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从 Acer mandshuricum 中分离得到的三萜类化合物及其抗炎活性。

Triterpene compounds isolated from Acer mandshuricum and their anti-inflammatory activity.

机构信息

College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.

出版信息

Bioorg Med Chem Lett. 2010 Mar 1;20(5):1528-31. doi: 10.1016/j.bmcl.2010.01.096. Epub 2010 Jan 25.

Abstract

In our preliminary screening study on the anti-inflammatory activity, a new triterpene compound, aceranol acetate (1), was isolated along with five known compounds: beta-amyrin acetate (2); glutinol acetate (3); friedelin (4); glutinol (5); (3beta)-d-glucopyranoside-stigmast-5-en-3-yl (6), from the stems and leaves of Acer mandshuricum. The structure of the new triterpene was determined to be 5alpha,6alpha-epidioxy-5beta,6beta-epoxy-9,13-dimethyl-25,26-dinoroleanan-3beta-ol acetate by spectroscopic studies. Compounds 2-6 were isolated from this plant for the first. Five triterpene compounds (1-5) showed significant cytotoxic activity with GI(50) in the range of 11.1-17.9microM, whereas steroid compound (6) exhibited moderate activity against four human cancer cell lines (HL-60, SK-OV-3, A549, and HT-29). Furthermore, the anti-inflammatory effects of compounds 1-6 in the non-cytotoxic concentrations (1-100nM) were evaluated for the inhibitory activity of TNF-alpha secretion in the lipopolysaccharide (LPS)-stimulated murine RAW264.7 macrophage cell line. Among the compounds tested, compound 2 showed the strongest anti-inflammatory activity with the inhibition rate up to 38.40% at the concentration of 100nM, whereas other five compounds (2-6) exhibited moderate activity.

摘要

在我们对抗炎活性的初步筛选研究中,从 Acer mandshuricum 的茎和叶中分离得到了一种新的三萜化合物 aceranol 乙酸酯(1),以及五种已知化合物:乙酸-β-香树脂醇(2);乙酸谷甾醇(3);friedelin(4);谷甾醇(5);(3β)-D-吡喃葡萄糖基-豆甾-5-烯-3-基(6)。通过光谱研究确定新三萜的结构为 5α,6α-表环氧-5β,6β-表环氧-9,13-二甲基-25,26-降胆甾烷-3β-醇乙酸酯。化合物 2-6 是从这种植物中首次分离出来的。五种三萜化合物(1-5)表现出显著的细胞毒性,GI(50)在 11.1-17.9μM 范围内,而甾体化合物(6)对四种人类癌细胞系(HL-60、SK-OV-3、A549 和 HT-29)表现出中等活性。此外,在非细胞毒性浓度(1-100nM)下评估了化合物 1-6 的抗炎作用,以评估其对脂多糖(LPS)刺激的鼠 RAW264.7 巨噬细胞系中 TNF-α分泌的抑制活性。在所测试的化合物中,化合物 2 在 100nM 浓度下表现出最强的抗炎活性,抑制率高达 38.40%,而其他五种化合物(2-6)则表现出中等活性。

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