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MedKoo Cat#: 529604 | Name: Secoisolariciresinol diglucoside
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Secoisolariciresinol diglucoside (SDG) is a lignan that has been found in flaxseed with antioxidant, antiproliferative, antidiabetic, and cardioprotective biological activities.

Chemical Structure

Secoisolariciresinol diglucoside
Secoisolariciresinol diglucoside
CAS#158932-33-3

Theoretical Analysis

MedKoo Cat#: 529604

Name: Secoisolariciresinol diglucoside

CAS#: 158932-33-3

Chemical Formula: C32H46O16

Exact Mass: 686.2786

Molecular Weight: 686.70

Elemental Analysis: C, 55.97; H, 6.75; O, 37.28

Price and Availability

Size Price Availability Quantity
5mg USD 280.00 2 weeks
10mg USD 450.00 2 weeks
20mg USD 600.00 2 weeks
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Related CAS #
No Data
Synonym
SDG
IUPAC/Chemical Name
(2R,2'R,3S,3'S,4S,4'S,5R,5'R,6R,6'R)-6,6'-(((2R,3R)-2,3-bis(4-hydroxy-3-methoxybenzyl)butane-1,4-diyl)bis(oxy))bis(2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol)
InChi Key
SBVBJPHMDABKJV-PGCJWIIOSA-N
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
SMILES Code
O[C@H]1[C@H](OC[C@H](CC2=CC=C(O)C(OC)=C2)[C@@H](CC3=CC=C(O)C(OC)=C3)CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)O[C@H](CO)[C@@H](O)[C@@H]1O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, DMF, and ethanol
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
SDG scavenges 2,2-diphenyl-1-picrylhydrazyl radicals (IC50 = 78.9 μg/ml) and dose-dependently inhibits the growth of SW480 human colon cancer cells in vitro. Dietary administration of SDG reduces the number of proliferating tumor cells in an MCF-7 human breast cancer mouse xenograft model. It also increases insulin and decreases glucose serum levels in rats with diabetes induced by streptozotocin. SDG decreases infarct size in rats with myocardial infarction.
In vitro activity:
In this study, SDG led to a dose- and time-dependent reduction in human colonic SW480 cancer cell numbers. SDG demonstrated similar effects on cell growth, cytotoxicity, and cell cycle arrest compared to enterolactone, its metabolite. However, only enterolactone was detected intracellularly in SW480 cells, suggesting that the metabolism of SDG, if exposed directly to colonic cells, might differ from its known degradation by gut microorganisms. Reference: Nutr Res. 2010 Nov;30(11):762-9. https://pubmed.ncbi.nlm.nih.gov/21130295/
In vivo activity:
In a postmenopausal osteoporosis rat model, SDG lessened the injury of bone and improve femoral parameters, including bone mineral content (BMC) and bone mineral density (BMD). Pathological results showed SDG could reduce pathological injury of femur in OVX rats. Meanwhile, SDG decreased the level of IL-6 and regulated bone formation and bone catabolism indexes. Besides, SDG increased the level of E2 and conversed OVX-induced decreased the expression of ERα and ERβ. Reference: J Orthop Surg Res. 2023 Oct 24;18(1):792. https://pubmed.ncbi.nlm.nih.gov/37875947/
Solvent mg/mL mM
Solubility
DMF 10.0 14.56
DMSO 5.0 7.28
Ethanol 2.0 2.91
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 686.70 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Özgöçmen M, Bayram D, Yavuz Türel G, Toğay VA, Şahin Calapoğlu N. Secoisolariciresinol diglucoside induces caspase-3-mediated apoptosis in monolayer and spheroid cultures of human colon carcinoma cells. J Food Biochem. 2021 May;45(5):e13719. doi: 10.1111/jfbc.13719. Epub 2021 Mar 29. PMID: 33778961. 2. Ayella A, Lim S, Jiang Y, Iwamoto T, Lin D, Tomich J, Wang W. Cytostatic inhibition of cancer cell growth by lignan secoisolariciresinol diglucoside. Nutr Res. 2010 Nov;30(11):762-9. doi: 10.1016/j.nutres.2010.10.002. PMID: 21130295. 3. Yang XY, Wu DD, Zhuang CC, Ma CM. Anti-osteoporosis effects of mammalian lignans and their precursors from flaxseed and safflower seed using zebrafish model. J Food Sci. 2023 Oct 27. doi: 10.1111/1750-3841.16816. Epub ahead of print. PMID: 37889085. 4. Chen G, Chen Y, Hong J, Gao J, Xu Z. Secoisolariciresinol diglucoside regulates estrogen receptor expression to ameliorate OVX-induced osteoporosis. J Orthop Surg Res. 2023 Oct 24;18(1):792. doi: 10.1186/s13018-023-04284-5. PMID: 37875947; PMCID: PMC10594807.
In vitro protocol:
1. Özgöçmen M, Bayram D, Yavuz Türel G, Toğay VA, Şahin Calapoğlu N. Secoisolariciresinol diglucoside induces caspase-3-mediated apoptosis in monolayer and spheroid cultures of human colon carcinoma cells. J Food Biochem. 2021 May;45(5):e13719. doi: 10.1111/jfbc.13719. Epub 2021 Mar 29. PMID: 33778961. 2. Ayella A, Lim S, Jiang Y, Iwamoto T, Lin D, Tomich J, Wang W. Cytostatic inhibition of cancer cell growth by lignan secoisolariciresinol diglucoside. Nutr Res. 2010 Nov;30(11):762-9. doi: 10.1016/j.nutres.2010.10.002. PMID: 21130295.
In vivo protocol:
1. Yang XY, Wu DD, Zhuang CC, Ma CM. Anti-osteoporosis effects of mammalian lignans and their precursors from flaxseed and safflower seed using zebrafish model. J Food Sci. 2023 Oct 27. doi: 10.1111/1750-3841.16816. Epub ahead of print. PMID: 37889085. 2. Chen G, Chen Y, Hong J, Gao J, Xu Z. Secoisolariciresinol diglucoside regulates estrogen receptor expression to ameliorate OVX-induced osteoporosis. J Orthop Surg Res. 2023 Oct 24;18(1):792. doi: 10.1186/s13018-023-04284-5. PMID: 37875947; PMCID: PMC10594807.
1: Pietrofesa RA, Velalopoulou A, Albelda SM, Christofidou-Solomidou M. Asbestos Induces Oxidative Stress and Activation of Nrf2 Signaling in Murine Macrophages: Chemopreventive Role of the Synthetic Lignan Secoisolariciresinol Diglucoside (LGM2605). Int J Mol Sci. 2016 Mar 1;17(3):322. doi: 10.3390/ijms17030322. PubMed PMID: 26938529; PubMed Central PMCID: PMC4813184. 2: Tan ZJ, Wang CY, Yang ZZ, Yi YJ, Wang HY, Zhou WL, Li FF. Ionic Liquid-Based Ultrasonic-Assisted Extraction of Secoisolariciresinol Diglucoside from Flaxseed (Linum usitatissimum L.) with Further Purification by an Aqueous Two-Phase System. Molecules. 2015 Sep 30;20(10):17929-43. doi: 10.3390/molecules201017929. PubMed PMID: 26437389. 3: Prasad K, Jadhav A. Prevention and treatment of atherosclerosis with flaxseed-derived compound secoisolariciresinol diglucoside. Curr Pharm Des. 2016;22(2):214-20. Review. PubMed PMID: 26561066. 4: Pietrofesa RA, Velalopoulou A, Arguiri E, Menges CW, Testa JR, Hwang WT, Albelda SM, Christofidou-Solomidou M. Flaxseed lignans enriched in secoisolariciresinol diglucoside prevent acute asbestos-induced peritoneal inflammation in mice. Carcinogenesis. 2016 Feb;37(2):177-87. doi: 10.1093/carcin/bgv174. PubMed PMID: 26678224; PubMed Central PMCID: PMC4745643. 5: Velalopoulou A, Tyagi S, Pietrofesa RA, Arguiri E, Christofidou-Solomidou M. The Flaxseed-Derived Lignan Phenolic Secoisolariciresinol Diglucoside (SDG) Protects Non-Malignant Lung Cells from Radiation Damage. Int J Mol Sci. 2015 Dec 22;17(1). pii: E7. doi: 10.3390/ijms17010007. PubMed PMID: 26703588; PubMed Central PMCID: PMC4730254. 6: Imran M, Ahmad N, Anjum FM, Khan MK, Mushtaq Z, Nadeem M, Hussain S. Potential protective properties of flax lignan secoisolariciresinol diglucoside. Nutr J. 2015 Jul 28;14:71. doi: 10.1186/s12937-015-0059-3. Review. PubMed PMID: 26215288; PubMed Central PMCID: PMC4517353. 7: Fang J, Ramsay A, Renouard S, Hano C, Lamblin F, Chabbert B, Mesnard F, Schneider B. Laser Microdissection and Spatiotemporal Pinoresinol-Lariciresinol Reductase Gene Expression Assign the Cell Layer-Specific Accumulation of Secoisolariciresinol Diglucoside in Flaxseed Coats. Front Plant Sci. 2016 Nov 21;7:1743. PubMed PMID: 27917190; PubMed Central PMCID: PMC5116464. 8: Shim YY, Olivia CM, Liu J, Boonen R, Shen J, Reaney MJ. Secoisolariciresinol Diglucoside and Cyanogenic Glycosides in Gluten-free Bread Fortified with Flaxseed Meal. J Agric Food Chem. 2016 Dec 21;64(50):9551-9558. doi: 10.1021/acs.jafc.6b03962. PubMed PMID: 27998066. 9: Mishra OP, Popov AV, Pietrofesa RA, Christofidou-Solomidou M. Gamma-irradiation produces active chlorine species (ACS) in physiological solutions: Secoisolariciresinol diglucoside (SDG) scavenges ACS - A novel mechanism of DNA radioprotection. Biochim Biophys Acta. 2016 Sep;1860(9):1884-97. doi: 10.1016/j.bbagen.2016.05.037. PubMed PMID: 27261092; PubMed Central PMCID: PMC5253237. 10: Shah NR, Patel BM. Secoisolariciresinol diglucoside rich extract of L. usitatissimum prevents diabetic colon cancer through inhibition of CDK4. Biomed Pharmacother. 2016 Oct;83:733-739. doi: 10.1016/j.biopha.2016.07.041. PubMed PMID: 27470575. 11: Puukila S, Bryan S, Laakso A, Abdel-Malak J, Gurney C, Agostino A, Belló-Klein A, Prasad K, Khaper N. Secoisolariciresinol diglucoside abrogates oxidative stress-induced damage in cardiac iron overload condition. PLoS One. 2015 Mar 30;10(3):e0122852. doi: 10.1371/journal.pone.0122852. PubMed PMID: 25822525; PubMed Central PMCID: PMC4379144. 12: Sherif IO. Secoisolariciresinol diglucoside in high-fat diet and streptozotocin-induced diabetic nephropathy in rats: a possible renoprotective effect. J Physiol Biochem. 2014 Dec;70(4):961-9. doi: 10.1007/s13105-014-0364-x. PubMed PMID: 25316298. 13: Zanwar AA, Hegde MV, Rojatkar SR, Sonawane KB, Rajamohanan PR, Bodhankar SL. Isolation, characterization and antihyperlipidemic activity of secoisolariciresinol diglucoside in poloxamer-407-induced experimental hyperlipidemia. Pharm Biol. 2014 Sep;52(9):1094-103. doi: 10.3109/13880209.2013.877492. PubMed PMID: 24649910. 14: Tao YL, Yang DH, Zhang YT, Zhang Y, Wang ZQ, Wang YS, Cai SQ, Liu SL. Cloning, expression, and characterization of the β-glucosidase hydrolyzing secoisolariciresinol diglucoside to secoisolariciresinol from Bacteroides uniformis ZL1. Appl Microbiol Biotechnol. 2014 Mar;98(6):2519-31. doi: 10.1007/s00253-013-5111-7. PubMed PMID: 23942877. 15: Edel AL, Patenaude AF, Richard MN, Dibrov E, Austria JA, Aukema HM, Pierce GN, Aliani M. The effect of flaxseed dose on circulating concentrations of alpha-linolenic acid and secoisolariciresinol diglucoside derived enterolignans in young, healthy adults. Eur J Nutr. 2016 Mar;55(2):651-63. doi: 10.1007/s00394-015-0885-2. PubMed PMID: 25808116. 16: Moree SS, Kavishankar GB, Rajesha J. Antidiabetic effect of secoisolariciresinol diglucoside in streptozotocin-induced diabetic rats. Phytomedicine. 2013 Feb 15;20(3-4):237-45. doi: 10.1016/j.phymed.2012.11.011. PubMed PMID: 23271000. 17: Fang J, Ramsay A, Paetz C, Tatsis EC, Renouard S, Hano C, Grand E, Fliniaux O, Roscher A, Mesnard F, Schneider B. Concentration kinetics of secoisolariciresinol diglucoside and its biosynthetic precursor coniferin in developing flaxseed. Phytochem Anal. 2013 Jan-Feb;24(1):41-6. doi: 10.1002/pca.2377. PubMed PMID: 22689568. 18: Christofidou-Solomidou M, Tyagi S, Pietrofesa R, Dukes F, Arguiri E, Turowski J, Grieshaber PA, Solomides CC, Cengel KA. Radioprotective role in lung of the flaxseed lignan complex enriched in the phenolic secoisolariciresinol diglucoside (SDG). Radiat Res. 2012 Dec;178(6):568-80. doi: 10.1667/RR2980.1. PubMed PMID: 23106213; PubMed Central PMCID: PMC3534769. 19: Moree SS, Rajesha J. Investigation of in vitro and in vivo antioxidant potential of secoisolariciresinol diglucoside. Mol Cell Biochem. 2013 Jan;373(1-2):179-87. doi: 10.1007/s11010-012-1487-4. PubMed PMID: 23108790. 20: Li XW, Yang JR. [Effects of secoisolariciresinol diglucoside combined with bortezomib on induction of apoptosis in lung cancer cell line A549]. Zhong Yao Cai. 2012 Feb;35(2):248-53. Chinese. PubMed PMID: 22822672.