Pauzi Research Spring 2016

Proposed Project Description

We are interested in understanding the enzymatic oxidation of biophenols. We will use the High Performance Liquid Chromatography (HPLC) to collect relevant data.

Abstract

Methyleugneol is a phenolic type of flavourant found in essential oils, which is primarily derived from cloves. This compound has been known to be a human carcinogen listed on the National Toxicology Program Report. Evidence suggests that Eugenol displays an extensive span of biological activities.Furthermore, studies has shown that Eugenol to be carcinogenic after long term dietary administration in animals at high doses. The mechanism of hepatic carcinogenesis resulted from the bioactivation of the Methyleugenol has also shown to occur in the liver. The mechanism behind the chemical oxidation of Eugenol is that it gives a one electron oxidation to form a Eugenol radical and the radical will recombine together in a couple of different ways to form polymers. In this study, we show that Eugenol undergoes Enzymatic oxidation with Hydrogen Peroxide and Horseradish peroxidase to form free radicals.

References

1) Sipe, H. J., Lardinois, O. M., & Mason, R. P. (2014). Free Radical Metabolism of Methyleugenol and Related Compounds. Chemical Research in Toxicology, 27(4), 483–489. http://doi.org/10.1021/tx400256b

2) Chowdhry, B. Z., Ryall, J. P., Dines, T. J., & Mendham, A. P. (2015). Infrared and Raman Spectroscopy of Eugenol, Isoeugenol, and Methyl Eugenol: Conformational Analysis and Vibrational Assignments from Density Functional Theory Calculations of the Anharmonic Fundamentals. The Journal of Physical Chemistry A, 119(46), 11280–11292. http://doi.org/10.1021/acs.jpca.5b07607

3) Mastelić, J., Jerković, I., Blažević, I., Poljak-Blaži, M., Borović, S., Ivančić-Baće, I., … Müller, N. (2008). Comparative Study on the Antioxidant and Biological Activities of Carvacrol, Thymol, and Eugenol Derivatives. Journal of Agricultural and Food Chemistry, 56(11), 3989–3996. http://doi.org/10.1021/jf073272v

4) Ruff, C., Hör, K., Weckerle, B., König, T., & Schreier, P. (2002). Authenticity Assessment of Estragole and Methyl Eugenol by On-Line Gas Chromatography−Isotope Ratio Mass Spectrometry. Journal of Agricultural and Food Chemistry, 50(5), 1028–1031. http://doi.org/10.1021/jf011204h

5) Olbert-Majkut, A., & Wierzejewska, M. (2008). Conformational Study of Eugenol by Density Functional Theory Method and Matrix-Isolation Infrared Spectroscopy. The Journal of Physical Chemistry A, 112(25), 5691–5699

Current Progress

March 2016

I have now been able to collect some chromatograms related to my research project.