ABSTRACT
From the hydromethanolic extract of the aerial parts of Globularia alypum grown in Morocco, a new chlorinated iridoid glucoside, globularioside has been isolated beside 5 known iridoid glycosides, globularin, globularicisin, globularidin, globularinin and globularimin. This is the first report of a chlorinated iridoid in G. alypum and in the Globulareaceae. Unlike all other known 7-chlorinated iridoid glucosides where the chlorine atom exhibits an alpha configuration, globularioside incorporate the chlorine atom as a 7beta substituent. The structures of the isolated compounds were established on the basis of ESI-MS, MS-MS, 1D and 2D NMR spectral analysis.
Subject(s)
Glucosides/chemistry , Iridoids/chemistry , Scrophulariaceae/chemistry , Antioxidants/chemistry , Antioxidants/isolation & purification , Antioxidants/pharmacology , Biphenyl Compounds , Carbohydrate Sequence , Chromatography, Liquid , Free Radicals/chemistry , Glucosides/isolation & purification , Glucosides/pharmacology , Iridoids/isolation & purification , Iridoids/pharmacology , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Sequence Data , Picrates/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, Ultraviolet , Spectroscopy, Fourier Transform InfraredABSTRACT
Three new phenolic compounds were isolated from the aerial parts of Globularia alypum. Their structures were determined as 6-hydroxyluteolin 7-O-laminaribioside (1), eriodictyol 7-O-sophoroside (2), and 6'-O-coumaroyl-1'-O-[2-(3,4-dihydroxyphenyl)ethyl]-beta-D-glucopyranoside (3). In addition, three phenylethanoid glycosides (acteoside, isoacteoside, and forsythiaside) and two flavonoid glycosides (6-hydroxyluteolin 7-O-beta-D-glucopyranoside and luteolin 7-O-sophoroside) were also isolated and are reported here for the first time in this plant. The structures of compounds 1-3 were established on the basis of their spectroscopic data analysis. Evaluation of the antioxidative activity, conducted in vitro, showed that the isolated phenylethanoids and flavonoid glycosides possess strong effects of this type.
