title: Three new and other limonoids from the hexane extract of Melia azedarach fruits and their cytotoxic activities.
abstract: A defatted fraction obtained from the hexane extract of the fruits of Melia azedarach L. (chinaberry tree; Meliaceae) exhibited cytotoxic activities against leukemia (HL60), lung (A549), stomach (AZ521), and breast (SK-BR-3) cancer cell lines with IC50 values in the range of 2.9-21.9 μg/ml. Three new limonoids, 3-deacetyl-4'-demethylsalannin (5), 3-deacetyl-28-oxosalannin (14), and 1-detigloylohchinolal (17), along with 16 known limonoids, 1-4, 6-13, 15, 16, 18, and 19, and one known triterpenoid, 20, were isolated from the fraction. The structures of new compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with literature. These compounds were evaluated for their cytotoxic activities against the four cancer cell lines mentioned above. 3-Deacetyl-4'-demethyl-28-oxosalannin (16), which exhibited potent cytotoxicity against AZ521 (IC50 3.2 μM) cells, induced typical apoptotic cell death in AZ521 cells upon evaluation of the apoptosis-inducing activity by flow cytometry. This work provided, furthermore, valuable information on the structural features of limonoids of the fruits and/or seeds of Melia azedarach and related Meliaceae plants, M. toosendan and Azadirachta indica.
authors.affiliation: College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan.
authors.forename: Xin
authors.initials: X
authors.lastname: Pan
authors.forename: Masahiro
authors.initials: M
authors.lastname: Matsumoto
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Nakamura
authors.forename: Takashi
authors.initials: T
authors.lastname: Kikuchi
authors.forename: Jie
authors.initials: J
authors.lastname: Zhang
authors.forename: Motohiko
authors.initials: M
authors.lastname: Ukiya
authors.forename: Takashi
authors.initials: T
authors.lastname: Suzuki
authors.forename: Kazuo
authors.initials: K
authors.lastname: Koike
authors.forename: Rima
authors.initials: R
authors.lastname: Akihisa
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Akihisa
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D005638:Fruit / Q000737:chemistry; D006586:Hexanes / Q000737:chemistry; D006801:Humans; D036701:Limonins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D031586:Melia azedarach / Q000737:chemistry*; D009369:Neoplasms / Q000188:drug therapy
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D006586:Hexanes; D036701:Limonins; C026385:n-hexane
keywords: Apoptosis-inducing activity; Cytotoxic activity; Limonoids; Melia azedarach