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Juglanin

Cat No.:V22846 Purity: ≥98%
Juglanin is a novel and potent antioxidant agent
Juglanin
Juglanin Chemical Structure CAS No.: 5041-67-8
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
100mg
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Product Description
Juglanin is a naturally occurring flavonoid, acting as a JNK acticator with inflammation and anti-tumor activities. Inducing apoptosis and autophagy on human breast cancer cells.
Juglanin (CAS#: 5041-67-8) is a naturally occurring flavonoid, specifically kaempferol-3-arabinofuranoside, that acts as a JNK (c-Jun N-terminal kinase) activator. It displays both anti-inflammatory and anti-tumor effects. Juglanin can induce apoptosis and autophagy in human breast cancer cells. It inhibits the proliferation of breast cancer cells in a dose- and time-dependent manner and presents less cytotoxicity against normal cells. Juglanin also has hepatoprotective activity and has been shown to protect against fructose-induced hepatitis in rats by inhibiting inflammation and apoptosis through the TLR4 and JAK2/STAT3 signaling pathways.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary target of Juglanin is JNK (c-Jun N-terminal kinase), a member of the mitogen-activated protein kinase (MAPK) family that plays a critical role in stress responses, inflammation, apoptosis, and autophagy. Juglanin acts as a JNK activator, stimulating JNK signaling pathways that regulate cell survival and death decisions. The compound also modulates TLR4 and JAK2/STAT3 signaling pathways, contributing to its anti-inflammatory and hepatoprotective effects. By activating JNK, Juglanin induces apoptosis and autophagy in cancer cells while showing less cytotoxicity against normal cells.
ln Vitro
In vitro, Juglanin inhibits the proliferation of breast cancer cells in a dose- and time-dependent manner. It induces apoptosis and autophagy in human breast cancer cells. The compound shows less cytotoxicity against normal cells, suggesting a favorable selectivity profile. Juglanin has anti-inflammatory activity and inhibits the TLR4 and JAK2/STAT3 signaling pathways. Its ability to activate JNK makes it a valuable tool for studying JNK-mediated signaling in cancer and inflammation.
ln Vivo
In vivo, Juglanin protects against fructose-induced hepatitis in rats by inhibiting inflammation and apoptosis through the TLR4 and JAK2/STAT3 signaling pathways. It has hepatoprotective activity. As an anti-tumor compound, Juglanin would be expected to have efficacy in cancer models. However, specific in vivo anti-tumor efficacy data from animal models is not detailed in the available sources. Juglanin's anti-inflammatory and hepatoprotective activities suggest potential applications in liver diseases.
Enzyme Assay
For JNK activators, standard cell-free assays involve measuring JNK kinase activity using recombinant JNK enzyme and peptide substrates (e.g., c-Jun). The compound is incubated with the enzyme, ATP, and substrate, and phosphorylation is detected by radioactive or fluorescent methods. For TLR4 and JAK2/STAT3 pathway modulation, standard enzyme activity or receptor binding assays can be employed.
Cell Assay
For JNK activators, standard cellular assays involve treatment of cancer cell lines with the test compound for 24-72 hours. JNK activation is assessed by measuring phosphorylation of JNK and its substrate c-Jun by western blot. Apoptosis is assessed by Annexin V/PI staining, caspase activity assays, and DNA fragmentation. Autophagy is assessed by LC3-II accumulation and autophagosome formation. Cell viability is measured using MTT or CellTiter-Glo assays.
Animal Protocol
For in vivo evaluation of hepatoprotective compounds, standard animal models include fructose-induced hepatitis in rats or CCl4-induced liver injury. The compound is typically administered orally or intraperitoneally, and liver function markers (ALT, AST), inflammatory cytokines, and apoptosis markers are assessed. For anti-tumor studies, tumor xenograft models are used. Juglanin has been evaluated in fructose-fed rats.
ADME/Pharmacokinetics
Detailed pharmacokinetic data for Juglanin is not provided in the available sources. The compound has a molecular weight of approximately 418.35 and formula C20H18O10 (kaempferol-3-arabinofuranoside). As a flavonoid glycoside, it would likely have limited oral bioavailability due to its hydrophilic nature and susceptibility to intestinal metabolism. Comprehensive pharmacokinetic studies would be required for therapeutic development.
Toxicity/Toxicokinetics
Detailed toxicology data for Juglanin is not provided in the available sources. As a naturally occurring flavonoid, it may have a favorable safety profile at moderate doses. Juglanin shows less cytotoxicity against normal cells, suggesting a favorable selectivity profile. However, comprehensive toxicological evaluation would be required for therapeutic development. The compound is for research use only and not for therapeutic applications.
References

[1]. Juglanin induces apoptosis and autophagy in human breast cancer progression via ROS/JNK promotion. Biomed Pharmacother. 2017 Jan;85:303-312.

[2]. Juglanin ameliorates LPS-induced neuroinflammation in animal models of Parkinson's disease and cell culture via inactivating TLR4/NF-κB pathway. Biomed Pharmacother. 2018 Jan;97:1011-1019.

[3]. Juglanin alleviates bleomycin-induced lung injury by suppressing inflammation and fibrosis via targeting sting signaling. Biomed Pharmacother. 2020 Jul;127:110119.

Additional Infomation
Kaempferol-3-arabinofuranoside belongs to the flavonoid family and is a type of glycoside. It has been reported that juglone is found in the herbaceous plant Hedyotis diffusa, Ficus taiwanensis, and other organisms with relevant data.
Juglanin is also known as Kaempferol-3-arabinofuranoside and belongs to the flavonoid family. It is a JNK activator with inflammation and anti-tumor activities. The compound induces apoptosis and autophagy in human breast cancer cells and inhibits proliferation in a dose- and time-dependent manner. Juglanin protects against fructose-induced hepatitis through TLR4 and JAK2/STAT3 pathways. No regulatory approval has been identified.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H24O7S
Molecular Weight
408.46536
Exact Mass
418.089
CAS #
5041-67-8
PubChem CID
5318717
Appearance
White to yellow solid powder
Density
1.8±0.1 g/cm3
Boiling Point
803.5±65.0 °C at 760 mmHg
Melting Point
230-231℃ (ethanol )
Flash Point
289.0±27.8 °C
Vapour Pressure
0.0±3.0 mmHg at 25°C
Index of Refraction
1.771
LogP
2.26
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
4
Heavy Atom Count
30
Complexity
673
Defined Atom Stereocenter Count
4
SMILES
C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H](O4)CO)O)O)O
InChi Key
POQICXMTUPVZMX-UXYNSRGZSA-N
InChi Code
InChI=1S/C20H18O10/c21-7-13-15(25)17(27)20(29-13)30-19-16(26)14-11(24)5-10(23)6-12(14)28-18(19)8-1-3-9(22)4-2-8/h1-6,13,15,17,20-25,27H,7H2/t13-,15-,17+,20-/m0/s1
Chemical Name
3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
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: Please store this product in a sealed and protected environment, avoid exposure to moisture.
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 : ~100 mg/mL (~239.03 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.98 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 25.0 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: ≥ 2.5 mg/mL (5.98 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 25.0 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.4482 mL 12.2408 mL 24.4816 mL
5 mM 0.4896 mL 2.4482 mL 4.8963 mL
10 mM 0.2448 mL 1.2241 mL 2.4482 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 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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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.

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