Part of the Ph.D. thesis of A. R.
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
Version of Record online: 20 FEB 2007
Copyright © 2007 Verlag Helvetica Chimica Acta AG, Zürich
Chemistry & Biodiversity
Volume 4, Issue 2, pages 154–162, February 2007
How to Cite
Ringl, A., Prinz, S., Huefner, A., Kurzmann, M. and Kopp, B. (2007), 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. Chemistry & Biodiversity, 4: 154–162. doi: 10.1002/cbdv.200790020
- Issue online: 20 FEB 2007
- Version of Record online: 20 FEB 2007
- Manuscript Received: 16 NOV 2006
- Crataegus species;
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.