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1.
Org Lett ; 26(18): 3889-3895, 2024 May 10.
Artículo en Inglés | MEDLINE | ID: mdl-38668739

RESUMEN

Two novel meroterpenoids, alliisativins A and B (1, 2) were discovered through a genome-based exploration of the biosynthetic gene clusters of the deep-sea-derived fungus Penicillium allii-sativi MCCC entry 3A00580. Extensive spectroscopic analysis, quantum calculations, chemical derivatization, and biogenetic considerations were utilized to establish their structures. Alliisativins A and B (1, 2) possess a unique carbon skeleton featuring a drimane sesquiterpene with a highly oxidized polyketide. Noteworthily, alliisativin A (1) showed dual activity in promoting osteogenesis and inhibiting osteoclast, indicating an antiosteoporosis potential.


Asunto(s)
Penicillium , Policétidos , Penicillium/química , Policétidos/química , Policétidos/farmacología , Estructura Molecular , Terpenos/química , Terpenos/farmacología , Animales , Osteoclastos/efectos de los fármacos , Ratones , Osteogénesis/efectos de los fármacos , Familia de Multigenes
2.
Mar Drugs ; 21(11)2023 Nov 16.
Artículo en Inglés | MEDLINE | ID: mdl-37999419

RESUMEN

A systematic investigation combined with a Global Natural Products Social (GNPS) molecular networking approach, was conducted on the metabolites of the deep-sea-derived fungus Samsoniella hepiali W7, leading to the isolation of three new fusaric acid derivatives, hepialiamides A-C (1-3) and one novel hybrid polyketide hepialide (4), together with 18 known miscellaneous compounds (5-22). The structures of the new compounds were elucidated through detailed spectroscopic analysis. as well as TD-DFT-based ECD calculation. All isolates were tested for anti-inflammatory activity in vitro. Under a concentration of 1 µM, compounds 8, 11, 13, 21, and 22 showed potent inhibitory activity against nitric oxide production in lipopolysaccharide (LPS)-activated BV-2 microglia cells, with inhibition rates of 34.2%, 30.7%, 32.9%, 38.6%, and 58.2%, respectively. Of particularly note is compound 22, which exhibited the most remarkable inhibitory activity, with an IC50 value of 426.2 nM.


Asunto(s)
Ácido Fusárico , Paecilomyces , Ácido Fusárico/farmacología , Macrófagos , Antiinflamatorios , Estructura Molecular
3.
Mar Drugs ; 21(10)2023 Sep 23.
Artículo en Inglés | MEDLINE | ID: mdl-37888439

RESUMEN

A systematic chemical investigation of the deep-sea-derived fungus Aspergillus versicolor 170217 resulted in the isolation of six new (1-6) and 45 known (7-51) compounds. The structures of the new compounds were established on the basis of exhaustive analysis of their spectroscopic data and theoretical-statistical approaches including GIAO-NMR, TDDFT-ECD/ORD calculations, DP4+ probability analysis, and biogenetic consideration. Citriquinolinones A (1) and B (2) feature a unique isoquinolinone-embedded citrinin scaffold, representing the first exemplars of a citrinin-isoquinolinone hybrid. Dicitrinones K-L (3-4) are two new dimeric citrinin analogues with a rare CH-CH3 bridge. Biologically, frangula-emodin (32) and diorcinol (17) displayed remarkable anti-food allergic activity with IC50 values of 7.9 ± 3.0 µM and 13.4 ± 1.2 µM, respectively, while diorcinol (17) and penicitrinol A (20) exhibited weak inhibitory activity against Vibrio parahemolyticus, with MIC values ranging from 128 to 256 µM.


Asunto(s)
Citrinina , Citrinina/química , Aspergillus/química , Hongos , Espectroscopía de Resonancia Magnética , Estructura Molecular
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