The Melanogenesis-Inhibitory, Anti-Inflammatory, and Chemopreventive Effects of Limonoids in n-Hexane Extract of Azadirachta indica A. Juss. (Neem) Seeds
The Melanogenesis-Inhibitory, Anti-Inflammatory, and Chemopreventive Effects of Limonoids in n-Hexane Extract of Azadirachta indica A. Juss. (Neem) Seeds
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DOI：
10.5650/jos.60.53
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发表时间：
2011-02-01
影响因子：
1.5
通讯作者：
Yasukawa, Ken
中科院分区：
文献类型：
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作者：
Akihisa, Toshihiro;Takahashi, Akitomo;Yasukawa, Ken
从印楝种子的正己烷提取物中分离出 17 种柠檬苦素类化合物（四降三萜 1-17）。通过光谱分析确定先前未鉴定的化合物16为17-defurano-17-oxosalannin。评估了六种化合物（6 和 11-15）对 B16 黑色素瘤细胞中黑色素生成的影响； 2 种化合物，salannin (13) 和 3-de乙酰salannin (15)，表现出显着的抑制作用（25 μg/mL 时黑色素含量降低 70-74%），而细胞毒性较小（细胞活力降低 79-85%）。评估了 11 种化合物 2、3、5、6 和 9-15 对 12-O-十四烷酰佛波醇-13-乙酸酯 (TPA) 诱导的小鼠炎症（1.7 nmol/耳）的抑制活性；均表现出显着的抗炎活性（ID50值0.22-0.57μmol/耳）。此外，化合物6和11-16对Raji细胞中TPA诱导的Epstein-Barr病毒早期抗原(EBV-EA)活化具有中等抑制作用(IC50值为410-471摩尔比/32 pmol TPA)。正己烷提取物的三酰甘油部分含有油酸（50.2%）作为最主要的脂肪酸成分。
Seventeen limonoids (tetranortriterpenoids 1-17) were isolated from the n-hexane extract of Azadirachta indica (neem) seeds. The previously unidentified compound 16 was established by spectroscopy to be 17-defurano-17-oxosalannin. The effects of six compounds, 6 and 11-15, on melanogenesis in B16 melanoma cells was evaluated; 2 compounds, salannin (13) and 3-deacetylsalannin (15), exhibited marked inhibitory effects (70-74% reduction of melanin content at 25 mu g/mL) with only minor cytotoxicity (79-85% of cell viability). Eleven compounds, 2, 3, 5, 6, and 9-15, were evaluated for inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1.7 nmol/ear) in mice; all exhibited marked anti-inflammatory activity (ID50 values 0.22-0.57 mu mol/ear). In addition, compounds 6 and 11-16 exerted moderate inhibition (IC50 values of 410-471 mol ratio/32 pmol TPA) of TPA-induced Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells. The triacylglycerol fraction of the n-hexane extract contained oleic acid (50.2%) as the most predominant fatty acid constituent.