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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 α 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.

marine drugs

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