title: Rapid isolation and identification of minor natural products by LC-MS, LC-SPE-NMR and ECD: isoflavanones, biflavanones and bisdihydrocoumarins from Ormocarpum kirkii.
abstract: The combination of the hyphenated techniques LC-MS and LC-SPE-NMR constitutes a powerful platform for the rapid isolation and identification of minor components from natural sources. Electronic circular dichroism (ECD) is a useful tool to determine the absolute configuration of small quantities of chiral molecules. In order to search for minor constituents present in an Ormocarpum kirkii extract, these techniques were applied for the separation and structure elucidation of a series of isoflavanones, biflavanones and biscoumarins. After optimization of chromatographic conditions and subsequent isolation, MS and 1D and 2D NMR data were collected. Experimental and calculated ECD spectra were used in conjunction with NMR data to confirm the absolute configuration of these compounds. Eight compounds were identified for the first time and six have been previously reported. The present approach offers a strategy for accelerating research on natural products.
authors.affiliation: Laboratory of Pharmacognosy and Pharmaceutical Analysis, Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B-2610 Antwerp, Belgium.
authors.forename: Yong-Jiang
authors.initials: YJ
authors.lastname: Xu
authors.forename: Kenn
authors.initials: K
authors.lastname: Foubert
authors.forename: Liene
authors.initials: L
authors.lastname: Dhooghe
authors.forename: Filip
authors.initials: F
authors.lastname: Lemière
authors.forename: Sheila
authors.initials: S
authors.lastname: Maregesi
authors.forename: Christina M
authors.initials: CM
authors.lastname: Coleman
authors.forename: Yike
authors.initials: Y
authors.lastname: Zou
authors.forename: Daneel
authors.initials: D
authors.lastname: Ferreira
authors.forename: Sandra
authors.initials: S
authors.lastname: Apers
authors.forename: Luc
authors.initials: L
authors.lastname: Pieters
mesh_terms: D001688:Biological Products / Q000032:analysis* / Q000737:chemistry / Q000302:isolation & purification*; D005591:Chemical Fractionation / Q000379:methods*; D002853:Chromatography, Liquid; D002942:Circular Dichroism; D003374:Coumarins / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D007887:Fabaceae / Q000737:chemistry*; D044950:Flavanones / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D007529:Isoflavones / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D008968:Molecular Conformation; D052616:Solid Phase Extraction; D013997:Time Factors
chemical_list: D001688:Biological Products; D003374:Coumarins; D044950:Flavanones; D007529:Isoflavones; C065753:isoflavanone