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Ginkgolide B (BN-52021)

Alias: BN-52021; Bilobalide B; BN 52051; BN52051; Ginkgolide B
Cat No.:V1493 Purity: ≥98%
COA Product Data Instructions for use SDS
Ginkgolide B (Bilobalide B; BN-52051; BN52051) is a naturally occuring compound acting as a PAFR (platelet-activating factor receptor) antagonist with an IC50 of 3.6 μM.
Ginkgolide B (BN-52021) Chemical Structure CAS No.: 15291-77-7
Product category: PAFR
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%

COA
MSDS
Instructions
Product Description

Ginkgolide B (Bilobalide B; BN-52051; BN52051) is a naturally occuring compound acting as a PAFR (platelet-activating factor receptor) antagonist with an IC50 of 3.6 μM.

Biological Activity I Assay Protocols (From Reference)
Targets
PAFR ( IC50 = 3.6 μM )
ln Vitro

In vitro activity: Ginkgolide B potently exhibits a platelet-activating factor (PAF) receptor.[1] Ginkgolide B (0.5 μM–12 μM) treatment of PMN causes a rapid and weak production of reactive oxygen species, as shown by chemiluminescence. Ginkgolide B potentiates the CL response induced by fMet-Leu-Phe and zymosan. Ras/MAPK signaling pathway is altered and cyst cell differentiation is induced by ginkgolide B.[2] Ginkgolide B encourages endothelial gene expression and proliferation, and it significantly improves the ability of endothelial cells to integrate into vascular networks and the migration response triggered by vascular endothelial growth factor. Ginkgolide B shields EPCs from cell death caused by H2O2. The phosphorylation of eNOS, Akt, and p38 is induced by ginkgolide B, and this promotes cell proliferation and function.[3]
ln Vivo
Ginkgolide B (2 μM) significantly inhibits the formation of MDCK cysts in a dose-dependent manner, with up to 69% reduction. Ginkgolide B also significantly inhibits cyst enlargement in the MDCK cyst model, embryonic kidney cyst model, and PKD mouse model.[2] Ginkgolide B (50 mg/kg p.o.) applied prior to ischemia significantly lessens neuronal damage.[4] In the mouse model of focal ischemia, 30 minutes of pretreatment with Ginkgolide B (100 mg/kg, s.c.) decreases the infarct area. Ginkgolide B (1 μM) shields hippocampal neurons and astrocytes from neonatal rats' primary cultures from glutamate-induced neuronal damage. Ginkgolide B (100 μM) reduces apoptotic damage induced by staurosporine.[5] Ginkgolide B (1 mg/kg i.v. or 10 mg/kg p.o.) inhibits bronchoconstriction, the hematocrit increase, and the concomitant thrombopenia and leukopenia induced by PAF-acether (33 ng/kg–100 ng/kg) in animals anesthetized with pentobarbitone or ethyl carbamate. Aerosolized PAF-acether-induced bronchoconstriction is lessened by ginkgolide B at a dose of 3 mg/kg. At a dosage of 300 μM, ginkgolide B also prevents PAF-acether-stimulated alveolar macrophages from producing superoxide. Injecting 100 ng of PAF-acether into a perfused lung causes thromboxane to form, but ginkgolide B prevents this from happening. Pretreating parenchyma lung strips with Ginkgolide B (100 μM) reduces the release of thromboxane and partially inhibits the contraction caused by PAF-acether (0.1 μM).[6] Ginkgolide B prevents ischemia injury from developing.[7] Ginkgolide B treatment shows a significant decrease in brain edema, neurological deficits, and the volume of the infarction. Moreover, ischemia/reperfusion (I/R)-induced NF-κB, microglia activation, and pro-inflammatory cytokine production are inhibited by ginkgolide B. In post-ischemic brains, ginkgolide B raises Bcl-2 protein levels while lowering Bax protein levels.[8] Ginkgolide B reduces platelet aggregation and prevents Akt phosphorylation and phosphatidylinositol 3 kinase (PI3K) activation in platelets activated by collagen and thrombin. Ginkgolide B reduces plasma PF4 and RANTES levels in ApoE−/− mice.Ginkgolide B reduces P-selectin, PF4, RANTES, and CD40L expression in aortic plaque in ApoE−/− mice.Furthermore, ginkgolide B inhibits macrophage and vascular cell adhesion protein 1 (VCAM-1) expression in aorta lesions in ApoE−/− mice.[9]
Animal Protocol
Dissolved in PBS; 0.6 mg/day; Intragastric administration
Eight-week-old male ApoE / mice
References

[1]. Biochem Pharmacol . 1987 Sep 1;36(17):2749-52.

[2]. Am J Physiol Renal Physiol . 2012 May 15;302(10):F1234-42.

[3]. Eur Cell Mater . 2011 May 28:21:459-69.

[4]. J Cereb Blood Flow Metab . 1990 Jan;10(1):133-5.

[5]. Pharmacopsychiatry . 2003 Jun:36 Suppl 1:S8-14.

[6]. Eur J Pharmacol . 1986 Aug 7;127(1-2):83-95.

[7]. J Neurochem . 1988 Dec;51(6):1900-5.

[8]. Eur J Pharm Sci . 2012 Nov 20;47(4):652-60.

[9]. PLoS One . 2012;7(5):e36237.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H24O10
Molecular Weight
424.4
Exact Mass
424.14
Elemental Analysis
C, 56.60; H, 5.70; O, 37.70
CAS #
15291-77-7
Related CAS #
15291-77-7
Appearance
Solid powder
SMILES
CC1C(=O)OC2C1(C34C(=O)OC5C3(C2O)C6(C(C5)C(C)(C)C)C(C(=O)OC6O4)O)O
InChi Key
SQOJOAFXDQDRGF-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H24O10/c1-6-12(23)28-11-9(21)18-8-5-7(16(2,3)4)17(18)10(22)13(24)29-15(17)30-20(18,14(25)27-8)19(6,11)26/h6-11,15,21-22,26H,5H2,1-4H3
Chemical Name
8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione
Synonyms
BN-52021; Bilobalide B; BN 52051; BN52051; Ginkgolide B
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: ~85 mg/mL (~200.3 mM)
Water: <1 mg/mL
Ethanol: ~2 mg/mL (~4.9 mM)
Solubility (In Vivo)
30%Propylene glycol, 5%Tween 80, 65% D5W: 10mg/mL
 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.3563 mL 11.7813 mL 23.5627 mL
5 mM 0.4713 mL 2.3563 mL 4.7125 mL
10 mM 0.2356 mL 1.1781 mL 2.3563 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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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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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.
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Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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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
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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
NCT03772847 Completed Drug: ginkgolide Intravenous Alteplase Thrombolysis
Neurological Improving		 Second Affiliated Hospital, School
of Medicine, Zhejiang University		 July 31, 2018 Phase 4
Biological Data
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