Chemical Constituents and Cytotoxicites from the Stem of Ardisia virens

• Main Authors: Yi-Ju Lin, 林宜如
• Other Authors: Ih-Sheng Chen
• Format: Others
• Language: zh-TW
• Published: 2006
• Online Access: http://ndltd.ncl.edu.tw/handle/29629952851036315922

碩士 === 高雄醫學大學 === 天然藥物研究所碩士班 === 94 === Abstract Ardisia virens Kurz. (Myrsinaceae) is a shrub, distributed in India, Indonesia, Malaysia, Thailand, Vietnam, China, and Taiwan. The methanolic extract of the stem of this species has shown cytotoxicity on high-throughput screening against MCF-7, NCI-H460 and SF-268 cancer cell lines and was partitioned into n-hexane, EtOAc and H2O-soluble layers. The n-hexane-soluble layer showed cytotoxicity against above three cancer cell lines. Investigation of the active n-hexane layer by column chromatography has led to the isolation of six new compounds: 1-(3-hydroxy-5-methoxyphenyl)pentan-1-one (1), 4-hydroxy-2-methoxy-6- pentadecylphenyl acetate (13), 4-hydroxy-2-methoxy-6-tridecylphenyl acetate (14), 6-(2’-acetoxytridecyl)-4-hydroxy-2-methoxyphenyl acetate (16), 6-(2’-acetoxypentadecyl)-4-hydroxy-2-methoxyphenyl acetate (17),, 1-(2-formyl-3,6-dihydroxy-5-methoxyphenyl)tridecan-2-yl acetate (18), one compound first isolated from plant origin：1-(3,5-dihydroxyphenyl)- pentadecan-1-one (4), together with twenty-seven known compounds：1-(3,5-dihydroxyphenyl)heptan-1-one (2), 1-(3,5-dihydroxyphenyl)nonan-1- one (3), olivetol (5), 5-heptylresorcinol (6), 5-nonylresorcinol (7), (+)-3- (2’S-hydroxytridecyl)-5-methoxyphenol (8), (+)-3-(2’S-hydroxypentadecyl)- 5-methoxyphenol (9), virenol A (10), virenol B (11), virenol C (12), ardisianol (15), ardisianone (19), cornudentanone (20), 6-(2-acetoxy- tridecyl)-5-hydroxy-2-methoxy-1,4-benzoquinone (21), 6-(2-acetoxy- pentadecyl)-5-hydroxy-2-methoxy-1,4-benzoquinone (22), 2-methoxy- 6-tridecyl-1,4-benzoquinone (23), 2-methoxy-6-pentadecyl-1,4-benzo- quinone (24), 5-O-methylrapanone (25), mixture of β-sitosterol (26) and stigmasterol (27), mixture of linoleic acid (28) and stearic acid (29), mixture of palmitic acid (30), pentadecanoic acid (31), tetradecanoic acid (32), tridecanoic acid (33), and octanoic acid (34).The structures of these compounds were elucidated by spectral analysis. Among the isolates, 4-hydroxy-2-methoxy-6-pentadecylphenyl acetate (13), 4-hydroxy-2-methoxy-6-tridecylphenyl acetate (14), and ardisianol (15) showed cytotoxicities against MCF-7 (IC50= 3.4, 2.6, 3.1 μg /ml), NCI-H460 (IC50= 0.1, 0.7, 0.6 μg /ml) and SF-268 (IC50= 2.7, 1.6, 2.6 μg /ml ) cancer cell lines. respectively and 6-(2’-acetoxytridecyl)-4-hydroxy-2-methoxy- phenyl acetate (16), ardisianone (19) 與cornudentanone (20) showed selectively cytotoxicities only against NCI-H460 (IC50= 2.4, 2.3, 2.5 μg /ml)cancer cell lines respectively.