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Scutellarein-7-O-glucoside

CAS# 26046-94-6

Scutellarein-7-O-glucoside

Catalog No. BCN8099----Order now to get a substantial discount!

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Quality Control of Scutellarein-7-O-glucoside

Number of papers citing our products

Chemical structure

Scutellarein-7-O-glucoside

3D structure

Chemical Properties of Scutellarein-7-O-glucoside

Cas No. 26046-94-6 SDF Download SDF
PubChem ID 5320623 Appearance Yellow powder
Formula C21H20O11 M.Wt 448.4
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 5,6-dihydroxy-2-(4-hydroxyphenyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O
Standard InChIKey VUGRLRAUZWGZJP-IAAKTDFRSA-N
Standard InChI InChI=1S/C21H20O11/c22-7-14-17(26)19(28)20(29)21(32-14)31-13-6-12-15(18(27)16(13)25)10(24)5-11(30-12)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21-/m1/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 Scutellarein-7-O-glucoside

The herbs of Cirsium japonicum

Biological Activity of Scutellarein-7-O-glucoside

DescriptionScutellarein-7-O-glucoside inhibites MMP-2 activity.
TargetsMMP
In vitro

Engineering Saccharomyces cerevisiae with the deletion of endogenous glucosidases for the production of flavonoid glucosides.[Pubmed: 27491546 ]

Microb Cell Fact. 2016 Aug 4;15(1):134.

Glycosylation of flavonoids is a promising approach to improve the pharmacokinetic properties and biological activities of flavonoids. Recently, many efforts such as enzymatic biocatalysis and the engineered Escherichia coli biotransformation have increased the production of flavonoid glucosides. However, the low yield of flavonoid glucosides can not meet the increasing demand for human medical and dietary needs. Saccharomyces cerevisiae is a generally regarded as safe (GRAS) organism that has several attractive characteristics as a metabolic engineering platform for the production of flavonoid glucosides. However, endogenous glucosidases of S. cerevisiae as a whole-cell biocatalyst reversibly hydrolyse the glucosidic bond and hinder the biosynthesis of the desired products. In this study, a model flavonoid, scutellarein, was used to exploit how to enhance the production of flavonoid glucosides in the engineered S. cerevisiae.
METHODS AND RESULTS:
To produce flavonoid glucosides, three flavonoid glucosyltransferases (SbGTs) from Scutellaria baicalensis Georgi were successfully expressed in E. coli, and their biochemical characterizations were identified. In addition, to synthesize the flavonoid glucosides in whole-cell S. cerevisiae, SbGT34 was selected for constructing the engineering yeast. Three glucosidase genes (EXG1, SPR1, YIR007W) were knocked out using homologous integration, and the EXG1 gene was determined to be the decisive gene of S. cerevisiae in the process of hydrolysing flavonoid glucosides. To further enhance the potential glycosylation activity of S. cerevisiae, two genes encoding phosphoglucomutase and UTP-glucose-1-phosphate uridylyltransferase involved in the synthetic system of uridine diphosphate glucose were over-expressed in S. cerevisiae. Consequently, approximately 4.8 g (1.2 g/L) of Scutellarein-7-O-glucoside (S7G) was produced in 4 L of medium after 54 h of incubation in a 10-L fermenter while being supplied with ~3.5 g of scutellarein.
CONCLUSIONS:
The engineered yeast harbouring SbGT with a deletion of glucosidases produced more flavonoid glucosides than strains without a deletion of glucosidases. This platform without glucosidase activity could be used to modify a wide range of valued plant secondary metabolites and to explore of their biological functions using whole-cell S. cerevisiae as a biocatalyst.

The influence of selected flavonoids from the leaves of Cirsium palustre (L.) Scop. on collagen expression in human skin fibroblasts.[Pubmed: 24643916 ]

Phytother Res. 2014 Sep;28(9):1399-405.

Ten flavonoids belonging to the subclasses of flavones, flavanones and aurones were isolated from methanolic extract of Cirsium palustre leaves after multistep chromatographic separation. Their structures were elucidated with spectroscopic methods.
METHODS AND RESULTS:
All compounds, except for luteolin 7-O-glucoside, were isolated for the first time. Four compounds-eriodictyol 7-O-glucoside (6), 6-hydroxyluteolin 7-O-glucoside (11), Scutellarein-7-O-glucoside (12) and pedalitin (14)-were tested for their effect on collagen expression in normal human dermal fibroblasts. Among them, compound 11 at 40 μM and compound 14, at all concentrations used (1, 20, 40 μM), significantly enhanced the level of total collagen secreted into the medium. Furthermore, compound 11 significantly stimulated type I collagen expression, whereas compound 14 activated type I and III collagen expression at the mRNA level, depending on concentration. MMP-2 activity was inhibited by all study compounds, with the greatest effect recorded with compound 14 at 20 μM. The lack of effect on collagen content in the medium of compound 6- and compound 12-treated cells, besides an increase in COL1A1 and COL1A2 expression, might be caused by diminished expression of HSP47 gene, resulting in decreased procollagen secretion.
CONCLUSIONS:
Future study of compounds 11 and 14 for their potential therapeutic use in conditions connected with collagen biosynthesis deficiency is required.

Protocol of Scutellarein-7-O-glucoside

Structure Identification
Nat Prod Commun. 2015 Mar;10(3):403-5.

Foliar flavonoids from Tanacetum vulgare var. boreale and their geographical variation.[Pubmed: 25924515]


METHODS AND RESULTS:
Foliar flavonoids of Tanacetum vulgare var. boreale were isolated. Eight flavonoid glycosides, 7-O-glucosides of apigenin, luteolin, scutellarein and 6- hydroxyluteolin, and 7-O-glucuronides of apigenin, luteolin, chrysoeriol and eriodictyol were identified. Moreover, eight flavonoid aglycones, apigenin, luteolin, hispidulin, nepetin, eupatilin, jaceosidin, pectolinarigenin and axillarin were also isolated and identified. The flavonoid composition of two varieties of T. vulgare, i.e. var. boreale and var. vulgare, were compared. All samples of var. boreale and one sample of var. vulgare had the same flavonoid pattern, and could be distinguished from almost all the samples of var. vulgare.
CONCLUSIONS:
Thus, the occurrence of chemotypes, which are characterized by either the presence or absence of Scutellarein-7-O-glucoside, eriodictyol 7-O-glucuronide and pectolinarigenin was shown in T. vulgare sensu lato.

Scutellarein-7-O-glucoside Dilution Calculator

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Scutellarein-7-O-glucoside Molarity Calculator

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Preparing Stock Solutions of Scutellarein-7-O-glucoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2302 mL 11.1508 mL 22.3015 mL 44.603 mL 55.7538 mL
5 mM 0.446 mL 2.2302 mL 4.4603 mL 8.9206 mL 11.1508 mL
10 mM 0.223 mL 1.1151 mL 2.2302 mL 4.4603 mL 5.5754 mL
50 mM 0.0446 mL 0.223 mL 0.446 mL 0.8921 mL 1.1151 mL
100 mM 0.0223 mL 0.1115 mL 0.223 mL 0.446 mL 0.5575 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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