Abstract:
Fourteen undescribed nitrogenous merosesquiterpenoids, purpurols A-D (1-4) and puraminones A-J (5-14), along with three known related compounds (15-17) were isolated from the sponge Pseudoceratina purpurea collected in the South China Sea. Their structures and absolute configurations were unambiguously elucidated by a combination of spectroscopic data, X-ray diffraction analysis, electronic circular dichroism calculations, and chemical derivatization. Purpurols A-D (1-4) incorporated nitrogenous heterocycles, compounds 1 and 2 feature an unusual benzothiazole ring, while 3 and 4 feature benzoxazole ring. Puraminones A-J (5-14) represent sesquiterpenoid aminoquinones with different amine and amino acid side chains at C-20. Additionally, twenty unreported sesquiterpenoid aminoquinone analogues were obtained through chemical derivatization. It is worth noting that all compounds are featured with unusual rearranged 4,9-friedodrimane subunit. In the bioassays, purpurols A and B showed weak anti-inflammation in zebrafish, as well as some compounds showed activities against tumor cells, therefore, preliminary structure-cytotoxicity relationships are also discussed.
摘要:
十四种未描述的含氮半萜,purpurolsA-D(1-4)和puraminoneA-J(5-14),从南中国海收集的海绵状紫癜中分离出三种已知的相关化合物(15-17)。通过光谱数据的组合明确阐明了它们的结构和绝对构型,X射线衍射分析,电子圆二色性计算,和化学衍生。PurpurolsA-D(1-4)掺入含氮杂环,化合物1和2具有不寻常的苯并噻唑环,而3和4以苯并恶唑环为特征。嘌呤酮A-J(5-14)代表在C-20处具有不同胺和氨基酸侧链的倍半萜类氨基醌。此外,通过化学衍生获得了20种未报道的倍半萜类氨基醌类似物。值得注意的是,所有化合物都具有异常重排的4,9-friedodrimane亚基。在生物测定中,斑马鱼A和B的抗炎能力较弱,以及一些化合物显示出对抗肿瘤细胞的活性,因此,还讨论了初步的结构-细胞毒性关系。