Potential anti-inflammatory phenolic glycosides from the medicinal plant Moringa oleifera fruits
Potential anti-inflammatory phenolic glycosides from the medicinal plant Moringa oleifera fruits
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DOI：
10.1016/j.bmc.2010.03.057
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发表时间：
2010-09-01
影响因子：
3.5
通讯作者：
Chang, Leng Chee
中科院分区：
文献类型：
--
作者：
Cheenpracha, Sarot;Park, Eun-Jung;Chang, Leng Chee
利用生物活性导向法从辣木果实乙酸乙酯提取物中分离纯化得到三个新的酚苷类化合物; 4-[（2 ′-O-乙酰基-α-L-鼠李糖氧基）苄基]异硫氰酸酯（1），4-[（3 ′-O-乙酰基-α-L-鼠李糖氧基）苄基]异硫氰酸酯（2），和S-甲基-N-{4-[（α-L-鼠李糖氧基）苄基]}硫代氨基甲酸酯（3），以及五种已知的酚糖苷（4-8）。新代谢产物的结构是根据光谱分析（包括1D-和2D-NMR和质谱）确定的。用脂多糖（LPS）诱导的鼠巨噬细胞RAW 264.7细胞系研究分离的化合物的抗炎活性。发现4-[（2 ′-O-乙酰基-α-L-鼠李糖氧基）苄基]异硫氰酸酯（1）具有有效的NO抑制活性，IC（50）值为1.67 μ M，其次分别为2（IC（50）= 2.66 μ M）、4（IC（50）= 2.71 μ M）和5（IC（50）= 14.4 μ M）。Western印迹证明这些化合物降低LPS介导的iNOS表达。在IC 50值的浓度范围内，未观察到明显的细胞毒性。NO释放后的构效关系表明：（1）异硫氰酸酯基团是活性所必需的，（2）在鼠李糖C-2'或C-3'处乙酰化的异硫氰酸酯衍生物活性更高，（3）未乙酰化的异硫氰酸酯衍生物活性比乙酰化的衍生物低8倍，（4）乙酰化的硫代氨基甲酸酯衍生物活性增强。这些数据表明，化合物1，2，4和5负责报道的辣木果实的NO抑制作用，并需要进一步的研究。(C)2010爱思唯尔有限公司版权所有。
Bioassay-guided isolation and purification of the ethyl acetate extract of Moringa oleifera fruits yielded three new phenolic glycosides; 4-[(2'-O-acetyl-alpha-L-rhamnosyloxy) benzyl] isothiocyanate (1), 4-[(3'-Oacetyl-alpha-L-rhamnosyloxy) benzyl] isothiocyanate (2), and S-methyl-N-{4-[(alpha-L-rhamnosyloxy) benzyl]}thiocarbamate (3), together with five known phenolic glycosides (4-8). The structures of the new metabolites were determined on the basis of spectroscopic analyses including 1D- and 2D-NMR and mass spectrometry. The anti-inflammatory activity of isolated compounds was investigated with the lipopolysaccharide (LPS)-induced murine macrophage RAW 264.7 cell line. It was found that 4-[(2'-O-acetyl-alpha-L-rhamnosyloxy) benzyl] isothiocyanate (1) possessed potent NO-inhibitory activity with an IC(50) value of 1.67 mu M, followed by 2 (IC(50) = 2.66 mu M), 4 (IC(50) = 2.71 mu M), and 5 (IC(50) = 14.4 mu M), respectively. Western blots demonstrated these compounds reduced LPS-mediated iNOS expression. In the concentration range of the IC50 values, no significant cytotoxicity was noted. Structure-activity relationships following NO-release indicated: (1) the isothiocyanate group was essential for activity, (2) acetylation of the isothiocyanate derivatives at C-2' or at C-3' of rhamnose led to higher activity, (3) un-acetylated isothiocyanate derivatives displayed eight times less activity than the acetylated derivatives, and (4) acetylation of the thiocarbamate derivatives enhanced activity. These data indicate compounds 1, 2, 4 and 5 are responsible for the reported NO-inhibitory effect of Moringa oleifera fruits, and further studies are warranted. (C) 2010 Elsevier Ltd. All rights reserved.