In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconia pearcei and related compounds

Hiroyuki Fuchino, Marii Kawano, Kanami Mori-Yasumoto, Setsuko Sekita, Motoyoshi Satake, Tsutomu Ishikawa, Fumiyuki Kiuchi, Nobuo Kawahara

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

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-C 3 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.

Original languageEnglish
Pages (from-to)1047-1050
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume58
Issue number8
DOIs
Publication statusPublished - 2010 Aug

Fingerprint

Benzophenanthridines
Alkaloids
Structure-Activity Relationship
Fruits
Skeleton
Inhibitory Concentration 50
Fruit
Substitution reactions
Nitrogen
Derivatives
In Vitro Techniques

Keywords

  • Alkaloid
  • Benzophenanthridine
  • Bocconia pearcei
  • Leishmaniasis
  • Papaveraceae

ASJC Scopus subject areas

  • Drug Discovery
  • Chemistry(all)

Cite this

Fuchino, H., Kawano, M., Mori-Yasumoto, K., Sekita, S., Satake, M., Ishikawa, T., ... Kawahara, N. (2010). In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconia pearcei and related compounds. Chemical and Pharmaceutical Bulletin, 58(8), 1047-1050. https://doi.org/10.1248/cpb.58.1047

In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconia pearcei and related compounds. / Fuchino, Hiroyuki; Kawano, Marii; Mori-Yasumoto, Kanami; Sekita, Setsuko; Satake, Motoyoshi; Ishikawa, Tsutomu; Kiuchi, Fumiyuki; Kawahara, Nobuo.

In: Chemical and Pharmaceutical Bulletin, Vol. 58, No. 8, 08.2010, p. 1047-1050.

Research output: Contribution to journalArticle

Fuchino, H, Kawano, M, Mori-Yasumoto, K, Sekita, S, Satake, M, Ishikawa, T, Kiuchi, F & Kawahara, N 2010, 'In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconia pearcei and related compounds', Chemical and Pharmaceutical Bulletin, vol. 58, no. 8, pp. 1047-1050. https://doi.org/10.1248/cpb.58.1047
Fuchino, Hiroyuki ; Kawano, Marii ; Mori-Yasumoto, Kanami ; Sekita, Setsuko ; Satake, Motoyoshi ; Ishikawa, Tsutomu ; Kiuchi, Fumiyuki ; Kawahara, Nobuo. / In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconia pearcei and related compounds. In: Chemical and Pharmaceutical Bulletin. 2010 ; Vol. 58, No. 8. pp. 1047-1050.
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