Lorenz, Peter and Knittel, Diana N. and Conrad, Juergen and Lotter, Eva M. and Heilmann, Joerg and Stintzing, Florian C. and Kammerer, Dietmar R. (2016) 1-Acetyl-3-[(3R)-hydroxyfatty acyl] glycerols: Lipid Compounds from Euphrasia rostkoviana HAYNE and E. tetraquetra (BREB.) ARROND. CHEMISTRY & BIODIVERSITY, 13 (5). pp. 602-612. ISSN 1612-1872, 1612-1880
Full text not available from this repository. (Request a copy)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-MSn). 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 (BREB.) ARROND. euphrasianins C and E were detected exclusively, indicating that this subclass of lipid constituents is possibly valuable for fingerprinting methods.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | 3-HYDROXY FATTY-ACIDS; MS DETERMINATION; SCROPHULARIACEAE; OROBANCHACEAE; GLYCOSIDES; DIACYLGLYCEROLS; IDENTIFICATION; OFFICINALIS; FLOWERS; LEAVES; Eyebright; Orobanchaceae; Acetyl monoacylglycerols; Hydroxyfatty acids; Euphrasianins |
| Subjects: | 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 15 Mar 2019 09:11 |
| Last Modified: | 15 Mar 2019 09:11 |
| URI: | https://pred.uni-regensburg.de/id/eprint/2966 |
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