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Vitexin-2''-O-rhamnoside

CAS# 64820-99-1

Vitexin-2''-O-rhamnoside

Catalog No. BCN5025----Order now to get a substantial discount!

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Quality Control of Vitexin-2''-O-rhamnoside

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Chemical structure

Vitexin-2''-O-rhamnoside

3D structure

Chemical Properties of Vitexin-2''-O-rhamnoside

Cas No. 64820-99-1 SDF Download SDF
PubChem ID 5282151 Appearance Light yellow powder
Formula C27H30O14 M.Wt 578.52
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms 2''-O-Rhamnosylvitexin; 4',5,7-Trihydroxyflavone 8-C-(2''-rhamnosylglucoside)
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
SMILES CC1C(C(C(C(O1)OC2C(C(C(OC2C3=C(C=C(C4=C3OC(=CC4=O)C5=CC=C(C=C5)O)O)O)CO)O)O)O)O)O
Standard InChIKey LYGPBZVKGHHTIE-HUBYJIGHSA-N
Standard InChI InChI=1S/C27H30O14/c1-9-19(33)21(35)23(37)27(38-9)41-26-22(36)20(34)16(8-28)40-25(26)18-13(31)6-12(30)17-14(32)7-15(39-24(17)18)10-2-4-11(29)5-3-10/h2-7,9,16,19-23,25-31,33-37H,8H2,1H3/t9-,16+,19-,20+,21+,22-,23+,25-,26+,27-/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 Vitexin-2''-O-rhamnoside

1 Crataegus sp. 2 Glycine sp.

Biological Activity of Vitexin-2''-O-rhamnoside

DescriptionVitexin-2''-O-rhamnoside contributes to the protection against H₂O₂ -mediated oxidative stress damage and could be safely used for a wide range of concentrations.It has low bioavailability, mainly related to its poor absorption in the intestine.
TargetsP450 (e.g. CYP17) | P-gp
In vitro

Effects of vitexin-2"-O-rhamnoside and vitexin-4"-O-glucoside on growth and oxidative stress-induced cell apoptosis of human adipose-derived stem cells.[Pubmed: 24533889]

J Pharm Pharmacol. 2014 Jul;66(7):988-97.

Vitexin-2''-O-rhamnoside(VOR) and vitexin-4"-O-glucoside (VOG) are the two main flavonoid glycosides of the leaves of Cratagus pinnatifida Bge. var. major N. E. Br. that has been widely used for the treatment of cardiovascular system diseases. In this study, we simultaneously investigated the influence of Vitexin-2''-O-rhamnoside and VOG on human adipose-derived stem cells (hADSCs) injury induced by hydrogen peroxide (H2 O2 ) to further characterize their anti-oxidative and anti-apoptotic activity.
METHODS AND RESULTS:
hADSCs were isolated, cultured in vitro and pretreated with 62.5 μm Vitexin-2''-O-rhamnoside or 120 μm VOG for 24 h and then exposed to 500 μm H2 O2 for an additional 4 h.Pretreatment of hADSCs with Vitexin-2''-O-rhamnoside and VOG was demonstrated to significantly ameliorate the toxicity and apoptosis effects, such as morphological distortion, nuclear condensation, decreased intracellular caspase-3 activity and percentage of cells in apoptosis/necrosis by using morphological assay, immunocytochemistry and flow cytometric evaluation. In addition, Vitexin-2''-O-rhamnoside and VOG caused no cytotoxic effect on hADSCs at concentrations up to 250 and 480 μm, respectively.
CONCLUSIONS:
Our results indicated that both Vitexin-2''-O-rhamnoside and VOG contribute to the protection against H2 O2 -mediated oxidative stress damage and could be safely used for a wide range of concentrations.

Protocol of Vitexin-2''-O-rhamnoside

Kinase Assay

Hepatic, gastric and intestinal first-pass effects of vitexin-2″-O-rhamnoside in rats by ultra-high performance liquid chromatography.[Pubmed: 26031900 ]

Biomed Chromatogr. 2015 May 29.

Previous research in our laboratory found that the absolute bioavailability of Vitexin-2''-O-rhamnoside (VR) was quite low at 4.89%.
METHODS AND RESULTS:
A rapid and sensitive UHPLC method using hesperidin as an internal standard was therefore developed and validated to investigate the reasons for this by determining VR in rat plasma after administering intravenously, intraportally (5 mg/kg), intraduodenally and intragastrically (40 mg/kg) to the rat model of the hepatic, gastric and intestinal first-pass effects. As only a high intestinal first-pass effect of VR was found, that is, there existed a low bioavailability of VR (2.40%), inhibitors of P-glycoprotein (P-gp) and cytochrome P450 3A (CYP3A), including verapamil, cyclosporin A and midazolam, and absorption enhancers, including bile salts and borneol, combined with VR, were instilled into duodenum to evaluate the effects on bioavailability of VR.
CONCLUSIONS:
The results demonstrated that area under the concentration-time curve (AUC) values of VR slightly increased after administration of verapamil, cyclosporin A and midazolam, indicating that CYP3A and P-gp do not play an important role in the first-pass effect in the intestine. AUC values of VR significantly increased after administering bile salts or borneol, indicating that the low bioavailability of VR was mainly related to its poor absorption in the intestine.

Structure Identification
J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Jul 1;878(21):1837-44.

Simultaneous determination of vitexin-4''-O-glucoside, vitexin-2''-O-rhamnoside, rutin and vitexin from hawthorn leaves flavonoids in rat plasma by UPLC-ESI-MS/MS.[Pubmed: 20570577]


METHODS AND RESULTS:
A sensitive and accurate ultra-performance liquid chromatography electrospray ionization tandem mass spectrometry (UPLC-ESI-MS/MS) method was developed and validated for the simultaneous determination of vitexin-4''-O-glucoside (VGL), Vitexin-2''-O-rhamnoside (VRH), rutin (RUT) and vitexin (VIT) in rat plasma after intravenous administration of hawthorn leaves flavonoids (HLF). Following protein precipitation by methanol, the analytes were separated on an ACQUITY UPLC BEH C(18) column packed with 1.7 microm particles by gradient elution using a mobile phase composed of acetonitrile and water (containing 0.1% formic acid) at a flow rate of 0.20 mL/min. The analytes and diphenhydramine (internal standard, IS) were detected in the multiple reaction monitoring (MRM) mode by means of an electrospray ionization (ESI) interface (m/z 292.96 for vitexin-4''-O-glucoside, m/z 293.10 for Vitexin-2''-O-rhamnoside, m/z 299.92 for rutin, m/z 310.94 for vitexin and m/z 166.96 for IS). The calibration curve was linear over the range 10-40,000 ng/mL for vitexin-4''-O-glucoside, 10-50,000 ng/mL for Vitexin-2''-O-rhamnoside, 8-1000 ng/mL for rutin and 16-2000 ng/mL for vitexin.

Vitexin-2''-O-rhamnoside Dilution Calculator

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Vitexin-2''-O-rhamnoside Molarity Calculator

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Preparing Stock Solutions of Vitexin-2''-O-rhamnoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.7285 mL 8.6427 mL 17.2855 mL 34.571 mL 43.2137 mL
5 mM 0.3457 mL 1.7285 mL 3.4571 mL 6.9142 mL 8.6427 mL
10 mM 0.1729 mL 0.8643 mL 1.7285 mL 3.4571 mL 4.3214 mL
50 mM 0.0346 mL 0.1729 mL 0.3457 mL 0.6914 mL 0.8643 mL
100 mM 0.0173 mL 0.0864 mL 0.1729 mL 0.3457 mL 0.4321 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 Vitexin-2''-O-rhamnoside

Simultaneous determination of vitexin-4''-O-glucoside, vitexin-2''-O-rhamnoside, rutin and vitexin from hawthorn leaves flavonoids in rat plasma by UPLC-ESI-MS/MS.[Pubmed:20570577]

J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Jul 1;878(21):1837-44.

A sensitive and accurate ultra-performance liquid chromatography electrospray ionization tandem mass spectrometry (UPLC-ESI-MS/MS) method was developed and validated for the simultaneous determination of vitexin-4''-O-glucoside (VGL), vitexin-2''-O-rhamnoside (VRH), rutin (RUT) and vitexin (VIT) in rat plasma after intravenous administration of hawthorn leaves flavonoids (HLF). Following protein precipitation by methanol, the analytes were separated on an ACQUITY UPLC BEH C(18) column packed with 1.7 microm particles by gradient elution using a mobile phase composed of acetonitrile and water (containing 0.1% formic acid) at a flow rate of 0.20 mL/min. The analytes and diphenhydramine (internal standard, IS) were detected in the multiple reaction monitoring (MRM) mode by means of an electrospray ionization (ESI) interface (m/z 292.96 for vitexin-4''-O-glucoside, m/z 293.10 for vitexin-2''-O-rhamnoside, m/z 299.92 for rutin, m/z 310.94 for vitexin and m/z 166.96 for IS). The calibration curve was linear over the range 10-40,000 ng/mL for vitexin-4''-O-glucoside, 10-50,000 ng/mL for vitexin-2''-O-rhamnoside, 8-1000 ng/mL for rutin and 16-2000 ng/mL for vitexin. The intra- and inter-run precisions (relative standard deviation, RSD) of these analytes were all within 15% and the accuracy (the relative error, RE) ranged from -10% to 10%. The stability experiment indicated that the four analytes in rat plasma samples and plasma extracts under anticipated conditions were stable. The developed method was applied for the first time to pharmacokinetic studies of the four bioactive compounds of hawthorn leaves flavonoids following a single intravenous administration of 20 mg/kg in rats.

Hepatic, gastric and intestinal first-pass effects of vitexin-2''-O-rhamnoside in rats by ultra-high-performance liquid chromatography.[Pubmed:26031900]

Biomed Chromatogr. 2016 Feb;30(2):111-6.

Previous research in our laboratory found that the absolute bioavailability of vitexin-2''-O-rhamnoside (VR) was quite low at 4.89%. A rapid and sensitive UHPLC method using hesperidin as an internal standard was therefore developed and validated to investigate the reasons for this by determining VR in rat plasma after administering intravenously, intraportally (5 mg/kg), intraduodenally and intragastrically (40 mg/kg) to the rat model of the hepatic, gastric and intestinal first-pass effects. As only a high intestinal first-pass effect of VR was found, that is, there existed a low bioavailability of VR (2.40%), inhibitors of P-glycoprotein (P-gp) and cytochrome P450 3A (CYP3A), including verapamil, cyclosporin A and midazolam, and absorption enhancers, including bile salts and borneol, combined with VR, were instilled into duodenum to evaluate the effects on bioavailability of VR. The results demonstrated that area under the concentration-time curve (AUC) values of VR slightly increased after administration of verapamil, cyclosporin A and midazolam, indicating that CYP3A and P-gp do not play an important role in the first-pass effect in the intestine. AUC values of VR significantly increased after administering bile salts or borneol, indicating that the low bioavailability of VR was mainly related to its poor absorption in the intestine.

Effects of vitexin-2"-O-rhamnoside and vitexin-4"-O-glucoside on growth and oxidative stress-induced cell apoptosis of human adipose-derived stem cells.[Pubmed:24533889]

J Pharm Pharmacol. 2014 Jul;66(7):988-97.

OBJECTIVES: Vitexin-2"-O-rhamnoside (VOR) and vitexin-4"-O-glucoside (VOG) are the two main flavonoid glycosides of the leaves of Cratagus pinnatifida Bge. var. major N. E. Br. that has been widely used for the treatment of cardiovascular system diseases. In this study, we simultaneously investigated the influence of VOR and VOG on human adipose-derived stem cells (hADSCs) injury induced by hydrogen peroxide (H2 O2 ) to further characterize their anti-oxidative and anti-apoptotic activity. METHODS: hADSCs were isolated, cultured in vitro and pretreated with 62.5 mum VOR or 120 mum VOG for 24 h and then exposed to 500 mum H2 O2 for an additional 4 h. KEY FINDINGS: Pretreatment of hADSCs with VOR and VOG was demonstrated to significantly ameliorate the toxicity and apoptosis effects, such as morphological distortion, nuclear condensation, decreased intracellular caspase-3 activity and percentage of cells in apoptosis/necrosis by using morphological assay, immunocytochemistry and flow cytometric evaluation. In addition, VOR and VOG caused no cytotoxic effect on hADSCs at concentrations up to 250 and 480 mum, respectively. CONCLUSIONS: Our results indicated that both VOR and VOG contribute to the protection against H2 O2 -mediated oxidative stress damage and could be safely used for a wide range of concentrations.

Description

Vitexin-2-O-rhamnoside, a main flavonoid glycoside of the leaves of Cratagus pinnatifida Bge, contributes to the protection against H2O2-mediated oxidative stress damage and has potential to treat cardiovascular system diseases.

Keywords:

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