Photochemical and Optical Properties of Water-Soluble Xanthophyll Antioxidants: Aggregation vs Complexation

Polyakov, Nikolay E.; Magyar, Adam; Kispert, Lowell D.

doi:10.1021/jp4062708

Cited by 63 publications

(84 citation statements)

References 66 publications

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“…This fact confirms the hypothesis for the dependence of the structure and properties of GA complexes on its concentration. It is assumed that interaction between carotenoids and peroxyl radicals occurs via hydrogen abstraction from the most acidic 4-H proton of carotenoids (Focsan et al, 2012;Polyakov et al, 2013). GA forms a donut like dimer in which the hydrophobic polyene chain of carotenoids lies protected within the donut hole, permitting the hydrophilic ends and most acidic proton to be exposed to the surroundings.…”

Section: Antioxidant and Redox Properties Of Supramolecular Complexesmentioning

confidence: 99%

“…9. Optical absorption spectra of lutein (6 M) in 25% ethanol/water mixture at different GA concentrations (adopted from (Polyakov et al, 2013)). …”

Section: Antioxidant and Redox Properties Of Supramolecular Complexesmentioning

confidence: 99%

“…Fundamental and applied research has recently been devoted to the inclusion complexes of carotenoids with natural oligosaccharides and polysaccharides, which are assumed to possess protective properties and to decrease the hydrophobic behavior of the included molecules (Polyakov, Leshina, Konovalova, Hand, & Kispert, 2004a;Polyakov, Leshina, Salakhutdinov, & Kispert, 2006a;Polyakov, Leshina, Salakhutdinov, Konovalova, & Kispert, 2006b;Polyakov et al, , 2010Polyakov, Magyar, & Kispert, 2013;Apanasenko et al, 2015;Gomes et al, 2014;Pinho, Grootveld, Soares, & Henriques, 2014;Gharibzahedi, Razavi, & Mousavi, 2014;Jose et al, 2014;Yuan, Du, Jin, & Xu, 2013;Yuan, Jin, & Xu, 2012;De Oliveira et al, 2011;Stancanelli et al, 2012;Tachaprutinun, Udomsup, Luadthong, & Wanichwecharungruang, 2009). For example, astaxanthin encapsulated into poly(ethylene oxide)-4-methoxycinnamoylphthaloyl chitosan showed minimal heat degradation after a twohour heating at 70 • C in an aqueous environment, in contrast to that of unencapsulated carotenoid molecules which were almost completely destroyed (Tachaprutinun et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

“…Another fundamental property of the carotenoids is their ability to form aggregates in the presence of water. In particular, xanthophyll carotenoids form J-or H-types of dimer aggregates that significantly changed their photophysical and chemical properties (Polyakov et al, 2013;Ruban, Horton, & Young, 1993;Billsten, Sundstrom, & Polivka, 2005;Wang, Berg, Hsu, Merrill, & Tauber, 2012;McHale, 2012;Wang & Tauber, 2010). It has been demonstrated that inclusion complexes protect carotenoids from aggregation and this property increases their antioxidant activity (Polyakov et al, 2013) for GA complexes.…”

Section: Introductionmentioning

confidence: 99%

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Water soluble biocompatible vesicles based on polysaccharides and oligosaccharides inclusion complexes for carotenoid delivery

Polyakov

Kispert

2015

Carbohydrate Polymers

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Since carotenoids are highly hydrophobic, air- and light-sensitive hydrocarbon compounds, developing methods for increasing their bioavailability and stability towards irradiation and reactive oxygen species is an important goal. Application of inclusion complexes of "host-guest" type with polysaccharides and oligosaccharides such as arabinogalactan, cyclodextrins and glycyrrhizin minimizes the disadvantages of carotenoids when these compounds are used in food processing (colors and antioxidant capacity) as well as for production of therapeutic formulations. Cyclodextrin complexes which have been used demonstrated enhanced storage stability but suffered from poor solubility. Polysaccharide and oligosaccharide based inclusion complexes play an important role in pharmacology by providing increased solubility and stability of lipophilic drugs. In addition they are used as drug delivery systems to increase absorption rate and bioavailability of the drugs. In this review we summarize the existing data on preparation methods, analysis, and chemical reactivity of carotenoids in inclusion complexes with cyclodextrin, arabinogalactan and glycyrrhizin. It was demonstrated that incorporation of carotenoids into the "host" macromolecule results in significant changes in their physical and chemical properties. In particular, polysaccharide complexes show enhanced photostability of carotenoids in water solutions. A significant decrease in the reactivity towards metal ions and reactive oxygen species in solution was also detected.

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Section: Antioxidant and Redox Properties Of Supramolecular Complexesmentioning

confidence: 99%

“…9. Optical absorption spectra of lutein (6 M) in 25% ethanol/water mixture at different GA concentrations (adopted from (Polyakov et al, 2013)). …”

Section: Antioxidant and Redox Properties Of Supramolecular Complexesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Water soluble biocompatible vesicles based on polysaccharides and oligosaccharides inclusion complexes for carotenoid delivery

Polyakov

Kispert

2015

Carbohydrate Polymers

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“…Several studies using a single antioxidant have been conducted using aspirin [27], indomethacin [27], and astaxanthin [28]. Although these compounds could inhibit spin adduct formation, in the presence of relatively high concentration of reactive oxygen species, the formation of new radical species cannot be avoided.…”

Section: Esr Analysismentioning

confidence: 99%

Egg White Albumin Form Complex With Aspirin and Caffeine and Its Role as Free Radical Scavenger

Jayanti

Widyarti

Sabarudin

2018

Asian J Pharm Clin Res

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Objective: Egg white protein (ovalbumin) is well known to be freshly consumed in Indonesia as traditional medicine, or it is usually known as "Jamu." Ovalbumin, as well as egg white albumin, is able to form complex compounds with other substances through the formation of weak chemical and physical bonds. The objective of this study is to understand the behavior of ovalbumin as radical scavenger when it binds to antioxidants such as aspirin and caffeine (as a complex). Methods:In this study, docking sites and ovalbumin as scavenger were studied using computer-modeling software. An ovalbumin was used only for computer modeling, whereas in the wet laboratory, the freeze-drying albumin was used for electron spin resonance (ESR) and Fourier transforminfrared (FTIR) spectroscopy to determine its ability as a scavenger and functional groups, respectively. Albumin solution was applied to measure the viscosity. Results:The variability of tridimensional structures of aspirin was investigated after binding with ovalbumin. However, these structures cannot be seen clearly on caffeine. The root-mean-square deviation analysis showed that aspirin, as well as caffeine, altered the dynamic conformation of ovalbumin. The complex of aspirin-ovalbumin-caffeine which was treated at a temperature of −70°C showed intermolecular force. ESR results showed that the complex compounds could effectively reduce more free radicals when compared to aspirin or caffeine. The existence of aromatic compounds (as confirmed by FTIR) was useful for the scavenger molecules and chemical interaction occurs. The viscosity of the complex was similar with normal gastric mucus, which associated with radical scavenger. Conclusion:The characters of albumin when it binds to aspirin and caffeine indicated that scavenging activity of the complex and the viscosity showed an important result to be physiological scavengers of free radicals.

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Resonance Raman optical activity of zeaxanthin aggregates

Dudek

Zając

Kaczor

et al. 2017

J Raman Spectroscopy

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New methods of enhancement in Raman optical activity (ROA) scattering are of great interest. So, previously reported by us, Aggregation-Induced Resonance ROA (AIRROA) may open new opportunities in a field of structural studies of many biologically important compounds. However, the AIRROA phenomenon, reported up until now for astaxanthin and lutein derivatives, requires a deeper understanding and investigation of other carotenoids. Zeaxanthin is a dominant macular pigment that protects human retina against photo-oxidative damage. In this work, we analyse two types of chiral zeaxanthin self-assembly, H and J1, and verify that aggregation process is not enough to enhance ROA signal. Essential for the AIRROA effect is the fact that the electronic circular absorption band of supramolecular species is in proximity with the ROA excitation line. We also compare and analyse the spectral differences between J aggregates of astaxanthin and zeaxanthin, with reference to the AIRROA phenomenon.

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Photochemical and Optical Properties of Water-Soluble Xanthophyll Antioxidants: Aggregation vs Complexation

Cited by 63 publications

References 66 publications

Water soluble biocompatible vesicles based on polysaccharides and oligosaccharides inclusion complexes for carotenoid delivery

Water soluble biocompatible vesicles based on polysaccharides and oligosaccharides inclusion complexes for carotenoid delivery

Egg White Albumin Form Complex With Aspirin and Caffeine and Its Role as Free Radical Scavenger

Resonance Raman optical activity of zeaxanthin aggregates

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