Investigations on the binding and antioxidant properties of the plant flavonoid fisetin in model biomembranes

Sengupta, Bidisa; Banerjee, Anwesha; Sengupta, Pradeep K.

doi:10.1016/j.febslet.2004.06.027

Cited by 112 publications

(72 citation statements)

References 32 publications

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“…Fluorescence anisotropy (r) measurements were also performed, since this parameter serves as a sensitive indicator for monitoring fluorophore binding to motionally constrained regions of biological membranes (16,28). r is very low in fluid solution, where the fluorophore can freely rotate, and high for a rigid environment.…”

Section: Fluorescence Anisotropy Measurementsmentioning

confidence: 99%

Ground‐ and excited‐state proton transfer and antioxidant activity of 3‐hydroxyflavone in egg yolk phosphatidylcholine liposomes: absorption and fluorescence spectroscopic studies

et al. 2008

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Excited-state intramolecular proton transfer (ESIPT) and dual luminescence behaviour of 3-hydroxyflavone (3-HF) have been utilized to monitor its binding to liposomal membranes prepared from egg yolk phosphatydilcholine (EYPC). Additionally, absorption spectrophotometric assay has been performed to evaluate the antioxidant activity of 3-HF against lipid peroxidation in this membrane system. When 3-HF molecules are partitioned into EYPC liposomes, a weak long-wavelength absorption band with lambda(abs)(max) approximately 410 nm appears in addition to the principal absorption at approximately lambda(abs)(max) = 345 nm. Selective excitation of the 410 nm band produces the characteristic emission (lambda(em)(max) approximately 460 nm) of the ground-state anionic species, whereas excitation at the higher energy absorption band leads to dual emission with predominatly ESIPT tautomer fluorescence (lambda(em)(max) = 528 nm). Both ESIPT tautomer and the anionic species exhibit fairly high fluorescence anisotropy (r) values (r = 0.122 and 0.180, respectively). Biexponential fluorescence decay kinetics are observed for the ESIPT tautomer as well as the ground-state anionic forms, indicating heterogeneity in the microenvironments of the corresponding emitting species. Furthermore, we demonstrate that lipid peroxidation of EYPC liposomes is significantly inhibited upon 3-HF binding, suggesting that 3-HF can be potentially useful as an inhibitor of peroxidative damage of cell membranes.

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Section: Fluorescence Anisotropy Measurementsmentioning

confidence: 99%

Ground‐ and excited‐state proton transfer and antioxidant activity of 3‐hydroxyflavone in egg yolk phosphatidylcholine liposomes: absorption and fluorescence spectroscopic studies

et al. 2008

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“…Currently, it is unclear what kind of molecules mediates this interaction. Flavonoids have been reported to bind membranes, so they could potentially associate with the tonoplast directly (Sengupta et al, 2004;Oteiza et al, 2005;Verstraeten et al, 2013;PawlikowskaPawlega et al, 2014). Some of the enzymes in the anthocyanin pathways have been shown to partially localize to the tonoplast (Saslowsky and Winkel-Shirley, 2001;Toda et al, 2012).…”

Section: Avis Arise From Microautophagy Of Cytoplasmic Anthocyanin Agmentioning

confidence: 99%

Anthocyanin Vacuolar Inclusions Form by a Microautophagy Mechanism

et al. 2015

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Anthocyanins are flavonoid pigments synthesized in the cytoplasm and stored inside vacuoles. Many plant species accumulate densely packed, 3-to 10-mm diameter anthocyanin deposits called anthocyanin vacuolar inclusions (AVIs). Despite their conspicuousness and importance in organ coloration, the origin and nature of AVIs have remained controversial for decades. We analyzed AVI formation in cotyledons of different Arabidopsis thaliana genotypes grown under anthocyanin inductive conditions and in purple petals of lisianthus (Eustoma grandiorum). We found that cytoplasmic anthocyanin aggregates in close contact with the vacuolar surface are directly engulfed by the vacuolar membrane in a process reminiscent of microautophagy. The engulfed anthocyanin aggregates are surrounded by a single membrane derived from the tonoplast and eventually become free in the vacuolar lumen like an autophagic body. Neither endosomal/prevacuolar trafficking nor the autophagy ATG5 protein is involved in the formation of AVIs. In Arabidopsis, formation of AVIs is promoted by both an increase in cyanidin 3-O-glucoside derivatives and by depletion of the glutathione S-transferase TT19. We hypothesize that this novel microautophagy mechanism also mediates the transport of other flavonoid aggregates into the vacuole.

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“…On the other hand penetration of hydrophobic bilayer core by a group of flavonoids and isoflavonoids was deduced by Arora et al [4] on the basis of fluorescence spectroscopic experiments. Intrinsic fluorescence properties of fisetin were used by Sengupta et al [7] to show that this molecule was localized and rigidly bound at the polar/apolar interfacial region of lipid bilayer. In a series of 1 H magic angel spinning NMR experiments it was shown that in fact flavonoid molecules are broadly distributed along the membrane normal with a maximal probability of localization close to polar/apolar interface [8].…”

Section: Introductionmentioning

confidence: 99%

Genistein derivatives decrease liposome membrane integrity — Calcein release and molecular modeling study

Środa

Michalak

Maniewska

et al. 2008

Biophysical Chemistry

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The ability of newly synthesized genistein benzyl and glycosylated derivatives to permeabilize the liposome membrane was studied by calcein-leakage method. All studied derivatives appeared to be more effective than their parent compound -genistein. Comparing the experimental results with theoretical calculations we found that in case of benzyl derivatives the dipole moment of added benzene ring (with its substitutions) might be important for the strength of flavonoids-lipid interactions. This conclusion may have some implications for QSAR studies in which mostly the dipole moments of entire molecules are considered.

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Investigations on the binding and antioxidant properties of the plant flavonoid fisetin in model biomembranes

Cited by 112 publications

References 32 publications

Ground‐ and excited‐state proton transfer and antioxidant activity of 3‐hydroxyflavone in egg yolk phosphatidylcholine liposomes: absorption and fluorescence spectroscopic studies

Ground‐ and excited‐state proton transfer and antioxidant activity of 3‐hydroxyflavone in egg yolk phosphatidylcholine liposomes: absorption and fluorescence spectroscopic studies

Anthocyanin Vacuolar Inclusions Form by a Microautophagy Mechanism

Genistein derivatives decrease liposome membrane integrity — Calcein release and molecular modeling study

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