Phenolic Compounds of Flax Seed

Year 2012, Volume: 10 Issue: 4, 85 - 90, 01.12.2012

Evrim Özkaynak Kanmaz Gülden Ova

Abstract

Flaxseed is a valuable source of phytochemicals such as lignans, phenolic acids and flavonoids with beneficial health effects. Flaxseed is also the richest source of secoisolariciresinol diglucoside SDG which is converted to mammalian lignans as enterodiol and enterolactone. Especially, phytoestrogenic, anticarcinogenic, antioxidative and cardioprotective effects of flaxseed were attributed to its content of SDG, phenolic acids and flavonoids. Flaxseed is increasingly used as a functional food or a functional ingredient in food products because of its valuable bioactive compounds in food industry

Keywords

Flaxseed, Functional food, SDG lignan, Phenolic acids, Flavonoids

Keten Tohumunun Yapısındaki Fenolik Bileşikler

Abstract

Keten tohumu lignanlar, fenolik asitler ve flavonoidler gibi sağlığa yararlı fitokimyasalların doğal kaynağı olup enterodiol ve enterolakton memeli lignanlarının öncüsü sekoisolarikirezinol diglukosid SDG lignan açısından da en zengin kaynaktır. Yapılan çalışmalar sonucunda keten tohumunun insanlar üzerinde özellikle fitoöstrojenik, antioksidan, antikarsinojenik ve kardioprotektiv etkilerinin yapısında bulunan SDG lignan ve diğer fenolik bileşiklerden kaynaklandığı ileri sürülmektedir. Bu önemli biyoaktif bileşiklerden dolayı keten tohumunun gıda sanayinde fonksiyonel gıda olarak veya gıda ürünlerinde fonksiyonel bileşen olarak kullanımı gün geçtikçe artmaktadır

Keywords

Keten tohumu, Fonksiyonel gıda, SDG lignan, Fenolik asitler, Flavonoidler

References

• Başer, K.H.C., 2002. Fonksiyonel gıdalar ve nutrasötikler. 14. Bitkisel İlaç Hammaddeleri Toplantısı, Bildiriler, 29-31 Mayıs,2004, Eskişehir
• Oomah, B.D., Kenaschuk, E.O., Mazza, G., 1995. Phenolic acids in flaxseed. J. Agric. Food Chem. 43: 2016-2019.
• Oomah, B.D., Mazza, G., Kenaschuk, E.O., 1996. Flavonoid content of flax seed. Influence of cultivar and environment. Euphytica 90: 163-167.
• Meagher, L., Beecher, G.R., 2000, Assessment of data on the lignan content of foods. Journal of Food Composition and Analysis 13: 935-947.
• Hu, C., Yuan, Y.V., Kitts, D.D., 2007. Antioxidant activities of the flaxseed lignan secoisolariciresinol diglucoside, its aglycone secoisolariciresinol and the enterolactone in vitro. Food and Chemical Toxicology 45(11): 2219-2227. enterodiol and
• Medina, L.S.A., 2006. Phenolic Compounds: Their Role during Olive Oil Extraction and in Flaxseed- transfer and Antioxidant Function. Doctorate thesis. University of Lleida Agronoöical, Forestal and Food Systems Doctorate Program Food Technology Department Lleida, Spain, 211p.
• Coşkuner, Y., Karababa, E., 2007. Some physical properties of flaxseed (Linum usitatissimum L.). Journal of Food Engineering 78: 1067-1073.
• Madhusudhan, B., Wiesenborn, D., Schwarz, J., Tostenson, K., Gillespie, J. A., 2000. Dry mechanical method for concentrating the lignan secoisolariciresinol Lebensm.-Wiss. u.-Technol. 33: 268-275. in flaxseed.
• Clifford, M.N., 2000. Chlorogenic acids and other cinnamates—nature, occurence, dietary burden, absorption and metabolism. Journal of the Science of Food and Agriculture 80: 1033–1043.
• Westcott, N.D., Muir, A.D., 2000. Overview of flaxseed lignans. Inform 11: 118–121.
• Webb, A.L., McCullough, M.L., 2005. Dietary lignans: potential role in cancer prevention. Nutrition and Cancer 51(2): 117–131.
• Liggins, J., Grimwood, R., Bingham, S.A., 2000. Extraction phytoestrogens in food and human samples. Anal. Biochem. 287: 102–109. of lignan
• Meagher, L.P., Beecher, G.R., Flanagan, V.P., Li, B.W., 1999. Isolation and characterization of the lignans, isolariciresinol and pinoresinol, in flaxseed meal. J. Agric. Food Chem. 47: 3173–3180.
• Sicilia, T., Niemeyer, H.B., Honig, D.M., Metzler, M., 2003. characterization of lignans in flaxseed and pumpkin seeds. J. Agric. Food Chem. 51: 1181-1188.
• Struijs, K., Vincken, J. P., Verhoef, R., Willemiek, H.M., Casteren, O., Voragen, A. G. J., Gruppen, H., 2007. The flavonoid herbacetin diglucoside as a constituent of the lignan macromolecule from flaxseed hulls. Phytochemistry 68: 1227–1235.
• Milder, I., 2007. Lignan Intake in the Netherlands and its Relation with Mortality. Doctorate thesis. Thesis Wageningen University, the Netherlands, Dutch, 159p.
• Charlet, S., Bensaddek, L., Raynaud, S., Gillet, F., Mesnard, F., Fliniaux, M.A. 2002. An HPLC procedure anhydrosecoisolariciresinol. Application to the evaluation of flax lignan content. Plant Physiol. Biochem. 40: 225–229. quantification of
• Tour´e, A., Xueming, X., 2010. Flaxseed lignans: source, biosynthesis, metabolism, antioxidant activity, bio-active components, and health benefits. Food Science and Food Safety 9:261-269.
• Kilkkinen, A., Stumpf, K., Pietinen, P., Valsta, L.M., Tapanainen, Determinants of serum enterolactone concentration. The American Journal of Clinical Nutrition 73: 1094–1100. H., 2001.
• Degenhardt, A., Habben, S., Winterhalter, P., 2002. Isolation diglucoside from flaxseed (Linum usitatissimum L.) by high-speed counter-current chromatography. Journal of Chromatography A 943: 299-302.
• Heinonen, S., Nurmi, T., Liukkonen, K., Poutanen, K., Wahala, K., Deyama, T., Nishibe, S., Adlercreutz, H., 2001. In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol. Journal of Agricultural and Food Chemistry 49: 3178– 3186.
• Nesbitt, P.D., Lam, Y.; Thompson, L.U., 1999. Human precursors in raw and processed flaxseed. Am. J. Clin. Nutr. 69: 549–555. of mammalian lignan
• Kamal-eldin, A., Peerlkamp, N., Johnson, P., Andersson, R., Andersson, R.E., Lundgren, L.N., Aman, P., 2001. An oligomer from flaxseed composed of secoisolariciresinoldiglucoside and 3- hydroxy-3-methyl Phytochem. 58: 587-590. acid residues.
• Mazza, G., 1998. Flaxseed Products for Disease Prevention. In: Functional Foods, Biochemical and Processing Company, Lancaster-Pennsylvania, 91-127. Technomic Publishing
• Coşkun, T., 2005. Fonksiyonel besinlerin sağlığımız üzerine etkileri. Çocuk Sağlığı ve Hastalıkları Dergisi 48: 69-84.
• Prasad K, Mantha S.V., Muir A.D., Westcott N.D., 2000. Protective effect of secoisolariciresinol diglucoside against streptozotocin-induced diabetes and its mechanism. Mol Cell Biochem. 206:141–50.
• Rickard, S.E., Thompson, L.U., 1997. Health effects of flaxseed mucilage, lignans. Inform 8: 860-865.
• Boccardo, F., Lunardi, G., Guglielmini, P., Parodi, M., Murialdo, R., Schettini, G., Rubagotti, A., 2004. Serum enterolactone levels and the risk of breast cancer in women with palpable cysts. Eur. J. Cancer 40: 84–89.
• Chen, J., Stavro, P.M., Thompson L.U., 2002. Dietary flaxseed inhibits human breast cancer growth and metastasis and downregulates expression of insulin-like growth factor and epidermal growth factor receptor. Nutr. Cancer 43:187-192.
• Chen, J., Thompson, L.U., 2003. Lignans and tamoxifen, alone or in combination, reduce human breast cancer cell adhesion, invasion and migration in vitro. Breast Cancer Res. Treat. 80: 163-170.
• Sung, M.K., Lautens, M., Thompson, L.U., 1998. Mammalian lignans inhibit the growth of estrogen- independent human colon tumor cells. Anticancer Res. 18: 1405–1408.
• Lucas, E.A., Lightfoot, S.A., Hammond, J.L., Devareddy, L., Khalil, D. A., Daggy, B. P., Smith, B. J., Westcott, N., Mocanu, V., Soung do, Y., Arjmandi, B.H., 2004. Flaxseed reduces plasma cholesterol and atherosclerotic lesion formation in ovariectomized Atherosclerosis 173: 223–229. Syrian hamsters.
• Bloedon, L.T., Szapary, O.P, 2004. Flaxseed and cardiovascular risk. Nutrition Reviews. 62:18-27.
• Collins, T. F. X., Sprando, R. L., Black, T. N., Olejnik, N., Wiesenfeld, P. W., Babu, U. S., Bryant, M., Flynn, T. J., Ruggles, D.I., 2003. Effects of flaxseed and defatted flaxseed meal on reproduction and development in rats. Food and Chemical Toxicology 41:819-834.
• Westcott, N.D., Muir, A.D., 1996. Process for extracting and purifying lignans and cinnamic acid derivatives No.WO9630468A2). flaxseed (PCTpatent
• Thompson, L.U., Rickard, S.E., Cheung, F., Kenaschuk, E.O., Obermeyer, W.R., 1997. Variability in anticancer lignan levels in flax seed. Nutr. Cancer 27: 26–30.
• Meagher, L.P., Beecher, G.R., Flanagan, V.P., Li, B.W., 1999. Isolation and characterization of the lignans, isolariciresinol and pinoresinol, in flaxseed meal. J. Agric. Food Chem. 47: 3173–3180.
• Eliasson, C., Kamal-Eldin, A., Andersson, R., Aman, chromatographic analysis of secoisolariciresinol diglucoside and hydroxycinnamic acid glucosides in flaxseed by alkaline extraction. J. Chromatography A 1012: 151-159. liquid
• Beejmohun, V., Fliniaux, O., Grand, E., Lamblin, F., Bensaddek, L., Christen, P., Kovensky, J., Fliniaux, M., Mesnard, F., 2007. Microwave- assisted extraction of the main phenolic compounds in flaxseed. Phytochem. Anal. 18: 275–282.
• Özkaynak, E., 2011. Türkiye’de Yetiştirilen Bazı Yağlık Keten Tohumlarının (Linum usitatissimum L.) ve Filizlerinin Biyoaktif Bileşikler Açısından İncelenmesi Üzerine Bir Araştırma, Fen Bilimleri Enstitüsü, İzmir, 2011.
• Wiesenborn, D., Tostenson, K., Kangas, N., 2003. Continuous abrasive method for mechanically fractionating flaxseed. JAOCS. 80: 295–300.
• Saldamlı, İ., 2005. Gıda Kimyası. Hacettepe Yayımları, Ankara.
• Dabrowski, K.J., Sosulski, F.W., 1984. Composition of free and hydrolyzable phenolic acids in defatted flours of ten oilseeds. J. Agric. Food Chem. 32:128- 130.
• Johnsson, P., Peerlkampa, N., Kamal-Eldina, A., Andersson, R.E., Anderssona, R., Lundgren, L.N., Åman, P., 2002. Polymeric fractions containing phenol glucosides in flaxseed. Food Chemistry 76: 207–212.
• Wanasundara, P.K.J.P.D., Shahidi, F., 1994. Alkanol ammonia water/hexane extraction of flaxseed. Food Chemistry 49:39–44.
• Oomah, B.D., Mazza, G., 1997. Effect of dehulling on chemical composition and physical properties of flaxseed. Lebensm.-Wiss. u.-Technol. 30: 135–140.
• Velioglu, Y.S., Mazza, G., Gao, L., Oomah, B.D., 1998. Antioxidant activity and total phenolics in selected fruits, vegetables, and grain products. J. Agric. Food Chem. 46(10): 4113–4117.
• Choo, W.S., Birch, J., Dufour, J.P., 2007. Physicochemical and quality characteristics of cold- pressed flaxseed oils. Journal of Food Composition and Analysis 20: 202-211.
• Bozan, B., Temelli, F., 2008. Chemical composition and oxidative stability of flax, safflower and poppy seed and seed oils. Bioresource Technology 99: 6354-6359.
• Pekkarinen, S.S., Heinonen, I.M., Hopia, A.I., 1999. Flavonoids quercetin, myricetin, kaemferol and (+)- catechin as antioxidants in methyl linoleate. Journal of the Science of Food and Agriculture 79: 499– 506.
• Qiu, S. X., Lu, Z. Z., Luyengi, L., Lee, S.K., Pezzuto, J.M., Farnsworth, N.R., Thompson, L.U., Fong, H.H.S., 1999. Isolation and characterization of flaxseed (Linum usitatissimum) constituents. Pharm. Biol. 37: 1–7.