Four New Tirucallane Triterpenoids from the Fruits of Melia azedarach and Their Cytotoxic Activities

Abstract

Four new tirucallane triterpenoids, (21S,23R,24R)-21,23-epoxy-21,24-dihydroxy-25-methoxytirucall-7-en-3-one (2), (3S,21S,23R,24S)-21,23-epoxy-21,25-dimethoxytirucall-7-ene-3,24-diol (8), (21S,23R,24R)-21,23-epoxy-24-hydroxy-21-methoxytirucalla-7,25-dien-3-one (11), and (21S,23R,24R)-21,23-epoxy-21,24-dihydroxytirucalla-7,25-dien-3-one (12), along with 16 known analogues, 1, 3 - 7, 9 - 10, and 13 - 20, were isolated from the fruits of Melia azedarach. Their structures were elucidated by spectroscopic methods including 1D- and 2D-NMR techniques and mass spectrometry. These compounds were evaluated for their cytotoxicities against HepG2 (liver), SGC7901 (stomach), K562 (leukemia), and HL60 (leukemia) cancer cell lines. Compound 20 exhibited potent cytotoxicity against HepG2 and SGC7901 cancer cells with the IC₅₀ values of 6.9 and 6.9 μm, respectively.

Keywords: Melia azedarach; Cytotoxic activities; Limonoids; Tirucallane triterpenoids.