Baeckeins F-I, four novel C-methylated biflavonoids from the roots of Baeckea frutescens and their anti-inflammatory activities
Baeckeins F-I, four novel C-methylated biflavonoids from the roots of Baeckea frutescens and their anti-inflammatory activities
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Baeckeins F-I，来自 Baeckea frutescens 根的四种新型 C-甲基化双黄酮类化合物及其抗炎活性
DOI：
10.1016/j.foodchem.2014.01.022
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发表时间：
2014-07-15
期刊：
影响因子：
8.8
通讯作者：
Wang, Qiang
中科院分区：
文献类型：
--
作者：
Jia, Bei-Xi;Zeng, Xian-Lei;Wang, Qiang
Baeckea frutescens 是一种芳香灌木，在中国南方用作观赏植物和香料。从 B. frutescens 的根中分离出四种不寻常的 C-甲基化双黄酮类化合物，命名为 baeckeins F-I (1-4)。 baeckeins F-I 具有独特的碳骨架，即通过 C-2-C-8(*) 和 C-3-0-C-7* 的不寻常连接与香豆色酮分子缀合的黄酮醇。通过分析一维（H-1/C-13）和二维核磁共振（HSQC/HMBC/NOESY）和HR-ESI-MS光谱数据阐明了它们的结构，并通过CD光谱法结合量子化学计算建立了C-2和C-3手性碳的绝对立体化学。还通过检测 LPS 诱导的 RAW264.7 鼠巨噬细胞系的 NO 产生来评估 Baeckeins F-I (1-4) 的抗炎活性；具有β-D-葡萄糖单元和(2R,3R)构型的baeckein I (4)表现出最高的NO抑制活性(IC50=15.2μM)，这与阳性对照吲哚美辛相似。皇冠版权所有 (C) 2014 由 Elsevier Ltd 出版。保留所有权利。
Baeckea frutescens is an aromatic shrub used in South China as an ornamental and as a spice. Four unusual C-methylated biflavonoids named baeckeins F-I (1-4) were isolated from the roots of B. frutescens. The baeckeins F-I possessed a unique carbon skeleton, a flavonol conjugated with a coumaronochromone molecule via the unusual linkages of C-2-C-8(*) and C-3-0-C-7*. Their structures were elucidated by analysis of the 1D (H-1/C-13) and 2D NMR (HSQC/HMBC/NOESY) and HR-ESI-MS spectroscopic data, and the absolute stereochemistry for chiral carbons of C-2 and C-3 was established by CD spectrometry combined with quantum chemical calculations. Baeckeins F-I (1-4) were also evaluated for their anti-inflammatory activities by detecting the NO production of LPS-induced RAW264.7 murine macrophage cell line; baeckein I (4) with the beta-D-glucose unit and configuration of (2R,3R) exhibited the highest NO inhibitory activity (IC50= 15.2 mu M), which was similar to that of the positive control indomethacin. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.