Synonym
Ononin; Ononoside; Formononetin Glucoside, Formononetin 7-O-Glucoside; Formononetin-7-O-glucoside; Formononetin 7-glucoside
IUPAC/Chemical Name
3-(4-methoxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
InChi Key
MGJLSBDCWOSMHL-MIUGBVLSSA-N
InChi Code
InChI=1S/C22H22O9/c1-28-12-4-2-11(3-5-12)15-10-29-16-8-13(6-7-14(16)18(15)24)30-22-21(27)20(26)19(25)17(9-23)31-22/h2-8,10,17,19-23,25-27H,9H2,1H3/t17-,19-,20+,21-,22-/m1/s1
SMILES Code
O=C1C2=CC=C(O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)C=C2OC=C1C4=CC=C(OC)C=C4
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
>3 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:
Ononin is an isoflavonoid, is an additional growth inhibitor in soils associated with the weed, Pluchea lanceolata.
In vitro activity:
The in vitro anti-tumorigenic and anti-migratory properties of ononin were determined by MTT, colony formation, invasion, and migration in MG-63 and U2OS osteosarcoma cell lines. The dose-dependent manners of ononin treatment increased the expression of apoptosis and inhibition of cell proliferation through the EGFR-Erk1/2 signaling pathways. Additionally, ononin significantly inhibited the invasion and migration of human osteosarcoma cells.
Reference: Cancers (Basel). 2023 Jan 26;15(3):758. https://pubmed.ncbi.nlm.nih.gov/36765716/
In vivo activity:
This study assessed the possible cardioprotective effects of ononin in DOX-induced cardiotoxicity and elucidated the underlying molecular mechanisms. Ononin treatment ameliorated DOX-induced myocardial injury as determined by echocardiography. Furthermore, ononin partially restored DOX-induced cardiac dysfunction; the left ventricular ejection fraction (LVEF) and left ventricular systolic fractional shortening (LVFS) increased after pre-treatment with ononin. Further, ononin suppressed DOX-induced ER stress and apoptosis in rat cardiomyocytes and H9C2 cells.
Reference: Toxicol Appl Pharmacol. 2022 Oct 1;452:116179. https://pubmed.ncbi.nlm.nih.gov/35914558/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
10.0 |
23.23 |
| DMSO |
65.3 |
151.79 |
| PBS (pH 7.2) |
0.3 |
0.58 |
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
430.41
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. Gong G, Ganesan K, Xiong Q, Zheng Y. Anti-Invasive and Anti-Migratory Effects of Ononin on Human Osteosarcoma Cells by Limiting the MMP2/9 and EGFR-Erk1/2 Pathway. Cancers (Basel). 2023 Jan 26;15(3):758. doi: 10.3390/cancers15030758. PMID: 36765716; PMCID: PMC9913877.
2. Gong G, Ganesan K, Xiong Q, Zheng Y. Antitumor Effects of Ononin by Modulation of Apoptosis in Non-Small-Cell Lung Cancer through Inhibiting PI3K/Akt/mTOR Pathway. Oxid Med Cell Longev. 2022 Dec 27;2022:5122448. doi: 10.1155/2022/5122448. PMID: 36605098; PMCID: PMC9810408.
3. Yu T, Lu X, Liang Y, Yang L, Yin Y, Chen H. Ononin alleviates DSS-induced colitis through inhibiting NLRP3 inflammasome via triggering mitophagy. Immun Inflamm Dis. 2023 Feb;11(2):e776. doi: 10.1002/iid3.776. PMID: 36840499; PMCID: PMC9910166.
4. Zhang H, Weng J, Sun S, Zhou J, Yang Q, Huang X, Sun J, Pan M, Chi J, Guo H. Ononin alleviates endoplasmic reticulum stress in doxorubicin-induced cardiotoxicity by activating SIRT3. Toxicol Appl Pharmacol. 2022 Oct 1;452:116179. doi: 10.1016/j.taap.2022.116179. Epub 2022 Jul 29. PMID: 35914558.
In vitro protocol:
1. Gong G, Ganesan K, Xiong Q, Zheng Y. Anti-Invasive and Anti-Migratory Effects of Ononin on Human Osteosarcoma Cells by Limiting the MMP2/9 and EGFR-Erk1/2 Pathway. Cancers (Basel). 2023 Jan 26;15(3):758. doi: 10.3390/cancers15030758. PMID: 36765716; PMCID: PMC9913877.
2. Gong G, Ganesan K, Xiong Q, Zheng Y. Antitumor Effects of Ononin by Modulation of Apoptosis in Non-Small-Cell Lung Cancer through Inhibiting PI3K/Akt/mTOR Pathway. Oxid Med Cell Longev. 2022 Dec 27;2022:5122448. doi: 10.1155/2022/5122448. PMID: 36605098; PMCID: PMC9810408.
In vivo protocol:
1. Yu T, Lu X, Liang Y, Yang L, Yin Y, Chen H. Ononin alleviates DSS-induced colitis through inhibiting NLRP3 inflammasome via triggering mitophagy. Immun Inflamm Dis. 2023 Feb;11(2):e776. doi: 10.1002/iid3.776. PMID: 36840499; PMCID: PMC9910166.
2. Zhang H, Weng J, Sun S, Zhou J, Yang Q, Huang X, Sun J, Pan M, Chi J, Guo H. Ononin alleviates endoplasmic reticulum stress in doxorubicin-induced cardiotoxicity by activating SIRT3. Toxicol Appl Pharmacol. 2022 Oct 1;452:116179. doi: 10.1016/j.taap.2022.116179. Epub 2022 Jul 29. PMID: 35914558.
1. Wang, T., Liu, Y., Li, X., et al. Isoflavones from green vegetable soya beans and their antimicrobial and antioxidant activities. J. Sci. Food Agric. 98(5), 2043-2047 (2018).
2. Yu, D., Duan, Y., Bao, Y., et al. Isoflavonoids from Astragalus mongholicus protect PC12 cells from toxicity induced by L-glutamate. J. Ethnopharmacol. 98(1-2), 89-94 (2005).
3. Dong, L., Yin, L., Zhang, Y., et al. Anti-inflammatory effects of ononin on lipopolysaccharide-stimulated RAW 264.7 cells. Mol. Immunol. 83, 46-51 (2017).
