Tocotrienols in plants: Occurrence, biosynthesis, and function

Tocotrienols: Vitamin E beyond Tocopherols, Second Edition

Volumn , Issue , 2012, Pages 1-16

  Müller, Maren ^a   Cela, Jana ^a   Asensi Fabado, María A ^a   Munné Bosch, Sergi ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84988968726     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/b12502     Document Type: Chapter

References (82)

1. Aitzetmüller, K., Xin, Y., Werner, G., Grönheim, M. 1992. High performance liquid chromatographic investigations of stillingia oil. Journal of Chromatography 603:165-173.
2. Amaral, J.S., Alves, M.R., Seabra, R.M., Oliviera, B.P. 2005. Vitamin E composition of walnuts (Juglans regia L.): A 3-year comparative study of different cultivars. Journal of Agricultural and Food Chemistry 53:5467-5472.
3. Amiguet, V.T., Petit, P., Ta, C.A. et al. 2006. Phytochemistry and antifungal properties of the newly discovered tree Pleodendron costaricense. Journal of Natural Products 69:1005-1009.
4. Asensi-Fabado, M.A., Munné-Bosch, S. 2010. Vitamins in plants: Occurrence, biosynthesis and antioxidant function. Trends in Plant Science 15:582-592.
5. Austin, J.R., Frost, E., Vidi, P.A., Kessler, F., Staehelin, L.A. 2006. Plastoglobules are lipoprotein subcompartments of the chloroplast that are permanently coupled to thylakoid membranes and contain biosynthetic enzymes. Plant Cell 18:1693-1703.
6. Bagci, E., Bruehl, L., Aitzetmüller, K., Altan, Y. 2004a. Fatty acid and tocochromanol patterns of some Turkish Boraginaceae-A chemotaxonomic approach. Nordic Journal of Botany 22:719-726.
7. Bagci, E., Bruehl, L., Özçelik, H., Aitzetmüller, K., Vural, M., Sahim, A. 2004b. A study of the fatty acid and tocochromanol patterns of some Fabaceae (Leguminosae) plants from Turkey I. Grasas y Aceites 55:378-384.
8. Bagci, E., Karaagaçli, Y. 2004. Fatty acid and tocochromanol patterns of Turkish pines. Acta Biologica Cracoviensia, Series Botanica 46:95-100.
9. Bagci, E., Vural, M., Dirmenci, T., Bruehl, L., Aitzetmüller, K. 2004c. Fatty acid and tocochromanol patterns of some Salvia L. species. Zeitschrift für Naturforschung 59c: 305-309.
10. Balz, M., Schulte, E., Their, H.P. 1992. Trennung von Tocopherolen und Tocotrienolen durch HPLC. Fat Science Technology 94:209-213.
11. Bereau, D., Benjelloun-Mlayah, B., Delmas, M. 2001. Maximiliana maripa drude mesocarp and kernel oils: Fatty acid and total tocopherol compositions. Journal of the American Oil Chemists’ Society 78:213-214.
12. Beringer, H., Nothdurft, F. 1979. Plastid development and tocochromanol accumulation in oil seeds. In Advances in Biochemistry and Physiology of Plant Lipids, eds. L.A. Appelqvist, and C. Liljenberg, pp. 133-137. Amsterdam, the Netherlands: Elsevier/North Holland Biomedical Press.
13. Bertoli, C., Fay, L.B., Stancanelli, M., Gumy, D., Lambelet, P. 1998. Characterization of Chilean hazelnut (Gevuina avellana Mol) seed oil. Journal of the American Oil Chemists’ Society 75:1037-1040.
14. Budin, J.T., Breene, W.M., Putnam, D.H. 1995. Some compositional properties of camelina (Camelina sativa L. Crantz) seeds and oils. Journal of the American Oil Chemists’ Society 72:309-315.
15. Cahoon, E.B., Hall, S.E., Ripp, K.G., Ganzke, T.S., Hitz, W.D., Coughlan, S.J. 2003. Metabolic redesign of vitamin E biosynthesis in plants for tocotrienol production and increased antioxidant content. Nature Biotechnology 21:1082-1087.
16. Cela, J., Müller, M., Munné-Bosch, S. 2011. Tocopherol and tocotrienol (vitamin E) composition of some edible fruits. In Vitamin E: Nutrition, Side Effects and Supplements, ed. A. Lindberg, pp. 277-287. Hauppauge, NY: Nova Science Publishers.
17. Choo, Y.M., Ma, A.N., Chuah, C.H., Khor, H.T., Bong, S.C. 2004. A developmental study on the appearance of tocopherols and tocotrienols in developing palm mesocarp (Elaeis guineensis). Lipids 39:561-564.
18. Chun, J., Lee, J., Ye, L., Exler, J., Eitenmiller, R.R. 2006. Tocopherol and tocotrienol contents of raw and processed fruits and vegetables in the United States diet. Journal of Food Composition and Analysis 19:196-200.
19. Clough, P.M. 2001. Specialty vegetable oils containing γ-linolenic acid and stearidonic acid. In Structured and Modified Lipids 4, ed. F.D. Gunstone, pp. 75-107. New York: Dekker.
20. Collakova, E., DellaPenna, D. 2001. Isolation and functional analysis of homogentisate phytyltransferase from Synechocystis sp. PCC 6803 and Arabidopsis. Plant Physiology 127:1113-1124.
21. Crane, S., Aurore, G., Joseph, H., Mouloungui, Z., Bourgeois, P. 2005. Composition of fatty acids triacylglycerols and unsaponifiable matter in Calophyllum calaba L. oil from Guadeloupe. Phytochemistry 66:1825-1831.
22. Crews, C., Hough, P., Godward, J. et al. 2005. Study of the main constituent of some authentic hazelnut oils. Journal of Agricultural and Food Chemistry 53:4843-4852.
23. Falk, J., Andersen, G., Kernebeck, B., Krupinska, K. 2003. Constitutive overexpression of barley 4-hydroxyphenylpyruvate dioxygenase in tobacco results in elevation of the vitamin E content in seeds but not in leaves. FEBS Letters 540:35-40.
24. Falk, J., Munné-Bosch, S. 2010. Tocochromanol functions in plants: Antioxidation and beyond. Journal of Experimental Botany 61:1549-1566.
25. Firestone, D. 1999. Physical and chemical characteristics of oils, fats, and waxes. Database ‘Seed Oil Fatty Acids’ (SOFA).
26. Fisk, I.D., White, D.A., Carvalho, A., Gray, D.A. 2006. Tocopherol-An intrinsic component of sunflower seed oil bodies. Journal of the American Oil Chemists Society 83:341-344.
27. Franzen, J., Bausch, J., Glatzle, D., Wagner, E. 1991. Distribution of vitamin E in spruce seedlings and mature tree organs, and within the genus. Phytochemistry 30:147-151.
28. Franzen, J., Haass, M. 1991. Vitamin E content during development of some seedlings. Phytochemistry 30:2911-2913.
29. Frega, N., Mozzon, M., Bocci, F. 1998. Identification and estimation of tocotrienols in the annatto lipid fraction by gas chromatography-mass spectrometry. Journal of the American Oil Chemists’ Society 75:1723-1727.
30. Grams, G.W., Blessin, C.W., Inglett, G.E. 1970. Distribution of tocopherol within the corn kernel. Journal of the American Oil Chemists’ Society 47:337-339.
31. Hall, G.S., Laidman, D.L. 1968. The pattern and control of isoprenoid quinone and tocopherol metabolism in the germinating grain of wheat (Triticum vulgare). Biochemical Journal 108:475-482.
32. Halloy, S., Garu, A., McKenzie, B. 1996. Gevuina nut (Gevuina avellana, Proteaceae), a cool climate alternative to macadamia. Economic Botany 50:224-235.
33. Harinantenaina, L., Asakawa, Y., De Clercq, E. 2007. Cinnamacrins A-C, cinnafragrin D, and cytostatic metabolites with α-glucosidase inhibitory activity from Cinnamosma macrocarpa. Journal of Natural Products 70:277-282.
34. Harinantenaina, L., Matsunami, K., Otsuka, H., Kawahata, M., Yamaguchi, K., Asakawa, Y. 2008. Secondary metabolites of Cinnamosma madagascariensis and their α-glucosidase inhibitory properties. Journal of Natural Products 71:123-126.
35. Harinantenaina, L., Takaoka, S. 2006. Cinnafragrins A-C, dimeric and trimeric drimane sesquiterpenoids from Cinnamosma fragrans, and structure revision of capsicodendrin. Journal of Natural Products 69:1193-1197.
36. Hassapidou, M.N., Manoukas, A.G. 1993. Tocopherol and tocotrienol compositions of raw table olive fruit. Journal of the Science of Food and Agriculture 61:277-280.
37. Herbers, K. 2003. Vitamin production in transgenic plants. Journal of Plant Physiology 160:821-829.
38. Hess, J.L. 1993. Vitamin E, α-tocopherol. In Antioxidants in Higher Plant, eds. R.G. Alscher, and J.L. Hess, pp. 111-134. Boca Raton, FL: CRC Press.
39. Hoa, T.T., Al-Babili, S., Schaub, P., Potrykus, I., Beyer, P. 2003. Golden indica and japonica rice lines amenable to deregulation. Plant Physiology 133:161-169.
40. Hofius, D., Hajirezaei, M.R., Geiger, M., Tschiersch, H., Melzer, M., Sonnewald, U. 2004. RNAi-mediated tocopherol deficiency impairs photoassimilate export in transgenic potato plants. Plant Physiology 135:1256-1268.
41. Horvath, G., Wessjohann, L., Bigirimana, J. et al. 2006. Differential distribution of tocopherols and tocotrienols in photosynthetic and non-photosynthetic tissues. Phytochemistry 67:1185-1195.
42. Ivanov, S.A., Aitzetmüller, K. 1995. Untersuchungen über die Tocopherol-und Tocotrienolzusammensetzung der Samenöle einiger Vertreter der Familie Apiaceae. Fat Science Technology 97:24-29.
43. Ivanov, S.A., Aitzetmüller, K. 1998. Untersuchungen über die Tocopherol-und Tocotrienolzusammensetzung der Samenlipide einiger Arten der bulgarischen Flora. Fett/Lipid 100:348-352.
44. Kallio, H., Yang, B., Peippo, P., Tahvonen, R., Pan, R. 2002. Triacylglycerols, glycerophospholipids, tocopherols, and tocotrienols in berries and seeds of two subspecies (ssp. sinensis and mongolica) of sea buckthorn (Hippophaë rhamnoides). Journal of Agricultural and Food Chemistry 50:3004-3009.
45. Kamal-Eldin, A., Appelqvist, L. 1996. The chemistry and antioxidant properties of tocopherols and tocotrienols. Lipids 31:671-701.
46. Kato, A., Yamaoka, M., Tanaka, A. 1983. Vitamin E extraction. UK Patent application GB 2117381 A.
47. van der Kooij, T.A.W., Krupinska, K., Krause, K. 2005. Tocochromanol content and composition in different species of the parasitic flowering plant genus Cuscuta. Journal of Plant Physiology 162:777-781.
48. Krishna, A.G.G., Prabhakar, J.V., Aitzetmüller, K. 1997. Tocopherol and fatty acid composition of some Indian pulses. Journal of the American Oil Chemists’ Society 74:1603-1606.
49. Lehmann, J.W., Putnam, D.H., Qureshi, A.A. 1994. Vitamin E isomers in grain amaranths (Amaranthus spp.). Lipids 29:177-181.
50. Matringe, M., Ksas, B., Rey, P., Havaux, M. 2008. Tocotrienols, the unsaturated forms of vitamin E, can function as antioxidants and lipid protectors in tobacco leaves. Plant Physiology 147:764-778.
51. Matthäus, B., Aitzetmüller, K., Friedrich, H. 2002. Description of the database ‘Seed Oil Fatty Acids’ (SOFA). Agro Food Industry Hi-tech 13:38-43.
52. Matthäus, B., Özcan, M. 2005. Glucosinolates and fatty acid, sterol, and tocopherol composition of seed oils from Capparis spinosa var. spinosa and Capparis ovata Desf. var. canescens (Coss.) Heywood. Journal of Agricultural and Food Chemistry 53:7136-7141.
53. Matthäus, B., Özcan, M. 2006. Quantitation of fatty acids, sterols, and tocopherols in turpentine (Pistacia terebinthus Chia) growing wild in Turkey. Journal of Agricultural and Food Chemistry 54:7667-7671.
54. Matthäus, B., Vosmann, K., Quoc Pham, L., Aitzetmüller, K. 2003. Fatty acids and tocopherol composition of Vietnamese oilseeds. Journal of the American Oil Chemists’ Society 80:1013-1020.
55. Merza, J., Aumond, M.C., Rondeau, D. et al. 2004. Prenylated xanthones and tocotrienols from Garcinia virgata. Phytochemistry 65:2915-2920.
56. Mölleken, H. 1999. Hanf (Cannabis sativa) als novel food. Bioforum-Forschung and Entwicklung 22:452-457.
57. Morrison, W.R., Conventry, A.M., Barnes, P.J. 1982. The distribution of acyl lipids and tocopherols in flour millstreams. Journal of the Science of Food and Agriculture 33:925-933.
58. Munné-Bosch, S., Alegre, L. 2002. The function of tocopherols and tocotrienols in plants. Critical Reviews in Plant Sciences 21:31-57.
59. Munné-Bosch, S., Oñate, M., Olivera, P.G., Garcia, Q.S. 2011. Changes in phytohormones and oxidative stress markers in buried seeds of Vellozia alata. Flora 206:704-711.
60. Murkovic, M., Hillebrand, A., Winkler, J., Pfannhauser, W. 1996. Variability of vitamin E content in pumpkin seeds (Cucurbita pepo L.). Zeitschrift für Lebensmittel-Untersuchung und-Forschung A 202:275-278.
61. Norris, S.R., Shen, X., DellaPenna, D. 1998. Complementation of the Arabidopsis pds1 mutation with the gene encoding p-hydroxyphenylpiruvate dioxygenase. Plant Physiology 117:1317-1323.
62. Ong, A.S.H. 1993. Natural sources of tocotrienols. In Vitamin E in Health and Disease, eds. L. Packer, and J. Fuchs, pp. 3-8. New York: Dekker.
63. Qureshi, A.A., Lehmann, J.W., Peterson, D.M. 1996. Amaranth and its oil inhibit cholesterol biosynthesis in 6-week-old female chickens. Journal of Nutrition 126:1972-1978.
64. Peterson, D.M. 1995. Oat tocols: Concentration and stability in oat products and distribution within in the kernel. Cereal Chemistry 72:21-24.
65. Porfirova, S., Bergmüller, E., Tropf, S., Lemke, R., Dörman, P. 2002. Isolation of an Arabidopsis mutant lacking vitamin E and identification of a cyclase essential for all tocopherol biosynthesis. Proceedings of the National Academy of Sciences USA 99:12495-12500.
66. Rippert, P., Scimemi, C., Dubald, M., Matringe, M. 2004. Engineering plant shikimate pathway for production of tocotrienol and improving herbicide resistance. Plant Physiology 134:92-100.
67. Rohmer, M. 2003. Mevalonate-independent methylerythritol phosphate pathway for isoprenoid biosynthesis. Pure and Applied Chemistry 75:375-387.
68. Sadre, R., Gruber, J., Frentzen, M. 2006. Characterization of homogentisate prenyltrasnferase involved in plastoquinone-9 and tocochromanol biosynthesis. FEBS Letters 580:5357-5362.
69. Seo, E.K., Kim, N.C., Wani, M.C. et al. 2002. Cytotoxic prenylated xanthones and the unusual compounds anthraquinobenzophenones from Cratoxylum sumatranum. Journal of Natural Products 65:299.
70. Sheppard, A.J., Weihrauch, J.L., Pennington, J.A.T. 1993. Analysis and distribution of vitamin E in vegetable oils and foods. In Vitamin E in Health and Disease, eds. L. Packer, and J. Fuchs, pp. 9-31. New York: Marcel Dekker.
71. Shintani, D., DellaPenna, D. 1998. Elevating the vitamin E content of plants through metabolic engineering. Science 282:2098-2100.
72. Silva, D.H.S., Pereira, F.C., Zanoni, M.V.B., Yoshida, M. 2001. Lipophyllic antioxidants from Iryanthera juruensis fruits. Phytochemistry 57:437-442.
73. Slover, H.T. 1971. Tocopherols in food and fats. Lipids 6:291-296.
74. Soll, J., Schultz, G. 1979. Comparison of geranylgeranyl and phytyl substituted methylquinols in the tocopherol synthesis of spinach chloroplasts. Biochemical Biophysical Research Communications 91:715-720.
75. Soulier, P., Lecerf, J.-C., Farines, M., Soulier, J. 1989. Composition chimique des beurres de sal et d’illipé. Revue Francaise des Corps Gras 36:361-365.
76. Sun, Q., Zybailov, B., Majeran, W., Friso, G., Olinares, P.D.B., van Wijk, K.J. 2009. PPDB, the plant proteomics database at Cornell. Nucleic Acids Research, 37:969-974.
77. Suzuki, Y., Tsuchiya, M., Wassall, S.R. et al. 1993. Structural and dynamic membrane properties of alphatocopherol and alpha-tocotrienol. Implication to the molecular mechanism of the antioxidant potency. Biochemistry 32:10692-10699.
78. Velasco, L., Goffman, F.D., Pujadas-Salva, A.J. 2000. Fatty acids and tocochromanols in seeds of Orobanche. Phytochemistry 54:295-300.
79. Vidi, P.A., Kanwischer, M., Baginsky, S. et al. 2006. Tocopherol cyclase (VTE1) localization and vitamin E accumulation on chloroplast plastoglobule lipoprotein particles. Journal of Biological Chemistry 281:11225-11234.
80. Wang, X., Quinn, P.J. 2000. The location and function of vitamin E in membranes. Molecular Membrane Biology 17:143-156.
81. Yang, W., Cahoon, R.E., Hunter, S.C. et al. 2011. Vitamin E biosynthesis: Functional characterization of the monocot homogentisate geranylgeranyl transferase. Plant Journal 65:206-211.
82. Zlatanov, M.D. 1999. Lipid composition of Bulgarian chokeberry, black currant and rose hip seed oils. Journal of Agricultural and Food Chemistry 79:1620-1624.