In Vitro Leishmanicidal Activity of Benzophenanthridine Alkaloids from Bocconia pearcei and Related Compounds

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  • Fuchino Hiroyuki
    Research Center for Medicinal Plant Resources, National Institute of Biomedical Innovation
  • Kawano Marii
    Faculty of Pharmaceutical Sciences, Josai International University
  • Mori-Yasumoto Kanami
    Department of Pharmaceutical Technology, Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University
  • Sekita Setsuko
    Department of Pharmaceutical Technology, Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University
  • Satake Motoyoshi
    Institute of Environmental Science for Human Life, Ochanomizu University
  • Ishikawa Tsutomu
    Faculty of Pharmaceutical Sciences, Chiba University
  • Kiuchi Fumiyuki
    Faculty of Pharmacy, Keio University
  • Kawahara Nobuo
    Research Center for Medicinal Plant Resources, National Institute of Biomedical Innovation

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Leishmanicidal activities of benzophenanthridine alkaloids isolated from fruits of Bocconia pearcei and their derivatives were examined. Seven benzophenanthridine compounds were isolated from the methanolic extracts of B. pearcei. Among them, dihydrosanguinarine showed the most potent leishmanicidal activities (IC50 value: 0.014 μg/ml, respectively). To examine the structure–activity relationship of the benzophenanthridine skeleton, the leishmanicidal activities for 32 synthetic samples were examined. The existence of bulky groups at the C7–C8 position was found to enhance the activity. On the other hand, the bulkiness at the C2–C3 position on the D-ring, a carbonyl group at C-6, substitution at C-6 and cleavage or saturation of the C5–C6 bond reduced activity. A methyl group on nitrogen of the C-ring was thought to be necessary for significant activity.

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