Cancer chemopreventive activity of lupane- and oleanane-type triterpenoids from the cones of Liquidamber styraciflua.
In a search for cancer chemopreventive agents from natural sources, four lupane-type and seven oleanane-type triterpenoids, and ten synthetic analogs were screened as potential anti-tumor promoters by using the in vitro short-term 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced Epstein-Barr virus early antigen (EBV-EA) activation assay. Among them, 25-acetoxy-3alpha-hydroxyolean-12-en-28-oic acid (1) and 3beta,25-epoxy-3alpha-hydroxylup-20(29)-en-28-oic acid (2) were examined for anti-tumor promoting activity in a two-stage carcinogenesis assay on mouse skin with 7,12-dimethylbenz[a]anthracene (DMBA) and TPA as promoter. 25-Acetoxy-3alpha-hydroxyolean-12-en-28-oic acid (1) and 3beta,25-epoxy-3alpha-hydroxylup-20(29)-en-28-oic acid (2) showed moderate inhibitory activities.
Fukuda
Yuko
Y
Department of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
Sakai
Kuniyoshi
K
Matsunaga
Shunyo
S
Tokuda
Harukuni
H
Tanaka
Reiko
R
D015127:9,10-Dimethyl-1,2-benzanthracene / Q000633:toxicity; D000818:Animals; D016588:Anticarcinogenic Agents / Q000494:pharmacology*; D002273:Carcinogens / Q000633:toxicity; D002460:Cell Line; D002850:Chromatography, Gel; D006801:Humans; D031317:Liquidambar / Q000737:chemistry*; D051379:Mice; D009374:Neoplasms, Experimental / Q000517:prevention & control*; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D013755:Tetradecanoylphorbol Acetate / Q000633:toxicity; D014315:Triterpenes / Q000737:chemistry / Q000494:pharmacology*; D053978:Pentacyclic Triterpenes
D015127:9,10-Dimethyl-1,2-benzanthracene; D016588:Anticarcinogenic Agents; D002273:Carcinogens; D009828:Oleanolic Acid; D013755:Tetradecanoylphorbol Acetate; D014315:Triterpenes; C413246:oleanane; C480546:lupane; D053978:Pentacyclic Triterpenes