The mechanism of the bactericidal activity of hinokitiol

Biocontrol Science

Volumn 12, Issue 3, 2007, Pages 101-110

  Morita, Yasuhiro ^a   Sakagami, Yoshikazu ^b   Okabe, Toshihiro ^c   Ohe, Tatsuhiko ^d   Inamori, Yoshihiko ^e   Ishida, Nakao ^f  

^a Osaka Organic Chemical Industry Ltd   (Japan)

^b KINKI UNIVERSITY   (Japan)

^c Aomori Industrial Research Center   (Japan)

^d Osaka Manicipal Research Institute   (Japan)

^e OSAKA MEDICAL COLLEGE   (Japan)

^f Sendai Research Institute for Microbiology   (Japan)

Author keywords

Bactericidal activity; Cell membrane; Hinokitiol; Mechanism

Indexed keywords

BACTERIA; BIOACTIVITY; CELL MEMBRANES; ESCHERICHIA COLI; NUCLEIC ACIDS; PROTEINS;

BACTERICIDAL ACTIVITY; HINOKITIOL; PROTEIN MOIETIES;

ANTIBIOTICS;

4 METHYLTROPOLONE; ADENINE; ALPHA THUJAPLICIN; BETA DOLABRIN; HINOKITIOL ACETATE; HINOKITIOL SODIUM; THUJAPLICIN; TROPOLONE; TROPONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BACTERICIDAL ACTIVITY; CELL MEMBRANE; CELL MEMBRANE PERMEABILITY; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; ESCHERICHIA COLI; GROWTH INHIBITION; METABOLIC INHIBITION; NONHUMAN; OXYGEN CONSUMPTION; STAPHYLOCOCCUS AUREUS;

ESCHERICHIA COLI; STAPHYLOCOCCUS AUREUS; THUJOPSIS DOLABRATA;

EID: 34548707554     PISSN: 13424815     EISSN: None     Source Type: Journal    
DOI: 10.4265/bio.12.101     Document Type: Article

References (32)

1. Asao, A., Machiguchi, T., and Kitamura, T. (1970) Novel Rearrangement of the Adduct of 6,6-Dimetylfulvene and Dichloroketen. Chem. Commum., 89-90.
2. Cook, J.W., Gibb, A. R., Raphael, R. A., and Somerville. A. R. (1951) Tropolones. Part 1. The Preparation and General Characteristics. J. Chem. Soc., 503-511.
3. Doering, W. von. E., and Knox, L. H. (1951) Tropolone. J. Am. Chem. Soc., 73, 828-838.
4. Frederick, J. J., Corner, D. R., and Gerhardt, P. (1974) Antimicrobial Actions of Hexachlorophene: Inhibition of Respiration in Bacillus megaterium. Antimicrob. Agents Chemother., 6, 712-721.
5. Freese,E., Sheu, C. W., and Galliers, E. (1973) Function of Lipophilic Acids as Antimicrobial Food Additives. Nature, 241, 321-325.
6. Fukazawa, R., and Sato, M., Jpn. Kokai Tokkyo Koho JP 61117289 [Chem. Abstr, 105, 170928n (1986)].
7. Fukazawa, R., and Sato, M., Jpn. Kokai Tokkyo Koho JP 62236440 [Chem. Abstr, 108, 130284e (1988)].
8. Hanzlik, R.P. (1988) Selective Epoxidation of Terminal Double Bonds: 10, 11-Epoxyfarnesyl Acetate. Org. Synth., I , 560-564.
9. Inamori, Y., Shinohara, S., Tsujibo, H., Okabe, T., Morita, Y., Sakagami, Y., Kumeda, Y., and Ishida, N. (1999) Antimicrobial Activity and Metalloprotease Inhibition of Hinokitiol-Related Compounds, the Constituents of Thujopsis dolabrata S. and Z. hondai Mak., Biol. Pharm. Bull., 22, 990-993.
10. Inamori, Y., Sakagami, Y., Morita, Y., Shibata, M., Sugiura, M., Kumeda, Y., Okabe, T., Tsujibo, H., and Ishida, N. (2000) Antifungal Activity of Hinokitiol-Related Compounds on Wood-Rotting Fungi and Their Insecticidal Activities. Biol. Pharm. Bull., 23, 995-997.
11. Kamiyokote, S., Izumi, K., and Hirota, N., Jpn. Kokai Tokkyo Koho JP 02157201 [Chem. Abstr, 113, 128087c (1990)].
12. Katagiri, Y., (1955) Experimental and Clinical Studies on Unsaturated, Seven-Membered Ring Compounds. J. Jpn. Soc. Int. Med., 44, 32-40.
13. Kubo, M., Nozoe, T., and Kurita, K. (1955) Dipole Moments of Tropolone and Related Compounds. Nature, 167, 688.
14. Levin, B., and Freese, E. (1974) Comparison of the Effects of Two Lipophilic Acids, Hexachlorophene and Decanoate, on Bacillus subtilis. Antimtiicrob. Agents. Chemother., 6, 357-367.
15. Lucchini, J. J., Corre, J., and Cremieux, A. (1990) Antibacterial Activity of Phenolic Compounds and Aromatic Alcohol. Res. Microbiol, 141, 499-510.
16. Matsumura, E., Morita, Y., Date, T., Tsujibo, H., Yasuda, M., Okabe, T., Ishida, N., and Inamori, Y. (2001) Cytotoxicity of the Hinokitiol-Related Compounds, γ -Thujaplicin and β -Dolabrin. Biol. Pharm. Bull., 24, 299-302.
17. Morita, Y., Matsumura, E., Tsujibo, H., Yasuda, M., Sakagami, Y., Okabe, T., Ishida, N., and Inamori, Y. (2001) Biological Activity of α -Thujaplicin, the Minor Component of Thujopsis dolabrata Sieb. et Zucc. var. hondai Makino. Biol. Pharm. Bull., 24, 607-611.
18. Morita, Y., Matsumura, E., Tsujibo, H., Yasuda, M., Okabe, T., Sakagami, Y., Ishida, N., and Inamori, Y. (2002) Biological Activity of 4-Acetyltropolone, the Minor Component of Thujopsis dolabrata Sieb. et Zucc. var. hondai Mak. Biol. Pharm. Bull., 25, 981-985.
19. Morita, Y., Matsumura, E., Okabe, T., Shibata, M., Sugiura, M., Ohe, T., Tsujibo, H., Ishida, N., and Inamori, Y. (2003) Biological Activity of Tropolone. Biol. Pharm. Bull., 26, 1487-1490.
20. Morita, Y., Matsumura, E., Fukui, T., Okabe, T., Shibata, M., Sugiura, M., Ohe, T., Tsujibo, H., Ishida, N., and Inamori, Y. (2004a) Biological Activity of α -Thujaplicin, the Isomer of Hinokitiol, Biol. Pharm. Bull., 27, 899-902.
21. Morita, Y., Matsumura, E., Okabe, T., Fukui, T., Ohe, T., Ishida, N., Inamori, Y. (2004b) Biological Activity of β - Dolabrin, γ -Thujaplicin, and 4-Acetyltropolone, Hinokitiol-Related Compounds, Biol. Pharm. Bull., 27, 1666-1669.
22. Nozoe, T. (1936) Uber die Farbstoffe Im Holzteile des "Hinoki" Baumes. I. Hinokitin and Hinoktiol, Bull. Chem. Soc. Japan., 11, 295-298.
23. Nozoe, T., Seto, S., Kikuchi, K., and Takrds, H. (1951) On the Synthesis of γ - Thujaplicin (p-Isopropyltropolone), Proc. Japan. Acad., 27, 146-148.
24. Nozoe, T., Takase, K., and Ogata, M. (1957) β -Dolabrin: A new natural tropolone, Chem. Ind. (London), 1070.
25. Okabe, T., Ootomo, Y., Saito, K., Jpn. Kokai Tokkyo Koho JP (1988b) [Chem. Abstr, 111, 148877x (1989)].
26. Okabe, T., Ootomo, Y., Saito, K., Jpn. Kokai Tokkyo Koho JP (1988a) [Chem. Abstr, 111, 148877y (1989)].
27. Okazaki, K., Homma, A. (1953) Antibacterial Activity of Higher Plants XXVI. Antimicrobial Effect of Essential Oils.(7). On the Oil of Thuja dolabrata and Its Components. J. Pharm. Soc.Jpn., 74, 174-176.
28. AKINO. Biol. Pharm. Bull., 23, 645-648.
29. Schneider, W. C. (1945) Phosphorus Componds in Animal Tissues. J. Biol. Chem., 161, 293-303.
30. Sheu, C. W., and Freese, E. J. (1972) Effects of Fatty Acids on Growth and Envelope Proteins of Bacillus subtilis. J. Bacteriol., 111, 516-524.
31. Shibasaki, I., and Terui, G. (1955) Study on Anitfungal Agent (4), The Comparison of antibacterial Activity of Synthetic Compounds as the Preservatives. J. Ferment. Technol., 33, 216-223.
32. Trust, T. J., Coombs, R. W. (1973) Antibacterial Activity of β -Thujaplicin. Can. J. Microbiol., 19, 1341-1347.