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In order to study the pilot production process for supercritical CO2 extraction of fat-soluble substances from Lycium barbarum L., and for obtaining the preparation process of zeaxanthin dipalmitate monomer. The effect of pressure, temperature, time and co-solvent on the extraction yield of Lycium barbarum L. fat-soluble substances was studied, the orthogonal test was then used to optimize the extraction rate based on single factor experiment. The carotenoids and fatty acids in the fat-soluble substance of Lycium barbarum L. were analyzed by colorimetry, HPLC and GC-MS, and the zeaxanthin dipalmitate monomer was prepared by high performance preparative liquid chromatography. The results showed that the best pilot production process was that 15% ethanol was added, the extract temperature reached 50 ℃ and pressure reached 30 MPa, and extract for 1.5 h, when the yield and quality of fat-soluble substances were both considered. Under this process, the extraction rate of fat-soluble substances, unsaturated fatty acids and their proportion in total fatty acids, and the content of total carotenoids were relatively higher. While the extraction rate of fat-soluble substances was 8.55%, the content of unsaturated fatty acids was 80.958%, which accounts for 87.94% of the total fatty acid content, the content of total carotenoid and zeaxanthin dipalmitate was 37.64 mg·g−1 and 29.54 mg·g−1, respectively. The monomer of zeaxanthin dipalmitate with purity greater than 99% was prepared by pre-HPLC. In this study, the pilot-scale extraction process for supercritical CO2 extract of fat-soluble substance and the preparation conditions of the zeaxanthin dipalmitate monomer from Lycium barbarum L. were obtained, which provided a basis for the research, development and utilization of the fat-soluble substances of Lycium barbarum L..

The emulsion gel composed of proteins and polysaccharides exhibits significant potential as a targeted delivery system for bioactives in the gastrointestinal tract. In this study, a composite emulsion was prepared by using sodium caseinate (NaCas) and gellan gum (GG), which was subsequently crosslinked with transglutaminase (TG), glucono-δ-lactone (GDL), and calcium ions (Ca2+) to form emulsion gels. The physicochemical properties of the NaCas/GG emulsion gels were characterized to verify the effects of zeaxanthin dipalmitate encapsulation and protection, and a possible mechanism was discussed. The appearance and microscopy analyses revealed that the Ca2+-induced NaCas/GG emulsion gel exhibited superior shape retention and a denser network structure compared to GDL or TG crosslinking methods. The rheological analysis demonstrated that the Ca2+-crosslinked emulsion gels had higher modulus and hardness than their TG- or GDL- crosslinked counterparts. Infrared spectroscopy, molecular docking, and gelling force analysis revealed that the gelation mechanism of these emulsion gels primarily involved carbonyl-amide group crosslinking reactions, hydrogen bonding, and hydrophobic interactions. Furthermore, the Ca2+-crosslinked emulsion gel encapsulating zeaxanthin dipalmitate exhibited excellent thermal stability, resistance to gastrointestinal conditions, and stability. Overall, the above findings highlight that using Ca2+ crosslinking in NaCas/GG composite emulsion yields edible composite materials with enhanced functional performance, thereby expanding the possibilities for food gel design strategies. [Display omitted] • Significant differences in NaCas/GG properties for TG, GDL, and Ca2+ crosslinking • Ca2+ addition have better stability and higher viscoelasticity of NaCas/GG • The amide group and carbonyl group are involved in the Ca2+-crosslinked NaCas/GG • NaCas/GG with Ca2+ had higher zeaxanthin bipalmitate bioaccessibility [ABSTRACT FROM AUTHOR]

In the present study, protein-polysaccharide Maillard conjugates were used as novel emulsifiers and bioactive carriers. Effects and potential mechanisms of zeaxanthin dipalmitate (ZD)-enriched emulsion stabilized with whey protein isolate (WPI)-gum Arabic (GA) conjugate (WPI-GA-ZD) and ZD-free emulsion (WPI-GA) on gut microbiota and inflammation were investigated using a model of dextran sulfate sodium (DSS)-induced colitis in mice. As a result, supplementation with WPI-GA and WPI-GA-ZD improved the serum physiological and biochemical indicators, decreased the expression of pro-inflammatory cytokines and related mRNA, as well as increased the tight junction proteins to a certain extent. 16S rDNA sequencing analyses showed that supplementation with WPI-GA and WPI-GA-ZD presented differential modulation of gut microbiota and played regulatory roles in different metabolic pathways to promote health. Compared with WPI-GA, the relative abundances of Akkermansia, Lactobacillus and Clostridium_IV genera were enriched by the intervention of WPI-GA-ZD. Overall, the designed carotenoid-enriched emulsion stabilized with protein-polysaccharide conjugates showed potential roles in promoting health. [ABSTRACT FROM AUTHOR]

Carotenoids from Lycium barbarum fruits have possessed pharmacological efficacy against eye diseases, cardiovascular disorders, cancer, and benign prostatic hyperplasia. However, the efficient extraction, rapid characterization and activities evaluation of Lycium carotenoids remains a challenge. To concentrate and characterize Lycium carotenoids, we have developed ultrasound-assisted extraction methods with different deep eutectic solvents (DESs) and analyzed carotenoids by ultra-performance convergence chromatography coupled with photo diode array detector and quadrupole time-of-flight mass spectrometry (UPC2-PDA-Q-TOF-MSE). DESs containing choline chloride and malonic acid presented better extraction efficiency and were more environmentally friendly than other extraction methods. Carotenoids were more quickly profiled (in 11 min) by UPC2 compared to by UPLC (in 35 min), with seventeen main peaks were characterized in the MS fragmentation patterns. The in vitro 5α-reductase inhibitory activity of DESs extracts, fractions and components were subsequently assessed, and the predominant component zeaxanthin dipalmitate (ZD) exhibited potent inhibitory activity. Our study provides a chemical and pharmacological basis for the further development of potential new drugs based on Lycium carotenoids.

In the present study, protein-polysaccharide Maillard conjugates were used as novel emulsifiers and bioactive carriers. Effects and potential mechanisms of zeaxanthin dipalmitate (ZD)-enriched emulsion stabilized with whey protein isolate (WPI)-gum Arabic (GA) conjugate (WPI-GA-ZD) and ZD-free emulsion (WPI-GA) on gut microbiota and inflammation were investigated using a model of dextran sulfate sodium (DSS)-induced colitis in mice. As a result, supplementation with WPI-GA and WPI-GA-ZD improved the serum physiological and biochemical indicators, decreased the expression of pro-inflammatory cytokines and related mRNA, as well as increased the tight junction proteins to a certain extent. 16S rDNA sequencing analyses showed that supplementation with WPI-GA and WPI-GA-ZD presented differential modulation of gut microbiota and played regulatory roles in different metabolic pathways to promote health. Compared with WPI-GA, the relative abundances of Akkermansia, Lactobacillus and Clostridium_IV genera were enriched by the intervention of WPI-GA-ZD. Overall, the designed carotenoid-enriched emulsion stabilized with protein-polysaccharide conjugates showed potential roles in promoting health.

Zeaxanthin dipalmitate (3) and two zeaxanthin dipalmitate derivatives, including one new compound (1), were obtained from wolfberry [the fruit of Lycium barbarum L. (Solanaceae)]. Their structures were unambiguously elucidated by spectroscopic analyses. Compound 2 is isolated from the genus Lycium for the first time, and its 1D/2D NMR data are firstly reported. All the compounds belong to carotenoids which are a kind of major bioactive constituents in wolfberry and are also responsible for wolfberry's red color. [ABSTRACT FROM AUTHOR]

Nowadays the xanthophylls lutein and zeaxanthin are used, in ophthalmic preparations for the prevention of age-related degeneration of the retina and cataracts. It is known that the carotenoids enter the body with plant foods or food additives derived from plant or microbial raw materials. They can be also obtained by means of chemical synthesis. Lutein is used in food industry as a colorant. Its source are the flowers of marigold ( ), which is are a common plant. Zeaxanthin is less available than lutein, so the search for new sources with a high content of xanthophyll is relevant. The plants, accumulating zeaxanthin and its esters are the fruits of Goji ( ), known in Chinese medicine as the Goji berry. In the berries zeaxanthin is present mostly in the esterified form, in the form of zeaxanthin dipalmitate. Water- and oil-soluble extracts of dried Goji berries (fruit of Wolfberry, ) have been obtained as a result of the experiment. The conditions of the chromatographic analysis were described with a thin layer chromatography (TLC) method and a high performance liquid chromatography (HPLC) method, and with the preparative separation of zeaxanthin with the method of column chromatography on aluminium oxide. Ultraviolet (UV) spectra of the samples obtained show that the absorption maximum of zeaxanthin standard and that of the sample obtained from the berries of Goji are the same. The optimum conditions to carry out saponification have been established. The content of xanthophyll in extracts is 13.5 mg/100 before saponification, 62 mg/100 g after saponification, 44 mg/100 g in purified ones. An aqueous extract of the berries can be used as a raw material for obtaining biologically active substances (BAS) or can be used as biologically active additives (BAA). It can be used to create a balanced xanthophyll drugs as well.

Fruits of Lycium barbarum L. have been used in Chinese traditional medicine for centuries. In the last decade, there has been much interest in the potential health benefits of many biologically constituents of these fruits. The high level of carotenoids offers protection against development of cardiovascular diseases, diabetes and related comorbidities. In the present work two different selections of Lycium barbarum L., cultivated in Italy and coming from three discrete harvest stages, were subjected to two different grinding procedure and to a simplified extraction method of carotenoid component. CIELAB colorimetric analysis of the freshly prepared purees and HPLC-DAD analysis of carotenoid extracts were performed and compared. Different harvesting dates and grinding procedures deeply influence the carotenoids content and statistical analysis showed high correlation between carotenoid content and colorimetric data. The final model provides a reliable tool to directly assess carotenoid content by performing cheap and routinely colorimetric analyses for food industry. [ABSTRACT FROM AUTHOR]

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Due to the increasing popularity of goji berries, efforts are made to enlarge the offer of goji containing foods. In this study, rice flour based extrudates enriched with goji berries were investigated. The extrusion was performed using a twin screw extruder with constant feed moisture and screw speed. Raw mixtures as well as extruded products obtained were analysed in order to determine antioxidant activity and contents of rutin, zeaxanthin dipalmitate and 2-O-β- d -glucopyranosyl- l -ascorbic acid. The antioxidant activity of goji extrudates was boosted up to 20 times compared to the extrudates without any addition. The process of extrusion increased the antioxidant activity despite of decrease in rutin content. Regardless of extrusion conditions rutin retention in the extrudates was not lower than 60% compared to the respective raw mixtures. In the case of zeaxanthin dipalmitate the retention level was around 40%. 2-O-β- d -glucopyranosyl- l -ascorbic acid was stable at the conditions applied. [ABSTRACT FROM AUTHOR]

A hepatitis B virus (HBV) transgenic mice model was used to establish the fatty liver superimposed model by feeding the methionine choline-deficient (MCD) diet for 8 weeks, with or without the gavage of 2 mg/kg zeaxanthin dipalmitate (ZD) three times per week. Both wild-type and HBV transgenic mice, with MCD diet, gained typical non-obese non-alcoholic steatohepatitis (NASH) and HBV symptoms. Coadministration with ZD exhibited evident therapeutic effects through alleviating those pathological events. Moreover, long-term vehicle-ZD treatment was found to be safe. Thus, ZD is a promising and safe hepato-protective agent against hepatic injury induced by superimposed HBV and NASH in non-obese mice. [ABSTRACT FROM AUTHOR]

BACKGROUND: Goji berries, traditionally used in Chinese medicine, are nowadays gaining popularity in the Western world. The efforts are made to establish their cultivation in Europe. Goji berries might derive from two closely related species: Lycium barbarum and Lycium chinense, however, plant species is rarely stated by commercial suppliers. OBJECTIVE: The aim of this study was to evaluate the antioxidant activity and the bioactive compounds profile of fruits from six goji berries cultivars cultivated in Switzerland and to provide their genetic characterisation. METHODS: Goji fruits were cultivated at the experimental field of the Agroscope Research Center in Wallis, Switzerland. The genetic characterization was carried out by amplifying and sequencing two nuclear genes and one chloroplastic gene. The comparison with L. barbarum and L. chinense obtained from the Conservatory and Botanical Garden of Geneva (CBGG) was made. The profile of carotenoids and polyphenols was analysed using an HPLC-DAD. The antioxidant capacity was determined by ORAC and TEAC assays. RESULTS: DNA sequencing and phylogenetics confirmed that all the cultivars belonged to the Lycium genus. 'Tibet', 'Red Life', 'Sweet Lifeberry', 'Big Lifeberry' seemed to be closely related to a L. barbarum, whereas 'Number One' segregated closer to L. chinense. The individual Saxon, appeared genetically different from all other cultivars and the L. barbarum and L. chinense individuals from CBGG. Zeaxanthin esters were the predominant carotenoid in all six cultivars. 'Number One' had the highest content of phenolic compounds such as rutin and ferulic, chlorogenic, caffeic and p-coumaric acid. CONCLUSIONS: The study confirmed the importance of combining the quantification of bioactive compounds with genetic characterisation in the analysis of goji species. The dissimilarity of 'Number One' and Saxon from four remaining cultivars investigated in this study was evident from the DNA sequencing and Principal Component Analysis of chemical results. [ABSTRACT FROM AUTHOR]

Carotenoids from Lyciu m barbarum fruits have possessed pharmacological efficacy against eye diseases, cardiovascular disorders, cancer, and benign prostatic hyperplasia. However, the efficient extraction, rapid characterization and activities evaluation of Lycium carotenoids remains a challenge. To concentrate and characterize Lycium carotenoids, we have developed ultrasound-assisted extraction methods with different deep eutectic solvents (DESs) and analyzed carotenoids by ultra-performance convergence chromatography coupled with photo diode array detector and quadrupole time-of-flight mass spectrometry (UPC 2 -PDA-Q-TOF-MS E ). DESs containing choline chloride and malonic acid presented better extraction efficiency and were more environmentally friendly than other extraction methods. Carotenoids were more quickly profiled (in 11 min) by UPC 2 5α-reductase inhibitory activity of DESs extracts, fractions and components were subsequently assessed, and the predominant component zeaxanthin dipalmitate (ZD) exhibited potent inhibitory activity. Our study provides a chemical and pharmacological basis for the further development of potential new drugs based on in vitro 5α-reductase inhibitory activity of DESs extracts, fractions and components were subsequently assessed, and the predominant component zeaxanthin dipalmitate (ZD) exhibited potent inhibitory activity. Our study provides a chemical and pharmacological basis for the further development of potential new drugs based on Lycium carotenoids., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2022 Yu, Xia, Li, Wang, Liu, Zheng, Wang, Yang and Shi.)

A nano-emulsion enriched with zeaxanthin dipalmitate (ZDP) was prepared by high-pressure homogenisation to improve the bioavailability of ZDP in Lycium barbarum L. The visual differences, rheology and microstructure of the emulsion were evaluated, which indicated that sodium caseinate (SC), SC/sucrose esters (SE) and SC/octyl succinic anhydride (OSA) modified starch have excellent emulsifying effect. The Fourier transform infrared spectroscopy (FTIR) results revealed that hydrogen bonding and hydrophobic interactions were involved in the formation of ZDP nanocomplexes. The SC/SE-fabricated nano-emulsion achieved the smallest particle size of 152.2 nm and highest ZDP encapsulation efficiency (EE) of 90.65%. The EE of ZDP in the nano-emulsion minor changed with pH, light and heat conditions, except at pH 2.5. The in vitro ZDP release rate in the delivery system was (67.5%) was significantly higher than goji puree (26.6%). These findings may have important implications in designing emulsion systems with improved release rates of lipid-soluble carotenoids. • Nano-emulsions enriched goji carotenoids were prepared. • Nano-emulsion prepared by sodium caseinate/sucrose esters present ideal stability. • ZDP nano-emulsion encapsulation efficiency was 90.6%, exhibiting stronger stability. • Release rate of ZDP in nanoemulsion was significantly higher than that of goji puree. [ABSTRACT FROM AUTHOR]

Abstract: A rapid, high-throughput method was developed to evaluate zeaxanthin levels in Chinese wolfberry fruit, based on the official AOAC (970.64) method. The sample preparation was optimized from the AOAC method with supporting material added to disperse the sample thoroughly. An HPLC method was adopted to replace the time-consuming column separation and spectrophotometric method used previously. Dried Chinese wolfberry fruit was extracted and saponified, simultaneously, in a volumetric flask with a four-solvent blend of hexane:ethanol:acetone:toluene (10:6:7:7); and 40% methanolic potassium hydroxide in order to convert the extracted zeaxanthin dipalmitate to free zeaxanthin in a single step. The flask was placed in a 56°C water bath and shaken at 200rpm for 20min. A normal-phase HPLC method was developed on a silica gel column with an isocratic mobile phase of hexane and ethyl acetate (70:30, v:v). Zeaxanthin was determined to be the dominant carotenoid in Chinese wolfberry fruit. This method was found to be rapid, sensitive and cost-effective for quantitating zeaxanthin in wolfberries compared to the column separation and the spectrophotometric methods traditionally used. Using the developed method, a total of 30 Chinese wolfberry samples from different growers/locations of China were investigated as potential sources of zeaxanthin. The fruit produced in the Ningxia Hui autonomous region had the highest level of zeaxanthin at greater than 1500mg/kg. The zeaxanthin content was not positively correlated to the size of fruit; suggesting that the low cost, smaller fruits may be an economical source for zexanthin extraction. [Copyright &y& Elsevier]

Abstract: This study employed ultrasonic extraction, column elution fractionation and supercritical anti-solvent (SAS) recrystallization in purifying and in preparing micro-sized particles containing zeaxanthin dipalmitate (ZDP) from the Lycium barbarum fruits. Column fractionation of the ultrasonic acetone extract coupled with the SAS process of the ZDP-laden ethyl-acetate solution enhanced the amount of ZDP to 931.5mg/g in the SAS precipitates (about 64.9% recovery) compared to 72.25mg/g from the ultrasonic extract alone. A two-factor experimental design by response surface method showed that feed concentration and feed flow rate were important for SAS in obtaining the highest purity and the smallest mean size of the ZDP particles. The purest ZDP compound (98.3%) also led to the proliferation of anti-hydrogen peroxide oxidation of human adult retinal pigment epithelial cells. [Copyright &y& Elsevier]

A CHCl3: MeOH extract of the fruit of Lycium chinense Mill. (Solanaceae) was found to afford significant protection against carbon tetrachloride-induced toxicity in primary cultures of rat hepatocytes. Subsequent activity-guided fractionation resulted in the isolation of zeaxanthin and zeaxanthin dipalmitate as antihepatotoxic components. Incubation of injured hepatocytes with zeaxanthin dipalmitate reduced the levels of glutamic pyruvic transaminase (GPT) and sorbitol dehydrogenase (SDH) released from damaged cells to 60.5% and 76.3% of those released from untreated controls, respectively. Zeaxanthin also reduced the levels of GPT and SDH to 68.5% and 61.3% of the levels of those released from the untreated control. The results confirm the hepatoprotective activities of zeaxanthins. Antihepatotoxic activities of zeaxanthins are comparable to that of silybin. [ABSTRACT FROM AUTHOR]

Zeaxanthin dipalmitate (ZD) is the main constituent of carotenoids in the fully ripe fruits of Lycium barbarum. In the present study, the effect of the unsaturation degree of oil on the bioaccessibility of ZD in oil-in-water (O/W) emulsions and the bioaccessibility of ZD in the mixture of L. barbarum fruit (L F) and emulsion (L F-E) were investigated. The coarse O/W emulsions were prepared with 5 wt% oil phase and 95 wt% aqueous phase which containing 1.5 wt% lecithin and 0–0.4 wt% xanthan gum (XG). The viscosity and stability of emulsions increased with the increasing of XG concentration, and the emulsion with 0.4 wt% XG had the largest particle size, whereas XG concentration showed a limited effect on ξ-potential. Furthermore, the bioaccessibility of ZD in different unsaturated degree oil emulsions were investigated by in vitro digestion. The results showed that the particle sizes of O/W emulsions decreased significantly from gastric phase to intestinal phase, whereas the ξ-potential absolute values decreased in gastric phase but increased significantly in intestinal phase. Monounsaturated fatty acid-rich oil emulsions led to higher bioaccessibility compared with polyunsaturated fatty acids-rich oil emulsions, and the olive oil emulsion exhibited the highest bioaccessibility of 25.67%. Finally, the powder of L F (50% w/v) was added to the olive oil emulsion (5 wt% oil content) to investigate the effect of lipid on digestion. The bioaccessibility of ZD in L F-E increased 14.8% than that in L F. The results might facilitate the rational design of emulsions that boost the bioaccessibility of carotenoids in fruits and vegetables. Image 10730 • Bioaccessibility of zeaxanthin dipalmitate (ZD) from L. barbarum fruit was evaluated. • Xanthan gum (0.3 wt%) was used to stabilize the oil-in-water (O/W) emulsion. • Oil unsaturation degree affected the bioaccessibility of ZD in O/W emulsion. • Excipient emulsion improved the bioaccessibility of ZD in fruits. [ABSTRACT FROM AUTHOR]

• The fruits of Lycium barbarum L. is a good source of zeaxanthin dipalmitate (ZDP). • Ultrasonic-assisted extraction (UAE) conditions for carotenoid were optimized by RSM. • UAE was efficient due to the high content of ZDP and the short extraction time. • HSCCC was firstly proposed to purify ZDP from the fruits of L. barbarum. • A solvent system of n -hexane/dichloromethane/acetonitrile was developed for HSCCC. Zeaxanthin dipalmitate (ZDP) is a major non-saponified carotenoid in fully ripe fruits of Lycium barbarum L. In the present study, response surface methodology was used to optimize the ultrasonic-assisted extraction (UAE) conditions of carotenoids from the fruits of L. barbarum , and the optimal extraction conditions were determined as follows: ultrasonic power of 360 W, ultrasonic time of 40 min and the ratio of extraction solvent to sample of 30 mL/g. An actual value of ZDP content of 5.40 mg/g and short extraction time indicated the efficiency of UAE. Furthermore, a promising high-speed counter-current chromatography (HSCCC) method was established for the purification of ZDP from the fruits of L. barbarum. With a developed two-phase solvent system composed of n -hexane/dichloromethane/acetonitrile (10/3/7, v/v/v), ZDP with a purity of higher than 95% was successfully isolated from the crude extract. This is the first report on the purification of ZDP by using HSCCC. [ABSTRACT FROM AUTHOR]

Scope: Besides abstinence and nutritional support, there is no proven clinical treatment for patients with alcoholic fatty liver disease (AFLD). Here, the therapeutic effects and mechanisms of action of wolfberry-derived zeaxanthin dipalmitate (ZD) on AFLD models are demonstrated., Methods and Results: The hepatoprotective effects of ZD are evaluated in vitro and in vivo. Direct interacting receptors of ZD on cell membranes are identified by liver-specific knockdown and biophysical measurements. Downstream signaling pathways are delineated using molecular and cellular biological methods. It is demonstrated that ZD attenuates hepatocyte and whole-liver injury in ethanol-treated cells (dose: 1 µm) and a chronic binge AFLD rat model (dose: 10 mg kg -1 ), respectively. The direct targets of ZD on the cell membrane include receptor P2X7 and adiponectin receptor 1 (adipoR1). Signals from P2X7 and adipoR1 modulate the phosphatidylinositide 3-kinase-Akt and/or AMP-activated protein kinase-FoxO3a pathways, to restore mitochondrial autophagy (mitophagy) functions suppressed by ethanol intoxication. In addition, ZD alleviates hepatic inflammation partially via the inhibition of Nod-like receptor 3 inflammasome, whose activation is a direct consequence of suppressed mitophagy. Liver-specific inhibition of receptors or mitophagy significantly impairs the beneficial effects of ZD., Conclusions: ZD is an effective and promising agent for the potential treatment of AFLD., (© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)