Cytotoxic alkyl benzoquinones and alkyl phenols from Ardisia virens

Add time:09/25/2019    Source:sciencedirect.com

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 (IC50 values ⩽4 μg/mL) against MCF-7, NCI-H460 and SF-268 cancer cell lines in vitro.

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