Catechin-Bound Ceanothane-Type Triterpenoid Derivatives from the Roots of Zizyphus jujuba

  • J Nat Prod. 2017 Apr 28;80(4):1048-1054. doi: 10.1021/acs.jnatprod.6b01103.
Kyo Bin Kang  1 ,  Hyun Woo Kim  1 ,  Jung Wha Kim  1 ,  Won Keun Oh  1 ,  Jinwoong Kim  1 ,  Sang Hyun Sung  1
Affiliations
  • 1. College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University , Seoul 08826, Republic of Korea.
PMID: 28257196 DOI: 10.1021/acs.jnatprod.6b01103
Abstract

Three unprecedented ceanothane-type triterpenoids, ent-epicatechinoceanothic acid A (1), ent-epicatechinoceanothic acid B (2), and epicatechino-3-deoxyceanothetric acid A (3), containing C-C bond linkages with catechin moieties, were isolated from the roots of Zizyphus jujuba. Their chemical structures, including absolute configurations, were established by spectroscopic analysis and calculation of their ECD spectra. A possible biogenetic pathway for C-C bond formation between the catechin and the triterpenoid moieties is presented. Compound 1 was evaluated for its antiproliferative activity on HSC-T6 hepatic stellate cells.