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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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 | |
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3D model (JSmol)
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PubChem CID
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UNII |
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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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Infobox references
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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]
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]
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