RESUMEN
Ginkgo biloba L. has been used in traditional Chinese medicine (TCM) for thousands of years. However, the anti-cancer properties of ginkgolic acids (GAS) isolated from G. biloba have not been investigated in human nasopharyngeal carcinoma cells. In this study, GAS exhibited an inhibitory effect on the ATPase activity of heat shock protein 90 (Hsp90) and anti-proliferative activities against four human cancer cell lines, with IC50 values ranging from 14.91 to 23.81 µg·mL-1. In vivo experiments confirmed that GAS inhibited tumor growth in CNE-2Z cell-xenografted nude mice with low hepatotoxicity. We further demonstrated that GAS suppressed migration and invasion and induced the apoptosis of CNE-2Z cells by inducing the degradation of Hsp90 client proteins (MMP-2, MMP-9, Her-2, c-Raf, Akt, and Bcl-2). Together, GAS are new Hsp90 inhibitors by binding to Hsp90 (hydrogen bond and hydrophobic interaction). Thus, GAS from G. biloba might represent promising Hsp90 inhibitors for the development of anti-nasopharyngeal carcinoma agents.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Ginkgo biloba/química , Proteínas HSP90 de Choque Térmico/antagonistas & inhibidores , Carcinoma Nasofaríngeo/tratamiento farmacológico , Neoplasias Nasofaríngeas/tratamiento farmacológico , Salicilatos/farmacología , Animales , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Movimiento Celular/efectos de los fármacos , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Femenino , Proteínas HSP90 de Choque Térmico/metabolismo , Humanos , Ratones , Ratones Endogámicos BALB C , Ratones Desnudos , Carcinoma Nasofaríngeo/metabolismo , Carcinoma Nasofaríngeo/patología , Neoplasias Nasofaríngeas/metabolismo , Neoplasias Nasofaríngeas/patología , Salicilatos/química , Salicilatos/aislamiento & purificación , Células Tumorales CultivadasRESUMEN
Salix cortex-containing medicine is used against pain conditions, fever, headaches, and inflammation, which are partly mediated via arachidonic acid-derived prostaglandins (PGs). We used an activity-guided fractionation strategy, followed by structure elucidation experiments using LC-MS/MS, CD-spectroscopy, and 1D/2D NMR techniques, to identify the compounds relevant for the inhibition of PGE2 release from activated human peripheral blood mononuclear cells. Subsequent compound purification by means of preparative and semipreparative HPLC revealed 2'-O-acetylsalicortin (1), 3'-O-acetylsalicortin (2), 2'-O-acetylsalicin (3), 2',6'-O-diacetylsalicortin (4), lasiandrin (5), tremulacin (6), and cinnamrutinose A (7). In contrast to 3 and 7, compounds 1, 2, 4, 5, and 6 showed inhibitory activity against PGE2 release with different potencies. Polyphenols were not relevant for the bioactivity of the Salix extract but salicylates, which degrade to, e.g., catechol, salicylic acid, salicin, and/or 1-hydroxy-6-oxo-2-cycohexenecarboxylate. Inflammation presents an important therapeutic target for pharmacological interventions; thus, the identification of relevant key drugs in Salix could provide new prospects for the improvement and standardization of existing clinical medicine.
Asunto(s)
Inflamación/tratamiento farmacológico , Salicilatos/aislamiento & purificación , Salix/química , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Células Cultivadas , Cromatografía Liquida , Dinoprostona/metabolismo , Humanos , Leucocitos Mononucleares/efectos de los fármacos , Leucocitos Mononucleares/metabolismo , Terapia Molecular Dirigida/métodos , Terapia Molecular Dirigida/tendencias , Dolor/tratamiento farmacológico , Fitoterapia/métodos , Corteza de la Planta/química , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Extractos Vegetales/uso terapéutico , Salicilatos/análisis , Salicilatos/farmacología , Espectrometría de Masas en TándemRESUMEN
Fall armyworm (Spodoptera frugiperda) is a major global pest of many crops, including maize (Zea mays). This insect is known to use host plant-derived volatile organic compounds to locate suitable hosts during both its adult and larval stages, yet the function of individual compounds remains mostly enigmatic. In this study, we use a combination of volatile profiling, electrophysiological assays, pair-wise choice behavioral assays, and chemical supplementation treatments to identify and assess specific compounds from maize that influence S. frugiperda host location. Our findings reveal that methyl salicylate and (E)-alpha-bergamotene are oviposition attractants for adult moths but do not impact larval behavior. While geranyl acetate can act as an oviposition attractant or repellent depending on the host volatile context and (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT) is an oviposition deterrent. These compounds can also be attractive to the larvae when applied to specific maize inbreds. These data show that S. frugiperda uses different plant volatile cues for host location in its adult and larval stage and that the background volatile context that specific volatiles are perceived in, alters their impact as behavioral cues.
Asunto(s)
Herbivoria/efectos de los fármacos , Oviposición/efectos de los fármacos , Spodoptera/fisiología , Compuestos Orgánicos Volátiles/farmacología , Zea mays/química , Animales , Compuestos Bicíclicos con Puentes/aislamiento & purificación , Compuestos Bicíclicos con Puentes/farmacología , Cromatografía de Gases y Espectrometría de Masas , Larva/fisiología , Hojas de la Planta/química , Hojas de la Planta/metabolismo , Análisis de Componente Principal , Salicilatos/aislamiento & purificación , Salicilatos/farmacología , Spodoptera/crecimiento & desarrollo , Terpenos/aislamiento & purificación , Terpenos/farmacología , Compuestos Orgánicos Volátiles/química , Zea mays/metabolismoRESUMEN
Methyl salicylate (MeSA) is a plant metabolite that induces plant defence resistance and an odorous volatile compound presenting green nuances. This volatile compound was shown to be present in wine samples, sometimes at concentrations above its olfactory detection threshold. MeSA is localized in grapes, particularly in the skins and stems, and is extracted during red wine vinification. It was detected at the highest concentrations in wines of several grape varieties, made from grapes affected by cryptogamic diseases, namely downy mildew caused by Plasmopara viticola, and black rot caused by Guignardia bidwellii. It has also been detected in wines from vines affected by Esca, a Grapevine Trunk Disease. MeSA can also be considered to be a chemical marker in grapes and wine indicative of the level of development of several vine cryptogamic diseases.
Asunto(s)
Salicilatos/análisis , Vitis/química , Vino/análisis , Ascomicetos/crecimiento & desarrollo , Ascomicetos/metabolismo , Cromatografía Líquida de Alta Presión , Frutas/química , Frutas/metabolismo , Cromatografía de Gases y Espectrometría de Masas , Humanos , Enfermedades de las Plantas/microbiología , Salicilatos/aislamiento & purificación , Extracción en Fase Sólida , Gusto/fisiología , Vitis/metabolismoRESUMEN
This study reports the inâ vitro anticoagulation activity of acetonic extract (AE) of 42 lichen species and the identification of potential bioavailable anticoagulant compounds from Umbilicaria decussata as a competent anticoagulant lichen species. Lichens' AEs were evaluated for their anticoagulant activity by monitoring activated partial thromboplastin time (APTT) and prothrombin time (PT) assays. A strong, positive correlation was observed between total phenolics concentration (TPC) of species and blood coagulation parameters. U. decussata was the only species with the longest clotting time in both APTT and PT assays. The research was moved forward by performing inâ vivo assays using rats. The results corroborated the dose-dependent impact of U. decussata's AE on rats' clotting time. Major secondary metabolites of U. decussata and their plasma-related bioavailability were also investigated using LC-ESI-MS/MS. Atranol, orsellinic acid, D-mannitol, lecanoric acid, and evernic acid were detected as possible bioavailable anticoagulants of U. decussata. Our findings suggest that U. decussata might be a potential anticoagulant lichen species that can be used for the prevention or treatment of coagulation-related issues such as cardiovascular diseases (CVDs).
Asunto(s)
Anticoagulantes/farmacología , Líquenes/química , Extractos Vegetales/farmacología , Anticoagulantes/química , Anticoagulantes/aislamiento & purificación , Benzaldehídos/química , Benzaldehídos/aislamiento & purificación , Benzaldehídos/farmacología , Coagulación Sanguínea/efectos de los fármacos , Pruebas de Coagulación Sanguínea , Relación Dosis-Respuesta a Droga , Hidroxibenzoatos/química , Hidroxibenzoatos/aislamiento & purificación , Hidroxibenzoatos/farmacología , Manitol/química , Manitol/aislamiento & purificación , Manitol/farmacología , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Resorcinoles/química , Resorcinoles/aislamiento & purificación , Resorcinoles/farmacología , Salicilatos/química , Salicilatos/aislamiento & purificación , Salicilatos/farmacologíaRESUMEN
The decontamination of exposed persons is a priority following the release of toxic chemicals. Efficacious decontamination reduces the risk of harm to those directly affected and prevents the uncontrolled spread of contamination. Human studies examining the effectiveness of emergency decontamination procedures have primarily focused on decontaminating skin, with few examining the decontamination of hair and scalp. We report the outcome of two studies designed to evaluate the efficacy of current United Kingdom (UK) improvised, interim and specialist mass casualty decontamination protocols when conducted in sequence. Decontamination efficacy was evaluated using two chemical simulants, methyl salicylate (MeS) and benzyl salicylate (BeS) applied to and recovered from the hair of volunteers. Twenty-four-hour urinary MeS and BeS were measured as a surrogate for systemic bioavailability. Current UK decontamination methods performed in sequence were partially effective at removing MeS and BeS from hair and underlying scalp. BeS and MeS levels in urine indicated that decontamination had no significant effect on systemic exposure raising important considerations with respect to the speed of decontamination. The decontamination of hair may therefore be challenging for first responders, requiring careful management of exposed persons following decontamination. Further work to extend these studies is required with a broader range of chemical simulants, a larger group of volunteers and at different intervention times.
Asunto(s)
Descontaminación/métodos , Cabello/química , Salicilatos/aislamiento & purificación , Adulto , Femenino , Voluntarios Sanos , Humanos , Masculino , Incidentes con Víctimas en Masa , Salicilatos/orina , Cuero Cabelludo/química , Reino UnidoRESUMEN
The UK Initial Operational Response (IOR) to chemical incidents includes improvised decontamination procedures, which use readily available materials to rapidly reduce risk to potentially exposed persons. A controlled, cross-over human volunteer study was conducted to investigate the effectiveness of improvised dry and wet decontamination procedures on skin, both alone, and in sequence. A simulant contaminant, methyl salicylate (MeS) in vegetable oil with a fluorophore was applied to three locations (shoulder, leg, arm). Participants then received no decontamination (control) or attempted to remove the simulant using one of three improvised protocols (dry decontamination; wet decontamination; combined dry and wet decontamination). Simulant remaining on the skin following decontamination was quantified using both Gas Chromatography Tandem Mass Spectrometry (GC-MSMS) for analysis of MeS and UV imaging to detect fluorophores. Additionally, urine samples were collected for 24 hours following application for analysis of MeS. Significantly less simulant was recovered from skin following each improvised decontamination protocol, compared to the no decontamination control. Further, combined dry and wet decontamination resulted in lower recovery of simulant when compared to either dry or wet decontamination alone. Irrespective of decontamination protocol, significantly more simulant remained on the shoulders compared to either the arms or legs, suggesting that improvised decontamination procedures are less effective for difficult to reach areas of the body. There was no effect of decontamination on excreted MeS in urine over 24 hours. Overall, findings indicate that improvised decontamination is an effective means of rapidly removing contaminants from skin, and combinations of improvised approaches can increase effectiveness in the early stages of decontamination and in the absence of specialist resources at an incident scene. However, the variable control and consistency of improvised decontamination techniques means that further intervention is likely to be needed, particularly for less accessible areas of the body.
Asunto(s)
Liberación de Peligros Químicos/prevención & control , Descontaminación/métodos , Aceites de Plantas/aislamiento & purificación , Salicilatos/aislamiento & purificación , Piel , Adulto , Brazo , Estudios Cruzados , Femenino , Cromatografía de Gases y Espectrometría de Masas/métodos , Voluntarios Sanos , Humanos , Pierna , Masculino , Persona de Mediana Edad , Aceites de Plantas/análisis , Reproducibilidad de los Resultados , Salicilatos/análisis , Salicilatos/orina , HombroRESUMEN
Parmelia that belongs to the Parmeliaceae Family is a foliose lichen combined with one or two groups of fungi in Phylum Ascomycota or Basidiomycota and algae, which might be green algae or blue-green algae (cyanobacteria). It is generally called "Stone Flower," "Charila," "Pattharphool," or "Shilaaapushpa" in India. Lichen can be generally found growing on walls, old trees and spread largely across India, especially in the mountain area. It is a source of edible organisms for people residing in some regions of Nepal and it is also cultivated in hillsides of Kashmir. It has been found that lichen contains a lot of distinctive chemical compounds such as evernic acid, lecanoric acid, lobaric acid, norstictic acid, physodic acid, and salazinic acid. Some species of this lichen are recommended traditionally for controlling diseases such as boils, bronchitis, inflammations, excessive salivation, toothache, vomiting, etc. It has also applied as an indicator for biomonitoring, astringent, carminative, demulcent, bitter, resolvent, emollient, laxative, sporofic, sedative, diuretic and considered for treating sores, bronchitis, excessive salivation, vomiting, tooth-ache, boils and inflammations. It has been utilized for preparing traditional food and acts as a bioindicator for air pollution and radiation. It shows antibacterial, antioxidant, antimycobacterial and antifungal activities, including haemolytic, anaesthetic, spasmolytic and antispasmodic and antitumour activities. It also has several unique phytoconstituents that could be in charge of different therapeutic activities, but the majority of them are still unexplored. The review mainly focuses on various facets, such as common names, synonyms, traditional uses, botanical descriptions, and pharmacological activities of seven species of Parmelia.
Asunto(s)
Hidroxibenzoatos/farmacología , Lactonas/farmacología , Parmeliaceae/crecimiento & desarrollo , Salicilatos/farmacología , Depsidos/aislamiento & purificación , Depsidos/farmacología , Humanos , Hidroxibenzoatos/aislamiento & purificación , Lactonas/aislamiento & purificación , Medicina Tradicional , Parmeliaceae/química , Parmeliaceae/clasificación , Salicilatos/aislamiento & purificaciónRESUMEN
Glycosides are ubiquitous plant secondary metabolites consisting of a non-sugar component called an aglycone, attached to one or more sugars. One of the most interesting aglycones in grapes and wine is methyl salicylate (MeSA), an organic ester naturally produced by many plants, particularly wintergreens. To date, nine different MeSA glycosides from plants have been reported, mainly spread over the genera Gaultheria, Camellia, Polygala, Filipendula, and Passiflora. From a sensorial point of view, MeSA has a balsamic-sweet odor, known as Wintergreen. MeSA was found in Vitis riparia grapes, in Vitis vinifera sp. and in the Frontenac interspecific hybrid. We found that the MeSA glycosides content in Verdicchio wines and in some genetically related varieties (Trebbiano di Soave and Trebbiano di Lugana) was very high. In order to understand which glycosides were present in wine, the methanolic extract of Verdicchio wine was injected into a UPLC-Q-TOF-HDMS and compared to the extracts of different plants rich in such glycosides. Using pure standards, we confirmed the existence of two glycosides in wine: MeSA 2-O-ï¢-d-glucoside and MeSA 2-O-ï¢-d-xylopyranosyl (1-6) ï¢-d-glucopyranoside (gaultherin). For the first time, we also tentatively identified other diglycosides in wine: MeSA 2-O-ï¡-l-arabinopyranosyl (1-6)-ï¢-d-glucopyranoside (violutoside) and MeSA 2-O-ï¢-d-apiofuranosyl (1-6)-ï¢-d-glucopyranoside (canthoside A), MeSA 2-O-ï¢-d-glucopyranosyl (1-6)-O-ï¢-d-glucopyranoside (gentiobioside) and MeSA 2-O-ï¡-l-rhamnopyranosyl (1-6)-ï¢-d-glucopyranoside (rutinoside). Some of these glycosides have been isolated from Gaultheria procumbens leaves by preparative liquid chromatography and structurally annotated by 1H- and 13C-NMR analysis. Two of the peaks isolated from Gaultheria procumbens leaves, namely MeSA sambubioside and MeSA sophoroside, were herein observed for the first time. Six MeSA glycosides were quantified in 64 Italian white wines, highlighting the peculiar content and pattern in Verdicchio wines and related cultivars. The total concentration in bound and free MeSA in Verdicchio wines varied in the range of 456-9796 ïg/L and 5.5-143 ïg/L, respectively, while in the other wines the bound and free MeSA was below 363 ïg/L and 12 ïg/L, respectively. As this compound's olfactory threshold is between 50 and 100 ïg/L, our data support the hypothesis that methyl salicylate can contribute to the balsamic scent, especially in old Verdicchio wines.
Asunto(s)
Glicósidos/química , Salicilatos/química , Vitis/química , Vino/análisis , Cromatografía Liquida , Disacáridos/química , Disacáridos/aislamiento & purificación , Glicósidos/clasificación , Glicósidos/aislamiento & purificación , Humanos , Extractos Vegetales/química , Hojas de la Planta/química , Salicilatos/clasificación , Salicilatos/aislamiento & purificaciónRESUMEN
A valid and reliable method was established to separate six compounds from pigeon pea leaves via elution-extrusion counter-current chromatography. A solvent system composed of n-hexane/methanol/formic acid aqueous solution with pH = 3 (10:6:4, v/v) was screened to achieve satisfactory isolation from the ethanol extract of pigeon pea leaves. Four compounds, 9.2 mg of compound 1 (96.8%), 3.2 mg of 2 (88.0%), 6.2 mg of 4 (94.2%) and 25.2 mg of 5 (94.2%), were obtained by conventional elution from 100 mg of the precipitation fraction, respectively. Two compounds, 14.4 mg of 3 (96.3%) and 28.1 mg of 6 (96.6%), with high K values were obtained by the subsequent extrusion procedure. The compounds 1-6 were identified as 3-methoxy-5-(2-phenylethenyl)-phenol, pinostrobin chalcone, pinostrobin, 2-hydroxy-4-methoxy-6-(2-phenylvinyl)-benzoic acid, longistylin C and cajaninstilbene acid by quadrupole time-of-flight mass spectrometry, and 1 H and 13 C NMR spectroscopy. The in vitro antiproliferation activities of compounds 1, 5 and 6 against human hepatoma cell were evaluated and the half-maximum inhibitory concentrations were acquired.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Ácido Benzoico/farmacología , Flavanonas/farmacología , Fenoles/farmacología , Pisum sativum/química , Salicilatos/farmacología , Estilbenos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Ácido Benzoico/química , Ácido Benzoico/aislamiento & purificación , Proliferación Celular/efectos de los fármacos , Distribución en Contracorriente , Ensayos de Selección de Medicamentos Antitumorales , Flavanonas/química , Flavanonas/aislamiento & purificación , Células Hep G2 , Humanos , Estructura Molecular , Fenoles/química , Fenoles/aislamiento & purificación , Hojas de la Planta/química , Salicilatos/química , Salicilatos/aislamiento & purificación , Estilbenos/química , Estilbenos/aislamiento & purificaciónRESUMEN
Herein we report the anti-inflammatory activity of lobaric acid and pseudodepsidones isolated from the nordic lichen Stereocaulon paschale. Lobaric acid (1) and three compounds (2, 7 and 9) were found to inhibit the NF-κB activation and the secretion of pro-inflammatory cytokines (IL-1ß and TNF-α) in LPS-stimulated macrophages. Inhibition and docking simulation experiments provided evidence that lobaric acid and pseudodepsidones bind to PPAR-γ between helix H3 and the beta sheet, similarly to partial PPAR-γ agonists. These findings suggest that lobaric acid and pseudodepsidones reduce the expression of pro-inflammatory cytokines by blocking the NF-κB pathway via the activation of PPAR-γ.
Asunto(s)
Antiinflamatorios no Esteroideos/farmacología , Depsidos/farmacología , Lactonas/farmacología , Líquenes/química , FN-kappa B/antagonistas & inhibidores , PPAR gamma/agonistas , Salicilatos/farmacología , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/aislamiento & purificación , Supervivencia Celular/efectos de los fármacos , Depsidos/química , Depsidos/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Humanos , Lactonas/química , Lactonas/aislamiento & purificación , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Macrófagos/efectos de los fármacos , Simulación del Acoplamiento Molecular , Estructura Molecular , FN-kappa B/metabolismo , PPAR gamma/metabolismo , Salicilatos/química , Salicilatos/aislamiento & purificación , Transducción de Señal/efectos de los fármacos , Relación Estructura-Actividad , Células U937RESUMEN
An efficient coordination high-speed counter-current chromatography method for the preparative separation of ginkgolic acids from the sarcotesta of Ginkgo biloba L was developed. The type, concentration, and mechanism of the coordination agent were investigated. Following the use of four types of metal salts including silver nitrate, copper chloride, ferric chloride, and aluminium nitrate, n-heptane/ethyl acetate/methanol/acetic acid 5:4:1:1, v/v with 0.20 mol/L silver nitrate as the coordination agent was chosen as the optimum two-phase solvent system. Five main ginkgolic acids including C13:0, C15:0, C15:1, C17:1, and C17:2 were successfully separated with purities greater than 98%. The sample loading was 500 mg, the flow-rate was 2.0 mL/min, rotation speed was 800 rpm and temperature was 20°C. The structures of the separated ginkgolic acids were identified by comparison with standard samples and electrospray ionization mass spectrometry. The introduction of coordination chemistry in high-speed counter-current chromatography is novel and effective for the preparative separation and isolation of ginkgolic acids from the sarcotesta of Ginkgo biloba L and could also be applied to separate compounds which form coordination bonds in other complex natural products.
Asunto(s)
Ginkgo biloba/química , Extractos Vegetales/aislamiento & purificación , Salicilatos/aislamiento & purificación , Distribución en Contracorriente , Estructura Molecular , Extractos Vegetales/química , Salicilatos/químicaRESUMEN
Lobaric acid and lobarstin, secondary metabolites derived from the antarctic lichen Stereocaulon alpnum, exert various biological activities, including antitumor, anti-proliferation, anti-inflammation, and antioxidant activities. However, the underlying mechanisms of these effects have not yet been elucidated in human cervix adenocarcinoma and human colon carcinoma. In the present study, we evaluated the anticancer effects of lobaric acid and lobarstin on human cervix adenocarcinoma HeLa cells and colon carcinoma HCT116 cells. We show that the proliferation of Hela and HCT116 cells treated with lobaric acid and lobarstin significantly decreased in a dose- and time-dependent manner. Using flow cytometry analysis, we observed that the treatment with these compounds resulted in significant apoptosis in both cell lines, following cell cycle perturbation and arrest in G2/M phase. Furthermore, using immunoblot analysis, we investigated the expression of cell cycle and apoptosis-related marker genes and found a significant downregulation of the apoptosis regulator B-cell lymphoma 2 (Bcl-2) and upregulation of the cleaved form of the poly (ADP-ribose) polymerase (PARP), a DNA repair and apoptosis regulator. These results suggest that lobaric acid and lobarstin could significantly inhibit cell proliferation through cell cycle arrest and induction of apoptosis via the mitochondrial apoptotic pathway in cervix adenocarcinoma and colon carcinoma cells. Taken together, our data suggests that lobaric acid and lobarstin might be novel agents for clinical treatment of cervix adenocarcinoma and colon carcinoma.
Asunto(s)
Antineoplásicos/farmacología , Benzofuranos/farmacología , Neoplasias del Colon/metabolismo , Hidroxibenzoatos/farmacología , Lactonas/farmacología , Líquenes/química , Salicilatos/farmacología , Neoplasias del Cuello Uterino/metabolismo , Antineoplásicos/aislamiento & purificación , Benzofuranos/química , Benzofuranos/aislamiento & purificación , Puntos de Control del Ciclo Celular/efectos de los fármacos , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Neoplasias del Colon/tratamiento farmacológico , Depsidos/química , Depsidos/aislamiento & purificación , Depsidos/farmacología , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Femenino , Regulación Neoplásica de la Expresión Génica/efectos de los fármacos , Células HCT116 , Células HeLa , Humanos , Hidroxibenzoatos/química , Hidroxibenzoatos/aislamiento & purificación , Lactonas/química , Lactonas/aislamiento & purificación , Estructura Molecular , Poli(ADP-Ribosa) Polimerasas/metabolismo , Proteínas Proto-Oncogénicas c-bcl-2/metabolismo , Salicilatos/química , Salicilatos/aislamiento & purificación , Neoplasias del Cuello Uterino/tratamiento farmacológicoRESUMEN
A method to introduce target analytes to a chromatograph from a single drop of whole blood was investigated for minimally invasive monitoring of anionic pharmaceuticals. In this work, salicylate and loxoprofen were examined as organic anions. A micro ion extractor (MIE) has been developed for extraction of inorganic trace anions from whole blood, but this device is not suitable for extraction of pharmaceuticals. In the present study, we improved and optimized the MIE device for organic anion extraction. Various supported liquid membranes were evaluated for use as the ion transfer membrane, with each membrane placed between a droplet sample (donor) and an acceptor solution. A supported liquid membrane of porous polypropylene impregnated with 1-butanol was selected. In addition, the methods for electric field creation and electrode contact were examined to improve the characteristics of the MIE device. The current and extraction time were also optimized. With the optimized method, salicylate and loxoprofen were successfully extracted from a single drop of whole blood. Changes in the concentrations of these pharmaceuticals in blood over time were monitored after administration. As only 25µL of whole blood was required for analysis, repeat measurements could be conducted to monitor changes in the concentrations. This MIE will be useful for monitoring pharmaceutical concentrations in blood.
Asunto(s)
Análisis Químico de la Sangre/métodos , Recolección de Muestras de Sangre/métodos , Membranas Artificiales , Preparaciones Farmacéuticas/aislamiento & purificación , Animales , Aniones/química , Técnicas Electroquímicas/instrumentación , Técnicas Electroquímicas/métodos , Caballos , Humanos , Preparaciones Farmacéuticas/sangre , Preparaciones Farmacéuticas/química , Fenilpropionatos/sangre , Fenilpropionatos/química , Fenilpropionatos/aislamiento & purificación , Diálisis Renal/instrumentación , Diálisis Renal/métodos , Reproducibilidad de los Resultados , Salicilatos/sangre , Salicilatos/química , Salicilatos/aislamiento & purificación , Factores de TiempoRESUMEN
Three new salicylic acid derivatives (1-3) and a known one, 6-(3'-hydroxypropyl)-2-hydroxybenzoic acid (4), together with seven known phenylspirodrimanes (5-11), were isolated from the sponge-associated fungus Hansfordia sinuosae, collected from the South China Sea. HRESIMS, FT-IR Spectroscopy, and NMR techniques including COSY, HSQC, and HMBC were used to elucidate the structures of these compounds. The inhibitory effects of the isolated compounds (1-11) against HIV-1 virus were evaluated, and most of the phenylspirodrimanes (5, 8-11) showed varying degrees of anti-HIV activity.
Asunto(s)
Hongos/química , Poríferos/microbiología , Salicilatos/aislamiento & purificación , Sesquiterpenos/aislamiento & purificación , Animales , Fármacos Anti-VIH/farmacología , VIH-1/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Sesquiterpenos Policíclicos , Salicilatos/química , Salicilatos/farmacología , Sesquiterpenos/química , Sesquiterpenos/farmacologíaRESUMEN
A novel method based on direct analysis in real time integrated with mass spectrometry was established and applied into rapid determination of ginkgolic acids in Ginkgo biloba kernels and leaves. Instrument parameter settings were optimized to obtain the sensitive and accurate determination of ginkgolic acids. At the sample introduction speed of 0.2 mm/s, high intensity of [M-H]- ions for ginkgolic acids were observed in the negative ion mode by utilization of high-purity helium gas at 450°C. Two microliters of methanol extract of G. biloba kernels or leaves dropped on the surface of Quick-Strip module was analyzed after solvent evaporated to dryness. A series of standard solutions of ginkgolic acid 13:0 in the range of 2-50 mg/L were analyzed with a correlation coefficient r = 0.9981 and relative standard deviation (n = 5) from 12.5 to 13.7%. The limit of detection was 0.5 mg/L. The results of direct analysis in real time-mass spectrometry were in agreement with those observed by thermochemolysis gas chromatography. The proposed method demonstrated significant potential in the application of the high-throughput screening and rapid analysis for ginkgolic acids in dietary supplements.
Asunto(s)
Ginkgo biloba/química , Hojas de la Planta/química , Salicilatos/aislamiento & purificación , Suplementos Dietéticos/análisis , Espectrometría de MasasRESUMEN
Ten new salicyloid derivatives, namely vaccinols J-S (1-10), along with five known compounds (11-15) were isolated from Pestalotiopsis vaccinii (cgmcc3.9199) endogenous with the mangrove plant Kandelia candel (L.) Druce (Rhizophoraceae). Their structures including absolute configurations were established on the basis of spectroscopic analysis, optical rotation, CD spectra, quantum ECD calculations. To the best of our knowledge, vaccinol J (1) is the first example of salicyloid derivatives containing 2-methylfuran moiety. All of the new compounds were tested for their anti-enterovirus 7l (EV71) and cytotoxic activities. Among them, vaccinol J (1) exhibited in vitro anti-EV71 with IC50 value of 30.7µM (IC50 177.0µM for the positive control ribavirin).
Asunto(s)
Rhizophoraceae/microbiología , Salicilatos/farmacología , Xylariales/química , Antivirales/aislamiento & purificación , Antivirales/farmacología , Línea Celular Tumoral , Enterovirus Humano A/efectos de los fármacos , Humanos , Estructura Molecular , Salicilatos/aislamiento & purificaciónRESUMEN
Chemical investigation of the methanol extract of the fertile form of Roccella montagnei collected in Vietnam afforded twelve secondary metabolites, including five new montagnetol derivatives, orsellinylmontagnetols A-D and a furanyl derivative together with seven known compounds. Their chemical structures were elucidated by analysis of 1D and 2D NMR and high resolution mass spectroscopic data. The relative stereochemistry of two chiral centers (C-2 and C-3) of orsellinylmontagnetols A and B was elucidated by comparison of their coupling constants and the specific rotation with those reported in the literature while the absolute stereochemistry was determined by the application of a modified Mosher method for the hydroxy group at C-3. The absolute configuration (2R,3S) of the butanetetraol moiety of these compounds is in accordance with that of erythrin, a recognized chemotaxonomic marker of the genus Roccella. Five of these compounds were evaluated for their cytotoxic activities against four cancer cell lines. Only orsellinylmontagnetol A exerted a moderate activity against MCF-7 cell line with an IC50 value of 68.39 ± 3.46 µM.
Asunto(s)
Antineoplásicos/química , Ascomicetos/química , Eritritol/química , Líquenes/química , Antineoplásicos/aislamiento & purificación , Línea Celular Tumoral , Eritritol/análogos & derivados , Eritritol/aislamiento & purificación , Humanos , Estructura Molecular , Salicilatos/química , Salicilatos/aislamiento & purificación , VietnamRESUMEN
In recent years, the increased popularity of functional beverages such as herbal teas and decoctions has led to the search for new sources of raw materials that provide appropriate taste and functionality to consumers. The objective of this study was to investigate the nutritional, phytochemical profiles and bioactivities of possible functional beverages produced from F. ulmaria and its alternative substitutes (F. camtschatica, F. denudata, F. stepposa). The investigated decoctions were analyzed regarding their macronutrient, carbohydrate, organic acid, amino acid and mineral composition. Quantification of the main phenolic compounds in the decoctions of meadowsweet floral teas was performed by a microcolumn RP-HPLC-UV procedure; the highest content was revealed in F. stepposa tea. The investigation of the essential oil of four meadowsweet teas revealed the presence of 28 compounds, including simple phenols, monoterpenes, sesquiterpenes and aliphatic components. The dominance of methyl salicylate and salicylaldehyde was noted in all samples. Studies on the water soluble polysaccharides of Filipendula flowers allowed us to establish their general affiliation to galactans and/or arabinogalactans with an admixture of glucans of the starch type and galacturonans as minor components. The bioactivity data demonstrated a good ability of meadowsweet teas to inhibit amylase, α-glucosidase and AGE formation. Tea samples showed antioxidant properties by the DPPHâ¢, ABTSâ¢+ and Br⢠free radicals scavenging assays and the carotene bleaching assay, caused by the presence of highly active ellagitannins. The anti-complement activity of the water-soluble polysaccharide fraction of meadowsweet teas indicated their possible immune-modulating properties. Filipendula beverage formulations can be expected to deliver beneficial effects due to their unique nutritional and phytochemical profiles. Potential applications as health-promoting functional products may be suggested.
Asunto(s)
Antioxidantes/aislamiento & purificación , Filipendula/química , Flavonoides/aislamiento & purificación , Factores Inmunológicos/aislamiento & purificación , Extractos Vegetales/química , Tés de Hierbas/análisis , Aldehídos/química , Aldehídos/aislamiento & purificación , Aldehídos/farmacología , Amilasas/antagonistas & inhibidores , Amilasas/genética , Amilasas/metabolismo , Antioxidantes/química , Antioxidantes/farmacología , Benzotiazoles/antagonistas & inhibidores , Compuestos de Bifenilo/antagonistas & inhibidores , Cromatografía Líquida de Alta Presión/métodos , Proteínas del Sistema Complemento/química , Filipendula/clasificación , Flavonoides/química , Flavonoides/farmacología , Humanos , Taninos Hidrolizables/química , Taninos Hidrolizables/aislamiento & purificación , Taninos Hidrolizables/farmacología , Factores Inmunológicos/química , Factores Inmunológicos/farmacología , Monoterpenos/química , Monoterpenos/aislamiento & purificación , Monoterpenos/farmacología , Fenoles/química , Fenoles/aislamiento & purificación , Fenoles/farmacología , Picratos/antagonistas & inhibidores , Polisacáridos/química , Polisacáridos/aislamiento & purificación , Polisacáridos/farmacología , Receptor para Productos Finales de Glicación Avanzada/antagonistas & inhibidores , Receptor para Productos Finales de Glicación Avanzada/genética , Receptor para Productos Finales de Glicación Avanzada/metabolismo , Salicilatos/química , Salicilatos/aislamiento & purificación , Salicilatos/farmacología , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Especificidad de la Especie , Ácidos Sulfónicos/antagonistas & inhibidores , alfa-Glucosidasas/genética , alfa-Glucosidasas/metabolismoRESUMEN
Microbes belonging to the genus Verrucosispora possess significant chemical diversity and biological properties. They have attracted the interests of many researchers and are becoming promising resources in the marine natural product research field. A bioassay-guided isolation from the crude extract of Verrucosispora sp. strain MS100047, isolated from sediments collected from the South China Sea, has led to the identification of a new salicylic derivative, glycerol 1-hydroxy-2,5-dimethyl benzoate (1), along with three known compounds, brevianamide F (2), abyssomicin B (3), and proximicin B (4). Compound 1 showed selective activity against methicillin-resistant Staphylococcus aureus (MRSA) with a minimum inhibitory concentration (MIC) value of 12.5 µg/mL. Brevianamide F (2), which was isolated from actinomycete for the first time, showed a good anti-BCG activity with a MIC value of 12.5 µg/mL that has not been reported previously in literatures. Proximicin B (4) showed significant anti-MRSA (MIC = 3.125 µg/mL), anti-BCG (MIC = 6.25 µg/mL), and anti-tuberculosis (TB) (MIC = 25 µg/mL) activities. This is the first report on the anti-tubercular activities of proximicins. In addition, Verrucosispora sp. strain MS100047 was found to harbor 18 putative secondary metabolite gene clusters based on genomic sequence analysis. These include the biosynthetic loci encoding polyketide synthase (PKS) and non-ribosomal peptide synthetase (NRPS) consistent with abyssomicins and proximicins, respectively. The biosynthetic pathways of these isolated compounds have been proposed. These results indicate that MS100047 possesses a great potential as a source of active secondary metabolites.