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Linalool: A review on a key odorant molecule with valuable biological properties

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Abstract

This paper reports on the occurrence, biosynthesis, metabolism, biological and toxicological profile, and assessment of the authenticity of linalool. The main biological properties of linalool – sedative, anxiolytic, analgesic, anticonvulsant, anti-inflammatory, local anaesthetic – are discussed in terms of the molecule's chirality influence, the mechanisms of activity and type of study (in vitro, in vivo, clinical studies). Also, there is a discussion of the recent data on the skin sensitizing potential of linalool based on numerous scientific studies which have been performed in the last few years. Comments of the authenticity assessment of linalool are made considering the limitations imposed by the chemical structure, vegetal matrix or processing methods, but also from the perspective of the powerful and sophisticated analytical techniques available today (GC-C-IRMS, enantio-MDGC coupled to GC-C-IRMS, SNIF-NMR). Copyright © 2014 John Wiley & Sons, Ltd.

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... Gas chromatography-mass spectrometry (GC-MS) analysis indicated that linalool is a characteristic floral scent of D. officinale [9]. Due to its pleasant scent, linalool has tremendous economic value in hygiene products and detergents, including lotions, shampoos, and soaps, and is both stable and does not discolor [15][16][17]. Notably, linalool plays an important role in mediating the communication between plant defense and pollinator attraction, especially in night-blooming, moth-pollinated flowers, and thus helps to promote pollen dispersal and fertilization [18]. Linalool also functions as an antibacterial compound against Campylobacter coli and Campylobacter jejuni [19]. ...
... Linalool also functions as an antibacterial compound against Campylobacter coli and Campylobacter jejuni [19]. With such extensive applications, approximately 1000 tons of linalool are used globally per year [15,17]. Therefore, understanding the biosynthesis and regulation of linalool will provide new avenues for the accelerated accumulation of floral terpenes, for example linalool, with distinct economic and commercial value. ...
... Terpenes are the largest and most diverse group of secondary metabolites produced by plants. Linalool, a plant-derived monoterpene with a broad market value and various biological activities, has been extensively used in cosmetics, as a flavoring agent, in medical science, and in perfumes [15,16]. However, monoterpenes, including linalool, are naturally produced in limited quantities. ...
Article
Linalool is an aromatic monoterpene produced in the Chinese medicinal plant Dendrobium officinale, but little information is available on the regulation of linalool biosynthesis. Here, a novel basic helix-loop-helix (bHLH) transcription factor, DobHLH4 from D. officinale, was identified and functionally characterized. The expression profile of DobHLH4 was positively correlated with that of DoTPS10 (R² = 0.985, p < 0.01), which encodes linalool synthase that is responsible for linalool production, during floral development. DobHLH4 was highly expressed in petals, and was significantly induced by methyl jasmonate. Analysis of subcellular localization showed that DobHLH4 was located in the nucleus. Yeast one-hybrid and dual-luciferase assays indicated that DobHLH4 bound directly to the DoTPS10 promoter harboring the G-box element, and up-regulated DoTPS10 expression. A yeast two-hybrid screen confirmed that DobHLH4 physically interacted with DoJAZ1, suggesting that DobHLH4 might function in the jasmonic acid-mediated accumulation of linalool. Furthermore, transient overexpression of DobHLH4 in D. officinale petals significantly increased linalool production by triggering linalool biosynthetic pathway genes, especially DoTPS10. We suggest a hypothetical model that depicts how jasmonic acid signaling may regulate DoTPS10 by interacting with DobHLH4 and DoJAZ1. In doing so, the formation of linalool is controlled. Our results indicate that DobHLH4 is a positive regulator of linalool biosynthesis and may be a promising target for in vitro-based metabolic engineering to produce linalool.
... Apart from its aroma, vanillin and vanilla extracts have been reported to have beneficial properties, such as antioxidant, anti-mutagenic, hypolipidemic, and anticarcinogen activity (4). Another widespread valuable flavor compound is linalool, which represents approximately 70% of the terpenoids of a wide variety of herbal scents (5). In particular, linalool is among the most abundant compounds present in the herbal mixture at the basis of vermouth wine production (6). ...
... In particular, linalool is among the most abundant compounds present in the herbal mixture at the basis of vermouth wine production (6). Several studies have been published reporting different biological activities of linalool, such as central nervous system depressant effects, as well as analgesic and anti-inflammatory activities (5,7). ...
... Lauraceae, and Rutaceae families, which make up the vermouth mixture (5). However, it is worth noting that no significant (p < 0.05) differences could be detected between the concentrations of linalool in ethanolic and glycolic control extracts (Table 3). ...
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In this work, the effect of pulsed electric field (PEF) pre-treatment on the extractability in green solvents (i. e., ethanol–water mixture and propylene glycol) of target aroma and bioactive compounds, such as vanillin from vanilla pods, theobromine and caffeine from cocoa bean shells, linalool from vermouth mixture, and limonene from orange peels, was investigated. The effectiveness of PEF as a cell disintegration technique in a wide range of field strength (1–5 kV/cm) and energy input (1–40 kJ/kg) was confirmed using impedance measurements, and results were used to define the optimal PEF conditions for the pre-treatment of each plant tissue before the subsequent solid–liquid extraction process. The extracted compounds from untreated and PEF-treated samples were analyzed via GC-MS and HPLC-PDA analysis. Results revealed that the maximum cell disintegration index was detected for cocoa bean shells and vanilla pods ( Z p = 0.82), followed by vermouth mixture ( Z p = 0.77), and orange peels ( Z p = 0.55). As a result, PEF pre-treatment significantly enhanced the extraction yield of the target compounds in both solvents, but especially in ethanolic extracts of vanillin (+14%), theobromine (+25%), caffeine (+34%), linalool (+114%), and limonene (+33%), as compared with untreated samples. Moreover, GC-MS and HPLC-PDA analyses revealed no evidence of degradation of individual compounds due to PEF application. The results obtained in this work suggest that the application of PEF treatment before solid–liquid extraction with green solvents could represent a sustainable approach for the recovery of clean labels and natural compounds from aromatic plants and food by-products.
... 1,2 Linalool is widely distributed in essential oils of over 200 monocotyledonous and dicotyledonous plant species around the globe. 3,4 It is often found in plants of genus Cinnamomum (family Lauraceae), Coriandrum (family Apiaceae), Lavandula (family Lamiaceae) and Citrus (family Rutaceae) (Table 1). 4,6 Factors affecting the linalool content in essential oils include plant tissues used, geographical environment, harvest time, extraction techniques and drying time and temperature. ...
... 3,4 It is often found in plants of genus Cinnamomum (family Lauraceae), Coriandrum (family Apiaceae), Lavandula (family Lamiaceae) and Citrus (family Rutaceae) (Table 1). 4,6 Factors affecting the linalool content in essential oils include plant tissues used, geographical environment, harvest time, extraction techniques and drying time and temperature. 7,8 Besides essential oils, linalool also exists in floral volatiles, herbal extracts, and tea. ...
... Linalool can be oxidized into furanoid and pyranoid. 4 Moreover, linalool can form hydroperoxides after prolonged exposure to air, which is a potent sensitizer. 17,18 The physical and chemical properties of linalool are displayed in Table 2. ...
Article
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Natural products, including essential oils and their components, have been used for their bioactivities. Linalool (2,6-dimethyl-2,7-octadien-6-ol) is an aromatic monoterpene alcohol that is widely found in essential oils and is broadly used in perfumes, cosmetics, household cleaners and food additives. This review covers the sources, physicochemical properties, application, synthesis and bioactivities of linalool. The present study focuses on the bioactive properties of linalool, including anticancer, antimicrobial, neuroprotective, anxiolytic, antidepressant, anti-stress, hepatoprotective, renal protective, and lung protective activity and the underlying mechanisms. Besides this, the therapeutic potential of linalool and the prospect of encapsulating linalool are also discussed. Linalool can induce apoptosis of cancer cells via oxidative stress, and at the same time protects normal cells. Linalool exerts antimicrobial effects through disruption of cell membranes. The protective effects of linalool to the liver, kidney and lung are owing to its anti-inflammatory activity. On account of its protective effects and low toxicity, linalool can be used as an adjuvant of anticancer drugs or antibiotics. Therefore, linalool has a great potential to be applied as a natural and safe alternative therapeutic.
... Most likely, the biosynthesis of these compounds proceeds through the regioselective monoepoxidation of the linalool trisubstituted double bond, followed by the intramolecular cyclization of the obtained epoxy-alcohol [2]. Due to the natural occurrence of both (R)-and (S)-linalool [3] as precursors, this mechanism justifies the formation of both furanoid and pyranoid isomers, as well as the presence in nature of all their possible stereoisomeric forms. Despite the differences in structure, the aromas of the different forms of linalool oxide have a strong family resemblance [4]. ...
... Study of the chemoselective benzoylation of the crude mixture of the linalool oxide isomers obtained from linalool. Percentage of the pyranoid benzoate esters in relation to the sum of all the linalool oxide benzoate ester isomers.3 Percentage of the furanoid benzoate esters in relation to the sum of all the linalool oxide benzoate ester isomers.4 ...
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In this work, we describe a user-friendly procedure for the preparation of all the isomeric forms of the terpene linalool oxide. The presented method is based on the transformation of the linalool enantiomers into the corresponding diastereoisomeric mixtures of the two furanoid oxides and two pyranoid oxides. Taking advantage of the different steric hindrance of the hydroxyl functional groups, the pyranoid forms were separated as a diastereoisomeric mixtures of their benzoate esters. Conversely, the cis- and trans-furanoid isomers were transformed in the corresponding acetates, which were directly separated by chromatography. The hydrolysis of the latter esters afforded cis- and trans-furanoid linalool oxides whereas the same reaction performed on the benzoates mixture afforded a separable mixture of cis- and trans-pyranoid linalool oxide. Overall, the method features, as a unique mandatory requirement, the availability of both linalool enantiomers, and can be conveniently performed from a milligram to a multigram scale.
... Linalool exists as two optical isomers, such as (R)-(−)-& (S)-(+)-isomer. Importantly, (R)-(−)form has a flowery-fresh, lavender-like note reminiscent of lily of the valley [18] while (S)-(+)-linalool exhibits sweet, floral with the citric note [11,12,40,41]. ...
... The first enantiomer separation work on chiral terpenoids in essential oils had been published in the mid-nineties [35], followed by other significant publications [7,33]. Some reports affirm that linalool possessed odor-induced anxiolytic effects [16], sedative, fungicidal and bactericidal action [13,31,40] it has analgesic and anti-inflammatory activities (Aprotosoaie et al. 2014). Toxicological and dermatologic assessment of linalool for their use as fragrance ingredients has also been reported [4]. ...
Article
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ndia is an emerging basil essential oil producer in South-east Asia. Two high essential oil yielding hybrids, namely one inter specific hybrid between of O. basilicum and O. kilimandscharicum Gürke (HYBL-1) and another intraspecific hybrid of O. basilicum × O. basilicum (OBL-1) of basil were analyzed using GC, enantiomeric GC, NMR, enantio-GC–MS and GC–MS methods. Inter specific hybrid HYBL-1 contained high essential oil-rich in linalool (68.5%), camphor (8%), and 1,8-cineole (4.6%) as characteristic constituents among monoterpenoids, whereas β-caryophyllene (1.9%), germacrene D (1.0%), and epi-α-cadinol (1.9%) were the sesquiterpenoids at the Lucknow (North Indian conditions) and linalool (71.8%), camphor (9.4%) and 1,8-cineole (4.3%) at Hyderabad (South Indian conditions) locations. Intraspecific hybrid (OBL-1) possessed linalool (66.1%), 1,8-cineole (5.4%) and geraniol (8.6%) with sesquiterpenoids in low proportions. Inter specific hybrid HYBL-1 showed superiority over OBL-1 in the multi-location trials conducted at Lucknow and Hyderabad. Average mean performance of inter specific hybrid over locations was: herb yield 44.80 t/ha, oil content 0.63%, oil yield 188.50 kg/ha, linalool content 67.65%, camphor content 8.90% v/s OBL-1 herb yield 21.32 t/ha, oil content 0.53%, oil yield 97.50 kg/ha, linalool content 65.55%, camphor content 0.00%, respectively. The essential oil of these two hybrids subjected to enantiomer differentiation revealed a high enantiomeric excess for (3R) -(−)-linalool, whereas (1R)- (+)-camphor was recorded exclusively in inter specific hybrid. The extensive NMR experiments were performed to confirm constituents in these hybrids and found that NMR spectroscopy could also be an ideal tool for the differentiation of essential oils from commercial samples declared as natural.
... Nonetheless, topically applied herbal medicinal preparations made of L. angustifolia may lead to such side-effects as contact dermatitis (Gangemi et al., 2015). Biological properties of linalool, namely sedative, anxiolytic, analgesic, anticonvulsant, anti-inflammatory, local anaesthetic, are discussed in the context of the molecule's chirality influence, the mechanisms of activity and type of study (in vitro, in vivo, clinical studies) (Aprotosoaie et al., 2014). The recently obtained data on properties of linalool to skin synthesis are considered in report by Aprotosoaie et al. (2014). ...
... Biological properties of linalool, namely sedative, anxiolytic, analgesic, anticonvulsant, anti-inflammatory, local anaesthetic, are discussed in the context of the molecule's chirality influence, the mechanisms of activity and type of study (in vitro, in vivo, clinical studies) (Aprotosoaie et al., 2014). The recently obtained data on properties of linalool to skin synthesis are considered in report by Aprotosoaie et al. (2014). ...
Article
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Plant food additives are becoming more and more popular and broadly applied products, though the information on risks they poses to the organism is limited and contradictive. Obesity and overeating are some of the commonest health issues around the world, and people are increasingly consuming workability-enhancing preparations as a simple and fast method of weight control. The plant-based preparations are considered less harmful than the synthetic chemical ones. Lavandula angustifolia Mill., Melissa officinalis L. and Vitex angus-castus L. are broadly used as food additives and medicinal plants, despite the fact that their complex physiological assessment on model animals in the conditions of obesity has not yet been performed. We carried out a 30-day experiment on white male rats. All the animals were given high-fat diet, and the experimental animals, in addition to this diet, received 5% crumbled dry herbs of L. angustifolia, M. officinalis or V. angus-castus. Taking into account the overall amount of consumed food, the mean daily gain in body weight; at the end of the experiment, we determined the index of the weight of the internal organs, biochemical and morphological blood parameters. At the beginning and the end of the experiment, the rats were examined for motor and orienting activities, and emotional status. Rats on high-fat diet gained up to 112% body weight by the end of the experiment, while rats that had received V. angus-castus gained up to 119%, M. officinalis – 135%, L. angustifolia – 139%, compared with the initial body weight. Addition of medicinal plants to the diet led to increase in average daily weight increment, significantly and reliably after consuming lavender and lemon balm, less significantly and unreliably after eating Vitex. L. angustifolia and M. officinalis reduced the relative brain weight, and ingestion of L. angustifolia and M. officinalis caused notable decrease in the relative mass of the thymus (down to 58% and 47% of the relative weight of thymus in animals of the control group respectively). Also, these plants decreased the motor and orienting activities of the rats by the end of the experiment. As for the biochemical parameters of blood, the activity of alkaline phosphatase significantly increased to 406% following consumption of Melissa, to 350% after consuming lavender, and to 406% after Vitex, compared to the control group. Furthermore, all the groups were observed to have increased AST and ALT activities. Intake of lavender led to increases in cholesterol (to 125%) and LDL cholesterol (to 228%), whereas the groups that consumed lemon balm were observed to have decreases in urea nitrogen (to 79%), totalbilirubin (to 63%) and triglycerides (to 63%). Addition of Vitex led to increase in the index of aterogenecity against the background of notable fall in HDL cholesterol (to 52% of the control group). The medicinal plants also contributed to the normalization of the glucose level. Morphological analysis of blood revealed no significant changes, except heightened content of monocytes in blood, which is characteristic of all groups, including the control. Effects of L. angustifolia, M. officinalis and V. angus-castus on the organism of rats on excessive-fat diet require additional histological, histochemical and immunological surveys.
... Therefore, scaffolds containing naturally derived (e.g., curcumin, essential oils) compounds have gained increasing attention for tissue engineering applications [11][12][13][14]. Among antimicrobial essential oils, linalool (3,7-dimethyl-1,6-octadien-3-ol) has demonstrated antimicrobial activity against Gramnegative and Gram-positive bacteria [15][16][17] and potential effects over periodontal pathogens [18]. Linalool is an acyclic monoterpene tertiary alcohol found in several plant species [19,20] and its antimicrobial activity results from bacterial membrane disruption and enzymatic activity suppression [21]. ...
... Furthermore, products released from CIT and LIN scaffolds demonstrated high cytocompatibility and reinforced the previous findings of these essential oils in contact with different cell types [28]. Even though 40% CIT and 40% LIN presented the lowest values at the initial time point, their cytocompatibility increased after 7 and 14 days, which could indicate a burst release of the components in a short period, as previously evidenced for linalool [16]. Although this is the first in vitro study testing electrospun scaffolds containing these monoterpenes for endodontic disinfection, citral and linalool scaffolds presented promising results to support further investigation for different bacterial models and complex biofilm structures in the root canal area. ...
Article
This investigation aimed to synthesize poly(d,l-lactide) (PLA)-based fibrous scaffolds containing natural essential oils (i.e., linalool and citral) and determine their antimicrobial properties and cytocompatibility as a clinically viable cell-friendly disinfection strategy for regenerative endodontics. PLA-based fibrous scaffolds were fabricated via electrospinning with different concentrations of linalool and citral. The micromorphology and average diameter of the fibers was investigated through scanning electron microscopy (SEM). The chemical composition of the scaffolds was inferred by Fourier-transform infrared spectroscopy (FTIR). Antimicrobial efficacy against Enterococcus faecalis and Actinomyces naeslundii was also evaluated by agar diffusion and colony-forming units (CFU) assays. The scaffolds’ cytocompatibility was determined using dental pulp stem cells (DPSCs). Statistical analyses were performed and the significance level was set at α = 5%. Linalool and citral’s incorporation in the PLA fibrous scaffolds was confirmed in the FTIR spectra. SEM images indicate no morphological changes upon inclusion of the essential oils, except the reduced diameter of 40% linalool-laden fibers (p < 0.05). Importantly, significant antimicrobial properties were reported for citral-containing scaffolds for CFU/mL counts (p < 0.05), while only 20% and 40% linalool-laden scaffolds reduced CFU/mL (p < 0.05). Meanwhile, the inhibition halos were verified in a concentration-dependent manner for all monoterpenes-laden scaffolds. Citral- and linalool-laden PLA-based fibrous scaffolds showed acceptable cytocompatibility. The incorporation of natural monoterpenes did not alter the scaffolds’ fibrous morphology, promoted antimicrobial action against endodontic pathogens, and preserved DPSCs viability. Linalool- and citral-laden electrospun scaffolds hold promise as naturally derived antimicrobial therapeutics for applications in regenerative endodontics.
... Linalool exists as two optical isomers, such as (R)-(−)-& (S)-(+)-isomer. Importantly, (R)-(−)form has a flowery-fresh, lavender-like note reminiscent of lily of the valley [18] while (S)-(+)-linalool exhibits sweet, floral with the citric note [11,12,40,41]. ...
... The first enantiomer separation work on chiral terpenoids in essential oils had been published in the mid-nineties [35], followed by other significant publications [7,33]. Some reports affirm that linalool possessed odor-induced anxiolytic effects [16], sedative, fungicidal and bactericidal action [13,31,40] it has analgesic and anti-inflammatory activities (Aprotosoaie et al. 2014). Toxicological and dermatologic assessment of linalool for their use as fragrance ingredients has also been reported [4]. ...
Article
India is an emerging basil essential oil producer in South-east Asia. Two high essential oil yielding hybrids, namely one inter specific hybrid between of O. basilicum and O. kilimandscharicum Gürke (HYBL-1) and another intraspecific hybrid of O. basilicum × O. basilicum (OBL-1) of basil were analyzed using GC, enantiomeric GC, NMR, enantio-GC–MS and GC–MS methods. Inter specific hybrid HYBL-1 contained high essential oil-rich in linalool (68.5%), camphor (8%), and 1,8-cineole (4.6%) as characteristic constituents among monoterpenoids, whereas β-caryophyllene (1.9%), germacrene D (1.0%), and epi-α-cadinol (1.9%) were the sesquiterpenoids at the Lucknow (North Indian conditions) and linalool (71.8%), camphor (9.4%) and 1,8-cineole (4.3%) at Hyderabad (South Indian conditions) locations. Intraspecific hybrid (OBL-1) possessed linalool (66.1%), 1,8-cineole (5.4%) and geraniol (8.6%) with sesquiterpenoids in low proportions. Inter specific hybrid HYBL-1 showed superiority over OBL-1 in the multi-location trials conducted at Lucknow and Hyderabad. Average mean performance of inter specific hybrid over locations was: herb yield 44.80 t/ha, oil content 0.63%, oil yield 188.50 kg/ha, linalool content 67.65%, camphor content 8.90% v/s OBL-1 herb yield 21.32 t/ha, oil content 0.53%, oil yield 97.50 kg/ha, linalool content 65.55%, camphor content 0.00%, respectively. The essential oil of these two hybrids subjected to enantiomer differentiation revealed a high enantiomeric excess for (3R) -(−)-linalool, whereas (1R)- (+)-camphor was recorded exclusively in interspecific hybrid. The extensive NMR experiments were performed to confirm constituents in these hybrids and found that NMR spectroscopy could also be an ideal tool for the differentiation of essential oils from commercial samples declared as natural.
... In Guangdong and Southeast Asia, An-tea is known as "holy tea", somewhat reflecting its medicinal value. Linalool has been found to have analgesic, anti-anxiety, sedative, hypnotic, anti-inflammatory, antitumor, antibacterial, and other pharmacological activities among common volatile substances [24]. β-Ionone also has a wide range of biological activities, especially some anticancer cell activity. ...
Article
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To investigate the effects of different aging times, three An–tea samples were selected for comparison with a non-aged sample as the control (CK, one-year-old) and labeled as high-aged (HAS, 12 years old), medium-aged (MAS, 7 years old), and low-aged samples (LAS, 2 years old). Changes in the volatile components of the different An–tea samples were investigated using headspace–solid-phase microextraction (HS-SPME) combined with gas chromatography–mass spectrometry (GC-MS). The volatile components of An–tea consisted of eight types of compounds. Aldehydes and hydrocarbons were dominant in LAS, while esters, ketones, alcohols, nitrogen-containing compounds, and ethers were the most abundant compound in MAS. Esters were dominant in HAS, while phenols were only present in LAS and CK. As aging time increased, the number of identical compounds gradually decreased, while the relative contents of the alcohols also decreased. Except for CK, the contents of ketones and aldehydes gradually decreased as the aging time increased. The content of aldehydes greatly increased during the initial aging period. Ketones and esters had markedly increased in HAS, while their abundance in LAS was close to that in CK. The comprehensive quality score of the volatile components obtained by principal component analysis was highest for MAS, followed by HAS and LAS, with CK having the lowest score.
... Therefore, a high level of alkanes (heptadecane and eicosane) might be a possible explanation for the light fragrances in 'Luoyanghong'. Linalool is an acyclic monoterpene alcohol (Aprotosoaie et al., 2014) and leads to a lily of the valley flavor (Parreira et al., 2017). At the same time, linalool has been shown to play an important role in communication between plant defense and attracting pollinators, especially in night flowers and moth-borne flowers, to promote pollen transmission and pollination (Yu et al., 2021). ...
Article
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Tree peony (Paeonia suffruticosa) is an ornamental and medicinal plant in China. The fresh eating of flower petals has gradually become a new idea for further development. This study analyzed the sensory indexes, nutritional indexes and antioxidant indexes of fresh flowers of five cultivars, namely, ‘Fengdan’ (P. ostia ‘Fengdan’), ‘Xiangyu’ (P. suffruticosa ‘Xiangyu’), ‘Zhaofen’ (P. suffruticosa ‘Zhanfen’), ‘Luoyanghong’ (P. suffruticosa ‘Luoyanghong’) and ‘High Noon’ (P. ‘High Noon’), to provide a theoretical basis for eating fresh tree peony flowers. The aroma volatiles of petals mainly comprised terpenes, alcohols and alkanes. ‘Luoyanghong’ and ‘High Noon’ have brighter colors. The taste test showed that ‘Luoyanghong’, ‘High Noon’ and ‘Xiangyu’ were the most palatable. ‘High Noon’ contained the highest soluble sugar content, ‘Luoyanghong’ contained the highest starch and vitamin C (VC) levels, and ‘Zhaofen’ contained the highest soluble protein content. The contents of bioactive compounds were the highest in ‘Luoyanghong’, and superoxide dismutase (SOD) activity was the highest in ‘Xiangyu’. The petals were rich in essential amino acids, with the highest amount in ‘Xiangyu’. ‘Luoyanghong’ and ‘High Noon’ showed strong antioxidant capacity. Therefore, tree peony flowers have excellent sensory qualities, abundant nutrients and strong antioxidant activity and could be further developed as a food to be eaten fresh. The results showed that tree peony flowers had great edible potential. Flowers of red and yellow cultivars can be considered for fresh eating on the basis of the traditional consumption of white and pink tree peony flowers.
... Linalool (3,7-dimethyl-1,6-octadien-3-ol, C 10 H 18 O), an alcohol of monoterpene origin with tertiary and acyclic structures (linalyl alcohol), is recognized as major bioactive component of Coriandrum. sativum, Lavandula angustifolia, Thymus vulgaris and Cinnamomum camphora essential oils with significant anti-inflammatory, antimicrobial, analgesic, anti-hyperlipidemia, anticancer, antidepressant and neuroprotective activities [14]. Moreover, linalool has been successfully used in therapeutic experiments as neurotransmitter receptor having promising avenue in drug delivery [15]. ...
Article
The aim of the present study was to encapsulate linalool into chitosan nanocomposite (Nm-linalool) for developing novel controlled release delivery system in order to protect stored rice against fungal infestation, aflatoxin B1 (AFB1) contamination, and lipid peroxidation. The chitosan-linalool nanocomposite showed spherical shapes, smooth surface with monomodal distribution as revealed by SEM and AFM investigation. FTIR and XRD represented peak shifting and changes in degree of crystallinity after incorporation of linalool into chitosan nanocomposite. Nanoencapsulation of linalool showed higher zeta potential and lowered polydispersity index. TGA analysis reflected the stability of Nm-linalool with reduced weight loss at varying temperatures. Biphasic pattern, with initial rapid release followed by sustained release illustrated controlled delivery of linalool from chitosan nanocomposite, a prerequisite for shelf-life enhancement of stored food products. Chitosan nanocomposite incorporating linalool displayed prominent antifungal and antiaflatoxigenic activity during in vitro as well as in situ investigation in rice with improved antioxidant potentiality. Further, Nm-linalool displayed considerable reduction of lipid peroxidation in rice without exerting any adverse impact on organoleptic attributes. In conclusion, the investigation strengthens the application of chitosan-linalool nanocomposite as an innovative controlled nano-delivery system for its practical application as novel environmentally friendly eco-smart preservative in food and agricultural industries.
... This compound is frequently used as an ingredient of perfumes, food and household detergents (Mei et al., 2015). Linalool is also an important intermediate in the synthesis of vitamin E during industrial production (Aprotosoaie et al., 2014). LINS, the TPS that synthesizes linalool, has been identified in many plants, such as RcLINS from rose and LaLINS from lavender (Landmann et al., 2007;Magnard et al., 2018). ...
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The fruits of Amomum villosum and Amomum longiligulare are both used medicinally as Fructus Amomi the famous traditional Chinese medicine, however, the medicinal quality of A. villosum is better than that of A. longiligulare. Volatile terpenoids in the seeds, especially bornyl acetate and borneol, are the medicinal components of Fructus Amomi. The volatile terpenoids and transcriptome of developing seeds of A. villosum and A. longiligulare were compared in this study. The result revealed that the bornyl acetate and borneol contents were higher in A. villosum than in A. longiligulare. Additionally, six terpenoid synthase genes (AlTPS1–AlTPS6) were screened from the transcriptome of A. longiligulare, and AlTPS2 and AlTPS3 were found to share 98 and 83% identity with AvTPS2 and AvBPPS (bornyl diphosphate synthase) from A. villosum, respectively. BPPS is the key enzyme for the biosynthesis of borneol and bornyl acetate. Biochemical assays improved that AlTPS2 had an identical function to AvTPS2 as linalool synthase; however, AlTPS3 produced camphene as the major product and bornyl diphosphate (BPP) as the secondary product, whereas AvBPPS produced BPP as its major product. There was only one different amino acid between AlTPS3 (A496) and AvBPPS (G495) in their conserved motifs, and the site-directed mutation of A496G in DTE motif of AlTPS3 changed the major product from camphene to BPP. Molecular docking suggests that A496G mutation narrows the camphene-binding pocket and decreases the BPP-binding energy, thus increases the product BPP selectivity of enzyme. In addition, the expression level of AvBPPS was significantly higher than that of AlTPS3 in seeds, which was consistent with the related-metabolites contents. This study provides insight into the TPS-related molecular bases for the biosynthesis and accumulation differences of the bioactive terpenoids between A. villosum and A. longiligulare. BPPS, the key gene involved in the biosynthesis of the active compound, was identified as a target gene that could be applied for the quality-related identification and breeding of Fructus Amomi.
... Many studies, including our previous studies, have shown that essential oils exhibited strong antibacterial activities [8][9][10][11][12]. Linalool (3,7-dimethyl-1,6-octadien-3-ol) is a vital constituent found in many essential oils with good antibacterial activity against different kinds of microorganisms [13], such as Listeria monocytogenes (our previous study) [14], Pseudomonas fluorescens [15], P.aeruginosa [16], Salmonella senftenberg [17], and S.putrefaciens [18] etc. It is generally recognized as safe (GRAS) as a food additive. ...
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Aeromonas hydrophila is one of the most important aquatic pathogens causing huge economic losses to aquaculture. Linalool, a vital ingredient of a variety of essential oils, was proved as a good antimicrobial agent in our previous studies. However, the low solubility and volatility of Linalool obstruct its application in the field of aquatic drugs. Thus, in this study, Linalool nano-emulsion (LN) was prepared to solve these obstructions. We investigated the physicochemical properties, antibacterial activity, and mode of action of LN against A. hydrophila. LN with different medium chain triglycerides (MCT) concentrations were prepared by ultrasonic method. The results showed that the emulsion droplet size of LN was the smallest when MCT was not added to the formulation. Nano-emulsions are usually less than 500 nm in diameter. In our study, LN in this formulation were spherical droplet with a diameter of 126.57 ± 0.85 nm and showed good stability. LN showed strong antibacterial activity, the MIC and MBC values were 0.3125% v/v and 0.625% v/v, respectively. The bacterial population decreased substantially at 1 × MIC of LN. LN exhibited disruptive effect on cell membranes by scanning electron microscope (SEM) and transmission electron microscope (TEM). The present study provided a formulation of Linalool nano-emulsion preparation. Moreover, the good antibacterial activity of LN showed in our study will promote the application of Linalool for the control and prevention of A. hydrophila in aquaculture.
... Part of such absorbed compounds reached the brain, crossing the blood-brain barrier. A number of studies showed that systemic administration of linalool induced analgesic, anxiolytic, and other physiological effects [484]. Though it is still under debate whether the serum concentration of linalool could reach the effective dose (cf, 50-200 mg/kg for analgesia) by linalool inhalation, it is possible that the absorbed compounds cause neuropharmacological effects in the CNS. ...
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The year 2020 became the year of the outbreak of coronavirus, SARS-CoV-2, which escalated into a worldwide pandemic and continued into 2021. One of the unique symptoms of the SARS-CoV-2 disease, COVID-19, is the loss of chemical senses, i.e., smell and taste. Smell training is one of the methods used in facilitating recovery of the olfactory sense, and it uses essential oils of lemon, rose, clove, and eucalyptus. These essential oils were not selected based on their chemical constituents. Although scientific studies have shown that they improve recovery, there may be better combinations for facilitating recovery. Many phytochemicals have bioactive properties with anti-inflammatory and anti-viral effects. In this review, we describe the chemical compounds with anti- inflammatory and anti-viral effects, and we list the plants that contain these chemical compounds. We expand the review from terpenes to the less volatile flavonoids in order to propose a combination of essential oils and diets that can be used to develop a new taste training method, as there has been no taste training so far. Finally, we discuss the possible use of these in clinical settings.
... (R)-Linalool, (-)-alpha-pinene, peruviol, (L)-alpha-terpineol, and cymol were identified as the top five hot-specific ingredients. (R)-Linalool is a natural monoterpene with anti-inflammatory and analgesic effects [23]. (-)-Alpha-pinene is also a monoterpene that has neuroprotective and anti-nociceptive effects [24]. ...
Article
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Effective treatments for patients experiencing temperature-related symptoms are limited. The hot and cold effects of traditional herbal medicines have been utilized to treat and manage these symptoms, but their molecular mechanisms are not fully understood. Previous studies with arbitrarily selected herbs and ingredients may have produced biased results. Here, we aim to systematically elucidate the molecular mechanisms of the hot and cold properties of herbal medicines through an unbiased large-scale investigation of herbal ingredients, their target genes, and the transcriptome signatures induced by them. Using data regarding 243 herbs retrieved from two herbal medicine databases, we statistically identify (R)-Linalool, (-)-alpha-pinene, peruviol, (L)-alpha-terpineol, and cymol as five new hot-specific ingredients that share a common target, a norepinephrine transporter. However, no significant ingredients are cold-specific. We also statistically identify 14 hot- and 8 cold-specific new target genes. Pathway enrichment analysis of hot-specific target genes reveals the associated pathways including neurotransmitter reuptake, cold-induced thermogenesis, blood pressure regulation, adrenergic receptor signaling, and cation symporter activity. Cold-specific target genes are associated with the steroid pathway. Transcriptome analysis also shows that hot herbs are more strongly associated with coagulation and synaptic transmission than cold herbs. Our results, obtained from novel connections between herbal ingredients, target genes, and pathways, may contribute to the development of pharmacological treatment strategies for temperature-related pain using medicinal plants.
... The two enantiomers have considerably different perception thresholds for humans. (R)-linalool has the odor perception of 0.008 ppm in air which is around 10 times lower than that of (S)-linalool [4,5]. The difference in linalool enantiomer ratio leads to different taste and odor of linalool-containing products. ...
Article
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Linalool, a volatile terpene alcohol, is responsible for a characteristic aroma in food, beverages, and cosmetics. However, linalool’s low aqueous solubility and high volatility limit the applications and shelf life of linalool-containing products. Nanoencapsulation using beta-cyclodextrin (BCD), methyl-beta-cyclodextrin (MBCD) and hydroxypropyl-beta-cyclodextrin (HPBCD) was studied to improve the aqueous solubility and stability of linalool. Linalool has two enantiomers with distinct flavors and odors which affect product quality. The enantiomeric selectivity of the cyclodextrins (CDs) toward racemic linalool standard was evaluated. A computational simulation was performed to predict the conformations and interactions of the inclusion complexes. The 1:1 host-guest ratio from the computer simulation was implemented in the experimental study. Phase solubility study shows an improvement in linalool aqueous solubility after being encapsulated by CDs. The encapsulation efficiencies of linalool/BCD, linalool/MBCD, and linalool/HPBCD inclusion complexes are 66.30%, 51.38% and 32.31%, respectively. Nanoencapsulation by CDs can preserve linalool in the form of inclusion complexes compared to its free form. The amount of remaining linalool in linalool/BCD, linalool/MBCD, and linalool/HPBCD inclusion complexes are 89.57%, 87.07%, and 74.86%, respectively which are considerably larger than that of pure linalool (42.30%). CDs also show the enantiomeric selectivity toward (R)-linalool as evident from (R)-linalool percentage of 54.53% in the inclusion complex.
... In addition, only the R -enantiomer and racemates have sedative effects 8 . Other biological effects have been ascribed to the enantiomers 9 and racemates of linalool, including anti-leishmanial activity in raclinalool 10 , anesthetic activity in S -+ -linalool 11 , and acaricidal activity in R ---linalool 12 . These enantiomers also have different fragrance properties 13,14 . ...
Article
The volatile components of kuromoji oil (Lindera umbellata Thunb.) obtained in Shizuoka Pref. were analyzed by GC/MS. Linalool, α-pinene, limonene, camphene, cis- and trans-dihydrocarvone, 1,8-cineol, 4-terpinenol, α-terpineol, piperitone, geranyl acetate, geraniol, and trans-nerolidol were identified as major components. Using enantio-MDGC-MS, the enantiomeric ratio ((R)-(-) vs (S)-(+)) of linalool in this oil was determined to be 67.8/32.2. Touch care treatment while sniffing this oil was done on cancer patients. We found that the relaxation effect persisted longer after the treatment compared to treatment without aroma. graphical abstract Fullsize Image
... The isolated linalool showed the lengthier time for anesthesia induction in some stages and recovery at 0.1 and 0.2 µL/mL, in comparison to standard linalool [118]. (3S)-(+)-Linalool and (3R)-(-)-linalool have different properties on the central nervous system, related to depressant effects, analgesic and anti-inflammatory activities [126]. ...
Article
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Lauraceae families have great diversity in the world’s tropical regions and are represented mainly by aromatic shrubs and trees with significant production of essential oils (EOs). This work presents a review of the EO chemical profiles from specimens of Aniba, including their seasonal variations, geographical distributions, and biological activities in the Amazon biome. Based on the survey, 15 species were reviewed, representing 167 oil samples extracted from leaves, twig barks, and woods. Brazilian Amazon was the most representative geographic area in the number of specimens, highlighting the locations Belém, (Pará state, PA) (3 spp., 37 samples), Santarém (PA) (3 spp., 10 samples), Carajás (PA) (3 spp., 7 samples), and Manaus (Amazonas state, AM) (3 spp., 16 samples). The main compound classes identified in oils were benzenoids and phenylpropanoids, represented by 1-nitro-2-phenylethane, benzyl salicylate, benzyl benzoate and methyleugenol, along with terpenoids, especially monoterpenes and sesquiterpenes, such as linalool, α-phellandrene, β-phellandrene, β-selinene, and spathulenol. The EOs from Aniba showed considerable variation in the chemical profiles according to season and collection site. The hierarchical cluster analysis classified the samples into two main groups according to chemical composition. This review highlights its comprehensive and up-to-date information on history, conservation, traditional uses, chemosystematics, pharmacological potential of Aniba species.
... The microbial drug resistance problem boosted the research on natural compounds, and among these we can cite pulegone, a constituent known for its proven antibacterial and anti-inflammatory activities that, although present in a higher amount in the flower EOs, its percentages exceed 30% and 70% in the leaf EOs of each A. 'Blue Boa' and A. aurantiaca, respectively [51,52]. Linalool, a monoterpene unsaturated alcohol, instead, is one of the major floral scents in nature [53], widely used in the perfumery, cosmetics, and food industries [54]. The leaf EO of M. didyma can be a good source, since its value was quadrupled in comparison with flowers and constitutes almost 40% of the identified fraction. ...
Article
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(1) Background: The leaves of some plants are reported for their culinary uses, while in edible flowers, they are one of the discarded products in the supply chain. We investigated the volatile profile (VP) and the essential oil (EO) compositions of leaves from 12 Lamiaceae species, of which nine belong to the Mentheae tribe and three to the Ocimeae tribe. (2) Methods: Phytochemical analyses were performed using a GC-MS instrument. (3) Results: More than 53% of the Ocimeae tribe VP was represented by sesquiterpene hydrocarbons (SH), followed by phenylpropanoids, except for O. × citriodorum, where oxygenated monoterpenes (OM) were the second main class. OM prevailed in six species of the Mentheae tribe except for Agastache ‘Arcado Pink’, Salvia discolor, and S. microphylla, where SH dominated. The EO composition of Ocimeae tribe showed a similar behavior to that of VP concerning the predominant classes. O. basilicum ‘Blue Spice’ (Ob-BS) was an exception, since it showed oxygenated sesquiterpenes (OS: 29.6%) as a second principal class. Sesquiterpene compounds were also present in a high amount in two species of the Salviinae subtribe (S. microphylla and S. discolor) and two of the Nepetinae subtribe (Nepeta × faasenii and A. ‘Arcado Pink’). The remaining species of the Mentheae tribe were characterized by OM. (4) Conclusions: Many of the main compounds found were reported for their importance in human health and thus are important as ingredients in several new industrial products.
... Similarly, the administration of purple basil essential oil improved hyperlipidemia, lowering triglyceride and total cholesterol levels, similar to our results [31]. Additionally, linalool has cholesterol-lowering, antioxidant, and anti-inflammatory activities [41]. Previous research showed that linalool decreased the LDL levels [6] and activated hepatic PPARα [21]. ...
Article
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We explored the physiological effects of inhaling basil essential oil (BEO) and/or linalool and identified odor-active aroma compounds in BEO using gas chromatography/mass spectrometry (GC–MS) and GC–olfactometry (GC–O). Linalool was identified as the major volatile compound in BEO. Three groups of rats were administered BEO and linalool via inhalation, while rats in the control group were not. Inhalation of BEO for 20 min only reduced the total weight gain (190.67 ± 2.52 g) and increased the forced swimming time (47.33 ± 14.84 s) compared with the control group (219.67 ± 2.08 g, 8.33 ± 5.13 s). Inhalation of BEO for 5 min (392 ± 21 beats/min) only reduced the pulse compared with the control group (420 ± 19 beats/min). Inhalation of linalool only reduced the weight of white adipose tissue (5.75 ± 0.61 g). The levels of stress-related hormones were not significantly different among the groups. The total cholesterol and triglyceride levels decreased after inhalation of BEO for 20 min (by more than −10% and −15%, respectively). Low-density lipoprotein cholesterol levels were lowered (by more than −10%) by the inhalation of BEO and linalool, regardless of the inhalation time. In particular, BEO inhalation for 20 min was associated with the lowest level of low-density lipoprotein cholesterol (53.94 ± 2.72 mg/dL). High-density lipoprotein cholesterol levels increased after inhalation of BEO (by more than +15%). The atherogenic index and cardiac risk factors were suppressed by BEO inhalation. Animals exposed to BEO and linalool had no significant differences in hepatotoxicity. These data suggest that the inhalation of BEO and linalool may ameliorate cardiovascular and lipid dysfunctions. These effects should be explored further for clinical applications.
... Essential oils act on bacteria by degradation of the cell wall (Gill and Holley, 2006), destruction of the cell membrane structure (Ultee et al., 2002) and membrane proteins (Lambert et al., 2001), inhibition of quorum sensing, influencing the proton dynamic potential energy (Ultee and Smid, 2001), and inhibiting intracellular ATP synthesis (Burt, 2004). Linalool (LL) is one of the main components of certain aromatic plant essential oils such as lavender essential oil and camphor essential oil (Aprotosoaie et al., 2014). Linalool is often added to food as an aromatic and flavoring agent. ...
Article
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A linalool/polycaprolactone (LL/PCL) antibacterial film was prepared by using a coaxial electrospinning process, and its physical and chemical properties were characterized. The antibacterial film was formed into an active antibacterial gasket, and its effect on salmon preservation was analyzed. The results show that the LL/PCL nanofiber membrane had a well-developed microstructure, and the fiber surface was smooth and uniform. The diameter of the fibers in the PCL membrane without the core material (linalool) was 113.92 ± 23.74 nm. In contrast, the diameter of the coaxial nanofiber membrane with linalool increased, and the diameter of the LL/PCL membranes with 20% and 40% linalool was 220.62 ± 44.01 and 232.22 ± 56.27 nm, respectively. The hydrophobicity and water vapor permeability were enhanced, whereas the tensile strength and elongation at break decreased slightly, while the thermal stability did not differ significantly with the incorporation of linalool. Analysis of the sustained release of linalool showed that the LL/PCL coaxial fiber membranes could release linalool into the reaction system for a long time. The LL/PCL nanofiber film was used to create an antibacterial active gasket for salmon preservation experiments. Sensory evaluation and analyses of the total bacterial count, total volatile basic nitrogen (TVB-N), thiobarbituric acid reactive substances (TBARS), pH, texture (hardness, elasticity, chewiness, and viscoelasticity), water distribution change, and aroma using an electronic nose were used to determine the quality of salmon. It was found that food-grade tinfoil and the PCL gasket had no significant effect on the freshness of salmon, while the active antibacterial gasket samples containing linalool could decrease the rate of decay salmon and effectively prolong the shelf-life of salmon by releasing linalool.
... During the ripening period, the terpene content of TH figs decreased markedly (46 ± 3.84-0%) while it remained constant (P < 0.05) in AZ (changing from 37.40 ± 1.37 to 37.06 ± 2.56%) and AV figs (changing from 41.11 ± 4.43 to 58.89 ± 10.40%) in AZ figs, which were characterized by high terpene contents. The major terpene molecule was linalool, which is recognized for its floral scents and has several biological properties (anti-inflammatory, antioxidant, and analgesic) (Aprotosoaie et al., 2014). This molecule is an important factor in the establishment of fig cultivar fingerprints, as all previous studies on fresh fig volatile molecules reported low terpene contents (Oliveira et al., 2010;Villalobos et al., 2018). ...
... Linalool (3,7-dimethyl-1,6-octadien-3-ol) is a widely known chiral terpene that is present in hundreds of botanical species [1][2][3]. Its contribution to flavor and fragrance is dependent not only on concentration but also on the dominant enantiomer form [4]. ...
Article
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The chiral analysis of terpenes in complex mixtures of essential oils, necessary for authentication, has been further developed using chiral tagging molecular rotational resonance (MRR) spectroscopy. One analyte that is of particular interest is linalool (3,7-dimethyl-1,6-octadien-3-ol), a common natural chiral terpene found in botanicals with its enantiomers having unique flavor, fragrance, and aromatherapy characteristics. In this MRR demonstration, resolution of the enantiomers is achieved through the addition of a chiral tag, which creates non-covalent diastereomeric complexes with distinct spectral signatures. The relative stereochemistry of the complexes is identified by the comparison of calculated spectroscopic parameters with experimentally determined parameters of the chiral complexes with high accuracy. The diastereomeric complex intensities are analyzed to determine the absolute configuration (AC) and enantiomeric excess (EE) in each sample. Here, we demonstrate the use of chiral tagging MRR spectroscopy to perform a quantitative routine enantiomer analysis of linalool in complex essential oil mixtures, without the need for reference samples or chromatographic separation.
... It occurs primarily via breath, urine, or feces, while the concrete pathways and partitions depend on various factors and can vary greatly. Even if the available evidence originates from distinct studies and therefore prevents direct comparison, this variability can be illustrated by exemplary reports on eugenol and linalool (and their metabolites), for which the renal pathway has been reported to account for 95% and 60% of excretion, respectively [92][93] . The pulmonary and fecal route were additionally mentioned to contribute to excretion of linalool. ...
Article
Odorants are relatively small molecules which are easily taken up and distributed in the human body. Despite their relevance in everyday life, however, only a limited amount of evidence about their metabolism, pathways, and bioactivities in the human body exists. With this review, we aim to encourage future interdisciplinary research on the function and mechanisms of the biotransformation of odorants, involving different disciplines such as nutrition, medicine, biochemistry, chemistry, and sensory sciences. Starting with a general overview of the different ways of odorant uptake and enzymes involved in the metabolism of odorants, a more precise description of biotransformation processes and their function in the oral cavity, the nose, the lower respiratory tract (LRT), and the gastrointestinal tract (GIT) is given together with an overview of the different routes of odorant excretion. Finally, perspectives for future research are discussed.
... During the ripening period, the terpene content of TH figs decreased markedly (46 ± 3.84-0%) while it remained constant (P < 0.05) in AZ (changing from 37.40 ± 1.37 to 37.06 ± 2.56%) and AV figs (changing from 41.11 ± 4.43 to 58.89 ± 10.40%) in AZ figs, which were characterized by high terpene contents. The major terpene molecule was linalool, which is recognized for its floral scents and has several biological properties (anti-inflammatory, antioxidant, and analgesic) (Aprotosoaie et al., 2014). This molecule is an important factor in the establishment of fig cultivar fingerprints, as all previous studies on fresh fig volatile molecules reported low terpene contents (Oliveira et al., 2010;Villalobos et al., 2018). ...
Article
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Aroma is one of the essential parameters that determine fruit quality. It is also an important feature of varietal characterization and so valuable for agro-biodiversity identification and preservation. In order to characterize changes in the aroma fingerprint through fig development, the main objective of the present research was to study the volatile organic compound (VOC) profiles of figs (Ficus carica L.) from three cultivars, Taamriwthe (TH), Azegzaw (AZ), and Averkane (AV), at three ripening stages (unripe, ripe, and fully ripe). Analyses was performed using Headspace Solid-phase Microextraction and gas chromatography coupled with mass spectrometry. Results revealed the presence of 29 compounds that were grouped into different chemical classes. Aldehydes comprised the most abundant VOCs identified in all the studied figs, while alcohols, ketones, and terpenes comprised the minor compounds found in TH, AZ, and AV figs, respectively. Different aroma descriptors were identified throughout the ripening stages of figs; fruity and green aromas were dominant in all cultivars, while a fatty aroma scarcely occurred in figs. A gallery plot representation demonstrated that certain VOCs differentiate the studied cultivars and the different ripening stages of figs. Principal component analysis findings demonstrated characteristic VOCs of distinct ripening stages and cultivars, those VOCs can be used as fingerprints to distinguish different cultivars and/or ripening stages.
... Other components, such as ethanol, pH, and pe-3-rut, were on the opposite side and correlated negatively with antioxidant capacity. Linalool has been reported to have similar antioxidative effects to vitamin E (Aprotosoaie, Hȃncianu, Costache, & Miron, 2014). Malic and acetic acids, ETs and free EA were located in the middle of the PLS model and showed little correlation with the antioxidant capacities in the fermented beverages. ...
Article
There is an increasing demand by consumers for low-alcohol beverages with enhanced flavors and potential health benefits. This study evaluated the effects of cultivars and fermentation with Saccharomyces cerevisiae or Torulaspora delbrueckii on the chemical composition, antioxidant capacity and sensory properties of low-alcohol strawberry beverages. Compared to juice, fermentation increased the contents of ethyl esters but reduced the contents of anthocyanins (∼60%) and organic acids (∼50%). The cultivar was the most important factor affecting the physicochemical characteristics and antioxidant capacity of fermented beverages. Among the cultivars, the beverages from the ‘Honeoye’ presented the highest sourness, opacity, redness and color density, total anthocyanins and phenolics, and antioxidant capacity but the lowest pungent aroma and ethanol content. Without added sugar, there was no significant difference in ethanol content between fermented beverages produced by S. cerevisiae and T. delbrueckii. Compared to S. cerevisiae, fermentation involving T. delbrueckii resulted in higher contents of anthocyanins and enhanced the color and flavor of the beverages. The results indicated that strawberry cultivars should be considered to produce fermented beverages with consistent physicochemical and sensory properties, and T. delbrueckii can be an alternative yeast for producing low-alcohol beverages from strawberries.
... Furthermore, several literature studies have underlined the biological activity of linalool, such as anti-inflammatory and antibacterial activity [54,55]. In addition, the hexane extract confirmed the presence of 1,8-cineole (2.47%), albeit at a much lower level than found in the headspace analysis. ...
Article
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The leaves of Rubus idaeus L., a by-product of the fruit food industry, are a known source of bioactive molecules, although the chemical composition has only been partially investigated. The main objective of this study was to examine the biological activities and the chemical composition of the extract of leaves of R. idaeus (RH), obtained by steam distillation (SD). The antioxidant capacity; the total phenolic content (TPC); the cytotoxic activity against tumor cell lines; and the antibacterial activity, in addition to the study of the chemical fingerprinting, carried out by Gas/Chromatography-Mass-Spectrometry (GC/MS) and Headspace (HS)-GC/MS, were established. The extract showed a strong antioxidant capacity and a modest antibacterial activity against two bacterial strains, as well as significant cytotoxic activity against tumor cell lines (Caco-2 and HL60) and being proliferative on healthy cells. Many of the GC-identified volatile molecules (1,8-cineol, β-linalool, geraniol,caryophyllene, τ-muurolol, citral, α-terpineol, 3- carene, α-terpinen-7-al, etc.) can explain most of the biological properties exhibited by the extract of R. idaeus L. The high biological activity of the RH and the high compatibility with the various matrices suggest good prospects for this extract, both in the food and cosmetic fields or in dietary supplements for improving human health.
... They are classified as monoterpenes and are renowned for their ability to fight against deleterious oxidative stress (Bialon et al., 2019, Batista et al., 2010, Peana et al., 2004. These compounds contain an unsaturated allyl moiety, which allows it to act as an antilipoperoxidant agent and predisposes to auto-oxidation potential, possibly increasing their antioxidant capacity and free radical scavenger properties (Aprotosoaie et al., 2014, Singh et al., 2013. ...
... Linalool (3,7-dimethyl-octa-1,6-dien-3-ol) is another important compound found in the essential oils of some plants, which is terpenic alcohol and belongs to the monoterpene family (Aprotosoaie et al., 2014;Dutra et al., 2016). Linalool is an aromatic compound used in the pharmaceutical, perfumery, cosmetics, and food industries (Lapczynski et al., 2008). ...
Article
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The aim of this research was to evaluate the effect of active polyethylene film (PE) containing linalool and thymol active components on the microbial shelf life of mozzarella cheese. PE films containing different concentrations of linalool or thymol (0%, 1%, 1.5% and 2%) were prepared. The antimicrobial properties of the films were examined, and mozzarella cheese was packed with these active films. The antimicrobial properties of packed samples during 30 days of storage were studied. The obtained results from film tests showed that by increasing the concentration of active agents (linalool and thymol) in PE films, the antimicrobial activities of film samples against Escherichia coli, Staphylococcus aureus, Listeria innocua, and Saccharomyces cervicea were increased. The cheese tests result demonstrated that mozzarella cheese packaging with PE films containing different concentrations of linalool and thymol leads to a decreased growth rate of molds and yeasts in cheeses. At the end of the storage period, the lowest number of molds and yeasts was for a sample packed in PE film containing 2% thymol, which increased from 1.00 to 1.21 Log CFU/g during the storage period. From E. coli and S. aureus contamination, the samples packed in active films were safe until the last day of storage (30th day), while the control sample was unacceptable at 17th day of storage. According to obtained results from this study, it was concluded that the addition of linalool and thymol active components to PE film had a positive effect on the extension of the mozzarella scheese shelf life.
... VOCs are emitted from a number of flowering plants. One of the most ubiquitous constituents is a terpene alcohol, linalool, which exists as one of two stereoisomers, (R)-(-)-linalool or (S)-(+)-linalool (Pereira et al. 2018;Aprotosoaie et al. 2014). Linalool is also emanated from the surfaces of human skin in association with the composition of the skin microbiome and may play a role in blood-host selection by anthropophilic mosquito species (Logan et al. 2008;Roodt et al. 2018). ...
Preprint
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Insects rely on olfactory receptors to detect and respond to diverse environmental chemical cues. Detection of semiochemicals by these receptors modulates insect behavior and has a direct impact on species fitness. Volatile organic compounds (VOCs) are released by animals and plants and can provide contextual cues that a blood meal host or nectar source is present. One such VOC is linalool, an enantiomeric monoterpene, that is emitted from plants and bacteria species. This compound exists in nature as one of two possible stereoisomers, (R)-(-)-linalool or (S)-(+)-linalool. In this study, we use a heterologous expression system to demonstrate differential responsiveness of a pair of Anopheline odorant receptors (Ors) to enantiomers of linalool. The mosquitoes Anopheles gambiae and Anopheles stephensi encode single copies of Or29 and Or53, which are expressed in the labella of An. gambiae. (S)-(+)-linalool activates Or29 orthologs with a higher potency than (R)-(-)-linalool, while the converse is observed for Or53 orthologs. The conservation of these receptors across a broad range of Anopheline species suggests they may function in the discrimination of linalool stereoisomers, thereby influencing the chemical ecology of mosquitoes. One potential application of this knowledge would be in the design of novel attractants or repellents to be used in integrated pest management practices.
... The acyclic monoterpene alcohol linalool (3,7-dimethyl-1,6-octadien-3-ol) is produced by the enzyme linalool synthase (LIS) [26,27], which is the source of the floral smells found in many different plants, flowers, and spices. Due to its flavorful and aromatic qualities, it is widely used in processed foods, drinks, fragrances, cosmetics, waxes, soaps, and household detergents [28] (Figure 1). ...
Article
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The medicinal herb coriander (Coriandrum sativum L.), with a high linalool (LIN) content, is widely recognized for its therapeutic benefits. As a novel report, the goals of this study were to determine how methyl jasmonate (MeJA) affects total phenolic content (TPC), LIN content, flavonoid content (TFC), and changes in gene expression involved in the linalool biosynthesis pathway (CsgTRPS and CsLINS). Our findings showed that, in comparison to the control samples, MeJA treatment substantially enhanced the TPC, LIN, and TFC content in both ecotypes. Additionally, for both Iranian coriander ecotypes, treatment-induced increases in CsɣTRPS and CsLINS expression were connected to LIN accumulation in all treatments. A 24 h treatment with 150 μM MeJA substantially increased the LIN content in the Mashhad and Zanjan ecotypes, which was between 1.48 and 1.69 times greater than that in untreated plants, according to gas chromatography–mass spectrometry (GC-MS) analysis. Our findings demonstrated that MeJA significantly affects the accumulation of LIN, TPC, and TFC in Iranian C. sativum treated with MeJA, which is likely the consequence of gene activation from the monoterpene biosynthesis pathway. Our discoveries have improved the understanding of the molecular mechanisms behind LIN synthesis in coriander plants.
Article
This article surveys a range of important platform and high value chemicals that may be considered primary and secondary 'xylochemicals'. A summary of identified xylochemical substances and their natural sources is provided in tabular form. In detail, this review is meant to provide useful assistance for the consideration of potential synthetic strategies using xylochemicals, new methodologies and the development of potentially sustainable, xylochemistry-based processes. It should support the transition from petroleum-based approaches and help to move towards more sustainability within the synthetic community. This feasible paradigm shift is demonstrated with the total synthesis of natural products and active pharmaceutical ingredients as well as the preparation of organic molecules suitable for potential industrial applications.
Article
Submerged cultures of the basidiomycota Cystostereum murrayi emit an intensive coconut-like, sweetish, and buttery smell. For identification of the key aroma compounds, an aroma dilution analysis using dynamic headspace was performed by adjusting the split ratio of the GC inlet system. Flavor dilution (FD) factors varied from 22 up to ≥218, whereby the largest class of compounds represented terpenoids, including two rare stereoisomers of 3,6-dimethyl-2,3,3a,4,5,7a-hexahydrobenzofuran (dill ether, ee ≥ 99.9). By means of nuclear magnetic resonance spectroscopy, the substances with the highest FD factors (29, 212, and 218) were identified as diastereomers of 3,6-dimethyl-3a,4,5,6,7,7a-hexayhydro-3H-1-benzofuran-2-one (dihydromenthofurolactone) and as its corresponding C3-unsaturated lactone. The latter two compounds have not been described for Cystostereum murrayi or for any other basidiomycota previously. Supplementation studies using 2-13C-d-glucose indicated that these lactones as well as the two stereoisomers of dill ether and other terpenoids were formed de novo by the fungus.
Chapter
The consumers’ demand for natural flavors and fragrances has resulted in a decrease in natural resources, making the development of cost-effective biotechnological processes that fulfill consumer needs. The extraction of these compounds from natural sources and chemical synthesis are the most common methods for their production. However, plant extraction has a number of drawbacks, including the low concentration of the desired product, seasonal variation, risk of plant diseases, and ecological problems. In fact, chemical synthesis still represents the cheaper technology for production of these compounds which are commonly labelled as “artificial” or “nature identical” decreasing their economic value. Biotechnological production emerges as an attractive alternative for its production since the products obtained are identified as “natural.” Yarrowia lipolytica is a nonconventional and strictly aerobic yeast with the Generally Recognized as Safe (GRAS) status which has different biotechnological applications due to its ability to consume a wide range of carbon sources and create a huge variety of metabolites with industrial interest. This yeast has been shown to be a robust cell for the biotechnological synthesis of compounds that can be used as additives in food industry, such as enzymes, sweeteners, biosurfactants, organic acids, and flavor and fragrance compounds. This chapter addresses the use of the nonconventional yeast Y. lipolytica as a microbial cell factory to produce flavor and aroma compounds, thereby providing a path towards a sustainable and efficient means of producing these compounds.
Article
Aquatic food products, including fish and crustaceans, are some of the most consumed foods globally and are highly prone to microbial contamination. Such products have been preserved using conventional processing techniques such as freezing, cold storage, modified atmospheric packaging (MAP) and vacuum packaging. However, these techniques have been used since decades and are not cost‐effective. Therefore, alternative sustainable strategies need to be explored. One viable option is the application of biopolymer‐based films and coatings loaded with active antimicrobial agents (peptides and essential oil components) for the preservation of aquatic food products. Nisin is the most widely used peptide for the development of antimicrobial coatings, while eugenol, carvacrol, and cinnamaldehyde are among the most popular essential oil compounds. Findings reveal that both peptides and essential oils, when applied in combination within a coating system, demonstrate robust antimicrobial activity, delayed lipid oxidation, and retain the overall quality of the aquatic food system.
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Abstract. Molecular chirality is a property of the nature and life, it is present everywhere and at all scales of magnitude. A fundamental aspect of molecules that is generally overlooked in scientific aromatherapy yet based on the use of the chemistry of functional groups. This update attempts to provide information on molecular stereochemistry in the composition of essential oils and its impact on their biological activities. Notions of stereochemistry are introduced and new light is shed with numerous examples on the main molecules making up EO. The importance of the enantiomeric profile of EOs is shown with a more precise evaluation of the consequences on their biological properties.
Article
Fried huajiao oil (FHO) samples prepared with red or green huajiao are widely applied in different Chinese cuisines due to their own aroma characteristics. To investigate their different aroma profiles, 2 red and 3 green FHOs were analyzed by quantitative descriptive sensory analysis (QDA) and gas chromatography–olfactometry/aroma intensity (GC–O/AI). QDA results showed a distinct difference among FHOs in terms of all sensory attributes. Thirty odorants with high OAVs and AIs were screened from 5 FHOs, among which β-myrcene, (E)-2-heptenal, limonene, α-terpineol and p-cymene were the major characteristic compounds of FHOs. In addition, through orthogonal partial least square discriminate analysis (OPLS-DA), linalool, linalyl acetate, and 1,8-cineole were considered as the volatile markers for classification of FHOs with red and green huajiao. Thereafter, aroma recombination and omission tests were performed to characterize the key aroma compounds of red and green FHOs.
Article
A novel undergraduate analytical chemistry experiment involving the identification and quantification of linalool in essential oils was developed. The experiment uses the internal standard method with headspace solid phase microextraction (SPME) and gas chromatography–mass spectrometry (GC-MS). This method is applicable to any linalool-containing essential oil sample but could be expanded to quantify other components. Initial experiments demonstrated the effectiveness of the internal standard method, with the regression analysis of the internal standard calibration curve having excellent linearity (R2 ≥ 0.98) compared to external standard calibration (R2 < 0.50). Several essential oils were tested, and the quantified concentrations were typically within 20% of the expected concentrations from manufacturer data or literature results. With >30% linalool, lavender oil was found to contain the highest concentration of linalool compared to all oils tested. This experiment introduces method development, SPME, GC-MS, and the internal standard method to sophomore and junior level chemistry students. This lab was used in analytical and organic chemistry classes but could be used with any students interested in quantitative instrumental analysis methods. In a survey of three separate groups of students who performed the lab, most students responded that the experiment provided them a better understanding of SPME, GC-MS, and the internal standard calibration method.
Article
To characterize the key odorants in ripe Capparis spinosa L. fruit (RCF) and to investigate changes in the odorants after storage, volatiles were captured by both solid-phase microextraction and solvent extraction combined with solvent-assisted flavor evaporation; a total of 22 aroma-active regions were detected in the isolates by gas chromatography–olfactometry. Of 19 odor-active compounds identified positively, 13 odorants were found in RCF for the first time; their flavor dilution factors ranging from 1 to 512 were measured by an aroma extract dilution assay. Eleven odorants were determined as the key odorants by stable isotope dilution analysis, odor activity value (OAV) calculation, and recombination experiments. To further investigate the changes in odorants after storage, their concentrations and OAVs were determined. The results showed that the number of key odorants did not change before and after storage, but the concentrations of octanoic acid, sotolon, and 3-methylbutanoic acid increased markedly.
Article
Homalomena aromatica is a herb of tremendous ethnomedicinal importance to various communities residing in northeast India. In this study, a high-performance thin-layer chromatography–based densitometric method was developed for identification, quantification and stability study of linalool. Mass spectrometry was hyphenated to HPTLC for streamlining the method. The stability of linalool was studied by analyzing the effect of acid, base, UV, sunlight, thermal stress and H2O2 on linalool. The chromatographic plates were developed to a height of 70 mm in toluene:ethyl acetate solvent system at a ratio of 9.5:0.5 and visualized with p-anisaldehyde reagent. The developed method was found to be precise, accurate and reproducible according to International Conference on Harmonization guidelines, and compact bands of linalool were observed at Rf of 0.351 ± 0.001. The content of linalool in the volatile oil of H. aromatica was found to be 58% v/v. By application of the hyphenated MS technique, linalool was identified at m/z 137, (M + H)+. It was observed that acidic pH has the highest effect on linalool with a percentage degradation of 65. The developed method can be used in the analysis and quality control of herbal materials and volatile oils containing linalool and quality control of rhizomes of H. aromatica.
Article
The present investigation was carried out for a comparative volatile study and aroma profiling of Hedychium flavescens. The headspace gas chromatography mass spectrometry (GC-MS) analysis of flowers (HS-F) and rhizome (HS-R); GC-MS analysis of flower essential oil (EO-F), flower absolute (AB-F) and rhizome essential oil (EO-R) revealed 27, 19, 19, 15 and 12 compounds which constitute 96.22%, 96.93% 97.43%, 86.79% and 97.62% composition, respectively. The identification results demonstrated that flowers and rhizome were rich in β-pinene, 1,8-cineol, linalool and E-β-caryohyllene components. β-Pinene was the most abundant component in HS-R (38.99%), EO-R (26.61%); linalool in HF-F (25.34%) and EO-F (25.99%) and ρ-vinyl-guaiacol in AB-F (32.19%), respectively. The aroma profile of H. flavescens was dominated with floral and jasmine (flowers); spicy, earthy and herbal (EO-F); floral and balsamic (AB-F); herbal, pungent, spicy and earthy (rhizome and EO-R) notes. Based on aroma profile, AB-F was evaluated as potential ingredient for perfume industry.
Article
Odorants are relatively small molecules which are easily taken up and distributed in the human body. Despite their relevance in everyday life, however, only a limited amount of evidence about their metabolism, pathways, and bioactivities in the human body exists. With this review, we aim to encourage future interdisciplinary research on the function and mechanisms of the biotransformation of odorants, involving different disciplines such as nutrition, medicine, biochemistry, chemistry, and sensory sciences. Starting with a general overview of the different ways of odorant uptake and enzymes involved in the metabolism of odorants, a more precise description of biotransformation processes and their function in the oral cavity, the nose, the lower respiratory tract (LRT), and the gastrointestinal tract (GIT) is given together with an overview of the different routes of odorant excretion. Finally, perspectives for future research are discussed.
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Abstract Alzheimer’s disease (AD) is a neurological disorder in which the neuronal degeneration is associated with inflammatory processes and oxidative stress. Since alpha-terpineol was shown to possess antioxidant and anti-inflammatory effects, the administration of this compound was studied on a rat model of AD. To create this model, Aβ1-42 was injected into the hippocampus of male Wistar rats. Generated AD models were divided into simple AD models and AD models in which short-term immobilization stress was added. Preventive and therapeutic (post-AD induction) effects of alpha-terpineol consumption (100 mg/Kg) were subsequently investigated in AD models, which were compared with control groups. Biochemical factors (superoxide dismutase and malondialdehyde), histological manifestations (amyloid plaques and neuron counts) and possible memory impairment (shuttle-box experiment) were investigated in all groups. For the in vitro experiment, alpha-terpineol effect was checked on Aβ1-42 fibril formation. In preventive and therapeutic modes, alpha-terpineol consumption could improve neurogenesis and long-term memory while reducing amyloid plaque counts and ameliorating biochemical factors (higher levels of superoxide dismutase and malondialdehyde and reduced levels of MDA). In vitro, shorter fibrillar structures were formed in the presence of alpha-terpineol, which indicates an anti-amyloid effect for this compound. In conclusion, alpha-terpineol significantly counteracted AD consequences.
Article
La cannelle de Ceylan est une épice très appréciée pour ses qualités alimentaires dont est extraite de l’huile essentielle issue des feuilles ou du bois. Elle contient un aldéhyde aromatique, le cinnamaldéhyde, puissant et caustique, ainsi qu’un phénol considéré comme moins caustique que les autres. Ces deux molécules ont des propriétés anti-infectieuses importantes et à large spectre.
Article
A novel extraction method of volatile aroma compounds (VACs) from walnut oil (WO) using monolithic material adsorption extraction (MMSE) was developed herein, and its efficiency was compared with the conventional extraction method based on solid-phase microextraction (SPME) combined with gas chromatography-olfactory-mass spectrometry (GC-O-MS). After protocol optimization of MMSE-RSC18, 77 volatile compounds (38 ones can be sniffed) were extracted from WO, thus having a better performance compared to SPME (56 volatile compounds, 35 ones can be sniffed). Subsequently, based on flavor dilution factors (FDs), odor activity values (OAVs), and recombination and omission experiments, key aroma-active compounds in WO were 1-octen-3-ol (OAV = 82.58), (E)-2-decenal (OAV = 4.10), linalool (OAV = 2.37), γ-dodecalactone (OAV = 2.30), 2-pentylfuran (OAV = 1.62), (E)-2-nonenal (OAV = 1.14) and pentanal (OAV = 1.04). Collectively, compared to HS-SPME, MMSE-RSC18 provided higher capture efficiency of VACs, enabling efficient extraction and analysis of sample aromas.
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Numerous studies have indicated the pharmacological properties of linalool, a volatile terpene alcohol found in many flowers and spice plants, including anti‐nociceptive, anti‐inflammatory, and neuroprotective activities. The aim of this study was to explore the mechanisms of neuroprotection provided by (±) linalool and its enantiomer, (R)‐(−) linalool against oxygen, and glucose deprivation/reoxygenation (OGD/R) in PC12 cells. PC12 cells were treated with (±) linalool and (R)‐(−) linalool before exposure to OGD/R condition. Cell viability, reactive oxygen species (ROS) production, malondialdehyde (MDA) level, DNA damage, and the levels of proteins related to apoptosis were evaluated using MTT, comet assay, and western blot analysis, respectively. IC50 values for the PC12 cells incubated with (±) linalool and (R)‐(−) linalool were 2700 and 2600 μM after 14 h, as well as 5440 and 3040 μM after 18 h, respectively. Survival of the ischemic cells pre‐incubated with (±) linalool and (R)‐(−) linalool (100 μM of both) increased compared to the cells subjected to the OGD/R alone (p < .001). ROS and MDA formation were also decreased following incubation with (±) linalool and (R)‐(−) linalool compared to the OGD/R group (p < .01). In the same way, pre‐treatment with (±) linalool and (R)‐(−) linalool significantly reduced OGD/R‐induced DNA injury compared to that seen in OGD/R group (p < .001). (±) Linalool and (R)‐(−) linalool also restored Bax/Bcl‐2 ratio and cleaved caspase‐3 and caspase‐9 (p < .001, p < .01) following ischemic injury. The neuroprotective effect of linalool against ischemic insult might be mediated by alleviation of oxidative stress and apoptosis. This study indicated, for the first time, that (±) linalool and its enantiomer, (R)‐(‐) linalool protected PC12 cells against injury induced by oxygen and glucose deprivation/reoxygenation (OGD/R) via the mitigation of oxidative stress and the downregulation of Bax/Bcl‐2, caspase‐3 and caspase‐9, resulting in decreased apoptotic cell death.
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Thymus vulgaris Linn. is a medicinal and culinary herb from the Southern European region known for its anti-infective, cardioprotective, gastroprotective, anti-inflammatory, and immunomodulatory activities since the Egyptian era. The reported pharmacological activities of T. vulgaris L. include antibacterial, antioxidant, anti-inflammatory, antiviral, and anti-cancerous activities. In this review, a comprehensive approach is put forth to scrutinize and report the available data on phytochemistry, ethnopharmacology, pharmacology, and toxicology of the plant. The different extracts and essential oil obtained from the plant have been assessed and reported to treat ailments like microbial infections, inflammation, non-communicable diseases like cancer, and sexually transmitted diseases like HIV-1 and Herpes. The literature review has also indicated the use of volatile oils, phenolic acids, terpenoids, flavonoids, saponins, steroids, tannins, alkaloids, and polysaccharides in pharmacotherapy. Applications of these compounds including antidiabetic, anti-Alzheimer's, cardio, neuro and hepatoprotective, anti-osteoporosis, sedative, immunomodulatory, antioxidant, anti-tyrosinase, antispasmodic, antinociceptive, gastroprotective, anticonvulsant, antihypertensive, antidepressant, anti-amnesia, and anti-helminthic activities have been mentioned. Further, based on research gaps, recommendations have been provided to evaluate T. vulgaris L. systematically to develop plant-based drugs, nutraceuticals, and to evaluate their clinical efficiency and safety.
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Cananga odorata is a tropical tree from the Annonaceae family, native of Indonesia. Only the forma genuina can be called ylang-ylang. Nowadays, it is mainly cultivated in the Indian Ocean Islands in order to extract the ylang-ylang essential oil for the cosmetic industry. Ylang-ylang develops on many types of soils, under high temperatures and average precipitations of 1,500 mm per year. The pollarding, the maintenance, the elimination of water sprouts and the weeding must be performed to insure a high flower yield and facilitate harvesting. Flower harvest takes place all year long but flowers and essential oils yields are higher during the dry season. Mature and fresh flowers are then distillated and fractionated to obtain essential oil. Generated incomes are important for the economy of the three main producers: Union of Comoros, Madagascar and Mayotte. However, this plant is still poorly known despite its great economic value. This lack of information is a bottleneck for solving the ylang-ylang industry problems which endanger it. Moreover, there is no improvement program of this plant despite the high added value of its essential oil, probably due to the fact that its reproduction biology is far from being known. A thorough study of the plant and its essential oil could generate information necessary to solve the aforementioned problems, maintain and develop the ylang-ylang industry.
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The essential oils of Romanian coriander fruits (cultivar "Sandra") were obtained by hydrodistillation and analyzed by means of GC and GC-MS. Sixty compounds were identified in the total essential oils. Monoterpenes were the most dominant class of compounds, with linalool (48.4-54.3%) being the major component. Other significant compounds were γ-terpinene (9.2-12.1%), α-pinene (5.5-9.3%) and limonene (4.7- 6.3%).
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Pollination is an essential biological process in higher plant reproduction that involves the transfer of pollen to the female sexual organs of flowers or cones. It plays a critical role in the reproductive success and evolution of most plant species by allowing plants to share genetic material from other members of the same or closely-related species, thus increasing genetic diversity. In many cases, non-plant organisms are involved in carrying out this cross-pollination, including insects, bats, mammals, and birds. In order to attract such pollinators, plants have evolved the ability to produce a mind-boggling array of volatile compounds that have also found abundant use for humans when collected as essential oils. In this review, we focus on the role of essential oil compounds that are produced by flowers as chemical attractants used to draw in their often highly- specific pollinators. We examine in some detail various questions behind the biology of floral scent, including how these compounds are produced in flowers, how they are detected by potential pollinators, and how biotechnology can be used to alter their activity.
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Headspace hanging drop liquid phase micro-extraction (HS-HD-LPME) is studied as a novel solvent-based sample pretreatment method for floral volatile aroma compounds. This paper reports on application of the HSHD-LPME combined with GC-MS for the analysis of linalool component emitted from evening primrose flowers. The effect of several variables on the method performance was investigated. Additionally, the separation of enantiomers on a cyclodextrin capillary column was performed to identify chirality of (-)-linalool component. Since the unsurpassed volume of a few micro-liters of solvent is used, there is minimal waste or exposure to toxic organic solvents. This method enables to combine extraction, enrichment, clean-up, and sample introduction into a single step prior to the chromatographic process.
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Abstract: The essential oil from the aerial parts of Salvia sclarea L., growing wild in Tajikistan, were obtained by hydrodistillation and analyzed by gas chromatography – mass spectrometry. A total of 59 compounds were identified representing 94.2% of total oil composition. Major components of the essential oil were linalyl acetate (39.2%), linalool (12.5%), germacrene D (11.4%), �-terpineol (5.5%), geranyl acetate (3.5%), and (E)-caryophyllene (2.4%). The chemical composition, the large concentrations of linalool and linalyl acetate, and a cluster analysis based on principal components; of Tajik S. sclarea oil reveal it to be comparable to commercial S. sclarea oils.
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The essential oils of two varieties of Camphor tree (Cinnamomum camphora Nees & Eberm, Lauraceae), known as Hon-Sho and Ho-Sho cultivated in experimental stands in Southern Brazil were studied. The essential oils were obtained from the leaves and twigs of young plants by hydrodistillation. The identification of the components was performed using GC, GC/MS and retention indexes on methyl silicone and carbowax phases. The main components identified were linalool in the Ho-Sho and camphor in the Hon-Sho.
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The quality assessment of bergamot essential oils was established employing the gas chromatography-combustion- isotope ratio mass spectrometer (GC-C-IRMS) technique. An authenticity range was obtained investigating the carbon stable isotope ratio of genuine Italian bergamot essential oils (harvest period 2008–2009), in order to compare the GC-C-IRMS data of several industrial, commercial and foreign bergamot essential oil samples. Moreover, with the aim to test the efficiency and the sensibility of IRMS device, self-adulterated in laboratory bergamot oil samples were analyzed. The data were compared with those achieved by conventional enantioselective gas chromatography (Es-GC) and high resolution gas chromatography (GC-FID). Results of this work indicated that GC-C-IRMS was able not only to detect the presence of adulterants in the samples, but also to discriminate the bergamot oil samples according to their geographic provenance and the nature of the adulterants added.
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Gas Chromatography–Combustion-Isotope Ratio Mass Spectrometry (GC–C-IRMS) can provide information useful to discriminate among essential oils of different geographical origin and to reveal frauds on essential oils by addition of synthetic or natural compounds from different botanical origin. The present work reports the combination of information obtained by GC–C-IRMS, Enantioselective Gas Chromatography (Es-GC), high resolution Gas Chromatography (GC-FID) and spectrophotometry (CD values). All these techniques represent useful tools to evaluate the authenticity control on lemon essential oils. The GC–C-IRMS was applied to determine the authenticity range of carbon stable isotope ratios in genuine Italian lemon essential oils industrially cold-pressed. Several commercial samples were evaluated to assess their genuineness. The IRMS results are discussed in function of the values also obtained by GC-FID, es-GC and CD values. Stable isotope ratio analysis, by GC–C-IRMS, proved to be useful to detect the presence of sophistications in lemon essential oils, even when other techniques of analysis fail. However for subtle sophistications (e.g. addition of distilled lemon oil) quality assessment must be performed by the auxiliary of more than one technique.
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There is still the need for efficacious therapies for pain. In the search for new therapeutic options, plants are a major source of novel biomolecules. Monoterpenes constitute 90% of essential oils, and there is a growing interest in understanding the mechanisms underlying their pharmacological activity. This systematic review reports what is so far known about the analgesic activity of monoterpenes and also provides an overview of their mechanisms of action. The search terms analgesia, anti-inflammatory, anaesthetic and antioxidant were used to retrieve English language articles in SCOPUS, PUBMED and EMBASE published between 1990 and 2012. Forty-five papers were found concerning the potential analgesic activity of 27 monoterpenes. The data reviewed here suggest these compounds are possible candidates for the treatment of painful conditions. Copyright © 2012 John Wiley & Sons, Ltd.
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Background: Linalool is a common fragrance terpene that, in pure form, is not allergenic or is a very weak allergen. However, linalool autoxidizes on air exposure, and the oxidation products can cause contact allergy. In a Swedish study, oxidized linalool 6.0% in petrolatum (pet.) gave 5% positive patch test reactions in 2500 dermatitis patients. Objectives: To investigate whether oxidized linalool 6%, with a stable concentration of the main haptens, the linalool hydroperoxides (Lin-OOHs) in pet., could be a useful tool for the detection of contact allergy in an international setting. Methods. Oxidized linalool 6.0% (Lin-OOHs 1%) pet. was tested in 2900 consecutive dermatitis patients in Denmark, the United Kingdom, Singapore, Spain, Sweden, and Australia. Results: Overall, 6.9% (range 3-13%) of the patients showed positive patch test reactions to oxidized linalool. Doubtful reactions were found in 9.2% of the patients (range 0-36%). Few irritant reactions were seen. Conclusions: In an international setting, oxidized linalool has been shown to be a common allergen. Oxidized linalool 6.0% (Lin-OOHs 1%) pet. is a useful, standardized and stable tool for the detection of contact allergy in dermatitis patients. Many patients showing positive patch test reactions to oxidized linalool would not have been informed of their fragrance allergy if this specific test had not been performed.
Article
The geographical origin of Citrus fruits is localised in a large region of Southeast Asia comprising southern China, India, Indo-China, Indonesia and the Malay Archipelago. Very slowly, and thanks mainly to nomads, merchants, conquest wars and explorers, Citrus fruits became known in Africa and Europe. Several witnesses to the presence of Citrus fruits during Alexander the Great’s reign and the Greek and Roman periods may be found in literature, sculptures, mosaics and so on. However, it was under Arab rule throughout most of the Mediterranean basin, in a long period between the end of the first and the beginning of the second millennium, that the diffusion as well as the first cultivation of Citrus plants occurred (Webber 1967). Indeed, in this period an Arab botanist, Al-Beithâr, reported, in his treatise “Dictionary of the Simple Remedies” (1200), the first technical description of essential oil extraction from citron fruits (Calabrese 1990). However, for many centuries the cultivation of Citrus plants was limited to their ornamental use. Their industrial exploitation started in Sicily between 1500 and 1600 precisely with the extraction of essential oil from lemon fruits. The process entailed the removal of the peel from the pulp, which was considered a waste product, and only successively was the pulp used industrially to prepare the juice, called “agro”, exclusively for the preparation of calcium citrate (Safina 1984).
Article
Get a good start in flavor and fragrance chemistry!. This book presents a survey of those natural and synthetic fragrance and flavor materials which are commercially available, produced and used on a relatively large scale and which are important ingredients for the creation of fragrance and flavor compositions because of their specific sensory characteristics, e.g., smell, taste. It provides information on their properties, methods employed in their manufacture, and their areas of application. This is the 5th edition of the classic "Bauer-Garbe". '...The excellent and concise introduction to this unique industry is followed by extensive information on nearly 500 of the most used fragrance and flavor compounds. Names, molecular formula, physical data, odor and flavor descriptions, uses, and a number of processes for the larger scale production of chemicals are all included. Successive chapters deal with essential oils, animal secretions, quality control, toxicology and literature. The formula, name and CAS registry number index are an invaluable and timely addition.' - Parfumer and Flavorist. '...Data that would normally have to be selected from many different books are available in one source with this book...with over 800 citations throughout the text, this is a nearly inexhaustible source of information.' - Euromaterials.
Chapter
This chapter looks at the genus Lavandula (lavender), a plant for which 32 species have been described. The chapter describes the phytochemistry of the genus and the chemistry of the essential oils of different lavenders. Production methods for lavender are discussed including production of lavender oil and organic lavender oil and also lavenders grown for drying and pot pourri. The uses of lavender in the food processing, perfumery and paramedical spheres are covered, together with the functional properties, pharmacological, physiological, psychological and antimicrobial effects, and toxicity. The chapter concludes with coverage of quality issues and adulteration.
Article
Contents and enantiomeric distributions of linalool (3,7-dimethyl-1,6-octadien-3-ol) were investigated in raw and roasted cocoa beans (seeds of Theobroma cacao) of defined origin as well as in commercial products, such as cocoa powders or chocolates. The stereodifferentiation of linalool was achieved by enantioselective multidimensional gas chromatography using heptakis (2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin as chiral stationary phase. Simultaneous steam distillation–extraction at pH 7 allowed sample preparation without racemization of linalool. Cocoa beans contain linalool primarily as (S)-enantiomer. Model experiments and analyses of commercial products such as cocoa powders and chocolates revealed that technological procedures employed in the manufacturing of cocoa products do not result in significant changes of the original enantiomeric distribution of linalool.
Article
A comparison between the chemical composition of basil oils produced by distillation from fresh or dried leaves or extraction (using CH2Cl2 at 25°C) from frozen or dried leaves was made. Although 19 compounds were characterized by GC/MS, the linalool, estragole, and eugenol contents were found to vary from 26.6–50.0%, 0.4–45.1%, and 2.5–27.0%, respectively.
Article
Chirality evaluation is proved to be an efficient tool for the authenticity control of neroli, petitgrain and bergamot oils by enantioselective multidimensional gas chromatography (enantio-MDGC). The simultaneous stereochemical analysis of the main compounds linalool, linalyl acetate, α-terpineol using heptakis-(2,3-di-o-acetyl-6-o-tert.-butyldimethyl-silyl)-β-cyclodextrin as the chiral main column is described. α-Pinene, β-pinene, limonene, terpinen-4-ol and nerolidol are simultaneously stereoanalyzed with heptakis-(2,3-di-o-methyl-6-o-tert.-butyldimethylsi-lyl)-β-cyclodextrin. Characteristic authenticity profiles of neroli, petitgrain, bergamot and other citrus oils are deduced by enantioselective cGC as well as isotope ratio mass spectrometry (IRMS), online coupled with capillary gas chromatography. Enantiomeric ratios, isotopic data as well as quantification of bergamot oil compounds are evaluated integrally. Scope and limitations of the techniques are discussed.
Article
This chapter focuses on the work that explores the chemistry and metabolism of skin sensitizers. The chapter also includes some dermatological aspects on the topic showing that contact with skin sensitizers is an important problem from both a society point of view and from an individual perspective. Clinically relevant examples illustrate common hapten–protein interactions. Allergic contact dermatitis (ACD) is the clinical result of skin contact with chemicals to which an individual is sensitized. A wide range of chemicals are known to cause skin sensitization after prolonged or repeated contact and ACD is an important occupational and consumer health problem. An increasing number of structure activity relationship (SAR) and quantitative structure activity relationship (QSAR) studies of potential relationships between physicochemical properties and contact allergenic effect have been published. The ultimate challenge for developing non-animal test methods is applyied in the mechanistic understanding of contact allergy and ACD to the design of predictive in vitro alternative test methods. Because environmental exposure is of major importance for the development of ACD, regulatory work and legislation to decrease or forbid exposure of potent contact allergens are important.
Article
This chapter discusses the relationship between essential oil analysis and gas chromatography (GC). GC, particularly when combined with mass spectrometry (MS), contributes to the development of the science of essential oils and fragrances in the areas of phytochemistry, chemotaxonomy, olfactory research, biochemistry, plant-insect research, the search for new sources of odoriferous compounds for industry, and quality control. Essential oils are analyzed to determine the qualitative and/or quantitative composition of a product; control the quality and authenticity of the product; and detect the presence of adulteration or contamination. One of the major objectives of plant extract analysis by 2D gas chromatography (GCxGC) is to determine a sample composition. Characterization of volatile plant extracts relies heavily on the retention index-based identification of the separated components, and this is usually supported by MS. A simple procedure that permits the direct method translation of retention times in 2D for GCxGC–FID and GCxGC–ToF MS analyses is described in the chapter. The chapter discusses the use of retention indices in the GCxGC analyses of essential oils and fragrance compounds. Retention indices are extremely important in identification strategies of essential oil and fragrance components because mass spectral data alone are generally insufficient to provide positive identification.
Article
The elution profiles of several essential oils of the Myrtaceae family were acquired using a single enantioselective stationary phase column. These chromatograms were compared with those obtained by using a two-column coupled system, which comprised a low-polarity stationary phase column connected to the terminal end of the enantioselective column. The enantiomeric distributions of β-pinene, sabinene, -phellandrene, limonene, trans- and cis-sabinene hydrate, linalool, terpinen-4-ol and -terpineol were determined. The use of a two-column coupled system is demonstrated to be useful for improving the resolution of target (chiral) compounds from otherwise interfering matrix components. Copyright © 2004 John Wiley & Sons, Ltd.
Article
The sedative properties of linalool were examined using the optically active linalools, (R)-(−)-, (S)-(+)- and (RS)-(±)-forms. (R)-(−)-linalool with specific rotation of [α]D= −15.1° was isolated by repeated flash column chromatography from lavender oil, while (S)-(−)-linalool with [α]D= +17.4° and (RS)-(±)-linalool with [α]D=0° 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. The effect of (RS)-(±)-linalool in our experiments, which was quite similar to that of linalool, with much more favorable impressions accompanied by a tendency to a greater decrease of the beta wave after hearing environmental sound after, rather than before work, appeared to be identical to that observed for (R)-(−)-linalool. The feature was just the reverse in the case of (S)-(+)-linalool.
Article
Chemical composition, antioxidant and antimicrobial activities of the essential oils from aerial parts of basil (Ocimum basilicum L.) as affected by four seasonal, namely summer, autumn, winter and spring growing variation were investigated. The hydro-distilled essential oils content ranged from 0.5% to 0.8%, the maximum amounts were observed in winter while minimum in summer. The essential oils consisted of linalool as the most abundant component (56.7-60.6%), followed by epi-α-cadinol (8.6-11.4%), α-bergamotene (7.4-9.2%) and γ-cadinene (3.2-5.4%). Samples collected in winter were found to be richer in oxygenated monoterpenes (68.9%), while those of summer were higher in sesquiterpene hydrocarbons (24.3%). The contents of most of the chemical constituents varied significantly (p<0.05) with different seasons. The essential oils investigated, exhibited good antioxidant activity as measurements by DPPH free radical-scavenging ability, bleaching β-carotene in linoleic acid system and inhibition of linoleic acid oxidation. Evaluation of antimicrobial activity of the essential oils and linalool, the most abundant component, against bacterial strains: Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Pasteurella multocida and pathogenic fungi Aspergillus niger, Mucor mucedo, Fusarium solani, Botryodiplodia theobromae, Rhizopus solani was assessed by disc diffusion method and measurement of determination of minimum inhibitory concentration. The results of antimicrobial assays indicated that all the tested microorganisms were affected. Both the antioxidant and antimicrobial activities of the oils varied significantly (p<0.05), as seasons changed. Copyright © 2007 Elsevier Ltd. All rights reserved.
Article
Eighty-two samples of Aniba rosaeodora Ducke were collected from ten localities in French Guiana. Essential oils were extracted from different parts of the tree (trunk wood, branch wood, roots, leaves) and analyzed. Yield measurements were performed by hydrodistillation; total linalool content and percentages of (-)-linalool or (+)-linalool were obtained by gas chromatography. Variations in essential oil yield were correlated with various parameters such as part of the tree, age of the tree, season, phenological status and geographic origin. Oil yields from wood samples (trunk, branch, shoot) ranged from 0.4–3.2%, while yields from roots and leaves varied very little with an average of 0.15% and 0.43%, respectively. In young trees, wood yield was 1.6%, higher than in older trees (1.3%). Collection time had no obvious influence on wood and leaf yields. Nevertheless, fruit-bearing trees gave a higher yield than fruitless ones. For a given tree, a decreasing yield gradient was observed from trunk wood to branches, smaller branches, and leaves. Linalool percentage in oil ranged from 73–99%. All trunk wood oils contained a percentage of (-)-linalool close to 100%, except for two trees from Paracou station where a low proportion of (+)-linalool was present. Oils from small branches contained from 5–28% of (+)-linalool. All leaf oils showed a high percentage (78–89%) of (+)-linalool. The linalool form in oil from shoot, bark and root samples was purely (-)-linalool. Measures performed on different parts of the same tree showed that the linalool from trunk wood and thick branches was purely (-)-linalool, whereas the proportion of (+)-linalool increased with the thinness of the branches and reached 85% in leaves.
Article
A headspace solid-phase microextraction (HS-SPME) method coupled to gas chromatography–ion trap mass spectrometry (GC–ITMS) has been developed and applied for profiling of volatile compounds released from five Ocimum basilicum L. cultivars grown under both organic and conventional conditions. Comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry (GC×GC–TOFMS) was employed for confirmation of identity of volatiles extracted from the basil headspace by SPME. Linalool, methyl chavicol, eugenol, bergamotene, and methyl cinnamate were the dominant volatile components, the relative content of which was found to enable differentiating between the cultivars examined. The relative content of some sesquiterpenes, hydrocarbons benzenoid compounds, and monoterpene hydrocarbons was lower in dried and frozen leaves as compared to fresh basil leaves. A sensory analysis of the all examined samples proved the differences between evaluated cultivars.
Article
Aim: The inhalation of Lavandula angustifolia (lavender) essential oil has anxiolytic-like effects in animal models and humans, but its mechanism of action is still not fully understood. The inhalation of essential oils can induce anxiolytic effects through the central nervous system (e.g., lung absorption and bloodstream transport) or stimulation of the olfactory system and secondary activation of brain regions. Thus, the main objective of the present study was to evaluate whether the perception of lavender essential oil aroma, when inhaled, is necessary to obtain its anxiolytic-like effects in mice tested in the marble-burying test. Main methods: Anosmia was induced by irrigating the nasal cavity with zinc gluconate+zinc acetate so that the mice could not detect odors in the olfactory discrimination test. The marble-burying test was used to evaluate the anxiolytic-like effects of inhaled lavender essential oil. Key findings: Anosmia did not interfere with the anxiolytic-like effect of lavender essential oil inhalation in the marble-burying test at concentrations of 2.5% (number of marbles buried: vehicle, 4.7±1.0; zinc, 6.2±2.2; p>0.10) and 5% (number of marbles buried: vehicle, 3.4±0.8; zinc, 4.3±0.9; p>0.10). Lavender essential oil at a concentration of 0.5% was ineffective. Significance: These results suggest that olfactory system activation is unlikely to participate in the anxiolytic-like effect of lavender essential oil inhalation.
Article
Ethnopharmacological relevance: Lavandula angustifolia (lavender) inhalation has been used in folk medicine for the treatment of anxiety, and clinical and animal studies have corroborated its anxiolytic effect, although its mechanism of action is still not fully understood. Aims of the study: The objective of the present study was to determine whether the GABAA/benzodiazepine complex or serotonin neurotransmission mediates the anxiolytic-like effect of lavender essential oil. Materials and methods: Male Swiss mice were subjected to the marble-burying test after being exposed to the aroma of lavender essential oil (1-5%), amyl acetate (5%; used as a behaviorally neutral odor), or distilled water for 15 min via inhalation. Additionally, the effect of 5% lavender essential oil was also evaluated in mice subjected to the elevated plus maze. GABAA/benzodiazepine mediation was evaluated by pretreating the mice with the GABAA receptor antagonist picrotoxin before the marble burying test and [(3)H]flunitrazepam binding to the benzodiazepine site on the GABAA receptor. Serotonergic mediation was studied by pretreating the mice with O-methyl-[3H]-N-(2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl)-N-(2-pyridinyl) cyclohexanecarboxamide trihydrochloride (WAY100635), a serotonin 5-HT1A receptor antagonist before the marble burying test. We also evaluated changes in the pharmacologically induced serotonin syndrome and the effects of combined administration of subeffective doses of lavender essential oil and the 5-HT1A receptor agonist 8-hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT). Results: Lavender essential oil (1-5%) decreased the number of marbles buried compared with the control and amyl acetate groups. In the elevated plus maze, 5% lavender essential oil inhalation increased the percentage of time spent on and number of entries into the open arms compared with controls. No effect was seen in the number of closed arm entries or number of beam interruptions in the automated activity chamber. Pretreatment with the GABAA receptor antagonist picrotoxin (0.5mg/kg) did not modify the behavioral effect of 5% lavender essential oil in the marble-burying test. Lavender essential oil also did not alter [(3)H]flunitrazepam binding to the benzodiazepine site on the GABAA receptor. Pretreatment with the serotonin 5-HT1A receptor antagonist WAY100635 (3mg/kg) blocked the anxiolytic-like effect of lavender essential oil and the 5-HT1A receptor agonist 8-OH-DPAT (3mg/kg). A combination of ineffective doses of 8-OH-DPAT (0.5mg/kg) and lavender essential oil (0.1%) reduced the number of marbles buried. Finally, 5% lavender essential oil attenuated the serotonin syndrome induced by 40 mg/kg fluoxetine plus 80 mg/kg 5-hydroxytryptophan. Conclusions: These results indicate an important role for the serotonergic system in the anxiolytic-like effect of lavender essential oil.
Article
Background: Inflammation, characterized by redness, swelling, pain and a sensation of heat, is one of the body's self-defense systems. Although the inflammation response has an important role in host survival, it also leads to chronic inflammatory diseases. Linalool is a natural compound of the essential oils in several aromatic plants species. It possesses anti-inflammatory, antinociceptive, and other bioactive properties. In the present study, we investigated the protective effects of linalool on inflammation in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells and an LPS-induced in vivo lung injury model. Methods: We evaluated the effects of linalool on LPS-induced production of inflammatory mediators in Raw 264.7 murine macrophages by enzyme-linked immunosorbent assay and Western blot. To confirm the anti-inflammatory activity of linalool in vivo, we induced an acute lung injury in an LPS-induced mouse model. Results: Linalool attenuated the production of LPS-induced tumor necrosis-α and interleukin-6 both in vitro and in vivo. Furthermore, phosphorylation of IκBα protein, p38, c-Jun terminal kinase, and extracellular signal-regulated kinase in LPS-stimulated RAW 264.7 cells was blocked by linalool. Our in vivo study also found that linalool attenuated lung histopathologic changes in mouse models. Conclusions: The results suggest that linalool inhibits inflammation both in vitro and in vivo, and may be a potential therapeutic candidate for the treatment of inflammatory diseases.
Article
As malignant neoplasm is a major public health problem, there is a need for the development of a novel modulator that enhances antitumor activity and reduces adverse reactions to antitumor agents. In this study, the effects of some volatile oil components in Humulus lupulus on doxorubicin (DOX) permeability in tumor cells and DOX-induced antitumor activity were examined. In vitro, DOX levels in tumor cells by combined linalool as its component significantly increased in the DOX influx system, and the increased effect by linalool on DOX cytotoxicity was shown. In vivo, the combination of DOX with linalool significantly decreased tumor weight compared with that of DOX alone treated group. The promotion of DOX influx level by combined linalool did not depend on energy, whereas it was suppressed by the absence of Na+. This promoting effect was suppressed by the presence of S-(4-nitrobenzyl)-6-thioinosine and inhibited dependently on phlorizin concentration. It is considered that linalool promoted DOX influx in tumor cells because of its action on DOX transport through concentrative Na+-dependent nucleoside transporter 3, which increased DOX concentration in tumor cells and thus enhanced the antitumor activity of DOX. Therefore, linalool as a food component is anticipated to be an effective DOX modulator.