Three new alkaloids from Xylopia vielana and their antiinflammatory activities

• Published in: Fitoterapia Vol. 127; pp. 96 - 100
• Main Authors: Guo, Yi-Gong, Ding, Yun-He, Wu, Guo-Jing, Zhu, Sheng-Lan, Sun, Yuan-Fang, Yan, Shi-Kai, Qian, Feng, Jin, Hui-Zi, Zhang, Wei-Dong
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 01.06.2018; Elsevier Science Ltd
• Subjects: Alkaloids; Antiinflammatory activities; Cells; Chemical compounds; Crystallography; Lipopolysaccharides; Nitric oxide; Nitrogen; NMR; Nuclear magnetic resonance; Organic chemistry; Xylopia; Xylopia vielana; Alkaloids; Antiinflammatory activities; Xylopia vielana
• ISSN: 0367-326X; 1873-6971
• DOI: 10.1016/j.fitote.2018.02.001

Three new aporphine alkaloids, xylopialoids A-C (1–3), along with three known aporphine alkioids (4–6) and three other known compounds (7–9) were isolated from the roots of Xylopia vielana. Among these three new aporphine alkaloids, xylopialoid C (3) showed a special carbamido group directly connected to the nitrogen. The chemical structures of these nine compounds were determined by a combination of 1D and 2D NMR, MS, CD spectrum and Cu Kα X-ray crystallographic analyses. All these six alkaloids were firstly tested for the inhibitory activities against the production of NO in RAW264.7 cells stimulated by lipopolysaccharide (LPS). Among these compounds, 4 showed a potential inhibitory activity against the production of nitric oxide with IC50 value of 1.39 μM. Three newaporphine alkaloids, xylopialoids A–C (1–3), along with three known aporphine alkioids (4–6), and three other known compounds (7–9) were isolated from the roots of Xylopia vielana. The structures of new compounds were determined by extensive NMR, MS and IR spectroscopic analysis. Besides the absolute configurations were also elucidated by CD spectrum and X-ray analysis. All thesix alkaloids were first tested for their anti-inflammatory activities. [Display omitted]