Triterpenoids from the fruits of Azadirachta indica (Meliaceae).
Four new triterpenoids, indicalilacols A-D (1-4), were isolated from the MeOH extract of the fruits of Azadirachta indica, including a new 19(10→9β)abeo-tirucallane derivative, two new tirucallane-type triterpenoids, and a new euphane-type triterpenoid, along with three known tirucallane-type triterpenoids. Their structures were elucidated on the basis of spectroscopic analyses. The absolute configuration of 2 was elucidated by the chemical conversion of 2 into 21-oxo-melianodiol 24,25-acetonide. Compounds 2, 6-8 exhibited moderate cytotoxicity against three human cancer cell lines, including multidrug-resistant (MDR) cancer cells (KB-C2). Although compound 5 was not cytotoxic against any of the tested cancer cell lines, 5 showed cytotoxicity against KB-C2 cells in the presence of 2.5 μM colchicine, suggesting that 5 might have an MDR-reversal effect.
Graduate School of Pharmaceutical Sciences, University of Tokushima, Shomachi 1-78, Tokushima 770-8505, Japan.
Shin-ichiro
S
Kurimoto
Graduate School of Pharmaceutical Sciences, University of Tokushima, Shomachi 1-78, Tokushima 770-8505, Japan.
Yoshihisa
Y
Takaishi
Department of Botany, Faculty of Biological Sciences, Jahangirnagar University, Savar, Dhaka 1342, Bangladesh.
Fakhruddin Ali
FA
Ahmed
Graduate School of Pharmaceutical Sciences, University of Tokushima, Shomachi 1-78, Tokushima 770-8505, Japan. Electronic address: kasiwada@tokushima-u.ac.jp.
Yoshiki
Y
Kashiwada
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology / Q000627:therapeutic use; D031601:Azadirachta / Q000737:chemistry*; D045744:Cell Line, Tumor; D018432:Drug Resistance, Multiple / Q000187:drug effects*; D019008:Drug Resistance, Neoplasm / Q000187:drug effects*; D005638:Fruit / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D018515:Plant Leaves; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology / Q000627:therapeutic use
D000972:Antineoplastic Agents, Phytogenic; D010936:Plant Extracts; D014315:Triterpenes
Azadirachta indica; Cytotoxicity; Meliaceae; Triterpenoid