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1.
Molecules ; 29(15)2024 Jul 28.
Artículo en Inglés | MEDLINE | ID: mdl-39124956

RESUMEN

Eupatorium lindleyanum DC. (EL) is a traditional Chinese herb known for its phlegm-reducing, cough-relieving and asthma-calming properties. It is widely used for treating cough and bronchitis. However, preliminary experiments have revealed wide variations in the composition of its different medicinal parts (flowers, leaves and stems), and the composition and efficacy of its different medicinal parts remain largely underexplored at present. In this study, non-targeted rapid resolution liquid chromatography coupled with a quadruple time-of-flight mass spectrometry (RRLC-Q-TOF-MS)-based metabolomics approach was developed to investigate the differences in the chemical composition of different medicinal parts of EL. We identified or tentatively identified 9 alkaloids, 11 flavonoids, 14 sesquiterpene lactones, 3 diterpenoids and 24 phenolic acids. In addition, heatmap visualization, quantitative analysis by high-performance liquid chromatography (HPLC-PDA) and ultra-high-performance liquid chromatography-triple quadrupole tandem mass spectrometry (UPLC-MS/MS) showed particularly high levels of sesquiterpene lactones, flavonoids and phenolic acids in the flowers, such as eupalinolide A and B and chlorogenic acid, among others. The leaves also contained some flavonoid sesquiterpene lactones and phenolic acids, while the stems were almost absent. The findings of in vitro activity studies indicated that the flowers exhibited a notable inhibitory effect on the release of the inflammatory factors TNF-α and IL-6, surpassing the anti-inflammatory efficacy observed in the leaves. Conversely, the stems demonstrated negligible anti-inflammatory activity. The variations in anti-inflammatory activity among the flowers, leaves and stems of EL can primarily be attributed to the presence of flavonoids, phenolic acids and sesquiterpene lactones in both the flowers and leaves. Additionally, the flowers contain a higher concentration of these active components compared to the leaves. These compounds mediate their anti-inflammatory effects through distinct biochemical pathways. The results of this study are anticipated to provide a scientific basis for the rational and effective utilization of EL resources.


Asunto(s)
Antiinflamatorios , Eupatorium , Espectrometría de Masas en Tándem , Eupatorium/química , Antiinflamatorios/farmacología , Antiinflamatorios/química , Cromatografía Líquida de Alta Presión/métodos , Espectrometría de Masas en Tándem/métodos , Hojas de la Planta/química , Animales , Flavonoides/química , Flavonoides/farmacología , Flavonoides/análisis , Metaboloma , Metabolómica/métodos , Ratones , Extractos Vegetales/química , Extractos Vegetales/farmacología , Células RAW 264.7 , Flores/química , Tallos de la Planta/química , Plantas Medicinales/química
2.
Sci Rep ; 14(1): 10509, 2024 05 07.
Artículo en Inglés | MEDLINE | ID: mdl-38714697

RESUMEN

Chronic non-communicable diseases (CNCDs) pose a significant public health challenge. Addressing this issue, there has been a notable breakthrough in the prevention and mitigation of NCDs through the use of antioxidants and anti-inflammatory agents. In this study, we aim to explore the effectiveness of Eupatorium adenophora Spreng leaves (EASL) as an antioxidant and anti-inflammatory agent, and its potential applications. To construct a cellular model of oxidative damage and inflammation, Caco-2 cells were treated with tert-butyl hydroperoxide (t-BHP). The biocompatibility of EASL-AE with Caco-2 cells was assessed using the MTT assay, while compatibility was further verified by measuring LDH release and the protective effect against oxidative damage was also assessed using the MTT assay. Additionally, we measured intracellular oxidative stress indicators such as ROS and 8-OHdG, as well as inflammatory pathway signalling protein NFκB and inflammatory factors TNF-α and IL-1ß using ELISA, to evaluate the antioxidant and anti-inflammatory capacity of EASL-AE. The scavenging capacity of EASL-AE against free radicals was determined through the DPPH Assay and ABTS Assay. Furthermore, we measured the total phenolic, total flavonoid, and total polysaccharide contents using common chemical methods. The chemical composition of EASL-AE was analyzed using the LC-MS/MS technique. Our findings demonstrate that EASL-AE is biocompatible with Caco-2 cells and non-toxic at experimental levels. Moreover, EASL-AE exhibits a significant protective effect on Caco-2 cells subjected to oxidative damage. The antioxidant effect of EASL-AE involves the scavenging of intracellular ROS, while its anti-inflammatory effect is achieved by down-regulation of the NFκB pathway. Which in turn reduces the release of inflammatory factors TNF-α and IL-1ß. Through LC-MS/MS analysis, we identified 222 compounds in EASL-AE, among which gentianic acid, procaine and L-tyrosine were the compounds with high antioxidant capacity and may be the effective constituent for EASL-AE with antioxidant activity. These results suggest that EASL-AE is a natural and high-quality antioxidant and anti-inflammatory biomaterial that warrants further investigation. It holds great potential for applications in healthcare and other related fields.


Asunto(s)
Antiinflamatorios , Antioxidantes , Estrés Oxidativo , Extractos Vegetales , Hojas de la Planta , terc-Butilhidroperóxido , Humanos , Células CACO-2 , terc-Butilhidroperóxido/farmacología , Hojas de la Planta/química , Antioxidantes/farmacología , Antiinflamatorios/farmacología , Antiinflamatorios/química , Extractos Vegetales/farmacología , Extractos Vegetales/química , Estrés Oxidativo/efectos de los fármacos , Eupatorium/química , Especies Reactivas de Oxígeno/metabolismo , FN-kappa B/metabolismo
3.
Phytochemistry ; 219: 113984, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38266953

RESUMEN

Thirty-nine thymol and acetophenone derivatives, including eight pairs of enantiomers, were isolated from the aerial parts of Eupatorium fortunei. Their structures were assigned by detailed analyses of spectroscopic data and NMR calculations based on density functional theory, with 18 ones (1a/1b-14) being previously undescribed compounds. While the absolute configurations of 1a/1b, 2a/2b, 4, 6a/6b, 7, 11a/11b and 15a/15b-18a/18b were established by calculations of electronic circular dichroism data, that of 14 was determined by modified Mosher's method. Compounds 1a/1b and 2a/2b represent a previously unreported type of monoterpenoid dimers via an amide linkage, and compound 3 is a monoterpene-phenylpropanoid hybrid connected through an ester bond. Among the known molecules, the formerly mis-assigned structures of 15a/15b and 22 were revised, and pure natural enantiomers of 16a/16b-18a/18b were reported for the first time. Selective compounds showed antiradical and NO production inhibitory activities in the preliminary biological screening. Compound 31 was further demonstrated to alleviate oxidative stress by activating Nrf2 signaling pathway.


Asunto(s)
Eupatorium , Eupatorium/química , Monoterpenos/farmacología , Monoterpenos/análisis , Estructura Molecular , Componentes Aéreos de las Plantas/química , Acetofenonas/análisis
4.
Fitoterapia ; 171: 105700, 2023 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-37832878

RESUMEN

The well-known aromatic and medicinal plant Eupatorium fortunei Turcz. is widely cultivated in China, and previous studies on its bioactive constituents mainly focus on the essential oil ingredients especially thymol derivatives. However, reports on other type of constituents and the potential application are lacking. In the present project, an intensive chemical fractionation on the aerial part extract of E. fortunei led to the isolation and identification of a series of fatty acid derivatives (lipids, 1a/1b-19) including seven pairs of previously undescribed enantiomers (1a/1b-7a/7b), as well as a lignan (brachangobinan A (BBA), 20) and two monoterpenes (8S/8R-9-hydroxythymol, 21a/21b). A preliminary biological evaluation of these compounds in a NO production inhibitory assay model demonstrated compound BBA as the most active one. Network pharmacology analysis was used to predict and explore the possible anti-inflammatory targets and mechanism of BBA, which revealed some potential inflammation-related proteins and signaling pathways. Further experimental investigations validated that the anti-inflammatory effect of BBA could be achieved by suppressing pro-inflammatory factors and blocking the activation of NF-κB signaling pathway. Taken together, our work shows that E. fortunei can serve as a potential resource of lipids and anti-inflammatory agents.


Asunto(s)
Eupatorium , Plantas Medicinales , Eupatorium/química , Estructura Molecular , Plantas Medicinales/química , Antiinflamatorios/farmacología , Lípidos
5.
Molecules ; 28(13)2023 Jun 29.
Artículo en Inglés | MEDLINE | ID: mdl-37446767

RESUMEN

Eight samples of Eupatorium heterophyllum leaves were collected at different locations in Yunnan and Sichuan provinces in China, and their chemical constituents were investigated. Thirteen previously undescribed sesquiterpene lactones-seven germacranolides, three eudesmanolides, two guaianolides, and a 2-norelemanolide-were isolated, and their structures were elucidated based on extensive spectroscopic analyses. The major constituents in the six samples from northwestern Yunnan and Sichuan are hiyodorilactones A and B, whereas that in the two samples from the region near Kunming, Yunnan is eupatoriopicrin. These results and previously reported results suggest the presence of locality-dependent intra-specific diversity in the chemical constituents of E. heterophyllum leaves.


Asunto(s)
Asteraceae , Eupatorium , Sesquiterpenos , Eupatorium/química , China , Hojas de la Planta/química , Fitoquímicos/análisis , Sesquiterpenos/química , Lactonas/química , Asteraceae/química , Estructura Molecular
6.
Molecules ; 27(24)2022 Dec 13.
Artículo en Inglés | MEDLINE | ID: mdl-36557988

RESUMEN

The chemical constituents of two root samples of Eupatorium heterophyllum DC. collected in Yunnan Province, China, were investigated. Five new oligomeric benzofurans (1-5), nine new benzofuran/dihydrobenzofuran derivatives, and a new thymol analog were isolated, and their structures were determined using extensive spectroscopic techniques, such as 1D and 2D NMR spectroscopy and DFT calculations of the CD spectra. Most of the new compounds, including oligomeric benzofurans (1-5), were obtained from only one of the root samples. Furthermore, this is the first example that produces oligomeric benzofurans in this plant. These results imply that diversification of secondary metabolites in E. heterophyllum is ongoing. Plausible biosynthetic pathways for 1-5 are also proposed.


Asunto(s)
Benzofuranos , Eupatorium , Eupatorium/química , China , Benzofuranos/química , Espectroscopía de Resonancia Magnética , Raíces de Plantas/química , Estructura Molecular
7.
Toxins (Basel) ; 14(11)2022 11 05.
Artículo en Inglés | MEDLINE | ID: mdl-36356015

RESUMEN

The traditional Chinese herbal medicine Eupatorium fortunei Turcz. (E. fortunei) has been widely adopted to treat nausea, diabetes, siriasis, and poor appetite. However, E. fortunei contains multiple pyrrolizidine alkaloids (PAs). This study aimed to investigate the hepatotoxicity of total alkaloids in E. fortunei (EFTAs) and identify the toxic mechanisms of EFTAs on hepatocytes. Liquid chromatography with a tandem mass spectrometry assay with reference standards indicated that EFTAs mainly consisted of eight PAs whose content accounted for 92.38% of EFTAs. EFTAs markedly decreased mouse body and liver weights and increased the contents of AST and ALT. The histopathological assays demonstrated that, after exposition to EFTAs, the structures of hepatocytes were damaged and the fibrosis and apoptosis in hepatocytes were accelerated. Moreover, EFTAs increased the serum level of inflammatory cytokines and aggravated circulating oxidative stress. A combination of hepatic proteomics and metabolomics was used to investigate the toxic mechanisms of EFTAs. The study revealed that EFTAs seriously disrupted glycerophospholipid metabolism by upregulating the contents of lysophosphatidylglycerol acyltransferase 1 and phosphatidylinositol and downregulating the contents of choline/ethanolamine kinase beta, choline-ethanolamine phosphotransferase 1, phospholipase D4, 1-acylglycerophosphocholine, phosphatidylcholine, and dihydroxyacetone phosphate in the liver, resulting in detrimental inflammation, fibrosis, and apoptosis. This study revealed that EFTAs induced severe hepatotoxicity by disrupting glycerophospholipid metabolism.


Asunto(s)
Alcaloides , Enfermedad Hepática Inducida por Sustancias y Drogas , Eupatorium , Alcaloides de Pirrolicidina , Ratones , Animales , Eupatorium/química , Proteómica , Alcaloides de Pirrolicidina/análisis , Metabolómica , Fibrosis , Glicerofosfolípidos , Colina
8.
J Ethnopharmacol ; 282: 114627, 2022 Jan 10.
Artículo en Inglés | MEDLINE | ID: mdl-34509603

RESUMEN

ETHNOPHARMACOLOGICAL RELEVANCE: Dengue virus (DENV) is a re-emerging mosquito-borne flavivirus that has recently engendered large epidemics around the world. Consequently antivirals with effective anti-DENV therapeutic activity are urgently required. In the 18th century, Europeans, as well as native inhabitants of North America, were known to adapt the medicinal property of the common perennial plant Eupatorium perfoliatum L. to treat fever and infections. Previous studies have shown that Eupatorium perfoliatum L. possesses anti-inflammatory, anti-oxidative, anti-plasmodial, anti-bacterial and antiviral activities. However, to the best of our knowledge, no anti-DENV activity of E. perfoliatum L. has been investigated at the molecular level so far. AIM OF STUDY: Here, for the first time we have attempted to study the action of E. perfoliatum extract and its few bioactive components i.e., quercetin, caffeic acid and eupafolin against wild primary clinical isolate of DENV-2 infection in an in vitro model. MATERIALS AND METHODS: The presence of the bioactive components in the E. perfoliatum extract, were analyzed by HPLC- DAD. Then, CC50 as well as IC50 values of the extract and its bioactive components were measured against DENV in HepG2 cell line. After that, the antiviral activity was studied by Time of addition assay using qRT-PCR. Further, the downstream signalling action of E. perfoliatum extract, was studied by Human phosphorylation MAPK antibody array, followed by immunofluorescence microscopy. Moreover, a molecular docking analysis was done to study the binding affinity of bioactive components of E. perfoliatum extract with TIM-1 transmembrane receptor protein, which is known for viral internalization. RESULT: We found that E. perfoliatum extract has marked antiviral activity during pre-treatment against DENV infection in HepG2 cell line. The extract also significantly reduced the DENV induced autophagy in HepG2 cell line as detected by LC3 II localization. The presence of different bioactive compounds in E. perfoliatum extract were confirmed by HPLC-DAD. In the bioactive components, in parallel to earlier studies, quercetin showed the most significant preventive action against DENV infection. Further, in molecular docking analysis also, quercetin showed the strongest binding affinity towards DENV membrane receptor TIM-1 protein. CONCLUSION: Our findings suggests that E. perfoliatum extract has significant potential to be an anti-DENV therapeutic agent. Moreover, among the bioactive components, quercetin may have a prophylaxis role in executing the antiviral activity of E. perfoliatum extract against DENV infection.


Asunto(s)
Autofagia/efectos de los fármacos , Virus del Dengue/efectos de los fármacos , Eupatorium/química , Extractos Vegetales/farmacología , Serina-Treonina Quinasas TOR/metabolismo , Aedes , Animales , Antivirales/química , Antivirales/farmacología , Línea Celular , Supervivencia Celular/efectos de los fármacos , Virus del Dengue/fisiología , Regulación de la Expresión Génica/efectos de los fármacos , Humanos , Quinasas de Proteína Quinasa Activadas por Mitógenos/genética , Quinasas de Proteína Quinasa Activadas por Mitógenos/metabolismo , Simulación del Acoplamiento Molecular , Estructura Molecular , Fitoterapia , Extractos Vegetales/química , ARN Viral/genética , ARN Viral/metabolismo , Serina-Treonina Quinasas TOR/genética , Cultivo de Virus , Replicación Viral/efectos de los fármacos
9.
Bioorg Med Chem Lett ; 53: 128422, 2021 12 01.
Artículo en Inglés | MEDLINE | ID: mdl-34710624

RESUMEN

Three new germacrane-type sesquiterpene lactones (1-3) were isolated alongside seven known related congeners (4-10) from the leaves of Eupatorium chinense L. (Compositae). The planar structures of 1-3 were elucidated by their spectroscopic data, including 1D and 2D NMR spectra. The relative and absolute configurations of 1-3 were determined using NOESY experiments and electronic circular dichroism analyses. Compounds 1, 4, 5, and 7 inhibited protein tyrosine phosphatase (PTP) 1B activity with IC50 values of 25, 11, 28, and 24 µM, respectively. Among these, compound 4 exhibited an inhibitory effect on T-cell PTP (TCPTP) with an IC50 value of 25 µM. To our knowledge, this is the first study demonstrating the PTP inhibitory activity of the germacrane sesquiterpenes. The results show that compound 4 acts as an inhibitor of both PTP1B and TCPTP.


Asunto(s)
Inhibidores Enzimáticos/farmacología , Eupatorium/química , Hojas de la Planta/química , Proteína Tirosina Fosfatasa no Receptora Tipo 1/antagonistas & inhibidores , Sesquiterpenos de Germacrano/farmacología , Teoría Funcional de la Densidad , Relación Dosis-Respuesta a Droga , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/aislamiento & purificación , Humanos , Estructura Molecular , Proteína Tirosina Fosfatasa no Receptora Tipo 1/metabolismo , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/aislamiento & purificación , Relación Estructura-Actividad
10.
Int J Mol Sci ; 22(14)2021 Jul 12.
Artículo en Inglés | MEDLINE | ID: mdl-34299072

RESUMEN

Five new compounds, eupatodibenzofuran A (1), eupatodibenzofuran B (2), 6-acetyl-8-methoxy-2,2-dimethylchroman-4-one (3), eupatofortunone (4), and eupatodithiecine (5), have been isolated from the aerial part of Eupatorium fortunei, together with 11 known compounds (6‒16). Compounds 1 and 2 featured a new carbon skeleton with an unprecedented 1-(9-(4-methylphenyl)-6-methyldibe nzo[b,d]furan-2-yl)ethenone. Among the isolates, compound 1 exhibited potent inhibitory activity with IC50 values of 5.95 ± 0.89 and 5.55 ± 0.23 µM, respectively, against A549 and MCF-7 cells. The colony-formation assay demonstrated that compound 1 (5 µM) obviously decreased A549 and MCF-7 cell proliferation, and Western blot test confirmed that compound 1 markedly induced apoptosis of A549 and MCF-7 cells through mitochondrial- and caspase-3-dependent pathways.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Eupatorium/química , Neoplasias/tratamiento farmacológico , Fitoquímicos/química , Fitoquímicos/farmacología , Extractos Vegetales/farmacología , Acetofenonas/química , Antineoplásicos Fitogénicos/química , Apoptosis , Benzofuranos/química , Proliferación Celular , Cromonas/química , Humanos , Estructura Molecular , Neoplasias/patología , Relación Estructura-Actividad , Células Tumorales Cultivadas
11.
J Sep Sci ; 44(17): 3237-3247, 2021 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-34240803

RESUMEN

Pyrrolizidine alkaloids are toxins having hepatotoxic and carcinogenic effects on human health. A ultra high performance liquid chromatography tandem mass spectrometry technique was developed for the first time for the simultaneous determination of eight pyrrolizidine alkaloids, including four diastereoisomers (intermedine, lycopsamine, rinderine, and echinatine) and their respective N-oxide forms, in different parts of Eupatorium lindleyanum. The risk assessment method for pyrrolizidine alkaloids in Eupatorium lindleyanum was explored using the margin of exposure strategy for the first time based on a real-life exposure scenario. Differences were found in all eight pyrrolizidine alkaloids in various parts of Eupatorium lindleyanum. Besides, the total levels of pyrrolizidine alkaloids in Eupatorium lindleyanum followed the order of root > flower > stem > leaf. Moreover, the risk assessment data revealed that the deleterious effects on human health were unlikely at exposure times of less than 200, 37, and 12 days during the lifetimes of Eupatorium lindleyanum leaves, stems, and flowers, respectively. This study reported both the contents of and risk associated with Eupatorium lindleyanum pyrrolizidine alkaloids. The comprehensive application of the novel ultra high performance liquid chromatography tandem mass spectrometry technique alongside the risk assessment approach provided a scientific basis for quality evaluation and rational utilization of toxic pyrrolizidine alkaloids in Eupatorium lindleyanum to improve public health safety.


Asunto(s)
Eupatorium/química , Componentes Aéreos de las Plantas/química , Alcaloides de Pirrolicidina/análisis , Administración Oral , Cromatografía Líquida de Alta Presión , Humanos , Conformación Molecular , Alcaloides de Pirrolicidina/administración & dosificación , Alcaloides de Pirrolicidina/efectos adversos , Medición de Riesgo , Espectrometría de Masas en Tándem
12.
J Sep Sci ; 44(17): 3174-3187, 2021 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-34184412

RESUMEN

As a traditional Chinese medicine, Eupatorium lindleyanum DC. has an effect on resolving phlegm, relieving cough, and relieving asthma. In this study, an ultra high performance liquid chromatography with quadrupole time-of-flight mass spectrometry method was established for qualitative analysis of Eupatorium lindleyanum. Besides, we developed an ultra high performance liquid chromatography with triple quadrupole tandem mass spectrometry method in positive and negative multiple reaction monitor modes for the quantitative analysis of 27 chemical constituents from 19 different batches of Eupatorium lindleyanum. The methodology validated linearity, intraday and interday precision, stability, repeatability, and recovery. The results showed that there were some differences in different batches of Eupatorium lindleyanum, which might be attributed to the influence of different growth environments and climatic conditions on the accumulation of compounds. The variable importance of projection value of orthogonal partial least square discriminant analysis and anti-inflammatory activity test showed that eupalinolide A, B, C, and K have high content and strong activity, which could provide a reference for the follow-up study of the quality markers of Eupatorium lindleyanum. Collectively, we developed a rapid and efficient method for the qualitative analysis and simultaneous quantification of Eupatorium lindleyanum, which was beneficial for the comprehensive utilization and development of resources.


Asunto(s)
Antiinflamatorios/análisis , Medicamentos Herbarios Chinos/análisis , Eupatorium/química , Cromatografía Líquida de Alta Presión , Medicina Tradicional China , Estructura Molecular , Espectrometría de Masas en Tándem
13.
Bioorg Chem ; 113: 105030, 2021 08.
Artículo en Inglés | MEDLINE | ID: mdl-34089946

RESUMEN

Five new racemic alkyl-benzofuran dimers, (±)-dieupachinins I-M (1-5), were isolated from the root tubers of Eupatorium chinense, a well-known traditional Chinese medicine for the treatment of diphtheria in Guangdong province. The structures of these compounds, especially the first examples of 12,10'-epoxy dimer dieupachinin I (1), 12-nor-dimer dieupachinin J (2), and 12,12'-dinor-dimer dieupachinin K (3), were elucidated by spectroscopic data analysis. Chiral resolution were further carried out on a cellulose column by HPLC, and compounds 2-5 were successfully separated into two enantiomers, respectively. The absolute configurations of (+)-(2-5) and (-)-(2-5) were established by theoretical ECD calculation. All the compounds were evaluated for insulin-stimulated glucose uptake in C2C12 myotubes and (±)-dieupachinin I (1) exhibited the best activity. Compound 1 enhanced insulin-stimulated glucose uptake via activating the insulin receptor substrate 1/protein kinase B/glycogen synthase kinase-3ß signaling pathway. Moreover, all the isolates were tested for their nitric oxygen (NO) inhibitory effects in lipopolysaccharide-treated RAW264.7 macrophages, and compounds (±)-1, (±)-2, and (±)-4 showed promising inhibitory effects with IC50 values of 6.42 ± 1.85, 6.29 ± 1.94, and 16.03 ± 2.07 µM, respectively. (±)-Dieupachinin I (1) again dose-dependently suppressed LPS-induced expression of inducible NO synthase and nuclear translocation of p65.


Asunto(s)
Antiinflamatorios/química , Benzofuranos/química , Eupatorium/química , Animales , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Benzofuranos/aislamiento & purificación , Benzofuranos/farmacología , Supervivencia Celular/efectos de los fármacos , Dimerización , Eupatorium/metabolismo , Glucosa/metabolismo , Proteínas Sustrato del Receptor de Insulina/metabolismo , Lipopolisacáridos/farmacología , Macrófagos/citología , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Medicina Tradicional China , Ratones , Conformación Molecular , Mioblastos/citología , Mioblastos/efectos de los fármacos , Mioblastos/metabolismo , Óxido Nítrico/metabolismo , Óxido Nítrico Sintasa de Tipo II/genética , Óxido Nítrico Sintasa de Tipo II/metabolismo , Células RAW 264.7
14.
Food Chem Toxicol ; 151: 112151, 2021 May.
Artículo en Inglés | MEDLINE | ID: mdl-33774095

RESUMEN

This study was to analyze the pyrrolizidine alkaloids (PAs) in Eupatorium fortunei herbs and its derived finished products with a view to evaluating their effects on the proliferation and oligodendrogenesis of neural progenitor cells (NPCs). Using a LC-MS/MS method with 32 PAs reference standards, 8 PAs including intermedine, intermedine N-oxide, lycopsamine, lycopsamine N-oxide, retronecine, seneciphylline and senkirkine and 7-acetylintermedine N-oxide were identified with intermedine N-oxide and lycopsamine N-oxide being most abundant. The total PA amounts were found to vary from 0.18 to 61.81 µg/g in 30 batches of herbs and from 0.86 to 36.96 µg/g in 4 commercial finished products, respectively. Risk assessments indicated that the short-term intake seemed unlikely lead to acute toxic effects but the chronic use warranted cautions. Using NPCs derived from mouse induced pluripotent stem cells as an in vitro testing model, intermedine, intermedine N-oxide and lycopsamine N-oxide appeared to decrease cell viability at 30 µM whereas intermedine N-oxide inhibited oligodendrogenesis of NPCs at 10 µM. The present results suggested that the PAs in the majority of E. fortunei herbs and the derived products not only resulted in their exposure far exceeding the acceptable intake limit (i. e. 1.0 µg PA per day for adults) in herbal medicinal products recommended by the European Medicines Agency but also induced neurotoxicity to NPCs in vitro.


Asunto(s)
Eupatorium/química , Oligodendroglía/efectos de los fármacos , Alcaloides de Pirrolicidina/análisis , Alcaloides de Pirrolicidina/toxicidad , Animales , Cromatografía Liquida/métodos , Técnicas In Vitro , Ratones , Células-Madre Neurales/citología , Oligodendroglía/citología , Reproducibilidad de los Resultados , Espectrometría de Masas en Tándem/métodos
15.
Prep Biochem Biotechnol ; 51(6): 530-535, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-33135958

RESUMEN

Counter-current chromatography (CCC) target-guided by on-line HPLC with post-column DPPH assay was established for efficient screening and isolation of large amount of antioxidants from Eupatorium lindleyanum DC. On-line HPLC with post-column DPPH reaction was used to screen the antioxidants and optimize the biphasic solvent system of CCC, then the targeted peaks were purified using CCC. In the present study, three compounds, nepetin, cirsiliol and jaceosidin, were targeted and successively separated from n-butanol fraction of E. lindleyanum DC. by this strategy. All three compounds showed strong DPPH radical scavenging activity. These results confirmed that the strategy would be an efficient and effective method to isolate antioxidants from complex mixtures.


Asunto(s)
Antioxidantes , Eupatorium/química , Flavonas , Flavonoides , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Cromatografía Líquida de Alta Presión , Flavonas/química , Flavonas/aislamiento & purificación , Flavonoides/química , Flavonoides/aislamiento & purificación
16.
Chem Biodivers ; 17(12): e2000520, 2020 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-33184961

RESUMEN

Panax notoginseng (Burkill) F.H.Chen (Araliaceae), of which the dry root and rhizome are precious traditional Chinese medicine, suffers severely from diseases during planting. Essential oils (EOs) with antimicrobial activity are a possibility for the development of green pesticides. We extracted EOs from Pogostemon cablin (Blanco) Benth. and Eupatorium fortunei Turcz., respectively and tested their inhibitory rates on fungi isolated from diseased P. notoginseng by the Oxford cup method. The compounds of the EO were identified by GC/MS and the minimum inhibitory concentrations (MICs) of the EOs and their main components were evaluated by the 96-well plate method. We also mixed P. cablin EO, E. fortunei EO and hymexazol in pairs to explore whether their combinations produce stronger antifungal effects than individual components. Finally, we evaluated the effects of the EOs against Fusarium oxysporum in vivo. P. cablin EO and E. fortunei EO exhibited different antifungal activities against fungi, with the inhibitory rates of 21.02 %-100 % and 54.84 %-100 % and MICs of 0.07-0.88 mg/mL and 0.20-1.17 mg/mL, respectively. Pogostone (24.96 %) and thymol (15.64 %) were the major compounds of P. cablin EO and E. fortunei EO, respectively, and they exhibited stronger antifungal activities than EOs, with MICs of 0.008-0.078 mg/mL and 0.12-0.31 mg/mL, respectively. Moreover, hymexazol was mixed with E. fortunei EO, and the inhibitory effect against Cylindrocarpon destructans was enhanced with a synergistic effect. The disease incidence and disease index of EO treatments decreased significantly in vivo. Based on our study, P. cablin EO and E. fortunei EO have great potential to be developed into green fungicides for use in agriculture to control diseases of P. notoginseng.


Asunto(s)
Eupatorium/química , Hongos/efectos de los fármacos , Aceites Volátiles/farmacología , Panax notoginseng/química , Pogostemon/química , Cromatografía de Gases y Espectrometría de Masas , Pruebas de Sensibilidad Microbiana
17.
PLoS One ; 15(11): e0241666, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-33147299

RESUMEN

When developing new products to be used in honeybee colonies, further than acute toxicity, it is imperative to perform an assessment of risks, including various sublethal effects. The long-term sublethal effects of xenobiotics on honeybees, more specifically of acaricides used in honeybee hives, have been scarcely studied, particularly so in the case of essential oils and their components. In this work, chronic effects of the ingestion of Eupatorium buniifolium (Asteraceae) essential oil were studied on nurse honeybees using laboratory assays. Survival, food consumption, and the effect on the composition of cuticular hydrocarbons (CHC) were assessed. CHC were chosen due to their key role as pheromones involved in honeybee social recognition. While food consumption and survival were not affected by the consumption of the essential oil, CHC amounts and profiles showed dose-dependent changes. All groups of CHC (linear and branched alkanes, alkenes and alkadienes) were altered when honeybees were fed with the highest essential oil dose tested (6000 ppm). The compounds that significantly varied include n-docosane, n-tricosane, n-tetracosane, n-triacontane, n-tritriacontane, 9-tricosene, 7-pentacosene, 9-pentacosene, 9-heptacosene, tritriacontene, pentacosadiene, hentriacontadiene, tritriacontadiene and all methyl alkanes. All of them but pentacosadiene were up-regulated. On the other hand, CHC profiles were similar in healthy and Nosema-infected honeybees when diets included the essential oil at 300 and 3000 ppm. Our results show that the ingestion of an essential oil can impact CHC and that the effect is dose-dependent. Changes in CHC could affect the signaling process mediated by these pheromonal compounds. To our knowledge this is the first report of changes in honeybee cuticular hydrocarbons as a result of essential oil ingestion.


Asunto(s)
Abejas/efectos de los fármacos , Abejas/metabolismo , Eupatorium/química , Aceites Volátiles/metabolismo , Aceites Volátiles/toxicidad , Alcanos/metabolismo , Alquenos/metabolismo , Animales , Abejas/microbiología , Hidrocarburos/metabolismo , Nosema/patogenicidad
18.
Carbohydr Polym ; 247: 116700, 2020 Nov 01.
Artículo en Inglés | MEDLINE | ID: mdl-32829828

RESUMEN

To avoid the negative effects of chemical herbicides and prepare herbicide with long-term efficacy, the active ingredients of eupatorium adenophorum spreng (AIEAS, negatively charged) were used as a botanical herbicide, and based on electrostatic attraction, the self-assembled hydroxyl isopropyl chitosan (HPCTS, positively charged) and carboxymethyl chitosan (CMC, with good water solubility) were successfully employed as degradable and water-soluble carrier for AIEAS to realize its controlled release. The release of AIEAS from the chitosan carrier in water could be divided into two stages. In the first stage, a fast release of AIEAS was detected and the total amount of the released AIEAS reached 41.5 %, while the release rate effectively slowed down in the second stage, indicating that good balance between fast control of weeds and long-term efficacy was achieved through this controlled delivery system. The release kinetics of AIEAS during the whole release process showed good fit to the Ritger-Peppas model with Fickian diffusion as the dominant release mechanism. Moreover, it found that the released AIEAS from chitosan carrier showed fine herbicidal effect on barnyard grass.


Asunto(s)
Quitosano/análogos & derivados , Preparaciones de Acción Retardada , Eupatorium/química , Herbicidas/química , Herbicidas/metabolismo , Electricidad Estática , Quitosano/química
19.
Biomed Res Int ; 2020: 6859374, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-32685518

RESUMEN

Eupatorium japonicum Thunb and Foeniculum vulgare are two of the most widely used folk herbs and constituents in many traditional Chinese herbal formulas. Nonetheless, little toxicological and safety information associated with following daily repeated exposure is obtained according to previous research. The present study was performed to assess the toxicity of ethanol extract from Eupatorium japonicum Thunb and Foeniculum vulgare (EFE) in male rats administered by dietary oral gavage at target doses of 0.39, 0.78, and 1.56 g/kg body weight/day for 90 days. There were no significant adverse effects on clinical signs, body weight, food conversion efficiency, and vital hematological indices. However, some hematology and biochemical indices such as WCV, MCH, MCHC, LY, MPV, T-CHO, as well as TG revealed significant changes in Sprague-Dawley rats and organ weights in lung and spleen showed diminished in male rats. Necropsy and histopathology findings suggested that no significant differences in absolute weights were found in all organs except lung and spleen, and no treatment-related alteration was identified in any organs. All results obtained in the present study indicated that the proper use of EFE in traditional medicine at oral dosages up to 1.56 g/kg/day body weight may harbor no prolonged toxicity to rats. However, further studies of EFE are still necessary to assess its oral safety in patients.


Asunto(s)
Etanol/química , Eupatorium/química , Foeniculum/química , Extractos Vegetales/farmacología , Administración Oral , Animales , Femenino , Masculino , Extractos Vegetales/efectos adversos , Extractos Vegetales/química , Ratas , Ratas Sprague-Dawley , Factores de Tiempo
20.
Fitoterapia ; 146: 104674, 2020 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-32561423

RESUMEN

Three new sesquiterpenoids (1-3) and four new benzofuran dimers (+)-4 and (-)-4, (+)-5 and (-)-5, and four known benzofuran dimers (+)-6 and (-)-6, (+)-7 and (-)-7 were isolated from the underground parts of Eupatorium chinense. The enantiomers of racemates (±)-4 ~ (±)-7 were separated by chiral HPLC columns, and their absolute configurations were determined by circular dichroism experiments. The structures of all new compounds were elucidated on the basis of their NMR, and MS data as well as by comparison with literature values. The all of the isolated compounds were tested in vitro for their cytotoxic activities against the Caski, MDA-MB-231 and HepG2 cancer cell lines.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Benzofuranos/farmacología , Eupatorium/química , Sesquiterpenos/farmacología , Antineoplásicos Fitogénicos/aislamiento & purificación , Benzofuranos/aislamiento & purificación , China , Células Hep G2 , Humanos , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Raíces de Plantas/química , Sesquiterpenos/aislamiento & purificación
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