Ximaoglaucumins A − F, new cembranoids with anti-inflammatory activities from the South China Sea soft coral Sarcophyton glaucum

Abstract

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.