title: In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconia pearcei and related compounds.
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 (IC(50) value: 0.014 microg/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 C(7)-C(8) position was found to enhance the activity. On the other hand, the bulkiness at the C(2)-C(3) position on the D-ring, a carbonyl group at C-6, substitution at C-6 and cleavage or saturation of the C(5)-C(6) bond reduced activity. A methyl group on nitrogen of the C-ring was thought to be necessary for significant activity.
authors.affiliation: Research Center for Medicinal Plant Resources, National Institute of Biomedical Innovation, 1-2 Hachimandai, Tsukuba, Ibaraki, Japan. fuchino@nibio.go.jp
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Fuchino
authors.forename: Marii
authors.initials: M
authors.lastname: Kawano
authors.forename: Kanami
authors.initials: K
authors.lastname: Mori-Yasumoto
authors.forename: Setsuko
authors.initials: S
authors.lastname: Sekita
authors.forename: Motoyoshi
authors.initials: M
authors.lastname: Satake
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Ishikawa
authors.forename: Fumiyuki
authors.initials: F
authors.lastname: Kiuchi
authors.forename: Nobuo
authors.initials: N
authors.lastname: Kawahara
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D053119:Benzophenanthridines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005638:Fruit / Q000737:chemistry*; D007891:Leishmania / Q000187:drug effects* / Q000254:growth & development; D015394:Molecular Structure; D028101:Papaveraceae / Q000737:chemistry*; D021261:Parasitic Sensitivity Tests; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000981:Antiprotozoal Agents; D053119:Benzophenanthridines; D010936:Plant Extracts