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Dioxasampsones A and B, Two Polycyclic Polyprenylated Acylphloroglucinols with Unusual Epoxy-Ring-Fused Skeleton from Hypericum sampsonii

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posted on 2014-12-19, 00:00 authored by Wen-Jing Tian, Yu-Qin Qiu, Xiao-Jun Yao, Hai-Feng Chen, Yi Dai, Xiao-Kun Zhang, Xin-Sheng Yao
Dioxasampsones A and B (1 and 2), two new polycyclic polyprenylated acylphloroglucinols with an unusual epoxy-ring-fused skeleton by new ways of cyclization, along with a new nor-PPAPs hypersampson R (3) with the loss of C-31–33 in isopentenyl, were isolated from the aerial parts of Hypericum sampsonii. 1 possessed an unexpected hexacyclic skeleton with a rare 2,7-dioxabicyclo[2.2.1]­heptane moiety, and 2 featured a unique tetrahydrofuro­[3,4-b]­furan-fused tricycle­[,7]­undecane skeleton. The gross structures of the new compounds were determined by extensive NMR spectroscopic methods. Their absolute configurations were deduced by single-crystal X-ray diffraction and ECD calculations.