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Hyperforones A–C, benzoyl-migrated [5.3.1]-type polycyclic polyprenylated acylphloroglucinols from Hypericum forrestii

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Abstract

Three unprecedented benzoyl-migrated polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperforones A–C (1–3), were isolated from Hypericum forrestii, together with a new benzoyl-substituted analogue (4) of hyperforin. Compounds 1–3 are the first examples of naturally occurring benzoyl-PPAPs with a unique C-1 H-substituted bicyclo[5.3.1]hendecane scaffold. Their structures and absolute configurations were established by HRESIMS, NMR spectroscopy data, electronic circular dichroism (ECD) exciton chirality method, ECD calculations, and gauge-independent atomic orbital (GIAO) NMR calculations with DP4+ analyses. A plausible biosynthetic formation of the benzoyl-migrated C-1 H-substituted bicyclo[5.3.1]hendecane skeleton in 1–3 via a sterically favored hemiketalization/Retro-Claisen cascade was proposed. Bzhyperforin (4) showed significant cytotoxicity against MDA-MB-231 cells with an IC50 value of 6.88 ± 1.37 μM.

Graphical abstract: Hyperforones A–C, benzoyl-migrated [5.3.1]-type polycyclic polyprenylated acylphloroglucinols from Hypericum forrestii

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Article information


Submitted
31 Jan 2020
Accepted
02 Mar 2020
First published
03 Mar 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Hyperforones A–C, benzoyl-migrated [5.3.1]-type polycyclic polyprenylated acylphloroglucinols from Hypericum forrestii

W. Lu, W. Xu, Y. Zhang, Y. Li, X. Zhou, Q. Li, H. Zhang, J. Luo and L. Kong, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00152J

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