Two new compounds, coniferyl 9-O-[beta-D-apiofuranosyl(1-->6)]-O-beta-D-glucopyranoside (1) and sinapyl 9-O-[beta-d-apiofuranosyl(1-->6)]-O-beta-D-glucopyranoside (2), were isolated from the seeds of Punica granatum (pomegranate), together with five known compounds, 3,3'-di-O-methylellagic acid (3), 3,3',4'-tri-O-methylellagic acid (4), phenethyl rutinoside, icariside D1, and daucosterol. The structures of 1 and 2 were elucidated by spectroscopic data analysis. Compounds 1-4 exhibited antioxidant activity, which was evaluated by measurement of low-density lipoprotein (LDL) susceptibility to oxidation and by determination in vitro of malondialdehyde (MDA) levels in the rat brain.
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Wang et al. (2004) studied this question.