Two new anti-tumor promoting serratane-type triterpenoids from the stem bark of Picea jezoensis var. jezoensis.
Two new serratane-type triterpenoids, 1 and 2, were isolated from the stem bark of Picea jezoensis Carr. var. jezoensis (Pinaceae). Their structures were determined to be 3beta-methoxyserrat-13-en-21beta-ol (1) and 13beta, l4beta-epoxy-3beta-methoxyserratan-21beta-ol (2) on the basis of spectroscopic methods and partial syntheses. Compounds 1 and 2 and their acetates 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. IC50 value evaluation showed that compound 1 was more effective than others. In addition, compounds 1 and 2 were examined for anti-tumor promoting activities in a two-stage carcinogenesis assay of mouse skin tumors induced by 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter. Compounds 1 and 2 exhibited significant anti-tumor promoting effects on mouse skin carcinogenesis.
Tanaka
Reiko
R
Department of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, Osaka, Japan. tanakar@gly.oups.ac.jp
Ishikawa
Yohei
Y
Minami
Toshifumi
T
Minoura
Katsuhiko
K
Tokuda
Harukuni
H
Matsunaga
Shunyo
S
D000818:Animals; D000956:Antigens, Viral / Q000187:drug effects; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology*; D005260:Female; D004854:Herpesvirus 4, Human / Q000187:drug effects / Q000276:immunology; D020128:Inhibitory Concentration 50; D051379:Mice; D008813:Mice, Inbred ICR; D010212:Papilloma / Q000139:chemically induced / Q000517:prevention & control; D008517:Phytotherapy; D028222:Picea; D024301:Plant Bark; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D018547:Plant Stems; D012878:Skin Neoplasms / Q000139:chemically induced / Q000517:prevention & control; D013047:Specific Pathogen-Free Organisms; D013755:Tetradecanoylphorbol Acetate; D014315:Triterpenes / Q000737:chemistry / Q000494:pharmacology*
D000956:Antigens, Viral; D000972:Antineoplastic Agents, Phytogenic; D010936:Plant Extracts; D014315:Triterpenes; D013755:Tetradecanoylphorbol Acetate