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 (7a–11a, 13a, 17a) were obtained. Another chemical modification led to 9 oximes of O-alkyl naringenin derivatives (7b–13b, 16b–17b) 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).
Highlights
About half of pharmacologically active compounds introduced to the market originate from natural biogenic molecules [1]
We present the efficient synthesis of 18 compounds, including 7 novel O-alkyl naringenin derivatives (7a–11a, 13a, 17a) and 9 new oximes (7b–13b, 16b–17b), that have never been described in the scientific literature
We described an efficient method for synthesizing novel naringenin analogues—seven O-alkyl derivatives (7a–11a, 13a, 17a) and nine oximes (7b–13b, 16b–17b)
Summary
About half of pharmacologically active compounds introduced to the market originate from natural biogenic molecules [1]. They belong to polyphenolic compounds ubiquitous in photosynthesizing cells. Despite the structural homogeneity of the group, flavonoids play a wide variety of functions in plants, where they are responsible for bright coloring, cell protection, photosensitization, growth regulation, etc. Flavonoids interact with mammalian and microbial cells. This versatility of biological function can be explained as the result of the interaction of cell enzymes with different structural parts of the flavonoid molecule, e.g., carbohydrate or phenyl ring. Flavonoids are present on the consumer market as dietary supplements or their constituents
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