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Inhibition of bacterial urease by autoxidation of furan C‐18 fatty acid methyl ester products
Author(s) -
Rosenblat Gennady,
Tabak Mina,
Lie Ken Jie Marcel S. F.,
Neeman Ishak
Publication year - 1993
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02542584
Subject(s) - chemistry , autoxidation , urease , thiol , cysteine , organic chemistry , enzyme , reagent , chromatography
Autoxidation products of synthetic methyl 9,12‐epoxy‐octadeca‐9,11‐dienoate (MEFA) were investigated by gas chromatography‐mass spectrometry analysis and tested for bacterial urease inhibition. A suspension of oxidized MEFA in 10% Tween 80 was an effective inhibitor for bacterial urease extract from Helicobacter pylori (I 50 =1.3 mM) and for commercial urease from Bacillus pasteurii (I 50 =0.06 mM). The urease inhibitory effect was cancelled by adding cysteine to the reaction mixture. The total content of biologically active oxidized products in the mixture was found to be 6.2%. Dioxo‐ene derivatives of MEFA on the thin‐layer chromatography plate surface were converted into more stable compounds, whose formation in the mixture reduced inhibition of B. pasteurii to about 2% of the former level. The mechanism of urease inhibition is supposed to involve the interaction of the thiol groups of the enzyme’s active center with the inhibitor molecules.