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Download filePsiguadiols A–J, Rearranged Meroterpenoids as Potent PTP1B Inhibitors from Psidium guajava
journal contribution
posted on 2019-11-18, 14:49 authored by Ji-Qin Hou, Chun-Lin Fan, Xin Pei, Pei-Lin Zhang, Fan Deng, Wan-Qiang Jiang, Guo-Cai Wang, Xiao-Qi Zhang, Wen-Cai Ye, Hao WangPsiguadiols A–J (1–10),
new meroterpenoids with rearranged skeletons, were isolated from the
leaves of Psidium guajava. Compounds 1–3 represent the first examples of 6,8-diformyl-5,7-dihydroxy-4-phenylchromane-coupled
sesquiterpenoids with an unprecedented C-8-spiro-fused 6/6/9/4 tetracyclic
ring system. Compounds 4 and 5 represent
two unusual scaffolds featuring 1β,6β- and 3α,5α-epoxy
rings, respectively. The combination of spectroscopic data analyses,
comparison of experimental and calculated ECD data, and single-crystal
X-ray diffraction data of 1, 6, and 8 allowed for the assignment of the structures. A putative
biosynthetic pathway for 1–10 is
discussed. Compounds 1, 7, and 8 exhibited inhibitory activities against PTP1B with IC50 values of 4.7, 6.2, and 9.2 μM, respectively. In addition,
molecular docking was performed to investigate the mechanism of action.