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.
Highlights
Cholestasis, a clinical syndrome of hepatobiliary diseases, is usually caused by accumulation of bile acids in the liver and systemic circulation [1]
We reported isolated from mangrove plants X. granatum, X. moluccensis, and E. agallocha
Based on the the absolute configurations of C-3, C-23, and C-24 were assigned as S, R, and S, respectively
Summary
Cholestasis, a clinical syndrome of hepatobiliary diseases, is usually caused by accumulation of bile acids in the liver and systemic circulation [1]. Due to the regulation capability of a suite of genes involved in the metabolism, transport, and elimination of bile acids, FXR and PXR are considered to be the key target proteins for the treatment of cholestasis and liver injury [1,3,4,5]. Previous chemical investigation of this plant resulted in the isolation and and identification of diterpenoid, triterpenoid, tanninoid, and flavonoid natural compounds [10,17–. As part of our ongoing investigation of bioactive natural products from mangrove plants, 10 new new triterpenoid compounds, including nine tirucallanes (1–9) and one apotirucallane (10) (Figure triterpenoid compounds, including nine tirucallanes (1–9) and one apotirucallane (10) (Figure 1), were. We reported isolated from mangrove plants X. granatum, X. moluccensis, and E. agallocha.
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