Antimicrobial Activity and Metalloprotease Inhibition of Hinokitiol-Related Compounds, the Constituents of Thujopsis dolabrata S. and Z. hondai MAK

• Published in: Biological & pharmaceutical bulletin Vol. 22; no. 9; pp. 990 - 993
• Main Authors: INAMORI, Yoshihiko, SHINOHARA, Sayo, TSUJIBO, Hiroshi, OKABE, Toshihiro, MORITA, Yasuhiro, SAKAGAMI, Yoshikazu, KUMEDA, Yuko, ISHIDA, Nakao
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 01-09-1999; Maruzen; Japan Science and Technology Agency
• Subjects: Anti-Bacterial Agents; Anti-Infective Agents - pharmacology; antimicrobial activity; Bacteria - drug effects; Biological and medical sciences; Carboxypeptidases - antagonists & inhibitors; Carboxypeptidases A; Cycadopsida - chemistry; General pharmacology; hinokitiol; hinokitiol-related compound; Matrix Metalloproteinase Inhibitors; Medical sciences; Metalloendopeptidases - antagonists & inhibitors; metalloprotease inhibition; Monoterpenes; Penicillium - drug effects; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Protease Inhibitors - pharmacology; Thermolysin - antagonists & inhibitors; Tropolone - analogs & derivatives; Tropolone - chemistry; Tropolone - pharmacology; β-dolabrin; γ-thujaplicin; Drug susceptibility test; Enzyme; Pharmacognosy; Metalloendopeptidases; In vitro; Medicinal plant; Peptidases; Antifungal agent; Staphylococcus epidermidis; Thuja plicata; Gymnospermae; Minimum inhibitory concentration; Plant origin; Bacteria; Hydrolases; Micrococcales; Coniferales; Micrococcaceae; Spermatophyta; Activity spectrum; Antibacterial agent; Mechanism of action; Comparative study
• DOI: 10.1248/bpb.22.990
• EISSN: 1347-5215
• ISSN: 0918-6158

γ-Thujaplicin, β-dolabrin and hinokitiol(β-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 β-dolabrin on Staphylococcus epidermidis IFO-12993 was found, with a minimum inhibitory concentration (MIC) of 0.2 μg/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, γ-thujaplicin showed the strongest antifungal activity and its MIC was found to be around 1.5 μg/ml. The three compounds also inhibited metalloproteases. The inhibitory activity of hinokitiol on carboxypeptidase A was especially strong, its 50%-inhibitory concentration (IC50) being 2.76×10-6 M. Considering that metaloproteases 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.