RESUMO
A new monoterpenoid, neoroseoside (1), along with two previously reported compounds, 2â³-O-α-l-rhamnosyl-6-C-fucosylluteolin (2) and farobin A (3) were isolated from the Zea mays. The structure of compound 1 was determined through the analysis spectroscopic data, including mass spectrometry (MS), infrared (IR) spectroscopy, and nuclear magnetic resonance (NMR) data. The absolute configurations of 1 were deduced from the comparing the values of optical rotations and from the interpretation of electronic circular dichroism (ECD) spectra. Compounds 2 and 3 displayed moderate antibacterial activity against Streptococcus mutans ATCC 25175 (inhibition rates 24 % and 28 %, respectively) and Streptococcus sobrinus ATCC 33478 (inhibition rate of 26 %), at a concentration of 100 µg/mL, whereas compound 1 did not have any significant antibacterial activities. The compounds 1-3 also showed anti-inflammatory activity on cytokine IL-6 and TNF-α.
Assuntos
Antibacterianos , Testes de Sensibilidade Microbiana , Monoterpenos , Zea mays , Zea mays/química , Antibacterianos/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Monoterpenos/farmacologia , Monoterpenos/química , Monoterpenos/isolamento & purificação , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Relação Estrutura-Atividade , Estrutura Molecular , Streptococcus mutans/efeitos dos fármacos , Interleucina-6/metabolismo , Interleucina-6/antagonistas & inibidores , Descoberta de Drogas , Fator de Necrose Tumoral alfa/antagonistas & inibidores , Fator de Necrose Tumoral alfa/metabolismo , Relação Dose-Resposta a Droga , Streptococcus/efeitos dos fármacosRESUMO
Four new compounds, racemic chalcone-monoterpene hybrids (1-3) and a chalcone (9), along with nine known compounds (4-8, 10-13), have been isolated from the buds of Cleistocalyx operculatus. The chemical structures of the isolated compounds were identified through NMR data analysis and confirmed by computational methods, including electronic circular dichroism (ECD) calculations, and further synthetic approaches. Compounds 1-5 were synthesized via a Diels-Alder reaction, a process informed by biomimetic condensation studies that combined chalcones and monoterpenes. These synthetic approaches also yielded various unnatural chalcone-monoterpene derivatives (14-23). The inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) of both naturally isolated and synthetically obtained compounds were evaluated. Compounds 4, 9, 13, and 16b exhibited potent PTP1B inhibitory activity, with IC50 values ranging from 0.9 ± 0.2 to 3.9 ± 0.7 µM. The enantiomers (+)-4 and (-)-16b showed enhanced activity compared to their respective enantiomers. Kinetic studies indicate that all active compounds inhibit PTP1B through mixed mechanisms, and molecular docking simulations agree with the experimental assays on PTP1B. Our results suggest that chalcone-meroterpene adducts from the buds of C. operculatus exhibit potential as antidiabetic agents, partly due to their PTP1B enzyme inhibition.
Assuntos
Monoterpenos , Proteína Tirosina Fosfatase não Receptora Tipo 1 , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Estrutura Molecular , Monoterpenos/farmacologia , Monoterpenos/química , Monoterpenos/isolamento & purificação , Chalconas/farmacologia , Chalconas/química , Chalconas/isolamento & purificação , Chalcona/farmacologia , Chalcona/química , Inibidores Enzimáticos/farmacologia , Inibidores Enzimáticos/química , Humanos , Syzygium/químicaRESUMO
Sheep haemonchosis is a disease that causes serious losses in livestock production, particularly with the increase of cases of anthelmintic resistance around the world. This justifies the urgent need of alternative solutions. The aim of this study was to determine the chemical profile, in vitro, and, in vivo, anthelmintic properties of Thymus capitatus essential oil. To evaluate the, in vitro, anthelmintic activity of the T. capitatus EO on Haemonchus contortus, two tests were used: egg hatch assay (EHA) and adult worm motility (AWM) assay. The nematicidal effect of this oil was evaluated, in vivo, in mice infected artificially with Heligmosomoides polygyrus using faecal egg count reduction (FECR) and total worm count reduction (TWCR). Chromatographic characterization of T.capitatus composition using gas chromatography coupled to mass spectrometry (GC-MS) demonstrated the presence of carvacrol (81.16%), as the major constituents. The IC50 values obtained was 1.9 mg/mL in the EHT. In the AWM assay; T. capitatus essential oil achieved 70.8% inhibition at 1 mg/mL after 8 h incubation. The in vivo, evaluation on H. polygyrus revealed a significant nematicidal effect 7 days post-treatment by inducing 49.5% FECR and 64.5% TWCR, using the highest dose (1600 mg/kg). The results of present study, demonstrate that T.capitatus EO possess a significant anthelmintic properties. Furthermore, it could be an alternative source of anthelmintic agents against gastrointestinal infections caused by H. contortus.
Assuntos
Anti-Helmínticos , Fezes , Flores , Cromatografia Gasosa-Espectrometria de Massas , Hemoncose , Haemonchus , Nematospiroides dubius , Óleos Voláteis , Contagem de Ovos de Parasitas , Infecções por Strongylida , Thymus (Planta) , Animais , Haemonchus/efeitos dos fármacos , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Camundongos , Nematospiroides dubius/efeitos dos fármacos , Thymus (Planta)/química , Hemoncose/veterinária , Hemoncose/tratamento farmacológico , Hemoncose/parasitologia , Infecções por Strongylida/tratamento farmacológico , Infecções por Strongylida/veterinária , Infecções por Strongylida/parasitologia , Anti-Helmínticos/farmacologia , Anti-Helmínticos/isolamento & purificação , Anti-Helmínticos/uso terapêutico , Anti-Helmínticos/química , Fezes/parasitologia , Contagem de Ovos de Parasitas/veterinária , Flores/química , Feminino , Ovinos , Concentração Inibidora 50 , Monoterpenos/farmacologia , Monoterpenos/isolamento & purificação , Monoterpenos/química , Masculino , Doenças dos Ovinos/parasitologia , Doenças dos Ovinos/tratamento farmacológico , CimenosRESUMO
Propolis is a natural resinous product produced by Apis mellifera bees from the exudates of various plants. The color of propolis (green) is a consequence of its botanical origin, as bees collect young tissues and leaves of Baccaris dracunculifolia. This study evaluated the chemical composition and extraction kinetics of essential oils obtained from Brazilian green propolis by hydrodistillation. Hydrodistillation was performed for 360â min and analyzed at different times (30, 60, 120, 240, and 360â min), allowing the calculation of the accumulated content (% w/w) and the identification of the essential oil chemical profile. The GC/FID and GC/MS analysis led to the annotation of 60 compounds with estragole (13.30 %), benzyl propanoate (14.59 %), and (E)-nerolidol (13.57 %) as the main compounds. The optimum conditions for extraction of phenylpropanoids (PP), hydrocarbons (HD), monoterpenes (MT), and oxygenated monoterpenes (OMT) are between 30 and 120â min. In comparison, sesquiterpenes (ST) and oxygenated sesquiterpenes (OST) are extracted more efficiently between 240 and 360â min. The optimal extraction speed determination is essential for industrial-scale processing to obtain components such as sesquiterpenes, which have a high economic value in the cosmetic/perfumery and pharmaceutical industries.
Assuntos
Cromatografia Gasosa-Espectrometria de Massas , Óleos Voláteis , Própole , Animais , Abelhas/química , Brasil , Cinética , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Própole/química , Monoterpenos/química , Monoterpenos/isolamento & purificaçãoRESUMO
The red algal genus Portieria is a prolific producer of halogenated monoterpenoids. In this study, we isolated and characterised monoterpenoids from the Okinawan red algae Portieria hornemannii. A new polyhalogenated cyclic monoterpenoid, 2(R)-chloro-1,6(S)-dibromo-3(8)(Z)-ochtoden-4(R)-ol (1), along with three known monoterpenoids, (2R,3(8)E,4S,6R)-6-bromo-2-chloro-1,4-oxido-3(8)-ochtodene (2), 1-bromo-2-chloroochtoda-3(8),5-dien-4-one (3), and 2-chloro-1-hydroxyochtoda-3(8),5-dien-4-one (4) were isolated from the methanol extract of three populations of P. hornemannii. These compounds were characterised using a combination of spectroscopic methods and chemical synthesis, and the absolute stereochemistry of compounds 1 and 2 was determined. In addition, all isolated compounds were screened for their anti-biofouling activity against the mussel Mytilus galloprovincialis, and 1 exhibited strong activity. Therefore, halogenated monoterpenoids have the potential to be used as natural anti-biofouling drugs.
Assuntos
Incrustação Biológica , Monoterpenos , Rodófitas , Animais , Incrustação Biológica/prevenção & controle , Halogenação , Estrutura Molecular , Monoterpenos/isolamento & purificação , Monoterpenos/química , Monoterpenos/farmacologia , Rodófitas/química , Guanetidina/química , Guanetidina/isolamento & purificação , Guanetidina/farmacologiaRESUMO
There is a burgeoning focus on utilizing the antifungal and antioxidant properties of essential oils derived from various plants as a modern and natural approach to combat the growth of fungi that contaminate food. In this study, we used essential oils extracted from Thymus daenensis Celak. subsp. daenensis to address three mycotoxin-producing species of Aspergillus, specifically A. flavus, A. parasiticus, and A. niger, all of which are recognized contaminants of food and agricultural products. Concurrently, the antioxidant properties of the essential oils were evaluated, revealing their noteworthy role in the antifungal activity. Essential oils were derived from T. daenensis subsp. daenensis was observed to have a significant inhibitory effect on all three species of Aspergillus, as evidenced by the minimum inhibitory concentration (MIC) ranging from 575 to 707â ppm and the half-maximal inhibitory concentration (IC50) ranging from 237 to 280â ppm. These results confirm the strong antifungal activity of the essential oils. Furthermore, the essential oil exhibited free radical scavenging activity, resulting in an EC50 value of 37.1â µg/ml. In summary, T. daenensis subsp. daenensis essential oil demonstrated a competitive advantage over other similar plants and synthetic antibiotics. This indicates the promising potential of this essential oil as a natural antifungal agent to control Aspergillus growth and mycotoxin contamination. It offers an alternative or complementary approach to conventional antifungal agents and could be a valuable addition to the arsenal of natural remedies to address fungal contamination in food and agricultural products.
Assuntos
Antifúngicos , Aspergillus , Sequestradores de Radicais Livres , Testes de Sensibilidade Microbiana , Óleos Voláteis , Timol , Thymus (Planta) , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Aspergillus/efeitos dos fármacos , Aspergillus/química , Thymus (Planta)/química , Antifúngicos/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Sequestradores de Radicais Livres/farmacologia , Sequestradores de Radicais Livres/química , Timol/farmacologia , Timol/química , Monoterpenos/farmacologia , Monoterpenos/química , Monoterpenos/isolamento & purificaçãoRESUMO
Four new monoterpene rhamnosides, graphiumisides A-D (1-4), along with four known steroid compounds (5-8) were isolated from the fermentation extract of animal-derived endophytic fungus, Graphium sp. GD-11. The chemical structures of all compounds were elucidated using 1D and 2D NMR, HRESIMS spectroscopic analyses, and other spectroscopic methods. Compounds 1-4 exhibit a distinctive structure connected by one p-menthane type monoterpene and one L-rhamnose. This is the first report of monoterpene glycosides from Graphium sp. All compounds (1-8) were tested for cytotoxic activities against four cancer cell lines (HepG2, SMMC7721, SW480, and A549), and only compound 1 showed weak anti-tumor activity against SMMC7721 cells.
Assuntos
Antineoplásicos , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos , Monoterpenos , Glicosídeos/química , Glicosídeos/farmacologia , Glicosídeos/isolamento & purificação , Humanos , Monoterpenos/química , Monoterpenos/farmacologia , Monoterpenos/isolamento & purificação , Linhagem Celular Tumoral , Animais , Antineoplásicos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Estrutura Molecular , Conformação Molecular , Relação Estrutura-AtividadeRESUMO
Three undescribed sesquiterpenes (1-3), two enantiomeric pairs of monoterpenes (4a/4b-5a/5b), one alkyne (6), two known alkynes (7-8) and eight known coumarins (9-16) were isolated from the aerial parts extracts of Artemisia scoparia. The structures of these compounds were fully elucidated by their 1D and 2D NMR, HRESIMS spectral data analyses, and comparison with literature. The absolute configurations of compounds were determined by single-crystal X-ray crystallography (1), a comparison of experimental and calculated electronic circular dichroism (ECD) data (2-6). 15 showed moderate inhibitory activity with the NO release in LPS-induced RAW264.7 cells. 9-16 showed varying degrees of promoting melanogenesis and tyrosinase activity in B16 cells.
Assuntos
Artemisia , Óxido Nítrico , Artemisia/química , Camundongos , Animais , Células RAW 264.7 , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Óxido Nítrico/metabolismo , Monofenol Mono-Oxigenase/antagonistas & inibidores , Monofenol Mono-Oxigenase/metabolismo , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Cristalografia por Raios X , Componentes Aéreos da Planta/química , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Sesquiterpenos/isolamento & purificação , Estrutura Molecular , Monoterpenos/química , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Cumarínicos/química , Cumarínicos/farmacologia , Cumarínicos/isolamento & purificação , Conformação Molecular , Melaninas/antagonistas & inibidores , Melaninas/metabolismo , Modelos Moleculares , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Extratos Vegetais/isolamento & purificaçãoRESUMO
This work used headspace solid-phase microextraction with gas chromatography-mass spectrometry (HS-SPME-GC-MS) to analyze the volatile components of hydrosols of Citrus × aurantium 'Daidai' and Citrus × aurantium L. dried buds (CAVAs and CADBs) by immersion and ultrasound-microwave synergistic-assisted steam distillation. The results show that a total of 106 volatiles were detected in hydrosols, mainly alcohols, alkenes, and esters, and the high content components of hydrosols were linalool, α-terpineol, and trans-geraniol. In terms of variety, the total and unique components of CAVA hydrosols were much higher than those of CADB hydrosols; the relative contents of 13 components of CAVA hydrosols were greater than those of CADB hydrosols, with geranyl acetate up to 15-fold; all hydrosols had a citrus, floral, and woody aroma. From the pretreatment, more volatile components were retained in the immersion; the relative contents of linalool and α-terpineol were increased by the ultrasound-microwave procedure; and the ultrasound-microwave procedure was favorable for the stimulation of the aroma of CAVA hydrosols, but it diminished the aroma of the CADB hydrosols. This study provides theoretical support for in-depth exploration based on the medicine food homology properties of CAVA and for improving the utilization rate of waste resources.
Assuntos
Monoterpenos Acíclicos , Citrus , Monoterpenos Cicloexânicos , Cromatografia Gasosa-Espectrometria de Massas , Microextração em Fase Sólida , Compostos Orgânicos Voláteis , Cromatografia Gasosa-Espectrometria de Massas/métodos , Citrus/química , Microextração em Fase Sólida/métodos , Compostos Orgânicos Voláteis/análise , Compostos Orgânicos Voláteis/química , Compostos Orgânicos Voláteis/isolamento & purificação , Monoterpenos Acíclicos/análise , Monoterpenos Cicloexânicos/análise , Terpenos/análise , Terpenos/química , Monoterpenos/análise , Monoterpenos/isolamento & purificação , Odorantes/análise , Destilação/métodos , AcetatosRESUMO
The whole Hypericum patulum Thunb. plant is utilized in traditional medicine for its properties of clearing heat, detoxifying, soothing meridians, relaxing the liver, and stopping bleeding. In folk medicine, it is frequently used to treat hepatitis, colds, tonsillitis, and bruises. Phytochemical investigation of a 30% ethanol extract of the fresh ripe fruits of H. patulum has resulted in the isolation of two new pinane-type monoterpenoid glycosides 1-2, named patulumside E-F, and three new chain-shaped monoterpenoid glycosides 3-5, named patulumside G-H, J. Their structures were determined using extensive spectroscopic techniques, such as HR-ESI-MS, 1D and 2D NMR spectroscopy, and electronic circular dichroism (ECD) calculation. The anti-inflammatory activities of these compounds were evaluated in the LPS-induced RAW264.7 cells. This research represents the inaugural comprehensive phytochemical study of H. patulum, paving the way for further exploration of monoterpenoid glycosides.
Assuntos
Frutas , Glicosídeos , Hypericum , Monoterpenos , Extratos Vegetais , Hypericum/química , Glicosídeos/química , Glicosídeos/farmacologia , Glicosídeos/isolamento & purificação , Camundongos , Animais , Células RAW 264.7 , Frutas/química , Monoterpenos/química , Monoterpenos/farmacologia , Monoterpenos/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Estrutura Molecular , Lipopolissacarídeos/farmacologia , Espectroscopia de Ressonância Magnética , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/isolamento & purificaçãoRESUMO
Continued interest in the bioactive alkaloids led to the isolation of five undescribed alkaloids (1-5), ophiorglucidines A-E, and seven known analogues (6-12) from the water-soluble fraction of Ophiorrhiza japonica. The structures were elucidated based on spectroscopic data and quantum calculations as well as X-ray crystallographic analysis. The structure of 1 was characterized as a hexacyclic skeleton including a double bridge linking the indole and the monoterpene moieties, which is the first report of a single crystal with this type of structure. Moreover, the inhibitory effect of zwitterionic indole alkaloid glycosides on xanthine oxidase was found for the first time. The alkaloids 2 and 3, both of which have a pentacyclic zwitterionic system, were more active than the reference inhibitor, allopurinol (IC50 = 11.1 µM) with IC50 values of 1.0 µM, and 2.5 µM, respectively. Structure-activity relationships analyses confirmed that the carbonyl group at C-14 was a key functional group responsible for the inhibitory effects of these alkaloids.
Assuntos
Inibidores Enzimáticos , Alcaloides Indólicos , Monoterpenos , Rubiaceae , Xantina Oxidase , Xantina Oxidase/antagonistas & inibidores , Xantina Oxidase/metabolismo , Rubiaceae/química , Relação Estrutura-Atividade , Alcaloides Indólicos/química , Alcaloides Indólicos/farmacologia , Alcaloides Indólicos/isolamento & purificação , Inibidores Enzimáticos/farmacologia , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Monoterpenos/química , Monoterpenos/farmacologia , Monoterpenos/isolamento & purificação , Estrutura Molecular , Relação Dose-Resposta a Droga , Modelos Moleculares , Cristalografia por Raios XRESUMO
Ten new cyclopentanoid monoterpenes (1-10) were isolated from the whole plant of Rehmannia piasezkii. The structures of these compounds were elucidated based on spectroscopic data analysis. In in-vitro assays, compounds 3, 7, and 9 exhibited weak hepatoprotective activities against APAP-induced HepG2 cell damage. Compound 9 exhibited protective effect on hapassocin carbon tetrachloride model.
Assuntos
Monoterpenos , Compostos Fitoquímicos , Rehmannia , Rehmannia/química , Humanos , Estrutura Molecular , Células Hep G2 , Monoterpenos/farmacologia , Monoterpenos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Ciclopentanos/farmacologia , Ciclopentanos/isolamento & purificação , ChinaRESUMO
In this study, a novel magnetic bead-based ligand fishing method was developed for rapid discovery of monoterpene indoles as monoamine oxidase A inhibitors from natural products. In order to improve the screening efficiency, two different magnetic beads, i.e. amine and carboxyl terminated magnetic beads, were comprehensively compared in terms of their ability to immobilize monoamine oxidase A (MAOA), biocatalytic activity and specific adsorption rates for affinity ligands. Carboxyl terminated magnetic beads performed better for MAOA immobilization and demonstrated superior performance in ligand fishing. The MAOA immobilized magnetic beads were applied to screen novel monoamine oxidase inhibitors in an alkaloid-rich plant, Hunteria zeylanica. Twelve MAOA affinity ligands were screened out, and ten of them were identified as monoterpene indole alkaloids by HPLC-Obitrap-MS/MS. Among them, six ligands, namely geissoschizol, vobasinol, yohimbol, dihydrocorynanthenol, eburnamine and (+)-isoeburnamine which exhibited inhibitory activity against MAOA with low IC50 values. To further explore their inhibitory mechanism, enzyme kinetic analysis and molecular docking studies were conducted.
Assuntos
Simulação de Acoplamento Molecular , Inibidores da Monoaminoxidase , Monoaminoxidase , Inibidores da Monoaminoxidase/química , Inibidores da Monoaminoxidase/farmacologia , Inibidores da Monoaminoxidase/isolamento & purificação , Monoaminoxidase/metabolismo , Monoaminoxidase/química , Ligantes , Indóis/química , Monoterpenos/química , Monoterpenos/isolamento & purificação , Cinética , Espectrometria de Massas em Tandem/métodos , Cromatografia Líquida de Alta Pressão/métodos , Enzimas Imobilizadas/química , Enzimas Imobilizadas/metabolismo , Enzimas Imobilizadas/antagonistas & inibidores , Humanos , Extratos Vegetais/químicaRESUMO
A phytochemical study of the ethanol extract from Ailanthus altissima (Mill.) Swingle leaves resulted in the isolation of four new monoterpenoids (1-3, 5). The structures were elucidated using HRESIMS data, NMR spectroscopic data, quantum chemical calculations for NMR and ECD, and custom DP4+ probability analysis. Additionally, the absolute configuration of sugar was determined by acid hydrolysis. Compounds 1-4 are cyclogeraniane monocyclic monoterpenes, while compound 5 contains an acyclic mycrane monoterpenes skeleton. Anti-tyrosinase, anti-acetylcholinesterase, and anti-butyrylcholinesterase activities were tested. Compound 1 showed notable anti-acetylcholinesterase activity, and compound 3 exhibited significant inhibitory effects on anti-tyrosinase activity. Furthermore, the potential binding sites of compounds 1 and 3 were predicted by molecular docking.
Assuntos
Ailanthus , Simulação de Acoplamento Molecular , Monoterpenos , Compostos Fitoquímicos , Folhas de Planta , Ailanthus/química , Estrutura Molecular , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Inibidores da Colinesterase/isolamento & purificação , Inibidores da Colinesterase/farmacologia , Inibidores da Colinesterase/química , Monofenol Mono-Oxigenase/antagonistas & inibidores , Acetilcolinesterase/metabolismo , Butirilcolinesterase/metabolismoRESUMO
Seven pairs of undescribed monoterpenoid polyprenylated acylphloroglucinol enantiomers [(±)-hypermonanones A-G (1-7)], together with three known analogues, were identified from the whole plant of Hypericum monanthemum Hook. The structures of these compounds were determined by analyses of their UV, HRESIMS, 1D/2D NMR spectroscopic data, and NMR calculations. The absolute configurations of these compounds were assigned by ECD calculations after chiral HPLC separation. Diverse monoterpene moieties were fused at C-3/C-4 of the dearomatized acylphloroglucinol core, which led to 3,4-dihydro-2H-pyran-integrated angular or linear type 6/6/6 tricyclic skeletons in 1-7. Compounds (-)-2 and (+)-2 exhibited significant NO inhibitory activity against LPS induced RAW264.7 cells with the IC50 values of 7.07 ± 1.02 µM and 11.39 ± 0.24 µM, respectively.
Assuntos
Hypericum , Monoterpenos , Floroglucinol , Compostos Fitoquímicos , Hypericum/química , Camundongos , Estrutura Molecular , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Floroglucinol/isolamento & purificação , Floroglucinol/farmacologia , Floroglucinol/química , Células RAW 264.7 , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Animais , Óxido Nítrico/metabolismo , Estereoisomerismo , ChinaRESUMO
In this study, high-performance liquid chromatography was used to determine four components of Shaoyao Gancao Decoction (SGD), and the effect of purification was evaluated using fingerprints, similarity analysis and cell experiments. An effective method for isolation and purification of SGD was established. The adsorption/desorption properties of SGD were evaluated using resin screening, isothermal analysis, adsorption kinetics, and dynamic adsorption-desorption experiments. It was shown that the Langmuir equation fitted the isotherm data well and that a pseudo-second-order model accurately described kinetic adsorption on AB-8 resin. Analysis of thermodynamic parameters showed that the adsorption process was exothermic. Under the optimal process conditions, the concentrations of albiflorin, paeoniflorin, liquiritin and ammonium glycyrrhizinate in the product were 73.05, 134.04, 45.04 and 75.00 mg/g, respectively. The yields of the four components were 71.89 %-86.19 %. Cell experiments showed that the purified SGD retained anti-inflammatory activity. This research lays the foundation for the separation and purification of SGD and subsequent preparation research.
Assuntos
Medicamentos de Ervas Chinesas , Glucosídeos , Monoterpenos , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Cromatografia Líquida de Alta Pressão/métodos , Glucosídeos/isolamento & purificação , Glucosídeos/química , Monoterpenos/isolamento & purificação , Monoterpenos/química , Adsorção , Flavanonas/isolamento & purificação , Flavanonas/química , Flavanonas/análise , Animais , Ácido Glicirrízico/isolamento & purificação , Ácido Glicirrízico/química , Ácido Glicirrízico/análise , Hidrocarbonetos Aromáticos com Pontes/química , Hidrocarbonetos Aromáticos com Pontes/isolamento & purificação , Camundongos , Resinas Sintéticas/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/química , Humanos , Células RAW 264.7RESUMO
Five undescribed monoterpene-chalcone conjugates (1-5), one undescribed hypothetical precursor of diarylheptanoid (6), two undescribed diarylheptanoids (7-8), and fourteen known compounds (9-22) were isolated from the seeds of Alpinia katsumadai. Their structures were elucidated through the interpretation of HRESIMS, NMR, ECD, and X-ray diffraction data. MTT assays on human cancer cell lines (HepG2, A549, SGC7901, and SW480) revealed that compounds 3-8, 11, and 13 exhibited broad-spectrum antiproliferative activities with IC50 values ranging from 3.59 to 21.78 µM. B cell lymphoma 2 was predicted as the target of sumadain C (11) by network pharmacology and verified by homogeneous time-resolved fluorescence assay and molecular docking.
Assuntos
Alpinia , Antineoplásicos Fitogênicos , Proliferação de Células , Diarileptanoides , Ensaios de Seleção de Medicamentos Antitumorais , Monoterpenos , Sementes , Alpinia/química , Humanos , Diarileptanoides/química , Diarileptanoides/farmacologia , Diarileptanoides/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Sementes/química , Estrutura Molecular , Proliferação de Células/efeitos dos fármacos , Monoterpenos/química , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Relação Estrutura-Atividade , Chalconas/química , Chalconas/farmacologia , Chalconas/isolamento & purificação , Chalcona/química , Chalcona/farmacologia , Chalcona/isolamento & purificação , Linhagem Celular Tumoral , Relação Dose-Resposta a Droga , Simulação de Acoplamento MolecularRESUMO
Five new compounds, including two sesquiterpenoid glycosides (1 and 2), two monoterpenoid glycosides (3 and 4), and a quinovose ester (5), together with four known compounds (6-9) were isolated from branches and leaves of Pittosporum pulchrum Gagnep. Their structures were established by 1D and 2D NMR, HR-ESI-MS, IR and UV spectral analyses. This is the first time to investigate the chemical constituents of P. pulchrum. Subsequently, the anti-inflammatory and antioxidant activities of different solvent fractions of ethanol extract and isolated compounds were evaluated. Dichloromethane and ethyl acetate fractions dramatically inhibited the production of NO in a concentration-dependent manner in LPS-induced RAW264.7 cells. Ethyl acetate and n-butanol fractions showed excellent DPPH radical scavenging activities with IC50 values of 24.31 µg/mL and 27.81 µg/mL, respectively. Compounds 7 and 8 might be potential natural antioxidants with IC50 values of 16.13 µM and 24.81 µM, respectively.
Assuntos
Anti-Inflamatórios , Antioxidantes , Compostos Fitoquímicos , Folhas de Planta , Folhas de Planta/química , Camundongos , Células RAW 264.7 , Animais , Estrutura Molecular , Antioxidantes/farmacologia , Antioxidantes/isolamento & purificação , Antioxidantes/química , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/química , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Glicosídeos/química , Óxido Nítrico/metabolismo , Caules de Planta/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Sesquiterpenos/química , China , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologiaRESUMO
ABSTRACT INTRODUCTION: Schistosomiasis, a parasitic disease caused by trematode flatworms of the genus Schistosoma, affects more than 200 million people worldwide, and its control is dependent on a single drug, praziquantel. Here, we report the in vitro effect of rotundifolone, a monoterpene isolated from Mentha x villosa (Lamiaceae), on Schistosoma mansoni adult worms. METHODS: The in vitro effect of rotundifolone on adult Schistosoma mansoni was evaluated by analysis of behavior and mortality and through a scanning electron microscopic analysis of ultrastructural changes in the tegument of the worms. RESULTS: At concentrations of 3.54 and 7.09μg/mL-1 rotundifolone, no worm mortality was observed at any of the sampling intervals. A minor reduction in movement of the tail, suckers, and gynecophoral canal membrane was observed after 96 h of exposure to 7.09μg/mL-1 rotundifolone. At 70.96μg/mL-1, a lack of movement was observed from 72h onwards and all worms were deemed dead; similar effects were observed at 48h with 177.4μg/mL-1, and at 24h with 354.8μg/mL-1 and 700.96μg/mL-1. Rotundifolone also caused death of all parasites and separation of coupled pairs into individual males and females after 24h at 354.8μg/mL-1. CONCLUSIONS: The main changes in the tegument induced by the different ROT treatments were: after 24h incubation, bubble lesions spread over the entire body and loss of tubercles occurred in some regions of the ventral region.
Assuntos
Animais , Masculino , Feminino , Schistosoma mansoni/efeitos dos fármacos , Mentha/química , Monoterpenos/farmacologia , Schistosoma mansoni/ultraestrutura , Microscopia Eletrônica de Varredura , Testes de Sensibilidade Parasitária , Monoterpenos/isolamento & purificaçãoRESUMO
ABSTRACT Linalool is the main compound of many essential oils and occurs in two isomeric forms: S-(+)- and R-(-)-linalool. This study aimed to determine if linalool isomers have different antimicrobial and anesthetic properties in fish. For this purpose, these compounds were previously isolated from Lippia alba (Mill.)N. E. Brown and Ocimum americanum L. essential oils. Antimicrobial effects were evaluated through the microdilution test against Aeromonas hydrophila, an important fish disease etiologic agent. Induction time until sedation, anesthesia and recovery time were determined in silver catfish (Rhamdia quelen) through bath exposure (60, 180, 300 or 500 μL L-1). The results showed different biological properties for the isomers being S-(+)-linalool the only active against A. hydrophila at 3.2 mg mL-1. The sedation was induced without differences between the compounds, however R-(-)-linalool promoted faster anesthesia. There were no differences regarding the recovery time of the animals exposed to the linalool isomers. Although both S-(+)- and R-(-)-linalool can be used for sedative purposes, their use in A. hydrophila infection is inadvisable due to the high effective concentration. Considering anesthesia as the main objective, the R-(-)-linalool demonstrated clear advantages at lower concentration.