Dysifragilones A-C, Unusual Sesquiterpene Aminoquinones and Inhibitors of NO Production from the South China Sea Sponge Dysidea fragilis

• Published in: European journal of organic chemistry 2015-02, Vol.2015 (5), p.960-966
• Main Authors: Jiao, Wei-Hua, Xu, Ting-Ting, Zhao, Feng, Gao, Hao, Shi, Guo-Hua, Wang, Jie, Hong, Li-Li, Yu, Hao-Bing, Li, Yu-Shan, Yang, Fan, Lin, Hou-Wen
• Format: Article
• Language: English
• Subjects: Configuration determination; Inhibitors; Marine sponges; Natural products; Structure elucidation; Terpenoids
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201403487

Dysifragilones A–C (1–3), three unusual sesquiterpene aminoquinones based on a rearranged avarone skeleton, were isolated from the South China Sea sponge Dysidea fragilis. Their structures were elucidated by detailed spectroscopic and spectrometric analysis, and their absolute configurations were assigned from calculated electronic circular dichroism (ECD) spectra. The inhibitory activity of each compound on the production of nitric oxide (NO) stimulated by lipopolysaccharide (LPS) in mouse RAW 264.7 macrophages was evaluated. Of the three metabolites, dysifragilone A (1) showed the most potent inhibitory activity, with an IC50 value of 6.61 ± 0.54 μM. Dysifragilones A–C (1–3), three unusual sesquiterpene aminoquinones based on a rearranged avarone skeleton, were isolated from the marine sponge Dysidea fragilis. Their structures were determined by spectroscopy and from calculated ECD spectra. Dysifragilone A (1) showed potent inhibitory activity on NO production stimulated by LPS in RAW 264.7 macrophages, with an IC50 value of 6.61 ± 0.54 μM.