1. Isolation and Structural Characterization of Echinocystic Acid Triterpenoid Saponins from the Australian Medicinal and Food Plant Acacia ligulata
- Author
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Chi P. Ndi, Bekzod Khakimov, Susan J. Semple, Xiaohui Xing, Bradley S Simpson, John D. Hayball, Vincent Bulone, Christoph Crocoll, Ruth Marian Guzman-Genuino, Birger Lindberg Møller, Diana Jæger, Philip Weinstein, Jaeger, Diana, Ndi, Chi P, Crocoll, Christoph, Simpson, Bradley S, Khakimov, Bekzod, Guzman-Genuino, Ruth Marian, Hayball, John D, Xing, Xiaohui, Bulone, Vincent, Weinstein, Philip, Moller, Birger L, and Semple, Susan J
- Subjects
0301 basic medicine ,Food plant ,Glycan ,Pharmaceutical Science ,Acacia ,Biology ,01 natural sciences ,Gas Chromatography-Mass Spectrometry ,Analytical Chemistry ,03 medical and health sciences ,chemistry.chemical_compound ,Triterpenoid ,Acacia ligulata ,Drug Discovery ,Botany ,Humans ,Oleanolic Acid ,Nuclear Magnetic Resonance, Biomolecular ,Pharmacology ,Molecular Structure ,010405 organic chemistry ,Organic Chemistry ,Australia ,Fibroblasts ,Saponins ,biology.organism_classification ,Antineoplastic Agents, Phytogenic ,Triterpenes ,0104 chemical sciences ,030104 developmental biology ,Aglycone ,Complementary and alternative medicine ,chemistry ,biology.protein ,Molecular Medicine ,Human melanoma ,Drug Screening Assays, Antitumor ,Echinocystic acid - 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. Refereed/Peer-reviewed
- Published
- 2017
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