118244-13-6Relevant articles and documents
Nitrogen-containing naringenin derivatives for reversing multidrug resistance in cancer
Ferreira, Maria-José U.,Ferreira, Ricardo J.,Gajdács, Márió,Kincses, Annamária,Spengler, Gabriella,dos Santos, Daniel J. V. A.
, (2020)
Naringenin (1), isolated from Euphorbia pedroi, was previously derivatized yielding compounds 2–13. In this study, aiming at expanding the pool of analogues of the flavanone core towards better multidrug resistance (MDR) reversal agents, alkylation reactions and chemical modification of the carbonyl moiety was performed (15–39). Compounds structures were assigned mainly by 1D and 2D NMR experiments. Compounds 1–39 were assessed as MDR reversers, in human ABCB1-transfected mouse T-lymphoma cells, overexpressing P-glycoprotein (P-gp). The results revealed that O-methylation at C-7, together with the introduction of nitrogen atoms and aromatic moieties at C-4 or C-4′, significantly improved the activity, being compounds 27 and 37 the strongest P-gp modulators and much more active than verapamil. In combination assays, synergistic interactions of selected compounds with doxorubicin substantiated the results. While molecular docking suggested that flavanone derivatives act as competitive modulators, molecular dynamics showed that dimethylation promotes binding to a modulator-binding site. Moreover, flavanones may also interact with a vicinal ATP-binding site in both nucleotide-binding domains, hypothesizing an allosteric mode of action.
Effect of naringenin and its derivatives on the probing behavior of myzus persicae (Sulz.)
Aniol, Miroslaw,Gabrys, Beata,Kordan, Bozena,Kozlowska, Joanna,Stec, Katarzyna,Wróblewska-Kurdyk, Anna
, (2020/08/24)
Substances that alter insect behavior have attracted a lot of attention as potential crop protection agents. Naringenin (5,7,40-trihydroxyflavanone) is a naturally occurring bioactive flavanone. We evaluated the influence of naringenin on aphid activities during individual phases of probing and feeding and the effect of structural modifications of naringenin on its activity towards aphids. We monitored the probing behavior of Myzus persicae (Sulz.) (Hemiptera: Aphididae) using the Electrical Penetration Graph (EPG) technique. The chemical modifications were the substitution of hydrogen atoms with methyl, ethyl or pentyl groups and the replacement of the carbonyl group in naringenin and its derivatives with an oxime moiety. Depending on the substituents, the activity of naringenin-derived compounds varied in potency and mode of action. Naringenin was an attractant of moderate activity, which enhanced sap ingestion. The naringenin derivative with two methyl groups-7,40-di-O-methylnaringenin-was a deterrent, which hindered aphid probing in non-phloem tissues. Naringenin oxime derivatives with methyl substituents-7,40-di-O-methylnaringenin oxime, 7-O-methylnaringenin oxime, and 5,7,40-tri-O-methylnaringenin oxime-and the derivative with a pentyl substituent-7-O-pentylnaringenin oxime-were strong attractants which stimulated aphid probing in non-phloem tissues and the ingestion of phloem sap.
Cyclohexanoid protoflavanones from the stem-bark and roots of Ongokea gore
Jerz, Gerold,Waibel, Reiner,Achenbach, Hans
, p. 1698 - 1706 (2008/02/01)
Phytochemical investigation of root and stem-bark of the West African medicinal plant Ongokea gore resulted in the isolation of four novel flavonoids with an unusual cyclohexyl substituent instead of the common aromatic ring B. The structures of the isolated compounds were elucidated by spectroscopic methods, mainly 1D and 2D NMR, and subsequently, the structures were corroborated by chemical conversion to (-)-(S)-sakuranetin. The absolute configurations, and preferred conformations were determined by NOE experiments and CD measurements.
