Scutellarein-7-O-glucoside | CAS:26046-94-6

Scutellarein-7-O-glucoside

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Description:

Scutellarein-7-O-glucoside inhibites MMP-2 activity.

Targets:

MMP

In vitro:

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

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

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.

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

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

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.

Scutellarein-7-O-glucoside Description

Source:	The herbs of Cirsium japonicum
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.

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.

CAS No.	26046-94-6	Price	$318 / 5mg
Catalog No.	CFN95082	Purity	>=98%
Molecular Weight	448.4	Type of Compound	Flavonoids
Formula	C₂₁H₂₀O₁₁	Physical Description	Yellow powder
Download	COA MSDS	Similar structural	Comparison (Web) (SDF)

Product Name	Scutellarein-7-O-glucoside
CAS No.:	26046-94-6
Catalog No.:	CFN95082
Molecular Formula:	C₂₁H₂₀O₁₁
Molecular Weight:	448.4 g/mol
Purity:	>=98%
Type of Compound:	Flavonoids
Physical Desc.:	Yellow powder
Targets:	MMP
Source:	The herbs of Cirsium japonicum
Solvent:	DMSO, Pyridine, Methanol, Ethanol, etc.
Price:	$318 / 5mg
Download:	COA MSDS
Similar structural:	Comparison (Web) (SDF)

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Flavonoids Compound Library

	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

CFN95249	Vicinin 2	90456-53-4	626.5	C₂₇H₃₀O₁₇
CFN95276	Apigenin 4'-O-(2'',6''-di-O-E-p-coumaroyl)glucoside	71781-79-8	724.7	C₃₉H₃₂O₁₄
CFN98981	Cosmosiin	578-74-5	432.4	C₂₁H₂₀O₁₀
CFN95163	Apigenin 7-O-(6''-O-malonylglucoside)	86546-87-4	518.4	C₂₄H₂₂O₁₃
CFN70289	Chamaemeloside	173356-77-9	576.5	C₂₇H₂₈O₁₄
CFN98500	Apigenin-7-glucuronide	29741-09-1	446.36	C₂₁H₁₈O₁₁
CFN98894	Apigenin 7-O-methylglucuronide	53538-13-9	460.4	C₂₂H₂₀O₁₁
CFN98352	Apigenin 5-O-beta-D-glucopyranoside	28757-27-9	432.4	C₂₁H₂₀O₁₀
CFN90165	Apiin	26544-34-3	564.49	C₂₆H₂₈O₁₄
CFN95352	Apigenin 7-[rhamnosyl-(1->2)-galacturonide]	124167-97-1	592.5	C₂₇H₂₈O₁₅