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1.
HPLC analysis of Echium plantagineum seed oil shows a complex triacylglycerol (TAG) profile. TAG species were separated on an analytical scale by HPLC and their fatty acid (FA) composition is reported. GLC analyses showed that some TAG fractions reached a stearidonic acid (SDA, 18:4n‐3) percentage significantly higher than that in the original oil. TAG separation on a bigger scale was also essayed, by means of a gravimetric normal‐phase chromatographic column, using silver ion‐silica gel as stationary phase. Gradient elution with solvents of increasing polarity was applied, allowing the separation of valuable TAG species containing γ‐linolenic acid (GLA, 18:3n‐6), α‐linolenic acid (ALA, 18:3n‐3) and SDA as the main constituents (more than 85% of the total FA). An enzymatic hydrolysis reaction showed the distribution of FA in the isolated species of TAG. SDA was the major FA in the sn‐2 position (more than 50% of total FA), followed by ALA (19%) and GLA (18.5%).  相似文献   

2.
This study investigated the levels of γ-linolenic (GLA, 18:3n-6) and stearidonic acid (SDA, 18:4n-3) in various parts of the borage plant (Borago officinalis L.) to elucidate Δ6-desaturase activity. Lipid class and fatty acid (FA) composition during germination of the seeds and FA composition of various borage parts were determined as well as FA compositions of neutral lipids (NL), polar lipids (PL), glycolipids (GL) and monogalactosyl diacylglycerols (MGDG) of borage leaves. When seeds were germinated for 12 days in the dark then exposed to light for 8 h, an overall decrease in oil content was seen with a significant increase in PL from 0.2 to 39.1%. An increase in SDA (from 0.2 to 0.6 g/100 g oil) indicated minor FA synthesis during germination and therefore, Δ6-desaturase activity with the most marked increase after light exposure. The FA compositions of developing and mature seeds were similar, suggesting oil/FA synthesis takes place at the initial stage of seed development. Among all the borage parts, the leaves had the highest amounts of α-linolenic acid (ALA, 18:3n-3) (36.2%), indicating Δ15-desaturase activity, and SDA (25.2%), indicating Δ6-desaturase activity. In leaves, the GL and especially, MGDG fractions had the highest amounts of SDA (31.8 and 39.8%, respectively), indicating that Δ6-desaturase is most active in chloroplasts. Leaves and developing seeds appear to be the major sources of Δ6-desaturase in borage, associated with different organelles in the different tissues.  相似文献   

3.
Various plant seeds have received little attention in fatty acid research. Seeds from 30 species mainly of Boraginaceae and Primulaceae were analysed in order to identify potential new sources of the n‐3 PUFA α‐linolenic acid (ALA) and stearidonic acid (SDA) and of the n‐6 PUFA γ‐linolenic acid (GLA). The fatty acid distribution differed enormously between genera of the same family. Echium species (Boraginaceae) contained the highest amount of total n‐3 PUFA (47.1%), predominantly ALA (36.6%) and SDA (10.5%) combined with high GLA (10.2%). Further species of Boraginaceae rich in both SDA and GLA were Omphalodes linifolia (8.4, 17.2%, resp.), Cerinthe minor (7.5, 9.9%, resp.) and Buglossoides purpureocaerulea (6.1, 16.6%, resp.). Alkanna species belonging to Boraginaceae had comparable amounts of ALA (37.3%) and GLA (11.4%) like Echium but lower SDA contents (3.7%). Different genera of Primulaceae (Dodecatheon and Primula) had varying ALA (14.8, 28.8%, resp.) and GLA portions (4.1, 1.5%, resp.), but similar amounts of SDA (4.9, 4.5%, resp.). Cannabis sativa cultivars (Cannabaceae) were rich in linoleic acid (57.1%), but poor in SDA and GLA (0.8, 2.7%, resp.). In conclusion, several of the presented plant seeds contain considerable amounts of n‐3 PUFA and GLA, which could be relevant for nutritional purposes due to their biological function as precursors for eicosanoid synthesis. Practical applications: N‐3 PUFA are important for human health and nutrition. Unfortunately, due to the increasing world population, overfishing of the seas and generally low amounts of n‐3 PUFA in major oil crops, there is a demand for new sources of n‐3 PUFA. One approach involves searching for potential vegetable sources of n‐3 PUFA; especially those rich in ALA and SDA. The conversion of ALA to SDA in humans is dependent on the rate‐limiting Δ6‐desaturation. Plant‐derived SDA is therefore a promising precursor regarding the endogenous synthesis of n‐3 long‐chain PUFA in humans. The present study shows that, in addition to seed oil of Echium, other species of Boraginaceae (Cerinthe, Omphalodes, Lithospermum, Buglossoides) and Primulaceae (Dodecatheon, Primula), generally high in n‐3 PUFA (30–50%), contain considerable amounts of SDA (5–10%). Therefore, these seed oils could be important for nutrition.  相似文献   

4.
Seeds from 20 species belonging to Boraginaceae, subfamilies Boraginoideae and Heliotropioideae, were surveyed in a search for new sources of γ‐linolenic acid (GLA) and stearidonic acid (SDA). Seed oil content ranged from 7.5% in Echium humile ssp. pycnanthum to 28.8% in Anchusa undulata. GLA ranged from 0.2% of total fatty acids in Heliotropium undulatum to 20.2% in Lithodora maroccana. This last species may be considered as new source of GLA. GLA content was also tested in other Lithodora species from the south east of Spain, to compare GLA percentages among related taxa. GLA amounts in all Echium species reached approximately 12%, in good agreement with previous findings in other European Echium species. SDA ranged from an absence in several Cynoglossum species to 16.2% in Echium humile ssp. pycnanthum, which may be considered as a new source of this fatty acid.  相似文献   

5.
Forty-nine plant species from Spain, belonging to the Boraginaceae, Scrophulariaceae, Onagraceae, and Ranunculaceae families, were surveyed in a search of new sources of γ-linolenic acid (18∶3ω6, GLA). Fatty acid profiles from seeds, stems, roots, flowers and leaves were determined. GLA was detected mainly in seed and root tissues. High GLA amounts were found in seeds of Boraginaceae species, with a maximum of 20.25% of total fatty acids in Myosotis nemorosa. Within the Scrophulariaceae the highest GLA content (10.17%) was found in Scrophularia sciophila. Variable amounts of stearidonic acid, (18∶4ω3, SDA) were present in Boraginaceae species, ranging from 0.08% of total seed fatty acids in Anchusa azurea to 21.06% in Echium asperrimum. SDA was also very abundant in all organs of Asperugo procumbens. A multivariate analysis was performed using our results and those reported for other plant species belonging to the same families in order to investigate a possible correlation between the fatty acid profile and the genera within these families.  相似文献   

6.
Bixa orellana L. seeds possess a resinous lipid (6.3 %), which has a pungent and spicy odour. The seed is known for its medicinal properties such as anti‐inflammatory, antipyretic activity and as a cure for tonsilitis. Trachyspermum copticum L. seed is a well known digestive aid and relief from colic pain. T. copticum possesses essential oil rich in thymol (>50 %) and lipid (15.6 %). The present study was aimed to quantify lipid classes of these two species by silicic acid chromatography and analyze their fatty acid composition by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). It was observed that the seed lipids are rich in neutral lipids with 98.1 and 95.2 % and lower quantities of glycolipids of 1.5 and 3.8 % and phospholipids of 0.36 and 1.0 % in B. orellana and T. copticum, respectively. The fatty acid composition of B. orellana seed lipid showed major quantities of palmitic (26.9 %), linoleic (26.1 %), oleic (17.5 %), linolenic (15.1 %), stearic acid (10.8 %) and small quantities of eicosanoic acid (3.6 %). In T. copticum seed lipids, petroselinic acid (68.3 %) and linoleic acid (25.3 %) together constituted 93 % of the total lipid. The results revealed that the lipids after recovery of the essential components namely, bixin and volatile oil from B. orellana and T. copticum, respectively can be further explored for industrial applications.  相似文献   

7.
Acidolysis of triolein (tri C18:1) with selected long-chain fatty acids (LCFA) was carried out using Candida antarctica (Novozym 435), Rhizomucor miehei (Lipozyme RM IM), Pseudomonas sp. (PS-30), Aspergillus niger (AP-12), and Candida rugosa (AY-30). A better incorporation of stearic acid (SA), α-linolenic acid (ALA), γ-linolenic acid (GLA), arachidonic acid (AA), and docosapentaenoic acid (DPA) was achieved using lipase from Rhizomucor miehei. Lipase from Pseudomonas sp. catalyzed a better incorporation of linoleic acid (LA), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA) into triolein. Thus, Rhizomucor miehei and to a lesser extent Pseudomonas sp. might be considered as providing the most effective enzymes for acidolysis of triolein with selected LCFA. In general, incorporation of LCFA into triolein (tri C18:1) may be affected by chain length, number of double bonds, and the location and geometry of the double bonds as well as reaction conditions and reactivity and specificity of lipases used. As the ratio of the number of moles of a mixture of equimole quantities of C18 FA to triolein changed from 1 to 3, incorporation of C18 FA into triolein increased accordingly with Rhizomucor miehei lipase. Similarly, incorporation of n-3 FA into triolein increased when ALA, DPA, DHA, and EPA were used. The same trend was noticed for a mixture of n-6 FA (LA + GLA + AA) and triolein.  相似文献   

8.
Hemp seeds (HS) constitute a rich nutrient source and contain γ‐linolenic acid (GLA, 18:3, n‐6), which is a healthy fatty acid (FA). The objectives of this research are i) to look for GLA‐rich varieties of unhusked hemp seeds (UHS) and commercial hulled hemp seeds (HHS); ii) to check the influence of different extracting systems on both oil yield and FA profiles; iii) to test a simultaneous oil extraction/GLA‐enrichment process looking to improve GLA content. Hop and European hackberry seeds (both from Cannabaceae family) are also analyzed for comparative purposes. GLA is the most discriminant FA among UHS varieties, ranging in both UHS and HHS seeds from 0.5% to 4.5% of total FA, while hop seeds are the richest GLA source from Cannabaceae (7.2% of total FA). The extraction system selected for hemp seeds processing has a clear influence on oil yields, although, the FA profiles are slightly modified. The use of n‐hexane and n‐hexane:acetone in extractions allows an improvement in oil yields at the same GLA percentage. A process comprising saponification and subsequent cooling allows the improvement of GLA percentage in both hemp and hop seeds extracts at values higher than 10% of total FA, at high yields (>70%). Practical Applications: The global HS market increases significantly year after year and the demand of hemp products is increasing rapidly. The natural GLA sources in nature are limited, and although hemp contains GLA, this reaches low percentages in the oil. Hemp is a well‐established crop with highly standardized agricultural technologies, thus, the development of any well‐designed processes feasible for application in oil extraction industries, would allow the development of new GLA‐based functional seed oils. This would boost the development of the agricultural and food industries dedicated to revaluing hemp products.  相似文献   

9.
BACKGROUND: Olive mill wastewaters (OMWs) are an important residue and several physico‐chemical and/or biotechnological methods have been proposed for their treatment. RESULTS: The ability of three Yarrowia lipolytica strains to grow on and convert glucose‐enriched OMWs into added‐value compounds in carbon‐ and nitrogen‐limited shake‐flask cultures was assessed. Remarkable decolorization (up to 63%) and non‐negligible removal of phenolic compounds (up to 34%, w/w) occurred. In nitrogen‐limited cultures, the accumulation of cellular lipids was favored by OMW addition into the medium. In contrast, although remarkable quantities of citric acid (Cit) were produced in control experiments (cultures without OMW addition), in which Cit up to 18.9 g L?1 was produced with yield of Cit synthesized per sugar consumed ~0.73 g g?1), adaptation of cultures to media supplemented with OMWs reduced the final Cit quantity and conversion yield values achieved. In OMW‐based media, the highest concentration of citric acid produced was 18.1 g L?1, with conversion yield ~0.51 g g?1. In carbon‐limited cultures, despite the presence of inhibitory compounds in the medium (e.g. phenols), biomass production was enhanced with the addition of OMWs. The highest biomass concentration achieved was 12.7 g L?1, with biomass conversion yield per sugar consumed ~0.45 g g?1. Fatty acid analysis of cellular lipid produced demonstrated that adaptation of all strains in OMW‐based media favored the synthesis of cellular lipids that contained increased concentrations of cellular oleic acid. CONCLUSIONS: The Y. lipolytica strains tested can be regarded as possible candidates for simultaneous OMWs remediation and production of added‐value compounds. Copyright © 2011 Society of Chemical Industry  相似文献   

10.
Novel structured monoacylglycerol (MAG)-based phenolic lipids are synthesized from11-bromoundecanoic acid, phenolic acids, and solketal. Selected phenolic acids namely 4-hydroxy benzoic, vanillic, syringic, cinnamic, p-coumaric, sinapic, 4-fluorocinnamic, 4-hydroxyphenyl acetic acid, 3-(4-hydroxyphenyl) propanoic and dihydrocaffeic acids are employed for the synthesis of ten novel MAG-based phenolic lipids. The synthesized phenolic lipids are characterized by FT-IR, NMR, and mass spectra analysis. All the compounds are evaluated for antioxidant, antimicrobial, and cytotoxic activities. MAG derivative 8g of sinapic acid exhibits excellent antioxidant activity in both DPPH assay and inhibition of lipid oxidation assay. MAG derivative 8f bearing p-coumaric acid shows good antimicrobial activity against both Gram-positive and Gram-negative bacterial strains with a minimum inhibitory concentration (MIC) value of 6.25 µm mL−1. All the synthesized compounds are found to exhibit cytotoxicity against B16, DU145, and CHO cell lines, while sinapic and p-coumaric acid derivatives exhibit better activities compared to other derivatives.  相似文献   

11.
The aim of this work was to establish the richness in γ-linolenic acid (GLA, 18:3n-6) and stearidonic acid (SDA, 18:4n-3) of the seed oil of several restricted-range Boraginaceae species, in a search for new valuable oils as advantageous alternatives to the commercially available sources of both polyunsaturated fatty acids. To this end, seeds of selected Boraginaceae species were collected and analyzed. The highest GLA contents (% total fatty acids) were found in the seed oils of Symphytum caucasicum M.Bieb. (22.9 %), Anchusa undulata subsp. undulata (Ten.) Cout. (22.0 %), Anchusa puechii Valdés (20.0 %), Glandora nitida Thomas (19.2 %), Echium pininana Webb & Berth. (17.1 %) and Pentaglottis sempervirens (L.) L. H. Bailey (17.0 %). With regard to SDA, the highest percentage was found in the seed oil of Echium cantabricum (M. Laínz) Fdez. Casas & M. Laínz (14.7 %), followed by Lappula patula (Lehm.) Asch ex Gürke (13.6 %). It is noticeable that several GLA-enriched species stand under a great threat of extinction, thus revealing the importance of the preservation of the natural ecosystems for endangered species.  相似文献   

12.
The content and composition of fatty acids, sterols, tocopherols, and γ-oryzanol in wild rice (Zizania palustris) grown in North America were compared with those in regular brown rice (Oryza sativa L.). The lipid content of wild rice ranged from 0.7 to 1.1%, compared with 2.7% in regular brown rice. The lipids of wild rice comprised mainly linoleic (35–37%) and linolenic (20–31%) acids. Other fatty acids included palmitic (14.1–18.4%), stearic (1.1–1.3%), and oleic (12.8–16.2%). Wild rice lipids contained very large amounts of sterols, ranging from 70 g/kg for a Saskatchewan sample to 145 g/kg for Minnesota Naturally Grown Lake and River Rice. The main sterols found in an unsaponified fraction were: campesterol (14–52%), β-sitosterol (19–33%), Δ5-avenasterol (5–12%), and cycloartenol (5–12%). Some of sterols, γ-oryzanols, were present as the phenolic acid esters; the amount ranged from 459 to 730 mg/kg in wild rice lipids. The largest amounts of tocopherols and tocotrienols, 3682 and 9378 mg/kg, were observed in North Western Ontario wild rice samples, whereas the lowest were 251 mg/kg in an Athabasca Alberta sample and 224 mg/kg in regular long-grain brown rice. The α isomer was the most abundant among tocopherols and tocotrienols. The results of this study showed that wild rice lipids contain large amounts of nutraceuticals with proven positive health effects.  相似文献   

13.
Seed oils from six legume cultivars of Phaseolus vulgaris, grown in the Kingdom of Lesotho, were extracted and their physicochemical properties and FA compositions were determined in order to compare their dietary lipids with those in P. vulgaris cultivars grown in other parts of the world. The oil content of the beans was very low, ranging from 1.5 to 2.0% (w/w). The acid values ranged from 11.0 to 19.2 mg KOH/g, whereas a combination of the PV and the p-anisidine values in Holm's equation gave oxidation values that ranged from 11.0 to 15.0. Thus, considerable enzymatic hydrolysis and oxidation had taken place in the beans during storage. Iodine values ranged from 80.5 to 92.3 (Wijs method), indicating moderate unsaturation in the oils. However, capillary GC analysis, supported by proton NMR analysis of the FAME, gave a total unsaturation range from 79.67 to 84.24%. The dominant FA were α-linolenic acid (36.47–48.81%) and linoleic acid (20.96–36.10%), with appreciable amounts of palmitic acid (14.33–18.23%). This FA composition pattern is quite similar to the FA distribution reported for low oil-bearing legume seeds. Thus, notwithstanding the different climatic and soil conditions, the general properties of lipids in the southern African legume cultivars were quite similar to those of lipids in P. vulgaris cultivars grown in other parts of the world. The high content of α-linolenic acid in the cultivars of P. vulgaris could very likely play a beneficial role in reducing the risk of coronary heart disease among the large populations consuming them in the southern African region.  相似文献   

14.
The lipophilic and hydrophilic antioxidants were evaluated in eight plants: safflower (Carthamus tinctorius), viper’s bugloss (Echium vulgare), quince (Cydonia vulgaris), evening primrose (Oenothera biennis), rose mosqueta (Rosa affinis rubiginosa), black seed (Nigella sativa), sea buckthorn (Hippophae rhamnoides) and borage (Borago officinales). The highest amounts of tocopherols were contained in seeds of borage and sea buckthorn (66.9 mg/100 g and 45.9 mg/100 g, respectively). The sea buckthorn seed lipids had the highest amount of total sterols (10.4 mg/g of lipids). The predominant form was campesterol. Sitosterol was the major sterol in the lipids of other tested seeds. The content of phenolic compounds ranged from 736.5 mg/100 g dry matter (d.m.) (evening primrose) to 74.8 mg/100 g d.m. (safflower). The highest antioxidant activity, expressed in % scavenged DPPH· free radicals, was observed for evening primrose (91.2%), while the lowest for safflower (36.2%). The correlation coefficient between the level of phenolic compounds and antioxidant activity was 0.53.  相似文献   

15.
Schizochytrium limacinum sp. was commercially utilized to produce single cell oil (SCO), but its detailed lipid profile remains unknown. In order to analyze the composition and structure of SCO produced by Schizochytrium limacinum SR31, the SCO extracted at stationary growth phase was separated into neutral lipids (NL), polar lipids and glycolipids by using silica gel column chromatography. The result of lipid classes in NL revealed that triacylglycerol (TAG) was the primary glyceride (93.81 %). Fatty acid (FA) analysis by gas chromatography–mass spectrometer (GC–MS) proved that palmitic acid (29.78 %) and docosahexaenoic acid (25.64 %) were the major FA. Quadrupole time of flight mass spectrometry in electrospray ionization mode coupled with ultra‐performance liquid chromatography was carried out to investigate TAG structures. More than 80 species were identified. Positional distribution of FA in TAG might contribute to further study of the FA shifts during the lipid turnover stage and nutritional evaluation of the SCO.  相似文献   

16.
The FA composition of selected tissues of all six species of eastern Canadian phocid seals: bearded seal (Erignathus barbatus), gray seal (Halichoerus grypus), harbor seal (Phoca vitulina), harp seal (P. groenlandica), hooded seal (Cystophora cristata), and ringed seal (P. hispida) was determined to detect possible differences among different tissues and species. A univariate approach was used to examine differences among different tissues and species separately, and a multivariate approach was taken in examining differences among different species and tissues simultaneously. Findings indicated that FA composition depended on both tissue and species of seal. However, differences were most apparent among tissues. Several unique features of the FA compositions were identified. Blubber was found to be high in the monounsaturated FA, but low in arachidonic acid and dimethyl acetals. Brain tissue lipids, on the other hand, were high in dimethyl acetals and DHA. Lung tissue lipids were very high in palmitic acid, and heart tissue lipids had a higher content of linoleic acid than did lipids of other tissues examined. Thus, the proportions of FA constituents in different tissues were different, most probably due to their varying functional requirements.  相似文献   

17.
Plant sources of omega-3 fatty acids (FA) are needed that can materially raise tissue levels of long-chain omega-3 FA [i.e., eicosapentaenoic acid (EPA; 20:5n-3) and docosahexaenoic acid (DHA; 20:6n-3)]. Stearidonic acid (SDA; 18:4n-3) is the delta-6 desaturase product of alpha-linolenic acid (ALA; 18:3n-3), and when fed to humans, increases red blood cell (RBC) content of EPA to a greater extent than does ALA. This study was undertaken to determine the dose-dependence and time course of the increase in the EPA and DHA content of the heart and RBC in dogs. Adult male Beagles were fed 21, 64, or 193 mg/kg of SDA in in their food daily for up to 12 weeks. Positive and negative controls were given EPA (43 mg/kg) or high oleic acid sunflower oil, respectively. The baseline EPA content of RBC was 0.38 ± 0.03% which increased (P < 0.01) in a dose-dependent manner, with the high dose of SDA and EPA achieving levels of 1.33 ± 0.26 and 1.55. ± 0.28%, respectively. In the heart, the content of EPA rose from 0.06 ± 0.01 to 1.24 ± 0.22% in the EPA group and to 0.81 ± 0.32% in the high SDA group (both P < 0.01). In both tissues, DHA did not change. Compared to dietary EPA, SDA was 20–23% as efficient in raising tissue EPA levels. In conclusion, SDA supplementation increased the EPA content of RBC and heart and may have utility as a plant-based source of omega-3 FA.  相似文献   

18.
Seeds from 50 species belonging to the family Caryophyllaceae, subfamilies Alsinoideae, Silenoideae, and Spergulaceae, were surveyed in a search for new sources of γ-linolenic acid (GLA) having low levels of other interfering PUFA and therefore appropriate for GLA purification. It was detected mainly in Alsinoideae species, with a maximum of 15.6% of total FA in Minuartia laricifolia subsp. ophiolitica. Different amounts of stearidonic acid (18∶4n−3) were present in the Alsinoideae species, ranging from undetectable levels in seven species to 3.30% of total FA in Stellaria media. An ANOVA showed a taxonomical correlation between GLA percentages and the genus/subfamily within this family.  相似文献   

19.
The oil content, FA, and lipid class composition of the mature seeds of six Cordia species were analyzed. Mature seeds of each species were collected in their natural habitat from 2002 to 2004. The total lipid content varied from 1.9% to 13.2%, there beings significant differences between the results found in different years for each species and between the species analyzed. The contents of FFA varied from 2.0% to 7.9% of total lipids. Neutral lipids (NL) were the largest class, making up between 89.6% and 96.4% of the total lipids; the phospholipids (PL) were the second largest class (3.0% to 8.9% of the toal lipids), and the glycolipids (GL) were the smallest class (0.6 to 3.4%). The presence of GLA was determined in each class of lipids; it is predominant in the NL. Levels of GLA ranged from 1.2% to 6.8% of total seed FA. This is, to our knowledge the first study of lipid composition in seeds of species of Cordia from Brazil.  相似文献   

20.
Strains of Zygomycetes, belonging to the genera Zygorhynchus, Mortierella, Rhizopus, Mucor, and Cunninghamella, when cultivated on glucose produced significant quantities of γ-linolenic acid (GLA). After exhaustion of the nitrogen source from the culture medium, all strains accumulated cellular lipids in concentrations ranging from 10 to 28% (oil/dry mycelium). However, in some strains after the depletion of the carbon source (glucose) from the culture medium, a reconsumption of the accumulated oil and synthesis of fat-free cell material was observed. Accumulation of large amounts of oil in the mycelium resulted in the production of oil with low GLA content. Rhizopus stolonifer strain LGAM (9)1, and Cunninghamella sp. strain LGAM (9)2 produced more than 30 mg GLA/g of dry cellular mass. Cunninghamella sp. accumulated 28.1% oil/dry cellular mass, which contained 11.9% GLA. The production of GLA was 260 mg/L of culture medium.  相似文献   

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