Osajin

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

MedKoo CAT#: 584963

CAS#: 482-53-1

Description: Osajin is a bioactive isoflavone present in the fruit of Maclura pomifera, commonly referred to as the Osage orange, and has antioxidant properties. Osajin has potent cardioprotective effects in perfused rat hearts and kidney subjected to global ischemia and reperfusion. Its effects may be mediated through the inhibition of lipid peroxidation. Osajin can antagonize myocardial injury induced by I/R through inhibiting oxidative stress. Osajin had a noticeable inhibition of AChE with IC(50) values of 2.239 mM.


Chemical Structure

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Osajin
CAS# 482-53-1

Theoretical Analysis

MedKoo Cat#: 584963
Name: Osajin
CAS#: 482-53-1
Chemical Formula: C25H24O5
Exact Mass: 404.1624
Molecular Weight: 404.462
Elemental Analysis: C, 74.24; H, 5.98; O, 19.78

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Osajin

IUPAC/Chemical Name: 4H,8H-Benzo(1,2-b:3,4-b')dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)- (8CI)

InChi Key: DCTLJGWMHPGCOS-UHFFFAOYSA-N

InChi Code: InChI=1S/C25H24O5/c1-14(2)5-10-17-21(27)20-22(28)19(15-6-8-16(26)9-7-15)13-29-24(20)18-11-12-25(3,4)30-23(17)18/h5-9,11-13,26-27H,10H2,1-4H3

SMILES Code: O=C1C2=C(O)C(C/C=C(C)\C)=C3C(C=CC(C)(C)O3)=C2OC=C1C4=CC=C(O)C=C4

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: >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

Preparing Stock Solutions

The following data is based on the product molecular weight 404.462 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

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1: Kim JE, Heo YS, Lee KW. Osajin Inhibits Solar UV-Induced Cyclooxygenase-2 Expression Through Direct Inhibition of RSK2. J Cell Biochem. 2017 Nov;118(11):4080-4087. doi: 10.1002/jcb.26063. Epub 2017 May 23. PubMed PMID: 28409880.

2: Moon HI. Effect of osajin and pomiferin on antidiabetic effects from normal and streptozotocin-induced diabetic rats. Nat Prod Commun. 2014 Dec;9(12):1723-4. PubMed PMID: 25632468.

3: Florian T, Necas J, Bartosikova L, Klusakova J, Suchy V, Naggara EB, Janostikova E, Bartosik T. Effects of prenylated isoflavones osajin and pomiferin in premedication on heart ischemia-reperfusion. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2006 Jul;150(1):93-100. PubMed PMID: 16936909.

4: Diopan V, Babula P, Shestivska V, Adam V, Zemlicka M, Dvorska M, Hubalek J, Trnkova L, Havel L, Kizek R. Electrochemical and spectrometric study of antioxidant activity of pomiferin, isopomiferin, osajin and catalposide. J Pharm Biomed Anal. 2008 Sep 10;48(1):127-33. doi: 10.1016/j.jpba.2008.05.025. Epub 2008 May 28. PubMed PMID: 18597965.

5: Dilek E, Erol HS, Cakir A, Koc M, Halici MB. Natural product inhibitors of carbonic anhydrase I and II isoenzymes: osajin and pomiferin. Arch Physiol Biochem. 2017 Oct;123(4):219-224. doi: 10.1080/13813455.2017.1303742. Epub 2017 Mar 24. PubMed PMID: 28338341.

6: Huang TT, Liu FG, Wei CF, Lu CC, Chen CC, Lin HC, Ojcius DM, Lai HC. Activation of multiple apoptotic pathways in human nasopharyngeal carcinoma cells by the prenylated isoflavone, osajin. PLoS One. 2011 Apr 12;6(4):e18308. doi: 10.1371/journal.pone.0018308. PubMed PMID: 21532751; PubMed Central PMCID: PMC3075243.

7: Veselá D, Kubínová R, Muselík J, Zemlicka M, Suchý V. Antioxidative and EROD activities of osajin and pomiferin. Fitoterapia. 2004 Mar;75(2):209-11. PubMed PMID: 15030927.

8: Ribaudo G, Vendrame T, Bova S. Isoflavones from Maclura pomifera: structural elucidation and in silico evaluation of their interaction with PDE5. Nat Prod Res. 2017 Sep;31(17):1988-1994. doi: 10.1080/14786419.2016.1269101. Epub 2016 Dec 27. PubMed PMID: 28025893.

9: Bartosíková L, Necas J, Suchý V, Janostíková E, Bartosík T, Jurica J, Florian T, Klusáková J, Frydrych M. Protective effects of osajin in ischemia-reperfusion of laboratory rat kidney. Pharmazie. 2006 Jun;61(6):552-5. PubMed PMID: 16826976.

10: Necas J, Bartosíková L, Florian T, Klusáková J, Suchý V, Naggar EM, Janostíková E, Bartosík T, Lisková M. [Protective effects of the flavonoids osajin and pomiferin on heart ischemia-reperfusion]. Ceska Slov Farm. 2006 Jul;55(4):168-74. Czech. PubMed PMID: 16921735.

11: Fránová J, Pavlík M. [Testing of antidiabetic and antioxidative effect of the flavonoid osajin in an experiment]. Ceska Slov Farm. 2007 Jul;56(4):200-4. Czech. PubMed PMID: 17969319.

12: Chaichamnong N, Temkitthawon P, Khorana N, Pitpakdeeanan P, Taepavarapruk P, Nuengchamnong N, Siriwattanasathien Y, Suksamrarn A, Ingkaninan K. Phosphodiesterase 5 Inhibitors from Derris scandens. Planta Med. 2018 Oct;84(15):1134-1140. doi: 10.1055/a-0619-5547. Epub 2018 Apr 27. PubMed PMID: 29702722.

13: Hošek J, Toniolo A, Neuwirth O, Bolego C. Prenylated and geranylated flavonoids increase production of reactive oxygen species in mouse macrophages but inhibit the inflammatory response. J Nat Prod. 2013 Sep 27;76(9):1586-91. doi: 10.1021/np400242e. Epub 2013 Aug 16. PubMed PMID: 23947936.

14: Gruber JV, Holtz R, Sikkink SK, Tobin DJ. In vitro and ex vivo examination of topical Pomiferin treatments. Fitoterapia. 2014 Apr;94:164-71. doi: 10.1016/j.fitote.2014.01.023. Epub 2014 Feb 8. PubMed PMID: 24513505.

15: WOLFROM ML, HARRIS WD, et al. Osage orange pigments; complete structures of osajin and pomiferin. J Am Chem Soc. 1946 Mar;68:406-18. PubMed PMID: 21015734.

16: Gascon AL, Walaszek EJ. Inhibition of valyl angiotensinamide II by osajin. J Pharm Pharmacol. 1966 Jul;18(7):478-9. PubMed PMID: 4381734.

17: Ribaudo G, Pagano MA, Pavan V, Redaelli M, Zorzan M, Pezzani R, Mucignat-Caretta C, Vendrame T, Bova S, Zagotto G. Semi-synthetic derivatives of natural isoflavones from Maclura pomifera as a novel class of PDE-5A inhibitors. Fitoterapia. 2015 Sep;105:132-8. doi: 10.1016/j.fitote.2015.06.020. Epub 2015 Jun 29. PubMed PMID: 26136059.

18: Darji K, Miglis C, Wardlow A, Abourashed EA. HPLC determination of isoflavone levels in osage orange from the Midwest and southern United States. J Agric Food Chem. 2013 Jul 17;61(28):6806-11. doi: 10.1021/jf400954m. Epub 2013 Jul 2. PubMed PMID: 23772950; PubMed Central PMCID: PMC3774050.

19: Orhan I, Senol FS, Kartal M, Dvorská M, Zemlicka M, Smejkal K, Mokrý P. Cholinesterase inhibitory effects of the extracts and compounds of Maclura pomifera (Rafin.) Schneider. Food Chem Toxicol. 2009 Aug;47(8):1747-51. doi: 10.1016/j.fct.2009.04.023. Epub 2009 Apr 24. PubMed PMID: 19394400.

20: Orazbekov Y, Ibrahim MA, Mombekov S, Srivedavyasasri R, Datkhayev U, Makhatov B, Chaurasiya ND, Tekwani BL, Ross SA. Isolation and Biological Evaluation of Prenylated Flavonoids from Maclura pomifera. Evid Based Complement Alternat Med. 2018 Jan 14;2018:1370368. doi: 10.1155/2018/1370368. eCollection 2018. PubMed PMID: 29552078; PubMed Central PMCID: PMC5820588.