Isolation and structural characterization of echinocystic acid triterpenoid saponins from the Australian medicinal and food plant Acacia ligulata

Research output: Contribution to journalJournal articleResearchpeer-review

  • Diana Jæger Knudsen
  • Chi P. Ndi
  • Christoph Crocoll
  • Bradley S. Simpson
  • Khakimov, Bekzod
  • Ruth Marian Guzman-Genuino
  • John D. Hayball
  • Xiaohui Xing
  • Vincent Bulone
  • Philip Weinstein
  • Møller, Birger Lindberg
  • Susan J. Semple

The Australian plant Acacia ligulata has a number of traditional food and medicinal uses by Australian Aboriginal people, although no bioactive compounds have previously been isolated from this species. Bioassay-guided fractionation of an ethanolic extract of the mature pods of A. ligulata led to the isolation of the two new echinocystic acid triterpenoid saponins, ligulatasides A (1) and B (2), which differ in the fine structure of their glycan substituents. Their structures were elucidated on the basis of 1D and 2D NMR, GC-MS, LC-MS/MS, and saccharide linkage analysis. These are the first isolated compounds from A. ligulata and the first fully elucidated structures of triterpenoid saponins from Acacia sensu stricto having echinocystic acid reported as the aglycone. Compounds 1 and 2 were evaluated for cytotoxic activity against a human melanoma cancer cell line (SK-MEL28) and a diploid fibroblast cell line (HFF), but showed only weak activity.

Original languageEnglish
JournalJournal of Natural Products
Volume80
Issue number10
Pages (from-to)2692-2698
Number of pages7
ISSN0163-3864
DOIs
Publication statusPublished - 2017

    Research areas

  • Journal Article

ID: 184420941