J. Agric. Food Chem
| Autor: | Jia-rong Zhang, Béatrice Langlois d'Estaintot, Katell Bathany, Jean Chaudiere, James Tolchard |
|---|---|
| Přispěvatelé: | Chimie et Biologie des Membranes et des Nanoobjets (CBMN), École Nationale d'Ingénieurs des Travaux Agricoles - Bordeaux (ENITAB)-Institut de Chimie du CNRS (INC)-Université de Bordeaux (UB)-Centre National de la Recherche Scientifique (CNRS), Institut Européen de Chimie et de Biologie (IECB), IECB |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
0106 biological sciences
reverse-phase HPLC Stereochemistry Electrospray ionization [SDV]Life Sciences [q-bio] Tandem mass spectrometry 01 natural sciences High-performance liquid chromatography Fragmentation (mass spectrometry) tandem mass spectrometry Leucocyanidin ComputingMilieux_MISCELLANEOUS Flavonoids [SDV.BBM.BS]Life Sciences [q-bio]/Biochemistry Molecular Biology/Structural Biology [q-bio.BM] Molecular Structure Chemistry 010401 analytical chemistry Leucoanthocyanidin reductase Stereoisomerism fragmentation pathways General Chemistry Nuclear magnetic resonance spectroscopy Reversed-phase chromatography [CHIM.MATE]Chemical Sciences/Material chemistry leucoanthocyanidin reductase NMR 0104 chemical sciences Epimer General Agricultural and Biological Sciences 010606 plant biology & botany |
| Zdroj: | Journal of Agricultural and Food Chemistry Journal of Agricultural and Food Chemistry, American Chemical Society, 2018, 66 (1), pp.351-358 Journal of Agricultural and Food Chemistry, American Chemical Society, 2018, 66 (1), pp.351-358. ⟨10.1021/acs.jafc.7b04380⟩ |
| ISSN: | 0021-8561 1520-5118 |
| Popis: | (+)-2,3-trans-3,4-cis-Leucocyanidin was produced by acidic epimerization of (+)-2,3-trans-3,4-trans-leucocyanidin synthesized by reduction of (+)-dihydroquercetin with NaBH4, and structures of the two stereoisomers purified by C18- and phenyl-reverse-phase high-performance liquid chromatography (HPLC) were confirmed by NMR spectroscopy. We confirm that only 3,4-cis-leucocyanidin is used by leucoanthocyanidin reductase as substrate. The two stereoisomers are quite stable in aqueous solution at -20 degrees C. Characterization of the two stereoisomers was also performed using electrospray ionization tandem mass spectrometry (ESI-MS/MS), and we discuss here for the first time the corresponding MS/MS fragmentation pathways, which are clearly distinct. The main difference is that of the mode of dehydration of the 3,4-diol in positive ionization mode, which involves a loss of hydroxyl group at either C-3 or C-4 for the 3,4-cis isomer but only at C-3 for the 3,4-trans isomer. Tandem mass spectrometry therefore proves useful as a complementary methodology to NMR to identify each of the two stereoisomers. |
| Databáze: | OpenAIRE |
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