Cytotoxic alkyl benzoquinones and alkyl phenols from Ardisia virens.
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 < or =4 microg/mL) against MCF-7, NCI-H460 and SF-268 cancer cell lines in vitro.
Chang
Hsun-Shuo
HS
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC.
Lin
Yi-Ju
YJ
Lee
Shiow-Ju
SJ
Yang
Cheng-Wei
CW
Lin
Wei-Yu
WY
Tsai
Ian-Lih
IL
Chen
Ih-Sheng
IS
D000473:Alkanes / Q000302:isolation & purification; D000478:Alkylation; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D031644:Ardisia / Q000737:chemistry*; D016227:Benzoquinones / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D045744:Cell Line, Tumor; D006536:Heptanes / Q000302:isolation & purification; D006801:Humans; D020128:Inhibitory Concentration 50; D009369:Neoplasms / Q000188:drug therapy*; D010636:Phenols / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use*; D018517:Plant Roots; D018547:Plant Stems
C548526:1-(3,5-dihydroxyphenyl)heptan-1-one; C548527:1-(3,5-dihydroxyphenyl)pentadecan-1-one; D000473:Alkanes; D000972:Antineoplastic Agents, Phytogenic; D016227:Benzoquinones; D006536:Heptanes; D010636:Phenols; D010936:Plant Extracts