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
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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).
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