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

Beppu, Fumiaki; Sakuma, Aimi; Kasatani, Satoshi; Aoki, Yosuke; Gotoh, Naohiro

doi:10.5650/jos.ess20233

Cited by 3 publications

(6 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[21,34] The observed differences in the extent of metabolism of T3 and T1 suggest that the degree of saturation and/or the position of double bonds in the sidechain may influence the affinity of tocochromanols for their metabolizing enzymes. These data might partially explain the bioavailability of T1 congeners observed in rodents [20,24] and humans. [25] One might further speculate that differences in physicochemical properties, such as the slightly more polar sidechain of T3 compared to T, [44] might lead to differences in intracellular distribution in general or to the endoplasmic reticulum in particular, where the rate-limiting enzymes catalyzing the first step in vitamin E metabolism are localized.…”

Section: The Rate Of Metabolism Of Tocochromanols Increases With the ...mentioning

confidence: 83%

Section: Resultsmentioning

confidence: 99%

“…The biological activities of T1 thus warrant further investigation, not the least because 𝛼T1 isomers have been detected in the blood of nonsupplemented human subjects, [25] in different tissues of free-living fishes [6,25,47] and in blood [29,30] and tissues of supplemented rodents [30] while 𝛾T1 and 𝛽T1 have been reported in adipose tissue of supplemented rodents. [20]…”

Section: The Rate Of Metabolism Of Tocochromanols Increases With the ...mentioning

confidence: 99%

See 2 more Smart Citations

Metabolism of 11′‐α‐ and 11′‐γ‐Tocomonoenols in HepG2 Cells Favors the γ‐Congener and Results Predominantly in Carboxymethylbutyl‐Hydroxychromans

Montoya‐Arroyo,

Brand,

Kröpfl

et al. 2024

Molecular Nutrition Food Res

View full text Add to dashboard Cite

ScopeTocomonoenols (T1) are little‐known vitamin E derivatives naturally occurring in foods. Limited knowledge exists regarding the cellular uptake and metabolism of α‐tocomonoenol (αT1) and none about that of γ‐tocomonoenol (γT1).Methods and resultsThe study investigates the cytotoxicity, uptake, and metabolism of αT1 and γT1 in HepG2 cells compared to the α‐ and γ‐tocopherols (T) and ‐tocotrienols (T3). None of the studied tocochromanols are cytotoxic up to 100 µmol L−1. The uptake of the γ‐congeners is significantly higher than that of the corresponding α‐forms, whereas no significant differences are observed based on the degree of saturation of the sidechain. Carboxymethylbutyl‐hydroxychromans (CMBHC) are the predominant short‐chain metabolites of all tocochromanols and conversion is higher for γT1 than αT1 as well as for the γ‐congeners of T and T3. The rate of metabolism increases with the number of double bonds in the sidechain. The rate of metabolic conversion of the T1 is more similar to tocopherols than to that of the tocotrienols.ConclusionThis is the first evidence that both αT1 and γT1 follow the same sidechain degradation pathway and exert similar rates of metabolism than tocopherols. Therefore, investigation into the biological activities of tocomonoenols is warranted.

show abstract

Section: The Rate Of Metabolism Of Tocochromanols Increases With the ...mentioning

confidence: 83%

Section: Resultsmentioning

confidence: 99%

Section: The Rate Of Metabolism Of Tocochromanols Increases With the ...mentioning

confidence: 99%

See 1 more Smart Citation

Metabolism of 11′‐α‐ and 11′‐γ‐Tocomonoenols in HepG2 Cells Favors the γ‐Congener and Results Predominantly in Carboxymethylbutyl‐Hydroxychromans

Montoya‐Arroyo,

Brand,

Kröpfl

et al. 2024

Molecular Nutrition Food Res

View full text Add to dashboard Cite

show abstract

“…For example, PC-8 has been obtained from plastoquinone-9 [ 64 ]. α-T1 and α-T2 have been obtained by saturating double bonds in the side-chain of α-T3 using a partial hydrogenation reaction with palladium-activated carbon ethylenediamine complex as a catalyst [ 131 ]. (2R,8′ S,3′ E)-δ-T2 has been obtained in an eight-step synthetic route from δ-T3 [ 77 ].…”

Section: Extraction Of Tocochromanolsmentioning

confidence: 99%

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

2022

View full text Add to dashboard Cite

Free and esterified (bound) tocopherols, tocotrienols and other tocochromanol-related compounds, often referred to “tocols”, are lipophilic antioxidants of great importance for health. For instance, α-tocopherol is the only tocochromanol with vitamin E activity, while tocotrienols have a positive impact on health and are proposed in the prevention and therapy of so-called modern diseases. Tocopherols, tocotrienols and plastochromanol-8 are the most well-known tocochromanols; in turn, knowledge about tocodienols, tocomonoenols, and other rare tocochromanol-related compounds is limited due to several challenges in analytical chemistry and/or low concentration in plant material. The presence of free, esterified, and non-extractable tocochromanols in plant material as well as their biological function, which may be of great scientific, agricultural and medicinal importance, is also poorly studied. Due to the lack of modern protocols as well as equipment and tools, for instance, techniques suitable for the efficient and simultaneous chromatographical separation of major and minor tocochromanols, the topic requires attention and new solutions, and/or standardization, and proper terminology. This review discusses the advantages and disadvantages of different chromatographic techniques, tools and approaches used for the separation and detection of different tocochromanols in plant material and foodstuffs. Sources of tocochromanols and procedures for obtaining different tocochromanol analytical standards are also described. Finally, future challenges are discussed and perspective green techniques for tocochromanol determination are proposed along with best practice recommendations. The present manuscript aims to present key aspects and protocols related to tocochromanol determination, correct identification, and the interpretation of obtained results.

show abstract

“…Recently, we proposed a liquid chromatography with tandem MS (LC-MS/MS) method for the quantification of ␣, ␤/␥ and δ-series Toc, T1, T2 and T3 in multiple reaction monitoring (MRM) mode [51]. To date, reference standards for T1 and T2 are not available.…”

Section: Detectionmentioning

confidence: 99%

Analysis of minor vitamin E homologues in natural products

Beppu

Gotoh

2021

JBR

Self Cite

View full text Add to dashboard Cite

Fruits and seeds are naturally rich in antioxidants, which provide protection against UV light and oxygen. Vitamin E is a typical antioxidant, and offers radical scavenging activity to prevent the oxidation of the polyunsaturated fatty acids in cell membranes, contribute to homeostasis, and support the biological functions of animals and plants. Tocopherol and tocotrienol are forms of vitamin E widely found in natural products. In addition, recent studies have demonstrated the existence of minor homologues, namely tocomonoenol and tocodienol. The characteristic physiological functions of vitamin E homologues are dependent on their structure. Consequently, the nutritional functionality of the minor homologues has attracted much research interest, which relies on highly accurate analytical methods. This review aimed to summarize the literature concerning the diversity of tocomonoenol and tocodienol, as well as reports on the various methods for their analysis and detection in different sample matrices. This paper is expected to contribute to future exploratory research and the functional evaluation of minor homologues.

show abstract

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

Cited by 3 publications

References 26 publications

Metabolism of 11′‐α‐ and 11′‐γ‐Tocomonoenols in HepG2 Cells Favors the γ‐Congener and Results Predominantly in Carboxymethylbutyl‐Hydroxychromans

Metabolism of 11′‐α‐ and 11′‐γ‐Tocomonoenols in HepG2 Cells Favors the γ‐Congener and Results Predominantly in Carboxymethylbutyl‐Hydroxychromans

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

Analysis of minor vitamin E homologues in natural products

Contact Info

Product

Resources

About