Chemical constituents from Notopterygium incisum and their anti-neuroinflammatory activity

Li-Mei Ma; Jiao-Tai Shi; Tian Chai; Mohammad Reza Naghavi; Huan-Yan Liu; Ai-Mei Yang; Jun Wang; Jun-Li Yang

doi:10.1016/j.fitote.2024.105976

Chemical constituents from Notopterygium incisum and their anti-neuroinflammatory activity

Fitoterapia. 2024 Apr 27:176:105976. doi: 10.1016/j.fitote.2024.105976. Online ahead of print.

Authors

Li-Mei Ma¹, Jiao-Tai Shi², Tian Chai³, Mohammad Reza Naghavi⁴, Huan-Yan Liu⁵, Ai-Mei Yang⁶, Jun Wang⁷, Jun-Li Yang⁸

Affiliations

¹ CAS 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 (CAS), Lanzhou 730000, People's Republic of China; Guangdong Key Laboratory of Natural Medicine Research and Development, College of Pharmacy, Guangdong Medical University, Dongguan 523808, People's Republic of China.
² School of Life Science and Engineering, Lanzhou University of Technology, Lanzhou 730050, People's Republic of China.
³ CAS 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 (CAS), Lanzhou 730000, People's Republic of China.
⁴ Department of Agronomy and Plant Breeding, Agricultural and Natural Resources College, University of Tehran, Karaj, Iran.
⁵ Guangdong Key Laboratory of Natural Medicine Research and Development, College of Pharmacy, Guangdong Medical University, Dongguan 523808, People's Republic of China.
⁶ School of Life Science and Engineering, Lanzhou University of Technology, Lanzhou 730050, People's Republic of China. Electronic address: aimeiyang@163.com.
⁷ Shandong Laboratory of Yantai Advanced Materials and Green Manufacturing, Yantai 264010, People's Republic of China. Electronic address: licpwangjun@163.com.
⁸ CAS 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 (CAS), Lanzhou 730000, People's Republic of China. Electronic address: yangjl@licp.cas.cn.

PMID: 38685511
DOI: 10.1016/j.fitote.2024.105976

Abstract

Phytochemical research on an extract of Notopterygium incisum yielded fifteen compounds (1-15), including four previously undescribed compounds (10-13). The structures of the unreported compounds were elucidated by spectroscopic and spectrometric data analysis such as 1D and 2D NMR, IR and HR-ESI-MS. Compounds 1-5 and 10-14 were isolated from N. incisum for the first time. 7S^⁎,8R^⁎-Phenethyl-(7-methoxy-8-isoeugenol)-ferulate (10), 7S^⁎,8R^⁎-p-hydroxyphenethyl-(7-methoxy-8-isoeugenol)-ferulate (11), 7S^⁎,8R^⁎-benzyl-(7-methoxy-8-isoeugenol)-ferulate (12) and p-hydroxyphenethyl-(4-benzoy-3-methoxy)-cinnamate (13) are the undescribed ferulic acid derivatives. Additionly, the anti-neuroinflammatory effects of compounds were evaluated in lipopolysaccharide (LPS)-induced BV2 cells. The pharmacological results showed that 6β,10β-epoxy-4α-hydroxy-guaiane (6), teuclatriol (7) and 7S^⁎,8R^⁎-p-hydroxyphenethyl-(7-methoxy-8-isoeugenol)-ferulate (11) inhibited the production and expression of nitric oxide (NO) in the LPS-induced BV2 cells in a concentration-dependent manner. Acorusnol (4), teucladiol (9), 7S^⁎,8R^⁎-benzyl-(7-methoxy-8-isoeugenol)-ferulate (12) and p-hydroxyphenethyl-(4-benzoy-3-methoxy)-cinnamate (13) only inhibited the release of NO at concentration of 20 μM. Moreover, 7S^⁎,8R^⁎-p-hydroxyphenethyl-(7-methoxy-8-isoeugenol)-ferulate (11) reduced the level of tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) in LPS-stimulated BV2 cells. The results demonstrated 7S^⁎,8R^⁎-p-hydroxyphenethyl-(7-methoxy-8-isoeugenol)-ferulate (11) could be a potential anti-neuroinflammatory agent and is worthy of further study.

Keywords: Anti-neuroinflammatory activity; BV2 cells; Chemical constituents; Notopterygium incisum; Umbelliferae.