Secoisolariciresinol diglucoside

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Secoisolariciresinol diglucoside
Chemical structure of SDG
Names
Other names
SDG
Identifiers
158932-33-3 YesY
ChemSpider 8093627 YesY
Jmol 3D model Interactive image
PubChem 9917980
  • 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 YesY
    Key: SBVBJPHMDABKJV-PGCJWIIOSA-N YesY
  • 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
  • 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
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).
YesY verify (what is YesYN ?)
Infobox references

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

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.[4]

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.[5]

References

  1. ↑ 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
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ U.S. Patent 6,806,356 Process for recovering secoisolariciresinol diglycoside from de-fatted flaxseed.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.

External links

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