Showing papers in "Flavour and Fragrance Journal in 2017"
TL;DR: In this article, a fundamental review of the impact protein-flavour interactions on flavour retention and release with a special emphasis on plant protein materials is provided, with a focus on how they influence flavour perception.
Abstract: As the loss of free volatile compounds in aqueous protein systems is known to greatly influence the quality, and therefore the consumer acceptability, of protein-containing foods, examination of the ability of different proteins to react with volatile flavour compounds as well as the nature of the interaction are of great interest to flavour chemists. It is generally believed that the affinity of flavour to proteins is a multi-factor function related to protein source, protein conformation and stereochemistry of the flavour compound. However, the nature of protein-flavour interactions has not been explicit. Less focus has been put on plant-based proteins in comparison to animal proteins. With an increase in the use of plant-based proteins in food systems, this article provides a fundamental review of the impact protein-flavour interactions on flavour retention and release with a special emphasis on plant protein materials. Flavour-food matrix interactions have been examined with a focus on how they influence flavour perception. Current knowledge on methodologies involved in protein-flavour binding studies, binding mechanisms and factors affecting the interaction have been discussed. The implication of protein-flavour interaction on protein functionality specifically protein thermal gelation properties has also been considered. Copyright © 2016 John Wiley & Sons, Ltd.
58 citations
TL;DR: In this paper, four types of Chinese congou black tea were analyzed by quantitative descriptive sensory analysis, gas chromatography-mass spectrometry (GC-MS) and gas chromation-olfactometry (GC O).
Abstract: To characterise the volatile aroma compositions of Chinese congou black teas, four types were analysed by quantitative descriptive sensory analysis, gas chromatography–mass spectrometry (GC–MS) and gas chromatography–olfactometry (GC–O). The aroma of Chinese congou black tea was described using six sensory terms: ‘Roasted’, ‘Sweet’, ‘Malty’, ‘Green grassy’, ‘Floral’ and ‘Woody’. A total of 64 compounds including alcohols (20), aldehydes (12), ketones (12), esters and lactones (9), pyrazines (7) and other compounds (4) were identified and quantified in four Chinese black tea samples. The highest amount of volatile aroma compounds was found in Tanyang congou black tea (TY) (29.8 mg/kg), followed by Dianhong congou black tea (DH) (29.4 mg/kg), Keemun congou black tea (KM) (24.1 mg/kg) and Yixing congou black tea (YH) (23.6 mg/kg). Through aroma extract dilution analysis (AEDA) on the black tea extract, the flavour dilution factor (FD factor) ranged from 41 to 46. Trans-linalool oxide in DH, geraniol in TY, DH and KM were identified with the highest flavour dilution (FD = 4096) factors. The relationship between tea samples, sensory attributes and aroma-active compounds was modelled by partial least squares regression (PLSR), and the PLSR analysis revealed that pentanal showed a significant and positive correlation with the ‘Malty’ attribute, (Z)-3-hexen-1-ol showed a significant and negative correlation with the ‘Green grassy’ attribute, 2-methylpyrazine showed a significant and negative correlation with the ‘Floral’ attribute, cis-linalool oxide, trans-linalool oxide and nerolidol showed a significant and positive correlation with the ‘Woody’ attribute, cis-6-nonen-1-ol and 2-methylpyrazine showed a significant and negative correlation with the ’Woody‘ attribute.
53 citations
TL;DR: In this article, the essential oil extracted from Smyrnium olusatrum (AEO) was formulated as microemulsions known for their thermodynamic stability and easiness of preparation.
Abstract: Smyrnium olusatrum L. is a horticultural crop cultivated during the Roman age for culinary and curative uses. The essential oil extracted from this plant (AEO) is rich in bioactive constituents such as isofuranodiene and germacrone. Several previous studies revealed that AEO and its isolated components possess interesting therapeutic features, such as antiproliferative, neuritogenic, hepatoprotective and antioxidant properties. Nevertheless, AEO has stability problems because of the high concentration of its main components. This issue makes AEO very difficult to handle and use. Thus, AEO was formulated as microemulsions known for their thermodynamic stability and easiness of preparation. AEO was hydrodistilled from inflorescences of S. olusatrum and its composition determined by different chromatographic methods. The microemulsions were developed using a central composite design and their activity tested using the MTT assay. The present study demonstrated the possibility to formulate stable AEO microemulsions where the crystallization of isofuranodiene is avoided, and the AEO biological activity is maintained. Copyright © 2016 John Wiley & Sons, Ltd.
29 citations
TL;DR: In this article, the authors investigated the effect of room scents on attention, anxiety and mood in a large group of healthy people during exposure to various pleasant odours compared with the same situation in a non-odourous environment.
Abstract: With a special focus on the potential benefits of widely used room scents, the aim of the present blinded study was to investigate attention, anxiety and mood in a large group of healthy people during exposure to various pleasant odours compared with the same situation in a non-odourous environment. A psychological test battery (d2 test of attention, State-Trait-Anxiety-Inventory, Beck Depression Inventory and Multidimensional Mood State Questionnaire) was applied to 200 normosmic subjects, placed in rooms with four different room fragrance conditions (rose odour; grapefruit odour; a combination of orange, lime and lemon odour; and a odourless control). After exposure, subjects were asked to rate occurrence and severity of heart problems (tachycardia/palpitations), headaches or breathing problems. Results revealed no significant effects of room fragrance on attention, anxiety and mood. Exposure to odours seemed to affect men and women differentially with men presenting unfavourable results in rose-fragranced rooms whereas they seemed positively affected by the smell of grapefruit. However, these effects could only be observed when no corrections for multiple comparisons were applied. Exposure to the fragrances was not associated with a higher incidence of physical symptoms. These results suggest that the grapefruit odour may be a more suitable room fragrance for mixed-gender groups than rose odour to reduce anxiety and to improve attention and mood. Copyright © 2016 John Wiley & Sons, Ltd.
26 citations
23 citations
TL;DR: In this article, a method based on headspace solid-phase microextraction and gas chromatography coupled to isotope ratio mass spectrometry was proposed to determine the carbon isotope ratios (δ13C) of vanillin extracted from vanilla pods, commercial flavoured foodstuff and in vanillin samples of different origins.
Abstract: Vanillin can be obtained by extraction from the pods of Vanilla (organic vanillin), by synthetic pathways using different precursors (mainly lignin and guaiacol), and by enzymatic bioconversion (biovanillin) from natural precursors, (mainly ferulic acid, eugenol and isoeugenol, and turmeric acid). Based on the origins its commercial value greatly changes. At the same time the European Regulation allows to label food discriminating between the sources of the ingredient indicating the term ‘natural’ even if the ingredient is obtained by biosynthetic pathways. However from literature it is apparent that the distinction between synthetic and biosynthetic vanillin is not always possible, while the natural one can be easily discriminated, although rarely used. The method here proposed is based on head-space solid-phase microextraction and gas chromatography coupled to isotope ratio mass spectrometry to determine the carbon isotope ratio (δ13C) of vanillin extracted from vanilla pods, commercial flavoured foodstuff and in vanillin samples of different origins. Isotope fractionation during SPME extraction has been determined based on sample's isotopic composition. The results confirm the literature ones and allow to reveal which biovanillin can be easily characterized and distinguished from the synthetic ones. In most cases it has been possible to evaluate the origin of vanillin used in the different food preparations. Copyright © 2016 John Wiley & Sons, Ltd.
21 citations
TL;DR: In this paper, the authors describe the principles of NMR Position-Specific Isotopic Analysis and the applications and perspectives for aroma-chemical authentication in food, confectionery, beverages, perfumery and cosmetics.
Abstract: Consumers are increasingly interested in the authenticity and traceability of food products. This review aims at describing the principles of NMR Position-Specific Isotopic Analysis and the applications and perspectives for aroma-chemical authentication. Vanillin is an excellent example since, owing to its organoleptic qualities; it is undoubtedly one of the most used aroma-chemicals in food, confectionery, beverages, perfumery, cosmetics and pharmaceutical industries. 2H-NMR was first used, but it required several hours of spectrometer time and fairly large sample amounts. 13C NMR enabled the reduction of both the experimental time and the needed quantity of vanillin. Recent developments will soon make the analysis of vanillin possible in manufactured products. Copyright © 2016 John Wiley & Sons, Ltd.
20 citations
TL;DR: EOs incorporated in emulsion showed preservative activity against all microorganisms tested and T. capitata EO emulsions showed powerful reactive oxygen species (ROS) scavenging effects, which may constitute a powerful alternative to the current preservatives and antioxidants for use in topical formulations.
Abstract: As the personal care industry evolves, formulators are seeking innovative solutions for their formulations' needs, and for ingredients that can offer multiple functions within formulations. Considering that essential oils (EOs) may present a wide spectrum of biological activities, the composition, antimicrobial and antioxidant activity of Portuguese Thymbra capitata, Thymus caespititius and Myrtus communis EOs were assessed in order to evaluate them as preservatives and antioxidants in topical emulsions. The in vivo safety application of some emulsions was also tested. T. capitata EO was mainly constituted by carvacrol (73%), whereas α-terpineol (27%), p-cymene (14%) and carvacrol (10%) dominated Th. caespititius EO, and 1,8-cineole (37%) was dominant in M. communis EO. The minimum inhibitory concentration of T. capitata, Th. caespititius and M. communis EOs was 0.4 μg/mL against C. albicans and ranged between 0.4 and 30.7 μg/mL against A. brasiliensis. Gram-positive bacteria were more susceptible to each EO than Gram-negative bacteria. T. capitata EO showed significantly higher antioxidant activity than Th. caespititius and M. communis EOs. EOs incorporated in emulsions showed preservative activity against all microorganisms tested and T. capitata EO emulsions showed powerful reactive oxygen species (ROS) scavenging effects. A safety evaluation study was performed with 0.10% and 0.01% T. capitata EO emulsions according to the Human Repeat Insult Patch Test (HRIPT). All emulsions were considered safe for topical application. T. capitata, Th. caespititius and M. communis significantly improved the microbiological quality of the prepared emulsions and may constitute a powerful alternative to the current preservatives and antioxidants for use in topical formulations.
18 citations
TL;DR: In this article, the authors evaluated the ability of Captisol® and Captisol-G to encapsulate the main volatile components of six essential oils (EOs), to enhance the aqueous solubility of these EOs and to generate controlled release systems.
Abstract: Essential oils (EOs) and their individual components have several biological properties and are used in cosmetics, food and pharmaceutical industries. However, their application still presents a challenge owing mainly to their volatility and their poor aqueous solubility and stability. The aim of this study was to evaluate, for the first time, the ability of Captisol® (sulfobutylether-β-cyclodextrin, SBE-β-CD) and Captisol-G® (sulfobutylether-γ-cyclodextrin, SBE-γ-CD) to encapsulate the main volatile components of six essential oils (EOs), to enhance the aqueous solubility of these EOs and to generate controlled release systems. The performance of these CDs was compared to hydroxypropyl-β-cyclodextrin (HP-β-CD) and γ-cyclodextrin (γ-CD), respectively. Formation constants (Kf) of the 40 inclusion complexes were determined by Static Headspace-Gas Chromatography (SH-GC). Then, Total Organic Carbon (TOC) was used to explore and quantify the efficiency of Captisol® and HP-β-CD to enhance the solubility of the six EOs. Finally, multiple headspace extraction (MHE) was applied to perform release studies. Kf values underlined the best binding potential of Captisol® towards all guests. Phase solubility diagrams showed that both Captisol® and HP-β-CD greatly increased the apparent solubility of EOs. The solubilizing potential was inversely proportionate to the EOs intrinsic solubility (SEO). Results indicated that Captisol® can successfully encapsulate EOs, increase their apparent aqueous solubility and decrease their release kinetics. Thus, Captisol® could be considered as a promising carrier to enlarge the application of EOs and their components.
17 citations
TL;DR: In this article, new features were described to discriminate vanillin from different origins using the δ13C and δ2H ratios of the methoxy group after derivatization with hydriodic acid and subsequent measurement of the released gaseous methyl iodide (CH3I) with sIRMS.
Abstract: Originating from the seedpods of orchids, Vanilla belongs to the most widely appreciated flavours worldwide. Besides the seedpods (beans) also Vanilla extracts and isolated vanillin as the major characteristic aroma compound are commercially used. Different consumer demands and national regulations require appropriate quality control of products arising from the Vanilla plants. Depending on the kind of product and its position in the supply or value chain, different methods for quality control and authentication have to be applied. When examining plant material for instance DNA barcoding can be used, whereas for Vanilla extracts and vanillin analytical quality control is frequently employed. As one of the first chemically synthesized flavouring substances with its first production in the late 19th century vanillin is nowadays manufactured via multiple different chemical and natural routes. To discriminate commercial vanillin qualities by their precursors with respect to the chemical and natural origin stable isotope ratio mass spectrometry (sIRMS) and 1H nuclear resonance spectroscopy (NMR) are the most recognized techniques. This article describes new features to discriminate vanillin from different origins using the δ13C and δ2H ratios of the methoxy group after derivatization with hydriodic acid and subsequent measurement of the released gaseous methyl iodide (CH3I) with sIRMS. The combination of available analytical data by means of multiparametric statistical tools allows for the clear segregation of critical provenience clusters for vanillin, such as (natural) eugenol-derived qualities from (synthetic) lignin- or curcumin-based products. The approach supports quality and authenticity control for Vanilla-based products, aiding in meeting customer expectations in this demanding market segment.
17 citations
TL;DR: Results suggest that treatment with eugenol involved amelioration of diabetic nephropathy by decreasing TGF-β1 expression and also amelIORated the histological changes in the diabetic kidney.
Abstract: Eugenol is an important phenylpropanoid present in essential oil obtained from a number of plant species. It is responsible for the typical flavour and the aroma of these plants. Eugenol is known for its various pharmacological activities including anti-diabetic activity. No systematic and scientific reports were available on its effect in diabetic nephropathy. Transforming growth factor β (TGF-β) plays a central role in the progression of diabetic nephropathy. Down regulation of TGF-β can prove a better approach for treatment of diabetic nephropathy. The present study was designed to evaluate the effect of eugenol in streptozotocin (STZ) induced type I diabetic nephropathy.
Diabetes was induced in male Sprague Dawley rats by administration of streptozotocin (55 mg kg-1, i.p.). The effect of eugenol was studied at the dose of 5 and 10 mg kg-1 day-1. Treatment was done for 28 days. Assessment of plasma biochemical and urine parameters was done at the end of study. Oxidative stress markers in kidney were also evaluated. Changes in kidney histology were observed by Hematoxylin-Eosin, Periodic Acid Schiff and Masson Trichrome staining. Expression of TGF-β1 was determined by measuring the optical density in immunostained kidney sections.
Parameters associated with diabetic nephropathy were significantly shifted towards the normal level after treatment with eugenol. Eugenol also ameliorated the histological changes in the diabetic kidney. Expression of TGF-β1 was increased significantly in the diabetic control group. However, eugenol treatment decreases this increased expression.
Results suggest that treatment with eugenol involved amelioration of diabetic nephropathy by decreasing TGF-β1 expression. Copyright © 2016 John Wiley & Sons, Ltd.
TL;DR: In this paper, a comprehensive two-dimensional gas chromatography (GC×GC) elucidation of an essential oil appeared in 2000 (J High Resol Chromatogr 2000;23:208-214); since then, a variety of investigations have been published also involving complex samples related to essential oils, such as perfumes.
Abstract: The first description of a comprehensive two-dimensional gas chromatography (GC×GC) elucidation of an essential oil appeared in 2000 (J High Resol Chromatogr 2000;23:208-214); since then, a variety of investigations have been published also involving complex samples related to essential oils, such as perfumes In many instances, there was no mismatch between the use of GC×GC, and the analytical scope; on the other hand, in some specific cases the use of GC×GC appeared to be less adequate
The present contribution is focused on the application of GC×GC, within the context of essential oil analysis Perfumes are also tightly related to essential oils, and so are herein considered Rather than to describe and critically-review all the research related to such investigations, attention has been devoted to the general analytical usefulness of GC×GC in the aforementioned application fields, over more established approaches, such as conventional GC and heart-cutting multidimensional GC
TL;DR: The authors investigated the effects of inhaled rosemary and lavender essential oils (EOs) on alertness and heart rate, as well as actual and perceived performance in a sustained attention task.
Abstract: Essential oils (EOs) are widely used for various purposes, however, their claimed effects are often not supported by empirical data Previous findings have highlighted the importance of psychological factors (eg expectations) in their mechanism of action The present study investigated the effects of an ingested placebo pill and inhaled rosemary and lavender oils on alertness and heart rate, as well as actual and perceived performance in a sustained attention task 128 young adults, randomly allocated to four groups (rosemary, lavender, placebo pill with stimulant suggestion, and control), completed a vigilance task before and after the respective intervention Compared to the control condition, no effects of the three interventions were found on actual changes in sustained attention, alertness, or heart rate Both EOs and the placebo pill evoked positive expectations regarding cognitive performance and alertness Expectations predicted perceived changes in alertness and heart rate, but not in cognitive performance No differences between the two EOs and the placebo intervention were found in any respect Psychological mechanisms behind the effects of inhaled EOs and placebos might be overlapping
TL;DR: In this article, the effects of two crude enzymes from Aspergillus niger on the aromas of instant green tea have been investigated, and the results indicate that both ETS and EPD contain some novel enzymes, which could modulate the aroma and thus provide potential enzyme resources for modulating the aroma of tea products.
Abstract: The effects of two crude enzymes from Aspergillus niger on the aromas of instant green tea have been investigated. The crude enzymes from tea stalk (ETS) and potato dextrose (EPD) were respectively prepared by fermentation. Both enzyme extracts significantly changed the volatile composition and aroma profile. ETS treatment increased the content of 2-ethylfuran, ethyl 2-methylbutyrate and decanal and decreased the content of trans-limonene oxide and 2-heptanone; EPD treatment increased the concentrations of 2-ethylfuran and ethyl 2-methylbutyrate and decreased the concentrations of octanal, methyl salicylate and trans-limonene oxide. After ETS treatment, the floral and fermented notes increased, while green, woody and sweet notes decreased. EPD treatment decreased green and floral notes. These results indicate that both ETS and EPD contain some novel enzymes, which could modulate the aroma of instant green tea, and thus provide potential enzyme resources for modulating the aroma of tea products.
TL;DR: In this article, the transport of essential oils to the brain following inhalation, which is the main method of administration in aromatherapy, is investigated. And the results revealed that α-pinene and linalool showed maximal transport to brain with 30 min inhalation.
Abstract: The main volatile components of essential oils are monoterpenes. It is known that olfactory receptors recognize monoterpenes as a fragrance, and that they can affect emotions. On the other hand, the components of essential oils may act directly on the central nervous system as well as the olfactory nerve. However, the transport of monoterpenes to the brain following inhalation, which is the main method of administration in aromatherapy, is unclear. In this study, we investigated major monoterpenes of essential oils, such as (+)-α-pinene, (+)-limonene, (-)-linalool, and 1,8-cineole. After the inhalation of each compound, the mice brains were dissected, and brain extracts prepared with n-hexane. The extracts were then subjected to gas chromatography-mass spectrometry analysis. The results revealed that α-pinene was transported to the brain maximally with 30 min inhalation, which may be due to its high volatility. Limonene and linalool showed maximal transport to the brain with 90 min inhalation. Brain concentrations of 1,8-cineole showed minimal level after 30 min inhalation. Moreover, 1,8-cineole was easily transported to the brain following intraperitoneal administration. These results could be applied as one of the indices for the effective use of essential oils in aromatherapy. Copyright © 2016 John Wiley & Sons, Ltd.
Abstract: The present study investigated the volatile constituents of fermented meat sauce (FMS) and identified some of the potent odour-active components. The FMS was prepared by fermenting a mixture of ground pork, koji, and salt for 12 months. After 12 months' fermentation, four potent odour components: 3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolon), 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (ethyl furaneol), 4-hydroxy-2,5-dimethyl-3(2H)-furanone, and 3-methylbutanoic acid, were found in FMS by gas chromatography-olfactometry analysis. The most characteristic components were sotolon and ethyl furaneol and contributed strongly to the FMS odour. These two components were detected in the FMS after 6 and 9 months' fermentation, respectively; especially sotolon concentration was 147.43 mg/l after 12 months' fermentation. These components were generated by fermentation and might play an important role in the FMS odour after 12 months' fermentation.
TL;DR: In this paper, β-cyclodextrin(CD) was incorporated in cotton fabric following pad-dry-cure technique employing maleic anhydride as modifying agent under the dual influence of free radical polymerization catalyst ammonium peroxodisulfate [(NH4)2S2O8] and esterification catalyst tetrasodium pyrophosphate (Na4P2O7).
Abstract: β-cyclodextrin(CD) was incorporated in cotton fabric following pad-dry-cure technique employing maleic anhydride as modifying agent under the dual influence of free radical polymerization catalyst ammonium peroxodisulfate [(NH4)2S2O8] and esterification catalyst tetrasodium pyrophosphate (Na4P2O7). β-cyclodextrin(CD) can be esterified if treated with maleic anhydride (an unsaturated dicarboxylic acid) due to the presence of hydroxyl groups in β-cyclodextrins and also such compound can form inclusion complex with essential oils. The retention of essential oil and its sustained release after repeated post wash treatments was determined quantitatively by UV–vis spectrophotometry.
TL;DR: In this article, the authors investigated and evaluated the permeation and release kinetics of TTO marker compounds from several semisolid formulations (creams, ointments, gels) containing TTO in different percentages.
Abstract: Melaleuca alternifolia essential oil (tea tree oil, TTO) is well known for its antimicrobial, antifungal and anti-inflammatory properties, which it is currently used as an active ingredient in skin care products. This study investigates and evaluates the permeation and release kinetics of TTO marker compounds from several semisolid formulations (creams, ointments, gels) containing TTO in different percentages (5–30% w/w). In vitro permeation and release tests were run in vertical Franz diffusion cells with synthetic and pig-skin membranes for different times (from 10 minutes to 50 hours). The recovered receiving phases were analyzed by Headspace Solid-Phase Microextraction (HS-SPME) in combination with Gas Chromatography coupled with Mass Spectrometry (GC–MS). The method adopted is completely automatic and provides on-line monitoring of the release and permeation kinetics, while avoiding time-consuming solvent extraction. The study examined both the total amount of essential oil and some selected markers known to be responsible for TTO's biological activities, i.e. 1,8-cineole, 4-terpineol and α-terpineol. The results of in vitro release and permeation tests demonstrated that all compounds show the same kinetics profiles, although amount released differs significantly. The markers were quantified by external calibration curves constructed through HS-SPME-GC–MS. Some preliminary experiments were also run to monitor the presence of the above markers within the skin.
TL;DR: In this article, the β-cyclodextrin (β-CD) inclusion complex of Estragole was prepared by a co-precipitation method with the aim of enhancing its thermal stability and realize its controlled release.
Abstract: Estragole (ES) has multiple biological activities and is widely used in food preservation. However, the applications of ES are limited because of its low water solubility and high volatility nature. In this paper, the β-cyclodextrin (β-CD) inclusion complex of ES was prepared by a co-precipitation method with the aim of enhancing its thermal stability and realize its controlled release. Solubility experiments were performed to evaluate the effect of β-CD on ES aqueous solubility. Release experiments of ES from its inclusion complexes were carried out at different temperatures with a relative humidity (RH) and Avrami's equation was used to analyse the release data. The antimicrobial activity of the free and included ES was also examined. The results indicated that the host–guest interactions played a crucial role in enhancing the properties of ES. The inclusion complex was investigated using physico-chemical techniques such as Fourier transform infrared spectroscopy (FTIR), thermal analysis (TGA and DSC), 1H and 2D nuclear magnetic resonance (NMR). The inclusion processes between β-CD and ES were simulated using the semi-empirical PM3 and ONIOM [B3LYP/6-31g(d):PM3] methods. Copyright © 2016 John Wiley & Sons, Ltd.
TL;DR: The chemical composition of Frullania tamarisci essential oil from Corsica was investigated using GC-FID, GC-MS and NMR analyses as discussed by the authors, and the main components were tamariscol coeluted with pacifigorgiol (30.4-41.5%), germacra-1(10)E,5E-dien-11-ol (3.6-7.1%), γ-cylocostunolide (1.8-20.0%), and frullanolide ( 1.7-
Abstract: The chemical composition of Frullania tamarisci essential oil from Corsica was investigated using GC-FID, GC–MS and NMR analyses. The essential oil compositions were further studied analyzing samples prepared from three different Corsican locations and during a seasonal vegetative cycle. 40 components, which accounted for 78.3–89.8% of the total amount of F. tamarisci essential oils were identified. The main components were tamariscol coeluted with pacifigorgiol (30.4–41.5%), germacra-1(10)E,5E–dien-11-ol (3.6–7.1%), γ-cylocostunolide (1.8–20.1%), γ-dihydrocyclocostunolide (1.2–8.0%) and frullanolide (1.7–4.9%). Among them, germacra-1(10)E,5E–dien-11-ol was never reported in the Frullania genus and pacifigorgiol, a tamariscol GC-overlapped compound, was for the first time reported in Bryophytes. Finally using 1D and 2D NMR experiments, we reported γ-dihydrocyclocostunolide as a new natural compound. Two Corsican F. tamarisci essential oils with different GC profiles were assessed for their phytotoxic behavior against onion seeds and seedling in order to evaluate their capacity to inhibit germination and alter the development of plantlets. According to the essential oil-compositions, a stimulation of the onion seedling was observed when sesquiterpene lactones amount was higher, whilst the inhibition of roots growth occurs when sesquiterpene alcohols were predominantly.
TL;DR: The vapour-phase-mediated patch assay is introduced, a simple bioassay that uses standard microtitre plates to test a small but chemically diverse set of selected essential oils with known antifungal activities against two pathogenic Candida species and concludes that it is a rather common characteristic of essential oils and their components, that should always be taken into consideration.
Abstract: Antimicrobial activity assays can be carried out in aqueous solutions using multi-well plates. However, some bioactive compounds are volatile and can cause effects at a distance. To detect such vapour-phase-mediated antimicrobial activity, we introduce the vapour-phase-mediated patch assay, a simple bioassay that uses standard microtitre plates. As a proof-of-principle, we use the vapour-phase-mediated patch assay to test a small but chemically diverse set of selected essential oils with known antifungal activities i.e. Origanum compactum, Artemisia dracunculus, Cinnamomum camphora ct linalool, Cinnamomum cassia and Melissa officinalis, as well as their corresponding major components carvacrol, estragole, linalool, trans-cinnamaldehyde and citral, against two pathogenic Candida species. As all but one of the tested essential oils i.e. Artemisia dracunculus and its corresponding component estragole, showed vapour-phase-mediated antimicrobial activity, we conclude that it is a rather common characteristic of essential oils and their components, that should always be taken into consideration. Additionally, we provide suggestions to prevent false positive results due to possible vapour-phase-mediated antimicrobial activities in bioactivity tests.
TL;DR: In this article, four stereoisomers of whisky lactone were selectively synthesized in over 99% enantiomeric excess using an amino acid derivative as a resolving agent and Cbz-L-proline was the most effective resolving agent.
Abstract: Four stereoisomers of whisky lactone were selectively synthesized in over 99% enantiomeric excess using an amino acid derivative as a resolving agent. Cbz-L-proline was the most effective resolving agent, and both trans- and cis-stereoisomers were comparatively easily separated. Odour characteristics of whisky thionolactone were different among four stereomeric isomers, and only (3S,4R)-whisky thionolactone had mushroom and cis-jasmone like note. Among all isomers, only (3R,4S)-whisky lactone showed antibacterial activities against Staphylococcus aureus. Whisky thionolactone had higher activities than whisky lactone, and (3R,4S)-whisky thionolactone showed the strongest activities of all tested samples. Copyright © 2016 John Wiley & Sons, Ltd.
TL;DR: In this paper, the composition of volatile compounds isolated from ten Salvia spp. by simultaneous distillation/extraction in a Likens-Nickerson apparatus (L-N) and supercritical fluid extraction with carbon dioxide (SFE-CO2) is reported.
Abstract: The composition of volatile compounds isolated from ten Salvia spp., namely S. amplexicaulis, S. austriaca, S. forsskaolei, S. glutinosa, S. nemorosa, S. officinalis, S. pratensis, S. sclarea, S. dumetorum and S. verticillata, by simultaneous distillation/extraction in a Likens-Nickerson apparatus (L-N) and supercritical fluid extraction with carbon dioxide (SFE-CO2) is reported. S. officinalis and S. sclarea are the most thoroughly studied Salvia spp., whereas other selected in this study Salvia spp. remain underinvestigated; to the best of our knowledge, there are no available publications on the composition of volatiles in S. forsskaolei and S. dumetorum. It was demonstrated that S. officinalis accumulates the highest amount of volatiles compounds, followed by S. sclarea; while other studied species are poor sources of volatiles. Regarding extraction method, the amount of volatiles isolated from 1 kg of dried plant material by SFE-CO2 was 1.4–5.9 times lower comparing to L-N method, most likely due to the losses of volatiles with exhausting from the system CO2 after depressurizing extraction equipment. Taking into account these findings, further studies should be focused on improving the method of collection of volatiles in SFE-CO2 process and on the determination of other, non-volatile valuable compounds, which may be present in the lipophilic CO2 extracts of under-investigated Salvia spp.
TL;DR: In this article, the authors examined whether the host tree influences the aroma of Tuber melanosporum truffles and found that truffels gathered from the Portuguese oak had a more intense aroma than the rest of the samples.
Abstract: This work examines whether the host tree influences the aroma of Tuber melanosporum truffles. Samples were gathered in the same place (Teruel, Spain) and on the same day from four host trees: hazel, Portuguese oak, kermes oak and holm oak. The truffles were subjected to sensory and chemical analysis. The sensory analysis comprised two stages. The first was based on a sorting task while the second consisted of a descriptive analysis of the samples selected from the first test. The chemical analysis examined the volatile compounds having the greatest influence on the aroma of Tuber melanosporum by means of headspace-solid phase microextraction followed by analysis by gas chromatography mass spectrometry (HS-SPME-GC-MS). The sensory tests demonstrated that truffles gathered from the Portuguese oak had a more intense aroma than the rest of the samples, and significantly more than the holm oak truffles. The same pattern occurred for the animal descriptor which was considerably more intense in Portuguese oak truffles and significantly higher than that of holm oak truffles. Chemically, these differences can be explained by the levels of isoamyl alcohol and 3-ethyl-5-methylphenol which were significantly greater in the Portuguese oak than the holm oak samples. Copyright © 2016 John Wiley & Sons, Ltd.
TL;DR: In this paper, essential oils and CO2 extracts of Timur (Zanthoxylum armatum DC syn. Hemsl) from fruits cropped in the Nepalese districts Surkhet, Jajarkot and Salyan from 2012 to 2015 were analysed to explain their typical odour and characterize their volatile profile.
Abstract: Essential oils and CO2 extracts of Timur (Zanthoxylum armatum DC syn. Zanthoxylum alatum Hemsl.) from fruits cropped in the Nepalese districts Surkhet, Jajarkot and Salyan from 2012 to 2015 were analysed to explain their typical odour and characterize their volatile profile. Best extraction conditions to ensure the right balance of the terpenic fresh notes compared with the sulphury fruity character were obtained with milled fruits and CO2 extraction. Volatile composition allowed supplying zones discrimination. Among more than 130 volatile constituents, identified by GC–MS and quantified by GC-FID with the use of predicted relative response factors, only 20 were found to have an odour impact by GC-O using a hybrid methodology between detection frequency and time intensity methods. Limonene, α-pinene and myrcene explain the terpenic notes. Linalool, citronellal, 6-methyl heptanal and octanal bring the fatty and aldehydic tone. The spicy facet is linked to (E)-methyl cinnamate and (Z)-ethyl cinnamate. 4-mercapto-4-methylpentan-2-one, 3-mercaptohexanol, 3-mercaptohexyl acetate and 1-p-menthene-8-thiol are the key olfactive constituents contributing to the typical tropical and grapefruit odours. Their presence was confirmed using the stable isotope dilution assay and reported for the first time in Timur.
TL;DR: In this paper, two simple binary combinations of fragrance aldehydes were studied, hydroxycitronellal-citral and citral-cinnamaldehyde, and their reactivity towards DPRA peptides was compared with that of the single constituents.
Abstract: Most perfume compositions and cosmetics contain mixtures of fragrance ingredients, synthetic or extracted from natural sources. Many of these are known to be weak or moderate allergens when tested individually. However, fragrances are one of the most common causes of allergic contact dermatitis to consumer products, ranking second after nickel. As consumers are exposed to mixtures of ingredients when using products that contain perfume, it was suggested that mixtures could enhance induction and elicitation of skin allergy to fragrances. Prediction of skin sensitization to chemicals is crucial for the cosmetics industry. Nowadays, methods to assess skin sensitization hazard replacing the use of animals have been developed and validated for the testing of pure substances. However, there is practically no experience with testing of mixtures. Here we evaluated in a very preliminary approach, and from a chemical reactivity perspective, if the validated DPRA, hapten-peptide reactivity based assay, could be used at a first sight to evaluate the chemical reactivity of mixtures. Two simple binary combinations of fragrance aldehydes were studied, hydroxycitronellal-citral and citral-cinnamaldehyde. Their reactivity towards DPRA peptides was compared with that of the single constituents. In general, the chemical described as the most potent sensitizer was driving the reactivity in the mixtures. Therefore, it could be hypothesized that the DPRA would estimate the mixture chemical reactivity similar to that of the stronger sensitizer component. This will be reinforced by conditions described for the DPRA where the tested chemical or mixture of chemicals will be added in large excess to the peptides. Copyright © 2016 John Wiley & Sons, Ltd.
TL;DR: This review provides an overview of drugs that have been identified as inducing olfactory disorders and discusses underlying causes and mechanisms.
Abstract: A well-functioning sense of smell is essential not only for human wellbeing and the quality of life, it is also important to protect the organism from harmful influences it is exposed to, such as gas, toxic agents or rotten food. Various drugs interfere with human olfaction and are able to elicit olfactory dysfunction, but little is known about the underlying mechanisms. To date, a wide range of drugs have not been sufficiently investigated with respect to their impact on olfaction. This review provides an overview of drugs that have been identified as inducing olfactory disorders and discusses underlying causes and mechanisms.
TL;DR: In this article, the effects of the interaction of xanthan and sugar on the release of aroma compounds (α-pinene, ethyl acetate and ethyl butyrate, perillaldehyde, hexenal, and d-limonene) were investigated in model solutions.
Abstract: The effects of the interaction of xanthan and sugar on the release of aroma compounds (α-pinene, ethyl acetate, ethyl butyrate, perillaldehyde, hexenal, and d-limonene) were investigated in model solutions (xanthan, sugar and xanthan-sugar solutions). The released aroma compounds were analysed by solid-phase microextraction and gas chromatography-mass spectrometer (SPME/GC-MS). The results showed that the six aroma compounds decreased differently in the 0.4 g·L-1 xanthan solution. A slightly stronger release of these aroma compounds in glucose solution was observed than that in sucrose solution. The release of these aroma compounds increased in the xanthan solution after the addition of the sucrose. This indicated that the release of these aroma compounds was inhibited in the xanthan solution. But the addition of sucrose in the xanthan solution could promote the release of the aroma compounds. Additionally, the rheology results showed that the xanthan solution exhibited a gradual shear thinning and the C* of xanthan was 2 g·L-1. However, the concentrations of the xanthan solution which could inhibit the release of the six aroma compounds were not fully consistent with C*. And this indicated that viscosity was not the main factor influencing the release of aroma compounds in the xanthan solution. Copyright © 2016 John Wiley & Sons, Ltd.
TL;DR: In this paper, an ionic gelification of alginate with calcium chloride (CaCl2) and subsequent addition of glutaraldehyde to improve the crosslinking degree is presented.
Abstract: In this work, sodium alginate microcapsules containing cedarwood essential oil (CWO) for uses in anti-acne tonic were prepared by ionic gelification of alginate with calcium chloride (CaCl2) and subsequent addition of glutaraldehyde to improve the crosslinking degree. Alginate microcapsules with cedarwood essential oil were obtained in an encapsulator with a 600 μm nozzle using different alginate concentrations (1, 3 and 4% w/v) , and different compositions of the coagulation solution with CaCl2 concentrations of 0.1, 0.25 and 0.5 M, and addition of glutaraldehyde at two concentrations: 12.5% and 50% (0.1 g L−1 and 10 g L−1, respectively). The effect of alginate concentration was followed by viscosimetry and the influence of the CaCl2 concentration and presence of glutaraldehyde on the microcapsules' shape as well as the total content on encapsulated cedarwood essential oil were evaluated by means of stereoscopic magnifying glass, scanning electron microscopy (SEM) and UV–vis spectrophotometry. Results show that proper shape formation is obtained for an alginate concentration of 3% w/v. With regard to the total encapsulated cedarwood oil, as the CaCl2 concentration in the gelifying-coagulating solution increases the efficiency of the encapsulated oil. Best results in terms of micro-bead shape and total amount of encapsulated oil were obtained for a CaCl2 concentration of 0.5 M without glutaraldehyde with a maximum encapsulation of 177.2 mg per gram of microcapsule.
TL;DR: In this article, a method based on hydroperoxide reduction combined with GC-MS was tested for reproducibility in fine fragrances with four different terpene hydroperoxides.
Abstract: The fragrant terpenes limonene and linalool can form skin sensitizing hydroperoxides upon prolonged exposure to air Recently, high frequencies of positive patch tests to oxidized linalool and limonene were reported from multiple dermatological centres However, there is a lack of data indicating potential sources of consumer exposure to sensitizing doses of terpene hydroperoxides which explains this frequent contact allergy Within the IDEA project (International Dialogue for the Evaluation of Allergens; http://ideaprojectinfo/), a taskforce was formed to drive analytical method development and evaluation In an inter-laboratory study in five laboratories, a method based on hydroperoxide reduction combined with GC–MS was tested for reproducibility Blinded samples of commercial fine fragrances were spiked with four different hydroperoxides In samples spiked with 100–200 μg/ml, an average recovery of 86–105% with a relative standard deviation between laboratories of 74–22% was found In samples spiked with 20–50 μg/ml, the recovery was 85–91% The reduction approach offers a transferable and reproducible method to indirectly detect low levels of hydroperoxides, at least in fine fragrances Ideally, one would prefer to directly detect the parent hydroperoxide Therefore the same samples were further tested with three LC-based methods directly detecting the parent hydroperoxide LC coupled to chemiluminescence, LC-Q-TOF-MS or LC-orbitrap-MS were used Results indicate that with specific gradients a separation of the four analytes and quantification in the fragrance matrix can be achieved Results of this method evaluation study present a toolbox of methods to detect terpene hydroperoxides to further investigate consumer exposure