RESUMO
A comprehensive phytochemical investigation of aerial parts obtained from Centaurea sicula L. led to the isolation of 14 terpenoids (1-14) and nine polyphenols (15-23). The sesquiterpenoid group (1-11) included three structural families, namely, elemanolides (1-6), eudesmanolides (7 and 8), and germacranolides (9-11) with four unreported secondary metabolites (5-8), whose structure has been determined by extensive spectroscopic analysis, including 1D/2D NMR, HR-MS, and chemical conversion. Moreover, an unprecedented alkaloid, named siculamide (24), was structurally characterized, and a possible biogenetic origin was postulated. Inspired by the traditional use of the plant and in the frame of ongoing research on compounds with potential activity on metabolic syndrome, all the isolated compounds were evaluated for their stimulation of glucose uptake, disclosing remarkable activity for dihydrocnicin (10) and the lignan salicifoliol (15).
Assuntos
Centaurea , Glucose , Componentes Aéreos da Planta , Componentes Aéreos da Planta/química , Centaurea/química , Estrutura Molecular , Glucose/metabolismo , Terpenos/química , Terpenos/isolamento & purificação , Terpenos/farmacologia , Polifenóis/química , Polifenóis/farmacologia , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Sesquiterpenos/isolamento & purificaçãoRESUMO
The antitumor activity of different ent-kaurane diterpenes has been extensively studied. Several investigations have demonstrated the excellent antitumor activity of synthetic derivatives of the diterpene atractyligenin. In this research, a series of new synthetic amides and their 15,19-di-oxo analogues obtained from atractyligenin by modifying the C-2, C-15, and C-19 positions were designed in order to dispose of a set of derivatives with different substitutions at the amidic nitrogen. Using different concentrations of the obtained compounds (10-300 µM) a reduction in cell viability of HCT116 colon cancer cells was observed at 48 h of treatment. All the di-oxidized compounds were more effective than their alcoholic precursors. The di-oxidized compounds had already reduced the viability of two colon cancer cells (HCT116 and Caco-2) at 24 h when used at low doses (2.5-15 µM), while they turned out to be poorly effective in differentiated Caco-2 cells, a model of polarized enterocytes. The data reported here provide evidence that di-oxidized compounds induced apoptotic cell death, as demonstrated by the appearance of condensed and fragmented DNA in treated cells, as well as the activation of caspase-3 and fragmentation of its target PARP-1.
Assuntos
Atractilosídeo/análogos & derivados , Neoplasias do Colo , Diterpenos do Tipo Caurano , Humanos , Diterpenos do Tipo Caurano/farmacologia , Células CACO-2 , Neoplasias do Colo/tratamento farmacológico , Amidas , ApoptoseRESUMO
Triterpene acids are a class of pentacyclic natural carboxylic compounds endowed with a variety of biological activities including antitumor, antimicrobial, and hepatoprotective effects. In this work, several oleanolic acid derivatives were synthesized by structurally modifying them on the C-3 position. All synthesized derivatives were evaluated for possible antibacterial and antiviral activity, and among all the epimers, 6 and 7 demonstrated the best biological activities. Zone-of-inhibition analyses were conducted against two strains, E. coli as a Gram-negative and S. aureus as a Gram-positive model. Subsequently, experiments were performed using the microdilution method to determine the minimum inhibitory concentration (MIC). The results showed that only the derivative with reduced hydrogen bonding ability on ring A possesses remarkable activity toward E. coli. The conversion from acid to methyl ester implies a loss of activity, probably due to a reduced affinity with the bacterial membrane. Before the antiviral activity, the cytotoxicity of triterpenes was evaluated through a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Samples 6 and 7 showed less than 50% cytotoxicity at 0.625 and 1 mg/mL, respectively. The antiviral activity against SARS-CoV-2 and PV-1 did not indicate that triterpene acids had any inhibitory capacity in the sub-toxic concentration range.
Assuntos
Antibacterianos , Antivirais , Escherichia coli , Testes de Sensibilidade Microbiana , Ácido Oleanólico , Ácido Oleanólico/química , Ácido Oleanólico/farmacologia , Ácido Oleanólico/análogos & derivados , Antivirais/farmacologia , Antivirais/química , Antivirais/síntese química , Antibacterianos/farmacologia , Antibacterianos/química , Antibacterianos/síntese química , Escherichia coli/efeitos dos fármacos , Escherichia coli/crescimento & desenvolvimento , Humanos , Staphylococcus aureus/efeitos dos fármacos , SARS-CoV-2/efeitos dos fármacos , Animais , Relação Estrutura-AtividadeRESUMO
This study was aimed at investigating the phytochemical profile and bioactivity of Diplotaxis harra subsp. crassifolia (Brassicaceae), a species from central-southern Sicily (Italy), where it is consumed as a salad. For this purpose, LC-ESI/HRMSn analysis of the ethanolic extract was performed, highlighting the occurrence, along with flavonoids, hydroxycinnamic acid derivatives, and oxylipins, of sulfated secondary metabolites, including glucosinolates and various sulfooxy derivatives (e.g., C13 nor-isoprenoids, hydroxyphenyl, and hydroxybenzoic acid derivatives), most of which were never reported before in the Brassicaeae family or in the Diplotaxis genus. Following ethnomedicinal information regarding this species used for the treatment of various pathologies such as diabetes and hypercholesterolemia, D. harra ethanolic extract was evaluated for its antioxidant potential using different in vitro tests such as 2,2-diphenyl-1-picrylhydrazyl, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), Ferric Reducing Ability Power, and ß-carotene bleaching tests. The inhibitory activity of carbohydrate-hydrolyzing enzymes (α-amylase and α-glucosidase) and pancreatic lipase was also assessed. In the 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid assay, an IC50 value comparable to the positive control ascorbic acid (2.87 vs. 1.70 µg/mL, respectively) was obtained. The wild-wall rocket salad extract showed a significant α-amylase inhibitory effect. Obtained results indicate that Sicilian wild-wall rocket contains phytochemicals that can prevent hyperglycemia, hyperlipidemia, and obesity.
Assuntos
Antioxidantes , Compostos Fitoquímicos , Extratos Vegetais , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Sicília , Flavonoides/química , Flavonoides/farmacologia , Flavonoides/análiseRESUMO
P. maritimum L., belonging to the Amaryllidaceae family, is a species that grows on beaches and coastal sand dunes mainly on both sides of the Mediterranean Sea and Black Sea, the Middle East, and up to the Caucasus region. It has been largely investigated due to its several interesting biological properties. With the aim of providing new insights into the phytochemistry and pharmacology of this species, the ethanolic extract of the bulbs from a local accession, not previously studied, growing in Sicily (Italy), was investigated. This chemical analysis, performed by mono- and bi-dimensional NMR spectroscopy, as well as LC-DAD-MSn, allowed to identify several alkaloids, three of which were never detected in the genus Pancratium. Furthermore, the cytotoxicity of the preparation was assessed in differentiated human Caco-2 intestinal cells by trypan blue exclusion assay, and its antioxidant potential was evaluated using the DCFH-DA radical scavenging method. The results obtained demonstrate that P. maritimum bulbs' extract exerts no cytotoxic effect and is able to remove free radicals at all the concentrations tested.
Assuntos
Amaryllidaceae , Antineoplásicos , Humanos , Antioxidantes/farmacologia , Sicília , Células CACO-2 , Extratos Vegetais/farmacologiaRESUMO
The genus Thymus L., belonging to the Lamiaceae family, contains about 220 species with a distribution that mainly extends in Europe, northwest Africa, Ethiopia, Asia, and southern Greenland. Due to their excellent biological properties, fresh and/or dried leaves and aerial parts of several Thymus ssp. have been utilized in the traditional medicine of many countries. To evaluate not only the chemical aspects but also the biological properties, the essential oils (EOs), obtained from the pre-flowering and flowering aerial parts of Thymus richardii subsp. nitidus (Guss.) Jalas, endemic to Marettimo Island (Sicily, Italy), were investigated. The chemical composition of the EOs, obtained by classical hydrodistillation and GC-MS and GC-FID analyses, showed the occurrence of similar amounts of monoterpene hydrocarbons, oxygenated monoterpenes, and sesquiterpene hydrocarbons. The main constituents of the pre-flowering oil were ß-bisabolene (28.54%), p-cymene (24.45%), and thymol methyl ether (15.90%). The EO obtained from the flowering aerial parts showed as principal metabolites ß-bisabolene (17.91%), thymol (16.26%), and limonene (15.59%). The EO of the flowering aerial parts, and its main pure constituents, ß-bisabolene, thymol, limonene, p-cymene, and thymol methyl ether were investigated for their antimicrobial activity against oral pathogens and for their antibiofilm and antioxidant properties.
Assuntos
Óleos Voláteis , Thymus (Planta) , Óleos Voláteis/química , Timol/farmacologia , Timol/análise , Limoneno/análise , Monoterpenos/análise , Thymus (Planta)/química , Etiópia , SicíliaRESUMO
Mead is a beverage produced by alcoholic fermentation of honey-must. The starter yeasts that are commonly used for the alcoholic fermentation of honey-must are oenological Saccharomyces cerevisiae strains. The objective of the present work was, for the first time, to apply yeasts of honey by-products origin to evaluate the influences the taste-olfactory attributes of mead. For this purpose, three experimental productions were set up, which included: (i) single inoculation of S. cerevisiae; (ii) single inoculation of Hanseniaspora uvarum; (iii) sequential inoculation of H. uvarum/S. cerevisiae. Two control trials were performed, using a commercial strain of S. cerevisiae of oenological origin and a spontaneous fermentation. The results of the chemical parameters showed differences between the trials in terms of residual sugars, acetic acid, glycerol, ethanol and volatile organic compounds. Sensorial analysis also showed a high heterogeneity among trials. The attributes of sweetness, honey and floral were found in mead fermented with H. uvarum, whereas all meads obtained with S. cerevisiae were dry, balanced and without off-odors and off-flavours. The results obtained showed that the controlled application of conventional and non-conventional yeast strains isolated from honey by-products origin could be a promising approach to improve the quality of meads.
Assuntos
Hanseniaspora , Mel , Vinho , Fermentação , Mel/análise , Saccharomyces cerevisiae , Sicília , Vinho/análiseRESUMO
"Spiritu re fascitrari" is a Sicilian alcoholic beverage obtained through distillation of a decoction of spontaneously fermented honey by-products (FHP). The production process often leads to sensorial defects due to the unstable alcoholic fermentation. The objective of this work was to select Saccharomyces cerevisiae strains from FHP to be used as starter in decoction fermentation. Based on chemical, microbiological and technological data, from a total of 91 strains three S. cerevisae were selected for further testing to produce FHP at laboratory scale level. After FHP distillation, the analysis of volatile organic compounds showed a complex mixture of sensory active molecules, mainly alcohols and aldehydes. Among the alcohols, 3-methyl-1-butanol, 2-methyl-1-butanol, phenylethyl alcohol, hexadecanol and octadecanol were found at the highest concentrations. Among the carboxylic acids, acetic acid was mainly detected in the spontaneously fermented samples. FHP fermented with the three selected strains were not characterized by the presence of off-odors or off-flavours. The results obtained in this work demonstrate that the selected S. cerevisiae strains are promising starters to stabilize the production of distilled alcoholic beverages produced from honey by-products.
Assuntos
Mel , Saccharomyces cerevisiae , Bebidas Alcoólicas/microbiologia , Bebidas , Fermentação , Mel/microbiologiaRESUMO
Oleanolic acid (OA) and Lupeol (LU) belong to the class of natural triterpenes and are endowed with a wide range of biological activities, including cytotoxicity toward several cancer cell lines. In this context, we investigated a set of compounds obtained from the two natural precursors for the cytotoxicity against leukemia HL60 cells and the multidrug-resistant (MDR) variant HL60R. Six new semi-synthetic triterpenes have been synthetized, fully characterized, and were investigated together with other triterpenes compounds for their pharmacological mechanism of action. The interaction of the more cytotoxic compounds with the nuclear factor kappa B (NF-κB) pathway has been also evaluated with the aid of docking. The lupane-like compounds were more active than the precursor, while the oleane-like compounds showed more complex behavior. Both OA and LU derivatives possess a similar interaction pattern with the p65 subunit of NF-κB, justifying the similar trend in their ability to inhibit the binding of p65 to DNA. Further, some of the derivatives tested were able to increase IκB-α levels preventing the translocation of NF-κB to the nucleus. In conclusion, this study offers a deeper insight on the pharmacological action of triterpenes toward leukemia cells, and it improves the background useful for the development of new anti-cancer drugs.
Assuntos
Leucemia , Neoplasias , Ácido Oleanólico , Triterpenos , Linhagem Celular , Humanos , Leucemia/tratamento farmacológico , NF-kappa B/metabolismo , Triterpenos Pentacíclicos , Triterpenos/química , Triterpenos/farmacologiaRESUMO
Prangos ferulacea (L.) Lindl, which belongs to the Apiaceae family, is a species that mainly grows in the eastern Mediterranean region and in western Asia. It has been largely used in traditional medicine in several countries and it has been shown to possess several interesting biological properties. With the aim to provide new insights into the phytochemistry and pharmacology of this species, the essential oils of flowers and leaves from a local accession that grows in Sicily (Italy) and has not yet been previously studied were investigated. The chemical composition of both oils, obtained by hydrodistillation from the leaves and flowers, was evaluated by GC-MS. This analysis allowed us to identify a new chemotype, characterized by a large amount of (Z)-ß-ocimene. Furthermore, these essential oils have been tested for their possible antimicrobial and antioxidant activity. P. ferulacea essential oils exhibit moderate antimicrobial activity; in particular, the flower essential oil is harmful at low and wide spectrum concentrations. They also exhibit good antioxidant activity in vitro and in particular, it has been shown that the essential oils of the flowers and leaves of P. ferulacea caused a decrease in ROS and an increase in the activity of superoxide dismutase (SOD), catalase (CAT) and glutathione S-transferase (GST) in OZ-stimulated PMNs. Therefore, these essential oils could be considered as promising candidates for pharmaceutical and nutraceutical preparations.
Assuntos
Anti-Infecciosos , Apiaceae , Óleos Voláteis , Óleos Voláteis/química , Antioxidantes/farmacologia , Antioxidantes/análise , Apiaceae/química , Folhas de Planta/química , Anti-Infecciosos/química , Antibacterianos/farmacologia , SicíliaRESUMO
The aim of the present study is to investigate the chemical profile, antioxidant activity, carbohydrate-hydrolysing enzyme inhibition, and hypolipidemic effect of essential oils (EOs) extracted from Sicilian Citrus maxima (pomelo) flavedo. Using gas-chromatography-mass spectrometry analysis (GC-MS) we analysed the Eos of five cultivars of C. maxima, namely, 'Chadock', 'Maxima', 'Pyriformis', 'Terracciani', and 'Todarii', and their blends. The antioxidant activity was performed by using a multi-target approach using 2,2'-Azino-Bis-3-Ethylbenzothiazoline-6-Sulfonic acid (ABTS), 2,2-Diphenyl-1-picrylhydrazyl (DPPH), ferric reducing ability power (FRAP), and ß-carotene bleaching tests. The α-amylase, α-glucosidase, and lipase-inhibitory activities were also assessed. GC-MS analyses revealed D-limonene as the main monoterpene hydrocarbon in all cultivars, albeit with different percentages in the range of 21.72-71.13%. A good content of oxygenated monoterpenes was detected for all cultivars, especially for 'Todarii'. The analysis of the principal components (PCA), and related clusters (HCA), was performed to find chemo-diversity among the analysed samples. EOs from 'Chadock' and 'Maxima' were statistically similar to each other, and they differed from P3 in the smaller amount of sesquiterpene hydrocarbons, while the oils from 'Terracciani' and 'Todarii' were found to be chemically and statistically different. 'Chadock' EO was the most active to scavenge radicals (IC50 values of 22.24 and 27.23 µg/mL in ABTS and DPPH tests, respectively). 'Terracciani' EO was the most active against both lipase and α-amylase, whereas the blends obtained by the combination (1:1 v/v) of C. maxima 'Maxima' + 'Todarii' were the most active against α-glucosidase. Generally, the blends did not exert a unique behaviour in potentiating or reducing the bioactivity of the pomelo EOs.
Assuntos
Citrus , Óleos Voláteis , Eliminação de Resíduos , Antioxidantes/química , Citrus/química , Frutas/química , Lipase/análise , Monoterpenos/análise , Óleos Voláteis/química , alfa-Amilases , alfa-GlucosidasesRESUMO
In this work, seven Citrus aurantium essential oils (EOs) derived from flavedo of cultivars 'Canaliculata', 'Consolei', 'Crispifolia', 'Fasciata', 'Foetifera', 'Listata', and 'Bizzaria' were investigated. EOs were also combined in 1:1 (v/v) ratio to identify possible synergism or antagonism of actions. GC-MS analysis was done to investigate Eos' phytochemical profiles. The antioxidant activity was studied by using a multi-target approach based on FRAP, DPPH, ABTS, and ß-carotene bleaching tests. A great difference was observed in EOs' phytochemical profiles. d-limonene (33.35-89.17%) was the main monoterpene hydrocarbon, and α-Pinene, ß-myrcene, and ß-linalool were identified in almost all samples. Among EOs, only C3 showed high quantitative and qualitative variability in its chemical composition. The chemical diversity of EOs was also demonstrated by PCA and HCA statistical analysis. Samples C2, C4, C5, C6, and C7 were statistically similar to each other, while C1 and C3 were characterized as having a different amount of other compounds and oxygenated monoterpenes, respectively, with respect to the other EOs mentioned. The global antioxidant score (GAS) revealed that among the tested EOs, C. aurantium 'Fasciata' EO had the highest antioxidant potential, with a GAS value of -0.47, whereas among combinations, the EO obtained by mixing 'Canaliculata' + 'Bizzaria' was the most active. Comparison by theoretical and real data on inhibitory concentration (IC50) and FRAP values did not reveal any significant effect of synergism or antagonism of actions to be valid in all biological applied tests. These findings, considered together, represent an important starting point to understand which compounds are responsible for the activities and their future possible industrial application.
Assuntos
Óleos VoláteisRESUMO
The problems of the environment and human health related to the use of synthetic and broad-spectrum insecticides have increasingly motivated scientific research on different alternatives and among these, the use of green systems, such as essential oils, have been explored. Several species of the Apiaceae and Asteraceae families, aromatic herbs rich in secondary bioactive metabolites, are used in the industrial field for pharmaceutical, cosmetic, and food purposes. Different essential oils extracted from some species of these families have shown acute toxicity and attractive and/or repellent effects towards different insects. In our work, we investigated the toxic potential of Calendula incana subsp. maritima and Laserpitium siler subsp. siculum essential oils against four insect species, Sitophilus oryzae, Lasioderma serricorne, Necrobia rufipes, and Rhyzoperta dominica, which are common pests of stored products. The composition of both oils, extracted by hydrodistillation from the aerial parts of the two plants, was evaluated by GC×GC-MS. Calendula incana subsp. maritima essential oil was rich in oxygenated sesquiterpenoids, such as cubebol (35.39%), 4-epi-cubebol (22.99%), and cubenol (12.77%), while the Laserpitium siler subsp. siculum essential oil was composed mainly of monoterpene hydrocarbons, such as ß-phellandrene (42.16%), limonene (23.87%), and ß-terpinene (11.80%). The toxicity Petri dish bioassays indicated that C. maritima oil killed a mean of 65.50% of S. oryzae and 44.00% of R. dominica adults, indicating a higher biocidal activity in comparison with L. siculum oil, while toward the other species, no significant differences in mortality were recorded. Calendula maritima oil could be, then, considered a promising candidate for further tests as an alternative biocide toward S. oryzae and R. dominica. The possibility that the relatively high content of oxygenated sesquiterpenoids in C. maritima essential oil determines its higher biocidal activity is discussed.
Assuntos
Apiaceae/química , Asteraceae/química , Besouros/efeitos dos fármacos , Inseticidas/farmacologia , Óleos Voláteis/análise , Óleos Voláteis/farmacologia , Gorgulhos/efeitos dos fármacos , Animais , Inseticidas/análise , Óleos de Plantas/análise , Óleos de Plantas/farmacologiaRESUMO
The genus Teucrium is a large and polymorphic genus of the Lamiaceae family distributed in mild climate zones, particularly in the Mediterranean basin and Central Asia. Studies of nonvolatile constituents of Teucrium species showed that they are a rich source of neo-clerodane diterpenoids, considered as chemotaxonomic markers of the genus. In addition to the nonvolatile metabolites, there has been a large interest in the essential oils of this genus. In this review, a complete survey of the chemical composition and biological properties of the essential oils isolated from Teucrium taxa is provided. In traditional medicine, since ancient times, species of this genus have been widely implemented for their biological properties, including antimicrobial, anti-inflammatory, antispasmodic, insecticidal, anti-malaria, etc. Therefore, a complete review of all of the traditional uses of Teucrium taxa are also reported.
Assuntos
Lamiaceae , Óleos Voláteis , Teucrium , Medicina Tradicional , Óleos Voláteis/farmacologia , Extratos Vegetais/farmacologiaRESUMO
The genus Doronicum, belonging to tribe Senecioneae (Fam. Asteraceae), is found mainly in the Asia, Europe and North Africa. This genus of plant has always been used in traditional medicinal treatments due to the many biological properties shown such as killing parasitic worms and for relieving constipation, as well as to improve heart health, to alleviate pain and inflammation, to treat insect bites, etc. According to the World Flora the genus Doronicum contains 39 subordinate taxa.[1-3] The purpose of this article, which covers data published from 1970 to 2021 with more than 110 articles, aims to carry out a complete and critical review of the Doronicum genus, examining traditional uses and reporting the antioxidant, antimicrobial, anti-inflammatory and antitumor activity shown from crude extracts or essential oils, and from single isolated compounds. Furthermore, critical considerations of the published data have been highlighted by comparing them with the results obtained from species of other genus belonging to the Asteraceae family.
Assuntos
Antibacterianos/farmacologia , Anti-Inflamatórios não Esteroides/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Asteraceae/química , Alcaloides de Pirrolizidina/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Humanos , Estrutura Molecular , Alcaloides de Pirrolizidina/química , Alcaloides de Pirrolizidina/isolamento & purificaçãoRESUMO
The blackberry's color is composed mainly of natural dyes called anthocyanins. Their color is red-purple, and they can be used as a natural colorant. Anthocyanins are flavonoids, which are products of plants, and their colors range from orange and red to various shades of blue, purple and green, according to pH. In this study, the chemical composition of an extract obtained from blackberries was defined by LC-ESI/LTQOrbitrap/MS in positive and negative ionization mode. Furthermore, we investigated the adsorption process of blackberry extract using several inorganic fillers, such as metakaolin, silica, Lipari pumice, white pozzolan and alumina. The pigments exhibit different colors as a function of their interactions with the fillers. The analysis of the absorption data allowed the estimation of the maximum adsorbing capacity of each individual filler tested. Through thermogravimetric measurements (TGA), the thermal stability and the real adsorption of the organic extract were determined.
Assuntos
Corantes/química , Pigmentos Biológicos/química , Extratos Vegetais/química , Rubus/química , Adsorção , Colorimetria , Estabilidade de Medicamentos , Flavonoides/química , Espectrometria de Massas/métodosRESUMO
The chemical composition and the qualitative and quantitative variability of the essential oils of three taxa belonging to the Teucrium genus were studied. The investigated taxa, that grow wild in Sicily, were Teucrium flavum L. (section Chamaedrys (Mill.) Scheb.), Teucrium montanum and Teucrium capitatum L. of section Polium (Mill.) Scheb. Essential oils were extracted by hydrodistillation and analyzed by GC-MS. In total, 74 compounds were identified. Sesquiterpene hydrocarbons were found to be the main group for T. flavum (48.3%). T. capitatum consisted essentially of monoterpene hydrocarbons (72.7%), with α-pinene (19.9%), ß-pinene (27.6%) and sylvestrene (16.6%) as the most abundant compounds whereas ledene oxide (12.1%), epiglobulol (13.5%) and longifolenaldehyde (14.5%) were identified as the main constituents among the oxygenated sesquiterpenes (63.5%) of T. montanum. Furthermore, a complete literature review on the composition of the essential oils of all the other accessions of these Teucrium taxa, studied so far, was performed. Hierarchical Cluster Analysis (HCA) and Principal Component Analyses (PCA) were used in order to demonstrate geographical variations in the composition of the essential oils.
Assuntos
Óleos Voláteis/isolamento & purificação , Teucrium/classificação , Teucrium/crescimento & desenvolvimento , Análise por Conglomerados , Cromatografia Gasosa-Espectrometria de Massas , Óleos Voláteis/química , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/crescimento & desenvolvimento , Óleos de Plantas/química , Análise de Componente Principal , Sicília , Especificidade da Espécie , Teucrium/químicaRESUMO
BACKGROUND: This study investigated the chemical profile and biological activity of Diplotaxis erucoides subsp. erucoides (L.) DC. (Brassicaceae) collected in Sicily (Italy). RESULTS: Liquid chromatography coupled with electrospray ionization and high-resolution mass spectrometry (LC-ESI/HRMS) analysis of the ethanol extract revealed the presence of 42 compounds - glucosinolates, hydroxycinnamic acids, flavonoids, and oxylipins. The extract was tested for its antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic) acid (ABTS), ferric reducing ability power (FRAP), and ß-carotene bleaching tests. Promising protection from lipid peroxidation was observed after 30 min of incubation in a ß-carotene bleaching test (IC50 of 3.32 µg mL-1 ). The inhibition of carbohydrates-hydrolyzing enzymes resulted in IC50 values of 85.18 and 92.36 µg mL-1 for α-amylase and α-glucosidase, respectively. Significant inhibition against lipase enzyme was observed (IC50 of 61.27 µg mL-1 ). CONCLUSION: Diplotaxis erucoides can be considered a potential source of antioxidant, hypoglycemic, and hypolipidemic bioactives. © 2021 Society of Chemical Industry.
Assuntos
Brassicaceae/química , Glucosinolatos/química , Oxilipinas/química , Extratos Vegetais/química , Antioxidantes/química , Cromatografia Líquida , Inibidores Enzimáticos/química , Flavonoides/química , Inibidores de Glicosídeo Hidrolases , Humanos , Espectrometria de Massas , Saladas/análise , Sicília , alfa-Amilases/antagonistas & inibidores , alfa-Amilases/química , alfa-Glucosidases/químicaRESUMO
Essential oils (EOs) have been known for a long time, and they are used in several fields such as medicine and aromatherapy, as well as in the food and pharmaceutical industries. In the last decade, EOs have also been applied to contrast the biodeterioration of cultural heritage, representing a powerful resource in green conservation strategies. In this study, an integrated approach based on microscopic observation, in vitro culture, and molecular investigation was preliminarily employed to identify biological systems colonizing wooden artworks. In order to contrast the biodeterioration processes induced by fungal colonization (Aspergillus flavus) or insect infestation (Anobium punctatum), wooden artworks were exposed to the volatile compound of Origanum vulgare or Thymus vulgaris essential oils (EOs), the chemical composition of which was determined by GC-MS using both polar and apolar columns. Artwork exposure was performed in ad-hoc-assembled "clean chambers." Evaluating the effects on biological systems, the compatibility with artwork constitutive materials, and the lack of negative effects on human health and environmental pollution, the use of EOs as a valid alternative to traditional biocides must be considered.
Assuntos
Desinfetantes/farmacologia , Óleos Voláteis/farmacologia , Animais , Antifúngicos/farmacologia , Aspergillus flavus/efeitos dos fármacos , Cromatografia Gasosa-Espectrometria de Massas/métodos , Insetos/microbiologia , Testes de Sensibilidade Microbiana/métodos , Origanum/química , Thymus (Planta)/microbiologiaRESUMO
This study aimed to evaluate the chemical composition by gas chromatography-mass spectrometry (GC-MS) and Nuclear Magnetic Resonance (NMR) analyses, the antioxidant activities evaluated by different in vitro assays namely 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS), Ferric Reducing Ability Power (FRAP), and ß-carotene bleaching tests, and the inhibitory effects of enzymes linked to obesity (lipase, α-amylase, and α-glucosidase) of fixed seed oil of Ceiba speciosa (A. St.-Hil.). Fourteen compounds were identified. Linoleic acid (28.22%) was the most abundant followed by palmitic acid (19.56%). Malvalic acid (16.15%), sterculic acid (11.11%), and dihydrosterculic acid (2.74%) were also detected. C. speciosa fixed oil exerted a promising ABTS radicals scavenging activity with an IC50 value of 10.21 µg/mL, whereas an IC50 of 77.44 µg/mL against DPPH+ radicals was found. C. speciosa fixed oil inhibited lipase with an IC50 value of 127.57 µg/mL. The present investigation confirmed the functional properties of C. speciosa fixed oil, and proposes its use as valuable source of bioactive constituents.