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Secoisolarisiresinol Diglucoside

CAS# 158932-33-3

Secoisolarisiresinol Diglucoside

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Chemical structure

Secoisolarisiresinol Diglucoside

3D structure

Chemical Properties of Secoisolarisiresinol Diglucoside

Cas No. 158932-33-3 SDF Download SDF
PubChem ID 9917980 Appearance White powder
Formula C32H46O16 M.Wt 686.7
Type of Compound Phenylpropanes Storage Desiccate at -20°C
Synonyms SDG
Solubility DMSO : 125 mg/mL (182.03 mM; Need ultrasonic)
Chemical Name (2R,3R,4S,5S,6R)-2-[(2R,3R)-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
SMILES COC1=C(C=CC(=C1)CC(COC2C(C(C(C(O2)CO)O)O)O)C(CC3=CC(=C(C=C3)O)OC)COC4C(C(C(C(O4)CO)O)O)O)O
Standard InChIKey SBVBJPHMDABKJV-PGCJWIIOSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Secoisolarisiresinol Diglucoside

1 Helianthus sp. 2 Linum sp. 3 Sesamum sp.

Protocol

Animal Administration [1]
Rabbits: New Zealand White rabbits 6 to 8 weeks old weighing between 1.8 and 2.0 kg, after 1 week of adaptation, are assigned to 4 groups. Those in group 1 are fed rabbit laboratory chow pellets. The other groups receive Secoisolariciresinol diglucoside (SDG) or cholesterol or cholesterol plus SDG in addition to rabbit chow. The diet does not contain any antioxidants. SDG (15 mg/kg body wt) is fed orally, wrapped in leafy vegetables (lettuce). Water is given ad libitum. The rabbits are housed in cages under a 12-hour-light/12-hour-dark cycle. The rabbits are anesthetized at the end of 8 weeks, and aortas are removed under pentobarbital sodium anesthesia (40 mg/kg IV) for assessment of atherosclerotic plaques and measurement of tissue MDA and antioxidant reserve. Blood samples (from ear marginal artery) for measurement of serum TG, TC, HDL-C, LDL-C, and VLDL-C are collected before (time 0) and after 4 and 8 weeks on the respective experimental diets. No food is supplied for 18 hours before withdrawal of blood samples. Weights of the rabbits are recorded at 0, 4, and 8 weeks.

References:
[1]. Prasad K. Reduction of serum cholesterol and hypercholesterolemic atherosclerosis in rabbits by secoisolariciresinol diglucoside isolated from flaxseed. Circulation. 1999 Mar 16;99(10):1355-62. [2]. Velalopoulou A, et al. 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).

Secoisolarisiresinol Diglucoside Dilution Calculator

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Secoisolarisiresinol Diglucoside Molarity Calculator

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Preparing Stock Solutions of Secoisolarisiresinol Diglucoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.4562 mL 7.2812 mL 14.5624 mL 29.1248 mL 36.406 mL
5 mM 0.2912 mL 1.4562 mL 2.9125 mL 5.825 mL 7.2812 mL
10 mM 0.1456 mL 0.7281 mL 1.4562 mL 2.9125 mL 3.6406 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
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Secoisolarisiresinol Diglucoside

HPLC method with fluorescence detection for the quantitative determination of flaxseed lignans.[Pubmed:20970390]

J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Nov 15;878(30):3076-82.

We report a rapid and simple HPLC method with fluorescence detection for the quantification of the major flaxseed lignan, Secoisolarisiresinol Diglucoside (SDG) and its major metabolites. The method is specific for SDG, secoisolarisiresinol (SECO), enterodiol (ED) and entrolactone (EL) in rat serum. The assay procedure involves chromatographic separation using a Waters Symmetry C(18) reversed-phase column (4.6 mm x 150 mm, 5 mum) and mobile phase gradient conditions consisting of acetonitrile (0.1% formic acid) and water (0.1% formic acid). SDG extraction from serum requires the use of Centrifuge filters while SECO, ED and EL are extracted with diethyl ether. The organic layer is evaporated and reconstituted in 100 muL of mobile phase and 50 muL of reconstituted sample or filtrate is injected onto the column. Total run time is 25 min. Calibration curves are linear (r(2) >/= 0.997) from 0.05 to 10 mug/mL for SDG and EL and 0.01-10 mug/mL for SECO and ED. Precision and accuracy are within USFDA specified limits. The stability of all lignans is established in auto-injector, bench-top, freeze-thaw and long-term stability at -80 degrees C for 30 days. The method's reasonable sensitivity and reliance on more widely available HPLC technology should allow for its straightforward application to pharmacokinetic evaluations of lignans in animal model systems such as the rat.

Description

(R,R)-Secoisolariciresinol diglucoside ((R,R)-SDG) is the minor isomer of Secoisolariciresinol diglucoside in flaxseed. (R,R)-Secoisolariciresinol diglucoside ((R,R)-SDG) possesses antioxidant and free radical scavenging activities and DNA-radioprotective properties. (R,R)-Secoisolariciresinol diglucoside ((R,R)-SDG) inhibits myeloperoxidase (MPO) activity by suppressing both the peroxidase and chlorination cyclesin inflammatory cells.

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