来自海绵 Pseudoceratina purpurea 的抗炎和细胞毒性含氮半月半萜类化合物。
Anti-inflammatory and cytotoxicity nitrogenous merosesquiterpenoids from the sponge Pseudoceratina purpurea.
发表日期:2024 Jul 10
作者:
Xiaoli Yu, Xiao Han, Yue Mi, Yongpeng Cui, Anran Fu, Kun Liu, Xiaobin Li, Xuli Tang, Guoqiang Li
来源:
PHYTOCHEMISTRY
摘要:
从南海采集的海绵 Pseudoceratina purpurea 中分离出 14 种未描述的含氮半倍半萜类化合物、紫嘌呤醇 A-D (1-4) 和嘌呤酮 A-J (5-14),以及三种已知的相关化合物 (15-17)。通过光谱数据、X射线衍射分析、电子圆二色性计算和化学衍生化的结合,明确地阐明了它们的结构和绝对构型。紫紫醇 A-D (1-4) 结合了含氮杂环,化合物 1 和 2 具有不寻常的苯并噻唑环,而 3 和 4 则具有苯并恶唑环。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氨基醌。此外,通过化学衍生化获得了二十种未报道的倍半萜氨基醌类似物。值得注意的是,所有化合物都具有不寻常的重排 4,9-friedodrimane 亚基。在生物测定中,紫紫醇 A 和 B 在斑马鱼中表现出较弱的抗炎作用,并且某些化合物表现出抗肿瘤细胞的活性,因此还讨论了初步的结构-细胞毒性关系。版权所有 © 2024。由 Elsevier Ltd 出版。
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.Copyright © 2024. Published by Elsevier Ltd.