RESUMEN
Five triterpenes with a D:C-friedo-oleanane skeleton, D:C-friedo-oleana-7,9(11)-diene-3 beta,29-diol (3-epikarounidiol), 7-oxo-D:C-friedo-olean-8-en-3 beta-ol (7-oxoisomultiflorenol), 7-oxo-8 beta-D:C-friedo-olean-9(11)-ene-3 alpha,29-diol, D:C-friedo-olean-8-ene-3 alpha,29-diol (3-epibryonolol), and D:C-friedo-olean-8-ene-3 beta,29-diol (bryonolol), the first four of which are new naturally occurring compounds, were isolated from the seeds of Trichosanthes kirilowii Maxim. The structures were determined by spectral and chemical methods. 3-Epikarounidiol, 7-oxoisomultiflorenol, and 3-epibryonolol showed marked inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear inflammation in mice. The 50% inhibitory dose of these triterpenes for TPA-induced inflammation (1 microgram) was 0.2-0.6 mg/ear.
Asunto(s)
Antiinflamatorios no Esteroideos/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Otitis/tratamiento farmacológico , Triterpenos/aislamiento & purificación , Animales , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/uso terapéutico , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/uso terapéutico , Femenino , Espectroscopía de Resonancia Magnética , Ratones , Ratones Endogámicos ICR , Semillas/química , Triterpenos/química , Triterpenos/uso terapéuticoRESUMEN
The EtOAc extract of the sponge Xestospongia muta collected in Colombus Island, Bahamas, yielded eleven straight-chain unsaturated, polyacetylenic, brominated acids, seven of which were identified on the basis of spectral data, including the unknown acids 2-7. These acetylenic acids are the first known examples that have been shown to inhibit HIV protease, a critical enzyme in the replication of human immunodeficiency virus.
Asunto(s)
Compuestos de Boro/farmacología , Ácidos Grasos Insaturados/farmacología , Inhibidores de la Proteasa del VIH/farmacología , Poríferos/química , Extractos de Tejidos/farmacología , Animales , Compuestos de Boro/aislamiento & purificación , Células Cultivadas , Ácidos Grasos Insaturados/aislamiento & purificación , Liofilización , Inhibidores de la Proteasa del VIH/aislamiento & purificación , Humanos , L-Lactato Deshidrogenasa/metabolismo , ConejosRESUMEN
The structure of 7-oxodihydrokarounidiol [7-oxo-D:C-friedo-olean-8-ene-3 alpha,29-diol], isolates from the seeds of Trichosanthes kirilowii (Cucurbitaceae), was determined by chemical correlation with karounidiol [D:C-friedo-oleana-7,9(11)-diene-3 alpha,29-diol] from the same source. Two other natural products, viz. bryonolic acid (3 beta-hydroxy-D:C-friedo-olean-8-en-29-oic acid) and bryononic acid (3-oxo-D:C-friedo-olean-8-en-29-oic acid), were also correlated with karounidiol.
Asunto(s)
Ácido Oleanólico/análogos & derivados , Extractos Vegetales/química , Espectroscopía de Resonancia Magnética , Ácido Oleanólico/química , Plantas/químicaRESUMEN
An x-ray crystal structure determination of a dinostanol from the dinoflagellate Protoceratium reticulatum and zooxanthellae from Orbulina universa was completed. The novel sterol was shown to be 3 beta-hydroxy-4 alpha, 23R,24R-trimethyl-5 alpha-cholestane and may be one of the molecular fossils found in sediment cores from the deepest Black Sea trench.
Asunto(s)
Colestanoles , Fenómenos Químicos , Química , Modelos Moleculares , Difracción de Rayos XRESUMEN
The isolation and structure elucidation of nine new trace sterols with highly branched side chains from a Pseudaxinyssa species from the Australian Great Barrier Reef are described.
Asunto(s)
Poríferos/análisis , Esteroles/análisis , Animales , Australia , Fenómenos Químicos , Química , Cromatografía de Gases , Cromatografía Líquida de Alta Presión , Peso Molecular , Agua de MarRESUMEN
13C/12C ratios of sets of compounds, algal sterols and terpenes, isolated from dinoflagellate symbiont (zooxanthellae)-bearing soft corals and gorgonians were determined. In most cases, a significant difference was found between the delta 13C values of the terpenes and of the algal sterols from the same set, the algal sterols containing less 13C than the terpenes. These results can only be explained if terpenes are synthesized by the host. Cultured zooxanthellae, isolated from symbiotic associations, do not make terpenes. Algal sterols of the various sets do not all have the same delta 13C value: average values range from -18.2 to -24.3%. A consistent difference of about 7% in the delta 13C values of sterols of cultured symbionts isolated from two of the gorgonians was found. This has potential applications for the taxonomy of zooxanthellae, most of which are believed by some specialists to be one discrete species.
Asunto(s)
Cnidarios/fisiología , Eucariontes/fisiología , Simbiosis , Terpenos/análisis , Animales , Isótopos de Carbono , Espectrometría de Masas/métodos , Agua de Mar , Especificidad de la Especie , Esteroles/análisis , Terpenos/metabolismoRESUMEN
The sterol mixture isolated from the marine alga Eutreptia viridis consists mainly of delta 5,7-dienes which account for 80% of the free sterols. Eighteen different sterols were detected, including a novel sterol with the rare delta 23-unsaturation, viz. 24-ethylcholesta-5,7,23Z-trien-3 beta-o1.
Asunto(s)
Colestenos/aislamiento & purificación , Euglena/análisis , Esteroles/aislamiento & purificación , Cromatografía de Gases/métodos , Espectroscopía de Resonancia Magnética , Espectrometría de Masas/métodos , Relación Estructura-ActividadRESUMEN
Eighteen components of the sterol fraction of Pyrocystis lunula have been identified. In addition to 4 alpha-methyl sterols (typical dinoflagellate sterols), regular sterols, both with a saturated and delta 5-unsaturated skeleton, were isolated, together with delta 4-3-keto steroids including the hitherto unknown 23,24R-dimethyl-4,22E-cholestadien-3-one.
Asunto(s)
Dinoflagelados/análisis , Esteroles/análisis , Animales , Cromatografía Líquida de Alta Presión , Espectrometría de MasasRESUMEN
QUANTITATIVE STEROL COMPOSITIONS OF CULTURED ZOOXANTHELLAE ISOLATED FROM VARIOUS PACIFIC AND ATLANTIC INVERTEBRATE HOSTS: Zoanthus sociatus (a zoanthid), Oculina diffusa (a scleractian coral), Tridacna gigas (a giant clam), Melibe pilosa (a nudibranch), and Aiptasia pulchella (a sea anemone) are reported. The results clearly demonstrate large differences in sterol patterns of zooxanthellae and that there is no obvious relationship between the taxonomic affiliation of the host and the sterol pattern of its isolated symbiont. The sterols of the zooxanthellae of O. diffusa (Cnidaria) and T. gigas (Mollusca) are qualitatively equivalent. Based on the structures of the two major free sterols synthesized by each alga, the zooxanthellae from different hosts were separated into three distinct groups. It was also found that an aposymbiotic alga can synthesize the unique marine sterols gorgosterol and 23-desmethylgorgosterol. Most of the sterols were identified by using mass spectroscopy and 360-MHz proton magnetic resonance. Spectroscopic data are reported for four novel sterols-(23,24R)-dimethyl-5alpha-cholest-(22E)-en-3beta-o l, 23-methyl-5alpha-cholest-22E-en-3beta-ol, cholesta-5,14-dien-3beta-ol, and 4alpha-methyl-5alpha-cholesta-8(14)-24-dien-3beta-ol.
RESUMEN
Two new sterols, (24E)-24-n-propylidenecholesterol and 24 epsilon-n-propylcholesterol, were isolated from a cultured marine Chrysophyte. Since most of the steroids found in marine invertebrates are unchanged or modified sterols of algal or symbiotic origin, the discovery of these two unusual sterols in a unicellular alga grown under well-defined conditions contributes to our knowledge of sterols in marine food chains and offers a potential substrate for biosynthetic labeling experiments.