RESUMEN
A new 3,4-seco-cycloartane, identified as (24R,25S)-dihydroxy-26-O-nonadecylcarbonyloxy-3,4-secocycloarta-4(28)-en-3-oic acid (1), has been isolated from the leaves of Hopea odorata Roxb. (Dipterocarpaceae), together with the rare 3,4-seco-cycloart-4(28),24-diene-3,26-dioic acid (2 or abiesatrine J) and six other known compounds (3-8). Their structures were elucidated on the basis of both chemical and spectroscopic methods.
Asunto(s)
Dipterocarpaceae/química , Hojas de la Planta/química , Triterpenos/química , Estructura Molecular , Plantas Medicinales/química , Secoesteroides/química , Secoesteroides/aislamiento & purificación , Tailandia , Triterpenos/aislamiento & purificaciónRESUMEN
Antioxidative, skin protective activities, and cytotoxicity of three extracts (water, methanol, and hexane) from the fruit hull of mangosteen (Garcinia mangostana Linn. (Guttiferae)) and their phenolic constituents such as alpha-mangostin, epicatechin, and tannin, were evaluated. The amounts of alpha-mangostin, total flavonoid, and total tannin were different among the three extracts, except those of total tannin in methanol and hexane extracts. For the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free-radical scavenging, hydroxyl radical-scavenging, and inhibition of lipid peroxidation experiment, the water extract showed higher activity than the methanol extract and hexane extract. alpha-Mangostin, epicatechin, and tannin also revealed these antioxidant and free radical-scavenging activities. When added simultaneously with H(2)O(2) (200 microM) to keratinocyte cells, the water extract (50 microg/mL), epicatechin (200 microM), and tannin (200 microM) effectively protected cells from oxidative damage, but the methanol extract, hexane extract, and alpha-mangostin did not. The methanol extract and hexane extract exhibited moderate cytotoxicity, whereas alpha-mangostin showed strong cytotoxicity. The present study provides the evidence that Garcinia mangostana extracts, especially the G. mangostana water extract, act as antioxidants and cytoprotective agents against oxidative damage, which is at least partly due to its phenolic compounds in mangosteen.
Asunto(s)
Antioxidantes/aislamiento & purificación , Citotoxinas/aislamiento & purificación , Depuradores de Radicales Libres/aislamiento & purificación , Garcinia mangostana , Extractos Vegetales/aislamiento & purificación , Xantonas/aislamiento & purificación , Animales , Antioxidantes/farmacología , Células Cultivadas , Citotoxinas/farmacología , Depuradores de Radicales Libres/farmacología , Frutas , Humanos , Queratinocitos/efectos de los fármacos , Queratinocitos/patología , Masculino , Ratones , Ratones Endogámicos BALB C , Persona de Mediana Edad , Fenoles/aislamiento & purificación , Fenoles/farmacología , Extractos Vegetales/farmacología , Solventes , Xantonas/farmacologíaRESUMEN
Electrospinning is a process used to produce ultrafine fibers with diameters in the nanometer range. Electrospun fiber mats have high potentials for biomedical uses, due to their high surface area and ease of drug incorporation into the fibers. They can be used as carriers for drug delivery and can enhance drug release and skin permeability. The aim of this study was to prepare electrospun fiber mats and to incorporate extracts from the fruit hull of mangosteen. Antioxidant activity and extract release were determined and compared between the extract incorporated in the electrospun fiber mats and in the cast films. Poly(vinyl alcohol) (PVA) was selected as the polymer matrix. Extracts in the amount of 2.5%, 5%, and 10% w/w, based on the weight of PVA, were incorporated with 10% w/w PVA to finally obtain electrospun fiber mats and cast films. The extract content was evaluated by antioxidative activity using the 2,2-diphenyl-1-picryhydrazyl (DPPH) method. The morphology of the electrospun fiber mats was analyzed using a scanning electron microscope (SEM). The results showed that the diameters of the fibers were in nanoscales and that no crystal of the extract was found at any concentration of the extract. The extract contents in the electrospun fiber mats prepared at 2.5%, 5%, and 10% w/w of the extract were 9.6%, 9.7%, and 10.8% of the initial loading concentration, respectively, whereas, those in the cast films were 23.9%, 14.5%, and 21.0%, respectively. The release of the extract from the electrospun fiber mats prepared at 2.5%, 5%, and 10% w/w of the extract at 120 min were 73.2%, 83.6%, and 81.3% w/w, respectively. However, much slower release from the cast films was observed (i.e., 4.3%, 29.1%, and 40.8% w/w, respectively).
Asunto(s)
Garcinia mangostana/química , Alcohol Polivinílico/química , Microscopía Electrónica de RastreoRESUMEN
Condensation of 2-hydroxy-1-naphthalenecarboxylic acid with phloroglucinol afforded 9,11-dihydroxy-12H-benzo[a]xanthen-12-one (6). Construction of an additional dimethylpyran ring onto this skeleton, by alkylation with 3-chloro-3-methyl-1-butyne followed by Claisen rearrangement, gave access to 6-hydroxy-3,3-dimethyl-3H,7H-benzo[a]pyrano[3,2-h]xanthen-7-one (12) and 5-hydroxy-2,2-dimethyl-2H,6H-benzo[a]pyrano[2,3-i]xanthen-6-one (13), which were methylated into 6-methoxy-3,3-dimethyl-3H,7H-benzo[a]pyrano[3,2-h]xanthen-7-one (14) and 5-methoxy-2,2-dimethyl-2H,6H-benzo[a]pyrano[2,3-i]xanthen-6-one (15), respectively. Osmium tetroxide oxidation of 14 and 15 gave the corresponding (+/-)-cis-diols 16 and 17, which afforded the corresponding esters 18-21 upon acylation. Similarly, condensation of 2-hydroxy-1-naphthalenecarboxylic acid with 3,5-dimethoxyaniline gave 11-amino-9-methoxy-12H-benzo[a]xanthen-12-one (23) which was converted into 11-amino-9-hydroxy-12H-benzo[a]xanthen-12-one (24) upon treatment with hydrogen bromide in acetic acid. Alkylation with 3-chloro-3-methyl-1-butyne followed by Claisen rearrangement afforded 6-amino-3,3-dimethyl-3H,7H-benzo[a]pyrano[3,2-h]xanthen-7-one (25) and 5-amino-2,2-dimethyl-2H,6H-benzo[a]pyrano[2,3-i]xanthen-6-one (26). The new benzopyranoxanthone derivatives only displayed marginal antiproliferative activity when tested against L1210 and KB-3-1 cell lines. The only compounds found significantly active against L1210 cell line, 16 and 20, belong to the benzo[a]pyrano[3,2-h]xanthen-7-one series, which possess a pyran ring fused angularly onto the xanthone basic core.
Asunto(s)
Acronina/análogos & derivados , Acronina/química , Benzo(a)pireno/química , Xantonas/química , Xantonas/farmacología , Acronina/síntesis química , Acronina/farmacología , Animales , Antineoplásicos/síntesis química , Antineoplásicos/química , Antineoplásicos/farmacología , Benzo(a)pireno/análogos & derivados , Benzo(a)pireno/farmacología , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Concentración 50 Inhibidora , Ratones , Estructura Molecular , Xantonas/síntesis químicaRESUMEN
Twenty-two derivatives belonging to the cis-1,2-diacyloxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[a]pyrano[3,2-h]acridin-7-one series were synthesized in nine steps starting from 3,5-dimethoxyacetanilide (5) and 2-methoxy-1-naphthalenecarboxylic acid (7). Most of them exhibited submicromolar cytotoxicity when tested against murine leukemia (L1210) and human epidermoid carcinoma (KB-3-1) cell lines. The cytotoxic activity correlated strongly with the ability of the compounds to form covalent adducts with purified DNA. Among the most active compounds, 25, with IC50 values of 0.7 and 0.15 microM against L1210 and KB-3-1, respectively, was selected for evaluation in vivo against Colon 38 adenocarcinoma implanted in mice. This compound was active at 3 mg/kg i.v. (day 12 and 24) with 3/7 tumor free mice by day 80.