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1.
Nutrients ; 13(4)2021 Apr 13.
Article in English | MEDLINE | ID: mdl-33924335

ABSTRACT

Obesity and its related complications are a world-wide health problem. Dietary tocotrienols (TT) have been shown to improve obesity-associated metabolic disorders, such as hypercholesterolemia, hyperglycemia, and gut dysbiosis. This study examined the hypothesis that the antioxidant capacity of TT alters metabolites of oxidative stress and improves systemic metabolism. C57BL/6J mice were fed either a high-fat diet (HFD control) or HFD supplemented with 800 mg annatto-extracted TT/kg (HFD+TT800) for 14 weeks. Sera from obese mice were examined by non-targeted metabolite analysis using UHPLC/MS. Compared to the HFD group, the HFD+TT800 group had higher levels of serum metabolites, essential amino acids (lysine and methionine), sphingomyelins, phosphatidylcholine, lysophospholipids, and vitamins (pantothenate, pyridoxamine, pyridoxal, and retinol). TT-treated mice had lowered levels of serum metabolites, dicarboxylic fatty acids, and inflammatory/oxidative stress markers (trimethylamine N-oxide, kynurenate, 12,13-DiHOME, and 13-HODE + 9-HODE) compared to the control. The results suggest that TT supplementation lowered inflammation and oxidative stress (oxidized glutathione and GSH/GSSH) and improved macronutrient metabolism (carbohydrates) in obese mice. Thus, TT actions on metabolites were beneficial in reducing obesity-associated hypercholesterolemia/hyperglycemia. The effects of a non-toxic dose of TT in mice support the potential for clinical applications in obesity and metabolic disease.


Subject(s)
Antioxidants/administration & dosage , Bixaceae/chemistry , Carotenoids/chemistry , Dietary Supplements , Obesity/diet therapy , Plant Extracts/chemistry , Tocotrienols/administration & dosage , Animals , Antioxidants/isolation & purification , Diet, High-Fat/adverse effects , Disease Models, Animal , Humans , Inflammation/blood , Inflammation/diagnosis , Inflammation/diet therapy , Inflammation/immunology , Male , Mice , Mice, Inbred C57BL , Nutrients/metabolism , Obesity/blood , Obesity/etiology , Obesity/metabolism , Oxidative Stress/drug effects , Tocotrienols/isolation & purification
2.
J Nat Prod ; 84(4): 972-978, 2021 04 23.
Article in English | MEDLINE | ID: mdl-33667092

ABSTRACT

Two tocotrienol derivatives, garcipaucinones A (1) and B (2), and a biosynthetically related known analogue (3) were isolated from the fruit of Garcinia paucinervis. Their structures including absolute configurations were unequivocally determined by spectroscopic methods complemented with electronic circular dichroism (ECD) calculations and gauge-independent atomic orbital (GIAO) NMR calculations. Compounds 1 and 2 are the first naturally occurring tocotrienol derivatives with a 3,10-dioxatricyclo-[7.3.1.02,7]tridecane skeleton incorporating an unusual γ-pyrone motif. A reasonable biosynthetic pathway for formation of the two compounds is proposed. The antiproliferative and anti-inflammatory activities of compounds 1 and 2 were also evaluated.


Subject(s)
Garcinia/chemistry , Tocotrienols/pharmacology , Animals , Anti-Inflammatory Agents , Antineoplastic Agents, Phytogenic , Cell Line, Tumor , China , Fruit/chemistry , Humans , Mice , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , RAW 264.7 Cells , Tocotrienols/isolation & purification
3.
Fitoterapia ; 146: 104688, 2020 Oct.
Article in English | MEDLINE | ID: mdl-32702430

ABSTRACT

Three undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) and three tocotrienols derivatives, named as paucinochymol A-F (1-3 and 10-12), together with six known PPAPs, were isolated from the fruits of Garcinia paucinervis. Their structures and absolute configurations were determined by extensive NMR analysis and electronic circular dichroism (ECD) calculation methods. Paucinochymol A (1) is the first compound of this type featuring a ω-isogeranyl with tetrahydrofuran unit at C-1. Paucinochymols D and E (4-5) belong to rare tocotrienol with one glorious macrocyclic and an ortho-quinone moiety, respectively. The antiproliferative and anti-inflammatory activities of all isolates were tested. Four PPAPs exhibited weak inhibitory activities against three human cancer cell lines (HepG2, T98, MCF-7) with IC50 values ranging from 10.0 to 16.0 µM. Paucinochymol D (10) displayed moderate inhibitory effects against nitric oxide (NO) production with the IC50 value of 19.8 µM.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Antineoplastic Agents, Phytogenic/pharmacology , Garcinia/chemistry , Phloroglucinol/pharmacology , Tocotrienols/pharmacology , Animals , Anti-Inflammatory Agents/isolation & purification , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Line, Tumor , China , Fruit/chemistry , Humans , Mice , Molecular Structure , Nitric Oxide/metabolism , Phloroglucinol/isolation & purification , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , RAW 264.7 Cells , Tocotrienols/isolation & purification
4.
Nutrients ; 12(2)2020 Feb 18.
Article in English | MEDLINE | ID: mdl-32085610

ABSTRACT

BACKGROUND: Several natural products have been reported to elicit beneficial effects against neurodegenerative disorders due to their vitamin E contents. However, the neuroprotective efficacy of palm oil or its tocotrienol-rich fraction (TRF) from the pre-clinical cell and animal studies have not been systematically reviewed. METHODS: The protocol for this systematic review was registered in "PROSPERO" (CRD42019150408). This review followed the Preferred Reporting Items for Systematic Reviews and Meta-Analysis (PRISMA) guidelines. The Medical Subject Heading (MeSH) descriptors of PubMed with Boolean operators were used to construct keywords, including ("Palm Oil"[Mesh]) AND "Nervous System"[Mesh], ("Palm Oil"[Mesh]) AND "Neurodegenerative Diseases"[Mesh], ("Palm Oil"[Mesh]) AND "Brain"[Mesh], and ("Palm Oil"[Mesh]) AND "Cognition"[Mesh], to retrieve the pertinent records from PubMed, Scopus, Web of Science and ScienceDirect from 1990 to 2019, while bibliographies, ProQuest and Google Scholar were searched to ensure a comprehensive identification of relevant articles. Two independent investigators were involved at every stage of the systematic review, while discrepancies were resolved through discussion with a third investigator. RESULTS: All of the 18 included studies in this review (10 animal and eight cell studies) showed that palm oil and TRF enhanced the cognitive performance of healthy animals. In diabetes-induced rats, TRF and α-tocotrienol enhanced cognitive function and exerted antioxidant, anti-apoptotic and anti-inflammatory activities, while in a transgenic Alzheimer's disease (AD) animal model, TRF enhanced the cognitive function and reduced the deposition of ß-amyloid by altering the expression of several genes related to AD and neuroprotection. In cell studies, simultaneous treatment with α-tocotrienols and neurotoxins improved the redox status in neuronal cells better than ϒ- and δ-tocotrienols. Both pre-treatment and post-treatment with α-tocotrienol relative to oxidative insults were able to enhance the survival of neuronal cells via increased antioxidant responses. CONCLUSIONS: Palm oil and its TRF enhanced the cognitive functions of healthy animals, while TRF and α-tocotrienol enhanced the cognitive performance with attenuation of oxidative stress, neuroinflammation and apoptosis in diabetes-induced or transgenic AD animal models. In cell studies, TRF and α-tocotrienol exerted prophylactic neuroprotective effects, while α-tocotrienol exerted therapeutic neuroprotective effects that were superior to those of ϒ- and δ-tocotrienol isomers.


Subject(s)
Alzheimer Disease/psychology , Cognition/drug effects , Neuroprotective Agents , Oxidative Stress/drug effects , Palm Oil/pharmacology , Tocotrienols/pharmacology , Alzheimer Disease/metabolism , Alzheimer Disease/therapy , Amyloid beta-Peptides/metabolism , Animals , Anti-Inflammatory Agents , Antioxidants , Cells, Cultured , Chemical Fractionation , Disease Models, Animal , Humans , Mice , Palm Oil/chemistry , Palm Oil/therapeutic use , Phytotherapy , Rats , Tocotrienols/isolation & purification , Tocotrienols/therapeutic use
5.
Fitoterapia ; 136: 104175, 2019 Jul.
Article in English | MEDLINE | ID: mdl-31095982

ABSTRACT

Four new compounds (1-4) together with six known compounds (5-10) were isolated from the leaf extract of Garcinia nigrolineata. Compound 4 is a rare tocotrienol quinone dimer. The structures were elucidated based on NMR and MS data. All isolated compounds were evaluated for their antibacterial activities.


Subject(s)
Garcinia/chemistry , Plant Extracts/chemistry , Plant Leaves/chemistry , Tocotrienols/pharmacology , Microbial Sensitivity Tests , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Thailand , Tocotrienols/isolation & purification
6.
J Nat Prod ; 82(1): 51-58, 2019 01 25.
Article in English | MEDLINE | ID: mdl-30629440

ABSTRACT

Recent studies have highlighted the biological potential of tocotrienols, a vitamin E subfamily. The major natural sources of tocotrienols are complex mixtures requiring particularly challenging purification processes. The present study describes efficient semi-synthetic strategies toward relevant δ-( R)-tocotrienol derivatives, using as a starting material δ-( R)-garcinoic acid, the major vitamin E derivative isolated from Garcinia kola nuts, a renewable vegetal source.


Subject(s)
Garcinia/metabolism , Tocotrienols/metabolism , Tocotrienols/isolation & purification
7.
J Oleo Sci ; 68(1): 13-20, 2019 Jan 01.
Article in English | MEDLINE | ID: mdl-30542005

ABSTRACT

To develop and use the hazelnut, the main composition, and the physicochemical characteristics, fatty acid compositions, triacylglycerol (TAG) distribution and tocol contents of Hazelnut (Corylus mandshurica Maxim.) which growing in Changbai mountain of Jilin province (HO1) and Anshan city of Liaoning province (HO2) in China were investigated, and the comparative study between the two hazelnut oils and American hazelnut / Turkish hazelnut were also explored. The content of crude lipid and protein in HO1 and HO2 were approximately 54% and 17%, 55% and 16%, respectively. The two hazelnut oils were abundant in unsaturated fatty acids, with the primary unsaturated fatty acids were oleic acid (78%-80%) and linoleic acid (14-16%), which accounted for above 90% of the oils. Therefore, both of the hazelnut oils were important sources of essential fatty acid. In addition, the main saturated fatty acid of the two hazelnut oils were palmitic acid (3%) and stearic acid (1-2%). The main triacylglycerols (TGA) profile were dioleolinolein (OOL), oleodilinolein (OLL) and triolein (OOO). The contents of tocol were 574.44 µg/g, 647.49 µg/g oil in HO1 and HO2, respectively, both of them were higher than that of grape seed oils (454 µg/g), olive oils (209 µg/g) and walnut oils (255 µg/g). The total phytosterol contents were over 2000µg/g and ß-sitosterol was the most predominant sterol in two oils.


Subject(s)
Corylus/chemistry , Lipids/analysis , Fatty Acids/analysis , Fatty Acids/isolation & purification , Lipids/isolation & purification , Phytosterols/analysis , Phytosterols/isolation & purification , Plant Oils/analysis , Plant Oils/isolation & purification , Tocopherols/analysis , Tocopherols/isolation & purification , Tocotrienols/analysis , Tocotrienols/isolation & purification , Triglycerides/analysis , Triglycerides/isolation & purification
8.
Drug Des Devel Ther ; 12: 1715-1726, 2018.
Article in English | MEDLINE | ID: mdl-29942115

ABSTRACT

PURPOSE: Annatto-derived tocotrienol (AnTT) has been shown to improve bone formation in animal models of osteoporosis. However, detailed studies of the effects of AnTT on preosteoblastic cells were limited. This study was conducted to investigate the osteogenic effect of AnTT on preosteoblast MC3T3-E1 cells in a time-dependent manner. MATERIALS AND METHODS: Murine MC3T3-E1 preosteoblastic cells were cultured in the different concentrations of AnTT (0.001-1 µg/mL) up to 24 days. Expression of osteoblastic differentiation markers was measured by qPCR (osterix [OSX], collagen 1 alpha 1 [COL1α1], alkaline phosphatase [ALP], and osteocalcin [OCN]) and by fluorometric assay for ALP activity. Detection of collagen and mineralized nodules was done via Direct Red staining and Alizarin Red staining, respectively. RESULTS: The results showed that osteoblastic differentiation-related genes, such as OSX, COL1α1, ALP, and OCN, were significantly increased in the AnTT-treated groups compared to the vehicle group in a time-dependent manner (P<0.05). Type 1 collagen level was increased from day 3 to day 15 in the AnTT-treated groups, while ALP activity was increased from day 9 to day 21 in the AnTT-treated groups (P<0.05). Enhanced mineralization was observed in the AnTT-treated groups via increasing Alizarin Red staining from day 3 to day 21 (P<0.05). CONCLUSION: Our results suggest that AnTT enhances the osteogenic activity by promoting the bone formation-related genes and proteins in a temporal and sequential manner.


Subject(s)
Bixaceae , Osteoblasts/drug effects , Osteogenesis/drug effects , Stem Cells/drug effects , Tocotrienols/pharmacology , 3T3 Cells , Alkaline Phosphatase/genetics , Alkaline Phosphatase/metabolism , Animals , Bixaceae/chemistry , Cell Proliferation/drug effects , Cell Shape/drug effects , Cell Survival/drug effects , Collagen Type I/genetics , Collagen Type I/metabolism , Collagen Type I, alpha 1 Chain , Dose-Response Relationship, Drug , Gene Expression Regulation/drug effects , Mice , Osteoblasts/metabolism , Osteocalcin/genetics , Osteocalcin/metabolism , Osteogenesis/genetics , Phytotherapy , Plants, Medicinal , Seeds , Sp7 Transcription Factor/genetics , Sp7 Transcription Factor/metabolism , Stem Cells/metabolism , Time Factors , Tocotrienols/isolation & purification
9.
J Oleo Sci ; 67(6): 669-678, 2018 Jun 01.
Article in English | MEDLINE | ID: mdl-29760331

ABSTRACT

Rice bran contains a great amount of functional lipids and phytochemicals including γ-oryzanols, tocotrienols, and tocopherols. However, utilization of those compounds is limited and needs some proven guidelines for better implementation. We introduce some effective strategies for the utilization of rice functional lipids, including an introduction of pigmented rice varieties for better bioactive compounds, biofortification of rice tocotrienols, plasma technology for improving rice phytochemicals, supercritical CO2 extraction of high quality rice bran oil, and an example on the development of tocotrienol-fortified foods.


Subject(s)
Food, Fortified , Oryza/chemistry , Phytochemicals/isolation & purification , Rice Bran Oil/chemistry , Rice Bran Oil/isolation & purification , Antioxidants/isolation & purification , Liquid-Liquid Extraction/methods , Phenylpropionates/isolation & purification , Tocopherols/isolation & purification , Tocotrienols/isolation & purification
10.
Biomed Pharmacother ; 103: 453-462, 2018 Jul.
Article in English | MEDLINE | ID: mdl-29674281

ABSTRACT

INTRODUCTION: Osteoporosis is a debilitating skeletal side effect of androgen deprivation therapy based on gonadotropin-releasing hormone (GnRH) agonist in men. Tocotrienol from Bixa orellana (annatto) has been demonstrated to offer protection against osteoporosis by exerting anabolic effects on bone. Thus, it may prevent osteoporosis among GnRH agonist users. OBJECTIVE: This study aimed to determine the effectiveness of annatto-tocotrienol on the bone turnover markers and bone histomorphometry in a model of male osteoporosis induced by buserelin (a GnRH agonist). METHODS: Forty-six three-months-old male Sprague-Dawley rats (three months old; 300-350 g) were randomly divided into six groups. The baseline control group (n = 6) was sacrificed at the onset of the study. The normal control group (n = 8) received corn oil (the vehicle of tocotrienol) orally daily and normal saline (the vehicle of buserelin) subcutaneously daily. The buserelin control (n = 8) received corn oil orally daily and subcutaneous buserelin injection 75 µg/kg/day daily. The calcium control (n = 8) received 1% calcium in drinking water and subcutaneous buserelin injection 75 µg/kg/day. The remaining rats were treated with two different treatments, i.e., (1) oral annatto tocotrienol at 60 mg/kg/day plus subcutaneous buserelin injection 75 µg/kg/day (n = 8); (2) oral annatto tocotrienol at 100 mg/kg/day plus subcutaneous buserelin injection 75 µg/kg/day (n = 8). The rats were injected with calcein twice before being sacrificed to label the bones. The rats were euthanized, and their blood and right femur were harvested at the end of the treatment for bone turnover markers and bone histomorphometry examination. RESULTS: Both serum osteocalcin and C-telopeptide of type 1 collagen were not significantly different between treated groups and buserelin control (P > 0.05). The buserelin control group had a significantly lower bone volume and higher eroded surface compared with the normal control group (P < 0.05). Both groups treated with annatto tocotrienol (60 mg/kg/day and 100 mg/kg/day) had significantly higher bone volume, trabecular thickness and osteoblast number, as well as a significantly lower single-labelled surface compared with the buserelin control (P < 0.05). Only rats treated with annatto tocotrienol 60 mg/kg/day had a significantly higher double-labelled surface compared with buserelin control (P < 0.05). CONCLUSION: Annatto tocotrienol can prevent trabecular bone loss by increasing the mineralising surface and osteoblasts number. Thus, it has a potential role in preventing bone loss in men using GnRH agonist.


Subject(s)
Bixaceae , Bone Remodeling/drug effects , Buserelin/toxicity , Carotenoids/therapeutic use , Osteoporosis/drug therapy , Plant Extracts/therapeutic use , Tocotrienols/therapeutic use , Animals , Bone Remodeling/physiology , Carotenoids/isolation & purification , Carotenoids/pharmacology , Disease Models, Animal , Fertility Agents, Female/toxicity , Male , Osteoporosis/chemically induced , Osteoporosis/pathology , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Rats , Rats, Sprague-Dawley , Sex Factors , Tocotrienols/isolation & purification , Tocotrienols/pharmacology , Treatment Outcome
11.
Drug Des Devel Ther ; 12: 555-564, 2018.
Article in English | MEDLINE | ID: mdl-29588572

ABSTRACT

BACKGROUND: Patients receiving androgen deprivation therapy experience secondary hypogonadism, associated bone loss, and increased fracture risk. It has been shown that tocotrienol from Bixa orellana (annatto) prevents skeletal microstructural changes in rats experiencing primary hypogonadism. However, its potential in preventing bone loss due to androgen deprivation therapy has not been tested. This study aimed to evaluate the skeletal protective effects of annatto tocotrienol using a buserelin-induced osteoporotic rat model. METHODS: Forty-six male Sprague Dawley rats aged 3 months were randomized into six groups. The baseline control (n=6) was sacrificed at the onset of the study. The normal control (n=8) received corn oil (the vehicle of tocotrienol) orally daily and normal saline (the vehicle of buserelin) subcutaneously daily. The buserelin control (n=8) received corn oil orally daily and subcutaneous buserelin injection (75 µg/kg) daily. The calcium control (n=8) was supplemented with 1% calcium in drinking water and daily subcutaneous buserelin injection (75 µg/kg). The remaining rats were given daily oral annatto tocotrienol at 60 mg/kg (n=8) or 100 mg/kg (n=8) plus daily subcutaneous buserelin injection (75 µg/kg) (n=8). At the end of the experiment, the rats were euthanized and their blood, tibia, and femur were harvested. Structural changes of the tibial trabecular and cortical bone were examined using X-ray micro-computed tomography. Femoral bone calcium content and biomechanical strength were also evaluated. RESULTS: Annatto tocotrienol at 60 and 100 mg/kg significantly prevented the deterioration of trabecular bone and cortical thickness in buserelin-treated rats (P<0.05). Both doses of annatto tocotrienol also improved femoral biomechanical strength and bone calcium content in buserelin-treated rats (P<0.05). The effects of annatto tocotrienol were comparable to calcium supplementation. CONCLUSION: Annatto tocotrienol supplementation is effective in preventing degeneration of the bone induced by buserelin. Therefore, it is a potential antiosteoporotic agent for men receiving androgen deprivation therapy.


Subject(s)
Bixaceae/chemistry , Bone and Bones/drug effects , Bone and Bones/pathology , Buserelin , Calcium/analysis , Disease Models, Animal , Osteoporosis/chemically induced , Osteoporosis/prevention & control , Tocotrienols/pharmacology , Animals , Bone and Bones/chemistry , Calcium/metabolism , Carotenoids/chemistry , Dose-Response Relationship, Drug , Male , Molecular Structure , Osteoporosis/drug therapy , Plant Extracts/chemistry , Rats , Rats, Sprague-Dawley , Structure-Activity Relationship , Tocotrienols/chemistry , Tocotrienols/isolation & purification
12.
J Oleo Sci ; 67(2): 135-142, 2018 Feb 01.
Article in English | MEDLINE | ID: mdl-29367480

ABSTRACT

Rice bran oil (RBO) especially from colored rice is rich in phytochemicals and has become popular in food, cosmetic, nutraceutical and pharmaceutical applications owing to its offering health benefits. This study determined the contents of phytochemicals including oryzanols, phytosterols, tocopherols (Toc) and tocotrienols (T3) in RBOs extracted using different methods namely cold-press extraction (CPE), solvent extraction (SE) and supercritical CO2 extraction (SC-CO2). Two colored rice, Red Jasmine rice (RJM, red rice) and Hom-nin rice (HN, black rice), were studied in comparison with the popular Thai fragrant rice Khao Dawk Mali 105 (KDML 105, white rice). RBOs were found to be the rich source of oryzanols, phytosterols, Toc and T3. Rice varieties had a greater effect on the phytochemicals concentrations than extraction methods. HN rice showed the significantly highest concentration of all phytochemicals, followed by RJM and KDML 105 rice, indicating that colored rice contained high concentration of phytochemicals in the oil than non-colored rice. The RBO samples extracted by the CPE method had a greater concentration of the phytochemicals than those extracted by the SC-CO2 and SE methods, respectively. In terms of phytochemical contents, HN rice extracted using CPE method was found to be the best.


Subject(s)
Liquid-Liquid Extraction/methods , Oryza/chemistry , Phytochemicals/isolation & purification , Rice Bran Oil/analysis , Phenylpropionates/analysis , Phenylpropionates/isolation & purification , Phytochemicals/analysis , Phytosterols/analysis , Phytosterols/isolation & purification , Tocopherols/analysis , Tocopherols/isolation & purification , Tocotrienols/analysis , Tocotrienols/isolation & purification
13.
J Agric Food Chem ; 65(34): 7476-7482, 2017 Aug 30.
Article in English | MEDLINE | ID: mdl-28756671

ABSTRACT

Palm oil is one of the richest sources of tocotrienols and may contain other non-tocopherol vitamin E congeners. The vitamin E profiles of fully ripened fruit mesocarp of three Elaeis guineensis, two Elaeis oleifera, and one hybrid O × G palm fruit genotypes from Costa Rica were analyzed by high-performance liquid chromatography with fluorescence detection and gas chromatography-mass spectrometry after mechanical extraction by a screw press and chemical extraction with hexane. γ-Tocotrienol, α-tocotrienol, and α-tocopherol were the most abundant tocochromanols, while other tocopherols (ß-tocopherol, γ-tocopherol, and δ-tocopherol) and α-tocomonoenol were detected at minor concentrations. Significant differences in vitamin E profiles between genotypes were observed, and the variety E. oleifera Quepos (CB9204) had by far the highest content of total tocotrienols (890 µg/g of oil) and total vitamin E (892 µg/g of oil). Chemical extraction with hexane afforded up to 2.5-fold higher vitamin E yields than screw press extraction. α-Tocomonoenol co-eluted with γ-tocopherol in reversed-phase high-performance liquid chromatography analyses and is a possible source of error in the quantification of γ-tocopherol in foods.


Subject(s)
Arecaceae/chemistry , Fruit/chemistry , Plant Oils/chemistry , Tocopherols/chemistry , Tocotrienols/chemistry , Arecaceae/classification , Chromatography, High Pressure Liquid , Costa Rica , Fruit/classification , Gas Chromatography-Mass Spectrometry , Palm Oil , Plant Oils/isolation & purification , Tocopherols/isolation & purification , Tocotrienols/isolation & purification
14.
Molecules ; 22(9)2017 Aug 29.
Article in English | MEDLINE | ID: mdl-28850073

ABSTRACT

There are six tocol analogs present in palm oil, namely α-tocopherol (α-T), α-tocomonoenol (α-T1), α-tocotrienol (α-T3), γ-tocotrienol (γ-T3), ß-tocotrioenol (ß-T3) and δ-tocotrienol (δ-T3). These analogs were difficult to separate chromatographically due to their similar structures, physical and chemical properties. This paper reports on the effect of pressure and injection solvent on the separation of the tocol analogs in palm oil. Supercritical CO2 modified with ethanol was used as the mobile phase. Both total elution time and resolution of the tocol analogs decreased with increased pressure. Ethanol as an injection solvent resulted in peak broadening of the analogs within the entire pressure range studied. Solvents with an eluent strength of 3.4 or less were more suitable for use as injecting solvents.


Subject(s)
Palm Oil/chemistry , Tocopherols/chemistry , Tocopherols/isolation & purification , Chromans/chemistry , Chromans/isolation & purification , Chromatography, Supercritical Fluid/methods , Molecular Structure , Pressure , Solvents , Tocotrienols/chemistry , Tocotrienols/isolation & purification , Vitamin E/analogs & derivatives , Vitamin E/chemistry , Vitamin E/isolation & purification , alpha-Tocopherol/chemistry , alpha-Tocopherol/isolation & purification
15.
Crit Rev Food Sci Nutr ; 57(14): 2935-2942, 2017 Sep 22.
Article in English | MEDLINE | ID: mdl-26207585

ABSTRACT

During the past few years the scientific and medical community has been confronted with a continual interest in vitamin E with the interest prompted by new discoveries. Tocopherols and tocotrienols, commonly known as vitamin E, are extremely invaluable compounds and have various nutritional functionalities and benefits to human health. Great deals of research projects have been launched in order to develop effective methods for the extraction of vitamin E. By and large, three distinct extractive methods are usually employed: supercritical fluid extraction (SFE), molecular distillation, and adsorption methods. These methods are sensitive to different experimental conditions, such as pressure, temperature, and flow rate with noticeable effects on the efficiency of the extraction and enrichment of vitamin E. This review has covered the most commonly adapted extraction methods and has probed into the extraction yields under variable operational parameters.


Subject(s)
Food Analysis/methods , Food Technology/methods , Tocopherols/analysis , Tocotrienols/analysis , Humans , Temperature , Tocopherols/isolation & purification , Tocotrienols/isolation & purification
16.
J Chromatogr A ; 1476: 77-87, 2016 Dec 09.
Article in English | MEDLINE | ID: mdl-27887701

ABSTRACT

Tocopherols and tocotrienols (usually summed up as vitamin E) are a class of structurally related natural antioxidants. Commonly, only some of the eight classic representatives (four tocopherols and four tocotrienols) are found with varied composition in food. In this study we fractionated 230mg oil from commercial vitamin E supplement capsules by countercurrent chromatography (CCC) and subsequent analysis by gas chromatography with mass spectrometry (GC/MS) of silylated CCC fractions showed that these eight isomers represented only about 70% of total tocopherol compounds. Detailed analysis enabled the detection of 161T3 isomers (α-, γ- and δ-T3) along with 18 tetra- and several penta-unsaturated isomers (tocools), two tocomonoenol isomers, and several degradation products with shorter isoprenoid side chain (apo-tocools). Altogether, over 170 tocool compounds, most likely artefacts which originated from an inappropriate oil refining process were described in this study. Silver ion high performance liquid chromatography (Ag+-HPLC) was used to separate one fraction rich in γ-T3 into four peaks each consisting of at least five peaks according to GC/MS. About ten γ-T3 isomers were also detected in rice bran oils from one producer bought retail in Germany.


Subject(s)
Antioxidants/analysis , Artifacts , Countercurrent Distribution , Dietary Supplements/analysis , Gas Chromatography-Mass Spectrometry , Tocopherols/analysis , Tocotrienols/analysis , Antioxidants/chemistry , Antioxidants/isolation & purification , Capsules , Chromatography, High Pressure Liquid , Tocopherols/chemistry , Tocopherols/isolation & purification , Tocotrienols/chemistry , Tocotrienols/isolation & purification , Vitamin E/administration & dosage
17.
Anal Bioanal Chem ; 407(17): 5133-42, 2015 Jul.
Article in English | MEDLINE | ID: mdl-25822159

ABSTRACT

For the most effective analytical strategies, development and validation include optimization of such analytical variables as resolution, detectability, sensitivity, simplicity, cost effectiveness, flexibility, and speed. However, other aspects concerning operator safety and environmental impact are not considered at the same level. The result has been many unintended negative effects of analytical methods developed to investigate different kinds of sample, especially hydrophobic compounds that generate a large amount of chemical waste and have a strong negative environmental impact. In this context, quantification of tocopherols and tocotrienols, i.e. the vitamin E family, is usually achieved by normal-phase liquid chromatography using large volumes of toxic organic solvents, or reversed-phase liquid chromatography using a high percentage of methanol for elution. We propose here a "greener" analytical strategy, including the hyphenation of supercritical-fluid chromatography, using CO2 and ethanol as mobile phase, NH2 as stationary phase, and mass spectrometry for the detection and quantification of vitamin E congeners in soybean oil. An atmospheric-pressure photoionization (APPI) source seemed significantly more sensitive and robust than electrospray or atmospheric-pressure chemical ionization (APCI). This method led to shortened analysis time (less than 5 min) and was revealed to be as sensitive as more traditional approaches, with limits of detection and quantification in the tens of µg L(-1).


Subject(s)
Chromatography, Supercritical Fluid/methods , Mass Spectrometry/methods , Soybean Oil/chemistry , Tocopherols/analysis , Tocotrienols/analysis , Green Chemistry Technology/methods , Limit of Detection , Reproducibility of Results , Tocopherols/isolation & purification , Tocotrienols/isolation & purification
18.
Phytochemistry ; 109: 103-10, 2015 Jan.
Article in English | MEDLINE | ID: mdl-25468538

ABSTRACT

Ten tocotrienol derivatives, i.e., amplexichromanols (1-10), were isolated from stem bark of Garcinia amplexicaulis Vieill. ex Pierre collected in Caledonia. The structures of the compounds 1-5 were determined to be chromanol derivatives substituted by a polyprenyl chain oxidized in terminal position. The remaining compounds 6-10 are the corresponding dimeric derivatives. Eleven known compounds, including xanthones, tocotrienol derivatives, triterpenes and phenolic compounds, were also isolated. Their structures were mainly determined using one and two-dimensional NMR and mass spectroscopy analysis. The compounds and some amplexichromanol molecules formerly isolated from G. amplexicaulis exhibited significant antioxidant activity against lipid peroxidation and in the ORAC assay.


Subject(s)
Antioxidants/chemistry , Garcinia/chemistry , Tocotrienols/chemistry , Antioxidants/isolation & purification , Lipid Peroxidation/drug effects , Molecular Structure , Plant Bark/chemistry , Tocotrienols/isolation & purification
19.
Nat Prod Res ; 29(22): 2137-40, 2015.
Article in English | MEDLINE | ID: mdl-25515603

ABSTRACT

Tocotrienols have been reported to possess anticancer effects other than anti-inflammatory and antioxidant activities. This study explored the potential synergism of antiproliferative effects induced by individual alkaloid extracts of Ficus fistulosa, Ficus hispida and Ficus schwarzii combined with δ- and γ-tocotrienols against human brain glioblastoma (U87MG), lung adenocarcinoma (A549) and colorectal adenocarcinoma (HT-29) cells. Cell viability and morphological results demonstrated that extracts containing a mixture of alkaloids from the leaves and bark of F. schwarzii inhibited the proliferation of HT-29 cells, whereas the alkaloid extracts of F. fistulosa inhibited the proliferation of both U87MG and HT-29 cells and showed synergism in combined treatments with either δ- or γ-tocotrienol resulting in 2.2-34.7 fold of reduction in IC50 values of tocotrienols. The observed apoptotic cell characteristics in conjunction with the synergistic antiproliferative effects of Ficus species-derived alkaloids and tocotrienols assuredly warrant future investigations towards the development of a value-added chemotherapeutic regimen against cancers.


Subject(s)
Alkaloids/pharmacology , Ficus/chemistry , Plant Extracts/pharmacology , Plant Oils/chemistry , Tocotrienols/pharmacology , Alkaloids/isolation & purification , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Drug Synergism , Humans , Palm Oil , Plant Bark/chemistry , Plant Leaves/chemistry , Tocotrienols/isolation & purification
20.
Talanta ; 130: 299-306, 2014 Dec.
Article in English | MEDLINE | ID: mdl-25159413

ABSTRACT

A sensitive and rapid reversed-phase ultra performance liquid chromatographic (UPLC) method for the simultaneous determination of tocopherols (α-, ß-, γ-, δ-), tocotrienols (α-, ß-, γ-, δ-), α-tocopherol acetate and α-tocopherol nicotinate is described. The separation was achieved using a Kinetex pentafluorophenyl (PFP) column (150 × 2.1mm, 2.6 µm) with both photodiode array (PDA) and fluorescence (FL) detectors that were connected in series. Column was thermostated at 42°C. Under a gradient system consisting of methanol and water at a constant flow rate of 0.38 mL min(-1), all the ten analytes were well separated in less than 9.5 min. The method was validated in terms of linearity, limits of detection and quantitation, precision and recoveries. Calibration curves of the ten compounds were well correlated (r(2)>0.999) within the range of 100 to 25,000 µg L(-1) for α-tocopherol acetate and α-tocopherol nicotinate, 10 to 25,000 µg L(-1) for α-tocotrienol and 5 to 25,000 µg L(-1) for the other components. The method is simple and sensitive with detection limits (S/N, 3) of 1.0 to 3.0 µg L(-1) (FL detection) and 30 to 74 µg L(-1) (PDA detection). Relative standard deviations for intra- and inter-day retention times (<1%) and peak areas (≤ 4%) were obtained. The method was successfully applied to the determination of vitamin E in vegetable oils (extra virgin olive, virgin olive, pomace olive, blended virgin and refined olive, sunflower, soybean, palm olein, carotino, crude palm, walnut, rice bran and grape seed), margarines and supplements.


Subject(s)
Antioxidants/analysis , Dietary Supplements/analysis , Isothiocyanates/chemistry , Margarine/analysis , Plant Oils/chemistry , Tocopherols/analysis , Tocotrienols/analysis , Capsules , Chromatography, Liquid , Chromatography, Reverse-Phase , Limit of Detection , Tocopherols/isolation & purification , Tocotrienols/isolation & purification
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