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Dihydroarteannuin B

Cat No.:V60823 Purity: ≥98%
Dihydroarteannuin B is a dihydroartemisinin, a microbial metabolite of artemisinin B.
Dihydroarteannuin B
Dihydroarteannuin B Chemical Structure CAS No.: 87206-33-5
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
Other Sizes
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Product Description
Dihydroarteannuin B is a dihydroartemisinin, a microbial metabolite of artemisinin B.
Dihydroarteannuin B (CAS# 87206-33-5) is a dihydroartemisinin and a microbial metabolite of artemisinin B found in Artemisia annua. It has the molecular formula C₁₅H₂₂O₃ and molecular weight 250.33 g/mol. Dihydroarteannuin B is also known as (3R)-dihydroarteannuin B. As a derivative of artemisinin, a well-known antimalarial compound, dihydroarteannuin B is of interest for its potential biological activities.
Biological Activity I Assay Protocols (From Reference)
Targets
Dihydroarteannuin B is a microbial metabolite of artemisinin B, suggesting that it may share some biological targets with artemisinin and its derivatives. Artemisinin compounds are known to target the malaria parasite through generation of reactive oxygen species and interaction with heme. Dihydroarteannuin B may also have anti-inflammatory activity through inhibition of TNF-α production and NF-κB signaling. However, specific molecular targets have not been fully characterized.
ln Vitro
In vitro, Dihydroarteannuin B is a microbial metabolite of artemisinin B. It has been reported to ameliorate lupus symptoms in BXSB mice by inhibiting TNF-α production and blocking NF-κB signaling pathway translocation, suggesting anti-inflammatory activity. As a dihydroartemisinin derivative, it may also exhibit antimalarial activity. However, detailed in vitro activity data including IC₅₀ values are not extensively published for this specific compound.
ln Vivo
In vivo, Dihydroarteannuin B has been reported to ameliorate lupus symptoms in BXSB mice by inhibiting TNF-α production and blocking the NF-κB signaling pathway translocation. This suggests potential anti-inflammatory and immunomodulatory activity. The compound's ability to modulate NF-κB signaling indicates possible therapeutic applications in autoimmune and inflammatory conditions. However, detailed in vivo efficacy data are not extensively published.
Enzyme Assay
In vitro assays for Dihydroarteannuin B are not extensively documented. As a microbial metabolite of artemisinin B, potential assays could include evaluation of anti-inflammatory activity by measuring TNF-α production in immune cells or NF-κB reporter gene assays. Antimalarial activity could be assessed using Plasmodium falciparum cultures. The compound's structure can be confirmed by NMR and MS.
Cell Assay
In vitro cellular assays for Dihydroarteannuin B could include evaluation of anti-inflammatory activity in immune cell lines. Cells are treated with the compound and stimulated with LPS or other inflammatory stimuli, and cytokine production (TNF-α, IL-1β, IL-6) is measured by ELISA. NF-κB signaling can be assessed using reporter gene assays or by measuring NF-κB nuclear translocation. Cytotoxicity may be assessed in relevant cell lines using MTT or similar assays.
Animal Protocol
In vivo animal experiments for Dihydroarteannuin B have been reported in BXSB lupus mice. The compound is administered to mice and endpoints include lupus symptom scores, autoantibody levels, cytokine levels (TNF-α), and NF-κB signaling pathway activity. However, detailed experimental protocols including dosing regimens and administration routes are not extensively published in the available literature.
ADME/Pharmacokinetics
Pharmacokinetic properties of Dihydroarteannuin B are characteristic of artemisinin derivatives. The compound has a molecular weight of 250.33 g/mol and molecular formula C₁₅H₂₂O₃. As a lipophilic sesquiterpene, it is expected to have good oral absorption and tissue distribution. Like other artemisinin derivatives, it may undergo metabolism in the liver. Storage: powder at -20°C for 3 years or 4°C for 2 years; in solvent at -80°C for 6 months or -20°C for 1 month.
Toxicity/Toxicokinetics
The toxicological profile of Dihydroarteannuin B is not extensively documented. As a derivative of artemisinin, which has a well-established safety profile in antimalarial therapy, dihydroarteannuin B is expected to have manageable toxicity. However, comprehensive toxicological evaluations including acute toxicity, genotoxicity, and repeated-dose studies have not been reported. Standard laboratory safety precautions should be followed.
References

[1]. Dihydroarteannuin ameliorates lupus symptom of BXSB mice by inhibiting production of TNF-alpha and blocking the signaling pathway NF-kappa B translocation. Int Immunopharmacol. 2006 Aug;6(8):1243-50.

[2]. A novel endoperoxide and related sesquiterpenes from Artemisia annua which are possibly derived from allylic hydroperoxides. Tetrahedron Volume 54, Issue 17, 23 April 1998, Pages 4345-4356.

Additional Infomation
Reports have indicated that Artemisia annua contains dihydroartemisinin B, and relevant data is available for reference.
Dihydroarteannuin B (CAS# 87206-33-5, molecular formula C₁₅H₂₂O₃, molecular weight 250.33) is a microbial metabolite of artemisinin B from Artemisia annua. It ameliorates lupus symptoms by inhibiting TNF-α production and NF-κB signaling. Also known as (3R)-dihydroarteannuin B. No clinical trials or regulatory approvals have been identified. Storage: powder at -20°C for 3 years.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H22O3
Molecular Weight
250.3334
Exact Mass
250.157
CAS #
87206-33-5
PubChem CID
14018832
Appearance
Typically exists as solid at room temperature
LogP
2.531
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Heavy Atom Count
18
Complexity
420
Defined Atom Stereocenter Count
0
SMILES
O1[C@]2(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]3([H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]4([H])[C@@]([H])(C([H])([H])[H])C(=O)OC34C12[H]
InChi Key
VWGPQZZLIAQJCE-BRQFDVKVSA-N
InChi Code
InChI=1S/C15H22O3/c1-8-4-5-11-9(2)12(16)17-15(11)10(8)6-7-14(3)13(15)18-14/h8-11,13H,4-7H2,1-3H3/t8-,9-,10?,11+,13-,14-,15?/m1/s1
Chemical Name
(4R,5S,8R,12R,14R)-4,8,12-trimethyl-2,13-dioxatetracyclo[7.5.0.01,5.012,14]tetradecan-3-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 3.9947 mL 19.9736 mL 39.9473 mL
5 mM 0.7989 mL 3.9947 mL 7.9895 mL
10 mM 0.3995 mL 1.9974 mL 3.9947 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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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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