title: Chemosystematic value of flavonoids from Crataegus x macrocarpa (Rosaceae) with special emphasis on (R)- and (S)-eriodictyol-7-O-glucuronide and luteolin-7-O-glucuronide.
abstract: The chemotaxonomic investigation of Crataegus x macrocarpa, a hybrid of C. laevigata and C. rhipidophylla, presents the qualitative and quantitative composition of its flavonoid pattern in relationship to its parent species for the first time. Six flavonoids were identified as vitexin-2''-O-rhamnoside (1), vitexin (2), isovitexin (3), rutin (4), hyperoside (5), and isoquercitrin (6). Furthermore, two flavonoids were isolated from C. x macrocarpa and identified as a diastereoisomeric mixture of (R)- and (S)-eriodictyol-7-O-beta-D-glucuronide (7) and luteolin-7-O-beta-D-glucuronide (8) by means of 1D- and 2D-NMR, MS, and UV experiments. Compounds 7 and 8 were isolated for the first time from Crataegus species. While missing in C. laevigata, their occurrence in C. rhipidophylla additionally emphasizes its chemotaxonomic relationship to C. x macrocarpa.
authors.affiliation: Department of Pharmacognosy, University of Vienna, Althanstrasse 14, A-1090 Vienna, Austria.
authors.forename: Alexandra
authors.initials: A
authors.lastname: Ringl
authors.forename: Sonja
authors.initials: S
authors.lastname: Prinz
authors.forename: Antje
authors.initials: A
authors.lastname: Huefner
authors.forename: Michael
authors.initials: M
authors.lastname: Kurzmann
authors.forename: Brigitte
authors.initials: B
authors.lastname: Kopp
mesh_terms: D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D027825:Crataegus / Q000737:chemistry*; D044950:Flavanones / Q000032:analysis* / Q000737:chemistry; D005965:Glucuronates / Q000032:analysis* / Q000737:chemistry; D047311:Luteolin / Q000032:analysis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D044950:Flavanones; D005965:Glucuronates; C068767:eriodictyol 7-glucuronide; C075406:luteolin-7-glucuronide; D047311:Luteolin