New acylphloroglucinol derivatives with diverse architectures from Hypericum henryi

Org Lett. 2014 May 2;16(9):2434-7. doi: 10.1021/ol500808p. Epub 2014 Apr 16.

Abstract

Hyphenrones A-F (1-6), six polycyclic polyprenylated acylphloroglucinol derivatives with four architectures including three unprecedented cores as exemplified by 1, 3, and 4, were isolated from Hypericum henryi. Compounds 3 and 4 possess two unique 5/8/5 and 6/6/5/8/5 fused ring systems, respectively. Their absolute configurations were defined by experimental and calculated ECD of 4 and X-ray diffractions of 5 and 6, coupled with their putative biosynthetic origins. Three compounds exhibited interesting AChE inhibitory activities.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Line, Tumor
  • Cholinesterase Inhibitors / chemistry*
  • Cholinesterase Inhibitors / isolation & purification
  • Cholinesterase Inhibitors / pharmacology
  • HL-60 Cells
  • Humans
  • Hypericum / chemistry*
  • Molecular Structure
  • Phloroglucinol / analogs & derivatives
  • Phloroglucinol / chemistry*
  • Phloroglucinol / isolation & purification
  • Phloroglucinol / pharmacology
  • Polycyclic Compounds / chemistry*
  • Polycyclic Compounds / isolation & purification
  • Polycyclic Compounds / pharmacology
  • X-Ray Diffraction

Substances

  • Antineoplastic Agents, Phytogenic
  • Cholinesterase Inhibitors
  • Polycyclic Compounds
  • Phloroglucinol