Research Article

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

  1. Alexandra Ringl1,†,
  2. Sonja Prinz1,
  3. Antje Huefner2,
  4. Michael Kurzmann3,
  5. Brigitte Kopp1

Article first published online: 20 FEB 2007

DOI: 10.1002/cbdv.200790020

Issue

Chemistry & Biodiversity

Chemistry & Biodiversity

Volume 4, Issue 2, pages 154–162, February 2007

Additional Information

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

Author Information

  1. 1

    Department of Pharmacognosy, University of Vienna, Althanstrasse 14, A-1090 Vienna, (phone: +43 1 4277 55255; fax: +43 1 4277 55256)

  2. 2

    Department of Pharmaceutical Chemistry, University of Graz, Universitätsplatz 1, A-8010 Graz

  3. 3

    Pharmaceutical Biology, University of Erlangen-Nürnberg, Staudtstraße 5, D-91058 Erlangen

  1. †

    Part of the Ph.D. thesis of A. R.

  1. †

    Part of the Ph.D. thesis of A. R.

Publication History

  1. Issue published online: 20 FEB 2007
  2. Article first published online: 20 FEB 2007
  3. Manuscript Received: 16 NOV 2006

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Keywords:

  • Crataegus species;
  • D-Glucuronides;
  • Flavonoids;
  • Chemotaxonomy

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-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.

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