Degraded and oxetane-bearing limonoids from the roots of Melia azedarach.
Brine shrimp lethality test (BST)-guided fractionation of a methanol extract of the roots of Melia azedarach resulted in the isolation of two new limonoids, 9alpha-hydroxy-12alpha-acetoxyfraxinellone (1) and 7,14-epoxy-azedarachin B (2), together with the known compounds, 12alpha-hydroxyfraxinellone (4), 9alpha-hydroxyfraxinellone (5), azedarachin B (6), and neoazedarachin B (7). The structures of 1 and 2 were elucidated by analysis of spectroscopic data and comparison of their NMR data with those of the known compounds. Compounds 1, 2 and 4-7 exhibited significant activity in the BST, in particular, azedarachin B (6) showed remarkable BST activity with an LC(50) value of 0.0098 microM.
Fukuyama
Yoshiyasu
Y
Institute of Pharmacognosy, Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan. fukuyama@ph.bunri-u.ac.jp
Nakaoka
Momoko
M
Yamamoto
Tomoko
T
Takahashi
Hironobu
H
Minami
Hiroyuki
H
D000818:Animals; D001156:Artemia / Q000187:drug effects; D001572:Benzofurans / Q000737:chemistry* / Q000494:pharmacology; D001681:Biological Assay; D004988:Ethers, Cyclic / Q000737:chemistry*; D036701:Limonins / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D031586:Melia azedarach / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D013256:Steroids / Q000737:chemistry* / Q000494:pharmacology
C514006:7,14-epoxyazedarachin B; C514005:9-hydroxy-12-acetoxyfraxinellone; D001572:Benzofurans; D004988:Ethers, Cyclic; D036701:Limonins; D013256:Steroids; C005287:oxetane; D000432:Methanol