Planta Med 2010; 76 - O_1
DOI: 10.1055/s-0030-1264187

Catechin derivatives from Parapiptadenia rigida: biological studies and conformational analysis

C Schmidt 1, M Fronza 1, R Murillo 2, V Wray 3, G Bringmann 4, T Bruhn 4, B Heinzmann 5, S Laufer 6, I Merfort 1
  • 1Albert-Ludwigs-Universität Freiburg, Pharmaceutical Biology and Biotechnology, Stefan-Meier Str, 19, 79104 Freiburg im Breisgau, Germany
  • 2Universidad de Costa Rica, Escuela de Quimica and CIPRONA, San Jose, 2060 San Jose, Costa Rica
  • 3Helmholtz Centre for Infection Research, Structural Biology, Inhoffenstraße 7, 13824 Braunschweig, Germany
  • 4Würzburg Universität, Institute of Organic Chemistry, Am Hubland, 97074 Würzburg, Germany
  • 5Universidade Federal de Santa Maria, Departament of Pharmaceutical Industry, Campus, 97050–900 Santa Maria, Brazil
  • 6Eberhard-Karls-Universität, Department of Pharmaceutical and Medical Chemistry, Auf der Morgenstelle 8, 72076 Tübingen, Germany

Parapiptadenia rigida (Benth.) Brenan (Fabaceae), popularly known in Brazil as „Angico vermelho“, is a perennial tree native in South America. Preparations from its bark are used in traditional medicine because of its astringent, expectorant, antiseptic and antihemorrhagic properties [1–2], but no detailed phytochemical analysis has yet been performed. To increase our knowledge on the biologically active compounds from P. rigida, the ethanolic extract of its bark was phytochemically analysed and 10 catechin derivatives were isolated and identified by 1D and 2D NMR (1H, 13C, COSY, HSQC, HMBC, NOESY, 2D-ROESY) and ESI-MS spectroscopy analyses. 3″, 4′-O-methyl-apocynin (1), 3″,4′-O-methyl-apocynin-B (2), epigallocatechin-(4β-8)-4′-O-methyl-gallocatechin (3), 4′-O-methyl-gallocatechin-(4α-8)-4′-O-methyl-gallocatechin (4) and (–)-epigallocatechin-3-O-ferulate (5) have been found for the first time and 4′-O-methyl-(–)-epigallocatechin-3-O-gallate (6) for the first time from natural sources, in addition to the four known compounds 4′-O-methyl-gallocatechin (7), 4′-O-methyl-epigallocatechin (8), 3′-O-methyl-(–)-epicatechin (9) and (–)-epigallocatechin-3-O-gallate (10). Comprehensive conformational analyses were performed for the dimeric procyanidins 3 and 4. Absolute configuration of 2 was determined by CD analysis. The extract and some of the catechin derivatives were studied for their wound healing effect in the scratch assay and gave promising results which suggest that plant preparations from P. rigida and their effective ingredients may have beneficial effects as a wound healing remedy.

Acknowledgements: Government of Baden-Württemberg (Zukunftsoffensive IV). Brecht, V., Dept. of Pharm. Med. Chem., Uni Freiburg, Germany.

References: 1. Souza, G.C. et al. (2004) Rev. Bras. Pl. Med. 6:83–91.

2. Souza, G.C. et al. (2004)J. Ethnopharmacol. 90:135–143.