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Cannabis sativa L. is a plant that has been cultivated since ancient times thanks to its various uses. Even its extraction products, such as essential oil and hydrolate, having a varied chemical composition and rich in bioactive components, find wide use in different sectors, gathering ever-increasing interest over time. In this work, the essential oil of Cannabis sativa L. cv. Carmagnola was characterized by using Gas Chromatography/Mass Spectrometry (GC/MS) and, for the first time, the chemical profile of the hydrolate was also described through different analytical techniques such as Large-Volume Injection Gas Chromatography/Mass Spectrometry (LVI-GC/MS) and Direct Immersion-Solid Phase Microextraction-Gas Chromatography/Mass spectrometry (DI-SPME-GC/MS), in order to provide a more complete compositional profile. The results of the analyses conducted on the hydrolate highlighted a high content of α-terpineol; on the other side, in the essential oil, a prevalence of monoterpenes, with α-pinene and limonene as the characterizing components, was detected. Both matrices were also investigated to evaluate their cytotoxic activity by using a panel of cancer cell lines derived from different histotypes such as melanoma (A375, LOX IMVI), non-small cell lung cancer (H1299, A549), colon (HT29) and pancreatic (L3.6) cancer cell lines. The obtained data demonstrated that essential oil was more effective than hydrolate in terms of reduction in cell viability.
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Cannabis , Cromatografía de Gases y Espectrometría de Masas , Aceites Volátiles , Microextracción en Fase Sólida , Aceites Volátiles/química , Aceites Volátiles/farmacología , Aceites Volátiles/análisis , Cromatografía de Gases y Espectrometría de Masas/métodos , Cannabis/química , Humanos , Microextracción en Fase Sólida/métodos , Línea Celular Tumoral , Compuestos Orgánicos Volátiles/análisis , Compuestos Orgánicos Volátiles/química , Supervivencia Celular/efectos de los fármacos , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/químicaRESUMEN
Honeybees are insects very sensitive to environmental pollution and at the same time very good indicators of the pollution levels for certain types of pollutants. The morphology and ethology of these insects make them perfect vectors for dust and substances, including heavy metals produced by anthropic activities or naturally generated and deposited on foraged flora. When bees are raised to produce foods such as honey and pollen, they can easily transfer pollutants collected from contaminated flower affecting the quality of these products. However, depending on geographical location of the apiaries and their distance from pollution sources, the risk to contaminate bee products can be higher or lower requiring deep investigations. In this study, two apiaries were built near ground transport infrastructures and used as monitoring stations for investigating heavy metal presence in beehive products such as bee wax, pollen, and honey. Another apiary was placed between these two locations at a distance of 500 m from each one and used as central node to asses possible diffusion trends. Parallel, air quality was monitored in the proximity of each apiary to verify the air pollution of the environments close to these sites. The results of the study suggest that the presence of the highway and the train station affected the levels of heavy metal presence in the apiary products. Air quality near apiaries was also negatively affected by ground transport, especially in proximity of the highway. Wax resulted significantly more polluted in the apiary close to train station with elements such as Al, Zn, and Ni, while honey and pollen were significantly more polluted in the proximity of the highway with elements such as Al, Fe, Cu, and Zn. Honey was the product suffering less the contamination by heavy metals while pollen was the worse. In conclusion, the presence of transportation nodes determined a higher accumulation of heavy metals in beehive products respect the apiary placed in between, suggesting to pay particular attention in the site selection for the placement of apiaries to protect both bees and human health.
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Monitoreo del Ambiente , Miel , Metales Pesados , Abejas , Metales Pesados/análisis , Animales , Miel/análisis , Polen/químicaRESUMEN
The preservation of agricultural biodiversity and socioeconomic development are relevant both to enhance domestic production and to support innovation. In the search for new biomolecules, we have focused on the "Carciofo Ortano" landrace, growth in the northern part of the Lazio region. Artichoke cultivation generates substantial by-products, including leaves, stems, and roots, which could serve as valuable sources of biomolecules and prebiotic dietary fiber. To valorize the leaf waste of the "Carciofo Ortano" landrace, a multidisciplinary approach was applied. Chemical analysis using HPLC-DAD identified mono-O- and di-O-caffeoylquinic acids and the sesquiterpene cynaropicrin in all artichoke leaf extracts. SPME-GC/MS analyses detected aliphatic alcohols in the fresh leaf samples. Antiproliferative and cytotoxic studies on cancer (SH-SY5Y, MCF-7, MDA) and normal (MCF-10A) human cell lines revealed that leaf extracts induced a selective dose and time-dependent biological effect. While showing slight activity against environmental bacterial strains, artichoke leaf extracts exhibited significant antifungal activity against the phytopathogenic fungus Alternaria alternata. Overall, the results highlight the potential of "Carciofo Ortano" cultivation by-products as a rich source of biomolecules with versatile applications in humans, animals, and the environment.
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Acidolysis lignins from the species Quercus cerris L. and Eucalyptus camaldulensis Dehnh. were isolated and characterized using high pressure size exclusion chromatography (HP-SEC), Fourier-transform (FTIR) infrared spectroscopy, analytical pyrolysis-gas chromatography-mass spectrometry (Py-GCMS), and two-dimensional heteronuclear single quantum coherence (2D HSQC) NMR spectroscopy. The acidolysis lignins from the two different species varied in chemical composition and structural characteristics, with Q. cerris L. lignin having a higher S/G ratio and higher molar mass averages with a bimodal molar mass distribution. The different analytical techniques FTIR spectroscopy, Py-GCMS, and 2D NMR spectroscopy provided consistent results regarding the S/G ratio of the lignins from the two wood species. Based on the determined high S/G ratio of both oak and eucalypt lignin, the two wood sources could be promoted as substrates for efficient lignin isolation in modern forest biorefineries in order to develop innovative lignin-based value-added biorefinery products.
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Currently, the leaves of the hop plant (Humulus lupulus L.) are an unexploited and still little-investigated agricultural by-product. In our study, with the aim of exploring the metabolome of dried hop leaves (Chinook cultivar), a metabolomic approach was applied using multiple analytical tools such as SPME/GC-MS, GC-MS, PTR-ToF-MS, and NMR to identify the secondary metabolites. The obtained results showed the presence of a high number of components belonging to different chemical classes. In fact, thanks to the multi-methodological approach, volatile organic compounds (VOCs) with low molecular weight, terpenic compounds, fatty acids, sugars, amino acids, organic acids, and alcohols have been detected and identified. Among the revealed terpenes in the untreated matrix, the sesquiterpenes α-humulene, ß-caryophyllene, and α-copaene were the most abundant. Among the saturated and unsaturated fatty acids, palmitic and linolenic acids, respectively, were those with the highest relative percentages. Particularly relevant was the sugar content, where sucrose was the main exponent while glutamate and asparagine were the principal detected amino acids. Conversely, alcohols and organic acids were the least abundant compound classes, and xanthohumol was also identified in the methanolic extract.
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Humulus , Metabolómica , Aminoácidos , Metaboloma , Ácido GlutámicoRESUMEN
In this study, for the first time, the chemical composition of Echinacea purpurea (L.) Moench. and propolis (EAP) hydroalcoholic solution from the Trentino Alto Adige region of northern Italy was investigated by using SPME-GC-MS to describe the volatile content and GC-MS after silylation to detect the non-volatile compounds in the extractable organic matter. The antimicrobial activity of EAP hydroalcoholic solution was evaluated by Minimum Inhibitory Concentration (MIC) determination on 13 type strains, food and clinical isolates. Time Kill Kinetics (TKK) assays and the determination on swimming and swarming motility for 48 h gave more details on the mode of action of EAP solution. The results highlighted the presence of some terpenes and a large number of compounds belonging to different chemical classes. Among these, sugars and organic acids excelled. The EAP hydroalcoholic solution exhibited a strong antimicrobial activity in terms of MIC, with a clear decrease in the cellular load after 48 h. However, the bacterial motility may not be affected by the EAP treatment, displaying a dynamic swarming and swimming motility capacity over time. Given the complexity of chemical profile and the strong antimicrobial effectiveness, the EAP hydroalcoholic solution can be considered a source of bioactive molecules, deserving further investigation for the versatility of application.
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Antiinfecciosos , Echinacea , Própolis , Própolis/farmacología , Própolis/química , Echinacea/química , Antiinfecciosos/farmacología , Cromatografía de Gases y Espectrometría de Masas/métodos , ItaliaRESUMEN
Considering the large number of volatile molecules that characterize Cannabis sativa L., adequate investigation supported by the application of robust and effective analytical methods is essential to better understand the impact of these low- and medium-molecular-weight molecules on the entire phytocomplex. This work aimed to characterize the volatile fraction of the chemical profile of three different cultivars of Cannabis sativa L. pollen, grown in Italy, which were thoroughly investigated by the application of two complementary techniques: SPME-GC-MS and PTR-ToF-MS. Furthermore, in order to provide more information on the chemical profile of the matrices under study, the cannabinoid content of the hexane extracts was also measured by GC-MS. Until now, no similar study, in terms of survey techniques applied, has been performed on C. sativa pollen. The obtained results showed a high content of volatile molecules, which differentiated the three matrices. The data relating to the content of cannabinoids were also interesting as they showed that one of the three cultivars was richer than the others. Finally, an in-depth statistical survey was performed to better compare the investigated samples and identify the molecules that most contribute to differentiating them. The findings of this study may be useful for integrating the compositional information on C. sativa L.
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Cannabinoides , Cannabis , Cannabinoides/química , Cannabis/química , Cromatografía de Gases y Espectrometría de Masas/métodos , Microextracción en Fase Sólida/métodos , Polen/químicaRESUMEN
Three different formulations of bio-based polyurethane (PU), varying the weight ratio between Organosolv lignin and a commercial isocyanate, were synthesized. The coating formulations were characterized by SEM, pyrolysis-GC/MS, FTIR spectroscopy and FTIR mapping, which confirmed the successful formation of urethane bonds between commercial isocyanate and hydroxyl groups deriving from lignin. The coatings were applied on beech wood samples to measure color and contact angles, and eventually FTIR mapping of the coated wood samples was performed. FTIR mapping is an interesting tool to monitor the distribution of PU chemical bonds on the coating surface and to evaluate the homogeneity of the applied coating films. Increasing the lignin content of the PU coatings results in more red-yellow and darker tones, while the commercial PU coating is transparent. For a higher lignin concentration, the solid content as well as the weight gain of the applied coatings increase. A higher percentage of lignin in the prepared PU formulations leads to superficial cracks and therefore higher coating permeability compared to the commercial PU, but the prepared lignin-based PU coating still makes a raw wood surface significantly more hydrophobic. Apparently, additives such as film-formers with low surface tension to counteract cracks' formation are necessary to improve the performance of lignin-based PU coatings.
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Biting midges of the genus Culicoides (Diptera: Ceratopogonidae) play a paramount role in medical and veterinary entomology worldwide, particularly as vectors of pathogens which cause animal diseases. Biting midges are also infamous for the nuisance they provoke to people involved in outdoor activities. Nonetheless, attacks to man by midges from any Culicoides species have not been reported in Italy. An entomological investigation was performed following repeated attacks to man in a nature park near Rome (central Italy). The study area is a natural degassing zone, characterized by widespread hazardous gas emissions of CO2 and H2S, with several water bodies including permanent lakes, ponds, and pools. The biting midge C. riethi Kieffer, 1914 was very active during daytime in the period April-June. The species has been identified as responsible for attacks on people in the area. An in-depth analysis of the extreme environmental conditions revealed the ability of larvae to thrive in several water bodies, characterized by an extremely low pH and a high concentration of sulfates.
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Ceratopogonidae , Animales , Cruzamiento , Humanos , Insectos Vectores , Italia , Larva , AguaRESUMEN
Citrus secondary metabolites, such as terpene compounds, are very important for human health due to their bioactivity including anti-inflammatory, anti-cancer, and antioxidant effects. In this work, for the first time, the volatile chemical composition of peels and juices from four different Citrus species (C. junos, Citrus × aurantium, C. aurantium 'Bizzarria' and C. medica 'Florentina', commonly known as Yuzu jeune, Oni Yuzu, Bizzarria orange and Florence cedar, respectively) was investigated by Solid-Phase Microextraction-Gas Chromatography/Mass Spectrometry (SPME-GC/MS) technique and the antiradical activity was also examined. The results showed that limonene and γ-terpinene were the main volatile substances detected both in the juices and in the peels, followed by other minority compounds responsible for the phyto-complex of the unique aromas which characterize each individual analyzed Citrus species. Principal component analysis (PCA), performed on volatile compounds, showed both some correlation as well as a clear separation between the juice and the peel of each species. Among them, Oni Yuzu juice was found to be the richest in total polyphenols and flavonoids while its capacity to scavenge ABTSâ¢+ and DPPH⢠radicals was similar to that of Yuzu Jeune and Bizzarria orange.
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Citrus/química , Depuradores de Radicales Libres/química , Aceites Volátiles/química , Extractos Vegetales/química , Cromatografía de Gases , Citrus/clasificación , Flavonoides/química , Espectrometría de Masas , Polifenoles/químicaRESUMEN
Stinging nettle (Urtica dioica L.) is a ubiquitous, multi-utility, and under-utilized crop with potential health benefits owing to its nutritional and bioactive components. The objective of the work is to produce powders by drying wild stinging nettle leaves as a storable, low-cost functional additive to be used in bakery and ready-to-cook products. Convective drying (CD) and freeze-drying (FD) were applied on unblanched (U) or blanched (B) leaves, which were then milled to nettle powders (NPs). The obtained NPs were evaluated for selected physicochemical (moisture, color), techno-functional (flow indices, hygroscopicity), and phytochemical (pigments, phenols) characteristics as well as mineral contents. Blanching improved mass transfer and reduced the oxidative degradation of pigments during drying, but it caused a loss of total phenols content, antioxidant activity, and potassium content. As for the drying method, CD resulted in better flow properties (i.e., Carr Index and Hausner Ratio), while FD retained better the color, pigments, magnesium content, phenolic, and antioxidant parameters. Overall, the evaluated processing methods resulted in different technological properties that can allow for better evaluation of NPs as a food additive or ingredient. Among the NPs, blanched and freeze-dried powders despite showing inferior technological properties can be recommended as more suitable ingredients targeted f or food enrichment owing to better retention of bio-active components.
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Site conditions and forest management affect dendrometric parameters of chestnut (Castanea sativa Mill.) coppices, but there is modest knowledge on the effect of stand dendrometric characters on physical and mechanical wood characteristics. The aim of this study was to verify these relationships in chestnut coppices that were 12-14 years old. Wood density, compression and bending strength, shrinkages were measured on shoots of five different stand in a vulcanic site in Monte Amiata (Central - Italy). Investigated stands differ in number of stools/ha and dominant height, diameter/basal area of the shoots. The main difference in the physical characters among the stands is density. The initial results of the study showed that physical, mechanical wood characters are more dependent by the shoot than by the site. There is a positive relationships between the number of stools/ha and density and a negative one among shoot dominant height and basal area with wood density. Spectroscopic profile by FTIR has not showed relevant differences among the stands. Wood anatomy has showed the breakpoint at cellular level.
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Agricultura/métodos , Fagaceae/metabolismo , Fagaceae/fisiología , Conservación de los Recursos Naturales/métodos , Agricultura Forestal/métodos , Bosques , Italia , Árboles/crecimiento & desarrollo , Madera/análisisRESUMEN
Sustainability and ecotoxicity issues call for innovations regarding eco-friendly adhesives in the production of biocomposite wood materials, and solutions involving nano-scale and bio-based compounds represent a valid and promising target. One possible approach is to increase the performance of adhesives such as polyvinyl acetate (PVAc) or melamine-urea-formaldehyde (MUF) by means of nanoparticles in order to obtain a material with better mechanical and environmental resistance. When applying cellulose-based nanoparticles or tannin, the concept of a circular economy is successfully implemented into the forest/wood value chain, and chances are created to develop new value chains using byproducts of forestry operations. In this study, assortments coming from young sweet chestnut (Castanea sativa Mill.) coppice stands were utilized for the preparation of single lap joint assemblies using different commercial adhesives (PVAc, MUF) and cellulose nanocrystals (CNC) and tannin as additives. The results showed that addition of CNC and tannin to PVAc glue increased tensile shear strength in lap joint tests presenting a promising base for future tests regarding the addition of CNC and tannin in MUF or PVAc adhesive formulations. Unfortunately, the tested bio-based additives did not reveal the same encouraging results when tested in the wet state.
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Lignin isolated from beech sawdust was used for the preparation of lignin nanoparticles (LNPs) with entrapped essential oil (EO) from cinnamon bark (Cinnamomum zeylanicum Blume), common thyme (Thymus vulgaris L.), and wild thyme (Thymus serpyllum L.) using a fast antisolvent method. Analysis of EO-loaded LNPs by pyrolysis-gas chromatography-mass spectrometry and Fourier transform infrared spectroscopy confirmed molecular interaction between EOs and LNPs. Quantification of EO incorporation into the LNPs and their in vitro release profiles were assessed by reversed phase high-performance liquid chromatography. Utilized EOs were, to different extents, successfully entrapped inside LNPs, which were attributed to extensive π-stacking between aromatic compounds in EOs like cinnamaldehyde, thymol, and carvacrol on one side and aromatic lignin units on the other side. In vitro release of common thyme and wild thyme EOs from EO-loaded LNPs was strongly delayed compared to the use of pure oil, giving a promising outlook for the development of new bio-based biocide delivery systems for wood preservation.
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BACKGROUND: Chestnuts are gluten-free, low-fat, cholesterol-free products. Postharvest decay reduces chestnut shelf life and can cause severe economic losses. In this study we investigated the effect of ozone (O3 ) gaseous treatment on chestnut rot caused by Gnomoniopsis castanea and the quality parameters of chestnuts. RESULTS: The results showed that ozone treatment (150 ppb during the day, and 300 ppb during the night) reduced the decay of chestnuts and had a fungistatic effect on isolates of G. castanea. The exposure of chestnuts to ozone did not alter weight losses, sugar content and titratable acidity. The concentration of total phenolics decreased during the storage period, both for treated and untreated nuts. However, after 150 days of treatment the polyphenol content of the chestnuts exposed to ozone was significantly higher than in control nuts. CONCLUSIONS: Our results suggested that ozone is an appropriate and economical tool to maximize the quality of chestnut shelf life, enabling it to be stored for long periods. © 2019 Society of Chemical Industry.
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Fagaceae/química , Conservación de Alimentos/métodos , Conservantes de Alimentos/farmacología , Nueces/química , Ozono/farmacología , Ascomicetos/efectos de los fármacos , Ascomicetos/fisiología , Carbohidratos/química , Fagaceae/microbiología , Conservación de Alimentos/instrumentación , Conservantes de Alimentos/química , Almacenamiento de Alimentos , Nueces/microbiología , Ozono/química , Fenoles/química , Control de CalidadRESUMEN
Lignin was isolated from wood wastes comprising Iroko sawdust (IR) and mixed sawdust from Iroko and Norway spruce (IRNS), furnished by a local wood houses producer. The respective acidolysis lignin fractions were structurally characterized using pyrolysis (Py)-GCMS, two-dimensional heteronuclear single quantum correlation nuclear magnetic resonance (2D HSQC NMR), Fourier-transform infrared FTIR and ultraviolet-visible (UV-VIS) spectroscopies, size exclusion chromatography, and standard wet-chemistry methods for Klason lignin and polysaccharides determination. The isolated lignin fractions were subsequently used for the preparation of lignin nanoparticles (LNPs) using a non-solvent method. LNPs were then used for wood surface treatment using a dip-coating technique. The coated wood samples were analyzed by colorimetry and scanning electron microscopy (SEM) before and after artificial weathering experiments in a UV chamber to investigate the UV protection potential of the LNPs coatings. Wood samples dip-coated with LNPs showed promising surface modifications resembling a sort of film of fused LNPs. Coatings made from IR-LNPs and IRNS-LNPs performed significantly better in artificial weathering experiments than uncoated reference samples.
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The composition of the essential oils (EOs) of O. vulgare L. EO and T. vulgaris EO, were analyzed by GC and GC-MS. Antifungal activities of the EOs and its main component, carvacrol, were evaluated against 27 clinical isolates of Malassezia furfur. Minimum inhibitory concentrations (MICs) were measured according to the broth microdilution protocols by Clinical and Laboratory Standards Institute (CLSI) modified for Malassezia spp. EOs and carvacrol showed low MIC values ranged 450-900 µg/ml against M. furfur. No differences in EOs antifungal activity were observed in sensitive to resistant fluconazole isolates. The antifungal activity obtained showed O. vulgare EO, T. vulgaris EO and carvacrol, their compound, as potential antimicrobial agents against M. furfur, yeast associated with human mycoses.
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Antifúngicos/aislamiento & purificación , Cimenos/aislamiento & purificación , Malassezia/efectos de los fármacos , Aceites Volátiles/aislamiento & purificación , Origanum/toxicidad , Thymus (Planta)/toxicidad , Antiinfecciosos/farmacología , Antifúngicos/farmacología , Cimenos/farmacología , Fluconazol/farmacología , Cromatografía de Gases y Espectrometría de Masas , Humanos , Pruebas de Sensibilidad Microbiana , Aceites Volátiles/química , Aceites Volátiles/farmacología , Origanum/química , Thymus (Planta)/química , Levaduras/efectos de los fármacosRESUMEN
INTRODUCTION: The genus Leonurus L. (fam: Lamiaceae) is represented in Uzbekistan by two species, L. panzerioides Popov. and L. turkestanicus V. I. Krecz. & Kuprian, which are used to treat nervous disorders and also as sedative and hypotensive agents. OBJECTIVES: To establish the taxonomic status of Leonurus panzerioides and L. turkestanicus based on their chemical constituents analysed by GC-MS and q-NMR. MATERIALS AND METHODS: Quantitative (1) H-NMR (q-NMR) was used to identify and quantify known major components in the methanol extracts of these two species. Additionally, the chemical composition of the essential oils obtained from the aerial parts of these plants were analysed by GC-MS. RESULTS: The q-NMR analyses of Leonurus panzerioides and L. turkestanicus revealed the presence of 8-acetylharpagide, harpagide, leonurine and stachydrine as major components. Using the GC-MS method, overall 24 and 39 constituents were identified, respectively, from L. panzerioides and L. turkestanicus oils. The major constituents of the essential oil of L. panzerioides were eugenol (30.9%) and p-vinyl guaiacol (15.8%), whereas thymol (40.1%) and octen-3-ol (13.1%) were the principal compounds in the essential oil of L. turkestanicus. CONCLUSION: The major components in Leonurus panzerioides and L. turkestanicus as identified by the GC-MS and q-NMR analyses, were similar to those present in other Leonurus species and thus provided chemotaxonomic evidence for the placement of these species under the genus Leonurus. Copyright © 2016 John Wiley & Sons, Ltd.
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Cromatografía de Gases y Espectrometría de Masas/métodos , Leonurus/química , Espectroscopía de Resonancia Magnética/métodos , Leonurus/clasificación , Espectroscopía de Protones por Resonancia Magnética , Especificidad de la EspecieRESUMEN
The chemical composition, antifungal, antioxidant and cytotoxic activities of the essential oils (EOs) of mint (Mentha suaveolens), thyme (Coridothymus capitatus), oregano (Origanum hirtum) and rosemary (Rosmarinus officinalis) were investigated. The antifingal properties of the EOs were investigated againstfour species of Candida by a microdilution method. Cytotoxicity was tested on human keratinocyte (HaCaT) and lung cancer (A549) cell lines using the MTT test. DPPH· and ABTS·+ spectrophotometric assays and DPPH-- ABTS-+(HP)TLC-bioautographic assays were used to evaluate the antioxidant activity. The main compounds of thyme and oregano EOs were carvacrol and thymol, respectively; piperitenone oxide and y-terpinene were the most abundant compounds ofmint and rosemary EOs, respectively. All EOs showed activity against all Candida species in a range between 760 ± 290 to 3120 ± 0.0 µg/mL. Among the EOs, that of M suaveolens showed a stronger cytotoxic activity on HaCaT cells. Thyme, oregano and rosemary EQs exhibited important antioxidant activities by ABTS` assay compared with trolox.
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Aceites Volátiles/química , Aceites Volátiles/farmacología , Plantas/química , Células A549 , Antifúngicos/farmacología , Antineoplásicos Fitogénicos/farmacología , Antioxidantes/química , Candida/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Mentha/química , Pruebas de Sensibilidad Microbiana , Origanum/química , Rosmarinus/química , Thymus (Planta)/químicaRESUMEN
The aggregation behavior of 6-isocassine and N-methyl-6-isocassine, two piperidin-3-ol alkaloids isolated respectively from the barks of Prosopis nigra and P. affinis, was investigated using a combination of NOE experiments and diffusion measurements in solvents of varying polarity and hydrogen bonding capacity. While the NOE enhancements for N-methyl-6-isocassine are positive, regardless of the solvent, those for 6-isocassine shift from negative to positive when going from chloroform-d to methanol-d(4) solution. In addition, despite the self-diffusion coefficients of both compounds being virtually identical in methanol-d4, N-methyl-6-isocassine diffuses nearly twice as fast as the non-methylated alkaloid in chloroform-d. The changes in rotational and translational dynamics observed between solvents for 6-isocassine suggest that the molecule forms dimeric head-to-head aggregates in non-polar aprotic environments, a behavior that could help explain the biological mode of action that has been proposed for this type of alkaloids.