RESUMO
Ten new (1-10) and 26 known (11-36) compounds were isolated from Penicillium griseofulvum MCCC 3A00225, a deep sea-derived fungus. The structures of the new compounds were determined by detailed analysis of the NMR and HRESIMS spectroscopic data. The absolute configurations were established by X-ray crystallography, Marfey's method, and the ICD method. All isolates were tested for in vitro anti-food allergic bioactivities in immunoglobulin (Ig) E-mediated rat basophilic leukemia (RBL)-2H3 cells. Compound 13 significantly decreased the degranulation release with an IC50 value of 60.3 µM, compared to that of 91.6 µM of the positive control, loratadine.
Assuntos
Antialérgicos/farmacologia , Basófilos/efeitos dos fármacos , Degranulação Celular/efeitos dos fármacos , Hipersensibilidade Alimentar/tratamento farmacológico , Penicillium/metabolismo , Animais , Antialérgicos/isolamento & purificação , Basófilos/imunologia , Linhagem Celular Tumoral , Hipersensibilidade Alimentar/imunologia , Sedimentos Geológicos/microbiologia , Imunoglobulina E/imunologia , Estrutura Molecular , Ratos , Relação Estrutura-AtividadeRESUMO
From the deep-sea-derived fungus Aspergillus candidus, one novel (1) and three known (2-4) p-terphenyl derivates were isolated. The structure of the new compound was established mainly on the basis of extensive analysis of 1D and 2D NMR data. All four isolates were tested for in vitro anti-food allergic and antitumor bioactivities. Compounds 3 and 4 showed potent antiproliferative effect against four cancer cells of Hela, Eca-109, Bel-7402, and PANC-1 with IC50 values ranging from 5.5 µM to 9.4 µM.
Assuntos
Aspergillus/química , Oceanos e Mares , Compostos de Terfenil/farmacologia , Antineoplásicos/farmacologia , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Morte Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Humanos , Espectroscopia de Prótons por Ressonância Magnética , Compostos de Terfenil/química , Compostos de Terfenil/isolamento & purificaçãoRESUMO
Viridicatol is a quinoline alkaloid isolated from the deep-sea-derived fungus Penicillium griseofulvum. The structure of viridicatol was unambiguously established by X-ray diffraction analysis. In this study, a mouse model of ovalbumin-induced food allergy and the rat basophil leukemia (RBL)-2H3 cell model were established to explore the anti-allergic properties of viridicatol. On the basis of the mouse model, we found viridicatol to alleviate the allergy symptoms; decrease the levels of specific immunoglobulin E, mast cell protease-1, histamine, and tumor necrosis factor-α; and promote the production of interleukin-10 in the serum. The treatment of viridicatol also downregulated the population of B cells and mast cells (MCs), as well as upregulated the population of regulatory T cells in the spleen. Moreover, viridicatol alleviated intestinal villi injury and inhibited the degranulation of intestinal MCs to promote intestinal barrier repair in mice. Furthermore, the accumulation of Ca2+ in RBL-2H3 cells was significantly suppressed by viridicatol, which could block the activation of MCs. Taken together, these data indicated that deep-sea viridicatol may represent a novel therapeutic for allergic diseases.
Assuntos
Antialérgicos/farmacologia , Hidroxiquinolinas/farmacologia , Penicillium/química , Penicillium/metabolismo , Quinolonas/farmacologia , Anafilaxia/tratamento farmacológico , Animais , Antialérgicos/isolamento & purificação , Organismos Aquáticos/química , Organismos Aquáticos/metabolismo , Linfócitos B/efeitos dos fármacos , Cálcio/metabolismo , Linhagem Celular Tumoral , Modelos Animais de Doenças , Hipersensibilidade Alimentar/tratamento farmacológico , Hipersensibilidade Alimentar/etiologia , Histamina/sangue , Hidroxiquinolinas/química , Hidroxiquinolinas/isolamento & purificação , Imunoglobulina E/sangue , Interleucina-10/sangue , Intestinos/efeitos dos fármacos , Intestinos/patologia , Mastócitos/efeitos dos fármacos , Camundongos , Ovalbumina/toxicidade , Peptídeo Hidrolases/sangue , Quinolonas/química , Quinolonas/isolamento & purificação , Ratos , Linfócitos T Reguladores/metabolismo , Fator de Necrose Tumoral alfa/sangue , beta-N-Acetil-Hexosaminidases/metabolismoRESUMO
Four new (penigrisacids A-D, 1-4) and one known (5) carotane sesquiterpenoids were isolated from the deep-sea-derived fungus Penicillium griseofulvum, along with four known compounds (6-9). The planar structures and relative configurations of the new compounds were determined by extensive analysis of the NMR and HRESIMS data. The absolute configurations were established by comparison of the experimental and calculated ECD (electronic circular dichroism) spectra or OR (optical rotation) value. Compound 9 exhibited potent anti-food allergic activity with IC50 value of 28.7 µM, while 4 showed weak cytotoxicity against ECA-109 tumor cells (IC50 = 28.7 µM).
Assuntos
Organismos Aquáticos/química , Penicillium/química , Sesquiterpenos/química , Linhagem Celular Tumoral , Dicroísmo Circular , Células HeLa , Humanos , Espectroscopia de Ressonância Magnética/métodos , Oceanos e Mares , Sesquiterpenos/farmacologiaRESUMO
A novel ergostane, sarocladione (1), was isolated from the deep-sea-derived fungus Sarocladium kiliense, along with 20 known compounds. The structure of 1 was determined mainly by a detailed analysis of its experimental and calculated NMR spectroscopic data. It is worth noting that 1 was the first steroid bearing a 5,10:8,9-diseco moiety. All 21 compounds were tested for in vitro antitumor activities against five cancer cell lines. ß-Sitostenone (7) and 4,6-dihydroxyeudesmane (20) showed significant effects on HeLa-S3 cells with the IC50 values of 9.2 µM and 9.3 µM, respectively.