5438-67-5Relevant academic research and scientific papers
Identification of enterodiol as a masker for caffeine bitterness by using a pharmacophore model based on structural analogues of homoeriodictyol
Ley, Jakob P.,Dessoy, Marco,Paetz, Susanne,Blings, Maria,Hoffmann-Lücke, Petra,Reichelt, Katharina V.,Krammer, Gerhard E.,Pienkny, Silke,Brandt, Wolfgang,Wessjohann, Ludger
body text, p. 6303 - 6311 (2012/08/28)
Starting from previous structure-activity relationship studies of taste modifiers based on homoeriodictyol, dihydrochalcones, deoxybenzoins, and trans-3-hydroxyflavones as obvious analogues were investigated for their masking effect against caffeine. The most active compounds of the newly investigated taste modifiers were phloretin, the related dihydrochalcones 3-methoxy-2′,4,4′-trihydroxydihydrochalcone and 2′,4- dihydroxy-3-methoxydihydrochalcone, and the deoxybenzoin 2-(4-hydroxy-3- methoxyphenyl)-1-(4-hydroxyphenyl)ethanone. Starting with the whole set of compounds showing activity >22%, a (Q)SAR pharmacophore model for maskers of caffeine bitterness was calculated to explain the structural requirements. After docking of the pharmacophore into a structural model of the broadly tuned bitter receptor hTAS2R10 and docking of enterolactone and enterodiol as only very weakly related structures, it was possible to predict qualitatively their modulating activity. Enterodiol (25 mg L-1) reduced the bitterness of the 500 mg L-1 caffeine solution by about 30%, whereas enterolactone showed no masking but a slight bitter-enhancing effect.
The early oxidative biodegradation steps of residual kraft lignin models with laccase
Crestini, Claudia,Argyropoulos, Dimitris S.
, p. 2161 - 2169 (2007/10/03)
A number of model compounds resembling the fundamental bonding patterns of residual kraft lignin, including a series of stilbenes, were incubated with laccase from Trametes versicolor in the presence and absence of delignification 'mediators' ABTS and HBT. The condensed kraft lignin model compounds seem to undergo initial degradation by laccase mainly via benzylic oxidation, demethylation and hydroxylation reactions. Phenolic 5-5', diphenylmethane and α-5 lignin models were found to be degraded mainly via side-chain oxidation reactions. Among the models studied, a phenolic stilbene was found to be the most reactive, yielding several products showing side-chain oxidation/transposition, demethoxylation and hydroxylation reactions. Non-phenolic 5-5', diphenylmethane and stilbene model compounds were found unreactive even in the presence of the laccase-mediator system. Copyright (C) 1997 Elsevier Science Ltd.
