4.7 Article

Discovery and photosynthesis of sinuaustones A and B, diterpenoids with a novel carbon scaffold isolated from soft coral Sinularia australiensis from Hainan

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ORGANIC CHEMISTRY FRONTIERS
卷 9, 期 21, 页码 5921-5928

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01265k

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  1. National Natural Science Foundation of China [81991521]
  2. SKLDR/SIMM Project [SIMM2013ZZ-06]

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Two novel diterpenoids with unprecedented carbon framework were isolated from South China Sea soft coral. These compounds exhibited inhibitory effects on inflammatory responses.
Two novel diterpenoids, sinuaustones A (1) and B (2), featuring an unprecedented tricyclo[9.3.1.0(3,15)]tetradecane carbon framework, along with a new spatane-type diterpenoid 3 and two related known compounds 4 and 5, were isolated from the South China Sea soft coral Sinularia australiensis. The structures of the new compounds were established by detailed spectroscopic, X-ray diffraction analysis and quantum chemical computation methods. Photosynthesis of 1 and 2 starting from co-isolated 5 was completed giving insight into the plausible biosynthetic pathway of 1 and 2, as well as their structural relationship with co-occurring 3-5. In the in vitro bioassay, compounds 1, 2, 3, and 5 exhibited inhibitory effects on lipopolysaccharide (LPS)-induced inflammatory responses in RAW264.7 cells with IC50 values of 20.9, 75.1, 9.1, and 30.4 mu M, respectively.

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