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Kaempferol 3-gentiobioside

CAS# 22149-35-5

Kaempferol 3-gentiobioside

Catalog No. BCN3345----Order now to get a substantial discount!

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Quality Control of Kaempferol 3-gentiobioside

Number of papers citing our products

Chemical structure

Kaempferol 3-gentiobioside

3D structure

Chemical Properties of Kaempferol 3-gentiobioside

Cas No. 22149-35-5 SDF Download SDF
PubChem ID 9960512 Appearance Yellowish powder
Formula C27H30O16 M.Wt 610.5
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms 3,4',5,7-Tetrahydroxyflavone 3-gentiobioside
Solubility Soluble in methanol; insoluble in water
Chemical Name 5,7-dihydroxy-2-(4-hydroxyphenyl)-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]oxychromen-4-one
SMILES C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)O)O)O)O)O)O)O
Standard InChIKey BITPRCODIALMOV-DEFKTLOSSA-N
Standard InChI InChI=1S/C27H30O16/c28-7-14-17(32)20(35)22(37)26(41-14)39-8-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-12(31)5-11(30)6-13(16)40-24(25)9-1-3-10(29)4-2-9/h1-6,14-15,17-18,20-23,26-33,35-38H,7-8H2/t14-,15-,17-,18-,20+,21+,22-,23-,26-,27+/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 Kaempferol 3-gentiobioside

1 Glycine sp. 2 Sauropus sp.

Biological Activity of Kaempferol 3-gentiobioside

DescriptionKaempferol 3-O-gentiobioside has antiinflammatory activity, shows weak inhibitory effects on Concanavalin A-induced histamine release, 5-lipoxygenase, and COX-1.
TargetsHistamine Receptor | COX
In vitro

Chemical constituents isolated from Polygala japonica leaves and their inhibitory effect on nitric oxide production in vitro.[Pubmed: 18825536]

J Enzyme Inhib Med Chem. 2009 Feb;24(1):230-3.

A methanolic extract of dried leaves of Polygala japonica Houtt (Polygalaceae) significantly attenuated nitric oxide production in lipopolysaccharide-simulated BV2 microglia.
METHODS AND RESULTS:
Five anthraquinones chrysophanol (1), emodin (2), aloe-emodin (3), emodin 8-O-beta-D-glucopyranoside (4) and trihydroxy anthraquinone (5), and four flavonoids kaempferol (6), chrysoeriol (7), Kaempferol 3-gentiobioside (8) and isorhamnetin (9) were isolated from the methanolic extract using bioactivity-guided fractionation. Among them, compounds 1-4, 6 and 7 showed significant inhibitory effect on lipopolysaccharide-induced nitric oxide production in BV2 microglia at the concentrations ranging from 1.0 to 100.0 microM.

Protocol of Kaempferol 3-gentiobioside

Structure Identification
Yakugaku Zasshi. 2001 Nov;121(11):817-20.

A stabilized flavonoid glycoside in heat-treated Cassia alata leaves and its structural elucidation.[Pubmed: 11725550]

Heat-treated leaves of Cassia alata were studied for any change in chemical constituents using sun dried leaves as the reference standard.
METHODS AND RESULTS:
A high concentration of a constituent was observed in the heat-treated leaves. Spectroscopic studies revealed the structure of the constituent as Kaempferol 3-gentiobioside, which has not yet been detected in the Cassia species. In a stability study disappearance of Kaempferol 3-gentiobioside was noted in the sun dried leaves while there was little or no change in the Kaempferol 3-gentiobioside concentration in the heat-treated leaves when incubated in an aqueous solution, suggesting a possible presence of enzymatic activities in the sun dried leaves.
CONCLUSIONS:
Therefore, heat-treatment may be a good method to stabilize Kaempferol 3-gentiobioside in Cassia alata leaves.

Kaempferol 3-gentiobioside Dilution Calculator

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Kaempferol 3-gentiobioside Molarity Calculator

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Preparing Stock Solutions of Kaempferol 3-gentiobioside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.638 mL 8.19 mL 16.38 mL 32.76 mL 40.95 mL
5 mM 0.3276 mL 1.638 mL 3.276 mL 6.552 mL 8.19 mL
10 mM 0.1638 mL 0.819 mL 1.638 mL 3.276 mL 4.095 mL
50 mM 0.0328 mL 0.1638 mL 0.3276 mL 0.6552 mL 0.819 mL
100 mM 0.0164 mL 0.0819 mL 0.1638 mL 0.3276 mL 0.4095 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 Kaempferol 3-gentiobioside

A stabilized flavonoid glycoside in heat-treated Cassia alata leaves and its structural elucidation.[Pubmed:11725550]

Yakugaku Zasshi. 2001 Nov;121(11):817-20.

Heat-treated leaves of Cassia alata were studied for any change in chemical constituents using sun dried leaves as the reference standard. A high concentration of a constituent was observed in the heat-treated leaves. Spectroscopic studies revealed the structure of the constituent as Kaempferol 3-gentiobioside, which has not yet been detected in the Cassia species. In a stability study disappearance of Kaempferol 3-gentiobioside was noted in the sun dried leaves while there was little or no change in the Kaempferol 3-gentiobioside concentration in the heat-treated leaves when incubated in an aqueous solution, suggesting a possible presence of enzymatic activities in the sun dried leaves. Therefore, heat-treatment may be a good method to stabilize Kaempferol 3-gentiobioside in Cassia alata leaves.

Chemical constituents isolated from Polygala japonica leaves and their inhibitory effect on nitric oxide production in vitro.[Pubmed:18825536]

J Enzyme Inhib Med Chem. 2009 Feb;24(1):230-3.

A methanolic extract of dried leaves of Polygala japonica Houtt (Polygalaceae) significantly attenuated nitric oxide production in lipopolysaccharide-simulated BV2 microglia. Five anthraquinones chrysophanol (1), emodin (2), aloe-emodin (3), emodin 8-O-beta-D-glucopyranoside (4) and trihydroxy anthraquinone (5), and four flavonoids kaempferol (6), chrysoeriol (7), Kaempferol 3-gentiobioside (8) and isorhamnetin (9) were isolated from the methanolic extract using bioactivity-guided fractionation. Among them, compounds 1-4, 6 and 7 showed significant inhibitory effect on lipopolysaccharide-induced nitric oxide production in BV2 microglia at the concentrations ranging from 1.0 to 100.0 microM.

Description

Kaempferol 3-O-gentiobioside is a flavonoid isolated from C. alata leaves with antidiabetic activity. Kaempferol 3-O-gentiobioside possesses activity against α-glucosidase and displays carbohydrate enzyme inhibitory effect with an IC50 of 50.0 µM.

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