Vibralactone

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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]

Chemical structures

Vibralactone.svg
Vibralactone A
Vibralactone B.svg
Vibralactone B
Vibralactone C.svg
Vibralactone C
Vibralactone D.svg
Vibralactone D
Vibralactone E.svg
Vibralactone E
Vibralactone F.svg
Vibralactone F

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References

  1. 1 2 Dong-Ze Liu, Fei Wang, Tou-Gen Liao, Jian-Guo Tang, Wolfgang Steglich, Hua-Jie Zhu, and Ji-Kai Liu (2006). "Vibralactone: A Lipase Inhibitor with an Unusual Fused β-Lactone Produced by Cultures of the Basidiomycete Boreostereum vibrans". Org. Lett. 8 (25): 5749–5752. doi:10.1021/ol062307u. PMID   17134263.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. Yu Liang, Qin Li, Mengsha Wei, Chunmei Chen, Weiguang Sun, Lianghu Gu, Hucheng Zhu, Yonghui Zhang (2020). "Structurally diverse vibralactones produced by the fungus Stereum hirsutum". Bioorganic Chemistry. 99: 103760. doi:10.1016/j.bioorg.2020.103760. PMID   32251946. S2CID   215408310.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. 1 2 Alexander J. Leeder†, Robert J. Heap†, Lynda J. Brown†, Xavier Franck, and Richard C. D. Brown (2016). "A Short Diastereoselective Total Synthesis of (±)-Vibralactone". Org. Lett. 18 (23): 5971–5973. doi:10.1021/acs.orglett.6b03007. PMID   27797210. S2CID   26599940.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. Sepand K. Nistanaki, Luke A. Boralsky, Roy D. Pan, Hosea M. Nelson (2019). "A Concise Total Synthesis of (±)-Vibralactone". Angewandte Chemie. 58 (6): 1724–1726. doi:10.1002/anie.201812711. PMC   6351154 . PMID   30548983.{{cite journal}}: CS1 maint: multiple names: authors list (link)