WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H464808
CAS#: 82-57-5
Description: Visnagin is a polyketide synthase-derived furanochromone originally isolated from A. visnaga that has diverse biological activities. It inhibits the germination and growth of ryegrass (IC50s = 502 and 214 µM, respectively). Visnagin (100 µg/ml) is cytotoxic to, and induces apoptosis in, HT-144 melanoma cells. It reduces LPS-stimulated increases in the secretion of TNF-α, IL-1β, and IFN-γ in BV-2 microglial cells when used at concentrations of 50 and 100 µM.4 Visnagin (25 mg/kg) protects against cardiomyopathy induced by doxorubicin in mice.
Hodoodo Cat#: H464808
Name: Visnagin
CAS#: 82-57-5
Chemical Formula: C13H10O4
Exact Mass: 230.06
Molecular Weight: 230.219
Elemental Analysis: C, 67.82; H, 4.38; O, 27.80
Synonym: Visnagin; NSC 100593; NSC 100593; NSC 100593;
IUPAC/Chemical Name: 4-methoxy-7-methyl-5H-furo[3,2-g]chromen-5-one
InChi Key: NZVQLVGOZRELTG-UHFFFAOYSA-N
InChi Code: InChI=1S/C13H10O4/c1-7-5-9(14)12-11(17-7)6-10-8(3-4-16-10)13(12)15-2/h3-6H,1-2H3
SMILES Code: O=C1C=C(OC2=C1C(OC)=C3C=COC3=C2)C
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: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMF | 10.0 | 43.44 | |
| DMF:PBS (pH 7.2) (1:5) | 0.2 | 0.69 | |
| DMSO | 5.0 | 21.72 | |
| Ethanol | 1.0 | 4.34 |
The following data is based on the product molecular weight 230.22 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Khalil N, Bishr M, El-Degwy M, Abdelhady M, Amin M, Salama O. Assessment of Conventional Solvent Extraction vs. Supercritical Fluid Extraction of Khella (Ammi visnaga L.) Furanochromones and Their Cytotoxicity. Molecules. 2021 Feb 27;26(5):1290. doi: 10.3390/molecules26051290. PMID: 33673560; PMCID: PMC7956847.
2: Ajarem JS, Hegazy AK, Allam GA, Allam AA, Maodaa SN, Mahmoud AM. Effect of Visnagin on Altered Steroidogenesis and Spermatogenesis, and Testicular Injury Induced by the Heavy Metal Lead. Comb Chem High Throughput Screen. 2021;24(6):758-766. doi: 10.2174/1386207323999200918124639. PMID: 32957877.
3: Fu HR, Li XS, Zhang YH, Feng BB, Pan LH. Visnagin ameliorates myocardial ischemia/reperfusion injury through the promotion of autophagy and the inhibition of apoptosis. Eur J Histochem. 2020 Sep 7;64(s2):3131. doi: 10.4081/ejh.2020.3131. PMID: 32909422; PMCID: PMC7482183.
4: Hassanein EHM, Sayed AM, Hussein OE, Mahmoud AM. Coumarins as Modulators of the Keap1/Nrf2/ARE Signaling Pathway. Oxid Med Cell Longev. 2020 Apr 22;2020:1675957. doi: 10.1155/2020/1675957. PMID: 32377290; PMCID: PMC7196981.
5: Lam PY, Kutchukian P, Anand R, Imbriglio J, Andrews C, Padilla H, Vohra A, Lane S, Parker DL Jr, Cornella Taracido I, Johns DG, Beerens M, MacRae CA, Caldwell JP, Sorota S, Asnani A, Peterson RT. Cyp1 Inhibition Prevents Doxorubicin-Induced Cardiomyopathy in a Zebrafish Heart-Failure Model. Chembiochem. 2020 Jul 1;21(13):1905-1910. doi: 10.1002/cbic.201900741. Epub 2020 Mar 6. PMID: 32003101; PMCID: PMC7500981.
6: Khalil N, Bishr M, Desouky S, Salama O. Ammi Visnaga L., a Potential Medicinal Plant: A Review. Molecules. 2020 Jan 12;25(2):301. doi: 10.3390/molecules25020301. PMID: 31940874; PMCID: PMC7024292.
7: Khalil HS, Sedky NK, Amin KM, Abd Elhafez OM, Arafa RK. Visnagin and benzofuran scaffold-based molecules as selective cyclooxygenase-2 inhibitors with anti-inflammatory and analgesic properties: design, synthesis and molecular docking. Future Med Chem. 2019 Apr;11(7):659-676. doi: 10.4155/fmc-2018-0398. Epub 2019 Apr 8. PMID: 30958028.
8: Pasari LP, Khurana A, Anchi P, Aslam Saifi M, Annaldas S, Godugu C. Visnagin attenuates acute pancreatitis via Nrf2/NFκB pathway and abrogates associated multiple organ dysfunction. Biomed Pharmacother. 2019 Apr;112:108629. doi: 10.1016/j.biopha.2019.108629. Epub 2019 Feb 22. PMID: 30798137.
9: Chen S, Elzaki MEA, Ding C, Li ZF, Wang J, Zeng RS, Song YY. Plant allelochemicals affect tolerance of polyphagous lepidopteran pest Helicoverpa armigera (Hübner) against insecticides. Pestic Biochem Physiol. 2019 Feb;154:32-38. doi: 10.1016/j.pestbp.2018.12.009. Epub 2018 Dec 18. PMID: 30765054.
10: Aydoğmuş-Öztürk F, Jahan H, Beyazit N, Günaydın K, Choudhary MI. The anticancer activity of visnagin, isolated from Ammi visnaga L., against the human malignant melanoma cell lines, HT 144. Mol Biol Rep. 2019 Apr;46(2):1709-1714. doi: 10.1007/s11033-019-04620-1. Epub 2019 Jan 29. PMID: 30694454.
11: Fu H, Li X, Tan J. NIPAAm-MMA nanoparticle-encapsulated visnagin ameliorates myocardial ischemia/reperfusion injury through the promotion of autophagy and the inhibition of apoptosis. Oncol Lett. 2018 Apr;15(4):4827-4836. doi: 10.3892/ol.2018.7922. Epub 2018 Feb 1. PMID: 29552122; PMCID: PMC5840612.
12: Asnani A, Zheng B, Liu Y, Wang Y, Chen HH, Vohra A, Chi A, Cornella-Taracido I, Wang H, Johns DG, Sosnovik DE, Peterson RT. Highly potent visnagin derivatives inhibit Cyp1 and prevent doxorubicin cardiotoxicity. JCI Insight. 2018 Jan 11;3(1):e96753. doi: 10.1172/jci.insight.96753. PMID: 29321375; PMCID: PMC5821184.
13: Kasote DM, Jagtap SD, Thapa D, Khyade MS, Russell WR. Herbal remedies for urinary stones used in India and China: A review. J Ethnopharmacol. 2017 May 5;203:55-68. doi: 10.1016/j.jep.2017.03.038. Epub 2017 Mar 23. PMID: 28344029.
14: Travaini ML, Sosa GM, Ceccarelli EA, Walter H, Cantrell CL, Carrillo NJ, Dayan FE, Meepagala KM, Duke SO. Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides. J Agric Food Chem. 2016 Dec 21;64(50):9475-9487. doi: 10.1021/acs.jafc.6b02462. Epub 2016 Dec 12. PMID: 27936681.
15: Kuriakose RK, Kukreja RC, Xi L. Potential Therapeutic Strategies for Hypertension-Exacerbated Cardiotoxicity of Anticancer Drugs. Oxid Med Cell Longev. 2016;2016:8139861. doi: 10.1155/2016/8139861. Epub 2016 Oct 17. PMID: 27829985; PMCID: PMC5086499.
16: Winderl B, Schwaiger S, Ganzera M. Fast and improved separation of major coumarins in Ammi visnaga (L.) Lam. by supercritical fluid chromatography. J Sep Sci. 2016 Oct;39(20):4042-4048. doi: 10.1002/jssc.201600734. Epub 2016 Sep 8. PMID: 27514847.
17: Xi L. Visnagin-a new protectant against doxorubicin cardiotoxicity? Inhibition of mitochondrial malate dehydrogenase 2 (MDH2) and beyond. Ann Transl Med. 2016 Feb;4(4):65. doi: 10.3978/j.issn.2305-5839.2015.10.43. PMID: 27004212; PMCID: PMC4779788.
18: Pavela R, Vrchotová N, Tříska J. Larvicidal activity of extracts from Ammi visnaga Linn. (Apiaceae) seeds against Culex quinquefasciatus Say. (Diptera: Culicidae). Exp Parasitol. 2016 Jun;165:51-7. doi: 10.1016/j.exppara.2016.03.016. Epub 2016 Mar 16. PMID: 26995534.
19: Liu Y, Asnani A, Zou L, Bentley VL, Yu M, Wang Y, Dellaire G, Sarkar KS, Dai M, Chen HH, Sosnovik DE, Shin JT, Haber DA, Berman JN, Chao W, Peterson RT. Visnagin protects against doxorubicin-induced cardiomyopathy through modulation of mitochondrial malate dehydrogenase. Sci Transl Med. 2014 Dec 10;6(266):266ra170. doi: 10.1126/scitranslmed.3010189. PMID: 25504881; PMCID: PMC4360984.
20: Abu-Hashem AA, El-Shazly M. Synthesis, reactions and biological activities of furochromones: a review. Eur J Med Chem. 2015 Jan 27;90:633-65. doi: 10.1016/j.ejmech.2014.12.001. Epub 2014 Dec 2. PMID: 25499986.
