Undescribed steroidal alkaloids from the bulbs of Fritillaria ussuriensis Maxim and their anti-inflammatory activities

• Published in: Phytochemistry (Oxford) 2024-09, Vol.225, p.114172, Article 114172
• Main Authors: Lu, Dongxv, Jiang, Peng, Wang, Yanfu, Li, Yanying, Naseem, Anam, Mohammed Algradi, Adnan, Pan, Juan, Guan, Wei, Wu, Jiatong, Kuang, Haixue, Yang, Bingyou, Liu, Yan
• Format: Article
• Language: English
• Subjects: 16-Hydroxyl cevanine alkaloids; Anti-inflammatory activity; Fritillaria ussuriensis; Liliaceae; plant biochemistry; skeleton; spectroscopy; Steroidal alkaloids
• ISSN: 0031-9422; 1873-3700; 1873-3700
• DOI: 10.1016/j.phytochem.2024.114172

In total, 16 undescribed steroidal alkaloids (1–16), along with nine known ones (17–25), were isolated from the bulbs of Fritillaria ussuriensis Maxim. Among the undescribed compounds mentioned, compounds 1–6, 8 bearing an 16β-hydroxy substituent, as well as compounds 13 and 14 exhibited an unusual seven-membered skeleton. Their structures were established based on extensive spectroscopic analyses, including HRESIMS and NMR (1D and 2D), and comparison with the data reported in the literature. Furthermore, all the compounds were evaluated for their anti-inflammatory effect on the NO production of LPS-stimulated RAW264.7 cells. Compounds 1, 4, 11, 15, 22 and 24 could significantly inhibit NO production with IC50 values below 10 μM. [Display omitted] •Sixteen undescribed steroidal alkaloids were isolated from the bulbs of Fritillaria ussuriensis.•The seven-membered skeleton and 16β-hydroxy substituent of steroidal alkaloids are rare in natural products.•Compound 11 had a significant inhibitory effect on the production of NO.