Antiproliferative Constituents in Plants. 10. Flavones from the Leaves of Lantana montevidensis BRIQ. and Consideration of Structure-Activity Relationship.

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The flavonoid fraction from the leaves of Lantana montevidensis BRIQ. (Verbenaceae) showed antiproliferative activity against human gastric adenocarcinoma (MK-1, GI50: 12 μg/ml), human uterus carcinoma (HeLa, 5 μg/ml), and murine melanoma (B16F10, 5 μg/ml) cells in vitro. Bioactivity-guided chemical investigation of the fraction has resulted in the isolation of apigenin (10) and ten 5,6,7-oxygenated flavones: cirsilineol (1), eupatorin (2), 5,4′-dihydroxy-6,7,3′,5′-tetramethoxyflavone (3), 5,6-dihydroxy-7,3′,4′-trimethoxyflavone (4), 5,6,4′-trihydroxy-7,3′,5′-trimethoxyflavone (5), 5,6,3′-trihydroxy-7,4′-dimethoxyflavone (6), 5,3′,4′-trihydroxy-6,7,5′-trimethoxyflavone (7), cirsiliol (8), hispidulin (9), and eupafolin (11). Antiproliferative activity of the isolated flavones, some other related flavones (luteolin, baicalein, 6-hydroxyluteolin, pectolinarigenin, jaceosidin, desmethoxycentaureidin, eupatilin, and chrysin) from other plant materials, and synthetic 6- and 7-methoxyflavones was evaluated, and the structure–activity relationships were examined.

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