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Croatian journal of food science and technology, Vol. 9 No. 1, 2017.

Original scientific paper

https://doi.org/10.17508/CJFST.2017.9.1.08

Inhibitory effect of coumarin derivatives on apple (cv. Idared) polyphenol oxidase

I. Strelec ; Josip Juraj Strossmayer University of Osijek, Faculty of Food Technology Osijek, Franje Kuhača 20, HR-31000, Osijek, Croatia
P. Burić ; Josip Juraj Strossmayer University of Osijek, Faculty of Food Technology Osijek, Franje Kuhača 20, HR-31000, Osijek, Croatia
Irena Janković ; Josip Juraj Strossmayer University of Osijek, Faculty of Food Technology Osijek, Franje Kuhača 20, HR-31000, Osijek, Croatia
T. Kovač ; Josip Juraj Strossmayer University of Osijek, Faculty of Food Technology Osijek, Franje Kuhača 20, HR-31000, Osijek, Croatia
Maja Molnar ; Josip Juraj Strossmayer University of Osijek, Faculty of Food Technology Osijek, Franje Kuhača 20, HR-31000, Osijek, Croatia

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Abstract

Inhibitory effect of 32 coumarin derivatives (20 Schiff bases, 5 thiosemicarbazides, 5 thiazolidinones, and their precursors,
7-hydroxy-4-methylcoumarin and 4-methylcoumarin-7-yl hydrazine carboxylate) on partially purified apple polyphenol oxidase was investigated. Thirteen coumarin derivatives inhibited polyphenol oxidase (5 Schiff bases, 5 thiosemicarbazides,
1 thiazolidinone, 4-methyl-7-hydroxycoumarin and 4-methylcoumarin-7-yl hydrazine carboxylate), while 19 derivatives showed no effect on enzyme activity. The most effective inhibitors were thiosemicarbazides, with 4-methyl-1-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl) thiosemicarbazide (compound C23) being the most prominent inhibitor (IC50 = 10.45 µM). The importance of thiosemicarbazide moiety as crucial structure element for strong apple PPO inhibition was confirmed by its cyclisation to thiazolidinone bearing the same substituents as corresponding thiosemicarbazide. Capture of the sulphur atom of thiosemicarbazide group within tiazolidinone ring caused significant loss of inhibitory effect against apple PPO.

Keywords

apple polyphenol oxidase; coumarin derivatives; inhibition

Hrčak ID:

182642

URI

https://hrcak.srce.hr/182642

Publication date:

7.6.2017.

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