Interactions of the monomeric and dimeric flavones apigenin and amentoflavone with the plasma membrane of L929 cells; a fluorescence study.
Flavonoids are ubiquitous polyphenolic compounds, found in vascular plants, which are endowed with a large variety of biological effects. Some of these effects have been assumed to result from interactions with the cell plasma membrane. In order to investigate the nature of these interactions a fluorescence study was performed with two flavonoids, currently used in one of the laboratories: apigenin and its homologous dimer amentoflavone. After preliminary assays with DPH in several types of phospholipid liposomes, the effects of these flavonoids on the membrane of mouse L929 fibroblasts were compared, using the non-permeant probe TMA-DPH. Amentoflavone, unlike apigenin, induced a static quenching effect, which denoted an important, but reversible, association of the molecule with the plasma membrane. In addition, amentoflavone treatment induced a dose-dependent increase in TMA-DPH fluorescence anisotropy, which could be interpreted as an increase in membrane lipidic order. For apigenin, the effect was much less important. Moreover, exploiting the capacity of TMA-DPH to label endocytic compartments, it was shown that, after association with the membrane, amentoflavone is not internalized into the cell. Possible correlations of these membrane effects with other biological properties are discussed.
Faculté de Pharmacie de Strasbourg, Illkirch, France.
A F
AF
Lenne-Gouverneur
A
A
Lobstein
G
G
Haan-Archipoff
G
G
Duportail
R
R
Anton
J G
JG
Kuhry
D000818:Animals; D016880:Anisotropy; D044946:Biflavonoids; D002460:Cell Line; D002462:Cell Membrane / Q000378:metabolism; D020843:Chamomile; D019281:Dimerization; D004161:Diphenylhexatriene / Q000031:analogs & derivatives*; D005419:Flavonoids / Q000737:chemistry / Q000378:metabolism*; D005456:Fluorescent Dyes; D041743:Herb-Drug Interactions; D008081:Liposomes / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D009822:Oils, Volatile / Q000737:chemistry / Q000378:metabolism*; D010743:Phospholipids / Q000378:metabolism; D010946:Plants, Medicinal; D013050:Spectrometry, Fluorescence
D044946:Biflavonoids; D005419:Flavonoids; D005456:Fluorescent Dyes; D008081:Liposomes; D009822:Oils, Volatile; D010743:Phospholipids; D004161:Diphenylhexatriene; C033628:1-(4-(trimethylamino)phenyl)-6-phenylhexa-1,3,5-triene; C011164:amentoflavone