Antinociceptive Activities of α-Truxillic Acid and β-Truxinic Acid Derivatives(Pharmacognosy)

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概要

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• Our recent study demonstrated that the dimeric structure of α-truxillic acid derivatives played an important role in the expression of their anti-inflammatory activities. In the present report, to investigate the correlation between the structure and anti-inflammatory activity, α-truxillic acid (1) and its derivatives (2-6), β-truxinic acid (7) and its derivatives (8-10) were prepared, and their activities were evaluated in the formalin test. All compounds showed only weak or no activities against the neurogenic pain response, but demonstrated significant activities against the inflammatory pain response induced by formalin. The highest anti-inflammatory activities were observed for α-truxillic acid (1) and its derivative 4,4'-dihydroxy-α-truxillic acid (2). In addition, α-truxillic acid (1) and its derivative, α-truxillic acid bis(p-nitrophenyl)ester (5), showed higher anti-inflammatory activities than β-truxinic acid (7) and the corresponding derivative (10). Furthermore, free carboxylic acids (1, 2) showed higher activities than their dimethyl esters (3, 4) and bis(p-nitrophenyl)ester (5). These results confirmed that the α-formation of dimeric structure and the free carboxylic acid were also important for the expression of anti-inflammatory activities. Otherwise, 4,4'-dichloro-β-truxinic acid (8) had higher activity than its parent compound 7; furthermore, 1,3-dibenzoyl-2,4-di(4-chlorophenyl)cyclobutane (6) also showed strong anti-inflammatory activity. These results suggested that substituents in the phenyl groups were also important for the expression of anti-inflammatory activity. In order to gain information about their activity intensity, the anti-inflammatory activities of 2 and 4,4'-dichlorolated derivatives (6, 8) were compared with that of indomethacin (a nonsteroidal anti-inflammatory drug) in the formalin test. As a result, compounds 2, 6 and 8 showed stronger anti-inflammatory activities than indomethacin. These results suggested that α-truxillic acid and β-truxinic acid derivatives might be developed into a new type of anti-inflammatory drug.

• 社団法人日本薬学会の論文
• 2006-03-01

著者

• Nohara Toshihiro

  Faculty of Pharmaceutical Sciences, Sojo University

• 金城 順英

  熊本大学 医薬

• SAKURADA Shinobu

  Department of Pharmacology, Tohoku College of Pharmacy

• Sakurada Shinobu

  Department Of Pharmacology Tohoku Pharmaceutical University

• Sakurada Shinobu

  中華人民共和国

• KINJO Junei

  Faculty of Pharmaceutical Sciences, Fukuoka University

• Nohara T

  Fac. Of Pharmaceutical Sciences Sojo Univ.

• Kinjo Junei

  Faculty Of Pharmaceutical Sciences Fukuoka University

• Kinjo Junei

  東海大学 農学部

• Kinjo Junei

  Department Of Pharmacognosy Faculty Of Pharmaceutical Sciences Fukuoka University

• Kinjo Junei

  福岡大学 薬学部

• Kinjo Junei

  Faculty Of Pharmaceutical Sciences Kumamoto University

• Kinjo Junei

  熊本大学 薬

• Nohara T

  Faculty Of Pharmaceutical Sciences Kumamoto University

• CHI Yu-Ming

  Seiwa Pharmaceutical Ltd.

• NAKAMURA Motoyuki

  Seiwa Pharmaceutical Ltd.

• ZHAO Xi-Ying

  Seiwa Pharmaceutical Ltd.

• YOSHIZAWA Toyokichi

  Seiwa Pharmaceutical Ltd.

• YAN Wen-Mei

  Beijing University of Traditional Chinese Medicine and Pharmacy

• HASHIMOTO Fumio

  Faculty of Pharmaceutical Sciences, Kumamoto University

• YAN Wen

  Beijing University of Traditional Chinese Medicine and Pharmacy

• Zhao Xi

  Seiwa Pharmaceutical Ltd.

• Yoshizawa Toyokichi

  Seiwa Pharmaceutical Co. Ltd.

• Chi Yu

  Seiwa Pharmaceutical Ltd.

• Hashimoto Fumio

  Faculty Of Pharmaceutical Sciences Kumamoto University

• Hashimoto F

  Faculty Of Agriculture Kagoshima University

• 金城 順英

  熊本大学 薬

• Nakamura M

  Seiwa Pharmaceutical Ltd.

• Jung K

  Laboratory Of Immunomodulator Korea Research Institute Of Bioscience And Biotechnology

• Nohara Toshihiro

  Fac. Of Pharmaceutical Sciences Sojo Univ.

• KIM Jin-Cheol

  Korea Research Institute of Chemical Technology

• Kinjo J

  Faculty Of Pharmaceutical Sciences Fukuoka University

• Kim J-h

  Faculty Of Pharmaceutical Sciences Fukuoka University

• Jung K

  Korea Res. Inst. Biosci. And Biotechnol. Taejon Kor

• Hashimoto Fumio

  Department Of Orthodontics Graduate School Of Biomedical Sciences Nagasaki University

• Hashimoto Fumio

  Laboratory Of Ornamental Horticulture Kagoshima University

• Nohara Toshihiro

  Faculty Of Medical And Pharmaceutical Science Kumamoto University

• Nakamura Takanori

  Faculty Of Pharmaceutical Sciences Kumamoto University

• Nakamura Takanori

  Hitachi Zosen Co.

• Nohara T

  Faculty Of Medical And Pharmaceutical Sciences Kumamoto University

• Kinjyo Junei

  Faculty Of Pharmaceutical Sciences Kumamoto University

• Hashimoto Fumio

  Faculity Of Science Osaka City University

• Nakamura Takanori

  Faculty of Medical and Pharmaceutical Sciences, Kumamoto University

• SAKURADA Shinobu

  Department of Chemical Pharmacology Tohoku College of Pharmacy

• Nohara Toshihiro

  Faculty of Medical and Pharmaceutical Scieces, Sojo University

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