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ACS Applied Bio Materials Oct 2023Functionalization of thymol (Thy) on nanocarriers is a key step in achieving prolonged antimicrobial activity. This requires nanomaterials with uniform particle...
Functionalization of thymol (Thy) on nanocarriers is a key step in achieving prolonged antimicrobial activity. This requires nanomaterials with uniform particle diameters and suitable thymol sorption. Herein, hollow carbon (HC) and SiO-carbon core-shell (SiO@C) were investigated due to their diverse morphologies and ease of surface modification. HC (14 ± 1 nm size) and SiO@C (10 ± 1.5 nm size) were synthesized by the Stöber method before thymol was loaded by incipient wetness impregnation. Nanoparticle physicochemical properties were characterized by advanced techniques, including X-ray photoelectron spectroscopy (XPS) and near-edge X-ray absorption fine structure (NEXAFS). Adsorption energies of thymol on the carbon and SiO surfaces were elucidated by density functional theory (DFT) simulations. Moreover, the thymol release profiles and antibacterial activity were evaluated. The experimental results indicated that the oxy-carbon surface species of HC led to longer thymol release profiles than the -OH group of SiO@C. The DFT calculations revealed that the weaker physical interaction of thymol on HC was better for drug release than that on SiO@C. Thus, a longer thymol release profile of HC with hollow structures showed better antibacterial performance against Gram-positive bacteria than that of SiO@C with core-shell structures. This work confirms the important role of carbon morphology and specific functional groups in thymol release profiles for the further development of inhibition products.
Topics: Thymol; Silicon Dioxide; Nanospheres; Adsorption; Carbon; Anti-Bacterial Agents
PubMed: 37756496
DOI: 10.1021/acsabm.3c00460 -
Assessment of Sex-Specific Toxicity and Physiological Responses to Thymol in a Common Bean Pest Say.Frontiers in Physiology 2022Say (Coleoptera: Chrysomelidae: Bruchinae), is one of the most important pests of the common bean L. Without appropriate management it may cause significant seed loss...
Say (Coleoptera: Chrysomelidae: Bruchinae), is one of the most important pests of the common bean L. Without appropriate management it may cause significant seed loss in storages. In search for means of environmentally safe and effective protection of beans we assessed biological activity of thymol, an oxygenated monoterpene present in essential oils of many aromatic plants. We studied contact toxicity of thymol on bean seeds and its effects on adult longevity and emergence in F1 generation. Furthermore, we determined acetylcholinesterase (AChE), superoxide dismutase (SOD), catalase (CAT), mixed-function oxidase (MFO), carboxylesterases (CarE) and glutathione S-transferase (GST) activities in response to 24 h exposure of beetles to sublethal and lethal thymol concentrations. Our results showed that thymol decreased adult survival, longevity and percentage of adult emergence. Higher median lethal concentration (LC) was recorded in females indicating their higher tolerance comparing to males. Overall, activities of SOD, CAT and CarE increased at sublethal and MFO increased at both sublethal and lethal thymol concentrations. On the other hand, GST and AChE activities decreased along with the increase in thymol concentrations from sublethal (1/5 of LC, 1/2 of LC) to lethal (LC). Enzyme responses to the presence of thymol on bean seed were sex-specific. In the control group females had lower CarE and higher SOD, CAT and GST activity than males. In treatment groups, females had much higher CAT activity and much lower CarE activity than males. Our results contribute to deeper understanding of physiological mechanisms underlying thymol toxicity and tolerance which should be taken into account in future formulation of a thymol-based insecticide.
PubMed: 35250641
DOI: 10.3389/fphys.2022.842314 -
Journal of Cancer Research and... Oct 2023Cancer is a major malignancy and one of the leading causes of death; it calls for a proactive strategy for the cure. Herbs are reservoirs of novel chemical entities and...
BACKGROUND
Cancer is a major malignancy and one of the leading causes of death; it calls for a proactive strategy for the cure. Herbs are reservoirs of novel chemical entities and their phytochemical exploration has contributed considerably to the discovery of new anticancer drugs. Thymol, a natural phenolic monoterpenoid, has been implicated with many medicinal properties, including anticancer ones. However, the anti-proliferative and apoptosis-inducing ability of thymol on MDA-MB-231 and HCT-8 cell lines has not been studied yet in detail, and hence this study was conceived.
MATERIALS AND METHODS
We studied the cytotoxicity, morphological alterations of the cell, oxidative stress, cell cycle modulation, apoptosis and expression of apoptosis-related proteins that ensued due to thymol treatment in these cancer cells.
RESULTS
Thymol inhibited the cell proliferation, altered the morphology of the cells, increased the intracellular ROS level, arrested the cells in G0/G1 phase, induced apoptosis, upregulated pro-apoptotic protein p53 expression, downregulated anti-apoptotic protein Bcl-xL expression, and activated caspase-9 and -3.
CONCLUSION
These findings elucidate that thymol induces apoptosis through the intrinsic pathway, in MDA-MB-231 breast and HCT-8 colorectal cancer cells through ROS generation and G0/G1 phase cell cycle arrest. This reiterates the broad-spectrum anti-tumor potential of thymol and provides an insight to study further to be developed into an anticancer drug.
Topics: Humans; Thymol; Caspase 9; Reactive Oxygen Species; Apoptosis; Cell Line; Colorectal Neoplasms
PubMed: 38376297
DOI: 10.4103/jcrt.jcrt_308_22 -
Pharmacokinetic study of thymol after intravenous injection and high-dose inhalation in mouse model.Pharmacology Research & Perspectives Oct 2019Thymol is generally recognized as a safe substance by the FDA and has been widely used in the pharmaceutical, food, and cosmetic industries. Pharmacokinetic (PK) studies... (Comparative Study)
Comparative Study
Thymol is generally recognized as a safe substance by the FDA and has been widely used in the pharmaceutical, food, and cosmetic industries. Pharmacokinetic (PK) studies of thymol have been previously conducted for oral administration, but there has been no PK study for inhalation administration or intravenous (IV) injection. This study aims at exploring and comparing the inhalation and IV PK profile of thymol in a mouse model. The inhalation PK for mouse model was corrected with fur/skin absorption. Thirty-two male CD-1 mice were randomized into two study arms, Arm-A for intravenous (n = 16) and Arm-B for inhalation (n = 16). The amount of thymol in the mouse serum was measured for Arm-A and for Arm-B at the highest dose. Furthermore, 48 mice were utilized for fur/skin absorption of thymol. In total, 320 mouse serum samples for thymol were analyzed by LC/MS method. After inhalation, the peak concentration of thymol in mouse serum was 42.3 ng/mL ( ) and occurred at 2 minutes ( ). The AUC of the inhaled thymol at 0-60 minutes (AUC) was 464 ng/mL/min. From 10-60 minutes post-dose, the PK inhalation curve appeared to be higher than that for the IV injection. This is likely attributed to the effect of absorption of thymol through the fur/skin of mice. After an adjustment by fur/skin absorption, the PK profile for net inhalation closely matched the two-compartment model. In fact, the bioavailability for the net inhalation of thymol was 74% and 77% relative to that for IV injection per AUC and AUC, respectively.
Topics: Administration, Inhalation; Animals; Biological Availability; Chromatography, Liquid; Injections, Intravenous; Male; Mass Spectrometry; Mice; Models, Animal; Random Allocation; Thymol
PubMed: 31452900
DOI: 10.1002/prp2.515 -
Bioorganic & Medicinal Chemistry Nov 2014In Northeastern Brazil visceral leishmaniasis is endemic with lethal cases among humans and dogs. Treatment is toxic and 5-10% of humans die despite treatment. The aim...
In Northeastern Brazil visceral leishmaniasis is endemic with lethal cases among humans and dogs. Treatment is toxic and 5-10% of humans die despite treatment. The aim of this work was to survey natural active compounds to find new molecules with high activity and low toxicity against Leishmania infantum chagasi. The compounds thymol and eugenol were chosen to be starting compounds to synthesize acetyl and benzoyl derivatives and to test their antileishmanial activity in vitro and in vivo against L. i. chagasi. A screening assay using luciferase-expressing promastigotes was used to measure the growth inhibition of promastigotes, and an ELISA in situ was performed to evaluate the growth inhibition of amastigote. For the in vivo assay, thymol and eugenol derivatives were given IP to BALB/c mice at 100mg/kg/day for 30 days. The thymol derivatives demonstrated the greater activity than the eugenol derivatives, and benzoyl-thymol was the best inhibitor (8.67 ± 0.28 μg/mL). All compounds demonstrated similar activity against amastigotes, and acetyl-thymol was more active than thymol and the positive control drug amphotericin B. Immunohistochemistry demonstrated the presence of Leishmania amastigote only in the spleen but not the liver of mice treated with acetyl-thymol. Thus, these synthesized derivatives demonstrated anti-leishmanial activity both in vitro and in vivo. These may constitute useful compounds to generate new agents for treatment of leishmaniasis.
Topics: Animals; Antiprotozoal Agents; Cell Line; Eugenol; Humans; Leishmania infantum; Leishmaniasis, Visceral; Macrophages; Male; Mice; Mice, Inbred BALB C; Thymol
PubMed: 25281268
DOI: 10.1016/j.bmc.2014.08.020 -
Molecules (Basel, Switzerland) Jun 2023Antioxidant activities of five essential oils (cinnamon, thyme, clove, lavender and peppermint oils) and their major components (eugenol, thymol, linalool, and menthol)...
Antioxidant activities of five essential oils (cinnamon, thyme, clove, lavender and peppermint oils) and their major components (eugenol, thymol, linalool, and menthol) were evaluated on scavenging DPPH (2,2-diphenyl-1 picrylhydrazyl) free radicals, inhibiting polyunsaturated fatty acid oxidation in fish oil emulsion (FOE), and reducing oxidative stress in human red blood cells (RBC). The essential oils from cinnamon, thyme, clove and their main components, eugenol and thymol, exhibited the highest antioxidant activity in the FOE and RBC systems. It was found that the antioxidant activity of essential oils was positively correlated to the content of eugenol and thymol, while lavender and peppermint oils and their main components, linalool and menthol, had very low antioxidant activity. Compared with scavenging DPPH free radical activity, the antioxidant activity in FOE and RBC systems could better reflect the actual antioxidant potential of essential oil in preventing lipid oxidation and reducing oxidative stress in biological system.
Topics: Humans; Antioxidants; Oils, Volatile; Eugenol; Thymol; Menthol; Free Radicals; Oxidative Stress
PubMed: 37299039
DOI: 10.3390/molecules28114559 -
Molecules (Basel, Switzerland) May 2021Polyvinyl chloride (PVC), polypropylene (PP), polyethylene (PE), and stainless steel (SS) are commonly used in medicine and food production technologies. During contact...
Polyvinyl chloride (PVC), polypropylene (PP), polyethylene (PE), and stainless steel (SS) are commonly used in medicine and food production technologies. During contact with microorganisms on the surface of these materials, a microbial biofilm is formed. The biofilm structure is difficult to remove and promotes the development of pathogenic bacteria. For this reason, the inhibition of biofilm formation in medical and food production environments is very important. For this purpose, five naturally occurring compounds were used for antimicrobial screening tests. The two with the best antimicrobial properties were chosen to inhibit the biofilm formation of and . After 3 days of exposure, thymol reduced the amount of biofilm of within the range of 70-77% and 52-75% for . Carvacrol inhibited the formation of biofilms by up to 74-88% for and up to 86-100% for . Those phenols decreased the enzyme activity of the biofilm by up to 40-100%. After 10 days of exposure to thymol, biofilm formation was reduced by 80-100% for and by about 79-100% for . Carvacrol reduced the amount of biofilm by up to 91-100% for and up to 95-100% for .
Topics: Anti-Bacterial Agents; Anti-Infective Agents; Biofilms; Chemistry, Pharmaceutical; Cymenes; Food Technology; Hydrolysis; Materials Testing; Microbial Sensitivity Tests; Pseudomonas aeruginosa; Stainless Steel; Staphylococcus aureus; Surface Properties; Thymol
PubMed: 34066411
DOI: 10.3390/molecules26092723 -
Molecules (Basel, Switzerland) Aug 2022A method based on dynamic headspace vacuum transfer in trap extraction, followed by gas chromatography coupled with a mass spectrometer (DHS-VTT-GC-MS), was validated...
A method based on dynamic headspace vacuum transfer in trap extraction, followed by gas chromatography coupled with a mass spectrometer (DHS-VTT-GC-MS), was validated for the fast quantitation of 1,4-dichlorobenzene (p-dichlorobenzene; PDCB) and thymol residues in beeswax. The quantitation limits (LOQ) were 0.05 mg/kg (PDCB) and 0.25 mg/kg (thymol). Recoveries above 80% were obtained for PDCB concentrations between 0.05 and 10 mg/kg and for thymol concentrations between 0.25 and 200 mg/kg. Analysis of beeswax samples showed a good correlation between the results obtained by DHS-VTT-GC-MS analysis and those of a previous method based on SPE extraction followed by gas chromatography and triple- quadrupole mass spectrometry (GC-MS/MS) (R = 0.9770 for PDCB and 0.9666 for thymol). However, the sample preparation and chromatography were much shorter using the DHS-VTT-GC-MS method. Forty comb foundations samples produced in Switzerland in 2019 and 2021 were analysed using DHS-VTT-GC-MS. Fourteen samples contained PDCB above the LOQ of 0.05 mg/kg, ranging up to a maximum of 1.53 mg/kg. The mean concentration of the positive samples was 0.22 mg/kg. All samples contained thymol residues ranging between 3.9 and 84.4 mg/kg with mean and median concentrations of 22.7 mg/kg and 17.4 mg/kg. Residue levels of PCDB and thymol in Swiss beeswax were substantially below those measured 20 (PDCB) and 10 (thymol) years ago, respectively.
Topics: Chlorobenzenes; Gas Chromatography-Mass Spectrometry; Tandem Mass Spectrometry; Thymol; Vacuum; Waxes
PubMed: 36080133
DOI: 10.3390/molecules27175367 -
BioMed Research International 2014Carum copticum L. commonly known as "Ajwain" is cultivated in many regions of the world including Iran and India, states of Gujarat and Rajasthan. Traditionally, C.... (Review)
Review
Carum copticum L. commonly known as "Ajwain" is cultivated in many regions of the world including Iran and India, states of Gujarat and Rajasthan. Traditionally, C. copticum has been used in the past for various therapeutic effects including bloating, fatigue, diarrhea, abdominal tumors, abdominal pain, respiratory distress, and loss of appetite. It has other health benefits such as antifungal, antioxidant, antibacterial, antiparasitic, and hypolipidemic effects. This plant contains different important components such as carbohydrates, glucosides, saponins and phenolic compounds (carvacrol), volatile oils (thymol), terpiene, paracymene and beta-pinene, protein, fat, fiber, and minerals including calcium, phosphorus, iron, and nicotinic acid (niacin). In the previous studies, several pharmacological effects were shown for C. copticum. Therefore, in this paper, the pharmacological effects of the plant were reviewed.
Topics: Animals; Anti-Infective Agents; Carum; Cymenes; Gastrointestinal Tract; Heart; Humans; Lung; Monoterpenes; Phytotherapy; Plant Extracts; Plant Preparations; Seeds; Thymol
PubMed: 25089273
DOI: 10.1155/2014/569087 -
Brazilian Journal of Biology = Revista... Nov 2018This study aimed to evaluate the in vitro antibacterial activity of the phytochemicals thymol, linalool, and citronellol against Streptococcus mutans, Streptococcus...
This study aimed to evaluate the in vitro antibacterial activity of the phytochemicals thymol, linalool, and citronellol against Streptococcus mutans, Streptococcus salivarius and Streptococcus oralis. Disk diffusion screening on solid medium and measurement of the diameter of the bacterial growth inhibition halos was the technique utilized. The Minimum Inhibitory Concentration (MIC) of the substances was determined using serial substance dilutions and microdilution technique in Brain Heart Infusion culture medium. After incubation for 24 hours in an oven at 37 °C, plate reading was completed and confirmed by visual method using 2,3,5 triphenyl tetrazolium chloride dye. The Minimum Bactericidal Concentration (MBC) was determined from MIC subcultures. Assays were performed in triplicate, and chlorhexidine was used as a positive control. The diameters in mm of the growth inhibition halos ranged between 7.3 and 10.7 for S. mutans, 7.3 and 10.0 for S. oralis, and 8.2 and 9.8 for S. salivarius. The MIC and MBC values obtained converged, ranging from maximum values in the presence of Linalool (1,250.0 mg/mL, 2,500.0 mg/mL and 2,500.0 mg/mL, respectively, for S. mutans, S. oralis, and S. salivarius); and minimum values with Thymol (312.5 μg/ml, 156.2 μg/mL and 156.2 μg/ml, respectively for S. mutans, S. oralis, and S. salivarius). All the tested phytochemicals displayed antibacterial activity, thus representing substances with potential applications in preventing tooth decay.
Topics: Acyclic Monoterpenes; Anti-Bacterial Agents; Dental Caries; Microbial Sensitivity Tests; Monoterpenes; Phytochemicals; Streptococcus; Thymol
PubMed: 29412250
DOI: 10.1590/1519-6984.174147