Effect of Filtration Process on Oxidative Stability and Minor Compounds of the Cold-Pressed Hempseed Oil during Storage.

Cold-pressed hempseed oil (HO) has been increasingly exploited in the human diet for its excellent nutritional and healthy properties. However, it has a high content of polyunsaturated fatty acids (PUFAs) and chlorophylls, which inevitably accelerate its oxidative deterioration, especially in the presence of light. In this scenario, the filtration technology may ameliorate the oxidative stability of the oil, with positive effects on its nutritional quality and shelf life. Therefore, in this study, the oxidative stability and minor compounds of non-filtered and filtered HO (NF-HO and F-HO) were monitored over 12 weeks of storage in transparent glass bottles. F-HO showed a better hydrolytic and oxidative status than NF-HO during storage. As a result, F-HO also displayed better preservation of total MUFAs and PUFAs in the autoxidation process. Filtration consistently reduced chlorophylls, thus causing a variation in the natural color of HO. Accordingly, F-HO not only revealed an increased resistance to photooxidation but it was also suitable for storage in clear bottles within 12 weeks. F-HO predictably showed lower carotenoids, tocopherols, polyphenols, and squalene compared to NF-HO. However, filtration appeared to play a "protective role" toward these antioxidants, which had lower degradation rates in F-HO than NF-HO for 12 weeks. Interestingly, the element profile of HO was not affected by filtration and remained stable during the study period. Overall, this study may be of practical use to both producers and marketers of cold-pressed HO.

Recent Research on Cannabis sativa L.: Phytochemistry, New Matrices, Cultivation Techniques, and Recent Updates on Its Brain-Related Effects (2018-2023).

Cannabis sativa L. is a plant that humankind has been using for millennia. The basis of its widespread utilization is its adaptability to so many different climatic conditions, with easy cultivability in numerous diverse environments. Because of its variegate phytochemistry, C. sativa has been used in many sectors, although the discovery of the presence in the plant of several psychotropic substances (e.g., Δ9-tetrahydrocannabinol, THC) caused a drastic reduction of its cultivation and use together with its official ban from pharmacopeias. Fortunately, the discovery of Cannabis varieties with low content of THC as well as the biotechnological development of new clones rich in many phytochemical components endorsed with peculiar and many important bioactivities has demanded the reassessment of these species, the study and use of which are currently experiencing new and important developments. In this review we focus our attention on the phytochemistry, new matrices, suitable agronomic techniques, and new biological activities developed in the five last years.

Large-scale preparation of two minor polar polyphenols from Phyllanthus emblica Linn. by macroporous resin column chromatography and high-temperature preparative high-speed counter-current chromatography.

In the present study, an efficient strategy for the large-scale preparation of two minor polar polyphenols from Phyllanthus emblica L. has been established by macroporous resin column chromatography and high-temperature preparative high-speed counter-current chromatography. Macroporous resin column chromatography was used for the enrichment of the target polyphenols. The target polyphenols could be well enriched in the 10% ethanol fraction and the peak area proportion increased from 2.2% in the crude extract to 85.3% in the 10% ethanol fraction. Then, the 10% ethanol fraction was introduced to preparative high-speed counter-current chromatography for separation using an n-butanol-ethyl acetate-water (17:3:20, v/v/v) solvent system. In order to improve the retention of the stationary phase, a high-temperature preparative high-speed counter-current chromatography had been developed by using a 316 L stainless steel pipe as a column. A 50°C of column temperature was used and the retention rate of the stationary phase could reach 75%. Finally, 871 mg of compound Ⅰ and 534 mg of compound Ⅱ with purities higher than 98% were obtained from 4 g of the sample. The chemical structures were identified as corilagin and 1, 6-di-O-galloyl-ß-D-glucoside by 1 H-NMR and 13 C-NMR.

Quality Evaluation of the Oil of Camellia spp.

The oil of Camellia spp. has become a well-known high-quality edible oil because of its rich nutrition. It is of great significance to breed fine varieties of Camellia spp. for the sustainable growth of the Camellia spp. industry. This study mainly evaluated the quality and antioxidant capacity of the camellia seed from several sources. The fatty acid composition and main active components of 40 kinds of C. oleifera, C. vietnamensis, C. osmantha, and C. gigantocarpa seeds, and so on, from different regions, were tested using GC-MS and HPLC. The quality of different Camellia spp. germplasm resources was comprehensively evaluated using multiple indices. The unsaturated fatty acid content and the antioxidant capacity of C. vietnamensis from Hainan were higher than those of C. oleifera Abel. In addition, there were a few differences in the fatty acid compositions of Camellia spp. oil from different species. Correlation analysis confirmed that rutin, total saponin, total flavonoids, squalene, and vitamin E were strongly correlated to the antioxidant capacity of Camellia spp. In the comprehensive evaluation, the best quality and strongest antioxidant activity were found for Chengmai Dafeng (C. vietnamensis). These methods in the study were applied for the first time for the quality evaluation of the Camellia spp. species. This study provided new insights into the quality evaluation of the Camellia spp. species, thus facilitating further development of variety breeding along with quality evaluation.

Influence of Olive Oil and Its Components on Breast Cancer: Molecular Mechanisms.

Breast cancer is the most frequent malignant neoplasia and a leading cause of mortality in women worldwide. The Mediterranean diet has been proposed as a healthy dietary pattern with protective effects in several chronic diseases, including breast cancer. This diet is characterized by the consumption of abundant plant foods and olive oil as the principal source of fat, which is considered one of the main components with potential antioxidant, anti-inflammatory and anticancer effects. Extra-virgin olive oil (EVOO) has several bioactive compounds, mainly including monounsaturated fatty acids, triterpenes and polyphenols, such as phenolic alcohols (e.g., hydroxytyrosol), secoiridoids (e.g., oleuropein and oleocanthal), lignans (e.g., pinoresinol) or flavonoids (e.g., luteolin). While epidemiological evidence is still limited, experimental in vivo and in vitro data have shown a protective effect of this oil and its compounds on mammary carcinogenesis. Such effects account through complex and multiple mechanisms, including changes in epigenetics, transcriptome and protein expression that modulate several signaling pathways. Molecular targets of EVOO compounds have a role in the acquisition of cancer hallmarks. Although further research is needed to elucidate their beneficial effects on human prevention and progression of the disease, evidence points to EVOO in the context of the Mediterranean diet as a heathy choice, while EVOO components may be promising adjuvants in anticancer strategies.

Crystallization of emulsified anhydrous milk fat: The role of confinement and of minor compounds. A DSC study.

We examined the crystallization and melting of anhydrous milk fat (AMF)-in-water emulsions stabilized by sodium caseinate. Various additives at low concentrations (<5 wt%), differing in their hydrocarbon chain length (propionic vs. palmitic acid), unsaturation (palmitic vs. oleic acid), and esterification state (palmitic acid vs. tripalmitin) were used to modulate AMF crystallization kinetics. Three emulsions with different average droplet diameters were cooled down from 60 °C to 4 °C. Fat crystallization was followed by DSC under dynamic (cooling) and static (isothermal) conditions. Propionic acid did not have any noticeable effect. Oleic acid favored supercooling and the formation of unstable polymorphs at short times but its impact faded after 48 h of isothermal storage. The impact of palmitic acid was related to its amphiphilic properties and vanished after 48 h. Tripalmitin influenced crystallization via volume effects that were persistent. It formed mixed crystals which extended the melting range of AMF.

In-House Validation of an SPE-GC-FID Method for the Detection of Free and Esterified Hydroxylated Minor Compounds in Virgin Olive Oils.

Minor compounds in vegetable oils are distributed between free and esterified forms, and the ratio of these two fractions could represent an important parameter for assessment of oil authenticity. A simple method based on offline SPE-GC-FID for the analysis of free and esterified hydroxylated minor compounds in olive and sunflower oils has been developed and in-house validated. A satisfactory repeatability relative standard deviation (<7.5%) was obtained in all cases. The method, which requires simple instrumentation, allows for reliable quantification in a single chromatographic run with the advantages of minimizing sample manipulation, use of toxic solvents and reagents, and time consumption. The analytical procedure was applied to pure oil samples, including 15 authentic extra virgin olive oils collected from different European countries (Spain, Italy, Greece, and Portugal). Finally, the proposed SPE-GC-FID methodology could detect changes in the ratio between the free and esterified forms in pure extra virgin olive oil when mixed with refined sunflower oil at different percentages of 2, 5, 10, 15, and 20% (w/w) to simulate adulteration.

The Potential of Apulian Olive Biodiversity: The Case of Oliva Rossa Virgin Olive Oil.

In this study, the drupes and virgin olive oils extracted from the Oliva Rossa landrace are characterized. Oliva Rossa is an old landrace part of the autochthonous Apulian olive germplasm for which only few data have been reported till now. During the study, the maturity patterns of the drupes had been followed. Four samplings per year were planned, one every 14 days starting from the middle of October. The pigmentation index, the oil content and the total phenolic content of the drupes were measured. Simultaneously, virgin olive oils were extracted at the lab scale and analyzed for the fatty acid composition, the basic quality parameters and the content of minor compounds. The pigmentation pattern of the drupes was different among the years and, despite this trend, at the third sampling time the stage of maximum oil accumulation was always over. The extracted virgin olive oils had a medium to high level of oleic acid. With colder temperatures, a higher level of monounsaturated fatty acids, oleic/linoleic ratio and antioxidants was observed. The phenolic profile was dominated by 3,4-DPHEA-EDA and p-HPEA-EDA while the volatile profile by (E)-2-hexenal and 3-ethyl-1,5-octadiene.

A Global Study by 1H NMR Spectroscopy and SPME-GC/MS of the in Vitro Digestion of Virgin Flaxseed Oil Enriched or not with Mono-, Di- or Tri-Phenolic Derivatives. Antioxidant Efficiency of These Compounds.

The effect of enriching virgin flaxseed oil with dodecyl gallate, hydroxytyrosol acetate or gamma-tocopherol on its in vitro digestion is studied by means of proton nuclear magnetic resonance and solid phase microextraction followed by gas chromatography/mass spectrometry. The extent and pattern of the lipolysis reached in each sample is analyzed, as is the bioaccessibility of the main oil components. None of the phenolic compounds provokes inhibition of the lipase activity and all of them reduce the lipid oxidation degree caused by the in vitro digestion and the bioaccessibility of oxidation compounds. The antioxidant efficiency of the three tested phenols is in line with the number of phenolic groups in its molecule, and is dose-dependent. The concentration of some minor oil components such as terpenes, sesquiterpenes, cycloartenol and 24-methylenecycloartenol is not modified by in vitro digestion. Contrarily, gamma-tocopherol shows very low in vitro bioaccessibility, probably due to its antioxidant behavior, although this increases with enrichment of the phenolic compounds. Oxidation is produced during in vitro digestion even in the presence of a high concentration of gamma-tocopherol, which remains bioaccessible after digestion in the enriched samples of this compound.

Monitoring of minor compounds in corn oil oxidation by direct immersion-solid phase microextraction-gas chromatography/mass spectrometry. New oil oxidation markers.

The aim of this study is to shed light on the evolution of the minor compounds in the corn oil oxidation process, through the information provided by direct immersion-microextraction in solid phase followed by gas chromatography/mass spectrometry (DI-SPME-GC/MS). This methodology enables one, in a single run, to establish the identity and abundance both of original oil minor components, some with antioxidant capacity, and of other compounds coming from both main and minor oil components oxidation. For the first time, some of the compounds formed from oil minor components degradation are proposed as new markers of oil incipient oxidation. Although the study refers to corn oil, the methodology can be applied to any other edible oil and constitutes a new approach to characterizing the oxidation state of edible oils.

Influence of fruit canopy position and maturity on yield determinants and chemical composition of virgin olive oil.

BACKGROUND: While both maturity and light exposure are important factors determining olive fruit physiology, the relationship between maturity, canopy position and optimal harvesting time has not been well-studied. To understand the interaction of these factors, olive fruits from upper and lower layers of the canopy were harvested from September to January. Maturity, moisture and fat content of the fruit as well as the quality and minor components of the oil extracted were measured. RESULTS: Lower light interception at the lower canopy positions resulted in differences in the fruits and oil extracted between canopy layers. Upper layer presented 60% of the overall production; fruit had one unit more of maturity index, 3% less moisture and 5% more fat content. Oil extracted from the upper layers presented higher concentration of oleuropein and ligstroside aglycone. Fruits from upper layers at maturity index of two had higher fat content and more total phenols in the oil extracted when compared with fruits from lower layer with the same maturity index. CONCLUSIONS: Differences in oil composition between layers do not correlate with differences in the fruit maturity index; instead, fruit position is a determining factor for physiological processes related to fruit growth and oil composition. © 2019 Society of Chemical Industry.

Physical and chemical behaviour of Nabali Mohassan single-cultivar olive oil during prolonged storage.

BACKGROUND: The effect of storage time on the fluorescence emission intensity and physico-chemical properties of olive oil from the Palestinian cultivar Nabali Mohassan was investigated. Olive oil samples stored up to 7 years were obtained from different olive orchards in Palestine, where prolonged storage is still in use. RESULTS: As a result of oxidation, all fluorescent minor compounds (tocopherols, chlorophylls, pheophytins and phenolic compounds) of olive oil significantly decreased as the storage time increased, whereas viscosity increased (P < 0.05). Until 1 year of storage, the physico-chemical properties of olive oil samples were within the limits of both Palestinian and European quality standards, and minor compounds, although affected by a marked decrease compared to freshly produced oil, were still detectable. After 5 years, a 90% decrease of the fluorescence attributed to tocopherols occurred and, after 7 years, phenolics reached a loss of 90%. CONCLUSION: The analysis of fluorescence, together with other physical measures, was demonstrated to be a useful tool for monitoring oil aging. This is the first report on fluorescent minor compounds of oils obtained from Nabali Mohassan olive cultivar. A better knowledge of this single-cultivar oil could enhance the adoption of the best practices by producers, improving the whole production chain. © 2018 Society of Chemical Industry.

Contribution of minor compounds present in the peppermint (Mentha piperita) to the iron-catalyzed lipid oxidation of soybean oil-in-water emulsion.

This study evaluated contribution of minor compounds naturally present in peppermint (Mentha piperita) to the iron-catalyzed lipid oxidation of oil-in-water emulsion. Emulsions consisted of tocopherol-stripped soybean oil and pH 4.0 citrate buffer (4:6, w/w) with iron. Minor compounds included α-tocopherol, rosmarinic acid, caffeic acid, ß-carotene, and chlorophyll b at natural concentration in 400 ppm of the peppermint extract. The emulsions were oxidized in the dark, and headspace oxygen contents, hydroperoxide contents, and p-anisidine values were determined. Addition of phenolic compounds decreased headspace oxygen consumption and hydroperoxide and p-anisidine values of emulsions, however, ß-carotene or chlorophyll b tended to increase them. The results suggest that tocopherols at low concentration were the most important to reduce lipid oxidation of emulsions via radical scavenging, followed by high contents of polyphenols via radical scavenging and iron-chelation. Carotenoids and chlorophylls should be precisely controlled even in the dark, possibly due to their oxidation products.

Characterisation of minor components in vegetable oil by comprehensive gas chromatography with dual detection.

The profile of minor compounds, such as alcohols, sterols, free and alkyl fatty acids, waxes, etc., was investigated in different vegetable oils by a comprehensive gas chromatographic system, coupled with a simultaneous dual detection (flame ionisation detector and mass spectrometer) for quantitative and qualitative purposes. Such a system generated a unique two-dimensional chromatogram to be used as a chemical fingerprint. Multi-level information, due not only to a more "comprehensive" preparation technique, but also thanks to the exploitation of a more powerful and sensitive analytical determination allowed the extrapolation of diagnostic information from the minor components profile of different vegetable oils, along with their characteristic profile. Furthermore, an admixture of an extra virgin olive oil with a low amount of sunflower and palm oils was evaluated, attesting to the powerful diagnostic information provided by the proposed approach.

Avaliação da composição química de óleos brasileiros de semente de uva (Vitis vinífera L) e seu efeito sobre parâmetros bioquímicos e inflamatórios em ratos / Brazilian grapeseed oils (Vitis vinífera L) evaluation and it effect of biochemical and inflammatory parameters in rats

O óleo de semente de uva (OSU) caracteriza-se como um importante subproduto do processamento agroindustrial (vinicultura) que vem recebendo destaque como fonte alternativa de óleos vegetais. Os componentes químicos presentes nos óleos vegetais sofrem influência de fatores relacionados ao cultivo e ao processamento industrial. Esses componentes são capazes de modular importantes funções fisiológicas no organismo. Este trabalho objetivou avaliar a composição química de OSU brasileiros e sua influência em parâmetros bioquímicos, de estresse oxidativo e inflamatório sérico e tecidual em ratos. Inicialmente, sete diferentes marcas de OSU disponíveis no mercado brasileiro foram avaliadas e comparadas em relação a dois processos de extração, refino e prensagem a frio. As amostras prensadas a frio apresentaram concentrações significativamente maiores de compostos fenólicos, teores do isômero γ-tocotrienol da vitamina E, de fitosteróis, tendo como principal constituinte o ß-sitosterol, e diversos compostos voláteis característicos. Para a investigação biológica, ratos saudáveis da linhagem Wistar foram suplementados com OSU - amostra comercial que possuía maior teor do isômero γ-tocotrienol e compostos fenólicos; e com o óleo de soja (ODS) - óleo mais consumido no país, utilizado para efeito comparativo. Os dois óleos foram suplementados por intubação orogástrica nas concentrações de 3,0 e 6,0 mL/Kg de peso corpóreo, por 65 dias. Observou-se que os resultados da intervenção não foram dose-dependente para os dois óleos e, apesar do elevado teor de lipídios oferecido aos animais, estes não modificaram o padrão de ganho de peso. Porém, foram observados elevados teores de peroxidação lipídica sérica nos animais tratados com OSU, quando comparados aos tratados com ODS na menor dose administrada. Nos animais do grupo suplementado com OSU na maior dose, verificou-se aumento do peso do tecido adiposo retroperitoneal, caracterizado pela hipertrofia dos adipócitos. Em relação ao tecido hepático, houve maior incorporação do ácido linoleico, principal ácido graxo presente nos OSU e ODS e precursor do ácido araquidônico na cadeia dos eicosanoides, interferindo no aumento da razão das citocinas inflamatórias TNF-α/IL- 4 e IL-6/IL-4, para todos os grupos suplementados com os dois óleos nas maiores concentrações. Quanto aos marcadores de estresse oxidativo no tecido cardíaco, pode-se verificar que os grupos administrados com OSU foram relacionados com a maior atividade das enzimas antioxidantes, acompanhado de maior peroxidação lipídica. Os resultados permitem concluir que os compostos bioativos presentes no OSU não ocasionaram a redução do estresse oxidativo causado pela alta presença do ácido linoleico, porém, os marcadores inflamatórios pouco se alteraram com o tratamento

Grapeseed oil (GSO) is characterized as an important by-product of the agro-industry (winemaking) which has received attention as an alternative source of vegetable oils. Chemical compounds are influenced by cultivation and industrial processing, and these components modulate some important physiological functions in the body. This study aimed to evaluate the chemical composition of Brazilian GSO and its influence on biochemical parameters and inflammation in rats' serum and tissue. Firstly, seven different GSO samples were obtained from Brazilian market and were evaluated and compared for two type of extraction processes, refining and cold pressing. Cold pressed samples showed high significant phenolic concentrations, γ-tocotrienol isomer content and phytosterols concentrations, and presence of several characteristic of volatiles compounds. For biological research, healthy Wistar rats were supplemented with GSO - commercial sample had higher levels of γ-tocotrienol isomer and phenolic compounds; and soybean oil (SBO) - the most consumed oil in the country, used for comparative purposes. Both oils were supplemented daily by orogastric intubation in concentrations of 3.0 and 6.0 mL/kg body weight for 65 days. After intervention was observed no dose dependency behavior for both oils, and despite high level of lipids provided to the animals, they did not change the pattern of the animals weight gain. However, high levels of lipid peroxidation were observed in the animal's serum within GSO treatment when compared to SBO. GSO6 group was an increase of final weight of retroperitoneal adipose tissue, characterized by hypertrophy of adipocytes. Regarding the hepatic tissue, it was observed that there was a greater uptake of linoleic acid, mainly fatty acids present in GSO and SBO and it is a precursor of arachidonic acid in eicosanoids chain, interfering with the ratio increase of the inflammatory cytokines TNF-α/IL-4 and IL-6/IL-4 for all groups supplemented with both oils at higher concentrations. For the parameters of oxidative stress in the cardiac tissue, it can be seen that GSO groups were related to increased activity of the antioxidant enzymes, followed by an increase in TBARS content. The results suggest that the bioactive compounds present in the GSO caused the reduction of the oxidative stress caused by the high presence of linoleic acid, though, inflammatory markers present few changes within treatment

Hydroxytyrosol protects against oxidative DNA damage in human breast cells.

Over recent years, several studies have related olive oil ingestion to a low incidence of several diseases, including breast cancer. Hydroxytyrosol and tyrosol are two of the major phenols present in virgin olive oils. Despite the fact that they have been linked to cancer prevention, there is no evidence that clarifies their effect in human breast tumor and non-tumor cells. In the present work, we present hydroxytyrosol and tyrosol's effects in human breast cell lines. Our results show that hydroxytyrosol acts as a more efficient free radical scavenger than tyrosol, but both fail to affect cell proliferation rates, cell cycle profile or cell apoptosis in human mammary epithelial cells (MCF10A) or breast cancer cells (MDA-MB-231 and MCF7). We found that hydroxytyrosol decreases the intracellular reactive oxygen species (ROS) level in MCF10A cells but not in MCF7 or MDA-MB-231 cells while very high amounts of tyrosol is needed to decrease the ROS level in MCF10A cells. Interestingly, hydroxytyrosol prevents oxidative DNA damage in the three breast cell lines. Therefore, our data suggest that simple phenol hydroxytyrosol could contribute to a lower incidence of breast cancer in populations that consume virgin olive oil due to its antioxidant activity and its protection against oxidative DNA damage in mammary cells.