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Molecules 2017, 22(11), 1835; doi:10.3390/molecules22111835

Semisynthesis, an Anti-Inflammatory Effect of Derivatives of 1β-Hydroxy Alantolactone from Inula britannica

1
Department of Immunology, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, China
2
Department of Infectious Disease, the First Hospital of Lanzhou University, Lanzhou 730000, China
3
Department of Pharmacy, the First Hospital of Lanzhou University, Lanzhou 730000, China
4
College of Chemistry & Pharmacy, Northwest A&F University, Yangling 712100, China
5
College of Plant Protection, Northwest A&F University, Yangling 712100, China
*
Authors to whom correspondence should be addressed.
Received: 14 September 2017 / Revised: 20 October 2017 / Accepted: 22 October 2017 / Published: 27 October 2017
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Abstract

1β-hydroxy alantolactone, a sesquiterpene lactone mainly isolated from Inula genus plants, exhibits potent anti-inflammatory and anticancer activities. In this work, 1β-hydroxy alantolactone was isolated and five derivatives were prepared through different reactions at the C1-OH and C13-methylene motifs. The structure–activity relationships (SAR) of anti-inflammatory effects against NO production in RAW264.7 cells showed that the α-methylene-γ-butyrolactone motif was essential for NO production suppression and that retaining the C1-OH group can remarkably improve this effect. The NF-κB signaling pathway plays a pivotal role in the regulation of NO expression. Moreover, the levels of p65 and p50 phosphorylation were investigated and active compound 1 inhibited phosphorylation of p65 and p50 in TNF-α-induced NF-κB signaling. Further molecular docking suggested that 1 may target the p65 of NF-κB. View Full-Text
Keywords: 1β-hydroxy alantolactone; semisynthesis; anti-inflammatory activity 1β-hydroxy alantolactone; semisynthesis; anti-inflammatory activity
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Chen, L.; Zhang, J.-P.; Liu, X.; Tang, J.-J.; Xiang, P.; Ma, X.-M. Semisynthesis, an Anti-Inflammatory Effect of Derivatives of 1β-Hydroxy Alantolactone from Inula britannica. Molecules 2017, 22, 1835.

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