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Ginkgetin

Alias: Ginkgetin; 481-46-9; 7,4'-Dimethylamentoflavone; Amentoflavone 7,4'-dimethyl ether; CHEBI:5353; HY5EZW8269; 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)chromen-4-one; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-(5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl)-2-(4-hydroxyphenyl)-;
Cat No.:V21589 Purity: ≥98%
Ginkgetin is a biflavonoid extracted from Ginkgo biloba leaves.
Ginkgetin
Ginkgetin Chemical Structure CAS No.: 481-46-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Ginkgetin is a biflavonoid extracted from Ginkgo biloba leaves. Ginkgetin has anti-tumor, anti~inflammatory, neuro-protective (neuro-protection), and antifungal effects. Ginkgetin is also a potent Wnt signaling inhibitor (antagonist) with IC50 of 5.92 μM.
Biological Activity I Assay Protocols (From Reference)
Targets
Natural biflavone; anti-inflammatory, anti-tumor, anti-oxidant, neuroprotective, anti-fungal activities
ln Vitro
Ginkgetin (2.5–20 μM; 48 hours) causes G2/M cell cycle arrest in Daoy cells and suppresses the growth of D283 and Daoy cell lines [2]. Osteosarcoma cells' apoptosis is markedly triggered by ginkgo (20–40 μM; 24 h) in a concentration-dependent manner [3]. In medulloblastoma cells, ginkgo (10–20 μM; 3–24 h) downregulates Wnt target gene expression without changing β-catenin expression [2]. In a concentration-dependent manner, ginkgo (1-10 μM) significantly inhibits the proliferation, migration, and wound recovery of endothelial cells induced by VEGF for 24 or 48 hours [1]. A549 cells die as a result of autophagy induced by ginkgo (5–10 μM; 48 hours) [5].
ln Vivo
Through the TLR4/NF-κB signaling pathway, ginkgo (25–100 mg/kg; intraperitoneally given two hours after ischemia) has anti-inflammatory effects on brain ischemia/reperfusion-induced damage in rat models [4]. ?In tumor-bearing nude mice, ginkgo (30 mg/kg; once daily gavage for 42 days) can prevent the formation of tumors in A549 cells [5].
Cell Assay
Cell viability assay [2]
Cell Types: Daoy and D283 cell lines
Tested Concentrations: 2.5, 5, 10, 20 μM
Incubation Duration: 48 hrs (hours)
Experimental Results: Inhibited cell growth, the IC50 of Daoy and D283 cells were 14.65 and 15.81 μM respectively.

Apoptosis analysis [3]
Cell Types: Osteosarcoma cells
Tested Concentrations: 20, 30, 40 μM
Incubation Duration: 24 hrs (hours)
Experimental Results: Dramatically induced osteosarcoma cell apoptosis in a concentration-dependent manner.

Cell cycle analysis [2]
Cell Types: Daoy cells
Tested Concentrations: 2.5, 5, 10, 20 μM
Incubation Duration: 24 hrs (hours)
Experimental Results: Compared with the control, the G2/M phase increased, indicating G2/M cell phase arrest.

Cell cycle analysis [2]
Cell Types: Daoy and D283 cell lines
Tested Concentrations: 10, 20 μM
Incubation Duration: 3, 6, 12, 24 hrs (hours)
Experimental Results: The expression of Wnt target genes, Axin2, cyclin D1 and survivin was attenuated at 20 μM. Daoy cells for 24 hrs (hours). Does not affect total beta-catenin levels and reduces beta-catenin phosphorylation levels in a time- and concentration-depen
Animal Protocol
Animal/Disease Models: Male SD (SD (Sprague-Dawley)) rat (200-220 g) [4]
Doses: 25, 50, 100 mg/kg
Route of Administration: intraperitoneal (ip) injection 2 hrs (hrs (hours)) after ischemia.
Experimental Results: diminished neurological deficit score. Inhibits the expression of NF-κB, TLR4 and IκBα in the ischemic penumbra cortex, and inhibits the degradation of IκBα. Reduce the expression of ICAM-1, COX-2 and iNOS. Downregulates the expression of downstream inflammatory factors PGE2 and TNF-α. IL-1β, IL-6, IL-8, and IL-10 protein expression was diminished.
References

[1]. Synergy of Ginkgetin and Resveratrol in Suppressing VEGF-Induced Angiogenesis: A Therapy in Treating Colorectal Cancer. Cancers (Basel). 2019 Nov 20;11(12):1828.

[2]. Biflavone Ginkgetin, a Novel Wnt Inhibitor, Suppresses the Growth of Medulloblastoma. Nat Prod Bioprospect. 2015 Mar 29;5(2):91-97.

[3]. Ginkgetin exerts growth inhibitory and apoptotic effects on osteosarcoma cells through inhibition of STAT3 and activation of caspase-3/9. Oncol Rep. 2016 Feb;35(2):1034-40.

[4]. Ginkgetin exerts anti-inflammatory effects on cerebral ischemia/reperfusion-induced injury in a rat model via the TLR4/NF-κB signaling pathway. Biosci Biotechnol Biochem. 2019 Apr;83(4):675-683.

[5]. Ginkgetin induces autophagic cell death through p62/SQSTM1-mediated autolysosome formation and redox setting in non-small cell lung cancer. Oncotarget. 2017 Oct 16;8(54):93131-93148.

Additional Infomation
Ginkgetin is a biflavonoid that is the 7,4'-dimethyl ether derivative of amentoflavone. Isolated from Ginkgo biloba and Dioon, it exhibits anti-HSV-1, antineoplastic and inhibitory activities towards arachidonate 5-lipoxygenase and cyclooxygenase 2. It has a role as an anti-HSV-1 agent, a cyclooxygenase 2 inhibitor, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an antineoplastic agent and a metabolite. It is a biflavonoid, a hydroxyflavone, a methoxyflavone and a ring assembly. It is functionally related to an amentoflavone.
Ginkgetin has been reported in Selaginella sinensis, Taxus cuspidata, and other organisms with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C32H22O10
Molecular Weight
566.518
Exact Mass
566.121
Elemental Analysis
C, 67.84; H, 3.91; O, 28.24
CAS #
481-46-9
PubChem CID
5271805
Appearance
Light yellow to yellow solid powder
Density
1.5±0.1 g/cm3
Boiling Point
863.7±65.0 °C at 760 mmHg
Melting Point
336ºC
Flash Point
287.2±27.8 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.714
LogP
4.45
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
5
Heavy Atom Count
42
Complexity
1080
Defined Atom Stereocenter Count
0
InChi Key
AIFCFBUSLAEIBR-UHFFFAOYSA-N
InChi Code
InChI=1S/C32H22O10/c1-39-18-10-20(34)30-23(37)13-27(41-28(30)11-18)16-5-8-25(40-2)19(9-16)29-21(35)12-22(36)31-24(38)14-26(42-32(29)31)15-3-6-17(33)7-4-15/h3-14,33-36H,1-2H3
Chemical Name
5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)chromen-4-one
Synonyms
Ginkgetin; 481-46-9; 7,4'-Dimethylamentoflavone; Amentoflavone 7,4'-dimethyl ether; CHEBI:5353; HY5EZW8269; 5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)chromen-4-one; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-(5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl)-2-(4-hydroxyphenyl)-;
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 : ≥ 20.83 mg/mL (~36.77 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2 mg/mL (3.53 mM) in 50% PEG300 + 50% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with heating and sonication.
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 mg/mL (3.53 mM) in 0.5% CMC-Na/saline water (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication (<60°C).
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.7652 mL 8.8258 mL 17.6516 mL
5 mM 0.3530 mL 1.7652 mL 3.5303 mL
10 mM 0.1765 mL 0.8826 mL 1.7652 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.

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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)
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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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