Het rijke werkingsveld van tocolen

4 februari 2019

Door: Brigitte Baumeister

In 1922 ontdekten de wetenschappers Evans en Bishop de vet-oplosbare vitamine E als essentiële voedingsstof voor de vruchtbaarheid.13 Haar antioxidantfunctie werd vastgesteld door Mattill.14 Veel later bleek dat ze ook een rol heeft bij het tot uiting komen van genetische eigenschappen, de signaalwerking binnen cellen en van cellulaire functies in het algemeen.15 Wat wij doorgaans vitamine E noemen is een hele reeks tocolen, vaak met opmerkelijke eigenschappen.

Vitamine E is de verzamelnaam voor acht tocolen. Dat zijn alfa(α)-tocoferol, bèta(β)-tocoferol, gamma(ƴ)-tocoferol en delta(δ)-tocoferol en alfa-tocotriënol, beta-tocotriënol, gamma-tocotriënol en delta-tocotriënol. Van deze acht wordt alfa-tocoferol doorgaans vitamine E genoemd.
Tocolen worden geproduceerd en opgeslagen in bladeren van planten, noten en zaden, waaruit spijsoliën worden gewonnen.2,3 Alfa-tocoferol (α-T) is vooral aanwezig in onder andere amandel-,16 pinda-,17 olijf-18 en zonnebloemolie.19 Het gehalte aan ƴ-T in koolzaad-, maïs-, camelina-, lijnzaad-, soja- en walnootolie is echter gelijk aan of hoger dan dat van α-T.2, 20, 21 Palmolie, de belangrijkste spijsolie ter wereld,22 bevat, behalve α-T, drie tocotriënolen (T3’s), namelijk α-, ƴ- en δ-tocotriënol.23 T3’s komen het meest voor in rijstzemelen, palm- en annatto-oliën. Andere bronnen van T3’s zijn rogge, amaranth, walnoot, hazelnoot, papaver, saffloer, maïs, vlaszaad, druiven-en pompoenpitten.24 Tabel 1 geeft een overzicht van de concentratie T’s en T3’s in spijsoliën.2

Qua chemische structuur hebben alle tocolen één chromanolring (bestaande uit zes C-atomen en een OH-groep) en een zijketen. Maar, in tegenstelling tot de T’s, hebben de T3’s drie dubbele bindingen in hun zijketen. Bovendien zijn er zowel bij de T’s als T3’s verschillen in aantal en plaats van hun methylgroepen. Deze komen tot uiting in de toevoegingen α-, β-, ƴ- en δ- (zie figuur 1).25,26

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Bronvermelding:

  1. Kanchi MM, Shanmugam MK, Rane G, Sethi G, Kumar AP. Tocotrienols: the unsaturated sidekick shifting new paradigms in vitamin E therapeutics. Drug Discovery Today. 2017;22(12):1765-81.
  2. Shahidi F, de Camargo AC. Tocopherols and Tocotrienols in Common and Emerging Dietary Sources: Occurrence, Applications, and Health Benefits. International Journal of Molecular Sciences. 2016;17(10):1745.
  3. Azzi A. Many tocopherols, one vitamin E. Molecular Aspects of Medicine. 2018;61:92-103.
  4. European Food Safety A. Dietary Reference Values for nutrients Summary report. EFSA Supporting Publications. 2017;14(12):e15121E-n/a.
  5. Rink C, Christoforidis G, Khanna S, Peterson L, Patel Y, Khanna S, et al. Tocotrienol vitamin E protects against preclinical canine ischemic stroke by inducing arteriogenesis. Journal of Cerebral Blood Flow & Metabolism. 2011;31(11):2218-30.
  6. Khanna S, Roy S, Slivka A, Craft TK, Chaki S, Rink C, et al. Neuroprotective properties of the natural vitamin E α-tocotrienol. Stroke. 2005;36(10):e144-e52.
  7. Jiang Q. Natural Forms of Vitamin E as Effective Agents for Cancer Prevention and Therapy. Advances in Nutrition. 2017;8(6):850-67.
  8. Yu W, Park S-K, Jia L, Tiwary R, Scott WW, Li J, et al. RRR-γ-tocopherol induces human breast cancer cells to undergo apoptosis via death receptor 5 (DR5)-mediated apoptotic signaling. Cancer letters. 2008;259(2):165-76.
  9. Smolarek AK, So JY, Burgess B, Kong A-NT, Reuhl K, Lin Y, et al. Dietary administration of δ-and γ-tocopherol inhibits tumorigenesis in the animal model of estrogen receptor–positive, but not HER-2 breast cancer. Cancer Prevention Research. 2012.
  10. Guan F, Li G, Liu B, Lee M-J, Yang Z, Chen Y-K, et al. δ-and γ-tocopherols, but not α-tocopherol, inhibit colon carcinogenesis in azoxymethane-treated F344 rats. Cancer Prevention Research. 2012:canprevres. 0521.2011.
  11. Li G-X, Lee M-J, Liu AB, Yang Z, Lin Y, Shih WJ, et al. δ-tocopherol is more active than α-or γ-tocopherol in inhibiting lung tumorigenesis in vivo. Cancer Prevention Research. 2011;4(3):404-13.
  12. Wang H, Hong J, Yang CS. δ‐Tocopherol inhibits receptor tyrosine kinase‐induced AKT activation in prostate cancer cells. Molecular carcinogenesis. 2016;55(11):1728-38.
  13. Evans HM, Bishop KS. On the existence of a hitherto unrecognized dietary factor essential for reproduction. Science. 1922;56(1458):650-1.
  14. Wolf G. The discovery of the antioxidant function of vitamin E: the contribution of Henry A. Mattill. The Journal of nutrition. 2005;135(3):363-6.
  15. Zingg J-M. Modulation of signal transduction by vitamin E. Molecular aspects of medicine. 2007;28(5-6):481-506.
  16. Kornsteiner M, Wagner K-H, Elmadfa I. Tocopherols and total phenolics in 10 different nut types. Food chemistry. 2006;98(2):381-7.
  17. de Camargo AC, Vieira TMFdS, Regitano-D’Arce MAB, de Alencar SM, Calori-Domingues MA, Canniatti-Brazaca SG. Gamma radiation induced oxidation and tocopherols decrease in in-shell, peeled and blanched peanuts. International journal of molecular sciences. 2012;13(3):2827-45.
  18. Caporaso N, Savarese M, Paduano A, Guidone G, De Marco E, Sacchi R. Nutritional quality assessment of extra virgin olive oil from the Italian retail market: Do natural antioxidants satisfy EFSA health claims? Journal of Food Composition and Analysis. 2015;40:154-62.
  19. Karmowski J, Hintze V, Kschonsek J, Killenberg M, Böhm V. Antioxidant activities of tocopherols/tocotrienols and lipophilic antioxidant capacity of wheat, vegetable oils, milk and milk cream by using photochemiluminescence. Food chemistry. 2015;175:593-600.
  20. Schwartz H, Ollilainen V, Piironen V, Lampi A-M. Tocopherol, tocotrienol and plant sterol contents of vegetable oils and industrial fats. Journal of Food Composition and Analysis. 2008;21(2):152-61.
  21. Grilo EC, Costa PN, Gurgel CSS, Beserra AFdL, Almeida FNdS, Dimenstein R. Alpha-tocopherol and gamma-tocopherol concentration in vegetable oils. Food Science and Technology (Campinas). 2014;34(2):379-85.
  22. Carter C, Finley W, Fry J, Jackson D, Willis L. Palm oil markets and future supply. European Journal of Lipid Science and Technology. 2007;109(4):307-14.
  23. Chun J, Lee J, Ye L, Exler J, Eitenmiller RR. Tocopherol and tocotrienol contents of raw and processed fruits and vegetables in the United States diet. Journal of Food Composition and Analysis. 2006;19(2-3):196-204.
  24. Kannappan R, Gupta SC, Kim JH, Aggarwal BB. Tocotrienols fight cancer by targeting multiple cell signaling pathways. Genes & nutrition. 2012;7(1):43.
  25. Rimbach G, Moehring J, Huebbe P, Lodge JK. Gene-regulatory activity of α-tocopherol. Molecules. 2010;15(3):1746-61.
  26. Birringer M, Pfluger P, Kluth D, Landes N, Brigelius-Flohe R. Identities and differences in the metabolism of tocotrienols and tocopherols in HepG2 cells. The Journal of nutrition. 2002;132(10):3113-8.
  27. Burton GW, Traber MG, Acuff RV, Walters DN, Kayden H, Hughes L, et al. Human plasma and tissue alpha-tocopherol concentrations in response to supplementation with deuterated natural and synthetic vitamin E. The American journal of clinical nutrition. 1998;67(4):669-84.
  28. Shahidi F, Ambigaipalan P. Phenolics and polyphenolics in foods, beverages and spices: Antioxidant activity and health effects–A review. Journal of functional foods. 2015;18:820-97.
  29. Krumova K, Friedland S, Cosa G. How lipid unsaturation, peroxyl radical partitioning, and chromanol lipophilic tail affect the antioxidant activity of α-tocopherol: Direct visualization via high-throughput fluorescence studies conducted with fluorogenic α-tocopherol analogues. Journal of the American Chemical Society. 2012;134(24):10102-13.
  30. Thoo YY, Abas F, Lai O-M, Ho CW, Yin J, Hedegaard RV, et al. Antioxidant synergism between ethanolic Centella asiatica extracts and α-tocopherol in model systems. Food chemistry. 2013;138(2-3):1215-9.
  31. Salah N, Miller NJ, Paganga G, Tijburg L, Bolwell GP, Riceevans C. Polyphenolic flavanols as scavengers of aqueous phase radicals and as chain-breaking antioxidants. Archives of biochemistry and biophysics. 1995;322(2):339-46.
  32. Jiang Q, Christen S, Shigenaga MK, Ames BN. γ-Tocopherol, the major form of vitamin E in the US diet, deserves more attention–. The American journal of clinical nutrition. 2001;74(6):714-22.
  33. Jiang Q. Natural forms of vitamin E: metabolism, antioxidant, and anti-inflammatory activities and their role in disease prevention and therapy. Free Radical Biology and Medicine. 2014;72:76-90.
  34. Chung S, Ghelfi M, Atkinson J, Parker R, Qian J, Carlin C, et al. Vitamin E and Phosphoinositides Regulate the Intracellular Localization of the Hepatic α-Tocopherol Transfer Protein. The Journal of Biological Chemistry. 2016;291(33):17028-39.
  35. Mariotti C, Gellera C, Rimoldi M, Mineri R, Uziel G, Zorzi G, et al. Ataxia with isolated vitamin E deficiency: neurological phenotype, clinical follow-up and novel mutations in TTPAgene in Italian families. Neurological sciences. 2004;25(3):130-7.
  36. Pryor WA. Vitamin E and heart disease:: Basic science to clinical intervention trials. Free Radical Biology and Medicine. 2000;28(1):141-64.
  37. Traber MG. Vitamin E Inadequacy in Humans: Causes and Consequences. Advances in Nutrition. 2014;5(5):503-14.
  38. Zingg J-M, Han SN, Pang E, Meydani M, Meydani SN, Azzi A. In vivo regulation of gene transcription by alpha-and gamma-tocopherol in murine T lymphocytes. Archives of biochemistry and biophysics. 2013;538(2):111-9.
  39. Zingg J-M, Azzi A. Non-antioxidant activities of vitamin E. Current medicinal chemistry. 2004;11(9):1113-33.
  40. Pryor WA. The antioxidant nutrients and disease prevention-what do we know and what do we need to find out? 1’2. 1991.
  41. Zingg J-M, Libinaki R, Meydani M, Azzi A. Modulation of phosphorylation of tocopherol and phosphatidylinositol by hTAP1/SEC14L2-mediated lipid exchange. PloS one. 2014;9(7):e101550.
  42. Patel V, Rink C, Gordillo GM, Khanna S, Gnyawali U, Roy S, et al. Oral Tocotrienols Are Transported to Human Tissues and Delay the Progression of the Model for End-Stage Liver Disease Score in Patients–4. The Journal of nutrition. 2012;142(3):513-9.
  43. Singh VK, Beattie LA, Seed TM. Vitamin E: tocopherols and tocotrienols as potential radiation countermeasures. Journal of Radiation Research. 2013;54(6):973-88.
  44. Saito Y, Yoshida Y, Nishio K, Hayakawa M, Niki E. Characterization of cellular uptake and distribution of vitamin E. Annals of the New York Academy of Sciences. 2004;1031(1):368-75.
  45. Serbinova EA, Packer L. [34] Antioxidant properties of α-tocopherol and α-tocotrienol. Methods in enzymology. 234: Elsevier; 1994. p. 354-66.
  46. Tsuzuki W, Yunoki R, Yoshimura H. Intestinal Epithelial Cells Absorb γ‐Tocotrienol Faster than α‐Tocopherol. Lipids. 2007;42(2):163.
  47. Azzi A, Boscoboinik D, Clément S, Özer N, Ricciarelli R, Stocker A. Vitamin E mediated response of smooth muscle cell to oxidant stress. Diabetes research and clinical practice. 1999;45(2-3):191-8.
  48. Meydani M. Vitamin E and atherosclerosis: beyond prevention of LDL oxidation. The Journal of nutrition. 2001;131(2):366S-8S.
  49. Parker RA, Pearce B, Clark R, Gordon D, Wright J. Tocotrienols regulate cholesterol production in mammalian cells by post-transcriptional suppression of 3-hydroxy-3-methylglutaryl-coenzyme A reductase. Journal of Biological Chemistry. 1993;268(15):11230-8.
  50. Khor H, Chieng D, Ong K. Tocotrienols inhibit liver HMG CoA reductase activity in the guinea pig. Nutrition Research. 1995;15(4):537-44.
  51. Meganathan P, Fu J-Y. Biological Properties of Tocotrienols: Evidence in Human Studies. International Journal of Molecular Sciences. 2016;17(11):1682.
  52. Goldstein JL, Brown MS. Regulation of the mevalonate pathway. Nature. 1990;343(6257):425.
  53. Qureshi AA, Qureshi N, Wright J, Shen Z, Kramer G, Gapor A, et al. Lowering of serum cholesterol in hypercholesterolemic humans by tocotrienols (palmvitee). The American journal of clinical nutrition. 1991;53(4):1021S-6S.
  54. Qureshi AA, Sami SA, Salser WA, Khan FA. Dose-dependent suppression of serum cholesterol by tocotrienol-rich fraction (TRF25) of rice bran in hypercholesterolemic humans. Atherosclerosis. 2002;161(1):199-207.
  55. Yuen KH, Wong JW, Lim AB, Ng BH, Choy WP. Effect of mixed-tocotrienols in hypercholesterolemic subjects. Functional Foods in Health and Disease. 2011;1(3):106-17.
  56. Wahlqvist ML, Krivokuca-Bogetic Z, Lo CS, Hage B, Smith R, Lukito W. Differential serum responses of tocopherols and tocotrienols during vitamin supplementation in hypercholesterolaemic individuals without change in coronary risk factors. Nutrition Research. 1992;12:S181-S201.
  57. Mensink RP, van Houwelingen AC, Kromhout D, Hornstra G. A vitamin E concentrate rich in tocotrienols had no effect on serum lipids, lipoproteins, or platelet function in men with mildly elevated serum lipid concentrations–. The American journal of clinical nutrition. 1999;69(2):213-9.
  58. Rasool AH, Yuen KH, Yusoff K, Wong AR, Rahman AR. Dose dependent elevation of plasma tocotrienol levels and its effect on arterial compliance, plasma total antioxidant status, and lipid profile in healthy humans supplemented with tocotrienol rich vitamin E. Journal of nutritional science and vitaminology. 2006;52(6):473-8.
  59. Chin S-F, Ibahim J, Makpol S, Hamid NAA, Latiff AA, Zakaria Z, et al. Tocotrienol rich fraction supplementation improved lipid profile and oxidative status in healthy older adults: A randomized controlled study. Nutrition & metabolism. 2011;8(1):42.
  60. Georgousopoulou EN, Panagiotakos DB, Mellor DD, Naumovski N. Tocotrienols, health and ageing: A systematic review. Maturitas. 2017;95:55-60.
  61. Miller ER, Pastor-Barriuso R, Dalal D, Riemersma RA, Appel LJ, Guallar E. Meta-analysis: high-dosage vitamin E supplementation may increase all-cause mortality. Annals of internal medicine. 2005;142(1):37-46.
  62. Galli F, Azzi A, Birringer M, Cook-Mills JM, Eggersdorfer M, Frank J, et al. Vitamin E: Emerging aspects and new directions. Free Radical Biology and Medicine. 2017;102(Supplement C):16-36.
  63. Lonn E, Bosch J, Yusuf S, Sheridan P, Pogue J, Arnold J, et al. Effects of long-term vitamin E supplementation on cardiovascular events and cancer: a randomized controlled trial. Jama. 2005;293(11):1338-47.
  64. Rondanelli M, Faliva MA, Peroni G, Moncaglieri F, Infantino V, Naso M, et al. Focus on pivotal role of dietary intake (diet and supplement) and blood levels of tocopherols and tocotrienols in obtaining successful aging. International journal of molecular sciences. 2015;16(10):23227-49.