RESUMEN
One new 18-oxygenated polyhydroxy steroid, (24S)-ergostan-3ß,5α,6ß,18,25-pentaol 18,25-diacetate (1), along with five known analogues (2-6), was isolated from a soft coral Sarcophyton sp. collected from the South China Sea. The structure of the new compound (1) was elucidated by 1D NMR, 2D NMR and mass spectrometry. The absolute configuration of 1 was determined by the application of the modified Mosher's method. The isolated compounds were assayed for their cytotoxic and antimicrobial activities.
Asunto(s)
Antozoos/química , Esteroides/química , Animales , China , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
Chemical investigation of the ethanol extract of soft coral Sinularia sp. collected from the South China Sea led to the isolation of three new polyoxygenated sterols, (3S,23R,24S)-ergost-5-ene-3ß,23α,25-triol (1), (24S)-ergostane-6-acetate-3ß,5α,6ß,25-tetraol (2), (24S)-ergostane-6-acetate-3ß,6ß,12ß,25-tetraol (3) together with three known ones (4-6). The structures, including relative configurations of the new compounds (1-3), were elucidated by detailed analysis of spectroscopic data (IR, UV, NMR, MS) and by comparison with related reported compounds. The absolute configuration of 1 was further determined by modified Mosher's method. Compound 5 exhibited moderate cytotoxicity against K562 cell line with an IC(50) value of 3.18 µM, but also displayed strong lethality toward the brine shrimp Artemia salina with a LC(50) value of 0.96 µM.
Asunto(s)
Antozoos/química , Esteroles/análisis , Animales , Artemia , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Humanos , Espectroscopía de Resonancia Magnética , Esteroles/química , Esteroles/farmacologíaRESUMEN
Two new prenylgermacrane-type diterpenoids, lobophytumins A and B (1 and 2), two new prenyleudesmane-type diterpenoids, lobophytumins C and D (3 and 4), and two new spatane-type diterpenoids, lobophytumins E and F (5 and 6), were isolated from the Hainan soft coral Lobophytum cristatum Tixier-Durivault. Their structures, including relative configuration, were elucidated by detailed analysis of spectroscopic data and by comparison with related known compounds. In addition, the absolute configuration of lobophytumin C (3) was tentatively assigned by comparing its specific rotation with that of the closely related model compound (-)-ß-selinene (8). On the basis of biogenetic considerations, the absolute configurations of lobophytumins A, B, and D-F were also tentatively suggested. This is the first report of spatane-type diterpenoids from a soft coral source. The present work supports Faulkner's proposal of prenylgermacrene as the precursor of many diterpenes. In a bioassay, lobophytumins C and D (3 and 4) showed weak in vitro cytotoxicities against the tumor cell lines A-549 and HCT-116.
Asunto(s)
Antozoos/química , Antineoplásicos/aislamiento & purificación , Diterpenos/aislamiento & purificación , Animales , Antineoplásicos/química , Antineoplásicos/farmacología , Diterpenos/química , Diterpenos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Sesquiterpenos de Eudesmano , Estereoisomerismo , Tetrahidronaftalenos/químicaRESUMEN
Four diterpenes, tritoniopsins A-D (1-4), have been isolated from the South China Sea nudibranch Tritoniopsis elegans and its prey, the soft coral Cladiella krempfi. They display an unprecedented pyran ring in the cladiellane framework, thus representing a novel cladiellane-based diterpene family. Their structures have been mainly characterized by NMR and mass spectrometric techniques, whereas the relative configuration of compound 1 was secured by X-ray analysis. Antiproliferative assays on tumor and nontumor cell lines have been carried out for the main metabolite, tritoniopsin B (2).
Asunto(s)
Antozoos/química , Antineoplásicos/aislamiento & purificación , Diterpenos/aislamiento & purificación , Gastrópodos/química , Animales , Antineoplásicos/química , Antineoplásicos/farmacología , Cristalografía por Rayos X , Diterpenos/química , Ensayos de Selección de Medicamentos Antitumorales , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Océanos y MaresRESUMEN
Seven new briarane diterpenoids, gemmacolides G-M (1-7), were isolated together with two known analogues, juncin O and junceellolide C, from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by detailed analysis of spectroscopic data and comparison with reported data. In an in vitro bioassay, these compounds exhibited different levels of growth inhibition activity against A549 and MG63 cells. In particular, compound 4 was more active than the positive control adriamycin against A549 cells. Compounds 4 and 7 also exhibited weak antimicrobial activity against the bacterium Bacillus megaterium and the fungus Septoria tritici, respectively.
Asunto(s)
Antozoos/química , Antiinfecciosos/aislamiento & purificación , Antineoplásicos/aislamiento & purificación , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Animales , Antiinfecciosos/química , Antiinfecciosos/farmacología , Antineoplásicos/química , Antineoplásicos/farmacología , Ascomicetos/efectos de los fármacos , Bacillus megaterium/efectos de los fármacos , Diterpenos/química , Doxorrubicina/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Océanos y MaresRESUMEN
Eight new marine steroids, characterized by either the presence of an aromatic ring or a cross-conjugated dienone system in ring A, were isolated from the Hainan soft coral Dendronephthya studeri Ridley. Their structures were elucidated on the basis of detailed spectroscopic analysis and by comparison of their NMR data with those reported in the literature.
Asunto(s)
Antozoos/química , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Esteroides/química , Esteroides/aislamiento & purificación , Animales , Antineoplásicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Células HL-60 , Humanos , Leucemia P388 , Ratones , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Esteroides/farmacologíaRESUMEN
One new cembrane diterpenoid, named sarcolactone A (1), along with five known compounds (2-6) were isolated from the soft coral Sarcophyton infundibuliforme collected from the South China Sea. The structure of sarcolactone A (1) was elucidated by comprehensive analysis of spectral data, especially 2D-NMR spectra (1H-1H COSY, HMBC and NOESY). All the compounds were evaluated for their brine shrimp lethality and antifouling activities.