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Secoisolariciresinol
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Product Name Secoisolariciresinol
Price: $288 / 10mg
CAS No.: 29388-59-8
Catalog No.: CFN98363
Molecular Formula: C20H26O6
Molecular Weight: 362.4 g/mol
Purity: >=98%
Type of Compound: Lignans
Physical Desc.: Powder
Source: The heartwoods of Podocarpus spicata
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download: COA    MSDS    SDF    Manual
Similar structural: Comparison (Web)  (SDF)
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Size /Price /Stock 10 mM * 1 mL in DMSO / $120.4 / In-stock
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Biological Activity
Description: Secoisolariciresinol is an enterolignan precursor, it has antioxidant, and estrogen-like activities, it can significantly suppress triglyceride (TG) accumulation in 3T3-L1 adipocytes. Secoisolariciresinol prevents d-GalN/LPS-induced hepatic injury by inhibiting hepatocyte apoptosis through the blocking of TNF-alpha and IFN-gamma production by activated macrophages and direct inhibition of the apoptosis induced by TNF-alpha. (-)-Secoisolariciresinol exerts a suppressive effect on the gain of body weight of mice fed a high-fat diet by inducing gene expression of adiponectin, resulting in the altered expression of various genes related to the synthesis and β-oxidation of fatty acids.
Targets: IFN-γ | TNF-α | Estrogen receptor | Progestogen receptor
In vitro:
Biosci Biotechnol Biochem. 2009 Jan;73(1):35-9.
The Effect of Secoisolariciresinol on 3T3-L1 Adipocytes and the Relationship between Molecular Structure and Activity.[Pubmed: 19129664 ]
As we have reported, flaxseed lignan, (+)-Secoisolariciresinol (SECO), (-)-SECO, and meso-SECO were stereoselectively synthesized and their biological functions were evaluated.
METHODS AND RESULTS:
In the present study, we focused on the effects of SECOs on the regulation of 3T3-L1 adipocytes, and identified the structure-activity relationships. Optically active SECO and meso-SECO were tested for their effects on lipid metabolism in 3T3-L1 adipocytes. (-)-SECO accelerated adiponectin production of 3T3-L1 adipocytes. On the other hand, (+)- and meso-SECO suppressed the production of adiponectin. In addition, triglyceride (TG) accumulation in 3T3-L1 adipocytes was significantly suppressed by all three SECOs tested here, as was 17beta-estradiol, when the SECOs were added to the medium during induction of 3T3-L1 preadipocytes to adipocytes. Especially, (-)-SECO strongly reduced TG accumulation.
CONCLUSIONS:
It is well-known that SECO has estrogen-like activity. Hence the estrogen-like activity of each SECO compound was assessed. Only (-)-SECO had estrogen-like activity.
Int J Angiol. 2000 Oct;9(4):220-225.
Antioxidant Activity of Secoisolariciresinol Diglucoside-derived Metabolites, Secoisolariciresinol, Enterodiol, and Enterolactone.[Pubmed: 11062311]

METHODS AND RESULTS:
Secoisolariciresinol diglucoside (SDG), an antioxidant isolated from flaxseed, is metabolized to Secoisolariciresinol (SECO), enterodiol (ED), and enterolactone (EL) in the body. The effectiveness of SDG in hypercholesterolemic atherosclerosis, diabetes, and endotoxic shock could be due to these metabolites. These metabolites may have antioxidant activity. However, the antioxidant activity of these metabolites is not known. The antioxidant activity of SECO, ED, and EL was investigated using chemiluminescence (CL) of zymosan-activated polymorphonuclear leukocytes (PMNLs) [PMNL-CL]. Other antioxidants (SDG and vitamin E) were also used for comparison. SDG, SECO, ED, EL, and vitamin E, each in the concentration of 0.5, 1.0, 2.5, 5.0 and 10.0 mg/ml, produced a concentration-dependent reduction in zymosan-activated PMNL-CL. SDG, SECO, ED, EL, and vitamin E, in the concentration of 2.5 mg/ml, produced a reduction of zymosan-activated PMNL-CL by 23.8%, 91.2%, 94.2%, 81.6% and 18.7%, respectively. Activated PMNLs produce reactive oxygen species and luminol-dependent CL reflects the amount of oxygen species generated from activated PMNLs. The reduction of PMNL-CL, therefore, reflects the antioxidant activity of the compounds studied.
CONCLUSIONS:
These results suggest that the metabolites of SDG have antioxidant activity. The antioxidant activity was highest with SECO and ED and lowest with vitamin E. The antioxidant potency of SECO, ED, EL, and SDG was 4.86, 5.02, 4.35, and 1.27 respectively, as compared to vitamin E. SECO, ED and EL are respectively 3.82, 3.95, and 3.43 more potent than SDG.
In vivo:
Food Funct. 2014 Mar;5(3):491-501.
Metabolism of secoisolariciresinol-diglycoside the dietary precursor to the intestinally derived lignan enterolactone in humans.[Pubmed: 24429845]
Secoisolariciresinol-diglycoside (SDG), a natural dietary lignan of flaxseeds now available in dietary supplements, is converted by intestinal bacteria to the mammalian lignans enterodiol and enterolactone.
METHODS AND RESULTS:
Our objective was to determine the bioavailability and pharmacokinetics of Secoisolariciresinol-diglycoside in purified flaxseed extracts under dose-ranging and steady-state conditions, and to examine whether differences in Secoisolariciresinol-diglycoside purity influence bioavailability. Pharmacokinetic studies were performed on healthy postmenopausal women after oral intake of 25, 50, 75, 86 and 172 mg of Secoisolariciresinol-diglycoside. Extracts differing in Secoisolariciresinol-diglycoside purity were compared, and steady-state lignan concentrations measured after daily intake for one week. Blood and urine samples were collected at timed intervals and Secoisolariciresinol, enterodiol and enterolactone concentrations measured by mass spectrometry. Secoisolariciresinol-diglycoside was efficiently hydrolyzed and converted to Secoisolariciresinol.
CONCLUSIONS:
This study defines the pharmacokinetics of Secoisolariciresinol-diglycoside and shows it is first hydrolyzed and then metabolized in a time-dependent sequence to Secoisolariciresinol, enterodiol and ultimately enterolactone, and these metabolites are efficiently absorbed.
Secoisolariciresinol Description
Source: The heartwoods of Podocarpus spicata
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

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After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

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Calculate Dilution Ratios(Only for Reference)
1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7594 mL 13.7969 mL 27.5938 mL 55.1876 mL 68.9845 mL
5 mM 0.5519 mL 2.7594 mL 5.5188 mL 11.0375 mL 13.7969 mL
10 mM 0.2759 mL 1.3797 mL 2.7594 mL 5.5188 mL 6.8985 mL
50 mM 0.0552 mL 0.2759 mL 0.5519 mL 1.1038 mL 1.3797 mL
100 mM 0.0276 mL 0.138 mL 0.2759 mL 0.5519 mL 0.6898 mL
* Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
Protocol
Animal Research:
Food Funct. 2012 Jan;3(1):76-82.
(-)-Secoisolariciresinol attenuates high-fat diet-induced obesity in C57BL/6 mice.[Pubmed: 22030618]
Flaxseed lignan, Secoisolariciresinol has been reported to possess health benefits. We previously synthesized each stereoisomer of Secoisolariciresinol and found that (-)-Secoisolariciresinol reduces lipid accumulation and induces adiponectin production in 3T3-L1 adipocytes.
METHODS AND RESULTS:
Here we show the effects of (-)-Secoisolariciresinol on high-fat diet-induced obesity in C57BL/6 male mice. Oral administration of (-)-Secoisolariciresinol for 28 consecutive days significantly suppressed the gain of body weight. Increased serum adiponectin level and decreased gene expression of fatty acid synthase and sterol regulatory element-binding protein-1c in liver, which are related to fatty acid synthesis, were observed in the mice orally administered with (-)-Secoisolariciresinol. In addition, subcutaneous injection of (-)-Secoisolariciresinol also significantly suppressed the gain of body weight. Serum leptin levels were significantly increased by treating with (-)-Secoisolariciresinol or (-)-enterolactone. Subcutaneous injection of (-)-Secoisolariciresinol, (-)-enterolactone, or (-)-enterodiol promoted gene expression of acyl-CoA oxidase, carnitine palmitoyl transferase-1, and peroxisome proliferator-activated receptor α, which are related to β-oxidation.
CONCLUSIONS:
Overall results suggest that (-)-Secoisolariciresinol exerts a suppressive effect on the gain of body weight of mice fed a high-fat diet by inducing gene expression of adiponectin, resulting in the altered expression of various genes related to the synthesis and β-oxidation of fatty acids.
Life Sci. 2004 Apr 16;74(22):2781-92.
Secoisolariciresinol and isotaxiresinol inhibit tumor necrosis factor-alpha-dependent hepatic apoptosis in mice.[Pubmed: 15043992 ]
The effects of Secoisolariciresinol (1) and isotaxiresinol (2), two major lignans isolated from the wood of Taxus yunnanensis, on tumor necrosis factor-alpha (TNF-alpha)-dependent hepatic apoptosis induced by D-galactosamine (d-GalN)/lipopolysaccharide (LPS) were investigated in mice.
METHODS AND RESULTS:
Co-administration of d-GalN (700 mg/kg) and LPS (10 microg/kg) resulted in a typical hepatic apoptosis characterized by DNA fragmentation and the formation of apoptotic bodies. Serum glutamic pyruvic transaminase (sGPT) and glutamic oxaloacetic transaminase (sGOT) levels were also raised at 8 h after d-GalN/LPS intoxication due to a severe necrosis of hepatocytes. Pre-administration of 1 or 2 (50, 10 mg/kg, i.p.) 12 and 1 h before d-GalN/LPS significantly reduced DNA fragmentation and prevented chromatin condensation, apoptotic body formation and hepatitis. Pro-inflammatory cytokines such as TNF-alpha and interferon-gamma (IFN-gamma) secreted from LPS-activated macrophages are important mediators of hepatocyte apoptosis in this model. Pre-treatment with 1 or 2 significantly inhibited the elevation of serum TNF-alpha and IFN-gamma levels. In a separate experiment, both lignans had a significant dose-dependent protective effect on d-GalN/TNF-alpha-induced cell death in primary cultured mouse hepatocytes and TNF-alpha-mediated cell death in murine L929 fibrosarcoma cells.
CONCLUSIONS:
These results indicated that 1 and 2 prevent d-GalN/LPS-induced hepatic injury by inhibiting hepatocyte apoptosis through the blocking of TNF-alpha and IFN-gamma production by activated macrophages and direct inhibition of the apoptosis induced by TNF-alpha.
Structure Identification:
Br J Nutr. 2005 Mar;93(3):393-402.
Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol.[Pubmed: 15877880]

METHODS AND RESULTS:
Liquid chromatography-tandem mass spectrometry was used to quantify lariciresinol, pinoresinol, Secoisolariciresinol and matairesinol in eighty-three solid foods and twenty-six beverages commonly consumed in The Netherlands. The richest source of lignans was flaxseed (301,129 microg/100 g), which contained mainly Secoisolariciresinol. Also, lignan concentrations in sesame seeds (29,331 microg/100 g, mainly pinoresinol and lariciresinol) were relatively high. For grain products, which are known to be important sources of lignan, lignan concentrations ranged from 7 to 764 microg/100 g. However, many vegetables and fruits had similar concentrations, because of the contribution of lariciresinol and pinoresinol. Brassica vegetables contained unexpectedly high levels of lignans (185-2321 microg/100 g), mainly pinoresinol and lariciresinol. Lignan levels in beverages varied from 0 (cola) to 91 microg/100 ml (red wine). Only four of the 109 foods did not contain a measurable amount of lignans, and in most cases the amount of lariciresinol and pinoresinol was larger than that of Secoisolariciresinol and matairesinol.
CONCLUSIONS:
Thus, available databases largely underestimate the amount of enterolignan precursors in foods.
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