Mangrove Tirucallane- and Apotirucallane-Type Triterpenoids: Structure Diversity of the C-17 Side-Chain and Natural Agonists of Human Farnesoid/Pregnane⁻X⁻Receptor

红树林 Tirucallane 和 Apotirucallane 型三萜:人类法呢醇/孕烷⁻X⁻受体的 C-17 侧链和天然激动剂的结构多样性

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作者:Zhong-Ping Jiang, Zhi-Lin Luan, Ruo-Xi Liu, Qun Zhang, Xiao-Chi Ma, Li Shen, Jun Wu

Abstract

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 Kα 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 μM; 10 exhibited very significant agonistic effects on pregnane⁻X⁻receptor (PXR) at the concentration of 10.0 nM.

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