Dehydrozingerone and isoeugenol as inhibitors of lipid peroxidation and as free radical scavengers

D.V. Rajakumar; M.N.A. Rao

doi:10.1016/0006-2952(93)90649-H

Dehydrozingerone and isoeugenol as inhibitors of lipid peroxidation and as free radical scavengers

D.V. Rajakumar, M.N.A. Rao

Manipal College of Pharmaceutical Sciences, Manipal

Research output: Contribution to journal › Article › peer-review

125 Citations (Scopus)

Abstract

The antioxidant properties of three related compounds, dehydrozingerone, isoeugenol and eugenol, were investigated using various models. Isoeugenol was found to be the most active in inhibiting ferrous-ion-,ferric-ion-and cumene-hydroperoxide-induced lipid peroxidation in rat brain homogenates. These compounds also showed significant hydroxyl radical scavenging activity. Isoeugenol was potent in scavenging superoxide anion generated by the xanthine-xanthine oxidase system, whereas eugenol was found to inhibit xanthine oxidase. The high antioxidant activity of isoeugenol may be due to the presence of a conjugated double bond, which increases the stability of the phenoxyl radical by electron delocalization. Such electron delocalization is not possible with eugenol. In dehydrozingerone, the stability was decreased by an electron withdrawing keto group at the para position. © 1993.

Original language	Undefined/Unknown
Pages (from-to)	2067-2072
Number of pages	6
Journal	Biochemical Pharmacology
Volume	46
Issue number	11
DOIs	https://doi.org/10.1016/0006-2952(93)90649-H
Publication status	Published - 1993

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title = "Dehydrozingerone and isoeugenol as inhibitors of lipid peroxidation and as free radical scavengers",

abstract = "The antioxidant properties of three related compounds, dehydrozingerone, isoeugenol and eugenol, were investigated using various models. Isoeugenol was found to be the most active in inhibiting ferrous-ion-,ferric-ion-and cumene-hydroperoxide-induced lipid peroxidation in rat brain homogenates. These compounds also showed significant hydroxyl radical scavenging activity. Isoeugenol was potent in scavenging superoxide anion generated by the xanthine-xanthine oxidase system, whereas eugenol was found to inhibit xanthine oxidase. The high antioxidant activity of isoeugenol may be due to the presence of a conjugated double bond, which increases the stability of the phenoxyl radical by electron delocalization. Such electron delocalization is not possible with eugenol. In dehydrozingerone, the stability was decreased by an electron withdrawing keto group at the para position. {\textcopyright} 1993.",

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AU - Rajakumar, D.V.

AU - Rao, M.N.A.

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N2 - The antioxidant properties of three related compounds, dehydrozingerone, isoeugenol and eugenol, were investigated using various models. Isoeugenol was found to be the most active in inhibiting ferrous-ion-,ferric-ion-and cumene-hydroperoxide-induced lipid peroxidation in rat brain homogenates. These compounds also showed significant hydroxyl radical scavenging activity. Isoeugenol was potent in scavenging superoxide anion generated by the xanthine-xanthine oxidase system, whereas eugenol was found to inhibit xanthine oxidase. The high antioxidant activity of isoeugenol may be due to the presence of a conjugated double bond, which increases the stability of the phenoxyl radical by electron delocalization. Such electron delocalization is not possible with eugenol. In dehydrozingerone, the stability was decreased by an electron withdrawing keto group at the para position. © 1993.

AB - The antioxidant properties of three related compounds, dehydrozingerone, isoeugenol and eugenol, were investigated using various models. Isoeugenol was found to be the most active in inhibiting ferrous-ion-,ferric-ion-and cumene-hydroperoxide-induced lipid peroxidation in rat brain homogenates. These compounds also showed significant hydroxyl radical scavenging activity. Isoeugenol was potent in scavenging superoxide anion generated by the xanthine-xanthine oxidase system, whereas eugenol was found to inhibit xanthine oxidase. The high antioxidant activity of isoeugenol may be due to the presence of a conjugated double bond, which increases the stability of the phenoxyl radical by electron delocalization. Such electron delocalization is not possible with eugenol. In dehydrozingerone, the stability was decreased by an electron withdrawing keto group at the para position. © 1993.

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DO - 10.1016/0006-2952(93)90649-H

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