RESUMO
Eight undescribed sesquiterpene coumarins (1-8) and twenty known ones (9-28), were isolated from the aerial parts of Ferula sinkiangensis K. M. Shen. Their structures were elucidated based on the comprehensive analysis of UV, IR, HRESIMS, 1D, and 2D NMR data. The absolute configuration of 1 was determined by single crystal X-Ray diffraction, while the absolute configurations of 2-8 were determined by comparisons of experimental and calculated electrostatic circular dichroism spectra. Compound 2 is the first hydroperoxy sesquiterpene coumarin from the genus Ferula, while compound 8 has an unusual 5',8'-peroxo bridge. Griess reaction results indicated compound 18 significantly decreased nitric oxide production of the lipopolysaccharide-stimulated RAW 264.7 macrophages with an IC50 value of 2.3 µM, and ELISA results revealed that compound 18 effectively inhibited tumor necrosis factor-α, interleukin (IL)-1ß, and IL-6 expressions.
Assuntos
Ferula , Sesquiterpenos , Estrutura Molecular , Ferula/química , Lipopolissacarídeos/farmacologia , Anti-Inflamatórios/farmacologia , Macrófagos/metabolismo , Cumarínicos/farmacologia , Cumarínicos/química , Componentes Aéreos da Planta/metabolismo , Sesquiterpenos/farmacologia , Sesquiterpenos/química , Óxido Nítrico/metabolismoRESUMO
Arsenic exposure is associated with the induction of hepatotoxicity. Current study was aimed to investigate the hepato-protective ability of polyphenolic components of Tamarix aphylla (TA) ethanolic extract against sodium arsenite (SA)-induced liver injury of rats. Significantly higher quantities of phenolic (318.7±2.5 mgg-1GAE) and flavonoid (250.69 ±3.3 mgg-1QE) contents were present. Inhibitory concentration (IC50) exhibited an excellent potential for antioxidant (IC50= 25.99 µg/mL) assay. High performance liquid chromatography (HPLC) confirmed the existence of myercetin (10.40ppm), sinapic acid (2.131ppm), kaempferol (0.486ppm), caffeic acid (5.094 ppm). Forty-two rats were divided into 7 groups. Group 1 received normal saline (2 mL/kg/day, orally for 21 days), Group 2 received SA (10mg/kg/day for 21 days), and Group 3 received SA alone for 7 days (10mg/kg) and continues with silymarine for 21 days (25mg/kg orally). Group 4, 5, 6 received SA alone for 7 days and continue with TA extract up to 21 days (125mg/kg, 250mg/kg, and 500mg/kg orally) respectively, and Group 7 received TA extract (500mg/kg) for 21 days. SA was administered to all treated groups for 21 days. Treatment with polyphenolic ethanolic extract of TA restored the hepatic indices and oxidative markers in a dose-dependent manner. The upregulation in tumor necrosis factor-α, interleukin-6, and cyclooxygenase-2 upon SA treatment suggesting inflammation was normalized by the treatment of rats. Above mentioned biochemical findings were supported well with histopathological screening. Present findings suggest that TA polyphenolic ethanolic extract could mitigate the oxidative stress and inflammation induced by SA in liver tissue.
Assuntos
Doença Hepática Induzida por Substâncias e Drogas , Tamaricaceae , Ratos , Animais , Tamaricaceae/metabolismo , Polifenóis/farmacologia , Antioxidantes/farmacologia , Antioxidantes/metabolismo , Estresse Oxidativo , Fígado/metabolismo , Doença Hepática Induzida por Substâncias e Drogas/prevenção & controle , Componentes Aéreos da Planta/metabolismo , Inflamação , Extratos Vegetais/farmacologiaRESUMO
Bupleurum chinense DC. is a traditional Chinese medicine with a long medicinal history and is often used as the main ingredient in prescription drugs for epilepsy. The aerial parts of B. chinense DC. have similar efficacy and composition to B. chinense DC. Therefore, we speculated that the aerial parts of B. chinense DC. could be used in the treatment of epilepsy. Polysaccharides from the aerial parts of B. chinense DC. were selected to explore their therapeutic effects on epilepsy and their potential mechanism of action. The study is aimed at clarifying the antiepileptic effects of the polysaccharides from the aerial parts of B. chinense DC. and their potential underlying mechanisms. The chemical profile of the aerial parts of B. chinense DC. polysaccharides (ABP) was characterized by FT-IR spectrum and HPLC chromatogram. To determine the therapeutic effects of ABPs on epilepsy, we established a kainic acid- (KA-) induced rat model of epilepsy, and through H&E staining, Nissl staining, immunohistochemistry, biochemical analysis, ELISA, and Western blot analysis, we explored the mechanisms underlying the therapeutic effects of ABPs on epilepsy. The monosaccharide content of ABP included galacturonic acid (45.19%), galactose (36.63%), arabinose rhamnose (12.13%), and mannose (6.05%). Moreover, the average molecular weight of ABP was 1.38 × 103 kDa. ABP could improve hippocampal injuries and neuronal function in the KA-induced epilepsy rat model. ABP significantly inhibited oxidative stress in the hippocampus of KA-induced rats. More importantly, ABP could regulate TREM2 activation in the PI3K/Akt/GSK-3ß pathway to inhibit neuronal apoptosis, including increasing the expression of superoxide dismutase and lactate dehydrogenase and decreasing the expression of malondialdehyde. The current study defined the potential role of ABP in inhibiting the development of epilepsy, indicating that ABP could upregulate TREM2 to alleviate neuronal apoptosis, by activating the PI3K/Akt/GSK-3ß pathway and oxidative stress in epilepsy.
Assuntos
Bupleurum , Epilepsia , Animais , Bupleurum/química , Bupleurum/metabolismo , Epilepsia/tratamento farmacológico , Glicogênio Sintase Quinase 3 beta/metabolismo , Estresse Oxidativo , Fosfatidilinositol 3-Quinases/metabolismo , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Polissacarídeos/farmacologia , Polissacarídeos/uso terapêutico , Proteínas Proto-Oncogênicas c-akt/metabolismo , Ratos , Transdução de Sinais , Espectroscopia de Infravermelho com Transformada de FourierRESUMO
The present study aimed to assess the effects of epileptic treatment of the aerial part of Bupleurum chinense DC. in kainic acid (KA)-induced epilepsy rats and LPS-induced BV2 cells, as well as to identify the active chemical constituents. The in vivo and vitro results showed that 20% ethanol elution fractions of the aerial part of B. chinense DC. (BCE-20) and 70% ethanol elution fractions of the aerial part of B. chinense DC. (BCE-70) could improve the epileptic state of the rats and status epilepticus (SE%). Moreover, ultra-high-performance liquid chromatography (UPLC)-Orbitrap- mass spectrometry (MS) analysis identified BCE-20 and 70 as flavonoids and phenylpropanoids, respectively. The mechanistic analysis also showed that BCE-20 and 70 could regulate neurotransmitter abnormalities and suppresses the expression and secretion of pro-inflammatory cytokines. Notably, BCE-20 and 70 could regulate the Triggering receptor expressed on myeloid cells 2 (TREM2)/nuclear factor-k-gene binding (NF-κB)/inhibitor of NF-κB α (IκBα) pathway to inhibit the neuroinflammation. Our findings support the ethnopharmacological use of the constituent polyphenols and flavonoids from the aerial part of B. chinense DC., as the strong anti-epileptic agents.
Assuntos
Bupleurum , Epilepsia , Ratos , Animais , Bupleurum/química , NF-kappa B/metabolismo , Flavonoides/farmacologia , Componentes Aéreos da Planta/metabolismo , Etanol , Epilepsia/induzido quimicamente , Epilepsia/tratamento farmacológicoRESUMO
Carpesium divaricatum Sieb. & Zucc., a traditional medicinal plant used as an inflammation-relieving remedy, is a rich source of terpenoids. At least 40 germacrane-type sesquiterpene lactones, representatives of four different structural groups, were isolated from the plant. Cytotoxicity against cancer cells in vitro is the most frequently described biological activity of the compounds. However, little is known about the selectivity of the cytotoxic effect. The anti-inflammatory activity of the germacranolides is also poorly documented. The objective of the present study was to assess the cytotoxic activity of selected C. divaricatum germacranolides-derivatives of 4,5,8,9-tetrahydroxy-3-oxo-germacran-6,12-olide towards cancer and normal cell lines (including cells of different p53 status). Moreover, to assess the anti-inflammatory effect of the compounds, the release of four proinflammatory cytokines/chemokines (IL-1ß, IL-8, TNF-α and CCL2) by lipopolysaccharide-stimulated human neutrophils was measured by ELISA. The investigated sesquiterpene lactones demonstrated nonselective activity towards prostate cancer (Du145 and PC3) and normal prostate epithelial cells (PNT2) as well as against melanoma cells (A375 and HTB140) and keratinocytes (HaCaT). Cytotoxic activity against osteosarcoma cells was independent of their p53 status. In sub-cytotoxic concentrations (0.5-2.5 µM) the studied compounds significantly decreased cytokine/chemokine release by lipopolysaccharide-stimulated human leukocytes.
Assuntos
Anti-Inflamatórios/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Asteraceae/química , Citotoxinas/farmacologia , Sesquiterpenos de Germacrano/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/classificação , Anti-Inflamatórios/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/classificação , Antineoplásicos Fitogênicos/isolamento & purificação , Asteraceae/metabolismo , Linhagem Celular , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Quimiocina CCL2/genética , Quimiocina CCL2/imunologia , Citotoxinas/química , Citotoxinas/classificação , Citotoxinas/isolamento & purificação , Doxorrubicina/farmacologia , Regulação Neoplásica da Expressão Gênica , Humanos , Concentração Inibidora 50 , Interleucina-1beta/genética , Interleucina-1beta/imunologia , Interleucina-8/genética , Interleucina-8/imunologia , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Neutrófilos/citologia , Neutrófilos/efeitos dos fármacos , Neutrófilos/imunologia , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Extratos Vegetais/química , Plantas Medicinais , Polônia , Cultura Primária de Células , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/classificação , Sesquiterpenos de Germacrano/isolamento & purificação , Transdução de Sinais , Fator de Necrose Tumoral alfa/genética , Fator de Necrose Tumoral alfa/imunologia , Proteína Supressora de Tumor p53/genética , Proteína Supressora de Tumor p53/imunologiaRESUMO
The genus Rhanterium (Asteraceae) is a widely distributed medicinal plant throughout western North Africa and some Rhanterium species are used in folk medicine. The aim of research was to investigate methanolic extracts from different parts (flowers, leaves, and stems) of Tunisian Rhanterium suaveolens as potential sources of bioactive products useful for healthy purposes. In particular, were analyzed the phenolic composition of these extracts and their antioxidant, anti-inflammatory, and anti-tyrosinase properties. The phytochemical analyses were performed using standard colorimetric procedures, HPLC-DAD and HPLC-DAD-ESI-MS. Then, several inâ vitro cell-free assays have been used to estimate the antioxidant/free radical scavenging capability of the extracts. Moreover, inâ vitro, and inâ vivo anti-melanogenesis activities of these extracts were tested, respectively, with the tyrosinase inhibition assay and the Zebrafish embryo model. Finally, the anti-inflammatory potential of these extracts in an inâ vitro model of acute intestinal inflammation in differentiated Caco-2 cells was evaluated. The R. suaveolens extracts under study appeared particularly rich in flavonols and hydroxycinnamic acids and all extracts appeared endowed with good antioxidant/free radical scavenging properties, being the flower extracts slightly more active than the others. Moreover, R. suaveolens flowers extract was able to inhibit inâ vitro tyrosinase activity and exhibited bleaching effects on the pigmentation of zebrafish embryos. Furthermore, all extracts showed good anti-inflammatory activity in intestinal epithelial cells as demonstrated by the inhibition of TNF-α-induced gene expression of IL-6 and IL-8. R. suaveolens aerial parts may be considered as a potential source of whitening agents, as well as of agents for the treatment of disorders related to oxidative stress and inflammation.
Assuntos
Anti-Inflamatórios/química , Asteraceae/química , Inibidores Enzimáticos/química , Monofenol Mono-Oxigenase/antagonistas & inibidores , Extratos Vegetais/química , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/metabolismo , Anti-Inflamatórios/farmacologia , Antioxidantes/química , Asteraceae/metabolismo , Células CACO-2 , Diferenciação Celular/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Ácidos Cumáricos/química , Ácidos Cumáricos/isolamento & purificação , Ácidos Cumáricos/metabolismo , Ácidos Cumáricos/farmacologia , Embrião não Mamífero/citologia , Embrião não Mamífero/efeitos dos fármacos , Embrião não Mamífero/metabolismo , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/metabolismo , Inibidores Enzimáticos/farmacologia , Flavonóis/química , Flavonóis/isolamento & purificação , Flavonóis/metabolismo , Flavonóis/farmacologia , Humanos , Melaninas/metabolismo , Monofenol Mono-Oxigenase/metabolismo , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Plantas Medicinais/química , Plantas Medicinais/metabolismo , Espectrometria de Massas por Ionização por Electrospray , Tunísia , Peixe-Zebra/metabolismoRESUMO
A decoction prepared from the aerial parts of Melampodium divaricatum showed antinociceptive and antihyperalgesic responses when tested in the formalin model in mice. From the CH2 Cl2 fraction of the decoction, two non-previously reported secondary metabolites, 3-O-ß-D-glucopyranosyl-16α-hydroxy-ent-kauraneâ (1) and melampodiamideâ (2) [(2'R*,4'Z)-2'-hydroxy-N-[(2S*,3S*,4R*)-1,3,4-trihydroxyoctadec-2-yl]tetracos-4-enamide] were separated and characterized by spectroscopic, spectrometric, and computational techniques. The flavonoids isoquercitrin and hyperoside, which possessed noted antinociceptive properties, were obtained from the active AcOEt fraction of the decoction. The chemical composition of the essential oil of the plant was also analyzed by gas chromatography-mass spectrometry. The major constituents were (E)-caryophyllene, germacreneâ D, ß-elemene, δ-elemene, γ-patchoulene, and 7-epi-α-selinene. Headspace solid-phase microextraction analysis detected (E)-caryophyllene as the main volatile compound of the plant.
Assuntos
Analgésicos/química , Asteraceae/química , Óleos Voláteis/química , Extratos Vegetais/química , Analgésicos/isolamento & purificação , Analgésicos/uso terapêutico , Animais , Asteraceae/metabolismo , Diterpenos do Tipo Caurano/química , Diterpenos do Tipo Caurano/isolamento & purificação , Diterpenos do Tipo Caurano/uso terapêutico , Cromatografia Gasosa-Espectrometria de Massas , Masculino , Camundongos , Camundongos Endogâmicos ICR , Conformação Molecular , Neuralgia/induzido quimicamente , Neuralgia/tratamento farmacológico , Neuralgia/patologia , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Extratos Vegetais/uso terapêutico , Microextração em Fase Sólida , EstereoisomerismoRESUMO
Chemical investigation of the aerial parts (except fruits) of the medicinal, hallucinogen and toxic plant Datura innoxia Mill. [Solanaceae] led to the isolation of the new withanolide, dinnoxolide A (1), along with the known compounds 21,27-dihydroxy-1-oxowitha-2,5,24-trienolide (2), daturamalakin B (3) and withametelin (4). Their structures were established by analysis of their spectroscopic data, including 1D and 2D NMR experiments and MS. Compounds 2 and 3 were isolated as natural products for the first time and the name dinnoxolide B was given to compound 2. The four withanolides showed in vitro cytotoxic activity against U251 (glioblastoma) and SK-LU-1 (lung adenocarcinoma) human cancer cell lines, with IC50 values ranging from 1.2 to 19.6 µM, and also against the noncancerous monkey kidney cell line (COS-7), with IC50 values ranging from 5.0 to 19.7 µM. Compound 4 was two times more active than the reference compound, etoposide, against lung adenocarcinoma cells.
Assuntos
Antineoplásicos Fitogênicos/química , Datura/química , Vitanolídeos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Datura/metabolismo , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Extratos Vegetais/química , Vitanolídeos/isolamento & purificação , Vitanolídeos/farmacologiaRESUMO
Menopause, caused by decreases in estrogen production, results in symptoms such as facial flushing, vaginal atrophy, and osteoporosis. Although hormone replacement therapy is utilized to treat menopausal symptoms, it is associated with a risk of breast cancer development. We aimed to evaluate the estrogenic activities of Spartina anglica (SA) and its compounds and identify potential candidates for the treatment of estrogen reduction without the risk of breast cancer. We evaluated the estrogenic and anti-proliferative effects of extracts of SA and its compounds in MCF-7 breast cancer cells. We performed an uterotrophic assay using an immature female rat model. Among extracts of SA, belowground part (SA-bg-E50) had potent estrogenic activity. In the immature female rat model, the administration of SA-bg-E50 increased uterine weight compared with that in the normal group. Among the compounds isolated from SA, 1,3-di-O-trans-feruloyl-(-)-quinic acid (1) had significant estrogenic activity and induced phosphorylation at serine residues of estrogen receptor (ER)α. All extracts and compounds from SA did not increase MCF-7 cell proliferation. Compound 1 is expected to act as an ERα ligand and have estrogenic effects, without side effects, such as breast cancer development.
Assuntos
Fitoestrógenos/farmacologia , Extratos Vegetais/farmacologia , Poaceae/metabolismo , Útero/efeitos dos fármacos , Animais , Neoplasias da Mama/patologia , Proliferação de Células/efeitos dos fármacos , Receptor alfa de Estrogênio/agonistas , Receptor alfa de Estrogênio/metabolismo , Feminino , Humanos , Ligantes , Células MCF-7 , Estrutura Molecular , Tamanho do Órgão , Fitoestrógenos/isolamento & purificação , Fitoestrógenos/toxicidade , Componentes Aéreos da Planta/metabolismo , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Raízes de Plantas/metabolismo , Poaceae/crescimento & desenvolvimento , Ratos Sprague-Dawley , Relação Estrutura-Atividade , Útero/crescimento & desenvolvimento , Útero/metabolismoRESUMO
Column chromatography (CC) analysis of methanol and butanol extracts of the aerial parts of Calortopis procera as well as the methanol extract of its latex, led to the isolation of 8 cardenolides, of which the structures were elucidated by NMR and HRESIMS spectroscopy. They also revealed several triterpenes and flavonoid glycoside. Based on the antiproliferative activity reported for cardenolides, the activity of calotropin and calotoxin was tested against two common cancer cell lines, human triple-negative breast cancer cell line (MDA-MB-231) and human lung adenocarcinoma cell line (A549). The high toxicity of the latex also encouraged performing the same test on the same cancer cell lines. The anti-proliferative activity of calotropin and calotoxin was compared to the methanol extract and the wax of the latex. The results showed that calotropin and calotoxin have significant cytotoxicity against MDA-MB-231 and A549 cell lines ranging from 0.046 to 0.072 µM compared to the methanol extract and the wax of its latex ranging from 0.47 to 58.41 µM. Moreover, the results showed lower toxicity of all treatments to the human skin fibroblasts compared to the toxicity to both MDA-MB-231 and A549 cancer cells lines except the higher toxicity of Methanolic extracts of C. procera latex to the MDA-MB-231 cells. In conclusion, C. procera is a medicinal plant with a wide spectrum of cardinolides including calotropin and calotoxin, which are promising agents for targeted cancer phytotherapy.
Assuntos
Antineoplásicos Fitogênicos/química , Apocynaceae/química , Cardenolídeos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Apocynaceae/metabolismo , Cardenolídeos/isolamento & purificação , Cardenolídeos/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Extratos Vegetais/químicaRESUMO
The MeOH extract from dried aerial parts of Oxypetalum caeruleum (Apocynaceae) plants yielded seventeen compounds, including four new tetracyclic triterpenoids, one pregnane glycoside, two lignane glycosides, and ten known compounds. The structures of the new compounds were established using NMR, MS spectroscopic analysis and chemical evidence.
Assuntos
Apocynaceae/química , Lignanas/química , Esteroides/química , Triterpenos/química , Apocynaceae/metabolismo , Espectroscopia de Ressonância Magnética , Conformação Molecular , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Extratos Vegetais/química , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
In the current study the pyrrolizidine alkaloid profiles of the species Echium sabulicola ssp. decipiens (Pomel) Klotz and Solenanthus lanatus DC were studied in various extracts. In addition, a chemotaxonomic study within the genus and the family was carried out. The analysis was carried out by using gas chromatography coupled to mass spectrometry and by comparing the Kovats Indices and molecular and fragment ions with literature data. Twenty-three alkaloids were tentatively identified. The results showed the presence of already reported compounds as well as previously unreported ones leading both to a confirmation of the botanical classification of the two studied species and to a brand new path in the chemotaxonomy of Boraginaceae family. The presence of some pyrrolizidine alkaloids sets limits for the usage of these plants for medicinal purposes. The identified compounds confirm the botanical classification of the studied species as members of the Boraginaceae family and their presence advices against their use in the ethnopharmacological field.
Assuntos
Boraginaceae/química , Alcaloides de Pirrolizidina/química , Argélia , Boraginaceae/metabolismo , Frutas/química , Frutas/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Conformação Molecular , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Alcaloides de Pirrolizidina/isolamento & purificaçãoRESUMO
Rheum ribes L. (Rhubarb) is one of the most important edible medicinal plants in the Eastern Anatolia region and is called "Iskin" by local people. Resveratrol and 6-O-methylalaternin were isolated from the Rhubarb for the first time in addition to well-known secondary metabolites including emodin, aloe-emodin, ß-sitosterol and rutin. The new semi-synthetic anthraquinone derivatives with the NαFmoc-l-Lys and ethynyl group were synthesized from the isolated anthraquinones emodin and aloe-emodin of Rhubarb to increase the bioactivities. Aloe-emodin derivative with NαFmoc-l-Lys shows the highest inhibition values by 94.11 ± 0.12 and 82.38 ± 0.00% against HT-29 and HeLa cell lines, respectively, at 25 µg/mL. Further, modification of the aloe-emodin with both the ethynyl and the NαFmoc-l-Lys groups showed an antioxidant activity-enhancing effect. From molecular docking studies, the relative binding energies of the emodin and aloe-emodin derivatives to human serum albumin ranged from -7.30 and -10.62 kcal/mol.
Assuntos
Antraquinonas/química , Antineoplásicos/síntese química , Resveratrol/química , Rheum/química , Antraquinonas/síntese química , Antraquinonas/isolamento & purificação , Antraquinonas/metabolismo , Antraquinonas/farmacologia , Antineoplásicos/farmacologia , Sítios de Ligação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Emodina/química , Emodina/isolamento & purificação , Emodina/metabolismo , Emodina/farmacologia , Humanos , Simulação de Acoplamento Molecular , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Resveratrol/isolamento & purificação , Resveratrol/farmacologia , Rheum/metabolismo , Albumina Sérica/química , Albumina Sérica/metabolismoRESUMO
Mass spectrometry-based molecular imaging has been utilized to map the spatial distribution of target metabolites in various matrixes. Among the diverse mass spectrometry techniques, matrix-assisted laser desorption/ionization-mass spectrometry (MALDI-MS) is the most popular for molecular imaging due to its powerful spatial resolution. This unparalleled high resolution, however, can paradoxically act as a bottleneck when the bio-imaging of large areas, such as a whole plant, is required. To address this issue and provide a more versatile tool for large scale bio-imaging, direct analysis in real-time-time of flight-mass spectrometry (DART-TOF-MS), an ambient ionization MS, was applied to whole plant bio-imaging of a medicinal plant, Ephedrae Herba. The whole aerial part of the plant was cut into 10-20 cm long pieces, and each part was further cut longitudinally to compare the contents of major ephedra alkaloids between the outer surface and inner part of the stem. Using optimized DART-TOF-MS conditions, molecular imaging of major ephedra alkaloids of the whole aerial part of a single plant was successfully achieved. The concentration of alkaloids analyzed in this study was found to be higher on the inner section than the outer surface of stems. Moreover, side branches, which are used in traditional medicine, represented a far higher concentration of alkaloids than the main stem. In terms of the spatial metabolic distribution, the contents of alkaloids gradually decreased towards the end of branch tips. In this study, a fast and simple macro-scale MS imaging of the whole plant was successfully developed using DART-TOF-MS. This application on the localization of secondary metabolites in whole plants can provide an area of new research using ambient ionization mass spectroscopy and an unprecedented macro-scale view of the biosynthesis and distribution of active components in medicinal plants.
Assuntos
Alcaloides/metabolismo , Ephedra/metabolismo , Espectrometria de Massas/métodos , Plantas Medicinais/metabolismo , Efedrina/análogos & derivados , Efedrina/metabolismo , Espectrometria de Massas/instrumentação , Imagem Molecular/instrumentação , Imagem Molecular/métodos , Componentes Aéreos da Planta/metabolismo , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por MatrizRESUMO
INTRODUCTION: Herb, Zanthoxylum armatum DC., commonly called Indian prickly ash, and Nepal pepper (family Rutaceae), is widely utilized in the traditional medicinal system. OBJECTIVE: The current review provides requisite data for collecting descriptive information on the organoleptic, microscopical, ethnobotanical use, and phytochemicals and pharmacological properties of Z. armatum; therefore, it may help in forming a bridge between research gaps and the upcoming future findings for most of the researches. MATERIALS AND METHODS: The systematic literature survey was conducted using the PRISMA methodology. The collective information was gathered from books, renowned journals, and electronic databases including Science Direct, Web of Science, Scopus and PubMed from 1966 to 2020. RESULTS: Most of the bioactive metabolites are isolated and characterized till date, such as monoterpenes in essential oil and lignan components are reported to be present in the herbs. Several in vitro and in vivo pharmacological bioassays revealed the potential of Z. armatum having as possessing antimicrobial, antifungal, antibacterial, and hepatoprotective effects and so on. CONCLUSION: Therefore, the current review summarizes the organoleptic, microscopy, phytochemistry and biological activities of Z. armatum, providing more emphasis on in vitro as well as in-vivo studies along with clinical research, helpful in exploring the potential efficacy of the plant.
Assuntos
Compostos Fitoquímicos/química , Zanthoxylum/química , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Fungos/efeitos dos fármacos , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Medicina Tradicional , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Extratos Vegetais/química , Zanthoxylum/metabolismoRESUMO
To comprehensively annotate miRNAs and their targets in tea plant, Camellia sinensis, we sequenced small and messenger RNAs of 9 samples of Camellia sinensis var. assamica (YK-10), a diploid elite cultivar widely grown in southwest China. In order to identify targets of miRNAs, we sequenced two degradome sequencing profiles from leaves and roots of YK-10, respectively. By analyzing the small RNA-Seq profiles, we newly identified 137 conserved miRNAs and 23 species specific miRNAs in the genome of YK-10, which significantly improved the annotation of miRNAs in tea plant. Approximately 2000 differently expressed genes were identified when comparing RNA-Seq profiles of any two of the three organs selected in the study. Totally, more than 5000 targets of conserved miRNAs were identified in the two degradome profiles. Furthermore, our results suggest that a few miRNAs play roles in the biosynthesis pathways of theanine, caffeine and flavonoid. These results enhance our understanding of small RNA guided gene regulations in different organs of tea plant.
Assuntos
Camellia sinensis/genética , Redes Reguladoras de Genes , MicroRNAs/genética , Camellia sinensis/classificação , Evolução Molecular , MicroRNAs/metabolismo , Filogenia , Componentes Aéreos da Planta/metabolismo , RNA Mensageiro/genética , RNA Mensageiro/metabolismo , Metabolismo Secundário/genéticaRESUMO
Phytochemical investigation of the aerial parts of Siegesbeckia pubescens led to seventeen diterpenoids (1-17) and twelve sesquiterpenoids (18-29). Their structures were varied including twelve ent-pimarane (1-12), three ent-kaurane (13-15), two acyclic diterpenoids (16-17), ten germacrene (18-27), one guaiane (28), and one caryolane (29) sesquiterpenoids. Eight of twenty-nine were new ones (1, 3, 4, 16-18, 23, and 28). Their structures were elucidated by extensive spectroscopic analysis. The absolute configurations of compounds 1 and 2 were identified using X-ray diffraction analysis, and of compounds 18, 23, and 28 were elucidated by the experimental and calculated electronic circular dichroism (ECD) spectra. All the isolated compounds (1-29) were assayed for their inhibition of RANKL-induced osteoclastogenesis in bone marrow macrophages (BMMs). Four sesquiterpenoids 18, 25, 26, and 27 exhibited potent inhibition of osteoclastogenesis with IC50 value of 0.51, 0.80, 0.50, and 0.83 µM, respectively. Here we demonstrated that S. pubescens may be a resource for discovery of anti-osteoporosis agents.
Assuntos
Asteraceae/química , Diferenciação Celular/efeitos dos fármacos , Diterpenos/química , Osteogênese/efeitos dos fármacos , Sesquiterpenos/química , Animais , Asteraceae/metabolismo , Sobrevivência Celular/efeitos dos fármacos , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Macrófagos/citologia , Macrófagos/metabolismo , Espectroscopia de Ressonância Magnética , Camundongos , Conformação Molecular , NF-kappa B/genética , NF-kappa B/metabolismo , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Extratos Vegetais/química , Ligante RANK/farmacologia , Células RAW 264.7 , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Ativação Transcricional/efeitos dos fármacosRESUMO
Allium species are widely consumed as food all over the world. The phenolic profile of ethanol extracts of aerial parts and roots of 12 Allium species, collected from five different Eastern Anatolia regions, were studied using LC-MS/MS. In vitro antioxidant, anticholinesterase, cytotoxic and antimicrobial activities were also tested. The multivariate analyses were performed using principal component and hierarchical cluster analyses. Seventeen of 27 standard compounds were detected in all Allium species. The major components were mainly identified as quinic acid, malic acid, vanillin, and p-coumaric acid. The aerial parts possessed better antioxidant activity than roots. Aerial parts of A. atroviolaceum, A. chrysantherum, A. kharputense, and A. shirnakiense exhibited high cytotoxic activity against DLD-1 colon cancer cell lines (IC50 12.5â µg/mL). A. shatakiense and A. vineale demonstrated good antimicrobial activity against S. aureus and E. coli (MIC 75â µg/mL). According to chemometric analysis, differences were detected between aerial parts and the roots. The aerial parts of A. atroviolaceum, A. chrysantherum, A. kharputense, and A. shirnakiense could be potent in the pharmaceutical industry while A. shatakiense and A. vineale in the food industry after further investigations.
Assuntos
Allium/química , Anti-Infecciosos/química , Fenóis/química , Extratos Vegetais/química , Acetilcolinesterase/química , Acetilcolinesterase/metabolismo , Allium/metabolismo , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Antioxidantes/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Análise por Conglomerados , Escherichia coli/efeitos dos fármacos , Humanos , Testes de Sensibilidade Microbiana , Fenóis/isolamento & purificação , Fenóis/metabolismo , Fenóis/farmacologia , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Análise de Componente Principal , Staphylococcus aureus/efeitos dos fármacos , Espectrometria de Massas em TandemRESUMO
Previous studies have reported that Hedyotis diffusa Willdenow extract shows various biological activities on cerebropathia, such as neuroprotection and short-term memory enhancement. However, there has been a lack of studies on the inhibitory activity on neurodegenerative diseases such as Alzheimer's disease (AD) through enzyme assays of H. diffusa. Therefore, H. diffusa extract and fractions were evaluated for their inhibitory effects through assays of enzymes related to AD, including acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), and ß-site amyloid precursor protein cleaving enzyme 1 (BACE1), and on the formation of advanced glycation end-product (AGE). In this study, ten bioactive compounds, including nine iridoid glycosides 1-9 and one flavonol glycoside 10, were isolated from the ethyl acetate and n-butanol fractions of H. diffusa using a bioassay-guided approach. Compound 10 was the strongest inhibitor of cholinesterase, BACE1, and the formation of AGEs of all isolated compounds, while compound 5 had the lowest inhibitory activity. Compounds 3, 6, and 9 exhibited better inhibitory activity than other compounds on AChE, and two pairs of diastereomeric iridoid glycoside structures (compounds 4, 8, and 6, 7) showed higher inhibitory activity than others on BChE. In the BACE1 inhibitory assay, compounds 1-3 were good inhibitors, and compound 10 showed higher inhibitory activity than quercetin, the positive control. Moreover, compounds 1 and 3 were stronger inhibitors of the formation of AGE than aminoguanidine (AMG), the positive control. In conclusion, this study is significant since it demonstrated that the potential inhibitory activity of H. diffusa on enzymes related to AD and showed the potential use for further study as a natural medicine for AD treatment on the basis of the bioactive components isolated from H. diffusa.
Assuntos
Acetilcolinesterase/metabolismo , Doença de Alzheimer/tratamento farmacológico , Secretases da Proteína Precursora do Amiloide/metabolismo , Ácido Aspártico Endopeptidases/metabolismo , Bioensaio/métodos , Hedyotis/metabolismo , Ácido Aspártico Endopeptidases/antagonistas & inibidores , Calibragem , Cromatografia Líquida de Alta Pressão , Flavonóis/química , Produtos Finais de Glicação Avançada , Glicosídeos/química , Humanos , Concentração Inibidora 50 , Glicosídeos Iridoides , Análise dos Mínimos Quadrados , Modelos Lineares , Simulação de Acoplamento Molecular , Componentes Aéreos da Planta/metabolismo , Extratos Vegetais/química , Ligação Proteica , Quercetina/química , Solventes , Espectrometria de Massas por Ionização por Electrospray , EstereoisomerismoRESUMO
BACKGROUND: Entada phaseoloides (L.) Merr. is an important traditional medicinal plant. The stem of Entada phaseoloides is popularly used as traditional medicine because of its significance in dispelling wind and dampness and remarkable anti-inflammatory activities. Triterpenoid saponins are the major bioactive compounds of Entada phaseoloides. However, genomic or transcriptomic technologies have not been used to study the triterpenoid saponin biosynthetic pathway in this plant. RESULTS: We performed comparative transcriptome analysis of the root, stem, and leaf tissues of Entada phaseoloides with three independent biological replicates and obtained a total of 53.26 Gb clean data and 116,910 unigenes, with an average N50 length of 1218 bp. Putative functions could be annotated to 42,191 unigenes (36.1%) based on BLASTx searches against the Non-redundant, Uniprot, KEGG, Pfam, GO, KEGG and COG databases. Most of the unigenes related to triterpenoid saponin backbone biosynthesis were specifically upregulated in the stem. A total of 26 cytochrome P450 and 17 uridine diphosphate glycosyltransferase candidate genes related to triterpenoid saponin biosynthesis were identified. The differential expressions of selected genes were further verified by qPT-PCR. CONCLUSIONS: The dataset reported here will facilitate the research about the functional genomics of triterpenoid saponin biosynthesis and genetic engineering of Entada phaseoloides.