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Bilobalide

Alias: (-)-Bilobalide; Bilobalide; Bilobalid
Cat No.:V2002 Purity: ≥98%
Bilobalide (BB)is a naturally occuring and biologically active terpenic trilactoneisolated from Ginkgo biloba (GB).
Bilobalide
Bilobalide Chemical Structure CAS No.: 33570-04-6
Product category: Apoptosis
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Bilobalide (BB) is a naturally occuring and biologically active terpenic trilactone isolated from Ginkgo biloba (GB). In vitro experiments showed that inhibition by BB and GB was eliminated in mutant receptors containing T6'S and S12'A substitutions, but their potencies were increased (42 and 125-fold, respectively) in S2'A mutant receptors, demonstrating the neuroprotective effects of this compound. By decreasing the β amyloid protein (A), a Aβ by-product of amyloidogenic processing of APP, and increasing the secretion of -secretase-cleaved soluble amyloid precursor protein (sAPPα), BB improved non-amyloidogenic processing of APP.

Biological Activity I Assay Protocols (From Reference)
Targets
Human Endogenous Metabolite
ln Vitro
Bilobalide (1-100 µM) completely suppresses the NMDA-evoked release of choline in a concentration-dependent manner with IC50 value of 2.3 µM[1].
Bilobalide (1, 5 and 10 μM) alone for 24 h does not affect cell viability of SH-SY5Y cells. The best protective effect was obtained at 10 μM[2], and pre-treating cells with bilobalide prevents Aβ 1-42, H2O2, and serum deprivation-induced decreases in cell viability.
Bilobalide (5 and 10 μM; 24 h) treatment dose-dependently raises levels of p-Akt (Ser473 and Thr308) in SH-SY5Y cells[2].
ln Vivo
Bilobalide (20 mg/kg) completely suppresses the NMDA-induced release of choline in vivo while basal choline levels were not significantly affected. When NMDA is retrograde dialyzed into the hippocampus of freely moving rats, this results in the release of choline in vivo. The effect caused by NMDA is completely inhibited by bilobalide (20 mg/kg intravenously)[1].
Animal Protocol
10-30 mg/kg; oral
Rats
References

[1]. Bilobalide, a constituent of Ginkgo biloba, inhibits NMDA-induced phospholipase A2 activation and phospholipid breakdown in rat hippocampus. Naunyn Schmiedebergs Arch Pharmacol. 1999 Dec;360(6):609-15.

[2]. Bilobalide prevents apoptosis through activation of the PI3K/Akt pathway in SH-SY5Y cells. Apoptosis. 2010 Jun;15(6):715-27.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H18O8
Molecular Weight
326.3
Exact Mass
326.10
Elemental Analysis
C, 55.21; H, 5.56; O, 39.23
CAS #
33570-04-6
Related CAS #
33570-04-6
Appearance
Solid powder
SMILES
CC(C)(C)[C@@]1(C[C@H]2[C@@]3([C@]14[C@H](C(=O)O[C@H]4OC3=O)O)CC(=O)O2)O
InChi Key
MOLPUWBMSBJXER-YDGSQGCISA-N
InChi Code
InChI=1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8-,11-,13-,14+,15+/m0/s1
Chemical Name
(1S,4R,7R,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.01,11.04,8]tetradecane-2,6,13-trione
Synonyms
(-)-Bilobalide; Bilobalide; Bilobalid
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)
DMSO: > 10 mM
Water: N/A
Ethanol: N/A
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.37 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 20.8 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: ≥ 2.08 mg/mL (6.37 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 20.8 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: ≥ 2.08 mg/mL (6.37 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 20.8 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 3.0647 mL 15.3233 mL 30.6466 mL
5 mM 0.6129 mL 3.0647 mL 6.1293 mL
10 mM 0.3065 mL 1.5323 mL 3.0647 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)
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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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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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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.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT02425436 Completed Drug: Ginkgo Biloba Extract
Other: Placebo
Intrauterine Growth Restriction
(IUGR)
Assiut University May 2014 Phase 2
NCT03475823 Completed Dietary Supplement: Ginkgo
biloba
Dietary Supplement: Placebo
control
Affect
Neuroimaging
Northumbria University February 17, 2017 Not Applicable
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