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Cassiaside C (Cassiaside C; Toralactone 9-O-β-D-gentiobioside)

Cat No.:V72610 Purity: ≥98%
Cassiaside C (Toralactone 9-O-β-D-gentiobioside) is a naphthol compound extracted from Cassia seeds and has an inhibitory effect on the formation of advanced glycation end products (AGE).
Cassiaside C (Cassiaside C; Toralactone 9-O-β-D-gentiobioside)
Cassiaside C (Cassiaside C; Toralactone 9-O-β-D-gentiobioside) Chemical Structure CAS No.: 119170-52-4
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes
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Product Description
Cassiaside C (Toralactone 9-O-β-D-gentiobioside) is a naphthol compound extracted from Cassia seeds and has an inhibitory effect on the formation of advanced glycation end products (AGE).
Cassiaside C (Toralactone 9-O-β-D-gentiobioside) is a naphthopyrone glycoside naturally isolated from the seeds of Cassia tora, belonging to the class of naphthopyranone glycosides with a carbohydrate moiety linked to a naphthopyranone structure. With a molecular weight of 596.53 and formula C27H32O15, this compound has been detected in various foods including coffee and pulses, suggesting its potential as a dietary biomarker.
Biological Activity I Assay Protocols (From Reference)
Targets
IC50: AGE formation[1]
Cassiaside C does not have a definitively established primary molecular target in conventional pharmacological terms. It is classified as an endogenous metabolite and its biological activity is primarily characterized through functional assays rather than specific receptor binding studies. The compound is recognized for its interaction with the biochemical pathways involved in advanced glycation end-product (AGE) formation, indicating that its targets may include proteins or intermediates in the glycation cascade rather than a single defined receptor or enzyme.
ln Vitro
Cassiaside C exhibits significant in vitro inhibitory activity against the formation of advanced glycation end products (AGEs), which are harmful compounds associated with aging and diabetic complications. This activity suggests that the compound can interfere with the non-enzymatic glycation of proteins, a process that involves the reaction of reducing sugars with free amino groups of proteins. The compound’s naphthopyrone glycoside structure is believed to be responsible for this bioactivity, potentially through its ability to trap reactive carbonyl species or chelate metal ions involved in the glycation process.
ln Vivo
In vivo activity data for Cassiaside C is currently limited in the available scientific literature. As a natural product isolated from Cassia tora, its in vivo pharmacological effects have not been extensively characterized in animal models. However, based on its in vitro AGE inhibitory activity, it is hypothesized that the compound could potentially exhibit anti-glycation effects in living organisms, which might translate to benefits in conditions like diabetes and age-related diseases. Further in vivo studies are required to confirm its efficacy, bioavailability, and therapeutic potential in mammalian systems.
Enzyme Assay
Typical in vitro enzyme assays for AGE inhibition involve incubating a protein (such as bovine serum albumin, BSA) with a reducing sugar (like glucose or ribose) in the presence of the test compound. The formation of fluorescent AGEs is measured over time using a fluorescence spectrophotometer at excitation/emission wavelengths (e.g., 370/440 nm). The inhibitory activity of Cassiaside C is calculated by comparing the fluorescence intensity of the compound-treated group to a control group without the inhibitor. Assays are often performed in 96-well plates at 37°C for several days under sterile conditions, with aminoguanidine used as a positive control.
Cell Assay
For in vitro cellular studies, appropriate cell lines such as renal mesangial cells, endothelial cells, or macrophages are cultured in standard media containing high glucose concentrations to stimulate AGE formation. Cells are treated with varying concentrations of Cassiaside C (e.g., 1-100 µM) for defined periods (24-72 hours). Cellular AGE accumulation can be assessed by fluorescence microscopy or flow cytometry using anti-AGE antibodies. Additional endpoints include the measurement of oxidative stress markers (e.g., reactive oxygen species, ROS), inflammatory cytokines (e.g., TNF-α, IL-6), and cell viability via MTT or CCK-8 assays to evaluate the compound's cytoprotective effects against glycation-induced cellular damage.
Animal Protocol
In vivo animal studies for Cassiaside C would typically involve the use of diabetic rodent models such as streptozotocin (STZ)-induced diabetic rats or db/db mice to evaluate its anti-glycation effects. Animals would be administered the compound via oral gavage or intraperitoneal injection at various doses (e.g., 10-50 mg/kg) for a period of 4-12 weeks. Key parameters to monitor include blood glucose levels, body weight, and biomarkers of glycation such as serum AGEs, hemoglobin A1c (HbA1c), and fructosamine. Renal function markers (urinary albumin, serum creatinine) and histopathological examination of kidney tissues would be assessed to determine protection against diabetic nephropathy.
ADME/Pharmacokinetics
Pharmacokinetic (PK) properties of Cassiaside C have not been systematically reported. As a glycoside with a molecular weight of 596.53, it is expected to have relatively low oral bioavailability due to poor permeability and potential efflux by transporters. The compound likely undergoes deglycosylation in the gastrointestinal tract by microbial enzymes, and the resulting aglycone (toralactone) may be absorbed. PK studies would involve LC-MS/MS methods to quantify the compound and its metabolites in plasma, urine, and tissues. Parameters such as Cmax, Tmax, AUC, half-life, and volume of distribution would need to be determined in future studies.
Toxicity/Toxicokinetics
Toxicological information for Cassiaside C is not well documented. As a natural compound isolated from Cassia tora, which has a history of use in traditional medicine, it is presumed to have a reasonable safety profile at typical dietary exposure levels. However, systematic toxicity studies including acute, subacute, and chronic toxicity assessments in animal models have not been published. The compound's in vitro cytotoxicity against normal cell lines would be an initial step in evaluating its safety margin. Based on its chemical class as a glycoside, it is not expected to be highly toxic, but caution should be exercised until comprehensive toxicological data are available.
References

[1]. A new comprehensive procedure for the quality control of Semen Cassiae and its application in evaluating commercially available material in China. Chin J Nat Med. 2013 Jul;11(4):433-41.

[2]. Extract of Cassiae Semen and its major compound inhibit S100b-induced TGF-beta1 and fibronectin expression in mouse glomerular mesangial cells. Eur J Pharmacol. 2010 Sep 1;641(1):7-14.

Additional Infomation
Cassiaside C is a benzochromene ketone compound and also a glycoside. It has been reported that Cassiaside C exists in Cassia obtusifolia and Cassia tora, and relevant data are available for reference.
Cassiaside C is primarily a research tool compound rather than a therapeutic drug. Its significance lies in being a natural product with demonstrated anti-AGE activity, making it a valuable lead compound for the development of potential treatments for diabetes-related complications such as nephropathy, retinopathy, and neuropathy. As a naphthopyranone glycoside, it also contributes to the chemical diversity of natural products. The compound's presence in food sources positions it as a potential dietary biomarker. Currently, there are no clinical trials or approved drug status for Cassiaside C, and its use remains strictly within the scope of laboratory research for studying glycation inhibition and metabolic pathways.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C27H32O15
Molecular Weight
596.53
Exact Mass
596.174
CAS #
119170-52-4
PubChem CID
5317701
Appearance
White to off-white solid powder
LogP
-0.6
Hydrogen Bond Donor Count
8
Hydrogen Bond Acceptor Count
15
Rotatable Bond Count
7
Heavy Atom Count
42
Complexity
979
Defined Atom Stereocenter Count
10
SMILES
CC1=CC2=CC3=CC(=CC(=C3C(=C2C(=O)O1)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)OC
InChi Key
GBGJNKYTLIUCMX-YUMVGKRXSA-N
InChi Code
InChI=1S/C27H32O15/c1-9-3-10-4-11-5-12(37-2)6-13(16(11)20(31)17(10)25(36)39-9)40-27-24(35)22(33)19(30)15(42-27)8-38-26-23(34)21(32)18(29)14(7-28)41-26/h3-6,14-15,18-19,21-24,26-35H,7-8H2,1-2H3/t14-,15-,18-,19-,21+,22+,23-,24-,26-,27-/m1/s1
Chemical Name
10-hydroxy-7-methoxy-3-methyl-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxybenzo[g]isochromen-1-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

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 1.6764 mL 8.3818 mL 16.7636 mL
5 mM 0.3353 mL 1.6764 mL 3.3527 mL
10 mM 0.1676 mL 0.8382 mL 1.6764 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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  • 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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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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