Supramolecular Carotenoid Complexes of Enhanced Solubility and Stability—The Way of Bioavailability Improvement

Focsan, A. Ligia; Polyakov, Nikolay E.; Kispert, Lowell D.

doi:10.3390/molecules24213947

Cited by 55 publications

(57 citation statements)

References 143 publications

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“…Yields for the monotriazoles were calculated from the starting carotenoid pentynoates, as if they were the sole products. The capsanthin pentynoate (15) did not give a complete conversion, as approximately 10% of the starting pentynoate was recovered.…”

Section: Introductionmentioning

confidence: 95%

“…Molecules 2020, 24, x FOR PEER REVIEW 4 of 22 carotenoid pentynoates, as if they were the sole products. The capsanthin pentynoate (15) did not give a complete conversion, as approximately 10% of the starting pentynoate was recovered. All the prepared compounds were fully characterized by their NMR, MS, UV, and IR spectra.…”

Section: Introductionmentioning

confidence: 95%

“…In the case of the daidzein-capsanthin conjugates (20a and 20b), these regioisomers could be separated and identified. In the 1 H-NMR spectra of 20a and 20b, the chemical shifts of H-3 are slightly but characteristically different (Table 1), and in comparison with the parent capsanthin dipentynoate (15), as well as with the bistriazole 19, the substituents on C-3 can be distinguished. Similar differences in the chemical shifts of H-3 can also be observed.…”

Section: Introductionmentioning

confidence: 99%

“…Chrysin is a flavone with low bioavailability and rapid excretion; however, it showed cancer chemopreventive activity [12], decreased the symptoms of colitis [13], and was also found to be beneficial in connection with the insulin resistance and type II diabetes mellitus [14].Both carotenoids and flavonoids are rather sensitive to oxidation, but their stability and bioavailability can be significantly increased by additives. Water-soluble carbohydrate-based nanoparticles were described to form host-guest complexes with carotenoids, improving their properties [15]. The effect of mixing carotenoids with flavonoids is of particular interest, as synergy arises in their protective effect on low-density lipoprotein oxidation, which plays an important role in the development of atherosclerosis [16].…”

mentioning

confidence: 99%

“…Both carotenoids and flavonoids are rather sensitive to oxidation, but their stability and bioavailability can be significantly increased by additives. Water-soluble carbohydrate-based nanoparticles were described to form host-guest complexes with carotenoids, improving their properties [15]. The effect of mixing carotenoids with flavonoids is of particular interest, as synergy arises in their protective effect on low-density lipoprotein oxidation, which plays an important role in the development of atherosclerosis [16].…”

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confidence: 99%

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Study on the Synthesis, Antioxidant Properties, and Self-Assembly of Carotenoid–Flavonoid Conjugates

et al. 2020

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Flavonoids and carotenoids possess beneficial physiological effects, such as high antioxidant capacity, anticarcinogenic, immunomodulatory, and anti-inflammatory properties, as well as protective effects against UV light. The covalent coupling of hydrophobic carotenoids with hydrophilic flavonoids, such as daidzein and chrysin, was achieved, resulting in new amphipathic structures. 7-Azidohexyl ethers of daidzein and chrysin were prepared in five steps, and their azide-alkyne [4 + 2] cycloaddition with pentynoates of 8′-apo-β-carotenol, zeaxanthin, and capsanthin afforded carotenoid–flavonoid conjugates. The trolox-equivalent antioxidant capacity against ABTS•+ radical cation and self-assembly of the final products were examined. The 1:1 flavonoid–carotenoid hybrids generally showed higher antioxidant activity than their parent flavonoids but lower than that of the corresponding carotenoids. The diflavonoid hybrids of zeaxanthin and capsanthin, however, were found to exhibit a synergistic enhancement in antioxidant capacities. ECD (electronic circular dichroism) and UV-vis analysis of zeaxanthin–flavonoid conjugates revealed that they form different optically active J-aggregates in acetone/water and tetrahydrofuran/water mixtures depending on the solvent ratio and type of the applied aprotic polar solvent, while the capsanthin derivatives showed no self-assembly. The zeaxanthin bis-triazole conjugates with daidzein and with chrysin, differing only in the position of a phenolic hydroxyl group, showed significantly different aggregation profile upon the addition of water.

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Section: Introductionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Study on the Synthesis, Antioxidant Properties, and Self-Assembly of Carotenoid–Flavonoid Conjugates

et al. 2020

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A Review of the Chemistry and Biological Activities of Natural Colorants, Dyes, and Pigments: Challenges, and Opportunities for Food, Cosmetics, and Pharmaceutical Application

Pasdaran

Zare

Hamedi

et al. 2023

Chemistry & Biodiversity

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Natural pigments are important sources for the screening of bioactive lead compounds. This article reviewed the chemistry and therapeutic potentials of over 570 colored molecules from plants, fungi, bacteria, insects, algae, and marine sources. Moreover, related biological activities, advanced extraction, and identification approaches were reviewed. A variety of biological activities, including cytotoxicity against cancer cells, antioxidant, anti‐inflammatory, wound healing, anti‐microbial, antiviral, and anti‐protozoal activities, have been reported for different pigments. Considering their structural backbone, they were classified as naphthoquinones, carotenoids, flavonoids, xanthones, anthocyanins, benzotropolones, alkaloids, terpenoids, isoprenoids, and non‐isoprenoids. Alkaloid pigments were mostly isolated from bacteria and marine sources, while flavonoids were mostly found in plants and mushrooms. Colored quinones and xanthones were mostly extracted from plants and fungi, while colored polyketides and terpenoids are often found in marine sources and fungi. Carotenoids are mostly distributed among bacteria, followed by fungi and plants. The pigments isolated from insects have different structures, but among them, carotenoids and quinone/xanthone are the most important. Considering good manufacturing practices, the current permitted natural colorants are: Carotenoids (canthaxanthin, β‐carotene, β‐apo‐8′‐carotenal, annatto, astaxanthin) and their sources, lycopene, anthocyanins, betanin, chlorophyllins, spirulina extract, carmine and cochineal extract, henna, riboflavin, pyrogallol, logwood extract, guaiazulene, turmeric, and soy leghemoglobin.

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Innovative Encapsulation Strategies for Food, Industrial, and Pharmaceutical Applications

Aanniz,

El Omari,

Elouafy

et al. 2024

Chemistry & Biodiversity

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Encapsulation has emerged as a vitally important tool for protecting the integrity of critical chemicals and improving the delivery mechanisms of natural/synthetic drugs, enabling the controlled release of ingredients and the maintenance of their chemical, physical, and biological properties. It is well known that essential oils (EOs) provide a valuable alternative for food preservation, as they help reducing the deterioration of foodstuffs as well as the proliferation of pathogens. Nevertheless, EOs are highly volatile and lipophilic, rendering them insoluble in aqueous systems. In addition, their secondary metabolites are extremely susceptible to environmental factors such as humidity, temperature, light, and oxygen. Therefore, encapsulation of EOs is an innovative option not only for preserving these substances but also for promoting their stability, controlling their release, and optimizing their efficiency and bioavailability. In this sense, this review aimed to describe current techniques and approaches used to incorporate natural hydrophobic compounds, covering EOs. It also examines whether encapsulation technology can be used efficiently in drug discovery and development. Studies have shown that microencapsulation, the use of nanoparticle, and liposomal are the most effective techniques for encapsulating EOs. Other encapsulation systems included spray drying, coacervation, and emulsification.

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Supramolecular Carotenoid Complexes of Enhanced Solubility and Stability—The Way of Bioavailability Improvement

Cited by 55 publications

References 143 publications

Study on the Synthesis, Antioxidant Properties, and Self-Assembly of Carotenoid–Flavonoid Conjugates

Study on the Synthesis, Antioxidant Properties, and Self-Assembly of Carotenoid–Flavonoid Conjugates

A Review of the Chemistry and Biological Activities of Natural Colorants, Dyes, and Pigments: Challenges, and Opportunities for Food, Cosmetics, and Pharmaceutical Application

Innovative Encapsulation Strategies for Food, Industrial, and Pharmaceutical Applications

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