Biological activity of 4-acetyltropolone, the minor component of Thujopsis dolabrata SIeb. et Zucc. hondai Mak.
4-Acetyltropolone, a minor component of Thujopsis dolabrata SIEB. et Zucc. hondai MAKINO, showed antimicrobial activity against various microorganisms including wood-rotting fungi, a phytogrowth-inhibitory effect with chlorophyll biosynthesis inhibition, cytotoxic effect and inhibitory activity on metalloproteases. This compound had strong antifungal activity on Daedalea dickinsii IFO-4979 [minimum inhibitory concentration (MIC): 0.2 microg/ml] and Coriolus versicolor IFO-4940 (MIC: 0.39 microg/ml). Its cytotoxic effect at 20.0/microg/ml on human stomach cancer KATO-III and Ehrich's ascites carcinoma was stronger than those of podophyllotoxin, vincristine and vinblastine, the anticancer agents isolated from higher plants and used clinically. This compound also had potent antibacterial activity against Staphylococcus epidermidis IFO-12993, its MIC being 1.56 microg/ml. However, other biological activities of 4-acetyltropolone were lower than those of hinokitiol which is the main component of this plant, suggesting that the contribution of the acetyl group at C-4 to biological activity is smaller than that of the isopropyl group at that position. The acute toxicity of 4-acetyltropolone (LD50: 335.2 mg/kg) to mice was much lower than that of hinokitiol (LD50: 191 mg/kg).
Morita
Yasuhiro
Y
Osaka Organic Chemical Industry, Ltd, Kashiwara, Japan.
Matsumura
Eiko
E
Tsujibo
Hiroshi
H
Yasuda
Masahide
M
Okabe
Toshihiro
T
Sakagami
Yoshikazu
Y
Kumeda
Yuko
Y
Ishida
Nakao
N
Inamor
Yoshihiko
Y
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects / Q000502:physiology; D006801:Humans; D051379:Mice; D008826:Microbial Sensitivity Tests / Q000379:methods / Q000706:statistics & numerical data; D039821:Monoterpenes / Q000737:chemistry* / Q000494:pharmacology*; D014334:Tropolone / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology*; D014407:Tumor Cells, Cultured / Q000166:cytology / Q000187:drug effects / Q000502:physiology
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D039821:Monoterpenes; D014334:Tropolone; C009479:beta-thujaplicin