Cytotoxic and Antioxidative Phenolic Compounds from the Traditional Chinese Medicinal Plant, Myristica fragrans

Two new phenolic compounds were isolated from the fruits of Myristica fragrans and their structures were elucidated as (-)-1-(2,6-dihydroxyphenyl)-9-[4-hydroxy-3-(p-menth-1-en-8-oxy)phenyl]-1-nonanone (1) and (7R,8R)-7,8-dihydro-7-(3,4-dihydroxyphenyl)-3'-methoxy-8- methyl-1'-(E-propenyl)benzofuran (2). In addition, the absolute configuration of (+)-Delta 8'-7-acetoxy-3,4,3',5'-tetramethoxy-8-O-4'-neolignan (3) was determined for the first time through spectroscopic and chemical methods. Their antioxidative activities against 2,2-diphenyl-1-picrylhydrazyl radical and cytotoxicity against K-562 cells were tested, and (7S,8S,7'R,8'S)-4,5'-diliydroxy-3,3'-dimethoxy-7,7'-epoxylignan (4) showed the corresponding activities with IC50 values of 39.4 and 2.11 mu M, respectively.