Synthesis and Biological Activity of Novel O-Alkyl Derivatives of Naringenin and Their Oximes

Abstract

O-Alkyl derivatives of naringenin (1a–10a) were prepared from naringenin using the corresponding alkyl iodides and anhydrous potassium carbonate. The resulting products were used to obtain oximes (1b–10b). All compounds were tested for antimicrobial activity against Escherichia coli ATCC10536, Staphylococcus aureus DSM799, Candida albicans DSM1386, Alternaria alternata CBS1526, Fusarium linii KB-F1, and Aspergillus niger DSM1957. The resulting biological activity was expressed as the increase in optical density (ΔOD). The highest inhibitory effect against E. coli ATCC10536 was observed for 7,4′-di-O-pentylnaringenin (8a), 7-O-dodecylnaringenin (9a), naringenin oxime (NG-OX), 7,4′-di-O-pentylnaringenin oxime (8b), and 7-O-dodecylnaringenin oxime (9b) (ΔOD = 0). 7-O-dodecylnaringenin oxime (9b) also inhibited the growth of S. aureus DSM799 (ΔOD = 0.35) and C. albicans DSM1386 (ΔOD = 0.22). The growth of A. alternata CBS1526 was inhibited as a result of the action of 7,4′-di-O-methylnaringenin (2a), 7-O-ethylnaringenin (4a), 7,4′-di-O-ethylnaringenin (5a), 5,7,4′-tri-O-ethylnaringenin (6a), 7,4′-di-O-pentylnaringenin (8a), and 7-O-dodecylnaringenin (9a) (ΔOD in the range of 0.49–0.42) in comparison to that of the control culture (ΔOD = 1.87). In the case of F. linii KB-F1, naringenin (NG), 7,4′-di-O-dodecylnaringenin (10a), 7-O-dodecylnaringenin oxime (9b), and 7,4′-di-O-dodecylnaringenin oxime (10b) showed the strongest effect (ΔOD = 0). 7,4′-Di-O-pentylnaringenin (8a) and naringenin oxime (NG-OX) hindered the growth of A. niger DSM1957 (ΔOD = 0).

Synthesis, Cancer‐Selective Antiproliferative and Apoptotic Effects of Some (±)‐Naringenin Cycloaminoethyl Derivatives

“…Naringenin, a polyphenolic compound that is found naturally in citrus fruits and has a wide range of biological activities including anticancer effects . However, its clear application is limited due to its low solubility in water as well as in organic solvents.…”

Cascade biotransformation of dehydroepiandrosterone (DHEA) by Beauveria species

“…For sequence analysis, PCR-amplified DNA fragments were purified as described earlier 60 . DNA fragments were labelled using a forward primer and the BigDyeTerminator 3.1 kit (Applied Biosystems, Foster City, CA, USA), according to the producer’s recommendations and precipitated with 96% ethanol.…”

Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC6H3C=NOH (X= Me, OH and MeO)

“…Aldoximes, RCH NOH, are found in many biologically active compounds (Abele et al, 2008;Nikitjuka & Jirgensons 2014), having a diverse range of uses including as anti-tumor agents (Martínez-Pascual et al, 2017;Qin et al, 2017;Canario et al, 2018;Huang et al, 2018), acaricidal and insecticidal agents (Dai et al, 2017), thymidine phosphorylase inhibitors (Zhao et al, 2018), anti-microbial agents (Yadav et al, 2017), bacteriocides (Kozlowska et al, 2017), anti-inflammatory agents (Mohassab et al, 2017) and in the treatment of nervegas poisoning (Lorke et al, 2008;Voicu et al, 2010;Katalinić et al, 2017;Radić et al, 2013). In the plant kingdom, oximes play a vital role in metabolism (Sørensen et al, 2018).…”