Dietary astaxanthin: an excellent carotenoid with multiple health benefits.

Astaxanthin is a carotenoid widely found in marine organisms and microorganisms. With extensive use in nutraceuticals, cosmetics, and animal feed, astaxanthin will have the largest share in the global market for carotenoids in the near future. Owing to its unique molecular features, astaxanthin has excellent antioxidant activity and holds promise for use in biochemical studies. This review focuses on the observed health benefits of dietary astaxanthin, as well as its underlying bioactivity mechanisms. Recent studies have increased our understanding of the role of isomerization and esterification in the structure-function relationship of dietary astaxanthin. Gut microbiota may involve the fate of astaxanthin during digestion and absorption; thus, further knowledge is needed to establish accurate recommendations for dietary intake of both healthy and special populations. Associated with the regulation of redox balance and multiple biological mechanisms, astaxanthin is proposed to affect oxidative stress, inflammation, cell death, and lipid metabolism in humans, thus exerting benefits for skin condition, eye health, cardiovascular system, neurological function, exercise performance, and immune response. Additionally, preclinical trials predict its potential effects such as intestinal flora regulation and anti-diabetic activity. Therefore, astaxanthin is worthy of further investigation for boosting human health, and wide applications in the food industry.

Effects of microencapsulation in dairy matrix on the quality characteristics and bioavailability of docosahexaenoic acid astaxanthin.

BACKGROUND: Compared with free astaxanthin (Asta), docosahexaenoic acid astaxanthin monoester (Asta-C22:6) has higher stability and bioavailability. However, Asta-E is still unable to be used in the water system. Hence it is necessary to build a water-soluble delivery system. In this study, Asta-C22:6 microemulsion and microcapsule using whey protein isolate (WPI) and hydroxypropyl-ß-cyclodextrin (HPß-CD) as composite wall material were prepared. They were added to three dairy products (milk powder, yogurt and flavored dairy product). A dairy product rich in Asta-C22:6 with high bioavailability was designed by measuring quality characteristics, sensory evaluation and in vivo experiments. RESULTS: Compared with spray drying, the freeze-drying microcapsule had a higher encapsulation efficiency (72.5%), water content (4%) and better solubility, and Asta-C22:6 microcapsule (1 g L-1 ) yogurt had the best quality. The bioavailability of Asta-C22:6 microcapsule yogurt was further evaluated. After a single oral dose in mice, the bioavailability of Asta-C22:6 microcapsule in yogurt was significantly increased (Cmax  = 0.31 µg mL-1 , AUC0-T  = 3.20 h µg mL-1 ). CONCLUSION: We successfully prepared Asta-C22:6 microcapsule yogurt, which improved the stability and bioavailability of Asta. The present research is meaningful for delivering unstable bioactive small molecules based on WPI and HPß-CD. It provides an experimental basis for the application of Asta-C22:6 and the development of functional dairy products. © 2022 Society of Chemical Industry.

Influence of oil matrixes on stability, antioxidant activity, bioaccessibility and bioavailability of astaxanthin ester.

BACKGROUND: Astaxanthin ester (Asta-E) is used as functional nutraceuticals in many food products. Unfortunately, Asta-E utilization is currently limited owing to its chemical instability and low bioavailability. The purpose of this study is to investigate the promotion effect of oil matrixes on the stability, antioxidant activity, bioaccessibility and bioavailability of Asta-E. RESULTS: The results showed that the stability of Asta-E in six oil matrixes was improved. Based on the 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity experiment, the antioxidant activity of Asta-E was positively correlated with the degree of unsaturation of the oil matrixes, but not with the side chain length. The in vitro gastrointestinal tract (GIT) simulation model and in vivo experiment using mice were also employed to investigate the digestion and absorption characteristics of Asta-E in various oil matrixes. The results demonstrated that the bioaccessibility and bioavailability of Asta-E increased with the increase of fatty acid chain length of oil matrixes (triglyceride oleate > triglyceride caprylate > triglyceride butyrate), as well as with the decrease of unsaturation degree (olive oil > corn oil > fish oil). CONCLUSION: Monounsaturated fatty acids (MUFA) and long-chain triglyceride (LCT) in an oil matrix were the factors that could efficiently improve the bioavailability of Asta-E. Moreover, the size of the mixed micelles of Asta-E during digestion was the main factor influencing the bioaccessibility of Asta-E. This study provides references for the design of suitable oil matrixes for Asta-E. © 2020 Society of Chemical Industry.

Preparation, characterization and antioxidant activity of astaxanthin esters with different molecular structures.

BACKGROUND: Astaxanthin (Asta) is widely used in the nutraceutical and food industry because of its strong antioxidant properties. However, natural Asta mainly exists in the esterified form with various fatty acid chains, making it difficult to understand the particular molecular structure of astaxanthin esters (Asta-Es) that have better antioxidant capacity. In this study, Asta-Es with different molecular structures was systematically prepared, and identified by using thin-layer chromatography (TLC), ultraviolet-visible (UV-visible), high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS), and proton nuclear magnetic resonance (1 H-NMR). In addition, their antioxidant properties were evaluated by 2,2'-diphenylpicrylhydrazyl (DPPH) and ABTS scavenging activity. RESULTS: Fourteen Asta-Es with different molecular structures were systematically synthesized. This study used a simple and efficient method for the separation and purification of astaxanthin monoester (Asta-ME) and astaxanthin diester (Asta-DE) with high purity (86%-94%) by silica gel column chromatography. 13-cis-Asta-E and 9-cis-Asta-E were firstly identified from Asta-E. The DPPH clearance rates and ABTS scavenging rates of Asta-C4:0, Asta-C8:0, Asta-C12:0, and Asta-C18:0 were relatively close, but the DPPH and ABTS scavenging rates of Asta-C18:0, Asta-C18:1, Asta-C18:2, and Asta-C22:6 increased gradually. Among all Asta-Es, Asta-C22:6/C22:6 showed the highest antioxidant capacity, with the DPPH and ABTS scavenging rates of 77.22 ± 3.29% and 51.84 ± 1.65%, respectively. CONCLUSION: In this study, it was concluded that chemically synthesized Asta-Es contained cis-astaxanthin ester and polyunsaturated fatty acid chain increased the antioxidant activity of Asta, showing less effect of the length of fatty acid chain. These results provide useful information for the production and use of highly efficient Asta-E as functional food and pharmaceutical ingredients. © 2020 Society of Chemical Industry.

A smartphone-assisted portable sensing hydrogel modules based on UCNPs and Co3O4 NPs for fluorescence quantitation of hypoxanthine in aquatic products.

Hypoxanthine is a promising index for evaluating the freshness of various aquatic products. Combined the hydrogels containing upconversion nanoparticles (UCNPs), Co3O4 NPs, and N-ethyl-N-(3-sulfopropyl)-3-methylaniline sodium salt/4-amino-antipyrine (TOPS/4-AAP) with a smartphone, a portable sensor was developed for the convenient, sensitive detection of hypoxanthine. With the H2O2 from xanthine oxidase (XOD)-catalyzed reactions of hypoxanthine, the fluorescence of UCNPs was effectively quenched by the purple product produced from the oxidization of TOPS/4-AAP catalyzed by Co3O4 NPs exhibiting peroxidase activity, among which the color change could be transformed into digital signals for quantification of hypoxanthine. The Green value in the RGB analysis of the fluorescence image was negatively proportional to hypoxanthine concentration in the range of 2.5-20 mg/L with a detection limit of 0.69 mg/L and a quantitation limit of 2.30 mg/L. Finally, this sensor was applied for hypoxanthine detection in real aquatic products, showing potential application for freshness evaluation of aquatic products.

A smartphone-assisted sensing hydrogels based on UCNPs@SiO2-phenol red nanoprobes for detecting the pH of aquatic products.

For some aquatic products, pH has been considered a useful index to reflect the changes in materials during the loss of freshness. Based on the inner filter effect (IFE) between deprotonated phenol red (PR) and upconversion nanoparticles (UCNPs), UCNPs coated with PR-doped SiO2 shell were embedded in agarose hydrogel to develop a smartphone-assisted method for pH sensing. With the enhancement of pH response using a phase transfer agent (i.e., tetra butyl ammonium hydroxide, TBAH), the proposed senor realized the colorimetric and fluorescence detection of pH in the range of pH 6.6-8 and pH 6-8, respectively. The sensor also showed satisfied reversibility when switched between pH 6 and 8 for at least 5 cycles. Moreover, this sensor displayed great sensitivity, stability, and portability in analyzing actual fish, shrimp, and shellfish samples, providing a new sight for evaluating the freshness of aquatic products.

Nitrogen-doped carbon dots/Fe3+-based fluorescent probe for the "off-on" sensing of As(V) in seafood.

To better satisfy the application of rapid detection methods in the detection of As(V) in complex food substrates, we developed an "off-on" fluorescence assay to detect As(V) based on the competition between the electron transfer effect of nitrogen-doped carbon dots (N-CDs)/Fe3+ and the complexation reaction of As(V)/Fe3+, using N-CDs/Fe3+ as a fluorescence probe. Solid-phase extraction (SPE) was used to eliminate matrix interference during sample pretreatment. The detection limit was 7.6 ng g-1, with a linear range of 10-100 ng g-1. The method was further used to determine As(V) in different seafood products including snapper, shrimp, clams, and kelp. At the same time, the recovery of the method was validated by high-performance liquid chromatography-inductively coupled plasma mass spectrometry (HPLC-ICP/MS), indicating that the developed method had good recoveries from 86% to 117% and met the needs for accurate determination of As(V). This approach has shown excellent application potential in the field of As(V) detection in various seafood products.

Ratiometric fluorescent nanosystem based on upconversion nanoparticles for histamine determination in seafood.

Histamine is the prime culprit of toxicity resulting from seafood consumption, whereas conventional detection methods are not convenient to meet the needs of rapid histamine analysis nowadays. Based on upconversion nanoparticles (UCNPs) and inner filter effects (IFE), a novel ratiometric fluorescence nanosystem was developed for the efficient detection of histamine. Through pre-treatment with solid-phase extraction (SPE) and colorific azo coupling reaction of histamine, the fluorescence of UCNPs at 548 nm was quenched, while fluorescence at 664 nm was unchanged. Thus, ratiometric fluorescence I548/I664 was inversely proportional to histamine concentration at a wide range of 10-200 mg/L. The detection limit was 7.34 mg/L, one order of magnitude lower than that of the traditional colorimetric method (25 mg/L). In addition, such a convenient and environment-friendly detection system was further employed to quantify the histamine in fish, shrimp, and shellfish samples, showing excellent application potential in seafood safety.

Influence of molecular structure of astaxanthin esters on their stability and bioavailability.

The stability and bioavailability of fourteen astaxanthin esters (Asta-Es) with different molecular structures were investigated using in vitro and in vivo digestion models. The results demonstrated that Asta-E with long-chain and saturated fatty acids were more stable than other types of Asta-E. Astaxanthin diester (Asta-DE) was better than astaxanthin monoester (Asta-ME) and free astaxanthin (F-Asta), as determined based on the degradation rate constant at 60 °C. The absorbability of Asta-Es with different molecular structures was evaluated through the serum concentrations of astaxanthin (Asta). The results indicated that Asta-E with short-chain fatty acids had higher bioavailability than Asta-Es with long-chain fatty acids, whereas Asta-E with high-unsaturation fatty acids had higher bioavailability than Asta-E with low-unsaturation fatty acids. Asta-ME had significantly increased bioavailability compared with Asta-DE. We concluded that the molecular structure of Asta-E could significantly affect their stability and bioavailability.

Kinetic interactions of nanocomplexes between astaxanthin esters with different molecular structures and ß-lactoglobulin.

The influence of different fatty acid carbon chains on the kinetic interactions of nanocomplexes between esterified astaxanthin (E-Asta) and ß-lactoglobulin (ß-Lg) were investigated by multi-spectroscopy and molecular modeling techniques. We synthesized ten different E-Asta bound to ß-Lg and formed nanocomplexes (< 300 nm). Fluorescence spectroscopy showed moderate affinities (binding constants Ka = 103-104 M-1). Docosahexaenoic acid astaxanthin monoester (Asta-C22:6) had the strongest binding affinity towards ß-Lg (Ka = 3.77 × 104 M-1). The fluorescence quenching of ß-Lg upon binding of E-Asta displayed a static mechanism, with binding sites (n) equal to 1. Fourier transform infrared spectroscopy and ultraviolet-visible absorption spectroscopy revealed that E-Asta might enter the ß-Lg hydrophobic cavity, leading to unfolding of the peptide chain skeleton. In summary, ß-Lg and E-Asta can form stable nanocomplex emulsions to achieve an effective delivery process for E-Asta.

Recent advances of molecularly imprinted polymer-based sensors in the detection of food safety hazard factors.

With increasing economic globalization, food safety is becoming the most serious concern in the food production and distribution system. Food safety hazard factors (FSHFs) can be categorized into chemical hazards, biological hazards and physical hazards, with the detection of the former two having fascinated interdisciplinary research areas spanning chemistry, material science and biological science. Molecularly imprinted polymer (MIP) -based sensors overcome many limitations of traditional detection methods and provide opportunities for efficient, sensitive and low-cost detection using smart miniaturized equipment. With highly specific molecular recognition capacity and high stability in harsh chemical and physical conditions, MIPs have been used in sensing platforms such as electrochemical, optical and mass-sensitive sensors as promising alternatives to bio-receptors for food analysis. In this systemic review, we summarize recent advances of MIPs and MIP-based sensors, such as popular monomers, usual polymerization strategies, fresh modification materials and advanced sensing mechanisms. The applications of MIP-based sensors in FSHF detection are discussed according to sensing mechanisms, including electrochemistry, optics and mass-sensitivity. Finally, future perspectives and challenges are discussed.