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

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

doi:10.1021/acs.jnatprod.7b00437

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

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

4 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 language	English
Journal	Journal of Natural Products
Volume	80
Issue number	10
Pages (from-to)	2692-2698
Number of pages	7
ISSN	0163-3864
DOIs	https://doi.org/10.1021/acs.jnatprod.7b00437
Publication status	Published - 27 Oct 2017

Keywords

Journal Article

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/acs.jnatprod.7b00437

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Knudsen, D. J., Ndi, C. P., Crocoll, C., Simpson, B. S., Khakimov, B., Guzman-Genuino, R. M., Hayball, J. D., Xing, X., Bulone, V., Weinstein, P., Møller, B. L., & Semple, S. J. (2017). Isolation and structural characterization of echinocystic acid triterpenoid saponins from the Australian medicinal and food plant Acacia ligulata. Journal of Natural Products, 80(10), 2692-2698. https://doi.org/10.1021/acs.jnatprod.7b00437

Isolation and structural characterization of echinocystic acid triterpenoid saponins from the Australian medicinal and food plant Acacia ligulata. / Knudsen, Diana Jæger; Ndi, Chi P.; Crocoll, Christoph et al.
In: Journal of Natural Products, Vol. 80, No. 10, 27.10.2017, p. 2692-2698.

Research output: Contribution to journal › Journal article › Research › peer-review

Knudsen, DJ, Ndi, CP, Crocoll, C, Simpson, BS, Khakimov, B, Guzman-Genuino, RM, Hayball, JD, Xing, X, Bulone, V, Weinstein, P, Møller, BL & Semple, SJ 2017, 'Isolation and structural characterization of echinocystic acid triterpenoid saponins from the Australian medicinal and food plant Acacia ligulata', Journal of Natural Products, vol. 80, no. 10, pp. 2692-2698. https://doi.org/10.1021/acs.jnatprod.7b00437

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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.",

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AU - Knudsen, Diana Jæger

AU - Ndi, Chi P.

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AU - Simpson, Bradley S.

AU - Khakimov, Bekzod

AU - Guzman-Genuino, Ruth Marian

AU - Hayball, John D.

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AB - 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.

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

Abstract

Keywords

UN SDGs

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