Antimicrobial Activity and Metalloprotease Inhibition of Hinokitiol-Related Compounds, the Constituents of Thujopsis dolabrata S. and Z. hondai MAK
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...
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| Veröffentlicht in: | Biological & pharmaceutical bulletin 1999/09/15, Vol.22(9), pp.990-993 |
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| creator | INAMORI, Yoshihiko SHINOHARA, Sayo TSUJIBO, Hiroshi OKABE, Toshihiro MORITA, Yasuhiro SAKAGAMI, Yoshikazu KUMEDA, Yuko ISHIDA, Nakao |
| description | 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. |
| doi_str_mv | 10.1248/bpb.22.990 |
| format | Article |
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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.</description><identifier>ISSN: 0918-6158</identifier><identifier>EISSN: 1347-5215</identifier><identifier>DOI: 10.1248/bpb.22.990</identifier><identifier>PMID: 10513629</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>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. 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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.</description><subject>Anti-Bacterial Agents</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>antimicrobial activity</subject><subject>Bacteria - drug effects</subject><subject>Biological and medical sciences</subject><subject>Carboxypeptidases - antagonists & inhibitors</subject><subject>Carboxypeptidases A</subject><subject>Cycadopsida - chemistry</subject><subject>General pharmacology</subject><subject>hinokitiol</subject><subject>hinokitiol-related compound</subject><subject>Matrix Metalloproteinase Inhibitors</subject><subject>Medical sciences</subject><subject>Metalloendopeptidases - antagonists & inhibitors</subject><subject>metalloprotease inhibition</subject><subject>Monoterpenes</subject><subject>Penicillium - drug effects</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Protease Inhibitors - pharmacology</subject><subject>Thermolysin - antagonists & inhibitors</subject><subject>Tropolone - analogs & derivatives</subject><subject>Tropolone - chemistry</subject><subject>Tropolone - pharmacology</subject><subject>β-dolabrin</subject><subject>γ-thujaplicin</subject><issn>0918-6158</issn><issn>1347-5215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkU1v1DAQhiMEotvChR-ALIF6QCT4I87HcbUCWtEKCfbEJZo4E-LFa4fYQerv4A_jNKuCuIw1mmfmHc-bJC8YzRjPq3ft2GacZ3VNHyUbJvIylZzJx8mG1qxKCyars-Tc-wOltKRcPE3OGJVMFLzeJL-3NuijVpNrNRiyVUH_0uGOgO3ILQYwxo2TCwgeybUddKuDdpa4nlxp634smUm_oIGAHdm54-hm2_m3JAwYU-uDDjPa4JeO_TAf3Oi1J50z0E4QgHzN7qW-ZWRwtgNNbrefniVPejAen5_ei2T_4f1-d5XefP54vdvepEpSHlLJWp5DIYuqL6GCQlDedUJVfYdcgkKlKKfY94y3omwZ5wyhojWVgDmjtbhILtex8YM_Z_ShOWqv0Biw6GbflLTiUkgZwVf_gQc3Tzau1rA8jzcWjJaRerNS8ZbeT9g346SPMN01jDaLT030qeG8iT5F-OVp5NwesfsHXY2JwOsTAF6B6SewSvu_XF2LKl9Edyt28AG-40MdpqCVwUVyQe9l1xDVH6pqgKlBK_4AnB-zqg</recordid><startdate>19990901</startdate><enddate>19990901</enddate><creator>INAMORI, Yoshihiko</creator><creator>SHINOHARA, Sayo</creator><creator>TSUJIBO, Hiroshi</creator><creator>OKABE, Toshihiro</creator><creator>MORITA, Yasuhiro</creator><creator>SAKAGAMI, Yoshikazu</creator><creator>KUMEDA, Yuko</creator><creator>ISHIDA, Nakao</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QP</scope><scope>7QR</scope><scope>7TK</scope><scope>7U9</scope><scope>8FD</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>19990901</creationdate><title>Antimicrobial Activity and Metalloprotease Inhibition of Hinokitiol-Related Compounds, the Constituents of Thujopsis dolabrata S. and Z. hondai MAK</title><author>INAMORI, Yoshihiko ; SHINOHARA, Sayo ; TSUJIBO, Hiroshi ; OKABE, Toshihiro ; MORITA, Yasuhiro ; SAKAGAMI, Yoshikazu ; KUMEDA, Yuko ; ISHIDA, Nakao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c502t-51b24a6568f7a8a6302dd3c8fde25acecc020eff12b37b1221ea80905ae41093</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>Anti-Bacterial Agents</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>antimicrobial activity</topic><topic>Bacteria - drug effects</topic><topic>Biological and medical sciences</topic><topic>Carboxypeptidases - antagonists & inhibitors</topic><topic>Carboxypeptidases A</topic><topic>Cycadopsida - chemistry</topic><topic>General pharmacology</topic><topic>hinokitiol</topic><topic>hinokitiol-related compound</topic><topic>Matrix Metalloproteinase Inhibitors</topic><topic>Medical sciences</topic><topic>Metalloendopeptidases - antagonists & inhibitors</topic><topic>metalloprotease inhibition</topic><topic>Monoterpenes</topic><topic>Penicillium - drug effects</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Protease Inhibitors - pharmacology</topic><topic>Thermolysin - antagonists & inhibitors</topic><topic>Tropolone - analogs & derivatives</topic><topic>Tropolone - chemistry</topic><topic>Tropolone - pharmacology</topic><topic>β-dolabrin</topic><topic>γ-thujaplicin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>INAMORI, Yoshihiko</creatorcontrib><creatorcontrib>SHINOHARA, Sayo</creatorcontrib><creatorcontrib>TSUJIBO, Hiroshi</creatorcontrib><creatorcontrib>OKABE, Toshihiro</creatorcontrib><creatorcontrib>MORITA, Yasuhiro</creatorcontrib><creatorcontrib>SAKAGAMI, Yoshikazu</creatorcontrib><creatorcontrib>KUMEDA, Yuko</creatorcontrib><creatorcontrib>ISHIDA, Nakao</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Biological & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>INAMORI, Yoshihiko</au><au>SHINOHARA, Sayo</au><au>TSUJIBO, Hiroshi</au><au>OKABE, Toshihiro</au><au>MORITA, Yasuhiro</au><au>SAKAGAMI, Yoshikazu</au><au>KUMEDA, Yuko</au><au>ISHIDA, Nakao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antimicrobial Activity and Metalloprotease Inhibition of Hinokitiol-Related Compounds, the Constituents of Thujopsis dolabrata S. and Z. hondai MAK</atitle><jtitle>Biological & pharmaceutical bulletin</jtitle><addtitle>Biol Pharm Bull</addtitle><date>1999-09-01</date><risdate>1999</risdate><volume>22</volume><issue>9</issue><spage>990</spage><epage>993</epage><pages>990-993</pages><issn>0918-6158</issn><eissn>1347-5215</eissn><abstract>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.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>10513629</pmid><doi>10.1248/bpb.22.990</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Biological and Pharmaceutical Bulletin, 1999/09/15, Vol.22(9), pp.990-993 |
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| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| 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 |
| title | Antimicrobial Activity and Metalloprotease Inhibition of Hinokitiol-Related Compounds, the Constituents of Thujopsis dolabrata S. and Z. hondai MAK |
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