Planta Med 2010; 76 - SL_47
DOI: 10.1055/s-0030-1264285

Chemopreventive potential of rhamnosyl depsides from Inga laurina

S Marqui 1, L Santos 1, M Young 2, L Torres 2, V Bolzani 1, M Moraes 3, C Soares 3, D Silva 4
  • 1Institute of Chemistry – UNESP, rua prof Francisco Degni s/n, 14800–900 Araraquara, Brazil
  • 2Instituto de Botanica-SMA, av Miguel Stefano, 04301–902 Sao Paulo, Brazil
  • 3School of Pharmacy – Unesp, rodovia Araraquara-Jau km1, 14801–902 Araraquara, Brazil
  • 4Institute of Chemistry – UNESP, Organic Chemistry, rua prof Francisco Degni s/n, 14800–900 Araraquara, Brazil

Fabaceae family is composed of 650 genera with ca. 18.000 species and is found in tropical and subtropical regions as shrubs and trees1, including species as Inga laurina, I. edulis and I. marginata, which are used as popular medicines in Brazil to treat stomach and inflammatory disorders. Few species of Inga genus have been investigated although some present important biological properties. Recent studies have shown the presence of flavonoids and other phenolic compounds from Inga species, which might be associated to their reported uses. 1,2 Preliminary analysis of Inga laurina leaves crude EtOH extract by TLC test nebulized with beta-carotene solution and in a liposome model using Fe2+ as radicalar reactions initiator indicated the presence of antioxidant compounds. Its phytochemical study led to the isolation of four new gallic acid derivatives from the EtOAc fraction from liquid-liquid partition of the EtOH extract, followed by chromatographic procedures including RP-HPLC. Their structures were determined through extensive 1D and 2D NMR and MS analysis as: 3-(2-rhamnopyranosyl-1,5-dihydroxyphenyl) gallate (1), 2-(1-rhamnopyranosyl-3,5-dihydroxyphenyl) gallate (2), 2-[1-(4′-galloyl)rhamnopyranosyl-3,5-dihydroxyphenyl] gallate (3) and 5-[1-rhamnopyranosyl-2-galloyl-3-hydroxyphenyl) gallate (4). As observed in the literature, Inga genus presents compounds with antioxidant activity, which was confirmed by the results obtained from the TLC analysis with beta-carotene as spray reagent. The free radical scavenging activities of compounds 1–4 were confirmed by the DPPH and ABTS assays, and their chemopreventive index (CI), evaluated through the induction of quinone-reductase enzyme, was comparable to the positive control BNF3, suggesting the chemopreventive potential of Inga laurina.

Acknowledgements: FAPESP for research grant 04/07932–7 awarded to DHSS (PI), and scholarships to MCCM and LAS; CAPES, for scholarship to SRM; and CNPq, for research fellowships to DHSS, MCMY and CPS.

References: 1. Lokvam, J et al. (2005)J. Chemical Ecol. 31, 11.

2. Lokvam, J et al. (2007)J. Nat. Prod. 70, 134.

3. Cuendet, M. et al. (2006)J. Nat. Prod. 69, 460.