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Currently, Bixa orellana L. extracts are used as a color source in the food, pharmaceutical, and cosmetic industries because they are important as a potential source of antioxidant activity. The extraction is carried out by conventional methods, using alkaline solutions or organic solvents. These extraction methods do not take advantage of the lipid fraction of annatto (Bixa orellana L.) seeds, and the process is not friendly to the environment. In this work, the objective was to obtain an extract rich in nutraceuticals (bixin and tocols) of high antioxidant power from Peruvian annatto seeds as a potential source for a functional food or additive in the industry using supercritical fluid extraction (SFE). Experiments related to extraction yield, bixin, tocotrienols, tocopherols, and antioxidant activity were carried out. The SFE was performed at 40 °C, 50 °C, and 60 °C, and 100, 150, and 250 bar with 0.256 kg/h carbon dioxide as the supercritical solvent (solvent-to-feed ratio of 10.2). Supercritical extraction at 60 °C and 250 bar presented the best results in terms of global extraction yield of 1.40 ± 0.01 g/100 g d.b., extract concentration of 0.564 ± 0.005 g bixin/g extract, 307.8 mg α-tocotrienol/g extract, 39.2 mg ß-tocotrienol/g extract, 2 mg γ-tocopherol/g extract, and IC50 of 989.96 µg extract/mL. Economical evaluation showed that 60 °C, 250 bar, and 45 min presented the lowest cost of manufacturing (2 × 2000 L, COM of USD 212.39/kg extract). This extract is a potential source for functional food production.
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Vitamin E is a lipid-soluble nutrient found mainly in vegetable oils and oilseeds. It is divided into eight homologous compounds; however, only α-tocopherol exhibits vitamin activity. Many advantages are related to these compounds, including cellular protection through antioxidant and anti-inflammatory activity, and improving lipid metabolism. Physiopathology of many diseases incepts with reduced antioxidant defense, characterized by an increased reactive oxygen species production and activation of transcription factors involved in inflammation, such as nuclear factor-kappa B (NF-κB), that can be linked to oxidative stress. Moreover, disorders of lipid metabolism can increase the risk of cardiovascular diseases. In addition, intestinal dysbiosis plays a vital role in developing chronic non-communicable diseases. In this regard, vitamin E can be considered to mitigate those disorders, but data still needs to be more conclusive. This narrative review aims to elucidate the mechanisms of action of vitamin E and if supplementation can be beneficial in a disease scenario regarding non-communicable diseases.
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Doenças não Transmissíveis , Vitamina E , Humanos , Antioxidantes/uso terapêutico , Antioxidantes/farmacologia , Estresse Oxidativo , alfa-TocoferolRESUMO
INTRODUCTION: The genus Clusia L. is mostly recognised for the production of prenylated benzophenones and tocotrienol derivatives. OBJECTIVES: The objective of this study was to map metabolome variation within Clusia minor organs at different developmental stages. MATERIAL AND METHODS: In total 15 organs/stages (leaf, flower, fruit, and seed) were analysed by UPLC-MS and 1H- and heteronuclear multiple-bond correlation (HMBC)-NMR-based metabolomics. RESULTS: This work led to the assignment of 46 metabolites, belonging to organic acids(1), sugars(2) phenolic acids(1), flavonoids(3) prenylated xanthones(1) benzophenones(4) and tocotrienols(2). Multivariate data analyses explained the variability and classification of samples, highlighting chemical markers that discriminate each organ/stage. Leaves were found to be rich in 5-hydroxy-8-methyltocotrienol (8.5 µg/mg f.w.), while flowers were abundant in the polyprenylated benzophenone nemorosone with maximum level detected in the fully mature flower bud (43 µg/mg f.w.). Nemorosone and 5-hydroxy tocotrienoloic acid were isolated from FL6 for full structural characterisation. This is the first report of the NMR assignments of 5-hydroxy tocotrienoloic acid, and its maximum level was detected in the mature fruit at 50 µg/mg f.w. Seeds as typical storage organ were rich in sugars and omega-6 fatty acids. CONCLUSION: To the best of our knowledge, this is the first report on a comparative 1D-/2D-NMR approach to assess compositional differences in ontogeny studies compared with LC-MS exemplified by Clusia organs. Results derived from this study provide better understanding of the stages at which maximal production of natural compounds occur and elucidate in which developmental stages the enzymes responsible for the production of such metabolites are preferentially expressed.
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Clusia , Clusia/química , Frutas/química , Cromatografia Líquida , Espectrometria de Massas em Tandem , Benzofenonas/análise , Benzofenonas/química , Benzofenonas/metabolismo , Flores/química , Folhas de Planta/química , Metabolômica/métodos , Sementes/química , Açúcares/análiseRESUMO
All-trans retinoic acid and arsenic trioxide are the leading choices for the treatment of acute promyelocytic leukemia. Notwithstanding the impressive differentiative properties of all-trans retinoic acid and the apoptotic properties of arsenic trioxide, some problems still occur in acute promyelocytic leukemia treatment. These problems are due to patients' relapses, mainly related to changes in the ligand-binding domain of RARα (retinoic acid receptor α) and the cardiotoxic effects caused by arsenic trioxide. We previously developed a self-nanoemulsifying drug delivery system enriched with tocotrienols to deliver all-trans retinoic acid (SNEDDS-TRF-ATRA). Herein, we have evaluated if tocotrienols can help revert ATRA resistance in an APL cell line (NB4-R2 compared to sensitive NB4 cells) and mitigate the cardiotoxic effects of arsenic trioxide in a murine model. SNEDDS-TRF-ATRA enhanced all-trans retinoic acid cytotoxicity in NB4-R2 (resistant) cells but not in NB4 (sensitive) cells. Moreover, SNEDDS-TRF-ATRA did not significantly change the differentiative properties of all-trans retinoic acid in both NB4 and NB4-R2 cells. Combined administration of SNEDDS-TRF-ATRA and arsenic trioxide could revert QTc interval prolongation caused by ATO but evoked other electrocardiogram alterations in mice, such as T wave flattening. Therefore, SNEDDS-TRF-ATRA may enhance the antileukemic properties of all-trans retinoic acid but may influence ECG changes caused by arsenic trioxide administration. SNEDDS-TRF-ATRA presents cytotoxicity in resistant APL cells (NB4-R2). Combined administration of ATO and SNEDDS-TRF-ATRA in mice prevented the prolongation of the QTc interval caused by ATO but evoked ECG abnormalities such as T wave flattening.
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Leucemia Promielocítica Aguda , Tocotrienóis , Animais , Camundongos , Trióxido de Arsênio/farmacologia , Trióxido de Arsênio/uso terapêutico , Leucemia Promielocítica Aguda/tratamento farmacológico , Leucemia Promielocítica Aguda/metabolismo , Tocotrienóis/uso terapêutico , Tretinoína/farmacologia , Tretinoína/uso terapêutico , Eletrocardiografia , Óxidos/farmacologia , Óxidos/uso terapêuticoRESUMO
Bixa orellana L. is a plant popularly known as "ucurum", "annatto", and "achiote". It is native to South America, and its seeds are an abundant source of geranylgeraniol and tocotrienols. Nanoencapsulation is a valuable technique that can decrease the drug needed to achieve an effect, decreasing potential toxicity, side effects and potentiate the anti-inflammatory effect. This study aimed to evaluate the acute toxicity of an intramuscular application of a nanodispersion containing a standardized extract from the seeds of Bixa orellana (NBO) in Wistar rats. The chemical evaluation showed δ-tocotrienol at 0.725 ± 0.062 mg/mL (72.6 ± 0.9%). The stability study showed the nanoparticles had an average size from 53.15 ± 0.64 to 59.9 ± 3.63 nm, with a polydispersity index ranging from 0.574 ± 0.032 to 0.574 ± 0.32, Zeta potential from 18.26 ± 0.59 to 19.66 ± 1.45 mV. After testing the intramuscular application of NBO with doses from 1 to 5 mg/kg in animals, it was observed that the acute treatment did not elicit any toxic effects within this range. The dose of 10 mg/kg, although not affecting hematological and biochemical parameters (CPK, LDH, myoglobin, AST, ALT, TC, TG, glucose levels, creatinine, and urea), could induce some muscle tissue changes, including leukocyte infiltration, morphological chances, and potentially necrosis. In conclusion, the results showed that the treatments devoided toxicity between 1 and 5 mg/kg.
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Bixaceae , Tocotrienóis , Ratos , Animais , Ratos Wistar , Tocotrienóis/farmacologia , Tocotrienóis/uso terapêutico , Anti-Inflamatórios/toxicidade , Sementes , Extratos Vegetais/toxicidade , Extratos Vegetais/uso terapêuticoRESUMO
BACKGROUND: Vitamin E has been investigated for its antitumor potential, including the ability to change cancer gene pathways as well as promote antioxidant and pro-oxidant activity. OBJECTIVE: Therefore, this systematic review aimed to evaluate antitumor and chemopreventive activity of different vitamin E isoforms (tocopherols and tocotrienols) through in vitro and in vivo studies. METHOD: The systematic review was registered in PROSPERO (No. CRD4202126207) and the search was carried out in four electronic databases (PubMed, Science Direct, Scopus and Web of Science) in June 2021 by three independent reviewers. The search equation used was: "Supplementation" AND ("Vitamin E" OR Tocopherol OR Tocotrienol) AND "breast cancer" AND (chemotherapy OR therapy OR prevention). In vitro studies and animal models of breast cancer supplemented with tocopherol or tocotrienol vitamers, alone or in combination, were included. RESULTS: The results revealed 8546 relevant studies that were initially identified in our search. After analysis, a total of 12 studies were eligible for this systematic review. All studies included animal models, and 5 of them also performed in vitro experiments on cancer cell lines. The studies performed supplementation with tocopherols, mixtures (tocopherols and tocotrienols) and synthetic vitamin E forms. There was an significant association of estradiol, dendritic cells and pterostilbene in combined therapy with vitamin E. Vitamin E delayed tumor development, reduced tumor size, proliferation, viability, expression of anti-apoptotic and cell proliferation genes, and upregulated pro-apoptotic genes, tumor suppressor genes and increased immune response. The effects on oxidative stress markers and antioxidant activity were conflicting among studies. Only one study with synthetic vitamin E reported cardiotoxicity, but it did not show vitamin E genotoxicity. CONCLUSION: In conclusion, vitamin E isoforms, isolated or associated, showed antitumor and chemopreventive activity. However, due to studies heterogeneity, there is a need for further analysis to establish dose, form, supplementation time and breast cancer stage.
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Neoplasias , Tocotrienóis , Animais , Vitamina E/farmacologia , Tocotrienóis/farmacologia , Tocotrienóis/uso terapêutico , Antioxidantes/farmacologia , Tocoferóis/farmacologia , Neoplasias/tratamento farmacológico , VitaminasRESUMO
Tree nuts are rich in polar (phenolic compounds) and non-polar (tocols) antioxidants, with recognized effects in the prevention of diseases such as cancer. These biomolecules possess antiproliferative activity on cancer cells; however, the combined effect of both types of compounds has been scarcely studied, and this approach could give valuable information on the real anticancer potential of tree nuts. In the present study, the antiproliferative activity of pure tocols and phenolic compounds, tocol- and phenolic-rich extracts (TRE and PRE, respectively) from tree nuts and the extracts combinations, was evaluated in four cancer (HeLa, MCF7, PC3, A549) and one control (ARPE) cell lines. The most sensible cell lines were HeLa and MCF7. TRE and PRE from nuts were chemically characterized; γ and δ tocopherols, total tocols, total tocopherols and total phenolic compounds were negatively correlated with cell viability in MCF7 cells. In HeLa cells, only δ and total tocopherols were negatively correlated with cell viability. TRE and PRE had a low effect in reducing cell viability of the cancer cell lines, the most effective extracts were those of emory oak acorn (EOA), pecan nut (PEC) and walnut (WAL), and these were further studied for their pharmacological interactions, using the combination index and the isobologram methods. Combinations of both extracts showed a synergistic and strongly synergistic behavior in the three nuts (EOA, PEC and WAL), with combination indexes between 0.12 and 0.55. These results highlight the need to understand the interactions among components found in complex natural extracts or food products in order to fully understand their bioactivities.
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Neoplasias , Nozes , Células HeLa , Humanos , Nozes/química , Fenóis/análise , Fenóis/farmacologia , Extratos Vegetais/análise , Extratos Vegetais/farmacologia , Tocoferóis/análiseRESUMO
BACKGROUND: Local leafy vegetables are gaining attention as affordable sources of micronutrients, including vitamins, pro-vitamin carotenoids and other bioactive compounds. Stinging nettles (Urtica spp.) are used as source of fibers, herbal medicine and food. However, despite the relatively wide geographical spread of Urtica leptophylla on the American continent, little is known about its content of vitamin E congeners and carotenoids. We therefore investigated the particular nutritional potential of different plant structures of wild Costa Rican U. leptophylla by focusing on their vitamin E and carotenoid profiles. RESULTS: Young, mature and herbivore-damaged leaves, flowers, stems and petioles were collected and freeze-dried. Vitamin E and carotenoids were determined by high-performance liquid chromatography after liquid/liquid extraction with hexane. α-Tocopherol was the major vitamin E congener in all structures. Flowers had a high content of γ-tocopherol. Herbivore-damaged leaves had higher contents of vitamin E than undamaged leaves. Lutein was the major and ß-carotene the second most abundant carotenoid in U. leptophylla. No differences in carotenoid profiles were observed between damaged and undamaged leaves. CONCLUSION: The leaves of U. leptophylla had the highest nutritional value of all analyzed structures; therefore, they might represent a potential source of α-tocopherol, lutein and ß-carotene. © 2022 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
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Urtica dioica , Vitamina E , Carotenoides/análise , Costa Rica , Flores/química , Hexanos , Luteína/análise , Vitamina E/análise , Vitaminas/análise , alfa-Tocoferol/análise , beta Caroteno/análise , gama-Tocoferol/análiseRESUMO
Aim: All-trans retinoic acid (ATRA) shows erratic oral bioavailability when administered orally against leukemia, which can be solved through its incorporation in self-nanoemulsifying drug-delivery systems (SEDDS). The SEDDS developed contained a hydrophobic ion pair between benzathine (BZT) and ATRA and was enriched with tocotrienols by the input of a palm oil tocotrienol rich fraction (TRF) in its composition. Results: SEDDS-TRF-ATRA-BZT allowed the formation of emulsions with nanometric size that retained ATRA within their core after dispersion. Pharmacokinetic parameters after oral administration of SEDDS-TRF-ATRA-BZT in mice were improved compared with what was seen for an ATRA solution. Moreover, SEDDS-TRF-ATRA-BZT had improved activity against HL-60 cells compared with SEDDS without TRF. Conclusion: SEDDS-TRF-ATRA-BZT is a promising therapeutic choice over ATRA conventional medicine.
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Sistemas de Liberação de Medicamentos , Tretinoína , Administração Oral , Animais , Disponibilidade Biológica , Emulsões , CamundongosRESUMO
The ultimate health benefits of peanuts and tree nuts partially depend on the effective gastrointestinal delivery of their phytochemicals. The chemical composition and in vitro bioaccessibility of tocopherols, tocotrienols and phenolic compounds from peanuts and seven tree nuts were evaluated by analytical and chemometric methods. Total fat and dietary fiber (g 100 g-1) ranged from 34.2 (Emory oak acorn) to 72.5 (pink pine nut; PPN) and from 1.2 (PPN) to 22.5 (pistachio). Samples were rich in oleic and linoleic acids (56-87 g 100 g-1 oil). Tocopherols and tocotrienols (mg·kg-1) ranged from 48.1 (peanut) to 156.3 (almond) and 0 (almond, pecan) to 22.1 (PPN) and hydrophilic phenolics from 533 (PPN) to 12,896 (Emory oak acorn); flavonoids and condensed tannins (mg CE.100 g-1) ranged from 142 (white pine nut) to 1833 (Emory oak acorn) and 14 (PPN) to 460 (Emory oak acorn). Three principal components explained 90% of the variance associated with the diversity of antioxidant phytochemicals in samples. In vitro bioaccessibility of tocopherols, tocotrienols, hydrophilic phenolics, flavonoids, and condensed tannins ranged from 11-51%, 16-79%, 25-55%, 0-100%, and 0-94%, respectively. Multiple regression analyses revealed a potential influence of dietary fiber, fats and/or unsaturated fatty acids on phytochemical bioaccessibility, in a structure-specific manner.
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Antioxidantes/farmacocinética , Nozes/química , Compostos Fitoquímicos/farmacocinética , Disponibilidade Biológica , Flavonoides/farmacocinética , Humanos , Hidroxibenzoatos/farmacocinética , Análise de Componente Principal , Proantocianidinas/farmacocinética , Análise de Regressão , Tocoferóis/farmacocinética , Tocotrienóis/farmacocinéticaRESUMO
This study analyzes the lipid composition and the oxidative stability of oils of Sapindaceae and Meliaceae seeds. The oil content ranged from 14.7% (Guarea guidonia) to 30.1% (Allophylus puberulus and Paullinia elegans). Ten fatty acids were identified in seed oils. Guarea guidonia seeds accumulated mainly oleic (44.9%) and linoleic (24.1%) acid, whereas the unusual gondoic and paullinic acids were identified in A. puberulus (15.8%; 8.9%) and P. elegans (14.4%; 44.2%), respectively. The oil of P. elegans had the highest oxidative stability (16.2 h.). Tocopherol predominated in A. puberulus (10.4 mg/100 g) and tocotrienol predominated in G. guidonea and P. elegans (2.6 mg/100 g). The vitamers α-tocopherol, γ-tocopherol, and γ-tocotrienol were found in the studied oils. ß-carotene was predominantly detected in the oil of A. puberulus seeds (22.4 µg/g). Guarea guidonia seed oil has a high potential in food due to richness in essential fatty acids. In turn, A. puberulus and P. elegans oils could be suggested for other industrial purposes (e.g., biodiesel, varnishes, paints, soaps, or oleochemicals) due to their content of long-chain fatty acids.
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This study investigated and compared the occurrence and concentration of macronutrients, moisture, ash, dietary fiber, fatty acids, minerals, carotenoids, vitamins, flavonoids, phenolic compounds, antioxidant activity, phytate and tannin in Brazilian chia seeds grown in the states of Mato Grosso (MT) and Rio Grande do Sul (RS). High concentrations of lipids (31.2g.100g-1, on average), proteins (18.9g.100g-1, on average), dietary fiber (35.3g.100g-1, on average), vitamin E (8,203.6µg.100g-1, on average) were observed. Similar values for total phenolic compounds and phytic acid in chia seeds from both regions were observed. Chia grown in RS showed higher antioxidant activity than chia grown in MT, and the tannin concentrations were higher in chia seeds grown in Mato Grosso (19.08±1.08eq.catequina/gsample). In conclusion, Brazilian chia seeds showed high concentrations of lipids, proteins, total dietary fiber, minerals and vitamin E.
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Carotenoides/análise , Ácidos Graxos/análise , Fenóis/análise , Salvia/química , Sementes/química , Taninos/análise , Vitamina E/análise , Brasil , OxirreduçãoRESUMO
BACKGROUND: Biofortified maize is not only a good vehicle for provitamin A carotenoids for vitamin A deficient populations in developing countries but also a source of vitamin E, tocochromanols and phenolic compounds, which have antioxidant properties. Using high-performance liquid chromatography and a total antioxidant performance assay, the present study analyzed the antioxidant variation and antioxidant activity of 36 provitamin A improved maize hybrids and one common yellow maize hybrid. RESULTS: The ranges of major carotenoids in provitamin A carotenoids biofortified maize were zeaxanthin [1.2-13.2 µg g-1 dry weight (DW)], ß-cryptoxanthin (1.3-8.8 µg g-1 DW) and ß-carotene (1.3-8.0 µg g-1 DW). The ranges of vitamin E compounds identified in provitamin A carotenoids biofortified maize were α-tocopherol (3.4-34.3 µg g-1 DW), γ-tocopherol (5.9-54.4 µg g-1 DW), α-tocotrienol (2.6-19.5 µg g-1 DW) and γ-tocotrienol (45.4 µg g-1 DW). The ranges of phenolic compounds were γ-oryzanol (0.0-0.8 mg g-1 DW), ferulic acid (0.4-3.6 mg g-1 DW) and p-coumaric acid (0.1-0.45 mg g-1 DW). There was significant correlation between α-tocopherol and cis isomers of ß-carotene (P < 0.01). Tocotrienols were correlated with α-tocopherol and γ-oryzanol (P < 0.01). CONCLUSION: Genotype was significant in determining the variation in ß-cryptoxanthin, ß-carotene, α-tocopherol and γ-tocopherol contents (P < 0.01). A genotype × environment interaction was observed for γ-tocopherol content (P < 0.01). © 2016 Society of Chemical Industry.