Polycyclic polyprenylated acylphloroglucinols (PPAPs) are a class of hybrid natural products sharing the mevalonate/methylerythritol phosphate and polyketide biosynthetic pathways and showing considerable structural and bioactive diversity. In a systematic phytochemical investigation of Hypericum henryi, 40 PPAP-type derivatives, including the new compounds hyphenrones G-Q, were obtained. These compounds represent 12 different structural types, including four unusual skeletons exemplified by 5, 8, 10, and 17. The 12 different core structures found are explicable in terms of their biosynthetic origin. The structure of a known PPAP, perforatumone, was revised to hyphenrone A (5) by NMR spectroscopic and biomimetic synthesis methods. Several compounds exhibited inhibitory activities against acetylcholinesterase and human tumor cell lines. This study deals with the structural diversity, function, and biogenesis of natural PPAPs.
National Natural Sciences Foundation of China 
; Young Academic Leader Raising Foundation of Yunnan Province [2009CI073]
; National Science and Technology Support Program of China [2013BAI11B02]
; Chinese Academy of Sciences
; Program of "One Hundred Talented People"
1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China 2.Univ Mississippi, Sch Pharm, Div Pharmacognosy, Dept Biomol Sci, University, MS 38677 USA 3.Univ Mississippi, Sch Pharm, Natl Ctr Nat Prod Res, Res Inst Pharmaceut Sci, University, MS 38677 USA 4.Univ Chinese Acad Sci, Beijing 100049, Peoples R China