what is tocotrienol?

What is Tocotrienol?

Tocotrienol is one of two major subgroups of the vitamin E family, the other being the more well-known tocopherols. Each subgroup contains four structurally and chemically diverse molecules: alpha, beta, gamma, and delta. In nature, tocotrienol is derived from plant sources that include annatto, palm, and rice bran oil.

How Does It Work?

Although at first glance, the vitamin E particles appear the same, nuances in their molecular framework set them apart. While both are exceptional antioxidants, only tocotrienol is more flexible due to three double bonds in the tail region of the molecule, resulting in benefits other than protection from oxidation. Furthermore, smaller tocotrienol molecules, namely delta- and gamma-tocotrienol, were shown to be most potent for most applications, since their small size allows easier access to cell membranes to more readily quench free radicals.

Three Sources of Tocotrienol

Until 2003, the only commercial sources of natural tocotrienol were palm and rice. Hence, early studies utilized tocotrienol derived from these two sources. Both sources, however, contain significant amounts of alpha-tocopherol, which was established to interfere with tocotrienol benefits. “Palm tocotrienol” and “rice tocotrienol”, also sometimes called tocotrienol-rich fraction (TRF), are actually mixtures of tocopherol and tocotrienol, typically containing 25-50% tocopherol (mostly as alpha-tocopherol).
Annatto naturally provides only the most potent delta- and gamma-tocotrienol while being tocopherol-free, a composition never before seen.

Why Is Tocopherol-Free Important?

Tocopherol interferes with tocotrienol benefits. For the first time in 1996, the cholesterol-modulating properties of tocotrienol were found to be compromised by one of its very own vitamin E siblings, alpha-tocopherol [1]. The researchers concluded that effective tocotrienol preparations should contain less than 15% of alpha-tocopherol and more than 60% of desmethyl tocotrienols (gamma- and delta-tocotrienol). The only natural source of tocotrienols that fits this prerequisite is annatto, which is essentially tocopherol free and contains only the most potent delta- and gamma-tocotrienols (90% and 10%, respectively).  Today, more research is confirming that alpha-tocopherol interferes with tocotrienol benefits, both directly [1-6] and indirectly [1, 4, 7-11].

Benefits

As part of the vitamin E family, tocotrienol is a superb antioxidant. Lipid oxygen radical absorbance capacity (L-ORAC) studies point to delta-tocotrienol as the most potent antioxidant of the vitamin E series, followed by gamma-tocotrienol and delta- and gamma-tocopherols [12].

Aside from antioxidant benefits, research since the early 80s has repeatedly indicated that delta- and gamma-tocotrienol help in the maintenance of cholesterol levels that are already within the normal range [13-19].
As numerous new studies are published, tocotrienol reaches a new measure of research height, pointing towards promising benefits for overall optimum health and aging.

Vitamin E History

Herbert McLean Evans and Katherine Bishop discovered vitamin E in 1922 [20] as a vital nutrient to prevent birth defects. However, it was not until the late 1950s that the scientific community became aware that the vitamin E family consists of two major subgroups, namely tocopherols and tocotrienols. In 1936, vitamin E was first isolated from wheat germ oil [22]. While commercialization of natural soy-derived tocopherols began in the 1950s, tocotrienols were only recently brought to the market, starting with products derived from palm in 1992, rice in 1999, and finally annatto in 2003.
Today, American River Nutrition, Inc. is the only manufacturer of natural annatto-derived tocotrienols that are free of tocopherols.


References

1.            Qureshi, A.A., et al., Dietary alpha-tocopherol attenuates the impact of gamma-tocotrienol on hepatic 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in chickens. J Nutr, 1996. 126(2): p. 389-94.

2.            Guthrie, N., et al., Inhibition of proliferation of estrogen receptor-negative MDA-MB-435 and -positive MCF-7 human breast cancer cells by palm oil tocotrienols and tamoxifen, alone and in combination. J Nutr, 1997. 127: p. 544S-548S.

3.            Ikeda, S., et al., Dietary alpha-tocopherol decreases alpha-tocotrienol but not gamma-tocotrienol concentration in rats. J Nutr, 2003. 133(2): p. 428-34.

4.            Khor, H.T. and T.T. Ng, Effects of administration of alpha-tocopherol and tocotrienols on serum lipids and liver HMG CoA reductase activity. Int J Food Sci Nutr, 2000. 51 Suppl: p. S3-11.

5.            Shibata, A., et al., alpha-Tocopherol attenuates the cytotoxic effect of delta-tocotrienol in human colorectal adenocarcinoma cells. Biochem Biophys Res Commun, 2010.

6.            Sontag, T.J. and R.S. Parker, Influence of major structural features of tocopherols and tocotrienols on their omega-oxidation by tocopherol-omega-hydroxylase. J Lipid Res, 2007. 48(5): p. 1090-8.

7.            Brigelius-Flohe, R., Induction of drug metabolizing enzymes by vitamin E. J Plant
Physiol, 2005. 162(7): p. 797-802.

8.            Brigelius-Flohe, R., Adverse effects of vitamin E by induction of drug metabolism. Genes Nutr, 2007. 2(3): p. 249-56.

9.            Fujita, K., et al., Vitamin E decreases bone mass by stimulating osteoclast fusion. Nat Med, 2012. 18(4): p. 589-94.

10.          Klein, E.A., et al., Vitamin E and the risk of prostate cancer: the Selenium and Vitamin E Cancer Prevention Trial (SELECT). Jama, 2011. 306(14): p. 1549-56.

11.          Miyamoto, K., et al., Very-high-dose alpha-tocopherol supplementation increases blood pressure and causes possible adverse central nervous system effects in stroke-prone spontaneously hypertensive rats. J Neurosci Res, 2009. 87(2): p. 556-66.

12.          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.

13.          Houston, M.C., et al., Nonpharmacologic treatment of dyslipidemia. Prog Cardiovasc Dis, 2009. 52(2): p. 61-94.

14.          Houston, M.C. and W. Sparks, Effect of combination pantethine, plant sterols, green tea extract, delta-tocotrienol and phytolens on lipid profiles in patients with hyperlipidemia. JANA, 2010. 13(1): p. 15-20.

15.          Pearce, B.C., et al., Hypocholesterolemic activity of synthetic and natural tocotrienols. J Med Chem, 1992. 35(20): p. 3595-606.

16.          Qureshi, A.A., et al., Suppression of Nitric Oxide Production and Cardiovascular Risk Factors in Healthy Seniors and Hypercholesterolemic Subjects by a Combination of Polyphenols and Vitamins. J Clin Exp Cardiolog, 2012. S5: p. 8.

17.          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.

18.          Yu, S.G., et al., Dose-response impact of various tocotrienols on serum lipid parameters in 5-week-old female chickens. Lipids, 2006. 41(5): p. 453-61.



19.          Zaiden, N., et al., Gamma delta tocotrienols reduce hepatic triglyceride synthesis and VLDL secretion. J Atheroscler Thromb, 2010. 17(10): p. 1019-32.

20.          Evans, H.M. and K.S. Bishop, On the existence of a hitherto unrecognized dietary factor essential for reproduction. Science, 1922. 56: p. 650-651.


21.          Evans, H.M., The isolation from wheat germ oil of an alcohol alpha-tocopherol, having the properties of vitamin E. J Bio Chem, 1936. 113: p. 319-332.

22.          Olcott, H.S. and O.H. Emerson, Antioxidants and autoxidation of fats: the antioxidant properties of tocopherols. J Am Chem Soc, 1937. 59: p. 1008-1009.