Article

Tocopherols, Tocotrienols and Carotenoids in Kernel Oils Recovered from 15 Apricot (Prunus armeniaca L.) Genotypes

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  • Institute of Horticulture
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Abstract

We studied the content of tocopherols, tocotrienols and carotenoids in oil extracted from the kernels of 15 apricot (Prunus armeniaca L.) genotypes and the associated oil yield of the studied samples. The oil yield in apricot kernels was in a wide range of 27.2–61.4% (w/w) dry weight basis. For each class of studied compounds (tocochromanols and carotenoids), a three-fold difference was found between the lowest and the highest content (78.8–258.5 and 0.15–0.53 mg/100 g of oil, respectively). γ-Tocopherol accounted for 91–94% of total tocochromanols detected in all tested samples. Lutein, zeaxanthin, β-cryptoxanthin and β-carotene were the main compounds among the eight different carotenoids detected in apricot kernel oils; they comprised 76–94% of the total carotenoids content, and compositions were characteristic for specific genotypes. The oil yield and content of lipophilic antioxidants in apricot kernel oils were significantly affected by the genotype. The oil yield was negatively correlated with the total amount of tocochromanols (r = −0.910) and carotenoids (r = −0.704) in apricot kernel oils.

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... Table 3.1 groups the works devoted to the extraction and analysis of apricot kernel oil that have appeared in the last decade. Solvent extraction is the most popular choice (Dulf et al., 2017;Pop et al., 2015;Senica et al., 2017;Hassanien et al., 2014;Orhan et al., 2008;Górnaś et al., 2017;Manzoor et al., 2012;Popa et al., 2011;Ö zcan et al., 2010;Rai et al., 2013;Bachheti et al., 2012;Ö zcan, 2009, 2015; and petroleum ether or nhexane are the most usual solvents, although methanol or chloroform have also been used. Extractions have been carried out at room temperature, using an ultrasound bath, or with Soxhlet or Twisselmann extractors. ...
... Orhan et al. (2008) observed that the use of an ultrasound bath and the slight increase in temperature enabled a significant reduction in the extraction times previously employed (2 days) to extract the apricot kernel oil. In other work Górnaś et al. (2017) extracted the apricot kernel oil in an ultrasound bath in just 5 min at a temperature of 35 C. Soxhlet and Twisselmann extractors have also been used to obtain oilseeds. Both instruments enable extraction under reflux, using a discontinuous flow, in the case of the Soxhlet extractor, or a continuous flow, in the Twisselmann extractor (Noke et al., 2013). ...
... The variety with the highest tocochromanols content is Veselka with 258.5 mg/100 g oil . The most abundant vitamer in Veselka kernel oil is γ-tocopherol, followed by α-tocopherol, while the rest of tocopherol homologues and tocotrienols are in trace concentrations (Pop et al., 2015;Górnaś et al., 2017Górnaś et al., , 2015. As demonstrated by , bitter apricot kernels presented slightly higher contents of tocochromanols than sweet kernels. ...
Chapter
Apricot (Prunus armeniaca L.) is a stone fruit belonging to the Prunus genus and is highly consumed worldwide. Its processing generates large amounts of waste that can reach thousands of tons of residues per year. The recovery of this waste material kills two birds with one stone. On the one hand, it contributes to solving the environmental problem derived from the discarding or incineration of residues and, on the other hand, it enables the obtaining of valuable substances with a huge potential in the food, cosmetic, or pharmaceutical fields. The main by-product of the apricot is the stone. The most valued part of the stone is the kernel. Apricot kernel is a great source of oil, mainly composed of fatty acids, especially unsaturated fatty acids. This oil also presents high concentrations of triterpenoids, carotenoids, vitamin E active compounds, phytosterols, and polyphenols. Apricot kernels are also a source of proteins, peptides, and essential oil. This chapter groups the most recent works (2008–18) devoted to the study and application of apricot by-products.
... mg/kg of oil) has been observed by Aithammou et al. [22]. is variability in tocopherol concentration can be attributed to many factors, such as the climate [23], variety [24], extraction method [25], storage conditions [26], fruits form [27], and fruits maturity [28]. e genotype has an important impact on oil yield and composition [29]. In the case of apricots (Prunus armeniaca L.), the genetic factor influences the composition of tocopherol homologues [29]. ...
... e genotype has an important impact on oil yield and composition [29]. In the case of apricots (Prunus armeniaca L.), the genetic factor influences the composition of tocopherol homologues [29]. Furthermore, the variability of tocopherol composition in various seed oils recovered from the by-products of the apple industry has been attributed to cultivars [30]. ...
... In addition, Gharby et al. [50] mentioned that Argan oil has the highest concentration of α-and δ-tocopherols compared to cactus pear seed oil. As reported by Górnaś et al. [29], biotic factors (genotype) also affect the content of tocopherols in fruit kernel oils, such as apple cultivars (Malus domestica Borkh.), plums (Prunus domestica L.), and apricots (Prunus armeniaca L.). However, Dolde, Vlahakis, and Hazebrock [51] reported that the composition of tocopherols in oil seeds, such as sunflower and soybean, is highly dependent on environmental conditions rather than on genetic factors. ...
Article
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Valorisation of Argan oil requires the precise identification of different provenances markers. The concentration of tocopherol is regarded as one of the essential parameters that certifies the quality and purity of Argan oil. In this study, 39 Argan samples from six different geographical origins (Safi, Essaouira, Agadir, Taroudant, Tiznit, and Sidi Ifni) from the central west of Morocco were collected and extracted using cold pressing. The total tocopherol amount was found to range from 783.23 to 1,271.68 mg/kg. Generally, γ-tocopherol has the highest concentration in Argan oil. It should also be noted that the geographical origin was found to have a strong effect on the amounts of all tocopherol homologues studied. Principal component analysis of tocopherol concentrations highlighted a significant difference between the different provenances. The content of tocopherol has also been found to be strongly influenced by the distance from the coast and altitude, whereas no significant effect was found regarding other ecological parameters. The prediction ability of the LDA models was 87.2%. The highest correct classification was revealed in coastal provenances (100%), and the lowest values were from the continental ones (71.4%). These results provide the basis for determining the geographical origins of Argan oil production with well-defined characteristics to increase the product’s value and the income of local populations. In addition, this study provides a very promising basis for developing Argan varieties with a high content of tocopherol homologues, as well as contributing to the traceability and protection of Argan oil’s geographical indication.
... Stages of maturity apricot) [17]. Moreover, our results (Table 1) show highest levels total tocopherol contents compared to Turkish apricot ones but lowest than those of Gornas et al. [23]. The major vitamin E homologue was γ tocopherol in all three apricot seeds and founded as its highest level in 55.10 mg/100 g γ tocopherols at immature stage (IM) and 37.98 mg/100 g γ tocopherols at full maturity (MS) in AprO semi-sweet cultivar. ...
... In general, α and γ-Tocopherol comprise more than 60% of the total vitamin E content in most oils with an exception for palm oil, which the amount is about 30% (α-Tocopherol) and 60% (tocotrienol). When compared to many vegetable oils and nut oils, apricot oils especially semi sweet AprO contain a considerable content of tocopherols and mainly γ-tocopherol as reported for the Turkish Alyanak variety by Turan et al. [9] and Lativian genotype apricots by Gornas et al. [23]. ...
... The data presented by other authors also confirmed the high amount of β-carotene in apricot fruits [6] and the presence of α-carotene, γ-carotene, zeaxanthin and lutein in lower amounts [2,6,15,16,23]. Furthermore, carotenoid analysis of Croatian apricot cultivars among maturity showed existence of β-carotene in major amount along with γ-carotene and lutein at immature, semi-mature, and mature stages of the fruits but α-Carotene was only detected in one apricot variety (Velika rana) at full maturity stage [6]. Interestingly, it was reported by literature, that β-carotene content (12.2 mg/100 g of oil) was lower than irradiated ones (16.7 mg/100 g of oil). ...
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During the ripening of three apricots cultivars (“Bargoug”, “Chechi Bazza” and “Oud Rhayem”) grown in two different geographical regions of Tunisia (Testour and Gafsa regions), the changes of tocopherols, tocotrienols and carotenoids contents were determined by using high-performance liquid chromatography (HPLC) with UV–Vis photo diode array detection. The total tocopherols content ranged to from (30.43 mg/100 g of oil) to (70.69 mg/100 g of oil) with 7 compounds identified as α-T, α-T3 β-T, γ-T, γ-T3, δ-T and δ-T3 mainly consisted with γ-T (28.8 to 44.6 mg/100 g of oil). Furthermore, all apricot varieties were found to be a good source of carotenoid compounds with β- carotene as the major one ranging from 127 to 566 µg/100 g of oil followed by α-carotene ranging from 25.7 to 81.8 µg/100 g of oil and γ-carotene ranging from 7.7 to 56.38 µg/100 g of oil. Zeaxanthin and Lutein were found only in bitter apricot precisely at immature stage (14 DAP) with respectively 105.2 and 141.8 µg/100 g of oil values.
... Chandrasekara and Shahidi 22 determined that oil content was 41.30 to 42.58 in cashew nuts roasted at different temperatures. The oil yields of apricot kernels changed between 27.2 and 61. 4 w/w dry weight basis depending on the genotype 23 . Korekar et al. 24 determined 92.2 to 162.1 mg GAE/100 g total phenol in apricot kernels. ...
... Additionally, it has been stated that Folin-Ciocalteu reagent may not be precise for the determination of phenolic compounds as it may encounter certain analytical errors due to interaction and reaction with other non-phenolic components of samples being analyzed. Hence, chromatographic procedures HPLC may give better results during quantification of phenolic compounds 23,27 . Furthermore, this assay may be more useful in assessing the total antioxidants reducing capacity as being an electeon transfer-based assay it may measure the capacity of an antioxidant to reduce demonstrated by change in color an oxidant and the degree of color change is correlated with the sample s antioxidant concentrations 27,28 . ...
Article
The oil recovery from Alyanak apricot kernel was 36.65% in control (unroasted) and increased to 43.77% in microwave-roasted kernels. The total phenolic contents in extracts from apricot kernel were between 0.06 (oven-roasted) and 0.20 mg GAE/100 g (microwave-roasted) while the antioxidant activity varied between 2.55 (oven-roasted) and 19.34% (microwave-roasted). Gallic acid, 3,4-dihydroxybenzoic acid, (+)-catechin and 1,2-dihydroxybenzene were detected as the key phenolic constituents in apricot kernels. Gallic acid contents varied between 0.53 (control) and 1.10 mg/100 g (microwave-roasted) and 3,4-dihydroxybenzoic acid contents were between 0.10 (control) and 0.35 mg/100 g (microwave-roasted). Among apricot oil fatty acids, palmitic acid contents ranged from 4.38 (oven-roasted) to 4.76% (microwave-roasted); oleic acid contents were between 65.73% (oven-roasted) and 66.15% (control) and linoleic acid contents varied between 26.55 (control) and 27.12% (oven-roasted).
... The major antioxidant components present in the bitter apricot kernel are 2,2-azino-bis (3-ethlybenzothaizoline-6-sulfonic acid, 2,2-diphenyl-1-picrylhydrazyl, ferric reducing antioxidant power assay, oxygen radical absorbance capacity assay, and Trolox equivalent. The rich nutritional composition of apricot and apricot kernel, which contain phytonutrients, saccharides, organic acids, minerals, and vitamins, is the main fact for using this fruit in folk medicine [79]. ...
... These dietary fibers are effective in lowering LDL cholesterol [82]. Similarly, in vivo studies in animals showed a major effect of apricot feeding found to be reduced by up to 10-20% disease compared to the control group [79]. Furthermore, after supplementation of apricot to rats, the level of antioxidant capacities such as iron reducing power as total phenolic content, DPPH radical scavenging capacities have increased. ...
Article
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Apricot kernel, a by-product of apricot fruit, is a rich source of proteins, vitamins, and carbohydrates. Moreover, it can be used for medicinal purposes and the formation of food ingredients. Several techniques have been adopted for the extraction of bioactive compounds from the apricot kernel such as solvent extraction, ultra-sonication, enzyme-assisted, microwave-assisted, and aqueous extraction. Apricot kernels may help to fight against various diseases such as cancer and cancer immunotherapy, as well as reduce blood pressure. Additionally, the kernel is famous due to its diverse industrial applications in various industries and fields of research such as thermal energy storage, the cosmetic industry, the pharmaceutical industry, and the food industry. Especially in the food industry, the apricot kernel can be used in the preparation of low-fat biscuits, cookies, cakes, and the fabrication of antimicrobial films. Therefore, in this review article, the bioactivity of the apricot kernel is discussed along with its chemical or nutritional composition, characterizations, and applications.
... The Prunus seed oils present a great variation in the content and composition of vitamin E-active compounds [57]. γ-Tocopherol is the major constituent; its content in the seed oil of various sweet and bitter apricot cultivars was found to vary from 141.6 to 330.2 mg/kg [57] or from 424.8 to 732.7 mg/kg [67] while they were much higher in sour cherry seed oil (891-1333 mg/kg of oil) [58]. Noticeably, the content of these materials in γ-tocopherol is comparable to those of plant oils derived from nuts (e.g., peanuts) and oilseeds (corn, soya) [65]. ...
Article
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The inedible part (stones, husks, kernels, seeds) of the tree fruits that are currently processedin various regions of Greece constitutes a huge portion of the fruit processing solid waste that remainsunderexploited. In this review, the existing scientific background for the composition and content offruit stone and seed in bioactive ingredients is highlighted for olives, stone fruits and citrus fruits thatrepresent the economically most important tree crop products of the country. The content of bioactivecompounds may vary considerably depending on the quality of the raw material and the treatmentduring processing. However, both the hydrophilic and the lipophilic fractions of the seeds containsignificant amounts of the primary and the secondary plant metabolites. Among them, phytosterolsand several types of polyphenols, but also squalene, tocopherols and some other terpenoids witha unique structure are of particular importance for the utilization and valorization of stones andseeds. Official and scholar records about the current management practices are also presented tohighlight the dynamics of the Greek fruit sector. Prospects for the regionalization of fruit seed wastes,in line with EU-promoted Research and Innovation Strategies (RIS) for Smart Specialization arecritically discussed
... The impact of Japanese quince genotype on the seed oil yield was not studied previously, nevertheless, a similar oil extractability from Japanese quince seeds, as obtained in the present study, by the ultrasound-assisted and coldpress extraction methods were reported previously [5,6]. The importance of the genotype of ccep t e d A Arti cle 13 plants belonging to the Rosaceae family for potential oil extraction from seeds and kernels has been underlined as an important economic factor [37,38]. ...
Article
The impact of the extraction technique and genotype on the oil yield and profile/concentration of fatty acids, tocopherols, sterols, and squalene in oil obtained from the seeds of three Japanese quince (Chaenomeles japonica) cultivars (“Rondo,” “Darius,” and “Rasa”) are studied. The oil recovery from Japanese quince seeds is affected by two factors; extraction technique, and genotype. The lowest oil recovery is recorded for the cold‐press method and cv. “Rondo,” and the highest for ultrasonic extractions and cv. “Rasa.” The profile of fatty acids in Japanese quince seed oil is dominated by three fatty acids C18:2, C18:1, and C16:0. The extraction method does not impact fatty acid and tocopherol composition as well as squalene content, as opposed to genotype, which has a statistically significant impact. The composition of tocopherols in the Japanese quince seed oil is dominated by the α‐T (97%), while the β‐T and γ‐T constituted only minor level (below 2% of each). The extraction type and genotype have a significant impact on the composition of the most of sterols. Regardless of the type of extraction and genotype, the β‐sitosterol consists of over 80% of total sterols in Japanese quince seed oil. The plant genotype is the key factor, which determines the profile of the fatty acids and the concentration of bioactive compounds in the extracted oil from Japanese quince seed, while the extraction technique plays a secondary role. Practical Applications: The agro‐industrial by‐products generated by the fruit industry, for example, seeds, continue to rise year to year. One of the more popular processed fruit crop is Japanese quince (Chaenomeles japonica). This study demonstrates the impact of the extraction technique (four methods of extractions: cold‐pressing, supercritical CO2 fluid, ultrasound‐assisted, and Soxhlet) and genotype (three cultivars “Rondo,” “Darius,” and “Rasa”) on oil yield, fatty acid profile, and concentration of tocopherols, sterols, and squalene. Provided information can help with more efficient utilization of the tonnes of seeds generated by the fruit industry and consequently contributing to the more effective use of harvested plant material as well as health, economic, and environmental benefits. The impact of the extraction technique and genotype on the oil yield and profile/concentration of fatty acids, tocopherols, sterols and squalene in oil obtained from the seeds of three Japanese quince (Chaenomeles japonica) cultivars (“Rondo,” “Darius,” and “Rasa”) are studied. The plant genotype is the key factor which determines the profile of the fatty acids and the concentration of bioactive compounds in the extracted oil from Japanese quince seed, while the extraction technique plays a secondary role.
... The kernels of apricot, peach and nectarine were indicated as rich sources of oil (up to 54.5 g oil/100 g). It is relevant to comment that species and variety are relevant factors that affect the content of oil (Chamli et al. 2017;Górnaś et al. 2017;Maikhuri et al. 2021;Zhang et al. 2021b). Along with high content, the oil obtained from kernels is also rich in unsaturated fatty acids that composes up to 93.7 g/100 g oil (Yilmaz and Gökmen 2013;Amiran, Shafaghat, and Shafaghatlonbar 2015;Zhou et al. 2016;Chamli et al. 2017;Maikhuri et al. 2021;Sodeifian and Sajadian 2021). ...
Article
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Food processing, especially the juice industry, is an important sector that generate million tons of residues every. Due to the increasing concern about waste generation and the interest in its valorization, the reutilization of by-products generated from the processing of popular fruits of the Prunus genus (rich in high-added value compounds) has gained the spotlight in the food area. This review aims to provide an overview of the high added-value compounds found in the residues of Prunus fruits (peach, nectarine, donut peach, plum, cherry, and apricot) processing and applications in the food science area. Collective (pomace) and individual (kernels, peels, and leaves) residues from Prunus fruits processing contains polyphenols (especially flavonoids and anthocyanins), lipophilic compounds (such as unsaturated fatty acids, carotenes, tocopherols, sterols, and squalene), proteins (bioactive peptides and essential amino acids) that are wasted. Applications are increasingly expanding from the flour from the kernels to encapsulated bioactive compounds, active films, and ingredients with technological relevance for the quality of bread, cookies, ice cream, clean label meat products and extruded foods. Advances to increasing safety has also been reported against anti-nutritional (amygdalin) and toxic compounds (aflatoxin and pesticides) due to advances in emerging processing technologies and strategic use of resources.
... β-carotene amounted for 76-94% of the total carotenoids, ranging from 0.15 to 0.53 mg/100 g oil. Lutein, zeaxanthin, β-cryptoxanthin, and β-carotene were the main forms present in apricot kernel oil with a genotyperelated manner (Górnaś et al., 2017;Pop et al., 2015). Finally, among seeds of 5 apricot varieties grown in Poland extracted with Soxhlet extraction, the highest β-carotene level was detected in the "Somo" variety (66.8 μg/g), and the lowest in "Goldrich sungiant" (42.3 μg/g oil) (Stryjecka et al., 2019), ...
Article
Valorization of byproducts generated during food processing has recently attracted considerable attention, especially processes with high wastage rates. In this review we present a detailed analysis of the phytochemical composition of Prunus seed oil and extracts as potential sources of unsaturated fatty acids, phenolics, and phytosterols. Besides their nutritional value these seeds, especially apricot and peach seeds, could be exploited to produce value-added products such as food enhancers, and antioxidants. Optimum extraction methods of Prunus seeds are discussed to improve yield and lessen environmental hazards associated with typical solvent extraction-based methods. This review presents the best valorization practices for one of the largest cultivated fruit seeds worldwide and its different applications in food and functional food industries.
... β-carotene amounted for 76-94% of the total carotenoids, ranging from 0.15 to 0.53 mg/100 g oil. Lutein, zeaxanthin, β-cryptoxanthin, and β-carotene were the main forms present in apricot kernel oil with a genotyperelated manner (Górnaś et al., 2017;Pop et al., 2015). Finally, among seeds of 5 apricot varieties grown in Poland extracted with Soxhlet extraction, the highest β-carotene level was detected in the "Somo" variety (66.8 μg/g), and the lowest in "Goldrich sungiant" (42.3 μg/g oil) (Stryjecka et al., 2019), ...
... The β+ɣtocopherol were dominant in all oil samples, with 48.5 mg·100g -1 in PKBF, while in oil samples from PKAF and PKAD, this tocopherol homologues were represented by 57.7 and 56.4 mg·100g -1 , respectively. According to the literature, the remaining representatives of the Prunus genus also have γ-tocopherol as the dominant tocopherol in their kernel oils, with its content ranging up to 1333 mg·kg -1 , which was found in sour cherry kernel oil (Matthaus and Özcan, 2009;Manzooret al., 2012;Górnaś et al., 2016b;Górnaś et al., 2017b). ...
Article
Plum kernels of the “Čačanska rodna” variety, by-products from plum brandy production, were collected before and after fermentation and distillation, and used for cold-pressed oil production. Fatty acid and tocopherol contents were determined by capillary GC and HPLC, while the oxidation stability of the resulting cold-pressed oils was tested by the Rancimat method. The results showed that oleic fatty acid was dominant in the oil samples with a content of 56.6 to 61.8%, regardless of the plum kernels’ origin. The fermentation and distillation processes had a pronounced effect on the tocopherol content and oxidative stability of the resulting kernel oils. Tocopherol contents were 61.8 mg·100g-1, 87.4 mg·100g-1, 79.6 mg·100g-1 of oil, while the induction periods were 38.7, 44.4 and 33.6 hours for samples before fermentation, after fermentation and distillation, respectively. Based on the results, it could be concluded that the fermentation process increased the content of tocopherols in kernel oil whereas the high temperature during the distillation process adversely affected the tocopherol content and oxidative stability of the obtained kernel oil.
... Initial mobile phase composition was 95(A):5(B):0(C), which was gradually changed to 60(A):20(B):20(C) in 40 min and held for 10 min. The identification of the carotenoids was based on the comparison of UV/VIS data [maximum absorption wavelengths (λ max ), spectroscopic fine structures (% III/II)] and molecular weight according to a guide to carotenoid analysis in foods [11] and our previous report [12]. The mass spectrometric characteristics performed on Waters Micromass ZQ mass spectrometer (Waters Corporation, Milford, MA, USA) in positive electrospray mode under following conditions: capillary voltage, 3000 V; cone voltage, 30 V; ion source temperature, 120 °C; desolvation temperature, 300 °C; desolvation gas flow 300 L/h; cone gas flow 20L/h. ...
Article
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The composition of lipophilic and hydrophilic components in cultivated (C. tinctorius) and wild (C. oxyacantha) safflower seed oils was studied. By LC–HRMS/MS2, a total of seven highly abundant bioactive compounds with hydrophilic nature, a lignan glycoside (tracheloside), two flavonoids (acacetin–glucuronide pentoside and acacetin-7-O-D-glucuronide), and four alkaloids (N-coumaroylserotonin glucoside, N-feruloylserotonin glucoside, N-coumaroylserotonin, and N-feruloylserotonin), in seeds of both species, were identified. Only a minor part of the hydrophilic compounds (≤ 0.05%) present in the seeds was transferred into the seed oil during the extraction. The linoleic (~ 78%), oleic (~ 15%), palmitic (~ 5%), and stearic (~ 2%) acids—constituted 99% of all detected fatty acids in both species. α-Tocopherol was a main form of tocochromanols (over 94%) in both safflower seed oils. β-Sitosterol was the predominate form (over 36%) of phytosterols, while high levels were also recorded for gramisterol (17.1%) and avenasterol (19.6%) in C. oxyacantha and C. tinctorius seed oils, respectively. Zeaxanthin was a predominated form of carotenoids (over 37%), while high levels were recorded for lutein and β-carotene 15 and 25%, mainly in C. oxyacantha. The total amount of minor lipophilic compounds such as tocochromanols, carotenoids and sterols in C. oxyacantha vs. C. tinctorius seed oil was 57.9 vs. 58.2, 0.76 vs. 0.5, and 185.5 vs. 274 mg/100 g oil, respectively. The presence of squalene was detected only in C. oxyacantha (10.4 mg/100 g oil). Despite the similar composition and levels of fatty acids and tocochromanols, species differed by the phytosterols, carotenoids, and bioactive compounds with hydrophilic nature. The published paper can be read by the clicking on the link listed below: https://rdcu.be/b1CDx
... The associations between oil content and minor lipophilic molecules in oils recovered from seeds and kernels of different fruit such as diploid and hexaploid plum species (Prunus cerasifera Ehrh. and Prunus domestica L., respectively), [19] sweet cherry (Prunus avium L.), [20] sour cherry (Prunus cerasus L.), [21] apricots (Prunus armeniaca L.), [22] crab and dessert apple (Malus sp. and Malus domestica Borkh., respectively), [23] pears (Pyrus communis L.), [24] within the same species, between the genotypes, was previously reported. However, the reported correlations were linear, while in the present study logarithmic correlation was observed. ...
Article
Tocopherols, phytosterols, carotenoids, and squalene are present in mature seeds of Japanese quince. Yet, little is known about the relationship between these compounds and oil yield during fruit and seed development. The profile change of lipophilic compounds during fruit and seed development in Japanese quince cvs. “Darius”, “Rondo”, and “Rasa” was investigated. It is shown here that during fruit and seed development there is a significant reduction, three‐ to over ten‐fold, in the concentration of minor bioactive compounds in seed oil. It was recorded delay between synthesis of tocopherols and oil in Japanese quince seeds during the fruits development results in a logarithmic relationship between the oil content and tocopherols concentration in the seed oil (R2 = 0.980). Similar trends were observed between oil yield and phytosterols, and carotenoids (R2 = 0.927 and R2 = 0.959, respectively). The profile of fatty acids during the development of the seeds significantly has been changed. The reduction of linoleic, palmitic, and gondoic acids levels and increment of oleic acid was noted. The oil content, profile of fatty acids, and concentration of minor bioactive compounds in all three genotypes of Japanese quince seed oil did not change significantly statistically during the last month of fruit development. Practical applications: Some fruits are harvested at different degree of maturity mainly due to a logistic issue and uneven ripening of fruits, which affects the chemical composition of whole fruit including seeds. Therefore it would be good to know‐how is changing the chemical composition in plant material during development especially in the last month before harvest. Production of Japanese quince continues to rise year to year and with it the volume of generated by‐products such as seeds. This study demonstrates how it changes the oil content, profile of fatty acid, and concentration of tocopherols, squalene, phytosterols, and carotenoids in the seeds and seed oil of three Japanese quince cvs. “Rondo”, “Darius” and “Rasa” during plant development. The provided information can be very useful for the manufactories oriented on the processing of by‐products, mainly seeds, generated by other branches of industry, for instance, fruit‐processing. This article is protected by copyright. All rights reserved
... In the case of apricot (Prunus armeniaca L.), Górnaś et al. (2015a) found that the tocopherols content in the kernels depends on cultivar and Rudziń ska et al. (2017) reported that also the sterols and squalene content in kernel oils may be affected by apricot cultivar. The dependence of the content of carotenoids, tocotrienols and tocopherols in kernel oils on apricot genotype was reported by Górnaś et al. (2017a). Górnaś et al. (2017b) determined that also oil yield and content of fatty acids can depend on apricot genotype. ...
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The aim of this study was to develop the discriminative models based on selected textures of the outer surface of pit images to distinguish the different cultivars of sour cherry. The application of the image analysis technique ensured non-destructive, inexpensive and objective research. The textures for the images in the color channels R, G, B, L, a, b, X, Y, Z of the pits of four sour cherry cultivars ‘Debreceni botermo’, ‘Kelleris’, ‘Łutówka’ and ‘Nefris’ were calculated. In the case of discrimination of pits of all four cultivars, the accuracy was up to 96.25%. Slightly lower accuracies were observed for models built based on textures selected from Lab color space (94.12%) and color channel L (83.62%). However, all models allowed to completely distinguish the pits ‘Łutówka’ (100% correctly classified cases) from pits of other cultivars. In the case of analysis performed for pairs of cultivars, full discrimination of the pits ‘Łutówka’ against the other pits was confirmed and the accuracy of 100% was determined for pairs of ‘Łutówka’ and ‘Debreceni botermo’, ‘Łutówka’ and ‘Kelleris’, ‘Łutówka’ and ‘Nefris’. The pits ‘Debreceni botermo’ and ‘Nefris’ were distinguished with the accuracy of up to 99% for the discriminative models built based on a set of textures selected from all color channels (R, G, B, L, a, b, X, Y, Z) and based on a set of textures selected from Lab color space. The accuracy reaching 98% was observed for distinguishing the pits ‘Kelleris’ and ‘Nefris’, and 95% for the pits ‘Debreceni botermo’ vs. ‘Kelleris’, in the case of models including textures selected from all color channels (R, G, B, L, a, b, X, Y, Z).
... The epoxides obtained from the oleic fatty acids are used in oleochemistry mainly as PVC stabilizers (Bornscheuer, 2006), and omega-3 fatty acids are very renowned due to their preventive capacities for various disease. Furthermore, many studies have reported that oils are major sources of tocopherols (Górnas´, 2015;Soliven, 2014;Górnaś et al., 2017).The consumption of additional phytosterols at a maximum effective dose of 2 g/ day significantly reduced LDL levels from 9% to 14% (Kritchevsky and Chen, 2005). Phytosterols are also involved in regulation of membrane fluidity and thus influence membrane properties, functions, and structure (Korber et al., 2017;Ostlund, 2002), decrease cholesterol accumulation, risks of coronary heart disease and contribute to inhibiting the absorption of intestinal cholesterol, including recirculating endogenous biliary cholesterol (Ostlund, 2002). ...
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Fatty acids, phytosterols, total phenolic content, and radical‐scavenging activity were determined in seed oils of 12 wild plants from natural ecosystems in Burundi. Among the 13 fatty acids identified, palmitic, oleic, linoleic, and stearic acids were found predominant throughout all oils, except Parinari curatellifolia oil which showed a high amount of erucic acid (58.41% ± 0.77). The most dominant sterol was found to be β‐sitosterol in all oils and was followed by stigmasterol in 8 kinds of oils and campesterol in 3 kinds of oils. The highest total phenolic contents were observed in P. curatellifolia, Tephrosia vogelii, and Uvaria angolensis oils, with, respectively, 2.16 ± 0.26, 1.43 ± 0.33, and 1.27 ± 0.39 mg gallic acid equivalent/g oil. Some of these oils exhibited a higher ability to scavenge DPPH radicals. The antioxidant capacity of 8 species ranged from 1.18 to 18.08 mmol acid ascorbic equivalent/g oil. Based on these findings, such oils could be used in different domains such as food, cosmetic, pharmaceutical, and lipochemistry. This study showed 14 species of wild plants that can provide oils with a wide variety of chemical compositions. They have been characterized by high contents of polyunsaturated fatty acids while they exhibit several positive health effects. These results suggest the important utility in various domain such as energy, cosmetics and especially the diversification of edible oils.
... It was also reported that α, c, and δ-tocopherols of sour cherry pit oil were obtained as 61 (mg/ kg oil), 400 (mg/kg oil), and 64.2 (mg/kg oil), respectively [32]. It was found that the amounts of tocopherols, carotenoids, tocotrienols, and lipophilic antioxidants in the extracted oils from 15 apricot kernels (Prunus armeniaca L.) as well as oil yield were affected by the genotype [39]. ...
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This study aims to extract oil from fresh sour cherry kernel (Cerasus vulgaris Miller) using the cold press method. The oil content and moisture were obtained as 31.89% and 4%, respectively. The organoleptic assessment of the oil was acceptable and the free fatty acid value was obtained as 1.36 (mg KOH/g oil). In addition, peroxide value and anisidine index of sour cherry kernel oil were obtained as 0.99 meqO2/kg oil and 0.15, respectively. The predominant fatty acids were linoleic acid (42.34%), oleic acid (35.45%), α-eleostearic acid (9.34%), and palmitic acid (6.54%), respectively. The kernel oil contained nine major triacylglycerols consisting of OLL (20.44%), OOL (16.99%), LLL (8.20%), LLEl (7.28%), PLO (7.24%), OElO (5.03%), OOO (4.70%), ElLO (4.54%), PLL (4.35%), and POO (3%), respectively. The most abundant sterol compounds were β-sitosterol (83.55%), ∆5-avenasterol (6.8%), sitostanol (4.8%), campesterol (3.5%), and stigmasterol (0.53%), respectively. Also, antioxidant activity, total phenol content (TPC), total anthocyanin content (TAC), total flavonoid content (TFC), total tannin content (TTC), and total tocopherol content were obtained as 73.22%, 33.44 mg GA/g dry matter, 177.84 mg/L, 46.37 mg/g dry matter, and 1.21 mg GA/g dry matter, 832.5 mg/kg oil, respectively. The amount of amygdalin in the oil sample was not detectable.
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The beneficial and potentially harmful bioactive components in the seeds and seed oil of Trichodesma indicum L. (Boraginaceae) were investigated in the present study. The T. indicum seeds were rich in oil (29.0%), phenolic compounds (PC, 1881.2 mg per 100 g), and pyrrolizidine alkaloids (PA, 2,702,338 ng g−1). Seven PC were identified in T. indicum seeds by liquid chromatography‐quadrupole‐time‐of‐flight mass spectrometry system (LC‐Q‐TOF‐MS). Rosmarinic acid (67%) and isomers of salvianolic acid B/E/L (26%) were the main phenolics, while melitric acid A and sebestenoid C/D constituted 6% and 1%, respectively. Only a minor part of the total PC and PA was transferred from the seeds into the oil fraction during the extraction procedure (<0.03%). The T. indicum seed oil was predominated by the following polyunsaturated fatty acids (PUFA):linoleic (23.2%), γ‐linolenic (6.0%), α‐linolenic (26.8%), and stearidonic (5.9%). High levels were also observed for oleic (26.7%) and palmitic (7.4%) acids. Additionally, notable amounts of γ‐tocopherol (92% of total tocochromanols) and β‐sitosterol (53% of total sterols) were found in T. indicum seed oil. The total content of tocochromanols, sterols, and carotenoids in T. indicum seed oil was 102.7, 236.0, and 0.6 mg per 100 g oil, respectively. Among 10 detected hepatotoxic PA in T. indicum seeds, intermedine/lycopsamine/indicine (90.9%), intermedine N‐oxide (4.9%), and lycopsamine N‐oxide (4.1%) consisted 99.9% of the total PA concentration. The T. indicum seeds should be used carefully due to the presence of PA.
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The seeds and oil yield and profile/levels of fatty acids, tocopherols and phytosterols in seed oils of twelve Japanese quince (Chaenomeles japonica) genotypes were studied. The seeds and oil yield ranged from 3.8 to 5.7% w/w fresh fruit, and 10.9 to 14.6% w/w dry weight seeds, respectively. The range of three predominated fatty acids C16:0, C18:1 and C18:2 in the seed oil of twelve Japanese quince genotypes were 8.1–9.8, 37.5–48.1, and 40.1–50.3%, respectively. α-Tocopherol and β-sitosterol were the main minor lipophilic compounds detected in all investigated genotypes. The percentage of predomination of α-tocopherol and β-sitosterol in each investigated genotype was very similar and amounted to 97–99% of total tocopherols and 76–80% of total phytosterols, respectively. The range of total content tocopherols and phytosterols in 12 genotypes of Japanese quince were 91.9–129.3 and 7830–14166 mg/100 g oil, respectively.
Chapter
The apricot (Prunus armeniaca L.) is an important agricultural crop that widely cultıvated in most of the Mediterranean and Central Asian countries. As known, the fruit of apricot has an important place in human nutrition, and can be consumed as fresh or processed. World apricot production is about 2.5 million tonnes. However, apricot kernels are produced as byproducts and often considered a waste product of fruits processing industry. They have potential to be economically-valuable resource, since they are a rich source of dietary protein as well as fiber. In addition, the kernels are considered as potential sources of oils. Apricot kernels have a high oil yield, which is comparable to the commonly used oils of oilseed crops such as soybean, canola and sunflower. Oil from these kernels can be obtained by solvent extraction or cold pressing method. The oil contains a high percentage of unsaturated fatty acids and is a rich source of minor compounds such as sterols, tocochromanols and squalene, hence attracting interest for the utilization in food and pharmaceutical industry. Due to its nutritional chemical composition and functional properties, apricot kernel oil can be used as edible oil and in many applications like food products formulation, cosmetics as well as functional and medicinal supplements. In this chapter, particular attention has also been given to the composition and applications of kernel oil.
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The Japanese quince (Chaenomeles japonica) is a fruit crop that is processed for industry nearly 100% and generates considerable quantities of seeds. The seeds of Japanese quince can be an alternative raw material for the recovery of oil rich in phytosterols, tocopherols, and carotenoids. Despite having been reported for high content of carotenoids, their composition has not been determined yet. Therefore, in the present study, the profiles of carotenoids in the seed oil of 12 genotypes Japanese quince were studied. Overall, seven carotenoids were identified (β‐carotene, β‐cryptoxanthin, zeaxanthin, lutein, violaxanthin, trans‐, and cis‐neoxanthin), and one was unidentified. In eight and three of the investigated genotypes of Japanese quince all eight and seven forms of carotenoids, respectively, were found. While in genotype SR‐1‐1A only three carotenoids were detected. The content of total carotenoids in different seed oils of Japanese quince measured via HPLC was in the range of 2.05–3.81 mg/100 g of oil. The PCA showed that most of the studied samples (83%) were located in one group providing a similar composition and concentration of carotenoids in most genotypes of Japanese quince. A critical finding for industrial/manufacturing processes that require similar and reproducible quality parameters.
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To reveal the accumulation pattern of cyanogenic glycosides (amygdalin and prunasin) in bitter apricot kernels to further understand the metabolic mechanisms underlying differential accumulation during kernel development and ripening and explore the association between cyanogenic glycoside accumulation and the physical, chemical and biochemical indexes of fruits and kernels during fruit and kernel development, dynamic changes in physical characteristics (weight, moisture content, linear dimensions, derived parameters) and chemical and biochemical parameters (oil, amygdalin and prunasin contents, β-glucosidase activity) of fruits and kernels from ten apricot (Prunus armeniaca L.) cultivars were systematically studied at 10 day intervals, from 20 days after flowering (DAF) until maturity. High variability in most of physical, chemical and biochemical parameters was found among the evaluated apricot cultivars and at different ripening stages. Kernel oil accumulation showed similar sigmoid patterns. Amygdalin and prunasin levels were undetectable in the sweet kernel cultivars throughout kernel development. During the early stages of apricot fruit development (before 50 DAF), the prunasin level in bitter kernels first increased, then decreased markedly; while the amygdalin level was present in quite small amounts and significantly lower than the prunasin level. From 50 to 70 DAF, prunasin further declined to zero; while amygdalin increased linearly and was significantly higher than the prunasin level, then decreased or increased slowly until full maturity. The cyanogenic glycoside accumulation pattern indicated a shift from a prunasin-dominated to an amygdalin-dominated state during bitter apricot kernel development and ripening. β-glucosidase catabolic enzyme activity was high during kernel development and ripening in all tested apricot cultivars, indicating that β-glucosidase was not important for amygdalin accumulation. Correlation analysis showed a positive correlation of kernel amygdalin content with fruit dimension parameters, kernel oil content and β-glucosidase activity, but no or a weak positive correlation with kernel dimension parameters. Principal component analysis (PCA) showed that the variance accumulation contribution rate of the first three principal components totaled 84.56%, and not only revealed differences in amygdalin and prunasin contents and β-glucosidase activity among cultivars, but also distinguished different developmental stages. The results can help us understand the metabolic mechanisms underlying differential cyanogenic glycoside accumulation in apricot kernels and provide a useful reference for breeding high- or low-amygdalin-content apricot cultivars and the agronomic management, intensive processing and exploitation of bitter apricot kernels.
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Fruit seed is a by-product of fruit processing into juice and other products. Despite being treated as waste, fruit seed contains oil with health benefits comparable or even higher than the conventional seed oil from field crops. In addition to essential fatty acids, the fruit seed oil is a rich source of bioactive compounds such as tocopherols, carotenoids, flavonoids, phenolic acids and phytosterols, which have been implicated in the prevention of chronic and degenerative diseases such as cancer, diabetes and cardiovascular diseases. The emerging potential of fruit seed oil application in food and nutraceuticals has prompted researchers to study the effect of preharvest and processing factors on the seed oil quality with respect to nutritional qualities, antioxidant compounds and properties. Herein, the effect of cultivar, fruit-growing region, seeds pretreatment, seeds drying and seed oil extraction on tocopherols, polyphenols, phytosterols, carotenoids, fatty acids, antioxidant activity and oxidative stability of the fruit seed oil is critically discussed. Understanding the influence of these factors on seed oil bioactive phytochemicals, nutritional qualities and antioxidant properties is critical not only for genetically improving the oilseeds plants with desired characteristics, but also in seed oil processing and value addition. Therefore, preharvest and processing factors are essential considerations when determining the application of fruit seed oil.
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Vegetable oils obtained from different plants are known for their beneficial effects on prophylaxis and supportive treatment of a great deal of inflammatory-mediated conditions. Their wide range of saturated and unsaturated fatty acids, and the presence of other ingredients (e.g., tocopherols, chlorophylls), provide them with anti-inflammatory, antioxidant and anticancer properties, which are worth being exploited. In this study, we have carried out the spectrofluorometric analysis of selected vegetable oils, namely apricot (Prunus armeniaca) kernel oil; blueberry (Vaccinium spp.) seed oil; argan (Argania spinosa) nut oil; kiwi (Actinidia deliciosa) seed oil; grape (Vitis vinifera) seed oil; evening primrose (Oenothera biennis) oil and meadowfoam (Limnanthes alba) seed oil, with the purpose to detect their fluorescent ingredients for further identification and bioactivity comparison. The obtained two-(2D) and three-dimensional (3D) emission spectra offered a complete description of the fluorescent components of the mixture and revealed different features for studied oils.
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Fruits are important foods and may be processed into juice, jam and snack products. During the processing, fruit seeds are generated as byproducts and discarded at a cost and with potential environmental contamination. Fruit seeds contain high contents of lipids together with bioactive compounds such as phytosterols, tocopherols, phenolics including flavonoids, and carotenoids and, thus, can be used to produce functional food oils. In this review, the chemical profiles of fatty acids and bioactive compounds, as well as potential health beneficial properties of fruit seed oils, are introduced. The clarification of these pieces of information could stimulate further interest in research and commercialization of fruit seed oils and enhance the profitability of the fruit production and processing industries while reducing environmental hazards.
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In this paper, an investigation was conducted into the effects of different pH values of citric acid solutions combined with ultrasound irradiation on the amino acids of the apricot kernels during debitterizing. The concentrations and varieties of amino acids in the samples were determined using the automatic amino acid analyzer. In addition, the amino acid reference model proposed by WHO/FAO was adopted as the evaluation criteria, and the ratio of essential amino acids in debitterized samples was compared to assess the effect of ultrasonic debitterizing of different pH solutions on the nutritional value carried by apricot kernels amino acids. Finally, with the amino acid content as a parameter, principal component analysis (PCA) and cluster analysis (HCA) were carried out to thoroughly evaluate the nutritional value of amino acids contained in the debitterized apricot kernels. The results indicate that the citric acid solution with a pH value of 5 could be taken as the optimal ultrasonic solution to remove the bitterness of apricot kernels. Specifically, the total amino acid content and the nutritional value of the apricot kernel are high after debitterizing under the condition, which could shorten the debitterizing of apricot kernels and provide highly nutritious amino acids.
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Sour cherry seed oil (SCSO) and pomegranate seed oil (PSO) were extracted by using cold‐press technology and characterized in terms of physicochemical properties, bioactive compound contents, biological activity, and spectroscopic features. They were rich in unsaturated fatty acids (UFAs). The predominant carotenoid was Zeaxanthin (13.15 mg/kg) for SCSO and β‐carotene (33.45 mg/kg) for PSO. Naringenin, ellagic acid, resveratrol, kaempferol, catechin, gallic acid were found to be the major secondary metabolites in the samples by LC/MS‐MS. Further analysis of phenolic compounds and fatty acids were conducted by using 13C and 1H NMR. Functional groups of the oils were analyzed by FT‐IR spectra. DPPH, ABTS, FRAP, and CUPRAC assays were used to investigate the antioxidant activity. The α‐glucosidase inhibition activity of SCSO and PSO was 4.38 and 5.16 mg/mL, respectively. SCSO exhibited antimicrobial activity against Staphylococcus aureus although the growth of Staphylococcus aureus and Escherichia coli was inhibited by the PSO.
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In this paper, the experiments were conducted to investigate the effects of saturated hot air (SHA) pretreatment on the components in apricot kernels and skins compared with the traditional blanching (TB) method, so as to evaluate the feasibility of SHA for removing the skins. Furthermore, the heatmap was employed to correlate the phenolic components and the color values. The results indicate that the SHA temperature and time had a definite influence on some of the components including phenols, amygdalin, proteins and reducing sugars. Compared with the TB, not only the loss of amygdalin, proteins and reducing sugars in apricot kernels used in SHA pretreatment greatly decreased, but also the loss of the phenols, flavonoids, protocatechin, catechin, vanillic acid and chlorogenic acid in the skins decreased by 42.3%, 50.5%, 57.8%, 63.3%, 94.5% and 42.5%, respectively. The SHA pretreatment for removing skins could decrease the amount of wastewater discharge, and lower the loss of active substances in apricot kernels and its skins. In conclusion, the SHA might be as a novel green and efficient method for removing the apricot kernel skins.
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Structured lipids (SL) containing behenic acid have been produced in order to obtain low-calorie lipids for foods; however, the development of a high nutritional value and a stable nanoemulsion carrier system for these SL is an interesting breakthrough for this field of research, improving technologic and biological potential for food application. In this sense, the aim of this study was to evaluate the stability of a nanoemulsion containing SL NeSL (produced with olive oil, soybean oil and fully hydrogenated crambe oil), the behavior during in vitro digestion and the effects on biomarkers involved in the obesity in cell models. The samples showed good stability throughout storage (30 days) under refrigeration and room temperature and after the gastric digestion phase compared to the controls (nanoemulsion of olive and soybean oil). After the intestinal phase, there was an increase in oil droplet size and zeta potential, a characteristic of coalescence. In the lipid accumulation model in adipocytes, the highest concentration (50 µL/mL) of NeSL resulted in 42% less lipid accumulation, compared to the control. Furthermore, the sample was able to reduce inflammatory cytokines produced by macrophages provoked by LPS (lipopolysaccharide). The combination of the oils in NeSL resulted in a fatty acid profile with beneficial health properties, which may have contributed to less lipid accumulation and improved inflammatory parameters. This SL in the form of a nanoemulsion, may be used as a partial fat substitute in low-calorie food products.
Chapter
In recent years, much study has been devoted to the properties of unconventional seed oils and to exploring their potential as dietary sources. The nutritional values of plant oils generally depend on their contents of fatty acids (FAs), tocopherols, phytosterols, and other bioactive compounds, such as carotene and squalene. Agricultural factors have a great effect on the synthesis of FAs and bioactive compounds in seeds, and this further affects the quality of the seed oils. The oil extraction process and storage conditions also play important roles in oxidation and component changes in plant oils. The frying process also affects the quality of vegetable oil through changes in its various substances.
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Kernels recovered from fruit pits of fourteen apricot (Prunus armeniaca L.) genotypes were tested for future application as feedstock for biodiesel production. The difference between the lowest and the highest oil yield between studied samples was over two-fold and reached between 27.1 and 58.7% (w/w) dw. The oleic and linoleic acids were the two dominant fatty acids in apricot kernel oils; however, their content was affected meaningfully by the variety and amounted to 38.5–67.2% and 26.4-54.8%, respectively. Two significant correlations (p < 0.000005) were found between oil yield in kernels of different apricot genotypes and two fatty acids, oleic and linoleic (r = 0.947 and r = -0.927, respectively). The biodiesel parameters of fourteen apricot genotypes were calculated empirically according to previously developed equations based on the fatty acid methyl esters composition of the potential feedstock. The European biodiesel standards of kinematic viscosity, cetane number, density and iodine value were met for thirteen investigated samples. The exception was noted for genotype HL PSŠ 5. The recorded differences between minimum and maximum value of individual biodiesel parameters calculated empirically for various apricot genotypes differed as follows: 0.20 mm²/s (kinematic viscosity), 4.9 (cetane number), 0.06 MJ/kg (higher heating value), 0.0028 g/cm³ (density), 15.6 I2/100 g (iodine value), 1.67 °C (CFPP) and 2.15 h (induction period). The logarithmic regression model in comparison to linear regression model, better expressed the relationship between physicochemical properties of biofuel and the ΣPUFA/(ΣSFA+ΣMUFA) ratio. To confirm the usefulness of the applied empirical equations for biodiesel parameters prediction of the apricot feedstock, five cold-pressed apricot kernel oils of different origin and with a varied composition of fatty acids were tested experimentally and compared with the values calculated empirically.
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Lipophilic bioactive compounds in oils recovered from the kernels of seven sweet cherry (Prunus avium L.) cultivars, harvested at single location in 2013, were studied. Oil yield in sweet cherry ranged between 30.3-40.3 % (w/w) dw. The main fatty acids were oleic acid (39.62-49.92 %), linoleic acid (31.13-38.81 %), α-eleostearic acid (7.23-10.73 %) and palmitic acid (5.59-7.10 %), all four represented approximately 95 % of the total detected fatty acids. The ranges of total tocochromanols and sterols were between 83.1-111.1 and 233.6-419.4 mg/100 g of oil, respectively. Regardless of the cultivar, the γ-tocopherol and β-sitosterol were the main lipophilic minor bioactive compounds. The content of the carotenoids and squalene were between 0.38-0.62 and 60.9-127.7 mg/100 g of oil, respectively. Three significant correlations were found between oil yield and total contents of sterols (r = -0.852), tocochromanols (r = -0.880) and carotenoids (r = -0.698) in sweet cherry kernel oils. The oil yield, as well as the content of lipophilic bioactive compounds in oil was significantly affected by the cultivar. The full-text view-only version can be accessed from the following link: https://rdcu.be/6p46
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Lipophilic bioactive compounds in oils recovered from the seeds of eight pear (Pyrus communis L.) cultivars were studied. Oil yield in pear seeds ranged between 16.3 and 31.5 % (w/w) dw. The main fatty acids were palmitic acid (6.13–8.52 %), oleic acid (27.39–38.17 %) and linoleic acid (50.73–63.78 %), all three representing 96–99 % of the total detected fatty acids. The range of total tocochromanols was between 120.5 and 216.1 mg/100 g of oil. Independent of the cultivar, the γ-tocopherol was the main tocochromanol and constituted approximately 88 %. The contents of the carotenoids and squalene were between 0.69–2.99 and 25.5–40.8 mg/100 g of oil, respectively. The β-sitosterol constituted 83.4–87.6 % of total sterols contents, which ranged between 276.4 and 600.1 mg/100 g of oil. Three significant correlations were found between oil yield and total contents of sterols (r = −0.893), tocochromanols (r = −0.955) and carotenoids (r = −0.685) in pear seed oils.
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The physicochemical interactions between alpha-tocopherol and three phenolic acids, which constitute main phenolics in coffee brew: caffeic, chlorogenic and ferulic acid, in L-α-phosphatidylcholine liposome system were studied. Steady-state and fluorescence lifetime measurements were applied to elucidate location of investigated phenolic acids in liposomes, and the results have shown that ferulic acid is most embedded into membrane structure. Lipophilic studies have shown that at pH 7.4 the partition coefficients for all phenolic acids are similar. Antioxidant capacity measurements of studied antioxidants were taken using fluorescent probe BODIPY. The synergistic effect was observed in all tested antioxidant systems with the exception of sample consisting of chlorogenic acid (2.5 μM) and alpha-tocopherol (2.5 μM), where antagonistic effect was noted. Concentration of antioxidants was a significant factor in the observed phenomenon. The most effective antioxidant system against oxidation in liposomes was combination of alpha-tocopherol and ferulic acid. This phenomenon could be explained by interaction of ferulic acid with the interior of the phospholipids membrane.
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The profile of tocopherol (T) and tocotrienol (T3) homologues in kernels recovered from 28 various plum varieties of hexaploid species Prunus domestica L. and diploid plums Prunus cerasifera Ehrh. and its crossbreeds were studied. One tocotrienol (α-T3) and four tocopherol homologues (α, β, γ and δ) were determined in all studied samples by an RP-HPLC/FLD method. The concentration of tocochromanols varied considerably in kernels of different plum varieties and amounted, respectively: 3.55-11.84 (α-T), 0.01-0.13 (β-T), 30.58-73.63 (γ-T), 0.71-4.04 (δ-T), 0.24-1.47 mg/100 g dw (α-T3). The total content of tocochromanols was recorded in the range 36.86-83.38 mg/100 g dw. The average percentage of individual tocochromanols detected in the plum kernels was as follows: α-T (11.6 %), β-T (0.1 %), γ-T (83.6 %), δ-T (3.5 %) and α-T3 (1.2 %). Concentration of tocopherol homologues and α-T3 in kernels of the diploid plums P. cerasifera and its crossbreeds were on average ~20 % lower, with the exception of δ-T (50 % lower), in comparison with the P. domestica. The principal component analysis allowed to classify the tested samples in two main groups and several outliers.
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Composition of tocochromanols in kernels recovered from 16 different apricot varieties (Prunus armeniaca L.) was studied. Three tocopherol (T) homologues, namely α, γ and δ, were quantified in all tested samples by an RP-HPLC/FLD method. The γ-T was the main tocopherol homologue identified in apricot kernels and constituted approximately 93% of total detected tocopherols. The RP-UPLC-ESI/MSn method detected trace amounts of two tocotrienol homologues α and γ in the apricot kernels. The concentration of individual tocopherol homologues in kernels of different apricots varieties, expressed in mg/100 g dwb, was in the following range: 1.38–4.41 (α-T), 42.48–73.27 (γ-T) and 0.77–2.09 (δ-T). Moreover, the ratio between individual tocopherol homologues α:γ:δ was nearly constant in all varieties and amounted to approximately 2:39:1. Free access for the first 50 persons, link below: http://www.tandfonline.com/eprint/SZXNQ34PxCkrfp3eDKI3/full
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Tocochromanols profile in kernels recovered from fruit pits of seven sweet cherry (Prunus avium L., family: Rosaceae) cultivars was studied. Four tocopherol homologues (α-T, β-T, γ-T, and δ-T) were quantified in all tested samples by RP-HPLC/FLD method. The RP-UPLC-ESI/MSn analyses allowed to detect trace amounts of two tocotrienol homologues (α and γ). The concentration of individual tocopherol homologues in kernels of different sweet cherry cultivars, expressed in mg/100 g dwb, was in the follow range: 3.03–4.96 (α-T), 0.01–0.11 (β-T), 32.26–37.51 (γ-T), and 0.95–1.69 (δ-T). The γ-T was the main tocopherol homologue identified in sweet cherry kernels and constituted approximately 88 % of total detected tocochromanols. The percentage composition of the individual tocopherol homologues in kernels of different sweet cherry cultivars was comparable.
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Non-traditional plant oils, such as cold pressed black cumin (Nigella sativa) seeds oil and oils extracted by n-hexane in the lab conditions from food industry by-products, namely, apricot kernels (Prunus armeniaca), wheat germ (Triticum vulgare), grape seeds (Vitis vinifera), and tomato seeds (Lycopersicon esculentum) were investigated. Bioactive compounds such as phytosterols, tocopherols, and tocotrienols, and also fatty acid composition were determined by GLC and HPLC. The oxidative stability index of oils was evaluated by rancimat method. The fatty acid composition of lipids from apricot kernels was different from the other oils. The contribution of oleic acid in apricot oil amount 66.77%, while in the other oils ranged from 12.39% to 21.86%. The highest level of a-linolenic acid was determined in wheat germ oil (7.58%). Concerning phytosterols, b-sitosterol was major component in all oils extracted from non-traditional sources, with wheat germ oil being the richest in total phytosterol content. Wheat germ oil was very rich in campesterol and sitostanol. It was found that wheat germ, black cumin seed, tomato seed, and apricot kernel oils contained significant amount of citrostadienol. Concerning the vitamin E, it was found that black cumin seed oil contained highest amount of tocotrienols and gamma tocopherols, while, tomato seed oil contain highest amount of gamma-tocotrienols. Wheat germ oil was unique in having a high content of alpha-tocopherol. Apricot kernel and wheat germ oils showed the highest oxidative stability as shown from its induction period compared to the other investigated oils. It is recommended that these oils can be utilized as sources of value added products, natural antioxidants, edible, and healthy oils.
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IntroductionChemistrySources of Dietary CarotenoidsPostharvest and Processing EffectsAbsorption and MetabolismBiological Actions and Disease PreventionConclusions AcknowledgmentReferences
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Due to the importance of tocopherols for oil stability, and consequently in almond (Prunus amygdalus Batsch) kernel quality, the concentration of the three isomers α-, γ- and δ-tocopherol were determined over 2 years in oil from the kernels of a group of almond selections in five progenies obtained from crosses between eight parents. Oil content was highly variable between genotypes, ranging from 40-65% of the total kernel dry weight (DW), but was consistent over the 2 years. High variability in the concentrations of the three isomers, and of the total amount of tocopherol, were also observed, even among genotypes in the same progeny, with significant differences between progenies and individuals. In some genotypes, a significant year effect was observed, with higher concentrations in the first year, probably due to higher Summer temperatures. The concentration in α-tocopherol, the isomer with the major stabilising activity, was ten-times higher than the levels of γ- and δ-tocopherol, which were similar. A significant and positive correlation was also found between the concentrations of α- and γ-tocopherol. Tocopherol concentration was high in 'Marcona', a traditional high-quality Spanish cultivar, and in several late-blooming selections. The continuous distribution of tocopherol concentrations suggests polygenic control. Significant differences in concentrations of α- and γ-tocopherol indicate that high tocopherol concentration is a clearly attainable objective in almond breeding.
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Almond (Prunus dulcis (Miller) D.A. Webb) genetic resources (Marcona, Guara, Non Pareil, IXL, AI, Martinelli C, Emilito INTA, Cáceres Clara Chica, Javier INTA) were studied during two consecutive crop years in order to evaluate variations in kernel oil yield and composition, and oil oxidative parameters. Total oil, oleic acid, α-tocopherol and squalene contents were found to range between 48.0% and 57.5%, 65% and 77.5%, 370 and 675 μg/g oil, and 37.9 and 114.2 μg/g oil, respectively. The genotype was the main variability source for all these chemical traits. The α-tocopherol content seems to be the most important contributor to both the radical scavenging capacity and the oxidative stability of almond oils analysed. Results obtained from the local genotypes namely Martinelli C, Emilito INTA and Javier INTA may be of interest for almond breeding focused to improve kernel oil yield and composition.
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The profile of lipophilic compounds was studied in oils obtained from seeds of five dessert and six crab apple cultivars. Apple seeds were collected from by-products generated during the preparation of fruit salads and in juice pressing. The oil yield in the apple seeds ranged from 12.06 to 27.49 g/100 g dry weight base. The average level of oil obtained from crab apple seeds was higher by 30% when compared to dessert apple seeds. The fatty acid composition was dominated by palmitic acid (5.78–8.33%), oleic acid (20.68–29.00%) and linoleic acid (59.37–67.94%). Among the six detected phytosterols β-sitosterol was predominant (51–94%). Total phytosterol concentration as well as squalene varied in different apple seed oils and amounted to 1.13–7.80 and 0.01–0.34 mg/g, respectively. Four significant correlations were found between oil yield and contents of oleic acid (r = 0.822, p < 0.01), α-linolenic acid (r = 0.919, p < 0.0001), β-sitosterol (r = 0.931, p < 0.0001) and total phytosterols (r = 0.901, p < 0.001) in apple seed oils.
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Eight tocochromanols (alpha, beta, gamma and delta homologues of tocopherol and tocotrienol) naturally occurring in foods were successfully separated within a 13-minute run in the RP-HPLC mode. Analytes were separated on the Phenomenex Luna PFP column filled with the pentafluorophenyl stationary phase (3 um, 150 × 4.6 mm) using the mobile phase containing methanol:water (93:7, v/v) with an elution flow rate of 1 ml/min and column oven temperature of 40 C. The method was rapid, linear, accurate and precise, with detection limits in the range of 0.000184 µg to 0.000605 µg, preventing analyte losses due direct dissolution in 2-propanol. The developed RP-HPLC method in comparison with the NP-HPLC mode had a significantly higher sensitivity, speed and repeatability, but primarily it protected against the loss of analytes and thus reduced the risk of possible error measurements. It was found that tocopherol contents in the tested butter samples amounted to 2.00 - 16.92 mg/100g for samples coming from Poland and 2.61 – 2.98 mg/100g for samples from Latvia, respectively. The method is characterized by simplicity of implementation and it was successfully applied in the determination of tocochromanols in butter to verify product authenticity.
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New cold-pressed oil recovered from seeds of Japanese quince (Chaenomeles japonica (Thunb.) Lindl. ex Spach, family: Rosaceae), obtained as a by-product of fruit processing, were characterised and compared with nine well-known oils. The Japanese quince seed oil had the highest amounts of tocopherols, b-carotene and total phenolic compounds (726.20; 10.77 and 64.03 mg/kg, respectively) and the lowest amount of chlorophyll (0.12 mg/kg) and peroxide value (0.59 mEq O2/kg) compared to sesame, poppy, peanut, flaxseed, pumpkin, sunflower, almond, hazelnut and walnut oils. A correlation was found between the total contents of tocochromanols, b-carotene, phenolic compounds and the radical-scavenging capacity of the oils (0.94; 0.68; 0.63, respectively), and also between the amount of chlorophyll and the CIE a* coordinate (0.80) and the amount of b-carotene and the CIE b* coordinate (0.47). In Japanese quince seed oil thirteen fatty acids were identified with three predominating: palmitic acid (10.07%), oleic acid (34.55%) and linoleic acid (52.35%). The highest consumer acceptance was noted for hazelnut and walnut oils, while it was lowest for the poppy and flaxseed oils. Amygdalin was not detected in the Japanese quince seed oil.
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The present review compiles positive MS fragmentation data of selected carotenoids obtained using various ionization techniques and matrices. In addition, new experimental data from the analysis of carotenoids in transgenic maize and rice callus are provided. Several carotenes and oxygen-functionalized carotenoids containing epoxy, hydroxyl, and ketone groups were ionized by atmospheric pressure chemical ionization (APCI)-tandem mass spectrometry (MS/MS) in positive ion mode. Thus, on the basis of the information obtained from the literature and our own experiments, we identified characteristic carotenoid ions that can be associated to functional groups in the structures of these compounds. In addition, pigments with a very similar structure were differentiated through comparison of the intensities of their fragments. The data provide a basis for the structural elucidation of carotenoids by mass spectrometry (MS). © 2013 Wiley Periodicals, Inc. Mass Spec Rev. 9999: 1-20, 2013.
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ABSTRACT: We investigated the effect of long-term antioxidant supplementation (lutein and alpha-tocopherol) on serum levels and visual performance in patients with cataracts. Seventeen patients clinically diagnosed with age-related cataracts were randomized in a double-blind study involving dietary supplementation with lutein (15 mg; n = 5), alpha-tocopherol (100 mg; n = 6), or placebo (n = 6), three times a week for up to 2 y. Serum carotenoid and tocopherol concentrations were determined with quality-controlled high-performance liquid chromatography, and visual performance (visual acuity and glare sensitivity) and biochemical and hematologic indexes were monitored every 3 mo throughout the study. Changes in these parameters were assessed by General Linear Model (GLM) repeated measures analysis. Serum concentrations of lutein and alpha-tocopherol increased with supplementation, although statistical significance was reached only in the lutein group. Visual performance (visual acuity and glare sensitivity) improved in the lutein group, whereas there was a trend toward the maintenance of and decrease in visual acuity with alpha-tocopherol and placebo supplementation, respectively. No significant side effects or changes in biochemical or hematologic profiles were observed in any of the subjects during the study. Visual function in patients with age-related cataracts who received the lutein supplements improved, suggesting that a higher intake of lutein, through lutein-rich fruit and vegetables or supplements, may have beneficial effects on the visual performance of people with age-related cataracts.
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The aim of the study was to reveal antioxidant synergism or antagonism between quercetin, rutin and selected tocotrienols in linoleic acid emulsion. The oxidative stress was generated by 2,2′-azobis(2-amidinopropane) dihydrochloride (AAPH) or CuSO4; the increase of the concentration of peroxidation products was monitored using fluorescence probe 2,7-dichlorofluorescein (DCF). The antioxidant activity of tested substances depends on the form of the antioxidant (aglycone, glycoside), its concentration, localization in the emulsion, and the factors generating oxidative stress. The synergistic effect occurred when the effectiveness of individual antioxidant was relatively weak and mainly when the concentration of antioxidants was in the physiologically significant range of 1 μM. We suggest that tocotrienols were regenerated by flavonoids. The synergism benefitted from the proximity of the localization of interacting antioxidants (e.g. the presence of one of the antioxidants at the oil-water interface).
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Seed oils recovered from Rosaceae species such as dessert and cider apples (Malus domestica Borkh.), quince (Cydonia oblonga Mill.), and rose hip (Rosa canina L.) were analyzed for their tocopherol and carotenoid contents using HPLC-DAD-MS(n) following saponification. Qualitative and quantitative tocopherol and carotenoid compositions significantly differed, not only among the different genera but also among cultivars of one species. In particular, seed oils of cider apples were shown to contain higher amounts of both antioxidant classes than that of dessert apples. Total contents of tocopherols of the investigated Rosaceous seed oils ranged from 597.7 to 1099.9 mg/kg oil, while total carotenoid contents varied between 0.48 and 39.15 mg/kg oil. Thus, these seed oils were found to contain appreciable amounts of lipohilic antioxidants having health beneficial potential. The results of the present study contribute to a more economical and exhaustive exploitation of seed byproducts arising from the processing of these Rosaceous fruits.
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The oil content as well as the fatty acid and tocopherol composition of kernels from 15 Prunus spp. varieties from Turkey were determined. The oil yields from these kernels varied from 46.3 to 55.5%. The main fatty acids of Prunus spp. kernel oils were oleic acid (43.9–78.5%), linoleic acid (9.7–37%) and palmitic acid (4.9–7.3%). The total amount of vitamin-E-active compounds in the oils varied between 62.9 and 439.9 mg/kg. The predominant tocopherol in most kernel oils was γ-tocopherol. Only two varieties of P. amygdalus and one variety of P. persica showed α-tocopherol as the main vitamin-E-active compound. The composition of the oils was 9–164.5 mg/kg α-tocopherol, 21.5–41.6 mg/kg α-tocotrienol, 1.6–330.2 mg/kg γ-tocopherol and 0–39.1 mg/kg δ-tocopherol. From the results of the present study, it can be concluded that the kernels of the investigated species of Prunus fruits from Turkey may serve potential sources of valuable oil that might be used for edible and other industrial applications. The search for new sources of vegetable oils is an ongoing challenge and the further utilization of by-products from the food processing industry is an interesting option in this field. Seed oils from Prunus species contain high amounts of recommended monounsaturated oleic acid moderate contents of linoleic acid and low amounts of saturated fatty acids that may result in more favorable oil than olive oil with regard to their fatty acid compositions. Additionally, the oils contain vitamin-E-active compounds. Both fatty acid composition and vitamin-E-active compounds may justify the further processing of seeds from Prunus species for the production of oil for food and pharmaceutical applications.
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The Amazonian region from Brazil has a wide variety of native and wild noncommercially cultivated fruits. This article reports for the first time the composition of carotenoids and phenolic compounds from Caryocar villosum fruit pulp, and, in addition, its proximate composition and antioxidant capacity (ORAC assay) were determined. According to the nutritional composition, water (52%) and lipids (25%) were the major components found in the pulp, and the total energetic value was 291 kcal/100 g. The major phenolic compounds identified by HPLC-DAD-ESI-MS/MS were gallic acid (182.4 μg/g pulp), followed by ellagic acid rhamnoside (107 μg/g pulp) and ellagic acid (104 μg/g pulp). The main carotenoids identified by HPLC-DAD-APCI-MS/MS were all-trans-antheraxanthin (3.4 μg/g pulp), all-trans-zeaxanthin (2.9 μg/g pulp), and a lutein-like carotenoid (2.8 μg/g pulp). The antioxidant capacity of the pulp (3.7 mMol Trolox/100 g pulp) indicates that it can be considered a good peroxyl radical scavenger.
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This study further examines the factors which affect the chromatographic response of carotenoids and contribute to analytical variation and inaccuracies in their quantitative determination. A method for the analysis of carotenoids in vegetables and fruits is described and data are presented for the carotenoid content of vegetables and fruits commonly consumed in the UK. The addition of a solvent modifier (triethylamine) to the mobile phase was shown to improve the recovery of carotenoids from the column from around 60% to over 90%. The linearity and reproducibility of the chromatographic response was investigated and the robustness and reproducibility of the method was measured using a reference vegetable material developed in the laboratory. Short and longer term reproducibility showed an average CV of around 8% for all carotenoids. Analysis showed that good sources (>1000 μg/100 g) of lutein were broccoli, butterhead lettuce, parsley, peas, peppers, spinach and watercress; of lycopene: tomatoes and tomato products; and of β-carotene: broccoli, carrots, greens, butterhead lettuce, mixed vegetables, parsley, spinach and watercress. There was little or no loss of carotenoids on cooking, green vegetables showed an average increase in lutein levels of 24% and in β-carotene levels of 38%. This study and previous studies in our laboratory have demonstrated that a number of factors affect the validity of the ‘peak response’ and are likely to contribute to within and between laboratory variation. It is suggested that the development and use of standard reference materials would significantly improve the quality of data.
Article
The color and the biological activities of carotenoids are intimately related to their structures. Thus, conclusive identification is an important part of carotenoid analysis. Brazil has a wide variety of carotenoid-rich fruits with markedly varied carotenoid composition, qualitatively and quantitatively. Identification of the carotenoids can therefore be a delicate task. The present work had the objective of confirming the identity of carotenoids in acerola (Malpighia glabra L.), camu-camu (Myrciaria dubia), pequi (Caryocar brasiliense Camb.) and pitanga (Eugenia uniflora L.). The following identifying parameters were employed: chromatographic behavior in HPLC and TLC, UV–visible absorption spectra, chemical reactions and mass spectra. The HPLC analyses were carried out with a liquid chromatograph equipped with photodiode array and mass detectors and a monomeric C18 column ODS2, 3 μm, 4.6 i.d×150 mm. With carotenoids of known structures, conclusive identification in HPLC can be achieved by the combined use of the retention times and co-chromatography with authentic carotenoid standards, the UV–visible absorption spectra and the mass spectra. In the absence of a mass detector, the identification is conclusive if chemical tests, particularly with the xanthophylls, are done, along with the chromatographic data and UV–visible absorption spectra.
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The concentration of the different tocopherol homologues in almond kernel oil was determined in 17 almond cultivars grown in two different experimental orchards, in Spain and Morocco. The three main homologues showed a large variability, ranging from 210.9 to 553.4 mg/kg of oil for α-tocopherol, from 4.64 to 14.92 mg/kg for γ-tocopherol, and from 0.2 to 1.02 mg/kg for δ-tocopherol. The year effect was significant, independent of the experimental site, for all homologues and total tocopherol, the values of α-tocopherol, γ-tocopherol, and total tocopherol being higher in 2009 than in 2008, whereas the value of δ-tocopherol was higher in 2008. The location effect was also significant, the values of γ- and δ-tocopherol being higher in Spain than in Morocco, whereas for α-tocopherol the location effect was dependent on the genotype. These effects could not be explained by the temperature differences between sites, but probably other undetermined environmental factors might explain the effect of the location, such as rainfall and irrigation supplementation during fruit growing and ripening.
Article
The concept of photoprotection by dietary means is gaining momentum. Plant constituents such as carotenoids and flavonoids are involved in protection against excess light in plants and contribute to the prevention of UV damage in humans. As micronutrients, they are ingested with the diet and are distributed into light-exposed tissues, such as skin or the eye where they provide systemic photoprotection. beta-Carotene and lycopene prevent UV-induced erythema formation. Likewise, dietary flavanols exhibit photoprotection. After about 10-12 weeks of dietary intervention, a decrease in the sensitivity toward UV-induced erythema was observed in volunteers. Dietary micronutrients may contribute to life-long protection against harmful UV radiation.
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The fatty acid, sn-2 fatty acid, triacyglycerol (TAG), tocopherol, and phytosterol compositions of kernel oils obtained from nine apricot varieties grown in the Malatya region of Turkey were determined ( P<0.05). The names of the apricot varieties were Alyanak (ALY), Cataloglu (CAT), Cöloglu (COL), Hacihaliloglu (HAC), Hacikiz (HKI), Hasanbey (HSB), Kabaasi (KAB), Soganci (SOG), and Tokaloglu (TOK). The total oil contents of apricot kernels ranged from 40.23 to 53.19%. Oleic acid contributed 70.83% to the total fatty acids, followed by linoleic (21.96%), palmitic (4.92%), and stearic (1.21%) acids. The s n-2 position is mainly occupied with oleic acid (63.54%), linoleic acid (35.0%), and palmitic acid (0.96%). Eight TAG species were identified: LLL, OLL, PLL, OOL+POL, OOO+POO, and SOO (where P, palmitoyl; S, stearoyl; O, oleoyl; and L, linoleoyl), among which mainly OOO+POO contributed to 48.64% of the total, followed by OOL+POL at 32.63% and OLL at 14.33%. Four tocopherol and six phytosterol isomers were identified and quantified; among these, gamma-tocopherol (475.11 mg/kg of oil) and beta-sitosterol (273.67 mg/100 g of oil) were predominant. Principal component analysis (PCA) was applied to the data from lipid components of apricot kernel oil in order to explore the distribution of the apricot variety according to their kernel's lipid components. PCA separated some varieties including ALY, COL, KAB, CAT, SOG, and HSB in one group and varieties TOK, HAC, and HKI in another group based on their lipid components of apricot kernel oil. So, in the present study, PCA was found to be a powerful tool for classification of the samples.
Identification and quantification
  • R C Chiste
  • A Z Mercadante