Inhibition of Prostaglandin Biosynthesis by 4-O-Methylcryptochlorophaeic Acid ; : Synthesis of Monomeric Arylcarboxylic Acids for Inhibitory Activity Testing and X-Ray Analysis of 4-O-Methylcryptochlorophaeic Acid
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概要
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In order to clarify the structure-activity relationship of 4-O-methylcryptochlorophaeic acid (1), which is a lichen meta-depside and a potent inhibitor of prostaglandin (PG) biosynthesis found in our previous screening work, arylcarboxylic acids (5-8) corresponding to the monomeric moieties of 4-O-methylcryptochlorophaeic acid (1) were synthesized and tested for inhibitory effect against PG biosynthesis by an enzyme system prepared from rabbit renal medulla. They were a hundred times less active than 4-O-methylcryptochlorophaeic acid (1), indicating that the dimeric structure of the meta-depside is essential for inhibitory activity against PG biosynthesis. Kinetic studies on the mechanism of inhibition revealed that 4-O-methylcryptochlorophaeic acid (1) inhibits PG biosynthesis competitively with respect to the substrate, arachidonic acid. The three dimensional structure of 4-O-methylcryptochlorophaeic acid (1), which is expected to have a molecular structure able to fit into an active site that accommodates arachidonic acid, was determined by single crystal X-ray analysis with the direct approach. The obtained structure reveals that 4-O-methylcryptochlorophaeic acid (1) maintains a rigid conformation by forming a strong hydrogen bond between a hydroxy group and a methoxy group. Based on these findings, a new active site model of fatty acid cyclooxygenase is proposed in order to explain the inhibition by the meta-depside and acidic non-steroidal antiinflammatory drugs.
- 公益社団法人日本薬学会の論文
- 1983-02-25
著者
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三川 潮
Faculty of Pharmaceutical Sciences, University of Tokyo
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野口 博司
静岡県大薬
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飯高 洋一
Nishi-tokyo Science University
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飯高 洋一
Faculty of Pharmaceutical Sciences, The University of Tokyo
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野口 博司
静岡県立大学薬学部
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海老塚 豊
Faculty of Pharmaceutical Sciences, The University of Tokyo
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渋谷 雅明
Faculty of Pharmaceutical Sciences, The University of Tokyo
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三川 潮
Faculty Of Pharmaceuical Sciences The University Of Tokyo
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飯高 洋一
School Of Medicine Teikyo University
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飯高 洋一
Faculty Of Pharmaceutical Sciences University Of Tokyo
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飯高 洋一
西東京科学大学理工学部
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野口 博
Faculty of Pharmaceutical Sciences, University of Tokyo
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飯高 洋一
Faculty Of Pharmaceutical Sciences The University Of Tokyo
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