Twice acting antioxidants: Synthesis and antioxidant properties of selenium and sulfur-containing zingerone derivatives

Débora M. Martinez; Angelita M. Barcellos; Angela M. Casaril; Lucielli Savegnago; Gelson Perin; Carl H. Schiesser; Kimberley L. Callaghan; Eder J. Lenardão

doi:10.1016/j.tetlet.2015.03.030

Twice acting antioxidants: Synthesis and antioxidant properties of selenium and sulfur-containing zingerone derivatives

Débora M. Martinez, Angelita M. Barcellos, Angela M. Casaril, Lucielli Savegnago, Gelson Perin, Carl H. Schiesser, Kimberley L. Callaghan, Eder J. Lenardão

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

23 Scopus citations

Abstract

Abstract Two new organochalcogen-containing zingerone derivatives, 4-(4-hydroxy-3-methoxyphenyl)-4-(phenylseleno)-2-butanone (2b) and 4-(4-hydroxy-3-methoxyphenyl)-4-(phenylthio)-2-butanone (2c) were prepared and evaluated for their antioxidant properties. DPPH and lipid peroxidation studies show that 2b and 2c have significantly improved antioxidant activity over dehydrozingerone (1) despite having similar electron transfer capacity. We speculate that the improved activity of 2b and 2c is partly due to the ability of these compounds to act twice as phenolic antioxidants through a mechanism that eliminates phenylselenyl or phenylthiyl radicals.

Original language	English (US)
Article number	46033
Pages (from-to)	2243-2246
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2015.03.030
State	Published - Apr 22 2015
Externally published	Yes

Keywords

Antioxidants
Dehydrozingerone
Organoselenium compounds
Organosulfur compounds
Zingerone

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2015.03.030

Cite this

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title = "Twice acting antioxidants: Synthesis and antioxidant properties of selenium and sulfur-containing zingerone derivatives",

abstract = "Abstract Two new organochalcogen-containing zingerone derivatives, 4-(4-hydroxy-3-methoxyphenyl)-4-(phenylseleno)-2-butanone (2b) and 4-(4-hydroxy-3-methoxyphenyl)-4-(phenylthio)-2-butanone (2c) were prepared and evaluated for their antioxidant properties. DPPH and lipid peroxidation studies show that 2b and 2c have significantly improved antioxidant activity over dehydrozingerone (1) despite having similar electron transfer capacity. We speculate that the improved activity of 2b and 2c is partly due to the ability of these compounds to act twice as phenolic antioxidants through a mechanism that eliminates phenylselenyl or phenylthiyl radicals.",

keywords = "Antioxidants, Dehydrozingerone, Organoselenium compounds, Organosulfur compounds, Zingerone",

author = "Martinez, {D{\'e}bora M.} and Barcellos, {Angelita M.} and Casaril, {Angela M.} and Lucielli Savegnago and Gelson Perin and Schiesser, {Carl H.} and Callaghan, {Kimberley L.} and Lenard{\~a}o, {Eder J.}",

year = "2015",

month = apr,

day = "22",

doi = "10.1016/j.tetlet.2015.03.030",

language = "English (US)",

volume = "56",

pages = "2243--2246",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "17",

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TY - JOUR

T1 - Twice acting antioxidants

T2 - Synthesis and antioxidant properties of selenium and sulfur-containing zingerone derivatives

AU - Martinez, Débora M.

AU - Barcellos, Angelita M.

AU - Casaril, Angela M.

AU - Savegnago, Lucielli

AU - Perin, Gelson

AU - Schiesser, Carl H.

AU - Callaghan, Kimberley L.

AU - Lenardão, Eder J.

PY - 2015/4/22

Y1 - 2015/4/22

N2 - Abstract Two new organochalcogen-containing zingerone derivatives, 4-(4-hydroxy-3-methoxyphenyl)-4-(phenylseleno)-2-butanone (2b) and 4-(4-hydroxy-3-methoxyphenyl)-4-(phenylthio)-2-butanone (2c) were prepared and evaluated for their antioxidant properties. DPPH and lipid peroxidation studies show that 2b and 2c have significantly improved antioxidant activity over dehydrozingerone (1) despite having similar electron transfer capacity. We speculate that the improved activity of 2b and 2c is partly due to the ability of these compounds to act twice as phenolic antioxidants through a mechanism that eliminates phenylselenyl or phenylthiyl radicals.

AB - Abstract Two new organochalcogen-containing zingerone derivatives, 4-(4-hydroxy-3-methoxyphenyl)-4-(phenylseleno)-2-butanone (2b) and 4-(4-hydroxy-3-methoxyphenyl)-4-(phenylthio)-2-butanone (2c) were prepared and evaluated for their antioxidant properties. DPPH and lipid peroxidation studies show that 2b and 2c have significantly improved antioxidant activity over dehydrozingerone (1) despite having similar electron transfer capacity. We speculate that the improved activity of 2b and 2c is partly due to the ability of these compounds to act twice as phenolic antioxidants through a mechanism that eliminates phenylselenyl or phenylthiyl radicals.

KW - Antioxidants

KW - Dehydrozingerone

KW - Organoselenium compounds

KW - Organosulfur compounds

KW - Zingerone

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U2 - 10.1016/j.tetlet.2015.03.030

DO - 10.1016/j.tetlet.2015.03.030

M3 - Article

AN - SCOPUS:84939991724

SN - 0040-4039

VL - 56

SP - 2243

EP - 2246

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

M1 - 46033

ER -

Twice acting antioxidants: Synthesis and antioxidant properties of selenium and sulfur-containing zingerone derivatives

Abstract

Keywords

ASJC Scopus subject areas

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