Robinin

CAS# 301-19-9

Robinin

Catalog No. BCN5208----Order now to get a substantial discount!

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Quality Control of Robinin

Number of papers citing our products

Chemical structure

Robinin

3D structure

Chemical Properties of Robinin

Cas No. 301-19-9 SDF Download SDF
PubChem ID 5281693 Appearance Yellow powder
Formula C33H40O19 M.Wt 740.7
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in hot water
Chemical Name 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
SMILES CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)OC5C(C(C(C(O5)C)O)O)O)C6=CC=C(C=C6)O)O)O)O)O)O)O
Standard InChIKey PEFASEPMJYRQBW-HKWQTAEVSA-N
Standard InChI InChI=1S/C33H40O19/c1-10-19(36)23(40)26(43)31(47-10)46-9-17-21(38)25(42)28(45)33(51-17)52-30-22(39)18-15(35)7-14(49-32-27(44)24(41)20(37)11(2)48-32)8-16(18)50-29(30)12-3-5-13(34)6-4-12/h3-8,10-11,17,19-21,23-28,31-38,40-45H,9H2,1-2H3/t10-,11-,17+,19-,20-,21-,23+,24+,25-,26+,27+,28+,31+,32-,33-/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 Robinin

1 Pueraria sp. 2 Robinia sp. 3 Vigna sp.

Biological Activity of Robinin

DescriptionRobinin has cardioprotective effect on doxorubicin-induced cardiac toxicity by modulating TGF-β1 signaling pathway in Sprague Dawley rats. Robinin has protective effect against the ox-LDL induced inflammation stress in hPBMCs by inhibiting TLR4-NF-κB signaling pathway.
TargetsTLR | NF-kB | LDL | COX | LOX | NOS | PGE | p65 | TGF-β/Smad
In vitro

Robinin modulates TLR/NF-κB signaling pathway in oxidized LDL induced human peripheral blood mononuclear cells.[Pubmed: 24295649]

Int Immunopharmacol. 2014 Jan;18(1):191-7.

This study was designed to investigate whether Robinin administration modulates toll-like receptor (TLR) and nuclear factor-kappa B (NF-κB) signaling pathway in oxidized LDL induced human peripheral blood mononuclear cells (hPBMCs).
METHODS AND RESULTS:
The hPBMCs were isolated from healthy human volunteers and the cells were cultured in collagen coated plates at 37°C with 5% CO2 and RPMI as culture medium and were grouped as follows: Group I - control, group II - OxLDL treated and group III - OxLDL+Robinin (6μg/ml). We measured mRNA expression of TLR2 and TLR4 by reverse-transcriptase polymerase chain reaction (RT-PCR) and NF-κB transcription factor assay (ELISA), and western blotting studies were done for knowing expression of monocyte chemotactic protein-1 (MCP 1), tumor necrosis factor-alpha (TNF-α) interleukin-6 (IL-6) and vascular cell adhesion molecule 1 (VCAM-1). The result indicates that OxLDL that induces hPBMCs showed an upregulated expression of TLR2, TLR4, NF-κB, pro-inflammatory cytokines and VCAM-1.
CONCLUSIONS:
Robinin inhibited the ox-LDL induced TLR2 and TLR4 expression at mRNA level and inhibited the translocation of NF-κB p65 by modulating the TLR-NF-κB signaling pathway thereby inhibiting cytokine production and down regulated inflammatory enzymes like cyclooxygenase (COX), lipoxygenase (LOX), nitric oxide synthase (NOS) and prostaglandin E2 (PGE2), thus having protective effect against the ox-LDL induced inflammation stress in hPBMCs by inhibiting TLR4-NF-κB signaling pathway.

In vivo

Robinin modulates doxorubicin-induced cardiac apoptosis by TGF-β1 signaling pathway in Sprague Dawley rats.[Pubmed: 25443416]

Biomed Pharmacother. 2014 Oct;68(8):989-98.

The study focussed on the cardioprotective effect of Robinin on doxorubicin-induced cardio-toxicity in Sprague Dawley rats.
METHODS AND RESULTS:
After the experimental period, animals were sacrificed and the various parameters such as cardiac markers, toxicity parameters, antioxidant status, ROS generation, lipid peroxidation status and inflammatory parameters were assessed. Gene expression study by RT-PCR analysis and proteins expression study by western blotting were done. Doxorubicin causes significant increase in the levels of cardiac marker enzymes, namely lactate dehydrogenase (LDH), creatine phospokinase (CPK), toxicity parameters like serum glutamate oxaloacetate transaminase (SGOT) and serum glutamate pyruvate transaminase (SGPT). Antioxidant enzyme levels were decreased; lipid peroxidation products in heart tissue and inflammatory markers, namely cyclooxygenase (COX2) and lipooxygenase (LOX15) were significantly increased. Gene expression study by RT-PCR analysis of transforming growth factor-β1 (TGF-β1), Smad2, murine double minute (Mdm2), Smad3, cyclin-dependent kinase inhibitor 2A (CDKN2A), Smad4 and Smad7 were significantly altered. The western blotting study of p53, Bcl-2 and Bax also showed altered expression. The supplementation of the Robinin along with DOX caused normalised level of all the above parameters and cardio-toxicity.
CONCLUSIONS:
This study revealed the cardioprotective nature of Robinin on doxorubicin-induced cardiac toxicity by modulating TGF-β1 signaling pathway in Sprague Dawley rats.

Protocol of Robinin

Structure Identification
J Pharm Biomed Anal. 2011 Apr 28;55(1):109-13.

Simultaneous determination of the flavonoids robinin and kaempferol in human breast cancer cells by liquid chromatography-tandem mass spectrometry.[Pubmed: 21232900]

An accurate, precise and sensitive method was developed and validated for the simultaneous quantification of the flavonoid glycoside Robinin, and its algycone kaempferol in human breast cancer MCF-7 cells.
METHODS AND RESULTS:
The application of liquid chromatography-tandem mass spectrometry (LC/MS/MS) with a TurboIonspray interface in negative mode under multiple reactions monitoring was investigated. Chromatographic separation was achieved on a C(18) column using a mobile phase consisting of (A) water with 0.025% formic acid and 1mM ammonium formate and (B) acetonitrile with 0.025% formic acid. Rutin was used as the internal standard for Robinin and fisetin as the internal standard for kaempferol. The assay had a limit of detection of 0.1ng/ml for both compounds when present in cell lysate. The calibration curves were linear from 1 to 250ng/ml (r>0.999) for each compound. The intra- and inter-day coefficients of variation were less than 10% and intra- and inter-day accuracies were within 11%.
CONCLUSIONS:
This assay was successfully applied in a Robinin cellular uptake study to determine the intracellular concentrations of Robinin in MCF-7 cells.

Robinin Dilution Calculator

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Preparing Stock Solutions of Robinin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.3501 mL 6.7504 mL 13.5007 mL 27.0015 mL 33.7519 mL
5 mM 0.27 mL 1.3501 mL 2.7001 mL 5.4003 mL 6.7504 mL
10 mM 0.135 mL 0.675 mL 1.3501 mL 2.7001 mL 3.3752 mL
50 mM 0.027 mL 0.135 mL 0.27 mL 0.54 mL 0.675 mL
100 mM 0.0135 mL 0.0675 mL 0.135 mL 0.27 mL 0.3375 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 Robinin

Robinin modulates doxorubicin-induced cardiac apoptosis by TGF-beta1 signaling pathway in Sprague Dawley rats.[Pubmed:25443416]

Biomed Pharmacother. 2014 Oct;68(8):989-98.

The study focussed on the cardioprotective effect of Robinin on doxorubicin-induced cardio-toxicity in Sprague Dawley rats. After the experimental period, animals were sacrificed and the various parameters such as cardiac markers, toxicity parameters, antioxidant status, ROS generation, lipid peroxidation status and inflammatory parameters were assessed. Gene expression study by RT-PCR analysis and proteins expression study by western blotting were done. Doxorubicin causes significant increase in the levels of cardiac marker enzymes, namely lactate dehydrogenase (LDH), creatine phospokinase (CPK), toxicity parameters like serum glutamate oxaloacetate transaminase (SGOT) and serum glutamate pyruvate transaminase (SGPT). Antioxidant enzyme levels were decreased; lipid peroxidation products in heart tissue and inflammatory markers, namely cyclooxygenase (COX2) and lipooxygenase (LOX15) were significantly increased. Gene expression study by RT-PCR analysis of transforming growth factor-beta1 (TGF-beta1), Smad2, murine double minute (Mdm2), Smad3, cyclin-dependent kinase inhibitor 2A (CDKN2A), Smad4 and Smad7 were significantly altered. The western blotting study of p53, Bcl-2 and Bax also showed altered expression. The supplementation of the Robinin along with DOX caused normalised level of all the above parameters and cardio-toxicity. This study revealed the cardioprotective nature of Robinin on doxorubicin-induced cardiac toxicity by modulating TGF-beta1 signaling pathway in Sprague Dawley rats.

Robinin modulates TLR/NF-kappaB signaling pathway in oxidized LDL induced human peripheral blood mononuclear cells.[Pubmed:24295649]

Int Immunopharmacol. 2014 Jan;18(1):191-7.

This study was designed to investigate whether Robinin administration modulates toll-like receptor (TLR) and nuclear factor-kappa B (NF-kappaB) signaling pathway in oxidized LDL induced human peripheral blood mononuclear cells (hPBMCs). The hPBMCs were isolated from healthy human volunteers and the cells were cultured in collagen coated plates at 37 degrees C with 5% CO2 and RPMI as culture medium and were grouped as follows: Group I - control, group II - OxLDL treated and group III - OxLDL+Robinin (6mug/ml). We measured mRNA expression of TLR2 and TLR4 by reverse-transcriptase polymerase chain reaction (RT-PCR) and NF-kappaB transcription factor assay (ELISA), and western blotting studies were done for knowing expression of monocyte chemotactic protein-1 (MCP 1), tumor necrosis factor-alpha (TNF-alpha) interleukin-6 (IL-6) and vascular cell adhesion molecule 1 (VCAM-1). The result indicates that OxLDL that induces hPBMCs showed an upregulated expression of TLR2, TLR4, NF-kappaB, pro-inflammatory cytokines and VCAM-1. Robinin inhibited the ox-LDL induced TLR2 and TLR4 expression at mRNA level and inhibited the translocation of NF-kappaB p65 by modulating the TLR-NF-kappaB signaling pathway thereby inhibiting cytokine production and down regulated inflammatory enzymes like cyclooxygenase (COX), lipoxygenase (LOX), nitric oxide synthase (NOS) and prostaglandin E2 (PGE2), thus having protective effect against the ox-LDL induced inflammation stress in hPBMCs by inhibiting TLR4-NF-kappaB signaling pathway.

Simultaneous determination of the flavonoids robinin and kaempferol in human breast cancer cells by liquid chromatography-tandem mass spectrometry.[Pubmed:21232900]

J Pharm Biomed Anal. 2011 Apr 28;55(1):109-13.

An accurate, precise and sensitive method was developed and validated for the simultaneous quantification of the flavonoid glycoside Robinin, and its algycone kaempferol in human breast cancer MCF-7 cells. The application of liquid chromatography-tandem mass spectrometry (LC/MS/MS) with a TurboIonspray interface in negative mode under multiple reactions monitoring was investigated. Chromatographic separation was achieved on a C(18) column using a mobile phase consisting of (A) water with 0.025% formic acid and 1mM ammonium formate and (B) acetonitrile with 0.025% formic acid. Rutin was used as the internal standard for Robinin and fisetin as the internal standard for kaempferol. The assay had a limit of detection of 0.1ng/ml for both compounds when present in cell lysate. The calibration curves were linear from 1 to 250ng/ml (r>0.999) for each compound. The intra- and inter-day coefficients of variation were less than 10% and intra- and inter-day accuracies were within 11%. This assay was successfully applied in a Robinin cellular uptake study to determine the intracellular concentrations of Robinin in MCF-7 cells.

Description

Robinin is present in flavonoid fraction of Vigna unguiculata leaf. Robinin inhibits upregulated expression of TLR2 and TLR4. Robinin ameliorates oxidized low density lipoprotein (Ox-LDL) induced inflammatory insult through TLR4/NF-κB pathway.

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