Inhibition of in Vitro Prostaglandin and Leukotriene Biosyntheses by Cinnamoyl-β-phenethylamine and N-Acyldopamine Derivatives

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概要

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• N-trans- and N-cis-Feruloyltyramines were isolated as the inhibitors of in vitro prostaglandin (PG) synthesis from an Indonesian medicinal plant, Ipomoea aquatica (Convolvulaceae). In order to clarify structure activity relationships, cinnamoyl-β-phenethylamines with possible combinations of naturally occurring cinnamic acids and β-phenethylamines were synthesized and tested for their inhibitory activities against PG synthetase and arachidonate 5-lipoxygenase. The compounds containing catechol groups such as N-caffeoyl-β-phenethylamine (CaP) showed higher inhibitory effects on PG synthetase. The catechol group was found to be essential for the inhibition of arachidonate 5-lipoxygenase. The investigation of concentration dependent effects on PG biosynthesis revealed that CaP enhanced PG biosynthesis at a lower concentration range, whereas it inhibited the reaction at a higher concentration. The effects of CaP on each reaction step were investigated with purified PG endoperoxide synthase and microsomal PG synthetase. CaP inhibited the cyclooxygenase reaction, while it enhanced the hydroperoxidase reaction. N-Acyldopamines which contain catechol and lipophylic group were synthesized from dopamine and fatty acids to test their inhibitory effects on arachidonate 5-lipoxygenase. N-Linoleoyldopamine was the most active compound and its IC_<50> value was 2.3nM in our assay system, in which an IC_<50> value of AA 861,a specific inhibitor of 5-lipoxygenase, was 8nM.

• 社団法人日本薬学会の論文
• 1992-02-25

著者

• 三川 潮

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 海老塚 豊

  Faculty of Pharmaceutical Sciences, The University of Tokyo

• 渋谷 雅明

  Faculty of Pharmaceutical Sciences, The University of Tokyo

• 三川 潮

  富山医薬大薬

• 三川 潮

  Faculty Of Pharmaceuical Sciences The University Of Tokyo

• 三川 潮

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 岩上 敏

  Faculty Of Pharmaceuical Sciences The University Of Tokyo

• 花岡 文雄

  Faculty Of Pharmaceuical Sciences The University Of Tokyo

• 三川 潮

  東大 薬

• 曾 千芳

  Faculty of Pharmaceutical Sciences, The University of Tokyo

• 三ヶ尻 昭宏

  Faculty of Pharmaceutical Sciences, The University of Tokyo

• PADMAWINATA Kosashi

  Department of Pharmacy, Faculty of Science and Mathematics, Bandung Institute of Technology

• Padmawinata Kosasih

  Department Of Pharmacy Faculty Of Science And Mathematics Bandung Institute Of Technology

• 曽 千芳

  Faculty Of Pharmaceutical Sciences The University Of Tokyo

• Sankawa U

  International Research Center For Traditional Medicine

• Sankawa Ushio

  (present Address)faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• Sankawa Ushio

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 三ケ尻 昭博

  Faculty Of Pharmaceutical Sciences The University Of Tokyo

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