Hyperuralones A and B, New Acylphloroglucinol Derivatives with Intricately Caged Cores from Hypericum uralum.

Hyperuralones A and B, New Acylphloroglucinol Derivatives with Intricately Caged Cores from Hypericum uralum.

Org Lett. 2014 Sep 5;

Authors: Zhang JJ, Yang J, Liao Y, Yang XW, Ma JZ, Xiao QL, Yang LX, Xu G

Abstract

Hyperuralone A (1), a polycyclic polyprenylated acylphloroglucinol possessing an unprecedented tetracyclo-[5.3.1.1(4,9).0(4,11)]-dodecane core, was characterized from Hypericum uralum together with hyperuralone B (2), a congener with another complex caged skeleton. Their structures were determined by extensive spectroscopic analysis and ECD calculations. A plausible biosynthetic pathway of their intriguing architectures via intramolecular Diels-Alder reactions was also proposed. Compound 1 exhibited obviously cytotoxic activities against five human cancer cell lines in vitro (IC50 4.6-14.4 μM).

PMID: 25192496 [PubMed - as supplied by publisher]

Published Date: 
Saturday, September 6, 2014 - 11:28
Journal: 
Org Lett