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Flavonoids in Microheterogeneous Media, Relationship between Their Relative Location and Their Reactivity towards Singlet Oxygen.

Günther G, Berríos E, Pizarro N, Valdés K, Montero G, Arriagada F, Morales J - PLoS ONE (2015)

Bottom Line: In addition, these compounds do not produce changes in fluorescence anisotropy of DPH, discarding their location in deeper regions of the lipid bilayer.The determined chemical reactivity sequence is similar in all the studied media (kaempferol < quercetin < morin).Morin is approximately 10 times more reactive than quercetin and 20 to 30 times greater than kaempferol, depending on the medium.

View Article: PubMed Central - PubMed

Affiliation: Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Santiago, Chile.

ABSTRACT
In this work, the relationship between the molecular structure of three flavonoids (kaempferol, quercetin and morin), their relative location in microheterogeneous media (liposomes and erythrocyte membranes) and their reactivity against singlet oxygen was studied. The changes observed in membrane fluidity induced by the presence of these flavonoids and the influence of their lipophilicity/hydrophilicity on the antioxidant activity in lipid membranes were evaluated by means of fluorescent probes such as Laurdan and diphenylhexatriene (DPH). The small differences observed for the value of generalized polarization of Laurdan (GP) curves in function of the concentration of flavonoids, indicate that these three compounds promote similar alterations in liposomes and erythrocyte membranes. In addition, these compounds do not produce changes in fluorescence anisotropy of DPH, discarding their location in deeper regions of the lipid bilayer. The determined chemical reactivity sequence is similar in all the studied media (kaempferol < quercetin < morin). Morin is approximately 10 times more reactive than quercetin and 20 to 30 times greater than kaempferol, depending on the medium.

No MeSH data available.


GP curves in function of the concentration of flavonoid incorporated in POPC / POPC liposomes.morin (•), quercetin (blue dot) and kaempferol(red dot).
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pone.0129749.g005: GP curves in function of the concentration of flavonoid incorporated in POPC / POPC liposomes.morin (•), quercetin (blue dot) and kaempferol(red dot).

Mentions: Fig 5 shows Laurdan GP as a function of flavonoid concentration. The small difference among curves indicates that these three compounds promote similar alterations in liposomes and erythrocyte membranes. In the absence of flavonoids, the GP value in erythrocyte membrane was 0.47 and 0.32 at 25°C and 37°C, respectively, values that decreased to +0.17 and +0.11 when incorporating 7x10-5 M of flavonoid.


Flavonoids in Microheterogeneous Media, Relationship between Their Relative Location and Their Reactivity towards Singlet Oxygen.

Günther G, Berríos E, Pizarro N, Valdés K, Montero G, Arriagada F, Morales J - PLoS ONE (2015)

GP curves in function of the concentration of flavonoid incorporated in POPC / POPC liposomes.morin (•), quercetin (blue dot) and kaempferol(red dot).
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4476713&req=5

pone.0129749.g005: GP curves in function of the concentration of flavonoid incorporated in POPC / POPC liposomes.morin (•), quercetin (blue dot) and kaempferol(red dot).
Mentions: Fig 5 shows Laurdan GP as a function of flavonoid concentration. The small difference among curves indicates that these three compounds promote similar alterations in liposomes and erythrocyte membranes. In the absence of flavonoids, the GP value in erythrocyte membrane was 0.47 and 0.32 at 25°C and 37°C, respectively, values that decreased to +0.17 and +0.11 when incorporating 7x10-5 M of flavonoid.

Bottom Line: In addition, these compounds do not produce changes in fluorescence anisotropy of DPH, discarding their location in deeper regions of the lipid bilayer.The determined chemical reactivity sequence is similar in all the studied media (kaempferol < quercetin < morin).Morin is approximately 10 times more reactive than quercetin and 20 to 30 times greater than kaempferol, depending on the medium.

View Article: PubMed Central - PubMed

Affiliation: Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Santiago, Chile.

ABSTRACT
In this work, the relationship between the molecular structure of three flavonoids (kaempferol, quercetin and morin), their relative location in microheterogeneous media (liposomes and erythrocyte membranes) and their reactivity against singlet oxygen was studied. The changes observed in membrane fluidity induced by the presence of these flavonoids and the influence of their lipophilicity/hydrophilicity on the antioxidant activity in lipid membranes were evaluated by means of fluorescent probes such as Laurdan and diphenylhexatriene (DPH). The small differences observed for the value of generalized polarization of Laurdan (GP) curves in function of the concentration of flavonoids, indicate that these three compounds promote similar alterations in liposomes and erythrocyte membranes. In addition, these compounds do not produce changes in fluorescence anisotropy of DPH, discarding their location in deeper regions of the lipid bilayer. The determined chemical reactivity sequence is similar in all the studied media (kaempferol < quercetin < morin). Morin is approximately 10 times more reactive than quercetin and 20 to 30 times greater than kaempferol, depending on the medium.

No MeSH data available.