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Secoisolariciresinol monoglucoside

CAS# 63320-67-2

Secoisolariciresinol monoglucoside

Catalog No. BCN6990----Order now to get a substantial discount!

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Quality Control of Secoisolariciresinol monoglucoside

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Chemical structure

Secoisolariciresinol monoglucoside

3D structure

Chemical Properties of Secoisolariciresinol monoglucoside

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.
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 Secoisolariciresinol monoglucoside

The seeds of Linum usitatissimum L.

Biological Activity of Secoisolariciresinol monoglucoside

DescriptionSecoisolariciresinol monoglucoside is a natural product from Linum usitatissimum L.

Protocol of Secoisolariciresinol monoglucoside

Structure Identification
BMC Plant Biology 2014, 14:82

Evidence 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]


CONCLUSIONS:
All UGTs displayed the characteristic plant secondary product glycosyltransferase (PSPG) motif. Five of the UGTs were exclusively expressed in seed and the mRNA transcript expression of two revealed a clear correlation with SDG lignan biosynthesis in developing seed. The seed-specific UGTs were expressed in yeast and the proteins reacted with secoisolariciresinol (SECO) in presence of UDP-glucose. Only Lu-UGTCL809 used SECO as substrate, forming first Secoisolariciresinol monoglucoside (SMG) and then SDG from the SMG intermediate. 3D structural modeling and ligand docking identified the amino acids within the PSPG motif that bind the phosphate and hydroxyl groups of UDP-glucose for both Lu-UGTCL809 (SER357 and Trp355) and Lu-UGTRP250 (Gln351, Ala352 and Gly261). Furthermore, whereas Lu-UGTCL809 binds to SECO by three hydrogen bonds between Cys335 and Gln337 and 4-OH and 3-OCH3 of SECO, Lu-UGTRP250 binds to SECO by a single hydrogen bond between Ala352 and the 9’hydroxyl group of SECO. Binding of Lu-UGTRP250 to the 9’-OH glycosylation site may explain the impaired SECO glucosylation by Lu-UGTRP250 for SMG synthesis.
CONCLUSIONS:
We report the first direct functional evidence for SECO glucosylation by a family 1 UGT.

Secoisolariciresinol monoglucoside Dilution Calculator

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Preparing Stock Solutions of Secoisolariciresinol monoglucoside

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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References on Secoisolariciresinol monoglucoside

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.

Description

Secoisolariciresinol Monoglucoside is a natural product isolated from the seeds of Linum usitatissimum L..

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