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Spectroscopic Characterization and Cytotoxicity Assessment towards Human Colon Cancer Cell Lines of Acylated Cycloartane Glycosides from Astragalus boeticus L.

1
Dipartimento di Scienze e Tecnologie Ambientali Biologiche e Farmaceutiche (DiSTABiF), Università degli Studi della Campania “Luigi Vanvitelli”, via Vivaldi 43, I-81100 Caserta, Italy
2
Department of Biochemistry, Max Planck Institute for Chemical Ecology-Beutenberg Campus, Hans-Knöll-Straße, 8 D-07745 Jena, Germany
3
Dipartimento di Medicina di Precisione, Università degli Studi della Campania “Luigi Vanvitelli” - Via Pansini, 5, 80131 Napoli, Italy
4
Dipartimento di Biotecnologia Marina, Stazione Zoologica Anton Dohrn, Villa Comunale, 80121 Naples, Italy
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(9), 1725; https://doi.org/10.3390/molecules24091725
Received: 10 April 2019 / Revised: 29 April 2019 / Accepted: 1 May 2019 / Published: 3 May 2019
(This article belongs to the Special Issue Natural Products and Drug Discovery)
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Abstract

In several European countries, especially in Sweden, the seeds of the species Astragalus boeticus L. were widely used as coffee substitutes during the 19th century. Nonetheless, data regarding the phytochemistry and the pharmacological properties of this species are currently extremely limited. Conversely, other species belonging to the Astragalus genus have already been extensively investigated, as they were used for millennia for treating various diseases, including cancer. The current work was addressed to characterize cycloartane glycosides from A. boeticus, and to evaluate their cytotoxicity towards human colorectal cancer (CRC) cell lines. The isolation of the metabolites was performed by using different chromatographic techniques, while their chemical structures were elucidated by nuclear magnetic resonance (NMR) (1D and 2D techniques) and electrospray-ionization quadrupole time-of-flight (ESI-QTOF) mass spectrometry. The cytotoxic assessment was performed in vitro by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays in Caco-2, HT-29 and HCT-116 CRC cells. As a result, the targeted phytochemical study of A. boeticus enabled the isolation of three new cycloartane glycosides, 6-O-acetyl-3-O-(4-O-malonyl)-β-d-xylopyranosylcycloastragenol (1), 3-O-(4-O-malonyl)-β-d-xylopyranosylcycloastragenol (2), 6-O-acetyl-25-O-β-d-glucopyranosyl-3-O-β-d-xylopyranosylcycloastragenol (3) along with two known compounds, 6-O-acetyl-3-O-β-d-xylopyranosylcycloastragenol (4) and 3-O-β-d-xylopyranosylcycloastragenol (5). Importantly, this work demonstrated that the acetylated cycloartane glycosides 1 and 4 might preferentially inhibit cell growth in the CRC cell model resistant to epidermal growth factor receptor (EGFR) inhibitors. View Full-Text
Keywords: Astragalus boeticus L.; spectroscopic analysis; cytotoxic activity; human colon cancer cell lines; acetylated astragalosides; Fabaceae Astragalus boeticus L.; spectroscopic analysis; cytotoxic activity; human colon cancer cell lines; acetylated astragalosides; Fabaceae
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Graziani, V.; Esposito, A.; Scognamiglio, M.; Chambery, A.; Russo, R.; Ciardiello, F.; Troiani, T.; Potenza, N.; Fiorentino, A.; D’Abrosca, B. Spectroscopic Characterization and Cytotoxicity Assessment towards Human Colon Cancer Cell Lines of Acylated Cycloartane Glycosides from Astragalus boeticus L.. Molecules 2019, 24, 1725.

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