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Seven new phenylpropanoids, including two pairs of enantiomers of 8- O -4′-type neolignans, named (±)-xanthiifructins A-B ( 1a/1b - 2a/2b ), a pair of simple phenylpropanoid derivatives (±)-xanthiifructins C ( 3a/3b ), and a racemic phenylpropanoid derivative xanthiifructin D ( 4 ), together with four known analogues ( 5 - 8 ) were isolated from the fruits of  Xanthium sibiricum . Racemic xanthiifructins A-C were separated on chiral HPLC columns. Their structures were elucidated by comprehensive spectroscopic data analysis and comparison with the literatures. The anti-inflammatory and cytotoxic activities were evaluated for all isolates. Among them, (-)-xanthiifructin C ( 3b ) exhibited potent inhibitory effect against nitric oxide production in lipopolysaccharide-activated RAW 264.7 mouse macrophage cells with an IC 50  value of 9.94 ± 0.57 μM. All compounds obviously were inactive for three human tumor cell lines (MCF-7, HepG2, and A549) with IC 50  values much more than 10 μM.

New phenylpropanoids from the fruits of Xanthium sibiricum and their anti-inflammatory activity