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6'-O-beta-D-Glucosylgentiopicroside

CAS# 115713-06-9

6'-O-beta-D-Glucosylgentiopicroside

Catalog No. BCN2814----Order now to get a substantial discount!

Product Name & Size Price Stock
6'-O-beta-D-Glucosylgentiopicroside: 5mg $104 In Stock
6'-O-beta-D-Glucosylgentiopicroside: 10mg Please Inquire In Stock
6'-O-beta-D-Glucosylgentiopicroside: 20mg Please Inquire Please Inquire
6'-O-beta-D-Glucosylgentiopicroside: 50mg Please Inquire Please Inquire
6'-O-beta-D-Glucosylgentiopicroside: 100mg Please Inquire Please Inquire
6'-O-beta-D-Glucosylgentiopicroside: 200mg Please Inquire Please Inquire
6'-O-beta-D-Glucosylgentiopicroside: 500mg Please Inquire Please Inquire
6'-O-beta-D-Glucosylgentiopicroside: 1000mg Please Inquire Please Inquire

Quality Control of 6'-O-beta-D-Glucosylgentiopicroside

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Chemical structure

6'-O-beta-D-Glucosylgentiopicroside

3D structure

Chemical Properties of 6'-O-beta-D-Glucosylgentiopicroside

Cas No. 115713-06-9 SDF Download SDF
PubChem ID 10864232 Appearance Powder
Formula C22H30O14 M.Wt 518.47
Type of Compound Iridoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one
SMILES C=CC1C(OC=C2C1=CCOC2=O)OC3C(C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)O
Standard InChIKey BERNCPGDRADLCG-KEXDUYRESA-N
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 6'-O-beta-D-Glucosylgentiopicroside

The roots of Gentiana macrophylla Pall.

Biological Activity of 6'-O-beta-D-Glucosylgentiopicroside

Description1. 6'-O-beta-D-Glucosylgentiopicroside may have antifungal activity.
TargetsAntifection

6'-O-beta-D-Glucosylgentiopicroside Dilution Calculator

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6'-O-beta-D-Glucosylgentiopicroside Molarity Calculator

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Preparing Stock Solutions of 6'-O-beta-D-Glucosylgentiopicroside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.9288 mL 9.6438 mL 19.2875 mL 38.575 mL 48.2188 mL
5 mM 0.3858 mL 1.9288 mL 3.8575 mL 7.715 mL 9.6438 mL
10 mM 0.1929 mL 0.9644 mL 1.9288 mL 3.8575 mL 4.8219 mL
50 mM 0.0386 mL 0.1929 mL 0.3858 mL 0.7715 mL 0.9644 mL
100 mM 0.0193 mL 0.0964 mL 0.1929 mL 0.3858 mL 0.4822 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 6'-O-beta-D-Glucosylgentiopicroside

Acyl secoiridoids and antifungal constituents from Gentiana macrophylla.[Pubmed:9397205]

Phytochemistry. 1996 Jul;42(5):1305-13.

LC-UV-mass spectrometry and bioassay co-directed fractionation of an aqueous acetone extract of the roots of Gentiana macrophylla gave three new chromene derivatives and two novel and six known secoiridoids, along with kurarinone, kushenol I, beta-sitosterol, stigmasterol, daucosterol, beta-sitosterol-3-O-gentiobioside, alpha-amyrin, oleanolic acid, isovitexin, gentiobiose and methyl 2-hydroxy-3-(1-beta-D-glucopyranosyl)oxybenzoate. The structures of the new products were established from spectral and chemical evidence as 2-methoxyanofinic acid and macrophyllosides A-D. The six known secoiridoids were gentiopicroside, sweroside, 6'-O-beta-D-glucosylgentiopicroside, 6'-O-beta-D-glucosylsweroside, trifloroside and rindoside. The new acid (2-methoxyanofinic acid), its methyl ester, kurarinone and kushenol I were shown to be active against the plant pathogenic fungus Cladosporium cucumerinum. The methyl ester and kurarinone inhibited also the growth of the human pathogenic yeast Candida albicans. Structure-activity relationships were studied. Thus, addition of a methoxyl group to the benzene nucleus of anofinic acid (2,2-dimethyl-2H-1-benzopyran-6-carboxylic acid) increased the antifungal activity remarkably whereas glycosylation at the carboxylic moiety was found to remove the activity. Esterification of the new acid induced its activity against C. albicans, but decreased its growth inhibition properties against C. cucumerinum. Hydroxylation of kurarinone at the 3 beta-position removed its activity against C. albicans and decreased the inhibition of C. cucumerinum. In addition, the chemotaxonomic significance of the identified constituents is discussed.

Inhibitory effects of secoiridoids from the roots of Gentiana straminea on stimulus-induced superoxide generation, phosphorylation and translocation of cytosolic compounds to plasma membrane in human neutrophils.[Pubmed:21584870]

Phytother Res. 2012 Feb;26(2):168-73.

Gentiana straminea Maxim. has been used widely as a traditional Chinese medicine for the treatment of rheumarthritis, icterepatitis, constipation, pain and hypertension. Five secoiridoids, gentiopicroside (GTP), 6'-O-(2-hydroxy-3-O-beta-D-glucopyranosyl-benzoyl)-sweroside (HGBS), 6'-O-beta-D-glucosylgentiopicroside (GGTP), sweroside (SW) and swertiamarin (STM) were isolated from the roots of G. straminea. The effect of these secoiridoids on stimulus-induced superoxide generation in human neutrophils was assayed by measuring the reduction of ferricytochrome c. Tyrosyl or serine/threonine phosphorylation of neutrophil proteins, and translocation of the cytosolic compounds to the cell membrane were also investigated using specific monoclonal antibodies. The five secoiridoids used in the present experiment suppressed N-formyl-methionyl-leucyl-phenylalanine (fMLP)-induced superoxide generation in a concentration dependent manner. GTP and HGBS also suppressed phorbol 12-myristate 13-acetate (PMA) and arachidonic acid (AA)-induced superoxide generation. However, the other three secoiridoids showed no effect on PMA- and AA-induced superoxide generation. fMLP-, PMA- and AA-induced tyrosyl or serine/threonine phosphorylation and translocation of the cytosolic proteins to the cell membrane were suppressed in parallel with the suppression of the stimulus-induced superoxide generation.

Description

6'-O-beta-D-Glucosylgentiopicroside is a secoiridoid isolated from the roots of G. straminea. 6'-O-beta-D-Glucosylgentiopicroside strongly suppresses N-formyl-methionyl-leucyl-phenylalanine (fMLP)-induced superoxide generation.

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