Twelve novel sesquiterpenes with anti-inflammatory and cholesterol-lowering activities from burdock leaves.

Abstract

Nine new cadinane-type sesquiterpenoids (1-9) and three new eucalyptane -type sesquiterpenes (10-12) were isolated from the ethyl acetate extract of Burdock leaves, which were commonly used for preventing or treating atherosclerosis in China. Their structures were confirmed by extensive spectroscopic analysis, single-crystal X-ray diffraction analysis and ECD calculations. Compound 1 possessed the rare large conjugated skeleton. All the isolates were evaluated for anti-inflammatory and cholesterol-lowering activities by the LPS- and oxidized-low-density-lipoprotein-stimulated RAW 264.7 cells, respectively. As the results, all isolates could decrease the productions of NO, and down-regulate the accumulation of cholesterol. Among them, 4 showed the most potent cholesterol-lowering effect. For the high content of 4 in the herb, mechanistic study of 4 was performed and the results showed that 4 markedly reduced the release of pro-inflammatory mediators which was probably associated with inhibition of the PI3K/Akt and 5-LOX signaling pathways. The findings of this study demonstrated the anti-inflammatory/cholesterol-lowering effects of the new sesquiterpenes from burdock leaves, which provides chemical basis and scientific evidence for the herb used as anti-atherosclerosis agents for the further study. The sesquiterpene lactones of burdock leaves are expected to become new small molecule inhibitors for the treatment of AS.

• Authors: Hanjing Liang, Qingmei Feng, Hui Guo, Jiangnan Lv, Lingxia Zhang, Qingxia Li, Jun Chi, Qiuyan Liu, Zhimin Wang, Liping Dai
• Journal: Bioorganic chemistry (Bioorg Chem) Vol. 127 Pg. 105940 (10 2022) ISSN: 1090-2120 [Electronic] United States
• PMID: 35749853 (Publication Type: Journal Article, Review, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2022 Elsevier Inc. All rights reserved.

Chemical References

• Anti-Inflammatory Agents
• Sesquiterpenes
• Cholesterol

Topics

• Anti-Inflammatory Agents (chemistry)
• Arctium
• Cholesterol
• Molecular Structure
• Phosphatidylinositol 3-Kinases
• Sesquiterpenes (chemistry)