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Rubusoside

Alias: UNII-TCV5K3M3GX; Rubusoside
Cat No.:V14117 Purity: ≥98%
Rubusoside is a natural sweetener and solubilizer with excellent anti-angiogenic and anti-allergy properties.
Rubusoside
Rubusoside Chemical Structure CAS No.: 64849-39-4
Product category: Natural Products
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
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10mg
25mg
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Product Description
Rubusoside is a natural sweetener and solubilizer with excellent anti-angiogenic and anti-allergy properties.
Rubusoside (CAS#: 64849-39-4) is a natural diterpene glycoside that functions as a sweetener and solubilizing agent. It exhibits antiangiogenic, anticancer, anti-obesity, anti-allergic, and anti-asthmatic effects. Rubusoside is an excellent solubilizing agent that can enhance the solubility of pharmaceutically important compounds such as liquiritin, teniposide, curcumin, and etoposide. It attenuates airway hyperresponsiveness and reduces inflammatory cells in bronchoalveolar lavage fluid (BALF), reducing OVA-induced airway inflammation.
Biological Activity I Assay Protocols (From Reference)
Targets
Rubusoside does not have a specific pharmacological target but exerts its effects through multiple mechanisms. As a sweetener, it activates sweet taste receptors on the tongue. Its antiangiogenic effects are mediated through inhibition of vascular endothelial growth factor (VEGF) signaling. Its anti-inflammatory effects are associated with reduced inflammatory cell infiltration and cytokine production in airway inflammation models. As a solubilizing agent, rubusoside forms micelles that enhance the aqueous solubility of hydrophobic compounds.
ln Vitro
In vitro, rubusoside exhibits antiangiogenic activity by inhibiting VEGF-induced endothelial cell proliferation and tube formation. It also shows anticancer activity by inhibiting cancer cell proliferation. Rubusoside's anti-inflammatory effects have been demonstrated in cell-based assays measuring cytokine production. Its ability to enhance the solubility of hydrophobic compounds has been confirmed in various formulation studies. As a sweetener, rubusoside is approximately 100-200 times sweeter than sucrose.
ln Vivo
In vivo, rubusoside attenuates airway hyperresponsiveness and reduces inflammatory cells in bronchoalveolar lavage fluid (BALF) in OVA-induced airway inflammation models. It has been studied for its anti-obesity and anti-allergic effects. However, specific in vivo efficacy data in animal models are not extensively detailed in the available literature. The compound is primarily used as a sweetener and solubilizing agent in food and pharmaceutical applications.
Enzyme Assay
In vitro enzyme/receptor binding assays are not typical for rubusoside because it acts through multiple mechanisms rather than a single enzyme or receptor. However, its sweet taste receptor activation can be assessed using cell-based assays measuring calcium mobilization in sweet taste receptor-expressing cells. Its antiangiogenic activity can be assessed using endothelial cell proliferation and tube formation assays.
Cell Assay
In vitro cellular assays for rubusoside are performed using endothelial cells for antiangiogenic studies, cancer cells for anticancer studies, and immune cells for anti-inflammatory studies. Cells are treated with varying concentrations of rubusoside, and cell proliferation is measured using MTT assays. Tube formation is assessed in Matrigel-based assays. Cytokine production is measured by ELISA. Cell viability is evaluated using standard assays.
Animal Protocol
In vivo animal experiments for rubusoside are conducted in rodent models of airway inflammation, such as OVA-induced asthma models. Mice are sensitized and challenged with OVA, and rubusoside is administered orally or via inhalation. Airway hyperresponsiveness is measured using whole-body plethysmography. Inflammatory cells in bronchoalveolar lavage fluid (BALF) are counted, and cytokine levels are measured by ELISA. However, detailed protocols are not extensively documented in the available literature.
ADME/Pharmacokinetics
Rubusoside has a molecular weight of 642.73 g/mol and a molecular formula of C32H50O13. It is a natural diterpene glycoside that functions as a sweetener and solubilizing agent. The compound should be stored as a powder at -20°C for up to 3 years. Detailed pharmacokinetic parameters such as half-life, Cmax, and bioavailability have not been extensively reported. As a natural product, rubusoside is generally considered safe for consumption.
Toxicity/Toxicokinetics
The toxicological profile of rubusoside has not been extensively characterized, but it is generally recognized as safe (GRAS) as a sweetener. No significant toxicity has been reported at the concentrations used in food and pharmaceutical applications. The compound is considered safe for research use. However, comprehensive toxicology studies would be necessary for therapeutic applications.
References

[1]. Selective production of rubusoside from stevioside by using the sophorose activity of β-glucosidase from Streptomyces sp. GXT6. Appl Microbiol Biotechnol. 2015 Nov;99(22):9663-74.

[2]. Mass production of rubusoside using a novel stevioside-specific β-glucosidase from Aspergillus aculeatus. J Agric Food Chem. 2012 Jun 20;60(24):6210-6.

[3]. Metabolomics analysis of the protective effect of rubusoside on palmitic acid-induced lipotoxicity in INS-1 cells using UPLC-Q/TOF MS. Mol Omics. 2019 Jun 1;15(3):222-232.

Additional Infomation
Rubusoside glycoside is a steviol glycoside formed when the carboxyl and tert-allyl hydroxyl groups of steviol are converted to their corresponding β-D-glucosides. It is a valuable bioactive natural sweetener, primarily found in the Chinese sweet tea plant Rubus suavissimus. Rubusoside glycoside is both a sweetener and a plant metabolite. It is a β-D-glucoside, a tetracyclic diterpenoid, a bridging compound, and a steviol glycoside. Its function is related to steviol. Rubusoside glycoside has been reported to exist in the Chinese sweet tea plant Rubus chingii var. suavissimus, and relevant data have been reported.
Rubusoside is a natural diterpene glycoside that functions as a sweetener and solubilizing agent. It is also known as the sweet component of the Chinese sweet tea plant Rubus suavissimus. Rubusoside exhibits antiangiogenic, anticancer, anti-obesity, anti-allergic, and anti-asthmatic effects. It attenuates airway hyperresponsiveness and reduces inflammatory cells in bronchoalveolar lavage fluid. Rubusoside is a research compound with potential applications in inflammation, allergy, and metabolic studies.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C32H50O13
Molecular Weight
642.7316
Exact Mass
642.325
Elemental Analysis
C, 59.80; H, 7.84; O, 32.36
CAS #
64849-39-4
PubChem CID
24721373
Appearance
White to off-white solid powder
Density
1.5±0.1 g/cm3
Boiling Point
802.5±65.0 °C at 760 mmHg
Flash Point
251.9±27.8 °C
Vapour Pressure
0.0±6.4 mmHg at 25°C
Index of Refraction
1.628
LogP
1.83
Hydrogen Bond Donor Count
8
Hydrogen Bond Acceptor Count
13
Rotatable Bond Count
7
Heavy Atom Count
45
Complexity
1150
Defined Atom Stereocenter Count
16
SMILES
O([C@@]1([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C([H])([H])O[H])O1)O[H])O[H])O[H])C12C(=C([H])[H])C([H])([H])[C@@]3(C([H])([H])C([H])([H])[C@]4([H])[C@@](C(=O)O[C@@]5([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C([H])([H])O[H])O5)O[H])O[H])O[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]4(C([H])([H])[H])[C@]3([H])C([H])([H])C1([H])[H])C2([H])[H]
InChi Key
YWPVROCHNBYFTP-OSHKXICASA-N
InChi Code
InChI=1S/C32H50O13/c1-15-11-31-9-5-18-29(2,7-4-8-30(18,3)28(41)44-26-24(39)22(37)20(35)16(12-33)42-26)19(31)6-10-32(15,14-31)45-27-25(40)23(38)21(36)17(13-34)43-27/h16-27,33-40H,1,4-14H2,2-3H3/t16-,17-,18+,19+,20-,21-,22+,23+,24-,25-,26+,27+,29-,30-,31-,32+/m1/s1
Chemical Name
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-5,9-dimethyl-14-methylidene-13-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
Synonyms
UNII-TCV5K3M3GX; Rubusoside
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

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 : ~110 mg/mL (~171.14 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.75 mg/mL (4.28 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 27.5 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: ≥ 2.75 mg/mL (4.28 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 27.5 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: ≥ 2.75 mg/mL (4.28 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 27.5 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 1.5559 mL 7.7793 mL 15.5586 mL
5 mM 0.3112 mL 1.5559 mL 3.1117 mL
10 mM 0.1556 mL 0.7779 mL 1.5559 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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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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  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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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

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

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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  • 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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