4.6 Review

Free and Esterified Tocopherols, Tocotrienols and Other Extractable and Non-Extractable Tocochromanol-Related Molecules: Compendium of Knowledge, Future Perspectives and Recommendations for Chromatographic Techniques, Tools, and Approaches Used for Tocochromanol Determination

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Alexander Kroepfl et al.

Summary: The isolation and structural verification of rare vitamin E compound gamma-tocomonoenol (gamma-T1) was achieved from non-refined, organic pumpkin seed oil (PSO). In addition to gamma-T1, a total of 18 different tocochromanols were detected through CCC fractionation, some of which were reported for the first time in PSO.

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Quantification of tocochromanols in vitamin E dietary supplements by instrumental thin-layer chromatography

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Summary: In this study, an instrumental thin-layer chromatography (TLC) method was developed for the direct determination of various tocopherols and tocotrienols in vitamin E dietary supplement capsules. The method is fast, easy to perform, and suitable for quantification and screening of vitamin E capsules.

EUROPEAN FOOD RESEARCH AND TECHNOLOGY (2022)

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Fruit tree leaves as valuable new source of tocopherol and tocotrienol compounds

Aneta Wojdylo et al.

Summary: This study identified and quantified tocopherol and tocotrienol isomers in various fruit tree leaves for the first time, finding that apricot and peach leaves are the best sources of tocopherols. Fruit tree leaves could be a novel significant source for the isolation of alpha-tocopherol for cosmetic, pharmaceutical, or food industry applications.

JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE (2022)

Article Chemistry, Applied

11′-α-Tocomonoenol is the major α-tocomonoenol isomer in cyanobacteria and microalgae from Costa Rica

Alexander Montoya-Arroyo et al.

Summary: This study identified 11'-alpha-tocomonoenol as the predominant form of tocochromanol in cyanobacteria and microalgae, particularly Tetraselmis sp., and reported its presence in aquatic photosynthetic organisms for the first time.

JOURNAL OF FOOD COMPOSITION AND ANALYSIS (2022)

Article Chemistry, Analytical

Supercritical fluid chromatography with post-column addition of supporting electrolyte solution for electrochemical determination of tocopherol and tocotrienol isomers

Kazuhiro Yamamoto et al.

Summary: A system combining supercritical fluid chromatography with electrochemical detection was developed to simultaneously determine tocopherol and tocotrienol isomers. The system allows independent control of separation and detection by introducing a supporting electrolyte solution into the flow path. The method showed good linearity and repeatability, and was applicable to the determination of these compounds in nutrition supplements.

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Article Chemistry, Applied

Carotenoids, tocopherols and phylloquinone content of 26 green leafy vegetables commonly consumed in Southeast Asia

Hui Wen Lee et al.

Summary: This study analyzed the micronutrient composition of 26 commonly consumed green leafy vegetables in Southeast Asia using HPLC-APCI-MS/MS technology. The results revealed that underutilized vegetables such as sweet leaf bush contain high levels of carotenoids, tocopherols, and phylloquinone. These findings are important for improving the nutritional status of the population in the region.

FOOD CHEMISTRY (2022)

Article Chemistry, Applied

Analytical scale supercritical fluid chromatography for the analysis of nine tocochromanols in 24 different cold-pressed plant oils: Method development, validation, and isolation of tocotrienols and plastochromanol-8

Georgijs Baskirovs et al.

Summary: In this study, tocotrienol homologues and plastochromanol-8 were isolated from plant oils using supercritical fluid chromatography. The optimized method allowed for the rapid and sensitive analysis of tocochromanols in different plant oils.

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Deep eutectic solvent-based liquid-phase microextraction coupled with reversed-phase high-performance liquid chromatography for determination of α-, β-, γ-, and δ-tocopherol in edible oils

Qilong Xie et al.

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ANALYTICAL AND BIOANALYTICAL CHEMISTRY (2021)

Article Horticulture

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Elise Sipeniece et al.

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SCIENTIA HORTICULTURAE (2021)

Article Chemistry, Applied

Enzyme-assisted extraction of bioactive non-extractable polyphenols from sweet cherry (Prunus avium L.) pomace

Gloria Dominguez-Rodriguez et al.

Summary: An enzyme-assisted extraction (EAE) method was developed to extract non-extractable polyphenols (NEPs) from sweet cherry pomace, resulting in higher content of proanthocyanidins with higher bioactivity than alkaline and acid hydrolysis methods. Additionally, the extraction residue contained higher amounts of bioactive phenolics than the sweet cherry pomace extract, demonstrating the potential of EAE to produce bioactive compounds with high molecular weight.

FOOD CHEMISTRY (2021)

Article Biotechnology & Applied Microbiology

Berry by-products obtained from a decoction process are a rich source of low- and high-molecular weight extractable and non-extractable polyphenols

Rosalia Reynoso-Camacho et al.

Summary: This study conducted a comprehensive analysis of the polyphenol profiles in strawberry, raspberry, blueberry, and blackberry decoctions, revealing a greater variety of polyphenols in the extractable fraction of the decoction by-products. Ellagic acid and hydroxybenzoic acid were identified as the major polyphenols in the berry decoction by-products, with various proanthocyanidins also present. The results demonstrate that while berry decoctions are rich in polyphenols, the decoction by-products are even more abundant in a diverse range of polyphenols.

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Article Chemistry, Applied

Extraction, isolation, characterization and antimicrobial activities of non-extractable polyphenols from pomegranate peel

Shengwei Sun et al.

Summary: Non-extractable polyphenols (NEPPs) in pomegranate peel were released using acid hydrolysis and ethyl acetate extraction, leading to the identification of ten NEPPs. Six compounds were isolated and their structures determined, with compounds 3 and 5 showing significant antimicrobial activity. This study sheds new light on the composition of bound chemicals in pomegranate peel and serves as a foundation for further processing and utilization.

FOOD CHEMISTRY (2021)

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High-performance thin-layer chromatography and direct analysis in real time-high resolution mass spectrometry of non-extractable polyphenols from tropical fruit peels

Gloria Dominguez-Rodriguez et al.

Summary: Alkaline hydrolysis is the most efficient method to recover NEPs from fruit peels, and cherimoya peel extracts contain the richest antioxidant NEPs.

FOOD RESEARCH INTERNATIONAL (2021)

Article Chemistry, Applied

Unique bioactive molecule composition of sea buckthorn (Hippophae rhamnoides L.) oils obtained from the peel, pulp, and seeds via physical solvent-free approaches

Dalija Seglina et al.

Summary: Sea buckthorn is a valuable plant used in various industries due to its bioactive compounds. Peel oil from sea buckthorn berries was found to be a richer source of bioactive compounds compared to pulp and seed oils, with similar lipid profiles to pulp oil but with lower sterol content and the presence of squalene. Minor molecules such as tocochromanols, sterols, squalene, carotenoids, and flavonols were detected in concentrations ranging from 100.0-273.6, 427.4-575.0, 0-402.4, 0.9-72.0, 0.9-15.6 mg/100 g oil, respectively.

JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY (2021)

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Tocopherols, carotenoids and phenolics changes during Andean lupin (Lupinus mutabilis Sweet) seeds processing

Andrea Brandolini et al.

JOURNAL OF FOOD COMPOSITION AND ANALYSIS (2021)

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Analysis of minor vitamin E homologues in natural products

Fumiaki Beppu et al.

Summary: Fruits and seeds are naturally rich in antioxidants, with vitamin E being a typical antioxidant that plays a crucial role in preventing oxidation and supporting the biological functions of organisms. Recent studies have identified minor homologues like tocomonoenol and tocodienol, which have attracted research interest due to their unique structural characteristics and potential nutritional functionality.

JOURNAL OF BERRY RESEARCH (2021)

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Application of Partial Hydrogenation for the Generation of Minor Tocochromanol Homologs and Functional Evaluation of Hydrogenated Tocotrienol-rich Vitamin E Oil in Diabetic Obese Mice

Fumiaki Beppu et al.

Summary: Research has identified minor homologs of vitamin E, Ti and T2, which can be generated from tocotrienol through partial hydrogenation. Feeding the hydrogenated product can ameliorate hyperglycemia and improve lipid metabolism abnormalities.

JOURNAL OF OLEO SCIENCE (2021)

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Supradip Saha et al.

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Identification of two α-tocodienol isomers in palm oil after countercurrent chromatographic enrichment

Marco Mueller et al.

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Vitamin E and cancer prevention: Studies with different forms of tocopherols and tocotrienols

Chung S. Yang et al.

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Simultaneous determination of carotenoids, tocopherols and phylloquinone in 12 Brassicaceae vegetables

Hui Wen Lee et al.

LWT-FOOD SCIENCE AND TECHNOLOGY (2020)

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Fate of free and bound phytol and tocopherols during fruit ripening of two Capsicum cultivars

Stephanie Krauss et al.

SCIENTIFIC REPORTS (2020)

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Oak Quercus rubra L. and Quercus robur L. acorns as an unconventional source of gamma- and beta-tocopherol

Pawel Gornas

EUROPEAN FOOD RESEARCH AND TECHNOLOGY (2019)

Article Chemistry, Applied

Less widespread plant oils as a good source of vitamin E

Agnieszka Trela et al.

FOOD CHEMISTRY (2019)

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Article Chemistry, Applied

Borage oil: Tocopherols, sterols and squalene in farmed and endemic-wild Borago species

Dmitri Fabrikov et al.

JOURNAL OF FOOD COMPOSITION AND ANALYSIS (2019)

Article Agriculture, Multidisciplinary

Diversity of oil yield, fatty acids, tocopherols, tocotrienols, and sterols in the seeds of 19 interspecific grapes crosses

Pawel Gornas et al.

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Article Food Science & Technology

Effects of peeling and/or toasting on the presence of tocopherols and phenolic compounds in four Italian hazelnut cultivars

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Fruit peels as sources of non-extractable polyphenols or macromolecular antioxidants: Analysis and nutritional implications

Jara Perez-Jimenez et al.

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Frantisek Kreps et al.

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R. J. Sanchez et al.

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Charlene Muscat Galea et al.

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Enhanced plastochromanol-8 accumulation during reiterated drought in maize (Zea mays L.)

Eva Fleta-Soriano et al.

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Article Food Science & Technology

Synthesis and analysis of tocopheryl quinone and tocopherol esters with fatty acids in heated sunflower oil

Frantisek Kreps et al.

EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY (2016)

Article Food Science & Technology

Varied Composition of Tocochromanols in Different Types of Bran: Rye, Wheat, Oat, Spelt, Buckwheat, Corn, and Rice

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INTERNATIONAL JOURNAL OF FOOD PROPERTIES (2016)

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Lipophilic bioactive compounds in the oils recovered from cereal by-products

Pawel Gornas et al.

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E. Bartosinska et al.

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Fereidoon Shahidi et al.

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Aleksander Siger et al.

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Haseeb Ahsan et al.

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Jerzy Kruk et al.

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Luana Fernandes et al.

FOOD RESEARCH INTERNATIONAL (2013)

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Detection of Tocopherol in Oilseed Rape (Brassica napus L.) Using Gas Chromatography with Flame Ionization Detector

Nazim Hussain et al.

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Article Agriculture, Multidisciplinary

Identification and Quantitation of Carotenoids and Tocopherols in Seed Oils Recovered from Different Rosaceae Species

Matthias Fromm et al.

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Article Agriculture, Multidisciplinary

Preparation and Certification of Standard Reference Material 3278 Tocopherols in Edible Oils

Catherine A. Rimmer et al.

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Determination of lipophilic compounds in genetically modified rice using gas chromatography-time-of-flight mass spectrometry

Jae Kwang Kim et al.

JOURNAL OF FOOD COMPOSITION AND ANALYSIS (2012)

Article Plant Sciences

Novel vitamin E forms in leaves of Kalanchoe daigremontiana and Phaseolus coccineus

Jerzy Kruk et al.

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Bharat B. Aggarwal et al.

BIOCHEMICAL PHARMACOLOGY (2010)

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Abdalbasit Adam Mariod et al.

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Article Chemistry, Applied

δ-Tocomonoenol: A new vitamin E from kiwi (Actinidia chinensis) fruits

Antonio Fiorentino et al.

FOOD CHEMISTRY (2009)

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Evaluation of vacuum microwave-assisted extraction technique for the extraction of antioxidants from plant samples

Xiao-Hua Xiao et al.

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Article Biochemical Research Methods

Application of GC-MS for the detection of lipophilic compounds in diverse plant tissues

Anna Lytovchenko et al.

PLANT METHODS (2009)

Article Chemistry, Applied

Separation of individual tocopherols from soybean distillate by low pressure column chromatography

Jianchun Wan et al.

JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY (2008)

Article Biochemical Research Methods

RP-LC for determination of plastochromanol, tocotrienols and tocopherols in plant oils

Jolanta Gruszka et al.

CHROMATOGRAPHIA (2007)

Article Biochemistry & Molecular Biology

Glycosylation of tocopherols by cultured cells of Eucalyptus perriniana

Kei Shimoda et al.

PHYTOCHEMISTRY (2007)

Article Biochemistry & Molecular Biology

Influence of major structural features of tocopherols and tocotrienols on their ω-oxidation by tocopherol-ω-hydroxylase

Timothy J. Sontag et al.

JOURNAL OF LIPID RESEARCH (2007)

Article Biochemical Research Methods

Simple GC-FID method development and validation for determination of α-tocopherol (vitamin E) in human plasma

Fatma Demirkaya et al.

JOURNAL OF BIOCHEMICAL AND BIOPHYSICAL METHODS (2007)

Article Agriculture, Multidisciplinary

Quantification of tocopherols and tocotrienols in Portuguese olive oils using HPLC with three different detection systems

Sara C. Cunha et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2006)

Article Biochemistry & Molecular Biology

Differential distribution of tocopherols and tocotrienols in photosynthetic and non-photosynthetic tissues

Gyorgy Horvath et al.

PHYTOCHEMISTRY (2006)

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A decade of progress in understanding vitamin E synthesis in plants

D DellaPenna

JOURNAL OF PLANT PHYSIOLOGY (2005)

Article Agriculture, Multidisciplinary

Phenolic acid, tocopherol and carotenoid compositions, and antioxidant functions of hard red winter wheat bran

KQ Zhou et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2005)

Article Chemistry, Applied

A small-scale sample preparation method with HPLC analysis for determination of tocopherols and tocotrienols in cereals

M Ryynänen et al.

JOURNAL OF FOOD COMPOSITION AND ANALYSIS (2004)

Article Biochemistry & Molecular Biology

Separation of vitamin E (tocopherol, tocotrienol, and tocomonoenol) in palm oil

MH Ng et al.

LIPIDS (2004)

Article Chemistry, Applied

FA and tocopherol composition of Vietnamese oilseeds

B Matthaus et al.

JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY (2003)

Article Agriculture, Multidisciplinary

Normal phase high-performance liquid chromatography method for the determination of tocopherols and tocotrienols in cereals

G Panfili et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2003)

Article Biochemistry & Molecular Biology

Notothenioid fish, krill and phytoplankton from Antarctica contain a vitamin E constituent (α-tocomonoenol) functionally associated with cold-water adaptation

WC Dunlap et al.

COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY B-BIOCHEMISTRY & MOLECULAR BIOLOGY (2002)

Review Biochemical Research Methods

Chromatographic analysis of α-tocopherol and related compounds in various matrices

FJ Rupérez et al.

JOURNAL OF CHROMATOGRAPHY A (2001)

Article Agriculture, Multidisciplinary

Isolation and identification of novel tocotrienols from rice bran with hypocholesterolemic, antioxidant, and antitumor properties

AA Qureshi et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2000)

Review Biochemical Research Methods

Chromatographic analysis of tocol-derived lipid antioxidants

SL Abidi

JOURNAL OF CHROMATOGRAPHY A (2000)