RESUMO
Four new polyketides, namely furantides A-B (1-2), talamin E (3) and arugosinacid A (4), and two known polyketides were obtained from the mangrove-derived fungus Penicillium sp. HDN15-312 using the One Strain Many Compounds (OSMAC) strategy. Their chemical structures, including configurations, were elucidated by detailed analysis of extensive NMR spectra, HRESIMS and ECD. The DPPH radicals scavenging activity of 3, with an IC50 value of 6.79 µM, was better than vitamin C.
Assuntos
Penicillium , Policetídeos , Penicillium/química , Policetídeos/farmacologia , Policetídeos/química , Policetídeos/isolamento & purificação , Sequestradores de Radicais Livres/farmacologia , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Picratos , Rhizophoraceae/microbiologia , Compostos de BifeniloRESUMO
Six new fusarin derivatives, fusarins G-L (1-6), together with five known compounds (5-11) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 5-11 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 µM. The structure-activity relationships of the fusarins are discussed herein.
Assuntos
Anti-Inflamatórios/farmacologia , Fusarium , Lactamas/farmacologia , Óxido Nítrico/antagonistas & inibidores , Polienos/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Fermentação , Fusarium/química , Fusarium/metabolismo , Lactamas/isolamento & purificação , Lipopolissacarídeos/farmacologia , Camundongos , Óxido Nítrico/metabolismo , Polienos/isolamento & purificação , Células RAW 264.7 , Metabolismo Secundário , Relação Estrutura-AtividadeRESUMO
Two new cembrane-type diterpenoids, lobophytins A (1) and B (3), and four new prostaglandins, (5E)-PGB2 (10), (5E)-13,14-dihydro-PGB2 (11), 13,14-dihydro-PGB2 (12) and 13,14-dihydro-PGB2-Me (13), together with ten known compounds were isolated from the soft coral Lobophytum sarcophytoides. The structures of these new secondary metabolites were identified by high resolution mass spectrometry (HR-ESIMS), nuclear magnetic resonance (NMR) and electron circular dichroism (ECD) analyses, as well as the modified Mosher's method. Compounds 6, 7, 9, 10, 12, 13, 15 and 16 showed potential anti-inflammatory activity by inhibiting the production of nitric oxide (NO) in RAW264.7 cells that were activated by lipopolysaccharide, with IC50 values ranging from 7.1 to 32.1 µM and were better than the positive control indomethacin, IC50 = 39.8 µM.
Assuntos
Antozoários/química , Anti-Inflamatórios/farmacologia , Diterpenos/farmacologia , Prostaglandinas/farmacologia , Animais , Linhagem Celular , Lipopolissacarídeos/farmacologia , Espectroscopia de Ressonância Magnética/métodos , Espectrometria de Massas/métodos , Camundongos , Óxido Nítrico/metabolismo , Células RAW 264.7RESUMO
Five new naphthalenones, two enantiomers (−)-1 and (+)-1 leptothalenone A, (−)-4,8-dihydroxy-7-(2-hydroxy-ethyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one ((−)-2), (4S, 10R, 4’S)-leptotha-lenone B (5), (4R, 10S, 4’S)-leptothalenone B (6), and a new isocoumarine, 6-hydroxy-5,8-dimethoxy-3-methyl-1H-isochromen-1-one (4), along with two known compounds (+)-4,8-dihydroxy-7-(2-hydroxy-ethyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one ((+)-2) and (+)-10-norparvulenone (3) were isolated from the marine-derived fungus Leptosphaerulina chartarum 3608. The structures of new compounds were elucidated by HR-ESIMS, NMR, and ECD analysis. All compounds were evaluated for cytotoxicity and anti-inflammatory activity. Compound 6 showed moderate anti-inflammatory activity by inhibiting the production of nitric oxide (NO) in lipopolysaccharide-stimulated RAW264.7 cells, with an IC50 value of 44.5 μM.