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Anthocyanins as lipoxygenase inhibitors
Author(s) -
Knaup Bastian,
Oehme Anett,
Valotis Anagnostis,
Schreier Peter
Publication year - 2009
Publication title -
molecular nutrition and food research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.495
H-Index - 131
eISSN - 1613-4133
pISSN - 1613-4125
DOI - 10.1002/mnfr.200800234
Subject(s) - lipoxygenase , chemistry , glycoside , uncompetitive inhibitor , biochemistry , malvidin , delphinidin , arachidonate 5 lipoxygenase , glucoside , stereochemistry , cyanidin , enzyme , antioxidant , non competitive inhibition , medicine , alternative medicine , pathology , arachidonic acid
Health benefits associated with diets rich in anthocyanins are ascribed to multilevel biological activities including antioxidative and anti‐inflammatory effects. The present study addresses lipoxygenase inhibition as a mechanism by which anthocyanins may exert health promoting effects. The inhibitory potential of delphinidin (Dp), cyanidin (Cy), peonidin (Pn), and malvidin (Mv) glycosides, i.e ., 3‐ O ‐glucosides, 3‐ O ‐galactosides, and 3‐ O ‐arabinosides as well as their aglycons was analyzed by using soybean lipoxygenase‐1 and human neutrophil granulocyte 5‐lipoxygenase. The determined IC 50 values comprised a wide range, i.e ., from the sub‐μM level until practically no effect of inhibition (Mv and its glycosides). With IC 50 values of 0.43 and 0.49 μM Dp 3‐ O ‐glucoside (Dp3glc) and Dp 3‐ O ‐galactoside (Dp3gal) were found to be the most effective soybean lipoxygenase‐1 inhibitors; their strong inhibitory potential was also reflected by the IC 50 values determined for these anthocyanins in the 5‐lipoxygenase inhibition exhibiting 2.15 and 6.9 μM, respectively. As to the mechanism of inhibition, experiments carried out with lipoxygenase‐1 revealed the uncompetitive type. Considering the powerful inhibitory properties of Dp glycosides in relation to their currently known availability in human metabolism, in vivo prevention of inflammatory diseases by these anthocyanins could be envisaged.