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Tricyclic Polyprenylated Acylphloroglucinols from St John’s Wort, Hypericum perforatum

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posted on 26.04.2017, 17:03 authored by Yi Guo, Na Zhang, Chunmei Chen, Jinfeng Huang, Xiao-Nian Li, Junjun Liu, Hucheng Zhu, Qingyi Tong, Jinwen Zhang, Zengwei Luo, Yongbo Xue, Yonghui Zhang
The new polyprenylated acylphloroglucinol derivatives 115 and the known furohyperforin (16) were isolated from the stems and leaves of Hypericum perforatum. Their structures were determined by analyses of NMR and HRESIMS data. Their absolute configurations were elucidated by a combination of electronic circular dichroism (ECD) and Rh2(OCOCF3)4-induced ECD, as well as X-ray diffraction crystallography. The new hyperforatin F (9) contains a unique acetyl functionality at C-1 of the bicyclo[3.3.1]­nonane core. Hyperforatins G (10) and H (11) are similarly the first examples of naturally occurring [3.3.1]-type polycyclic prenylated acylphloroglucinols possessing a carbonyl functionality at C-32. The compounds were tested for their acetylcholinesterase (AChE) inhibitory activities and cytotoxic activities against a panel of human tumor cell lines. Compounds 3, 5, 6, 8, and 9 exerted moderate inhibitory activities (IC50 3.98–9.13 μM) against AChE.