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1.
Int J Mol Sci ; 25(4)2024 Feb 12.
Artigo em Inglês | MEDLINE | ID: mdl-38396868

RESUMO

Monoterpenes are secondary plant metabolites, and such volatile compounds have antioxidant, antibacterial, antiviral, and enzyme inhibitory properties. These compounds are also able to reduce the potentially pro-neurodegenerative trace metal ions that can be sources of free radicals. One basic method used to evaluate the ability of chemical compounds to reduce Fe(III) is FRAP. To date, most studies based on a FRAP assay were performed within several dozen minutes. However, taking into account the diversity of compounds, it is justified to observe their activity over a much longer period of time. The present study aimed to observe the activity of isopulegol, γ-terpinene, α-terpinene, linalool, carvone, citral, and α-phellandrene over a 48 h period. Our study indicates that the lengthened reaction period enhanced activity from several dozen to several hundred percent. The obtained results also revealed an explicit high correlation of the increase in the activity of compounds with the increase in monoterpene concentration. Due to the hydrophobic character of monoterpenes, the FRAP method was modified by the addition of Tween 20. The highest activity was obtained for α-terpinene and γ-terpinene.


Assuntos
Monoterpenos Cicloexânicos , Compostos Férricos , Monoterpenos , Monoterpenos/farmacologia , Antioxidantes/química , Antibacterianos
2.
J Chem Ecol ; 49(7-8): 363-368, 2023 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-37085723

RESUMO

The beetle family Disteniidae is currently considered to be closely related to the much larger family Cerambycidae, the longhorned beetles. The 300 + species of disteniids are mostly native to tropical and subtropical regions, with the only described North American species north of Mexico being Elytrimitatrix undata (F.). Here we describe the identification and field testing of (1R,4R)-quercivorol as a male-produced aggregation-sex pheromone component for E. undata. This is the first pheromone identified for any species within the family Disteniidae.


Assuntos
Besouros , Atrativos Sexuais , Animais , Masculino , Atrativos Sexuais/farmacologia , Feromônios , Monoterpenos
3.
Int J Mol Sci ; 23(16)2022 Aug 11.
Artigo em Inglês | MEDLINE | ID: mdl-36012223

RESUMO

Dermal papilla cells (DPCs) are growth factor reservoirs that are specialized for hair morphogenesis and regeneration. Due to their essential role in hair growth, DPCs are commonly used as an in vitro model to investigate the effects of hair growth-regulating compounds and their molecular mechanisms of action. Cyclic adenosine monophosphate (cAMP), an intracellular second messenger, is currently employed as a growth-promoting target molecule. In a pilot test, we found that α-phellandrene, a naturally occurring phytochemical, increased cAMP levels in DPCs. Therefore, we sought to determine whether α-phellandrene increases growth factors and proliferation in human DPCs and to identify the underlying mechanisms. We demonstrated that α-phellandrene promotes cell proliferation concentration-dependently. In addition, it increases the cAMP downstream effectors, such as protein kinase A catalytic subunit (PKA Cα) and phosphorylated cAMP-responsive element-binding protein (CREB). Also, among the CREB-dependent growth factor candidates, we identified that α-phellandrene selectively upregulated vascular endothelial growth factor (VEGF) mRNA expression in DPCs. Notably, the beneficial effects of α-phellandrene were nullified by a cAMP inhibitor. This study demonstrated the cAMP-mediated growth effects in DPCs and the therapeutic potential of α-phellandrene for preventing hair loss.


Assuntos
Folículo Piloso , Fator A de Crescimento do Endotélio Vascular , Proliferação de Células , Células Cultivadas , AMP Cíclico/metabolismo , Monoterpenos Cicloexânicos , Folículo Piloso/metabolismo , Humanos , Fator A de Crescimento do Endotélio Vascular/farmacologia
4.
Molecules ; 27(22)2022 Nov 17.
Artigo em Inglês | MEDLINE | ID: mdl-36432066

RESUMO

This study was conducted to investigate the chemical composition of essential oil (EO) extracted from an oleoresin of Canarium schweinfurthii widespread in the Gabonese tropical forest. A great variability in the chemical composition of EO was observed, among which a chemical profile rich in terpinolene and α-phellandrene (31.2 and 21.8%, respectively), was found and tested as a natural active ingredient for topical applications. After the evaluation of eye and skin irritancy and sensitization potentials of EO on in vitro and in chemico models, the in vitro modulating potential on a model of wound re-epithelialization was assessed. The terpinolene and α-phellandrene-rich chemotype have been proven to accelerate wound healing in a dose-dependent manner (concentration range from 1.8 to 9.0 µg/mL). In addition, the ability of this EO to modulate the pro-inflammatory response in human keratinocytes stimulated by UVB was observed in vitro by the reduction in levels of interleukin 6 (IL-6) and tumour necrosis factor-alpha (TNF-α), suggesting a possible implication during the inflammation phase of wound healing. Despite the high variability in EO composition, a method of solid-phase microextraction (SPME) of the oleoresin headspace is proposed for the in situ identification of the terpinolene and α-phellandrene-rich chemotype instead of conducting hydrodistillation. These results offer interesting perspectives for the development of innovative natural ingredients for the topical route, ingredients obtained in an eco-responsible and non-destructive way.


Assuntos
Burseraceae , Óleos Voláteis , Humanos , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Cicatrização
5.
Pharmacol Res ; 164: 105376, 2021 02.
Artigo em Inglês | MEDLINE | ID: mdl-33316383

RESUMO

Depression is a common global mental disorder that seriously harms human physical and mental health. With the development of society, the increase of pressure and the role of various other factors make the incidence of depression increase year by year. However, there is a lack of drugs that have a fast onset, significant effects, and few side effects. Some volatile oils from traditional natural herbal medicines are usually used to relieve depression and calm emotions, such as Lavender essential oil and Acorus tatarinowii essential oil. It was reported that these volatile oils, are easy to enter the brain through the blood-brain barrier and have good antidepressant effects with little toxicity and side effects. In this review, we summarized the classification of depression, and listed the history of using volatile oils to fight depression in some countries. Importantly, we summarized the anti-depressant natural volatile oils and their monomers from herbal medicine, discussed the anti-depressive mechanisms of the volatile oils from natural medicine. The volatile oils of natural medicine and antidepressant drugs were compared and analyzed, and the application of volatile oils was explained from the clinical use and administration routes. This review would be helpful for the development of potential anti-depressant medicine and provide new alternative treatments for depressive disorders.


Assuntos
Antidepressivos/administração & dosagem , Depressão/tratamento farmacológico , Transtorno Depressivo/tratamento farmacológico , Óleos Voláteis/administração & dosagem , Óleos de Plantas/administração & dosagem , Animais , Antidepressivos/química , Antidepressivos/classificação , Depressão/classificação , Transtorno Depressivo/classificação , Humanos , Óleos Voláteis/química , Óleos Voláteis/classificação , Fitoterapia , Óleos de Plantas/química , Óleos de Plantas/classificação , Plantas Medicinais
6.
Molecules ; 26(15)2021 Jul 29.
Artigo em Inglês | MEDLINE | ID: mdl-34361766

RESUMO

Hedyosmum racemosum (Ruiz & Pav.) G. is a native species of Ecuador used in traditional medicine for treatment of rheumatism, bronchitis, cold, cough, asthma, bone pain, and stomach pain. In this study, fresh H. racemosum leaves of male and female specimens were collected and subjected to hydrodistillation for the extraction of the essential oil. The chemical composition of male and female essential oil was determined by gas chromatography-gas chromatography equipped with a flame ionization detector and coupled to a mass spectrometer using a non-polar and a polar chromatographic column. The antibacterial activity was assayed against five Gram-positive and two Gram-negative bacteria, and two dermatophytes fungi. The scavenging radical properties of the essential oil were evaluated by DPPH and ABTS assays. The chemical analysis allowed us to identify forty-three compounds that represent more than 98% of the total composition. In the non-polar and polar column, α-phellandrene was the principal constituent in male (28.24 and 25.90%) and female (26.47 and 23.90%) essential oil. Other main compounds were methyl chavicol, germacrene D, methyl eugenol, and α-pinene. Female essential oil presented a strong activity against Klebsiella pneumoniae (ATCC 9997) with an minimum inhibitory concentration (MIC) of 500 µg/mL and a scavenging capacity SC50 of 800 µg/mL.


Assuntos
Antibacterianos/química , Antioxidantes/química , Monoterpenos Cicloexânicos/química , Magnoliopsida/química , Óleos Voláteis/química , Derivados de Alilbenzenos/química , Derivados de Alilbenzenos/isolamento & purificação , Anisóis/química , Anisóis/isolamento & purificação , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Arthrodermataceae/efeitos dos fármacos , Arthrodermataceae/crescimento & desenvolvimento , Benzotiazóis/antagonistas & inibidores , Monoterpenos Bicíclicos/química , Monoterpenos Bicíclicos/isolamento & purificação , Compostos de Bifenilo/antagonistas & inibidores , Monoterpenos Cicloexânicos/isolamento & purificação , Equador , Eugenol/análogos & derivados , Eugenol/química , Eugenol/isolamento & purificação , Feminino , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Negativas/crescimento & desenvolvimento , Bactérias Gram-Positivas/efeitos dos fármacos , Bactérias Gram-Positivas/crescimento & desenvolvimento , Humanos , Magnoliopsida/metabolismo , Masculino , Testes de Sensibilidade Microbiana , Picratos/antagonistas & inibidores , Folhas de Planta/química , Plantas Medicinais , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/isolamento & purificação , Fatores Sexuais , Ácidos Sulfônicos/antagonistas & inibidores
7.
Molecules ; 25(3)2020 Jan 28.
Artigo em Inglês | MEDLINE | ID: mdl-32012955

RESUMO

The intent of this study was to utilize distillation timeframes (DT) of nutmeg (Myristica fragrans) essential oil (EO) to generate fractions with differential chemical compositions and bioactivity. Ten fractions were captured at the following distillation timeframes: 0.0-0.5, 0.5-1.0, 1.0-2.5, 2.5-5.0, 5.0-10, 10-30, 30-60, 60-90, 90-120, and 120-240 min. In addition, a control EO was collected from a straight 0-240 min non-stop distillation. ANOVA and advanced regression modeling revealed that the produced EO fractions possess substantial variation in the concentration of potentially desired compounds. The concentrations (%) of α-phellandrene, 3-carene, p-cymene, limonene, α-thujene, α-pinene, camphene, sabinene, ß-pinene, and myrcene decreased, while the concentrations (%) of α-terpinene, γ-terpinene, terpinolene, and myristicin increased in later DT fractions. Nutmeg EO showed some antimalarial activity against Plasmodium falciparum D6, but did not exhibit significant antifungal activity. In general, nutmeg seed oil yields increased with an increase of DT. These results may be utilized by industries using nutmeg EO.


Assuntos
Antimaláricos/química , Myristica/química , Óleos Voláteis/química , Plasmodium falciparum/efeitos dos fármacos , Antimaláricos/farmacologia , Cromatografia Gasosa , Destilação , Óleos Voláteis/farmacologia , Óleos de Plantas/análise , Óleos de Plantas/química , Sementes/química
8.
Biotechnol Bioeng ; 116(8): 2041-2051, 2019 08.
Artigo em Inglês | MEDLINE | ID: mdl-30963538

RESUMO

The work aims to convert the secondary slow metabolism of the terpenoid biosynthetic pathway into a primary activity in cyanobacteria and to generate heterologous products using these photosynthetic microorganisms as cell factories. Case study is the production of the 10-carbon monoterpene ß-phellandrene (PHL) in Synechocystis sp. PCC 6803 (Synechocystis). Barriers to this objective include the slow catalytic activity of the terpenoid metabolism enzymes that limit rates and yield of product synthesis and accumulation. "Fusion constructs as protein overexpression vectors" were applied in the overexpression of the geranyl diphosphate synthase (GPPS) and ß-phellandrene synthase (PHLS) genes, causing accumulation of GPPS up to 4% and PHLS up to 10% of the total cellular protein. Such GPPS and PHLS protein overexpression compensated for their slow catalytic activity and enabled transformant Synechocystis to constitutively generate 24 mg of PHL per g biomass (2.4% PHL:biomass, w-w), a substantial improvement over earlier yields. The work showed that a systematic overexpression, at the protein level, of the terpenoid biosynthetic pathway genes is a promising approach to achieving high yields of prenyl product biosynthesis, on the way to exploiting the cellular terpenoid metabolism for commodity product generation.


Assuntos
Monoterpenos Cicloexânicos/metabolismo , Synechocystis/metabolismo , Vias Biossintéticas , Biotecnologia , Engenharia Metabólica , Fotossíntese , Synechocystis/genética , Terpenos/metabolismo
9.
Fish Shellfish Immunol ; 84: 1108-1114, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30414490

RESUMO

Innate immunity and resistance against Vibrio alginolyticus in white shrimp, Litopenaeus vannamei, that received α-phellandrene were examined. The results indicated that the percent survival of shrimp receiving 4, 8, and 12 µg g-1 α-phellandrene was significantly higher than that of control shrimp after 72 h (p < 0.05). In a separate experiment, the phenoloxidase (PO), respiratory bursts, superoxide dismutase (SOD), and phagocytic and lysozyme activity of L. vannamei receiving 8 and 12 µg g-1 α-phellandrene were significantly higher than those of the other groups upon challenge with V. alginolyticus at 24-60, 36-60, 12-60, 12-72 and 48-72 h, respectively. However, no significant differences in the total haemocyte counts (THC) of L. vannamei receiving any dose of α-phellandrene and of control shrimp were observed at 12-72 h. The expression (mRNA transcripts) of the immune genes prophenoloxidase (proPO), LPS- and ß-1,3-glucan-binding protein (LGBP) and peroxinectin (PE) of shrimp receiving α-phellandrene at 8 and 12 µg g-1 significantly increased after challenge with V. alginolyticus for 72 h (p < 0.05). We conclude that the immune ability and resistance against V. alginolyticus infection increased in L. vannamei receiving >4 µg g-1 α-phellandrene. These results indicated that α-phellandrene plays an important role in the innate immunity of white shrimp.


Assuntos
Expressão Gênica/efeitos dos fármacos , Hemócitos/efeitos dos fármacos , Imunidade Inata/efeitos dos fármacos , Monoterpenos/administração & dosagem , Penaeidae/imunologia , Vibrio alginolyticus/efeitos dos fármacos , Animais , Monoterpenos Cicloexânicos , Expressão Gênica/imunologia , Hemócitos/citologia , Imunidade Inata/genética , Penaeidae/efeitos dos fármacos , Penaeidae/genética , Penaeidae/microbiologia , Vibrio alginolyticus/fisiologia
10.
J Invertebr Pathol ; 149: 141-147, 2017 10.
Artigo em Inglês | MEDLINE | ID: mdl-28818498

RESUMO

The honeybee disease nosemosis type C is a serious problem since its causative agent, microsporidium Nosema ceranae, is widespread among adult honey bees. Some of the feasible alternative treatments that are used to control this disease are plant extracts. The aim of the present work was to evaluate the effects of essential oils of Chilean plant species, such as Cryptocarya alba, which is used against N. ceranae, and to identify and quantify the majority active compounds in the EO as well as their potential use for the control of nosemosis. Essential oils were obtained using the stripping steam technique with Clevenger equipment and were subsequently analyzed by Gas chromatography-mass spectrometry. Mortality was recorded daily over at least 8days as worker honeybees were exposed to a range of doses of EO dispersed in a sucrose solution. C. alba oil appears to be nontoxic to A. mellifera adults at the tested concentration (the same concentration inhibits the growth of N. ceranae), showing that this oil can be used for the treatment of nosemosis. EO effectiveness was demonstrated against N. ceranae by calculating the percentage of decrease in infected bees from untreated infected groups vs infected groups treated with EO or the reference drug fumagillin. It was determined that a dose of 4µg EO/bee was most effective in controlling N. ceranae development. We determined innocuous doses of C. alba essential oil for honeybees. We demonstrated the antifungal activity of C. alba EO at 4µg/bee against N. ceranae and compared it to its major monoterpenes, such as ß-phellandrene (20µg/bee), eucalyptol (20µg/bee) and α-terpineol (20µg/bee). The major compounds of C. alba EO, α-terpineol, eucalyptol and ß-phellandrene, had significant effects against Apis mellifera infection by N. ceranae, but the antifungal effect of the complete essential oil on N. ceranae was larger than the effect of α-terpineol, eucalyptol or ß- phellandrene separately, showing that C. alba oil may be a candidate for the treatment or prevention of nosemosis.


Assuntos
Antifúngicos/uso terapêutico , Abelhas/microbiologia , Cryptocarya , Microsporidiose/veterinária , Óleos Voláteis/uso terapêutico , Extratos Vegetais/uso terapêutico , Animais , Microsporidiose/tratamento farmacológico , Nosema
11.
Photosynth Res ; 130(1-3): 123-135, 2016 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-26895437

RESUMO

Cyanobacteria can be exploited as photosynthetic platforms for heterologous generation of terpene hydrocarbons with industrial application. However, the slow catalytic activity of terpene synthases (k cat = 4 s-1 or slower) makes them noncompetitive for the pool of available substrate, thereby limiting the rate and yield of product generation. Work in this paper applied transformation technologies in Synechocystis for the heterologous production of ß-phellandrene (monoterpene) hydrocarbons. Conditions were defined whereby expression of the ß-phellandrene synthase (PHLS), as a CpcB·PHLS fusion protein with the ß-subunit of phycocyanin, accounted for up to 20 % of total cellular protein. Moreover, CpcB·PHLS was heterologously co-expressed with enzymes of the mevalonic acid (MVA) pathway and geranyl-diphosphate synthase, increasing carbon flux toward the terpenoid biosynthetic pathway and enhancing substrate availability. These improvements enabled yields of 10 mg of ß-phellandrene per g of dry cell weight generated in the course of a 48-h incubation period, or the equivalent of 1 % ß-phellandrene:biomass (w:w) carbon-partitioning ratio. The work helped to identify prerequisites for the efficient heterologous production of terpene hydrocarbons in cyanobacteria: (i) requirement for overexpression of the heterologous terpene synthase, so as to compensate for the slow catalytic turnover of the enzyme, and (ii) enhanced endogenous carbon partitioning toward the terpenoid biosynthetic pathway, e.g., upon heterologous co-expression of the MVA pathway, thereby supplementing the native metabolic flux toward the universal isopentenyl-diphosphate and dimethylallyl-diphosphate terpenoid precursors. The two prerequisites are shown to be critical determinants of yield in the photosynthetic CO2 to terpene hydrocarbons conversion process.


Assuntos
Hidrocarbonetos/metabolismo , Synechocystis/metabolismo , Terpenos/metabolismo , Vias Biossintéticas , DNA Bacteriano/genética , Química Verde/métodos , Engenharia Metabólica/métodos , Organismos Geneticamente Modificados , Fotossíntese , Synechocystis/genética
12.
Environ Exp Bot ; 132: 1-15, 2016 12.
Artigo em Inglês | MEDLINE | ID: mdl-29367791

RESUMO

Plants frequently experience heat ramps of various severities, but how and to what degree plant metabolic activity recovers from mild and severe heat stress is poorly understood. In this study, we exposed the constitutive terpene emitter, Solanum. lycopersicum leaves to mild (37 and 41 °C), moderate (46 °C) and severe (49 °C) heat ramps of 5 min. and monitored foliage photosynthetic activity, lipoxygenase pathway volatile (LOX), and mono- and sesquiterpene emissions and expression of two terpene synthase genes, ß-phellandrene synthase and (E)-ß-caryophyllene/α-humulene synthase, through a 24 h recovery period upon return to pre-stress conditions. Leaf monoterpene emissions were dominated by ß-phellandrene and sesquiterpene emissions by (E)-ß-caryophyllene, and thus, these two terpene synthase genes were representative for the two volatile terpene classes. Photosynthetic characteristics partly recovered under moderate heat stress, and very limited recovery was observed under severe stress. All stress treatments resulted in elicitation of LOX emissions that declined during recovery. Enhanced mono- and sesquiterpene emissions were observed immediately after the heat treatment, but the emissions decreased even to below the control treatment during recovery between 2-10 h, and raised again by 24 h. The expression of ß-phellandrene and (E)-ß-caryophyllene synthase genes decreased between 2-10 h after heat stress, and recovered to pre-stress level in mild heat stress treatment by 24 h. Overall, this study demonstrates a highly sensitive heat response of terpenoid synthesis that is mainly controlled by gene level responses under mild stress, while severe stress leads to non-recoverable declines in foliage physiological and gene expression activities.

13.
Environ Toxicol ; 31(11): 1640-1651, 2016 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-26174008

RESUMO

Although reports have shown that α-phellandrene (α-PA) is one of the monoterpenes and is often used in the food and perfume industry, our previous studies have indicated that α-PA promoted immune responses in normal mice in vivo. However, there is no available information to show that α-PA induced cell apoptosis in cancer cells, thus, we investigated the effects of α-PA on the cell morphology, viability, cell cycle distribution, and apoptosis in mice leukemia WEHI-3 cells in vitro. Results indicated that α-PA induced cell morphological changes and decreased viability, induced G0/G1 arrest and sub-G1 phase (apoptosis) in WEHI-3 cells. α-PA increased the productions of reactive oxygen species (ROS) and Ca2+ and decreased the levels of mitochondrial membrane potential (ΔΨm ) in dose- and time-dependent manners in WEHI-3 cells that were analyzed by flow cytometer. Results from confocal laser microscopic system examinations show that α-PA promoted the release of cytochrome c, AIF, and Endo G from mitochondria in WEHI-3 cells. These results are the first findings to provide new information for understanding the mechanisms by which α-PA induces cell cycle arrest and apoptosis in WEHI-3 cells in vitro. © 2015 Wiley Periodicals, Inc. Environ Toxicol 31: 1640-1651, 2016.


Assuntos
Apoptose/efeitos dos fármacos , Monoterpenos/farmacologia , Animais , Caspases/metabolismo , Pontos de Checagem do Ciclo Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Monoterpenos Cicloexânicos , Leucemia/tratamento farmacológico , Leucemia/patologia , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Camundongos , Espécies Reativas de Oxigênio/metabolismo
14.
Nutr Neurosci ; 18(5): 217-24, 2015 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-24661285

RESUMO

OBJECTIVES: Previous studies have shown that essential oil containing (R)-(+)-limonene and α-phellandrene, extracted from fruits of Schinus terebinthifolius Raddi, exhibit anti-inflammatory activity. This work aimed to verify the antihyperalgesic and antidepressive actions of (R)-(+)-limonene, α-phellandrene, and essential oil from S. terebinthifolius fruits in spared nerve injury (SNI) model of neuropathic pain in rats. METHODS: In the present work, essential oil from fruits of S. terebinthifolius, as well as the pure (R)-(+)-limonene and α-phellandrene compounds, were assayed for their effects on SNI-induced mechanical and cold hyperalgesia, and depressive-like behavior (immobility in forced swim test) in rats. The locomotor activity was evaluated in open-field test. RESULTS: Oral administration for up to 15 days of essential oil of S. terebinthifolius (100 mg/kg), (R)-(+)-limonene (10 mg/kg), α-phellandrene (10 mg/kg), and also subcutaneous 10 mg/kg dose of ketamine (positive control) significantly inhibited SNI-induced mechanical hyperalgesia and increased immobility in the forced swim test. On the 15th day of oral treatment, α-phellandrene, but neither the essential oil from S. terebinthifolius nor (R)-(+)-limonene, prevented the SNI-induced increase in sensitivity to a cold stimulus. The oral treatment with essential oil (100 mg/kg) or with compounds (10 mg/kg) did not interfere on locomotor activity. DISCUSSION: Together, the results of the present work show that essential oil of S. terebinthifolius and compounds present in this oil, including (R)-(+)-limonene and α-phellandrene, exhibit antihyperalgesic effects against mechanical hyperalgesia, and are antidepressive, while only α-phellandrene inhibited cold hyperalgesia in SNI rats.


Assuntos
Anacardiaceae/química , Antidepressivos/farmacologia , Cicloexenos/farmacologia , Monoterpenos/farmacologia , Neuralgia/tratamento farmacológico , Óleos Voláteis/farmacologia , Terpenos/farmacologia , Animais , Monoterpenos Cicloexânicos , Modelos Animais de Doenças , Frutas/química , Hiperalgesia/tratamento farmacológico , Limoneno , Masculino , Condicionamento Físico Animal , Óleos de Plantas/farmacologia , Ratos , Ratos Wistar
15.
Environ Toxicol ; 30(11): 1322-30, 2015 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-24861204

RESUMO

Although there are few reports regarding α-phellandrene (α-PA), a natural compound from Schinus molle L. essential oil, there is no report to show that α-PA induced DNA damage and affected DNA repair associated protein expression. Herein, we investigated the effects of α-PA on DNA damage and repair associated protein expression in murine leukemia cells. Flow cytometric assay was used to measure the effects of α-PA on total cell viability and the results indicated that α-PA induced cell death. Comet assay and 4,6-diamidino-2-phenylindole dihydrochloride staining were used for measuring DNA damage and condensation, respectively, and the results indicated that α-PA induced DNA damage and condensation in a concentration-dependent manner. DNA gel electrophoresis was used to examine the DNA damage and the results showed that α-PA induced DNA damage in WEHI-3 cells. Western blotting assay was used to measure the changes of DNA damage and repair associated protein expression and the results indicated that α-PA increased p-p53, p-H2A.X, 14-3-3-σ, and MDC1 protein expression but inhibited the protein of p53, MGMT, DNA-PK, and BRCA-1.


Assuntos
Dano ao DNA , Reparo do DNA , Proteínas de Ligação a DNA/genética , Monoterpenos/farmacologia , Anacardiaceae/química , Animais , Western Blotting , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Ensaio Cometa , Monoterpenos Cicloexânicos , Proteína Quinase Ativada por DNA/genética , Relação Dose-Resposta a Droga , Expressão Gênica/efeitos dos fármacos , Camundongos , Microscopia Confocal , Monoterpenos/isolamento & purificação , Biossíntese de Proteínas
16.
Oncol Rep ; 51(4)2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38456489

RESUMO

α­Phellandrene (α­PA), a natural constituent of herbs, inhibits cancer cell viability and proliferation. 5­Fluorouracil (5­FU) is a frequently utilized chemotherapeutic medicine for the treatment of colon cancer, which works by triggering cancer cell apoptosis. The present study examined how the combination of α­PA and 5­FU affects the suppression of human colon cancer cells by promoting apoptosis. The impact of this treatment on cell viability, apoptosis, and the expression levels of Bcl­2 family members, caspase family members and mitochondria­related molecules in HT­29 cells was assessed by the MTT assay, immunocytochemistry, western blotting and quantitative PCR. The combination of 5­FU and α­PA had a synergistic inhibitory effect on cell viability, as determined by assessing the combination index value. Bax protein expression levels were higher in the 50, 100 or 250 µM α­PA combined with 5­FU groups compared with those in the 5­FU alone group (P<0.05). By contrast, Bcl­2 protein expression levels and mitochondrial membrane potential (MMP, ΔΨm) were lower in the 100 or 250 µM α­PA combined with 5­FU groups than those in the 5­FU alone group (P<0.05). In addition, hexokinase­2 (HK­2) protein expression levels were lower in the 50, 100 or 250 µM α­PA combined with 5­FU groups than those in the 5­FU alone group (P<0.05). Compared with 5­FU alone, after HT­29 cells were treated with 50, 100 or 250 µM α­PA combined with 5­FU, the mRNA expression levels of extrinsic­induced apoptotic molecules, including caspase­8 and Bid, were higher (P<0.05). Treatment with 50, 100 or 250 µM α­PA combined with 5­FU also increased the mRNA expression levels of cytochrome c, caspase­9 and caspase­3, regulating intrinsic apoptosis (P<0.05). These results showed that α­PA and 5­FU had a synergistic effect on reducing the viability of human colon cancer HT­29 cells by inducing extrinsic and intrinsic apoptosis pathways. The mechanism by which apoptosis is induced may involve the intrinsic apoptosis pathway that activates the mitochondria­dependent pathway, including regulating the expression levels of Bcl­2 family members, including Bax, Bcl­2 and Bid, regulating MMP and HK­2 expression levels, and increasing the expression of caspase cascade molecules, including caspase­9 and caspase­3. In addition, it may involve the extrinsic apoptosis pathway that activates caspase­8 and caspase­3 leading to apoptosis.


Assuntos
Neoplasias do Colo , Monoterpenos Cicloexânicos , Fluoruracila , Humanos , Fluoruracila/farmacologia , Caspase 3 , Caspase 9 , Caspase 8 , Células HT29 , Apoptose , Neoplasias do Colo/tratamento farmacológico , Neoplasias do Colo/genética , Caspases , Proteínas Proto-Oncogênicas c-bcl-2/genética , RNA Mensageiro
17.
J Ethnopharmacol ; 334: 118542, 2024 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-38992404

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Dried roots of Peucedanum decursivum, a traditional Chinese medicine (TCM), has historically respiratory diseases such as cough, thick phlegm, headache, fever, and gynecological diseases, rheumatoid arthritis, and nasopharyngeal carcinoma. AIM OF THE STUDY: Made an endeavor to evaluate the research trajectory of P. decursivum, comprehensively discern its developmental status, and offer a guideline for future investigations. MATERIALS AND METHODS: A meticulous search of literatures and books from 1955 to 2024 via databases like PubMed, Web of Science and CNKI was conducted, including topics and keywords of " P. decursivum" "Angelica decursivum" and "Zihua Qianhu". RESULTS: P. decursivum and its prescriptions have traditionally been used for treating phlegm-heat cough, wind-heat cough, gastrointestinal diseases, pain relief and so on. It contains 234 identified compounds, encompassing coumarins, terpenes, volatile oils, phenolic acids, fatty acids and derivatives. It exhibits diverse pharmacological activities, including anti-asthmatic, anti-inflammatory, antioxidant effects, anti-hypertensive, anti-diabetic, anti-Alzheimer, and anti-cancer properties, primarily attributed to coumarins. Microscopic identification, HPLC fingerprinting, and bioinformatics identification are the primary methods currently used for the quality control. CONCLUSION: P. decursivum demonstrates anti-asthmatic, anti-inflammatory, and antioxidant effects, aligning with its traditional use. However, experimental validation of its efficacy against phlegm and viruses is needed. Additionally, analgesic effects mentioned in historical texts lack modern pharmacological studies. Numerous isolated compounds exhibit highly valuable medicinal properties. Future research can delve into exploring these substances further. Rigorous of heavy metal contamination, particularly Cd and Pb, is necessary. Simultaneously, investigating its pharmacokinetics and toxicity in humans is crucial for the safety.


Assuntos
Apiaceae , Etnobotânica , Etnofarmacologia , Compostos Fitoquímicos , Controle de Qualidade , Humanos , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/uso terapêutico , Apiaceae/química , Animais , Medicamentos de Ervas Chinesas/farmacologia , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/uso terapêutico , Medicina Tradicional Chinesa/métodos
18.
Front Plant Sci ; 14: 1137840, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-37251761

RESUMO

Introduction: There are several factors that affect the quality and quantity of active ingredients and essential oil (EO) content, including pre and postharvest practices such as drying conditions. One of the most important factors in drying is temperature and then selective drying temperature (DT). In general, DT has a direct effect on the aromatic properties of Anethum graveolens. Methods: On this basis, the present study was conducted to evaluate the effects of different DTs on the aroma profile of A. graveolens ecotypes. Results and discussion: The results showed that different DTs, ecotypes, and their interaction significantly affect EO content and composition. The highest EO yield was obtained from the Parsabad ecotype (1.86%) followed by the Ardabil ecotype (1.4%), both at 40° C. More than 60 EO compounds were identified, mainly monoterpenes and sesquiterpenes, highlighting α-Phellandrene, Germacrene D, and Dill apiole as major components in all treatments. Besides α-Phellandrene, the major EO compounds at shad drying (ShD) were ß-Phellandrene and p-Cymene, while plant parts dried at 40° C showed l-Limonene and Limonene as the main constituents, and Dill apiole was detected in greater amounts in the samples dried at 60 °C. To determine the appropriate DT, simple and factorial based-ANOVA together multivariate analysis demonstrated significant differences in the compounds produced under different DTs. The results indicated that more EO compounds, mainly monoterpenes, were extracted at ShD than other DTs. On the other hand, the content and composition of sesquiterpenes increased significantly when DT was increased to 60 °C. From the genetic backgrounds point of view, the Parsabad ecotype (with 12 similar compounds) and Esfahan ecotype (with 10 similar compounds) were the most suitable ecotypes under all DTs in terms of EO compounds. Accordingly, the present study would help various industries to optimize specific DT(s) to obtain special EO compound(s) from different A. graveolens ecotypes based on commercial requirements.

19.
Nat Prod Res ; : 1-7, 2023 Nov 22.
Artigo em Inglês | MEDLINE | ID: mdl-37991440

RESUMO

Pink pepper (Schinus terebinthifolius Raddi) is a native species native from Central and South America that produces an essential oil (EOpp) with promising applications. This work aimed to investigate the chemical composition and cytotoxic activity of EOpp extracted from unripe (U-EOpp) and ripe (R-EOpp) pink pepper fruits. U-EOpp and R-EOpp were extracted using the hydrodistillation technique and analysed using NMR and GC-MS. U-EOpp and R-EOpp cytotoxic activity was assessed using HL-60 (acute promyelocytic leukemia) and SK-MEL-28 (malignant melanoma) cell lines by MTT assay. Results showed that α-pinene (29.16%), dl-Limonene (20.65%), and ρ-cymene (15.86%) were U-EOpp major components. In addition, l-phellandrene (38.91%), Sylvestrene (23.02%), and α-pinene (21.62%) were R-EOpp major components. U-EOpp showed cytotoxic activity at 37.5 and 18.7 µg/mL for SK-MEL-28 and HL-60, respectively. R-EOpp showed cytotoxic activity for HL-60 at 100 µg/mL. Therefore, EOpp may represent a remarkable source of active natural compounds used in traditional Brazilian medicine.

20.
J Biomol Struct Dyn ; 41(19): 9787-9796, 2023 11.
Artigo em Inglês | MEDLINE | ID: mdl-36411736

RESUMO

Malaria control efforts have been hampered due to the emergence of resistant malaria parasite strains and the coinciding events of Covid-19. The quest for more effective and safe treatment alternatives is driving a slew of new studies that must be accelerated if malaria can be overcome. Due to its reported antimalarial activity, we studied the effects of extract and fractions of Phyllanthus nivosus leaf on Plasmodium lactate dehydrogenase (pLDH) activity using an in vitro assay. This was followed by an anti-plasmodial study using Plasmodium berghei-infected mice and an in silico identification of the plant's phytochemicals with possible pLDH-inhibitory activity. The activity of pLDH was significantly reduced in the presence of ethanol extract and various solvent fractions of Phyllanthus nivosus leaf, with the ethyl acetate fraction having the best inhibitory activity, which was comparable to that of the standard drug (chloroquine). The ethyl acetate fraction at 100 and 200 mg/Kg also suppressed the parasitaemia of Plasmodium berghei-infected mice by 76 and 80% respectively. Among the 53 compounds docked against pLDH, (-)-alpha-Cadinol, (+)-alpha-phellandrene, and spathulenol, all terpenes from the ethyl acetate fraction of P. nivosus leaf extract, demonstrated docking scores comparable to that of chloroquine. The three chemicals, like chloroquine, displayed important molecular interactions with the amino acid residues of the enzyme's NADH-binding site. According to the in silico ADMET study, the three terpenes have suitable drug-like abilities, pharmacokinetic features, and safety profiles. Hence, they could be considered for further development as antimalarial drugs.Communicated by Ramaswamy H. Sarma.


Assuntos
Antimaláricos , Malária , Camundongos , Animais , L-Lactato Desidrogenase , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Malária/tratamento farmacológico , Malária/parasitologia , Antimaláricos/química , Cloroquina/farmacologia , Plasmodium berghei , Plasmodium falciparum
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