油松毛虫雌蛾对油松松针两种手性化合物的触角电位反应

采用触角电位技术测定了油松毛虫雌蛾触角对油松挥发物的两对手性单萜的剂量反应,并在饱和剂量下测定了α-蒎烯、β-蒎烯手性化合物及其消旋体的触角电位值。剂量反应测试表明,油松毛虫雌蛾对(-)-α-蒎烯的饱和剂量为1 600 μL,对(+)-α-蒎烯、(+)-β-蒎烯、(-)-β-蒎烯的饱和剂量为800 μL。α-蒎烯右旋异构体的反应值高于(-)-α-蒎烯的反应值,说明(+)-α-蒎烯能够更有效的与感受器中的分子受体结合;β-蒎烯则相反,(-)-β-蒎烯的EAG反应值高于(+)-β-蒎烯,说明β-蒎烯的右旋异构体不能有效的与多数感受器中的分子受体结合。在饱和剂量下的测定结果表明油松毛虫雌蛾对α-蒎烯和β-蒎烯消旋体的反应均与对其手性异构体反应相当,说明油松毛虫雌蛾用同一个感受细胞来接受α-蒎烯的两个对映异构体,同样β-蒎烯的两个对映异构体也是被同一个受体细胞来接受。结果提示,手性化合物的比例可能在油松毛虫寄主识别中有重要作用。     

Dr. Alfred Jeske 75 jahre

The chemical composition, phytotoxic and antifungal activities of the essential oils isolated by hydrodistillation from the needles of Tunisian Aleppo pine harvested from different provenances were evaluated. The chemical composition analysed by gas chromatography/mass spectrometry (GC/MS) revealed variability among provenances displaying interesting chemotypes, (Z)-caryophyllene (16.16–28.9%), β-myrcene (8.5–22.9%), α-pinene (11.7–13.14%), β-pinene (3.13–11.8%), bicyclogermacrene (5.2–12.37%), α-terpinolene (8.11–11.01%) and α-humulene (2.85–5.2%), which were the main components in the oil. Antifungal ability of Aleppo pine oils was tested by disc agar diffusion against 10 phytopathogenic fungi. Weak antifungal activity was observed for the essential oils isolated. Furthermore, in contrast, the herbicidal activity investigated for three common weeds in Tunisian cereal crops was very strong and seed germination was inhibited at a low concentration and their herbicidal effects were higher than those of a commercial herbicide.     

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.     

Components of essential oils extracted from leaves and shoots of abies species in Japan

The essential oils extracted from the leaves and the shoots of five Abies species (Pinaceae) growing in Japan, i.e., A. firma, A. homolepis, A. veitchii, A. mariesii, and A. sachalinensis, were characterized by GC-FID and GC/MS analyses. The yields of the essential oils extracted from A. sachalinensis were the highest among them. A significant amount of α-pinene was contained in the essential oils of all the Abies species examined. In A. homolepis and A. veitchii, significant differences in the content of the essential oils were found depending on whether these were extracted from the leaves or from the shoots. Regarding the enantiomeric ratio of α-pinene, the (+)-enantiomer was predominant in the oil extracted from the leaves of A. firma, while (-)-α-pinene was present in higher amounts in the oils of A. veitchii (leaves and shoots), A. mariesii (leaves and shoots), and A. sachalinensis (shoots). The fact that there may be a quantitative and qualitative difference in the components of the essential oils extracted from the different parts of a plant was investigated by cluster analysis.     

Essential oils in the ranunculaceae family: chemical composition of hydrodistilled oils from Consolida regalis, Delphinium elatum, Nigella hispanica, and N. nigellastrum seeds

In this study, we analyzed the chemical composition of volatile oils hydrodistilled from seeds of Consolida regalis, Delphinium elatum, Nigella hispanica, and N. nigellastrum using GC and GC/MS. In C. regalis, octadecenoic (77.79%) and hexadecanoic acid (8.34%) were the main constituents. Similarly, the oils from D. elatum and N. hispanica seeds consisted chiefly of octadecadienoic (42.83 and 35.58%, resp.), hexadecanoic (23.87 and 28.59%, resp.), and octadecenoic acid (21.67 and 19.76%, resp.). Contrastingly, the monoterpene hydrocarbons α-pinene (34.67%) and β-pinene (36.42%) were the main components of N. nigellastrum essential oil. Our results confirm the presence of essential oils in the family Ranunculaceae and suggest chemotaxonomical relationships within the representatives of the genera Consolida, Delphinium, and Nigella. In addition, the presence of various bioactive constituents such as linoleic acid, (-)-β-pinene, squalene, or carotol in seeds of D. elatum, N. hispanica, and N. nigellastrum indicates a possible industrial use of these plants.     

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.     

Studies on Chemical Constituents of Essential Oil from Leaves of Jiang-Zhang

Jiang-Zhang is a Physiological type of Cinnamomum porrectum (Roxb.) Kosterm. The essential oil of leaves of Jiang-Zhang can be extracted by steam distillation, with yields of 0.5–0.8%. It contained dtral (α-,β-citral) 64.11% and can be used in aromatic and medicinal industries. We used the methods of GC, IR, GC/MS/DS and prepared derivative and 47 chemical constituents were identified, as follows: α-thujene (0.06 %), α-pinene (2.42%), camphene (1.26%), sabinene (0.21%),β- pinene (1.38%) myrcene(0.38%), α-phellandrene (0.32%),△3-carene (0.01%), p-cymene(0.21%),α-limonene (1.57%), 1 8-cineole (0.82 % ), β-phellandrene (0.10 %), cis-linalool oxide(0.07 % ), linalool (8.43 % ) epicamphor(0.26 % ), camphor(1.10 %), borneol( 1.07 % ), β-citral (neral) (28.28 % ), geraniol (0.25%), nerol (0.47%), α-citral (geranial) (35.83%), methyl citronellate (0.12%), n-undecane (0.18), safrole (0.02), methyl geranate (0.23%), geranyl formate (0.09%), α-copaene (0.12%), trans-methyl cinnamate (0.02%), n-dodecane (0.20), β-elemene (0.12%), caryophyllene (4.67%), α-guaiene (0.04), β-guaiene (0.06%), β-selinene (0.97%), azulene (0.38%), β-cubebene (0.30%), n-pentadecane (0.05%), β-gurjunene (0.04 %), epi-β-santalene (0.46 %), aremophliene (0.05 % ), alloaromadendrene (0.03 % ), α-elemene (0.26%), trans-β-farnesene (0.04%), (z)-β-farnesene (0.30%), r-elemene (0.03%), β-bisaboiol(0.41%), cedrol (0.16%), respectively.     

茴香菖蒲精油化学成分的研究

利用色谱—质谱联用方法,结合薄层层析、气相层析、红外和核磁共振光谱等鉴定了茴香菖蒲全株的精油成分为:α-派烯,β-水芹烯,伪柠檬烯,异龙脑,胡椒酚甲醚,大茴香脑,榄香烯,β-石竹烯等17种以上。为进一步开发利用茴香菖蒲精油提供科学依据。     

Variability in essential oil composition of Piper dilatatum L.C. Rich

Twelve samples of air-dried aerial parts of Piper dilatatum L. C. Rich yielded essential oils and their volatile constituents were analyzed by GC and GC–MS. Sesquiterpenes, both hydrocarbons and oxygenated, were the most highly represented classes, the former ranging from 31.5% to 87.7% and the latter varying from 1.8% to 49.4%. Using hierarchical cluster analysis, the oils were divided into seven groups, whose main constituents were: (E)-caryophyllene, α-cadinol and germacrene D (group A); spathulenol, bicyclogermacrene and (Z)-β-ocimene, (group B); spathulenol, germacrene D and (E)-nerolidol, (group C); germacrene D, limonene, α-phellandrene and bicyclogermacrene (group D); β-elemene, germacrene D and β-pinene (group E); curzerene, p-cymene and α-eudesmol (group F); and (Z)-α-bisabolene, curzerene and germacrene D (group G). We have seen that Piper oils from the Amazon present as major constituents terpenoids and phenylpropanoids, always with the predominance of one over another. The essential oils of P. dilatatum presented in this paper, containing only mono- and sesquiterpenes as its major components, is further chemotaxonomic evidence of this dichotomy in the Piper genus.     

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。     

苘麻挥发油对小麦、玉米和大豆萌发及幼苗生长的化感作用

苘麻是旱田常见杂草,可造成作物减产,化感作用是造成减产的可能原因之一。本研究分析了苘麻挥发油成分对3种旱田作物小麦、玉米和大豆种子萌发和幼苗生长的化感作用。结果表明: 应用气相色谱-质谱(GC-MS),从苘麻挥发油中鉴定出26种化学成分,占总峰面积的98.1%,其中,低分子量萜类成分有α-蒎烯、桉树醇、α-松油烯、β-松油烯、反式α-紫罗兰酮、反式β-紫罗兰酮。苘麻挥发油饱和水溶液能通过滤纸和土壤2种基质抑制3种作物种子萌发。苘麻挥发油能通过空气、滤纸和土壤3 种基质抑制3种作物幼苗生长,对小麦的抑制作用最强,玉米和大豆次之。苘麻挥发油对小麦生长的抑制作用以空气载体最强,滤纸和土壤载体次之。挥发油中低分子量的萜类成分可能是重要的化感成分。     

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。     

Terpene composition of Pinus pinaster seedlings and plants

-The production of essential oils in Pinus pinaster increases with the age of the seedlings, being higher in plants grown under continuous illumination. In the seedlings, nearly all the terpene is α- and β-pinene, the relative proportions of which are completely reversed between the 6th and 10th days of growth, regardless of the illumination period. Another reversion takes place after 60–65 days, the proportion found in the adult pine being very constant with α-pinene as the main component. The amount of oil in seedlings from high resin yielding parent trees was 4-fold higher than that in seedlings of normal (wild type) seeds. This finding is interesting because it can be employed for the preselection at the early stage of seedling of seeds to be used in forestry to obtain plantations of a high resin yield.     

Bioherbicide Potential of Eucalyptus saligna Leaf Litter Essential Oil

We aimed to evaluate the bioherbicide potential of Eucalyptus saligna leaf litter essential oil, its fractions and major compounds. Six essential oil fractions were obtained by preparative thin‐layer chromatography and analyzed by gas chromatography/mass spectrometry. Effects of the oil, its fractions and major compounds (1,8‐cineole and/or α‐pinene) diluted in aqueous solution were assessed on germination and seedling growth. Recipient species were Lactuca sativa (model), Amaranthus viridis (weed), Eragrostis plana (weed), and Paspalum notatum (forage). The essential oil was more phytotoxic on A. viridis and L. sativa, followed by E. plana, and caused no effects on P. notatum. Amaranthus viridis was inhibited by all treatments, mainly the essential oil, α‐pinene and fraction 6, whereas E. plana was more affected by the oil fractions. Results revealed the species‐specific phytotoxic effects of E. saligna essential oil, indicating its potential use for controlling A. viridis and E. plana. Phytotoxic effects of essential oils or their components should not be generalized, as effects may change according to recipient species.     

β-Pinene inhibited germination and early growth involves membrane peroxidation

β-Pinene, an oxygenated monoterpene, is abundantly found in the environment and widely occurring in plants as a constituent of essential oils. We investigated the phytotoxicity of β-pinene against two grassy (Phalaris minor, Echinochloa crus-galli) and one broad-leaved (Cassia occidentalis) weeds in terms of germination and root and shoot growth. β-Pinene (0.02–0.80 mg/ml) inhibited the germination, root length, and shoot length of test weeds in a dose–response manner. The inhibitory effect of β-pinene was greater in grassy weeds and on root growth than on shoot growth. β-Pinene (0.04–0.80 mg/ml) reduced the root length in P. minor, E. crus-galli, and C. occidentalis over that in the control by 58–60, 44–92, and 26–85 %, respectively. In contrast, shoot length was reduced over the control by 45–97 % in P. minor, 48–78 % in E. crus-galli, and 11–75 % in C. occidentalis at similar concentrations. Further, we examined the impact of β-pinene on membrane integrity in P. minor as one of the possible mechanisms of action. Membrane integrity was evaluated in terms of lipid peroxidation, conjugated diene content, electrolyte leakage, and the activity of lipoxygenases (LOX). β-Pinene (≥0.04 mg/ml) enhanced electrolyte leakage by 23–80 %, malondialdehyde content by 15–67 %, hydrogen peroxide content by 9–39 %, and lipoxygenases activity by 38–383 % over that in the control. It indicated membrane peroxidation and loss of membrane integrity that could be the primary target of β-pinene. Even the enhanced (9–62 %) activity of protecting enzymes, peroxidases (POX), was not able to protect the membranes from β-pinene (0.04-0.20 mg/ml)-induced toxicity. In conclusion, our results show that β-pinene inhibits root growth of the tested weed species through disruption of membrane integrity as indicated by enhanced peroxidation, electrolyte leakage, and LOX activity despite the upregulation of POX activity.     

水翁花蕾和水翁叶精油的化学成分研究

水翁的花营和鲜叶经水蒸汽蒸馏得到一种淡黄色的精油,前者出油率为0.18％。后者为0.08％。我们应用毛细管气相色谱,气相色谱/质谱联用,红外光谱和紫外光谱等方法,对两种精油进行化学分成分析,分别鉴定出35个和27个已知化学成分。两者相同的化学成分有:β-罗勒烯(Z)、β-罗勒烯(E)、α-蒎烯、β-蒎烯、月桂烯、小茴香烯、香叶醇、顺式-丁香烯、橙花叔醇等23个化学成分,分别占花营精油全油的90％和叶精油95％以上。     

Chemodiversity of Essential Oils in Seseli libanotis (L.) W.D.J.Koch (Apiaceae) in Central Europe

Seseli libanotis is an aromatic umbelliferous plant distributed sporadically on dry grassland edges in Europe and Western Asia. The essential oil composition in the different plant parts was studied from plants collected on nine sites in Austria and one site in Alto Adige, Italy. Monoterpenes such as α‐pinene, sabinene and β‐myrcene and the sesquiterpene germacrene D were present in all essential oils from the aerial parts. Inflorescences and fruits had the highest essential oil contents. These essential oils from four sites were rich in acorenone B, while from other three sites they had carotol as a major component. Osthole as furocoumarin occurred in some oils. The root essential oils were dominated by α‐pinene. The essential oil variability has been studied by principal component analysis (PCA) and discriminant analysis (DA) with plant parts or sampling site as a priori groups. PCA could well separate inflorescence and fruit essential oil samples from leaf and stem essential oil samples. DA differentiated well between the plant parts and most of the sampling sites.     

Studies on the Chemical Constituents of the Hydrocarbon Fraction of the Essential Oils from Caryopteris tangutica and C. Glutinosa

The chemical constituents of the hydrocarbon fraction of essential oils of Caryopteris tangutica Maxim. and C. glutinosa Rehd were examined by means of GC-MS-COM and GC retention time data on a 45 m capillary column coated with OV- 101. 21 components have been saparated and identified, i.e. α-thujene, α-pinene, cam- phene, sabinene, β-pinene, β-myrcene, α-terpinene, p-cymene, limonene, β-ocimene-y, β- phellandrene, α-terpinolene, α-cubebene, α-copaene, α-cedrene, β-caryophyllene, γ-cadinene, 1-aromadendrene, α-humulene, β-bisabolene and δ-cadinene. The quantitative determination of these components was carried out by GLC also.     

Chemical Composition of the Essential Oils from Different Morphological Parts of Pinus cembra L.

The essential oils from needles, twigs, bark, wood, and cones of Pinus cembra were analyzed by GC‐FID, GC/MS, and ¹H‐NMR spectroscopy. More than 130 compounds were identified. The oils differed in the quantitative composition. The principal components of the oil from twigs with needles were α‐pinene (36.3%), limonene (22.7%) and β‐phellandrene (12.0%). The needle oil was dominated by α‐pinene (48.4%), whereas in the oil from bark and in the oil from twigs without needles there were limonene (36.2% and 33.6%, resp.) and β‐phellandrene (18.8% and 17.1%, resp.). The main constituents of the wood oil as well as cone oil were α‐pinene (35.2% and 39.0%, resp.) and β‐pinene (10.4% and 18.9%, resp.). The wood oil and the cone oil contained large amounts of oxygenated diterpenes in comparison with needle, twig, and bark oils.     

Influence of phosfon D and cycocel on growth and essential oil content of sage and peppermint

Foliar application of Phosfon D at 50–100 ppm stimulates the growth of Salvia officinalis (sage) and moderately retards the growth of Mentha piperita (peppermint), while increasing the essential oil yield of both species by 50–70 % Phosfon D increases the proportions of (−)-3-isothujone and (+)-3-thujone in sage oil and decreases the level of (−)-β-pinene and (+)-camphor, whereas this growth retardant increases the proportions of (+)-isomenthone and (+)-neoisomenthol in peppermint oil and decreases the level of(−)-menthone and (−)-menthoL Foliar application of Cycocel at 250–500 ppm slightly stimulates growth and essential oil formation in peppermint, and retards growth of sage with little effect on oil yield. The influence of Cycocel on sage oil composition was the opposite of that of Phosfon, with a tendency to increase the level of (−)-β-pinene and decrease the level of (−)-3-isothujone under severe stunting. The effect of Cycocel on the composition of peppermint varied with concentration. The influence of growth retardants on essential oil composition and yield are most readily explained by alterations in the levels or activities of the relevant enzymes.