In vitro anti-inflammatory effects of diterpenoids and sesquiterpenoids from traditional Chinese medicine Siegesbeckia pubescens

Bioorg Med Chem Lett. 2014 Aug 15;24(16):3944-7. doi: 10.1016/j.bmcl.2014.06.039.

Rui Wang ¹, Ying-Qian Liu ², Wei Ha ³, Yan-Ping Shi ⁴, Tsong-Long Hwang ⁵, Guan-Jhong Huang ⁶, Tian-Shung Wu ⁷, Kuo-Hsiung Lee ⁸

Affiliations

1 Key Laboratory of Biochemistry and Molecular Biology in Universities of Shandong Province, Weifang University, Weifang 261061, PR China.
2 School of Pharmacy, Lanzhou University, Lanzhou 730000, PR China.
3 Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China.
4 Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China. Electronic address: shiyp@licp.cas.cn.
5 Chinese Herbal Medicine Research Team, Healthy Aging Research Center, Chang Gung University, Taoyuan 333, Taiwan.
6 School of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, College of Pharmacy, China Medical University, Taichung 404, Taiwan.
7 Department of Chemistry, National Cheng Kung University, Tainan 701, Taiwan.
8 Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599-7568, United States; Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung, Taiwan. Electronic address: khlee@email.unc.edu.

PMID: 24997688 DOI: 10.1016/j.bmcl.2014.06.039

Abstract

Oxidative stress imposed by Reactive Oxygen Species plays a crucial role in pathophysiology of inflammatory diseases. In the present study, sesquiterpenoids and Diterpenoids isolated from Siegesbeckia pubescens, a Chinese traditional medicine used to treat arthritis, were evaluated for inhibition of NO production in activated RAW 264.7 macrophages and FMLP/CB induced O2(·-) generation and Elastase release in human neutrophils. In the former assay, sesquiterpenoids were more potent than Diterpenoids. The C-4 carbonyl group in the carabrane-type sesquiterpenoid 3 and the C-9 ether linkage in the germacrane sesquiterpene 7 were associated with the enhanced potency. Also, for the active ent-kaurane type Diterpenoids, esterification of 17-OH with isobutyric acid and acetylation of 18-OH affected the inhibition of O2(·-) generation and Elastase release. This report is the first to describe the inhibitory effects on oxidative stress of secondary metabolites from S. pubescens. Its findings suggest that active Terpenoids from the herb could be used as lead anti-inflammatory agents.

Keywords

Anti-inflammatory; Cytotoxicity; Elastase release; NO production; Siegesbeckia pubescens; generation.

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