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Cyanidin 3-sambubioside chloride (Cyanidin-3-O-sambubioside chloride)

Cat No.:V54328 Purity: ≥98%
Cyanidin 3-sambubioside chloride (Cyanidin-3-O-sambubioside chloride), a major anthocyanin, a natural colorant, is a potent NO inhibitor.
Cyanidin 3-sambubioside chloride (Cyanidin-3-O-sambubioside chloride)
Cyanidin 3-sambubioside chloride (Cyanidin-3-O-sambubioside chloride) Chemical Structure CAS No.: 33012-73-6
Product category: Influenza Virus
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
Cyanidin 3-sambubioside chloride (Cyanidin-3-O-sambubioside chloride), a major anthocyanin, a natural colorant, is a potent NO inhibitor. Cyanidin 3-sambubioside chloride is an H274Y mutation inhibitor that can suppress influenza neuraminidase activity with IC50 of 72 μM. Cyanidin 3-sambubioside chloride inhibits angiotensin-converting enzyme (ACE) activity and has antioxidant, anti-angiogenic, and antiviral properties.
Cyanidin 3-sambubioside chloride (CAS 33012-73-6), also known as cyanidin-3-O-sambubioside chloride, is an anthocyanin, a class of water-soluble plant pigments responsible for red, purple, and blue colors in flowers and fruits. This compound consists of the cyanidin aglycone (a flavylium cation) with a sambubiosyl (glucose-xylose disaccharide) moiety attached at the 3-position. Anthocyanins are known for their antioxidant activities and potential health benefits. The compound is a research chemical used in studies of plant pigments and their biological activities.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary biological targets of cyanidin 3-sambubioside chloride are related to its antioxidant properties. Anthocyanins scavenge free radicals, chelate metal ions, and modulate signaling pathways such as NF-κB and Nrf2. They may also interact with enzymes involved in inflammation and metabolism. The compound's effects are mediated through both direct antioxidant activity and modulation of cellular signaling pathways. Specific molecular targets require further elucidation.
ln Vitro
In vitro studies have demonstrated the antioxidant activity of cyanidin 3-sambubioside chloride and other anthocyanins. The compound scavenges DPPH, ABTS, and other free radicals. It may also exhibit anti-inflammatory activity through inhibition of pro-inflammatory cytokine production and suppression of inflammatory mediators. Anthocyanins have been shown to inhibit enzymes such as α-glucosidase and tyrosinase. Specific IC₅₀ values for radical scavenging and enzyme inhibition have been reported.
ln Vivo
In vivo studies have shown the health benefits of anthocyanins in animal models. Cyanidin glycosides have demonstrated antioxidant, anti-inflammatory, and cardioprotective effects. They may improve vascular function, reduce blood pressure, and have beneficial effects on metabolism. Cyanidin 3-sambubioside is a dietary anthocyanin found in various berries and fruits. Specific in vivo data for this compound have been reported in the nutritional and pharmacological literature.
Enzyme Assay
For antioxidant assays, DPPH radical scavenging, ABTS, and FRAP assays are used. The compound is incubated with the radical-generating system, and absorbance is measured. IC₅₀ values are calculated. For anti-inflammatory assays, macrophages or other cells are stimulated with LPS, and cytokine production is measured by ELISA. For enzyme inhibition assays, the compound is incubated with the enzyme and substrate, and product formation is monitored spectrophotometrically.
Cell Assay
For in vitro cell-based studies, various cell lines such as endothelial cells, macrophages, or cancer cells may be used. Cells are cultured in appropriate media and treated with serial dilutions of cyanidin 3-sambubioside chloride. Cell viability is assessed using MTT or other assays. Markers of oxidative stress, inflammation, or cell signaling are measured by Western blotting, ELISA, or qPCR. Standard protocols for these assays are described in the literature.
Animal Protocol
In vivo animal studies for cyanidin 3-sambubioside chloride typically use mouse or rat models. For antioxidant or anti-inflammatory studies, animals are treated with the compound via oral administration, and markers of oxidative stress or inflammation are measured. For cardioprotection studies, models of cardiovascular disease may be used. The compound may also be studied for its effects on metabolism and obesity. Standard protocols can be adapted from the literature.
ADME/Pharmacokinetics
Pharmacokinetic properties of cyanidin 3-sambubioside chloride have been characterized. Anthocyanins are generally poorly absorbed, with most of the ingested compound reaching the colon where it is metabolized by the gut microbiota. The compound is rapidly eliminated from the circulation. The half-life of anthocyanins in plasma is short (1-2 hours). Specific PK parameters have been reported for various anthocyanins. The chloride salt form is water-soluble.
Toxicity/Toxicokinetics
Toxicological data for cyanidin 3-sambubioside chloride are limited. As a dietary anthocyanin found in many fruits and vegetables, it is considered safe. No significant toxicity has been reported at dietary intake levels. High doses may have mild gastrointestinal effects. Comprehensive toxicological studies are available for anthocyanin-rich extracts rather than for the pure compound.
References

[1]. Detection of cyanidin in different-colored peanut testae and identification of peanut cyanidin 3-sambubioside. J Agric Food Chem. 2009 Oct 14;57(19):8805-11.

[2]. The inhibitory performance of flavonoid cyanidin-3-sambubiocide against H274Y mutation in H1N1 influenza virus. J Biomol Struct Dyn. 2018 Dec;36(16):4255-4269.

[3]. Cyanidin-3-O-sambubioside from Acanthopanax sessiliflorus fruit inhibits metastasis by downregulating MMP-9 in breast cancer cells MDA-MB-231. Planta Med. 2013 Nov;79(17):1636-40.

Additional Infomation
See also: Hibiscus sabdariffa Flower (partial).
Cyanidin 3-sambubioside chloride is a research compound used in studies of anthocyanins, plant pigments, and their biological activities. It is found in various berries and fruits. The compound is used as a reference standard for analytical method development (e.g., HPLC, LC-MS) for anthocyanin analysis in foods and biological samples. The compound has been studied for its antioxidant, anti-inflammatory, and potential health-promoting effects. No clinical trials or therapeutic applications have been reported.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C26H29CLO15
Molecular Weight
616.95
Exact Mass
616.119
CAS #
33012-73-6
PubChem CID
3084569
Appearance
Brown to black solid powder
Hydrogen Bond Donor Count
10
Hydrogen Bond Acceptor Count
15
Rotatable Bond Count
6
Heavy Atom Count
42
Complexity
852
Defined Atom Stereocenter Count
9
SMILES
C1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC4=C(C=C(C=C4[O+]=C3C5=CC(=C(C=C5)O)O)O)O)CO)O)O)O)O)O.[Cl-]
InChi Key
BWHXEGJOYVNGQH-XOBUMVIESA-N
InChi Code
InChI=1S/C26H28O15.ClH/c27-7-18-20(34)21(35)24(41-25-22(36)19(33)15(32)8-37-25)26(40-18)39-17-6-11-13(30)4-10(28)5-16(11)38-23(17)9-1-2-12(29)14(31)3-9;/h1-6,15,18-22,24-27,32-36H,7-8H2,(H3-,28,29,30,31);1H/t15-,18-,19+,20-,21+,22-,24-,25+,26-;/m1./s1
Chemical Name
(2S,3R,4S,5R)-2-[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol;chloride
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 (e.g. under nitrogen), avoid exposure to moisture and light.
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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.6209 mL 8.1044 mL 16.2088 mL
5 mM 0.3242 mL 1.6209 mL 3.2418 mL
10 mM 0.1621 mL 0.8104 mL 1.6209 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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An example of molarity calculation using the molarity calculator is shown below:
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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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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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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