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2.
Toxins (Basel) ; 13(12)2021 11 25.
Artículo en Inglés | MEDLINE | ID: mdl-34941680

RESUMEN

Many plants show significant biological activity against pests due to their unique chemical constituents. It is important to identify effective constituents for their development and utilization as botanical pesticides. Our previous study showed that Artemisia lavandulaefolia essential oil had biological activity against Plutella xylostella. Here, we isolated and identified the constituents of essential oil from A. lavandulaefolia by silica gel column chromatography. The main constituents identified were eucalyptol and caryophyllene oxide, and they were confirmed by gas chromatography-mass spectrometry (GC-MS). Eucalyptol and caryophyllene oxide showed strong contact toxicity against P. xylostella larvae after 24 h of application (Median lethal dose, LD50 = 76.97 µL/mL and 20.71 mg/mL. Furthermore, the two active constituents against P. xylostella adults showed significant fumigant activity (Mmedian lethal concentration, LC50 = 3.25 µL/L and 1.06 mg/L, respectively. Finally, we measured the detoxification enzymes and acetylcholinesterase of the larvae treated with active constituents. The eucalyptol-treated larvae displayed enhanced carboxylesterase (CarE) and glutathione-S-transferase (GST) activities in an in vivo experiment, but it was lower for acetylcholinesterase (AchE) activity. The activities of the CarE and GST significantly decreased when exposed to caryophyllene oxide. In general, the two active constituents, eucalyptol and caryophyllene oxide, showed high insecticidal activity, which demonstrates their potential to be used as natural insecticides.


Asunto(s)
Artemisia/química , Insecticidas/farmacología , Mariposas Nocturnas/efectos de los fármacos , Aceites de Plantas/química , Animales , Bioensayo , Eucaliptol/química , Eucaliptol/farmacología , Insecticidas/química , Larva/efectos de los fármacos , Dosificación Letal Mediana , Aceites Volátiles/química , Sesquiterpenos Policíclicos/química , Sesquiterpenos Policíclicos/farmacología
3.
Molecules ; 26(16)2021 Aug 14.
Artículo en Inglés | MEDLINE | ID: mdl-34443521

RESUMEN

One of the primary reasons for the search for new antimicrobial agents is the increasing and spreading resistance of microorganisms to previously used drugs. This is particularly important in the case of rapidly progressing infections that require the rapid administration of an appropriately selected antibiotic. However, along with the administration of antibiotics, complications in the disease-weakened body may arise in the form of systemic mycoses, viral infections, and protozoan infections. Therefore, there is an increasing interest among researchers focusing on the use of naturally occurring terpenic compounds in stand-alone or combined therapies with antibiotics. In this publication, the aim of our work is to present the results of a literature review on the antimicrobial activity of eucalyptol.


Asunto(s)
Antiinfecciosos/uso terapéutico , Farmacorresistencia Bacteriana/genética , Eucaliptol/uso terapéutico , Antibacterianos/efectos adversos , Antibacterianos/uso terapéutico , Antiinfecciosos/química , Eucaliptol/química , Humanos , Micosis/tratamiento farmacológico , Micosis/microbiología
4.
Chem Phys Lipids ; 239: 105113, 2021 09.
Artículo en Inglés | MEDLINE | ID: mdl-34216586

RESUMEN

1,8-cineole is a monoterpene commonly used by the food, cosmetic, and pharmaceutical industries owing to its flavor and fragrances properties. In addition, this bioactive monoterpene has demonstrated bactericidal and fungicidal activities. However, such activities are limited due to its low aqueous solubility and stability. This study aimed to develop nanoemulsion containing cineole and assess its stability and antibacterial activity in this context. The spontaneous emulsification method was used to prepare nanoemulsion (NE) formulations (F1, F2, F3, F4, and F5). Following the development of NE formulations, we chose the F1 formulation that presented an average droplet size (in diameter) of about 100 nm with narrow size distribution (PdI <0.2) and negative zeta potential (∼ - 35 mV). According to the analytical centrifugation method with photometric detection, F1 and F5 formulations were considered the most stable NE with lower droplet migration velocities. In addition, F1 formulation showed high incorporation efficiency (> 80 %) and TEM analyses demonstrated nanosized oil droplets with irregular spherical shapes and without any aggregation tendency. Antibacterial activity assessment showed that F1 NE was able to enhance the cineole action against Staphylococcus aureus, Enterococcus faecalis, and Streptococcus pyogenes. Therefore, using a simple and reproducible method of low energy emulsification we designed a stable nanoemulsion containing 1,8-cineole with improved antibacterial activity against Gram-positive strains.


Asunto(s)
Antibacterianos/química , Emulsiones/química , Eucaliptol/química , Nanoestructuras/química , Antibacterianos/farmacología , Estabilidad de Medicamentos , Enterococcus faecalis/efectos de los fármacos , Eucaliptol/farmacología , Pruebas de Sensibilidad Microbiana , Tamaño de la Partícula , Staphylococcus aureus/efectos de los fármacos
5.
Molecules ; 26(11)2021 May 27.
Artículo en Inglés | MEDLINE | ID: mdl-34071744

RESUMEN

This work aimed to study the chemical composition, cholinesterase inhibitory activity, and enantiomeric analysis of the essential oil from the aerial parts (leaves and flowers) of the plant Lepechinia paniculata (Kunth) Epling from Ecuador. The essential oil (EO) was obtained through steam distillation. The chemical composition of the oil was evaluated by gas chromatography, coupled to mass spectrometry (GC-MS) and a flame ionization detector (GC-FID). The analyses led to the identification of 69 compounds in total, of which 40 were found in the leaves and 29 were found in the flowers of the plant. The major components found in the oil were 1,8-Cineole, ß-Pinene, δ-3-Carene, α-Pinene, (E)-Caryophyllene, Guaiol, and ß-Phellandrene. Flower essential oil showed interesting selective inhibitory activity against both enzymes AChE (28.2 ± 1.8 2 µg/mL) and BuChE (28.8 ± 1.5 µg/mL). By contrast, the EO of the leaves showed moderate mean inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), with IC50 values of 38.2 ± 2.9 µg/mL and 47.4 ± 2.3 µg/mL, respectively.


Asunto(s)
Acetilcolinesterasa/química , Butirilcolinesterasa/química , Inhibidores de la Colinesterasa/farmacología , Lamiaceae/efectos de los fármacos , Aceites Volátiles/química , Extractos Vegetales/química , Hojas de la Planta/química , Monoterpenos Ciclohexánicos/química , Eucaliptol/química , Flores/química , Cromatografía de Gases y Espectrometría de Masas , Hidrocarburos , Concentración 50 Inhibidora , Sesquiterpenos Policíclicos/química , Sesquiterpenos de Guayano/química , Estereoisomerismo
6.
Molecules ; 26(9)2021 Apr 27.
Artículo en Inglés | MEDLINE | ID: mdl-33925478

RESUMEN

The present study examined the chemical composition and antimicrobial and gastrointestinal activity of the essential oils of Elettaria cardamomum (L.) Maton harvested in India (EC-I) and Guatemala (EC-G). Monoterpenes were present in higher concentration in EC-I (83.24%) than in EC-G (73.03%), whereas sesquiterpenes were present in a higher concentration in EC-G (18.35%) than in EC-I (9.27%). Minimum inhibitory concentrations (MICs) of 0.5 and 0.25 mg/mL were demonstrated against Pseudomonas aeruginosa in EC-G and EC-I, respectively, whereas MICs of 1 and 0.5 mg/mL were demonstrated against Escherichia coli in EC-G and EC-I, respectively. The treatment with control had the highest kill-time potential, whereas the treatment with oils had shorter kill-time. EC-I was observed to be more potent in the castor oil-induced diarrhea model than EC-G. At 100 and 200 mg/kg, P.O., EC-I exhibited 40% and 80% protection, respectively, and EC-G exhibited 20% and 60% protection, respectively, in mice, whereas loperamide (10 mg/kg, i.p., positive control) exhibited 100% protection. In the in vitro experiments, EC-I inhibited both carbachol (CCh, 1 µM) and high K+ (80 mM)-induced contractions at significantly lower concentrations than EC-G. Thus, EC-I significantly inhibited P. aeruginosa and E. coli and exhibited more potent antidiarrheal and antispasmodic effects than EC-G.


Asunto(s)
Elettaria/química , Enfermedades Gastrointestinales/tratamiento farmacológico , Bacterias Gramnegativas/efectos de los fármacos , Aceites Volátiles/farmacología , Animales , Antiinfecciosos/química , Antiinfecciosos/farmacología , Modelos Animales de Enfermedad , Eucaliptol/química , Eucaliptol/farmacología , Enfermedades Gastrointestinales/microbiología , Bacterias Gramnegativas/patogenicidad , Guatemala/epidemiología , Humanos , India/epidemiología , Ratones , Aceites Volátiles/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Sesquiterpenos/química , Sesquiterpenos/farmacología
7.
World J Microbiol Biotechnol ; 37(4): 66, 2021 Mar 19.
Artículo en Inglés | MEDLINE | ID: mdl-33740144

RESUMEN

Pseudomonas aeruginosa is one of the vulnerable opportunistic pathogens associated with nosocomial infections, cystic fibrosis, burn wounds and surgical site infections. Several studies have reported that quorum sensing (QS) systems are controlled the P. aeruginosa pathogenicity. Hence, the targeting of QS considered as an alternative approach to control P. aeruginosa infections. This study aimed to evaluate the anti-quorum sensing and antibiofilm inhibitory potential of Musa paradisiaca against Chromobacterium violaceum (ATCC 12472) and Pseudomonas aeruginosa. The methanol extract of M. paradisiacsa exhibits that better antibiofilm potential against P. aeruginosa. Then, the crude methanol extract was subjected to purify by column chromatography and collected the fractions. The mass-spectrometric analysis of a methanol extract of M. paradisiaca revealed that 1,8-cineole is the major compounds. 1, 8-cineole significantly inhibited the QS regulated violacein production in C. violaceum. Moreover, 1,8-cineole significantly inhibited the QS mediated virulence production and biofilm formation of P. aeruginosa without affecting their growth. The real-time PCR analysis showed the downregulation of autoinducer synthase and transcriptional regulator genes upon 1,8-cineole treatment. The findings of the present study strongly suggested that metabolite of M. paradisiaca impedes P. aeruginosa QS system and associated virulence productions.


Asunto(s)
Antibacterianos/farmacología , Biopelículas/efectos de los fármacos , Eucaliptol/química , Eucaliptol/farmacología , Musa/química , Pseudomonas aeruginosa/efectos de los fármacos , Percepción de Quorum/efectos de los fármacos , Alginatos/metabolismo , Biopelículas/crecimiento & desarrollo , Chromobacterium/efectos de los fármacos , Eucaliptol/aislamiento & purificación , Expresión Génica/efectos de los fármacos , Glucolípidos/biosíntesis , India , Pruebas de Sensibilidad Microbiana , Extractos Vegetales/farmacología , Polisacáridos Bacterianos , Pseudomonas aeruginosa/genética , Pseudomonas aeruginosa/crecimiento & desarrollo , Piocianina/biosíntesis , Virulencia/efectos de los fármacos , Factores de Virulencia
8.
Molecules ; 27(1)2021 Dec 21.
Artículo en Inglés | MEDLINE | ID: mdl-35011238

RESUMEN

Herbs, including basil, are used to enhance the flavor of food products around the world. Its potential is influenced by the quality of fresh herbs and processing practices, wherein conditions of heat treatment play an important role. The aim of the research was to determine the effect of sous-vide heat treatment on the volatile compounds profile, sensory quality, and color of basil infusions. The material used for research was aqueous basil infusion prepared conventionally at 100 °C, and using the sous-vide method (65, 75, and 85 °C). The composition of volatile compounds was identified by GC/MS analysis, the sensory profile was assessed using a group of trained panelists, while the color was instrumentally assessed in the CIE Lab system. No significant differences were found in the intensity of the taste and aroma of basil infusions at different temperatures. Seventy headspace volatile compounds were identified in the analyzed samples, ten of which exceeded 2% of relative area percentage. The most abundant compounds were eucalyptol (27.1%), trans-ocimene (11.0%), ß-linalool (9.2%), and ß-myrcene (6.7%). Most of the identified compounds belonged to the terpenes and alcohols groups. Our findings show that the conventional herbal infusion was more like a sous-vide infusion prepared at the lowest temperature SV65, while SV75 and SV85 were similar to each other but different from the conventional. However, a smaller number of volatile compounds in the samples heated at higher temperatures of sous-vide were identified. The sous-vide samples showed a higher content of alkanes. The sous-vide method (p ≤ 0.05) resulted in darker, less green, and less yellow basil leaves than fresh and traditionally steeped ones. Long heat treatment under vacuum at higher temperatures causes a pronounced change in the aroma composition.


Asunto(s)
Ocimum basilicum , Extractos Vegetales , Compuestos Orgánicos Volátiles , Monoterpenos Acíclicos/química , Alquenos/química , Cromatografía de Gases , Eucaliptol/química , Calor , Ocimum basilicum/química , Odorantes , Extractos Vegetales/química , Solventes/química , Gusto , Vacio , Compuestos Orgánicos Volátiles/química
9.
Fitoterapia ; 146: 104721, 2020 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-32919024

RESUMEN

The study of anatomical structure of the aerial part of Artemisia leucodes Schrenk. was carried out, and in this regard, the anatomical and diagnostic features of A. leucodes raw materials were revealed: epidermal cells of an elongated shape, mesophyll in the leaves is columnar, the stem has a fascicular structure, collenchymal mechanical structures are present in the stem ribs. Histochemical analysis shows that the secretory structures of A. leucodes produce sesquiterpene lactones and essential oils, as was confirmed by a chemical study of the aerial parts of A. leucodes. Sesquiterpene lactones anhydroaustricin, matricarin, leucomisin, grossmizin, 5ß(H)-austricin, were isolated from the ethanol extract of A. leucodes by column chromatography on silica gel. By hydrodistillation of anthodium, buds, and leaves an essential oil was obtained, according to chromatography-mass spectrometry, the major component of which was l-camphor - 39.00% and camphene - 9.31%, 1.8-cineole (eucalyptole) - 6.20%. The obtained data on diagnostic features, determination of the localization of secondary metabolites and chemical composition allow us to identify and standardize the medicinal raw materials of A. leucodes, what guarantees quality, and also allow more rational use of A. leucodes in pharmaceutical production.


Asunto(s)
Artemisia/anatomía & histología , Artemisia/química , Aceites Volátiles/química , Extractos Vegetales/química , Eucaliptol/química , Kazajstán , Lactonas/química , Fitoquímicos/química , Componentes Aéreos de las Plantas/anatomía & histología , Componentes Aéreos de las Plantas/química , Sesquiterpenos/química , Terpenos/química
10.
Molecules ; 25(16)2020 Aug 12.
Artículo en Inglés | MEDLINE | ID: mdl-32806608

RESUMEN

BACKGROUND/AIM: natural products are a potential source for drug discovery and development of cancer chemoprevention. Considering that drugs currently available for the treatment of inflammatory and cancer conditions show undesirable side effects, this research was designed to evaluate, for the first time, the in vitro anticancer activity of Algerian Lavandula stoechas essential oil (LSEO) against different cancer cell lines, as well as its in vitro and in vivo topical and acute anti-inflammatory properties. MATERIALS AND METHODS: the LSEO was extracted by steam distillation, and chemical composition analysis was performed using gas chromatography. The main compounds identified in LSEO were oxygenated monoterpenes, such as 1,8-Cineole (61.36%). LSEO exhibited a potent anti-inflammatory activity using the xylene-induced mouse ear edema model. RESULTS: LSEO (200 and 20 mg/kg) was able to significantly reduce (p < 0.05) the carrageenan-induced paw edema with a similar effect to that observed for the positive control. Topical application of LSEO at doses of 82 and 410 mg/kg significantly reduced acute ear edema in 51.4% and 80.1% of the mice, respectively. Histological analysis confirmed that LSEO inhibited the skin inflammatory response. Moreover, LSEO was tested for its antitumor activity against different cancer cell lines. LSEO was found to be significantly active against human gastric adenocarcinoma (AGS), Melanoma MV3, and breast carcinoma MDA-MB-231 cells, with median inhibitory concentration (IC50) values of 0.035 ± 0.018, 0.06 ± 0.022 and 0.259 ± 0.089 µL/mL, respectively. Altogether, these results open a new field of investigation into the characterization of the molecules involved in anti-proliferative processes. CONCLUSION: We suggest that LSEO, with 1,8-Cineole as the major active component, is a promising candidate for use in skin care products with anti-inflammatory and anticancer properties. The results of this study may provide an experimental basis for further systematic research, rational development, and clinical utilization of lavender resources.


Asunto(s)
Antiinflamatorios , Antineoplásicos Fitogénicos , Eucaliptol , Lavandula/química , Neoplasias/tratamiento farmacológico , Aceites Volátiles , Aceites de Plantas , Animales , Antiinflamatorios/química , Antiinflamatorios/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Eucaliptol/química , Eucaliptol/farmacología , Humanos , Inflamación/inducido químicamente , Inflamación/tratamiento farmacológico , Inflamación/metabolismo , Inflamación/patología , Ratones , Neoplasias/metabolismo , Neoplasias/patología , Aceites Volátiles/química , Aceites Volátiles/farmacología , Aceites de Plantas/química , Aceites de Plantas/farmacología
11.
Molecules ; 25(9)2020 May 09.
Artículo en Inglés | MEDLINE | ID: mdl-32397385

RESUMEN

: The present work evaluates for the first time two Lavandin (Lavandula × intermedia Emeric ex Loisel.) aromatic waters obtained from different plant organs, the flowers and the stems. Both extracts were analysed by GC-MS, which indicates semi-quantitative differences between the major metabolites including linalool, 1,8-cineole, camphor, linalyl acetate and 4-terpineol. 1H-NMR and LC-MS investigation confirmed the presence of these compounds. Moreover, behavioural tests with the food insect pest Tribolium confusum (Coleoptera Tenebrionidae) showed a good repellency for both hydrosols extracts with RD50 values of 3.6 and 3.3 µL cm-2 for the flowers and stems, respectively; at the higher concentrations, however, the hydrosol extract from the flowers is expected to be more effective than the one from the stems. The effect of the flowers and stems aromatic water of Lavandin on seed germination of Raphanus sativus was also evaluated. Results showed that seed germination was completely inhibited by flowers hydrolate, having a possible application as natural herbicide. The overall experience with these Lavandin extracts indicates the potential of improved hydrolates to become the main distillation products, rather than by-products, of the aromatic plants manufacturing; this stimulates further discussions about the potential positive impacts that such a shift could have in the context of ecopharmacognosy.


Asunto(s)
Repelentes de Insectos/farmacología , Lavandula/química , Extractos Vegetales/farmacología , Tribolium/fisiología , Monoterpenos Acíclicos/química , Monoterpenos Acíclicos/farmacología , Animales , Alcanfor/química , Alcanfor/farmacología , Eucaliptol/química , Eucaliptol/farmacología , Flores/química , Cromatografía de Gases y Espectrometría de Masas , Germinación , Repelentes de Insectos/química , Italia , Mentol/análogos & derivados , Mentol/química , Mentol/farmacología , Monoterpenos/química , Monoterpenos/farmacología , Aceites Volátiles , Extractos Vegetales/química , Aceites de Plantas , Tallos de la Planta/química , Raphanus/fisiología
12.
Molecules ; 25(10)2020 May 21.
Artículo en Inglés | MEDLINE | ID: mdl-32455788

RESUMEN

Myrtus communis L. is one of the important aromatic and medicinal species from the Mediterranean area. It is used in various fields such as culinary, cosmetic, pharmaceutical, therapeutic, and industrial applications. Thus, a Box-Wilson experimental plan was used in this study to select the optimal operating conditions in order to obtain high volumes of essential oils. The factorial design method was applied to evaluate at an industrial scale the effect of major process variables on the essential oil extraction from Myrtus communis L. herbs by the steam distillation method. The input variables considered as significant operating conditions were: X1-boiler occupancy rate (boilers were filled to 50%, 75%, and 100%), X2-distillation duration (distillation was continued 60, 75, and 90 min), and X3-particle size (herbs were cut in sizes of 10, 20, and 30 mm via guillotine). The dependent variable selected, coded as Y, was the essential oil volume obtained (mL). The steps of the classical statistical experimental design technique were complemented with the Taguchi method to improve the extraction efficacy of essential oil from Myrtus communis L., and the optimum parameter conditions were selected: boiler occupancy rate 100%, distillation duration 75 min, and particle size 20 mm. Following the optimum parameters, the GC-MS assay revealed for the Myrtus communis L. essential oil two predominant components, α-pinene-33.14% and eucalyptol-55.09%.


Asunto(s)
Monoterpenos Bicíclicos/química , Eucaliptol/química , Myrtus/química , Aceites Volátiles/química , Monoterpenos Bicíclicos/aislamiento & purificación , Destilación/métodos , Eucaliptol/aislamiento & purificación , Cromatografía de Gases y Espectrometría de Masas , Aceites Volátiles/aislamiento & purificación , Vapor
13.
Molecules ; 25(7)2020 Mar 30.
Artículo en Inglés | MEDLINE | ID: mdl-32235558

RESUMEN

Among the hundreds of reported Achillea species, A. membranacea (Labill.) DC. is one of the six that grow in Jordan. Many species of this genus are used in folk medicine to treat a variety of ailments and several biological and pharmacological activities have been ascribed to their essential oil (EO). For this study, the EO obtained from a specimen of A. membranacea grown in Jordan was analyzed by GC-MS. Ninety-six compounds were detected, of which oxygenated monoterpenes was the predominant class (47.9%), followed by non-terpene derivatives (27.9%), while sesquiterpenes represented 14.2% of the total composition. The most abundant compound in the EO was 1,8-cineole (21.7%). The cytotoxic activity of the EO was evaluated against three cancer cell lines (MCF7, A2780 and HT29), and one normal fibroblast cell line (MRC5) by MTT assay. Significant growth inhibition was observed in EO-exposed A2780 and HT29 cells (IC50 = 12.99 and 14.02 µg/mL, respectively), while MCF7 and MRC5 were less susceptible. The EO induced apoptosis and increased the preG1 events in A2780 cells. 1,8-Cineole, the major constituent of the EO, exhibited submicromolar cytotoxicity against A2780 cells, and was 42 times more selective against MRC5 cells. Its cytotoxicity against A2780 cells was comparable with that of doxorubicin, but 1,8-cineole was more selective for MRC5 normal cells. Interestingly, 1,8-cineole enhanced apoptosis in A2780, and caused a remarkable dose-dependent increase in preG1 events. Thus, 1,8-cineole has demonstrated promising cytotoxic and proapoptotic properties.


Asunto(s)
Achillea/química , Antineoplásicos Fitogénicos , Apoptosis/efectos de los fármacos , Eucaliptol , Aceites Volátiles , Neoplasias Ováricas/tratamiento farmacológico , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Eucaliptol/química , Eucaliptol/farmacología , Femenino , Células HT29 , Humanos , Células MCF-7 , Aceites Volátiles/química , Aceites Volátiles/farmacología , Neoplasias Ováricas/metabolismo , Neoplasias Ováricas/patología
14.
Chem Biodivers ; 17(3): e1900669, 2020 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-31984627

RESUMEN

1,8-Cineole is the main volatile produced by Thymus albicans Hoffmanns. & Link 1,8-cineole chemotype. To understand the contribution of distinct plant organs to the high 1,8-cineole production, trichome morphology and density, as well as emitted volatiles and transcriptional expression of the 1,8-cineole synthase (CIN) gene were determined separately for T. albicans leaves, bracts, calyx, corolla and inflorescences. Scanning electron microscopy (SEM) and stereoscope microscopy observations showed the highest peltate trichome density in leaves and bracts, significantly distinct from calyx and corolla. T. albicans volatiles were collected by solid phase micro extraction (SPME) and analyzed by gas chromatography-mass spectrometry (GC/MS) and by GC for component identification and quantification, respectively. Of the 23 components identified, 1,8-cineole was the dominant volatile (57-93 %) in all T. albicans plant organs. The relative amounts of emitted volatiles clearly separated vegetative from reproductive organs. Gene expression of CIN was assigned to all organs analyzed and was consistent with the relatively high emission of 1,8-cineole in leaves and bracts. Further studies will be required to analyze monoterpenoid biosynthesis by each type of glandular trichome.


Asunto(s)
Liasas de Carbono-Carbono/genética , Eucaliptol/metabolismo , Genitales/química , Aceites Volátiles/metabolismo , Thymus (Planta)/metabolismo , Liasas de Carbono-Carbono/metabolismo , Eucaliptol/química , Flores/química , Flores/metabolismo , Frutas/química , Frutas/metabolismo , Genitales/metabolismo , Aceites Volátiles/química , Hojas de la Planta/química , Hojas de la Planta/metabolismo , Thymus (Planta)/química
15.
Int J Pharm ; 575: 118920, 2020 Feb 15.
Artículo en Inglés | MEDLINE | ID: mdl-31863880

RESUMEN

The hypothesis for the investigation was that the overall mechanism of action of skin penetration enhancers is best explained by the Solubility-Physicochemical-Thermodynamic (SPT) theory. To our knowledge, this is the first report of the application of SPT theory in transdermal/topical/enhancer research. The SPT theory puts forward the concept that the mode of action of enhancers is related to solubility parameters, physicochemical interactions and thermodynamic activity. This paper discusses these concepts by using experimentally derived permeation data, various physicochemical and solubility parameters (ingredient active gap (IAG), ingredient skin gap (ISG), solubility of active in the formulation (SolV) and the formulation solubility in the skin (SolS)) generated by using FFE (Formulating for Efficacy™ - ACT Solutions Corp) software. These studies suggest that there is an inverse relationship between measured flux and IAG values given that there is an optimum ingredient skin gap, SolV and SolS ratio. The study demonstrated that the flux is actually proportional to a gradient of thermodynamic activity rather than the concentration and maximum skin penetration and deposition can be achieved when the drug is at its highest thermodynamic activity.


Asunto(s)
Benzoquinonas/administración & dosificación , Excipientes/administración & dosificación , Nicotina/administración & dosificación , Absorción Cutánea , Administración Cutánea , Azepinas/administración & dosificación , Azepinas/química , Benzoquinonas/química , Eucaliptol/administración & dosificación , Eucaliptol/química , Excipientes/química , Humanos , Técnicas In Vitro , Modelos Teóricos , Nicotina/química , Ácido Oléico/administración & dosificación , Ácido Oléico/química , Polisorbatos/administración & dosificación , Polisorbatos/química , Propilenglicol/administración & dosificación , Propilenglicol/química , Pirrolidinonas/administración & dosificación , Pirrolidinonas/química , Piel/metabolismo , Programas Informáticos , Solubilidad , Termodinámica
16.
Chembiochem ; 21(7): 985-990, 2020 04 01.
Artículo en Inglés | MEDLINE | ID: mdl-31682055

RESUMEN

Monoterpenoids are industrially important natural products with applications in the flavours, fragrances, fuels and pharmaceutical industries. Most monoterpenoids are produced by plants, but recently two bacterial monoterpene synthases have been identified, including a cineole synthase (bCinS). Unlike plant cineole synthases, bCinS is capable of producing nearly pure cineole from geranyl diphosphate in a complex cyclisation cascade that is tightly controlled. Here we have used a multidisciplinary approach to show that Asn305 controls water attack on the α-terpinyl cation and subsequent cyclisation and deprotonation of the α-terpineol intermediate, key steps in the cyclisation cascade which direct product formation towards cineole. Mutation of Asn305 results in variants that no longer produce α-terpineol or cineole. Molecular dynamics simulations revealed that water coordination is disrupted in all variants tested. Quantum mechanics calculations indicate that Asn305 is most likely a (transient) proton acceptor for the final deprotonation step. Our synergistic approach gives unique insight into how a single residue, Asn305, tames the promiscuous chemistry of monoterpene synthase cyclisation cascades. It does this by tightly controlling the final steps in cineole formation catalysed by bCinS to form a single hydroxylated monoterpene product.


Asunto(s)
Liasas Intramoleculares/metabolismo , Monoterpenos/metabolismo , Sitios de Unión , Dominio Catalítico , Ciclización , Monoterpenos Ciclohexánicos/química , Monoterpenos Ciclohexánicos/metabolismo , Eucaliptol/química , Eucaliptol/metabolismo , Hidroxilación , Liasas Intramoleculares/genética , Simulación de Dinámica Molecular , Monoterpenos/química , Mutagénesis Sitio-Dirigida , Estereoisomerismo , Streptomyces/enzimología , Agua/química , Agua/metabolismo
17.
Eur J Pharm Sci ; 142: 105135, 2020 Jan 15.
Artículo en Inglés | MEDLINE | ID: mdl-31682974

RESUMEN

The objective of this work was to develop low-energy nanoemulsions for enhanced dermal delivery of curcumin, using monoterpene compounds eucalyptol (EUC) and pinene (PIN) as chemical penetration enhancers. Spontaneous emulsification was the preparation method. All formulations contained 10% of the oil phase (medium-chain triglycerides (MCT), or their mixture with EUC or PIN). Formulations were stabilized by the combination of polysorbate 80 and soybean lecithin (surfactant-to-oil-ratio=1). Concentration of curcumin was set to 3 mg/ml. Average droplet diameter of all tested formulations ranged from 102 nm to 132 nm, but the ones containing monoterpenes had significantly smaller size compared to the MCT formulation. Such finding was profoundly studied through electron paramagnetic resonance spectroscopy, which proved that the presence of monoterpenes modified the nanoemulsions' interfacial environment, resulting in droplet size reduction. The release study of curcumin (using Franz cells) demonstrated that the cumulative amount released after 6 h of the experiment was 10.1 ±â€¯0.2% for the MCT nanoemulsions, 13.9 ±â€¯0.1% and 14.0 ±â€¯0.2% for PIN and EUC formulations, respectively. In vivo tape stripping revealed their performances in delivering curcumin into the skin, indicating the following order: EUC>MCT>PIN. The formulation with EUC was clearly the most successful, giving the highest cumulative amount of curcumin that penetrated per surface unit: 34.24±5.68 µg/cm2. The MCT formulation followed (30.62±2.61 µg/cm2) and, finally, the one with PIN (21.61±0.11 µg/cm2). These results corelated with curcumin's solubility in the chosen oils: 4.18±0.02 mg/ml for EUC, 1.67±0.04 mg/ml for MCT and 0.21±0.01 mg/ml for PIN. Probably, higher solubility in the oil phase of the nanoemulsion promoted curcumin's solubility in the superficial skin layers, providing enhanced penetration.


Asunto(s)
Curcumina/química , Emulsiones/química , Eucaliptol/química , Nanopartículas/química , Nanoestructuras/química , Terpenos/química , Administración Cutánea , Adulto , Curcumina/farmacología , Emulsiones/farmacología , Femenino , Humanos , Lecitinas/química , Monoterpenos/química , Aceites/química , Polisorbatos/química , Piel/efectos de los fármacos , Absorción Cutánea/fisiología , Solubilidad/efectos de los fármacos , Tensoactivos/química , Adulto Joven
18.
Biomolecules ; 9(10)2019 10 02.
Artículo en Inglés | MEDLINE | ID: mdl-31581691

RESUMEN

Given the importance of the genus Artemisia as a source of valuable natural products, the rare plant Artemisia pedemontana subspecies assoana, endemic to the Iberian Peninsula, has been experimentally cultivated in the greenhouse and aeroponically, to produce biomass for essential oil (EO) extraction. The chemical composition of the EOs was analyzed, and their plant protection (insects: Spodoptera littoralis, Rhopalosiphum padi, and Myzus persicae; plants: Lactuca sativa and Lolium perenne; fungi: Aspergillus niger; and nematode: Meloidogyne javanica) and antiparasitic (Trypanosoma cruzi, Phytomonas davidi, and antiplasmodial by the ferriprotoporphyrin biocrystallization inhibition test) properties were studied, in addition to the hydrolate by-product. The EOs showed a 1,8-cineole and camphor profile, with quantitative and qualitative chemical differences between the cultivation methods. These oils had moderate insect antifeedant, antifungal, and phytotoxic effects; were trypanocidel; and exhibited moderate phytomonacidal effects, while the hydrolate showed a strong nematicidal activity. Both EOs were similarly antifeedant; the EO from the greenhouse plants (flowering stage) was more biocidal (antifungal, nematicidal, and phytotoxic) than the EO from the aeroponic plants (growing stage), which was more antiparasitic. The major components of the oils (1,8-cineole and camphor), or their 1:1 combination, did not explain any of these effects. We can conclude that these EOs have potential applications as insect antifeedants, and as antifungal or antiparasitic agents, depending on the cultivation method, and that the hydrolate byproduct is a potent nematicidal.


Asunto(s)
Artemisia/crecimiento & desarrollo , Aceites Volátiles/química , Aceites Volátiles/farmacología , Animales , Áfidos/efectos de los fármacos , Artemisia/química , Alcanfor/química , Alcanfor/farmacología , Eucaliptol/química , Eucaliptol/farmacología , Hongos/efectos de los fármacos , Nematodos/efectos de los fármacos , Aceites de Plantas/química , Aceites de Plantas/farmacología
19.
J Chem Ecol ; 45(9): 779-788, 2019 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-31478157

RESUMEN

In China, the genus Adelphocoris (Hemiptera: Miridae) includes three dominant pest species (A. suturalis, A. lineolatus and A. fasciaticollis), which cause great damage to cotton, alfalfa and other crops. In this study, we examined the role of the major volatile organic compounds from plants in host location by these three insects. Gas chromatography-electroantennography and gas chromatography/mass spectrometry analyses identified seven electroantennogram (EAG)-active compounds from 11 host plants. Although the insects responded to all of these compounds in EAG trials, some compounds did not elicit behavioral responses in Y-tube olfactometer bioassays. Adelphocoris suturalis adults showed behavioral responses to four EAG-active compounds, n-butyl ether, butyl acrylate, butyl propionate and butyl butyrate. These four compounds, in addition to p-xylene, were also attractive to A. lineolatus adults. However, A. fasciaticollis adults were attracted only by butyl acrylate, butyl propionate and butyl butyrate. In field trials, A. suturalis and A. fasciaticollis were each attracted to five individual compounds (m-xylene, n-butyl ether, butyl acrylate, butyl butyrate and butyl propionate for A. suturalis and m-xylene, butyl acrylate, butyl butyrate, butyl propionate, and 1,8-cineole for A. fasciaticollis). By contrast, A. lineolatus aduts were attracted to six individual compounds, m-xylene, p-xylene, n-butyl ether, butyl acrylate, butyl butyrate, and butyl propionate. These compounds may be important in host plant location by the Adelphocoris species, and may be useful for developing attractants for adults of these species.


Asunto(s)
Productos Agrícolas , Heterópteros , Interacciones Huésped-Parásitos , Compuestos Orgánicos Volátiles/química , Animales , Conducta Animal , Ácidos Carboxílicos/química , Productos Agrícolas/química , Productos Agrícolas/metabolismo , Eucaliptol/química , Femenino , Cromatografía de Gases y Espectrometría de Masas , Heterópteros/química , Heterópteros/metabolismo , Masculino , Xilenos/química
20.
Int J Mol Sci ; 20(14)2019 Jul 17.
Artículo en Inglés | MEDLINE | ID: mdl-31319552

RESUMEN

Acne is an inflammatory skin disorder in puberty with symptoms including papules, folliculitis, and nodules. Propionibacterium acnes (P. acnes) is the main anaerobic bacteria that cause acne. It is known to proliferate within sebum-blocked skin hair follicles. P. acnes activates monocytic cell immune responses to induce the expression of proinflammatory cytokines. Although the anti-inflammatory function of the Laurus nobilis (L. nobilis) extract (LNE) on several immunological disorders have been reported, the effect of LNE in P. acnes-mediated skin inflammation has not yet been explored. In the present study, we examined the ability of the LNE to modulate the P. acnes-induced inflammatory signaling pathway, and evaluated its mechanism. LNE significantly suppressed the expression of P. acnes-mediated proinflammatory cytokines, such as IL-1ß, IL-6, and NLRP3. We also found that LNE inhibited the inflammatory transcription factor NF-κB in response to P. acnes. In addition, eucalyptol, which is the main constituent of LNE, consistently inhibited P. acnes-induced inflammatory signaling pathways. Moreover, LNE significantly ameliorated P. acnes-induced inflammation in a mouse model of acne. We suggest for the first time that LNE hold therapeutic value for the improvement of P. acnes-induced skin inflammation.


Asunto(s)
Acné Vulgar/tratamiento farmacológico , Antiinflamatorios/farmacología , Eucaliptol/farmacología , Infecciones por Bacterias Grampositivas/tratamiento farmacológico , Laurus/química , Extractos Vegetales/farmacología , Propionibacterium acnes/crecimiento & desarrollo , Acné Vulgar/metabolismo , Acné Vulgar/microbiología , Acné Vulgar/patología , Animales , Antiinflamatorios/química , Línea Celular , Eucaliptol/química , Infecciones por Bacterias Grampositivas/metabolismo , Infecciones por Bacterias Grampositivas/microbiología , Infecciones por Bacterias Grampositivas/patología , Inflamación/tratamiento farmacológico , Inflamación/metabolismo , Inflamación/microbiología , Inflamación/patología , Ratones , Extractos Vegetales/química
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