yingweiwo

Robinin

Alias: EINECS 206-113-3 NSC 9222 Robinin UNII-75RT1VGM60Kaempferol-3-O-gal-rham-7-O-rham Kaempferol-3-O-robinoside-7-O-rhamnoside
Cat No.:V8341 Purity: ≥98%
Robinin is a flavonoid found in purple cowpea leaves.
Robinin
Robinin Chemical Structure CAS No.: 301-19-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
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Product Description
Robinin is a flavonoid found in purple cowpea leaves. It inhibits the TGF-β, TLR4/NF-κB and TLR2-PI3k-AKT signaling pathways and exerts anti~inflammatory and anti-tumor effects. The combination of Robinin and Methotrexate reduces inflammation in experimental arthritis, and Robinin reduces the cardiotoxic effects induced by Doxorubicin .
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Robinin (1-10 μg/ml, 24 h) has no obvious cytotoxicity in hPBMCs cells [1]. Robinin (6 μg/mL, 24 h) suppresses MCP 1, TNF-α, IL-6 in hPBMCs cells. Robinin (1 μM, 24 h) can inhibit the proliferation and migration of Mia-PACA2 and PANC-1 cells [2]. And ICAM-1 protein expression and TLR2, TLR4 mRNA levels, have anti-inflammatory actions [1]. 1]
ln Vivo
The combination of Robinin and Methotrexate (MTX) (50 mg/kg and 0.3 mg/kg, minimum, twice a week) has anti-inflammatory and anti-arthritic effects in an adjuvant arthritis model [3]. 50 mg/kg, wall, 10 days) can provide cardioprotection against doxorubicin-induced cardiotoxicity by modulating TGF-β1 signaling [4].
Cell Assay
Western Blot Analysis[1]
Cell Types: hPBMC
Tested Concentrations: 6 μg/mL
Incubation Duration: 24 h
Experimental Results: Inhibits the up-regulated expression of MCP 1, TNF-α, IL-6 and ICAM-1, and has anti-inflammatory properties.

Cell viability assay[1]
Cell Types: hPBMC
Tested Concentrations: 1 μg/mL, 2 μg/mL, 4 μg/mL, 6 μg/mL, 8 μg/mL, 10 μg/mL
Incubation Duration: 24 h
Experimental Results: Concentration from 1μg/ml-10μg/ml has no obvious cytotoxicity to hPBMCs.

RT-PCR[1]
Cell Types: hPBMCs
Tested Concentrations: 1 μg/mL, 2 μg/mL, 4 μg/mL, 6 μg/mL, 8 μg/mL, 10 μg/mL
Incubation Duration: 24 h
Experimental Results: Inhibition of TLR2 and TLR4 expression was upregulated.

Cell proliferation assay [2]
Cell Types: Mia-PACA2 and PANC-1
Tested Concentrations: 1 μM
Incubation Duration: 24 h
Experimental Results: Cell proliferation was inhibited.

Cell migration assay[2]
Cell Types: Mia-PACA2 and PANC-1
Tested Concentrations: 1 μM
Incubation Duration: 24 hrs (hours)
Experimental Results: diminished cell migration area
Animal Protocol
Animal/Disease Models: Adjuvant arthritis mouse model [3]
Doses: 50 mg/kg Robinin and 0.3 mg/kg MTX
Route of Administration: po (oral gavage) twice a week
Experimental Results: Anti-inflammatory and anti-arthritic effects .

Animal/Disease Models: Sprague Dawley rat model [4]
Doses: 50 mg/kg Robinin for 10 days
Route of Administration: po (oral gavage)
Experimental Results: Reduction of doxorubicin-induced cardiotoxic effects
References

[1]. Robinin modulates TLR/NF-κB signaling pathway in oxidized LDL induced human peripheral blood mononuclear cells. Int Immunopharmacol. 2014 Jan;18(1):191-7.

[2]. Robinin inhibits pancreatic cancer cell proliferation, EMT and inflammation via regulating TLR2-PI3k-AKT signaling pathway, 10 May 2023.

[3]. Bioflavonoid Robinin from Astragalus falcatus Lam. Mildly Improves the Effect of Metothrexate in Rats with Adjuvant Arthritis. Nutrients. 2021 Apr 13;13(4):1268.

[4]. Robinin modulates doxorubicin-induced cardiac apoptosis by TGF-β1 signaling pathway in Sprague Dawley rats. Biomed Pharmacother. 2014 Oct;68(8):989-98.

Additional Infomation
Robinin is a glycosyloxyflavone that is kaempherol substituted by a 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-galactopyranosyl residue at position 3 and a 6-deoxy-alpha-L-mannopyranosyl residue at position 7 via a glycosidic linkage. It has a role as a plant metabolite. It is a glycosyloxyflavone and a dihydroxyflavone. It is functionally related to a kaempferol.
Robinin has been reported in Glycine max, Trifolium ambiguum, and other organisms with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C33H40O19
Molecular Weight
740.66
Exact Mass
740.216
CAS #
301-19-9
PubChem CID
5281693
Appearance
White to yellow solid powder
Density
1.7±0.1 g/cm3
Boiling Point
1064.4±65.0 °C at 760 mmHg
Melting Point
194-195ºC
Flash Point
335.7±27.8 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.728
LogP
0.89
Hydrogen Bond Donor Count
11
Hydrogen Bond Acceptor Count
19
Rotatable Bond Count
8
Heavy Atom Count
52
Complexity
1260
Defined Atom Stereocenter Count
15
SMILES
O1[C@]([H])([C@@]([H])([C@]([H])([C@]([H])([C@@]1([H])C([H])([H])O[C@@]1([H])[C@@]([H])([C@@]([H])([C@]([H])([C@]([H])(C([H])([H])[H])O1)O[H])O[H])O[H])O[H])O[H])O[H])OC1C(C2=C(C([H])=C(C([H])=C2OC=1C1C([H])=C([H])C(=C([H])C=1[H])O[H])O[C@@]1([H])[C@@]([H])([C@@]([H])([C@]([H])([C@]([H])(C([H])([H])[H])O1)O[H])O[H])O[H])O[H])=O
InChi Key
PEFASEPMJYRQBW-HKWQTAEVSA-N
InChi Code
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
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
Synonyms
EINECS 206-113-3 NSC 9222 Robinin UNII-75RT1VGM60Kaempferol-3-O-gal-rham-7-O-rham Kaempferol-3-O-robinoside-7-O-rhamnoside
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~250 mg/mL (~337.54 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (2.81 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (2.81 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (2.81 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.3501 mL 6.7507 mL 13.5015 mL
5 mM 0.2700 mL 1.3501 mL 2.7003 mL
10 mM 0.1350 mL 0.6751 mL 1.3501 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • The effects of Robinin and CU-T12-9 on HPNE, Mia-PACA2 and PANC-1 viability and proliferation. (A) HPNE, Mia-PACA2 and PANC-1 were exposed to different concentrations of Robinin (500 nM, 1 µM, 5 µM or 10 µM) and CU-T12-9 (1 µM or 5 µM) for 24 h. (B) Proliferation curve of Mia-PACA2 and PANC-1 exposed to control medium in presence with Robinin (1 µM/ml or 5 µM/ml) and Robinin co-cultivated with CU-T12-9 for 24, 48 and 72 h. Data are presented as the means ± standard deviation of 3 independent repeats. *P < 0.05, **P < 0.01, vs. the control group, #P < 0.05, ##P < 0.01, vs. the Robinin co-cultivated with CU-T12-9 group by one-way ANOVA followed by LSD test.[2]. wenwen Zhang, et al. Robinin inhibits pancreatic cancer cell proliferation, EMT and inflammation via regulating TLR2-PI3k-AKT signaling pathway, 10 May 2023.
  • Robinin (1 µM/mL) inhibits cell migration in Mia-PACA2 and PANC-1. Cell migration was evaluated by wound‑healing assay. (A) Representative images of the different treatment groups in Mia-PACA2 at 24 h after scratch. (B) Representative images of different treatment groups in PANC-1 at 24 h after scratch. (C) Quantitative analyses of denuded area percentages (denuded area at the specified time point/denuded area at 0 h) after different treatments at different times in Mia-PACA-2 and PANC-1. Data are presented as the means ± standard deviation of 3 independent repeats. *P < 0.05, **P < 0.01, vs. the control group, #P < 0.05, ##P < 0.01, vs. the Robinin co-cultivated with CU-T12-9 group by one-way ANOVA followed by LSD test. Original magnification, x4.[2]. wenwen Zhang, et al. Robinin inhibits pancreatic cancer cell proliferation, EMT and inflammation via regulating TLR2-PI3k-AKT signaling pathway, 10 May 2023.
  • Robinin (1 µM/mL) alleviated EMT and inflammation in Mia-PACA2 and PANC-1. (A) qRT-PCR of α-SMA and snail expression in Mia-PACA2 and PANC-1. (B) qRT-PCR of IL-6 and TNF-α expression in Mia-PACA2 and PANC-1. (C-D) Protein levels of EMT and inflammation in Mia-PACA2 and PANC-1 were analyzed by western blot analysis and normalized to β-actin expression. P < 0.05, **P < 0.01, vs. the control group, #P < 0.05, ##P < 0.01, vs. the Robinin co-cultivated with CU-T12-9 group. Measurement data were expressed as mean ± standard derivation; data between PC cell and HPNE were compared by t-test, and measurement data among multiple groups were analyzed by one-way analysis of variance with Tukey’s post hoc test. The experiment was repeated three times.[2]. wenwen Zhang, et al. Robinin inhibits pancreatic cancer cell proliferation, EMT and inflammation via regulating TLR2-PI3k-AKT signaling pathway, 10 May 2023.
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