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 | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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.
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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cite journal}}
: CS1 maint: multiple names: authors list (
link)
{{
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: CS1 maint: multiple names: authors list (
link)
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 | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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.
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]
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)