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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Synthesis of Four Eugenol Metabolites

Author(s): Xixi Jia, Hao Zhou, Xiwang Liu and Jianyong Li*

Volume 18, Issue 5, 2021

Published on: 07 August, 2020

Page: [415 - 418] Pages: 4

DOI: 10.2174/1570178617999200807213745

Price: $65

Abstract

Four eugenol metabolites were concisely synthesized and their structures were confirmed by 1H-NMR, 13C-NMR and high-resolution mass (HR-MS). Among them, the synthesis of eugenol-β-Dglucuronide (3) and eugenol sulfate (4) was reported for the first time. The successful synthesis of the four eugenol metabolites provides a material basis for further metabolic study of prodrug aspirin eugenol ester (AEE).

Keywords: Aspirin eugenol ester, Aspirin, Eugenol, Eugenol-β-D- glucuronide, Eugenol sulfate.

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[1]
Wick, J.Y. Consult Pharm., 2012, 27(5), 322-329.
[http://dx.doi.org/10.4140/TCP.n.2012.322] [PMID: 22591976]
[2]
Capodanno, D.; Angiolillo, D.J. Circulation, 2016, 134(20), 1579-1594.
[http://dx.doi.org/10.1161/CIRCULATIONAHA.116.023164] [PMID: 27729421]
[3]
Awtry, E.H.; Loscalzo, J. Circulation, 2000, 101(10), 1206-1218.
[http://dx.doi.org/10.1161/01.CIR.101.10.1206] [PMID: 10715270]
[4]
Barboza, J.N.; da Silva Maia Bezerra Filho, C.; Silva, R.O.; Medeiros, J.V.R.; de Sousa, D.P. Oxid. Med. Cell. Longev., 2018.20183957262
[http://dx.doi.org/10.1155/2018/3957262] [PMID: 30425782]
[5]
Li, J.Y.; Yu, Y.G.; Wang, Q.W.; Zhang, J.Y.; Yang, Y. J. Med. Chem. Res., 2012, 21, 995-999.
[http://dx.doi.org/10.1007/s00044-011-9609-1]
[6]
Huang, M.Z.; Yang, Y.J.; Liu, X.W.; Qin, Z.; Li, J.Y. Br. J. Pharmacol., 2019, 176(7), 906-918.
[http://dx.doi.org/10.1111/bph.14592] [PMID: 30706438]
[7]
Shen, Y.; Liu, X.; Yang, Y.; Li, J.; Ma, N.; Li, B. Biomed. Chromatogr., 2015, 29(1), 129-137.
[http://dx.doi.org/10.1002/bmc.3249] [PMID: 24935248]
[8]
Thompson, D.C.; Constantin-Teodosiu, D.; Moldéus, P. Chem. Biol. Interact., 1991, 77(2), 137-147.
[http://dx.doi.org/10.1016/0009-2797(91)90069-J] [PMID: 1991333]
[9]
Kajjout, M.; Rolando, C. Tetrahedron, 2011, 67, 4731-4741.
[http://dx.doi.org/10.1016/j.tet.2011.03.110]
[10]
Kenneth, M. Tetrahedron Lett., 2007, 48, 1359-1362.
[11]
Bashyal, P.; Pandey, R.P.; Thapa, S.B.; Kang, M.K.; Kim, C.J.; Sohng, J.K. ACS Omega, 2019, 4(5), 9367-9375.
[http://dx.doi.org/10.1021/acsomega.9b00535] [PMID: 31460026]
[12]
Casati, S.; Ottria, R.; Ciuffreda, P. Steroids, 2009, 74(2), 250-255.
[http://dx.doi.org/10.1016/j.steroids.2008.11.012] [PMID: 19071152]
[13]
Lucas, R.; Alcantara, D.; Morales, J.C. Carbohydr. Res., 2009, 344(11), 1340-1346.
[http://dx.doi.org/10.1016/j.carres.2009.05.016] [PMID: 19539271]
[14]
Zhang, Q.; Saki Raheem, K. Tetrahedron, 2012, 68, 4194-4201.
[http://dx.doi.org/10.1016/j.tet.2012.03.100]
[15]
Andrea, M.I.; Biasutto, L. Tetrahedron, 2015, 71, 3100-3106.
[http://dx.doi.org/10.1016/j.tet.2014.09.063]
[16]
Fairley, B.; Nigel, P. Tetrahedron, 2003, 59, 5407-5410.
[http://dx.doi.org/10.1016/S0040-4020(03)00869-X]
[17]
Gunnar, T. Bioorg. Med. Chem., 2005, 13, 1783-1789.
[18]
Sarah, R. Bioorg. Med. Chem., 2006, 14, 8386-8395.
[19]
Christopher, C. Steroids, 2014, 92, 74-80.
[20]
Paul, W.; Paul, A. Tetrahedron, 2006, 62, 6862-6868.
[21]
Daniel, A. J. Am. Chem. Soc., 1997, 119, 3385-3386.
[22]
Taber, D.F.; Paquette, C.M.; Gu, P.; Tian, W. J. Org. Chem., 2013, 78(19), 9772-9780.
[http://dx.doi.org/10.1021/jo4014996] [PMID: 23987140]
[23]
Elgendy, E.M.; Khayyat, S.A. Russ. J. Org. Chem., 2008, 44, 823-829.
[http://dx.doi.org/10.1134/S1070428008060079]
[24]
Kikuzaki, H.; Hara, S.; Kawai, Y.; Nakatani, N. Phytochemistry, 1999, 52, 1307-1312.
[http://dx.doi.org/10.1016/S0031-9422(99)00406-9]

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