Synthesis of 3-Substituted Isocoumarins and Their Inhibitory Effects on Degranulation of RBL-2H3 Cells Induced by Antigen

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  • Kurume Ai
    Department of Functional Molecular Chemistry, Kyoto Pharmaceutical University
  • Kamata Yasuhiro
    Department of Functional Molecular Chemistry, Kyoto Pharmaceutical University
  • Yamashita Masayuki
    Department of Functional Molecular Chemistry, Kyoto Pharmaceutical University
  • Wang Qilong
    Department of Pharmacognosy, 21st Century COE Program, Kyoto Pharmaceutical University
  • Matsuda Hisashi
    Department of Pharmacognosy, 21st Century COE Program, Kyoto Pharmaceutical University
  • Yoshikawa Masayuki
    Department of Pharmacognosy, 21st Century COE Program, Kyoto Pharmaceutical University
  • Kawasaki Ikuo
    Department of Functional Molecular Chemistry, Kyoto Pharmaceutical University School of Pharmaceutical Sciences, Mukogawa Women's University
  • Ohta Shunsaku
    Department of Functional Molecular Chemistry, Kyoto Pharmaceutical University

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Abstract

Eleven 3-substituted isocoumarins and a benzylidenephthalide were synthesized through thermal cyclization reaction of δ- and γ-ketoamides, respectively. Subsequent deprotection of the hydroxyl groups of the resulting isocoumarin and benzylidenephthalide compounds afforded thunberginols A, B, and F, respectively, which originated from the processed leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO. The synthesized isocoumarins and thunberginols were evaluated for their anti-allergic activity, in which thunberginol B exhibited the highest inhibitory potency on the degranulation of RBL-2H3 cells induced by antigen. Structure–activity relationship studies were carried out to determine the necessary substituents on the 3-phenylisocoumarin skeleton for inhibitory activity.

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