Document Detail

Antimicrobial activity and metalloprotease inhibition of hinokitiol-related compounds, the constituents of Thujopsis dolabrata S. and Z. hondai MAK.
MedLine Citation:
PMID:  10513629     Owner:  NLM     Status:  MEDLINE    
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.
Y Inamori; S Shinohara; H Tsujibo; T Okabe; Y Morita; Y Sakagami; Y Kumeda; N Ishida
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Biological & pharmaceutical bulletin     Volume:  22     ISSN:  0918-6158     ISO Abbreviation:  Biol. Pharm. Bull.     Publication Date:  1999 Sep 
Date Detail:
Created Date:  1999-11-24     Completed Date:  1999-11-24     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9311984     Medline TA:  Biol Pharm Bull     Country:  JAPAN    
Other Details:
Languages:  eng     Pagination:  990-3     Citation Subset:  IM    
Osaka University of Pharmaceutical Sciences, Japan.
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MeSH Terms
Anti-Bacterial Agents
Anti-Infective Agents / pharmacology*
Bacteria / drug effects
Carboxypeptidases / antagonists & inhibitors
Carboxypeptidases A
Collagenases / antagonists & inhibitors
Gymnosperms / chemistry
Metalloendopeptidases / antagonists & inhibitors*
Penicillium / drug effects
Protease Inhibitors / pharmacology*
Thermolysin / antagonists & inhibitors
Tropolone / analogs & derivatives*,  chemistry,  pharmacology
Reg. No./Substance:
0/2-hydroxy-5-isopropyl- 2,4,6-cycloheptatrienone; 0/Anti-Bacterial Agents; 0/Anti-Infective Agents; 0/Monoterpenes; 0/Protease Inhibitors; 499-44-5/beta-thujaplicin; 533-75-5/Tropolone; EC 3.4.-/Carboxypeptidases; EC A; EC 3.4.24.-/Collagenases; EC 3.4.24.-/Metalloendopeptidases; EC

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