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
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
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 |
comments |
| 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:
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.
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).
