Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2023-04-15 , DOI: 10.1016/j.bioorg.2023.106542
Zhenger Wu 1 , Heng Guo 1 , Qilin Wu 1 , Minghua Jiang 2 , Junjie Chen 1 , Bin Chen 3 , Hanxiang Li 4 , Lan Liu 2 , Senhua Chen 5
![]() |
Two new cyclopropane derivatives (1–2) and seven undescribed α-pyrone derivatives (3–9), along with one known congener (10) were obtained from the marine fungus Stagonospora sp. SYSU-MS7888, which was isolated from the South China Sea. Their planar structures were established through extensive spectroscopic analyses including 1D and 2D NMR and HR-ESIMS. The absolute configurations were identified on basis of the quantum chemical calculations of ECD and NMR, as well as the modified Mosher’s method. It's particularly noteworthy that the tetrasubstituted furopyrans, chenopodolans A-F, possessing phytotoxicity and zootoxicity, were structural misassignments. The structures of chenopodolans featuring with furopyran skeleton were revised as common trisubstituted α-pyrones by computational chemistry, NMR spectroscopic method, and empirical rule. Compounds 1, 2, 7, and 9 showed significant anti-inflammatory activity with IC50 values ranging from 3.6 to 22.8 μM, which is better than the positive control indomethacin (IC50 = 26.5 ± 1.13 μM). This discovery holds potential for the development of new anti-inflammatory agents.
中文翻译:

环丙烷的绝对构型和来自海洋衍生真菌 Stagonospora sp. 的 pyrones 的结构修正。SYSU-MS7888
从海洋真菌Stagonospora中获得了两种新的环丙烷衍生物 ( 1 – 2 ) 和七种未描述的α-吡喃酮衍生物 ( 3 – 9 ),以及一种已知的同类物 ( 10 )sp。SYSU-MS7888,从南海分离出来的。它们的平面结构是通过广泛的光谱分析建立的,包括一维和二维核磁共振和 HR-ESIMS。绝对构型是根据 ECD 和 NMR 的量子化学计算以及改进的 Mosher 方法确定的。特别值得注意的是,具有植物毒性和动物毒性的四取代呋喃吡喃藜藜 AF 是结构错误分配。通过计算化学、核磁共振光谱方法和经验法则,将具有呋喃吡喃骨架的藜多糖的结构修正为常见的三取代α-吡喃酮。化合物1、2、7和9显示出显着的抗炎活性,IC 50值范围为 3.6 至 22.8 μ M,优于阳性对照吲哚美辛 (IC 50 = 26.5 ± 1.13 μ M)。这一发现具有开发新抗炎药的潜力。