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The Different Forms of Vitamin E

Jun 24, 2016

Vitamin E was discovered in 1922 in green leafy vegetables by University of California researchers, Herbert Evans and Katherine Bishop. In 1924 it was named it vitamin E. It was not until the 1960s that tocotrienols were assessed to be part of the vitamin E family tree (4). Vitamin E is known as a “vitamin” because it is essential for reproduction, and sometimes dubbed as the “birth vitamin”. Its antioxidant activity was discovered earlier (1930s) (5).

Vitamin E is the term for a group of tocopherols and tocotrienols, of which alpha-tocopherol has the highest biological activity.   Tocotrienols are naturally derived from several sources, including rice bran, palm, and annatto.  Tocotrienols from current sources (rice, palm and annatto) were first developed and brought to the market by Dr. Barrie Tan, inventor of numerous tocotrienol extraction processes from natural sources. These discoveries include tocotrienols from palm (1992), then rice (1998), and finally annatto (2002). Tocotrienols are the primary form of vitamin E in the seed endosperm of most monocots, including agronomically important cereal grains such as wheat, rice, and barley. Tocotrienols are also found in the seed endosperm of a limited number of dicots, including Apiaceae species and certain Solanaeceae species, such as tobacco. These molecules are found only rarely in vegetative tissues of plants. Crude palm oil extracted from the fruits of Elaeis guineensis particularly contains a high amount of tocotrienols (up to 800 mg/kg), mainly consisting of γ- tocotrienol and α-tocotrienol. Tocopherols, by contrast, occur ubiquitously in plant tissues and are the exclusive form of vitamin E in leaves of plants and seeds of most dicots

 

Due to the potent antioxidant properties of tocopherols, the impact of α-tocopherol in the prevention of chronic diseases believed to be associated with oxidative stress has often been studied, and beneficial effects have been demonstrated.

Vitamin E is a potent lipid-soluble antioxidant that includes four tocopherals and four tocotrienols:

α-tocopherol
β-tocopherol
γ-tocopherol
δ-tocopherol

α-tocotrienol
β-tocotrienol
γ- tocotrienol
δ-tocotrienol

Vitamin E

α-Tocopherol gained recognition as the most important lipophilic antioxidant in tissues.  It was found that a deficiency of α-tocopherol made cellular membranes highly permeable and therefore vulnerable to degradation.  Fluidity of the membrane was influenced by α-Tocopherol in a similar way to that of cholesterol.  Studies of the antioxidant properties led to the recognition that α-tocopherol is only available as an antioxidant for a short period of time (25).  It was discovered however that Vitamin C That can regenerate α-tocopherol (26).   Studies demonstrated that maintenance of membrane tocopherol status may be an essential function of Vitamin C and ascorbate and Glutathione which operate in concert to ensure maximum membrane protection against oxidative damage (27).

The reaction kinetics and stability of the four tocopherols are not identical. The fast reacting α-tocopherol reacts more rapidly and traps free radicals more thoroughly and is only available as an antioxidant for a short period of time as compared with the slowly reacting δ-tocopherol. β- and γ-Tocopherols behave in an intermediate way (25).

Gamma-tocopherol has been proposed to have a distinct role other than just free radical scavenging.   In contrast to α-tocopherol, γ-tocopherol can donate electrons in order to trap electrophilic mutagens in lipophilic compartments (1-3). It thus complements glutathione, which similarly scavenges electrophilic mutagens in the aqueous phase of the cell.  γ-tocopherol protects lipids, DNA, and proteins from peroxynitrite dependent damage.  δ-tocotrienol has was the greatest antioxidant properties among the tocotrienol isomers (6), which is due to the molecule being more easily incorporated into cell membranes (7). A comparative in vitro study showed that γ- and δ-tocotrienol was 4-fold more efficient as scavenger of peroxyl radicals than other tocotrienol isomers (8).

The antioxidant efficiency of tocotrienols was evaluated as the ability of the compounds to inhibit lipid peroxidation, reactive oxygen species (ROS) production, and heat shock protein expression. δ-tocotrienol was found to have the greatest antioxidant properties among the tocotrienol isomers(9), which is due to the decreased methylation of the chromanol ring that allows the molecule to be more easily incorporated into cell membranes (10). A comparative in vitro study showed that γ- and delta- tocotrienol was 4-fold more efficient as a scavenger of peroxyl radicals than other tocotrienol isomers (11). In lipid ORAC studies, delta- and γ-tocotrienols had the highest antioxidant value of all vitamin E isomers at 5.5x and 3x the potency of alpha-tocopherol, respectively. Interestingly, δ- and γ- tocopherol were also strong antioxidants (12)

Tocotrienol’s Protective Effect on Skin: Vitamin E, and in particular delta- and γ-tocotrienol and tocotrienol-rich fractions (TRF), have been shown to be superior protectors against environmental stressors such as UV-irradiation of the skin (13). TRF has significantly higher potency than alpha- tocopherol, and is effective against protein oxidation and lipid peroxidation at low concentrations (14,15). Normally, UV-irradiation destroys the antioxidants of the skin, but prior application of TRF to mouse skin preserved the vitamin E (16). Also, the largest fraction of vitamin E was found in the subcutaneous layer of the skin, which shows that applied vitamin E penetrates rapidly through the skin (17), and therefore combats oxidative stress induced by UV or ozone efficiently (18). In addition, delta- and γ- tocotrienol have been shown to reduce inflammation (19-21), and are potent skin whitening agents via reduction of tyrosinase activity, while also blocking UV-induced melanogenesis (22). δ-tocotrienol has the greatest sun protection factor (SPF) of the tocotrienol isomers at SPF 5.5 (22).

Angiogenesis Inhibition: Recent studies showed that tocotrienols but not tocopherols inhibit abnormal angiogenesis, an indispensable step in tumor growth or progression beyond 1mm. Vascular endothelial growth factor (VEGF) regulates angiogenesis by binding to VEGF receptor (VEGFR) in endothelial cells. Tocotrienol downregulates VEGFR, therefore blocking intracellular signaling of VEGF and inhibiting angiogenesis (23). In addition, tocotrienol inhibits the proliferation and formation of tubes by bovine aortic endothelial cells, where delta-tocotrienol had the strongest inhibitory activity (24). Since angiogenesis is essential to tumor growth and this kind of angiogenesis is abnormal or aberrant, its inhibition likely stunts tumor growth and prevents cancer metastasis.

As you can see Tocopherol has many benefits.  There is one myth however that I want to address and that is that Vitamin E is good for scars and helps prevent them.  This is not true.  In fact the opposite is true.  A double-blinded, controlled study illustrated that treatment of scars with topical vitamin E did not help in scar reduction but was associated with an increased incidence of contact dermatitis.  The study showed that there is no benefit to the cosmetic outcome of scars by applying vitamin E after skin surgery and that the application of topical vitamin E may actually be detrimental to the cosmetic appearance of a scar. In 90% of the cases in this study, topical vitamin E either had no effect on, or actually worsened, the cosmetic appearance of scars.

Vitamin E has many benefits for skin care when used along with other antioxidants in a formula.  Use of Vitamin E Oil by itself should be avoided.

 

About the Author

Jacine Greenwood

Jacine Greenwood is an internationally recognised educator who is known within the industry for her up to date knowledge and her ability to deliver training in an easy to understand method.

Jacine holds 6 Diplomas and a Bachelor of Nursing and her knowledge is well respected by her peers.  With over 21 years experience in the industry and a background of cosmetic formulation, Jacine has an immense knowledge of current trends in research and new developments in the industry.

Jacine has been continually educating herself in all aspects of skin function and cosmetic chemistry for the past 21 years.  Jacine’s knowledge is current and has a vast knowledge of the active ingredients that are being released onto the market.

 
References:
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  2. Cooney, R. V., Harwood, P. J., Franke, A. A., Narala, K., Sundstrom, A. K., Berggren, P. O., and Mordan, L. J. (1995) Products of gamma-tocopherol reaction with NO2 and their formation in rat insulinoma (RINm5F) cells. Free Rad. Biol. Med. 19, 259 –269.
  3. Christen, S., Woodall, A. A., Shigenaga, M. K., Southwell-Keely, P. T., Duncan, M. W., and Ames, B. N. (1997) -Tocopherol traps mutagenic electrophiles such as NOx and complements -tocopherol: physiological implications. Proc. Natl. Acad. Sci. USA 94, 3217–3222
  4. Pennock, J.F., F.W. Hemming, and J.D. Kerr, A reassessment of tocopherol in chemistry. Biochem Biophys Res Commun, 1964. 17(5): p. 542-8.
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  6. Muller, L., K. Theile, and V. Bohm, In vitro antioxidant activity of tocopherols and tocotrienols and comparison of vitamin E concentration and lipophilic antioxidant capacity in human plasma. Mol Nutr Food Res, 2010. 54(5): p. 731-42.
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  8. Kim, H.J. and D.B. Min, Effects, quenching mechanisms, and kinetics of alpha-, beta-, gamma-, and delta-tocotrienol on chlorophyll photosynthesized oxidation of lard., in IFT. 2007.
  9. Palozza, P., et al., Comparative antioxidant activity of tocotrienols and the novel chromanyl- polyisoprenyl molecule FeAox-6 in isolated membranes and intact cells. Mol Cell Biochem, 2006. 287(1-2): p. 21-32.
  10. Tan, B., Appropriate spectrum vitamin E and new perspectives on desmethyl tocopherols and tocotrienols. JANA, 2005. 8(1): p. 35-42.
  11. Qureshi, A.A. and H. Mo, Isolation and structural identification of novel tocotrienols from rice bran with hypocholesterolemic, antioxidant and antitumor properties. J Agric Food Chem, 2000(131): p. 223-230.
  12. Traber, M.G., et al., Diet-derived and topically applied tocotrienols accumulate in skin and protect the tissue against ultraviolet light-induced oxidative stress. Asia Pac J Clin Nutr, 1997. 6(1): p. 63-67.
  13. Kamat, J.P., et al., Tocotrienols from palm oil as effective inhibitors of protein oxidation and lipid peroxidation in rat liver microsomes. Mol Cell Biochem, 1997. 170(1-2): p. 131-7.
  14. Mutalib, M.S.A., H. Khaza'ai, and K.W.J. Wahle, Palm-tocotrienol rich fraction (TRF) is a more effective inhibitor of LDL oxidation and endothelial cell lipid peroxidation than alpha-tocopherol in vitro. Food Res. Int., 2003(36): p. 405-413.
  15. Weber, C., et al., Efficacy of topically applied tocopherols and tocotrienols in protection of murine skin from oxidative damage induced by UV-irradiation. Free Radic Biol Med, 1997. 22(5): p. 761-9.
  16. Traber, M.G., et al., Penetration and distribution of alpha-tocopherol, alpha- or gamma-tocotrienols applied individually onto murine skin. Lipids, 1998. 33(1): p. 87-91.
  17. Packer, L., S.U. Weber, and G. Rimbach, Molecular aspects of alpha-tocotrienol antioxidant action and cell signalling. J Nutr, 2001. 131(2): p. 369S-73S.
  18. Qureshi, A.A., et al., Tocotrienols inhibit lipopolysaccharide-induced pro-inflammatory cytokines in macrophages of female mice. Lipids Health Dis, 2011. 9(1): p. 143.
  19. Qureshi, A.A., et al., delta-Tocotrienol and quercetin reduce serum levels of nitric oxide and lipid parameters in female chickens. Lipids Health Dis, 2011. 10: p. 39.
  20. Yam, M.L., et al., Tocotrienols suppress proinflammatory markers and cyclooxygenase-2 expression in RAW264.7 macrophages. Lipids, 2009. 44(9): p. 787-97.
  21. Yap, W.N., et al., Gamma- and delta-tocotrienols inhibit cutaneous melanosis (hallmark of melanoma) by suppressing constitutive and UV-induced tyrosinase activation., in 102nd Annual Meeting of the American Association for Cancer Research. 2011: Orlando, FL.
  22. He, L., et al., Isoprenoids suppress the growth of murine B16 melanomas in vitro and in vivo. JNutr, 1997. 127(5): p. 668-74.
  23. Mizushina, Y., et al., Inhibitory effect of tocotrienol on eukaryotic DNA polymerase lambda and angiogenesis. Biochem Biophys Res Commun, 2006. 339(3): p. 949-55.
  24. Lambelet P, Loliger J. The fate of antioxidant radicals during lipid autooxidation. I. The tocopheroxyl radicals. Chem Phys Lipids 1984;35 (3):185–198.

  25. Baumann LS, Spencer, J. The effects of topical Vitamin E on the cosmetic appearance of scars.  Dermatol Surg. 1999 Apr; 25 (4):311-5.

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