2. Academic Validation
  3. Bioactive polyoxygenated cembranoids from a novel Hainan chemotype of the soft coral Sinularia flexibilis

Bioactive polyoxygenated cembranoids from a novel Hainan chemotype of the soft coral Sinularia flexibilis

  • Bioorg Med Chem Lett. 2019 Jan 15;29(2):185-188. doi: 10.1016/j.bmcl.2018.12.004.
Qihao Wu 1,  Xu-Wen Li 2,  Heng Li 2,  Li-Gong Yao 2,  Wei Tang 2,  Ze-Hong Miao 2,  Hong Wang 3,  Yue-Wei Guo 4
Affiliations

Affiliations

  • 1 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; College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China.
  • 2 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.
  • 3 College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China. Electronic address: hongw@zjut.edu.cn.
  • 4 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; College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China. Electronic address: ywguo@simm.ac.cn.
PMID: 30528697 DOI: 10.1016/j.bmcl.2018.12.004
Abstract

Different chemotypes of Sinularia flexibilis exist in the Hainan island. Thus, a collection of this soft coral from a location different from the one of our previous study afforded three novel cembranoid esters featuring a n-butyl alcohol moiety, a structural element rare in natural products of both terrestrial and marine origin. The structures of the new compounds were elucidated by detailed spectroscopic analysis and by the comparison of their spectroscopic data with those reported in the literature. In addition, the absolute stereochemistry of the previously reported diepoxycembrene (9) was first time determined by the X-ray diffraction analysis. In bioassays, compounds 6-8 exhibited strong anti-inflammatory effect with IC50 values of 2.7, 4.7, and 4.2 μM, respectively, whereas compound 5 displayed cytotoxicity against several Cancer cells with IC50 values ranging from 8.9 to 27.4 μM. A preliminary structural-activity relationship (SAR) was also described.

Keywords

Absolute configuration; Anti-inflammatory effect; Cembrane; Sinularia flexibilis; South China Sea.

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