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1‐Acetyl‐3‐[(3 R) ‐hydroxyfatty acyl]glycerols: Lipid Compounds from Euphrasia rostkoviana Hayne and E. tetraquetra ( Bréb .) Arrond.
Author(s) -
Lorenz Peter,
Knittel Dia.,
Conrad Jürgen,
Lotter Eva M.,
Heilmann Jörg,
Stintzing Florian C.,
Kammerer Dietmar R.
Publication year - 2016
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201500233
Subject(s) - chemistry , mass spectrometry , chromatography , electrospray ionization , high performance liquid chromatography , tandem mass spectrometry , hydrolysis , organic chemistry
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.