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Mar. Drugs 2018, 16(12), 488; https://doi.org/10.3390/md16120488

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

1
Marine Drugs Research Center, College of Pharmacy, Jinan University, 601 Huangpu Avenue West, Guangzhou 510632, China
2
College of Pharmacy and Advanced Institute for Medical Sciences, Dalian Medical University, Dalian 116044, China
3
School of Pharmaceutical Sciences, Southern Medical University, 1838 Guangzhou Avenue North, Guangzhou 510515, China
These authors contributed equally.
*
Authors to whom correspondence should be addressed.
Received: 8 November 2018 / Revised: 27 November 2018 / Accepted: 4 December 2018 / Published: 6 December 2018
(This article belongs to the Special Issue Bioactive Compounds from Mangroves and Their-Associated Microbes)
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Abstract

Ten new triterpenoid compounds with structure diversity of the C-17 side-chain, including nine tirucallanes, named xylocarpols A–E (15) and agallochols A–D (69), 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, 68 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. View Full-Text
Keywords: mangrove; triterpenoid; tirucallane; apotirucallane; farnesoid–X–receptor; pregnane–X–receptor mangrove; triterpenoid; tirucallane; apotirucallane; farnesoid–X–receptor; pregnane–X–receptor
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Jiang, Z.-P.; Luan, Z.-L.; Liu, R.-X.; Zhang, Q.; Ma, X.-C.; Shen, L.; Wu, J. Mangrove Tirucallane- and Apotirucallane-Type Triterpenoids: Structure Diversity of the C-17 Side-Chain and Natural Agonists of Human Farnesoid/Pregnane–X–Receptor. Mar. Drugs 2018, 16, 488.

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