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Hyphenrones R–X (1–7), seven new polyprenylated acylphloroglucinols derivatives, were isolated from the fruits of Hypericum henryi, together with eight know analogues. Compounds 1 and 2 were elucidated to possess complex caged skeleton, while compounds 3–6 shared a common 3,9-epoxy moiety deriving from the normal polyprenylated acylphloroglucinols with a bicyclo[3.3.1]nonane-2,4,9-trione core. The new structures were elucidated on the basis of the interpretation of nuclear magnetic resonance (NMR) data, circular dichroism (CD) comparison, and single-crystal X-ray diffraction. In the bioassay, several compounds exhibited inhibitory activities against human tumor cell lines in vitro.

Hypercohin K (1), the first polycyclic polyprenylated acylphloroglucinol possessing a unique spiro-fused cyclopropane ring, together with hyphenrone L (2) representing the most complex congeners featured with a hexacyclic core, was isolated from Hypericum cohaerens. The structure of 1 was elucidated by extensive MS and NMR spectroscopic data. The absolute configuration was defined by comparison of the experimental and calculated ECD. Compound 1 was evaluated for the inhibitory activities against acetylcholinesterase and four human tumor cell lines. (C) 2015 Elsevier Ltd. All rights reserved.

Hypercohin K (1), the first polycyclic polyprenylated acylphloroglucinol possessing a unique spiro-fused cyclopropane ring, together with hyphenrone L (2) representing the most complex congeners featured with a hexacyclic core, was isolated from Hypericum cohaerens. The structure of 1 was elucidated by extensive MS and NMR spectroscopic data. The absolute configuration was defined by comparison of the experimental and calculated ECD. Compound 1 was evaluated for the inhibitory activities against acetylcholinesterase and four human tumor cell lines. (C) 2015 Elsevier Ltd. All rights reserved.