Antiinflammatory activity and identification of molecules isolated from Caesalpinia paraguariensis (D. Parodi) Burk

SGARIGLIA, M. A.; SOBERÓN, J. R.; SAMPIETRO D.A.; VATTUONE, M. A.

Tafi del Valle

Congreso; XXVII Annual scientific meeting of the Tucuman biology association; 2010

Tucuman biology association

Previous reports showed the anti-inflammatory activity of C. paraguariensis bark infusion by hyaluronidase inhibition assay. AIF (antiinflammatory fraction) was obtained by bioguided-fractionation of the extract. The aims of this study were to isolate bioactive constituents, to assay enzymatic inhibition, and to structurally identify the bioactive molecules. AIF was analyzed by RP-HPLC and its components were isolated and purified. Hyaluronidase inhibition assay was carried out by  Reissig´s method. Identification was achieved by spectrometric techniques (UV-Vis, MS-ESI, and 1HRMN).Two eluates were isolated from AIF (M25 and M29), which showed inhibitory concentration 50% (IC50 at microg/ml): M25  1.5 +/- 0.1 and M29 2.3+/-0.1. Spectral analysis allowed us to identify them. M25 = ellagic acid: MS-ESI: [M-H]- mass/charge (m/z) 301.14; Exact mass: 302.1480 atomic mass units (u). Elemental composition: C14H6O8. 1HNMR in DMSO-d6 deltaH (ppm): H5,5 7.5 (s,2H). UV spectrum: lamda max (MeOH) (nm): 255.5, 258.0. M29=3Omethyl ellagic acid: MS-ESI: [M-H]- mass/charge (m/z) 315.0142. Exact mass: 316.0141 u. Elemental composition: C15H8O8. 1HNMR in DMSO-d6 deltaH (ppm):H5 7.51 (s, 1H), H5. 7.48 (s,1H), 3-OCH3, 4.06 (s,3H), UV spectrum: lambda max (MeOH) (nm): 249.9, 346sh, 367.2