RESUMEN
In the present study, four new compounds including a pair of 2-benzoyl tetrahydrofuran enantiomers, namely, (-)-1S-myrothecol (1a) and (+)-1R-myrothecol (1b), a methoxy-myrothecol racemate (2), and an azaphilone derivative, myrothin (3), were isolated along with four known compounds (4-7) from cultures of the deep-sea fungus Myrothecium sp. BZO-L062. Enantiomeric compounds 1a and 1b were separated through normal-phase chiral high-performance liquid chromatography. The absolute configurations of 1a, 1b, and 3 were assigned by ECD spectra. Among them, the new compound 1a and its enantiomer 1b exhibited anti-inflammatory activity, inhibited nitric oxide formation in lipopolysaccharide-treated RAW264.7 cells, and exhibited antioxidant activity in the 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) and oxygen radical absorbance capacity assays.
Asunto(s)
Antiinflamatorios/farmacología , Antioxidantes/farmacología , Hypocreales/metabolismo , Macrófagos/efectos de los fármacos , Animales , Antiinflamatorios/aislamiento & purificación , Antioxidantes/aislamiento & purificación , Sedimentos Geológicos/microbiología , Mediadores de Inflamación/metabolismo , Macrófagos/metabolismo , Ratones , Estructura Molecular , Óxido Nítrico/metabolismo , Capacidad de Absorbancia de Radicales de Oxígeno , Células RAW 264.7 , Relación Estructura-ActividadRESUMEN
Four new meroterpenoids 1â»4 and four new isocoumarinoids 5â»8, along with five known isocoumarinoids (9â»13), were isolated from the fungus Myrothecium sp. OUCMDZ-2784 associated with the salt-resistant medicinal plant, Apocynum venetum (Apocynaceae). Their structures were elucidated by means of spectroscopic analysis, X-ray crystallography, ECD spectra and quantum chemical calculations. Compounds 1â»5, 7, 9 and 10 showed weak α-glucosidase inhibition with the IC50 values of 0.50, 0.66, 0.058, 0.20, 0.32, 0.036, 0.026 and 0.37 mM, respectively.
Asunto(s)
Apocynum/química , Hongos/química , Terpenos/química , Cristalografía por Rayos X/métodos , Inhibidores de Glicósido Hidrolasas/químicaRESUMEN
A new alkylresorcinol, myrothecol A (1), along with two known ones (2 and 3), were isolated from a fungal strain Myrothecium sp. GY170016. Their structures were elucidated by extensive spectroscopic analysis. The absolute configuration of 1 was determined by electronic circular dichroism experiment. This is the first case of the presence of alkylresorcinols in genus Myrothecium. All the isolates were evaluated for their cytotoxic activities against human cancer cell line MCF-7 with IC50 values of 16.7, 13.2, 21.3 µM, respectively.
Asunto(s)
Antineoplásicos , Hypocreales , Hongos Mitospóricos , Neoplasias , Antineoplásicos/farmacología , Humanos , Estructura MolecularRESUMEN
@#Using a series of purification methods including silica gel, Sephadex LH-20 and preparative high performance liquid chromatography, secondary metabolites of Myrothecium sp. were purified from the ethyl acetate extract of the solid fermentation product. Based on structure characterization and investigation on the physical and chemical properties a, twelve monomeric compounds were identified as 3''-hydroxyverrucarin A (1), verrucarin A (2), verrucarin L acetate (3), verrucarin J (4), verrucarin K (5), roridin A (6), roridin D (7), roridin H (8), roridin J (9), verrol 4-acetate (10), (3S, 3aS, 6α, 6aR)-dihydrosporothrioride (11) and 4,6-dihydroxy-1(3H)-isobenzofuranone (12). Compounds 1, 5 and 9 -12 were isolated from Myrothecium sp. for the first time.Compounds 2, 3, 4, 7 and 8 exhibited strong inhibitory effects on Candida albicans, with a minimal inhibitory concentration (MIC50) of 0.318, 0.218, 0.047, 0.569 and 0.558 μg/mL, respectively.