RESUMEN
Two new nervogenic acid derivatives liparisnervosides Q (1) and R (5), as well as five known nervogenic acid derivatives (2-4, 6, 7) and four phenanthrenes (8-11) were isolated from the whole plant of Liparis nervosa (Thunb. ex A. Murray) Lindl.. Their structures were detremined using extensive spectroscopic techniques, including 1D, 2D NMR, and HR-ESI-MS, and acid hydrolysis. Furthermore, their antimicrobial and immunosuppressive activities were evaluated. Nervosine VII (3) exhibited antimicrobial activity against Staphylococcus aureus with an MIC of 62.5â µg/mL and inhibited the proliferation of human T cells with an IC50 value of 9.67±0.96â µM. These findings contribute to our understanding of the potential pharmacological properties of these compounds.
Asunto(s)
Proliferación Celular , Inmunosupresores , Pruebas de Sensibilidad Microbiana , Fenantrenos , Staphylococcus aureus , Humanos , Inmunosupresores/farmacología , Inmunosupresores/química , Inmunosupresores/aislamiento & purificación , Staphylococcus aureus/efectos de los fármacos , Proliferación Celular/efectos de los fármacos , Fenantrenos/farmacología , Fenantrenos/química , Fenantrenos/aislamiento & purificación , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Linfocitos T/efectos de los fármacos , Relación Estructura-Actividad , Estructura Molecular , Relación Dosis-Respuesta a DrogaRESUMEN
Ulcerative colitis (UC), belonging to inflammatory bowel disease (IBD), is a chronic and relapsing inflammatory disorder of the gastrointestinal tract, which has not been completely cured in patients so far. Valeriana jatamansi is a Chinese medicine used clinically to treat "diarrhea," which is closely related to UC. This study was to elucidate the therapeutic effects of V. jatamansi extract (VJE) on dextran sodium sulfate (DSS)-induced UC in mice and its underlying mechanism. In this work, VJE effectively ameliorates the symptoms and histopathological scores and reduces the production of inflammatory factors in UC mice. The colon untargeted metabolomics analysis and 16S rDNA sequencing showed remarkable differences in colon metabolite profiles and intestinal microbiome composition between the control and DSS groups, and VJE intervention can reduce these differences. Thirty-two biomarkers were found and modulated the primary pathways including pyrimidine metabolism, arginine biosynthesis, and glutathione metabolism. Meanwhile, twelve significant taxa of gut microbiota were found. Moreover, there is a close relationship between endogenous metabolites and intestinal flora. These findings suggested that VJE ameliorates UC by inhibiting inflammatory factors, recovering intestinal maladjustment, and regulating the interaction between intestinal microbiota and host metabolites. Therefore, the intervention of V. jatamansi is a potential therapeutic treatment for UC.
Asunto(s)
Colitis Ulcerosa , Colitis , Microbioma Gastrointestinal , Microbiota , Valeriana , Animales , Ratones , Colitis Ulcerosa/inducido químicamente , Colitis Ulcerosa/tratamiento farmacológico , Metabolómica , Colon , Sulfato de Dextran , Modelos Animales de Enfermedad , Colitis/inducido químicamente , Colitis/tratamiento farmacológico , Ratones Endogámicos C57BLRESUMEN
Terpene-conjugated curcuminoids are conjugates of curcuminoids and bisabolanes in the rhizomes of Curcuma longa L. The fragmentation pathways of known three terpene-conjugated curcuminoids (bisabolocurcumin-ether, bisabocurcumin, and demethoxybisabolocurcumin ether) and curcumin, demethoxycurcumin, and bisdemethoxycurcumin were investigated using high-performance liquid chromatography-electrospray ionization tandem mass spectrometry in negative mode to rapidly search and discover similar unknown compounds of the acetone fraction of turmeric. Subsequently, compounds 1-3 were founded in the acetone fraction based on molecular weight and above fragmentation pathways (the characteristic fragment ions, the most and second most abundant fragment ions produced in MS2 spectra). Terpecurcumin X (1) and terpecurcumin Y (3) were further separated by liquid chromatography-tandem mass spectrometry guided isolation technique to verify their structures by nuclear magnetic resonance, electrospray ionization high-resolution mass spectroscopy, ultraviolet and visible spectra and infrared spectra. Interestingly, 1 and 3 were new compounds. The results indicate the feasibility and significant advantages of liquid chromatography-tandem mass spectrometry for the rapid discovery and analysis of new constituents in traditional Chinese medicine. In vitro, Terpene-conjugated curcuminoids had better nitric oxide inhibitory activity than the other seven curcuminoids (demethoxycurcumin, bisdemethoxycurcumin, curdione, curcumenone, bisacurone, curcumenol, and germacron).
Asunto(s)
Curcumina , Terpenos , Terpenos/análisis , Espectrometría de Masas en Tándem/métodos , Acetona , Diarilheptanoides , Cromatografía Liquida , Curcumina/análisis , Cromatografía Líquida de Alta Presión/métodos , Antiinflamatorios , Curcuma/químicaRESUMEN
Investigation on the chemical components of Valeriana jatamansi Jones (Caprifoliaceae), a new lignan with pyran-ring, dipsalignan G (1), along with eight known compounds (2-9) were isolated. Their structures were elucidated by extensive analysis of 1D, 2D NMR and HR-ESI-MS spectroscopic data. Additionally, possible biosynthetic pathway of 1 was proposed. Finally, biological evaluation results showed that 8 had significant scavenging ability to ABTS and DPPH free radicals, with IC50 values of 1.35 ± 0.01 and 2.94 ± 0.01 µg/ml, respectively.
RESUMEN
Plant phenolic compounds have attracted considerable attention because of their health benefits. This study aimed to investigate the composition and antioxidant activity of phenol extracts from Polygonatum zanlanscianense Pamp. steam and leaf (PPP). The FTIR, UPLC-Q-Obtrip-MS, and HPLC-DAD methods were used to analyze the composition of PPP, and 20 phenolic compounds were preliminarily identified. Among them, the contents of hyperin, astragalin, and diosmetin levels were the highest. Treatment with PPP can significantly reduce t-BHP-induced cell damage in HepG2 cells, reactive oxygen species (ROS) accumulation, and malondialdehyde (MDA) content. Meanwhile, the superoxide dismutase (SOD), catalase (CAT), glutathione (GSH), and glutathione peroxidase (GSH-Px) activities can be increased. Moreover, PPP enhanced Nrf2 expression, which was consistent with that of heme oxygenase-1 (HO-1), glutamate-cysteine ligase catalytic subunit (GCLC), and NAD(P)H quinone oxidoreductase-1 (NQO1), whereas the expression of Keap1, the Nrf2 inhibitor, was decreased. All findings indicate that PPP can serve as a natural bioactive substance for preventing oxidative stress.
Asunto(s)
Polygonatum , Humanos , Proteína 1 Asociada A ECH Tipo Kelch/metabolismo , Vapor , Factor 2 Relacionado con NF-E2/metabolismo , Células Hep G2 , Estrés Oxidativo , Antioxidantes/farmacología , Antioxidantes/metabolismo , Especies Reactivas de Oxígeno/metabolismo , Glutatión/metabolismo , Fenoles/farmacología , Hemo-Oxigenasa 1/metabolismoRESUMEN
Although the fruit of Ficus tikoua Bur. has been consumed by montanic people in China for centuries, its chemical and biological composition was still unclear. A series of comprehensive investigations on its chemical constituents and bioactivities were carried out for the first time. As a result, six compounds were isolated and identified as the main components in this fruit. GC-MS analysis of the lipid components demonstrated that Ficus tikoua Bur. fruit contains some wholesome constituents such as fatty acids, vitamins, triterpenoids, and phytosterols. The fatty acids are mainly composed of linolenic acid (61.27%) and linoleic acid (22.79%). Furthermore, this fruit contains a relative high content of crude protein (9.41 ± 0.03%), total amino acids (9.28%), and total polyphenols (0.86 ± 0.01 g/100 g). The analysis of monosaccharide composition showed that the total polysaccharide mainly consists of glucose, glucuronic acid, xylose, arabinose, mannose, galactose, galacturonic acid, and rhamnose. The polysaccharide, polyphenol, water, ethanol, and flavonoid extracts exhibited prominent antioxidant activity determined by ABTS, DPPH, and FRAPS methods. Meanwhile, the total polysaccharide exhibited significant immunomodulatory effect by enhancing the release of cytokines and expression of iNOS and COX-2 in RAW264.7 cells, significantly decreasing the expression of c-Jun and p65 proteins in the cytoplasm; increasing the translocation of c-Jun and p65 to the nucleus; and regulating the phosphorylation level of Akt, PI3K, and PDK1 in the PI3K/AKT signaling pathway. This study proved that the fruit of F. tikoua is a reliable source of functional food.
Asunto(s)
Ficus , Fitosteroles , Triterpenos , Humanos , Ficus/química , Antioxidantes/química , Frutas/química , Polifenoles/farmacología , Polifenoles/análisis , Ciclooxigenasa 2 , Galactosa/análisis , Manosa/análisis , Arabinosa/análisis , Ramnosa/análisis , Xilosa/análisis , Fosfatidilinositol 3-Quinasas , Proteínas Proto-Oncogénicas c-akt , Polisacáridos/química , Flavonoides/análisis , Monosacáridos/análisis , Citocinas/análisis , Agua/análisis , Lípidos/análisis , Vitaminas/análisis , Triterpenos/análisis , Fitosteroles/análisis , Glucosa/análisis , Etanol/análisis , Aminoácidos/análisis , Glucuronatos , Ácidos Linolénicos , Ácidos Linoleicos/análisisRESUMEN
In this study, the sorption properties of Cr(VI), As(III), and Pb(II) on chitosan-modified magnetic biochar (CMBC) derived from residues of Ligusticum chuanxiong Hort. were investigated. CMBC was found to be a valuable material for removing three heavy metals from water simultaneously. Kinetic analysis suggested Cr(VI), As(III), and Pb(II) were chemisorbed onto CMBC, while isotherm data conformed well to Langmuir model, the maximum adsorption capacity of CMBC was found to be 65.74 mg/g for Cr(VI), 49.32 mg/g for As(III), and 69.45 mg/g for Pb(II). Experiments, characterization, and density functional theory (DFT) calculations were employed to explore the mechanisms. Furthermore, CMBC demonstrated excellent removal rates of over 95% for Cr(VI), 99% for As(III) and Pb(II) from contaminated water bodies. This work shows that CMBC holds significant potential for wastewater treatment of heavy metals and provides an effective solution for the utilization of Chinese herb residues in environmental remediation.
Asunto(s)
Carbón Orgánico , Quitosano , Metales Pesados , Contaminantes Químicos del Agua , Quitosano/química , Carbón Orgánico/química , Adsorción , Contaminantes Químicos del Agua/química , Cinética , Purificación del Agua/métodos , Cromo/química , Medicamentos Herbarios Chinos/químicaRESUMEN
Materials and Methods: The macroscopic characteristics of CR as well as its moisture, ethanol extract, essential oil, total ash, and acid-insoluble ash contents were examined and calculated. In addition, qualitative identification and quantitative determination of α-cyperone, cyperotundone, and nootkatone were simultaneously performed, and a high-performance liquid chromatography (HPLC) fingerprint chromatogram was established. Inductively coupled plasma mass spectrometry and gas chromatography methods recorded in ChP were used to measure the contents of residues of heavy metal and deleterious elements as well as residues of organochlorine pesticide, respectively. Hierarchical cluster analysis and typical canonical correlation analysis were performed using Origin 9.1 and SPSS 23.0 to explore the correlation between CR's growth area, morphological characteristics, and quality. Results: Of the 47 batches of CR analyzed, only 4 collected from the province of Shandong had a flat appearance, which did not accord with the macroscopic characteristics of CR. Overall, only 4 batches met ChP standards for CR. In addition, 30 and 38 batches did not meet the requirements for moisture content and essential oil content, respectively. The similarity values of HPLC fingerprints ranged from 0.568 to 0.986. Results of hierarchical cluster analysis for ethanol extracts, essential oil, α-cyperone, cyperotundone, and nootkatone and the HPLC fingerprints (total peak time and peak area) suggested that the samples could be classified into four clusters, with no significant difference in growth geographic areas among them. Results of canonical correlation analysis indicated that the first canonical pair could represent the correlation between macroscopic characteristics (vector 1) and chemical quality (vector 2), with shorter diameter and length denoting lower ethanol extract content and higher nootkatone content in a single grain of CR. Conclusions: Crude medicinal materials were collected and examined in this study to reflect the overall quality status of CR in China. The methods chosen to detect, calculate, and analyze the quality of CR were suitable to the investigation, and the results are crucial not only for estimating the current quality status of CR, but also for conducting further research into its cultivation, quality assurance, and commodity specification. Besides, this mode of investigation could be used to evaluate other medicines.
RESUMEN
Lignans, with various biological activities, such as antitumor, antioxidant, antibacterial, and antiviral activities, are widely distributed in nature and mainly exist in the xylem of plants. In this paper, we summarized the structures and bioactivities of lignans reported in recent years (2019-2021) from five parts, including (1) a summary and classification of newly reported compounds; (2) the pharmacological activities of lignans; (3) molecular resources and activity distribution; (4) the structure-activity relationships; and (5) the clinical application of lignans. This review covers all undescribed compounds that were reported within the covered period of time and all bioactivity data about previously isolated lignans. The distribution of lignans in different plants and families is visualized, which improves the efficiency of searching for specific molecules. The diverse activities of different types of lignans provide an important reference for the rapid screening of these compounds. Discussion about the structure-activity relationships of lignans provides a direction for the structural modification of skeleton molecules. Combined with the clinical application of such molecules, this work will provide a valuable reference for pharmaceutical chemists.
Asunto(s)
Lignanos , Antioxidantes/química , Antivirales/química , Antivirales/farmacología , Lignanos/química , Estructura Molecular , Plantas/química , Relación Estructura-ActividadRESUMEN
ETHNOPHARMACOLOGICAL RELEVANCE: The species of the genus Cirsium have been used as traditional Chinese medicine for hundreds of years. It is believed that Cirsium has the efficacies of cooling blood and stopping bleeding, dispelling blood stasis, detoxifying and eliminating carbuncle. At present, they are mainly used in treatment of the hemoptysis, hematemesis, hemoptysis, hematuria, traumatic bleeding and Henoch-Schonlein purpura. They are widely used in traditional Chinese medicine. AIM: This paper systematically collated the classification, traditional use, pharmacological action, phytochemistry and clinical application of Cirsium plants in the past ten years, intending to provide a critical appraisal of current knowledge for future in-depth study and rational development and utilization of Cirsium plants. MATERIAL AND METHODS: This paper searched various databases (SciFinder, Science Direct, CNKI, Wiley online library, Spring Link, Web of Science, PubMed, Wanfang Data, Weipu Data), Chinese Pharmacopoeia 2020 Edition, Chinese Flora, Chinese Materia Medica and some local books on ethnopharmacology. RESULTS: More than ten species of Cirsium have been used as folk medicine, and modern pharmacological studies have shown that Cirsium has the effects of protecting liver, antioxidation, anti-tumor, anti-inflammation, antibacterial, etc. More than 200 chemical constituents such as flavonoids, triterpenes, sterols, phenylpropanoids have been isolated from Cirsium. Some ingredients show a wide variety of bioactivities including hepatoprotective, anti-inflammatory, antioxidant, anti-tumor and other activities. At present, Cirsium medicinal plants, as traditional Chinese medicine, were mainly used to treat nephritis, Henoch-Schonlein purpura and hemorrhage, although some species used in folk lack of quality control systems. CONCLUSION: Cirsium plants are a safe and effective medicine for cooling blood and hemostasis. Recent studies on pharmacology and phytochemistry also provide solid scientific evidences for the traditional application of this genus. It also shows significant hepatoprotective activity and may be a potential clinical candidate for the treatment of liver disease. However, the qualitative and quantitative analysis, pharmacokinetics-pharmacodynamics and mechanism of action also need in-depth study.
Asunto(s)
Cirsium/química , Medicamentos Herbarios Chinos/farmacología , Medicina Tradicional China/métodos , Animales , China , Medicamentos Herbarios Chinos/química , Etnofarmacología , HumanosRESUMEN
Polygonatum cyrtonema is a known tonic herb in Chinese Materia Medica, extensively consumed in China, but the structure and activity of its polysaccharide components remain to be clarified. Herein, two new polysaccharides (a fructan and a galactan) were purified from the dried and the processed P. cyrtonema rhizome, respectively. Structural analysis suggested that the fructan consisted of a (2 â 6) linked ß-d-Fruf residues backbone with an internal α-d-Glcp residue and two (2 â 1) linked ß-d-Fruf residues branches, and that the galactan was a (1 â 4)-ß-d-galactan branched with a single ß-d-galactose at C-6 at about every nine residues in its main chain. The bioactive assay showed that the fructan and the galactan remarkably promoted growth of Bifidobacterium and Lactobacillus strains, indicating that they possess prebiotic activity. These findings may help expand the application of the polysaccharides from the tonic herb P. cyrtonema as functional ingredients in food products.
Asunto(s)
Fructanos/química , Fructanos/metabolismo , Galactanos/química , Galactanos/metabolismo , Polygonatum/química , Bifidobacterium/metabolismo , Secuencia de Carbohidratos , Fructanos/aislamiento & purificación , Galactanos/aislamiento & purificación , Lactobacillus/metabolismo , Peso Molecular , PrebióticosRESUMEN
The serotonin (5-hydroxytryptamine) type 3 receptor is an important target in the control of digestive dysfunction such as anorexia and bulimia, and 5-HT3 receptor antagonists are effective against eating disorder and the early-phase chemotherapy and radiotherapy evoked vomiting. Our previous research of Valeriana jatamansi revealed the presence of iridoids, which showed potent antitumor activities. Here, we explored the effects of 10π aromatic iridoid desacylbaldrinal isolated from V. jatamansi on the 5-HT3 receptor current. We performed whole cell recordings of 5-HT3A receptor currents in the presence of the compound. The result indicated that desacylbaldrinal inhibited the 5-HT-mediated 5-HT3A receptor current.
Asunto(s)
Iridoides/farmacología , Receptores de Serotonina 5-HT3 , Antagonistas del Receptor de Serotonina 5-HT3/farmacología , Serotonina , Valeriana/química , Humanos , Iridoides/aislamiento & purificación , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Antagonistas del Receptor de Serotonina 5-HT3/aislamiento & purificaciónRESUMEN
A new abietane diterpenoid glycoside, ajugaside B (1), along with three known compounds (2-4), were isolated from the whole plants of Ajuga ovalifolia var. calantha. The structure of the new compound (1) was elucidated by means of spectroscopic analyses (HRESIMS, IR, NMR and ECD). All of the isolated compounds were evaluated for their antitumor activities against MGC803, MCF-7, A549, HT29 and HepG2 cell lines. Compounds 3-4 showed moderate cytotoxicity against all tested cell lines with IC50 values of 1.8-7.3 µM.
Asunto(s)
Abietanos/farmacología , Ajuga/química , Antineoplásicos Fitogénicos/farmacología , Abietanos/química , Antineoplásicos Fitogénicos/química , Línea Celular Tumoral , Glicósidos/química , Glicósidos/farmacología , Humanos , Estructura Molecular , Extractos Vegetales/químicaRESUMEN
The ethyl acetate extract from the seeds of Herpetospermum caudigerum was found to show protective effects on carbon tetrachloride (CCl(4)) and thioacetamide (TAA)-induced acute hepatic injuries in mice. From the ethyl acetate extract, two new coumarins, herpetolide A (1) and herpetolide B (2), along with four known compounds, herpetone (3), dehydrodiconiferyl alcohol (4), 2,4-dihydroxypyrimidine (5) and stigmasterol (6) were isolated. The structures of the new coumarins were elucidated on the basis of chemical and physicochemical evidences. Herpetone exhibited protective effects on CCl(4)-induced hepatocyte injury.