RESUMEN
The leaf extract of Suregada zanzibariensis gave two new modified ent-abietane diterpenoids, zanzibariolides A (1) and B (2), and two known triterpenoids, simiarenol (3) and ß-amyrin (4). The structures of the isolated compounds were elucidated based on NMR and MS data analysis. Single-crystal X-ray diffraction was used to establish the absolute configurations of compounds 1 and 2. The crude leaf extract inhibited the infectivity of herpes simplex virus 2 (HSV-2, IC50 11.5 µg/mL) and showed toxicity on African green monkey kidney (GMK AH1) cells at CC50 52 µg/mL. The isolated compounds 1-3 showed no anti-HSV-2 activity and exhibited insignificant toxicity against GMK AH1 cells at ≥100 µM.
Asunto(s)
Abietanos , Antivirales , Suregada , Triterpenos , Abietanos/química , Abietanos/aislamiento & purificación , Abietanos/farmacología , Animales , Antivirales/química , Antivirales/aislamiento & purificación , Antivirales/farmacología , Chlorocebus aethiops , Herpesvirus Humano 2/efectos de los fármacos , Estructura Molecular , Extractos Vegetales/química , Suregada/química , Triterpenos/química , Triterpenos/aislamiento & purificación , Triterpenos/farmacologíaRESUMEN
The stem bark extract of Suregada zanzibariensis afforded a previously undescribed ent-abietane diterpenoid trivially named mangiolide (1) and a known jolkinolide B (2) via anticancer bioassay-guided fractionation. The CH2Cl2:MeOH extract of S. zanzibariensis was initially analysed for its anticancer properties against three cancer cell lines, renal (TK10), melanoma (UACC62), and breast (MCF7) and was found to be potent at low µg/mL ranges. Compound 1, 6α-acetoxy-14-keto-ent-abieta-7(8),13(15)-diene-16,12-olide (mangiolide) inhibited the growth of renal (TK10) with a GI50 of 0.02 µg/mL; a GI50 of 0.03 µg/mL for melanoma (UACC62) and a GI50 of 0.05 µg/mL for breast (MCF7) cancer cell lines. Compound 2, 8,13-diepoxy-13,15-ent-abietene-16,12-olide (jolkinolide B) inhibited the growth (GI50) of the cell lines at 3.31 µg/mL for renal (TK10), 0.94 µg/mL for melanoma (UACC62) and 2.99 µg/mL for the breast (MCF7). The structures were established on the basis of their spectroscopic analysis and the absolute stereostructures assigned using electronic circular dichroism (ECD).
Asunto(s)
Abietanos/farmacología , Suregada/química , Abietanos/química , Abietanos/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Euphorbiaceae/química , Humanos , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/farmacología , Análisis Espectral , EstereoisomerismoRESUMEN
The triterpenoid, bauerenol, from Suregada angustifolia (Baill. ex Muell.-Arg.) Airy Shaw (Euphorbiaceae) was screened for anti-cancer property using hepatocellular carcinoma cell line, HepG2. Bauerenol exhibited growth inhibitory and apoptosis inducing potential against HepG2 cancer cells. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide cytotoxic assay revealed that bauerenol treatment significantly reduced the growth of HepG2 cells in a time- and dose-dependent manner with 50% growth inhibitory concentration doses of 45 and 25 µg/mL at 24 and 48 h treatments, respectively. Bauerenol-induced cell death reflected apoptotic morphological features, that is, cell membrane blebbing, vacuolization, chromatin condensation, and nuclear fragmentation. In addition, bauerenol treatment diminished the mitochondrial membrane potential, by inducing the efflux of cytochrome c, downregulating the levels of anti-apoptotic Bcl-2 as well as upregulating the levels of pro-apoptotic Bax, and inducing caspase activation and poly (ADP-ribose) polymerase cleavage. Moreover, bauerenol treatment activates p38MAPK and inactivates the anti-apoptotic kinases Akt and ERK1/2 through the induction of reactive oxygen species. Furthermore, bauerenol-mediated S-phase arrest was associated with downregulation of cell cycle-rate-limiting factor (cyclin D1) and upregulation of cyclin-dependent kinase inhibitor p21 and tumor suppressor p53. Interestingly, pre-treatment of cells with reactive oxygen species inhibitor and p38 inhibitor significantly decreases bauerenol-induced cytotoxicity, Bax upregulation, and p38 activation. This study clearly states that bauerenol induces cell cycle arrest and apoptosis through the reactive oxygen species-dependent p38MAPK activation in HepG2 cancer cells.
Asunto(s)
Carcinoma Hepatocelular/tratamiento farmacológico , Neoplasias Hepáticas/tratamiento farmacológico , Triterpenos/administración & dosificación , Proteínas Quinasas p38 Activadas por Mitógenos/biosíntesis , Apoptosis/efectos de los fármacos , Carcinoma Hepatocelular/genética , Carcinoma Hepatocelular/patología , Ciclina D1/biosíntesis , Regulación Neoplásica de la Expresión Génica/efectos de los fármacos , Células Hep G2 , Humanos , Neoplasias Hepáticas/genética , Extractos Vegetales/administración & dosificación , Extractos Vegetales/química , Especies Reactivas de Oxígeno/metabolismo , Suregada/química , Triterpenos/química , Proteína X Asociada a bcl-2/biosíntesis , Proteínas Quinasas p38 Activadas por Mitógenos/genéticaRESUMEN
Three new water-soluble alkaloids (1-3) together with twelve known compounds (4-15) have been isolated from the water extract of leaves of Suregada glomerulata. Their structures were determined by spectroscopic analysis and chemical method. Compounds 1-3 were evaluated for their in vitro inhibitory activity against α-glucosidase and HIV-1 replication. However, no significant activities were found.
Asunto(s)
Extractos Vegetales/química , Piranos/aislamiento & purificación , Pirrolidinas/aislamiento & purificación , Suregada/química , VIH-1 , Estructura Molecular , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta , Piranos/química , Pirrolidinas/química , alfa-Glucosidasas/metabolismoRESUMEN
Twelve ENT-abietane and ENT-kaurane type diterpenoids, 1- 12, including five new compounds 1- 5, were isolated from the roots of Suregada glomerulata. The structures of the new compounds were elucidated on the basis of 1D and 2D NMR and other spectroscopic studies, and the structures of 1 and 2 were confirmed by X-ray crystallography. Cytotoxic activities against five human tumor cell lines were evaluated.
Asunto(s)
Abietanos/aislamiento & purificación , Antineoplásicos Fitogénicos/aislamiento & purificación , Diterpenos de Tipo Kaurano/aislamiento & purificación , Extractos Vegetales/química , Suregada/química , Abietanos/química , Abietanos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Diterpenos de Tipo Kaurano/química , Diterpenos de Tipo Kaurano/farmacología , Humanos , Estructura Molecular , Extractos Vegetales/farmacología , Raíces de PlantasRESUMEN
Six new diterpenoids, 7beta,8alpha-dihydroxy-12-oxo- ent-abietan-16,14-olide ( 1), 3,4,18beta-cyclopropa-7beta,17-dihydroxy- ent-abieta-8(14),13(15)-dien-16,12-olide ( 2), 3alpha,7beta-dihydroxy- ent-abieta-8(14),13(15)-dien-16,12-olide ( 3), 3-oxo-8beta,14beta-epoxy- ent-abieta-11,13(15)-dien-16,12-olide ( 4), 17-hydroxy- ent-pimara-8(14),15-dien-3-one ( 5), and 3alpha,6beta-dihydroxy- ent-kaur-16-ene ( 6), and two known compounds, 7beta-hydroxy- ent-abieta-8(14),13(15)-dien-16,12-olide ( 7) and jolkinolide B, were isolated from roots of Suregada glomerulata. The structures of the new compounds were elucidated on the basis of 1D and 2D NMR and other spectroscopic studies. The structure of compound 1 was confirmed by X-ray crystallography. Cytotoxic activities were evaluated against five human tumor cell lines.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Diterpenos/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Plantas Medicinales/química , Suregada/química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Cristalografía por Rayos X , Diterpenos/química , Diterpenos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Humanos , Conformación Molecular , Estructura Molecular , Raíces de Plantas/químicaRESUMEN
OBJECTIVE: To study the chemical constituents of Suregada glomeruldata. METHOD: Isolation and purification were carried out on silica gel, sephardex LH -20, ODS column chromatography etc. Constituents were identified by physicochemical properties and spectral analysis. RESULT: Nine compounds, Jolkinolide B (1), 8alpha, 14-dihydro-7-oxo-jolkinolide E (2), helioscopinolide B (3), ent-kauran-16beta, 17-diol (4), 7-oxo-beta-sitosterol (5), scopoletin (6), adenosine (7), 1'-sinapoylglucose (8), sucrose (9), were obtained and identified. CONCLUSION: Compounds 2-9 were isolated from S. glomerulata for the first time.
Asunto(s)
Abietanos/aislamiento & purificación , Plantas Medicinales/química , Escopoletina/aislamiento & purificación , Sacarosa/aislamiento & purificación , Suregada/química , Abietanos/química , Cromatografía en Gel , Escopoletina/química , Sacarosa/químicaRESUMEN
Two ent-kaurene diterpenes, ent-16-kaurene-3beta,15beta,18-triol (1) and ent-3-oxo-16-kaurene-15beta,18-diol (2), were isolated from a dichloromethane extract of the bark of Suregada multiflora along with five known diterpenes:ent-16-kaurene-3beta,15beta-diol (3), abbeokutone (4), helioscopinolide A (5), helioscopinolide C (6) and helioscopinolide I (7). Their structures were elucidated on the basis of spectroscopic analysis. Compounds 1-7 possessed appreciable anti-allergic activities in RBL-2H3 cells model with IC50 values ranging from 22.5 to 42.2 microM.
Asunto(s)
Antialérgicos/química , Diterpenos de Tipo Kaurano/química , Corteza de la Planta/química , Suregada/química , Animales , Antialérgicos/aislamiento & purificación , Antialérgicos/farmacología , Línea Celular Tumoral , Diterpenos de Tipo Kaurano/aislamiento & purificación , Diterpenos de Tipo Kaurano/farmacología , Espectroscopía de Resonancia Magnética , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , beta-N-Acetilhexosaminidasas/antagonistas & inhibidores , beta-N-Acetilhexosaminidasas/metabolismoRESUMEN
Phytochemical analysis of the leaves from Indian Suregada angustifolia (Baill. ex Muell. Arg.) Airy Shaw (Euphorbiaceae) resulted in the isolation and identification of six known compounds, viz. friedelin, epi-friedelinol, n-octacosanol, alpha-amyrin, beta-sitosterol and beta-sitosterol-3-beta-D-glucopyranoside. Aqueous (room temperature, boiled and autoclaved) and various solvent (methanol, chloroform and hexane) extracts of leaves were tested against 12 human pathogenic bacteria by the agar well-diffusion method. Aqueous extracts did not express any activity. Antibacterial activity was recorded in the order of methanol, hexane and chloroform extracts. Maximum activity recorded against Staphylococcus aureus (skin infections) in methanol and hexane extracts and moderate activity recorded against diarrhoea causing bacteria, Vibrio vulnificus (hexane extract) and Vibrio cholerae (chloroform extract).
Asunto(s)
Antibacterianos/farmacología , Extractos Vegetales/farmacología , Suregada/química , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Cloroformo/química , Hexanos/química , Humanos , India , Klebsiella pneumoniae/efectos de los fármacos , Klebsiella pneumoniae/crecimiento & desarrollo , Pruebas de Sensibilidad Microbiana/métodos , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta/química , Proteus vulgaris/efectos de los fármacos , Proteus vulgaris/crecimiento & desarrollo , Staphylococcus aureus/efectos de los fármacos , Staphylococcus aureus/crecimiento & desarrollo , Vibrio cholerae/efectos de los fármacos , Vibrio cholerae/crecimiento & desarrollo , Vibrio parahaemolyticus/efectos de los fármacos , Vibrio parahaemolyticus/crecimiento & desarrolloRESUMEN
Six new diterpenoids were isolated from a CH(2)Cl(2)-MeOH extract of the bark of Suregada multiflora. The structures were established on the basis of one- and two-dimensional NMR and other spectroscopic studies and chemical derivatizations. Two compounds, suregadolides C (1) and D (2), were identified as new diterpene lactones of two antipodal series, containing a cyclopropane ring bridging C-3 and C-4 of the basic abietane skeleton. Suremulide A (3) was found to be a new abietene diterpene lactone. Bannaringaolide A (4), a diterpene lactone, based on a novel carbon skeleton with a seven-membered ring, possibly formed by the rearrangement of the exocyclic C-17 in ring C of an ent-pimarane framework, has also been isolated. A kaurane triol, suremulol A (5), and a kaurane diol, suremulol B (6), were also identified as new metabolites.