Boropinic acid and other natural prenyloxycinnamic and benzoic acids were easily synthesized in high yield by a two-step sequence from the corresponding p-hydroxy aromatic acids and were assayed for radical scavenging activity using the DPPH test and for inhibition of enzymatic lipid peroxidation mediated by soybean 5-lipoxygenase. Compared to other acids and to known antioxidant compounds like BHT, Trolox and ascorbic acid, boropinic acid was far more active in the lipoxygenase test IC50 7.6 ng/mL, p < 0.05). The recorded inhibition value suggested that boropinic acid acted as an enzyme inhibitor rather than a mere radical or peroxide scavenger. This hypothesis was confirmed by studying the interaction between boropinic acid and soybean 5-lipoxygenase by molecular modelling techniques.

Lipoxygenase Inhibitory Activity of Boropinic Acid, Active Principle of Boronia pinnata.

CURINI, Massimo;
2006

Abstract

Boropinic acid and other natural prenyloxycinnamic and benzoic acids were easily synthesized in high yield by a two-step sequence from the corresponding p-hydroxy aromatic acids and were assayed for radical scavenging activity using the DPPH test and for inhibition of enzymatic lipid peroxidation mediated by soybean 5-lipoxygenase. Compared to other acids and to known antioxidant compounds like BHT, Trolox and ascorbic acid, boropinic acid was far more active in the lipoxygenase test IC50 7.6 ng/mL, p < 0.05). The recorded inhibition value suggested that boropinic acid acted as an enzyme inhibitor rather than a mere radical or peroxide scavenger. This hypothesis was confirmed by studying the interaction between boropinic acid and soybean 5-lipoxygenase by molecular modelling techniques.
2006
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11391/108296
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