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Aureusidin

Cat No.:V45596 Purity: ≥98%
Aureusidin is a flavonoid compound with antioxidant and lipoxygenase inhibitory activities.
Aureusidin
Aureusidin Chemical Structure CAS No.: 38216-54-5
Product category: New3
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
Aureusidin is a flavonoid compound with antioxidant and lipoxygenase inhibitory activities. Aureusidin also has anti~inflammatory activity.
Aureusidin is a naturally occurring aurone, a class of flavonoids characterized by a benzofuranone ring system. It has the molecular formula C₁₅H₁₀O₆ and a molecular weight of 286.24. Aureusidin is a yellow pigment found in various plant species, including Antirrhinum majus (snapdragon) and other members of the Scrophulariaceae family. The compound exhibits antioxidant, anti-inflammatory, and anti-cancer activities. Aureusidin is used in natural product research to study the biological activities of aurones and to explore their potential therapeutic applications.
Biological Activity I Assay Protocols (From Reference)
Targets
Aureusidin targets multiple cellular pathways involved in oxidative stress and inflammation. As a flavonoid, it acts as a potent antioxidant by scavenging free radicals and chelating metal ions. It may modulate the activity of enzymes such as cyclooxygenases (COX) and lipoxygenases (LOX), reducing the production of pro-inflammatory mediators. Aureusidin also influences signaling pathways such as NF-κB, MAPK, and PI3K/Akt, contributing to its anti-inflammatory and anti-cancer effects. Specific molecular targets are not extensively characterized.
ln Vitro
Aureusidin exhibits antioxidant activity through DPPH, ABTS, and FRAP radical scavenging assays. It shows anti-inflammatory activity by inhibiting the production of nitric oxide, prostaglandins, and pro-inflammatory cytokines in LPS-stimulated macrophages. Aureusidin also exhibits anti-cancer activity, including inhibition of cancer cell proliferation and induction of apoptosis. Specific IC₅₀ values for various activities depend on the assay system and are not extensively documented.
ln Vivo
In vivo activity data for aureusidin are limited in the available literature. Based on its in vitro antioxidant, anti-inflammatory, and anti-cancer activities, it is anticipated to have potential in vivo efficacy in models of oxidative stress, inflammation, and cancer. However, specific animal studies detailing its therapeutic effects and pharmacokinetics are not extensively documented.
Enzyme Assay
Non-cellular assays for aureusidin typically involve measuring its antioxidant activity using chemical assays such as DPPH, ABTS, and FRAP. The compound's ability to scavenge free radicals is measured spectrophotometrically. Anti-inflammatory activity can be assessed using enzyme inhibition assays for COX-1, COX-2, and LOX. The compound is incubated with the enzyme and substrate, and the inhibition of product formation is measured. IC₅₀ values are calculated from dose-response curves.
Cell Assay
In vitro cellular assays for aureusidin typically use macrophage cell lines such as RAW 264.7 to evaluate anti-inflammatory activity. Cells are treated with various concentrations of the compound, followed by stimulation with lipopolysaccharide (LPS) to induce inflammation. Nitric oxide production is measured using the Griess assay. Pro-inflammatory cytokine levels (TNF-α, IL-1β, IL-6) are quantified by ELISA. Cell viability is assessed using MTT assays to ensure that observed effects are not due to cytotoxicity. For anti-cancer activity, cancer cell lines are treated with aureusidin, and cell proliferation and apoptosis are assessed.
Animal Protocol
In vivo animal studies for aureusidin are not extensively documented in the available literature. Based on its potential anti-inflammatory and anti-cancer activities, typical study designs would involve rodent models of inflammation or cancer. The compound would be administered orally or intraperitoneally. Inflammatory markers, tumor growth, and histopathological changes would be evaluated.
ADME/Pharmacokinetics
Pharmacokinetic properties of aureusidin are not characterized in the available literature. As a flavonoid with a molecular weight of 286.24, it is expected to have limited oral bioavailability due to poor membrane permeability and extensive first-pass metabolism. Flavonoids are generally metabolized via phase II conjugation (glucuronidation and sulfation) and phase I oxidation. Specific PK parameters such as half-life, Cmax, and bioavailability are not documented.
Toxicity/Toxicokinetics
Toxicological data for aureusidin are limited in the available literature. As a naturally occurring flavonoid, it is generally considered to have low toxicity. However, comprehensive toxicology studies are not available. The compound may cause skin and eye irritation upon contact. Standard laboratory safety precautions should be observed when handling this compound.
References

[1]. Mammalian Arginase Inhibitory Activity of Methanolic Extracts and Isolated Compounds from Cyperus Species. Molecules. 2021 Mar 18;26(6):1694.

Additional Infomation
Aureusidin is a hydroxyaurone with hydroxyl groups substituted at the 4, 6, 3', and 4' positions. It is a plant metabolite functionally related to aurone and is the conjugate acid of Aureusidin-6-olate. Aureusidin has been reported in Lepironia articulata, Bulbostylis densa, and other organisms with relevant data.
Aureusidin is a research-grade natural product intended for laboratory use only and is not approved for clinical use. Its CAS number is 38216-54-5. The primary applications of aureusidin include studying the antioxidant, anti-inflammatory, and anti-cancer activities of aurones, investigating the mechanisms of flavonoid bioactivity, and exploring the therapeutic potential of natural aurones. The compound is a valuable tool for natural product chemistry and pharmacology research.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H10O6
Molecular Weight
286.2363
Exact Mass
286.048
CAS #
38216-54-5
PubChem CID
5281220
Appearance
Yellow to orange solid powder
Density
1.708g/cm3
Boiling Point
628.6ºC at 760 mmHg
Flash Point
244.3ºC
Vapour Pressure
2.14E-16mmHg at 25°C
Index of Refraction
1.832
LogP
2.125
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
1
Heavy Atom Count
21
Complexity
447
Defined Atom Stereocenter Count
0
SMILES
C1=CC(=C(C=C1/C=C\2/C(=O)C3=C(C=C(C=C3O2)O)O)O)O
InChi Key
WBEFUVAYFSOUEA-PQMHYQBVSA-N
InChi Code
InChI=1S/C15H10O6/c16-8-5-11(19)14-12(6-8)21-13(15(14)20)4-7-1-2-9(17)10(18)3-7/h1-6,16-19H/b13-4-
Chemical Name
(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3-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: 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 : ~62.5 mg/mL (~218.35 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.27 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 (7.27 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.4936 mL 17.4679 mL 34.9357 mL
5 mM 0.6987 mL 3.4936 mL 6.9871 mL
10 mM 0.3494 mL 1.7468 mL 3.4936 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.

Calculator

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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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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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