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1.
Bol. latinoam. Caribe plantas med. aromát ; 23(3): 382-389, mayo 2024. ilus, tab, graf
Article in English | LILACS | ID: biblio-1538151

ABSTRACT

The extraction of geraniol from palmarosa oil using hydrotropic solvents was investigated. Palmarosa oil possesses an appealing rose aroma and properties like anti - inflammatory, antifungal, and antioxidant due to the presence of geraniol. The extraction of geraniol from palmarosa oil by using distillation methods like steam dis tillation and fractional distillation was a laborious process. So hydrotropes were tried for extraction. The geraniol yield and purity depend on parameters like concentration of hydrotrope, solvent volume ratio, and time period. Using the Box Benkhem Desig n (BBD), the extraction process was optimized. One of the major advantages of using hydrotropic solvents is that they were classified as green solvents, and recovery of solvents is also possible. To reduce the extraction time probe sonication is carried ou t. Different hydrotropic solvents with probe sonication are done on palmarosa oil by altering various process parameters to study the separation, yield, and purity.


Se investigó la extracción de geraniol del aceite de palmarosa utilizando solventes hidrotrópicos. El aceite de palmarosa posee un atractivo aroma a rosa y propiedades antiinflamatorias, antifúngicas y antioxidantes debido a la pr esencia de geraniol. La extracción de geraniol del aceite de palmarosa mediante métodos de destilación como la destilación por vapor y la destilación fraccionada ha sido un proceso laborioso. Por lo tanto, se probaron los hidrotropos para la extracción. El rendimiento y la pureza del geraniol dependen de parámetros como la concentración del hidrotropo, la relación de volumen del solvente y el período de tiempo. Se optimizó el proceso de extracción usando el diseño Box Benkhem (BBD). Una de las principales v entajas de usar solventes hidrotrópicos es que se clasifican como solventes verdes y también es posible recuperar los solventes. Para reducir el tiempo de extracción, se lleva a cabo una sonda de ultrasonido. Se realizan diferentes solventes hidrotropos co n sonda de ultrasonido en el aceite de palmarosa alterando varios parámetros del proceso para estudiar la separación, el rendimiento y la pureza.


Subject(s)
Cymbopogon/chemistry , Acyclic Monoterpenes/pharmacology , Acyclic Monoterpenes/chemistry , Plant Oils/pharmacology , Plant Oils/chemistry
2.
Zhongguo Zhong Yao Za Zhi ; 49(9): 2364-2375, 2024 May.
Article in Chinese | MEDLINE | ID: mdl-38812137

ABSTRACT

To explore the active substances exerting anti-tumour effect in lemon essential oil and the molecular mechanism inhibiting the proliferation of head and neck cancer cells SCC15 and CAL33, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay(MTT) was utilized to identify the active component inhibiting the proliferation of head and neck cancer cells, namely citral. The IC_(50) of citral inhibiting the proliferation of head and neck cancer cells and normal cells were also determined. In addition, a 5-ethynyl-2'-deoxyuridine(EdU) staining assay was used to detect the effect of citral on the proliferation rate of head and neck cancer cells, and a colony formation assay was used to detect the effect of citral on tumor sphere formation of head and neck cancer cells in vitro. The cell cycle arrest and apoptosis induction of head and neck cancer cells by citral were evaluated by flow cytometry, and Western blot was used to detect the effect of citral on the expression levels of cell cycle-and apoptosis-related proteins in head and neck cancer cells. The findings indicated that citral could effectively inhibit the proliferation and growth of head and neck cancer cells, with anti-tumor activity, and its half inhibitory concentrations for CAL33 and SCC15 were 54.78 and 25.23 µg·mL~(-1), respectively. Furthermore, citral arrested cell cycle at G_2/M phase by down-regulating cell cycle-related proteins such as S-phase kinase associated protein 2(SKP2), C-MYC, cyclin dependent kinase 1(CDK1), and cyclin B. Moreover, citral increased the cysteinyl aspartate-specific proteinase-3(caspase-3), cysteinyl aspartate-specific proteinase-9(caspase-9), and cleaved poly ADP-ribose polymerase(PARP). It up-regulated the level of autophagy-related proteins including microtubule associated protein 1 light chain 3B(LC3B), sequestosome 1(P62/SQSTM1), autophagy effector protein Beclin1(Beclin1), and lysosome-associate membrane protein 1(LAMP1), suggesting that citral could effectively trigger cell apoptosis and cell autophagy in head and neck cancer cells. Furthermore, the dual-tagged plasmid system mCherry-GFP-LC3 was used, and it was found that citral impeded the fusion of autophagosomes and lysosomes, leading to autophagic flux blockage. Collectively, our findings reveal that the main active anti-proliferation component of lemon essential oil is citral, and this component has a significant inhibitory effect on head and neck cancer cells. Its underlying molecular mechanism is that citral induces apoptosis and autophagy by cell cycle arrest and ultimately inhibits cell proliferation.


Subject(s)
Acyclic Monoterpenes , Apoptosis , Cell Proliferation , Head and Neck Neoplasms , Monoterpenes , Oils, Volatile , Humans , Cell Proliferation/drug effects , Acyclic Monoterpenes/pharmacology , Acyclic Monoterpenes/chemistry , Head and Neck Neoplasms/drug therapy , Head and Neck Neoplasms/metabolism , Head and Neck Neoplasms/genetics , Apoptosis/drug effects , Cell Line, Tumor , Oils, Volatile/pharmacology , Oils, Volatile/chemistry , Monoterpenes/pharmacology , Monoterpenes/chemistry , Cell Cycle Checkpoints/drug effects , Citrus/chemistry , Plant Oils/pharmacology , Plant Oils/chemistry
3.
Pestic Biochem Physiol ; 201: 105886, 2024 May.
Article in English | MEDLINE | ID: mdl-38685252

ABSTRACT

This study evaluates the pediculicidal activity of nanoformulations containing different binary essential oil component mixtures (eugenol:linalool, 1,8 -cineole:linalool, and eugenol:thymol) using immersion bioassays. These have allowed us to evaluate the knockdown time affecting 50% of the individuals (KT50). In addition, the type of interaction between the components in each mixture was established in terms of the combination index (IC). The KT50 values were 6.07; 8.83; 7.17 and 27.23 h for linalool, 1,8 -cineole, eugenol, and thymol, respectively. For the eugenol:linalool mixtures, the efficacy was lower or equal to that obtained for the nanoformulations of the pure compounds, with values of KT50 about 13.33, 8.16 and 6.71 h for mixtures with ratios 3:1, 1:1 and 1:3, respectively. These mixtures present IC > 1, evidencing antagonistic interaction, which is enhanced with eugenol content. In the case of the binary mixtures of 1,8 -cineole: linalool, KT50 values were similar to those obtained for eugenol:linalool mixtures with similar ratios. In this case, IC assumes values close to unity, suggesting additive interactions independently of the mixture composition. On the other side, mixtures of eugenol:thymol with 1:1 and 1:3 ratios showed values of 9.40 and 32.93 h, while the mixture with a 3:1 ratio showed the greatest effectiveness (KT50 of 4.42 h). Eugenol:thymol mixtures show synergistic interaction (IC < 1) for combinations 3:1 and 1:1, while no interaction was observed for 1:3 combination. This indicates that eugenol enhances thymol activity. These results must be considered an important step forward to the development of effective pediculicidal nanoformulations based on botanical compounds.


Subject(s)
Acyclic Monoterpenes , Eucalyptol , Eugenol , Monoterpenes , Monoterpenes/pharmacology , Monoterpenes/chemistry , Animals , Eugenol/pharmacology , Eugenol/chemistry , Eucalyptol/pharmacology , Acyclic Monoterpenes/pharmacology , Acyclic Monoterpenes/chemistry , Pediculus/drug effects , Insecticides/pharmacology , Insecticides/chemistry , Thymol/pharmacology , Thymol/chemistry , Micelles , Oils, Volatile/pharmacology , Oils, Volatile/chemistry , Nanoparticles/chemistry , Lice Infestations/drug therapy
4.
Int J Biol Macromol ; 268(Pt 2): 131767, 2024 May.
Article in English | MEDLINE | ID: mdl-38657918

ABSTRACT

In this study, linalool-nanoparticles (L-NPs) were prepared (encapsulation efficiency was 68.54 %) and introduced pH-indicator film based on cranberry-extract (CEF) to develop multifunctional smart films. XRD analysis and FTIR spectroscopy indicated that cranberry-extract (CE) and L-NPs were uniformly distributed in the gelatin/agar matrix and could change the intermolecular structure of the film. Color change of smart films showed that CE endowed the film with pH-sensitive property. As CE and L-NPs were added to the film, the water contact angle (WCA) was increased from 57.03° to 117.73°, the elongation at break (EAB) was increased from 12.30 % to 34.60 %. Additionally, the introduction of L-NPs enhanced the antioxidant activity (DPPH free radical scavenging rate increased from 26.80 % to 36.35 %) and antibacterial activity (against S. aureus and E. coli) of the smart film, which were verified by its retarding effect on pork spoilage.


Subject(s)
Acyclic Monoterpenes , Antioxidants , Gelatin , Nanoparticles , Plant Extracts , Vaccinium macrocarpon , Acyclic Monoterpenes/chemistry , Acyclic Monoterpenes/pharmacology , Antioxidants/chemistry , Antioxidants/pharmacology , Hydrogen-Ion Concentration , Gelatin/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Nanoparticles/chemistry , Vaccinium macrocarpon/chemistry , Agar/chemistry , Escherichia coli/drug effects , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Staphylococcus aureus/drug effects , Anti-Infective Agents/pharmacology , Anti-Infective Agents/chemistry , Microbial Sensitivity Tests
5.
Int J Biol Macromol ; 266(Pt 2): 131344, 2024 May.
Article in English | MEDLINE | ID: mdl-38574923

ABSTRACT

In this study, we obtained triple-layer films based on furcellaran and gelatin, in which the middle layer was enriched with extract of Curcuma longa in citral. This newly developed material underwent a comprehensive characterisation process to identify significant improvements in its functional properties. Both SEM, XRD and FTIR analyzes indicated the formation of interactions not only between the components but also between the film layers. Notably, the incorporation of the natural extract led to a significant reduction in solubility, decreasing it from 74.79 % to 57.25 %, while enhancing thermal stability expressed as a melting point elevating it from 147.10 °C in the control film to 158.80 °C in the film with the highest concentration of the active ingredient. Simultaneously, the addition of this active ingredient resulted in decreased water contact angle (WCA) values, rendering the film more hydrophilic. The produced films exhibit great promise as packaging materials, particularly within the food industry, and the conducted research is marked by its forward-looking and developmental approach.


Subject(s)
Acyclic Monoterpenes , Alginates , Curcuma , Gelatin , Plant Extracts , Plant Gums , Curcuma/chemistry , Gelatin/chemistry , Plant Extracts/chemistry , Acyclic Monoterpenes/chemistry , Acyclic Monoterpenes/pharmacology , Solubility , Food Packaging/methods , Hydrophobic and Hydrophilic Interactions , Water/chemistry , Spectroscopy, Fourier Transform Infrared
6.
Food Chem ; 449: 139240, 2024 Aug 15.
Article in English | MEDLINE | ID: mdl-38599109

ABSTRACT

The study reports the efficacy of nanofabricated citronellal inside the chitosan biopolymer (NeCn) against Aspergillus flavus growth, aflatoxin B1 (AFB1) production, and active ingredient biodeterioration (Piperine) in Piper longum L. The prepared NeCn was characterized by Scanning Electron Microscopy (SEM), Dynamic Light Scattering (DLS), and Fourier Transform Infrared Spectroscopy (FTIR). The results revealed that the NeCn exhibited distantly improved antifungal (1.25 µL/mL) and AFB1 inhibition (1.0 µL/mL) compared to free Cn. The perturbances in membrane function, mitochondrial membrane potential, antioxidant defense system, and regulatory genes (Ver-1 and Nor-1) of AFB1 biosynthesis were reported as probable modes of action of NeCn. The NeCn (1.25 µL/mL) effectively protects the P. longum from A. flavus (78.8%), AFB1 contamination (100%), and deterioration of Piperine (62.39%), thus demonstrating its potential as a promising novel antifungal agent for food preservation.


Subject(s)
Acyclic Monoterpenes , Aflatoxin B1 , Aspergillus flavus , Chitosan , Piper , Aflatoxin B1/metabolism , Aspergillus flavus/drug effects , Aspergillus flavus/growth & development , Aspergillus flavus/metabolism , Chitosan/chemistry , Chitosan/pharmacology , Piper/chemistry , Biopolymers/chemistry , Biopolymers/pharmacology , Acyclic Monoterpenes/pharmacology , Acyclic Monoterpenes/chemistry , Aldehydes/pharmacology , Aldehydes/chemistry , Antifungal Agents/pharmacology , Antifungal Agents/chemistry , Food Preservation/methods , Monoterpenes/pharmacology , Monoterpenes/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology
7.
J AOAC Int ; 107(3): 506-511, 2024 May 02.
Article in English | MEDLINE | ID: mdl-38400759

ABSTRACT

BACKGROUND: Myrcene and cymene, aromatic monoterpenes found in plants and essential oils, possess distinctive aromatic qualities. However, their volatility and limited solubility pose challenges in precise handling and formulation. Meanwhile, nanoemulsions emerge as promising drug delivery systems, improving the bioavailability and stability of these active ingredients. OBJECTIVE: This article aimed to develop an HPLC method for the quantification of two monoterpenoids, p-cymene and myrcene, in nanoemulsions. METHOD: The method used a Phenomenex® Synergi™ Fusion-RP column (150 mm × 4.6 mm id, 4 µm particle size) on an HPLC system with isocratic elution. The mobile phase was composed of acetonitrile and water (60:40, v/v) and was validated in terms of specificity, linearity, accuracy, precision, robustness, and selectivity. RESULTS: The method provided accurate and precise results with a correlation coefficient of 0.999 and RSD values of less than 2%. The method can be used for quality control of nanoemulsions containing these monoterpenoids and as a reference for future studies on their efficacy and stability. CONCLUSIONS: The study demonstrates the feasibility of using HPLC for the quantification of monoterpenoids in nanoemulsions and its potential as a quality control tool for nanoemulsion-based drug delivery systems. HIGHLIGHTS: The method's accuracy, precision, and reliability, as evidenced by high correlation coefficients and low RSD values, underscore its suitability for ensuring the consistent formulation of these monoterpenoid-containing nanoemulsions, while also serving as a reference point for future research endeavors in this field.


Subject(s)
Acyclic Monoterpenes , Alkenes , Cymenes , Emulsions , Monoterpenes , Chromatography, High Pressure Liquid/methods , Cymenes/chemistry , Cymenes/analysis , Emulsions/chemistry , Monoterpenes/analysis , Monoterpenes/chemistry , Alkenes/analysis , Alkenes/chemistry , Acyclic Monoterpenes/analysis , Acyclic Monoterpenes/chemistry
8.
Nature ; 615(7953): 634-639, 2023 03.
Article in English | MEDLINE | ID: mdl-36859552

ABSTRACT

The selective conversion of natural or synthetic neral to (1R,6S)-trans-isopiperitenol would enable and expedite sustainable routes to menthol1,2 and cannabinoids3-5. However, this reaction has been considered impossible because its product is more reactive to the required acid catalysts than its starting material, resulting in several side products6-9. We now show that an unsymmetric, strong and confined chiral acid, a highly fluorinated imino-imidodiphosphate, catalyses this process with excellent efficiency and selectivity. Expanding the method to other α,ß-unsaturated aldehydes could enable access to new cannabinoids and menthol derivatives not readily accessible previously. Mechanistic studies suggest that the confined catalyst accomplishes this reaction by binding the product in an unreactive conformation, thereby preventing its decomposition. We also show how (1R,6S)-trans-isopiperitenol can be readily converted to pharmaceutically useful cannabinoids and menthol, each in the shortest and most atom-economic routes so far.


Subject(s)
Acyclic Monoterpenes , Cannabinoids , Catalysis , Chemistry Techniques, Synthetic , Menthol , Cannabinoids/chemical synthesis , Cannabinoids/chemistry , Menthol/analogs & derivatives , Menthol/chemical synthesis , Menthol/chemistry , Aldehydes/chemistry , Halogenation , Acyclic Monoterpenes/chemistry
9.
Org Lett ; 24(24): 4415-4420, 2022 06 24.
Article in English | MEDLINE | ID: mdl-35686936

ABSTRACT

C-2 fluorinated and methylated stereoisomers of the fragrance citronellol 1 and its oxalate esters were prepared from (R)-pulegone 11 and explored as agonists of the human olfactory receptor OR1A1 and assayed also against site-specific mutants. There were clear isomer preferences and C-2 difluorination as in 18 led to the most active compound suggesting an important hydrogen bond donor role for citronellol 1. C-2 methylation and the corresponding oxalate ester analogues were less active.


Subject(s)
Acyclic Monoterpenes , Receptors, Odorant , Acyclic Monoterpenes/chemistry , Esters/chemistry , Humans , Hydrogen Bonding , Oxalates , Receptors, Odorant/agonists
10.
Int J Mol Sci ; 23(2)2022 Jan 11.
Article in English | MEDLINE | ID: mdl-35054952

ABSTRACT

Using of plant essential oil that coevolved as a defense mechanism against agriculture insects is an alternative means of controlling many insect pests. In order to repel brown planthoppers (BPHs), the most notorious rice insect pest, a new film based on guar gum incorporated with citral (GC film) was formulated, which was effective while being environmentally friendly. In this paper, the effect and mechanism of GC film repellency against BPHs were determined. Repellent activity test and olfactory reaction analysis showed that GC film had repellency effect against BPHs, with repellency of 60.00% and 73.93%, respectively. The result of olfactory reaction indicated that GC film repellency against BPHs relied on smell. EPG analysis showed the proportion and mean duration of np waveform were significantly higher than in CK and increased following the treatment concentration, which indicated that GC film affected the recognition of BPHs to rice. Further analysis by RNA sequencing analysis showed a total of 679 genes were significantly upregulated and 284 genes were significantly downregulated in the BPHs fed on the rice sprayed with GC film compared to control. Odorant-binding protein (OBP) gene 797 and gustatory receptor gene (GR)/odorant receptor (OR) gene 13110 showed a significant decrease in differential expression and significant increase in differential expression, respectively. There were 0.66 and 2.55 differential expression multiples between treated BPHs and control, respectively. According to the results described above, we reasoned that GC film repellency against BPHs due to smell, by release of citral, caused the recognition difficulties for BPHs to rice, and OBP gene 797 and GR/OR gene 13110 appeared to be the crucial candidate genes for GC film repellency against BPHs. The present study depicted a clear and consistent repellency effect for GC film against BPHs and preliminarily clarified the mechanism of GC film as a repellent against BPHs, which might offer an alternative approach for control of BPHs in the near future. Our results could also help in the development and improvement of GC films.


Subject(s)
Acyclic Monoterpenes/chemistry , Galactans/chemistry , Hemiptera/drug effects , Insect Repellents/chemistry , Insect Repellents/pharmacology , Mannans/chemistry , Plant Gums/chemistry , Animals , Behavior, Animal/drug effects , Computational Biology/methods , Gene Expression Profiling , Gene Ontology , Hemiptera/genetics , High-Throughput Nucleotide Sequencing , Transcriptome
12.
J Ethnopharmacol ; 284: 114788, 2022 Feb 10.
Article in English | MEDLINE | ID: mdl-34718102

ABSTRACT

ETHNOPHARMACOLOGICAL RELEVANCE: Besides psyche-related symptoms, patients with anxiety disorders can have a large number of somatic symptoms as well. Although the treatment of these disorders is mainly focused on resolving their mental component, one cannot neglect the need for the treatment of accompanying somatic symptoms. Melissa officinalis L. (lemon balm), in various formulations, has been extensively used as an ethnomedicinal remedy for the treatment of different psyche-related symptoms, and its use is considered relatively safe. AIM OF THE STUDY: In the present study, the activity of M. officinalis (MO) essential oil was evaluated in several in vitro and in vivo models mimicking or involving anxiety-related somatic symptoms. MATERIALS AND METHODS: To address the effect of MO essential oil on the gastrointestinal and heart-related symptoms accompanying anxiety disorders, in vitro models were utilized that follow the function of the isolated mouse ileum and atria tissues, respectively, after exposure to MO essential oil. Effects of MO essential oil on BALB/c mice motor activity was estimated using the open field, rota-rod, and horizontal wire tests. Additionally, the essential oil was assayed for its potential in inhibiting acetylcholinesterase activity. RESULTS: The performance of mice treated with 25 mg/kg of the oil showed a statistically significant decrease in the motor impairment arising from acute anxiety (open field test), while there was a prolonged latency and a reduction of the frequency of falling from a rotating rod and/or a horizontal wire (signs of muscle weakness/spasms). Concentrations of the essential oil higher than 1 µg/mL were found to inhibit both spontaneous and induced ileum contractions. Moreover, the essential oil and citronellal were found to decrease isolated mouse atria contraction frequency, as well as contraction force. However, the oil was found to be a very weak acetylcholinesterase inhibitor. CONCLUSION: The modulation of anxiety-related symptoms by the oil was found not to be mediated through the inhibition of the acetylcholinesterase, nonetheless, the mechanistic studies involving the ileum and cardiac tissues, revealed that the activity of MO and citronellal might be related to the modification of either voltage-gated Ca2+ channels or muscarinic receptors. Mice locomotion, balance, and muscle strength were not impacted by the essential oil; however, its main constituent, citronellal, was found to exert a certain degree of muscle function inhibition. All these results suggest that the activity of MO essential oil arises from synergistic and/or antagonistic interactions of its constituents, and is not completely dependent on the oil's main constituent.


Subject(s)
Acyclic Monoterpenes/pharmacology , Aldehydes/pharmacology , Anxiety/drug therapy , Melissa/chemistry , Oils, Volatile/pharmacology , Phytotherapy , Plant Oils/pharmacology , Acetylcholine/pharmacology , Acyclic Monoterpenes/chemistry , Aldehydes/chemistry , Animals , Gastrointestinal Motility/drug effects , Heart Atria/drug effects , Ileum/drug effects , Male , Mice , Mice, Inbred BALB C , Oils, Volatile/chemistry , Plant Oils/chemistry
14.
Cells ; 10(12)2021 12 14.
Article in English | MEDLINE | ID: mdl-34944045

ABSTRACT

Acetylcholinesterase (AChE) inhibition is a key element in enhancing cholinergic transmission and subsequently relieving major symptoms of several neurological and neuromuscular disorders. Here, the inhibitory potential of geraniol and its mechanism of inhibition against AChE were elucidated in vitro and validated via an in silico study. Our in vitro enzyme inhibition kinetics results show that at increasing concentrations of geraniol and substrate, Vmax did not change significantly, but Km increased, which indicates that geraniol is a competitive inhibitor against AChE with an IC50 value 98.06 ± 3.92 µM. All the parameters of the ADME study revealed that geraniol is an acceptable drug candidate. A docking study showed that the binding energy of geraniol (-5.6 kcal mol-1) was lower than that of acetylcholine (-4.1 kcal mol-1) with AChE, which exhibited around a 12.58-fold higher binding affinity of geraniol. Furthermore, molecular dynamics simulation revealed that the RMSD of AChE alone or in complex with geraniol fluctuated within acceptable limits throughout the simulation. The mean RMSF value of the complex ensures that the overall conformation of the protein remains conserved. The average values of Rg, MolSA, SASA, and PSA of the complex were 3.16 Å, 204.78, 9.13, and 51.58 Å2, respectively. We found that the total SSE of AChE in the complex was 38.84% (α-helix: 26.57% and ß-sheets: 12.27%) and remained consistent throughout the simulation. These findings suggest that geraniol remained inside the binding cavity of AChE in a stable conformation. Further in vivo investigation is required to fully characterize the pharmacokinetic properties, optimization of dose administration, and efficacy of this plant-based natural compound.


Subject(s)
Acetylcholinesterase/metabolism , Acyclic Monoterpenes/pharmacology , Cholinesterase Inhibitors/pharmacology , Molecular Docking Simulation , Molecular Dynamics Simulation , Acetylcholine/chemistry , Acyclic Monoterpenes/chemistry , Acyclic Monoterpenes/pharmacokinetics , Animals , Cholinesterase Inhibitors/chemistry , Kinetics , Ligands , Protein Binding/drug effects , Protein Structure, Secondary , Tacrine/pharmacology
15.
Molecules ; 26(24)2021 Dec 18.
Article in English | MEDLINE | ID: mdl-34946753

ABSTRACT

Levoglucosenone (LGO) is a cellulose-derived molecule that is present commercially on a multi-ton/year scale. Taking advantage of the α,ß-conjugated ketone of LGO, a new citronellol-containing 5-membered lactone (HBO-citro) was synthesized through a one-pot two-step pathway involving oxa-Michael addition and Baeyer-Villiger oxidation. The solvent-free treatment of HBO-citro with NaBH4 at room temperature led to the full reduction of the lactone moiety which gave a novel fully renewable triol monomer having a citronellol side chain (Triol-citro). Noticeably, by simply changing the reducing agent, temperature and reaction duration, the partial reduction of HBO-citro can be achieved to yield a mixture of 5- and 6-membered Lactol-citro molecules. Triol-citro was chosen to prepare functional renewable polyesters having citronellol pendant chains via polycondensation reactions with diacyl chlorides having different chain lengths. Good thermal stability (Td5% up to 170 °C) and low glass transition temperatures (as low as -42 °C) were registered for the polyesters obtained. The polymers were then hydrolyzed using a commercial lipase from Thermomyces lanuginosus (Lipopan® 50 BG) to assess their biodegradability. A higher degradation profile was found for the polyesters prepared using co-monomers (acyl chlorides) having longer chain lengths. This is likely due to the decreased steric hindrance around the ester bonds which allowed enhanced accessibility of the enzyme.


Subject(s)
Acyclic Monoterpenes/metabolism , Cellulose/metabolism , Lipase/metabolism , Polyesters/metabolism , Acyclic Monoterpenes/chemistry , Biodegradation, Environmental , Cellulose/chemistry , Eurotiales/enzymology , Lipase/chemistry , Molecular Structure , Polyesters/chemical synthesis , Polyesters/chemistry , Temperature
16.
Molecules ; 26(21)2021 Oct 27.
Article in English | MEDLINE | ID: mdl-34770901

ABSTRACT

Essential oils (EOs) are widely recognized as efficient and safe alternatives for controlling pest insects in foods. However, there is a lack of studies evaluating the toxicological stability of botanical insecticides in stored grains in order to establish criteria of use and ensure your efficiency. The objective of this work was to evaluate the toxicological stability of basil essential oil (O. basilicum) and its linalool and estragole components for Sitophilus zeamais (Motschulsky) adults in corn grains by fumigation. The identification of the chemical compounds of the essential oil was performed with a gas chromatograph coupled to a mass selective detector. Mortality of insects was assessed after 24 h exposure. After storage for six (EO) and two months (linalool and estragole) under different conditions of temperature (5, 20, and 35 °C) and light (with and without exposure to light), its toxicological stability was evaluated. Studies revealed that the essential oil of O. basilicum and its main components exhibited insecticidal potential against adults of S. zeamais. For greater toxicological stability, suitable storage conditions for them include absence of light and temperatures equal to or less than 20 °C.


Subject(s)
Coleoptera/drug effects , Insect Control , Insecticides/pharmacology , Ocimum basilicum/chemistry , Oils, Volatile/pharmacology , Plant Oils/pharmacology , Acyclic Monoterpenes/chemistry , Acyclic Monoterpenes/pharmacology , Animals , Drug Stability , Insecticides/chemistry , Lethal Dose 50 , Oils, Volatile/chemistry , Plant Oils/chemistry , Toxicity Tests
17.
Food Funct ; 12(21): 10370-10389, 2021 Nov 01.
Article in English | MEDLINE | ID: mdl-34611674

ABSTRACT

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.


Subject(s)
Acyclic Monoterpenes/chemistry , Acyclic Monoterpenes/pharmacology , Anti-Infective Agents/pharmacology , Anti-Inflammatory Agents/pharmacology , Antineoplastic Agents/pharmacology , Neuroprotective Agents/pharmacology , Animals , Anti-Infective Agents/chemistry , Anti-Inflammatory Agents/chemistry , Antineoplastic Agents/chemistry , Humans , Mice , Neuroprotective Agents/chemistry
18.
Int J Mol Sci ; 22(20)2021 Oct 12.
Article in English | MEDLINE | ID: mdl-34681662

ABSTRACT

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.


Subject(s)
Acyclic Monoterpenes/chemistry , Aeromonas hydrophila/drug effects , Anti-Infective Agents/pharmacology , Emulsions/chemistry , Acyclic Monoterpenes/pharmacology , Anti-Infective Agents/chemistry , Microbial Sensitivity Tests , Nanotechnology , Particle Size
19.
Molecules ; 26(20)2021 Oct 19.
Article in English | MEDLINE | ID: mdl-34684884

ABSTRACT

Cinnamomum verum is widely used in traditional medicines, and the different parts of the plant, such as bark, leaves, and flowers, are used for essential oil production. The present study compared the chemical composition of the essential oil of C. verum extracted from the leaves and flowers. In addition, efficacy of these essential oils against the two common pests Sitophilus oryzae and Callosobruchus maculatus was also evaluated. The results indicated the presence of cinnamaldehyde, eugenol, caryophyllene, and linalool in these essential oils, however, at different concentrations. The leaf essential oil was found to be 10-20% more effective as a fumigant against both the pests. Likewise, the leaf essential oil found to repel these pests even at lower concentrations than that of flower essential oil of C. verum. Besides, these essential oils were also effective in controlling the growth of various gram positive and gram negative microbial pathogens and possibly a safeguard for human health. On contrary, both the essential oils were found to be safe for the application on grains, as indicated by their germination potentials. It was also observed that these essential oils do not cause any significant toxicity to guppy fishes, thus confirming their ecological safety for use as a biopesticide.


Subject(s)
Anti-Bacterial Agents/chemistry , Cinnamomum zeylanicum/chemistry , Flowers/chemistry , Insect Repellents/chemistry , Insecticides/chemistry , Oils, Volatile/chemistry , Plant Leaves/chemistry , Acrolein/analogs & derivatives , Acrolein/chemistry , Acrolein/pharmacology , Acyclic Monoterpenes/chemistry , Acyclic Monoterpenes/pharmacology , Anti-Bacterial Agents/pharmacology , Insect Repellents/pharmacology , Insecticides/pharmacology , Oils, Volatile/pharmacology , Plant Oils/chemistry , Plant Oils/pharmacology
20.
J Food Sci ; 86(10): 4554-4565, 2021 Oct.
Article in English | MEDLINE | ID: mdl-34519054

ABSTRACT

Combinations of phytochemical(s) and engineered nanoparticles have attracted immense research interest due to their superior antimicrobial effects against contaminations. Herein, a Pickering emulsion is developed with capsulized phytochemicals including borneol and citral (BC-Cap) stabilized by hydrophilic amine-functionalized silica nanoparticles (SiO2 ─NH2 NPs). The droplet sizes of Pickering emulsion were 5.2 ± 1.4 µm under the condition that the concentrations of SiO2 ─NH2 NPs ranged from 0.6 to 1.2 wt.%, and the emulsion showed desirable stability during storage at 40°C for 365 days. In addition, the antibacterial and antibiofilm activities of the Pickering emulsion were investigated. The antibacterial effect of BC-Cap increased by two- to fourfold compared with citral or borneol alone. Treatment of BC/BC-Cap for 4 h eliminated the formation of biofilms generated by Listeria monocytogenes (at 5/1.25 mg/ml; 2 × MIC concentration) and Pseudomonas aeruginosa (at 5/2.5 mg/ml; 2 × MIC concentration). Further mechanistic studies revealed that the antibiofilm effects of BC-Cap were attributed to its ability to increase the porosity and lytic effects on the cell membrane of bacteria. Findings from the current study support the antibacterial and antibiofilm effects of BC-Cap Pickering emulsion as a promising food additive. PRACTICAL APPLICATION: The Pickering emulsion has potential applications as bacteriostatic agent in packaging materials and general surface disinfectant. The combination of borneol and citral is stabilized by hydrophilic amine-functionalized silica nanoparticles (SiO2 ─NH2 NPs). With the synergistic effects of borneol and citral, the Pickering emulsion shows a promising elimination effect against the formation of biofilms produced by Listeria monocytogenes and Pseudomonas aeruginosa.


Subject(s)
Acyclic Monoterpenes , Anti-Bacterial Agents , Camphanes , Nanoparticles , Acyclic Monoterpenes/chemistry , Anti-Bacterial Agents/pharmacology , Camphanes/chemistry , Emulsions/chemistry , Listeria monocytogenes/drug effects , Nanoparticles/chemistry , Particle Size , Pseudomonas aeruginosa/drug effects , Silicon Dioxide
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