Secoisolariciresinol diglucoside

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Secoisolariciresinol diglucoside
Chemical structure of SDG
Names
IUPAC name
(8R,8′R)-4,4′-Dihydroxy-3,3′-dimethoxylignane-9,9′-diyl di(β-D-glucopyranoside)
Systematic IUPAC name
(2R,2′R,3R,3′R,4S,4′S,5S,5′S,6R,6′R)-2,2′-[{(2R,3R)-2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diyl}bis(oxy)]bis[6-(hydroxymethyl)oxane-3,4,5-triol]
Other names
SDG
Identifiers
3D model (JSmol)
ChemSpider
KEGG
UNII
  • 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 checkY
    Key: SBVBJPHMDABKJV-PGCJWIIOSA-N checkY
  • 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 686.704 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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]

Studies on biological effects

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]

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. doi:10.1017/S0007114509992753. PMID 20003621.{{cite journal}}: 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. PMID 26047292.{{cite journal}}: 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. ^ Puukila, S.; Bryan, S.; Laakso, A.; Abdel-Malak, J.; Gurney, C.; Agostino, A.; Belló-Klein, A.; Prasad, K.; Khaper, N. (2015). "Secoisolariciresinol diglucoside abrogates oxidative stress-induced damage in cardiac iron overload condition". PLOS ONE. 10 (3): e0122852. Bibcode:2015PLoSO..1022852P. doi:10.1371/journal.pone.0122852. PMC 4379144. PMID 25822525.
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