Tocotrienols

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Tocotrienols (short T3 or TCT) hot four forms of vitamin E . They correspond to the tocopherols in the functional group (alpha-, beta-, gamma-, delta-) but have a triple unsaturated side chain. Tocotrienols basically act like vitamin E and as an antioxidant. They also have some functions that are not found in tocopherols.

Occurrence

Tocotrienols are widespread in plants and appear predominantly with other vitamin E analogs.

Foods high in tocotrienols are:

  • Clove oil (1073 mg / 100 g mainly as delta-tocotrienol)
  • Cranberry oil (170 mg / 100 g as alpha-tocotrienol)
  • Annattosaat (143 mg / 100 g, mainly as delta-tocotrienol)
  • Chinese horse chestnut (96 mg / 100 g)
  • Palm oil (red) (40–140 mg / 100 g)
  • Barley oil (23–92 mg / 100 g)
  • Grapeseed oil (33–75 mg / 100 g)
  • Rice germ oil (30 mg / 100 g)
  • Black cumin (16 mg / 100 g as beta-tocotrienol)
  • Macadamia nut oil (5–9 mg / 100 g)
  • Wheat germ oil (4 mg / 100 g)
  • Coconut oil (3.9 mg / 100 g)

In annatto seeds , black cumin oil, clove oil, red palm oil and grape seed oil, tocotrienols even make up the majority of vitamin E, while many other vegetable oils only have a relatively low percentage of tocotrienols.

Due to their abundance in barley (including grapes, annatto and palm oil), tocotrienols have been a normal part of the diet for millennia.

construction

Tocotrienols contain a chroman ring which is hydroxylated at position 6 and linked to an unsaturated side chain at position 2. The derivatives are subdivided into an α, β, γ or δ form, depending on the methylation of the chroman ring. Tocotrienols are of course in an ( R ) configuration .

Surname Structure of the ( R ) isomer R 1 R 2
α-tocotrienol (R) -Tocotrienol (R3 = CH3) V.1.svg CH 3 CH 3
β-tocotrienol CH 3 H
γ-tocotrienol H CH 3
δ-tocotrienol H H

Differences between tocotrienols and tocopherols

From a chemical point of view, tocotrienols only differ from tocopherols in terms of their side chain. While it is completely saturated in the latter, tocotrienols have a tri-unsaturated side chain. These unsaturated double bonds lead to a significantly increased vitamin activity in the tocotrienols. This is explained by:

  • A faster reactivation from chromanoxyl radicals,
  • a more uniform distribution in the membrane layers,
  • a stronger integration into the membrane lipids, which enables a more effective interaction of the chromanols with the lipid radicals.

Effect as an antioxidant

Compared to alpha-tocopherol, alpha-tocotrienol has a 40 to 60-fold higher effect as an antioxidant against lipid peroxidation in cell membranes in vitro .

Bioavailability

When taken orally, tocotrienols are only about 30% as well absorbed as tocopherol in the body. They are also eliminated more quickly. However, tocotrienols are absorbed through the skin much better than tocopherols. The consumption of alpha-tocopherol, especially synthetic dl-alpha-tocopheryl acetate , blocks the absorption of tocotrienols in food and accelerates the rate of degradation in the tissue.

Technical extraction

Tocotrienols are currently obtained on a large scale from red palm oil, rice germ oil and annatto seeds. The concentrated vitamin oil is called TRF ( Tocotrienol Rich Fraction ). The composition of the isomers varies considerably depending on the origin.

Influence on NFkappaB

Tocotrienols have a clear influence on the transcription factor NF-κB , which is also known as the redox-sensitive transcription factor. NF-κB regulates genes that play a central role in inflammation, apoptosis and aging. According to the current state of research, this property, which is predominantly found in the isomers gamma-tocotrienol and delta-tocotrienol, has been linked to anti-inflammatory and cancer effects.

Tocotrienols in chemotherapy

A number of studies in recent years have shown that gamma-tocotrienol and delta-tocotrienol can increase the effectiveness of various chemotherapy drugs ( gemcitabine , erlotinib and gefitinib doxorubicin and paclitaxel and others).

Tocotrienols for ionizing radiation and UV radiation

In 2008, 2010 and 2012 it was found in animal experiments and in experiments on stem cells that high-dose delta-tocotrienol can develop a considerable protective effect against ionizing radiation . 80% of the mice that were treated subcutaneously with delta-tocotrienol survived an otherwise fatal exposure to gamma radiation . Mice that were fed a tocotrienol mixture suffered less skin damage ( sunburn and tumor development) from UVB light than mice that received only alpha-tocopherol.

Other effects

Since 1991 further biological functions of tocotrienols have been reported that are predominantly not found in tocopherols: These are antiproliferative, neuroprotective, cholesterol-lowering and anti-inflammatory properties. For the most part, however, these effects have not been proven in humans, but only seen in cell cultures or in animal experiments .

Individual evidence

  1. ↑ Ibrahim et al .: Biochemical characterization, anti-inflammatory properties and ulcerogenic traits of some cold-pressed oils in experimental animals In: Journal Pharmaceutical Biology 140 (2), Jan 6, 2017, pp. 740-748. PMID 28056572 doi ; accessed March 30, 2017.
  2. ↑ Bertrand MatthauS and Mehmet Musa Özcan: Fatty Acids, Tocopherol, and Sterol Contents of Some Nigella Species Seed Oil In: Czech J. Food Sci., 29: 145-150. [1] ; Retrieved November 2, 2017.
  3. ↑ Natural sources of tocotrienols (sortable overview) ; accessed March 30, 2017
  4. ↑ a b E. Serbinova, V. Kagan, D. Han, L. Packer: Free radical recycling and intramembrane mobility in the antioxidant properties of alpha-tocopherol and alpha-tocotrienol . In: Free Radic Biol Med . tape 10 , no. 5 , 1991, pp. 263-275 , PMID 1649783 .
  5. ^ A b L. Packer, SU Weber, G. Rimbach: Molecular aspects of alpha-tocotrienol antioxidant action and cell signaling . In: J. Nutr. tape 131 , no. 2 , February 2001, p. 369S-373S , PMID 11160563 .
  6. ^ AS Adler, TL Kawahara, E. Segal, HY Chang: Reversal of aging by NFkappaB blockade. In: Cell Cycle. 7 (5), Mar 1, 2008, pp. 556-559. Epub 2007 Dec 26. PMID 18256548 .
  7. ↑ a b Mary Kaileh, Ranjan Sen: Role of NF-kB in the Anti-Inflammatory Effects of Tocotrienols. In: J Am Coll Nutr. 29 (3 Suppl), Jun 2010, pp. 334S-339S. PMID 20823493 .
  8. ↑ a b K. Husain, RA Francois, T. Yamauchi, M. Perez, SM Sebti, MP Malafa: Vitamin E δ-tocotrienol augments the antitumor activity of gemcitabine and suppresses constitutive NF-κB activation in pancreatic cancer. In: Mol Cancer Ther . 10 (12), Dec 2011, pp. 2363-2372. Epub 2011 Oct 4. PMID 21971120 .
  9. ↑ SV Bachawal, VB Wali, PW Sylvester: Combined gamma-tocotrienol and erlotinib / gefitinib treatment suppresses stat and Akt signaling in murine mammary tumor cells. In: Anticancer Res . 30 (2), Feb 2010, pp. 429-437. PMID 20332450 .
  10. ↑ Sunitha V Bachawal, Vikram B Wali, Paul W Sylvester: Enhanced antiproliferative and apoptotic response to combined treatment of γ-tocotrienol with erlotinib or gefitinib in mammary tumor cells. In: BMC Cancer . 10, 2010, p. 84. PMC 2841143 (free full text).
  11. ↑ Peramaiyan Rajendran et al .: γ-Tocotrienol is a novel inhibitor of constitutive and inducible STAT3 signaling pathway in human hepatocellular carcinoma: potential role as an antiproliferative, pro-apoptotic and chemosensitizing agent. In: Br J Pharmacol . 163 (2), May 2011, pp. 283-298. PMC 3087132 (free full text).
  12. ↑ Tocotrienols in cancer treatment with chemotherapy .
  13. ^ XH Li, D. Fu, NH Latif, CP Mullaney, PH Ney, SR Mog, MH Whitnall, V. Srinivasan, M. Xiao: Delta-tocotrienol protects mouse and human hematopoietic progenitors from gamma irradiation through extracellular signal-regulated kinase / mammalian target of rapamycin signaling. In: Hematologica. 95 (12), Dec 2010, pp. 1996-1200. PMID 20823133 .
  14. ↑ Y. Yamada, M. Obayashi, T. Ishikawa, Y. Kiso, Y. Ono, K. Yamashita: Dietary tocotrienol reduces UVB-induced skin damage and sesamin enhances tocotrienol effects in hairless mice. In: J Nutr Sci Vitaminol (Tokyo). 54 (2), Apr 2008, pp. 117-123. PMID 18490840 .
  15. ↑ JY Fu, DR Blatchford, L. Tetley, C. Dufès: Tumor regression after systemic administration of tocotrienol entrapped in tumor-targeted vesicles. In: J Control Release . 140 (2), Dec 3, 2009, pp. 95–. PMID 19709637 .
  16. ^ Vitamin E and Breast Cancer. In: J Nutr. 134 (12 Suppl), Dec 2004, pp. 3458S-3462S. PMID 15570054 .
  17. ↑ N. Guthrie, A. Gapor, AF Chambers, KK Carroll: 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. 127 (3), Mar 1997, pp. 544S-548S. PMID 9082043 .
  18. ↑ Shibata et al.: Tocotrienol inhibits secretion of angiogenic factors from human colorectal adenocarcinoma cells by suppressing hypoxia-inducible factor-1alpha. In: J Nutr. 138 (11), Nov 2008, pp. 2136-2214. PMID 18936210 .
  19. ↑ S. Khanna, S. Roy, A. Slivka, T. Craft, S. Chaki, C. Rink, M. Notestine, A. DeVries, N. Parinandi, C. Sen: Neuroprotective properties of the natural vitamin E alpha tocotrienol . In: Stroke . tape 36 , no. 10 , 2005, pp. 2258–2264 , doi : 10.1161 / 01.STR.0000181082.70763.22 , PMID 16166580 .
  20. ↑ Lowering of serum cholesterol in hypercholesterolemic humans by tocotrienols (palmvitee. PMID 2012010 .
  21. ↑ Dietary tocotrienols reduce concentrations of plasma cholesterol, apolipoprotein B, thromboxane B2, and platelet factor 4 in pigs with inherited hyperlipidemia. PMID 2012015 .
  22. ^ SJ Wu et al: Tocotrienol-rich fraction of palm oil exhibits anti-inflammatory property by suppressing the expression of inflammatory mediators in human monocytic cells. In: Mol Nutr Food Res. 52 (8), Aug 2008, pp. 921-992. PMID 18481320 .
  23. ↑ ML Yam et al.: Tocotrienols suppress proinflammatory markers and cyclooxygenase-2 expression in RAW264.7 macrophages. In: Lipids. 44 (9), Sep 2009, pp. 787-797. PMID 19655189 .

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