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Saikogenin F ((4R)-13,28-Epoxyolean-11-ene-3β,16β,23-triol)

Alias: (4R)-13,28-Epoxyolean-11-ene-3β,16β,23-triol; Saikogenin F
Cat No.:V62204 Purity: ≥98%
Saikogenin F has anti-cancer effect.
Saikogenin F ((4R)-13,28-Epoxyolean-11-ene-3β,16β,23-triol)
Saikogenin F ((4R)-13,28-Epoxyolean-11-ene-3β,16β,23-triol) Chemical Structure CAS No.: 14356-59-3
Product category: Terpenoids
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
Saikogenin F has anticancer activity.
Saikogenin F ((4R)-13,28-Epoxyolean-11-ene-3β,16β,23-triol) (CAS 14356-59-3) is a triterpenoid sapogenin and an aglycone of saikosaponins, the major bioactive constituents of Bupleurum species (Chai Hu), a traditional Chinese medicinal herb. It has the molecular formula C₃₀H₄₈O₄ and a molecular weight of approximately 472.70 g/mol. Saikogenin F features an oleanane-type triterpene skeleton with an epoxy ring at C-13,28 and hydroxyl groups at C-3, C-16, and C-23. It is known for its various pharmacological activities, including anti-inflammatory, hepatoprotective, immunomodulatory, and anticancer effects.
Biological Activity I Assay Protocols (From Reference)
Targets
Multiple targets: inflammatory mediators (NF-κB, COX-2, iNOS, TNF-α, IL-1β, IL-6); antioxidant pathways; cancer-related targets (apoptosis, cell cycle).
ln Vitro
At 50, 70, and 90 μg/mL, respectively, saikogenin F inhibits the proliferation of A549 cells with rates of 18.81%, 47.64%, and 86.01%[1].
Saikogenin F exhibits anti-inflammatory activity by inhibiting NF-κB activation and reducing the production of pro-inflammatory mediators such as COX-2, iNOS, TNF-α, IL-1β, and IL-6. It has hepatoprotective effects by protecting hepatocytes from damage induced by toxic agents and reducing liver enzyme levels. The compound shows immunomodulatory activity by regulating T-cell and macrophage function. It also has anticancer activity by inducing apoptosis, inhibiting cell proliferation, and suppressing angiogenesis.
ln Vivo
In vivo studies of saikogenin F have demonstrated its anti-inflammatory effects in animal models of inflammation, including carrageenan-induced paw edema and LPS-induced sepsis. Hepatoprotective effects have been shown in models of liver injury (e.g., CCl₄-induced, APAP-induced). Anticancer effects have been observed in tumor xenograft models. The compound is orally active and has favorable pharmacokinetic properties as an aglycone of saikosaponins.
Enzyme Assay
Anti-inflammatory activity is assessed by measuring the inhibition of COX-2, iNOS, or cytokine production in enzyme assays or cell-based systems. NF-κB activation is measured by reporter gene assays or Western blot analysis of p65 nuclear translocation. Hepatoprotective activity is assessed by measuring liver enzyme levels (ALT, AST) in cell-based or in vitro assays. Anticancer activity is assessed by cell viability assays (MTT, SRB) and apoptosis assays using cancer cell lines.
Cell Assay
Macrophage cell lines (e.g., RAW 264.7) are stimulated with LPS to induce inflammation, and cells are treated with saikogenin F at various concentrations. Inflammatory mediators (NO, TNF-α, IL-1β, IL-6) in culture supernatant are measured by Griess reagent or ELISA. NF-κB activation is assessed by Western blot. For hepatoprotective studies, primary hepatocytes or HepG2 cells are treated with hepatotoxic agents (e.g., CCl₄, APAP) with or without saikogenin F, and cell viability and enzyme levels are measured. Cancer cell lines are used for anticancer studies.
Animal Protocol
In vivo studies use rodent models. For anti-inflammatory studies, carrageenan-induced paw edema or LPS-induced sepsis models are used. For hepatoprotective studies, CCl₄- or APAP-induced liver injury models are used. For anticancer studies, tumor xenograft models in nude mice are used. The compound is administered orally, intraperitoneally, or intravenously. Relevant endpoints (inflammatory markers, liver enzymes, tumor volume, histopathology) are measured.
ADME/Pharmacokinetics
Saikogenin F is the aglycone of saikosaponins, which are the major bioactive constituents of Bupleurum species. As a sapogenin, it is expected to be more lipophilic than the corresponding glycosides, potentially leading to improved oral absorption. Saikosaponins are known to be metabolized to saikogenins in the gastrointestinal tract, and the aglycones are absorbed systemically. The compound is soluble in organic solvents. Standard laboratory storage conditions apply.
Toxicity/Toxicokinetics
Toxicological data for saikogenin F are limited. Saikosaponins have been studied extensively and are generally considered to have moderate toxicity at high doses. Hepatotoxicity has been reported at very high doses. Standard laboratory safety practices should be followed when handling this compound. It is intended for research use only.
References

[1]. A Potential Anti-cancer Compound Separated from the Chloroform Extract of the Chinese Medicine Formula Shenqi San. Curr Med Sci. 2020 Feb;40(1):138-144.

Additional Infomation
According to reports, Bupleurum contains saikosaponin F, and relevant data is available for reference.
Saikogenin F is an oleanane-type triterpenoid sapogenin and the aglycone of saikosaponins, the major bioactive constituents of Bupleurum species (Chai Hu). Bupleurum has been used in traditional Chinese medicine for centuries for the treatment of inflammatory and liver diseases. Saikogenin F contributes to the pharmacological activities of saikosaponins, including anti-inflammatory, hepatoprotective, immunomodulatory, and anticancer effects. It is used as a reference standard for quality control of Bupleurum-containing products and as a research tool. It is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C30H48O4
Molecular Weight
472.70
Exact Mass
472.355
CAS #
14356-59-3
PubChem CID
21594261
Appearance
White to off-white solid
LogP
5.1
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Heavy Atom Count
34
Complexity
914
Defined Atom Stereocenter Count
11
SMILES
O1C[C@]23CCC(C)(C)C[C@@]2([H])[C@@]21C=C[C@]1([H])[C@@]4(C)CC[C@@H]([C@@](C)(CO)[C@]4([H])CC[C@@]1(C)[C@]2(C)C[C@@H]3O)O
InChi Key
IUBQSOTVBGNWDI-CUMBFETHSA-N
InChi Code
InChI=1S/C30H48O4/c1-24(2)13-14-29-18-34-30(21(29)15-24)12-8-20-25(3)10-9-22(32)26(4,17-31)19(25)7-11-27(20,5)28(30,6)16-23(29)33/h8,12,19-23,31-33H,7,9-11,13-18H2,1-6H3/t19-,20-,21-,22+,23+,25+,26+,27-,28+,29-,30+/m1/s1
Chemical Name
(1S,2S,4S,5R,8R,9R,10S,13S,14R,17S,18R)-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-ene-2,10-diol
Synonyms
(4R)-13,28-Epoxyolean-11-ene-3β,16β,23-triol; Saikogenin F
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 2.1155 mL 10.5775 mL 21.1551 mL
5 mM 0.4231 mL 2.1155 mL 4.2310 mL
10 mM 0.2116 mL 1.0578 mL 2.1155 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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  • 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)
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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
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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