Fate of ferulic acid in overmixed wheat flour doughs : Partial characterization of a cysteine-ferulic acid adduct

To examine the fate of ferulic acid in overmixed dough, a covalent adduct between ferulic acid and cysteine was synthesized to serve as a standard. Spectral data confirmed the loss of the double bond in ferulic acid. The adduct had a negligible effect on dough rheology (Mixograph) indicating loss of...

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Bibliographic Details
Published inJournal of cereal science Vol. 4; no. 1; pp. 87 - 95
Main Authors Jackson, G.M., Hoseney, R.C.
Format Journal Article
LanguageEnglish
Published Kidlington Elsevier Ltd 1986
Elsevier
Subjects
Biological and medical sciences
Cereal and baking product industries
CHA
cysteine
dough
ferulic acid
flour
Food industries
Fundamental and applied biological sciences. Psychology
high performance liquid chromatography
HPLC
mixing
p-toluenesulfonic acid
PTSA
S-cysteinohydroferulic acid
wheat
CHA
HPLC
PTSA
Complexation
Mixing
Spoilage
Paste
Ferrulic acid
Phenols
Rheological properties
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Summary:To examine the fate of ferulic acid in overmixed dough, a covalent adduct between ferulic acid and cysteine was synthesized to serve as a standard. Spectral data confirmed the loss of the double bond in ferulic acid. The adduct had a negligible effect on dough rheology (Mixograph) indicating loss of the thiol group of cysteine. Crystals of the adduct compound, L-S-[β-(4-hydroxy-3-methoxyphenyl) propionic acid] cysteine or S-cysteinohydroferulic acid (CHA), melted with decomposition at 238 °C and showed a good agreement between elemental analysis and theoretical values for C 18H 17NO 6S (C = 49/sd51 % ; H = 5/sd42% ; N = 4/sd41 % ; O = 30/sd47% ; S = 10/sd39%). 13C-NMR was used to confirm the structure of the adduct. Overmixed doughs were hydrolyzed with protease and fractionated on Sephadex G-10. The fraction corresponding to the V e for standard CHA was analyzed by high performance liquid chromatography (HPLC). The chromatogram showed a reproducible shoulder peak. When standard CHA was spiked into the sample just prior to HPLC analysis, that shoulder peak co-eluted with standard CHA. The shoulder peak was thus identified tentatively as being CHA. The data are consistent with the formation of the cysteine-ferulic acid adduct in overmixed doughs.
ISSN:0733-5210
1095-9963
DOI:10.1016/S0733-5210(86)80010-8