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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.


First derivative absorption spectrum of quercetin.
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pone.0129749.g002: First derivative absorption spectrum of quercetin.

Mentions: In the present work, we employed the absolute difference between the maximum and the minimum (1Dmax-min) expressed in arbitrary units, eg. for quercetin, the absolute difference between the maximum at 356 nm and the minimum at 396 nm (1D 356–396) (Fig 2).


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)

First derivative absorption spectrum of quercetin.
© Copyright Policy
Related In: Results  -  Collection

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

pone.0129749.g002: First derivative absorption spectrum of quercetin.
Mentions: In the present work, we employed the absolute difference between the maximum and the minimum (1Dmax-min) expressed in arbitrary units, eg. for quercetin, the absolute difference between the maximum at 356 nm and the minimum at 396 nm (1D 356–396) (Fig 2).

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.