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Molecules 2019, 24(4), 679; https://doi.org/10.3390/molecules24040679

Novel O-alkyl Derivatives of Naringenin and Their Oximes with Antimicrobial and Anticancer Activity

1
Department of Chemistry, Faculty of Biotechnology and Food Science, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
2
Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland
3
Department of Molecular and Cellular Biology, Faculty of Pharmacy with Division of Laboratory Diagnostics, Wroclaw Medical University, Borowska 211A, 50-556 Wrocław, Poland
*
Author to whom correspondence should be addressed.
Received: 8 January 2019 / Revised: 1 February 2019 / Accepted: 12 February 2019 / Published: 14 February 2019
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Abstract

In our investigation, we concentrated on naringenin (NG)—a widely studied flavanone that occurs in citrus fruits. As a result of a reaction with a range of alkyl iodides, 7 novel O-alkyl derivatives of naringenin (7a11a, 13a, 17a) were obtained. Another chemical modification led to 9 oximes of O-alkyl naringenin derivatives (7b13b, 16b17b) that were never described before. The obtained compounds were evaluated for their potential antibacterial activity against Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. The results were reported as the standard minimal inhibitory concentration (MIC) values and compared with naringenin and its known O-alkyl derivatives. Compounds 4a, 10a, 12a, 14a, 4b, 10b, 11b, and 14b were described with MIC of 25 µg/mL or lower. The strongest bacteriostatic activity was observed for 7-O-butylnaringenin (12a) against S. aureus (MIC = 6.25 µg/mL). Moreover, the antitumor effect of flavonoids was examined on human colon cancer cell line HT-29. Twenty-six compounds were characterized as possessing an antiproliferative activity stronger than that of naringenin. The replacement of the carbonyl group with an oxime moiety significantly increased the anticancer properties. The IC50 values below 5 µg/mL were demonstrated for four oxime derivatives (8b, 11b, 13b and 16b). View Full-Text
Keywords: naringenin; O-alkyl derivatives; oximes; antibacterial activity; anticancer activity naringenin; O-alkyl derivatives; oximes; antibacterial activity; anticancer activity
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Kozłowska, J.; Grela, E.; Baczyńska, D.; Grabowiecka, A.; Anioł, M. Novel O-alkyl Derivatives of Naringenin and Their Oximes with Antimicrobial and Anticancer Activity. Molecules 2019, 24, 679.

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