title: Enantiomeric determination and evaluation of the racemization process of atropine in Solanaceae seeds and contaminated samples by high performance liquid chromatography-tandem mass spectrometry.
abstract: A new method has been developed for the enantioselective separation of (-) and (+) hyoscyamine in Solanaceaes seeds and contaminated buckwheat. Chromatographic separation was optimized, evaluating two chiral columns, Chirobiotic V and Chiralpal-AY3. Better resolution was obtained using a Chiralpak-AY3 column, utilizing as mobile phase ethanol (0.1% diethanolamine). An extraction procedure based on a modified QuEChERS (Quick, Easy, Cheap, Effective, Rugged and Safe) was applied, using water and acetonitrile containing 1% of acetic acid, and a clean-up step utilizing primary secondary amine (PSA) and graphitized carbon black (GCB) as sorbents. The extract was diluted with ethanol (50/:50, v/v) prior to chromatographic analysis, and the separation was carried out avoiding the racemization during this stage. Enantiomerization process of atropine was studied in samples at different conditions such as temperature (30, 50 and 80°C) and pH (3, 5, 7 and 9), observing that racemization occurs at high pH (9) and temperature (80°C). Stramonium and Brugmansia seeds were analyzed and the concentration of (-)-hyoscyamine was 1500mg/kg and 320mg/kg respectively. Contaminated buckwheat was also determined and (-)-hyoscyamine was detected at 170μg/kg.
authors: Department of Chemistry and Physics, Analytical Chemistry Area, University of Almería, Research Centre for Agricultural and Food Biotechnology (BITAL), Agrifood Campus of International Excellence ceiA3(,) Carretera de Sacramento s/n, E-04120, Almería, Spain.
authors: Jesús
authors: J
authors: Marín-Sáez
authors: Department of Chemistry and Physics, Analytical Chemistry Area, University of Almería, Research Centre for Agricultural and Food Biotechnology (BITAL), Agrifood Campus of International Excellence ceiA3(,) Carretera de Sacramento s/n, E-04120, Almería, Spain.
authors: Roberto
authors: R
authors: Romero-González
authors: Department of Chemistry and Physics, Analytical Chemistry Area, University of Almería, Research Centre for Agricultural and Food Biotechnology (BITAL), Agrifood Campus of International Excellence ceiA3(,) Carretera de Sacramento s/n, E-04120, Almería, Spain. Electronic address: agarrido@ual.es.
authors: Antonia
authors: A
authors: Garrido Frenich
mesh_terms: D001285:Atropine / Q000737:chemistry* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D013286:Datura stramonium / Q000737:chemistry; D019612:Fagopyrum / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D064692:Hyoscyamine / Q000032:analysis; D007202:Indicators and Reagents; D057230:Limit of Detection; D015203:Reproducibility of Results; D012639:Seeds / Q000737:chemistry; D019657:Solanaceae / Q000737:chemistry*; D012997:Solvents; D013237:Stereoisomerism; D053719:Tandem Mass Spectrometry; D013696:Temperature
chemical_list: D007202:Indicators and Reagents; D012997:Solvents; D001285:Atropine; D064692:Hyoscyamine
keywords: (−)-Hyoscyamine; Atropine; Buckwheat; Chiral separation; Racemization process; Solanaceaes seeds