Planta Med 2006; 72 - P_110
DOI: 10.1055/s-2006-949910

Modification of the polarity of an anthocyanin pigment. Structure determination and antioxidant activity

E Palé 1, P Duez 2, M Luhmer 3, M Nacro 1
  • 1Laboratoire de Chimie Organique Appliquée, Département de Chimie, UFR-SEA, Université de Ouagadougou, 03 BP 7021 Ouagadougou 03, Burkina Faso
  • 2Laboratoire de Pharmacognosie, de Bromatologie et de Nutrition Humaine, Institut de Pharmacie, Université Libre de Bruxelles, Campus de la Plaine CP 205–4, Bld Triomphe, B-1050 Bruxelles, Belgique
  • 3Laboratoire de RMN haute résolution, Département de Chimie Université Libre de Bruxelles, CP 160–08, 50 avenue Franklin Roosevelt, B-1050 Bruxelles, Belgique

In the aim to develop antioxidant compounds with cellular membrane anchoring potential, Cyanidin (3-O-(2-O-β-D-glucopyranosyl)-β-D-glucopyranosyl -5- O-β-D-glucopyranoside), an anthocyanin extracted from Ipomoea asarifolia (convolvulaceae), was acylated with a palmityl group to yield two new acylated anthocyanins. Their structures were elucidated using chemical, mass and NMR spectroscopy methods (1H and 13C, TOCSY-1D, DQF-COSY and HMBC).

Theses new pigments were found to consist of cyanidin 3-O-(2-O-β-D-glucopyranosyl)-β-D-glucopyranosyl-5-O-β-D-glucopyranosyl-7-O-palmitoyl and cyanidine 3-O-(2-O-β-D-glucopyranosyl)-β-D-glucopyranosyl -5- O-β-D-glucopyranosyl-7,3'-O-dipalmitoyl.

Using MTT and DPPH assays for measuring the cytotoxic and antioxidant properties of these compounds, it was found that the acylated anthocyanins retain the non-toxicity and antioxidant properties of the parent cyanidin. Work is in progress to further characterize the antioxidant profile of these interesting compounds.