| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg | |||
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| Other Sizes |
| Targets |
The primary targets of secoisolariciresinol diglucoside are not specific protein targets but rather the gut microbiota that convert it to the bioactive enterolignans. SDG is a precursor of the mammalian lignans enterodiol (ED) and enterolactone (EL), which are produced by intestinal bacteria through a series of metabolic reactions. These enterolignans have weak estrogenic and anti-estrogenic activities and can modulate estrogen receptor signaling. They also have antioxidant and anti-inflammatory properties, which may contribute to their health benefits. SDG itself is not considered to be the bioactive form but rather a prodrug that is activated by the gut microbiota.
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| ln Vitro |
Secoisolariciresinol diglucoside (1-500 μM) exhibits great reducing capacity and good free radical scavenging activity towards hydroxyl, peroxyl radicals and DPPH free radicals [1]. Secoisolariciresinol diglucoside (1-50 μM; 24 hours) attenuates human monocyte adherence and migration to human brain endothelial monolayers [2].
In vitro, secoisolariciresinol diglucoside is a plant lignan that is used as a research tool to study lignan metabolism and its biological activities. The compound itself has limited direct biological activity, as it requires conversion by gut microbiota to the bioactive enterolignans, enterodiol and enterolactone. However, in cell-based assays, SDG has been shown to have antioxidant activity and may modulate estrogen receptor signaling. It is also used in studies to investigate the metabolism of lignans and the role of gut microbiota in producing bioactive metabolites. |
| ln Vivo |
In neuroinflammation, a single oral dose of 4 mg/mouse of secoisolariciresinol diglucoside decreases leukocyte adherence and migration across the blood-brain barrier (BBB) [2].
In vivo, secoisolariciresinol diglucoside is converted by intestinal bacteria to enterodiol and subsequently to enterolactone, the putative bioactive forms. These mammalian lignans have been associated with various health benefits, including reduced risk of cardiovascular disease, breast cancer, and prostate cancer. SDG has been shown to decrease blood cholesterol levels in animal models. The compound is also used in pharmacokinetic studies to evaluate its absorption, metabolism, and the production of its bioactive metabolites. |
| Enzyme Assay |
Cell-free assays for secoisolariciresinol diglucoside are limited, as the compound requires conversion by gut microbiota to its bioactive metabolites. However, its antioxidant activity can be assessed using cell-free assays such as DPPH radical scavenging or ABTS radical cation decolorization assays. A typical protocol involves incubating the compound with the radical-generating system and measuring the decrease in absorbance. The IC50 value is determined by plotting the percentage of scavenging against the compound concentration. These assays provide a measure of the compound's intrinsic antioxidant capacity.
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| Cell Assay |
For in vitro cellular experiments, cells (e.g., cancer cell lines, intestinal epithelial cells) are cultured in appropriate media and treated with secoisolariciresinol diglucoside or its metabolites (enterodiol, enterolactone) at various concentrations (typically 1-100 uM). For estrogen receptor studies, cells expressing estrogen receptors are treated with the compound in the presence or absence of estradiol, and estrogen-responsive gene expression is measured by qRT-PCR or reporter gene assays. For antioxidant studies, cells are exposed to oxidative stress, and oxidative stress markers are measured. Cell viability is assessed using MTT or CCK-8 assays.
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| Animal Protocol |
Animal/Disease Models: Hand-fed mice (10 weeks old, male) were injected with TNFα[2].
Doses: 4 mg/mouse. Route of Administration: Po 2 hrs (hrs (hours)) before injection of TNFα. Experimental Results: The adhesion between leukocytes and endothelium was weakened by 50% and the penetration of leukocytes was weakened. Migration across the BBB increased by 64%. In vivo animal experiments with secoisolariciresinol diglucoside typically involve oral administration in rodents. A common dosing regimen is 10-50 mg/kg body weight, administered as a single dose or daily for 1-4 weeks. Blood, urine, and tissue samples are collected to measure the levels of SDG and its metabolites (SECO, ED, EL) using LC-MS/MS. Pharmacokinetic parameters, such as Cmax, Tmax, and AUC, are determined. For efficacy studies, animals are fed a high-fat diet or subjected to other disease models, and the effects of SDG on disease progression are assessed. |
| ADME/Pharmacokinetics |
Secoisolariciresinol diglucoside has a molecular weight of approximately 686 g/mol and a molecular formula of C32H46O16. As a glycosylated lignan, its oral bioavailability is limited, and it is primarily metabolized by the gut microbiota to its bioactive metabolites. The compound is stable as a powder and should be stored at -20degC. Its pharmacokinetic profile is characterized by conversion to enterodiol and enterolactone, which are absorbed and distributed to tissues. The enterolignans have a half-life of several hours and are excreted in urine and feces.
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| Toxicity/Toxicokinetics |
The toxicity profile of secoisolariciresinol diglucoside has been well characterized due to its widespread use as a dietary supplement. It is generally recognized as safe (GRAS) and is well-tolerated at dietary intake levels. High doses may cause gastrointestinal discomfort or other mild adverse effects. The compound has low acute toxicity and is not considered genotoxic or carcinogenic. It should be handled with standard laboratory precautions and is intended for research use.
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| References |
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| Additional Infomation |
Secoisolariciresinol diglucoside (SDG) (CAS 257930-74-8) is the principal lignan found in flaxseed and is a precursor of the mammalian lignans enterodiol (ED) and enterolactone (EL). It is converted by intestinal bacteria to these bioactive metabolites, which have been associated with reduced risk of cardiovascular disease, breast cancer, and prostate cancer. SDG has been shown to decrease blood cholesterol levels in animal models. It is used as a dietary supplement and in research to study lignan metabolism and its effects on chronic diseases. SDG is available as a research compound and is not approved for clinical use.
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| Molecular Formula |
C32H46O16
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| Molecular Weight |
686.698051929474
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| Exact Mass |
686.278
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| CAS # |
257930-74-8
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| Related CAS # |
Secoisolariciresinol;29388-59-8;(R,R)-Secoisolariciresinol diglucoside;158932-33-3;Secoisolariciresinol Monoglucoside;63320-67-2
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| PubChem CID |
72189390
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| Appearance |
White to off-white solid powder
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| LogP |
-0.7
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| Hydrogen Bond Donor Count |
10
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| Hydrogen Bond Acceptor Count |
16
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| Rotatable Bond Count |
15
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| Heavy Atom Count |
48
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| Complexity |
861
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| Defined Atom Stereocenter Count |
12
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| SMILES |
O([C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C[C@@H](CC1C=CC(=C(C=1)OC)O)[C@H](CC1C=CC(=C(C=1)OC)O)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
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| InChi Key |
SBVBJPHMDABKJV-NNSPVXBOSA-N
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| 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-/m1/s1
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| Chemical Name |
(2R,3R,4S,5S,6R)-2-[(2S,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ≥ 100 mg/mL (~145.62 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 50 mg/mL (72.81 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.4562 mL | 7.2812 mL | 14.5624 mL | |
| 5 mM | 0.2912 mL | 1.4562 mL | 2.9125 mL | |
| 10 mM | 0.1456 mL | 0.7281 mL | 1.4562 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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