Secoisolariciresinol Diglucoside | CAS:148244-82-0

Secoisolariciresinol Diglucoside

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Description:

Secoisolariciresinol diglucoside(SDG) is a phytoestrogen, estrogens and phytoestrogen from soy have been reported to have mild hypotensive effects, and SDG is a long-acting hypotensive agent, and that the hypotensive effect is mediated through the guanylate cyclase enzyme. SDG has strong antioxidant activity, cardioprotective effects, reduces the blood levels of low-density lipoprotein cholesterol, and reduces the risk of hormone related cancer.

Targets:

HO-1 | VEGFR | NOS | AMPK | NF-kB | TNF-α | Bcl-2/Bax | ROS | LDL

In vivo:

J Physiol Biochem. 2014 Dec;70(4):961-9.

Secoisolariciresinol diglucoside in high-fat diet and streptozotocin-induced diabetic nephropathy in rats: a possible renoprotective effect.[Pubmed: 25316298]

Due to substantial morbidity and high complication rate of diabetes mellitus, which is considered as the third killer in the world, a search for the effective blockade of the progression of diabetic nephropathy (DN) remains a therapeutic challenge. Alternative antidiabetic drugs from natural plants are highly demanded nowadays. The aim of this study was to investigate the renoprotective effect of Secoisolariciresinol Diglucoside (SDG) on DN induced in rats.
METHODS AND RESULTS:
Diabetes was induced in male Sprague-Dawley rats by a high-fat diet (HFD) and an intraperitoneal 35 mg/kg streptozotocin (STZ) injection. Rats were divided into four groups: normal control rats, diabetic control rats, diabetic rats treated with SDG at 10 mg/kg/day for 4 weeks, and diabetic rats treated with SDG at 20 mg/kg/day for 4 weeks. At the end of the treatment, blood and renal tissue samples were collected for biochemical examination. The results revealed that SDG treatment significantly increased insulin level and decreased blood glucose, fructosamine, creatinine, and blood urea nitrogen levels in diabetic rats. Also, SDG significantly increased renal reduced glutathione, superoxide dismutase and decreased malondialdehyde and nitric oxide levels. In addition, SDG downregulated the renal nuclear factor kappa-B (NF-κB), tumor necrosis factor (TNF)-α, and inducible nitric oxide synthase (iNOS) and upregulated renal survivin and B-cell lymphoma-2 (Bcl-2) expressions when compared with untreated diabetic control rats.
CONCLUSIONS:
This study demonstrated, for the first time, the renoprotective effects of SDG in HFD/STZ-induced DN in rats through correction of hyperglycemia; attenuation of oxidative/nitrosative stress markers; downregulation of renal expressions of inflammatory markers NF-κB, TNF-α, and iNOS; along with upregulation of renal expressions of antiapoptotic markers survivin and Bcl-2.

Int J Angiol. 2013 Dec;22(4):235-8.

Secoisolariciresinol Diglucoside (SDG) Isolated from Flaxseed, an Alternative to ACE Inhibitors in the Treatment of Hypertension.[Pubmed: 24436618]

Secoisolariciresinol Diglucoside(SDG) is a plant lignan isolated from flaxseed and is phytoestrogen. SDG is a potent and long-acting hypotensive agent. Plant phytoestrogens have inhibitory effects on angiotensin-converting enzyme (ACE). The hypotensive effects of SDG, a phytoestrogen, may be mediated through inhibition of ACE. The objective of this study was to investigate if SDG-induced hypotension is mediated through inhibition of ACE.
METHODS AND RESULTS:
The Sprague Dawley male rats were anesthetized and trachea was cannulated. The right jugular vein was cannulated to administer the drug and the carotid artery was cannulated to record arterial pressures using PIOEZ-1 miniature model transducer (Becton, Dickinson and Company, Franklin Lakes, NJ) and Beckman dynograph (Beckman Instruments, Inc., Schiller Park, IL).
CONCLUSIONS:
The data suggest that SDG reduced the angiotensin I-induced rise in the arterial pressures and hence SDG is a potent ACE inhibitor.

Secoisolariciresinol Diglucoside Description

Source:	The seeds of Linum usitatissimum L.
Solvent:	DMSO, Pyridine, Methanol, Ethanol, 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. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
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.

Cell Research:

PLoS One. 2015 Mar 30;10(3):e0122852.

Secoisolariciresinol diglucoside abrogates oxidative stress-induced damage in cardiac iron overload condition.[Pubmed: 25822525]

Cardiac iron overload is directly associated with cardiac dysfunction and can ultimately lead to heart failure.
METHODS AND RESULTS:
This study examined the effect of Secoisolariciresinol Diglucoside (SDG), a component of flaxseed, on iron overload induced cardiac damage by evaluating oxidative stress, inflammation and apoptosis in H9c2 cardiomyocytes. Cells were incubated with 50 μ5M iron for 24 hours and/or a 24 hour pre-treatment of 500 μ M SDG. Cardiac iron overload resulted in increased oxidative stress and gene expression of the inflammatory mediators tumor necrosis factor-α, interleukin-10 and interferon γ, as well as matrix metalloproteinases-2 and -9. Increased apoptosis was evident by increased active caspase 3/7 activity and increased protein expression of Forkhead box O3a, caspase 3 and Bax. Cardiac iron overload also resulted in increased protein expression of p70S6 Kinase 1 and decreased expression of AMP-activated protein kinase. Pre-treatment with SDG abrogated the iron-induced increases in oxidative stress, inflammation and apoptosis, as well as the increased p70S6 Kinase 1 and decreased AMP-activated protein kinase expression. The decrease in superoxide dismutase activity by iron treatment was prevented by pre-treatment with SDG in the presence of iron.
CONCLUSIONS:
Based on these findings we conclude that SDG was cytoprotective in an in vitro model of iron overload induced redox-inflammatory damage, suggesting a novel potential role for SDG in cardiac iron overload.

Animal Research:

J Mol Cell Cardiol. 2008 Jan;44(1):170-9.

Secoisolariciresinol diglucoside induces neovascularization-mediated cardioprotection against ischemia-reperfusion injury in hypercholesterolemic myocardium.[Pubmed: 18001768 ]

Hypercholesterolemia (HC) induced endothelial cell dysfunction and decreased endothelial nitric oxide formation results in impaired angiogenesis and subsequent cardiovascular disorders. Therapeutic angiogenesis is known to be a novel strategy for treatment of patients with ischemic heart disease. We have shown that Secoisolariciresinol Diglucoside (SDG) is angiogenic as well as cardioprotective against myocardial ischemia.
METHODS AND RESULTS:
In the present study, we examined the efficacy of SDG in a hypercholesterolemic myocardial infarction (MI) model. The rats were maintained on a normal and high cholesterol diet (2%) for 8 weeks followed by oral administration of SDG (20 mg/kg) for 2 weeks. The rats were divided into four groups (n=24 in each): Control (C); SDG control (SDG); HC; and HC+SDG (HSDG). Isolated hearts subjected to 30 min of global ischemia followed by 120 min of reperfusion were used to measure the cardiac functions, infarct size and to examine the protein expression profile. After treatment, MI was induced by ligating the left anterior descending artery. Echocardiographic parameters were examined 30 days after MI. Significant reduction in total cholesterol, LDL-cholesterol, triglycerides and an increase in HDL-cholesterol levels were observed in HSDG as compared to the HC. Decreased infarct size was observed in the HSDG group (43%) compared to the HC (54%). Increased phosphorylation of endothelial nitric oxide synthase (p-eNOS) (3.1-fold), vascular endothelial growth factor (1.9-fold) and heme oxygenase-1 (2.3-fold) was observed in the HSDG group as compared to the HC group. Significant improvement in left ventricular functions was also observed in the HSDG group as evidenced by increased ejection fraction (55% vs. 45%), fractional shortening (28% vs. 22%) and decreased left ventricular inner diameter in systole (8 vs. 6 mm) in HSDG compared to HC. Moreover, MI model has shown increased capillary density (2531 vs. 1901) and arteriolar density (2.6 vs. 1.8) in SDG-treated rats as compared to the HC. The increased capillary and arteriolar density along with increased left ventricular functions on SDG treatment might be due to increased HO-1, VEGF and p-eNOS expression.
CONCLUSIONS:
In conclusion, our study demonstrates for the first time that SDG treatment reduces ventricular remodeling by neovascularization of the infarcted HC myocardium.

Circulation. 1999 Mar 16;99(10):1355-62.

Reduction of serum cholesterol and hypercholesterolemic atherosclerosis in rabbits by secoisolariciresinol diglucoside isolated from flaxseed.[Pubmed: 10077521]

Secoisolariciresinol Diglucoside (SDG) is a plant lignan isolated from flaxseed. Lignans are platelet-activating factor-receptor antagonists that would inhibit the production of oxygen radicals by polymorphonuclear leukocytes.
METHODS AND RESULTS:
SDG is an antioxidant. Antioxidants studied thus far are known to reduce hypercholesterolemic atherosclerosis. The objective of this study was to determine the effect of SDG on various blood lipid and aortic tissue oxidative stress parameters and on the development of atherosclerosis in rabbits fed a high-cholesterol diet. CONCLUSIONS:
CONCLUSIONS:
These results suggest that SDG reduced hypercholesterolemic atherosclerosis and that 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.

Product Name	Secoisolariciresinol Diglucoside
Price:	$30 / 20mg
CAS No.:	148244-82-0
Catalog No.:	CFN99722
Molecular Formula:	C₃₂H₄₆O₁₆
Molecular Weight:	686.71 g/mol
Purity:	>=98%
Type of Compound:	Lignans
Physical Desc.:	Powder
Source:	The seeds of Linum usitatissimum L.
Solvent:	DMSO, Pyridine, Methanol, Ethanol, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
Guestbook:

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	1.4562 mL	7.2811 mL	14.5622 mL	29.1244 mL	36.4055 mL
5 mM	0.2912 mL	1.4562 mL	2.9124 mL	5.8249 mL	7.2811 mL
10 mM	0.1456 mL	0.7281 mL	1.4562 mL	2.9124 mL	3.6405 mL
50 mM	0.0291 mL	0.1456 mL	0.2912 mL	0.5825 mL	0.7281 mL
100 mM	0.0146 mL	0.0728 mL	0.1456 mL	0.2912 mL	0.3641 mL

CFN89236	Anhydrosecoisolariciresinol	29388-33-8	344.40	C₂₀H₂₄O₅
CFN96711	4,4'-Dihydroxy-3,3',9-trimethoxy-9,9'-epoxylignan	1206464-65-4	374.43	C₂₁H₂₆O₆
CFN98363	Secoisolariciresinol	29388-59-8	362.4	C₂₀H₂₆O₆
CFN96682	Secoisolariciresinol monoglucoside	63320-67-2	524.56	C₂₆H₃₆O₁₁
CFN99722	Secoisolariciresinol Diglucoside	148244-82-0	686.71	C₃₂H₄₆O₁₆
CFN95601	Secoisolariciresinol 9,9'-diacetate	848844-79-1	446.5	C₂₄H₃₀O₈
CFN98956	9,9'-Di-O-(E)-feruloylsecoisolariciresinol	56973-66-1	714.8	C₄₀H₄₂O₁₂
CFN91423	Dihydrocubebin	24563-03-9	358.4	C₂₀H₂₂O₆
CFN70261	Cubebin	1242843-00-0	356.4	C₂₀H₂₀O₆
CFN92963	5,5'-Dimethoxysecoisolariciresinol	1002106-91-3	422.47	C₂₂H₃₀O₈