ABSTRACT
The use of liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) in dereplication studies of medicinal plants is a common strategy, but the analyses of polyacetylenes by LC-ESI-MS are little explored and require huge efforts, especially if there are low concentrations in the extracts. A post-column sodiation strategy was successfully applied to enhance the detection of polyacetylene glycosides. Their molecular formulae were proposed by HRESI, whereas the polyacetylene chromophores were determined by UV data. The use of acetic acid in the mobile phase was essential to obtain satisfactory chromatographic resolution, and only the addition of sodium chloride solution allowed good mass spectra, internal calibration and undoubtedly the molar mass determination of polyacetylenes. This new approach has allowed the identification of polyacetylene glycosides from Bidens gardneri extract, guiding the isolation procedures, and two new compounds were obtained. The structures of the isolated polyacetylenes have been confirmed by 1D and 2D NMR, HRMS.
Subject(s)
Bidens , Glycosides/analysis , Plant Extracts/chemistry , Polyynes/analysis , Chromatography, Liquid , Plant Leaves , Plant Stems , Spectrometry, Mass, Electrospray Ionization , Tandem Mass SpectrometryABSTRACT
2D DOSY 1H NMR has proved to be a useful technique in the identification of the molecular skeleton of the four major compounds of ethyl acetate extract of aerial parts of Bidens sulphurea (Asteraceae). The combination of this technique with HPLC, mass spectrometry and other NMR techniques enabled the identification of four flavonoid glycosides: quercetin-3-O-beta-D-galactopyranoside, quercetin-3-O-beta-D-glycopyranoside, quercetin-3-O-alpha-L-arabinofuranoside and quercetin-3-O-beta-D-rhamnopyranoside.
Subject(s)
Asteraceae/chemistry , Flavonoids/analysis , Glycosides/analysis , Magnetic Resonance Spectroscopy , Reference StandardsABSTRACT
The dichloromethane extract of Calea uniflora afforded a mixture of two novel chromanones, uniflorol-A (1) and uniflorol-B (2), and one known chromanone, 2,2-dimethyl-6-(1-hydroxyethyl)-chroman-4-one (3). The structures of these compounds were determined by spectroscopic methods. Biological activity of the compounds against Leishmania major promastigotes was evaluated. Mixture of the novel chromanones 1 and 2 showed significant growth inhibition of the parasite in the micrograms per milliliter range.
Subject(s)
Anthraquinones/isolation & purification , Antiprotozoal Agents/isolation & purification , Asteraceae/chemistry , Leishmania major/drug effects , Plant Roots/chemistry , Animals , Anthraquinones/chemistry , Anthraquinones/pharmacology , Antiprotozoal Agents/chemistry , Antiprotozoal Agents/pharmacology , Chromones , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacologyABSTRACT
A new 5-deoxyflavone glycoside, identified as 7-O-(alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl)-3',4',7-trihydroxyflavone (1), was isolated from the aerial parts of Calea clausseniana. Its structure was determined by spectral analysis.
