1-Acetyl-3-[(3R)-hydroxyfatty acyl]glycerols: Lipid Compounds from Euphrasia rostkoviana Hayne and E. tetraquetra (Bréb.) Arrond.
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- 作者：Peter Lorenz ; Diana N. Knittel ; Jü ; rgen Conrad ; Eva M. Lotter ; Jö ; rg Heilmann ; Florian C. Stintzing and Dietmar R. Kammerer
- 刊名：Chemistry & Biodiversity
- 出版年：2016
- 出版时间：May 2016
- 年：2016
- 卷：13
- 期：5
- 页码：602-612
- 全文大小：1389K
- ISSN：1612-1880
文摘
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 (Bréb.) Arrond. euphrasianins C and E were detected exclusively, indicating that this subclass of lipid constituents is possibly valuable for fingerprinting methods.