Isolation and cytotoxicity of the lignanoids from Chamaecyparis formosensis.
In this study, we assessed the antitumor activity of the methanol extract from wood chips of the heartwood of the Taiwan red cypress, Chamaecyparis formosensis Matsumura, which is a precious tree species endemic to Taiwan. A brine shrimp lethality test (BST) indicated that the ethyl acetate (EtOAc)-soluble extract from the MeOH extract was a suitable candidate (LC (50) = 15.36 microg/mL) for further studies of the antitumor activity of its components. From this EtOAc fraction, we isolated six lignans and two norlignans and tested their cytotoxic activities IN VITRO against promyelocytic leukemia (HL-60) and hepatoma (Hepa-G2) cell lines. Among these compounds, 7,7'-( S)-dihydrotaiwanin C, isolated for the first time from nature, with its single crystal structure depicted in this study, exhibited significant cytotoxic activity against HL-60 cell lines IN VITRO (IC (50) = 4.03 microg/mL) after 24 hours. BST:brine shrimp lethality test Hepa-G2:human hepatoma HL-60:human leukemia IC (50):half-maximal inhibitory concentration SARs:structure-activity relationships AS:adenine sulfate.
Chen
Tai-Hung
TH
Department of Chemistry, National Chung Hsing University, Taichung, Taiwan.
Liau
Bing-Chung
BC
Wang
Sheng-Yang
SY
Jong
Ting-Ting
TT
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000494:pharmacology*; D001156:Artemia / Q000187:drug effects; D052117:Benzodioxoles / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006528:Carcinoma, Hepatocellular / Q000188:drug therapy / Q000473:pathology; D045744:Cell Line, Tumor; D029780:Chamaecyparis / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003603:Cytotoxins / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D008031:Lignin / Q000302:isolation & purification / Q000494:pharmacology*; D010936:Plant Extracts / Q000302:isolation & purification / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014934:Wood / Q000737:chemistry
C539086:7,7'-dihydrotaiwanin C; D000972:Antineoplastic Agents, Phytogenic; D052117:Benzodioxoles; D001572:Benzofurans; D003603:Cytotoxins; D010936:Plant Extracts; D008031:Lignin