secoisolariciresinol diglucoside
{{Short description|Antioxidant phytoestrogen}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 448843590
| Name =
| ImageFile = Secoisolarisiresinol diglucoside.svg
| ImageName = Chemical structure of SDG
| IUPACName = (8R,8′R)-4,4′-Dihydroxy-3,3′-dimethoxylignane-9,9′-diyl di(β-D-glucopyranoside)
| SystematicName = (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]
| OtherNames = SDG
|Section1={{Chembox Identifiers
| CASNo = 158932-33-3
| CASNo_Ref = {{cascite|correct|??}}
| CASNoOther =
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = T9281L29MV
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C22584
| SMILES = 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
| PubChem = 9917980
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8093627
| 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
| InChIKey = SBVBJPHMDABKJV-PGCJWIIOBK
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SBVBJPHMDABKJV-PGCJWIIOSA-N
| MeSHName =
}}
|Section2={{Chembox Properties
| C = 32
| H = 46
| O = 16
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
}}
Secoisolariciresinol diglucoside (SDG) is an antioxidant{{cite journal | author = Adolphe, J. L., Whiting, S. J., Juurlink, B. H. J., Thorpe, L. U., & Alcorn, J. | date = 2010 | title = Health effects with consumption of the flax lignan secoisolariciresinol diglucoside | journal = The British Journal of Nutrition | volume = 103 | issue = 7 | pages = 929–38 | doi = 10.1017/S0007114509992753 | pmid = 20003621 | doi-access = free }} phytoestrogen present in flax, sunflower, sesame, and pumpkin seeds. In food, it can be found in commercial breads containing flaxseed.{{cite journal | title = Phenolic glucosides in bread containing flaxseed | author = C. Strandås, A. Kamal-Eldin, R. Andersson and P. Åman | journal = Food Chemistry| volume = 110 | issue = 4 | date = 2008 | pages = 997–999 | doi = 10.1016/j.foodchem.2008.02.088| pmid = 26047292 }} It is a precursor of mammal lignans{{cite journal | pmid = 1656395 | year = 1991 | last1 = Thompson | first1 = LU | last2 = Robb | first2 = P | last3 = Serraino | first3 = M | last4 = Cheung | first4 = F | title = Mammalian lignan production from various foods | volume = 16 | issue = 1 | pages = 43–52 | doi = 10.1080/01635589109514139 | journal = Nutrition and Cancer}} 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.{{cite patent | number = 6806356 | country = US | title = Process for recovering secoisolariciresinol diglycoside from de-fatted flaxseed }}
Studies on biological effects
Secoisolariciresinol diglucoside slows the growth of human breast cancer in mice.{{cite journal |url=http://jn.nutrition.org/content/139/11/2061.full |title=Flaxseed and Pure Secoisolariciresinol Diglucoside, but Not Flaxseed Hull, Reduce Human Breast Tumor Growth (MCF-7) in Athymic Mice |author=Chen |year=2009 |display-authors=1 |pmid=19776177 |doi=10.3945/jn.109.112508 |last2=Saggar |first2=JK |last3=Corey |first3=P |last4=Thompson |first4=LU |volume=139 |issue=11 |pages=2061–6 |journal=The Journal of Nutrition |doi-access=free }}
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).{{cite journal |title=Daily intake of antioxidants in relation to survival among adult patients diagnosed with malignant glioma |year=2010 |doi=10.1186/1471-2407-10-215 |last1=Delorenze |first1=Gerald N |last2=McCoy |first2=Lucie |last3=Tsai |first3=Ai-Lin |last4=Quesenberry Jr |first4=Charles P |last5=Rice |first5=Terri |last6=Il'Yasova |first6=Dora |last7=Wrensch |first7=Margaret |journal=BMC Cancer |volume=10 |pages=215 |pmid=20482871 |pmc=2880992 |doi-access=free }} 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.{{Cite journal|doi = 10.1161/01.CIR.99.10.1355|pmid = 10077521|title = Reduction of Serum Cholesterol and Hypercholesterolemic Atherosclerosis in Rabbits by Secoisolariciresinol Diglucoside Isolated from Flaxseed|journal = Circulation|volume = 99|issue = 10|pages = 1355–1362|year = 1999|last1 = Prasad|first1 = K|doi-access = free}}
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|date=July 2019}}, and counters (in-vitro) oxidative stress on heart cells caused by Iron overload.{{cite journal |pmid=25822525|title=Secoisolariciresinol diglucoside abrogates oxidative stress-induced damage in cardiac iron overload condition |year=2015 |last1=Puukila |first1=S. |last2=Bryan |first2=S. |last3=Laakso |first3=A. |last4=Abdel-Malak |first4=J. |last5=Gurney |first5=C. |last6=Agostino |first6=A. |last7=Belló-Klein |first7=A. |last8=Prasad |first8=K. |last9=Khaper |first9=N. |journal=PLOS ONE |volume=10 |issue=3 |pages=e0122852 |doi=10.1371/journal.pone.0122852 |pmc=4379144 |bibcode=2015PLoSO..1022852P |doi-access=free }}