Ginkgetin | CAS#481-46-9 | anti-inflammatory

MedKoo Cat#: 584464 | Name: Ginkgetin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ginkgetin is a biflavonoid that has been isolated from G. biloba and has diverse biological activities, including pro-apoptotic, antiproliferative, anti-inflammatory, anti-atherosclerosis, and neuroprotective properties.

Chemical Structure

Ginkgetin

CAS#481-46-9

Theoretical Analysis

MedKoo Cat#: 584464

Name: Ginkgetin

CAS#: 481-46-9

Chemical Formula: C32H22O10

Exact Mass: 566.1213

Molecular Weight: 566.52

Elemental Analysis: C, 67.84; H, 3.91; O, 28.24

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 600.00	2 Weeks
25mg	USD 1,050.00	2 Weeks

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Synonym

Ginkgetin; Ginkgotin; Amentoflavone 7,4'-dimethyl ether; 7,4'-Dimethylamentoflavone;

IUPAC/Chemical Name

5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl]-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

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

SMILES Code

O=C1C=C(C2=CC=C(O)C=C2)OC3=C(C4=CC(C5=CC(C6=C(O)C=C(OC)C=C6O5)=O)=CC=C4OC)C(O)=CC(O)=C13

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ginkgetin is a potent inhibitor of Wnt signaling, with an IC50 of 5.92 μΜ.

In vitro activity:

Extensive apoptotic cells were observed after cells were subjected to H/R, whereas ginkgetin successfully reduced the number of apoptotic cells (Figure 2(e)). Determinations of apoptosis-related proteins Bcl-2, Bax, and caspase-9 validated the antiapoptotic effect of ginkgetin (Figure 2(f)). Collectively, ginkgetin could alleviate H/R-induced oxidative stress and apoptosis. Reference: Biomed Res Int. 2020 Nov 4;2020:1928410. https://pubmed.ncbi.nlm.nih.gov/33204684/

In vivo activity:

To further explore the anticancer activity of ginkgetin, this study established a xenograft nude mouse model. A robust decrease in body weight (> 20%) was observed after cisplatin treatment (Figure 6A). The tumor size and tumor weight were markedly decreased in groups treated with ginkgetin and cisplatin (Figure 6B-6D). The tumor inhibitory rates of ginkgetin and cisplatin groups were 50% and 48%, respectively (Figure 6E). These results indicated that ginkgetin exhibited promising anticancer effects without obvious toxicity. Reference: Oncotarget. 2017 Oct 16;8(54):93131-93148. https://pubmed.ncbi.nlm.nih.gov/29190983/

	Solvent	mg/mL	mM
Solubility
	DMSO	64.0	112.97
	DMSO:PBS (pH 7.2) (1:7)	0.1	0.21

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 566.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Liu X, Bian H, Dou QL, Huang XW, Tao WY, Liu WH, Li N, Zhang WW. Ginkgetin Alleviates Inflammation, Oxidative Stress, and Apoptosis Induced by Hypoxia/Reoxygenation in H9C2 Cells via Caspase-3 Dependent Pathway. Biomed Res Int. 2020 Nov 4;2020:1928410. doi: 10.1155/2020/1928410. PMID: 33204684; PMCID: PMC7661124. 2. Bai Y, Wang W, Shi M, Wei X, Zhou X, Li B, Zhang J. Novel Antibiofilm Inhibitor Ginkgetin as an Antibacterial Synergist against Escherichia coli. Int J Mol Sci. 2022 Aug 8;23(15):8809. doi: 10.3390/ijms23158809. PMID: 35955943; PMCID: PMC9369100. 3. Pan J, Li X, Guo F, Yang Z, Zhang L, Yang C. Ginkgetin attenuates cerebral ischemia-reperfusion induced autophagy and cell death via modulation of the NF-κB/p53 signaling pathway. Biosci Rep. 2019 Sep 6;39(9):BSR20191452. doi: 10.1042/BSR20191452. PMID: 31420372; PMCID: PMC6732367. 4. Lou JS, Bi WC, Chan GKL, Jin Y, Wong CW, Zhou ZY, Wang HY, Yao P, Dong TTX, Tsim KWK. 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. doi: 10.18632/oncotarget.21862. PMID: 29190983; PMCID: PMC5696249.

In vitro protocol:

In vivo protocol:

1. Pan J, Li X, Guo F, Yang Z, Zhang L, Yang C. Ginkgetin attenuates cerebral ischemia-reperfusion induced autophagy and cell death via modulation of the NF-κB/p53 signaling pathway. Biosci Rep. 2019 Sep 6;39(9):BSR20191452. doi: 10.1042/BSR20191452. PMID: 31420372; PMCID: PMC6732367. 2. Lou JS, Bi WC, Chan GKL, Jin Y, Wong CW, Zhou ZY, Wang HY, Yao P, Dong TTX, Tsim KWK. 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. doi: 10.18632/oncotarget.21862. PMID: 29190983; PMCID: PMC5696249.

1. Y. Su, C. M. Sun, H. H. Chuang, et al. Studies on the cytotoxic mechanisms of ginkgetin in a human ovarian adenocarcinoma cell line. Naunyn Schmiedebergs Arch. Pharmacol. 362(10), 82-90 (2000). 2. H. Lim, K. H. Son, H. W. Chang, et al. Effects of anti-inflammatory biflavonoid, ginkgetin, on chronic skin inflammation. Biol. Pharm. Bull. 29(5), 1046-1049 (2006). 3. N. Lian, J. Tong, W. Li, et al. Ginkgetin ameliorates experimental atherosclerosis in rats. Biomed. Pharmacother. 102, 510-516 (2018). 4. Y. Q. Wang, M. Y. Wang, X. R. Fu, et al. Neuroprotective effects of ginkgetin against neuroinjury in Parkinson’s disease model induced by MPTP via chelating iron. Free Radic Res. 49(9), 1069-1080 (2015).