Ginkgetin
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MedKoo CAT#: 584464

CAS#: 481-46-9

Description: 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

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Ginkgetin
CAS# 481-46-9

Theoretical Analysis

MedKoo Cat#: 584464
Name: Ginkgetin
CAS#: 481-46-9
Chemical Formula: C32H22O10
Exact Mass: 566.12
Molecular Weight: 566.518
Elemental Analysis: C, 67.84; H, 3.91; O, 28.24

Price and Availability

Size Price Availability Quantity
1mg USD 210
5mg USD 405
10mg USD 640
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Synonym: Ginkgetin

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:
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/

Solubility Data

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

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.

Recalculate based on batch purity %
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: 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.
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.

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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).