Affordable Access

deepdyve-link
Publisher Website

Structures, chemotaxonomic significance, cytotoxic and Na(+),K(+)-ATPase inhibitory activities of new cardenolides from Asclepias curassavica.

Authors
  • Zhang, Rong-Rong1
  • Tian, Hai-Yan
  • Tan, Ya-Fang
  • Chung, Tse-Yu
  • Sun, Xiao-Hui
  • Xia, Xue
  • Ye, Wen-Cai
  • Middleton, David A
  • Fedosova, Natalya
  • Esmann, Mikael
  • Tzen, Jason T C
  • Jiang, Ren-Wang
  • 1 Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, P. R. China. [email protected] , (China)
Type
Published Article
Journal
Organic & Biomolecular Chemistry
Publisher
The Royal Society of Chemistry
Publication Date
Nov 28, 2014
Volume
12
Issue
44
Pages
8919–8929
Identifiers
DOI: 10.1039/c4ob01545b
PMID: 25270760
Source
Medline
License
Unknown

Abstract

Five new cardenolide lactates (1–5) and one new dioxane double linked cardenolide glycoside (17) along with 15 known compounds (6–16 and 18–21) were isolated from the ornamental milkweed Asclepias curassavica. Their structures were elucidated by extensive spectroscopic methods (IR, UV, MS, 1D- and 2D-NMR). The molecular structures and absolute configurations of 1–3 and 17 were further confirmed by single-crystal X-ray diffraction analysis. Simultaneous isolation of dioxane double linked cardenolide glycosides (17–21) and cardenolide lactates (1–5) provided unique chemotaxonomic markers for this genus. Compounds 1–21 were evaluated for the inhibitory activities against DU145 prostate cancer cells. The dioxane double linked cardenolide glycosides showed the most potent cytotoxic effect followed by normal cardenolides and cardenolide lactates, while the C21 steroids were non-cytotoxic. Enzymatic assay established a correlation between the cytotoxic effects in DU145 cancer cells and the Ki for the inhibition of Na(+),K(+)-ATPase. Molecular docking analysis revealed relatively strong H-bond interactions between the bottom of the binding cavity and compounds 18 or 20, and explained why the dioxane double linked cardenolide glycosides possessed higher inhibitory potency on Na(+),K(+)-ATPase than the cardenolide lactate.

Report this publication

Statistics

Seen <100 times