Mangrove Tirucallane- and Apotirucallane-Type Triterpenoids: Structure Diversity of the C-17 Side-Chain and Natural Agonists of Human Farnesoid/Pregnane-X-Receptor
Mangrove Tirucallane- and Apotirucallane-Type Triterpenoids: Structure Diversity of the C-17 Side-Chain and Natural Agonists of Human Farnesoid/Pregnane-X-Receptor
复制标题
红树林 Tirucallane 型和 Apotirucallane 型三萜类化合物：人 Farnesoid/Pregnane(-)X(-) 受体 C-17 侧链和天然激动剂的结构多样性。
DOI：
10.3390/md16120488
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发表时间：
2018-12-01
期刊：
影响因子：
5.4
通讯作者：
Wu, Jun
中科院分区：
文献类型：
--
作者：
Jiang, Zhong-Ping;Luan, Zhi-Lin;Wu, Jun
从红树林植物Xylocarpus granatum、Xylocarpus moluccensis和Excoecaria agallocha中分离得到10个C-17侧链结构多样的三萜类化合物，其中9个为tirucallane，命名为xylocarpols A-E（1-5）和agallochols A-D（6-9），1个为apotirucallane，命名为25-dehydroxy protoxyogranatin B（10）。这些化合物的结构通过HR-ESIMS和广泛的一维（1D）和二维（2D）NMR研究确定。1和2的绝对构型通过单晶X射线衍射分析明确确定，用Cu K辐射进行;而4，6-8的绝对构型通过修改的Mosher方法和实验电子圆二色性（ECD）光谱的比较来分配。最值得注意的是，5、6、7和9在10.0 nM的浓度下对类法尼醇-X-受体（FXR）表现出有效的激活作用; 10在10.0 nM的浓度下对孕烷-X-受体（PXR）表现出非常显著的激动作用。
Ten new triterpenoid compounds with structure diversity of the C-17 side-chain, including nine tirucallanes, named xylocarpols A-E (1-5) and agallochols A-D (6-9), and an apotirucallane, named 25-dehydroxy protoxylogranatin B (10), were isolated from the mangrove plants Xylocarpus granatum, Xylocarpus moluccensis, and Excoecaria agallocha. The structures of these compounds were established by HR-ESIMS and extensive one-dimensional (1D) and two-dimensional (2D) NMR investigations. The absolute configurations of 1 and 2 were unequivocally determined by single-crystal X-ray diffraction analyses, conducted with Cu K radiation; whereas those of 4, 6-8 were assigned by a modified Mosher's method and the comparison of experimental electronic circular dichroism (ECD) spectra. Most notably, 5, 6, 7, and 9 displayed potent activation effects on farnesoid-X-receptor (FXR) at the concentration of 10.0 M; 10 exhibited very significant agonistic effects on pregnane-X-receptor (PXR) at the concentration of 10.0 nM.