| 词条 | Secoisolariciresinol diglucoside |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 448843590 | Name = | ImageFile = Secoisolarisiresinol diglucoside.svg | ImageName = Chemical structure of SDG | IUPACName = | OtherNames = SDG |Section1={{Chembox Identifiers | CASNo = 158932-33-3 | CASNo_Ref = {{cascite|correct|??}} | CASNoOther = | UNII_Ref = {{fdacite|changed|FDA}} | UNII = T9281L29MV | 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 | Formula = C32H46O16 | MolarMass = 686.7 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} }} 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. ExtractionSecoisolariciresinol 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] Or, it can be extracted from the shell of whole flax through a cold-milled process without using chemicals. Studies on biological effectsSecoisolariciresinol diglucoside slows the growth of human breast cancer in mice.[5] Secoisolariciresinol diglucoside may play very different role in people with the already existent cancer. In the 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] Note however that glioma is located behind the Blood–brain barrier in which larger molecules such as SDG may not penetrate efficiently. In rabits 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.[8] References1. ^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. http://doi.org/10.1017/S0007114509992753 2. ^Phenolic glucosides in bread containing flaxseed. C. Strandås, A. Kamal-Eldin, R. Andersson and P. Åman, Food Chemistry, Volume 110, Issue 4, 15 October 2008, Pages 997–999, {{doi|10.1016/j.foodchem.2008.02.088}} 3. ^{{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}} 4. ^{{US patent|6806356}} Process for recovering secoisolariciresinol diglycoside from de-fatted flaxseed. 5. ^{{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 }} 6. ^{{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 |url=http://www.biomedcentral.com/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 }} 7. ^{{Cite journal|doi = 10.1161/01.CIR.99.10.1355|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}} 8. ^file:///Users/kurtiscollins/Downloads/CWSF_Report_Kurtis_Collins/CWSF_Report_Kurtis_Collins.html External links
2 : Lignans|Phenol glucosides |
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