A new flavonoid glucuronide, apigenin 7-O-β-D-(4′-caffeoyl)glucuronide (1), and the known compound, apigenin 7-O-β-D-glucurnoide, were isolated from the flowers of Chrysanthemum morifolium, along with five known flavonoids. The structure of 1 was elucidated by the aid of spectroscopic analyses. Among isolated compounds, apigenin 7-O-β-D-(4″-caffeoyl)glucuronide showed strong HIV-1 integrase inhibitory activity (IC50 = 7.2 ± 3.4 μg/ml) and anti-HIV activity in a cell culture assay (EC50 = 41.86 ± 1.43 μg/ml) using HIV-IIIIB infected MT-4 cells.
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