Determination of tocopherols and their metabolites by liquid-chromatography coupled with tandem mass spectrometry in human plasma and serum

Giusepponi, Danilo; Torquato, Pierangelo; Bartolini, Desirée; Piroddi, Marta; Birringer, Marc; Lorkowski, Stefan; Libetta, Carmelo; Cruciani, Gabriele; Moretti, Simone; Saluti, Giorgio; Galli, Francesco; Galarini, Roberta

doi:10.1016/j.talanta.2017.04.030

Cited by 38 publications

(38 citation statements)

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“…While there is convincing evidence for the systemic availability of the SCM of vitamin E in humans, there was a lack of studies to demonstrate this for the LCM. Our group first measured α‐13′‐OH and α‐13′‐COOH in serum of volunteers using an unbiased LC–MS/MS method . The serum concentrations of these LCM were recently reported to be about 1.2 and 0.8 n m at baseline and 2.4 and 8 n m after one week of supplementation with 1000 IU RRR‐ α‐TOH, respectively .…”

Section: Resultsmentioning

confidence: 99%

“…The principle hepatic metabolism of vitamin E is established and rather complex . It is known that the hepatic metabolism, as shown in Figure , starts with an oxidation of the aliphatic side chain by the cytochrome P (CYP) 450‐dependent enzymes CYP4F2 and/or CYP3A4, forming the first physiological long‐chain metabolites (LCM) 13′‐hydroxychromanol (13′‐OH) and 13′‐carboxychromanol (13′‐COOH), which also circulate within the blood of humans and may exert systemic effects . Further catabolism of the LCM shortens the side chain, leading to intermediate‐chain metabolites (ICM) and finally to water soluble short‐chain metabolites (SCM; carboxyethylhydroxychromanols, CEHC) .…”

Section: Introductionmentioning

confidence: 99%

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Structure–Function Relationship Studies In Vitro Reveal Distinct and Specific Effects of Long‐Chain Metabolites of Vitamin E

Schmölz

Wallert

Rozzino

et al. 2017

Molecular Nutrition Food Res

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The LCM effects depend on the presence of the chromanol ring system and on the modification of the side-chain but not on the substitution pattern of the chromanol ring. Therefore, it can be concluded that for mediation of effects by LCM the entire molecule is needed and that the effects are specific. We propose the LCM of the micronutrient vitamin E as a new class of regulatory metabolites, but further studies are needed to corroborate this hypothesis.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structure–Function Relationship Studies In Vitro Reveal Distinct and Specific Effects of Long‐Chain Metabolites of Vitamin E

Schmölz

Wallert

Rozzino

et al. 2017

Molecular Nutrition Food Res

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“…Vitamin E catabolism produces a short‐chain metabolite 2,5,7,8‐tetramethyl‐2(2α‐carboxyethyl)‐6‐hydroxychroman (α‐CEHC) and long‐chain metabolites with regulatory functions on cellular lipids as cyclooxygenase inhibitors or 5‐lipoxygenase inhibitors . Analysis protocols have been developed to measure vitamin E metabolites that have been utilized in the study of vitamin E metabolism in healthy subjects and in pathologic conditions . The extrapolation of the in vitro effects to in vivo physiological situations deserves further investigations.…”

Section: Toward a Molecular Understanding Of The Mechanisms Involved mentioning

confidence: 99%

Vitamin E – The Next 100 Years

Khadangi

Azzi

2018

IUBMB Life

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α‐Tocopherol is the only tocopherol that has been shown to prevent the human deficiency disease Ataxia with Isolated Vitamin E Deficiency (AVED), and thus it is the only one that, for humans, can be called vitamin E. Vitamin E in addition to preventing AVED has documented immune boosting properties and an activity against nonalcoholic hepatosteatosis and low‐grade inflammation. Epidemiological studies indicating that vitamin E could prevent cardiovascular events, neurodegenerative disease, macular degeneration, and cancer were in general not confirmed by clinical intervention studies. Vitamin E and some of its metabolites modulate cell signaling and gene transcription. Future research is needed to achieve a better understanding of the molecular events leading to gene regulation by vitamin E, especially in its phosphorylated form. Isolation and characterization of the vitamin E kinase and vitamin E phosphate phosphatase will help in the understanding of cell regulation processes modulated by vitamin E. A clarification of the pathogenesis of AVED remains an important goal to be achieved. © 2018 IUBMB Life, 71(4):411–415, 2019

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“…Long‐chain metabolites were detected in the range between 1 and 10 nM for α‐13′‐OH and between 8 and 49 nM for α‐13′‐COOH . After supplementation with RRR ‐α‐tocopherol, plasma concentrations of the LCMs can be increased 10‐fold.…”

Section: Metabolism and Relevance In Humansmentioning

confidence: 99%

Vitamin E: Regulatory role of metabolites

Birringer

Lorkowski

2018

IUBMB Life

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Vitamin E plays an important role as a lipophilic antioxidant in cellular redox homeostasis. Besides this function, numerous non‐antioxidant properties of this vitamin have been discovered in the past. DNA microarray technology revealed a complex regulatory network influenced by the different vitamin E forms (Rimbach et al., Molecules, 15, 1746 (2010); Galli et al., Free Radic. Biol. Med., 102, 16 (2017)); however, little is known about the biological activity of vitamin E metabolites. A new chapter of vitamin E research was been opened when endogenous long‐chain tocopherol metabolites were identified and their high biological activity in vitro and in vivo was recognized (Schmölz et al., World J. Biol. Chem., 7, 14 (2016); Torquato et al., J. Pharm. Biomed. Anal., 124, 399 (2016)). Just recently, it was shown that an endogenous metabolite of vitamin E inhibits 5‐lipoxygenase at nanomolar concentrations, thereby limiting inflammation (Pein et al., Nat. Commun., 9, 3834 (2018)). Furthermore, long‐chain vitamin E metabolites (LCM) exhibit hormone‐like activities similar to the lipid soluble vitamins A and D (Galli et al., Free Radic. Biol. Med., 102, 16 (2017); Schubert et al., Antioxidants, 7 (2018)). This review aims at summarizing recent findings on the regulatory activities of vitamin E metabolites, especially of LCMs. © 2018 IUBMB Life, 71(4):479–486, 2019

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Determination of tocopherols and their metabolites by liquid-chromatography coupled with tandem mass spectrometry in human plasma and serum

Cited by 38 publications

References 39 publications

Structure–Function Relationship Studies In Vitro Reveal Distinct and Specific Effects of Long‐Chain Metabolites of Vitamin E

Structure–Function Relationship Studies In Vitro Reveal Distinct and Specific Effects of Long‐Chain Metabolites of Vitamin E

Vitamin E – The Next 100 Years

Vitamin E: Regulatory role of metabolites

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