute to the host or habitat discrimination, antennae of Ips typographus were screened for sensitivity to volatiles released by spruce trap-trees using gas chromatography linked to electroantennography. The antennally active compounds were determined using comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometric detection. Data show that I. typographus antennae respond to compounds emitted by the host. In total, 18 of antennally active compounds were detected: α-pinene, camphene, sabinene, β-pinene, myrcene, Δ-3-carene, p-cymene, limonene, β-phellandrene, 1,8-cineole, γ-terpinene, terpinolene, nonanal, camphor, trans-pinocamphone, cis-pinocamphone, terpinen-4-ol, and verbenone. Unequivocal identification of all active minor compounds is provided and confirmed using synthetic standards. Compounds in minor quantities like 1,8-cineole, β-phellandrene, camphor, cis-pinocamphone, and trans-pinocamphone were more active than major spruce monoterpenes. We hypothesize that the minor spruce compounds may play so far unrecognized role in conveying information about host suitability for I. typographus.     

Volatile constituents in leaves of parsley

Volatile chemicals obtained from the leaves of parsley, Petroselinum sativum by steam distillation, isopentane extraction, and head-space analysis were identified by GLC-MS. The presence in leaf oil of α-pinene, β-pinene, myrcene, β-phellandrene, trans-β-ocimene, γ-terpinene, 1-methyl-4-isopropenyl benzene, and 1,3,8-p-menthatriene as shown by earlier investigators was confirmed. In the present studies, the number of volatile chemicals detected in the leaves was extended by an additional 42. Sniffing tests of effluent from a gas chromatograph of a concentrate from parsley leaves showed that 1,3,8-p-menthatriene was only one of several compounds that gave a parsley-like aroma.