Anti-inflammatory neolignans from the roots of Magnolia officinalis

Hung-Cheng Shih; Ping-Chung Kuo; Shwu-Jen Wu; Tsong-Long Hwang; Hsin-Yi Hung; De-Yang Shen; Po-Chuen Shieh; Yu-Ren Liao; E-Jian Lee; Qiong Gu; Kuo-Hsiung Lee; Tian-Shung Wu

doi:10.1016/j.bmc.2016.01.049

Anti-inflammatory neolignans from the roots of Magnolia officinalis

Bioorg Med Chem. 2016 Apr 1;24(7):1439-45. doi: 10.1016/j.bmc.2016.01.049. Epub 2016 Jan 27.

Authors

Affiliations

¹ School of Pharmacy, National Cheng Kung University Hospital, College of Medicine, National Cheng Kung University, Tainan 701, Taiwan, ROC.
² Department of Biotechnology, National Formosa University, Yunlin 632, Taiwan, ROC.
³ Department of Medical Technology, Chung Hua University of Medical Technology, Tainan 717, Taiwan, ROC.
⁴ Graduate Institute of Natural Products, Chang Gung University, Taoyuan 333, Taiwan, ROC; Chinese Herbal Medicine Research Team, Healthy Aging Research Center, Chang Gung University, Taoyuan 333, Taiwan, ROC.
⁵ Department of Pharmacy, Tajen University, Pintung 907, Taiwan, ROC.
⁶ Department of Surgery, and Institute of Biomedical Engineering, National Cheng Kung University, Medical Center and Medical School, Tainan 701, Taiwan, ROC; Department of Anesthesiology, and Institute of Biomedical Engineering, National Cheng Kung University, Medical Center and Medical School, Tainan 701, Taiwan, ROC.
⁷ Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA.
⁸ Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA; Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung 401, Taiwan, ROC. Electronic address: khlee@unc.edu.
⁹ School of Pharmacy, National Cheng Kung University Hospital, College of Medicine, National Cheng Kung University, Tainan 701, Taiwan, ROC; Department of Pharmacy, Tajen University, Pintung 907, Taiwan, ROC. Electronic address: tswu@mail.ncku.edu.tw.

PMID: 26928286
DOI: 10.1016/j.bmc.2016.01.049

Abstract

Nine neolignan derivatives (1-9) were characterized from the roots of Magnolia officinalis, and their structures were elucidated based on spectroscopic and physicochemical analyses. Among them, houpulins E (1) and M (9) possess novel homo- and trinor-neolignan skeletons. In addition, 15 known compounds (10-24) were identified by comparison of their spectroscopic and physical data with those reported in the literature. Some of the purified constituents were examined for anti-inflammatory activity and, among the tested compounds, houpulins G (3), I (5), J (6), and 2,2'-dihydroxy-3-methoxy-5,5'-di-(2-propenylbiphenyl) (19) significantly inhibited superoxide anion generation and elastase release with IC50 values ranging from 3.54 to 5.48 μM and 2.16 to 3.39 μM, respectively. Therefore, these neolignan derivatives have tremendous potential to be explored as anti-inflammatory agents.

Keywords: Anti-inflammatory activity; Houpulins E–M; Magnolia officinalis; Neolignans.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adult
Anti-Inflammatory Agents, Non-Steroidal / chemistry
Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
Dose-Response Relationship, Drug
Humans
Lignans / chemistry
Lignans / isolation & purification
Lignans / pharmacology*
Magnolia / chemistry*
Molecular Structure
Neutrophils / drug effects
Neutrophils / metabolism
Pancreatic Elastase / metabolism*
Plant Roots / chemistry*
Quantum Theory
Structure-Activity Relationship
Superoxides / metabolism*
Young Adult

Substances

Anti-Inflammatory Agents, Non-Steroidal
Lignans
Superoxides
Pancreatic Elastase