Vibralactone Explained

Vibralactones are a group of related terpenoid chemical compounds, the first of which were isolated from the Basidiomycete Boreostereum vibrans in 2006.^[1] Additional vibralactones have also been isolated from the fungus Stereum hirsutum.^[2]

Vibralactone A has attracted research interest because it is an inhibitor of pancreatic lipase (IC₅₀ 0.4 μg/mL) with in vitro activity comparable to that of the obesity drug orlistat.^{[1] [3]}

Several laboratory syntheses of vibralactone A have been developed.^{[3] [4]}

Notes and References

1. Vibralactone: A Lipase Inhibitor with an Unusual Fused β-Lactone Produced by Cultures of the Basidiomycete Boreostereum vibrans . Dong-Ze Liu, Fei Wang, Tou-Gen Liao, Jian-Guo Tang, Wolfgang Steglich, Hua-Jie Zhu, and Ji-Kai Liu . Org. Lett. . 2006 . 8 . 25 . 5749–5752 . 10.1021/ol062307u . 17134263 .
2. Structurally diverse vibralactones produced by the fungus Stereum hirsutum . Yu Liang, Qin Li, Mengsha Wei, Chunmei Chen, Weiguang Sun, Lianghu Gu, Hucheng Zhu, Yonghui Zhang . Bioorganic Chemistry . 99 . 2020 . 103760 . 10.1016/j.bioorg.2020.103760 . 32251946 . 215408310 .
3. A Short Diastereoselective Total Synthesis of (±)-Vibralactone . Alexander J. Leeder†, Robert J. Heap†, Lynda J. Brown†, Xavier Franck, and Richard C. D. Brown . Org. Lett. . 18 . 23 . 5971–5973 . 2016 . 10.1021/acs.orglett.6b03007 . 27797210 . 26599940 . free .
4. A Concise Total Synthesis of (±)-Vibralactone . Sepand K. Nistanaki, Luke A. Boralsky, Roy D. Pan, Hosea M. Nelson . Angewandte Chemie . 58 . 6 . 2019 . 1724–1726 . 10.1002/anie.201812711 . 30548983 . 6351154 .