title: Carapanolides C-I from the seeds of andiroba (Carapa guianensis, Meliaceae).
abstract: Five new mexicanolide-type limonoids, carapanolides C-G (1-5), together with two new phragmalin-type limonoids, carapanolides H-I (6, 7), were isolated from the oil of Carapa guianasis AUBLET (Meliaceae) seeds. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR spectra and FABMS. Carapanolides C (1), E (3), and I (7) exhibited moderate activity in the P388 (IC50 17.9 μM in 1, 15.8 μM in 3) and L1210 cell lines (IC50 13.3 μM in 1, 18.1 μM in 3, 16.9 μM in 7). On the other hand, Carapanolide D (2) exhibited a strong inhibitory effect in the HL-60 cell line (IC50 11.0 μM), Carapanolides F (4) showed inhibitory activity in the L1210 cell line (IC50 15.9 μM), and the cytotoxic activity of Carapanolides I (7) was moderate in all cell lines.
authors.affiliation: Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
authors.forename: Takanobu
authors.initials: T
authors.lastname: Inoue
authors.affiliation: Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
authors.forename: Yuuki
authors.initials: Y
authors.lastname: Matsui
authors.affiliation: Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Kikuchi
authors.affiliation: Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
authors.forename: Yasuko
authors.initials: Y
authors.lastname: In
authors.affiliation: Department of Organic Chemistry, Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashiosaka, Osaka 577-8502, Japan.
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
authors.affiliation: Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Yamada
authors.affiliation: Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. Electronic address: tanakar@gly.oups.ac.jp.
authors.forename: Reiko
authors.initials: R
authors.lastname: Tanaka
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D036701:Limonins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D029582:Meliaceae / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D010938:Plant Oils / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D012639:Seeds / Q000737:chemistry
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D036701:Limonins; D010938:Plant Oils; C554989:mexicanolide; C000593079:phragmalin
keywords: Carapa guianensis; Carapanolides C–I; Limonoid; Meliaceae; Seed