Secoisolariciresinol diglucoside

Wang, L.Q., Meselhy, M.R., Li, Y., Qin, G.W., and Hattori, M., Human intestinal bacteria capable of transforming secoisolariciresinol diglucoside to mammalian lignans, enterodiol and enterolactone, Chem. Pharm. Bull, 48, 1606, 2000. 

Frank, J., Eliasson, C., Leroy-Nivard, D., Budek, A., Lundh, T., Vessby, B., Aman, P., and Kamal-Eldin, A., Dietary secoisolariciresinol diglucoside and its oligomers with 3-hydroxy-3-methyl glutaric acid decrease vitamin E levels in rats, Br. J. Nutr., 92, 169, 2004. 

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. 

Eliasson, C., Kamal-Eldin, A., Andersson, R., and Aman, P. 2003. High-performance liquid chromatographic analysis of secoisolariciresinol diglucoside and hydroxycinnamic acid glucosides in flaxseed by alkaline extraction. J. Chromatogr. 1012, 151-159. 

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. 

Prasad, K. 1997a. Hydroxyl radical-scavenging property of secoisolariciresinol diglucoside (SDG) isolated from flax-seed. Mol. Cell. Biochem. 168, 117-123. 

Prasad, K. 1999. Reduction of serum cholesterol and hypercholesterolemic atherosclerosis in rabbits by secoisolariciresinol diglucoside isolated from flaxseed. Circulation 99, 1355-1362. 

Prasad, K. 2000b. Antioxidant activity of secoisolariciresinol diglucoside-derived metabolites, secoi-solariciresinol, enterodiol, and enterolactone. Inti. J. Angiol. 9, 220-225. 

Prasad, K. 2001. Secoisolariciresinol diglucoside from flaxseed delays the development of type 2 diabetes in Zucker rat. J. Lab. Clin. Med 138, 32-39. 

Prasad, K. 2002. Suppression of phosphoenolpyruvate carboxykinase gene expression by secoisolariciresinol diglucoside (SDG), a new antidiabetic agent. Inti. J. Angiol. 11, 107-109. 

Prasad, K., Mantha, S.V., Muir, A.D., and Westcott, N.D. 1998. Reduction of hypercholesterolemic atherosclerosis by CDC-flaxseed with very low alpha-linolenic acid. Atherosclerosis 136, 367-375. Prasad, K., Mantha, S.V., Muir, A.D., and Westcott, N.D. 2000. Protective effect of secoisolariciresinol diglucoside against streptozotocin-induced diabetes and its mechanism. Mol. Cell. Bio-chem. 206, 141-150. 

Johnsson, P. Kamal-Eldin, A. Lundgren, L.N. Aman, P. 2000. HPLC method for analysis of secoisolariciresinol diglucoside in flaxseeds. J. Agric. Food Chem. 48 5216-5219. 

J. Fritsche, R. Angoelal, and M. Dachtler, On-line hqnid-chromatography-nnclear magnetic resonance spectroscopy-mass spectrometry conpling for the separation and characterization of secoisolariciresinol diglucoside isomers in fiaxseed, /. Chromatogr. A 972 (2002), 195-203. 

Ford, J.D., Fluang, K.S., Wang, Fl.B., Davin, L.B. and Lewis, N.G. (2001) Biosynthetic pathway to the cancer chemopreventive secoisolariciresinol diglucoside-hydroxymethyl glutaryl ester-linked lignan oligomers in flax Linum usitatissimum) seed. ]. Nat. Prod., 64,1388-97. 

Hano, C., Martin, L, Fliniaux, O., Legrand, B., Gutierrez, L., Arroo, R.R.J., Mesnard, F., Lamblin, F. and Laine, E. (2006b) Pinoresinol-lariciresinol reductase gene expression and secoisolariciresinol diglucoside accumulation in developing flax (Linum usitatissimum) seeds. Planta, 224,1291-301. 

Lignans of flaxseed exist as secoisolariciresinol diglucoside (SDG 126). SDG is a potent antioxidant in biological systems because of its tendency to associate in the aqueous phase. Much of the work on antioxidant activity of SDG is related to its radical mediated disease prevention (127, 128). Lignans of both sesame (121, 122) and flax (129, 130) have shown hydrogen-donating abihty and scavenging activity for various free radicals. 

In ESI conditions, aside from the formation of protonated ([M + H]+) and deprotonated ([M - H] ) molecules arising from the oxidation-reduction reactions at the sprayer, some cationization and anionization reactions can take place, due to the presence, inside the solution, of cations and anions. As an example, the positive- and negative-ion spectra of secoisolariciresinol diglucoside (SDG), obtained by injecting the methanol solution (10 5M with 0.1% of formic acid) in the ESI source at a flow rate of 15pL/min, are reported in Fig. 1.6a and b, respectively. In the former case, the protonated molecule is detectable at m/z 687, but the most abundant peaks are present at m/z 704 and 709, due to cationization reactions with NHJ and Na respectively. A scarcely abundant adduct with K+ is also detectable at m/z 725. The negative-ion spectrum (Fig. 1.6b) shows an abundant peak due to a deprotonated molecule (m/z 685), together with those due to adducts with Cl and HCOO" (m/z 721 and 731, respectively). 

Secoisolariciresinol diglucoside was isolated from flaxseed and analyzed on a 25°C C]g column (A = 280nm) using a 30-min 100/0- 70/30 water (lOmM phosphate at pH 2.8)/acetonitrile gradient [1219]. Peak shape was good as was the overall resolution. Standards of 20-160pg/mL were used. 

Clavel T, Lippman R, Gavini F, Dore J, Blaut M. Clostridium saccharogumia sp. nov. and Lactonifactor longooiformis gen. nov., sp. nov., two novel human faecal bacteria involved in the conversion of the dietary phytoestrogen secoisolariciresinol diglucoside. Syst Appl Microbiol. 2007 30 16-26. 

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