vibralactone

Vibralactones are a group of related terpenoid chemical compounds, the first of which were isolated from the Basidiomycete Boreostereum vibrans in 2006.{{cite journal | title = Vibralactone: A Lipase Inhibitor with an Unusual Fused β-Lactone Produced by Cultures of the Basidiomycete Boreostereum vibrans | author = Dong-Ze Liu, Fei Wang, Tou-Gen Liao, Jian-Guo Tang, Wolfgang Steglich, Hua-Jie Zhu, and Ji-Kai Liu | journal = Org. Lett. | date = 2006 | volume = 8 | issue = 25 | pages = 5749–5752 | doi = 10.1021/ol062307u | pmid = 17134263 }} Additional vibralactones have also been isolated from the fungus Stereum hirsutum.{{cite journal | title = Structurally diverse vibralactones produced by the fungus Stereum hirsutum | author = Yu Liang, Qin Li, Mengsha Wei, Chunmei Chen, Weiguang Sun, Lianghu Gu, Hucheng Zhu, Yonghui Zhang | journal = Bioorganic Chemistry | volume = 99 | date = 2020 | pages = 103760 | doi = 10.1016/j.bioorg.2020.103760 | pmid = 32251946 | s2cid = 215408310 }}

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.{{cite journal | title = A Short Diastereoselective Total Synthesis of (±)-Vibralactone | author = Alexander J. Leeder†, Robert J. Heap†, Lynda J. Brown†, Xavier Franck, and Richard C. D. Brown | journal = Org. Lett. | volume = 18 | issue = 23 | pages = 5971–5973 | date = 2016 | doi = 10.1021/acs.orglett.6b03007 | pmid = 27797210 | s2cid = 26599940 | doi-access = free }}

Several laboratory syntheses of vibralactone A have been developed.{{cite journal | title = A Concise Total Synthesis of (±)-Vibralactone | author = Sepand K. Nistanaki, Luke A. Boralsky, Roy D. Pan, Hosea M. Nelson | journal = Angewandte Chemie | volume = 58 | issue = 6 | date = 2019 | pages = 1724–1726 | doi = 10.1002/anie.201812711 | pmid = 30548983 | pmc = 6351154 }}

Chemical structures

{{image array

| perrow = 3

| width = 200

| height = 150

| image1 = Vibralactone.svg | caption1 = Vibralactone A

| image2 = Vibralactone B.svg | caption2 = Vibralactone B

| image3 = Vibralactone C.svg | caption3 = Vibralactone C

| image4 = Vibralactone D.svg | caption4 = Vibralactone D

| image5 = Vibralactone E.svg | caption5 = Vibralactone E

| image6 = Vibralactone F.svg | caption6 = Vibralactone F

}}

References