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1.
Synthetic mixtures of 24 mono- and diesters of the asymmetric hydroxylated carotenoid lutein with lauric, myristic, palmitic, and stearic acids were analyzed by liquid chromatography-ultraviolet/visible spectroscopy (LC-UV-vis) and characterized by LC-mass spectrometry (MS) and nuclear magnetic resonance spectroscopy (NMR). These compounds were then used for identifying the composition of a commercial lutein supplement. This is the first report of chromatographic separation of mixed fatty acid lutein diesters. Preferential MS loss of fatty acids or water occurred initially at the 3'-hydroxy position in the epsilon-ionone ring and subsequently at the 3-hydroxy position in the beta-ionone ring. This selective fragmentation leads to facile assignment of the specific fatty acids to the appropriate regioisomeric ionone ring. A commercial lutein supplement contained low levels of two pairs of regioisomeric monoesters and nearly equal levels of three homogeneous diesters and five pairs of mixed diesters. Palmitic acid was the predominant fatty acid, with lower amounts of myristic, stearic, and lauric acids.  相似文献   

2.
This study analyzed 11 Chinese cultivars of marigold to determine their major phytochemical contents and antioxidant activities. Dried marigold flowers were extracted with ethanol, ethyl acetate, and n-hexane and the extracts were analyzed by high-performance liquid chromatography-mass spectrometry and chemical methods to determine their lutein esters, phenolic and flavonoid contents, and antioxidant activity, respectively. The different cultivars of marigold showed considerable variations in their lutein ester contents, ranging from 161.0 to 611.0 mg/100 g of flower (dry basis). The lutein esters in marigolds consisted predominantly of six all trans-diesters, but small amounts of cis isomers of the respective diesters were also present. The different cultivars of marigold also showed marked variations in total phenols and flavonoids, as well as antioxidant and radical-scavenging activities. Ethanol was confirmed to be the best solvent for extracting both phenols and flavonoids from marigold flowers, while n-hexane was the worst. The ethanolic extracts also exhibited the highest antioxidant and radical-scavenging activities. The cultivar Xinhong had the highest phenolic and flavonoid contents and radical-scavenging activity, as well as one of the highest lutein contents and antioxidant activities.  相似文献   

3.
Purified lutein diesters deposited on commercial nonporous glass beads were solubilized in supercritical CO(2) in a computerized batch extractor, and their solubilities were compared to their solubilities in hexane. Densities of 0.7, 0.8, and 0.9 g/mL were evaluated without modifiers. Both pressure and temperature increased solubility, although temperatures >50 degrees C promoted carotenoid loss as determined by mass balance. Solubility was enhanced by the use of modifiers and was related to their log P. Chloroform (log P = 2) increased 2.8 times the amount of solubilized lutein diesters compared to pure CO(2) at the same extraction conditions (0.9 g/mL and 40 degrees C) to yield 65% of the amount extracted with hexane. Supercritical CO(2) extraction of lutein diesters could represent a cleaner technology as compared to the current industrial use of hexane with important ecological and health-related implications.  相似文献   

4.
In the present work, the ability of a LC x LC-DAD/APCI-MS method developed at this laboratory to identify the native composition of carotenoid in an extremely complex matrix such as red orange essential oil was demonstrated. To carry out this task, two independent and orthogonal separation mechanisms were coupled through a 10-port switching valve that simultaneously collected the eluent from a microbore cyano column used as the first dimension in normal phase mode and injected it to a conventional reversed phase monolithic C(18) column in the second dimension separation. By using this novel analytical technique together with the use of DAD and APCI-MS detectors it was possible to identify in the sample, without the need of any pretreatment, 40 different carotenoids. Among them, 16 carotenoid monoesters were identified, mainly beta-cryptoxanthin palmitate (C(16:0)), myristate (C(14:0)), and laureate (C(12:0)) as well as several lutein, violaxanthin, antheraxanthin, and luteoxanthin monoesters. Moreover, 21 carotenoid diesters composed by several antheraxanthin, luteoxanthin, violaxanthin, and auroxanthin diesters were found in the native carotenoid composition of the orange oil. The main carotenoid diesters were the laureate palmitate (C(12:0), C(16:0)), myristate palmitate (C(14:0), C(16:0)), and dipalmitate (C(16:0), C(16:0)) diesters, although other diesters were also identified. Besides, two different free carotenes, zeta-carotene and phytofluene, and a xanthophyll, lutein, were also determined. To the authors' knowledge, this is the first time that carotenoid diesters are described and identified in orange essential oil. Likewise, it has been demonstrated that the LC x LC approach proposed in this study is capable of coping with the direct analysis and identification of a complex natural source of carotenoids such as the orange.  相似文献   

5.
Lutein, a naturally occurring carotenoid, is widely distributed in fruits and vegetables and is particularly concentrated in the Tagetes erecta flower. Epidemiological studies suggest that a high lutein intake (6 mg/day) increases serum levels that are associated with a lower risk of cataract and age-related macular degeneration. Lutein can either be free or esterified (myristate, palmitate, or stearate). Both are practically insoluble in aqueous systems, and their solubility in food grade solvents (oils) is very limited, resulting is low bioavailability. To improve its solubility and bioavailability, lutein was solubilized in U-type food grade microemulsions based on ethoxylated sorbitan fatty acid esters, glycerol, R-(+)-limonene, and ethanol. Some of the main findings are as follows: (1) reverse micellar and W/O compositions solubilized both luteins better than an O/W microemulsion, and maximum solubilization is obtained within the bicontinuous phase; (2) free lutein is solubilized better than the esterified one, in the W/O microemulsions, whereas the esterified lutein is better accommodated within the O/W microemulsion; (3) vegetable oils decrease the solubilization of free lutein; (4) glycerol and alcohol enhance the solubilization of both luteins; (5) solubilization is surfactant-dependent in all mesophase structures, but its strongest effect is in the bicontinuous phase.  相似文献   

6.
This study determined the lutein level in various green leafy vegetables (GLVs) and the influence of olive and sunflower oils on the postprandial plasma and eye response of dietary lutein in adult rats, previously induced with lutein depletion (LD). Fresh GLVs (n = 35) were assessed for lutein (L) and its isomer zeaxanthin (Z) levels by high-performance liquid chromatography and liquid chromatography-mass spectrometry. Among GLVs analyzed, Commelina benghalensis L. contained a higher level of L + Z (183 mg/100 g dry wt) and was used as a lutein source for feeding studies. Rats with LD were fed a diet containing powdered C. benghalensis (2.69 mg lutein/kg diet) with either olive oil (OO group), sunflower oil (SFO group), or groundnut oil (GNO group) for 16 days. The L + Z levels of the OO group were markedly (p > 0.05) higher than those of SFO and GNO groups, in plasma (37.6 and 40.9%) and eyes (22.7 and 30.8%), respectively. These results suggest that oleic acid or OO can be used as a suitable fat source to modulate the absorption of dietary lutein to manage age-related macular degeneration.  相似文献   

7.
Commercially prepared marigold flower (Tagetes erecta) extract was saponified and analyzed for carotenoid composition. HPLC analyses were performed on two normal-phase columns (beta-Cyclobond and silica) and on a C(30) reversed-phase column. The extract contained 93% utilizable pigments (detected at 450 nm), consisting of all-trans and cis isomers of zeaxanthin (5%), all-trans and cis isomers of lutein, and lutein esters (88%). All were identified by chromatographic retention, UV-visible spectra, and positive ion electrospray mass spectrometry in comparison to authentic standards. Contrary to previous findings, insignificant levels (<0.3%) of lutein oxidation products were detected in the saponified extract. This compositional determination is important for the application of marigold extract in nutritional supplements and increases its value as a poultry feed colorant because it contains more biologically useful lutein compounds than previously believed.  相似文献   

8.
(13Z,13'Z,3R,3'R,6'R)-Lutein has been isolated and purified from extracts of marigold flowers, fresh raw kale (Brassica oleracea var. Acephala), and human plasma and fully characterized by (1)H and (13)C NMR, UV/vis, and MS. While the concentration of (13Z, 13'Z)-lutein in kale and human plasma compared to (all-E,3R,3'R, 6'R)-lutein was found to be quite low, this compound was readily isolated by fractional crystallization of lutein from marigold extracts. Thus, the mother liquors from two consecutive crystallizations of lutein from a saponified extract of marigold flowers were enriched in (13Z,13'Z)-lutein (8.7% of total carotenoids) and employed for the isolation of this compound by HPLC. The identity of the di-Z-lutein in kale and human plasma has been established by comparison of the HPLC-UV/vis-MS profiles of the purified compounds with those of a fully characterized sample, isolated from marigolds. 3-Hydroxy-beta,epsilon-caroten-3'-one and 3'-epilutein have also been identified in extracts from marigolds.  相似文献   

9.
A simple and efficient method for the isolation and purification of lutein from the microalga Chlorella vulgaris was developed. Crude lutein was obtained by extraction with dichloromethane from the microalga after saponification. Partition values of lutein in the two-phase system of ethanol-water-dichloromethane at different ratios were measured by HPLC so as to assist the determination of an appropriate condition for washing water-soluble impurities in the crude lutein. Partition values of lutein in another two-phase system of ethanol-water-hexane at different ratios were also measured by HPLC for determining the condition for removing fat-soluble impurities. The water-soluble impurities in the crude lutein were removed by washing with 30% aqueous ethanol, and the fat-soluble impurities were removed by extraction with hexane. The final purity of lutein obtained was 90-98%, and the yield was 85-91%.  相似文献   

10.
Quantitative data with regard to dietary (3R,3'R,6'R)-lutein, (3R,3'R)-zeaxanthin, and their (E/Z)-geometrical isomers are scarce, and in most cases, only the combined concentrations of these two carotenoids in foods are reported. Lutein and zeaxanthin accumulate in the human macula and have been implicated in the prevention of age-related macular degeneration (AMD). The qualitative and quantitative distributions of lutein, zeaxanthin, and their (E/Z)-isomers in the extracts from some of the most commonly consumed fruits, vegetables, and pasta products were determined by HPLC employing a silica-based nitrile-bonded column. Green vegetables had the highest concentration of lutein (L) and zeaxanthin (Z), and the ratios of these carotenoids (L/Z) were in the range 12-63. The yellow-orange fruits and vegetables, with the exception of squash (butternut variety), had much lower levels of lutein in comparison to greens but contained a higher concentration of zeaxanthin. The ratio of lutein to zeaxanthin (L/Z) in two North American bread varieties of wheat (Pioneer, Catoctin) was 11 and 7.6, respectively, while in a green-harvested wheat (Freekeh) imported from Australia, the ratio was 2.5. Between the two pasta products examined, lasagne and egg noodles, the latter had a much higher concentration of lutein and zeaxanthin. The levels of the (E/Z)-geometrical isomers of lutein and zeaxanthin in these foods were also determined.  相似文献   

11.
In aqueous NaOH-extracts of top-soils (0-10 cm) from typic chromuderts, phosphorus was determined by NMR-spectroscopy. In addition to inorganic orthophosphate, orthophosphate monoesters and diesters were detected. Pyrophosphate was only found in traces after clear-cutting and burning of the forests. The result of clear-cutting and agricultural land use is an increase of inorganic P from 19% (forest) to 33% (maize field). Compost gardens and mature tree gardens contain only 9-13% inorganic P in the NaOH-extract. The organic P-fraction consists mainly of orthophosphate monoesters (57-72%). The orthophosphate diester content is only 10–21%. It could be shown, that the increase of inorganic P in the course of clear-cutting and ploughing is correlated with a decrease of orthophosphate mono- and diesters.  相似文献   

12.
The carotenoid profile of orange juice is very complex, a common characteristic for citrus products in general. This fact, along with the inherent acidity of the product, which promotes the isomerization of some carotenoids, makes the correct identification of some of these pigments quite difficult. Thus, one of the carotenoids occurring in orange juice has been traditionally identified as isolutein, a term used to refer to lutein epoxide, although enough evidence to support that identification has not been given. In this study, the carotenoid previously identified as isolutein/lutein epoxide in orange juice has been isolated and identified as a 9 or 9'-cis isomer of antheraxanthin as a result of different tests. To support this identification, a mixture of geometrical isomers of lutein epoxide isolated from petals of dandelions was analyzed under the same conditions used for orange juice carotenoids to check that neither their retention times nor their spectroscopic features matched with those of the orange juice carotenoid now identified as a cis isomer of antheraxanthin.  相似文献   

13.
We investigated an improved method for the separation of high-purified lutein from a commercially available spray-dried Chlorella powder (CP) using fine grinding by jet mill and flash column chromatography on a silica gel. Saponification and extraction of lutein were enhanced 2.3-2.9-fold in jet mill-treated CP (mean particle size, 20 microm) as compared to untreated CP (mean particle size, 67 microm). The carotenoid extract was dissolved in ether-hexane (1:1 v/v) and subjected to flash column chromatography on silica gel. A mixture of alpha- and beta-carotene was eluted with hexane, followed by elution with hexane-acetone-chloroform (7:2:1 v/v). Lutein (dark-orange band) was collected after the elution of an unknown colorless compound (detected based on UV absorbance). The purity of lutein in this fraction was over 99%, and the yield was 60%. The present study provides key information for obtaining highly purified lutein using flash column chromatography on a silica gel.  相似文献   

14.
The composition of organic phosphorus compounds was studied using the 31P NMR spectroscopy method in agrogray soils with periodic water logging. The phosphorus content was determined by the specific difference between the hydrological and the redox regimes of these soils. The phosphorus of the organic compounds in the agrogray soils with contrasting water regimes is composed mostly of phosphoric monoesters and diesters, including nucleic and teichoic acids. The relative distribution of the monoesters and inorganic orthophosphates is shown depending on the climate and the soil’s position in the relief. The area of the monoester peaks increases by two times and that of the mineral orthophosphate decreases by six times in the agro-gray soils of Bryansk opolie with an optimal regime of moistening and evaporation in comparison with the agro-gray gleyed soils of Kolomna opolie. As the degree of the soil hydromorphism in the sequence of deeply gleyed soils and gleyic soils increased, the portion of monoesters decreased. Favorable conditions for the microbial activity are formed in soils with a contrasting redox regime, and this is expressed in the accumulation of labile diesters. Inverse relationships were found between the distributions of the mono- and diesters in iron-manganic nodules and in the soils enclosing them; this was caused by the different mechanisms of the stabilization of the stable and labile phosphorus containing compounds. A high percentage of mineral orthophosphate in the nodules allows assuming the presence of chemisorbed orthophosphate ions in organomineral phosphate-metal-humus complexes. The transformation of iron-manganic nodules under the influence of drying demonstrates the more direct participation of microorganisms in the nodules’ formation than the contribution of the physicochemical processes.  相似文献   

15.
The different forms of phosphorus (P) in 0.5 m sodium hydroxide extracts of soils from long-term field experiments at Rothamsted were characterized by 31P-nuclear magnetic resonance spectroscopy (NMR). The extract from an old grassland soil (pH 4.6) from a plot of the Park Grass Continuous Hay Experiment that had received no fertilizer or lime for at least 125 years contained the following forms of P: inorganic orthophosphate (22% of the extracted P), orthophosphate monoesters (49%), orthophosphate diesters (14%), phosphonates (3%), pyrophosphate (4%) and two unidentified forms of P (7%). The soil extract from a Park Grass plot given inorganic phosphate fertilizer (35 kg P ha?1) annually for 121 years contained the same forms of P and, in addition, a small amount of polyphosphate. There was also evidence of an increase in the orthophosphate monoester fraction. Another old grassland soil, of pH 6.1, contained more total and organic P than Park Grass but the extract contained fewer forms of P: inorganic orthophosphate (14% of the extracted P), orthophosphate monoesters (39%), orthophosphate diesters (34%) and an unidentified form (13%). An area of this grassland that had been ploughed up 20 years previously, and kept bare since, contained less organic P. The extract contained less of the phosphate diesters but the more stable monoesters remained relatively unchanged.  相似文献   

16.
Carotenoids, lutein and zeaxanthin, found in fruits and vegetables, comprise the macula pigment of the eye. These carotenoids exist in plants as the all-trans geometric form; however, in human plasma, cis isomers of these carotenoids have also been identified. Thermal processing can induce carotenoid trans to cis isomerization. The aim of this research was to determine if thermal processing induces isomerization of lutein and zeaxanthin and to quantify the extent of this reaction. High-performance liquid chromatography was used to separate and quantitate geometric isomers of lutein and zeaxanthin. Isomers were tentatively identified by UV-visible absorbance spectra, comparison of retention times to those of isomerized standards using C(30) chromatography, and mass spectrometry. Thermal processing increased the percent cis isomers of lutein and zeaxanthin up to 22 and 17%, respectively. Further studies are needed to consider the physiological impact of consuming carotenoid isomers in processed vegetables.  相似文献   

17.
The influence of thermal treatment and light exposure on degradation and isomerization of the predominant carotenoids (lutein and beta-carotene) occurring in green leafy vegetables was assessed. The effect of lipid addition on carotenoid stability was also evaluated. For the first time, the stabilities of pure carotenoids and chloroplast-bound carotenoids were compared. Besides degradation, heating caused carotenoid isomerization in all samples. Whereas pure carotenoids favor 13-cis isomers, in native chloroplasts and heated chloroplasts 9-cis isomers were predominant. Illumination of freshly prepared chloroplast isolates caused an initial increase in the level of lutein (9.6%) and beta-carotene (29.8%), while pure carotenoids exhibited time-dependent degradation. The addition of lipids to chloroplast preparations had the reverse effects on the retention of both carotenoids after heating; isomerization was not significantly affected. It was demonstrated that carotenoid stability has to be evaluated for every individual pigment in its genuine environment. Stability data based on model systems (e.g., pure carotenoids) may not be transferred to complex food matrices without intensive investigation.  相似文献   

18.
Chlorella is a nutrient-rich microalga that contains protein, lipid, minerals, vitamins, and high levels of lutein. This study evaluated the bioavailability of lutein from Chlorella vulgaris using a coupled in vitro digestion and human intestinal Caco-2 cell model. Lutein bioaccessibility was low, and approximately 75% of total C. vulgaris lutein was not micellized during the digestion process but remained in the insoluble digestate. Microfluidization improved lutein micellization efficiency during C. vulgaris digestion. C. vulgaris was microfluidized at a pressure exceeding 10000 psi, and the cell surface disruption was visualized by scanning electron microscopy. The mean C. vulgaris particle size was reduced from 3.56 to 0.35 μm with the microfluidization treatment. C. vulgaris microfluidization at 20000 psi was three times more efficient for aqueous lutein micelles production as compared with untreated C. vulgaris, and the final lutein content accumulated by intestinal Caco-2 cells was also higher with microfluidization. C. vulgaris lutein stability was not affected by microfluidization. These results indicate that microfluidization may be useful for improving lutein bioaccessibility from C. vulgaris during food processing.  相似文献   

19.
The objectives of this study were to develop a high-performance liquid chromatography method for analysis of carotenoids in spear shrimp shells (Parapenaeopsis hardwickii) and to compare the extraction efficiency of carotenoids by supercritical carbon dioxide (SCD) and solvents. Results showed that the most appropriate HPLC method was accomplished by employing a Cosmosil 5C18-AR-II column and a mobile phase of methanol-dichloromethane-acetonitrile (90:5:5, v/v/v) (A) and water (100%) (B) with the following gradient elution: 92% A and 8% B in the beginning, decreased to 4% B in 9.5 min, 1% B in 26 min, 0% B in 35 min, maintained for 25 min, and returned to 92% A and 8% B in 61 min. All-trans-astaxanthin and its two cis isomers, as well as five astaxanthin monoesters and 11 diesters were resolved within 60 min with a flow rate at 2 mL/min and detection at 480 nm. Astaxanthin diesters were found to contain 12 fatty acids, of which palmitic acid and stearic acid constituted a large portion, whereas astaxanthin monoesters were found to contain 10 fatty acids with arachidonic acid dominating. Solvent extraction could generate a higher content of trans-astaxanthin and astaxanthin esters, while SCD extraction could produce greater levels of 9-cis-astaxanthin and 13-cis-astaxanthin.  相似文献   

20.
Economically viable and environmentally acceptable methods to recycle organic wastes are needed by the pulp and paper industry. We assessed the potential for composting the Virginia Fibre Corporation's (VFC) combined primary and secondary dewatered paper mill sludge (PMS) and evaluated the suitability of the finished product as a potting soil substitute. Composting treatments were: 1) PMS with no supplemental N (control), 2) PMS + 15 kg N/Mg PMS (dry weight), and 3) PMS + 30 kg N/Mg PMS (dry weight). Composting was conducted for 129 days and treatment effects were evaluated by windrow temperature trends. A container plant growth study employing various particle size fractions and proportions of the control PMS compost and a commercial potting medium (Promixtm) was conducted in a greenhouse to assess the capability of the compost to support growth of radish (Raphanus sativus L.), snap bean (Phaseolus vulgaris L.), marigold (Tagetes erecta L.), and green pepper (Capsicum sp.). Windrow temperatures were lower with no supplemental N than with the N additions during the initial three weeks and were higher with increasing N rate during the last month of composting, which indicated that the unamended sludge may have been N-limited for maximum biological activity. Reduced temperatures in the high N treatments during the midpoint of the composting process may have been induced by ammonia toxicity. However, cured compost chemical properties and stability were not influenced by treatment and were indicative of good quality compost. The lower amount of plant-available water and greater amounts of plant-available nutrients supplied by the compost than the commercial potting medium resulted in less dry matter produced by all plants except green pepper, whose higher nutrient needs were supplied better by the compost than the commercial potting medium alone. Therefore, the paper mill sludge compost may best be used as an organic fertilizer, soil amendment, or supplemental nutrient source for potting media, rather than as a potting medium alone.  相似文献   

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