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Special Issue "Vitamins"

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A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (30 November 2009)

Special Issue Editor

Guest Editor
Dr. Thomas Netscher

Research and Development, DSM Nutritional Products, Bldg. 214/27, P.O. Box 2676, CH-4002 Basel, Switzerland
Fax: +41 (0)61 815 8750

Special Issue Information

Dear Colleagues,

Vitamins are essential organic copmpounds which are either not synthesized in the human and animal organism or formed only in insufficient amounts. Nutraceuticals are the active ingredients in functional food or nutraceutical supplements that deliver a health benefit. Both groups of compounds must be taken up by nutrition and are of great economical importance as additives in food and feed (human and animal nutrition), in pharma, health and personal care products of daily life, as well as technical applications, for example as stabilizers.

Contributions for this special issue may cover all aspects of their chemistry, like investigations of biosynthesis, biological activity, metabolism, sourcing from nature, analytics, and the broad range of activities accompanied with organic chemical synthesis. This is preparation of stereoisomers, derivatives, labelled compounds, metabolites, analogues and intermediates, elucidation of reaction mechanisms, and development of efficient catalytic methods, including biotransformations, in particular directed towards environmentally benign large-scale production.

Thomas Netscher, Ph. D.
Guest Editor


Related Journals

Keywords

  • organic synthesis
  • catalysis
  • biotransformation
  • reaction mechanism
  • biosynthesis
  • analytics
  • natural sources
  • biological activity
  • metabolism
  • nutrition

Published Papers (10 papers)

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Research

Jump to: Review

Open AccessArticle Synergistic Chondroprotective Effect of α-Tocopherol, Ascorbic Acid, and Selenium as well as Glucosamine and Chondroitin on Oxidant Induced Cell Death and Inhibition of Matrix Metalloproteinase-3—Studies in Cultured Chondrocytes
Molecules 2010, 15(1), 27-39; doi:10.3390/molecules15010027
Received: 1 December 2009 / Revised: 16 December 2009 / Accepted: 23 December 2009 / Published: 24 December 2009
Cited by 6 | PDF Full-text (665 KB)
Abstract
Overproduction of reactive oxygen species and impaired antioxidant defence accompanied by chronic inflammatory processes may impair joint health. Pro-inflammatory cytokines such as interleukin-1β (IL-1β) and tumor necrosis factor alpha (TNF-α) stimulate the expression of metalloproteinases which degrade the extracellular matrix. Little is [...] Read more.
Overproduction of reactive oxygen species and impaired antioxidant defence accompanied by chronic inflammatory processes may impair joint health. Pro-inflammatory cytokines such as interleukin-1β (IL-1β) and tumor necrosis factor alpha (TNF-α) stimulate the expression of metalloproteinases which degrade the extracellular matrix. Little is known regarding the potential synergistic effects of natural compounds such as α-tocopherol (α-toc), ascorbic acid (AA) and selenium (Se) on oxidant induced cell death. Furthermore studies regarding the metalloproteinase-3 inhibitory activity of glucosamine sulfate (GS) and chondroitin sulfate (CS) are scarce. Therefore we have studied the effect of α-toc (0.1–2.5 µmol/L), AA (10–50 µmol/L) and Se (1–50 nmol/L) on t-butyl hydroperoxide (t-BHP, 100–500 µmol/L)-induced cell death in SW1353 chondrocytes. Furthermore we have determined the effect of GS and CS alone (100–500 µmol/L each) and in combination on MMP3 mRNA levels and MMP3 secretion in IL-1β stimulated chondrocytes. A combination of α-toc, AA, and Se was more potent in counteracting t-BHP-induced cytotoxicity as compared to the single compounds. Similarly a combination of CS and GS was more effective in inhibiting MMP3 gene expression and secretion than the single components. The inhibition of MMP3 secretion due to GS plus CS was accompanied by a decrease in TNF-α production. Combining natural compounds such as α-toc, AA, and Se as well as GS and CS seems to be a promising strategy to combat oxidative stress and cytokine induced matrix degradation in chondrocytes. Full article
(This article belongs to the Special Issue Vitamins)
Open AccessArticle Production of β-Maltooligosaccharides of α- and δ-Tocopherols by Klebsiella pneumoniae and Cyclodextrin Glucanotransferase as Anti-Allergic Agents
Molecules 2009, 14(8), 3106-3114; doi:10.3390/molecules14083106
Received: 14 July 2009 / Revised: 19 August 2009 / Accepted: 20 August 2009 / Published: 20 August 2009
Cited by 7 | PDF Full-text (139 KB) | HTML Full-text | XML Full-text
Abstract
The glycosylation of α- and δ-tocopherols using Klebsiella pneumoniae and cyclodextrin glucanotransferase (CGTase) was investigated. K. pneumoniae converted α- and δ-tocopherols into the corresponding β-glucosides in 10 and 8% yield, respectively. CGTase glycosylated α-tocopheryl β-glucoside to α-tocopheryl β-maltoside (51%) and α-tocopheryl β-maltotrioside [...] Read more.
The glycosylation of α- and δ-tocopherols using Klebsiella pneumoniae and cyclodextrin glucanotransferase (CGTase) was investigated. K. pneumoniae converted α- and δ-tocopherols into the corresponding β-glucosides in 10 and 8% yield, respectively. CGTase glycosylated α-tocopheryl β-glucoside to α-tocopheryl β-maltoside (51%) and α-tocopheryl β-maltotrioside (35%). On the other hand, δ-tocopheryl β-glucoside was converted into the corresponding β-maltoside (45%) and β-maltotrioside (29%) by CGTase. The β-glucoside of α-tocopherol, and β-glucoside and β-maltoside of δ-tocopherol showed inhibitory effects on IgE antibody production and on histamine release from rat peritoneal mast cells. Full article
(This article belongs to the Special Issue Vitamins)

Review

Jump to: Research

Open AccessReview Vitamin B12: Unique Metalorganic Compounds and the Most Complex Vitamins
Molecules 2010, 15(5), 3228-3259; doi:10.3390/molecules15053228
Received: 30 March 2010 / Revised: 27 April 2010 / Accepted: 28 April 2010 / Published: 30 April 2010
Cited by 58 | PDF Full-text (2029 KB)
Abstract
The chemistry and biochemistry of the vitamin B12 compounds (cobalamins, XCbl) are described, with particular emphasis on their structural aspects and their relationships with properties and function. A brief history of B12, reveals how much the effort of chemists, [...] Read more.
The chemistry and biochemistry of the vitamin B12 compounds (cobalamins, XCbl) are described, with particular emphasis on their structural aspects and their relationships with properties and function. A brief history of B12, reveals how much the effort of chemists, biochemists and crystallographers have contributed in the past to understand the basic properties of this very complex vitamin. The properties of the two cobalamins, the two important B12 cofactors Ado- and MeCbl are described, with particular emphasis on how the Co-C bond cleavage is involved in the enzymatic mechanisms. The main structural features of cobalamins are described, with particular reference to the axial fragment. The structure/property relationships in cobalamins are summarized. The recent studies on base-off/base-on equilibrium are emphasized for their relevance to the mode of binding of the cofactor to the protein scaffold. The absorption, transport and cellular uptake of cobalamins and the structure of the B12 transport proteins, IF and TC, in mammals are reviewed. The B12 transport in bacteria and the structure of the so far determined proteins are briefly described. The currently accepted mechanisms for the catalytic cycles of the AdoCbl and MeCbl enzymes are reported. The structure and function of B12 enzymes, particularly the important mammalian enzymes methyltransferase (MetH) and methyl-malonyl-coenzymeA mutase (MMCM), are described and briefly discussed. Since fast proliferating cells require higher amount of vitamin B12 than that required by normal cells, the study of B12 conjugates as targeting agents has recently gained importance. Bioconjugates have been studied as potential agents for delivering radioisotopes and NMR probes or as various cytotoxic agents towards cancer cells in humans and the most recent studies are described. Specifically, functionalized bioconjugates are used as “Trojan horses” to carry into the cell the appropriate antitumour or diagnostic label. Possible future developments of B12 work are summarized. Full article
(This article belongs to the Special Issue Vitamins)
Open AccessReview An Update on Vitamin E, Tocopherol and Tocotrienol—Perspectives
Molecules 2010, 15(4), 2103-2113; doi:10.3390/molecules15042103
Received: 6 February 2010 / Revised: 15 March 2010 / Accepted: 23 March 2010 / Published: 24 March 2010
Cited by 51 | PDF Full-text (159 KB)
Abstract
Vitamin E, like tocotrienols and tocopherols, is constituted of compounds essential for animal cells. Vitamin E is exclusively synthesized by photosynthetic eukaryotes and other oxygenic photosynthetic organisms such as cyanobacteria. In order to prevent lipid oxidation, the plants mainly accumulate tocochromanols in [...] Read more.
Vitamin E, like tocotrienols and tocopherols, is constituted of compounds essential for animal cells. Vitamin E is exclusively synthesized by photosynthetic eukaryotes and other oxygenic photosynthetic organisms such as cyanobacteria. In order to prevent lipid oxidation, the plants mainly accumulate tocochromanols in oily seeds and fruits or in young tissues undergoing active cell divisions. From a health point of view, at the moment there is a great interest in the natural forms of tocochromanols, because they are considered promising compounds able to maintain a healthy cardiovascular system and satisfactory blood cholesterol levels. Some evidence suggests that the potency of the antioxidant effects may differ between natural or synthetic source of tocochromanols (vitamin E). Full article
(This article belongs to the Special Issue Vitamins)
Open AccessReview Synthesis and Use of Stable Isotope Enriched Retinals in the Field of Vitamin A
Molecules 2010, 15(3), 1825-1872; doi:10.3390/molecules15031825
Received: 15 January 2010 / Revised: 18 February 2010 / Accepted: 2 March 2010 / Published: 15 March 2010
Cited by 5 | PDF Full-text (366 KB)
Abstract
The role of vitamin A and its metabolites in the life processes starting with the historical background and its up to date information is discussed in the introduction. Also the role of 11Z-retinal in vision and retinoic acid in the [...] Read more.
The role of vitamin A and its metabolites in the life processes starting with the historical background and its up to date information is discussed in the introduction. Also the role of 11Z-retinal in vision and retinoic acid in the biological processes is elucidated. The essential role of isotopically enriched systems in the progress of vision research, nutrition research etc. is discussed. In part B industrial commercial syntheses of vitamin A by the two leading companies Hoffmann-La Roche (now DSM) and BASF are discussed. The knowledge obtained via these pioneering syntheses has been essential for the further synthetic efforts in vitamin A field by other scientific groups. The rest of the paper is devoted to the synthetic efforts of the Leiden group that gives an access to the preparation of site directed high level isotope enrichment in retinals. First the synthesis of the retinals with deuterium incorporation in the conjugated side chain is reviewed. Then, 13C-labeled retinals are discussed. This is followed by the discussion of a convergent synthetic scheme that allows a rational access to prepare any isotopomer of retinals. The schemes that provide access to prepare any possible isotope enriched chemically modified systems are discussed. Finally, nor-retinals and bridged retinals that give access to a whole (as yet incomplete) library of possible isotopomers are reviewed. Full article
(This article belongs to the Special Issue Vitamins)
Open AccessReview Gene-Regulatory Activity of α-Tocopherol
Molecules 2010, 15(3), 1746-1761; doi:10.3390/molecules15031746
Received: 28 January 2010 / Revised: 5 March 2010 / Accepted: 9 March 2010 / Published: 12 March 2010
Cited by 34 | PDF Full-text (404 KB)
Abstract
Vitamin E is an essential vitamin and a lipid soluble antioxidant, at least, under in vitro conditions. The antioxidant properties of vitamin E are exerted through its phenolic hydroxyl group, which donates hydrogen to peroxyl radicals, resulting in the formation of stable [...] Read more.
Vitamin E is an essential vitamin and a lipid soluble antioxidant, at least, under in vitro conditions. The antioxidant properties of vitamin E are exerted through its phenolic hydroxyl group, which donates hydrogen to peroxyl radicals, resulting in the formation of stable lipid species. Beside an antioxidant role, important cell signalling properties of vitamin E have been described. By using gene chip technology we have identified α-tocopherol sensitive molecular targets in vivo including christmas factor (involved in the blood coagulation) and 5α-steroid reductase type 1 (catalyzes the conversion of testosterone to 5α-dihydrotestosterone) being upregulated and γ-glutamyl-cysteinyl synthetase (the rate limiting enzyme in GSH synthesis) being downregulated due to a-tocopherol deficiency. α-Tocopherol regulates signal transduction cascades not only at the mRNA but also at the miRNA level since miRNA 122a (involved in lipid metabolism) and miRNA 125b (involved in inflammation) are downregulated by α-tocopherol. Genetic polymorphisms may determine the biological and gene-regulatory activity of a-tocopherol. In this context we have recently shown that genes encoding for proteins involved in peripheral α-tocopherol transport and degradation are significantly affected by the apoE genotype. Full article
(This article belongs to the Special Issue Vitamins)
Open AccessReview Vitamins and Prostate Cancer Risk
Molecules 2010, 15(3), 1762-1783; doi:10.3390/molecules15031762
Received: 1 February 2010 / Revised: 5 March 2010 / Accepted: 10 March 2010 / Published: 12 March 2010
Cited by 7 | PDF Full-text (173 KB)
Abstract
Prostate cancer (PC) is the second most common cancer in men worldwide. Its prevention and treatment remain a challenge to clinicians. Here we review the relationship of vitamins to PC risk. Many vitamins and related chemicals, including vitamin A, retinoids, several B [...] Read more.
Prostate cancer (PC) is the second most common cancer in men worldwide. Its prevention and treatment remain a challenge to clinicians. Here we review the relationship of vitamins to PC risk. Many vitamins and related chemicals, including vitamin A, retinoids, several B vitamins, vitamin C, vitamin D and vitamin E have shown their anti-cancer activities as anti-oxidants, activators of transcription factors or factors influencing epigenetic events. Although laboratory tests including the use of animal models showed these vitamins may have anti-PC properties, whether they can effectively prevent the development and/or progression of PC in humans remains to be intensively studied subjects. This review will provide up-to-date information regarding the recent outcomes of laboratory, epidemiology and/or clinical trials on the effects of vitamins on PC prevention and/or treatment. Full article
(This article belongs to the Special Issue Vitamins)
Open AccessReview Vitamin K2 in Electron Transport System: Are Enzymes Involved in Vitamin K2 Biosynthesis Promising Drug Targets?
Molecules 2010, 15(3), 1531-1553; doi:10.3390/molecules15031531
Received: 21 December 2009 / Revised: 11 February 2010 / Accepted: 3 March 2010 / Published: 10 March 2010
Cited by 22 | PDF Full-text (654 KB)
Abstract
Aerobic and anaerobic respiratory systemsallow cells to transport the electrons to terminal electron acceptors. The quinone (ubiquinone or menaquinone) pool is central to the electron transport chain. In the majority of Gram-positive bacteria, vitamin K2 (menaquinone) is the sole quinone in [...] Read more.
Aerobic and anaerobic respiratory systemsallow cells to transport the electrons to terminal electron acceptors. The quinone (ubiquinone or menaquinone) pool is central to the electron transport chain. In the majority of Gram-positive bacteria, vitamin K2 (menaquinone) is the sole quinone in the electron transport chain, and thus, the bacterial enzymes catalyzing the synthesis of menaquinone are potential targets for the development of novel antibacterial drugs. This manuscript reviews the role of vitamin K in bacteria and humans, and especially emphasizes on recent aspects of menaquinones in bacterial electron transport chain and on discoveries of inhibitor molecules targeting bacterial electron transport systems for new antibacterial agents. Full article
(This article belongs to the Special Issue Vitamins)
Open AccessReview Vitamin B6: A Molecule for Human Health?
Molecules 2010, 15(1), 442-459; doi:10.3390/molecules15010442
Received: 5 November 2009 / Revised: 16 January 2010 / Accepted: 20 January 2010 / Published: 20 January 2010
Cited by 35 | PDF Full-text (634 KB)
Abstract
Vitamin B6 is an intriguing molecule that is involved in a wide range of metabolic, physiological and developmental processes. Based on its water solubility and high reactivity when phosphorylated, it is a suitable co-factor for many biochemical processes. Furthermore the vitamin [...] Read more.
Vitamin B6 is an intriguing molecule that is involved in a wide range of metabolic, physiological and developmental processes. Based on its water solubility and high reactivity when phosphorylated, it is a suitable co-factor for many biochemical processes. Furthermore the vitamin is a potent antioxidant, rivaling carotenoids or tocopherols in its ability to quench reactive oxygen species. It is therefore not surprising that the vitamin is essential and unquestionably important for the cellular metabolism and well-being of all living organisms. The review briefly summarizes the biosynthetic pathways of vitamin B6 in pro- and eukaryotes and its diverse roles in enzymatic reactions. Finally, because in recent years the vitamin has often been considered beneficial for human health, the review will also sum up and critically reflect on current knowledge how human health can profit from vitamin B6. Full article
(This article belongs to the Special Issue Vitamins)
Open AccessReview The Vitamin Nicotinamide: Translating Nutrition into Clinical Care
Molecules 2009, 14(9), 3446-3485; doi:10.3390/molecules14093446
Received: 17 August 2009 / Revised: 8 September 2009 / Accepted: 8 September 2009 / Published: 9 September 2009
Cited by 87 | PDF Full-text (790 KB)
Abstract
Nicotinamide, the amide form of vitamin B3 (niacin), is changed to its mononucleotide compound with the enzyme nicotinic acide/nicotinamide adenylyltransferase, and participates in the cellular energy metabolism that directly impacts normal physiology. However, nicotinamide also influences oxidative stress and modulates multiple [...] Read more.
Nicotinamide, the amide form of vitamin B3 (niacin), is changed to its mononucleotide compound with the enzyme nicotinic acide/nicotinamide adenylyltransferase, and participates in the cellular energy metabolism that directly impacts normal physiology. However, nicotinamide also influences oxidative stress and modulates multiple pathways tied to both cellular survival and death. During disorders that include immune system dysfunction, diabetes, and aging-related diseases, nicotinamide is a robust cytoprotectant that blocks cellular inflammatory cell activation, early apoptotic phosphatidylserine exposure, and late nuclear DNA degradation. Nicotinamide relies upon unique cellular pathways that involve forkhead transcription factors, sirtuins, protein kinase B (Akt), Bad, caspases, and poly (ADP-ribose) polymerase that may offer a fine line with determining cellular longevity, cell survival, and unwanted cancer progression. If one is cognizant of the these considerations, it becomes evident that nicotinamide holds great potential for multiple disease entities, but the development of new therapeutic strategies rests heavily upon the elucidation of the novel cellular pathways that nicotinamide closely governs. Full article
(This article belongs to the Special Issue Vitamins)

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