Stabilization of alpha-lipoic acid by complex formation with octenylsuccinylated high amylose starch

Li, Yi Xuan; Park, Eun Young; Lim, Seung Taik

doi:10.1016/j.foodchem.2017.09.028

Cited by 27 publications

(9 citation statements)

References 28 publications

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“…It should be noted that no works devoted to development of silica-based composites of LA were found in literature. Only "soft" materials, that are deformed or structurally altered by thermal or mechanical stress and subject to enzymatic degradation, such as cyclodextrins, polysaccharides and lipids have been proposed to enhance thermal stability [25][26][27] and photostability [26][27][28] of the drug. Colloid silica is very promising material for development of oral pharmaceutical formulations, because it is recognized as a safe food additive [29].…”

Section: Introductionmentioning

confidence: 99%

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Development of Novel Silica-Based Formulation of α-Lipoic Acid: Evaluation of Photo and Thermal Stability of the Encapsulated Drug

2020

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Powerful antioxidant α-lipoic acid (LA) is easily degraded under light and heating. This creates difficulties in its manufacture, storage and reduces efficiency and safety of the drug. The purpose of this work was to synthesize novel silica-based composites of LA and evaluate their ability to increase photo and thermal stability of the drug. It was assumed that the drug stabilization can be achieved due to LA-silica interactions. Therefore, the composites of LA with unmodified and organomodified silica matrixes were synthesized by sol-gel method at the synthesis pH below or above the pKa of the drug. The effects of silica matrix modification and the synthesis pH on the LA-silica interactions and kinetics of photo and thermal degradation of LA in the composites were studied. The nature of the interactions was revealed by FTIR spectroscopy. It was found that the rate of thermal degradation of the drug in the composites was significantly lower compared to free LA and mainly determined by the LA-silica interactions. However, photodegradation of LA in the composites under UV irradiation was either close to that for free drug or significantly more rapid. It was shown that kinetics of photodegradation was independent of the interactions and likely determined by physical properties of surface of the composite particles (porosity and reflectivity). The most promising composites for further development of novel silica-based formulations were identified.

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Section: Introductionmentioning

confidence: 99%

“…The interactions of drugs with mesoporous silica [4], cyclodextrins [32], liposomal phosphatidylcholine [33] and polysaccharide microparticles [34] led to their increasing photo stability. Thermal stability of drugs was enhanced by complex formation with β-cyclodexrin [26,35] and amylose [26].…”

Section: Introductionmentioning

confidence: 99%

Development of Novel Silica-Based Formulation of α-Lipoic Acid: Evaluation of Photo and Thermal Stability of the Encapsulated Drug

2020

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“…3 However, α-LA has poor water solubility and it is not stable under thermal process; therefore, encapsulation of α-LA is of interest in order to improve its thermal and oxidative stability and enhance its solubility and bioavailability. 4,5 Cyclodextrins are cyclic oligosaccharides produced from starch and they are well-known for their molecular encapsulation capability by forming inclusion complexes with bioactive molecules; therefore, they are used in foods. 6−9 The solubility and bioavailability of the bioactive compounds (e.g., essential oils, vitamins, flavors, food supplements, etc.)…”

Section: ■ Introductionmentioning

confidence: 99%

Encapsulation and Stabilization of α-Lipoic Acid in Cyclodextrin Inclusion Complex Electrospun Nanofibers: Antioxidant and Fast-Dissolving α-Lipoic Acid/Cyclodextrin Nanofibrous Webs

Çelebioğlu

Uyar

2019

J. Agric. Food Chem.

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In this study, electrospinning of nanofibers from alpha-lipoic acid/cyclodextrin inclusion complex systems was successfully performed without having any polymeric matrix. Alpha-lipoic acid (α-LA) is a natural antioxidant compound which is widely used as a food supplement. However, it has limited water solubility and poor thermal and oxidative stability. Nevertheless, it is possible to enhance its water solubility and thermal stability by inclusion complexation with cyclodextrins. Here, hydroxypropyl-beta-cyclodextrin (HP-β-CyD) and hydroxypropyl-gamma-cyclodextrin (HP-γ-CyD) were chosen as host molecules for forming inclusion complexation with α-LA. Accordingly, α-LA was inclusion complexed with HP-β-CyD and HP-γ-CyD by using very high concentrated aqueous solutions of CyD (200%, w/v) having 1/1 and 2/1 molar ratio of α-LA/CyD. Except α-LA/HP-β-CyD (1/1) solution, other α-LA/CyD solutions were turbid indicating the presence of some noncomplexed α-LA whereas α-LA/HP-β-CyD (1/1) solution was very homogeneous signifying that α-LA was fully complexed with HP-β-CyD. Even so, electrospinning was performed for all of the α-LA/HP-β-CyD (1/1 and 2/1) and α-LA/HP-γ-CyD (1/1 and 2/1) aqueous solutions, and defect-free bead-less and uniform nanofibers were successfully obtained for all of the α-LA/CyD solutions. However, the electrospinning process for α-LA/CyD (1/1) systems was much more efficient than the α-LA/CyD (2/1) systems, and we were able to produce self-standing and flexible nanofibrous webs from α-LA/CyD (1/1) systems. α-LA was efficiently preserved during the electrospinning process of α-LA/CyD (1/1) systems and the resulting electrospun α-LA/HP-β-CyD and α-LA/HP-γ-CyD nanofibers were produced with the molar ratios of ∼1/1 and ∼0.85/1 (α-LA/CyD), respectively. The better encapsulation efficiency of α-LA in α-LA/HP-β-CyD nanofibers was due to higher solubility increase and higher binding strength between α-LA and HP-β-CyD as revealed by the phase solubility test. α-LA was in the amorphous state in α-LA/CyD nanofibers and both α-LA/HP-β-CyD and α-LA/HP-γ-CyD nanofibers were dissolved very quickly in water and also when they wetted with artificial saliva. Additionally, the antioxidant activity of pure α-LA and α-LA/CyD nanofibers was comparatively evaluated using ABTS radical cation assay. α-LA/CyD nanofibers have shown significantly higher antioxidant performance compared to pure α-LA owing to improved water solubility by CyD inclusion complexation. The thermal stability enhancement of α-LA in α-LA/CyD nanofibers was achieved compared to pure α-LA under heat treatment (100 °C for 24 h). These promising results support that antioxidant α-LA/CyD nanofibers may have potential applications as orally fast-dissolving food supplements.

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“…High availability and economical aspects, make this biopolymer suitable for use as a carrier. [ 11–15 ] Starch consists of two parts: amylose and amylopectin. [ 16 ]…”

Section: Introductionmentioning

confidence: 99%

Characterization and Antibacterial Activity of Encapsulated Rosemary Essential Oil within Amylose Nanostructures as a Natural Antimicrobial in Food Applications

2021

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Rosemary essential oil (REO) is a natural phenolic compound with high antimicrobial activity. However, its application is limited due to the poor solubility in water, instability, and high volatility. In this study, REO is incorporated into the high amylose corn starch (HACS) nanostructures by inclusion complexation. The characterization of the obtained nanostructures is done by SEM, TGA, FTIR, and XRD. Encapsulation efficiency, loading capacity, stability, release, and antibacterial activity of encapsulated REO are analyzed. The nanostructures show spherical nanoparticles with an average size lower than 200 nm. The results of XRD and FTIR confirm the incorporation of REO into the amylose nanostructures. Thermogravimetric analysis indicates that the inclusion complex of REO and HACS increases the thermal stability of REO significantly. The solubility and antibacterial activity of REO are enhanced after complexation with amylose nanostructures. Minimum inhibitory concentration (MIC) of free REO is 3.52 mg mL−1 or 0.39% v/v and for encapsulated REO is decreased to 2.5 mg mL−1. The results suggest that HACS can be used as a potential carrier for sensitive and hydrophobic compounds to enhance their application in the pharmaceutical and food industries.

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Stabilization of alpha-lipoic acid by complex formation with octenylsuccinylated high amylose starch

Cited by 27 publications

References 28 publications

Development of Novel Silica-Based Formulation of α-Lipoic Acid: Evaluation of Photo and Thermal Stability of the Encapsulated Drug

Development of Novel Silica-Based Formulation of α-Lipoic Acid: Evaluation of Photo and Thermal Stability of the Encapsulated Drug

Encapsulation and Stabilization of α-Lipoic Acid in Cyclodextrin Inclusion Complex Electrospun Nanofibers: Antioxidant and Fast-Dissolving α-Lipoic Acid/Cyclodextrin Nanofibrous Webs

Characterization and Antibacterial Activity of Encapsulated Rosemary Essential Oil within Amylose Nanostructures as a Natural Antimicrobial in Food Applications

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