Secoisolariciresinol diglucoside
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| IUPAC name
(8R,8′R)-4,4′-Dihydroxy-3,3′-dimethoxylignane-9,9′-diyl di(β-D-glucopyranoside)
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| 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
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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).
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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
[edit]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
[edit]Secoisolariciresinol diglucoside slows the growth of human breast cancer in mice.[5]
Secoisolariciresinol diglucoside may be manipulated by different CYP enzymes in Eukaryotes. Due to it's inherent size of 687Da, it will not pass the Blood–Brain Barrier (which is somewhat limited to molecules smaller than 500Da). For example, in one Histology group of adult patients with malignant glioma (Grade IV), consuming Secoisolariciresinol, resulted in 'poorer' survival outcomes, while the Grade III patients resulted in more positive outcomes (SDG with vitamin E).[6] In other malignancies, of soft tissue and osteogenic origin, SDG and matairesinol metabolites derivatives show physicochemical features that may yield further investigative advances.
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
[edit]- ^ 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) - ^ 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) - ^ 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.
- ^ US 6806356, "Process for recovering secoisolariciresinol diglycoside from de-fatted flaxseed"
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.