Secoisolariciresinol monoglucosideCAS# 63320-67-2 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 63320-67-2 | SDF | Download SDF |
PubChem ID | 101138945 | Appearance | Powder |
Formula | C26H36O11 | M.Wt | 524.56 |
Type of Compound | Lignans | Storage | Desiccate at -20°C |
Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
Chemical Name | (2R,3R,4S,5S,6R)-2-[(2R,3R)-4-hydroxy-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butoxy]-6-(hydroxymethyl)oxane-3,4,5-triol | ||
SMILES | COC1=C(C=CC(=C1)CC(CO)C(CC2=CC(=C(C=C2)O)OC)COC3C(C(C(C(O3)CO)O)O)O)O | ||
Standard InChIKey | DRLPXFRWJUZTMG-DNABOVRESA-N | ||
Standard InChI | InChI=1S/C26H36O11/c1-34-20-9-14(3-5-18(20)29)7-16(11-27)17(8-15-4-6-19(30)21(10-15)35-2)13-36-26-25(33)24(32)23(31)22(12-28)37-26/h3-6,9-10,16-17,22-33H,7-8,11-13H2,1-2H3/t16-,17-,22+,23+,24-,25+,26+/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. |
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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. |
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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. |
Description | Secoisolariciresinol monoglucoside is a natural product from Linum usitatissimum L. |
Structure Identification | BMC Plant Biology 2014, 14:82Evidence for a Sequential Glucosylation of Secoisolariciresinol (SECO) into Secoisolariciresinol Monoglucoside (SMG) and Diglucoside (SDG) Lignans by the Flax Lu-UGT74S1 (Lu-UGTCL809) UDP-Glycosyltransferase[Reference: WebLink]
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Secoisolariciresinol monoglucoside Dilution Calculator
Secoisolariciresinol monoglucoside Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 1.9064 mL | 9.5318 mL | 19.0636 mL | 38.1272 mL | 47.659 mL |
5 mM | 0.3813 mL | 1.9064 mL | 3.8127 mL | 7.6254 mL | 9.5318 mL |
10 mM | 0.1906 mL | 0.9532 mL | 1.9064 mL | 3.8127 mL | 4.7659 mL |
50 mM | 0.0381 mL | 0.1906 mL | 0.3813 mL | 0.7625 mL | 0.9532 mL |
100 mM | 0.0191 mL | 0.0953 mL | 0.1906 mL | 0.3813 mL | 0.4766 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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Identification and functional characterization of a flax UDP-glycosyltransferase glucosylating secoisolariciresinol (SECO) into secoisolariciresinol monoglucoside (SMG) and diglucoside (SDG).[Pubmed:24678929]
BMC Plant Biol. 2014 Mar 28;14:82.
BACKGROUND: Lignans are a class of diphenolic nonsteroidal phytoestrogens often found glycosylated in planta. Flax seeds are a rich source of secoisolariciresinol diglucoside (SDG) lignans. Glycosylation is a process by which a glycosyl group is covalently attached to an aglycone substrate and is catalyzed by uridine diphosphate glycosyltransferases (UGTs). Until now, very little information was available on UGT genes that may play a role in flax SDG biosynthesis. Here we report on the identification, structural and functional characterization of 5 putative UGTs potentially involved in secoisolariciresinol (SECO) glucosylation in flax. RESULTS: Five UGT genes belonging to the glycosyltransferases' family 1 (EC 2.4.x.y) were cloned and characterized. They fall under four UGT families corresponding to five sub-families referred to as UGT74S1, UGT74T1, UGT89B3, UGT94H1, UGT712B1 that all display the characteristic plant secondary product glycosyltransferase (PSPG) conserved motif. However, diversity was observed within this 44 amino acid sequence, especially in the two peptide sequences WAPQV and HCGWNS known to play a key role in the recognition and binding of diverse aglycone substrates and in the sugar donor specificity. In developing flax seeds, UGT74S1 and UGT94H1 showed a coordinated gene expression with that of pinoresinol-lariciresinol reductase (PLR) and their gene expression patterns correlated with SDG biosynthesis. Enzyme assays of the five heterologously expressed UGTs identified UGT74S1 as the only one using SECO as substrate, forming SECO monoglucoside (SMG) and then SDG in a sequential manner. CONCLUSION: We have cloned and characterized five flax UGTs and provided evidence that UGT74S1 uses SECO as substrate to form SDG in vitro. This study allowed us to propose a model for the missing step in SDG lignan biosynthesis.
Hydrolysis kinetics of secoisolariciresinol diglucoside oligomers from flaxseed.[Pubmed:18925741]
J Agric Food Chem. 2008 Nov 12;56(21):10041-7.
Flaxseed is the richest dietary source of the lignan secoisolariciresinol diglucoside (SDG) and contains the largest amount of SDG oligomers, which are often hydrolyzed to break the ester linkages for the release of SDG and the glycosidic bonds for the release of secoisolariciresinol (SECO). The alkaline hydrolysis reaction kinetics of SDG oligomers from flaxseed and the acid hydrolysis process of SDG and other glucosides were investigated. For the kinetic modeling, a pseudo-first-order reaction was assumed. The results showed that the alkaline hydrolysis of SDG oligomers followed first-order reaction kinetics under mild alkaline hydrolytic conditions and that the concentration of sodium hydroxide had a strong influence on the activation energy of the alkaline hydrolysis of SDG oligomers. The results also indicated that the main acid hydrolysates of SDG included Secoisolariciresinol monoglucoside (SMG), SECO, and anhydrosecoisolariciresinol (anhydro-SECO) and that the extent and the main hydrolysates of the acid hydrolysis reaction depended on the acid concentration, hydrolysis temperature, and time. In addition, the production and change of p-coumaric acid glucoside, ferulic acid glucoside and their methyl esters and p-coumaric acid, ferulic acid, and their methyl esters during the process of hydrolysis was also investigated.
Separation and determination of secoisolariciresinol diglucoside oligomers and their hydrolysates in the flaxseed extract by high-performance liquid chromatography.[Pubmed:18272161]
J Chromatogr A. 2008 Mar 28;1185(2):223-32.
Flaxseed contains the largest amount of lignan secoisolariciresinol diglucoside (SDG) oligomers and is the richest dietary source of SDG. SDG oligomers in the flaxseed extract are often hydrolyzed to break the ester linkages for the release of SDG and the glycosidic bonds for the release of secoisolariciresinol (SECO). The hydrolysates of SDG oligomers are complicated because of the production of esters in an alcohol-containing medium. In this study, a new gradient reversed-phase high-performance liquid chromatography (HPLC) method has been developed to be suitable for the separation and determination of: (1) SDG oligomers extracted from the defatted flaxseed powder by a 70% aqueous methanol solution; (2) SDG oligomers and their alkaline hydrolysates, including SDG, p-coumaric acid glucoside and its methyl ester, ferulic acid glucoside and its methyl ester in an alkaline hydrolytic solution; and (3) the succedent acid hydrolysates, including Secoisolariciresinol monoglucoside (SMG), SECO, anhydrosecoisolariciresinol (anhydro-SECO), p-coumaric acid and its methyl ester, ferulic acid and its methyl ester, 5-hydroxymethyl-2-furfural (HMF) and its degradation product in an acid hydrolytic solution. The content of SDG oligomers in a defatted flaxseed powder was found to be 38.5 mg/g on a dry matter basis, corresponding to a SDG content of 15.4 mg/g, which was determined after alkaline hydrolysis. Furthermore, this study presented a major reaction pathway for the hydrolysis of SDG oligomers.