In our previous paper, 1) antimicrobial activity, phytogrowth-inhibitory effect, cytotoxic activity and metalloprotease inhibition have been found as biological activities of athujaplicin (Chart 1), a minor component of Thujopsis dolabrata SIEB. et ZUCC. var. hondai MAKINO. At the same time, as the yield of a-thujaplicin was too small to permit examination of various biological activities, it was also reported to be chemically synthesized.1) As reported already, in addition to a-thujaplicin, hinokitiol-related compounds such as 4-acetyltropolone, hinokitiol (b-thujaplicin), b-dolabrin and g-thujaplicin have also been isolated from this plant.
2)As regards the biological activities of hinokitiol-related compounds, it has previously been reported by the authors that hinokitiol, b-dolabrin, g-thujaplicin and 4-acetyltropolone have antimicrobial activity, 1,3,4) metalloprotease inhibition, 1,3,4) cytotoxic effect, 1,4,5) phytogrowth-inhibitory activity 6,7) and an insecticidal effect. 8) However, no work has yet been done on other biological tests, except for the abovementioned activities of a-thujaplicin, because of its low yield.In this work, to determine the range of biological activity of hinokitiol-related compounds, the antifungal activity on plant-pathogenic fungi, antibacterial effect on Legionella species and acaricidal and insecticidal activities against Dermatophagoides farinae and Reticulitermes speratus of a-thujaplicin were investigated. The cytotoxic effect on the murine P388 lymphocytic leukemia cell line in vitro of a-thujaplicin was also examined.
MATERIALS AND METHODSChemicals a-Thujaplicin, which was synthesized according to the method of the previous paper, 1) was used for various biological activities. Hinokitiol, isolated from T. dolabrata SIEB. et ZUCC. var. hondai MAKINO, was used for tests of insecticidal and acaricidal effects and antifungal activity on plant-pathogenic fungi as a comparative agent. N,NDiethyl-m-toluamide (DEET, a positive control for insecticidal activity testing on Dermatophagoides farinae) was obtained from Yoshitomi Pharmaceutical Industries, Ltd., Osaka, Japan. Chloropyrifos (a positive control for insecticidal activity testing on Reticulitermes speratus) was purchased from Hoechst Schering Agro Evo, Japan, Ltd., Osaka, Japan. Vinblastine and vincristine were also obtained from Sigma Chemical Co. (U.S.A. Sciences; 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan: c Aomori Industrial Research Center; 4-11-6 Daini-tonyamachi, Aomori 030-0113, Japan: d Japan: e Fumakilla Ltd.; Japan: f Osaka Municipal Technical Research Institute; Japan: and g The Sendai Institute of Microbiology; ICR Building 2F, ). At 24 h after treatment, a a-thujaplicin at 0.63 m mg/ml inhibited the cell growth of murine P388 lymphocytic leukemia by 78%, and its cytotoxic activity at a concentration higher than 0.63 m mg/ml was as high as that of vincristine, used as a positive control. On the other hand, the cytotoxic effect of a a-thujaplicin at 0.63 m mg/ml was weaker than that of vi...