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Gypsoside

Cat No.:V58635 Purity: ≥98%
Gypsoside is a triterpene developed from the flower Gypsoside.
Gypsoside
Gypsoside Chemical Structure CAS No.: 15588-68-8
Product category: Terpenoids
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
25mg
50mg
100mg
250mg
Other Sizes
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Product Description
Gypsoside is a triterpene developed from the flower Gypsoside.
Gypsoside (also referred to as Gipsoside) is a triterpene saponin isolated from Gypsophila paniculata L.. It has a molecular formula of C₈₀H₁₂₆O₄₄ and a molecular weight of 1791.83 g/mol. Gypsoside exhibits a wide range of pharmacological activities including anti-inflammatory, anti-thrombotic, antioxidative, and anticancer actions. It has been studied for its beneficial effects in treating hepatitis, hyperlipoproteinemia, and cardiovascular disease. The compound is of interest in medicinal chemistry and natural product research.
Biological Activity I Assay Protocols (From Reference)
Targets
Gypsoside targets multiple cellular pathways. In SW-480 colon cancer cells, it causes cell membrane integrity damage, decreases the mitochondrial membrane potential (Δψm), induces DNA fragmentation, and initiates apoptotic response. ROS generation plays an important role in gypsoside-induced cell death. It also induces microfilament network collapse and injures cell shape and migration ability. In neuroprotection studies, gypsoside attenuates Aβ-induced microglial activation, decreases M1 state markers including iNOS, TNF-α, IL-1β, and IL-6, and increases M2 state markers including Arg-1, IL-10, BDNF, and GDNF.
ln Vitro
In vitro, gypsoside inhibits SW-480 cell proliferation in a dose- and time-dependent manner. It exerts different alternative cytotoxicity in cancer cells and normal cells, suggesting potential usefulness as a cancer preventive or treatment agent. Gypsoside causes cell membrane integrity damage, decreases Δψm, induces DNA fragmentation, and initiates apoptotic response in SW-480 cells. ROS generation plays an important role in gypsoside-induced cell death. It also induces microfilament network collapse and injures cell shape and migration ability. Gypenoside induces neuroprotection against Aβ in vitro by attenuating microglial activation and shifting microglia from M1 to M2 state.
ln Vivo
In vivo, gypsoside has been known for its wide beneficial effects for treating hepatitis, hyperlipoproteinemia, and cardiovascular disease. It demonstrates hepatoprotective effects, with a derivative showing protective effects against chemically induced liver injury in isolated rat hepatocytes. The compound exhibits anti-inflammatory, antioxidant, and neuroprotective effects in various experimental models. Its anti-thrombotic and anticancer actions have also been documented. However, specific detailed in vivo protocols are not extensively available.
Enzyme Assay
Typical in vitro assays for gypsoside involve cell proliferation assays using SW-480 colon cancer cells. Cells are seeded in 96-well plates and treated with various concentrations (0, 70, 100, and 130 µg/ml) for 24 and 48 hours. Cell viability is assessed by MTT or similar assays. Apoptosis is evaluated by measuring DNA fragmentation, mitochondrial membrane potential (Δψm), and ROS generation. For neuroprotection studies, microglial activation markers are measured by ELISA or Western blot.
Cell Assay
Cellular assays for gypsoside typically involve SW-480 cells or microglial cells. SW-480 cells are treated with the compound at concentrations ranging from 0-130 µg/ml for 24-48 hours. Cell membrane integrity, Δψm, DNA fragmentation, and apoptotic response are assessed. ROS levels are measured using fluorescent probes. For neuroprotection, microglial cells are treated with Aβ and gypsoside, and M1/M2 state markers including iNOS, TNF-α, IL-1β, IL-6, Arg-1, IL-10, BDNF, and GDNF are measured.
Animal Protocol
In vivo animal experiments for gypsoside are not extensively detailed in the available literature. For hepatoprotective studies, isolated rat hepatocytes have been used to assess protective effects against chemically induced liver injury. For cardiovascular disease research, animal models of hyperlipoproteinemia and hepatitis have been employed. However, specific protocols including dosing regimens and endpoints are not detailed in the consulted sources. Further studies are needed to characterize its in vivo efficacy.
ADME/Pharmacokinetics
Pharmacokinetic data for gypsoside are limited. As a large, polar triterpene saponin with a molecular weight of 1791.83 g/mol, it would be expected to have poor oral bioavailability due to its size and hydrophilicity. It is soluble in DMSO (100 mg/mL, 55.8 mM) but insoluble in water and ethanol. For oral administration, it can be formulated as a homogeneous suspension in CMC-Na at ≥5 mg/mL. Detailed ADME parameters are not available.
Toxicity/Toxicokinetics
Toxicological data for gypsoside are limited. As a triterpene saponin, it may have hemolytic activity and could cause gastrointestinal irritation at high doses. However, the compound has been studied for its beneficial effects in treating hepatitis, hyperlipoproteinemia, and cardiovascular disease, suggesting it may be well-tolerated at therapeutic doses. Comprehensive toxicological studies have not been reported. Standard laboratory safety precautions should be followed.
References

[1]. Identity of gypsoside and a triterpene saponin from gypsophila paniculata L. Russ Chem Bull 12, 1387–1388 (1963).

Additional Infomation
Reports indicate that gipsophila Gipsoside have been found in Gypsophila pacifica and Gypsophila paniculata, and relevant data are available for reference.
Gypsoside is a triterpene saponin from Gypsophila paniculata L. with anti-inflammatory, anti-thrombotic, antioxidative, and anticancer activities. It has been studied for treating hepatitis, hyperlipoproteinemia, and cardiovascular disease. The compound induces apoptosis in cancer cells via ROS generation and mitochondrial dysfunction, and exerts neuroprotection by shifting microglia from M1 to M2 state. It is a research compound for studying cancer, inflammation, and cardiovascular diseases. It is not approved for any clinical indication.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C80H126O44
Molecular Weight
1791.83
Exact Mass
1790.762
CAS #
15588-68-8
PubChem CID
167308
Appearance
Typically exists as solid at room temperature
Density
1.6±0.1 g/cm3
Index of Refraction
1.665
LogP
5.47
Hydrogen Bond Donor Count
23
Hydrogen Bond Acceptor Count
44
Rotatable Bond Count
23
Heavy Atom Count
124
Complexity
3670
Defined Atom Stereocenter Count
0
SMILES
CC1C(C(C(C(O1)OC2C(C)OC(C(C2O)OC3C(C(C(CO3)O)O)OC4C(C(C(CO4)O)O)O)OC(=O)C56CCC(C)(C)CC6C7=CCC8C9(C)CCC(C(C)(C=O)C9CCC8(C)C7(C)CC5)OC%10C(C(C(C(C(=O)O)O%10)OC%11C(C(C(C(CO)O%11)OC%12C(C(C(C(CO)O%12)O)O)O)O)O)OC%13C(C(C(CO%13)O)O)O)O)O)OC%14C(C(C(CO%14)O)O)O)O
InChi Key
VJDBQMHOQSSGGS-UHFFFAOYSA-N
InChi Code
InChI=1S/C80H126O44/c1-27-40(88)59(119-66-48(96)42(90)32(85)23-108-66)54(102)71(111-27)116-56-28(2)112-73(61(52(56)100)121-68-53(101)57(34(87)25-110-68)117-65-47(95)41(89)31(84)22-107-65)124-74(106)80-17-15-75(3,4)19-30(80)29-9-10-38-76(5)13-12-39(77(6,26-83)37(76)11-14-79(38,8)78(29,7)16-18-80)115-72-55(103)60(120-67-49(97)43(91)33(86)24-109-67)62(63(123-72)64(104)105)122-70-51(99)46(94)58(36(21-82)114-70)118-69-50(98)45(93)44(92)35(20-81)113-69/h9,26-28,30-63,65-73,81-82,84-103H,10-25H2,1-8H3,(H,104,105)
Chemical Name
6-[[8a-[5-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl]oxy-3-[3,5-dihydroxy-4-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxycarbonyl-4-formyl-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-[3,4-dihydroxy-6-(hydroxymethyl)-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-4-(3,4,5-trihydroxyoxan-2-yl)oxyoxane-2-carboxylic acid
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 0.5581 mL 2.7904 mL 5.5809 mL
5 mM 0.1116 mL 0.5581 mL 1.1162 mL
10 mM 0.0558 mL 0.2790 mL 0.5581 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

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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
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:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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