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New tirucallane triterpenoids from Picrasma quassioides with their potential antiproliferative activities on hepatoma cells.

Abstract
Seven new tirucallane-type triterpenoids (1-7), kumuquassin A-G, along with 20 known analogues (8-27) were isolated from the stems of Picrasma quassioides. The structures and the absolute configurations of new compounds were elucidated by spectroscopic data, electronic circular dichroism (ECD) spectroscopic analyses and quantum ECD calculations. Notably, kumuquassin A (1) contains a rare Δ17, 20 double bond, kumuquassin B (2) is the first example of tirucallane triterpenoid possessing a 5/3 biheterocyclic ring system at the side chain. All the compounds were screened for the cytotoxicity against two human hepatoma cell lines, HepG2 and Hep3B, and several compounds exhibited promising activity. The most potential compound 3 was selected for cell cycle analysis, which showed that 3 could cause an accumulation of HepG2 cells at subG1 peak. Annexin V-FITC/PI staining further confirmed that compound 3 caused death of hepatoma cells through apoptosis induction.
AuthorsWen-Yu Zhao, Jing-Jie Chen, Chun-Xin Zou, Ying-Ying Zhang, Guo-Dong Yao, Xiao-Bo Wang, Xiao-Xiao Huang, Bin Lin, Shao-Jiang Song
JournalBioorganic chemistry (Bioorg Chem) Vol. 84 Pg. 309-318 (03 2019) ISSN: 1090-2120 [Electronic] United States
PMID30530072 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
CopyrightCopyright © 2018 Elsevier Inc. All rights reserved.
Chemical References
  • Antineoplastic Agents, Phytogenic
  • Triterpenes
  • tirucallane
Topics
  • Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
  • Carcinoma, Hepatocellular (metabolism, pathology)
  • Cell Cycle Checkpoints (drug effects)
  • Cell Line, Tumor
  • Cell Proliferation (drug effects)
  • Humans
  • Liver Neoplasms (metabolism, pathology)
  • Molecular Conformation
  • Picrasma (chemistry, metabolism)
  • Plant Stems (chemistry, metabolism)
  • Triterpenes (chemistry, isolation & purification, pharmacology)

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