Secoisolariciresinol diglucoside
Antioxidant phytoestrogen
From Wikipedia, the free encyclopedia
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.
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| Names | |
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| 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) |
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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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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 be manipulated by different CYP enzymes in Eukaryotes. Due to its inherent size of 687Da, it will not pass the blood–brain barrier (which is somewhat limited to molecules smaller than 500Da).[citation needed]
In one histology group of adult patients with Grade IV malignant glioma, consuming secoisolariciresinol is associated with poorer survival outcomes, while for Grade III patients it is associated with more positive outcomes.[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]