Secoisolariciresinol diglucoside

Secoisolariciresinol diglucoside

Names
Other names SDG
Identifiers
CAS Number	158932-33-3
3D model (Jmol)	Interactive image
ChemSpider	8093627
PubChem	9917980
UNII	T9281L29MV
InChI InChI=1S/C32H46O16/c1-43-21-9-15(3-5-19(21)35)7-17(13-45-31-29(41)27(39)25(37)23(11-33)47-31)18(8-16-4-6-20(36)22(10-16)44-2)14-46-32-30(42)28(40)26(38)24(12-34)48-32/h3-6,9-10,17-18,23-42H,7-8,11-14H2,1-2H3/t17-,18-,23+,24+,25+,26+,27-,28-,29+,30+,31+,32+/m0/s1 Key: SBVBJPHMDABKJV-PGCJWIIOSA-N InChI=1/C32H46O16/c1-43-21-9-15(3-5-19(21)35)7-17(13-45-31-29(41)27(39)25(37)23(11-33)47-31)18(8-16-4-6-20(36)22(10-16)44-2)14-46-32-30(42)28(40)26(38)24(12-34)48-32/h3-6,9-10,17-18,23-42H,7-8,11-14H2,1-2H3/t17-,18-,23+,24+,25+,26+,27-,28-,29+,30+,31+,32+/m0/s1 Key: SBVBJPHMDABKJV-PGCJWIIOBK
SMILES OC1=C(OC)C=C(C[C@H]([C@H](CO[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)CC3=CC(OC)=C(O)C=C3)CO[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O4)C=C1
Properties
Chemical formula	C32H46O16
Molar mass	686.7 g/mol
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.

Extraction

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

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

Secoisolariciresinol diglucoside may play very different role in people with the already existent cancer. In the 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]

References

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. http://doi.org/10.1017/S0007114509992753
2. Phenolic glucosides in bread containing flaxseed. C. Strandås, A. Kamal-Eldin, R. Andersson and P. Åman, Food Chemistry, Volume 110, Issue 4, 15 October 2008, Pages 997–999, doi:10.1016/j.foodchem.2008.02.088
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. U.S. Patent 6,806,356 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. BMC Cancer. 10: 215. doi:10.1186/1471-2407-10-215. PMC 2880992. PMID 20482871.

External links

• Flaxseed Lignans & the Immune System Lists many academic sources.