title: 1-Acetyl-3-[(3R)-hydroxyfatty acyl]glycerols: Lipid Compounds from Euphrasia rostkoviana Hayne and E. tetraquetra (Bréb.) Arrond.
abstract: Five homologous acetylated acylglycerols of 3-hydroxyfatty acids (chain lengths C(14) - C(18)), named euphrasianins A - E, were characterized for the first time in Euphrasia rostkoviana Hayne (Orobanchaceae) by gas chromatography/mass spectrometry (GC/MS) and high-performance liquid chromatography/atmospheric pressure chemical ionization-mass spectrometry (HPLC/APCI-MS(n) ). In addition to mass spectrometric data, structures of euphrasianins were verified via a three-step total synthesis of one representative homologue (euphrasianin A). The structure of the latter was confirmed by 1D- and 2D-NMR experiments as well as high-resolution electrospray ionization-mass spectrometry (HR-ESI-MS). The absolute configuration of the 3-hydroxyfatty acid moiety at C(3) was found to be R in the natural euphrasianins, which was determined by alkaline hydrolysis and methylation of a purified fraction, followed by chiral GC analysis. Furthermore, in extracts of Euphrasia tetraquetra (Bréb.) Arrond. euphrasianins C and E were detected exclusively, indicating that this subclass of lipid constituents is possibly valuable for fingerprinting methods.
authors.affiliation: Department of Analytical Development & Research, Section Phytochemical Research, WALA Heilmittel GmbH, Dorfstr. 1, DE-73087, Bad Boll/Eckwälden. peter.lorenz@wala.de.
authors.forename: Peter
authors.initials: P
authors.lastname: Lorenz
authors.affiliation: Department of Analytical Development & Research, Section Phytochemical Research, WALA Heilmittel GmbH, Dorfstr. 1, DE-73087, Bad Boll/Eckwälden.
authors.forename: Diana N
authors.initials: DN
authors.lastname: Knittel
authors.affiliation: Institute of Chemistry, Bioorganic Chemistry, Hohenheim University, Garbenstraße 30, DE-70599, Stuttgart.
authors.forename: Jürgen
authors.initials: J
authors.lastname: Conrad
authors.affiliation: Pharmaceutical Biology Department, University of Regensburg, Universitätsstraße 31, DE-93053, Regensburg.
authors.forename: Eva M
authors.initials: EM
authors.lastname: Lotter
authors.affiliation: Pharmaceutical Biology Department, University of Regensburg, Universitätsstraße 31, DE-93053, Regensburg.
authors.forename: Jörg
authors.initials: J
authors.lastname: Heilmann
authors.affiliation: Department of Analytical Development & Research, Section Phytochemical Research, WALA Heilmittel GmbH, Dorfstr. 1, DE-73087, Bad Boll/Eckwälden.
authors.forename: Florian C
authors.initials: FC
authors.lastname: Stintzing
authors.affiliation: Department of Analytical Development & Research, Section Phytochemical Research, WALA Heilmittel GmbH, Dorfstr. 1, DE-73087, Bad Boll/Eckwälden.
authors.forename: Dietmar R
authors.initials: DR
authors.lastname: Kammerer
mesh_terms: D002851:Chromatography, High Pressure Liquid; D032201:Euphrasia / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D005990:Glycerol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification*; D008055:Lipids / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D031670:Orobanchaceae / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D008055:Lipids; D010936:Plant Extracts; D005990:Glycerol
keywords: Acetyl monoacylglycerols; Euphrasianins; Eyebright; Hydroxyfatty acids; Orobanchaceae