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Functional Mechanism of B-Vitamins and Their Metabolites 2.0

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A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Bioactives and Nutraceuticals".

Deadline for manuscript submissions: closed (31 March 2021) | Viewed by 74789

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Dr. Elena Azzini

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CREA—Research Centre for Food and Nutrition, Rome, Italy
Interests: food and nutrition; functional food; antioxidants; phytochemical; food biochemistry
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Dr. Ilaria Peluso

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Research Centre for Food and Nutrition, Council for Agricultural Research and Economics (CREA-AN), Rome, Italy
Interests: nutraceuticals; inflammation; immunonutrition; pharmanutrition; food-drug interactions
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Dr. Angela Polito

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CREA—Research Centre for Food and Nutrition, 00178 Rome, Italy
Interests: nutritional status; energy metabolism; energy requirements; physical activity; body composition; obesity; anorexia nervosa; elderly
Special Issues, Collections and Topics in MDPI journals

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Dear Colleagues,

Based on the interest of our Special Issue, as well as future directions of research suggested by authors, we would like to propose a new Edition of "Functional Mechanism of B-vitamins and Its Metabolites". In this field still there are a lot to investigate, and new and updated techs or information can be include. As known the activity of Vitamin B12 (cobalamin) is particularly crucial for two enzymes methionine synthase (coenzymatic form: methyl-Cbl) and L-methylmalonylCoA mutase (coenzymatic form: 5'-deoxydendenosyl-Cbl). The first citoplasmatic reaction includes the one-carbon metabolism pathway leading to nucleic acid synthesis and cellular methylation reactions. The second, the propionic acid oxidation, occurs at the mitochondrial level, and it converts odd-chain fatty acids and branched-chain amino acids into energy. The availability of modern biomarkers and the preventive supplementation have dramatically reduced clinically manifested cobalamin deficiency. Mild to moderate B12 deficiency conditions are associated with several age-related diseases. A combination of biomarkers of cobalamin status, i.e. serum cobalamin, holotranscobalamin (holoTC), methylmalonic acid (MMA) and plasma total homocysteine (tHcy), represents the most suitable approach to evaluate the presence of its adequate dietary intake.

This Special Issue gives insight in the evolving field of vitamin B group as well as its metabolites regarding its mechanisms of action, deficiency, supplementation, health benefits, primary prevention as well as assessment.

Dr. Elena Azzini
Dr. Ilaria Peluso
Dr. Angela Polito
Guest Editors

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Keywords

Vitamin B12 dietary sources and malabsorption
assessment and determinants of vitamin B12 status

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Published Papers (10 papers)

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Research

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13 pages, 1613 KiB

Open AccessArticle

Equilibrative Nucleoside Transporters Mediate the Import of Nicotinamide Riboside and Nicotinic Acid Riboside into Human Cells

by Andrey Kropotov, Veronika Kulikova, Kirill Nerinovski, Alexander Yakimov, Maria Svetlova, Ljudmila Solovjeva, Julia Sudnitsyna, Marie E. Migaud, Mikhail Khodorkovskiy, Mathias Ziegler and Andrey Nikiforov

Int. J. Mol. Sci. 2021, 22(3), 1391; https://doi.org/10.3390/ijms22031391 - 30 Jan 2021

Cited by 42 | Viewed by 5289

Abstract

Nicotinamide riboside (NR), a new form of vitamin B3, is an effective precursor of nicotinamide adenine dinucleotide (NAD⁺) in human and animal cells. The introduction of NR into the body effectively increases the level of intracellular NAD⁺ and thereby restores physiological functions that are weakened or lost in experimental models of aging and various pathologies. Despite the active use of NR in applied biomedicine, the mechanism of its transport into mammalian cells is currently not understood. In this study, we used overexpression of proteins in HEK293 cells, and metabolite detection by NMR, to show that extracellular NR can be imported into cells by members of the equilibrative nucleoside transporter (ENT) family ENT1, ENT2, and ENT4. After being imported into cells, NR is readily metabolized resulting in Nam generation. Moreover, the same ENT-dependent mechanism can be used to import the deamidated form of NR, nicotinic acid riboside (NAR). However, NAR uptake into HEK293 cells required the stimulation of its active utilization in the cytosol such as phosphorylation by NR kinase. On the other hand, we did not detect any NR uptake mediated by the concentrative nucleoside transporters (CNT) CNT1, CNT2, or CNT3, while overexpression of CNT3, but not CNT1 or CNT2, moderately stimulated NAR utilization by HEK293 cells. Full article

(This article belongs to the Special Issue Functional Mechanism of B-Vitamins and Their Metabolites 2.0)

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22 pages, 4648 KiB

Open AccessArticle

Folinate Supplementation Ameliorates Methotrexate Induced Mitochondrial Formate Depletion In Vitro and In Vivo

by Nga-Lai Sou, Yu-Hsuan Huang, Der-Yuan Chen, Yi-Ming Chen, Feng-Yao Tang, Hsin-An Ko, Yi-Hsuan Fan, Yi-Ying Lin, Yi-Cheng Wang, Hui-Ming Chih, Barry Shane, Wen-Nan Huang and En-Pei Isabel Chiang

Int. J. Mol. Sci. 2021, 22(3), 1350; https://doi.org/10.3390/ijms22031350 - 29 Jan 2021

Cited by 6 | Viewed by 4090

Abstract

(1) Background: Antifolate methotrexate (MTX) is the most common disease-modifying antirheumatic drug (DMARD) for treating human rheumatoid arthritis (RA). The mitochondrial-produced formate is essential for folate-mediated one carbon (1C) metabolism. The impacts of MTX on formate homeostasis in unknown, and rigorously controlled kinetic studies can greatly help in this regard. (2) Methods: Combining animal model (8-week old female C57BL/6JNarl mice, n = 18), cell models, stable isotopic tracer studies with gas chromatography/mass spectrometry (GC/MS) platforms, we systematically investigated how MTX interferes with the partitioning of mitochondrial and cytosolic formate metabolism. (3) Results: MTX significantly reduced de novo deoxythymidylate (dTMP) and methionine biosyntheses from mitochondrial-derived formate in cells, mouse liver, and bone marrow, supporting our postulation that MTX depletes mitochondrial 1C supply. Furthermore, MTX inhibited formate generation from mitochondria glycine cleavage system (GCS) both in vitro and in vivo. Folinate selectively rescued 1C metabolic pathways in a tissue-, cellular compartment-, and pathway-specific manner: folinate effectively reversed the inhibition of mitochondrial formate-dependent 1C metabolism in mouse bone marrow (dTMP, methionine, and GCS) and cells (dTMP and GCS) but not methionine synthesis in liver/liver-derived cells. Folinate failed to fully recover hepatic mitochondrial-formate utilization for methionine synthesis, suggesting that the efficacy of clinical folinate rescue in MTX therapy on hepatic methionine metabolism is poor. (4) Conclusion: Conducting studies in mouse and cell models, we demonstrate novel findings that MTX specifically depletes mitochondrial 1C supply that can be ameliorated by folinate supplementation except for hepatic transmethylation. These results imply that clinical use of low-dose MTX may particularly impede 1C metabolism via depletion of mitochondrial formate. The MTX induced systematic and tissue-specific formate depletion needs to be addressed more carefully, and the efficacy of folinate with respect to protecting against such depletion deserves to be evaluated in medical practice. Full article

(This article belongs to the Special Issue Functional Mechanism of B-Vitamins and Their Metabolites 2.0)

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18 pages, 2919 KiB

Open AccessArticle

Molecular Properties of Bare and Microhydrated Vitamin B5–Calcium Complexes

by Davide Corinti, Barbara Chiavarino, Debora Scuderi, Caterina Fraschetti, Antonello Filippi, Simonetta Fornarini and Maria Elisa Crestoni

Int. J. Mol. Sci. 2021, 22(2), 692; https://doi.org/10.3390/ijms22020692 - 12 Jan 2021

Cited by 6 | Viewed by 3541

Abstract

Pantothenic acid, also called vitamin B5, is an essential nutrient involved in several metabolic pathways. It shows a characteristic preference for interacting with Ca(II) ions, which are abundant in the extracellular media and act as secondary mediators in the activation of numerous biological functions. The bare deprotonated form of pantothenic acid, [panto-H]⁻, its complex with Ca(II) ion, [Ca(panto-H)]⁺, and singly charged micro-hydrated calcium pantothenate [Ca(panto-H)(H₂O)]⁺ adduct have been obtained in the gas phase by electrospray ionization and assayed by mass spectrometry and IR multiple photon dissociation spectroscopy in the fingerprint spectral range. Quantum chemical calculations at the B3LYP(-D3) and MP2 levels of theory were performed to simulate geometries, thermochemical data, and linear absorption spectra of low-lying isomers, allowing us to assign the experimental absorptions to particular structural motifs. Pantothenate was found to exist in the gas phase as a single isomeric form showing deprotonation on the carboxylic moiety. On the contrary, free and monohydrated calcium complexes of deprotonated pantothenic acid both present at least two isomers participating in the gas-phase population, sharing the deprotonation of pantothenate on the carboxylic group and either a fourfold or fivefold coordination with calcium, thus justifying the strong affinity of pantothenate for the metal. Full article

(This article belongs to the Special Issue Functional Mechanism of B-Vitamins and Their Metabolites 2.0)

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18 pages, 7152 KiB

Open AccessArticle

Amorphization of Thiamine Mononitrate: A Study of Crystallization Inhibition and Chemical Stability of Thiamine in Thiamine Mononitrate Amorphous Solid Dispersions

by Seda Arioglu-Tuncil, Adrienne L. Voelker, Lynne S. Taylor and Lisa J. Mauer

Int. J. Mol. Sci. 2020, 21(24), 9370; https://doi.org/10.3390/ijms21249370 - 9 Dec 2020

Cited by 3 | Viewed by 3279

Abstract

This study investigated thiamine degradation in thiamine mononitrate (TMN):polymer solid dispersions, accounting for the physical state of the vitamin and the recrystallization tendency of TMN in these dispersions. Results were compared with those from solid dispersions containing a different salt form of thiamine (thiamine chloride hydrochloride (TClHCl)). TMN:polymer dispersions were prepared by lyophilizing solutions containing TMN and amorphous polymers (pectin and PVP (polyvinylpyrrolidone)). Samples were stored in controlled temperature and relative humidity (RH) environments for eight weeks and monitored periodically by X-ray diffraction and high performance liquid chromatography (HPLC). Moisture sorption, glass transition temperature (T_g), intermolecular interactions, and pH were also determined. Similar to the TClHCl:polymer dispersions, thiamine was more chemically labile in the amorphous state than the crystalline state, when present in lower proportions in amorphous TMN:polymer dispersions despite increasing T_g values, when environmental storage conditions exceeded the T_g of the dispersion, and when co-formulated with PVP compared to pectin. When thiamine remained as an amorphous solid, chemical stability of thiamine did not differ as a function of counterion present (TMN vs. TClHCl). However, storage at 75% RH led to hydration of thiamine:PVP dispersions, and the resulting pH of the solutions as a function of thiamine salt form led to a higher chemical stability in the acidic TClHCl samples than in the neutral TMN samples. Full article

(This article belongs to the Special Issue Functional Mechanism of B-Vitamins and Their Metabolites 2.0)

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21 pages, 3283 KiB

Open AccessArticle

Tracing Metabolic Fate of Mitochondrial Glycine Cleavage System Derived Formate In Vitro and In Vivo

by Yee-Ling Tan, Nga-Lai Sou, Feng-Yao Tang, Hsin-An Ko, Wei-Ting Yeh, Jian-Hau Peng and En-Pei Isabel Chiang

Int. J. Mol. Sci. 2020, 21(22), 8808; https://doi.org/10.3390/ijms21228808 - 20 Nov 2020

Cited by 13 | Viewed by 5938

Abstract

Folate-mediated one-carbon (1C) metabolism is a major target of many therapies in human diseases. Studies have focused on the metabolism of serine 3-carbon as it serves as a major source for 1C units. The serine 3-carbon enters the mitochondria transferred by folate cofactors and eventually converted to formate and serves as a major building block for cytosolic 1C metabolism. Abnormal glycine metabolism has been reported in many human pathological conditions. The mitochondrial glycine cleavage system (GCS) catalyzes glycine degradation to CO₂ and ammonium, while tetrahydrofolate (THF) is converted into 5,10-methylene-THF. GCS accounts for a substantial proportion of whole-body glycine flux in humans, yet the particular metabolic route of glycine 2-carbon recycled from GCS during mitochondria glycine decarboxylation in hepatic or bone marrow 1C metabolism is not fully investigated, due to the limited accessibility of human tissues. Labeled glycine at 2-carbon was given to humans and primary cells in previous studies for investigating its incorporations into purines, its interconversion with serine, or the CO₂ production in the mitochondria. Less is known on the metabolic fate of the glycine 2-carbon recycled from the GCS; hence, a model system tracing its metabolic fate would help in this regard. We took the direct approach of isotopic labeling to further explore the in vitro and in vivo metabolic fate of the 2-carbon from [2-¹³C]glycine and [2-¹³C]serine. As the 2-carbon of glycine and serine is decarboxylated and catabolized via the GCS, the original 13C-labeled 2-carbon is transferred to THF and yield methyleneTHF in the mitochondria. In human hepatoma cell-lines, 2-carbon from glycine was found to be incorporated into deoxythymidine (dTMP, dT + 1), M + 3 species of purines (deoxyadenine, dA and deoxyguanine, dG), and methionine (Met + 1). In healthy mice, incorporation of GCS-derived formate from glycine 2-carbon was found in serine (Ser + 2 via cytosolic serine hydroxy methyl transferase), methionine, dTMP, and methylcytosine (mC + 1) in bone marrow DNA. In these experiments, labeled glycine 2-carbon directly incorporates into Ser + 1, A + 2, and G + 2 (at C2 and C8 of purine) in the cytosol. It is noteworthy that since the serine 3-carbon is unlabeled in these experiments, the isotopic enrichments in dT + 1, Ser + 2, dA + 3, dG + 3, and Met + 1 solely come from the 2-carbon of glycine/serine recycled from GCS, re-enters the cytosolic 1C metabolism as formate, and then being used for cytosolic syntheses of serine, dTMP, purine (M + 3) and methionine. Taken together, we established model systems and successfully traced the metabolic fate of mitochondrial GCS-derived formate from glycine 2-carbon in vitro and in vivo. Nutritional supply significantly alters formate generation from GCS. More GCS-derived formate was used in hepatic serine and methionine syntheses, whereas more GCS-derived formate was used in dTMP synthesis in the bone marrow, indicating that the utilization and partitioning of GCS-derived 1C unit are tissue-specific. These approaches enable better understanding concerning the utilization of 1C moiety generated from mitochondrial GCS that can help to further elucidate the role of GCS in human disease development and progression in future applications. More studies on GCS using these approaches are underway. Full article

(This article belongs to the Special Issue Functional Mechanism of B-Vitamins and Their Metabolites 2.0)

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11 pages, 684 KiB

Open AccessCommunication

The Stimulation of Neurogenesis Improves the Cognitive Status of Aging Rats Subjected to Gestational and Perinatal Deficiency of B9–12 Vitamins

by Grégory Pourié, Nicolas Martin, Jean-Luc Daval, Jean-Marc Alberto, Rémy Umoret, Jean-Louis Guéant and Carine Bossenmeyer-Pourié

Int. J. Mol. Sci. 2020, 21(21), 8008; https://doi.org/10.3390/ijms21218008 - 28 Oct 2020

Cited by 9 | Viewed by 2504

Abstract

A deficiency in B-vitamins is known to lead to persistent developmental defects in various organs during early life. The nervous system is particularly affected with functional retardation in infants and young adults. In addition, even if in some cases no damage appears evident in the beginning of life, correlations have been shown between B-vitamin metabolism and neurodegenerative diseases. However, despite the usual treatment based on B-vitamin injections, the neurological outcomes remain poorly rescued in the majority of cases, compared with physiological functions. In this study, we explored whether a neonatal stimulation of neurogenesis could compensate atrophy of specific brain areas such as the hippocampus, in the case of B-vitamin deficiency. Using a physiological mild transient hypoxia within the first 24 h after birth, rat-pups, submitted or not to neonatal B-vitamin deficiency, were followed until 330-days-of-age for their cognitive capacities and their hippocampus status. Our results showed a gender effect since females were more affected than males by the deficiency, showing a persistent low body weight and poor cognitive performance to exit a maze. Nevertheless, the neonatal stimulation of neurogenesis with hypoxia rescued the maze performance during adulthood without modifying physiological markers, such as body weight and circulating homocysteine. Our findings were reinforced by an increase of several markers at 330-days-of-age in hypoxic animals, such as Ammon’s Horn 1hippocampus (CA1) thickness and the expression of key actors of synaptic dynamic, such as the NMDA-receptor-1 (NMDAR1) and the post-synaptic-density-95 (PSD-95). We have not focused our conclusion on the neonatal hypoxia as a putative treatment, but we have discussed that, in the case of neurologic retardation associated with a reduced B-vitamin status, stimulation of the latent neurogenesis in infants could ameliorate their quality of life during their lifespan. Full article

(This article belongs to the Special Issue Functional Mechanism of B-Vitamins and Their Metabolites 2.0)

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15 pages, 1782 KiB

Open AccessArticle

Amorphization of Thiamine Chloride Hydrochloride: Effects of Physical State and Polymer Type on the Chemical Stability of Thiamine in Solid Dispersions

by Seda Arioglu-Tuncil, Adrienne L. Voelker, Lynne S. Taylor and Lisa J. Mauer

Int. J. Mol. Sci. 2020, 21(16), 5935; https://doi.org/10.3390/ijms21165935 - 18 Aug 2020

Cited by 9 | Viewed by 3128

Abstract

Thiamine is an essential micronutrient, but delivery of the vitamin in supplements or foods is challenging because it is unstable under heat, alkaline pH, and processing/storage conditions. Although distributed as a crystalline ingredient, thiamine chloride hydrochloride (TClHCl) likely exists in the amorphous state, specifically in supplements. Amorphous solids are generally less chemically stable than their crystalline counterparts, which is an unexplored area related to thiamine delivery. The objective of this study was to document thiamine degradation in the amorphous state. TClHCl:polymer dispersions were prepared by lyophilizing solutions containing TClHCl and amorphous polymers (pectin and PVP (poly[vinylpyrrolidone])). Samples were stored in controlled temperature (30–60 °C) and relative humidity (11%) environments for 8 weeks and monitored periodically by X-ray diffraction (to document physical state) and HPLC (to quantify degradation). Moisture sorption, glass transition temperature (T_g), intermolecular interactions, and pH were also determined. Thiamine was more labile in the amorphous state than the crystalline state and when present in lower proportions in amorphous polymer dispersions, despite increasing T_g values. Thiamine was more stable in pectin dispersions than PVP dispersions, attributed to differences in presence and extent of intermolecular interactions between TClHCl and pectin. The results of this study can be used to control thiamine degradation in food products and supplements to improve thiamine delivery and decrease rate of deficiency. Full article

(This article belongs to the Special Issue Functional Mechanism of B-Vitamins and Their Metabolites 2.0)

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Review

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15 pages, 1008 KiB

Open AccessReview

A Brief Review on Vitamin B₁₂ Deficiency Looking at Some Case Study Reports in Adults

by Elena Azzini, Anna Raguzzini and Angela Polito

Int. J. Mol. Sci. 2021, 22(18), 9694; https://doi.org/10.3390/ijms22189694 - 7 Sep 2021

Cited by 30 | Viewed by 15188

Abstract

In the era of evidence-based medicine, the randomized clinical trial corresponds to the top step in the qualitative scale of the evidence available in the literature, while small series of cases or the description of individual cases occupy the last place. However, the latter represent an important part of clinical practice and have significantly influenced the evolution of medicine, contributing significantly to the advancement of scientific knowledge. Vitamin B₁₂ deficiency shares several common symptoms that affect several tissues and organs with health aliments, so its diagnosis could be unobvious for the broad array of its effects and investigation methods used. In this review, we focused our attention on some case reports related to the vitamin B₁₂ deficiency associated to anemia, neurologic disorders, and hyperhomocysteinemia. B₁₂ deficiency reversal is simply achieved by prompt therapy, even though it is not the same for several disorders. Full article

(This article belongs to the Special Issue Functional Mechanism of B-Vitamins and Their Metabolites 2.0)

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19 pages, 1794 KiB

Open AccessReview

Neuroprotective Effects of Thiamine and Precursors with Higher Bioavailability: Focus on Benfotiamine and Dibenzoylthiamine

by Margaux Sambon, Pierre Wins and Lucien Bettendorff

Int. J. Mol. Sci. 2021, 22(11), 5418; https://doi.org/10.3390/ijms22115418 - 21 May 2021

Cited by 32 | Viewed by 12850

Abstract

Thiamine (vitamin B1) is essential for brain function because of the coenzyme role of thiamine diphosphate (ThDP) in glucose and energy metabolism. In order to compensate thiamine deficiency, several thiamine precursors with higher bioavailability were developed since the 1950s. Among these, the thioester benfotiamine (BFT) has been extensively studied and has beneficial effects both in rodent models of neurodegeneration and in human clinical studies. BFT has antioxidant and anti-inflammatory properties that seem to be mediated by a mechanism independent of the coenzyme function of ThDP. BFT has no adverse effects and improves cognitive outcome in patients with mild Alzheimer’s disease (AD). Recent in vitro studies show that another thiamine thioester, dibenzoylthiamine (DBT) is even more efficient that BFT, especially with respect to its anti-inflammatory potency. Thiamine thioesters have pleiotropic properties linked to an increase in circulating thiamine concentrations and possibly in hitherto unidentified metabolites in particular open thiazole ring derivatives. The identification of the active neuroprotective derivatives and the clarification of their mechanism of action open extremely promising perspectives in the field of neurodegenerative, neurodevelopmental and psychiatric conditions. Full article

(This article belongs to the Special Issue Functional Mechanism of B-Vitamins and Their Metabolites 2.0)

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18 pages, 1079 KiB

Open AccessReview

Vitamin B6 and Diabetes: Relationship and Molecular Mechanisms

by Elisa Mascolo and Fiammetta Vernì

Int. J. Mol. Sci. 2020, 21(10), 3669; https://doi.org/10.3390/ijms21103669 - 23 May 2020

Cited by 87 | Viewed by 17190

Abstract

Vitamin B6 is a cofactor for approximately 150 reactions that regulate the metabolism of glucose, lipids, amino acids, DNA, and neurotransmitters. In addition, it plays the role of antioxidant by counteracting the formation of reactive oxygen species (ROS) and advanced glycation end-products (AGEs). Epidemiological and experimental studies indicated an evident inverse association between vitamin B6 levels and diabetes, as well as a clear protective effect of vitamin B6 on diabetic complications. Interestingly, by exploring the mechanisms that govern the relationship between this vitamin and diabetes, vitamin B6 can be considered both a cause and effect of diabetes. This review aims to report the main evidence concerning the role of vitamin B6 in diabetes and to examine the underlying molecular and cellular mechanisms. In addition, the relationship between vitamin B6, genome integrity, and diabetes is examined. The protective role of this vitamin against diabetes and cancer is discussed. Full article

(This article belongs to the Special Issue Functional Mechanism of B-Vitamins and Their Metabolites 2.0)

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