Leontopodic acid -: a novel highly substituted glucaric acid derivative from Edelweiss (Leontopodium alpinum Cass.) and its antioxidative and DNA protecting properties

Leontopodic acid-a novel full substituted hexaric acid derivative, was isolated from the aerial parts of Edelweiss (Leontopodium alpinum Cass.) as one of the major compounds. The complex structure of leontopodic acid-2-[(3S)-3-hydroxybutanoate]-3,4,5-tris-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate]-D-glucaric acid-was elucidated by mass spectrometry, 1D- and 2D NMR spectroscopy and HPLC monitored transesterification. Leontopodic acid exhibited pronounced antioxidative effects in the Briggs-Rauscher (BR) model [(r.a.c.). 3.4 +/- 0.5] and the trolox equivalent antioxidant capacity (TEAC) method (TEAC value of 1.53 +/- 0.11). The antioxidative properties of this compound were confirmed by the 3D method, an in vitro assay evaluating DNA protection against oxidative damage (IC50: 1.89 mu M). (c) 2005 Elsevier Ltd. All rights reserved.