Anti-neuroinflammatory terpenes from Magnolia grandiflora

Ding-Xun Wu; Jue Yang; Li-Hua Chen; Shuang-Yu Xu; Jun Jin; Ya-Nan Li; Xiao-Jiang Hao; Chun-Mao Yuan

doi:10.1016/j.phytochem.2024.114370

Anti-neuroinflammatory terpenes from Magnolia grandiflora

Phytochemistry. 2024 Dec 18:232:114370. doi: 10.1016/j.phytochem.2024.114370. Online ahead of print.

Authors

Ding-Xun Wu¹, Jue Yang², Li-Hua Chen², Shuang-Yu Xu², Jun Jin², Ya-Nan Li², Xiao-Jiang Hao³, Chun-Mao Yuan⁴

Affiliations

¹ School of Pharmaceutical Sciences, Guizhou University, Huaxi Avenue 2708, Guiyang, 550025, PR China; State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, 550014, PR China; Natural Products Research Center of Guizhou Province, Guiyang, 550014, PR China.
² State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, 550014, PR China; Natural Products Research Center of Guizhou Province, Guiyang, 550014, PR China.
³ State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, 550014, PR China; Natural Products Research Center of Guizhou Province, Guiyang, 550014, PR China; State Key Laboratory of Phytochemistry and Natural Medicine, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, PR China. Electronic address: haoxj@mail.kib.ac.cn.
⁴ State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, 550014, PR China; Natural Products Research Center of Guizhou Province, Guiyang, 550014, PR China. Electronic address: yuanchunmao01@126.com.

PMID: 39706541
DOI: 10.1016/j.phytochem.2024.114370

Abstract

Six previously undescribed sesquiterpenes, magnogranoides A-F (1-6), along with 10 known terpenes, were isolated from the leaves of Magnolia grandiflora L. Six previously undescribed sesquiterpene derivatives (11a-11e and 14a) were synthesized using chemical methods. Those structures were identified through extensive spectroscopic data and quantum chemical calculations. Notably, compound 1 represents the first sesquiterpene with a previously undescribed 8/5/5 tricyclic ring, and compound 2 was elucidated to be the first 13-norguaiane-type sesquiterpenoid with a 5/7/5 tricyclic ring system. Four compounds (3, 7, 8, and 16) exhibited better anti-neuroinflammatory activities in BV-2 cells with IC₅₀ values ranging from 3.23 ± 0.23 μM to 15.98 ± 1.79 μM than the positive control, minocycline (IC₅₀: 20.56 ± 0.93). Furthermore, the chemotaxonomic significance of the isolates was also discussed.

Keywords: Anti-inflammatory activity; Chemotaxonomic significance; Magnolia grandiflora; Magnoliaceae; Sesquiterpenes.