N-alkylamides from Litsea cubeba (Lour.) Pers. with potential anti-inflammatory activity

• Published in: Natural product research Vol. 38; no. 10; pp. 1727 - 1738
• Main Authors: Shen, Guo-Dong, Zhang, Yin-Yan, Yang, Nian-Qi, Yang, Tong, Wang, Ting, Lu, Shi-Cheng, Wang, Jin-Yun, Wang, Yun-Song, Yang, Jing-Hua
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 18.05.2024; Taylor & Francis Ltd
• Subjects: Amides; anti-inflammatory; Anti-Inflammatory Agents; Herbal medicine; Inflammatory diseases; Lauraceae; Lead compounds; Liquid oxygen; Litsea - chemistry; Litsea cubeba; Litsea cubeba (Lour.) Pers; Molecular docking; Molecular Docking Simulation; Nicotinamide; NMR; Nuclear magnetic resonance; pharmacophore model; anti-inflammatory; pharmacophore model; amides; molecular docking; Lauraceae; Litsea cubeba (Lour.) Pers
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2023.2222216

Six amides, including a new N-alkylamide (1), four known N-alkylamides (2-5) and one nicotinamide (6) were isolated from Litsea cubeba (Lour.) Pers., which is a pioneer herb traditionally utilized in medicine. Their structures were elucidated on the basis of 1D and 2D NMR experiments and by comparison of their spectroscopic and physical data with the literature values. Cubebamide (1) is a new cinnamoyltyraminealkylamide and possessed obvious anti-inflammatory activity against NO production with IC 50 values of 18.45 μM. Further in-depth pharmacophore-based virtual screening and molecular docking were carried out to reveal the binding mode of the active compound inside the 5-LOX enzyme. The results indicate that L. cubeba, and the isolated amides might be useful in the development of lead compounds for the prevention of inflammatory diseases.