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Molecules 2018, 23(5), 1093; https://doi.org/10.3390/molecules23051093

Synthesis of New Glycosylated Flavonoids with Inhibitory Activity on Cell Growth

1
Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
2
Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), University of Porto, Terminal de Cruzeiros do Porto de Leixões, Avenida General Norton de Matos, S/N 4450-208 Matosinhos, Portugal
3
CESPU, Institute of Research and Advanced Training in Health Sciences and Technologies (IINFACTS), Rua Central de Gandra, 1317, 4585-116 Gandra, Portugal
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editors: Tsukasa Iwashina and Thomas J. Schmidt
Received: 3 April 2018 / Revised: 2 May 2018 / Accepted: 2 May 2018 / Published: 5 May 2018
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Abstract

Natural flavonoids and xanthone glycosides display several biological activities, with the glycoside moiety playing an important role in the mechanism of action of these metabolites. Herein, to give further insights into the inhibitory activity on cell growth of these classes of compounds, the synthesis of four flavonoids (5, 6, 9, and 10) and one xanthone (7) containing one or more acetoglycoside moieties was carried out. Acetyl groups were introduced using acetic anhydride and microwave irradiation. The introduction of one or two acetoglycoside moieties in the framework of 3,7-dihydroxyflavone (4) was performed using two synthetic methods: the Michael reaction and the Koenigs-Knorr reaction. The in vitro cell growth inhibitory activity of compounds 5, 6, 7, 9, and 10 was investigated in six human tumor cell lines: A375-C5 (malignant melanoma IL-1 insensitive), MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), U251 (glioblastoma astrocytoma), U373 (glioblastoma astrocytoma), and U87MG (glioblastoma astrocytoma). The new flavonoid 3-hydroxy-7-(2,3,4,6-tetra-O-acetyl-β-glucopyranosyl) flavone (10) was the most potent compound in all tumor cell lines tested, with GI50 values < 8 μM and a notable degree of selectivity for cancer cells. View Full-Text
Keywords: flavonoids; xanthones; growth inhibitory activity; acetylation; glycosylation flavonoids; xanthones; growth inhibitory activity; acetylation; glycosylation
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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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Neves, A.R.; Correia-da-Silva, M.; Silva, P.M.A.; Ribeiro, D.; Sousa, E.; Bousbaa, H.; Pinto, M. Synthesis of New Glycosylated Flavonoids with Inhibitory Activity on Cell Growth. Molecules 2018, 23, 1093.

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