Hanultarin, a cytotoxic lignan as an inhibitor of actin cytoskeleton polymerization from the seeds of Trichosanthes kirilowii.
Bioactivity-directed fractionation of extracts from the seeds of Trichosanthes kirilowii led to the isolation of (-)-1-O-feruloylsecoisolariciresinol (2), named hanultarin, In addition, four known lignans were also isolated, including (-)-secoisolariciresinol (1), 1,4-O-diferuloylsecoisolariciresinol (3), (-)-pinoresinol (4), and 4-ketopinoresinol (5). Their structures were elucidated on the basis of spectroscopic data. Compounds 2 and 3 exhibited strong cytotoxic effects against human lung carcinoma A549 cells, melanoma SK-Mel-2 cells, and mouse skin melanoma B16F1 cells with IC(50) ranges of 3-13 microg/mL. Compound 2 showed an inhibitory effect on the polymerization of the actin cytoskeleton in normal epidermal keratinocyte (HaCaT cells), suggesting unique biological properties of compound 2 compared to those of the other isolates.
Moon
Surk-Sik
SS
Department of Chemistry, Kongju National University, 182 Shinkwangdong, Kongju 314-701, Republic of Korea. ssmoon@kongju.ac.kr
Rahman
Aziz Abdur
AA
Kim
Joo-Young
JY
Kee
Sun-Ho
SH
D000199:Actins / Q000378:metabolism*; D002460:Cell Line; D003599:Cytoskeleton / Q000187:drug effects* / Q000378:metabolism; D006801:Humans; D015603:Keratinocytes / Q000166:cytology / Q000187:drug effects; D017705:Lignans / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D012639:Seeds / Q000737:chemistry*; D013329:Structure-Activity Relationship; D029778:Trichosanthes / Q000737:chemistry*
D000199:Actins; D017705:Lignans; C532760:hanultarin