Isolation and Structural Characterization of Echinocystic Acid Triterpenoid Saponins from the Australian Medicinal and Food Plant Acacia ligulata

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

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

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
Pages (from-to)2692-2698
Number of pages7
JournalJournal of Natural Products
Volume80
Issue number10
Early online date4 Oct 2017
DOIs
Publication statusPublished - 27 Oct 2017

Keywords

  • Carbohydrates
  • Cells
  • Chemical structure
  • Hydrocarbons
  • Toxicity

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