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| Targets |
Robinin inhibits TLR4/NF-κB signaling in oxidized LDL-induced human PBMCs [1].
Robinin suppresses TLR2-PI3K-AKT signaling in pancreatic cancer cells [2]. Robinin modulates TGF-β1 signaling in doxorubicin-induced cardiac apoptosis [4]. |
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| 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].
In oxidized LDL (ox-LDL)-induced human peripheral blood mononuclear cells (PBMCs), Robinin (10, 20, 50 μM) concentration-dependently inhibited the activation of TLR4/MyD88/NF-κB signaling pathway. Western blot analysis showed that Robinin reduced the phosphorylation of NF-κB p65 and the degradation of IκBα, as well as the expression of TLR4 and MyD88. RT-PCR and ELISA results demonstrated that Robinin decreased the mRNA expression and secretion of pro-inflammatory cytokines TNF-α, IL-6, and IL-1β [1] In pancreatic cancer cell lines (PANC-1 and MIA PaCa-2), Robinin (5, 10, 20 μM) inhibited cell proliferation in a concentration-dependent manner, as shown by CCK-8 assay. It also suppressed epithelial-mesenchymal transition (EMT) by up-regulating E-cadherin and down-regulating N-cadherin, Snail, and Twist (detected by Western blot and PCR). Additionally, Robinin induced apoptosis, increased Bax/Bcl-2 ratio, and activated caspase-3. Mechanistically, it down-regulated the expression of TLR2, phosphorylated PI3K (p-PI3K), and phosphorylated AKT (p-AKT) via Western blot analysis, and silencing TLR2 attenuated these effects [2] |
| 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].
In adjuvant-induced arthritis rats, Robinin (combined with methotrexate) mildly enhanced the anti-arthritic effect of methotrexate, as evidenced by reduced paw swelling and decreased serum levels of pro-inflammatory cytokines (IL-1β, TNF-α, IL-6) [3] In doxorubicin-induced cardiac apoptosis in Sprague Dawley rats, Robinin (10, 20 mg/kg) alleviated cardiac apoptosis. It reduced serum levels of cardiac injury markers (CK-MB, LDH), decreased caspase-3 activity in heart tissues, up-regulated Bcl-2 expression, and down-regulated Bax expression. Moreover, Robinin inhibited the expression of TGF-β1 and phosphorylation of Smad2/3 in heart tissues, as shown by Western blot [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. For ox-LDL-induced human PBMCs: Cells were treated with ox-LDL (100 μg/ml) and Robinin (10, 20, 50 μM) for 24 hours. Western blot was used to detect the protein levels of TLR4, MyD88, phosphorylated NF-κB p65, and IκBα. RT-PCR was performed to measure mRNA levels of TNF-α, IL-6, and IL-1β. ELISA was used to determine the secretion of these cytokines in cell supernatants [1] For pancreatic cancer cells (PANC-1, MIA PaCa-2): Cells were treated with Robinin (5, 10, 20 μM) for 24-72 hours. CCK-8 assay was used to assess cell viability. Clone formation assay was performed to evaluate clonogenic capacity. Western blot analyzed the protein levels of TLR2, p-PI3K, p-AKT, E-cadherin, N-cadherin, Snail, Twist, Bax, Bcl-2, and cleaved caspase-3. RT-PCR detected the mRNA expression of related genes. Flow cytometry was used to detect cell apoptosis [2] |
| 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. For adjuvant-induced arthritis in rats: Rats were induced by complete Freund's adjuvant. They were divided into control group, model group, Robinin alone group, methotrexate alone group, and Robinin + methotrexate combination group. Drugs were administered for 21 days, and paw swelling was measured regularly. Serum levels of IL-1β, TNF-α, and IL-6 were detected, and joint histopathological changes were observed [3] For doxorubicin-induced cardiac toxicity in Sprague Dawley rats: Rats were divided into control group, doxorubicin model group, and doxorubicin + Robinin (10, 20 mg/kg) groups. Doxorubicin was injected intraperitoneally to induce cardiac toxicity, and Robinin was administered accordingly. The ratio of heart weight to body weight was calculated. Serum CK-MB and LDH activities were measured. Western blot analyzed the protein levels of caspase-3, Bax, Bcl-2, TGF-β1, and p-Smad2/3 in heart tissues [4] |
| Toxicity/Toxicokinetics |
Acute toxicity: No mortality or behavioral changes in mice after single i.p. dose of robinin (1000 mg/kg) [3].
Subacute toxicity: In arthritic rats, robinin (10 mg/kg) + methotrexate did not increase serum ALT/AST or creatinine vs. methotrexate alone [3].
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| References |
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| 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. Robinin is a flavonoid glycoside derived from Astragalus falcatus [3]. Its cardioprotection involves TGF-β1-mediated anti-apoptosis [4], while anti-pancreatic cancer effects rely on TLR2-PI3K-AKT suppression [2]. Synergy with methotrexate in arthritis suggests immunomodulatory potential [3]. |
| Molecular Formula |
C33H40O19
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|---|---|
| Molecular Weight |
740.66
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| Exact Mass |
740.216
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| Elemental Analysis |
C, 53.51; H, 5.44; O, 41.04
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| CAS # |
301-19-9
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| PubChem CID |
5281693
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| Appearance |
White to yellow solid powder
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| Density |
1.7±0.1 g/cm3
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| Boiling Point |
1064.4±65.0 °C at 760 mmHg
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| Melting Point |
194-195ºC
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| Flash Point |
335.7±27.8 °C
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| Vapour Pressure |
0.0±0.3 mmHg at 25°C
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| Index of Refraction |
1.728
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| LogP |
0.89
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| Hydrogen Bond Donor Count |
11
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| Hydrogen Bond Acceptor Count |
19
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
52
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| Complexity |
1260
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| Defined Atom Stereocenter Count |
15
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| 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
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| InChi Key |
PEFASEPMJYRQBW-HKWQTAEVSA-N
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| 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
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| 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
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| Synonyms |
EINECS 206-113-3; NSC 9222; Robinin; UNII-75RT1VGM60; Robinin; 301-19-9; 75RT1VGM60; CHEBI:8878; 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; 4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-galactopyranosyl)oxy)-7-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-; 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one; NSC-9222; Kaempferol-3-O-gal-rham-7-O-rham; Kaempferol-3-O-robinoside-7-O-rhamnoside
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~250 mg/mL (~337.54 mM)
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| 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. View More
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. |
| 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.
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.
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