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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
Author(s) -
Ringl Alexandra,
Prinz Sonja,
Huefner Antje,
Kurzmann Michael,
Kopp Brigitte
Publication year - 2007
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.200790020
Subject(s) - vitexin , eriodictyol , chemistry , crataegus , rutin , isovitexin , chemotaxonomy , botany , luteolin , hyperoside , flavonoid , stereochemistry , organic chemistry , biology , taxonomy (biology) , antioxidant
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‐β‐ D ‐glucuronide ( 7 ) and luteolin‐7‐ O‐β‐ 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.