Marine Biodiscovery Laboratory, School of Chemistry and Ryan Institute, National University of Ireland Galway, University Road, Galway H91 TK33, Ireland.
Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Parque Tecnológico de Ciencias de la Salud, Avenida del Conocimiento 34, Armilla, Granada E-18016, Spain.
Org Biomol Chem. 2022 Feb 2;20(5):1031-1040. doi: 10.1039/d1ob02297k.
An abundant sponge of the order Bubarida was selected for further chemical investigation following biological and chemical screening of sponges collected from Futuna Islands in the Indo-Pacific. Ten new nitrogenous bisabolene derivatives were isolated and identified: the monomeric theonellin formamide analogues named bubaridins A-F (1-6) with unusual oxidised linear chains, and the first isocyanide/formamide dimeric and cyclised bisabolenes 7-9. The structure elucidation of these nitrogenous bisabolenes involved HRESIMS, NMR, and ECD analyses, and the chiral compounds were found to be racemates. A biosynthetic hypothesis for the production of these metabolites is proposed and some chemotaxonomic considerations are discussed. Furthermore, the antimicrobial and antitumoral activity were evalutated and the -dimer theonellin isocyanide (7) was shown to exhibit potent and selective antifungal activity.
从印度洋-太平洋富图纳群岛采集的海绵经过生物和化学筛选后，选择了一种丰富的泡海绵目海绵进行进一步的化学研究。从海绵中分离并鉴定了 10 种新型含氮双甲烯化合物：单体桐螺素甲酰胺类似物命名为 bubaridins A-F（1-6），具有不寻常的氧化线性链，以及第一个异氰酸酯/甲酰胺二聚体和环状双甲烯 7-9。这些含氮双甲烯的结构阐明涉及高分辨率电喷雾质谱（HRESIMS）、NMR 和 ECD 分析，并且发现手性化合物为外消旋混合物。提出了这些代谢产物产生的生物合成假设，并讨论了一些化学生态分类学的考虑。此外，还评估了抗菌和抗肿瘤活性，并且 -二聚桐螺素异氰酸酯（7）表现出很强的选择性抗真菌活性。
