School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing 210023, China; State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555, Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555, Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China; Marine Biomedical Research Institute, Guangdong Key Laboratory for Research and Development of Natural Drugs, Guangdong Medical University, Zhanjiang 524023, China.
Bioorg Med Chem. 2021 May 15;38:116139. doi: 10.1016/j.bmc.2021.116139. Epub 2021 Apr 2.
Six new cembrane-type diterpenoids, namely ximaoglaucumins A-F (1-6), along with fifteen known related ones (7-10 and 14-24), have been isolated from the soft coral Sarcophyton glaucum collected off the Ximao Island in the South China Sea. Their structures, including absolute stereochemistry, were elucidated by extensive spectroscopic analysis, quantum mechanical nuclear magnetic resonance (QM-NMR) methods, X-ray diffraction analysis, chemical methods, as well as comparison with the reported data in the literature. Further, detailed analysis of spectroscopic data of 7 not only clarified the confusions regarding 7, 11 (sarcophytolol) and 12/13 (sarcotrocheliol) in the literature, but also led to revise the structure of 11, which was mis-assigned due to careless/erroneous interpretation of the 2D NMR spectra, and to correct the structures of 12/13, which were both wrongly depicted. In in vitro bioassay, compounds 8 and 20 exhibited potent inhibitory effects on lipopolysaccharide (LPS)-induced inflammatory responses in BV-2 microglial cells.
从南海西沙群岛采集的软珊瑚 Sarcophyton glaucum 中分离得到了 6 个新的海鞘烷型二萜,即 ximaoglaucumins A-F(1-6),以及 15 个已知的相关化合物(7-10 和 14-24)。通过广泛的光谱分析、量子力学核磁共振(QM-NMR)方法、X 射线衍射分析、化学方法以及与文献中报道的数据进行比较,阐明了它们的结构,包括绝对立体化学。此外,对 7 的光谱数据的详细分析不仅澄清了文献中关于 7、11(sarcophytolol)和 12/13(sarcotrocheliol)的混淆,还修正了 11 的结构,由于对二维 NMR 谱图的解释粗心/错误,导致 11 的结构被错误指定,并修正了 12/13 的结构,它们的结构都被错误地描绘了。在体外生物测定中,化合物 8 和 20 对 LPS 诱导的 BV-2 小胶质细胞炎症反应表现出强烈的抑制作用。