Odor distinctiveness between enantiomers of linalool: difference in perception and responses elicited by sensory test and forehead surface potential wave measurement

The effects on humans of inhalation of optically active linalools were examined in terms of sensory tests and portable forehead surface electroencephalographic (IBVA-EEG) measurements in order to assess their odor distinctiveness by chiral isomers. (R)-(-)-Linalools with specific rotation of [alpha](D) = -15.1 degrees were isolated by repeated flash column chromatography from lavender oil, while (S)-(+)-linalools with [alpha](D) = +17.4 degrees and (RS)-(+/-)-linalools with [alpha](D) = 0 degrees and content of (R)-form 50.9% and (S)-form 49.1% were obtained from coriander oil and commercial linalool, respectively, by using the same method. With the use of an inhalator, each was administered to subjects both before and after 10 min of work. It was found that administration after work evoked different subjective impressions when compared with that before work depending on the configuration of the isomers and the type of work employed. For instance, inhalation of (R)-(-)-linalool after hearing environmental sounds not only produced a much more favorable impression in the sensory test but was also accompanied by a greater decrease in beta waves after work in comparison with that before work. This is in contrast to the case of mental work, which resulted in a tendency for agitation accompanied by an increase in beta waves. These findings led us to conclude that enantiomeric stereospecificity of linalool evoked different odor perception and responses not only with chiral dependence but also with task dependence. In addition, in comparing these sensory profiling features and IBVA-EEG tendencies between hearing environmental sound and mental work, a tendency was observed for (R)-(-)-linalool to coincide with (RS)-(+/-)-linalool but not with (S)-(+)-linalool.     

Essential oils as spatial repellents for the brown marmorated stink bug,Halyomorpha halys (Stål) (Hemiptera: Pentatomidae)

The brown marmorated stink bug (BMSB), Halyomorpha halys (Stål), native to Northeastern Asia, is a serious invasive pest in the United States, Canada, Switzerland, Germany and France. Several common essential oils and their compositions were tested against BMSBs as potential repellents. All the tested individual essential oils and a ternary oil blend showed significant repellency to both BMSB nymphs and adults. Clove oil, lemongrass oil, spearmint oil, ylang‐ylang oil, and the ternary oil mixture (clove, lemongrass and spearmint) almost completely blocked attraction of BMSBs to the stink bug attractant‐baited traps; whereas wintergreen oil, geranium oil, pennyroyal oil and rosemary oil resulted in 60–85% trap catch reductions. Over 20 BMSB antennally active compounds were identified from SPME headspace samples of the eight repellent essential oils using GC‐EAD and GC‐MS techniques. Among the synthetic EAD‐active compounds tested in the field, eugenol, l‐carvone, p/l‐menthone, pulegone, methyl salicylate, trans/cis‐citral, methyl benzoate and β‐caryophyllene significantly reduced trap catches of BMSBs by 72–99%; these compounds are likely responsible for the repellency of their corresponding essential oils. Surprisingly, a synthetic mixture of the predacious spined soldier bug (SSB) [Podisus maculiventris (Say)] aggregation pheromone (trans‐2‐hexenal, α‐terpineol and benzyl alcohol) also showed a significant inhibition of BMSB response to its attractants. These repellent essential oils and their active compounds, as well as the synthetic SSB pheromone, are potentially useful as part of an efficient, environmentally sound semiochemical‐based IPM programme to combat this serious invasive stink bug.     

Acaricidal effects of herb essential oils against Dermatophagoides farinae and D. pteronyssinus (Acari: Pyroglyphidae) and qualitative analysis of a herb Mentha pulegium(pennyroyal)

This experiment was undertaken to screen the acaricidal effects of herb essential oils (pennyroyal, ylang ylang, citronella, lemon grass, tea tree, and rosemary) at different doses (0.1, 0.05, 0.025, 0.0125, and 0.00625 microliter/cm(2)) and exposure times (5, 10, 20, 20, 30 and 60 min) on house dust mites Dermatophgoides farinae and D. pteronyssinus. The most effective acaricidal components of pennyroyal (Mentha pulegium) were analyzed using a gas chromatography-mass spectrometer (GC-MS). Of these essential oils, the most effective was pennyroyal, which is composed essentially of pulegone (> 99%), at a dose of 0.025 microliter/cm(2), which at an exposure time of 5 min killed more than 98% of house dust mites. In the pennyroyal fumigation test, the closed method was more effective than the open method and maximum acaricidal effect was 100% at 0.025 microliter/cm(2), 60 min. The results show that herb essential oils, in particular, pennyroyal was proved to have potent acaricidal activity.     

Repellent effectiveness of seven plant essential oils,sunflower oil and natural insecticides against horn flies on pastured dairy cows and heifers

Plant essential oils (basil, geranium, balsam fir, lavender, lemongrass, peppermint, pine and tea tree), mixed with either sunflower oil or ethyl alcohol, were applied at 5% concentrations to the sides of Holstein cattle. Pastured cattle treated with essential oils diluted in sunflower oil had less flies than the untreated control for a 24‐h period. However, the essential oil treatments were not significantly different than the carrier oil alone. Barn‐held heifers treated with essential oils and sunflower oil alone had significantly less flies than the untreated control for up to 8 h after treatment. Basil, geranium, lavender, lemongrass and peppermint repelled more flies than sunflower oil alone for a period ranging from 1.5 to 4 h after treatments applied to heifers. All essential oils repelled > 75% of the flies on the treated area for 6 and 8 h on pastured cows and indoor heifers, respectively. Geranium, lemongrass and peppermint stayed effective for a longer duration. Essential oils mixed with ethyl alcohol demonstrated less repellence than when mixed with the carrier oil. Safer's soap, natural pyrethrins without piperonyl butoxide and ethyl alcohol alone were not efficient at repelling flies. Essential oils could be formulated for use as fly repellents in livestock production.     

Effects of essential oil inhalation on objective and subjective sleep quality in healthy university students

Aromatherapy with essential oils is one of the most popular complementary medical tools for improving sleep quality. However, only a few reports have objectively measured the effects of essential oils on sleep. Here, we used objective and subjective measures to analyze the effects of the essential oils of lavender (Lavandula angustifolia) and sweet orange (Citrus sinensis) on the sleep quality of healthy university students. The participants were monitored for 15 consecutive nights as they inhaled lavender oil and sweet orange oil, in a crossover design. Their sleep was monitored objectively by actigraphy, and total sleep time (TST), sleep efficiency, sleep latency, and wake after sleep onset (WASO) were analyzed. Their sleep was analyzed subjectively using Oguri–Shirakawa–Azumi (OSA) sleep inventory scores. Inhalation of an essential oil improved sleep measures only in participant whose sleep quality was poor in the control condition. Lavender seemed more effective than sweet orange in objective measures, especially in improving sleep latency. In the subjective sleep analysis, the essential oils improved sleep maintenance, dreaming, and sleep length in subjects who had poor sleep quality. Sweet orange seemed more effective than lavender in the subjective sleep measures. The difference between the two oils suggests that expectancy bias had little effect on the hypnotic effect of lavender on objective sleep. Although no obvious effect was observed in good sleepers, the inhalation of lavender oil could be effective for helping poor sleepers improve objective sleep quality.

     

Effects of inhalation of essential oils on EEG activity and sensory evaluation

The purpose of this study was to investigate EEG changes in subjects directly after inhalation of essential oils, and subsequently, to observe any effect on subjective evaluations. EEG and sensory evaluation were assessed in 13 healthy female subjects in four odor conditions. Four odor conditions (including lavender, chamomile, sandalwood and eugenol) were applied respectively for each subject in the experiment. The results were as follows. 1) Four basic factors were extracted from 22 adjective pairs by factor analysis of the sensory evaluation. The first factor was "comfortable feeling", the second "cheerful feeling", the third "natural feeling" and the fourth "feminine feeling". In the score of the first factor (comfortable feeling), the odors in order of high contribution are lavender, eugenol, chamomile and sandalwood. 2) Alpha 1 (8-10 Hz) of EEG at parietal and posterior temporal regions significantly decreased soon after the onset of inhalation of lavender oil (p < 0.01). Significant changes of alpha 1 were also observed after inhalation of eugenol or chamomile. The change after inhalation of sandalwood was not significant. These results showed that alpha 1 activity significantly decreased under odor conditions in which subjects felt comfortable, and showed no significant change under odor conditions in which subjects felt uncomfortable. These results suggest a possible correlation between alpha 1 activity and subjective evaluation.     

The Metabolic Responses to Aerial Diffusion of Essential Oils

Anxiety disorders are the most prevalent psychiatric disorders and affect a great number of people worldwide. Essential oils, take effects through inhalation or topical application, are believed to enhance physical, emotional, and spiritual well-being. Although clinical studies suggest that the use of essential oils may have therapeutic potential, evidence for the efficacy of essential oils in treating medical conditions remains poor, with a particular lack of studies employing rigorous analytical methods that capture its identifiable impact on human biology. Here, we report a comprehensive gas chromatography time-of-flight mass spectrometry (GC-TOFMS) based metabonomics study that reveals the aromas-induced metabolic changes and the anxiolytic effect of aromas in elevated plus maze (EPM) induced anxiety model rats. The significant alteration of metabolites in the EPM group was attenuated by aromas treatment, concurrent with the behavioral improvement with significantly increased open arms time and open arms entries. Brain tissue and urinary metabonomic analysis identified a number of altered metabolites in response to aromas intervention. These metabolic changes included the increased carbohydrates and lowered levels of neurotransmitters (tryptophan, serine, glycine, aspartate, tyrosine, cysteine, phenylalanine, hypotaurine, histidine, and asparagine), amino acids, and fatty acids in the brain. Elevated aspartate, carbohydrates (sucrose, maltose, fructose, and glucose), nucleosides and organic acids such as lactate and pyruvate were also observed in the urine. The EPM induced metabolic differences observed in urine or brain tissue was significantly reduced after 10 days of aroma inhalation, as noted with the loss of statistical significance on many of the metabolites in the aroma-EPM group. This study demonstrates, for the first time, that the metabonomics approach can capture the subtle metabolic changes resulting from exposure to essential oils and provide the basis for pinpointing affected pathways in anxiety-related behavior, which will lead to an improved mechanistic understanding of anxiolytic effect of essential oils.     

Comparative evaluation of the antimicrobial activities of essential oils of Artemisia afra, Pteronia incana and Rosmarinus officinalis on selected bacteria and yeast strains

Essential oils are frequently used for flavour and fragrance in the perfume, pharmaceutical, cosmetic and food industries. The antimicrobial activities of the essential oils of Artemisia afra, Pteronia incana and Rosmarinus officinalis were tested against 41 microbial strains. The test organisms were selected on the basis of their significance as food spoilage and/or poisoning, common human and plant pathogens. The agar diffusion assay was performed using nutrient agar and antibiotic medium. All the oils tested displayed some antimicrobial activities. However, the efficiency differed and depended both on the type and concentration of the oil, as well as the test microbial strain. Artemisia afra and R. officinalis showed similar and higher antimicrobial activity than P. incana. Due to their broad antimicrobial activities, the essential oils of the above plants growing in Eastern Cape may have preservative potential for the food and cosmetic industries.     

Vapor phase toxicity of plant essential oils to Cadra cautella (Lepidoptera: Pyralidae)

The toxicities of 44 plant essential oils against larvae of Cadra cautella (Walker) were examined using direct contact and vapor phase toxicity bioassays and compared with the lethal activity of chlorpyrifos-methyl, diazinon, dichlorvos, and fenthion, four widely used organophosphorus insecticides. Responses varied according to plant material used and exposure dose and time. In a filter paper contact toxicity bioassay, potent toxicity was produced from buchu leaf, niaouli, and rosemary oils at 2.4 mg/cm2 and armoise, cypress, galbanum, and mace oils at 4.7 mg/cm2. In vapor phase toxicity bioassays with larvae, cypress, galbanum, niaouli, and rosemary oils were much more effective in closed containers than in open containers, indicating that the lethal effects of these oils were largely because of action in the vapor phase. As judged by 24-h LC50 values, potent fumigant action was observed with niaouli oil (64.7 mg/liter air) and rosemary oil (64.6 mg liter/air). Cypress and galbanum oils exhibited weak fumigant activity. These essential oils were less active than dichlorvos (0.86 mg/liter air). Little or no fumigant action was observed with chlorpyrifos-methyl, diazinon, and fenthion. Essential oils described herein, particularly niaouli and rosemary oils, merit further study as potential larvicides for the control of C. cautella.     

Characterization of radicals arising from oxidation of commercially-important essential oils

Inappropriate use of essential oils may entail risks to human health due to mutational events, carcinogenic effects, genetic damages and sensitizing effect caused by generation of reactive oxygen species. In order to detect radicals that are expected to form during their oxidation, we measured the electron spin resonance (ESR) spectra of a standard reaction mixture (I) containing 25?μM flavin mononucleotide, 0.018% several essential oils (or 0.015% geraniol), 1.9 M acetonitrile, 20?mM phosphate buffer (pH 7.4), 0.1 M α-(4-pyridyl-1-oxide)-N-tert-butylnitrone (4-POBN) and 1.0?mM FeSO₄(NH₄)₂SO₄ irradiated with 436?nm visible light (7.8 J/cm²). The ESR peak heights of the standard reaction mixture (I) of the essential oils increased in the following order: tea tree?>?palmarosa?>geranium?>?clary sage?>?petitgrain?>?lavender?>?bergamot?>?frankincense?>?ravintsara?>?ylang ylang?>?lemongrass?>?niaouli?>?eucalyptus globulus?>?peppermint. The ESR peak height of the standard reaction mixture (I) of geraniol, a main component of palmarosa, was comparable to the one of palmarosa (97?±?19% of palmarosa). Furthermore, high performance liquid chromatography (HPLC)-ESR analyses of the standard reaction mixture (I) of palmarosa and geraniol gave the same peaks. The results suggest that the radicals formed in the standard reaction mixture (I) of palmarosa are derived from geraniol. HPLC-ESR-mass spectrometry analyses detected m/z 294 ions, 4-POBN/5-hydroxy-3-methyl-3-pentenyl radical adducts and m/z 320 ions, 4-POBN/C₇O₂H₉ radical adducts in the standard reaction (I) of geraniol. The 5-hydroxy-3-methyl-3-pentenyl and C₇O₂H₉ radicals may be implicated in the sensitizing effect of palmarosa.     

Suppression of carrageenan- and collagen II-induced inflammation in mice by geranium oil

To obtain experimental evidence on the therapeutic efficacy of essential oils in aromatherapy for inflammatory diseases, we examined the effects of geranium oil on carrageenan-induced and collagen II-induced inflammation in mice, to assess acute and chronic anti-inflammatory activities of the oil. Single intraperitoneal injection of 5 mu L of geranium oil clearly suppressed the carrageenan-induced footpaw edema and increase in tissue myeloperoxidase activity, and repeated administration of the oil suppressed collagen-induced arthritis. These results revealed that geranium oil suppressed both acute and chronic inflammatory responses in mice.     

11种植物精油对6种植物病原真菌的抑菌活性研究

为筛选有效的植物杀菌成分,采用菌丝生长法,测定了香茅油、薰衣草油、菊花油、月桂油、柠檬油、广藿香油、肉桂油、天竺葵油、迷迭香油、茶树油、薄荷油对6种植物病原真菌的抑菌活性。发现在2 g/L的浓度下,上述11种精油对6种供试病菌均有明显的抑制作用,其中香茅油、肉桂油、天竺葵油、月桂油、茶树油和薄荷油对6种病原真菌的抑制率均为100%。剂量效应试验表明,肉桂油对灰葡萄孢（Botrytis cinerea）和禾谷镰孢菌（Fusariumgraminearum）的EC50值分别为29.05μg/mL和42.96μg/mL,而天竺葵油对灰葡萄孢（Botrytis cinerea）和禾谷镰孢菌（Fusarium graminearum）的EC50值分别为34.02μg/mL和68.48μg/mL。     

Water soluble fractions of rose-scented geranium (Pelargonium species) essential oil

The essential oil of rose-scented geranium (Pelargonium species, family: Geraniaceae) obtained through steam or water plus steam distillation of shoot biomass is extensively used in the fragrance industry and in aromatherapy. During distillation, a part of the essential oil becomes dissolved in the distillation water (hydrosol) and is lost as this hydrosol is discarded. In this investigation, hydrosol was shaken for 30 min with hexane (10:1 proportion) and the hexane was distilled to yield 'secondary' or 'recovered' essential oil. The chemical composition of secondary oil was compared with that of 'primary' oil (obtained directly by distilling shoot biomass of the crop). Primary oil accounted for 93.0% and secondary oil 7.0% of the total oil yield (100.2 ml from 100 kg green shoot biomass). Fifty-two compounds making up 95.0-98.5% of the primary and the secondary oils were characterized through gas chromatography (GC) and gas chromatography-mass spectroscopy (GC--MS). Primary oil was richer in hydrocarbons (8.5-9.4%), citronellyl formate (6.2-7.5%), geranyl formate (4.1-4.7%), citronellyl propionate (1.0-1.2%), alpha-selinene (1.8-2.2%), citronellyl butyrate (1.4-1.7%), 10-epi-gamma-eudesmol (4.9-5.5%) and geranyl tiglate (1.8-2.1%). Recovered oil was richer in organoleptically important oxygenated compounds (88.9-93.9%), commercial rhodinol fraction (74.3-81.2%), sabinene (0.4-6.2%), cis-linool oxide (furanoid) (0.7-1.2%), linalool (14.7-19.6%), alpha-terpineol (3.3-4.8%) and geraniol (21.3-38.4%). Blending of recovered oil with primary oil is recommended to enhance the olfactory value of the primary oil of rose-scented geranium. Distillation water stripped of essential oil through hexane extraction can be recycled for distilling the next batch of rose-scented geranium.     

Toxicity of citrus essential oils against Ceratitis capitata (Diptera: Tephritidae) larvae

Citrus peel essential oils are considered to constitute the most important resistance factor of citrus fruits against fruit flies. Essential oils were obtained from three sweet orange varieties, one bitter orange and one lemon variety. Yield, chemical composition and toxicity against neonates of the Mediterranean fruit fly were determined. Based on chemical analysis, the toxicity of commercially purchased major and minor components (monoterpenes and sesquiterpenes) of essential oils was determined. In addition, fractions were prepared to evaluate the role of minor components in the toxicity of crude essential oils. Limonene was by far the most abundant ingredient (96.2–97.4%) in all sweet orange varieties and in bitter orange, while the concentration of limonene was much lower in lemon essential oils (74.3%). Orange and bitter orange essential oils were more toxic than lemon essential oils. The toxicity of orange and bitter orange essential oils was similar to that of their major component limonene. In tests of commercially purchased chemicals, the oxygenated components of essential oils were more toxic than hydrocarbons but their low concentration in citrus essential oils could not affect the toxic activity of essential oils. The presence of α-pinene and β-pinene seems to account for the lower toxicity of lemon essential oils in relation to other citrus essential oils. The importance of understanding the toxicity of essential oils in relation to their composition and their role regarding the resistance of citrus fruits to Ceratitis capitata infestation is discussed.     

Antifungal effect of essential oils on southern yellow pine

Moisture management remains the most critical factor for controlling mold growth on wood and wood products during storage, construction, and while in service. When moisture management practices fail to adequately control moisture, plant extracts demonstrating antifungal properties may provide protection for these applications. The objective of this study was to evaluate the antifungal properties of natural plant extracts, such as essential oils, for use on wood. Seven essential oils were evaluated for their ability to inhibit growth of Aspergillus niger, Trichoderma viride, and Penicillium chrysogenum on southern yellow pine (SYP) stakes that were either dip treated or exposed to vapors of the test oils. Thyme and Egyptian geranium oil inhibited growth of all test fungi for 20 weeks. Likewise, dill weed oil vapors inhibited all test fungi for at least 20 weeks. Comparison of two mold test apparatuses—Petri dish test and tank test chambers—gave similar results for thyme oil. These findings support the application of essential oils for surface treatment or vapor exposure of wood to prevent mold infestation.     

咸宁桂花精油的前驱脂肪细胞生长和人体舒压试验的研究

本文采用超临界CO2流体法萃取三个品种咸宁桂花的干桂花得到其精油;采用石油醚浸提法浸提鲜桂花得到其浸膏,用气质联用分析了萃取桂花精油和浸膏的香气成分及其相对含量。进一步探讨了获得的精油对前驱脂肪细胞株3T3-L1细胞培养及生长的影响,并行人体神经舒压试验。结果发现其可减少细胞中的中性脂肪量;心电图LF和HF数据显示桂花精油具有一定的神经舒缓功效。     

The chemical composition of Microbiota decussata

From the leaves of Microbiota decussata (Cupressaceae) biflavones: cupressuflavone, amentoflavone and 7-O-methylamentoflavone were isolated and identified. The amount of cupressuflavone in Microbiota decussata and xCupressocyparis leylandii (Leyland cypress) (Cupressaceae) was determined by HPLC (1.82% and 0.83%, respectively). The chemical composition of essential oils from bark and leaves of Microbiota decussata was established by GC-MS (GC-FID) analysis. As a major component thujopsene (39.2% and 45.9%, respectively) was identified. Wiridiflorol (3.0%) and tau-muurolol (0.3%) were present only in leaves but globulol (1.5%) exclusively in bark. The content of essential oils in M. decussata was high--5.4% in bark and 12.6% in leaves. The essential oils from M. decussata and xC. leylandii were bioassayed towards different fungi of the genus Fusarium. Leyland cypress essential oil at 2% concentration fully inhibited the growth of all fungi.     

Evidence of Increased Diversity of Methanogenic Archaea with Plant Extract Supplementation

This study evaluated the effects of selected essential oils on archaeal communities using the ovine rumen model. Forty weaned Canadian Arcott ewes, fed with barley-based diet, were allotted to one of three essential oil supplementation treatments or a control (10 ewes per treatment) for 13 weeks. The treatments were cinnamaldehyde, garlic oil, juniper berry oil, and a control with no additive. Rumen content was sampled after slaughter and grouped by treatment by combining subsamples from each animal. DNA was extracted from the pooled samples and analyzed for methanogenic archaea using quantitative polymerase chain reaction, denaturing gradient gel electrophoresis, cloning, and sequencing. Our results suggest that the total copy number of archaeal 16S rRNA was not significantly affected by the treatments. The phylogenetic analysis indicated a trend toward an increased diversity of methanogenic archaea related to Methanosphaera stadtmanae, Methanobrevibacter smithii, and some uncultured groups with cinnamaldehyde, garlic, and juniper berry oil supplementation. The trends in the diversity of methanogenic archaea observed with the essential oil supplementation may have resulted from changes in associated protozoal species. Supplementation of ruminant diets with essential oils may alter the diversity of rumen methanogens without affecting the methanogenic capacity of the rumen.     

Effect of 24-epibrassinolide on growth,photosynthesis, and essential oil content of <Emphasis Type="Italic">Pelargonium graveolens</Emphasis> (L.) Herit

The effects of 24-epibrassinolide on growth, photosynthesis, chlorophyll content, carbohydrate fractions, and essential oil content of rose scented geranium (Pelargonium graveolens (L.) Herit) were investigated. Foliar application of 24-epibrassinolide at 0.5, 1, and 3 μM concentrations substantially increased the growth. 24-epibrassinolide at all concentrations improved herbage yield as reflected in the increase of foliar biomass. Exogenous application of 24-epibrassinolide increased the rate of photosynthesis. Growth promotion was also associated with increased chlorophyll content and resulted in the accumulation of carbohydrate fractions. At 3-μM concentration, 24-epibrassinolide increased the total content of essential oils. The quantitative analysis of geranium oil from the geranium plant treated with 3-μM concentration revealed an increase in geraniol content and decrease in citronellol content. The present study demonstrates a positive impact of the new group of phytohormones on the performance of geranium plant, a highly valued aromatic plant.