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Ardisiacrispin A

Cat No.:V31287 Purity: ≥98%
Ardisiacrispin A (Deglucocyclamin) is a common triterpene saponin from Ardisia species.
Ardisiacrispin A
Ardisiacrispin A Chemical Structure CAS No.: 23643-61-0
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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5mg
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Product Description
Ardisiacrispin A (Deglucocyclamin) is a common triterpene saponin from Ardisia species. Some triterpene saponins from A. crenata have cytotoxic, Immune-modulatory and anti-viral effects on tumor cells, and Ardisiacrispin A has similar bioactivities.
Ardisiacrispin A (CAS 23643-61-0) is a triterpenoid saponin isolated from plants of the Ardisia genus, including Ardisia crispa and Myrsine australis. It exhibits diverse biological activities, including cytotoxic, antiviral, and immunomodulatory effects. Ardisiacrispin A has been shown to have cytotoxic activity against HepG2 cancer cells with a GI50 value of 1.56 microM. It also inhibits the proliferation of Bel-7402 cells by inducing apoptosis and disassembling microtubules. Additionally, the compound inhibits the cytopathic effects of poliovirus type I and herpes simplex virus 1 (HSV-1). Ardisiacrispin A is a valuable tool for studying the biological activities of triterpenoid saponins.
Biological Activity I Assay Protocols (From Reference)
Targets
The molecular targets of Ardisiacrispin A are not fully defined but are believed to involve the modulation of various signaling pathways. Its cytotoxic activity is associated with the induction of apoptosis and the disassembly of microtubules. The compound's ability to inhibit the cytopathic effects of poliovirus and HSV-1 suggests that it may target viral replication or entry. Its immunomodulatory effects may involve the modulation of immune cell function. Further studies are needed to identify its precise molecular targets and mechanisms of action. The compound's diverse biological activities make it a promising lead for drug development.
ln Vitro
In vitro, Ardisiacrispin A exhibits potent cytotoxic activity against various cancer cell lines. It has a GI50 value of 1.56 microM against HepG2 cancer cells. It inhibits the proliferation of Bel-7402 cells by inducing apoptosis and disassembling microtubules. The compound also inhibits the cytopathic effects of poliovirus type I and herpes simplex virus 1 (HSV-1) in filter paper disk assays. Its immunomodulatory effects include modulation of immune cell function. These in vitro activities are concentration-dependent and have been observed at micromolar concentrations. Ardisiacrispin A is a valuable tool for studying the biological activities of triterpenoid saponins.
ln Vivo
In vivo, Ardisiacrispin A has potential applications in cancer therapy and antiviral treatment. Its in vitro cytotoxic activity against cancer cells suggests that it may have antitumor activity in vivo. Its antiviral activity against poliovirus and HSV-1 indicates potential for treating viral infections. However, in vivo studies are limited, and further research is needed to evaluate its efficacy, pharmacokinetics, and safety in animal models. The compound's natural origin and diverse biological activities make it a promising candidate for further development.
Enzyme Assay
The in vitro cytotoxic activity of Ardisiacrispin A can be assessed using cell-free or cell-based assays. For cell-free assays, the compound's ability to disassemble microtubules can be assessed using purified tubulin and measuring tubulin polymerization by turbidity. For antiviral activity, cell-free assays can be used to assess the compound's ability to inhibit viral enzymes, such as viral proteases or polymerases. However, most studies on Ardisiacrispin A have used cell-based assays to assess its biological activity.
Cell Assay
For in vitro cellular experiments, cancer cell lines (e.g., HepG2, Bel-7402) are cultured in appropriate media and treated with Ardisiacrispin A at various concentrations (typically 0.1-100 microM). Cell viability is measured after 24-72 hours of treatment using MTT, CCK-8, or other cell proliferation assays. Apoptosis is assessed by flow cytometry using Annexin V/PI staining or by measuring caspase-3/7 activity. Microtubule integrity is assessed by immunostaining for alpha-tubulin or beta-tubulin. For antiviral studies, virus-permissive cells are infected with poliovirus or HSV-1 and treated with the compound, and viral replication is assessed by measuring viral titers or cytopathic effects.
Animal Protocol
In vivo animal experiments with Ardisiacrispin A are not well-documented in the available literature. However, given its in vitro anticancer and antiviral activities, it could be evaluated in xenograft mouse models or viral infection models. A typical study would involve administering the compound via intraperitoneal or oral administration to tumor-bearing or virus-infected animals. Tumor growth, viral load, and survival would be monitored. Pharmacokinetic and toxicity studies would also be required to determine the optimal dosing regimen and safety profile. Further preclinical studies are needed to fully characterize its in vivo activity.
ADME/Pharmacokinetics
Pharmacokinetic data for Ardisiacrispin A are not well-documented in the available literature. As a triterpenoid saponin with a molecular weight of 1061.23 g/mol and a molecular formula of C52H84O22, it is a large, polar molecule that is likely to have poor oral bioavailability. The compound may be administered by injection in preclinical studies. Its absorption, distribution, metabolism, and excretion properties would need to be characterized to support its development as a therapeutic agent. The compound is typically stored at -20degC.
Toxicity/Toxicokinetics
The toxicity profile of Ardisiacrispin A has not been extensively characterized. As a natural product with cytotoxic activity, it may have potential toxicity to normal cells. Its ability to disassemble microtubules and induce apoptosis could lead to toxicity in rapidly dividing tissues. In vitro cytotoxicity studies would be needed to assess its effects on normal cell lines. In vivo toxicity studies in animal models would also be required to determine its safety profile. The compound should be handled with standard laboratory precautions and is intended for research use only.
References

[1]. Pharmacokinetic study of ardisiacrispin A in rat plasma after intravenous administration by UPLC-MS/MS. Biomed Chromatogr. 2017 Mar;31(3).

Additional Infomation
Ardisiacrispin A has been reported to be found in marigolds, pearlwort, and other organisms with available data.
Ardisiacrispin A is a triterpenoid saponin isolated from Ardisia species. It exhibits cytotoxic activity against HepG2 cancer cells with a GI50 of 1.56 microM and inhibits the proliferation of Bel-7402 cells by inducing apoptosis and disassembling microtubules. It also inhibits the cytopathic effects of poliovirus type I and herpes simplex virus 1 (HSV-1). Ardisiacrispin A has immunomodulatory effects. It is a valuable tool for studying the biological activities of triterpenoid saponins. The compound is available as a research compound and is not approved for clinical use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C52H84O22
Molecular Weight
1061.2102
Exact Mass
1060.545
CAS #
23643-61-0
PubChem CID
10328746
Appearance
White to off-white solid powder
Density
1.48±0.1 g/cm3 (20 ºC 760 Torr)
Index of Refraction
1.635
LogP
3.78
Hydrogen Bond Donor Count
12
Hydrogen Bond Acceptor Count
22
Rotatable Bond Count
11
Heavy Atom Count
74
Complexity
2020
Defined Atom Stereocenter Count
29
SMILES
C[C@@]1(CC[C@@]23CO[C@]4([C@@H]2C1)CC[C@@H]5[C@]6(CC[C@@H](C([C@@H]6CC[C@]5([C@@]4(C[C@H]3O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@H](CO7)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)C)C=O
InChi Key
JXTOWLUQSHIIDP-VKKSEJOZSA-N
InChi Code
InChI=1S/C52H84O22/c1-46(2)27-7-11-49(5)28(8-12-52-29-15-47(3,21-55)13-14-51(29,22-68-52)30(57)16-50(49,52)6)48(27,4)10-9-31(46)72-44-40(74-43-39(65)36(62)33(59)24(17-53)69-43)35(61)26(20-67-44)71-45-41(37(63)34(60)25(18-54)70-45)73-42-38(64)32(58)23(56)19-66-42/h21,23-45,53-54,56-65H,7-20,22H2,1-6H3/t23-,24-,25-,26+,27+,28-,29-,30-,31+,32+,33-,34-,35+,36+,37+,38-,39-,40-,41-,42+,43+,44+,45+,47+,48+,49-,50+,51-,52+/m1/s1
Chemical Name
(1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,20S)-10-[(2S,3R,4S,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-hydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosane-20-carbaldehyde
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)
DMSO : ~100 mg/mL (~94.23 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.36 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 25.0 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: ≥ 2.5 mg/mL (2.36 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 25.0 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: ≥ 2.5 mg/mL (2.36 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 25.0 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 0.9423 mL 4.7116 mL 9.4232 mL
5 mM 0.1885 mL 0.9423 mL 1.8846 mL
10 mM 0.0942 mL 0.4712 mL 0.9423 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:

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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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  • 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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