Lignans Secoisolariciresinol

An inverse correlation between thyroid cancer risk and phytoestrogens was recently proposed as a result of a multi-ethnic population-based case control study conducted in the San Francisco Bay Area (Hom-Ross et al., 2002). In this study, dietary habits and phytoestrogen consumption were assessed by a food-frequency questionnaire and by a nutrient database. The outcome of the study was that soy-based foods and alfalfa sprouts were associated with a reduction of thyroid cancer risk, whereas a Western diet did not influence cancer risk. No difference was observed between American and Asian women or between pre- and postmenopausal women. Furthermore, among the few compounds examined, the isoflavones genistein and daidzein and the lignan secoisolariciresinol were the phytoestrogens most frequently associated with risk reduction (Horn-Ross et al., 2002). 

Umezawa T, Davin LB, Lewis NG (1991) Formation of lignans (-)-secoisolariciresinol and (-)-matairesinol with Forsythia intermedia ceU-free extracts. J Biol Chem 266 10210-10217 Okunishi T, Sakakibara N, Suzuki S et al (2004) Stereochemistry of matairesinol formation by Daphne secoisolariciresinol dehydrogenase. J Wood Sci 50 77-81 XiaZ-Q, Costa MA, Pelissier HC et al (2001) Secoisolariciresinol dehydrogenase purification, cloning, and functional expression. J Biol Chem 276 12614-12623... 

Degenhardt, A., Habben, S., and Winterhalter, P. 2002. Isolation of the lignan secoisolariciresinol diglucoside from flaxseed (Linum ustitatissimum L.) by high-speed counter-current chromatography. J. Chromatogr. 943, 299-302. 

Kitts, D.D., Yuan, Y.V., Wijewickreme, A.N., and Thompson, L.U. 1999. Antioxidant activity of the flaxseed lignan secoisolariciresinol diglycoside and its mammalian lignan metabolites enterodiol... 

Madhusudhan, B., Wiesenbom, D., Schwarz, J., Tostenson, K., and Gillespie, J. 2000. A dry mechanical method for concentrating the lignan secoisolariciresinol diglucoside in flaxseed. Leb. Wiss. Tech. 33, 268-275. 

Muir, A.D. and Westcott, N.D. 2000. Quantitation of the lignan secoisolariciresinol diglucoside in baked goods containing flax seed or flax meal. J. Agric. Food Chem. 48, 4048 4052. 

Umezawa T, Davin LB, Lewis NG (1990a) Formation of the lignan, (-)-secoisolariciresinol, by cell-free extracts of Forsythia intermedia. Biochem Biophys Res Commun 171 1008-1014... 

Lignans are formed of two phenylpropane units, which are commonly present in fruits like pears and prunes. The concentration of lignan secoisolariciresinol (SECO) in whole cranberry fruit is 10.5 mg/kg dry weight [24]. 

Clavel T, Henderson G, Engst W, Dore J, Blaut M. Phylogeny of human intestinal bacteria that activate the dietary lignan secoisolariciresinol diglucoside. FEMS Microbiol Ecol. 2006 55 471-478. 

Roncaglia L, Amaretti A, Raimondi S, Leonardi A, Rossi M. Role of bifidobacteria in the activation of the lignan secoisolariciresinol diglucoside. Appl Microbiol Biotechnol. 2011 92 159-168. 

Adolphe JL, Whiting SJ, Juurlink BHJ, Thorpe LU, Alcorn J. Health effects with consumption of the flax lignan secoisolariciresinol diglucoside. Br J Nutr. 2010 103 929-938. 

FIGURE 1.4 Biosynthesis of the lignan secoisolariciresinol diglucoside (SDG) in flaxseed. (From Ford, T.D., Davin, L.B., and Lewis, N.G., Proc. 58th Flax Inst. United States, March 23-25, Fargo, ND, 39 8, 2000.)... 

Milder, I.E.J., Arts, I.C.W., Venema, D.P., Lasaroms, J.J.P., Wahala, K., and HoUman, P.C.H., Optimization of a liquid chromatography-tandem mass spectrometry method for quantification of the plant lignans secoisolariciresinol, matairesinol, lariciresinol, and pinoresinol in foods, J. Agric. Food Chem., 52, 4643 651, 2004. 

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