Flavour and Fragrance Journal最新文献

Temperature-sensitive nanocapsules with controllable release properties were synthesized through miniemulsion free radical polymerization method. Temperature-sensitive N,N-diethylacrylamide/N,N-dimethylacrylamide (DEA/DMA) copolymer were systematically synthesized as shell materials, and the fragrance-dementholized peppermint oil (DPO) was encapsulated as hydrophobic core material. The as prepared nanocapsules had high encapsulation efficiencies of more than 90% and small average diameters of less than 150 nm, as well as narrow polydispersity index (PDI) below 0.17. Furthermore, decreased DEA contents in shell material resulted in higher phase transition temperature and slower release rate of fragrance under the same temperature. By varying the copolymer composition of shell materials, the controllable release property of as prepared nanocapsules were also varied under different temperatures.

(Z)-jasmone is the most important contribution to the scents of perfumes and cosmetics. However, (Z)-jasmone is water insoluble and highly volatile, which limits its development and application. Inclusion technology has become a promising strategy to improve the solubility and stability of hydrophobic small molecules. Here, we used saturated aqueous solution and freeze-drying method to prepare solid inclusion complexes of (Z)-jasmone and three acyclic cucurbit[n]urils (ACBs, M1-M3), and studied their binding behaviours by fluorescence spectroscopy, NMR, XRD, FT-IR, TG and DSC, confirming the formation of the host-guest inclusion complexes. The stoichiometry of inclusion complexes was 1:1 by Job's plot. The inclusion complexes exhibited better water solubility, higher thermal stability and heat-controlled release comparing with that of native (Z)-jasmone. This work uncloses a new strategy to enhance the performance of essential oil and flavours/fragrances and further application in the field of cosmetic and food industry.

Artemisia dracunculus L. (tarragon) is valuable for its medicinal uses such as antimalarial, antibacterial and anticancer. Biotechnological methods need to be developed for the production of phytochemical compounds in plants with high and stable quality. Elicitation is one of the best tools for increasing secondary metabolites in various in vitro cultures. The current study determines the application of different concentrations of chitosan (25, 50, 100 and 150 mg/L) and UV-C (5/10, 5/15, 10/10 and 10/15 min/cm) as biotic and abiotic elicitors in tarragon leaf callus cultures. The main aim was to increase the accumulation of artemisinin, quercetin, caffeic acid and essential oil content. For this purpose, callus formation rates and morphological features were also investigated. The results show that highest callus formation, weight and diameter were observed in UV-C treated cultures. HPLC analyses revealed significant high accumulation of artemisinin (1.9 μg/g), quercetin (4.2 μg/g) and caffeic acid (2.9 μg/g) contents in 5/10 min/cm UV-C treated samples. GC–MS analyses of callus cultures indicate high production of total amount of monoterpenes in all chitosan applications, best in 25 mg/L (90.75%). The major compound was β-phellandrene in chemical composition of tarragon (19.61%) and increased the most in 10/15 min/cm UV-C application (43.39%). The results show that the physical elicitor UV-C can be effectively used in tarragon callus culture for enhancing pharmacologically active compounds in industrial production.

A novel automated flow-cell coupled dynamic solid-phase microextraction (SPME) method was developed to study the emission of volatile fragrance compounds from fabric samples in a microchamber. Calibration curves were developed with the liquid-inner tube diffusion-film-emission (LIFE) vial technique to quantify the gas-phase concentration of nine significant volatile fragrance compounds. The linearity range for the various volatile fragrance compounds ranged from 0.001 to 37.9 mg/m³. The limit of quantitation (LOQ) for each fragrance compound was determined as ~3.6–12.1 μg/m³. Using this method, we obtained comprehensive emission curves of target volatiles to quantify the volatile emission profiles of fabric samples. Compared with traditional chamber test method procedures, this work provides a novel and automated method to allow the online monitoring of the emission of various volatiles from multiple samples in one experiment. The repeatability and sensitivity of the method are comparable to or better than existing offline techniques.

Studies have shown that olfactory experience during breastfeeding plays an important role in the later development of certain food preferences in life. Thus, the aim of this study was to predict partitioning of odorous terpenes and terpenoids into breast milk from a predictive QSAR model for drug transfer. A large heterogenous data set based on drugs and their active metabolites that were used to build a QSAR was collected from the literature. Due to the vast structural diversity of these compounds and possibly different mechanisms involved in M/P partitioning, a non-linear artificial neural network (ANN) model was used to develop a predictive QSAR model. The value of the correlation coefficient of predicted versus experimentally measured M/P values for the final model (14-2-1) was high (R = .82). The descriptors selected in the final model (14-2-1) belong to 3 main categories: (a) solubility/permeability descriptors (dipole moment, polar surface area, aromatic ring count and hydroxyl group count), (b) reactivity descriptors (i.e. HOMO energy) and (c) shape descriptors (different ring size counts, counts of methyl groups and molecular depth). Results of this study predict that many volatile terpenes from the essential oils are transferred into breast milk selectively. The highest M/P values (>3.5) were predicted for β-caryophyllene, aromadendrene, alloaromadendrene, and 1,4- and 1,8-cineole, high values for carvacrol (M/P = 3.2), eugenol (M/P = 3.0) and thymol (M/P = 3.6), and moderate values for α-pinene (M/P = 2.3) and low values (M/P = 0.4) for phellandrene and limonene. Our model helps to explain and expand on the current knowledge of volatile compounds in breast milk by predicting that a variety of volatile terpenoids can be found in breast milk.

This research aimed to evaluate the combined effects of chemical, biological and organic fertilizers on several features of Satureja khuzistanica. As an aromatic plant with medicinal properties, endemic to Iran, S. khuzistanica was studied for essential oil (EO%) and composition. Spanning for two growing seasons (2017–2019), the experiments involved 13 nutritional treatments, ie, (a) control (C), (b) nitrogen, phosphorus and potassium (NPK; 50-25-25 Kg ha⁻¹), (c) cattle manure (CM₃₀; 30 ton ha⁻¹), (d) CM₆₀ (60 ton ha⁻¹), (e) CM₃₀ + NPK, (f) CM₆₀ + NPK, (g) vermicompost (V₅, 5 ton ha⁻¹), (h) V₅ + NPK, (i) Glomus mosseae (GM), (j) Glomus Intra (GI), (k) sulphur (S₀; 0 Kg ha⁻¹) + thiobacillus (T), (l) S₂₅₀ + T (sulphur: 250 Kg ha⁻¹, ) and (m) V₅ + T. At full flowering stage, samples were taken from aerial segments of plants in all treatment groups. After shade-drying, the samples were hydro-distillated to obtain essential oil (EO) and were then evaluated by gas chromatography–mass spectrometry (GC–MS). The interaction between year and fertilizer, as two treatments, had a significant effect (P ≤ 0.01) on the oil percentage, oil constituents and essential oil yield (EO.Y) of S. khuzistanica. GM and S₀ + T caused the highest oil percentage in the first (3.7%) and second year (3.9%), respectively. V₅ + NPK and V₅ + T resulted in a substantial rise in EO.Y in the first (30.4 kg ha⁻¹) and second year (64.3 kg ha⁻¹), respectively. Carvacrol was highest in the first (92.1%) and second year (95.2%), as a result of using V₅ + T and NPK treatments, respectively. Biological and vermicompost fertilizers not only improved the amount of EO but also enhanced its quality and aroma, as reflected in the constituents of the EO. The GI treatment and the V₅ + NPK treatment led to high amounts of K in the branches. Meanwhile, high S contents were measured in the branches in response to the V₅ and the S₂₅₀ + T treatments. These findings suggested that biofertilizers and organic fertilizers can benefit the cultivation of S. khuzistanica because, when combined together, they can enhance the percentage and phenolic compounds in the EO.

The effect of lipid level and reaction temperature and time on the heated cysteine-xylose reaction to form meaty flavours was investigated. The presence of 1% or 2% methyl linoleate inhibited the formation of volatile sulfur-containing compounds and heterocyclic compounds via the Maillard reaction, that is Maillard compounds. However, the former was better because of the moderate inhibition and more compounds generated from the lipid-Maillard interaction, that is lipid-Maillard compounds. Partial least squares-discriminant analysis suggested the lipid-Maillard compounds were the main markers during varying dosage of methyl linoleate, reaction temperature (100–140°C) and reaction time (30–180 min). Lower temperatures increased formation of the Maillard compounds (eg, 2-furfurylthiol) or lipid-Maillard compounds (eg, 2-pentylpyridine) with reaction time. However, high temperatures caused their amounts changed in a curve or irregularly due to the complications from the Maillard and lipid oxidization reactions. By comparing time-courses of the levels of cysteine and Cys-Amadori compounds, and 294 and 420 nm UV absorbance values in the reaction systems under 120°C with or without 2% methyl linoleate, it was revealed that the underlying lipid effect mechanism was to initially inhibit and later attend the Maillard reaction, leading to less formation of the Maillard compounds and generation of the lipid-Maillard compounds.

The study aims to develop wash-resistant antibacterial cotton fabrics without using synthetic chemicals. Therefore, natural active agents of thyme, thymol and carvacrol were selected. The inclusion complexes were formed with β-cyclodextrin using kneading method which is a simple and reproducible method for the encapsulation with high production yield. Differential scanning calorimeter analysis showed that 1:1 and 1:2 β-CD: Guest Molecule (M:M) for thymol and carvacrol from different ratios studied has the highest complexation degree as 50% and 100%, respectively. It is also revealed that the volatile agents are retained and showed better thermal stability as a result of complexation. Carvacrol inclusion complexes were found relatively more stable (Zeta potential: −28.2 mV) than thymol complexes with smaller particle sizes (204.9 nm). Chemical structures of the inclusion complexes were revealed with Fourier transform-infrared spectroscopy and nuclear magnetic resonance analyses. The optimum formulations for each active agent were applied to cotton fabrics as per the impregnation method and the capsule treated fabrics were washed 1, 10 and 20 times. The images exhibited the presence of inclusion complexes on the fabrics after 20 washing cycles. Although the antibacterial efficacy of fabrics decreased with increasing washing, the fabrics showed the antibacterial effect after 20 washes against Klebsiella pneumoniae and Staphylococcus aureus. This study showed that the developed products can be an alternative to the other products in the market as the long-lasting fragrant natural antibacterial.

(−)-Menthol is one of the most popular aroma compounds worldwide. While in the past mostly extracted from mint plants, today (−)-menthol synthesis from other raw materials is becoming more relevant. Common starting materials for menthol synthesis are m-cresol, citral and myrcene, but also substrates like menthone, mono- and bicyclic terpenes and terpenoids have been used for this purpose in the past. As for many applications (−)-menthol of high purity is required, asymmetric syntheses and enantiomeric resolution of obtained raw products are applied for menthol production. This review gives an overview on the most important synthetic menthol production processes of the companies Symrise, Takasago and BASF and relevant literature in the field of menthol synthesis with a focus on the last 20 years.

Lipoxygenases (LOX) catalyse allylic oxidations and epoxidations of a co-substrate in the presence of an unsaturated fatty acid containing a 1,4-pentadiene moiety. One- and two-step enzyme assays were established to verify the role or involvement of LOX in such co-oxidations. It was shown that LOX is only involved in the formation of reactive hydroperoxides, but not in the oxidation of a co-substrate, assuming a mechanism involving free peroxy radicals for the latter. Ten mono- and sesquiterpenes were used as co-substrates and the resulting products were analysed by mass spectrometry. A semi-preparative approach was developed using (+)-valencene as an example, and the resulting products were isolated by preparative GC and their structures elucidated by NMR spectroscopy.