Structural elucidation of spiro cyclohexandienonyl naphthalenes with potential anti-neuroinflammatory activities from Caragana acanthophylla Kom

Di Zhou; Tiantian Zhang; Qingbo Liu; Jingyu Liu; Yanqiu Yang; Bin Lin; Gang Chen; Yue Hou; Ning Li

doi:10.1016/j.phytochem.2021.112976

Structural elucidation of spiro cyclohexandienonyl naphthalenes with potential anti-neuroinflammatory activities from Caragana acanthophylla Kom

Phytochemistry. 2021 Dec:192:112976. doi: 10.1016/j.phytochem.2021.112976. Epub 2021 Oct 19.

Authors

Di Zhou¹, Tiantian Zhang¹, Qingbo Liu¹, Jingyu Liu², Yanqiu Yang², Bin Lin³, Gang Chen¹, Yue Hou⁴, Ning Li⁵

Affiliations

¹ School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University; Key Laboratory for TCM Material Basis Study and Innovative Drug Development of Shenyang City, Shenyang, 110016, People's Republic of China.
² College of Life and Health Sciences, Northeastern University, Shenyang, 110004, People's Republic of China.
³ School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, 110016, People's Republic of China.
⁴ College of Life and Health Sciences, Northeastern University, Shenyang, 110004, People's Republic of China. Electronic address: [email protected].
⁵ School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University; Key Laboratory for TCM Material Basis Study and Innovative Drug Development of Shenyang City, Shenyang, 110016, People's Republic of China. Electronic address: [email protected].

PMID: 34678624
DOI: 10.1016/j.phytochem.2021.112976

Abstract

Four undescribed spiro cyclohexandienonyl naphthalenes (acanthophyllas A-D) and a revised compound were isolated from the roots of Caragana acanthophylla Kom. (Fabaceae). They were identified using extensive spectroscopic data and via chemical methods. Three of them were resolved into their enantiomers, and their absolute configurations were confirmed by comparing the experimental and calculated electronic circular dichroism spectra. Moreover, the anti-inflammatory activities of the compounds were investigated by evaluating their inhibitory effects on nitric oxide production in lipopolysaccharide-stimulated BV-2 cells. Some compounds showed significant inhibitory activities with IC₅₀ values of 8.8-13.4 μM (minocycline, IC₅₀ 7.8 μM), indicating that they might serve as potential therapeutic agents for neurodegenerative diseases.

Keywords: Anti-neuroinflammation; LPS-Induced BV-2 cell; Roots of Caragana acanthophylla Kom. (fabaceae); Spiro cyclohexandienonyl naphthalenes.

MeSH terms

Anti-Inflammatory Agents / pharmacology
Caragana*
Lipopolysaccharides / pharmacology
Molecular Structure
Naphthalenes / pharmacology
Nitric Oxide

Substances

Anti-Inflammatory Agents
Lipopolysaccharides
Naphthalenes
Nitric Oxide