RESUMO
In this study, we investigated the anti-allergic effects of 3,4-dihydroxybenzaldehyde (DHB) isolated from the marine red alga, Polysiphonia morrowii, in mouse bone-marrow-derived cultured mast cells (BMCMCs) and passive cutaneous anaphylaxis (PCA) in anti-dinitrophenyl (DNP) immunoglobulin E (IgE)-sensitized mice. DHB inhibited IgE/bovine serum albumin (BSA)-induced BMCMCs degranulation by reducing the release of ß-hexosaminidase without inducing cytotoxicity. Further, DHB dose-dependently decreased the IgE binding and high-affinity IgE receptor (FcεRI) expression and FcεRI-IgE binding on the surface of BMCMCs. Moreover, DHB suppressed the secretion and/or the expression of the allergic cytokines, interleukin (IL)-4, IL-5, IL-6, IL-13, and tumor necrosis factor (TNF)-α, and the chemokine, thymus activation-regulated chemokine (TARC), by regulating the phosphorylation of IκBα and the translocation of cytoplasmic NF-κB into the nucleus. Furthermore, DHB attenuated the passive cutaneous anaphylactic (PCA) reaction reducing the exuded Evans blue amount in the mouse ear stimulated by IgE/BSA. These results suggest that DHB is a potential therapeutic candidate for the prevention and treatment of type I allergic disorders.
Assuntos
Antialérgicos/farmacologia , Benzaldeídos/farmacologia , Catecóis/farmacologia , Mastócitos/efeitos dos fármacos , Rodófitas/metabolismo , Animais , Antialérgicos/administração & dosagem , Antialérgicos/isolamento & purificação , Benzaldeídos/administração & dosagem , Benzaldeídos/isolamento & purificação , Catecóis/administração & dosagem , Catecóis/isolamento & purificação , Células Cultivadas , Citocinas/imunologia , Modelos Animais de Doenças , Relação Dose-Resposta a Droga , Imunoglobulina E/imunologia , Masculino , Mastócitos/imunologia , Camundongos , Camundongos Endogâmicos BALB C , Camundongos Endogâmicos C57BL , Anafilaxia Cutânea Passiva/efeitos dos fármacos , Anafilaxia Cutânea Passiva/imunologia , Soroalbumina Bovina/imunologiaRESUMO
Ferulago nodosa (L.) Boiss. (Apiaceae) is a species occurring in the Balkan-Tyrrhenian area. The object of the present study is Sicilian F. nodosa subsp. geniculata (Guss.) Troia & Raimondo, classified as an endemic F. nodosa subspecies. Aerial parts of this plant species were subjected to hydrodistillation to obtain an essential oil. A total of 93 compounds were identified with 2,3,6-trimethyl benzaldehyde (19.0%), spathulenol (9.0%), (E)-caryophyllene (5.4%), and caryophyllene oxide (5.4%) as the main components. The biological activities of F. nodosa essential oil were also investigated. This oil showed an interesting antioxidant potential in a 2,2'-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) test (IC50 of 14.05 µg/mL). Additionally, hypoglycemic and antilipidemic effects were evaluated. Lipase enzyme was inhibited with an IC50 value of 41.99 µg/mL. Obtained data demonstrated that F. nodosa could be considered a promising source of bioactive compounds useful for the treatment and management of obesity.
Assuntos
Antioxidantes/química , Apiaceae/química , Óleos Voláteis/química , Sesquiterpenos/química , Antioxidantes/isolamento & purificação , Benzaldeídos/química , Benzaldeídos/isolamento & purificação , Benzotiazóis/química , Cromatografia Gasosa-Espectrometria de Massas , Óleos Voláteis/farmacologia , Sesquiterpenos Policíclicos/química , Sesquiterpenos Policíclicos/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Sicília , Ácidos Sulfônicos/químicaRESUMO
The present study investigates the anti-allergic activity of the marine algal bromophenol, 3-bromo-4,5-dihydroxybenzaldehyde (BDB), isolated from Polysiphonia morrowii Harvey in immunoglobulin (Ig)E/bovine serum albumin (BSA)-stimulated mouse bone marrow-derived cultured mast cells (BMCMCs) and a passive cutaneous anaphylaxis (PCA) mice ear model. BDB effectively inhibited ß-hexosaminidase release (IC50 = 80.12 µM), in IgE/BSA-stimulated BMCMCs without a cytotoxic response. Also, BDB down-regulated the expression or secretion of cytokines, interleukin (IL)-1ß, IL-4, IL-5, IL-6, IL-10, IL-13, interferon (IFN)-γ, and tumor necrosis factor (TNF)-α and the chemokine (thymus and activation-regulated chemokine (TARC). The above effects could be attributed to the dose-dependent decrease of FcεRI expression on the surface of BMCMCs and its stable IgE binding. Moreover, BDB suppressed the nuclear factor (NF)-κB and spleen tyrosine kinase (SYK)-linker for T-cell activation (LAT)-GRB2 associated binding protein 2 (Gab2) signaling axis activated by IgE/BSA stimulation. Furthermore, oral administration of BDB to IgE-sensitized mice effectively attenuated IgE-triggered PCA reaction. Collectively, the anti-allergic effects of BDB suggest its potential applicability as a candidate for in-depth test trials.
Assuntos
Benzaldeídos/farmacologia , Imunoglobulina E/farmacologia , Mastócitos/efeitos dos fármacos , Mastócitos/metabolismo , Anafilaxia Cutânea Passiva/efeitos dos fármacos , Rodófitas , Soroalbumina Bovina/farmacologia , Animais , Benzaldeídos/isolamento & purificação , Sobrevivência Celular/efeitos dos fármacos , Sobrevivência Celular/fisiologia , Masculino , Camundongos , Camundongos Endogâmicos C57BL , Anafilaxia Cutânea Passiva/fisiologia , Ligação Proteica/fisiologiaRESUMO
BACKGROUND: Phenylpropylene biosynthesis pathway plays a crucial role in the vanillin and their derivative(s) production in the plants. The intermediate of vanillin synthesis i.e. cinnamic acid (CA) is converted into 2-Hydroxy 4-MethoxyBenzaldehyde (HMB) in Decalepis arayalpathra having a number of therapeutic value. OBJECTIVE: Microwave-assisted modifications in cinnamic acid were planned for potential anticancer properties with better yield and efficiency. The present study also confirms the presence of HMB and its precursor i.e. cinnamic acid in D. arayalpathra tubers. METHODS: We used a single step Microwave Assisted Synthesis (MAS) to modify cinnamic acid, and then examined the synthetic and natural cinnamic acid derivatives anticancer potential against six human cancer (K-562, WRL-68, A549, A431, MCF-7, and COLO-201) and two normal (L-132 and HEK-293) cell lines at 2, 10 and 50 µg/ml concentrations. RESULTS: ß-bromostyrene and ß -nitrostyrene have shown inhibition with IC50 values ranging 0.10-21 µM and 0.03-0.06 µM, respectively to the cancer cell lines. ß-bromostyrene was the most potent anticancer derivative of CA with better cellular safety and biocompatibility. CONCLUSION: The present study of microwave-assisted synthesis demonstrates a single-step modification in cinnamic acid. MAS is a fast, reliable, and robust method. The resultant compounds have shown in-vitro anticancer activity against human lung carcinoma and breast adenocarcinoma.
Assuntos
Antineoplásicos/síntese química , Técnicas de Química Sintética/métodos , Cinamatos/química , Micro-Ondas , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Apocynaceae/química , Benzaldeídos/química , Benzaldeídos/isolamento & purificação , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Cinamatos/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Células HEK293 , Humanos , Camundongos , Rizoma/químicaRESUMO
The present study reports the antifungal, aflatoxin B1 inhibitory, and free radical scavenging activity of chitosan-based nanoencapsulatedBunium persicum Boiss. essential oil (Ne-BPEO). The chemical profile ofBPEO was identified through Gas chromatography mass spectrometry analysis where cuminaldehyde (21.23%), sabinene (14.66%), and γ-terpinen (12.49%) were identified as the major compounds. Ne-BPEO was prepared using chitosan and characterised by Scanning electron microscope (SEM), Atomic force microscope (AFM), Fourier-transform infrared spectroscopy (FTIR), and X-ray diffraction (XRD) assay. Ne-BPEO completely inhibited the growth and aflatoxin B1 production at a concentration of 0.3⯵L/mL. The antifungal and aflatoxin B1 inhibitory effects were related to decreasing in ergosterol content, leakage of membrane ions (Ca2+, K+, and Mg2+), impairment in carbohydrate catabolism, and functioning of ver-1 gene of A. flavus exposed to Ne-BPEO over the control. In addition, Ne-BPEO exhibited promising free radical scavenging activity through DPPH assay (IC50 12.64⯵L/mL) with high thermo-stability. Therefore, chitosan could be used as a carrier agent of plant-based preservative to enhance the shelf-life of food products against A. flavus and aflatoxin B1 contamination.
Assuntos
Antifúngicos/farmacologia , Apiaceae/química , Quitosana/farmacologia , Nanopartículas/química , Óleos Voláteis/química , Extratos Vegetais/química , Aflatoxina B1/metabolismo , Aspergillus flavus/efeitos dos fármacos , Benzaldeídos/isolamento & purificação , Monoterpenos Bicíclicos/isolamento & purificação , Monoterpenos Cicloexânicos/isolamento & purificação , Cimenos/isolamento & purificação , Cromatografia Gasosa-Espectrometria de Massas , Óleos Voláteis/farmacologia , Óleos de Plantas/química , Difração de Raios XRESUMO
In the present study, we hypothesized that the active compound extracted from Proso and Barnyard millets inhibits cell proliferation and apoptosis induction in colon cancer cell line. The bioactive compounds from these millets were purified by supercritical fluid extraction and their structure was elucidated using spectroscopic methods. Extracted bioactive components from these millets were similar in chemical structure to the phenolic aldehyde-Vanillin [4-Hydroxy-3-methoxybenzaldehyde]. Cell proliferative effect was assessed by MTT assay using HT-29 cell line. Compound 1 significantly inhibited the proliferation of HT-29 cells when treated with concentrations of 250 µg/ml and 1,000 µg/ml for 48 h, while compound 2 moderately inhibited the proliferation of the HT-29 cell line at the same concentration and time period. Cytotoxic activity of extracted compounds by the release of lactate dehydrogenase confirms that these compounds were not toxic to the cells at 250 µg/ml of compounds 1 and 2. In addition, flow cytometry results show a significant cell arrest in the G0/G1 phase and increase in the apoptotic cells in sub G0 phase, in a dose-dependent manner when compared with the control. The conclusion of this study suggests that the anticancer property of these millets is mediated through the presence of vanillin.
Assuntos
Benzaldeídos/farmacologia , Neoplasias do Colo/tratamento farmacológico , Echinochloa/química , Panicum/química , Antioxidantes/farmacologia , Apoptose/efeitos dos fármacos , Benzaldeídos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Neoplasias do Colo/metabolismo , Neoplasias do Colo/patologia , Células HT29 , Humanos , Extratos Vegetais/farmacologiaRESUMO
Three new benzaldehyde derivatives, sporulosaldeins Aâ-âC (1: -3: ), and 3 new benzopyran derivatives, sporulosaldeins Dâ-âF (4: -6: ), were discovered from an endophytic fungus, Paraphaeosphaeria sp. F03, which was isolated from Paepalanthus planifolius leaves. Compounds 1: -6: were elucidated by 1- and 2-dimensional nuclear magnetic resonance experiments and high-resolution mass spectrometry analysis. The absolute configuration of compound 5: was determined through the comparison of experimental and calculated electronic circular dichroism data. Compounds 1: -6: were found to exhibit antifungal activity with minimum inhibitory concentration (MIC) values of 7.8â-â250 µg/mL and racemic mixture of compound 6: exhibited weak cytotoxicity against MCF-7 and LM3 with IC50 values of 34.4 and 39.2 µM, respectively.
Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Ascomicetos/química , Benzaldeídos/farmacologia , Benzopiranos/farmacologia , Citotoxinas/farmacologia , Animais , Antibacterianos/química , Antifúngicos/química , Antifúngicos/isolamento & purificação , Benzaldeídos/química , Benzaldeídos/isolamento & purificação , Benzopiranos/química , Benzopiranos/isolamento & purificação , Linhagem Celular Tumoral , Citotoxinas/química , Citotoxinas/isolamento & purificação , Endófitos , Humanos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Camundongos , Testes de Sensibilidade Microbiana , Estrutura MolecularRESUMO
The present work is to study the chemical constituents from petroleum ether fraction of Tibetan medicine Swertia chirayita by column chromatography and recrystallization. The structures were identified by physical and chemical properties and spectral data as swerchirin (1), decussatin (2), 1,8-dihydroxy-3,5,7-trimethoxyxanthone (3), 1-hydroxy-3,5,7,8-tetramethoxyxanthone (4), bellidifolin (5), 1-hydroxy-3, 7-dimethoxyxanthone (6), methylswertianin (7), 1-hydroxy-3,5-dimethoxyxanthone (8), erythrodiol (9), oleanolic acid (10), gnetiolactone (11), scopoletin (12), sinapaldehyde (13), syringaldehyde (14), and ß-sitosterol (15). Compounds 3, 4, 9, 11-14 were isolated from S. chirayita for the first time. Compounds 9 and 12 were firstly isolated from the genus Swertia. The cytotoxic activities of compounds 1, 2, 5, 7 and 8 against human pancreatic cancer cell lines SW1990 and BxPC-3,and the protective effects of these compounds against hydrogen peroxide (H2O2)-induced oxidative stress in human endothelium-derived EA.hy926 were investigated in vitro. The results showed no obvious effect at the high concentration of 50 µmolâ¢L⻹.
Assuntos
Medicamentos de Ervas Chinesas/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Swertia/química , Acroleína/análogos & derivados , Acroleína/isolamento & purificação , Alcanos , Benzaldeídos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Peróxido de Hidrogênio , Ácido Oleanólico/isolamento & purificação , Estresse Oxidativo/efeitos dos fármacos , Escopoletina/isolamento & purificação , Sitosteroides/isolamento & purificação , Xantonas/isolamento & purificaçãoRESUMO
Skin exposure to ultraviolet B (UVB) irradiation leads to the generation of reactive oxygen species (ROS). Excessive ROS cause aging of the skin via basement membrane/extracellular matrix degradation by matrix metalloproteinases (MMPs). We recently demonstrated that 3-bromo-4,5-dihydroxybenzaldehyde (BDB), a natural compound of red algae, had a photo-protective effect against UVB-induced oxidative stress in human keratinocytes. The present study focused on the effect of BDB on UVB-irradiated photo-aging in HaCaT keratinocytes and the underlying mechanism. BDB significantly impeded MMP-1 activation and expression, and abrogated the activation of mitogen-activated protein kinases and intracellular Ca2+ level in UVB-irradiated HaCaT cells. Moreover, BDB decreased the expression levels of c-Fos and phospho-c-Jun and the binding of activator protein-1 to the MMP-1 promoter induced by UVB irradiation. These results offer evidence that BDB is potentially useful for the prevention of UVB-irradiated skin damage.
Assuntos
Benzaldeídos/farmacologia , Queratinócitos/efeitos dos fármacos , Estresse Oxidativo/efeitos dos fármacos , Rodófitas/química , Raios Ultravioleta/efeitos adversos , Benzaldeídos/química , Benzaldeídos/isolamento & purificação , Humanos , Proteínas Quinases JNK Ativadas por Mitógeno/efeitos dos fármacos , Metaloproteinase 1 da Matriz/metabolismo , Proteínas Proto-Oncogênicas c-fos/efeitos dos fármacosRESUMO
A starting material, 4-bromo-3-fluorobenzaldehyde, was used for active drug substance (API) AMG 369 production. The presence of the regioisomer impurities in the starting material 4-bromo-3-fluorobenzaldehyde presented significant challenges for the API synthetic route development due to the physical-chemical similarities of the impurities. These impurities significantly impact on the purity of the starting-material and final drug substance. Control of these impurities is important due to the potential genotoxicity of these impurities (p-GTI). Analytical development was carried out to develop GC methods with high resolving power and high sensitivity to quantify the regioisomers presented in starting material and therefore to control the purity of the starting material and the final drug substance. In the study, complete resolution of the ten regioisomers by 1D-GC and heart-cutting two-dimensional GC (2D-GC) was achieved. A sensitive GC/micro electron capture detection (µ-ECD) method with high resolving power and sensitivity to fully resolve all the ten regioisomers of 4-bromo-3-fluorobenzaldehyde was obtained by using a CHIRALDEX GC column (1D- GC). To facilitate the systematic GC method development, heart-cutting two-dimensional gas chromatography (2D-GC) using a Deans switch was exploited for the separation of the ten regioisomers. The resulting heart-cutting 2D-GC method successfully separated all the ten regioisomers with better sensitivity and resolution. Regioisomer impurities in the starting material were identified and quantified by these GC methods. The sensitivity for the methods is in the range of 0.004ng to 0.02ng for the regioisomers. Linearity for the methods is: R(2)=0.999 to 1.000. The methods were suitable for control of the regioisomer impurities, p-GTIs, in the starting material and final drug substance.
Assuntos
Benzaldeídos/análise , Benzaldeídos/química , Cromatografia Gasosa/métodos , Preparações Farmacêuticas/química , Benzaldeídos/isolamento & purificação , Contaminação de Medicamentos/prevenção & controleRESUMO
A new sample extraction procedure based on micro-solid-phase extraction (µSPE) using a mixture of sorbents of different polarities (polymeric reversed-phase sorbent HLB, silica-based sorbent C18, and multiwalled carbon nanotubes) was applied to extract benzene, toluene, butyraldehyde, benzaldehyde, and tolualdehyde present in saliva to avoid interference from moisture and matrix components and enhance sensitivity and selectivity of the ion mobility spectrometry (IMS) methodology proposed. The extraction of target analytes from saliva samples by using µSPE were followed by the desorption step carried out in the headspace vials placed in the autosampler of the IMS device. Then, 200 µL of headspace was injected into the GC column coupled to the IMS for its analysis. The method was fully validated in terms of sensitivity, precision, and recovery. The LODs and LOQs obtained, when analytes were dissolved in saliva samples to consider the matrix effect, were within the range of 0.38-0.49 and 1.26-1.66 µg mL(-1), respectively. The relative standard deviations were <3.5 % for retention time and drift time values, which indicate that the method proposed can be applied to determine toxic compounds in saliva samples. Graphical abstract Summary of steps followed in the experimental set up of this work.
Assuntos
Aldeídos/isolamento & purificação , Benzaldeídos/isolamento & purificação , Benzeno/isolamento & purificação , Saliva/química , Microextração em Fase Sólida/métodos , Tolueno/isolamento & purificação , Adsorção , Adulto , Cromatografia Gasosa/métodos , Feminino , Humanos , Espectrometria de Mobilidade Iônica/métodos , Limite de Detecção , Magnetismo/métodos , Masculino , Nanotubos de Carbono/química , Dióxido de Silício/química , Tolueno/análogos & derivadosRESUMO
Cinnamomum verum, also called true cinnamon tree, is employed to make the seasoning cinnamon. Furthermore, the plant has been used as a traditional Chinese herbal medication. We explored the anticancer effect of cuminaldehyde, an ingredient of the cortex of the plant, as well as the molecular biomarkers associated with carcinogenesis in human colorectal adenocarcinoma COLO 205 cells. The results show that cuminaldehyde suppressed growth and induced apoptosis, as proved by depletion of the mitochondrial membrane potential, activation of both caspase-3 and -9, and morphological features of apoptosis. Moreover, cuminaldehyde also led to lysosomal vacuolation with an upregulated volume of acidic compartment and cytotoxicity, together with inhibitions of both topoisomerase I and II activities. Additional study shows that the anticancer activity of cuminaldehyde was observed in the model of nude mice. Our results suggest that the anticancer activity of cuminaldehyde in vitro involved the suppression of cell proliferative markers, topoisomerase I as well as II, together with increase of pro-apoptotic molecules, associated with upregulated lysosomal vacuolation. On the other hand, in vivo, cuminaldehyde diminished the tumor burden that would have a significant clinical impact. Furthermore, similar effects were observed in other tested cell lines. In short, our data suggest that cuminaldehyde could be a drug for chemopreventive or anticancer therapy.
Assuntos
Adenocarcinoma/tratamento farmacológico , Antineoplásicos Fitogênicos/farmacologia , Benzaldeídos/farmacologia , Cinnamomum zeylanicum , Neoplasias Colorretais/tratamento farmacológico , DNA Topoisomerases Tipo II/metabolismo , DNA Topoisomerases Tipo I/metabolismo , Extratos Vegetais/farmacologia , Inibidores da Topoisomerase I/farmacologia , Inibidores da Topoisomerase II/farmacologia , Adenocarcinoma/enzimologia , Adenocarcinoma/patologia , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Apoptose/efeitos dos fármacos , Benzaldeídos/isolamento & purificação , Caspase 3/metabolismo , Caspase 9/metabolismo , Morte Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Cinnamomum zeylanicum/química , Neoplasias Colorretais/enzimologia , Neoplasias Colorretais/patologia , Cimenos , Relação Dose-Resposta a Droga , Humanos , Lisossomos/efeitos dos fármacos , Lisossomos/metabolismo , Masculino , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Camundongos Endogâmicos BALB C , Camundongos Nus , Fitoterapia , Extratos Vegetais/isolamento & purificação , Plantas Medicinais , Transdução de Sinais/efeitos dos fármacos , Inibidores da Topoisomerase I/isolamento & purificação , Inibidores da Topoisomerase II/isolamento & purificação , Ensaios Antitumorais Modelo de XenoenxertoRESUMO
Viscum album var. coloratum (Korean mistletoe; KM) is an herbal medicine that is used worldwide for the treatment of various immunological disorders and cancers. KM extract showed enhanced anti-oxidative effects in 2,2-diphenyl-1-picrylhydrazyl, Trolox equivalent antioxidant capacity, and 5-(and-6)-chloromethyl-2',7'-dichlorodihydrofluorescein diacetate acetyl ester assays after being fermented with a crude enzyme extract from a soybean paste fungus, Aspergillus kawachii. High-performance liquid chromatography analysis showed four increased peaks in enzyme treated KM. The increased peaks were isolated and identified as caffeic acid (1), hesperetin (2), syringaldehyde (3), and lyoniresinol (4). Among the four compounds, only 1 and 4 showed strong anti-oxidative activity. Therefore, the fermentation increased the contents of 1 and 4, which consequently increased the anti-oxidative activity of KM.
Assuntos
Anisóis/química , Antioxidantes/farmacocinética , Ácidos Cafeicos/química , Fermentação , Erva-de-Passarinho/química , Naftalenos/química , Animais , Anisóis/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Aspergillus/metabolismo , Benzaldeídos/química , Benzaldeídos/isolamento & purificação , Ácidos Cafeicos/isolamento & purificação , Linhagem Celular , Cromatografia Líquida de Alta Pressão , Sequestradores de Radicais Livres/análise , Ácido Glutâmico/metabolismo , Medicina Herbária , Hesperidina/química , Hesperidina/isolamento & purificação , Camundongos , Naftalenos/isolamento & purificação , Fármacos Neuroprotetores , Extratos Vegetais/química , Extratos Vegetais/farmacologia , SolventesRESUMO
A novel phenylethanoid glycoside, 3'-O-methyl isocrenatoside (1), along with two known compounds, methyl caffeate (2) and protocatechuic aldehyde (3), were isolated from the fresh whole plant of Orobanche cernua Loefling. All the isolated compounds (1-3) were elucidated on the basis of spectroscopic analysis including IR, MS and NMR data. The cytotoxic activities of these compounds were evaluated. Results showed that 3'-O-methyl isocrenatoside (1) and methyl caffeate (2) exhibited significant cytotoxicity, with IC50 values of 71.89, 36.97 µg/mL and 32.32, 34.58 µg/mL against the B16F10 murine melanoma and Lewis lung carcinoma cell lines, respectively.
Assuntos
Antineoplásicos Fitogênicos/química , Glicosídeos/química , Orobanche/química , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Benzaldeídos/química , Benzaldeídos/isolamento & purificação , Ácidos Cafeicos/química , Ácidos Cafeicos/isolamento & purificação , Catecóis/química , Catecóis/isolamento & purificação , Linhagem Celular Tumoral , Glicosídeos/isolamento & purificação , Humanos , Camundongos , Estrutura Molecular , Extratos Vegetais/químicaRESUMO
Eleven compounds were isolated and purified from Phellinus igniarius by column chromatography on silica gel, Sephedax LH-20, RP-8, MCI and preparative TLC. Their structures were identified as 3α-hydroxyfriedel-2-one (1), 3-hydroxyfriedel-3-en-2-one (2), ergosta-4, 6, 8 (14), 22-tetraen-3-one (3), ergosterol peroxide (4), uracil (5), uridine (6), 4-(3, 4-dihydroxyphenyl)-3-butene-2-one (7), protocatechualdehyde (8), inotilone (9), inoscavinA (10) and phellibaumin E (11), respectively, on the basis of NMR and MS data analysis. Among them, compounds 1, 2, 5, and 6 were firstly obtained from this genus. In vitro cytotoxic activity of compounds 1-11 was screened by Cell Titer-GLo Reagent, on 41 human tumor cell strains and 2 hamster normal cell strains via high-throughput screening. Compounds 2-4 exhibit significant cytotoxic activity against NOMO-1 and SKM-1 acute myeloid leukemia cell lines, and compounds 2 and 3 showed good selectivity to NOMO-1 with IC50 values of 0.795 5, 1.828 µmolâ¢L-1and SKM-1 with IC50 values of higher than 10 µmolâ¢L-1. Compound 7 showed remarkable antitumor activities against H526 Human lung cancer cell line, DU145 prostate cancer cell line and HEL erythroleukemia cell line with IC50 values of 0.533 4, 1.885, 1.057 µmolâ¢L⻹, respectively. Other compounds had no or weak antitumor effect. In addition, all compounds had no significant effect on hamster normal cell lines CHL and CHO with IC50 values of higher than 10 µmolâ¢L⻹, which showed that all compounds had no toxic effect on normal cells.
Assuntos
Antineoplásicos/isolamento & purificação , Basidiomycota/química , Animais , Benzaldeídos/isolamento & purificação , Catecóis/isolamento & purificação , Linhagem Celular , Linhagem Celular Tumoral , Cricetinae , Humanos , MasculinoRESUMO
Twelve French Asplenioideae ferns (genera Asplenium and subgenera Ceterach and Phyllitis) were investigated for the first time for volatile organic compounds (VOC) using GC-MS. Sixty-two VOC biosynthesized from the lipidic, shikimic, terpenic and carotenoid pathways were identified. Several VOC profiles can be highlighted from Asplenium jahandiezii and A. xalternifolium with exclusively lipidic derivatives to A. onopteris with an equal ratio of lipidic/shikimic compounds. Very few terpenes as caryophyllene derivatives were identified, but only in A. obovatum subsp. bilotii. The main odorous lipidic derivatives were (E)-2-decenal (waxy and fatty odor), nonanal (aldehydic and waxy odor with a fresh green nuance), (E)-2-heptenal (green odor with a fatty note) and 1-octen-3-ol (mushroom-like odor), reported for all species. A few VOC are present in several species in high content, i.e., 9-oxononanoic acid used as a precursor for biopolymers (19% in A. jahandiezii), 4-hydroxyacetophenone with a sweet and heavy floral odor (17.1% in A. onopteris), and 4-hydroxybenzoic acid used as a precursor in the synthesis of parabens (11.3% in A. foreziense). Most of the identified compounds have pharmacological activities, i.e., octanoic acid as antimicrobial, in particular against Salmonellas, with fatty and waxy odor (41.1% in A. petrarchae), tetradecanoic acid with trypanocidal activity (13.3% in A. obovatum subsp. bilotii), 4-hydroxybenzoic acid (8.7% in A. onopteris) with antimicrobial and anti-aging effects, 3,4-dihydroxybenzaldehyde as an inhibitor of growth of human cancer cells (6.7% in Ceterach officinarum), and phenylacetic acid with antifungal and antibacterial activities (5.8% in A. onopteris). Propionylfilicinic acid was identified in the twelve species. The broad spectrum of odorous and bioactive VOC identified from the Asplenium, Ceterach and Phyllitis species are indeed of great interest to the cosmetic and food industries.
Assuntos
Gleiquênias/química , Extratos Vegetais/química , Compostos Orgânicos Voláteis/química , Aldeídos/química , Aldeídos/isolamento & purificação , Aldeídos/farmacologia , Benzaldeídos/química , Benzaldeídos/isolamento & purificação , Benzaldeídos/farmacologia , Catecóis/química , Catecóis/isolamento & purificação , Catecóis/farmacologia , Gleiquênias/classificação , Octanóis/química , Octanóis/isolamento & purificação , Octanóis/farmacologia , Parabenos/química , Parabenos/isolamento & purificação , Parabenos/farmacologia , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Compostos Orgânicos Voláteis/isolamento & purificação , Compostos Orgânicos Voláteis/farmacologiaRESUMO
Stachybisbins A (1) and B (2), two new meroterpenoids with unprecedented seco-bisabosqual skeleton, together with three biogenetically related metabolites (3-5), were isolated from a wetland fungal strain of Stachybotrys bisbyi. The structures of the new compounds were determined by spectroscopic analyses, modified Mosher's method, and quantum chemical CD method. The cytotoxic activities of all compounds were tested against HL-60, SMMC-7721, A-549, MCF-7, and SW480 human cancer cell lines.
Assuntos
Stachybotrys/química , Terpenos/química , Benzaldeídos/química , Benzaldeídos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Terpenos/isolamento & purificaçãoRESUMO
The traditional knowledge of medicinal plants that are in use by the indigenous Jaintia tribes residing in few isolated pockets of North-East India is documented here. The present study was carried out through the personal discussion with the president of the Jaintia Indigenous Herbal Medicine Association, Dr.H.Carehome Pakyntein from Jowai, Meghalaya. The plants being used generation after generation by his family of herbalists to cure ailments like tuberculosis, cancer and diabetes were selected for the present study. In order to scientifically validate the use of these selected plants for the cure of selected diseases, phytochemical analyses, characterization and molecular docking studies of some of the selected compounds from these plants have been carried out. The compounds 2-hydroxy-4-methoxy- Benzaldehyde from methanolic extract of Strophanthus Wallichii and DL tetrahydropalmatine from Stephania Hernandifolia have been confirmed after determining their molecular structures, justifying the activity of these two plants against TB and cancer, respectively. The present study covers the potentials of some of the medicinal plants of North east India in curing common diseases due to which millions of people suffer and die. The presence of certain compounds in these plants related to the cure of the diseases deserves further studies.
Assuntos
Antineoplásicos Fitogênicos/química , Antituberculosos/química , Benzaldeídos/química , Alcaloides de Berberina/química , Hipoglicemiantes/química , Extratos Vegetais/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antituberculosos/isolamento & purificação , Benzaldeídos/isolamento & purificação , Alcaloides de Berberina/isolamento & purificação , Humanos , Hipoglicemiantes/isolamento & purificação , Índia , Medicina Tradicional , Simulação de Acoplamento Molecular , Plantas Medicinais , TermodinâmicaRESUMO
Increasing attention has been focused on the artificial flavorings added in foods, especially those for infants and children. For the first time, a sensitive and efficient analytical method based on gas chromatography-tandem mass spectrometry (GC-MS/MS) was developed for the simultaneous identification and quantification of four flavoring agents (vanillin, methylvanillin, ethylvanillin, and coumarin) in infant formula samples. The flavorings in samples were extracted with methanol/water (v/v, 1:1), cleaned up by solid-phase extraction, and determined by GC-MS/MS in selected reaction monitoring (SRM) mode. Both isotope-labeled internal standards and matrix-matched calibration solutions were used to correct the matrix effects. The limit of quantification (LOQ) was calculated as 10 times the standard deviation, and it was 10.0 µg kg (-1) for vanillin, methylvanillin, ethylvanillin, and coumarin. The average recoveries were in the range of 82.8-107.5% with relative standard deviations (RSDs) below 8.9% measured at three concentration levels (10, 50, and 100 µg kg(-1)). The proposed method is suitable for the sensitive and accurate simultaneous determination of four flavoring agents in infant formula samples and also provided potential use for reference in terms of real analysis of other foods.
Assuntos
Aromatizantes/química , Aromatizantes/isolamento & purificação , Cromatografia Gasosa-Espectrometria de Massas/métodos , Fórmulas Infantis/química , Extração em Fase Sólida/métodos , Benzaldeídos/química , Benzaldeídos/isolamento & purificação , Cumarínicos/química , Cumarínicos/isolamento & purificação , Humanos , Estrutura MolecularRESUMO
BACKGROUND: The treatment of leishmaniasis with pentavalent antimonials is problematic because of their toxicity. Investigations of potentially active molecules are important to discover less toxic drugs that are viable economic alternatives for the treatment of leishmaniasis. Thiosemicarbazones are a group of molecules that are known for their wide versatility and biological activity. In the present study, we examined the antileishmania activity, mechanism of action, and biochemical alterations produced by a novel molecule, 4-nitrobenzaldehyde thiosemicarbazone (BZTS), derived from S-limonene against Leishmania amazonensis. RESULTS: BZTS inhibited the growth of the promastigote and axenic amastigote forms, with an IC50 of 3.8 and 8.0 µM, respectively. Intracellular amastigotes were inhibited by the compound with an IC50 of 7.7 µM. BZTS also had a CC50 of 88.8 µM for the macrophage strain J774A1. BZTS altered the shape, size, and ultrastructure of the parasites, including damage to mitochondria, reflected by extensive swelling and disorganization of the inner mitochondrial membrane, intense cytoplasmic vacuolization, and the presence of concentric membrane structures inside the organelle. Cytoplasmic lipid bodies, vesicles inside vacuoles in the flagellar pocket, and enlargement were also observed. BZTS did not induce alterations in the plasma membrane or increase annexin-V fluorescence intensity, indicating no phosphatidylserine exposure. However, it induced the production of mitochondrial superoxide anion radicals. CONCLUSIONS: The present results indicate that BZTS induced dramatic effects on the ultrastructure of L. amazonensis, which might be associated with mitochondrial dysfunction and oxidative damage, leading to parasite death.