A New Compound Isolated from the Reduced Ribose–Tryptophan Maillard Reaction Products Exhibits Distinct Anti-inflammatory Activity,Journal of Agricultural and Food Chemistry

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A New Compound Isolated from the Reduced Ribose–Tryptophan Maillard Reaction Products Exhibits Distinct Anti-inflammatory Activity
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2018-06-12 00:00:00 , DOI: 10.1021/acs.jafc.8b01561
Dan Qin _{1,

2} , Lin Li _{1,

3,

4} , Jing Li ₅ , Jinlong Li ₆ , Di Zhao ₁ , Yuting Li ₃ , Bing Li _{1,

4} , Xia Zhang _{1,

4}

Affiliation

In this study, a compound of 532.24 Da named BF-4 was separated from the ribose–tryptophan Maillard reaction products by solvent extraction and purified through reverse phase high performance liquid chromatography. The purified compound BF-4 was identified as 3-((1H-indol-3-yl)methyl)-8-(5-((1H-indol-3-yl)methyl)-6-oxomorpholin-2-yl)-9-hydroxy-1,7,4-dioxazecan-2-one in accordance with 1D- and 2D-NMR spectra and LC-ESI-MS/MS analysis. BF-4 significantly reduced the production of nitric oxide (NO), interleukin-6 (IL-6), and tumor necrosis factor α (TNF-α) in lipopolysaccharide-stimulated RAW 264.7 cells. It inhibited nuclear factor κB (NF-κB) activation and mitogen-activated protein kinase (MAPK) phosphorylation through suppressing phosphorylation of IκBα, P65, P38 and c-Jun N-terminal kinase (JNK). The anti-inflammatory activity of BF-4 was comparable to dexamethasone, and more importantly, BF-4 showed less cytotoxicity than dexamethasone on the normal human liver cell LO2. The results indicate that BF-4 is a promising anti-inflammatory agent with pharmaceutical potential.

中文翻译：

从减少的核糖色氨酸美拉德反应产物中分离出来的新化合物具有独特的抗炎活性

在这项研究中，通过溶剂萃取从核糖-色氨酸美拉德反应产物中分离出532.24 Da的化合物BF-4，并通过反相高效液相色谱进行纯化。纯化的化合物BF-4被鉴定为3-（（1 H-吲哚-3-基）甲基）-8-（5-（（1 H-indol-3-yl）methyl）-6-oxomorpholin-2-yl）-9-hydroxy-1,7,4-dioxazecan-2-one根据1D-和2D-NMR光谱和LC-ESI-MS / MS分析。BF-4显着降低了脂多糖刺激的RAW 264.7细胞中一氧化氮（NO），白介素6（IL-6）和肿瘤坏死因子α（TNF-α）的产生。它通过抑制IκBα，P65，P38和c-Jun N端激酶（JNK）的磷酸化来抑制核因子κB（NF-κB）活化和有丝分裂原激活的蛋白激酶（MAPK）磷酸化。BF-4的抗炎活性与地塞米松相当，更重要的是，BF-4在正常人肝细胞LO2上显示出比地塞米松更少的细胞毒性。结果表明，BF-4是一种有前途的抗炎药，具有药物开发潜力。

更新日期：2018-06-12

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