RESUMEN
A new pregnane, 3α-hydroxy-7-ene-6,20-dione (1), and five known steroids (2-6), along with one known steroidal glycoside (7) were obtained from the fungus Cladosporium sp. WZ-2008-0042 cultured from a gorgonian Dichotella gemmacea collected from the South China Sea. The structure and absolute configuration of the new compound (1) were elucidated by comprehensive spectroscopic data and X-ray diffraction data. The compound has a rare configuration of 3α-OH that is different from most of pregnanes. All of the isolated compounds were evaluated for their antiviral activities against respiratory syncytial virus (RSV). Among them, 1 exhibited potential antiviral activity with the IC50 value of 0.12 mM.
Asunto(s)
Antivirales/farmacología , Cladosporium/química , Pregnanos/química , Animales , Antozoos/microbiología , Antibacterianos/química , Antibacterianos/farmacología , Antivirales/química , Inhibidores de la Colinesterasa/química , Inhibidores de la Colinesterasa/farmacología , Evaluación Preclínica de Medicamentos/métodos , Glicósidos/química , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Pregnanos/farmacología , Virus Sincitiales Respiratorios/efectos de los fármacos , Espectrometría de Masa por Ionización de Electrospray , Esteroides/química , Difracción de Rayos XRESUMEN
Seven new briarane diterpenoids, gemmacolides AZ-BF (1-7), were isolated together with eight known analogues (8-15) from the South China gorgonian Dichotella gemmacea. Their structures were elucidated based on detailed spectroscopic analysis and a comparison with reported data. In an in vitro bioassay, these compounds exhibited different levels of growth inhibition activity against A549 and MG63 cells, giving continuous evidences about the biological contribution of functional groups at C-2, C-12, C-13, and C-16. These compounds were also evaluated for their antibacterial and antifungal activities. Compound 8 exhibited a potential antibacterial activity against both Gram-positive bacterium Bacillus megaterium and Gram-negative bacterium Escherichia coli.
Asunto(s)
Antozoos/química , Diterpenos/química , Diterpenos/farmacología , Células A549 , Animales , Antibacterianos/química , Antibacterianos/farmacología , Antifúngicos/química , Antifúngicos/farmacología , Bacillus megaterium/efectos de los fármacos , Línea Celular Tumoral , China , Escherichia coli/efectos de los fármacos , HumanosRESUMEN
One new briarane-type diterpenoid, dichotellide V (1), along with four known analogues, gemmacolide N (2), dichotellide J (3), junceelin A (4) and junceellolide A (5), was isolated from the South China Sea gorgonian Dichotella gemmacea. All of the isolated compounds (1-5) were established by comprehensive analysis of the spectral data, especially 1D and 2D NMR (HMQC and HMBC) spectra. The cytotoxic activities of these compounds were evaluated.
Asunto(s)
Antozoos/química , Diterpenos/química , Animales , China , Diterpenos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
A new 19-oxygenated steroid, 25-acetate-nebrosteroid K (1), and five known steroids (2-6), along with one known 19-hydroxy steroidal glycoside (7) were obtained from the gorgonian Dichotella gemmacea collected from the South China Sea. The structure and relative configuration of 1 were elucidated by using comprehensive spectroscopic data including NOESY spectra. Compound 1 represents the first example of 19-oxygenated steroid with a 19-oic acid methyl ester group isolated from gorgonians. All of the isolated compounds were evaluated for lethal activity to brine shrimp Artemia salina and cytotoxicity against A549 and HL-60 cell lines. Among them, 1 showed strong lethality towards A. salina.
Asunto(s)
Antozoos/química , Esteroides/química , Animales , Artemia/efectos de los fármacos , China , Células HL-60/efectos de los fármacos , Humanos , Estructura Molecular , Esteroides/aislamiento & purificaciónRESUMEN
Six new (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids, gemmacolides N-S (1-6), were isolated together with four known analogues, juncenolide D, and juncins R, S and U (7-10), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by the detailed analysis of spectroscopic data in combination with the comparison with reported data. The absolute configuration of 1 was determined by a TDDFT calculation of its solution ECD spectrum, affording the determination of absolute configuration of other analogues by simply comparing their ECD spectra with that of 1. The cytotoxic and antimicrobial activities of these compounds were evaluated. In preliminary in vitro bioassays, compounds 4, 5, 6, 8 and 9 showed cytotoxicity against A549 and MG63, while compounds 1, 2, 4, 7-10 showed antimicrobial activity against the fungus Septoria tritici and the bacterium Escherichia coli.
Asunto(s)
Antozoos/química , Antiinfecciosos/química , Antiinfecciosos/farmacología , Diterpenos/química , Diterpenos/farmacología , Animales , Antiinfecciosos/aislamiento & purificación , Bacterias/efectos de los fármacos , Línea Celular Tumoral , China , Diterpenos/aislamiento & purificación , Hongos/efectos de los fármacos , Humanos , Espectroscopía de Resonancia Magnética/métodos , Modelos Moleculares , Océanos y MaresRESUMEN
Three new phenolic bisabolane-type sesquiterpenoids: (+)-methyl sydowate (1), 7-deoxy-7,14-didehydrosydonic acid (2), and 7-deoxy-7,8-didehydrosydonic acid (3), together with two known fungal metabolites were isolated from the fermentation broth of a marine-derived fungus Aspergillus sp., which was isolated in turn from a gorgonian Dichotella gemmacea collected from the South China Sea. Their structures were elucidated by combined spectroscopic methods, and the structure of 1 was further confirmed by single-crystal X-ray data.