Polycyclic Polyprenylated Acylphloroglucinol Congeners Possessing Diverse Structures from Hypericum henryi

  • J Nat Prod. 2015 Apr 24;78(4):885-95. doi: 10.1021/acs.jnatprod.5b00057.
Xing-Wei Yang  1  2 ,  Ming-Ming Li  1 ,  Xia Liu  1  2 ,  Daneel Ferreira ,  Yuanqing Ding ,  Jing-Jing Zhang  1  2 ,  Yang Liao  1  2 ,  Hong-Bo Qin  1 ,  Gang Xu  1
Affiliations
  • 1. †State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China.
  • 2. ⊥University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
PMID: 25871261 DOI: 10.1021/acs.jnatprod.5b00057
Abstract

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.