A lignan with diverse biological activities
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Secoisolariciresinol Diglucoside

Item No. 24974

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediyl bis-β-D-glucopyranoside
CAS Number
158932-33-3
Synonyms
  • SDG
Molecular Formula
C32H46O16
Formula Weight
686.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 5 mg/mlEthanol: 2 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
227, 279 nm
SMILES
O[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@H]1OC[C@]([C@@H](CC2=CC(OC)=C(O)C=C2)CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)([H])CC4=CC=C(O)C(OC)=C4
InChi Code
InChI=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
InChi Key
SBVBJPHMDABKJV-PGCJWIIOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $82

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    50 mg

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    100 mg

    $642

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    Cayman Chemical
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    Product Description

    Secoisolariciresinol diglucoside (SDG) is a lignan that has been found in flaxseed with antioxidant, antiproliferative, antidiabetic, and cardioprotective biological activities.1,2,3,4,5,6 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals (IC50 = 78.9 μg/ml) in a cell-free assay and dose-dependently inhibits the growth of SW480 human colon cancer cells in vitro.2,3 Dietary administration of SDG reduces the number of proliferating tumor cells in an MCF-7 human breast cancer mouse xenograft model in the presence of circulating estrogen.4 It also increases insulin and decreases glucose serum levels in rats with diabetes induced by streptozotocin (Item No. 13104) when administered at a dose of 20 mg/kg.5 SDG (20 mg/kg per day) decreases infarct size in rats with myocardial infarction induced by permanent occlusion of the left anterior descending coronary artery.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Imran, M., Ahmad, N., Anjum, F.M., et al. Potential protective properties of flax lignan secoisolariciresinol diglucoside. Nutr. J. 14:71, (2015).

    2. Moree, S.S., and Rajesha, J. Investigation of in vitro and in vivo antioxidant potential of secoisolariciresinol diglucoside. Mol. Cell Biochem. 373(1-2), 179-187 (2013).

    3. Ayella, A., Lim, S., Jiang, Y., et al. Cytostatic inhibition of cancer cell growth by lignan secoisolariciresinol diglucoside. Nutr. Res. 30(11), 762-769 (2010).

    4. Truan, J.S., Chen, J.-M., and Thompson, L.U. Comparative effects of sesame seed lignan and flaxseed lignan in reducing the growth of human breast tumors (MCF-7) at high levels of circulating estrogen in athymic mice. Nutr. Cancer 64(1), 65-71 (2012).

    5. Moree, S.S., Kavishankar, G.B., and Rajesha, J. Antidiabetic effect of secoisolariciresinol diglucoside in streptozotocin-induced diabetic rats. Phytomedicine 20(3-4), 237-245 (2013).

    6. Penumathsa, S.V., Koneru, S., Zhan, L., et al. Secoisolariciresinol diglucoside induces neovascularization-mediated cardioprotection against ischemia-reperfusion injury in hypercholesterolemic myocardium. J. Mol. Cell. Cardiol. 44(1), 170-179 (2008).