RESUMEN
The leaves of the kaffir lime (Citrus hystrix) are commonly used in cuisine and folk medicine. The aim of this study was to isolate a bioactive compound in kaffir lime leaves and characterize its biological activity. The compound was isolated from a hexane fractional extract and identified as agrostophillinol. This is the first report of agrostophillinol isolated from kaffir lime leaves. In terms of cytotoxicity, agrostophillinol exhibited IC50 values of 36.27 ± 7.30 and 53.44 ± 10.63 µg/mL against EoL-1 and HL60 cells, respectively. Agrostophillinol also exhibited potent anti-inflammatory activity, significantly inhibiting IL-6 secretion.
Asunto(s)
Antiinflamatorios/farmacología , Antineoplásicos Fitogénicos/farmacología , Antioxidantes/farmacología , Citrus/química , Interleucina-6/antagonistas & inhibidores , Lanosterol/análogos & derivados , Extractos Vegetales/farmacología , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Compuestos de Bifenilo/antagonistas & inhibidores , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Interleucina-6/metabolismo , Lanosterol/química , Lanosterol/aislamiento & purificación , Lanosterol/farmacología , Ratones , Conformación Molecular , Picratos/antagonistas & inhibidores , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta/química , Células RAW 264.7 , Relación Estructura-ActividadRESUMEN
Wolfiporia cocos is a fungus containing triterpenoids and is widely used as an herbal medicine. However, it is unknown whether its main triterpenoid contents differ in different tissues. In this study, we identified dehydrotumulosic acid, polyporenic acid C, pachymic acid, dehydrotrametenolic acid, and dehydroeburicoic acid as the five main triterpenoids in W. cocos. We also systematically profiled the contents and distribution of these main triterpenoids in different tissues of W. cocos. High contents of all five triterpenoids were found in the surface layer of W. cocos. Intriguingly, we noted that the highest contents of the five triterpenoids were found in the surface layer of the sclerotium grown under pollution-controlled cultivation; the second-highest contents were found in the surface layer of the natural sclerotium. These results indicate that environmentally friendly cultivation of the sclerotium of W. cocos is a practical way to increase the productivity of W. cocos. In addition, our findings suggest that the triterpenoids may contribute to the pharmacological activity of W. cocos, and the surface layer of sclerotium in W. cocos might be a promising raw material for applications in health care and the development of functional medical products.
Asunto(s)
Lanosterol/análogos & derivados , Triterpenos/aislamiento & purificación , Wolfiporia/química , Cromatografía Líquida de Alta Presión , Lanosterol/química , Lanosterol/aislamiento & purificación , Extracción Líquido-Líquido/métodos , Metanol/química , Micelio/química , Micelio/metabolismo , Solventes/química , Triterpenos/química , Wolfiporia/metabolismoRESUMEN
BACKGROUND/AIMS: Non-toxic fomitopsis is has been traditionally used in folk medicine in many countries for its anti-inflammatory and anti-vascular disease activities. The present study investigates the antitumor effect of Fomitopsis pinicola (Sw. Ex Fr.) Karst chloroform extract (FPKc) on S180 tumor cells in vitro and in vivo and we determined the underlying mechanisms. METHODS: HPLC was employed to analyze the constituents of FPKc. In-vitro 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay was performed to quantify the growth inhibition of FPKc; Propidium iodide (PI) exclusion assay and scanning electron microscopy (SEM) were used to observe the damage on the cell membrane and the changes of the cell morphology; Staining with Hoechst 33342/propidium iodide (HO/PI) and the application of the Annexin V-FITC/PI analysis permitted to observe the cell death triggered by FPKc; DNA damage and cell cycle arrest were detected by flow cytometry; Rhodamine 123 (RH123) and Cytochrome C were used as dyes to investigate the alterations of the mitochondria. In-vivo tumor inhibition and mice survival time were determined. RESULTS: The results of the HPLC assay indicated that FPKc might contain DA (dehydroeburiconic acid), PA (pachymic acid), and ES (ergosterol), at percentages of 0.25%, 17.8%, and 10.5%, respectively. Concerning the study of the biological function, the results showed that FPKc exhibited preferential and significant suppression of proliferation on specific cell lines including S180, HL-60, U937, K562, SMMC-7721, and Eca-109 cells, which induced plasma membrane and cell morphology damages, triggering S180 tumor-cells late apoptosis and leading to DNA damage and S phase arrest. Mitochondria were suspected to play a vital role in these changes. In vivo data indicated that FPKc inhibited the solid tumor growth and prolonged the survival time of tumor-bearing mice. Moreover, FPKc provoked only little damage on normal cells in vitro and also on normal tissues in vivo. CONCLUSION: FPKc inhibited S180 tumor cells growth and prolonged the lifespan of mice. In vitro, we found that FPKc induced S180 tumor cells apoptosis and cell cycle arrest, possibly via the mitochondrial pathway.
Asunto(s)
Coriolaceae/química , Extractos Vegetales/química , Animales , Línea Celular Tumoral , Membrana Celular/efectos de los fármacos , Membrana Celular/fisiología , Supervivencia Celular/efectos de los fármacos , Cloroformo/química , Coriolaceae/metabolismo , Daño del ADN/efectos de los fármacos , Ergosterol/química , Ergosterol/aislamiento & purificación , Ergosterol/farmacología , Células HL-60 , Humanos , Células K562 , Lanosterol/análogos & derivados , Lanosterol/química , Lanosterol/aislamiento & purificación , Lanosterol/farmacología , Leucocitos Mononucleares/citología , Leucocitos Mononucleares/efectos de los fármacos , Leucocitos Mononucleares/metabolismo , Longevidad/efectos de los fármacos , Potencial de la Membrana Mitocondrial/efectos de los fármacos , Ratones , Extractos Vegetales/farmacología , Puntos de Control de la Fase S del Ciclo Celular/efectos de los fármacos , Triterpenos/química , Triterpenos/aislamiento & purificación , Triterpenos/farmacologíaRESUMEN
Type 2 diabetes remains one of the leading causes of death worldwide. Persistent hyperglycemia within a diabetic state is implicated in the generation of oxidative stress and aggravated inflammation that is responsible for accelerated modification of pancreatic beta cell structure. Here we investigated whether a lanosteryl triterpene, methyl-3ß-hydroxylanosta-9,24-dien-21-oate (RA-3), isolated from Protorhus longifolia can improve glucose tolerance and pancreatic beta cell ultrastructure by reducing oxidative stress and inflammation in high fat diet and streptozotocin-induced type 2 diabetes in rats. In addition to impaired glucose tolerance, the untreated diabetic rats showed increased fasting plasma glucose and C-peptide levels. These untreated diabetic rats further demonstrated raised cholesterol, interleukin-6 (IL-6), and lipid peroxidation levels as well as a destroyed beta cell ultrastructure. Treatment with RA-3 was as effective as metformin in improving glucose tolerance and antioxidant effect in the diabetic rats. Interestingly, RA-3 displayed a slightly more enhanced effect than metformin in reducing elevated IL-6 levels and in improving beta cell ultrastructure. Although the involved molecular mechanisms remain to be established, RA-3 demonstrates a strong potential to improve pancreatic beta cell ultrastructure by attenuating impaired glucose tolerance, reducing oxidative stress and inflammation.
Asunto(s)
Anacardiaceae/química , Antioxidantes/farmacología , Diabetes Mellitus Tipo 2/tratamiento farmacológico , Hipoglucemiantes/farmacología , Células Secretoras de Insulina/efectos de los fármacos , Lanosterol/análogos & derivados , Triterpenos/química , Animales , Glucemia , Diabetes Mellitus Tipo 2/inducido químicamente , Diabetes Mellitus Tipo 2/patología , Dieta Alta en Grasa , Glucosa/metabolismo , Prueba de Tolerancia a la Glucosa , Hiperglucemia/tratamiento farmacológico , Inflamación/tratamiento farmacológico , Insulina/metabolismo , Células Secretoras de Insulina/ultraestructura , Interleucina-6/metabolismo , Lanosterol/química , Lanosterol/aislamiento & purificación , Lanosterol/metabolismo , Estrés Oxidativo/efectos de los fármacos , Extractos Vegetales/química , Ratas Sprague-Dawley , Estreptozocina , Triterpenos/aislamiento & purificación , Triterpenos/farmacologíaRESUMEN
Triterpene acids are among the major bioactive constituents of lucidum. However, submerged fermentation techniques for isolating triterpene acids from G. lucidum have not been optimized for commercial use, and the antitumor activity of the mycelial triterpene acids needs to be further proven. The aim of this work was to optimize the conditions for G. lucidum culture with respect to triterpene acid production, scaling up the process, and examining the in vitro antitumor activity of mycelial triterpene acids. The key conditions (i.e., initial pH, fermentation temperature, and rotation speed) were optimized using response surface methodology, and the in vitro antitumor activity was evaluated using the MTT method. The optimum key fermentation conditions for triterpene acid production were pH 6.0; rotation speed, 161.9 rpm; and temperature, 30.1°C, resulting in a triterpene acid yield of 291.0 mg/L in the validation experiment in a 5-L stirred bioreactor; this yield represented a 70.8% increase in titer compared with the nonoptimized conditions. Furthermore, the optimized conditions were then successfully scaled up to a production scale of 200 L, and a triterpene productivity of 47.9 mg/L/day was achieved, which is, to our knowledge, the highest reported in the large-scale fermentation of G. lucidum. In addition, the mycelial triterpene acids were found to be cytotoxic to the SMMC-7721 and SW620 cell lines in vitro. Chemical analysis showed that the key active triterpene acid compounds, ganoderic acids T and Me, predominated in the extract, at 69.2 and 41.6 mg/g, respectively. Thus, this work develops a simple and feasible batch fermentation technique for the large-scale production of antitumor triterpene acids from G. lucidum.
Asunto(s)
Antineoplásicos/farmacología , Lanosterol/análogos & derivados , Reishi/química , Triterpenos/farmacología , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Reactores Biológicos , Línea Celular Tumoral , Fermentación , Humanos , Lanosterol/química , Lanosterol/aislamiento & purificación , Lanosterol/farmacología , Medicina Tradicional , Temperatura , Triterpenos/química , Triterpenos/aislamiento & purificaciónRESUMEN
The metabolism of vitamin D is a very important pathway involved in the regulation of sterols and maintenance of cell health. The physiological activity of the human hormone 1α,25-dihydroxyvitamin D3, or calcitriol, is mediated by the vitamin D receptor (VDR), an endocrine member of the nuclear receptor superfamily that inhibits cell growth and stimulates cell differentiation, suggesting a potential application in cancer chemoprevention. Since nonpolar extracts obtained from Ganoderma mushrooms have also been shown to exert an antiproliferative effect on several cancer cell lines, it was suggested that at least part of its activity might be mediated by VDR. The aim of this work was to identify possible VDR ligands from an extensive library of lanostanoids isolated from several Ganoderma mushrooms. Using an in silico approach, 30 lanostanoids were found to interact with the VDR ligand-binding pocket in the same way as calcitriol. The possible implications of using these compounds are discussed here.
Asunto(s)
Lanosterol/análogos & derivados , Receptores de Calcitriol/metabolismo , Simulación por Computador , Ganoderma/metabolismo , Lanosterol/química , Lanosterol/aislamiento & purificación , Lanosterol/metabolismo , Ligandos , Unión Proteica , Receptores de Calcitriol/químicaRESUMEN
CONTEXT: The current rapid increase in the incidence of cardiovascular events indicates a need for the discovery of more effective cardioprotective agents. OBJECTIVE: This study evaluated the cardioprotective potential of a lanosteryl triterpene from Protorhus longifolia (Benrh.) Engl. stem bark. MATERIALS AND METHODS: Spectroscopic data analysis was used to confirm the structure of methyl-3ß-hydroxylanosta-9, 24-dien-21-oate (RA-3). The cardioprotective effect of RA-3 in isoproterenol-induced myocardial injury in hyperlipidemic rats was investigated. Rats were divided into the normal diet (ND) fed and high fat diet (HFD) fed groups. The HFD rats were further subdivided into three groups. The experimental group was orally administered with RA-3 (100 mg/kg) for 15 days. The rats were then injected with isoproterenol (85 mg/kg) to induce myocardial injury. At the end of the experiment, hearts and blood tissues were collected and used for histology and biochemical assays, respectively. RESULTS: RA-3 exhibited a cardioprotective effect as it minimized myocardial injury in HFD rats. Few lesions of acute hyaline degeneration and reduced fat deposition were observed in the heart tissue of the triterpene pretreated rats. Lactate dehydrogenase (LDH) activity was decreased in the blood of the RA-3 pretreated rats (44.1 mU/mL) compared to the untreated group (64.8 mU/mL). Increased glutathione (GSH) content and catalase (CAT) activity along with lower levels of malondialdehyde (MDA) in the triterpene pretreated animals (120.8 nmol/µL) than in the non-treated HFD fed rats (143.6 nmol/µL) were also observed. DISCUSSION AND CONCLUSION: The cardioprotective effect exhibited by RA-3 indicates its potential use in the management of cardiovascular diseases (CVD) and related health problems.
Asunto(s)
Anacardiaceae , Cardiotónicos/farmacología , Lanosterol/farmacología , Extractos Vegetales/farmacología , Triterpenos/farmacología , Animales , Cardiotónicos/aislamiento & purificación , Dieta Alta en Grasa/efectos adversos , Corazón/efectos de los fármacos , Lanosterol/aislamiento & purificación , Miocardio/metabolismo , Miocardio/patología , Corteza de la Planta , Extractos Vegetales/aislamiento & purificación , Tallos de la Planta , Ratas , Ratas Sprague-Dawley , Triterpenos/aislamiento & purificaciónRESUMEN
Ganoderic acid A (GAA) is one of the major Ganoderma triterpenes produced by medicinal mushroom belonging to the genus Ganoderma (Ganodermataceae). Due to its interesting pharmacological activities, Ganoderma species have been traditionally used in China for the treatment of various diseases. Herein, we developed a colloidal gold-based immunochromatographic strip assay (ICA) for the rapid detection of GAA using highly specific monoclonal antibody against GAA (MAb 12A) conjugated with gold nanoparticles. Using the developed ICA, the detection of GAA can be completed within 15min after dipping the test strip into an analyte solution with the limit of detection (LOD) for GAA of ~500ng/mL. In addition, this system makes it possible to perform a semi-quantitative analysis of GAA in Ganoderma lingzhi, where high reliability was evaluated by enzyme-linked immunosorbent assay (ELISA). The newly developed ICA can potentially be applied to the standardization of Ganoderma using GAA as an index because GAA is major triterpenoid present much in the mushroom.
Asunto(s)
Cromatografía de Afinidad , Ganoderma/química , Ácidos Heptanoicos/aislamiento & purificación , Lanosterol/análogos & derivados , Anticuerpos Monoclonales , Ensayo de Inmunoadsorción Enzimática , Lanosterol/aislamiento & purificación , Límite de Detección , Reproducibilidad de los ResultadosRESUMEN
Five new lanostanoid triterpenes were isolated from the ethanol extract of the fruiting bodies of Ganoderma atrum. The structures of the isolated compounds were established based on 1D and 2D ((1)H-(1)H COSY, HMQC, and HMBC) NMR spectroscopy, in addition to high resolution mass spectrometry. The isolated compounds were tested in vitro for neuroprotective activities against 6-OHDA-induced cell death in SH-SY5Y cells and radical scavenging activities. As a result, compounds 2 and 5 exhibited potent neuroprotective activity against 6-OHDA-induced cell death in SH-SY5Y cells with the lowest IC50 value (0.5 µM) while compounds 1, 3 and 4 possessed significant neuroprotective activity with IC50 value less than 10 µM. Additionally, all tested compounds 1-6 showed the comparable free radical scavenging activities with the standard drug trolox in both ABTS (+) and DPPH experiment.
Asunto(s)
Depuradores de Radicales Libres/química , Ganoderma/química , Lanosterol/análogos & derivados , Fármacos Neuroprotectores/aislamiento & purificación , Triterpenos/química , Línea Celular Tumoral/efectos de los fármacos , Depuradores de Radicales Libres/aislamiento & purificación , Cuerpos Fructíferos de los Hongos/química , Humanos , Lanosterol/química , Lanosterol/aislamiento & purificación , Estructura Molecular , Neuroblastoma/patología , Fármacos Neuroprotectores/química , Triterpenos/aislamiento & purificaciónRESUMEN
A new lanostanoid, 19-nor-lanosta-5(10),6,8,24-tetraene-1α,3ß,12ß,22S-tetraol (1), characterized by the presence of an aromatic B ring and hydroxylated at C-1, C-3, C-12, and C-22, was isolated from an endophytic fungus, Diaporthe sp. LG23, inhabiting leaves of the Chinese medicinal plant Mahonia fortunei. Six biosynthetically related known steroids were also isolated in parallel. Their structures were confirmed on the basis of detailed spectroscopic analysis in conjunction with the published data. Compound 1, an unusual fungus-derived 19-nor-lanostane tetracyclic triterpenoid with an aromatic B-ring system, exhibited pronounced antibacterial efficacy against both Gram-positive and -negative bacteria, especially the clinical isolates of Streptococcus pyogenes and Pseudomonas aeruginosa as well as a human pathogenic strain of Staphylococcus aureus. Our results reveal the potential of endophytes not only in conferring host fitness but also in contributing toward traditional host plant medicines.
Asunto(s)
Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Endófitos/química , Lanosterol/aislamiento & purificación , Lanosterol/farmacología , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Antibacterianos/química , Humanos , Lanosterol/análogos & derivados , Lanosterol/química , Mahonia/microbiología , Medicina Tradicional , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Hojas de la Planta , Plantas Medicinales/química , Plantas Medicinales/microbiología , Pseudomonas aeruginosa/efectos de los fármacos , Staphylococcus aureus/efectos de los fármacos , Streptococcus pyogenes/efectos de los fármacos , Triterpenos/químicaRESUMEN
Garcinia species are reported to possess antimicrobial, anti-inflammatory, anticancer, anti-HIV and anti-Alzheimer's activities. This study aimed to investigate the in vitro cholinesterase enzyme inhibitory activities of garcihombronane C (1), garcihombronane F (2), garcihombronane I (3), garcihombronane N (4), friedelin (5), clerosterol (6), spinasterol glucoside (7) and 3ß-hydroxy lup-12,20(29)-diene (8) isolated from Garcinia hombroniana, and to perform molecular docking simulation to get insight into the binding interactions of the ligands and enzymes. The cholinesterase inhibitory activities were evaluated using acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. In this study, compound 4 displayed the highest concentration-dependent inhibition of both AChE and BChE. Docking studies exhibited that compound 4 binds through hydrogen bonds to amino acid residues of AChE and BChE. The calculated docking and binding energies also supported the in vitro inhibitory profiles of IC50. In conclusion, garcihombronanes C, F, I and N (1-4) exhibited dual and moderate inhibitory activities against AChE and BChE.
Asunto(s)
Inhibidores de la Colinesterasa/aislamiento & purificación , Inhibidores de la Colinesterasa/farmacología , Garcinia/química , Lanosterol/análogos & derivados , Plantas Medicinales/química , Acetilcolinesterasa/efectos de los fármacos , Butirilcolinesterasa/efectos de los fármacos , Inhibidores de la Colinesterasa/química , Técnicas In Vitro , Concentración 50 Inhibidora , Lanosterol/química , Lanosterol/aislamiento & purificación , Lanosterol/farmacología , Conformación Molecular , Estructura Molecular , Resonancia Magnética Nuclear BiomolecularRESUMEN
Based on the fact that Synadenium grantii is used in folk medicine for the treatment of peptic ulcers and inflammatory diseases, this work describes its chemical and pharmacological properties. Pharmacological investigation of the crude bark extract showed a high antioxidant activity over several scavenger systems, such as 2,2'-azino-bis (3-ethylenebenzothiazoline-6-sulfonic acid)â¢â+, 1-diphenyl-2-picrylhydrazylâ¢, O2 â¢â- , and HOCl, as well as an enzymatic system with human myeloperoxidase and an ex vivo hemolysis system. Furthermore, the oral administration of the crude bark extract was able to reduce carrageenan-induced rat paw edema as effectively as ibuprofen. These biological activities may be associated with the presence of flavonoids and terpenes, as revealed by HPLC and NMR analyses of the crude stem bark extract. The phytochemical investigations in this study resulted in the isolation of friedelin and 3ß-friedelinol for the first time, while euphol and lanosterol were also isolated.
Asunto(s)
Antiinflamatorios/farmacología , Antioxidantes/farmacología , Euphorbia/química , Flavonoides/farmacología , Fitoterapia , Extractos Vegetales/farmacología , Triterpenos/farmacología , Administración Oral , Animales , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/uso terapéutico , Antioxidantes/aislamiento & purificación , Antioxidantes/uso terapéutico , Benzotiazoles/metabolismo , Compuestos de Bifenilo/metabolismo , Carragenina , Edema/inducido químicamente , Edema/tratamiento farmacológico , Femenino , Flavonoides/análisis , Flavonoides/uso terapéutico , Humanos , Inflamación/inducido químicamente , Inflamación/tratamiento farmacológico , Lanosterol/análogos & derivados , Lanosterol/aislamiento & purificación , Lanosterol/farmacología , Lanosterol/uso terapéutico , Peroxidasa/metabolismo , Picratos/metabolismo , Corteza de la Planta/química , Extractos Vegetales/química , Extractos Vegetales/uso terapéutico , Tallos de la Planta/química , Ratas Wistar , Ácidos Sulfónicos/metabolismo , Triterpenos/aislamiento & purificación , Triterpenos/uso terapéuticoRESUMEN
Two new lanostanoids, 3α-acetoxy-22-oxo-5α-lanosta-8,24-dien-21-oic acid, named tsugaric acid D (1) and 16α-hydroxy-3-oxo-5α-lanosta-6,8,24(24(1))-trien-21-oic acid, named tsugaric acid E (2) were isolated from the fruit bodies of Ganoderma tsugae. The structures 1 and 2 were determined by spectroscopic methods. Compound 1 and known compounds 3 and 6 exhibited significant inhibitory effects on xanthine oxidase (XO) activity with an IC50 values of 90.2±24.2, 116.1±3.0, and 181.9±5.8 µM, respectively. Known compound 5 was able to protect human keratinocytes against damage induced by UVB light, which showed 5 could protect keratinocytes from photodamage. The 1 and 5 µM 1 combined with 5 µM cisplatin, respectively, enhanced the cytotoxicity induced by cisplatin. It suggested that 1 and 5 µM 1 combined with low dose of cisplatin may enhance the therapeutic efficacy of cisplatin and reduce side effect and cisplatin resistant.
Asunto(s)
Antioxidantes/uso terapéutico , Productos Biológicos/uso terapéutico , Ganoderma/química , Queratinocitos/efectos de los fármacos , Lanosterol/análogos & derivados , Neoplasias de la Próstata/tratamiento farmacológico , Xantina Oxidasa/antagonistas & inhibidores , Animales , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/uso terapéutico , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Productos Biológicos/química , Productos Biológicos/farmacología , Cisplatino/farmacología , Cisplatino/uso terapéutico , Cuerpos Fructíferos de los Hongos/química , Interacciones de Hierba-Droga , Humanos , Concentración 50 Inhibidora , Queratinocitos/efectos de la radiación , Lanosterol/química , Lanosterol/aislamiento & purificación , Lanosterol/farmacología , Lanosterol/uso terapéutico , Masculino , Estructura Molecular , Fitoterapia , Traumatismos Experimentales por Radiación/tratamiento farmacológico , Enfermedades de la Piel/prevención & controlRESUMEN
A new lanostane triterpenoid, 2-hydroxy-24-methylenelanostan-1,8-dien-3-one named klainedoxalanostenone (1) with one new steroid, 6-O-acyl-ß-d-glucosyl-ß-sitosterol named klainedoxasterol (2) together with ten known compounds including six triterpenoids (3-8), two steroids (9, 10) and two tanins (11, 12) were isolated from the stem bark of Klainedoxa gabonensis. To the best of our knowledge, this is the first report of lanostane-type triterpenoids from this genus. Their structures were determined by extensive analysis of spectroscopic data (1D and 2D NMR, MS) and by comparison with literature data. The xanthine oxidase inhibitory activity of nine compounds (1-6, 8, 10 and 11) were evaluated. Compound 5 showed a good xanthine oxidase inhibitory activity; the other tested compounds were moderately active.
Asunto(s)
Inhibidores Enzimáticos/aislamiento & purificación , Lanosterol/análogos & derivados , Magnoliopsida/química , Extractos Vegetales/química , Triterpenos/aislamiento & purificación , Xantina Oxidasa/antagonistas & inhibidores , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/farmacología , Lanosterol/química , Lanosterol/aislamiento & purificación , Lanosterol/farmacología , Estructura Molecular , Corteza de la Planta , Extractos Vegetales/farmacología , Tallos de la Planta , Triterpenos/química , Triterpenos/farmacologíaRESUMEN
Five new 3,4-seco-lanostane-type triterpenoids, seco-coccinic acids G-K (1-5), and a known compound, seco-coccinic F, were isolated from the roots of Kadsura coccinea (Lem.) A.âC. Sm. Their structures were elucidated by spectroscopic methods, including 2D-NMR and HR-MS techniques. The cell growth inhibitory effects of these compounds were assayed in human leukemia HL-60 cells, and it was found that 1, 5, and 6 showed antiproliferative effects with GI50 values of 28.4, 15.2, and 16.6 µM, respectively.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Medicamentos Herbarios Chinos/farmacología , Kadsura/química , Lanosterol/farmacología , Triterpenos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Proliferación Celular/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Células HL-60 , Humanos , Lanosterol/química , Lanosterol/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura Molecular , Raíces de Plantas/química , Plantas Medicinales , Espectrometría de Masa por Ionización de Electrospray , Triterpenos/química , Triterpenos/aislamiento & purificaciónRESUMEN
ETHNOPHARMACOLOGICAL RELEVANCE: Evening primrose (Oenothera biennis L.) is a wild medicinal herb of Central American origin that is now globally widespread. Its traditional uses include treatment of rheumatoid arthritis and premenopausal pain both of which have an inflammatory component. The present study demonstrates the in vitro anti-inflammatory activity of three Oenothera biennis compounds. MATERIALS AND METHODS: Oenotheralanosterol A and B (Oen-A & Oen-B) along with gallic acid (GA) were isolated and characterized using column chromatography and NMR. The compounds were tested with LPS stimulated peritoneal mouse macrophages assaying for suppression of IL-6, TNF-α and NO synthesis. An HILIC method for the simultaneous quantitation of GA, Oen-A, and Oen-B in Oenothera biennis plant material was also developed as a means of monitoring quality of plant material. RESULTS: Significant inhibition of TNF-α and IL-6 by GA, Oen-A and Oen-B was observed (p<0.05). Inhibition was concentration dependent and no synergistic or antagonistic effect on pro-inflammatory cytokines was found when used in combination (1:1) (p>0.05). The HILIC analysis method was validated using Oenothera biennis root. CONCLUSION: The study demonstrates the anti-inflammatory activity of Oenothera biennis root compounds and supports its traditional use in arthritis management. Active anti-inflammatory compounds were identified and quantified by the HILIC method.
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Antiinflamatorios/farmacología , Cromatografía Liquida/métodos , Interleucina-6/metabolismo , Lanosterol/análogos & derivados , Macrófagos Peritoneales/efectos de los fármacos , Oenothera biennis , Extractos Vegetales/farmacología , Factor de Necrosis Tumoral alfa/metabolismo , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Supervivencia Celular/efectos de los fármacos , Células Cultivadas , Relación Dosis-Respuesta a Droga , Regulación hacia Abajo , Femenino , Ácido Gálico/farmacología , Interacciones Hidrofóbicas e Hidrofílicas , Lanosterol/química , Lanosterol/aislamiento & purificación , Lanosterol/farmacología , Macrófagos Peritoneales/inmunología , Espectroscopía de Resonancia Magnética , Ratones , Óxido Nítrico/metabolismo , Oenothera biennis/química , Fitoterapia , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Raíces de Plantas , Plantas Medicinales , Reproducibilidad de los ResultadosRESUMEN
INTRODUCTION: In Eastern Europe, especially Russia, the fruiting body of Inonotus obliquus has been used as a folk medicine for cancer since the sixteenth or seventeenth century. Inotodiol and trametenolic acid are considered to be the main bioactive compounds of the fruiting body of the mushroom. These compounds show various biological activities, including anti-tumour, anti-viral, hypoglycaemic, anti-oxidant and cyto-protective. However, effective methods for isolating and purifying inotodiol and trametenolic acid from the fruiting body of Inonotus obliquus are not currently available. OBJECTIVE: To develop a suitable preparative method in order to isolate inotodiol and trametenolic acid from a complex Inonotus obliquus extract by preparative high-speed counter-current chromatography (HSCCC). METHODOLOGY: Inotodiol and trametenolic acid were rapidly isolated and purified from the chloroform extract of Inonotus obliquus (Fr.) by HSCCC with evaporative light scatting detection (ELSD). The purity of the obtained target compounds was analysed by high-performance liquid chromatography (HPLC) with ELSD. The structures of the two compounds were identified by ¹H NMR and ¹³C NMR. RESULT: The target compounds were finally isolated and purified with a solvent system of hexane:ethyl acetate:methanol:water (1:0.4:1:0.4, v/v/v/v). In a single operation, 100 mg of the I. obliquus extracts yielded 13.0 mg of inotodiol and 7.0 mg of trametenolic acid. The entire separation and purification process took less than 5 h. The purities of obtained inotodiol and trametenolic acid were 97.51 and 94.04%, respectively. CONCLUSION: HSCCC-ELSD was an efficient and rapid method for the separation and purification of inotodiol and trametenolic acid from I. obliquus.
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Agaricales/química , Cromatografía Líquida de Alta Presión/métodos , Lanosterol/análogos & derivados , Triterpenos/aislamiento & purificación , Lanosterol/química , Lanosterol/aislamiento & purificación , Resonancia Magnética Nuclear Biomolecular , Triterpenos/químicaRESUMEN
Black cohosh (Actaea racemosa) is a frequently used herbal remedy for the treatment of mild climacteric symptoms. In the present study, the modulation of γ-aminobutryic acid (GABA)-induced chloride currents (I(GABA)) through GABA type A (GABA(A)) receptors by black cohosh extracts and isolated compounds was investigated. GABA(A) receptors, consisting of α(1), ß(2), and γ(2S) subunits, were expressed in Xenopus laevis oocytes, and potentiation of I(GABA) was measured using the two-microelectrode voltage clamp technique. In a bioactivity-guided isolation procedure the positive modulation of I(GABA) could be restricted to the plant terpenoid fractions, resulting in the isolation of 11 cycloartane glycosides, of which four significantly (p < 0.05) enhanced I(GABA). The most efficient effect was observed for 23-O-acetylshengmanol 3-O-ß-d-xylopyranoside (4, 100 µM), enhancing I(GABA) by 1692 ± 201%, while actein (1), cimigenol 3-O-ß-d-xylopyranoside (6), and 25-O-acetylcimigenol 3-O-α-l-arabinopyranoside (8) were significantly less active. In the absence of GABA, only 4 induced small (not exceeding 1% of I(GABA-max)) chloride inward currents through GABA(A) receptors. It is hypothesized that the established positive allosteric modulation of GABA(A) receptors may contribute to beneficial effects of black cohosh extracts in the treatment of climacteric symptoms.
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Cimicifuga/química , Glicósidos/aislamiento & purificación , Glicósidos/farmacología , Lanosterol/análogos & derivados , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Receptores de GABA-A/efectos de los fármacos , Saponinas/aislamiento & purificación , Saponinas/farmacología , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Animales , Austria , Relación Dosis-Respuesta a Droga , Glicósidos/química , Lanosterol/química , Lanosterol/aislamiento & purificación , Lanosterol/farmacología , Estructura Molecular , Oocitos/efectos de los fármacos , Extractos Vegetales/química , Rizoma/química , Saponinas/química , Triterpenos/química , Xenopus laevisRESUMEN
CHCl(3) extract of the fruiting body of Ganoderma lucidum was found to show inhibitory activity on human aldose reductase in vitro. From the acidic fraction, potent human aldose reductase inhibitors, ganoderic acid C2 (1) and ganoderenic acid A (2), were isolated together with three related compounds. It was found that the free carboxyl group of ganoderic acid C2 and ganoderenic acid A is essential in eliciting the inhibitory activity considering the much lower activity of their methyl esters.
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Aldehído Reductasa/antagonistas & inhibidores , Ganoderma/química , Ácidos Heptanoicos/química , Lanosterol/análogos & derivados , Triterpenos/química , Fraccionamiento Químico , Cromatografía Líquida de Alta Presión , Mezclas Complejas/química , Mezclas Complejas/aislamiento & purificación , Mezclas Complejas/farmacología , Ácidos Heptanoicos/aislamiento & purificación , Humanos , Lanosterol/química , Lanosterol/aislamiento & purificación , Triterpenos/aislamiento & purificaciónRESUMEN
In a screen of 880 extracts from plants and fungi for antiplasmodial, antitrypanosomal, and leishmanicidal activity, an ethyl acetate extract of the mushroom Ganoderma lucidum showed antiplasmodial activity with 79% inhibition at 4.9 microg/mL. HPLC-based activity profiling and subsequent isolation of the antiplasmodial compounds yielded seven lanostanes (1-7), of which three (2, 3, and 7) were new. A new benzofuran derivative (8) of the farnesyl hydroquinone ganomycin B was also identified. The structures and relative configurations of the new compounds were elucidated by comprehensive spectroscopic analysis and by comparison of their NMR data with those of related compounds. The lanostanes exhibited in vitro antiplasmodial activity with IC(50) values from 6 to greater than 20 microM.