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Traber MG. Human Vitamin E deficiency, and what is and is not Vitamin E? Free Radic Biol Med 2024; 213:285-292. [PMID: 38242248 PMCID: PMC10923111 DOI: 10.1016/j.freeradbiomed.2024.01.024] [Citation(s) in RCA: 8] [Impact Index Per Article: 8.0] [Reference Citation Analysis] [MESH Headings] [Grants] [Track Full Text] [Journal Information] [Submit a Manuscript] [Subscribe] [Scholar Register] [Received: 12/06/2023] [Revised: 01/04/2024] [Accepted: 01/16/2024] [Indexed: 01/21/2024]
Affiliation(s)
- Maret G Traber
- Linus Pauling Institute, Oregon State University, Corvallis, OR, 97331, USA
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Bouchet F, Atze H, Fonvielle M, Edoo Z, Arthur M, Ethève-Quelquejeu M, Iannazzo L. Diazabicyclooctane Functionalization for Inhibition of β-Lactamases from Enterobacteria. J Med Chem 2020; 63:5257-5273. [DOI: 10.1021/acs.jmedchem.9b02125] [Citation(s) in RCA: 8] [Impact Index Per Article: 1.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/27/2023]
Affiliation(s)
- Flavie Bouchet
- Université de Paris, UMR CNRS 8601, Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, 45 rue des Saints-Péres, F-75006 Paris, France
| | - Heiner Atze
- INSERM, Sorbonne Université, Université de Paris, Centre de Recherche des Cordeliers (CRC), F-75006 Paris, France
| | - Matthieu Fonvielle
- INSERM, Sorbonne Université, Université de Paris, Centre de Recherche des Cordeliers (CRC), F-75006 Paris, France
| | - Zainab Edoo
- INSERM, Sorbonne Université, Université de Paris, Centre de Recherche des Cordeliers (CRC), F-75006 Paris, France
| | - Michel Arthur
- INSERM, Sorbonne Université, Université de Paris, Centre de Recherche des Cordeliers (CRC), F-75006 Paris, France
| | - Mélanie Ethève-Quelquejeu
- Université de Paris, UMR CNRS 8601, Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, 45 rue des Saints-Péres, F-75006 Paris, France
| | - Laura Iannazzo
- Université de Paris, UMR CNRS 8601, Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, 45 rue des Saints-Péres, F-75006 Paris, France
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Guthrie G, Stoll B, Chacko S, Lauridsen C, Plat J, Burrin D. Rifampicin, not vitamin E, suppresses parenteral nutrition-associated liver disease development through the pregnane X receptor pathway in piglets. Am J Physiol Gastrointest Liver Physiol 2020; 318:G41-G52. [PMID: 31604032 PMCID: PMC6985848 DOI: 10.1152/ajpgi.00193.2019] [Citation(s) in RCA: 9] [Impact Index Per Article: 1.8] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Submit a Manuscript] [Subscribe] [Scholar Register] [Indexed: 01/31/2023]
Abstract
Infants receiving long-term parenteral nutrition (PN) develop PN-associated liver disease (PNALD). We previously (Ng K et al. JPEN J Parenter Enteral Nutr 40: 656-671, 2016. doi:10.1177/0148607114567900.) showed that PN containing soy-based lipid supplemented with vitamin E (α-tocopherol) prevents the development of PNALD. We hypothesize that this occurs via vitamin E activation of pregnane X receptor (PXR)-mediated pathways involved in bile acid metabolism. Neonatal piglets received PN for 14 days containing Intralipid (IL; soy-based lipid emulsion), IL supplemented with 12.6 mg·kg-1·day-1 vitamin E (VITE), or IL with 10 mg·kg-1·day-1 Rifadin IV (RIF), a PXR agonist. Pigs treated with IL and VITE, but not RIF, developed cholestasis and hyperbilirubinemia, markers of liver disease. The hepatic PXR target genes CYP3A29 and UGT1A6 increased during RIF treatment. RIF also modestly increased metabolism of chenodeoxycholic acid to the more hydrophilic bile acid hyocholic acid. Serum fibroblast growth factor (FGF)-19, a key regulator in suppressing hepatic bile acid synthesis, significantly increased in the RIF group. We conclude rifampicin modified markers of PNALD development by increased metabolism of bile acids and potentially suppressed bile acid synthesis. Vitamin E was ineffective at high lipid doses in preventing PNALD.NEW & NOTEWORTHY Intravenous vitamin E and rifampicin were administered to neonatal piglets receiving parenteral nutrition to determine their efficacy in reducing the progression of parenteral nutrition-associated liver disease (PNALD). Rifampicin increased serum FGF-19 concentrations and synthesis of the bile acid hyocholic acid which led to a reduction of PNALD parameters at 2 wk of administration. This result has potential clinical implications for the use of rifampicin as a safe and inexpensive treatment for short-term development of PNALD.
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Affiliation(s)
- Gregory Guthrie
- 1United States Department of Agriculture Agricultural Research Service, Children’s Nutrition Research Center, Section of Pediatric Gastroenterology, Hepatology, and Nutrition, Department of Pediatrics, Baylor College of Medicine, Houston, Texas
| | - Barbara Stoll
- 1United States Department of Agriculture Agricultural Research Service, Children’s Nutrition Research Center, Section of Pediatric Gastroenterology, Hepatology, and Nutrition, Department of Pediatrics, Baylor College of Medicine, Houston, Texas
| | - Shaji Chacko
- 1United States Department of Agriculture Agricultural Research Service, Children’s Nutrition Research Center, Section of Pediatric Gastroenterology, Hepatology, and Nutrition, Department of Pediatrics, Baylor College of Medicine, Houston, Texas
| | | | - Jogchum Plat
- 3Department of Nutrition and Movement Sciences, School of Nutrition and Translational Research in Metabolism, Maastricht University, Maastricht, The Netherlands
| | - Douglas Burrin
- 1United States Department of Agriculture Agricultural Research Service, Children’s Nutrition Research Center, Section of Pediatric Gastroenterology, Hepatology, and Nutrition, Department of Pediatrics, Baylor College of Medicine, Houston, Texas
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Michailidis D, Angelis A, Aligiannis N, Mitakou S, Skaltsounis L. Recovery of Sesamin, Sesamolin, and Minor Lignans From Sesame Oil Using Solid Support-Free Liquid-Liquid Extraction and Chromatography Techniques and Evaluation of Their Enzymatic Inhibition Properties. Front Pharmacol 2019; 10:723. [PMID: 31316384 PMCID: PMC6610769 DOI: 10.3389/fphar.2019.00723] [Citation(s) in RCA: 24] [Impact Index Per Article: 4.0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 02/13/2019] [Accepted: 06/05/2019] [Indexed: 12/14/2022] Open
Abstract
In this study, an integrated process for the recovery of sesamin and sesamolin, two high added-value lignans of sesame oil (SO) was developed, using synchronous extraction and chromatography techniques. The extraction of SO phenolic content was studied using two different extraction techniques: Annular centrifugal extraction (ACE) and centrifugal partition extraction (CPE). The derived data of each experiment were compared in terms of revealing the yields, time, and solvents consumption showing that CPE is the most effective technique, concerning the solvent consumption. The isolation of lignans was achieved using centrifugal partition chromatography (CPC) both on semi-preparative and preparative scale. The biphasic system used for this purpose consisted of the following solvents: n-Hex/EtOAc/EtOH/H2O in proportion 2:3:3:2 (v/v/v/v) and direct recovery of the two major lignans sesamin and sesamolin was achieved. In parallel the CPC analysis resulted in the isolation of four minor lignans of sesame oil, i.e., samin, sesamol, sesaminol, and episesaminol. Structure elucidation of isolated lignans was based on HRMS/MS and NMR experiments. High-performance liquid chromatography (HPLC) was employed for quantitative analysis of the obtained extracts to determine the purity of the isolated compounds as well. The results of this study demonstrated that sesamin and sesamolin were recovered in purity higher than 95%, verifying the effectiveness of the purposed separation methodology. Finally, due to the general application of sesame oil in cosmetic industry, all the pure compounds were evaluated for their tyrosinase, elastase, collagenase, and hyaluronidase inhibition activity.
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Affiliation(s)
- Dimitris Michailidis
- Faculty of Pharmacy, Department of Pharmacognosy and Natural Products Chemistry, University of Athens, Athens, Greece
| | - Apostolis Angelis
- Faculty of Pharmacy, Department of Pharmacognosy and Natural Products Chemistry, University of Athens, Athens, Greece
| | - Nektarios Aligiannis
- Faculty of Pharmacy, Department of Pharmacognosy and Natural Products Chemistry, University of Athens, Athens, Greece
| | - Sofia Mitakou
- Faculty of Pharmacy, Department of Pharmacognosy and Natural Products Chemistry, University of Athens, Athens, Greece
| | - Léandros Skaltsounis
- Faculty of Pharmacy, Department of Pharmacognosy and Natural Products Chemistry, University of Athens, Athens, Greece
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Schmölz L, Birringer M, Lorkowski S, Wallert M. Complexity of vitamin E metabolism. World J Biol Chem 2016; 7:14-43. [PMID: 26981194 PMCID: PMC4768118 DOI: 10.4331/wjbc.v7.i1.14] [Citation(s) in RCA: 135] [Impact Index Per Article: 15.0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Journal Information] [Submit a Manuscript] [Subscribe] [Scholar Register] [Received: 08/24/2015] [Revised: 11/25/2015] [Accepted: 01/19/2016] [Indexed: 02/05/2023] Open
Abstract
Bioavailability of vitamin E is influenced by several factors, most are highlighted in this review. While gender, age and genetic constitution influence vitamin E bioavailability but cannot be modified, life-style and intake of vitamin E can be. Numerous factors must be taken into account however, i.e., when vitamin E is orally administrated, the food matrix may contain competing nutrients. The complex metabolic processes comprise intestinal absorption, vascular transport, hepatic sorting by intracellular binding proteins, such as the significant α-tocopherol-transfer protein, and hepatic metabolism. The coordinated changes involved in the hepatic metabolism of vitamin E provide an effective physiological pathway to protect tissues against the excessive accumulation of, in particular, non-α-tocopherol forms. Metabolism of vitamin E begins with one cycle of CYP4F2/CYP3A4-dependent ω-hydroxylation followed by five cycles of subsequent β-oxidation, and forms the water-soluble end-product carboxyethylhydroxychroman. All known hepatic metabolites can be conjugated and are excreted, depending on the length of their side-chain, either via urine or feces. The physiological handling of vitamin E underlies kinetics which vary between the different vitamin E forms. Here, saturation of the side-chain and also substitution of the chromanol ring system are important. Most of the metabolic reactions and processes that are involved with vitamin E are also shared by other fat soluble vitamins. Influencing interactions with other nutrients such as vitamin K or pharmaceuticals are also covered by this review. All these processes modulate the formation of vitamin E metabolites and their concentrations in tissues and body fluids. Differences in metabolism might be responsible for the discrepancies that have been observed in studies performed in vivo and in vitro using vitamin E as a supplement or nutrient. To evaluate individual vitamin E status, the analytical procedures used for detecting and quantifying vitamin E and its metabolites are crucial. The latest methods in analytics are presented.
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Belskaya N, Subbotina J, Lesogorova S. Synthesis of 2H-1,2,3-Triazoles. TOPICS IN HETEROCYCLIC CHEMISTRY 2014. [DOI: 10.1007/7081_2014_125] [Citation(s) in RCA: 31] [Impact Index Per Article: 2.8] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 01/08/2023]
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Traber MG. Mechanisms for the prevention of vitamin E excess. J Lipid Res 2013; 54:2295-306. [PMID: 23505319 PMCID: PMC3735929 DOI: 10.1194/jlr.r032946] [Citation(s) in RCA: 80] [Impact Index Per Article: 6.7] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Grants] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 10/05/2012] [Revised: 03/04/2013] [Indexed: 02/07/2023] Open
Abstract
The liver is at the nexus of the regulation of lipoprotein uptake, synthesis, and secretion, and it is the site of xenobiotic detoxification by cytochrome P450 oxidation systems (phase I), conjugation systems (phase II), and transporters (phase III). These two major liver systems control vitamin E status. The mechanisms for the preference for α-tocopherol relative to the eight naturally occurring vitamin E forms largely depend upon the liver and include both a preferential secretion of α-tocopherol from the liver into the plasma for its transport in circulating lipoproteins for subsequent uptake by tissues, as well as the preferential hepatic metabolism of non-α-tocopherol forms. These mechanisms are the focus of this review.
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Affiliation(s)
- Maret G Traber
- Linus Pauling Institute, Oregon State University, Corvallis, OR, USA.
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Traber MG. Regulation of xenobiotic metabolism, the only signaling function of α-tocopherol? Mol Nutr Food Res 2010; 54:661-8. [DOI: 10.1002/mnfr.200900440] [Citation(s) in RCA: 21] [Impact Index Per Article: 1.4] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/14/2022]
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Synthesis of α-tocohexaenol (α-T6) a fluorescent, oxidatively sensitive polyene analogue of α-tocopherol. Bioorg Med Chem 2010; 18:777-86. [DOI: 10.1016/j.bmc.2009.11.051] [Citation(s) in RCA: 6] [Impact Index Per Article: 0.4] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 10/27/2009] [Revised: 11/20/2009] [Accepted: 11/21/2009] [Indexed: 11/20/2022]
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