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

• Published in: Molecules (Basel, Switzerland) Vol. 22; no. 9; p. 1485
• Main Authors: Kozłowska, Joanna, Potaniec, Bartłomiej, Żarowska, Barbara, Anioł, Mirosław
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 06.09.2017; MDPI
• Subjects: Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - pharmacology; Antifungal Agents - chemical synthesis; Antifungal Agents - pharmacology; Antimicrobial activity; Aspergillus niger - drug effects; Biological activity; Biological effects; Candida albicans; Candida albicans - drug effects; Escherichia coli; Escherichia coli - drug effects; Flavanones - chemical synthesis; Flavanones - pharmacology; Fusarium; Fusarium - drug effects; Humans; Iodides; Microbial Sensitivity Tests; Molecular Structure; Naringenin; O-alkyl derivatives; Optical density; Oximes; Oximes - chemical synthesis; Oximes - pharmacology; Potassium; Potassium carbonate; Staphylococcus aureus; Staphylococcus aureus - drug effects; Structure-Activity Relationship; naringenin; O-alkyl derivatives; antimicrobial activity; oximes
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules22091485

-Alkyl derivatives of naringenin ( - ) were prepared from naringenin using the corresponding alkyl iodides and anhydrous potassium carbonate. The resulting products were used to obtain oximes ( - ). All compounds were tested for antimicrobial activity against ATCC10536, DSM799, DSM1386, CBS1526, KB-F1, and DSM1957. The resulting biological activity was expressed as the increase in optical density (ΔOD). The highest inhibitory effect against ATCC10536 was observed for 7,4'-di- -pentylnaringenin ( ), 7- -dodecylnaringenin ( ), naringenin oxime ( ), 7,4'-di- -pentylnaringenin oxime ( ), and 7- -dodecylnaringenin oxime ( ) (ΔOD = 0). 7- -dodecylnaringenin oxime ( ) also inhibited the growth of DSM799 (ΔOD = 0.35) and DSM1386 (ΔOD = 0.22). The growth of CBS1526 was inhibited as a result of the action of 7,4'-di- -methylnaringenin ( ), 7- -ethylnaringenin ( ), 7,4'-di- -ethylnaringenin ( ), 5,7,4'-tri- -ethylnaringenin ( ), 7,4'-di- -pentylnaringenin ( ), and 7- -dodecylnaringenin ( ) (ΔOD in the range of 0.49-0.42) in comparison to that of the control culture (ΔOD = 1.87). In the case of KB-F1, naringenin ( ), 7,4'-di- -dodecylnaringenin ( ), 7- -dodecylnaringenin oxime ( ), and 7,4'-di- -dodecylnaringenin oxime ( ) showed the strongest effect (ΔOD = 0). 7,4'-Di- -pentylnaringenin ( ) and naringenin oxime ( ) hindered the growth of DSM1957 (ΔOD = 0).