Mild and Green Protocol for Selective Deuteration of Quercetin-3-ORutinoside (Rutin) Under Aqueous Basic Conditions

Page: [147 - 151] Pages: 5

  • * (Excluding Mailing and Handling)

Abstract

A convenient and cost-effective method for selective deuteration of rutin using biologically compatible bases and D2O both as a deuterium source and a solvent is herein reported. The protocol is benign and inexpensive affording good results in very mild conditions allowing to reduce the required amount of deuterium oxide. The position of the C-H/C-D exchange and the level of deuteration can be conveniently followed by 1H-NMR.

Keywords: Rutin, arginine, deuterium oxide, NMR, TRIS, solvent.

Graphical Abstract

[1]
Banjarnahor, S.D.S.; Artanti, N. Antioxidant properties of flavonoids. Med. J. Indones., 2015, 23, 239-244.
[http://dx.doi.org/10.13181/mji.v23i4.1015]
[2]
Procházková, D.; Boušová, I.; Wilhelmová, N. Antioxidant and prooxidant properties of flavonoids. Fitoterapia, 2011, 82(4), 513-523.
[http://dx.doi.org/10.1016/j.fitote.2011.01.018] [PMID: 21277359]
[3]
Hiraoka, K.; Miyamoto, T.; Baba, S.; Furuta, T. Preparation of Deuterium-labeled Rutin by hydrogen exchange reaction. J. Labelled Comp. Radiopharm., 1981, 18(5), 613-619.
[http://dx.doi.org/10.1002/jlcr.2580180502]
[4]
Faizi, S.; Siddiqui, H.; Naz, A.; Bano, S. Specific deuteration in patuletin and related flavonoids via keto-enol tautomeris: Solvent and temperature dependent 1H-NMR studies. Helv. Chim. Acta, 2010, 93, 466-480.
[http://dx.doi.org/10.1002/hlca.200900249]
[5]
Skaddan, M.B.; Yung, C.M.; Bergman, R.G. Stoichiometric and catalytic deuterium and tritium labeling of “unactivated” organic substrates with cationic Ir(III) complexes. Org. Lett., 2004, 6(1), 11-13.
[http://dx.doi.org/10.1021/ol0359923] [PMID: 14703338]
[6]
Yung, C.M.; Skaddan, M.B.; Bergman, R.G. Stoichiometric and catalytic H/D incorporation by cationic iridium complexes: A common monohydrido-iridium intermediate. J. Am. Chem. Soc., 2004, 126(40), 13033-13043.
[http://dx.doi.org/10.1021/ja046825g] [PMID: 15469302]
[7]
Sajiki, H.; Ito, N.; Esaki, H.; Maesawa, T.; Maegawa, T.; Hirota, K. Aromatic ring favorable and efficient H-D exchange reaction catalyzed by Pt/C. Tetrahedron Lett., 2005, 46, 6995-6998.
[http://dx.doi.org/10.1016/j.tetlet.2005.08.067]
[8]
Rasku, S.; Wahala, K. Synthesis of deuterium labeled polyhydroxy flavones and 3-flavonols. Tetrahedron, 2000, 56, 913-916.
[http://dx.doi.org/10.1016/S0040-4020(99)01085-6]
[9]
Vanderlocht, J.; van Beers, J.J.B.C.; Limburg, P.C.; Damoiseaux, J.; Roozendaal, C. Antigen-specific detection of autoantibodies against Myeloperoxidase (MPO) and Proteinase 3 (PR3).Autoantibodies;; Houen, G., Ed.; Springer New York: New York, NY, 2019, Vol. 1901, pp. 153-176.
[http://dx.doi.org/10.1007/978-1-4939-8949-2_12]
[10]
Brocks, D.R.; Jamali, F. Clinical pharmacokinetics of ketorolac tromethamine. Clin. Pharmacokinet., 1992, 23(6), 415-427.
[http://dx.doi.org/10.2165/00003088-199223060-00003] [PMID: 1458761]
[11]
Sarangi, D.K.; Mekap, S.K.; Panda, S.S.; Ghose, D.; Rana, R.; Mahapatra, M. Formulation and development of Ketorolac Tromethamine Ophthalmic solution. J. Drug Deliv. Ther., 2018, 8(3), 78-81.
[http://dx.doi.org/10.22270/jddt.v8i3.1710]
[12]
Los-Arcos, I.; Pigrau, C.; Rodríguez-Pardo, D.; Fernández-Hidalgo, N.; Andreu, A.; Larrosa, N.; Almirante, B. Long-Term Fosfomycin-Tromethamine Oral Therapy for Difficult-To-Treat Chronic Bacterial Prostatitis. Antimicrob. Agents Chemother., 2015, 60(3), 1854-1858.
[http://dx.doi.org/10.1128/AAC.02611-15] [PMID: 26666924]
[13]
Abou Alaiwa, M.H.; Launspach, J.L.; Sheets, K.A.; Rivera, J.A.; Gansemer, N.D.; Taft, P.J.; Thorne, P.S.; Welsh, M.J.; Stoltz, D.A.; Zabner, J. Repurposing tromethamine as inhaled therapy to treat CF airway disease. JCI Insight, 2016, 1(8), 1-11.
[http://dx.doi.org/10.1172/jci.insight.87535] [PMID: 27390778]
[14]
Acquaviva, R.; Lanteri, R.; Li Destri, G.; Caltabiano, R.; Vanella, L.; Lanzafame, S.; Di Cataldo, A.; Li Volti, G.; Di Giacomo, C. Beneficial effects of rutin and L-arginine coadministration in a rat model of liver ischemia-reperfusion injury. Am. J. Physiol. Gastrointest. Liver Physiol., 2009, 296(3), G664-G670.
[http://dx.doi.org/10.1152/ajpgi.90609.2008] [PMID: 19109403]