Enzymatic Synthesis of Ferulyl Oleins and their Inhibition Effects on Nitrosamine

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Ferulyl oleins were synthesized from ethyl ferulate and triolein with Lipopan lipase. The influences of reaction parameters, such as reaction system and water activity were evaluated. Among the tested lipases in different reaction system, Lipopan S BG appeared to be the most appropriate resulting in a overall yield of ferulyl oleins 28.31% within 120h in toluene system, whereas trans esterification degree with other lipases did not exceed 20% in any condition. Similarly, the Lipopan lipase expressed the highest transesterification yield at aw = 0.33. The inhibition of nitrosamine by ferulyl oleins in vitro experiments were performed. The results showed that ferulyl oleins had a greater ability to inhibit the N-nitrosodimethylamine formation than ferulic acid and ethyl ferulate did. Ferulyl oleins showed an inhibition rate as high as 76.9%. In the case of nitrite, the extent of the inhibition by ferulyl oleins was slightly lower than EF. They all exhibited the highest inhibition rate at the concentration of 1.5mg/mL. The results suggest that ferulyl oleins can inhibite nitrosamine formation efficiently.

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412-417

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August 2012

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© 2012 Trans Tech Publications Ltd. All Rights Reserved

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[1] Aiub, C. A., Pinto, L. F. and Felzenszwalb, I., N-Nitrosodimethylamine mutagenicity at low concentrations, Toxicol. Lett., vol. 145. pp.36-45, (2003).

DOI: 10.1016/s0378-4274(03)00263-7

Google Scholar

[2] Shahidi F, Pegg RB and Sen NP., Absence of volatile N-nitrosamines in cooked nitrite-free cured muscle foods, Meat Sci, vol. 37. p.327–336, March (1994).

DOI: 10.1016/0309-1740(94)90050-7

Google Scholar

[3] Kolb E, Haghg M, Janzowski C, Vetter A and Eisenbrand G., Potential nitrosamine formation and its prevention during biological identification of red beet juice, Food Chem Toxicol, vol. 35. p.219–224, (1997).

DOI: 10.1016/s0278-6915(96)00099-3

Google Scholar

[4] Vermeer ITM, Pachen DMFA, Dalliga JW, Kleinjans JCS and Mannnen JMS., Volatile N-nitrosamine formation after intake of nitrate at the ADI level in combination with an amine-rich diet, Environ Health Perspect, vol. 106. p.459–463, August (1998).

DOI: 10.1289/ehp.106-1533225

Google Scholar

[5] Chung, S. Y., Kim, J. S., Kim, M., Hong, M. K., Lee, J. O. and Kim, C. M., Survey of nitrate and nitrite contents of vegetables grown in Korea, Food Additives & Contaminants, vol. 20. p.621–628, (2003).

DOI: 10.1080/0265203031000124146

Google Scholar

[6] Yurchenko, S. and Molder, U., Volatile N-nitrosamine in various Wsh products, Food Chemistry, vol. 96. p.325–333, (2006).

Google Scholar

[7] Castelluccio, C., Paganga, G., Melikian, N., Bolwell, G. P., and Pridham, J., Antioxidant potential of intermediates in phenylpropanoid metabolism in higher plants, FEBS Lett, vol. 368. p.188–192, (1995).

DOI: 10.1016/0014-5793(95)00639-q

Google Scholar

[8] K. Yagi and N. Ohishi, Action of ferulic acid and its derivatives as Antioxidants, J. Nutr. Sci. Vitaminol, vol. 25. p.127–130, (1979).

DOI: 10.3177/jnsv.25.127

Google Scholar

[9] H. Kikuzaki, M. Hisamoto, K. Hirose, K. Akiyama and H. Taniguchi, Antioxidant properties of ferulic acid and its related compounds, J. Agric. Chem, vol. 50, p.2161–2168, (2002).

DOI: 10.1021/jf011348w

Google Scholar

[10] K. Enomoto, T. Miyamori, A. Sakimae and R. Numazawa, Eur. Pat. Appl, EP 401704, (1990).

Google Scholar

[11] K. Sakashita, S. Myamoto and A. Sakimae, Eur. Pat. Appl, EP 514694, (1992).

Google Scholar

[12] LC. J. Tramper and M.D. Lilly, Biocatalysis in organic solvents, Elsevier: Amsterdam, (1987).

Google Scholar

[13] Masayoshi Sawamura, Song H. Sun, Kumiko Ozaki, Junko Ishikawa, and Hiroyuki Ukeda, Inhibitory Effects of Citrus Essential Oils and Their Components on the Formation of N-Nitrosodimethylamine, J. Agric. Food Chem, vol. 47. pp.4868-4872, (1999).

DOI: 10.1021/jf9903206

Google Scholar

[14] Lin Ma, Mattias Persson and Patrick Adlercreutz, Water activity dependence of lipase catalysis in organic media explains successful transesterification reactions, Enzyme and Microbial Technology, vol. 31. p.1024–1029, (2002).

DOI: 10.1016/s0141-0229(02)00231-4

Google Scholar