The Melanogenesis-Inhibitory, Anti-Inflammatory, and Chemopreventive Effects of Limonoids in <i>n</i>-Hexane Extract of <i>Azadirachta indica</i> A. Juss. (Neem) Seeds

New triterpenoids from the kernels of Azadirachta indica

“…E-mail: mhchiu@mail.kib.ac.cn signals for 26 C-atoms in 1 were observed in the 1D NMR spectra, including seven quaternary C-atoms (three olefinic ones), eleven methines (four oxygenated ones and three olefinic groups), four methylenes, and four methyls. Detailed analysis of the 1 H and 13 C NMR spectral data of 1 revealed that they were similar to those of 3-deacetylsalannin (5). 16,17 The difference between 1 and 5 was that the tigloyl moiety in 5 was replaced by a benzoyl group in 1.…”

“…Finally, the structure of 2 was deduced as 7-tigloyl-12-oxo vilasini. 19 Compound 3 possessed a molecular formula of C 21 13 C NMR spectra further showed the presence of one ketone (δ C 204.7), one α,β-unsaturated-γ-lactone (δ C 172.6), one oxygenated methine (δ C 71.2) and one quaternary carbon (δ C 87.6). Above data suggested that 3 was the analogue of 7α-acetoxyl-4,4,8-trimethyl-5α-(13α-Me)-17-oxa-androsata-1,14-dien-3,16-dione, 20 except for less of an acetoxyl functionality.…”

“…[2][3][4] During the past four decades, more than 200 compounds, including terpenoids, 1 flavones, 5 steroids, 6 coumarins 7 and polysaccharides 8 had been isolated from different parts of A. indica, and some of them showed the significant bioactivities such as insecticides, 1,9,10 antifungal, 1,3 antitumor 1,2,11,12 and antimalarial. 1,13,14 Azadirachtin, as a well known natural pesticide, 3,15 was always extracted from the kernels of A. indica. However, we recently noticed that the kernals after extracting azadirachtin were always disposed as waste without good use.…”

Cytotoxic and Nitric Oxide Production‐Inhibitory Activities of Limonoids and Other Compounds from the Leaves and Bark of Melia azedarach

“…Thus, these compounds may be valuable as potential anti-inflammatory agents. It might be worthy to note that several vilasininand salannin-type limonoids [43], in addition to azadirone-, gedunin-, and nimbin-type limonoids [44], isolated from the seeds of Azadirachta indica, have been shown to possess potent inhibitory activities against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice.…”

Cytotoxic and Apoptosis-Inducing Activities of 12-<i>O</i>-Acetylazedarachin B from the Fruits of <i>Melia azedarach</i> in Human Cancer Cell Lines

“…[4][5][6][7][8] Several of the limonoids isolated from M. azedarach have been reported to possess cytotoxic, 9) antifeeding, 10) and insecticidal activities. 11) In the course of a search for potential bioactive compounds from Meliaceae plants, we have undertaken a detailed investigation on the limonoid constituents of Azadirachta indica (néem) seed extracts and have shown that some limonoids exhibit potent inhibitory activities against melanogenesis in B16 melanoma cells, against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice, and against TPA-induced Epstein-Barr virus early antigen (EBV-EA) activation, 12,13) as well as cytotoxic and apoptosisinducing activities. 14) In a continuing study on the limonoid constituents of Meliaceae plants, we have investigated the fruit extract of M. azedarach, and have isolated a trichilintype limonoid, 12-O-acetylazedarachin B (1), which exhibited about 100-times higher cytotoxic activities against leukemia (HL-60) and stomach (AZ521) cancer cell lines than those of a positive control, cisplatin.…”