Secoisolariciresinol diglucoside

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Secoisolariciresinol diglucoside
Chemical structure of SDG
Other names
3D model (JSmol)
Molar mass 686.704 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Secoisolariciresinol diglucoside (SDG) is an antioxidant[1] phytoestrogen present in flax, sunflower, sesame, and pumpkin seeds. In food, it can be found in commercial breads containing flaxseed.[2] It is a precursor of mammal lignans[3] which are produced in the colon from chemicals in foods.


Secoisolariciresinol diglucoside can be isolated from de-fatted (hexane extraction) flaxseed by extraction of the lignan polymer precursor with a water/acetone mixture, followed by acetone removal and alkaline hydrolysis.[4]

Or, it can be extracted from the shell of whole flax through a cold-milled process without using chemicals.

Studies on biological effects[edit]

Secoisolariciresinol diglucoside slows the growth of human breast cancer in mice.[5]

Secoisolariciresinol diglucoside may different roles in people. For example, due to 400-500Da size limit for Blood–Brain Barrier permeability, in one assessment of a Grade IV histology group of adult patients diagnosed with malignant glioma, high intake of secoisolariciresinol (for highest tertile compared to lowest tertile, in all cases) was associated with poorer survival.[6]

In rabbits, SDG reduced hypercholesterolemic atherosclerosis and this effect was associated with a decrease in serum cholesterol, LDL-C, and lipid peroxidation product and an increase in HDL-C and antioxidant reserve.[7]

SDG has been shown to counter oxidative stress in human colonic epithelial tissue and protect against mtDNA damage in vitro, by H2O2 exposure, in a dose-dependent manner[citation needed], and counters (in-vitro) oxidative stress on heart cells caused by Iron overload[8].


  1. ^ Adolphe, J. L., Whiting, S. J., Juurlink, B. H. J., Thorpe, L. U., & Alcorn, J. (2010). "Health effects with consumption of the flax lignan secoisolariciresinol diglucoside". The British Journal of Nutrition. 103 (7): 929–38. doi:10.1017/S0007114509992753. PMID 20003621.CS1 maint: multiple names: authors list (link)
  2. ^ C. Strandås, A. Kamal-Eldin, R. Andersson and P. Åman (2008). "Phenolic glucosides in bread containing flaxseed". Food Chemistry. 110 (4): 997–999. doi:10.1016/j.foodchem.2008.02.088.CS1 maint: multiple names: authors list (link)
  3. ^ Thompson, LU; Robb, P; Serraino, M; Cheung, F (1991). "Mammalian lignan production from various foods". Nutrition and Cancer. 16 (1): 43–52. doi:10.1080/01635589109514139. PMID 1656395.
  4. ^ US 6806356, "Process for recovering secoisolariciresinol diglycoside from de-fatted flaxseed" 
  5. ^ Chen; et al. (2009). "Flaxseed and Pure Secoisolariciresinol Diglucoside, but Not Flaxseed Hull, Reduce Human Breast Tumor Growth (MCF-7) in Athymic Mice". The Journal of Nutrition. 139 (11): 2061–6. doi:10.3945/jn.109.112508. PMID 19776177.
  6. ^ Delorenze, Gerald N; McCoy, Lucie; Tsai, Ai-Lin; Quesenberry Jr, Charles P; Rice, Terri; Il'Yasova, Dora; Wrensch, Margaret (2010). "Daily intake of antioxidants in relation to survival among adult patients diagnosed with malignant glioma". BMC Cancer. 10: 215. doi:10.1186/1471-2407-10-215. PMC 2880992. PMID 20482871.
  7. ^ Prasad, K (1999). "Reduction of Serum Cholesterol and Hypercholesterolemic Atherosclerosis in Rabbits by Secoisolariciresinol Diglucoside Isolated from Flaxseed". Circulation. 99 (10): 1355–1362. doi:10.1161/01.CIR.99.10.1355. PMID 10077521.
  8. ^ "Secoisolariciresinol diglucoside abrogates oxidative stress-induced damage in cardiac iron overload condition". PMID 25822525. Cite journal requires |journal= (help)