Inamori Y, Shinohara S, Tsujibo H, Okabe T, Morita Y, Sakagami Y, Kumeda Y, Ishida N
Osaka University of Pharmaceutical Sciences, Japan.
Biol Pharm Bull. 1999 Sep;22(9):990-3. doi: 10.1248/bpb.22.990.
Gamma-thujaplicin, beta-dolabrin and hinokitiol(beta-thujaplicin), hinokitiol-related compounds isolated from the wood of Thujopsis dolabrata S. and Z. hondai MAK have antimicrobial activity. In particular, strong antibacterial activity of hinokitiol and beta-dolabrin on Staphylococcus epidermidis IFO-12993 was found, with a minimum inhibitory concentration (MIC) of 0.2 microg/ml. This activity was higher than that of gentamicin, used as a positive control, and so the strong antibacterial activity of both compounds on this bacterium is of considerable interest. Of the three compounds, gamma-thujaplicin showed the strongest antifungal activity and its MIC was found to be around 1.5 microg/ml. The three compounds also inhibited metalloproteases. The inhibitory activity of hinokitiol on carboxypeptidase A was especially strong, its 50%-inhibitory concentration (IC50) being 2.76x10(-6) M. Considering that metalloproteases are involved in inflammation, the strong inhibitory activity of hinokitiol could be important. On the other hand, hinokitiol-acetate did not show any antimicrobial activity and metalloprotease inhibition, suggesting that at least part of the activity is due to metal chelation between the carbonyl group at C-1 and the hydroxyl group at C-2 in the tropolone skeleton.
γ-崖柏素、β-多拉布林和扁柏酚（β-崖柏素），这些从日本扁柏（Thujopsis dolabrata S. and Z. hondai MAK）木材中分离得到的与扁柏酚相关的化合物具有抗菌活性。特别是，发现扁柏酚和β-多拉布林对表皮葡萄球菌IFO-12993具有很强的抗菌活性，最低抑菌浓度（MIC）为0.2微克/毫升。该活性高于用作阳性对照的庆大霉素，因此这两种化合物对该细菌的强抗菌活性备受关注。在这三种化合物中，γ-崖柏素表现出最强的抗真菌活性，其MIC约为1.5微克/毫升。这三种化合物还抑制金属蛋白酶。扁柏酚对羧肽酶A的抑制活性尤为强烈，其50%抑制浓度（IC50）为2.76×10⁻⁶ M。鉴于金属蛋白酶与炎症有关，扁柏酚的强抑制活性可能很重要。另一方面，乙酸扁柏酚未表现出任何抗菌活性和金属蛋白酶抑制作用，这表明至少部分活性是由于卓酚酮骨架中C-1位的羰基与C-2位的羟基之间的金属螯合作用。
