Cytotoxic alkyl benzoquinones and alkyl phenols from Ardisia virens

Fourteen compounds ( 1– 14), together with thirty-four other known compounds, including three ( 15– 17) were isolated from Ardisia virens. Compounds 3, 10– 12, 18, 19, and 31 displayed cytotoxicity against MCF-7, NCI-H460 and SF-268 cancer cell lines in vitro. Bioassay-guided fractionation of roots and stems of Ardisia virens Kurz (Myrsinaceae) led to isolation of fourteen compounds, (2′ R)-6-(2′-acetoxypentadecyl)-5-hydroxy-2-methoxy-1,4-benzoquinone ( 1), (2′ R)-6-(2′-acetoxytridecyl)-5-hydroxy-2-methoxy-1,4-benzoquinone ( 2), (2′ R)-6-(2′-acetoxytridecyl)-2-methoxy-1,4-dihydroxybenzene ( 3), (2′ R)-6-(2′-acetoxytridecyl)-5-formyl-2-methoxy-1,4-dihydroxybenzene ( 4), 1-(3,5-dihydroxyphenyl)nonan-1-one ( 5), 1-(3-hydroxy-5-methoxyphenyl)pentan-1-one ( 6), (2′ S)-3-hydroxy-5-methoxyphenyl-2′-tridecanol ( 7), (2′ S)-3-hydroxy-5-methoxyphenyl-2′-pentadecanol ( 8), (2′ S)-5-acetoxy-3-hydroxyphenyl-2′-tetradecanol ( 9), 1-acetoxy-2-methoxy-6-pentadecyl-4-hydroxybenzene ( 10), 1-acetoxy-2-methoxy-6-tridecyl-4-hydroxybenzene ( 11), (2′ R)-1-acetoxy-6-(2′-acetoxy-tridecyl)-2-methoxy-4-hydroxybenzene ( 12), (2′ R)-1-acetoxy-6-(2′-acetoxypentadecyl)-2-methoxy-4-hydroxybenzene ( 13), and 1-acetoxy-6-(2′-ketopentadecyl)-2-methoxy-4-hydroxylbenzene ( 14), together with thirty-four other known compounds, of which three, 1-(3,5-dihydroxyphenyl)pentan-1-one ( 15), 1-(3,5-dihydroxyphenyl)heptan-1-one ( 16), and 1-(3,5-dihydroxyphenyl)pentadecan-1-one ( 17), were isolated for the first time from a natural source. Their structures were elucidated by analyses of spectroscopic data. Seven cytotoxic constituents were found to be 3, 10– 12, ardisianone ( 18), cornudentanone ( 19), and ardisianol ( 31) with cytotoxic properties (IC 50 values ⩽4 μg/mL) against MCF-7, NCI-H460 and SF-268 cancer cell lines in vitro.