RESUMO
Food contamination by mycotoxigenic fungi is one of the principal factors that cause food loss and economic losses in the food industry. The objective of this work was to incorporate the essential oil from Corymbia citriodora Hook and its constituents citronellal and ß-citronellol into poly(lactic acid) nanofibers; to characterize the nanofibers by scanning electron microscopy (SEM), Fourier transform infrared spectroscopy and differential scanning calorimetry; to evaluate the antifungal activity by the fumigation method; to evaluate the antimycotoxigenic activity against Aspergillus carbonarius, Aspergillus ochraceus, Aspergillus westerdijkiae, Aspergillus flavus, and Aspergillus parasiticus; and to evaluate the morphology of these microorganisms. All the nanofibers had a regular, smooth, and continuous morphology. FTIR analyses confirmed that the active ingredients were incorporated into the polymer matrix. All samples exhibited antifungal and ochratoxigenic inhibitory activities of up to 100% and 99%, respectively, with the best results observed for (PLA + 30 wt% ß-citronellol) nanofibers and (PLA + 30 wt% citronellal) nanofibers. However, 100% inhibition of the production of aflatoxin B1 and B2 was not observed. The images obtained by SEM indicated that the nanofibers caused damage to the hyphae, caused a decrease in the production of spores, and caused deformation, rupture, and non-formation of the conid head, might be an alternative for the control of mycotoxigenic fungi.
Assuntos
Monoterpenos Acíclicos , Antifúngicos , Aspergillus , Nanofibras , Óleos Voláteis , Poliésteres , Nanofibras/química , Poliésteres/química , Poliésteres/farmacologia , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Antifúngicos/farmacologia , Antifúngicos/química , Monoterpenos Acíclicos/farmacologia , Monoterpenos Acíclicos/química , Aspergillus/efeitos dos fármacos , Aldeídos/farmacologia , Aldeídos/química , Testes de Sensibilidade Microbiana , Monoterpenos/farmacologia , Monoterpenos/químicaRESUMO
BACKGROUND: Solid tumors often develop hypoxic regions, leading to aggressive behavior and increased drug resistance. METHODS: The chemical composition of Cymbopogon citratus essential oil (EO) was analyzed using GC-MS. Alginate nanoparticles containing the EO and its primary component, citral, were synthesized via the ionic gelation method. Encapsulation was confirmed using ATR-FTIR analysis. The anticancer efficacy of C. citratus EO, citral, and their respective alginate nanoparticles was evaluated under normoxic (21% oxygen) and hypoxic (1% oxygen) conditions on breast cancer (MDA-MB-231) and melanoma (A-375) cell lines. Additionally, qPCR and flow cytometry were used to assess apoptosis gene expression ratios (Bax/Bcl-2) and levels of apoptosis. RESULTS: Citral (80.98%) was identified as the major component of the EO. Alginate nanoparticles containing C. citratus EO and citral (C. citratus-AlgNPs and citral-AlgNPs) were synthesized with particle sizes of 195 ± 4 nm and 222 ± 9 nm, and zeta potentials of -22 ± 3 mV and - 17 ± 1 mV, respectively. Both samples demonstrated significantly greater efficacy under hypoxic conditions. Citral and C. citratus-AlgNPs had IC50 values of 27 (19-39) µg/mL and 25 (4-147) µg/mL, respectively, against MDA-MB-231 and A-375 cells. Flow cytometry showed increased apoptosis under hypoxic conditions, with the highest rates observed for citral-AlgNPs and C. citratus-AlgNPs (84 ± 5 and 92 ± 5% in MDA-MB-231 and A-375 cells, respectively). CONCLUSION: This study demonstrates that alginate nanoparticles enhance the anticancer activity of C. citratus-AlgNPs and citral, particularly under hypoxic conditions, highlighting their potential for hypoxia-targeted cancer therapies.
Assuntos
Monoterpenos Acíclicos , Alginatos , Neoplasias da Mama , Cymbopogon , Nanopartículas , Óleos Voláteis , Humanos , Cymbopogon/química , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Nanopartículas/química , Linhagem Celular Tumoral , Monoterpenos Acíclicos/farmacologia , Monoterpenos Acíclicos/química , Alginatos/farmacologia , Alginatos/química , Neoplasias da Mama/tratamento farmacológico , Melanoma/tratamento farmacológico , Feminino , Apoptose/efeitos dos fármacosAssuntos
Monoterpenos Acíclicos , Perfumes , Humanos , Perfumes/toxicidade , Perfumes/química , Animais , Medição de Risco , Monoterpenos Acíclicos/toxicidade , Monoterpenos Acíclicos/química , Odorantes , Monoterpenos/toxicidade , Monoterpenos/química , Qualidade de Produtos para o Consumidor , Determinação de Ponto Final , Testes de Toxicidade , Nível de Efeito Adverso não ObservadoRESUMO
Essential oils (EOs) and plant extracts, rich in beneficial chemical compounds, have diverse applications in medicine, food, cosmetics, and agriculture. This study investigates the antibacterial activity of nine essential oil constituents (EOCs) against Escherichia coli, focusing on the effects of treatment pH and biosynthetic requirements. The impact of EOCs on bacterial inactivation in E. coli strains was examined using both nonselective and selective culture media. Computer-assisted drug design (CADD) methods were employed to identify critical binding sites and predict the main binding modes of ligands to proteins. The EOCs, including citral, α-terpinyl acetate, α-terpineol, and linalool, demonstrated significant bacterial inactivation, particularly under acidic conditions. This study revealed that EOCs have an effect on the presence of sublethal damage to both the cytoplasmic membrane and the outer membrane in Gram-negative bacteria. Adding penicillin G to the repair medium prevents the recovery of sublethal injuries in E. coli treated with α-terpinyl acetate, α-terpineol, linalool, and citral, indicating that peptidoglycan synthesis is essential for recovering from these injuries. However, penicillin G did not hinder the recovery process of most sublethally injured cells treated with the other assessed EOCs. Molecular docking studies revealed the favorable binding interactions of α-terpinyl acetate, α-terpineol, linalool, and citral with the ß-lactamase enzyme Toho-1, indicating their potential as effective antibacterial agents. The findings suggest that EOCs could serve as viable alternatives to synthetic preservatives, offering new strategies for combating antibiotic-resistant bacteria.
Assuntos
Antibacterianos , Escherichia coli , Testes de Sensibilidade Microbiana , Óleos Voláteis , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Escherichia coli/efeitos dos fármacos , Antibacterianos/farmacologia , Antibacterianos/química , Simulação de Acoplamento Molecular , Monoterpenos Acíclicos/farmacologia , Monoterpenos Acíclicos/químicaRESUMO
Citrus black spot (CBS) is a fungal disease caused by Phyllosticta citricarpa Kiely, (McAlpine Van der Aa), with most cultivars being susceptible to infection. Currently, disease control is based on the application of protective fungicides, which is restricted due to resistance, health and environmental concerns. Although using natural products for disease management is gaining momentum, more advances are required. This study obtained the metabolic profiles of the essential oil and cuticular waxes of two citrus cultivars with a varying susceptibility to CBS infection using gas chromatography-mass spectrometry. A multivariate data analysis identified possible biomarker compounds that contributed to the difference in susceptibility between the two cultivars. Several identified biomarkers were tested in vitro for their antifungal properties against P. citricarpa. Two biomarkers, propanoic acid and linalool, were able to completely inhibit pathogen growth at 750 mg/L and 2000 mg/L, respectively.
Assuntos
Ascomicetos , Biomarcadores , Citrus , Óleos Voláteis , Doenças das Plantas , Doenças das Plantas/microbiologia , Citrus/química , Citrus/microbiologia , Ascomicetos/química , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Cromatografia Gasosa-Espectrometria de Massas , Antifúngicos/farmacologia , Antifúngicos/química , Monoterpenos Acíclicos/farmacologia , Monoterpenos Acíclicos/química , MetabolomaRESUMO
Tropical and subtropical regions face millions of deaths from mosquito-borne illnesses yearly. Insecticides prevent transmission but pose health risks like dermatitis and allergies. The primary objective was to mitigate the recurring dependence on synthetic insecticides, thereby curbing the development of mosquito resistance. Leaves of Cymbopogon flexuosus (lemongrass) was collected from Mayurbhanj, India, processed, then extracted by steam distillation for essential oils & analyzed spectroscopically. Larvicidal assays were performed across varying concentrations, revealing the significant mortality induced by the Cymbopogon flexuosus extract against Anopheles stephensi larvae. 3D structure was modelled by using G protein-coupled receptors (GPCR) sequence and structural stability was also validated. After docking the binding free energy was determined from GPCR protein with ß-citral complex. Molecular dynamics (MD) study was conducted on the docked pose that displayed an optimal interactome profile. The larvicidal assay at the 12th and 24th hour revealed the highest LC50 (lethal concentration) of 23.493 ppm and 19.664 ppm . ß-Citral has a high binding affinity and an identifiable binding site, which suggests that it may play a larvicidal role in regulating the receptor's function by creating stable complexes with it. ß-Citral from lemongrass oils has potential larvicidal activity and effective against GPCR family 1 of mosquito and highly effective repellents against mosquito-borne diseases.
Assuntos
Anopheles , Cymbopogon , Inseticidas , Larva , Simulação de Acoplamento Molecular , Simulação de Dinâmica Molecular , Animais , Larva/efeitos dos fármacos , Inseticidas/farmacologia , Inseticidas/química , Anopheles/efeitos dos fármacos , Cymbopogon/química , Índia , Folhas de Planta/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Monoterpenos Acíclicos/farmacologia , Monoterpenos Acíclicos/química , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Receptores Acoplados a Proteínas G/metabolismoRESUMO
With growing interest in natural compounds as alternative mosquito repellents, assessing the toxicity and structure of potential repellent naturals like thymol (monoterpene phenol) and geraniol (monoterpene alcohol) is vital for understanding their stability and human impact. This study aimed to determine the structural, toxicity, and binding profiles of thymol and geraniol using computational predictions, xTB metadynamics, quantum mechanics, and principal component analysis. Toxicity studies using Protox-II, T.E.S.T, and SwissADME indicated that thymol and geraniol belong to toxicity class 4 and 5, respectively, with low toxicity predictions in other endpoints. Overall pharmacokinetic profile was generated via pkCSM. Off-target predictions via SwissTarget Predictions, LigTMap, Pharmapper, and SuperPred showed that these molecules can bind to 614 human proteins. The degradation of thymol and geraniol were performed using xTB metadynamics and the outcomes showed that the degradants for both compounds were stable and had lower toxicity profile. Nine tautomers were generated via quantum mechanics for thymol and four for geraniol, with RMSD ranging from 3.8 to 6.3 Å for thymol and 3.6 to 4 Å for geraniol after superimpositions. DFT studies found that HOMO-LUMO values and electronegativity parameters of thymol and geraniol did not differ significantly from their isomers. Binding affinity studies against 614 proteins, analysed via PCA and violin plots, highlighted the probable range of binding. These multifaceted in-silico findings corroborate the stability and potential utility of thymol and geraniol as safer alternatives in repellent applications.
Assuntos
Monoterpenos Acíclicos , Repelentes de Insetos , Proteoma , Timol , Timol/química , Timol/farmacologia , Humanos , Monoterpenos Acíclicos/química , Repelentes de Insetos/química , Repelentes de Insetos/farmacologia , Teoria Quântica , Terpenos/químicaRESUMO
This work aimed to explore an alternative to the use of antibiotics for prevention and treatment of wounds infection caused by two common bacterial pathogens Staphylococcus aureus and Pseudomonas aeruginosa. For this purpose, three different essential oil components (EOCs), namely carvacrol, citronellol and cinnamic acid, were loaded into electrospun fibers of poly-ε-caprolactone (PCL) aided by alpha-cyclodextrin (αCD) and hydroxypropyl-ß-cyclodextrin (HPßCD). Electrospun-fibers prepared with each EOC and their mixtures were screened for antimicrobial capability and characterized regarding morphological, mechanical, thermal, surface polarity, antibiofilm and antioxidant properties. αCD formed poly(pseudo)rotaxanes with PCL and weakly interacted with EOCs, while HPßCD facilitated EOC encapsulation and formation of homogeneous fibers (500-1000 nm diameter) without beads. PCL/HPßCD fibers with high concentration of EOCs (mainly carvacrol and cinnamic acid) showed strong antibiofilm (>3 log CFU reduction) and antioxidant activity (10-50% DPPH scavenging effects). Different performances were recorded for the EOCs and their mixtures; cinnamic acid migrated to fiber surface and was released faster. Fibers biocompatibility was verified using hemolysis tests and in ovo tissue integration and angiogenesis assays. Overall, HPßCD facilitates complete release of EOCs from the fibers to the aqueous medium, being an environment-friendly and cost-effective strategy for the treatment of infected wounds.
Assuntos
Monoterpenos Acíclicos , Antioxidantes , Cinamatos , Cimenos , Monoterpenos , Cicatrização , Cicatrização/efeitos dos fármacos , Cimenos/farmacologia , Cimenos/química , Cinamatos/química , Cinamatos/farmacologia , Monoterpenos Acíclicos/farmacologia , Monoterpenos Acíclicos/química , Antioxidantes/farmacologia , Antioxidantes/química , Monoterpenos/farmacologia , Monoterpenos/química , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Staphylococcus aureus/efeitos dos fármacos , Ciclodextrinas/química , Ciclodextrinas/farmacologia , Biofilmes/efeitos dos fármacos , Nanofibras/química , Testes de Sensibilidade Microbiana , Antibacterianos/farmacologia , Antibacterianos/química , Poliésteres/química , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Pseudomonas aeruginosa/efeitos dos fármacosRESUMO
This investigation employed molten globule state ß-lactoglobulin nanoparticles (MG-BLGNPs) for encapsulating linalool (LN) combined with carboxymethyl chitosan (CMC) coating to enhance the shelf-life of fresh-cut apples. The effect of different MG structures on the encapsulation efficiency of BLGNPs and the properties of coating was studied. Structural characterization and molecular simulation showed structural differences between heat-induced MG state (70-BLGNPs, heated at 70 °C for 1 h) and sodium dodecyl sulfate-co-heat-induced MG state (SDS/70-BLGNPs, treated with 0.192 mg/mL SDS for 10 min, then heated at 70 °C for 1 h), with the latter being more unfolded. LN self-assembles into MG-BLGNPs, among the generated particles, SDS/70-BLG@LN exhibits stronger binding effect and higher LN loading capacity. Integration of MG-BLG@LN into CMC enhanced coating's mechanical properties and adhesion to fresh-cut apples. The SDS/70-BLG@LN/CMC coating showed superior preservation on fresh-cut apples during storage, reducing enzymatic browning, membrane lipid oxidation, and microbial growth while maintaining hardness and overall quality.
Assuntos
Monoterpenos Acíclicos , Quitosana , Conservação de Alimentos , Lactoglobulinas , Malus , Nanopartículas , Quitosana/química , Quitosana/análogos & derivados , Monoterpenos Acíclicos/química , Monoterpenos Acíclicos/farmacologia , Malus/química , Nanopartículas/química , Conservação de Alimentos/métodos , Lactoglobulinas/química , Frutas/químicaRESUMO
Genome wide analysis identified 14 OBPs in B. tabaci Asia II-1, of which six are new to science. Phylogenetic analysis traced their diversity and evolutionary lineage among Hemipteran insects. Comparative analysis reclassified the OBP gene families among B. tabaci cryptic species: Asia I, II-1, MEAM1, and MED. The 14 OBPs were clustered on four chromosomes of B. tabaci. RT-qPCR showed high expression of OBP3 and 8 across all body tissues and OBP10 in the abdomen. Molecular docking showed that OBP 3 and 10 had high affinity bonding with different candidate ligands, with binding energies ranging from -5.0 to -7.7 kcal/mol. Competitive fluorescence binding assays revealed that ß-caryophyllene and limonene had high binding affinities for OBP3 and 10, with their IC50 values ranging from 9.16 to 14 µmol·L-1 and KD values around 7 to 9 µmol·L-1. Behavioural assays revealed that ß-caryophyllene and carvacrol were attractants, ß-ocimene and limonene were repellents, and γ-terpinene and ß-ocimene were oviposition deterrents to B. tabaci. Functional validation by RNAi demonstrated that OBP3 and OBP10 modulated host recognition of B. tabaci. This study expands our understanding of the genomic landscape of OBPs in B. tabaci, offering scope for developing novel pest control strategies.
Assuntos
Hemípteros , Proteínas de Insetos , Filogenia , Receptores Odorantes , Sesquiterpenos , Animais , Hemípteros/genética , Receptores Odorantes/genética , Receptores Odorantes/metabolismo , Receptores Odorantes/química , Proteínas de Insetos/genética , Proteínas de Insetos/química , Proteínas de Insetos/metabolismo , Sesquiterpenos/farmacologia , Sesquiterpenos/metabolismo , Sesquiterpenos/química , Sesquiterpenos Policíclicos/farmacologia , Sesquiterpenos Policíclicos/química , Cimenos/farmacologia , Cimenos/química , Simulação de Acoplamento Molecular , Monoterpenos/farmacologia , Monoterpenos/metabolismo , Monoterpenos/química , Limoneno/farmacologia , Limoneno/química , Limoneno/metabolismo , Monoterpenos Acíclicos/metabolismo , Monoterpenos Acíclicos/farmacologia , Monoterpenos Acíclicos/química , Cicloexenos/metabolismo , Cicloexenos/farmacologia , Cicloexenos/química , Terpenos/metabolismo , Terpenos/química , Terpenos/farmacologia , Genoma de Inseto , Repelentes de Insetos/farmacologia , Repelentes de Insetos/química , Genômica/métodos , Monoterpenos Cicloexânicos , AlcenosRESUMO
Geraniol, a primary component of several essential oils, has been associated with broad-spectrum antiprotozoal activities, although moderate to weak. This study primarily concentrated on the synthesis of hydrazinated geraniol derivatives as potential antiprotozoal agents. The synthesised compounds were tested in vitro against different parasitic protozoans of clinical relevance, including Trypanosoma brucei brucei, Trypanosoma brucei rhodesiense, Trypanosoma cruzi and Leishmania infantum. Compounds 6, 8, 13, 14 and 15 demonstrated low micromolar activity against the different parasites. Compounds 8, 13, 14 and 15 had the highest efficacy against Trypanosoma brucei rhodesiense, as indicated by their respective IC50 values of 0.74, 0.56, 1.26 and 1.00 µM. Compounds 6, 14 and 15 displayed the best activity against Trypanosoma brucei brucei, with IC50 values of 1.49, 1.48 and 1.85 µM, respectively. The activity of compounds 6, 14 and 15 also extended to intracellular Trypanosoma cruzi, with IC50 values of 5.14, 6.30 and 4.90 µM, respectively. Compound 6, with an IC50 value of 11.73 µM, and compound 14, with an IC50 value of 8.14 µM, demonstrated some modest antileishmanial activity.
Assuntos
Monoterpenos Acíclicos , Antiprotozoários , Leishmania infantum , Testes de Sensibilidade Parasitária , Trypanosoma brucei brucei , Trypanosoma cruzi , Trypanosoma cruzi/efeitos dos fármacos , Leishmania infantum/efeitos dos fármacos , Relação Estrutura-Atividade , Antiprotozoários/farmacologia , Antiprotozoários/síntese química , Antiprotozoários/química , Trypanosoma brucei brucei/efeitos dos fármacos , Monoterpenos Acíclicos/farmacologia , Monoterpenos Acíclicos/síntese química , Monoterpenos Acíclicos/química , Concentração Inibidora 50 , Trypanosoma brucei rhodesiense/efeitos dos fármacos , Hidrazinas/farmacologia , Hidrazinas/síntese química , Hidrazinas/química , Estrutura Molecular , Relação Dose-Resposta a Droga , Animais , HumanosRESUMO
This comprehensive review endeavors to illuminate the nuanced facets of linalool, a prominent monoterpene found abundantly in essential oils, constituting a massive portion of their composition. The biomedical relevance of linalool is a key focus, highlighting its therapeutic attributes observed through anti-nociceptive effects, anxiolytic properties, and behavioral modulation in individuals affected by dementia. These findings underscore the compound's potential application in biomedical applications. This review further explores contemporary formulations, delineating the adaptability of linalool in nano-emulsions, microemulsions, bio-capsules, and various topical formulations, including topical gels and lotions. This review covers published and granted patents between 2018-2024 and sheds light on the evolving landscape of linalool applications, revealing advancements in dermatological, anti-inflammatory, and antimicrobial domains.
Assuntos
Monoterpenos Acíclicos , Humanos , Monoterpenos Acíclicos/farmacologia , Monoterpenos Acíclicos/uso terapêutico , Monoterpenos Acíclicos/química , Anti-Inflamatórios/uso terapêutico , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/administração & dosagem , Animais , Anti-Infecciosos/uso terapêutico , Anti-Infecciosos/farmacologia , Ansiolíticos/uso terapêutico , Ansiolíticos/farmacologia , Analgésicos/uso terapêutico , Analgésicos/farmacologia , Patentes como Assunto , Emulsões , Óleos Voláteis/uso terapêutico , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Fármacos Dermatológicos/uso terapêutico , Fármacos Dermatológicos/farmacologia , Fármacos Dermatológicos/administração & dosagemRESUMO
Oleogels containing bioactive substances such as citral (CT) are used as functional food ingredients. However, little information is available on the influence of different oleogel network structure caused by CT addition and fatty acid distribution on its digestion behavior. Coconut oil, palm oil, high oleic peanut oil, safflower seed oil, and perilla seed oil were used in this study. The results showed that perilla seed oil-CT-based oleogels had the highest oil-holding capacity (99.03 ± 0.3), whereas CT addition higher than 10 wt% could lead to the morphology collapse of oleogels. Physical and thermodynamic analyses revealed that CT could reduce oleogel hardness and higher unsaturated fatty acid content is more likely to form oleogel with stable and tight crystalline network. Moreover, the dense structure of oleogels hinders the contact between oleogels and lipase, thus weakening triglyceride digestion. These findings provide valuable insights into the design of oleogels loading with CT.
Assuntos
Monoterpenos Acíclicos , Digestão , Ácidos Graxos , Compostos Orgânicos , Óleos de Plantas , Monoterpenos Acíclicos/química , Óleos de Plantas/química , Ácidos Graxos/química , Ácidos Graxos/metabolismo , Compostos Orgânicos/química , Monoterpenos/química , Modelos Biológicos , Humanos , Óleo de Palmeira/química , Óleo de Coco/química , Ácido alfa-LinolênicoRESUMO
The thrust of the study was to determine the chemical composition of the essential oils extracted from Thymus pallescens de Noé and Cymbogon citratus Stapf. as well as to evaluate their efficacy in controlling Sitophilus zeamais Motschulsky and Tribolium castaneum (Herbst) in either single or combined populations. Carvacrol (56.04%) and geraniol (20.86%) were identified as the major constituents of T. pallescens and C. citratus respectively. The tested essential oils showed pronounced insecticidal activity against the pest species in relation with the applied doses. T. pallescens EO had the highest efficacy and S. zeamais was found to be more susceptible to both individual and combined treatments. With reference to the contact and fumigation assessments, T. pallescens EO effectuated corrected mortality rates ranging from 42.5-100% to 25-100% in S. zeamais with corresponding lethal concentration (LC50) values of 17.7 µl/ml and 15µL/L air respectively. Whereas, the T. pallescens EO exhibited corrected mortality rates of 42.5-100% and 20-100% with corresponding LC50 values of 18.1 µl/ml and 15.5 µL/L air against T. castaneum in contact and fumigation assessments, respectively. The corrected mortality rates increased for both insect species when using combination treatments, with significant increases in the LC50 values, ranging from 8.59 to 49.9% for both pest species. Analysis of energy biomarkers in the treated insects indicate significantly increased protein and carbohydrate contents and decreased lipids levels. The study therefore demonstrated the bio-insecticidal toxicity of the EOs from T. pallescens and C. citratus against two important maize post-harvest pests, concurrently revealing significant positive and negative insecticidal activity gradients in relation to single or combined populations.
Assuntos
Inseticidas , Óleos Voláteis , Thymus (Planta) , Tribolium , Animais , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Tribolium/efeitos dos fármacos , Inseticidas/farmacologia , Inseticidas/química , Thymus (Planta)/química , Monoterpenos Acíclicos/farmacologia , Monoterpenos Acíclicos/química , Gorgulhos/efeitos dos fármacos , Cimenos/farmacologia , Cimenos/químicaRESUMO
Ferulic acid (Fer) and geraniol (Ger) are natural compounds whose antioxidant and anti-inflammatory activity confer beneficial properties, such as antibacterial, anticancer, and neuroprotective effects. However, the short half-lives of these compounds impair their therapeutic activities after conventional administration. We propose, therefore, a new prodrug (Fer-Ger) obtained by a bio-catalyzed ester conjugation of Fer and Ger to enhance the loading of solid lipid microparticles (SLMs) designed as Fer-Ger delivery and targeting systems. SLMs were obtained by hot emulsion techniques without organic solvents. HPLC-UV analysis evidenced that Fer-Ger is hydrolyzed in human or rat whole blood and rat liver homogenates, with half-lives of 193.64 ± 20.93, 20.15 ± 0.75, and 3.94 ± 0.33 min, respectively, but not in rat brain homogenates. Studies on neuronal-differentiated mouse neuroblastoma N2a cells incubated with the reactive oxygen species (ROS) inductor H2O2 evidenced the Fer-Ger ability to prevent oxidative injury, despite the fact that it appears ROS-promoting. The amounts of Fer-Ger encapsulated in tristearin SLMs, obtained in the absence or presence of glucose, were 1.5 ± 0.1%, allowing the control of the prodrug release (glucose absence) or to sensibly enhance its water dissolution rate (glucose presence). These new "green" carriers can potentially prolong the beneficial effects of Fer and Ger or induce neuroprotection as nasal formulations.
Assuntos
Monoterpenos Acíclicos , Ácidos Cumáricos , Pró-Fármacos , Pró-Fármacos/química , Pró-Fármacos/farmacologia , Animais , Ácidos Cumáricos/química , Ratos , Camundongos , Humanos , Hidrólise , Monoterpenos Acíclicos/química , Monoterpenos Acíclicos/farmacologia , Linhagem Celular Tumoral , Ésteres/química , Terpenos/química , Terpenos/farmacologia , Espécies Reativas de Oxigênio/metabolismo , Antioxidantes/química , Antioxidantes/farmacologiaRESUMO
Hemerocallis L. possesses abundant germplasm resources and holds significant value in terms of ornamental, edible, and medicinal aspects. However, the quality characteristics vary significantly depending on different varieties. Selection of a high-quality variety with a characteristic aroma can increase the economic value of Hemerocallis flowers. The analytic hierarchy process (AHP) is an effective decision-making method for comparing and evaluating multiple characteristic dimensions. By applying AHP, the aromatic character of 60 varieties of Hemerocallis flowers were analyzed and evaluated in the present study. Headspace solid-phase microextraction gas chromatography-mass spectrometry (HS-SPME-GC-MS) was employed to identify volatile components in Hemerocallis flowers. Thirteen volatile components were found to contribute to the aroma of Hemerocallis flowers, which helps in assessing their potential applications in essential oil, aromatherapy, and medical treatment. These components include 2-phenylethanol, geraniol, linalool, nonanal, decanal, (E)-ß-ocimene, α-farnesene, indole, nerolidol, 3-furanmethanol, 3-carene, benzaldehyde and benzenemethanol. The varieties with better aromatic potential can be selected from a large amount of data using an AHP model. This study provides a comprehensive understanding of the characteristics of the aroma components in Hemerocallis flowers, offers guidance for breeding, and enhances the economic value of Hemerocallis flowers.
Assuntos
Flores , Cromatografia Gasosa-Espectrometria de Massas , Microextração em Fase Sólida , Compostos Orgânicos Voláteis , Compostos Orgânicos Voláteis/análise , Compostos Orgânicos Voláteis/química , Microextração em Fase Sólida/métodos , Flores/química , Odorantes/análise , Monoterpenos Acíclicos/química , Monoterpenos Acíclicos/análise , Óleos Voláteis/química , Óleos Voláteis/análise , Sesquiterpenos/análise , Álcool Feniletílico/análogos & derivados , Álcool Feniletílico/análise , Álcool Feniletílico/química , Alcenos , IndóisRESUMO
Although Enshi Yulu tea (ESYL) possesses a distinctive fragrance, there is a scarcity of studies focusing on its primary volatiles or aroma genesis. This study aims to elucidate the dynamics in the profiles of aromas and volatiles through aroma profiling analysis and headspace solid-phase microextraction/gas chromatography-mass spectrometry. A total of 10 aroma attributes and 128 volatiles were identified in ESYL, with geraniol and linalool exhibiting the highest levels, and alcohols constituting the predominant proportion. Besides, a relative odor activity value (ROAV) based molecular aroma wheel was constructed, revealing 12 key odorants with ROAVs >1, wherein linalool, ß-ionone, and nonanal ranked highest. Notably, steaming and final drying emerged as critical steps for ESYL aroma development, while the non-enzymatic degradation of fatty acids likely contributed to the formation of its fresh aroma. These findings significantly enhance our comprehension of ESYL aroma formation.
Assuntos
Cromatografia Gasosa-Espectrometria de Massas , Odorantes , Microextração em Fase Sólida , Compostos Orgânicos Voláteis , Compostos Orgânicos Voláteis/química , Odorantes/análise , Manipulação de Alimentos , Chá/química , Camellia sinensis/química , Monoterpenos Acíclicos/química , Monoterpenos Acíclicos/análiseRESUMO
Myrcene (ß-myrcene), found in essential oils from plant species such as hops and cannabis, has many advantageous properties, but its use is limited due to volatility and low solubility in water. One way to circumvent these limitations is to encapsulate the essential oils in a polymer matrix. However, these hydrophobic molecules are difficult to quantify when dispersed in water. Seeking to study the release of this terpene in drug release tests from polymeric matrices, this work aimed to develop an easy and cheap UV spectrophotometric method for the quantification of ß-myrcene in aqueous medium. To achieves this goal, samples were prepared in 0.05% (w/v) polysorbate 80 solution, with concentrations of ß-myrcene ranging from 0.01% to 0.1% (v/v), and were analyzed at 226 nm. Each sample was analyzed in triplicate and repeated on three different days, to evaluate the repeatability of the results. The results were subjected to Q, F and Student's t-tests. The regression parameters obtained for ß-myrcene were above 0.99 and through statistical analysis, it was possible to confirm the repeatability for the results. The values of the limits of detection and quantification indicated that the method is not affected by intrinsic factors of the equipment. The results of accuracy, robustness and selectivity showed recovery rates within acceptable limits. This demonstrates that the quantification of ß-myrcene in aqueous medium by UV spectrophotometry is feasible.
Assuntos
Quitosana , Espectrofotometria Ultravioleta , Água , Espectrofotometria Ultravioleta/métodos , Água/química , Quitosana/química , Monoterpenos Acíclicos/análise , Monoterpenos Acíclicos/química , Alcenos/análise , Alcenos/química , Polissorbatos/química , Polissorbatos/análise , Solubilidade , Reprodutibilidade dos Testes , Óleos Voláteis/análise , Óleos Voláteis/químicaRESUMO
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.
Assuntos
Monoterpenos Acíclicos , Apoptose , Proliferação de Células , Neoplasias de Cabeça e Pescoço , Monoterpenos , Óleos Voláteis , Humanos , Proliferação de Células/efeitos dos fármacos , Monoterpenos Acíclicos/farmacologia , Monoterpenos Acíclicos/química , Neoplasias de Cabeça e Pescoço/tratamento farmacológico , Neoplasias de Cabeça e Pescoço/metabolismo , Neoplasias de Cabeça e Pescoço/genética , Apoptose/efeitos dos fármacos , Linhagem Celular Tumoral , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Monoterpenos/farmacologia , Monoterpenos/química , Pontos de Checagem do Ciclo Celular/efeitos dos fármacos , Citrus/química , Óleos de Plantas/farmacologia , Óleos de Plantas/químicaRESUMO
One major challenge in predicting secondary organic aerosol (SOA) formation in the atmosphere is incomplete representation of biogenic volatile organic compounds (BVOCs) emitted from plants, particularly those that are emitted as a result of stress - a condition that is becoming more frequent in a rapidly changing climate. One of the most common types of BVOCs emitted by plants in response to environmental stress are acyclic terpenes. In this work, SOA is generated from the photooxidation of acyclic terpenes in an oxidation flow reactor and compared to SOA production from a reference cyclic terpene - α-pinene. The acyclic terpenes used as SOA precursors included ß-myrcene, ß-ocimene, and linalool. Results showed that oxidation of all acyclic terpenes had lower SOA yields measured after 4 days photochemical age, in comparison to α-pinene. However, there was also evidence that the condensed organic products that formed, while a smaller amount overall, had a higher oligomeric content. In particular, ß-ocimene SOA had higher oligomeric content than all the other chemical systems studied. SOA composition data from ultra-high performance liquid chromatography with electrospray ionization mass spectrometry (UHPLC-ESI-MS) was combined with mechanistic modeling using the Generator for Explicit Chemistry and Kinetics of Organics in the Atmosphere (GECKO-A) to explore chemical mechanisms that could lead to this oligomer formation. Calculations based on composition data suggested that ß-ocimene SOA was more viscous with a higher glass transition temperature than other SOA generated from acyclic terpene oxidation. This was attributed to a higher oligomeric content compared to other SOA systems studied. These results contribute to novel chemical insights about SOA formation from acyclic terpenes and relevant chemistry processes, highlighting the importance of improving underrepresented biogenic SOA formation in chemical transport models.