RESUMEN
Heterogeneous oxidation by gas-phase oxidants is an important chemical transformation pathway of secondary organic aerosol (SOA) and plays an important role in controlling the abundance, properties, as well as climate and health impacts of aerosols. However, our knowledge on this heterogeneous chemistry remains inadequate. In this study, the heterogeneous oxidation of α-pinene ozonolysis SOA by hydroxyl (OH) radicals was investigated under both low and high relative humidity (RH) conditions, with an emphasis on the evolution of molecular composition of SOA and its RH dependence. It is found that the heterogeneous oxidation of SOA at an OH exposure level equivalent to 12 hr of atmospheric aging leads to particle mass loss of 60% at 25% RH and 95% at 90% RH. The heterogeneous oxidation strongly changes the molecular composition of SOA. The dimer-to-monomer signal ratios increase dramatically with rising OH exposure, in particular under high RH conditions, suggesting that aerosol water stimulates the reaction of monomers with OH radicals more than that of dimers. In addition, the typical SOA tracer compounds such as pinic acid, pinonic acid, hydroxy pinonic acid and dimer esters (e.g., C17H26O8 and C19H28O7) have lifetimes of several hours against heterogeneous OH oxidation under typical atmospheric conditions, which highlights the need for the consideration of their heterogeneous loss in the estimation of monoterpene SOA concentrations using tracer-based methods. Our study sheds lights on the heterogeneous oxidation chemistry of monoterpene SOA and would help to understand their evolution and impacts in the atmosphere.
Asunto(s)
Aerosoles , Contaminantes Atmosféricos , Monoterpenos Bicíclicos , Humedad , Radical Hidroxilo , Oxidación-Reducción , Aerosoles/química , Radical Hidroxilo/química , Monoterpenos Bicíclicos/química , Contaminantes Atmosféricos/química , Contaminantes Atmosféricos/análisis , Ozono/química , Modelos Químicos , Atmósfera/química , Monoterpenos/químicaRESUMEN
Pistacia palaestina Boiss. is a common tree in the Mediterranean maquis. The leaves of this plant accumulate defensive monoterpenes, whose levels greatly increase in galls induced by the aphid Baizongia pistaciae. We previously found a significant chemopolymorphism in monoterpene content among individual trees, but the chirality of these monoterpenes was unknown. Although most plant species specifically accumulate one enantiomeric form of a given compound, P. palaestina individuals display chemopolymorphism in the chirality of the key monoterpenes accumulated. We report here a marked enantiomeric variation for the limonene, α- and ß-pinene, camphene, sabinene, δ-3-carene, and terpene-4-ol content in leaves and galls of nine different naturally growing P. palaestina trees. Interestingly, insect-induced gall monoterpene composition is an augmentation of the specific enantiopolymorphism originally displayed by each individual tree.
Asunto(s)
Monoterpenos , Pistacia , Hojas de la Planta , Hojas de la Planta/química , Monoterpenos/química , Pistacia/química , Estereoisomerismo , Animales , Áfidos , Tumores de Planta/parasitologíaRESUMEN
During the development of animal organs, various adverse stimuli or toxic environments can induce oxidative stress and delay ovarian development. Paeoniflorin (PF), the main active ingredient of the traditional Chinese herb Paeonia lactiflora Pall., has protective effects on various diseases by preventing oxidative stress. However, the mechanism by which PF attenuates oxidative damage in mouse ovaries remains unclear. We evaluated the protective effects of PF on ovaries in an H2O2-induced mouse oxidative stress model. The H2O2-induced mouse ovarian oxidative stress model was used to explore the protective effect of PF on ovarian development. Histology and follicular development were observed. We then detected related indicators of cell apoptosis, oxidative stress, and autophagy in mouse ovaries. We found that PF inhibited H2O2-induced ovarian cell apoptosis and ferroptosis and promoted granulosa cell proliferation. PF prevented oxidative stress by increasing nuclear factor erythroid 2-related factor 2 (Nrf2) and heme oxygenase-1 (HO-1) expression levels. In addition, the autophagic flux of ovarian cells was activated and was accompanied by increased lysosomal biogenesis. Moreover, PF-mediated autophagy was involved in clearing mitochondria damaged by H2O2. Importantly, PF administration significantly increased the number of primordial follicles, primary follicles, secondary follicles, and antral follicles. PF administration improved ovarian sizes compared with the H2O2 group. The present study suggested that PF administration reversed H2O2-induced ovarian developmental delay and promoted follicle development. PF-activated mitophagy is crucial for preventing oxidative stress and improving mitochondrial quality.
Asunto(s)
Glucósidos , Peróxido de Hidrógeno , Mitofagia , Ovario , Estrés Oxidativo , Animales , Femenino , Estrés Oxidativo/efectos de los fármacos , Glucósidos/farmacología , Ratones , Ovario/efectos de los fármacos , Ovario/metabolismo , Mitofagia/efectos de los fármacos , Peróxido de Hidrógeno/metabolismo , Monoterpenos/farmacología , Apoptosis/efectos de los fármacos , Autofagia/efectos de los fármacos , Hemo-Oxigenasa 1/metabolismo , Proliferación Celular/efectos de los fármacos , Factor 2 Relacionado con NF-E2/metabolismo , Células de la Granulosa/efectos de los fármacos , Células de la Granulosa/metabolismoRESUMEN
This work used headspace solid-phase microextraction with gas chromatography-mass spectrometry (HS-SPME-GC-MS) to analyze the volatile components of hydrosols of Citrus × aurantium 'Daidai' and Citrus × aurantium L. dried buds (CAVAs and CADBs) by immersion and ultrasound-microwave synergistic-assisted steam distillation. The results show that a total of 106 volatiles were detected in hydrosols, mainly alcohols, alkenes, and esters, and the high content components of hydrosols were linalool, α-terpineol, and trans-geraniol. In terms of variety, the total and unique components of CAVA hydrosols were much higher than those of CADB hydrosols; the relative contents of 13 components of CAVA hydrosols were greater than those of CADB hydrosols, with geranyl acetate up to 15-fold; all hydrosols had a citrus, floral, and woody aroma. From the pretreatment, more volatile components were retained in the immersion; the relative contents of linalool and α-terpineol were increased by the ultrasound-microwave procedure; and the ultrasound-microwave procedure was favorable for the stimulation of the aroma of CAVA hydrosols, but it diminished the aroma of the CADB hydrosols. This study provides theoretical support for in-depth exploration based on the medicine food homology properties of CAVA and for improving the utilization rate of waste resources.
Asunto(s)
Monoterpenos Acíclicos , Citrus , Monoterpenos Ciclohexánicos , Cromatografía de Gases y Espectrometría de Masas , Microextracción en Fase Sólida , Compuestos Orgánicos Volátiles , Cromatografía de Gases y Espectrometría de Masas/métodos , Citrus/química , Microextracción en Fase Sólida/métodos , Compuestos Orgánicos Volátiles/análisis , Compuestos Orgánicos Volátiles/química , Compuestos Orgánicos Volátiles/aislamiento & purificación , Monoterpenos Acíclicos/análisis , Monoterpenos Ciclohexánicos/análisis , Terpenos/análisis , Terpenos/química , Monoterpenos/análisis , Monoterpenos/aislamiento & purificación , Odorantes/análisis , Destilación/métodos , AcetatosRESUMEN
This research aimed to produce and analyze zinc oxide nanoparticles (ZNPs) loaded with linalool (LZNPs), and to evaluate their in vitro and in vivo efficacy through targeting the inflammation and oxidative stress. LZNPs were synthesized using an ethanolic solution of polyvinyl alcohol. The Malstat technique was used to evaluate the effectiveness of LZNPs against both sensitive and resistant strains of Plasmosium falciparum. In vivo effects of ZNPs and LZNPs on parasite growth suppression, survival rate, oxidative stress markers, antioxidant genes, and gene and protein levels of inflammatory cytokines were evaluated by Real-time PCR and Western blot techniques. The results indicated that LZNPs demonstrated noteworthy (P < 0.001) antiplasmodial activity against both susceptible and resistant strains of P. falciparum. P. berghei NK65 strain-infected mice treated with the ZNPs and LZNPs at doses of 5-15 mg/kg notably (p < 0.001) increased the survival rates and parasite growth suppression. LZNPs at 5-15 mg/kg demonstrated a significant (p < 0.001) decrease in oxidative stress markers, increased the expression level of antioxidant genes, and reduced the gene and protein expression level of inflammatory cytokines. The current experimental study demonstrated the potent in vitro antiplasmodial activity of LZNPs against chloroquine-resistant and sensitive strains of P. falciparum compared to ZNPs alone. Additionally, the study identified the potential benefits of this nanocomposite in suppressing the parasite and extending the survival rate in mice infected with P. berghei by targeting inflammation and oxidative stress. It also showed minimal toxicity in liver and kidney function in healthy mice. Nevertheless, further research is essential to elucidate the comprehensive mechanisms and practical effectiveness of LZNPs.
Asunto(s)
Monoterpenos Acíclicos , Antimaláricos , Monoterpenos , Nanopartículas , Estrés Oxidativo , Plasmodium berghei , Plasmodium falciparum , Óxido de Zinc , Animales , Monoterpenos Acíclicos/farmacología , Óxido de Zinc/farmacología , Óxido de Zinc/administración & dosificación , Óxido de Zinc/química , Ratones , Plasmodium berghei/efectos de los fármacos , Antimaláricos/farmacología , Antimaláricos/administración & dosificación , Nanopartículas/química , Estrés Oxidativo/efectos de los fármacos , Plasmodium falciparum/efectos de los fármacos , Monoterpenos/farmacología , Monoterpenos/administración & dosificación , Monoterpenos/química , Malaria/tratamiento farmacológico , Citocinas/metabolismo , Modelos Animales de Enfermedad , Masculino , Antioxidantes/farmacología , Antioxidantes/administración & dosificación , Portadores de Fármacos/químicaRESUMEN
Utilizing Density Functional Theory (DFT) calculations at the B3LYP/QZVP level and incorporating the Conductor-like Polarizable Continuum Model (C-PCM) for solvation, the thermodynamic and chemical activity properties of 21-(hydroxymethoxy)henicosadecaenal, identified in cultured freshwater pearls from the mollusk Hyriopsis cumingii, have been elucidated. The study demonstrates that this compound releases formaldehyde, a potent antimicrobial agent, through dehydrogenation and deprotonation processes in both hydrophilic and lipophilic environments. Moreover, this polyenal exhibits strong anti-reductant properties, effectively scavenging free radicals. These critical properties classify the pearl-derived ingredient as a natural multi-functional compound, serving as a coloring, antiradical, and antimicrobial agent. The 2-(hydroxymethoxy)vinyl (HMV) moiety responsible for the formaldehyde release can be transferred to other compounds, thereby enhancing their biological activity. For instance, tyrosol (4-(2-hydroxyethyl)phenol) can be modified by substituting the less active 2-hydroxyethyl group with the active HMV one, and hinokitiol (4-isopropylotropolone) can be functionalized by attaching this moiety to the tropolone ring. A new type of meso-carrier, structurally modeled on pearls, with active substances loaded both in the layers and the mineral part, has been proposed.
Asunto(s)
Alcohol Feniletílico , Tropolona , Tropolona/análogos & derivados , Tropolona/química , Tropolona/farmacología , Alcohol Feniletílico/análogos & derivados , Alcohol Feniletílico/química , Alcohol Feniletílico/farmacología , Monoterpenos/química , Monoterpenos/farmacología , Formaldehído/química , Animales , Antioxidantes/química , Antioxidantes/farmacología , Antiinfecciosos/química , Antiinfecciosos/farmacología , Estructura Molecular , TermodinámicaRESUMEN
Molecular hybridization is a widely used strategy in drug discovery and development processes that consists of the combination of two bioactive compounds toward a novel entity. In the current study, two libraries of hybrid derivatives coming from the linkage of sesquiterpene counterparts dihydroartemisinin and artesunic acid, with a series of monoterpenes, were synthesized and evaluated by cell viability assay on primary and metastatic melanoma cell lines. Almost all the obtained compounds showed micromolar antimelanoma activity and selectivity toward the metastatic form of this cancer. Four hybrid derivatives containing perillyl alcohol, citronellol, and nerol as monoterpene counterpart emerged as the best compounds of the series, with nerol being active in combination with both sesquiterpenes, dihydroartemisinin and artesunic acid. Preliminary studies on the mechanism of action have shown the dependence of the pharmacological activity of newly synthesized hybrids on the formation of carbon- and oxygen-centered radical species. This study demonstrated the positive modulation of the pharmacodynamic effect of artemisinin semisynthetic derivatives dihydroartemisinin and artesunic acid due to the hybridization with monoterpene counterparts.
Asunto(s)
Artemisininas , Monoterpenos , Artemisininas/farmacología , Artemisininas/química , Monoterpenos/química , Monoterpenos/farmacología , Humanos , Línea Celular Tumoral , Melanoma/tratamiento farmacológico , Melanoma/patología , Melanoma/genética , Melanoma/metabolismo , Antineoplásicos/farmacología , Antineoplásicos/química , Antineoplásicos/síntesis química , Supervivencia Celular/efectos de los fármacosRESUMEN
In this study, multiple analytical approaches, including simultaneous enantiomeric and isotopic analysis, were employed to thoroughly investigate the volatile fraction in Moscato giallo grape berries and wines. For the qualitative and quantitative profiling, a fast GC-QqQ/MS approach was successfully utilized. However, prior to isotopic analysis, the extracts underwent an additional concentration step, necessitating an assessment of isotopic fractionation during the concentration process. Once the absence of carbon isotopic fractionation was confirmed, this research aimed to develop a suitable gas chromatographic method for the simultaneous detection of both enantiomeric and isotopic ratios of target monoterpenoids in Moscato giallo samples. To address the limitations associated with a one-dimensional approach, multidimensional gas chromatography was employed to enhance separation before IRMS and qMS detections. Utilizing a Deans switch transfer device, the coupling of an apolar column in the first dimension and a chiral cyclodextrin-based stationary phase in the second dimension proved effective for this purpose. The data obtained from the analysis of Moscato giallo samples allowed for the assessment of natural isotopic and enantiomeric distributions in grapes and wines for the first time in the literature. Significant enantiomeric excesses were observed for the target terpenoids investigated. Regarding isotopic distribution, a consistent trend was observed for all detected target terpenols, including the linalool enantiomers. To date, this study represents the first investigation of simultaneous δ13C and chiral investigation of the main terpenoids in oenological products in the literature.
Asunto(s)
Cromatografía de Gases y Espectrometría de Masas , Vitis , Vino , Vitis/química , Vino/análisis , Estereoisomerismo , Cromatografía de Gases y Espectrometría de Masas/métodos , Isótopos de Carbono/análisis , Monoterpenos/análisis , Monoterpenos/química , Frutas/químicaRESUMEN
Chemical residues in food pose health risks such as cancer and liver issues. This has driven the search for safer natural alternatives to synthetic fungicides and preservatives. The aim of this study was to characterize the chemical composition of the essential oils (EO), determine the polyphenolic contents, and evaluate the in vitro antioxidant and antifungal activities of methanol extracts (ME), essential oils (EO), and powders from Rosmarinus officinalis L. (rosemary) and Thymus ciliatus (Desf) Benth. (thyme) from the M'sila region, Algeria. The chemical composition of the EOs was determined by GC-MS. R. officinalis EO was composed of 31 components, mainly camphor (41.22%), camphene (18.14%), and α-pinene (17.49%); T. ciliatus EO was composed of 58 components, mainly, in percentage, α-pinene (22.18), myrcene (13.13), ß-pinene (7.73), ß-caryophyllene (10.21), and germacrene D (9.90). The total phenols and flavonoids were determined spectrophotometrically, and the rosemary ME was found to possess the highest polyphenolic content (127.1 ± 2.40 µg GAE/mg), while the thyme ME had the highest flavonoid content (48.01 ± 0.99 µg QE/mg). The antioxidant activity was assessed using three methods: rosemary ME was the most potent, followed by DPPH (IC50 = 13.43 ± 0.14 µg/mL), ß-carotene/linoleic acid (IC50 = 39.01 ± 2.16 µg/mL), and reducing power (EC50 = 15.03 ± 1.43 µg/mL). Antifungal activity was assessed for 32 pathogenic and foodborne fungi. Four methods were applied to the solid medium. Incorporating the powdered plant into the culture medium (at 10%) reduced the fungal growth to greater than 50% in 21.88% and 6.25% of all fungal isolates, for R. officinalis and T. ciliatus, respectively. The ME, applied by the well diffusion method (0.1 g/mL), was less effective. Different concentrations of EO were tested. Incorporating the EO into the culture medium (1500 µL/L) inhibited 50% of the molds to levels of 50 and 75% for R. officinalis and T. ciliatus, respectively, with the complete inhibition of four fungi. Fumigated EO (15 µL) inhibited 65% of the molds to levels of 65 and 81.25% for R. officinalis and T. ciliatus, respectively, with the complete inhibition of five fungi. There was little to no sporulation in conjunction with the inhibition. Our results revealed some of the potential of the studied plants to fight foodborne molds and presented their promising characteristics as a source of alternatives to chemical pesticides and synthetic preservatives. Further studies are needed to find adequate application techniques in the food safety area.
Asunto(s)
Antifúngicos , Antioxidantes , Aceites Volátiles , Extractos Vegetales , Rosmarinus , Thymus (Planta) , Aceites Volátiles/farmacología , Aceites Volátiles/química , Thymus (Planta)/química , Rosmarinus/química , Antioxidantes/farmacología , Antioxidantes/química , Extractos Vegetales/farmacología , Extractos Vegetales/química , Antifúngicos/farmacología , Antifúngicos/química , Fitoquímicos/farmacología , Fitoquímicos/química , Fitoquímicos/análisis , Monoterpenos Bicíclicos/farmacología , Monoterpenos Bicíclicos/química , Metanol/química , Polvos , Monoterpenos Acíclicos/farmacología , Monoterpenos/farmacología , Monoterpenos/análisis , Monoterpenos/química , Alcanfor/farmacología , Alcanfor/análisis , Alcanfor/química , AlquenosRESUMEN
The whole Hypericum patulum Thunb. plant is utilized in traditional medicine for its properties of clearing heat, detoxifying, soothing meridians, relaxing the liver, and stopping bleeding. In folk medicine, it is frequently used to treat hepatitis, colds, tonsillitis, and bruises. Phytochemical investigation of a 30% ethanol extract of the fresh ripe fruits of H. patulum has resulted in the isolation of two new pinane-type monoterpenoid glycosides 1-2, named patulumside E-F, and three new chain-shaped monoterpenoid glycosides 3-5, named patulumside G-H, J. Their structures were determined using extensive spectroscopic techniques, such as HR-ESI-MS, 1D and 2D NMR spectroscopy, and electronic circular dichroism (ECD) calculation. The anti-inflammatory activities of these compounds were evaluated in the LPS-induced RAW264.7 cells. This research represents the inaugural comprehensive phytochemical study of H. patulum, paving the way for further exploration of monoterpenoid glycosides.
Asunto(s)
Frutas , Glicósidos , Hypericum , Monoterpenos , Extractos Vegetales , Hypericum/química , Glicósidos/química , Glicósidos/farmacología , Glicósidos/aislamiento & purificación , Ratones , Animales , Células RAW 264.7 , Frutas/química , Monoterpenos/química , Monoterpenos/farmacología , Monoterpenos/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/farmacología , Antiinflamatorios/farmacología , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Estructura Molecular , Lipopolisacáridos/farmacología , Espectroscopía de Resonancia Magnética , Fitoquímicos/química , Fitoquímicos/farmacología , Fitoquímicos/aislamiento & purificaciónRESUMEN
Citral, a common monoterpene found in numerous plants, is an interesting compound that has been shown to have various biological activities. Although it is widely distributed in nature and there are many studies presenting its biological activities, its anti-neurodegenerative activity, especially under in vivo conditions, is very poorly understood. Thus, this paper aimed to deepen knowledge about citral activity towards factors and symptoms of neurodegeneration. To accomplish this, several comprehensive tests were conducted, including the estimation of butyrylcholinesterase inhibition, the evaluation of hepatotoxicity and the detection of oxidative stress and lipid peroxidation in vitro, as well as an in vivo behavioral assessment using mice models. Additionally, ex vivo determination of level of the compound in the brain and blood of a tested animal was undertaken. The results obtained revealed that citral is able to inhibit butyrylcholinesterase activity and protect hepatic cells against oxidative stress and lipid peroxidation in vitro. Moreover, behavioral tests in vivo indicated that citral (50 mg/kg) improves memory processes associated with acquisition (passive avoidance test), both in acute and subchronic administration. Additionally, we found that the administration of citral at 25 mg/kg and 50 mg/kg did not significantly affect the locomotor activity. Beyond the aforementioned, gas chromatography-mass spectrometry analysis revealed the presence of the compound in the blood and brain after subchronic administration of citral. Taken together, the results obtained in vitro, in vivo and ex vivo clearly indicate that citral is a promising monoterpene that can potentially be used towards cognition improvement.
Asunto(s)
Monoterpenos Acíclicos , Cognición , Peroxidación de Lípido , Estrés Oxidativo , Animales , Monoterpenos Acíclicos/farmacología , Ratones , Cognición/efectos de los fármacos , Estrés Oxidativo/efectos de los fármacos , Peroxidación de Lípido/efectos de los fármacos , Masculino , Butirilcolinesterasa/metabolismo , Encéfalo/efectos de los fármacos , Encéfalo/metabolismo , Inhibidores de la Colinesterasa/farmacología , Humanos , Monoterpenos/farmacología , Hígado/metabolismo , Hígado/efectos de los fármacosRESUMEN
BACKGROUND: Bitter orange (Citrus aurantium) is a fruiting shrub native to tropical and subtropical countries around the world and cultivated in many regions due to its nutraceutical value. The current study investigated the metabolic profiling and enzyme inhibitory activities of volatile constituents derived from the C. aurantium peel cultivated in Egypt by three different extraction methods. METHODS: The volatile chemical constituents of the peel of C. aurantium were isolated using three methods; steam distillation (SD), hydrodistillation (HD), and microwave-assisted hydrodistillation (MAHD), and then were investigated by GC-MS. The antioxidant potential was evaluated by different assays such as DPPH, ABTS, FRAP, CUPRAC, and phosphomolybdenum and metal chelating potential. Moreover, the effect of enzyme inhibition of the three essential oils was tested using BChE, AChE, tyrosinase, glucosidase, as well as amylase assays. RESULTS: A total of six compounds were detected by GC/MS analysis. The major constituent obtained by all three extraction methods was limonene (98.86% by SD, 98.68% by HD, and 99.23% by MAHD). Differences in the composition of the compounds of the three oils were observed. The hydrodistillation technique has yielded the highest number of compounds, notably two oxygenated monoterpenes: linalool (0.12%) and α-terpineol acetate (0.1%). CONCLUSION: In our study differences in the extraction methods of C. aurantium peel oils resulted in differences in the oils' chemical composition. Citrus essential oils and their components showed potential antioxidant, anticholinesterase, antimelanogenesis, and antidiabetic activities. The presence of linalool and α-terpineol acetate may explain the superior activity observed for the oil isolated by HD in both radical scavenging and AChE inhibition assays, as well as in the enzyme inhibition assays.
Asunto(s)
Antioxidantes , Frutas , Aceites Volátiles , Aceites Volátiles/farmacología , Aceites Volátiles/química , Frutas/química , Antioxidantes/farmacología , Antioxidantes/química , Inhibidores Enzimáticos/farmacología , Inhibidores Enzimáticos/química , Cromatografía de Gases y Espectrometría de Masas , Citrus aurantiifolia/química , Citrus/química , Aceites de Plantas/farmacología , Aceites de Plantas/química , Extractos Vegetales/farmacología , Extractos Vegetales/química , Egipto , Monoterpenos/farmacología , Monoterpenos Acíclicos/farmacología , Limoneno/farmacologíaRESUMEN
BACKGROUND: Origanum species have been used in various commercial constructions as a remedy against burns and wounds, agriculture, alcoholic drinks, fragrance, and flavoring substances of food products. The essential oil of Origanum onites L. (EOOO) and its component carvacrol (CV) possesses a wide range of biological activities including anti-cancer activity. PURPOSE: The purpose of this study was to investigate the growth inhibitory activity of the essential oil and its major component CV and then hepatotoxicity pathway-related genes in HepG2 cells. METHODS: The effects of the EOOO and CV on cell growth and mRNA expressions of 84 hepatotoxicity pathway-related genes were investigated in HepG2, using trypan blue exclusion/ bromodeoxyuridine (BrdU) incorporation tests and real-time-polymerase chain reaction (RT-PCR) array, respectively. RESULTS: The EOOO and CV inhibited cell growth with IC50 values of 0.08 µg/mL and 45 µg/mL, respectively, after 24 h. Real-time, reverse-transcription-polymerase chain reaction (RT2-PCR) array analysis revealed that expressions of 32 genes out of 84 were changed at least 2-fold or more in the EOOO-treated cells. Among them, expression levels of 17 genes were elevated, while expression levels of 15 genes were diminished. Furthermore, after exposure of cells to 45 µg/mL of CV, the expression of 8 genes was increased while the other 8 genes were decreased. Both the EOOO and carvacrol affected the expression of 48 genes of HepG2 cells which are involved in the hepatotoxicity pathway, indicating their hepatoprotective and possible anti-hepatocarcinogenic effects. CONCLUSION: The present study demonstrates that the essential oil of Origanum onites and carvacrol can be used in various applications such as anticancer or herbal drugs, since its non-hepatotoxicity.
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Cimenos , Monoterpenos , Aceites Volátiles , Origanum , Humanos , Cimenos/farmacología , Aceites Volátiles/farmacología , Origanum/química , Células Hep G2 , Monoterpenos/farmacología , Proliferación Celular/efectos de los fármacosRESUMEN
Leukemia, particularly acute myeloid leukemia (AML) is considered a serious health condition with high prevalence among adults. Accordingly, finding new therapeutic modalities for AML is urgently needed. This study aimed to develop a biocompatible nanoformulation for effective oral delivery of the phytomedicine; baicalin (BAC) for AML treatment. Lipid nanocapsules (LNCs) based on bioactive natural components; rhamnolipids (RL) as a biosurfactant and the essential oil linalool (LIN), were prepared using a simple phase-inversion method. The elaborated BAC-LNCs displayed 61.1 nm diameter and 0.2 PDI. Entrapment efficiency exceeded 98 % with slow drug release and high storage-stability over 3 months. Moreover, BAC-LNCs enhanced BAC oral bioavailability by 2.3-fold compared to BAC suspension in rats with higher half-life and mean residence-time. In vitro anticancer studies confirmed the prominent cytotoxicity of BAC-LNCs on the human leukemia monocytes (THP-1). BAC-LNCs exerted higher cellular association, apoptotic capability and antiproliferative activity with DNA synthesis-phase arrest. Finally, a mechanistic study performed through evaluation of various tumor biomarkers revealed that BAC-LNCs downregulated the angiogenic marker, vascular endothelial growth-factor (VEGF) and the anti-apoptotic marker (BCl-2) and upregulated the apoptotic markers (Caspase-3 and BAX). The improved efficacy of BAC bioactive-LNCs substantially recommends their pharmacotherapeutic potential as a promising nanoplatform for AML treatment.
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Liberación de Fármacos , Flavonoides , Leucemia Mieloide Aguda , Nanocápsulas , Animales , Flavonoides/farmacología , Flavonoides/administración & dosificación , Flavonoides/química , Humanos , Leucemia Mieloide Aguda/tratamiento farmacológico , Nanocápsulas/química , Masculino , Apoptosis/efectos de los fármacos , Ratas , Glucolípidos/química , Glucolípidos/administración & dosificación , Glucolípidos/farmacología , Monoterpenos/farmacología , Monoterpenos/química , Monoterpenos/administración & dosificación , Células THP-1 , Disponibilidad Biológica , Administración Oral , Antineoplásicos Fitogénicos/administración & dosificación , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/farmacocinética , Antineoplásicos Fitogénicos/química , Ratas Sprague-Dawley , Proliferación Celular/efectos de los fármacos , Línea Celular Tumoral , Monoterpenos AcíclicosRESUMEN
In this study, high-performance liquid chromatography was used to determine four components of Shaoyao Gancao Decoction (SGD), and the effect of purification was evaluated using fingerprints, similarity analysis and cell experiments. An effective method for isolation and purification of SGD was established. The adsorption/desorption properties of SGD were evaluated using resin screening, isothermal analysis, adsorption kinetics, and dynamic adsorption-desorption experiments. It was shown that the Langmuir equation fitted the isotherm data well and that a pseudo-second-order model accurately described kinetic adsorption on AB-8 resin. Analysis of thermodynamic parameters showed that the adsorption process was exothermic. Under the optimal process conditions, the concentrations of albiflorin, paeoniflorin, liquiritin and ammonium glycyrrhizinate in the product were 73.05, 134.04, 45.04 and 75.00 mg/g, respectively. The yields of the four components were 71.89 %-86.19 %. Cell experiments showed that the purified SGD retained anti-inflammatory activity. This research lays the foundation for the separation and purification of SGD and subsequent preparation research.
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Medicamentos Herbarios Chinos , Glucósidos , Monoterpenos , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Cromatografía Líquida de Alta Presión/métodos , Glucósidos/aislamiento & purificación , Glucósidos/química , Monoterpenos/aislamiento & purificación , Monoterpenos/química , Adsorción , Flavanonas/aislamiento & purificación , Flavanonas/química , Flavanonas/análisis , Animales , Ácido Glicirrínico/aislamiento & purificación , Ácido Glicirrínico/química , Ácido Glicirrínico/análisis , Hidrocarburos Aromáticos con Puentes/química , Hidrocarburos Aromáticos con Puentes/aislamiento & purificación , Ratones , Resinas Sintéticas/química , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/química , Humanos , Células RAW 264.7RESUMEN
Five new compounds, including two sesquiterpenoid glycosides (1 and 2), two monoterpenoid glycosides (3 and 4), and a quinovose ester (5), together with four known compounds (6-9) were isolated from branches and leaves of Pittosporum pulchrum Gagnep. Their structures were established by 1D and 2D NMR, HR-ESI-MS, IR and UV spectral analyses. This is the first time to investigate the chemical constituents of P. pulchrum. Subsequently, the anti-inflammatory and antioxidant activities of different solvent fractions of ethanol extract and isolated compounds were evaluated. Dichloromethane and ethyl acetate fractions dramatically inhibited the production of NO in a concentration-dependent manner in LPS-induced RAW264.7 cells. Ethyl acetate and n-butanol fractions showed excellent DPPH radical scavenging activities with IC50 values of 24.31 µg/mL and 27.81 µg/mL, respectively. Compounds 7 and 8 might be potential natural antioxidants with IC50 values of 16.13 µM and 24.81 µM, respectively.
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Antiinflamatorios , Antioxidantes , Fitoquímicos , Hojas de la Planta , Hojas de la Planta/química , Ratones , Células RAW 264.7 , Animales , Estructura Molecular , Antioxidantes/farmacología , Antioxidantes/aislamiento & purificación , Antioxidantes/química , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Antiinflamatorios/farmacología , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/química , Glicósidos/aislamiento & purificación , Glicósidos/farmacología , Glicósidos/química , Óxido Nítrico/metabolismo , Tallos de la Planta/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Sesquiterpenos/química , China , Monoterpenos/aislamiento & purificación , Monoterpenos/farmacologíaRESUMEN
Linalool and linalyl acetate are major components of lavender essential oil. These substances possess many biological activities, such as anti-inflammatory activity, analgesic and anxiolytic effects, and anticonvulsant properties, and they also induce modulation of neuronal activity in the autonomic nervous system. However, there are no reports of the direct effects of linalool on respiratory activity. In the present study, we analyzed the effects of linalool and linalyl acetate on central respiratory activity in the brainstem-spinal cord preparation isolated from newborn rats. Linalool dose-dependently decreased the rate of respiratory activity. This effect was reversed by bicuculline, suggesting that linalool enhanced inhibitory synaptic connections via GABAA receptors. In addition, linalool reduced the coefficient of variation of inspiratory burst intervals and thus could work to stabilize the respiratory rhythm. Linalyl acetate did not cause inhibitory effects as observed in linalool treatment. Linalool depressed burst activity of pre-inspiratory neurons in the medullary respiratory networks and increased the amplitude of inspiratory inhibitory postsynaptic potentials of pre-inspiratory neurons. We concluded that linalool caused inhibitory effects on respiratory rhythm generation mainly through activation of presynaptic GABAA receptors of pre-inspiratory neurons.
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Monoterpenos Acíclicos , Animales Recién Nacidos , Tronco Encefálico , Monoterpenos , Neuronas , Médula Espinal , Animales , Monoterpenos Acíclicos/farmacología , Médula Espinal/efectos de los fármacos , Médula Espinal/metabolismo , Ratas , Monoterpenos/farmacología , Neuronas/efectos de los fármacos , Neuronas/metabolismo , Tronco Encefálico/efectos de los fármacos , Tronco Encefálico/fisiología , Receptores de GABA-A/metabolismo , Respiración/efectos de los fármacos , Bicuculina/farmacologíaRESUMEN
Objective: Trichomonas vaginalis is a sexually transmitted protozoan parasite that usually causes infections in women. Metronidazole is used as the first choice in the treatment of this parasitic disease, but there is a need for new drugs since 1980's with increasing numbers of reported resistance. In this study, it was aimed to determine the antitrichomonal activity of the major components of Cinnamomum zeylanicum (cinnamon) and Thymus vulgaris (thyme) essential oils, cinnamaldehyde, carvacrol and thymol against metronidazole resistant and susceptible T. vaginalis strains, and to determine their interaction with metronidazole by checkerboard method. Methods: Cinnamaldehyde, carvacrol, thymol and metronidazole were obtained commercially. Two clinical isolates and one metronidazole resistant T. vaginalis reference strain were used in the study. MIC50 and MLC values of essential oil components and metronidazole were determined by broth microdilution method. The combinations of essential oil components with metronidazole were determined by the checkerboard method. Results: According to in vitro activity tests, cinnamaldehyde was determined to be most effective essential oil component. Clinical isolates were susceptible to metronidazole. In combination study, metronidazole showed synergy with cinnamaldehyde and carvacrol, and partial synergy with thymol. Conclusion: It was determined that cinnamaldehyde, carvacrol and thymol, which are known to have high antimicrobial activity, also have strong activity against T. vaginalis isolates and show a synergistic interaction with metronidazole. The use of metronidazole at lower doses in the synergistic interaction may contribute to the literature in terms of reducing drug side effects, creating a versatile antimicrobial target, and reducing the rate of resistance development.
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Acroleína , Cimenos , Sinergismo Farmacológico , Metronidazol , Monoterpenos , Aceites Volátiles , Timol , Thymus (Planta) , Trichomonas vaginalis , Acroleína/análogos & derivados , Acroleína/farmacología , Timol/farmacología , Cimenos/farmacología , Metronidazol/farmacología , Humanos , Aceites Volátiles/farmacología , Thymus (Planta)/química , Trichomonas vaginalis/efectos de los fármacos , Monoterpenos/farmacología , Femenino , Cinnamomum zeylanicum/química , Antiprotozoarios/farmacología , Pruebas de Sensibilidad Microbiana , Resistencia a MedicamentosRESUMEN
The Ru(II)-nitrite complex, Ru4, is explored to release nitric oxide (NO) under acidic conditions and selectively induce a cytotoxic effect towards SK-MEL-28 cisplatin-resistant malignant melanoma cells. These findings suggest that targeting the tumor-associated pHe level could be an effective strategy for the drug function of Ru(II)-nitrite compounds.
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Antineoplásicos , Cisplatino , Complejos de Coordinación , Cimenos , Resistencia a Antineoplásicos , Melanoma , Óxido Nítrico , Nitritos , Rutenio , Cisplatino/farmacología , Cisplatino/química , Humanos , Rutenio/química , Rutenio/farmacología , Melanoma/tratamiento farmacológico , Melanoma/patología , Melanoma/metabolismo , Resistencia a Antineoplásicos/efectos de los fármacos , Antineoplásicos/farmacología , Antineoplásicos/química , Antineoplásicos/síntesis química , Cimenos/farmacología , Cimenos/química , Nitritos/química , Nitritos/farmacología , Complejos de Coordinación/química , Complejos de Coordinación/farmacología , Complejos de Coordinación/síntesis química , Línea Celular Tumoral , Óxido Nítrico/metabolismo , Monoterpenos/farmacología , Monoterpenos/química , Muerte Celular/efectos de los fármacosRESUMEN
Sodium chloride (NaCl) can cause oxidative stress in plants, which represents a potential obstacle to the development of monocultures worldwide. Onion (Allium cepa L.) is a famous vegetable consumed and used in world cuisine. In the present study, we analyzed the influence of soil physicochemical profile and the remedial capacity of linalool on seed emergence, roots, and leaf growth in onions subjected to salt stress, as well as its in vivo and in vitro antioxidant potential, Fe2+chelating activity, and reducing power of Fe3+. The outcome of the soil analysis established the following order of abundance: sulfur (S) > calcium (Ca) > potassium (K) > magnesium (Mg) > sodium (Na). NaCl (150 mM) significantly reduced the emergence speed index (ESI), leaf and root length, while increasing the peroxidation content. The length of leaves and roots significantly increased after treatment with linalool (300 and 500 µg/mL). Our data showed negative correlations between seed emergence and K+ concentration, which was reversed after treatments. Linalool (500 µg/mL) significantly reduced oxidative stress, but increased Fe2+ concentration and did not show potential to reduce Fe3+. The in vivo antioxidant effect of linalool is thought to primarily result from an enzymatic activation process. This mechanism underscores its potential as a therapeutic agent for oxidative stress-related conditions. Further investigation into this process could unveil new avenues for antioxidant therapy.